Hey, Justin here. 👋

Today, I have an important announcement: I’m extremely excited to share that the Just Go Grind newsletter has been acquired by Unicorner.

Unicorner is the premier startup community and newsletter highlighting promising Unicorns-to-be. They’ve written about over 250 early-stage companies since 2020, and they run startup and tech events across the country.

More than that, Arek and Ethan are good friends. They’re active members of the LA tech community, and I’ve known them for years. Over the last few months, we’ve worked closely together to define the future of covering world-class founders and determining what’s next for Just Go Grind.

I’ll leave it to the Unicorner team to talk more about what’s next in their follow-up email. Trust me, the newsletter is in good hands.

As far as what’s next for me: I’ll be doubling down on building The LA Grind and The SF Grind. If you’re looking for curated events and standout founder stories in LA and SF, be sure to check them out.

Pumped for this next stage of the journey!

Justin

Myself + the Unicorner team (Arek and Ethan)

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Today, we’ve got a throwback from the archives about the man, the myth, the legend… Walt Disney!

Few founders have left a mark on the world like Walt Disney.

From a single idea and a few short films in the 1920s, he built a company now worth more than $200 billion, a global force in storytelling, entertainment, and imagination.

What started as sketches of a mouse became a multigenerational empire that defined childhood for millions and reshaped how stories are told.

I’m revisiting this deep dive because Disney’s story is one of unshakable vision, endless reinvention, and refusal to quit when things fell apart.

It’s a reminder of what’s possible when creativity meets persistence and when the dreamer behind the scenes never stops pushing forward.

Here’s the full story of Walt Disney, one of the greatest builders of all time.

Let’s dive in.

Walt Disney was born on December 5, 1901.

After spending the first few years of his life in Chicago, he moved to Marceline, Missouri in 1906.

This was a highly influential experience, as his wife later mentioned:

Marceline was a place Walt’s brother, Roy, described as “heaven for city kids.”

Their Father, Elias Disney, worked hard, lived modestly, and worshiped devoutly, but also had an impulsive temper—opposite from Walt in nearly every regard.

In 1911, Walt and his family moved again, this time to Kansas City.

It was in Kansas City that Walt was forced to develop a strong work ethic, brought upon him by the crazy schedule of his paper route:

Walt later admitted it had a profound effect on him.

That work ethic was soon applied to drawing and two people encouraged Walt and gave him the confidence in his drawing to take it seriously—his Aunt Maggie, and his elderly neighbor, Doc Sherwood—but Doc’s words lasted Walt a lifetime:

That encouragement fueled Walt’s obsession:

Similarly, many years later, a young Patrick Collison, the co-founder of Stripe, would hide his obsessive reading habit from teachers in class.

In 1918, at only 16, Walt attempted to join the army, but, being too young, he was rejected. Instead, he joined the Red Cross after forging the date on his birth certificate.

He spent almost a year in France, arriving after the armistice, serving as an ambulance driver.

After returning to Kansas City in October 1919, he was ready to jumpstart his creative career…

KEEP READING ONLINE.

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Today, we’ve got a throwback from the archives about Whitney Wolfe Herd, the founder of Bumble.

Earlier in 2025, Whitney Wolfe Herd, the founder of Bumble, returned as CEO after stepping down in November of 2023.

A movie about the founding of Bumble, Swiped, was released on Hulu in September of 2025, making this a good time to bring back the deep dive I wrote on Whitney back in May of 2023.

Before we get into it, I’d love to get your feedback on something I’m working on.

I am planning a curated founder retreat in early 2026 within driving distance of Los Angeles. It will be a small group of about 8 founders, with all meals and accommodations included. You only need to get yourself there. The goal is to connect deeply and recharge with other ambitious founders.

Let’s dive in.

Whitney Wolfe Herd, Founder and CEO of Bumble, is the youngest woman ever to take her company public.

She did so in 2021 at the age of 31, about 7 years after going through one of the darkest periods of her life.

Her story, fueled by ambition and a mission to help women, shows what’s possible when you take a different view of the world, intimately understand your customer, and relentlessly execute to make your vision a reality.

Let’s get to it.

Whitney was born in 1989 in Salt Lake City, Utah.

After moving to Paris with her family at the age of 11, she moved back to Utah to finish high school.

By the time she went to college at Southern Methodist University, she had decided to get into marketing and advertising but was rejected because she failed an entrance exam.

If you already know anything about her story today, you’d see the hilarity in this.

More on that shortly.

Instead, she would major in international studies and become a member of one of the sororities, an important piece for later in her story.

While in college, Whitney showcased her desire to make an impact through entrepreneurship by starting a couple of businesses.

One of them, started in response to the BP oil spill, was a non-profit that sold bamboo totes, with proceeds going to the Ocean Futures Society.

The other, an experiment of sorts started during her senior year, was a clothing line meant to raise awareness of human trafficking and fair trade.

She also had a passion for photography, exploring this for a few months after graduating from SMU, and planting some of the very early seeds for the idea of Bumble:

After her trip to Southeast Asia, Whitney would find herself at a serendipitous dinner in Los Angeles, which led to her taking a job at an LA-based startup incubator, Hatch Labs, started by IAC in 2011.

This would turn into two unforgettable years.

In 2012, Whitney worked at the startup Cardify, one of the companies in the Hatch Labs incubator.

This project, led by Sean Rad, would ultimately end up being abandoned, but it led to Whitney working on a dating app called MatchBox which would become Tinder.

Whitney was the co-founder and VP of Marketing for Tinder and, although she never did get that marketing degree, she found creative ways to acquire Tinder’s early users:

But this wasn’t all she did.

She continually found ingenious ways to signup new users:

As I’ve written about previously with Sara Blakely and numerous other entrepreneurs, they’re all relentlessly resourceful - Whitney is clearly no different.

I’m reminded of Paul Graham’s insightful essay on this repeatedly when thinking about the world’s best founders.

And with Whitney, she was so close to the customer that it was easy for her to market to them. She knew them. She was in the target market herself.

The timing was also important:

And this contributed to Tinder’s insane early growth.

In the first two years, they had one billion matches and were getting 800 million swipes per day on the app.

But, it would be a tumultuous time for Whitney, and she’d leave the company in a very public way.

Without getting into all the details because I don’t think it’s worth resurfacing, Whitney filed a lawsuit against Tinder for sexual harassment on June 30, 2014, two months after resigning.

She ultimately reached a settlement in September 2014, but the lawsuit was very public, and, to put things bluntly, it was an absolute shitstorm for Whitney.

She’d describe it as one of the darkest times of her life, saying, “I was literally broken.”

But from the darkness, she found light.

After originally having the idea for a company called Merci, a female-only social network where “You could only be kind to one another,” she was convinced to start another dating company by the now multi-billionaire Andrey Andreev.

But first, Andrey tried to hire Whitney as the CMO of his dating company.

She described the start after Andrey’s attempt failed attempt:

She went further talking about the idea for Bumble in another interview, describing how she rebuffed Andrey’s attempts to become CMO of his company:

And the original name for Bumble was going to be Moxie, but Whitney couldn’t trademark it because others had already done so in a number of domains.

How did she land on Bumble as a name?

Someone on the early team came up with the name Bumble, Whitney hated it at first, but then it all clicked:

And she was obsessed with the details:

Of course, Whitney wasn’t alone.

When asked about early hiring at Bumble, she offered up this:

The team is everything.

And that team executed more great marketing ideas, fueled by a deep understanding of the customer:

Luck and timing. Definitely the underappreciated aspects of a successful business.

The other critical part of Bumble’s story that I just want to highlight again is the simple key differentiator that Whitney came up with: women go first.

It’s the whole premise that Bumble was built on.

And it seems so simple, maybe obvious in hindsight, but we have to remember - nobody was doing this.

My oh my did that pay off for them!

Bumble launched in December 2014, about 6 months after Whitney filed the lawsuit with Tinder.

By May 2015, they have 500k users, 200k messages being sent per day, and 15% week-over-week growth.

Bumble is a team of six people at this time.

By the end of 2015, Whitney would have a team of 13 and more than 15 million unique conversations had taken place on the platform, with 80 million matches made.

In March 2016, Bumble launches Bumble BFF, a feature in the app that helps people make new friends. This is at a time when they were still growing like crazy, having added 1.5 million Bumble users in the first couple of months of 2016. By the end of 2021, 15% of Bumble users had also tried BFF.

2016 was also the year they began monetizing via in-app purchases, charging $9.99 per month for three additional features:

For context, Tinder at this time had amassed 46 million registered users but had only a 10% annual growth rate.

Whitney also reportedly turned down a massive $450 million offer from Match Group to acquire Bumble in early 2017 and again later in 2017 for more than $1 billion. At this point, Whitney owns about 20% of Bumble.

And in October 2017 they launch Bumble Bizz, similar to Bumble BFF but with a focus on professional networking.

By November 2017, Bumble had gained 22+ million registered users since its launch, achieving 70% year-over-year growth. They’d do about $100 million in sales that year.

It’s clear Bumble Bizz and Bumble BFF were investments in the future, and given how well the Bumble product itself was doing, they didn’t necessarily need to expand, but did so in ways that seem to make sense.

In their 2022 annual report, this is mentioned:

This was obviously years after they had launched the products, and while Bizz and BFF aren’t significant revenue for Bumble yet, they very well could be in the not-too-distant future.

But my friends, we’ve gotten ahead of ourselves.

Let’s go back to 2018.

By June 2018, 3+ years in, Bumble has 29 million registrations and is approaching 100 employees.

Bumble, by all accounts, is crushing it.

And yet, things weren’t always rosy for Whitney:

Whitney is clearly incredibly mission-driven and in that interview with Tim Ferriss, she showcases her level of commitment to that mission.

But you can also see the toll the company has at times taken on her.

She’s very open about it all, which I really appreciate, and if you watch some of her interviews, you’ll see her talk about how she’s dealt with her anxiety over time, something I’ve included at the end of this piece in the “Whitney’s Wisdom” section.

Even with her personal challenges, Bumble continues to thrive, and in 2019 there would be a big change.

By 2019, Bumble did $240 million in revenue.

In November 2019, Andrey Andreev, who was instrumental in pushing Whitney to get back into the dating app world with Bumble, sold his entire stake in MagicLab to Blackstone.

MagicLab was the main backer of Bumble, and owned stakes in Bumble, Badoo, and other dating apps.

In the process, Whitney became CEO of the whole company, with her stake being around 19%.

Blackstone also made an additional investment in the company with the deal and valued the entire company, which included Bumble, at $3 billion.

And here was Whitney’s quote in the announcement:

Not long after, Whitney would take another big step for the company - going public.

The Bumble IPO in February 2021 raised $2.2 billion from investors and with it, Whitney became the youngest female founder to take a company public, at only 31 years old.

The stock debuted at $76 and has struggled since, but the stock price isn’t Whitney’s main concern:

It’s a sentiment you hear from a lot of CEOs - they’re trying to build great companies, not worry about stock price, because, if you build a great company, the rest will take care of itself.

Being a public company has its positives and negatives with one drawback being it takes focus away:

And with the level of scale Bumble is at, the importance is in what they choose NOT to do:

And to even get to this point is remarkable.

There are thousands of dating apps and websites, and yet only a few are used prominently.

Bumble is one of them.

And Whitney is the driving force behind that.

In 2021, Bumble did $765 million in revenue. The next year they did more than $900 million in revenue.

And in 2023, Whitney’s big focus, among other things, is Bumble BFF.

Given how prevalent the issue of loneliness has become in today’s society, it makes perfect sense.

It’s also a massive opportunity for growth.

But there’s a big challenge ahead too: AI.

Specifically, keeping AI from being harmful to their users.

More recently, Bumble acquired Official, an app that helps couples form stronger relationships, a continued effort of expansion for Bumble:

Overall, Whitney is looking at 3 major buckets for growing Bumble and their relationship ecosystem:

1. Bumble Date, Fruitz, and Badoo - The core of their business

2. Build or Buy Strategy - What extends the user lifecycle

3. Forray Beyond Love - Bumble BFF, Bumble Bizz, and more broadly, Kind Connections, but platonically

But why does Whitney continue to build Bumble?

She offers her thoughts in the perfect closing to this piece:

 In each edition of the Just Go Grind newsletter, I like to include a few more quotes at the end from my research into the founder who is featured, sharing their wisdom.

On dealing with anxiety:

On starting to take her health more seriously in 2018:

On her best investment:

On helping her team solve problems:

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Today, we’ve got a throwback from the archives about one of the world’s most successful entrepreneurs.

About a week ago, Larry Ellison briefly overtook Elon Musk as the richest person in the world.

It reminded me of the deep dive I wrote about his story and just how wild it was.

Today, I’m sharing it with you, covering the first 20 years of Larry building Oracle.

Before we get into it, I’d love to understand who’s reading. Click the option below that best describes you:

Let’s dive in.

As of this writing, Larry Ellison is the second-richest person in the world and the company he founded, Oracle, is valued at more than $800 billion.

By 1996, nearly 20 years after starting the company, he was already worth $6 billion and was the richest man in California.

Today, we’re diving into his story, before and during those first 20 years of building Oracle.

To write today’s deep dive, I read the insightful book The Difference Between God and Larry Ellison: *God Doesn't Think He's Larry Ellison by Mike Wilson. For the full story, I highly suggest you check it out.

Let’s get to it.

Larry Ellison was born on August 17, 1944 in Manhattan.

After nearly dying from pneumonia at just nine months old, his unmarried, nineteen-year-old mother, Florence, sent him to live with relatives in a middle-class suburb of Chicago.

Not until he was twelve years old did Larry know he was adopted and this was a powerful motivator for him, thinking he had something to prove.

But Larry’s desire to succeed wouldn’t yield tangible results for many years to come.

Along the way, he’d find other motivators, his unsupportive, adoptive father being one of them:

While in high school, Larry mostly flew under the radar, described by one classmate as, “very quiet, very withdrawn, not at all in the mainstream.”

He also started to display the rebelliousness he’d use later in life, refusing to read many of the books he was supposed to read, instead choosing to read what interested him most:

Nonconformist.

Classic entrepreneur, right?

After graduating high school in 1962 he attended the University of Illinois in Champaign-Urbana where his rebelliousness continued:

Larry didn’t stay in college long.

After his sophomore year, when his adoptive mother, Lillian, died of cancer, he left the University of Illinois.

Before leaving school, and after giving up his aspirations to become a doctor, Larry learned to program a computer and utilized that skill to get a job as a programmer at the university.

Not long after, in 1966, he left Illinois for California, a decision that proved incredibly fruitful.

Larry enrolled at Berkeley in the summer of 1966, though he wouldn’t attend long.

After getting married to Adda Quinn in January 1967, Larry worked as a systems programmer for IBM mainframes for a few years at several companies.

It was “monotonous and unchallenging” and, even though he wasn’t making much money, he was spending exorbitantly.

Adda said he had “champagne tastes on a beer budget.”

LOL.

His spending, among other reasons, caused his wife to leave him in 1974.

It was a turning point in his life:

She wasn’t the only one concerned about his prospects though.

Larry later said:

Adda later said of Larry:

This is the type of person that builds a multi-billion dollar company.

But it’d still be a few years before Larry started the company that made him a billionaire.

After losing his job at a company called Amdahl, Larry joined Ampex, an important company for our story.

At Ampex, Larry worked under Bob Miner, in what would later become a collaboration for the ages.

It was through Larry’s dissatisfaction with a manager at Ampex that he even started working with Bob in the first place:

Shows you the value of speaking up and surrounding yourself with great people, doesn’t it?

Larry and Bob would create an iconic, generational company together.

They’d also find their third future co-founder, Edward A. Oates, while at Ampex.

Working together at Ampex for a brief time, the three of them often discussed their disdain for the corporate world.

Soon, they’d start a company of their own.

After quitting Ampex to join a company called Precision Instrument, Larry jumped on an opportunity to work with his former colleagues, Bob and Ed.

Precision Instrument needed software for its hardware and didn’t have programmers who could write the code.

When bids came in from other companies to take on the work, they were overpriced, giving Larry an opening.

Wait, but why pursue this in the first place?

Larry had a good job as a VP, why shake things up?

Larry explained:

Larry, Bob, and Ed organized a bid of $400,000 for the Precision Instrument contract and won it.

They formed a company, Software Development Laboratories, Inc. (SDL) to fulfill it:

In their new venture, Ellison paid $1,200 for 60% of the company’s shares, with Bob and Ed each buying 20%.

Ed explained why Larry got the majority of the stock:

That chutzpah was on display for SDL’s first programmer, Bruce Scott:

With a team being built, Larry and his co-founders had to decide what kind of company they were creating.

Would they take on more contract work or build their own products?

Bob explained the simple rationale behind the decision to build their own products:

It’s also important to understand at this point in our story just how important it was that Larry and Bob had each other to build Oracle:

So we have the right co-founders working together.

They decide they want to be a product-oriented business.

Now… what product?

Well, thanks to IBM researchers, they’d have their answer.

It all started in 1970 with an article by IBM researcher Edgar H. “Ted” Codd.

The title was, “A Relational Model of Data for Large Shared Data Banks” and it was published in June 1970.

At the time, people didn’t make much of it, doubting the potential of relational databases.

As it turns out, years later, relational databases were exactly the product many companies needed.

Without going into too many of the technological details, of which I know very little anyway, here’s what’s important to know:

IBM researchers publicly published several papers about System R, their database research project that used SQL, a programming language built to be a better way to store and process information in a relational database.

But IBM didn’t release a product till years later.

That was Larry Ellison’s opening.

And boy oh boy did he make the most of it.

As Mike Wilson wrote in his book:

It’s a good example of how corporate bureaucracy slows down, and sometimes, kills companies.

IBM didn’t want to sell a product that would cannibalize the products they already had. That resistance by people at IBM slowed down the development of their relational database product.

In the meantime, Larry Ellison and his company took full advantage.

The first customer for Larry’s company?

The Central Intelligence Agency.

Once again, this came, in part, thanks to IBM.

With IBM not yet ready to sell relational database software, the CIA had to look elsewhere.

Relational Software Inc. (RSI), the new name for what would become Oracle, is where they ended up.

After landing the CIA deal, Larry also sold Oracle to the Navy.

Only one problem.

Between the two customers, there were three different operating systems they needed Oracle software to work on.

It forced Oracle to build portable software:

This turned out to be a critical part of the Oracle story.

Larry Ellison promoted the hell out of it too:

One of the computers Oracle software had to work on was the Virtual Address eXtension (VAX) which was developed and sold by the Digital Equipment Corporation (DEC).

But in 1979 Larry didn’t have money to buy a VAX machine.

What’d he do?

He made a deal with the University of California, Berkeley to use theirs.

Another time, Larry negotiated a deal with a different company to keep their VAX machine at Oracle and allow them to use it too.

Eventually, Larry borrowed money so that Oracle could buy its own VAX machine.

It was a worthy investment.

In the ensuing decade and beyond, Oracle made hundreds of millions of dollars from VAX users.

The person who helped Larry with the loan was Donald Lucas, who worked in the same office building as Larry and his team:

Don came into play when Ed Oates, Oracle’s third co-founder, decided to leave the company after his work was suffering and his marriage was dissolving.

They needed to know the fair market value of Ed’s stock and Don helped them do just that.

He’d eventually become the first Chairman of the Oracle Board.

To take Oracle beyond those first couple of customers, Larry did what many software companies at the time were doing - exaggerating both the number of customers they had and what their software could do.

Larry was trying to give Oracle more credibility in the early days.

He knew how important it was to win as much market share as possible as quickly as possible, as he later mentioned:

And although Oracle’s software didn’t always work as advertised in the early days, companies still bought it.

Part of the reason was Oracle’s phenomenal ability to sell it.

Another was that they were building a product on the bleeding edge of technology, a product the CIA, the Navy, and others desperately hoped would work, and so, early on, they got a lot of leeway.

As one member of the Navy said of Oracle software:

With Oracle selling a new sort of software product, Larry’s job was not just to sell Oracle itself, but relational database technology more broadly.

He did it to perfection.

In 1982, Oracle did $2.4 million in sales.

The next year, that number was $5 million.

By 1984, it was $12.7 million and Larry was leading a company of 150 employees.

The same year, Jenny Overstreet became Larry’s assistant, and a driving force for Oracle behind the scenes for years to come:

Of course, Ellison had his own view on time management, offering a lesson on the value of focus:

It’s hard to argue with the results of that approach.

Here’s a ridiculous growth streak for you.

Oracle’s sales doubled in 11 of its first 12 years.

Larry’s sales strategy for Oracle’s software focused on three things:

• Portability

• Connectability

• Compatibility

And he had a peculiar hiring strategy to build the team that would execute:

With that team, Larry had the highest of expectations:

He was also unforgiving:

The culture was ultra-competitive, with “frequent pickup basketball games among Oracle executives” in the 1980s.

I find that amusing and I’m not sure why. Seeing a young Larry Ellison take it to his executives in a pickup game just seems like it’d be fun to witness.

The culture included a high level of commitment as well, especially from salespeople, who were all expected to hit their numbers, and who used some questionable tactics to do so, which put Oracle in a bind later on.

With a salesforce humming along selling Oracle software, Larry ramped up advertising with the help of Rick Bennett.

In Rick’s first year at Oracle, after rarely spending on advertising, they spent $330,000 on ads. The next year, $1.33 million. And by 1987 that number was $4.8 million.

Unsurprisingly, Larry took an aggressive advertising approach as well:

Larry also found another creative way to get an advantage over his competitors:

When the founder of Ingres, Mike Stonebraker, one of Oracle’s main early competitors, was asked about the competition between the two, it was clear why Oracle won out:

Superb marketing certainly goes a long way.

For Oracle, it led them to an IPO in March 1986.

By 1989, Oracle was cruising, doing $583 million in sales.

The company had more than 4,000 employees at this point.

But a big problem, one that had been building for years, was about to show up in a major way.

The numbers told the story:

No bueno.

To grow at a rapid rate, Oracle got sloppy. Very sloppy.

They had negative cash flow, booked very questionable deals for years that included everything from extended payment terms to side letters, and the company took a massive hit.

After announcing their financial results for Q3 of the 1990 fiscal year on March 27, 1990, one where profits increased only 1% compared to the previous year, Oracle’s stock dropped from $25.38 to $17.50, losing 31% in a day.

Mike Wilson’s book goes into way more detail about what led to this, but all that is to say that it was a terrible situation.

Then, on September 6, Oracle announced its first quarterly loss in company history.

Larry had to lay off 10% of Oracle’s workforce, about 400 people in total.

A few weeks later, the stock fell to around $6. It had been above $28 only six months before.

The stock continued to dive, dipping below $5 in November.

Several people thought Larry would be on his way out of Oracle at this time.

Stephen Imbler, the VP of Finance, was not one of them and he made a good point about Larry:

After the dip, Oracle made changes.

Their new CFO, Jeff Henley, was one of the people leading the charge.

In 1989, revenue grew 102%.

In 1991, growth was only 12% and in 1992 it was 15%.

This was painful given what they were used to, but was completely necessary.

The crazy part?

In hindsight, the bad quarter didn’t matter much at all:

In 1996, nearly 20 years after Larry Ellison started Oracle, the company had 23,113 employees and did $4.2 billion in revenue with $603 million in profit.

The key to the success of Oracle in those first 20 years could be summed up with a quote by Gary Kennedy: We did what we had to do.

Larry built a company filled with people who played to win.

Yes, it caught up to them in 1990, but it also made Oracle remarkably successful.

Could a more passive founder have accomplished what Larry did in those first 20 years?

I doubt it.

There’s a reason why companies like Oracle and Microsoft came out on top at that time - they were both led by aggressive founders who played to win… and won.

Larry was ruthlessly competitive in all areas of life during that time and it made Oracle fabulously successful, but also came at a high personal cost, including multiple failed marriages.

Nonetheless, Larry built Oracle his way:

Thanks for reading! If you’d like to read the book by Mike Wilson, which includes way more details than I could include in this piece, check it out here.

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders!

Dara Ladjevardian sold his first startup within a year, then set out to tackle something far more ambitious: Delphi, a platform that creates a digital version of your mind, a 24/7 interactive presence that can coach, teach, and share your expertise long after you have left the room.

In this episode, Dara shares how he went from experimenting with recreating his grandfather’s wisdom to raising a $16 million Series A led by Sequoia, why he believes Delphi is the future of mentorship and digital legacy, and how persistence through “false fails” shaped the company’s journey.

Dara also breaks down finding the right co-founder, building a brand people trust with their identity, scaling entirely through word of mouth, and what it takes to create a product designed to last 500 years.

This was such a fun interview and I hope you enjoy it!

Thank you to today’s sponsor, Relay Human Cloud, for supporting the show!

Listen to Dara’s interview on YouTube, Spotify, or Apple Podcasts.

Let’s dive in.

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• Delphi lets you scale your mind through AI. The platform creates a digital version of you that others can interact with anytime, anywhere.

• The idea began with Dara’s grandfather. After reading Kurzweil’s How to Create a Mind, Dara experimented with building a digital version of his grandfather, inspiring the vision for Delphi.

• Early traction came without marketing. Delphi grew through word-of-mouth and organic adoption rather than paid channels.

• Top use cases include education, coaching, and mentorship. Experts and creators use Delphi to extend their reach and provide value beyond traditional books or courses.

• Identity verification is essential. Users must upload a photo holding their ID to ensure authenticity and trust.

• Delphi ingests content to keep your digital mind current. Tweets, blogs, podcasts, and videos help shape how your digital version engages.

• Investors include Sequoia and Founders Fund. Delphi also attracted prominent creators like Brendon Burchard and Tiago Forte.

• “Digital mind” is deliberate wording. Dara avoids terms like “clone” or “chatbot” to emphasize individuality and humanity.

• The technology goes beyond surface answers. Delphi’s “mind architecture” captures not just knowledge but reasoning, priorities, and worldview.

• Nuance is the differentiator. Digital minds reflect how you think—contradictions, associations, and evolving beliefs.

• Integrations make Delphi versatile. It can be accessed via websites, Slack, WhatsApp, and more.

• Lean but ambitious team. Delphi balances seasoned hires with young, high-slope talent who grow quickly.

• The vision is massive. Dara sees Delphi as a long-lasting “Library of Alexandria for minds.”

• False fails shaped the journey. Delphi faced slow traction at first, but persistence and iteration proved the idea’s strength.

• Product quality drives growth. Dara believes the best products don’t need paid ads because users become evangelists.

• In-person presence builds trust. Speaking at conferences and meeting customers face-to-face helps overcome skepticism.

• Hiring is deliberate and values-driven. Every team member has fully bought into the mission, often relocating to SF to be all-in.

• Delphi creates new forms of monetization. From courses to digital coaching, creators are using Delphi to engage and earn in unique ways.

Listen to Dara’s interview on YouTube, Spotify, or Apple Podcasts.

• What Delphi is and how it works

• The story of building a digital version of Dara’s grandfather

• Early traction and the first acquisition

• Use cases across coaching, mentorship, and education

• Why “digital mind” matters more than “clone”

• Building trust and verifying identity

• How content ingestion powers the experience

• Product iteration and overcoming false fails

• Raising $16M from Sequoia and others

• The role of in-person trust and conferences

• Lean team structure and unique hiring practices

• Inspirations from neuroscience and Kurzweil

• Branding, positioning, and deliberate messaging

• Balancing young talent with experienced hires

• Organic growth vs. paid marketing

• Strategic integrations across communication platforms

• Challenges of building in a new category

• Delphi as a brand and trusted steward of digital legacy

• Long-term vision: a global library of digital minds

Listen to Dara’s interview on YouTube, Spotify, or Apple Podcasts.

Best,
Justin

Founder of Just Go Grind

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders!

Andrew D’Souza built Clearco into a nine‑figure financing platform, then pivoted to start something completely different: Boardy, the AI super connector that hops on a call, learns what makes you tick, and matches you with the exact person who can unlock your next milestone.

In this episode Andrew explains how he seeded Boardy inside HF0, raised an $8 million seed round from investors who first vetted the product by talking to the bot, and is now turning a cartoon character with an Australian voice into a network‑effect business that could one day rival the Swiss economy.

Andrew shared his perspective on crafting AI products, solving the cold‑start problem, fundraising through pure product pull, and more.

Thank you to today’s sponsors, MACROFIT and Relay Human Cloud, for supporting the show!

Listen to Andrew’s interview on YouTube, Spotify, or Apple Podcasts.

Let’s dive in.

MACROFIT Is Building the Future of Fitness Hardware + Subscriptions

I use the MACROFIT Home Gym every day and it’s one of the best products out there for bodyweight and calisthenics training.

The team is now raising to turn MACROFIT into a holdco of premium fitness tech products with strong recurring revenue. They just acquired Flexia Pilates, a connected pilates platform tapping into one of the fastest-growing categories in wellness.

Next up: the launch of Newton, their smart strength trainer — think Tonal, but way better.

More on the acquisition here: LinkedIn Post

Check out MACROFIT: www.joinfitapp.com

Founder: Mike DeVerna (Former COO of Wag!, $400M+ raised)

• Design for network effects from day one. A product that becomes more valuable with every user compounds, but it also demands heavy early effort to reach critical mass.

• Solve the cold‑start problem by hand‑seeding quality users. Andrew personally invited accomplished founders and investors to give Boardy its first high‑signal data set.

• Turn early wins into social proof. Prompt users to share success stories publicly; these authentic testimonials outperform viral hacks.

• Let investors experience the product before pitching. A weekend of calls with Boardy convinced a VC to lead the $8 million seed with no formal process.

• Give your AI a memorable character. Boardy is “half OpenAI, half Pixar,” making every interaction feel human and sticky.

• Collect proprietary data. Fifty‑thousand human conversations already feed Boardy’s matchmaking engine, creating a moat no rival can scrape.

• Keep the core team tiny and mission‑driven. A lean crew preserves shared context and speeds iteration.

• Place strategic bets on emerging model capabilities. Boardy’s team projects where latency, memory, and context limits will land, then builds ahead of them.

• Meet users on their channel of choice. Phone, WhatsApp, email, LinkedIn, and X all funnel back to one continuous profile.

• Capture user priorities, not just profiles. Boardy asks what problem is most urgent right now so matches feel immediately relevant.

• Use storytelling to grow, not gimmicks. High‑value matches inspire organic word‑of‑mouth that beats shallow “AI tourist” traffic.

• Blend art and science in prompt engineering. An ex‑actor on the team writes “notes,” not rules, so the bot’s tone stays consistent across every medium.

• Aim for depth over feature breadth early on. Boardy has no dashboard; all engineering effort goes into smarter, faster matching.

• Benchmark your long‑term vision in plain numbers. Andrew’s near‑term KPI: Boardy’s facilitated economy exceeds Switzerland’s trillion‑dollar GDP.

• Leverage compounding data to improve judgment. Each match trains the system to predict who will accept future introductions.

Listen to Andrew’s interview on YouTube, Spotify, or Apple Podcasts.

• What Boardy is and how it works

• How HF0 sparked Boardy’s creation

• Seeding the first network and solving the cold‑start problem

• Building real network effects and a flywheel that compounds

• Raising an $8 million seed round by letting investors “meet” the product

• Designing a product with no dashboard

• Keeping the team lean and fast

• Blending art and science in prompt engineering

• Growth loop driven by user success stories, not gimmicks

• Why trust and double‑opt‑in intros matter

• A trillion‑dollar vision

Listen to Andrew’s interview on YouTube, Spotify, or Apple Podcasts.

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders!

Crazy idea…

I’m pouring more time into The LA Grind and weighing the best future for the Just Go Grind Newsletter and Podcast. I might keep building it myself, bring in a partner, or even sell it to a new owner.

Before I decide, I’d like to gauge real interest from this community. Please pick the option that fits you in the poll below.

I’m excited to bring you the latest Just Go Grind Podcast interview with David Lord, a serial entrepreneur and the Founder & CEO of Guidesly, a platform where you can book the world’s best outdoor trips & activities.

David Lord grew up chasing trout and tarpon, spotting the pain points of working guides long before most tech founders ever booked a charter.

Today he runs Guidesly, a vertical-SaaS marketplace that helps guides own their customer relationships, fill calendars, and automate marketing with JackAI.

In my conversation with David, you’ll hear how a stubborn “no-asshole” rule shapes every hire and investor decision, why David waited until after a $9.5 million Series A to spend a dollar on brand, and what it takes to cut churn to almost nothing when your customers live on the water.

If you are building a marketplace, wrestling with SaaS retention, or looking for a durable moat, this episode is for you.

And, if you’re interested in going through the same accelerator, 43North, that David went through with Guidesly, getting a $1M investment in the process, apply today, applications close July 9th!

Thank you to today’s sponsor, MACROFIT, for supporting the show!

Listen to David’s interview on YouTube, Spotify, or Apple Podcasts.

Let’s dive in.

MACROFIT Is Building the Future of Fitness Hardware + Subscriptions

I use the MACROFIT Home Gym every day and it’s one of the best products out there for bodyweight and calisthenics training.

The team is now raising to turn MACROFIT into a holdco of premium fitness tech products with strong recurring revenue. They just acquired Flexia Pilates, a connected pilates platform tapping into one of the fastest-growing categories in wellness.

Next up: the launch of Newton, their smart strength trainer — think Tonal, but way better.

More on the acquisition here: LinkedIn Post

Check out MACROFIT: www.joinfitapp.com

Founder: Mike DeVerna (Former COO of Wag!, $400M+ raised)

• Adopt a strict “no-asshole” policy. Vet every investor and hire by calling past partners; if the references say they’re difficult, walk away.

• Solve a problem you know cold. David built in fly-fishing because decades on the water let him spot pain points outsiders miss.

• Ride enabling tech waves. Vertical-SaaS toolkits, Stripe marketplaces and React Native made a once-impossible platform feasible. Watch for similar unlocks in your niche.

• Time fundraising to claim the market. He raced to raise once a federal report showed guiding was a $50 billion U.S. market, knowing fast capital would pre-empt copycats.

• Curate a value-add cap table. Hand-pick angels and funds that bring sector knowledge, AI talent or distribution, not just money.

• Filter hires for genuine passion. Require candidates to love the craft your customers live for; it keeps culture tight and service authentic.

• Leverage accelerators strategically. 43North gave capital, a supportive Buffalo network and early enterprise customers. Pick programs that fill your biggest gaps and lean in.

• Delay brand spend until Series A. Before product-market fit, every marketing dollar can be wasted; he waited, then funded a pro rebrand once the model was proven.

• Automate customer wins with domain-specific AI. JackAI turns guide photos into website updates, social posts and CRM emails without human effort. Look for analogous workflows to own in your vertical.

• Obsess over customer success to slash churn. Guidesly’s 0.5 % annual churn stems from hands-on best-practice coaching; invest here before pure growth hacks.

• Sell founder-led first. “Eat what you hunt” outreach validated demand before paid ads; direct calls teach you the real objections.

• Choose initial geos for year-round revenue. Florida charters fish 365 days and gross seven figures, beating seasonal Montana rivers. Start where unit economics are strongest.

• Seek brutal expert feedback early. A tough AI investor told David “you don’t know it,” prompting a full technical reboot that became a moat; invite hard critiques.

• Scale only after the platform is complete. He finished SaaS, marketplace, and AI layers before pouring dollars into marketing, ensuring capacity matched demand.

• Build for legacy, not just exit. A mission that matters—to improve working guides’ livelihoods—magnetizes talent, investors and customers for the long haul.

Listen to David’s interview on YouTube, Spotify, or Apple Podcasts.

• David’s fly-fishing pain point that sparked the idea (guides “get screwed”)

• Tech tailwinds (Stripe, React Native, vertical SaaS) that made the model viable

• The strict “no-asshole” rule for teammates and investors

• Discovering a $50B market and deciding to fund-raise fast to win it

• Hiring only people who treat outdoor guiding as a life craft

• Building a marketplace and vertical-SaaS platform in parallel

• Why Florida’s year-round charters became the launch beachhead

• Founder-led sales that onboarded 1.6 K+ SaaS guides

• “Guide happiness” and the 0.5 % annual churn superpower

• Winning 43North and how the accelerator turbo-charged growth

• Spreading to new verticals and why vertical-AI gives a durable moat

• Launching Guidesly Pro and the company’s first brand push

• Value-add investors: how Yeti Capital’s “brand whisperer” came aboard

• JackAI: zero-click content, CRM and Google posts from a single photo

• Scaling a 20-person AI team with heavy Amazon support

• Legacy over exits: aiming for a Yeti-sized, industry-changing outcome

Listen to David’s interview on YouTube, Spotify, or Apple Podcasts.

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders!

I’m a big fan of Macrofit and highly suggest it.

My schedule is packed—work, training, life. I needed something reliable, compact, and easy to use. That’s why I train with the Macrofit Home Gym.

I use it almost every day—pull-ups core, resistance bands. It’s sturdy, compact, and actually makes me want to workout.

Built for real strength in small spaces, the Macrofit Home Gym fits in your home, sets up in minutes, and pairs perfectly with your routine.

No bulky equipment. No commute. No excuses.

Get 20% off your own setup by clicking the button below or using promo code JUSTGOGRIND at checkout.

Check out the Macrofit Home Gym

We’re switching things up today.

The first half of the year has been a whirlwind and we published A LOT of newsletters and podcasts already.

Thanks for being here.

YOU make this newsletter possible.

Today, I wanted to recap the first half of 2025 in the Just Go Grind world by sharing with you 5 of the top articles and podcasts so far.

Let’s get to it…

Y Combinator: The Inside Story of Tech’s Most Influential Startup Accelerator

How HF0’s Dave Fontenot Helps Founders Birth Their Life’s Work

The $3.5B Maverick Studio That Took Over Hollywood

Zero to $80M in 4 years with John Andrew Entwistle of Wander

The Ultimate Guide To Funding Your Startup

A bit different than the rest, this piece covered:

• Foundational Knowledge: Startup Funding Basics

• Venture Capital Resources

• Alternative Funding Options

• Tools for Pitching & Building

• Platforms to Discover and Connect with Investors

• Essential Funding Toolkits and Lists

• Newsletters and Blogs to Source from

That’s it folks!

We’ll be focusing a bit more on the podcast moving forward, but we’re always experimenting with ways to deliver value to you, the reader.

Oh, and if you live in LA and want to know about all of the best events, venture deals, career opportunities, and more, check out The LA Grind.

See you next week 😊 

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Today’s deep dive is available for premium subscribers.

I’m a big fan of Macrofit and highly suggest it.

My schedule is packed—work, training, life. I needed something reliable, compact, and easy to use. That’s why I train with the Macrofit Home Gym.

I use it almost every day—pull-ups core, resistance bands. It’s sturdy, compact, and actually makes me want to workout.

Built for real strength in small spaces, the Macrofit Home Gym fits in your home, sets up in minutes, and pairs perfectly with your routine.

No bulky equipment. No commute. No excuses.

Get 20% off your own setup by clicking the button below or using promo code JUSTGOGRIND at checkout.

Check out the Macrofit Home Gym

The world Tammy Sun encountered before ever founding Carrot has now changed, and much for the better.

Education and culture around fertility have significantly evolved, and there is now more consciousness than ever about the importance of planned parenthood. There is still an accessibility gap, however, that threatens with stretching more and more in the future.

More than half of all Americans get their healthcare benefits through their job, and those benefits almost never include fertility practices.

So when Tammy realized the fertility space had been ignored for way too long and decided to do something about it, she knew it had to be through the largest healthcare distributor in the country - the job market.

Through comprehensive and personalized healthcare plans, Carrot allows for employers to cover their employees access to all things fertility as much as they do medical, dental and vision, positioning it as the fourth big pillar of patient care.

After nearly a decade leading Carrot, Tammy’s mission remains the same: not only to uphold everyone’s right to start a family, but also to ensure access to information, expand available options, and empower fertility decisions regardless of age, gender, race, income, or sexual orientation.

KEY TAKEAWAYS FROM TAMMY SUN

Don’t have time to read the whole piece?

Here’s what you need to know from Carrot’s Tammy Sun, tying her lessons into ones we’ve previously learned from other founders we’ve covered:

• Let the problem find you, then don’t let go. Tammy didn’t set out to become a founder. Instead, she discovered a problem that hit home, and she couldn’t walk away from it. Founding a company doesn’t always start with an idea; sometimes it starts with a personal experience that won’t let you ignore it.

• Deep understanding beats perfect credentials. She immersed herself in fertility science, attending medical conferences as the only non-doctor in the room. As a founder, becoming an expert in your space, even without formal training, can be your biggest asset.

• Mission clarity drives momentum. From bootstrapping to navigating rejections from investors, Tammy stuck with it because the mission was clear and urgent. Customers resonated with the need, even when VCs didn’t at first. The lesson: clarity and conviction in your “why” will carry you through hard seasons.

• Choose the right vehicle for your impact. Tammy considered government and non-profit routes before choosing the startup model; not because she idolized startups, but because it was the sharpest tool available. Founders should choose the structure that best aligns with the scale and speed their mission requires.

• Build for inclusivity from the start. Carrot’s reach today, 800+ companies across 170+ countries, comes from designing with inclusivity and flexibility baked in. Instead of narrowing the customer, Tammy asked: How can this work for everyone? Broad missions require infrastructure that can adapt and grow with your users.

Way before CEO life ever happened for Tammy Sun, the early days were already a bit of a frenzy.

She was born in Taiwan but at the age of 3 her family moved to Salt Lake City, where her dad was pursuing a Master’s Degree in Computer Science. Soon after, the family moved to New Jersey, this time to stay, since he got the opportunity to work for AT&T and Bell Labs - the very same place where Tammy would later have her first ever job as an intern.

Balancing her dad’s passion for numbers and metrics, her mom encouraged both Tammy and her sister to find other ways of expression and development outside of academics for a more comprehensive learning experience: art and piano lessons, athletics, horseback riding - they were free to explore and find what they liked best.

Pursuing her passion for International Relations and Women’s Studies, Tammy graduated from NYU and attended the London School of Economics. But even before completing her degree, she was already navigating the world of politics from inside the White House itself.

As an intern and Executive Assistant to Vice President Al Gore, Tammy gained an up-close understanding of how government can serve as a powerful platform for impact and change.

That’s also what the first few years of her career were spent on - she went on to work for the Clinton Foundation and later as a presidential appointee in President Barack Obama's administration at the Federal Communications Commission.

The first pivot in her career was in 2013 when she got the Director of Partnerships position at Evernote. It was during this time that the idea of Carrot sparked.

However, entrepreneurship had always been latent in the family, for both Tammy and her sister would grow up to become founders.

While her sister has spent the last decade working on the Opioid crisis and trying to serve those communities, Tammy has mainly focused on fertility healthcare since 2016, when Carrot was born.

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Premium subscribers get full access to this newsletter, exclusive events, event discounts, and more.

Colleen Heidinger is the president of 43North, a pioneering startup competition and venture program focused on building Buffalo into a thriving center for innovation and entrepreneurship.

Applications now open.

With a strong background in venture capital and startup ecosystems, Colleen has spent over a decade guiding 43North from its inception to becoming a powerful engine for early-stage companies.

She believes deeply in the long-term nature of building successful entrepreneurial communities and emphasizes the importance of patience, reinvestment, and collaboration.

Known for her approachable leadership and commitment to sharing knowledge, Colleen supports founders by encouraging them to reflect on their business goals and navigate the challenges of growth. Her work has helped transform Buffalo’s startup landscape and continues to inspire entrepreneurs to dream big and build with purpose.

Listen to Colleen’s interview on YouTube, Spotify, or Apple Podcasts.

Let’s dive in.

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I used Athyna to hire a writer for Just Go Grind, the experience was seamless, and I’ve been so happy with who I hired. Can’t recommend them enough!

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• Leading with ambition attracts serious founders. From the very beginning, 43North launched with $1 million investments per company. This level of ambition helped them stand out in a competitive landscape and signaled to founders that they were building something serious. If you want to attract great talent or partners, you have to lead with bold decisions that reflect your long-term vision.

• Treat every part of your company like a prototype. Over the years, 43North adjusted everything from check sizes to judging panels to the structure of their selection process. They improved retention, brand perception, and founder experience by listening and iterating. As a founder, you should constantly question what can be optimized, even in parts of the business that seem to be working.

• People do not just join companies, they join communities. One of 43North’s strengths is that it is not just an accelerator with funding. It is a shared experience. Founders relocate to Buffalo, work together in the same building, and build real relationships. If you are building a team or startup, remember that culture and connection are often what make people stay long term.

• Fewer but better applications can lead to stronger outcomes. At one point, 43North received over 12,000 applications, but they realized that quality mattered more than volume. They redesigned their process to require more thoughtful applications, and that led to stronger companies and better fit. For founders, this is a reminder that more leads or users is not always the goal. The right ones are what move the needle.

• Leadership will never come at the perfect time, and that is the point. Colleen became president of 43North just weeks before the COVID shutdown. She had to navigate a relocation, a pandemic, and a new role all at once. Her experience is a good reminder that founders rarely get to grow under ideal conditions. The most meaningful lessons come during chaos, not comfort.

• Be strategic with longer timelines because quality takes time. While four months might feel like a long wait for founders expecting capital, Colleen explains that the process is carefully structured to ensure thorough due diligence and strong decision-making. For founders, the takeaway is that well-run programs take time and it is worth being patient when the opportunity is built on quality.

• The funding is great but the network might be even better. Even companies that do not win 43North’s million dollar investment often benefit from exposure to investors, feedback on their business, and new opportunities. Founders should view accelerators and competitions not only as a chance to raise money but as a moment to build lasting relationships and gain valuable visibility.

• Standardized advice does not work for every founder so know what you need. 43North evolved away from giving all companies the same program because every founder is at a different stage. Now the support is based on each company’s individual needs. The lesson for founders is to clearly identify where they need the most help and seek programs or mentors that can provide targeted support.

• Bigger checks come with higher expectations so be ready to perform. 43North transitioned from funding a larger number of companies to focusing on fewer startups with larger investments. Now they invest one million dollars in five companies each year. That shift means they are looking for stronger founders who can truly deliver results. If you are aiming to raise significant capital, know that you will be held to a higher standard and need to show clear potential for success.

• Government funding can support long term growth and ecosystem building. Unlike private venture capital which often prioritizes fast returns, 43North benefits from state funding that allows them to focus on economic development and long term impact. For founders, this shows that government backed programs may offer more stability and a longer runway to grow, especially in regions looking to build their tech ecosystems.

Listen to Colleen’s interview on YouTube, Spotify, or Apple Podcasts.

00:00 What’s coming in the episode…

00:23 Introduction

01:01 What is 43North?

03:27 The early days of 43North

07:08 Covid days at 43North

09:14 Admission process

16:02 Getting the right partners

19:58 The first IPO from a 43N’s company

21:02 The long-year program

26:53 Why five “$1M” on investment money?

31:02 The impact of 43North

34:50 What’s next?

40:13 Why has 43N succeeded?

41:15 Take a look at the application!

42:22 Reach out to Colleen

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Premium subscribers get full access to this newsletter, exclusive events, event discounts, and more.

I'm looking for a few sponsors to partner across the Just Go Grind podcast and newsletter, as well as The LA Grind, my new LA-focused newsletter for founders, operators, and investors.

Each week, I interview world-class founders like John Andrew Entwistle (Wander), Waseem Daher (Pilot), Jacob Jaber (Philz Coffee), and Dave Fontenot (HF0), reaching a highly engaged audience of builders and decision-makers.

Sponsorship packages include:

• Pre-roll mentions on the podcast (distributed on all platforms including YouTube, with your logo featured in the video)

• Feature placement in the Just Go Grind newsletter (20,000+ subscribers, 52% open rate)

• Distribution through social clips across multiple channels (50k+ followers)

Optional add-ons:

• Shoutouts in The LA Grind (1,200+ LA-based subscribers and growing)

• Visibility at upcoming LA events

Packages start at $2,500.

If you're interested or know someone who should be, fill out this short form or reply directly to this email.

Thank you!

Mehul Nariyawala’s path to robotics started long before Matic ever existed.

With a background in computer vision and a sharp eye for consumer needs, he was fascinated by how machines perceive the world, and how that perception could transform everyday life.

After co-founding Flutter, a gesture-recognition startup acquired by Google for $40 million, Mehul took on product leadership at Google Nest, where he worked on the Nest Cam lineup. But the more he worked on smart devices, the more he saw a bigger opportunity: home robots weren’t living up to their promise.

He realized the gap wasn’t just in hardware; it was in perception, navigation, and autonomy. So in 2017, alongside co-founder Navneet Dalal, Mehul launched Matic to build a fully autonomous, vision-first floor-cleaning robot; one that could finally move intelligently through the unpredictable landscape of a real home.

Now, Mehul is pushing the boundaries of home robotics, creating products that aren’t just technically impressive but meaningfully useful, changing the way people live with technology.

Listen to Mehul’s interview on YouTube, Spotify, or Apple Podcasts.

Thank you to our sponsor:

• Rho - A business banking platform, purpose-built for startups.

Let’s dive in.

Rho is a business banking platform, purpose-built for startups and they work with everyone from two-person YC startups with world-changing ideas to publicly-traded enterprises.

With Rho, founders get:

• A single pane of glass they can use to run and scale their business from Day 1: Bank account, corporate cards to start running – and expense management, bill pay automation, and accounting to help you move fast as you scale.

• The big thing with Rho: Every customer has a "person" at Rho. 24/7 customer support - phone, text, email - they will be there at every critical milestone in your startup's journey.

To learn why startups choose Rho, visit www.rho.co today.

• Don’t chase cool tech, solve real problems instead. Mehul learned (especially after Paul Graham’s feedback) that building “sexy” or futuristic products doesn’t matter if you’re not solving an actual pain point. Basically, resist the temptation to tinker just because something is technically impressive.

• Build on top of experience and compound your learnings. Matic Robotics wouldn’t have been possible as a first startup; Mehul says his earlier ventures were essential for learning the hard lessons. You should see each startup or role as building blocks that help them tackle increasingly complex challenges later.

• Choose markets that already exist, but innovate on product. Instead of creating a market from scratch (which is much harder), Matic focused on a massive existing consumer pain -home cleaning- but approached it with radically better technology. Look for underserved but proven spaces.

• Define long-term alignment and “rules of engagement” before starting. Mehul and his co-founder had a clear framework for picking their next problem: it had to align with their skills (computer vision), have a known business model, be useful and iconic, and be challenging enough to keep them engaged for decades. Set your own criteria upfront will guide you to better decisions.

• Raise money at the right time, not just because you can. As a repeat founder, it’s tempting to raise money early just because you have the credibility. But they chose to bootstrap first to make sure they built a culture of capital efficiency and avoided the trap of raising just to survive. Venture capital is “rocket fuel”, and you don’t load up the rocket until it’s on the pad and ready.

• Build a long-term mission, and let people self-select. From the start, Matic was brutally upfront with hires: if you want a one- or two-year stint, this isn’t the place. They even set six-year vesting schedules to make sure people were truly signing on for the marathon, not a sprint. This helped them attract mission-driven people who believed deeply in the long game.

• Conviction grows over time. Watch for the signs. They used Scott Belsky’s framework: as you work, is your conviction strengthening or fading? Even though the robot wasn’t perfect early on, customer testing showed flashes of delight; those “wow” moments were a key signal to keep going. Stronger conviction, not just sunk time, justified pushing forward.

• You won’t get pricing, go-to-market, or messaging perfect on day one; plan to iterate. Even experienced founders with YC background and industry mentors admit they got pricing and subscription models wrong. The lesson: treat pricing and marketing as experiments, not permanent decisions. Build in flexibility to adjust based on real customer feedback.

• Stay laser-focused: don’t open too many battle fronts too early. The war analogy is powerful: you have to win and secure one front before expanding. Founders should resist the temptation to chase every opportunity or new idea too soon; scale what’s working first, then explore adjacent products or markets.

• Solve real, specific problems people don’t buy “robots,” they buy solutions. This is a great reminder: focus on solving meaningful, concrete pain points, not just building cool tech. Always work backwards from the problem, not forward from the gadget.

Listen to Mehul’s interview on YouTube, Spotify, or Apple Podcasts.

00:00 What’s coming in the episode…

00:13 Introduction

01:39 Mehul’s background

07:49 YC’s Paul Graham’s insight on Mehul’s previous startup

11:54 From Flutter to Matic

16:48 Matic’s first robot

22:14 Matic’s early days and fundraising

25:37 Building the right team

28:07 Known and unknown challenges in robotics

34:28 Last few days before launch

36:08 The mentality for a long job

40:23 Figuring out Matic’s market strategy and pricing

50:41 Building the present and planning the future of Matic

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Today’s deep dive is available for premium subscribers.

I'm looking for one great sponsor to partner with Just Go Grind.

Each week, I feature conversations with world-class founders like John Andrew Entwistle (Wander), Waseem Daher (Pilot), Jacob Jaber (Philz Coffee), and Dave Fontenot (HF0). The podcast runs weekly, and with the right partner, I’d love to ramp it up.

The sponsor package includes:

• Mentions on the podcast (Podcasting platforms & YouTube, 60s pre-roll)

• Feature in the newsletter (20k+ subscribers, 52% open rate)

• Distribution across social video clips and content (Thousands of views)

• Optional add-on: shoutouts in The LA Grind (a fast-growing local newsletter for LA’s most ambitious founders, 600+ subscribers and climbing) and visibility at events

Packages start at $5K for a full month. If you're serious about reaching high-quality builders or know someone who should be in the mix, fill out this quick form or reply directly to this email:

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Would love to lock in the next sponsor this week.

I’m hosting a hike for the LA startup community next week as part of The LA Grind.

​It’s a chance to take a break from your screen for a couple of hours, exercise outside in the lovely LA weather, and meet some great founders, operators, investors, and more in the LA startup ecosystem.

Move events coming up soon!

Join us for the hike here.

The story of David Holz is one driven by curiosity.

Curiosity that extended not only to the world around him but also to the one that, for decades now, has been quietly building behind our screens.

Exploring computers from an early age gave him just a glimpse of what technology could be like in the near future: pretty much limitless.

And so, he made it his mission to uncover the possibilities the digital world could offer when combined with human abilities; first through Leap Motion, and later, through Midjourney.

From excitable gamer to dedicated student, from innovation leader to “the man who said no to Apple, twice” — David has become one of the defining voices of the AI generation, and one of its most optimistic.

KEY TAKEAWAYS FROM DAVID HOLZ

Don’t have time to read the whole piece?

Here’s what you need to know from Midjourney’s David Holz, tying his lessons into ones we’ve previously learned from other founders we’ve covered:

• Balance passion with practical timing. David’s leap into gesture-based tech with Leap Motion was visionary, but the market wasn’t fully ready, making the road harder. When you’re pioneering, timing matters as much as the idea. Gauge the ecosystem’s readiness before committing massive resources.

• Stay independent when it matters. David turned down Apple twice because he believed Leap Motion’s potential was broader than what any one corporate acquisition could allow. Know when to say no, even to giants, if it means protecting the long-term vision of what you’re building.

• Make your product social early. Midjourney’s growth exploded by leaning into community from the start, using Discord not just as a platform but as a social amplifier. Think beyond the product itself and design ways for your users to co-create, share, and push each other’s imagination forward.

• Frame your tech as an amplifier, not a replacement. David’s philosophy with Midjourney is that AI should expand human creativity, not replace it. As you build, ask: how does this make my users more powerful, confident, or imaginative? Tools that empower people’s strengths have staying power.

• Bootstrap when it fits the mission. Midjourney runs with no investors, staying small and mission-driven. This has kept the focus on meaningful projects rather than constant growth or exits. Consider if staying lean and independent can give you more freedom to experiment and stay aligned with what really excites you.

The mastermind behind Midjourney was born in 1988 in Seattle, but raised in the sun-kissed Southern Florida, in the town of Fort Lauderdale.

Through his dad came an early exposure to innovation and technology, and maybe even subconscious inspiration for what later became Midjourney’s name and logo.

See, although David’s father was a dentist, he didn’t work at any conventional dental practice, but at a sailboat instead. He sailed around the Caribbean to treat his patients. And while he didn’t exactly bring many things along in his travels, he did have a computer to manage his onboard dental clinic. Keep in mind - the idea of portable technology we’ve gotten so used to nowadays was still a crazy thing to picture back in the mid 90’s.

This wasn’t David’s only encounter with technology from an early age. Having grown up in an “elderly neighborhood”, he found himself in solitude most days than not, which turned out to be the perfect environment to start exploring the vast potential of the technology around him, even beyond the conventional use his father gave to his computer.

On one hand, he spent time taking apart and analyzing any device he could get his hands on, this way grasping the complexity of the hardware. On the other hand, he discovered Scheme and dipped his toes into programming for the first time.

Believe it or not, a good part of Midjourney’s original story can be traced back to Star Wars: Jedi Knight Force 2. The fascination with the game led him to discover the potential behind programming: it wasn’t just about shooting rockets out of his character’s hands, it was about bringing to life any product of imagination by manipulating the digital world.

And as a domino effect, after an early awakening on his fascination with technology, he set up his very own design business by the time he was in high school, which unmasked a true passion for entrepreneurship as well.

David wasn’t only passionate about understanding the possibilities of the digital realm, however. He was equally interested in the natural realm too. He considered himself a “scientist at heart” from a very early age, which inspired him, many years later, to pursue a dual degree on both Mathematics and Physics.

He attended the University of North Carolina at Chapel Hill, and after graduating he was presented with a choice: whether to continue his advanced studies on either his preferred subjects. He made a deliberate choice then and there - a PhD in Applied Mathematics would leverage his theoretical background and computer science knowledge to drive technological advances.

David’s talent and capabilities quickly caught the attention of prestigious institutions such as the Max Planck Institute and none other than NASA Langley. This allowed him to work with some of the brightest minds in the field, and certainly catapulted him from being a university student to becoming a leading contributor at the forefront of aerospace and innovation.

This period, however, was also marked by an overwhelming feeling of pressure for David. Juggling the research work on top of the PhD was getting to be too much; and as if that weren't enough, there was still a thought going through around his head.

See, the hundreds of hours spent on scientific research didn't only mean learning and getting unparalleled experience in the field; but on a daily basis, it mainly meant a lot of typing. David got as familiar as any to the functionalities of keyboards, mice and screen touch on computers, and found himself inspired—what if technology could reach a more natural and intuitive form of interaction with human movement?

That was the beginning of his first startup, Leap Motion.

By 2010 David was living in San Francisco, and he was already working towards a revolutionary way for people to engage with technology.

Touchscreen system had significantly developed through the 2000’s, and 3D modeling was at its peak, but he still found gesture-based interfaces to be unexplored and underutilized in the field.

The realization struck him during a typing class: unless all the barriers of traditional input devices were removed, digital creation would never be able to fully replicate the fluidity and precision of real-life hand movement.

Under the idea that there was still a lot of room for innovation in human-computer interaction, David Holz and his childhood friend Michael Buckwald—CTO and CEO, respectively—founded Leap Motion in 2011.

Headquartered in SF, the startup was quickly eyed by Silicon Valley investors and raised $1.3 million in the seed round. And by January of 2013, it announced a $30 million Series B funding round from top-tier firms including Founders Fund and Highland Capital Partners.

Leap Motion’s hand-tracking technology used a number of camera sensors to map out a 3D workspace in which the user could operate as they normally would, with pretty much no distance restrictions yet extreme precision.

The product launched in July 2013, paired with Windows and Mac computers, and it cost $80. The initial feedback was more than positive.

It became clear, however, that for both users and for Leap Motion there was still so much more to be explored when it came to hand gesture features.

But imagination was never lacking for David Holz.

There was even a hint of David’s artsy side that would later manifest in his vision for Midjourney.

Through the years, Leap Motion prioritized the improvement of the tracking system by making it all the more intricate with each new version.

By late 2013, Leap Motion had raised its Series B at a valuation of $306 million, but according to Business Insider, “its founders told their team that the fledgling startup was worth more, announcing that Leap Motion was potentially even worth $1 billion”, which would make David’s first company already a unicorn.

Within this framework, at 25 years old, both Holz and Buckwald were listed in Forbes' "30 Under 30" list alongside tech luminaries like Snap’s Evan Spiegel, Pinterest’s Tracy Chou, and Stripe’s Patrick Collison.

Furthermore, the company itself became a true leader in the field during the rise of human-computer interaction innovation. Through the years, Leap Motion prioritized the improvement of the tracking system by making it all the more intricate with each new version.

So much so, that it caught the attention of one of the industry’s giants.

REJECTING APPLE NOT ONCE, BUT TWICE

At the height of their innovation wave of the 2010s, Apple was quick to show interest in integrating Leap Motion’s gesture control into their suite of products.

At the time, hardly any other company could match Apple; not just in global reach, but especially in its timely relevance. In theory, joining forces with such a mainstream platform promised unprecedented scale for Leap Motion, and marked a potential step toward truly shifting the paradigm.

A formal acquisition proposal was made in 2013. David said no.

Despite all the rumors surrounding the decline —and even the infamous claim that David called Apple “the devil”— the bottom line is: Leap Motion just wasn’t ready to bow to another company, no matter how big the tech giant.

It was a stance in favor of Leap Motion’s potential to impact a wide range of applications and industries, beyond what might have been possible under the umbrella of Apple or any other top technology player.

It reflected David’s belief that true innovation often requires the freedom to explore uncharted territory without being constrained by the priorities and strategies of a larger entity.

In 2018 there was a further attempt from Apple. Negotiations made it farther this time, but the deal for a figure between $30 million and $50 million fell through just a few days before it was expected to be closed.

By this point in time, however, David’s mind was already elsewhere.

In the end, Leap Motion was acquired by the UK-based company Ultrahaptics in 2019, and the merged entity was rebranded as Ultraleap.

One major lesson from David’s time leading Leap Motion was the critical importance of timing.

Leap Motion’s technology was arguably ahead of its time. The ecosystem wasn’t yet ready for such a shift, and it took time until device compatibility wasn’t an issue anymore. So, while being a pioneer defined much of David’s early career, the “uphill battle” aspect is not to be underestimated.

For his next project he took a different path: this time, he bet on the undeniable rise of generative AI.

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Premium subscribers get full access to this newsletter, exclusive events, event discounts, and more.

If you live in LA and are interested in startups, will you please subscribe to my new newsletter, The LA Grind?

The first edition was sent out this week and featured:

• Curated LA events for founders, builders, and investors

• Founder spotlight of David Daneshgar of Whippy

• LA Venture Deals

• LA Opportunities (Job openings, VCs raising a fund)

• Living in LA (My favorite work spot, fun events, and more)

The next newsletter edition will be sent out Monday!

Subscribe to The LA Grind

Waseem Daher co-founded Pilot in 2017, but the idea had been taking shape long before that.

While studying computer science and electrical engineering at MIT, he built strong technical foundations and met the co-founders he would go on to start three companies with.

But in his early startup experiences, Waseem ran into a recurring problem. Managing finances, bookkeeping, and taxes was always a painful distraction from building the actual business.

After two successful exits, first with Ksplice, which was acquired by Oracle, and then with Zulip, which was acquired by Dropbox, he realized that this pain point wasn’t just his. It was universal among founders.

So they built Pilot. Not another SaaS tool, but a full-stack finance firm designed to feel like an extension of your startup.

Waseem had lived the problem. Now, he was solving it, building a company that lets founders focus on growing their business while Pilot handles the rest.

Listen to Waseem’s interview on YouTube, Spotify, or Apple Podcasts.

Thank you to our sponsor:

• Rho - A business banking platform, purpose-built for startups.

Let’s dive in.

Rho is a business banking platform, purpose-built for startups and they work with everyone from two-person YC startups with world-changing ideas to publicly-traded enterprises.

With Rho, founders get:

• A single pane of glass they can use to run and scale their business from Day 1: Bank account, corporate cards to start running – and expense management, bill pay automation, and accounting to help you move fast as you scale.

• The big thing with Rho: Every customer has a "person" at Rho. 24/7 customer support - phone, text, email - they will be there at every critical milestone in your startup's journey.

To learn why startups choose Rho, visit www.rho.co today.

• The Hard Part Is Scaling, Not Starting. Early traction can feel validating, but Waseem emphasizes that the real challenge begins once the business is running and growing. Founders often obsess over launching, but sustaining operational excellence, service quality, and culture at scale is a completely different beast. Success means thinking far beyond the MVP.

• Solve a Pain You Deeply Understand. Pilot was born from a pain Waseem personally experienced. This founder-market fit gave the team clear insight into customer needs and a compelling starting point. If you're solving your own problem, you likely have an intuitive understanding of what "excellent" looks like.

• The Best Ideas Often Seem Boring. Great startups don’t always come from flashy ideas. Pilot succeeded by rethinking such a painful, overlooked part of running a business as accounting, and building a full-stack solution. Waseem highlights how "unsexy" problems can offer massive markets, especially if they’ve long been underserved.

• You Only Need One Yes. Even with a strong founding team and a good track record, Waseem emphasizes that every funding round almost didn’t happen. Rejection is common, and your job isn’t to convince everyone; you just need one investor who believes. Don’t be discouraged by no’s; keep going until you find your yes.

• Fundraising is a Means, Not the Mission. Fundraising is a “necessary evil,” not the goal of your company. Success isn't defined by which firms back you but by whether you're solving a real problem customers want to pay for. Don’t let investor interest (or lack thereof) become a proxy for validation.

• Pick Investors Like Long-Term Partners. The Series A investor will be in your life for years, possibly texting you weekly. Choose based on chemistry and alignment, not just valuation. Pilot used their seed round partly to "audition" future Series A investors by giving small checks to people they wanted to test working relationships with.

• Founder-Led Sales Is Non-Negotiable Early On. Waseem personally sold Pilot’s first 100+ customers and stayed deep in the process. Why? Because it’s your fastest feedback loop on what’s working. If you don’t understand objections firsthand, you can’t fix them. Founders often try to delegate sales too early, but you shouldn’t.

• Start Niche, Then Expand. Even though Pilot could theoretically serve every business, they started with startup founders. Going niche early makes everything easier: messaging, targeting, referrals, and building domain knowledge. It’s better to be beloved by a focused group than vaguely liked by a large one.

• Marketing Attribution Is Messy. Trust Customer Intimacy. While attribution models (first-touch, last-touch) are tempting, Waseem points out that they’re often misleading. He argues that real conviction in marketing bets comes from knowing your customers deeply, not spreadsheets. Founders should spend time talking to users and experiencing their world firsthand. That’s how you identify campaigns that resonate, even if ROI isn’t obvious upfront.

• Founders Must Reevaluate Their Role as the Company Grows. As Pilot scaled, Waseem stepped away from the CEO role to return to work he finds energizing. The lesson: your ideal role evolves over time, and it’s okay to shift. Founders often move from “building the thing” to “building the machine that builds the thing,” but that path isn’t always energizing. Founders should regularly ask: Does this role align with my strengths, my energy, and the company’s needs? If not, changes are worth exploring.

Listen to Waseem’s interview on YouTube, Spotify, or Apple Podcasts.

00:00 What’s coming in the episode…

00:27 Introduction

01:36 Waseem’s passion for startups

03:58 Starting Pilot

05:43 Why was it the right time to start Pilot

13:30 Early days at Pilot

19:27 Raising capital for Pilot

22:32 Waseem’s mentality on fundraising

26:36 The story behind Pilot’s Series A round

30:22 Pilot’s first sales

34:09 Pilot’s ICP

36:44 Growth strategies back then

40:09 Growth strategies today

48:34 The evolution of Waseem’s role as a founder

54:25 Be a part of Pilot

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Premium subscribers get full access to this newsletter, and much more.

If you live in LA and are interested in startups, will you please subscribe to my new newsletter, The LA Grind?

It’ll feature curated events and standout stories for LA’s founders, builders, and investors.

The first edition goes out tomorrow, May 19th, and I’m so excited for it!

Subscribe to The LA Grind

Abdul Al-Asaad co-founded Basic Capital and just came out of stealth in 2025, but the idea had been taking shape long before that.

On his days working at Goldman Sachs he experienced firsthand a vicious cycle—investors are expected to deliver growth, but they often lack the means to even get started.

The turning point was when Abdul realized he couldn’t even afford a share of Tesla; he learned then that “it takes money to make money”.

And while everyone was focusing on the key factors of financial literacy and access to the market, no-one was focusing on giving investors the basic capital to start with.

Abdul identified a gap in the market. Lived it, more like. And later capitalized it into a very promising system that’s sure to be explored more deeply.

Listen to Abdul’s interview on YouTube, Spotify, or Apple Podcasts.

Thank you to our sponsor:

Rho: A business banking platform, purpose-built for startups.

Let’s dive in.

Rho gives founders everything they need to scale. Banking, corporate cards, expense management, bill pay, and accounting, all in one platform.

Startups like Perplexity AI (a16z), Cal.com (YC), and Public.com (a16z) trust Rho to manage their finances as they grow.

What makes Rho different?

Every customer gets a real person. Call, text, or email anytime. Real support when it matters.

Rho is with you through every step of your startup’s journey.

To learn why startups choose Rho, visit www.rho.co today.

• Build from personal pain and conviction. Abdul created Basic Capital based on a problem he personally experienced: having financial literacy and access, but not enough capital to actually invest. This lived insight not only gave him deep conviction and clarity of purpose, but it also revealed a market gap ready to be tapped.

• Don’t wait for market validation; create your own market instead. When Goldman Sachs told him the TAM was zero, Abdul didn’t pivot—he doubled down. Incumbents look for existing pools of profit; founders create new ones. Basic Capital is a classic example of category creation: financing investing rather than consumption.

• Take asymmetric bets on exposure. From applying to just one business school (HBS) to printing a custom pitch deck for Bill Ackman and hand-delivering it at a talk, Abdul repeatedly took high-effort, high-upside swings. These moves aren’t scalable, but they are often what early success depends on.

• Work with the constraints you have, not the ones you wish you had. As an immigrant without a financial safety net, Abdul used business school not just for the degree, but as a de-risked way to incubate his idea. He didn’t have the privilege to “explore” full-time, so he manufactured his own on-ramp.

• Persistence matters more than polish in the early days. With no technical background or network, Abdul still managed to find his co-founder after a full year of cold outreach. He didn’t know who the “right” engineers were; he just knew he needed one. So he out-hustled most people to make it happen.

• Conviction is contagious, but it has to start with you. Before they had customers or investors, Abdul had to convince just one person: his co-founder. That first “yes” from Anjan Karanam was the spark. Founders often wait for traction, but belief starts by enrolling one person at a time.

• You don’t need credentials, just relentless curiosity. Abdul and Anjan had no background in ERISA, tax law, or securities. They learned everything from scratch, one cold DM and Google search at a time. Most people stop when they feel out of their depth. Passionate founders don’t.

• Abdul sees building a company like building a religion: once you truly convince one person, others start to follow faster. For months, nothing happened for Basic Capital. Then everything did. When a key investor said yes, it was like a domino effect.

• Breakthrough ideas often sound backward at first. Most retirement plans are built slowly over time. Abdul flipped it: front-load the savings and pay it off over decades. Big ideas often look weird early. That’s why they work.

Listen to Abdul’s interview on YouTube, Spotify, or Apple Podcasts.

00:00 What’s coming in the episode…

00:48 Introduction

02:18 Basic Capital’s origin

06:51 Abdul’s background

09:41 Hustling for Basic Capital and raising from billionaire Bill Ackman

16:55 The solution to a vicious cycle

24:00 Early days of Basic Capital

30:19 Raising capital

36:11 The logic behind Basic Capital

40:25 The vision for Basic Capital

43:34 Get involved in Basic Capital

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Premium subscribers get full access to this newsletter, exclusive events, event discounts, and more.

If you live in LA and are interested in startups, will you please subscriber to my new newsletter, The LA Grind?

It’ll feature curated events and standout stories for LA’s founders, builders, and investors.

The first edition goes out May 19th and I’m so excited for it!

Subscribe to The LA Grind

Jeremy Yamaguchi is a lifelong entrepreneur.

The founder and CEO of Cabana Pools got his start selling balloon animals at age 12 and, from then on, he never stopped building.

In his teens, he launched a design and development agency that grew into a full-blown growth marketing firm. And by his early 20s, he had bootstrapped a successful housekeeping marketplace, which he later sold to private equity, dodging the wave of overfunded, unsustainable competitors that crashed shortly after.

Next up was Lawn Love, an on-demand lawn care platform he built into a national brand and ran for nearly eight years. Jeremy has always gravitated toward “high-suck” industries because he knows how to bring order through smart software and sharp marketing. He’s less about hype, more about execution.

Today at Cabana he’s bringing the same marketplace and tech-driven playbook to the world of residential pool services, another old-school industry ripe for modernization.

Listen to Jeremy’s interview on YouTube, Spotify, or Apple Podcasts.

Thank you to our sponsor:

• Rho - A business banking platform, purpose-built for startups.

Let’s dive in.

Rho is a business banking platform, purpose-built for startups and they work with everyone from two-person YC startups with world-changing ideas to publicly-traded enterprises.

With Rho, founders get:

• A single pane of glass they can use to run and scale their business from Day 1: Bank account, corporate cards to start running – and expense management, bill pay automation, and accounting to help you move fast as you scale.

• The big thing with Rho: Every customer has a "person" at Rho. 24/7 customer support - phone, text, email - they will be there at every critical milestone in your startup's journey.

To learn why startups choose Rho, visit www.rho.co today.

• Rapid testing and data-driven validation to pick the next ventures. Before starting Lawn Love, Jeremy tested three business ideas (lawn care, pool cleaning, and personal training) simultaneously by building landing pages and driving traffic to see which had the best customer acquisition metrics. Lawn care won, not because of passion, but because of customer demand and scalable economics.

• Be strategic about timing and competition. Jeremy exited his first home services startup just before well-funded Silicon Valley competitors entered the space. While they burned through capital and ultimately struggled, he sold his bootstrapped business to private equity at the right time, demonstrating sharp awareness of market dynamics and risk mitigation.

• Jeremy values intrinsic motivation over external validation. When he applied to Y Combinator he didn’t pin his hopes on it, since he believed that true founders build regardless of outside recognition. A long-term grit mindset beats short-term credentials.

• Be intentional about investor selection. Rather than chasing a single big check, Jeremy chose a “party round” to bring in a diverse mix of operators and angels who could offer strategic value beyond capital, turning his cap table into a growth engine.

• Prioritize channels that align with user intent. Jeremy focused on SEO and SEM early on, recognizing that customers actively searching for home services were more valuable than passive social media users, leading to efficient, scalable growth.

• Jeremy treats customer service as a core growth lever. He built in-house support early because he believed that fast, empathetic help not only retained users but turned them into advocates, creating organic word-of-mouth that compounds over time.

• A hybrid of venture growth and private equity discipline was Cabana’s business strategy. To Jeremy, acquiring and vertically integrating home service businesses using custom-built software can yield venture-scale returns without traditional venture risk, creating a unique investment opportunity that’s increasingly gaining mainstream attention.

• Some of the best hires may not look great on paper. Jeremy learned not to over-index on pedigree. One of his best engineers had never worked at a big tech company or gone to a name-brand school, but could out-execute just about anyone. He focused on finding people who could actually build, not just talk about it.

• Bootstrapping builds discipline that venture money can’t replace. Before raising any capital, Jeremy bootstrapped multiple businesses, so he learned how to make every dollar count. That scrappy mindset stayed with him even after he raised funding for Lawn Love. He’s wary of founders who rely too heavily on outside capital to prove product-market fit or fund early growth: “Raising money should accelerate what’s working, not validate something that isn’t.”

Listen to Jeremy’s interview on YouTube, Spotify, or Apple Podcasts.

00:00 What’s coming in the episode…

00:55 Introduction

02:17 Jeremy’s background

08:34 Jeremy’s “origin story”

18:22 The process behind Lawn Love

26:18 Early days of Lawn Love

30:42 Lawn Love’s experience in YC

33:19 Angel raising with Lawn Love

35:47 Lawn Love’s growth

37:56 Selling Lawn Love

40:48 Founding Cabana Pools

49:19 Growing + buying companies

53:15 Fundraising for Cabana Pools

1:06:17 Cabana’s challenges

1:11:05 What’s next for Cabana Pools

1:13:17 Contact Jeremy

John Andrew Entwistle of Wander

Nick Huber of Bolt Storage

Everett Cook of Rho

Jacob Jaber of Philz Coffee

Dave Fontenot of HF0

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Premium subscribers get full access to this newsletter, exclusive events, event discounts, and more.

It’s been a crazy busy couple of weeks with the launch of Newsletter Founder and the May 19th launch of The LA Grind.

But I’m super excited about what’s to come with all of the things I’m working on and feeling rejuvenated after spending a day and a half in Palm Springs this week.

A few weeks back I ran a poll asking what your main challenges were right now.

The leading response?

Fundraising.

So we put together a few resources that will be helpful for you.

Some are recent, some are timeless, all can be useful in your process.

Do you have other resources that could be useful? Reply to this email with ones I should share in the future.

Also, I’m bringing back serendipity calls.

What are these?

15-minute calls with me to discuss anything.

We can talk about content strategy, newsletters, podcasts, growing media companies, fundraising, finding your life’s work, ANYTHING. I’ll help however I can.

I opened up a few spots in the next couple of weeks. Should be fun.

Alright, time for those fundraising resources.

Let’s dive in.

Foundational Knowledge: Startup Funding Basics

Learn the essentials from cap tables to how investors think.

• Y Combinator’s Startup Library: covers everything from how funding works to term sheets and pitch tips.

  • Recommended:

    • A Guide to Seed Fundraising

    • Modern Startup Funding

    • How Startup Fundraising Works

    • Understanding SAFEs and Priced Equity Rounds

    • How to Build Your Seed Round Pitch Deck

    • How to Build a Great Series A Pitch and Deck

    • Dalton & Michael: YC Founders Made These Fundraising Mistakes

    • Managing Startup Finances

• Startup School by YC: free course with videos on startup fundraising and business structure.

• First Round Capital’s “Field Guide”: great for founder stories and nuanced perspectives on early-stage fundraising.

  • Recommended:

    • The Fundraising Wisdom That Helped Our Founders Raise Billions in Follow-On Capital

    • Take Your Fundraising Pitch from Mediocre to Memorable with Storytelling

    • The Founder's Field Guide for Navigating a Crisis

    • A Founder's Step-by-Step Guide to Building a Community and Fundraising

    • You Aren't Getting the Most Out of Your Investors — This is How to Start

Venture Capital Resources

Master the VC game from finding investors to closing your round.

• Crunchbase: use to research VCs, their portfolios, and funding rounds.

• NFX’s Fundraising Guides: insider tips on how VCs think, pitch deck strategies, and network effects.

• DocSend Startup Fundraising Report: real data on how long investors spend reviewing decks, and what matters most.

• AngelList: learn about syndicates, scout funds, and access to angel investors.

• Adamant and Funded by Jason Yeh

Alternative Funding Options

Discover non-VC routes like crowdfunding grants and revenue-based financing.

• Revenue-Based Financing

  • Pipe 

  • Capchase

• Crowdfunding Platforms

  • Wefunder

  • Republic 

  • StartEngine

  • Kickstarter

• Investors in Individuals

  • Chisos Capital

  • Crowdsurf

• Grants & Government Programs

  • Grants.gov (U.S. based)

  • SBA Funding Programs

• Accelerators, Incubators, and Residencies

  • Y Combinator

  • HF0

  • Techstars

  • Velocity

  • PearX

  • Sequoia Arc

  • Antler

  • Z Fellows

  • The Residency

  • Grid110

Tools for Pitching & Building

Everything you need to build pitch and protect your startup.

• Pitch Deck Hunt: a growing library of real, investor-approved pitch decks from companies like Airbnb, Dropbox, and Front. Use it as inspiration for structure, storytelling, and visual clarity.

• Pitch Deck Design

  • Slidebean

  • Canva (search “startup pitch deck”)

  • Deck Doctors

  • Gamma

• Legal Templates & Tools

  • Clerky

  • Cooley GO

  • SeedLegals (UK/EU)

Platforms to Discover and Connect with Investors

Use these curated tools and databases to find VCs, angels, and startup-friendly capital sources.

• NFX Signal by NfX: A powerful free platform for discovering and contacting investors by industry, stage, and geography

• First Round Angel Track by First Round Capital: A curated network of active, founder-friendly angel investors backed by First Round

• Airtable: Community of Women Angel Investors by Lolita Taub: A crowdsourced list of venture funds with investment preferences, stage focus, and contact info.

• Airtable: Diverse Investors List by Yuliya Bel: A public tracker of diverse investors and funds supporting underrepresented founders

• OpenVC by Steph Nass: A global open database of investors, complete with filters and cold email guidelines

• Gen Z VCs by Meagan Loyst: A fast-growing network and deal flow community for young investors and emerging founders.

Essential Funding Toolkits and Lists

Explore these curated spreadsheets, databases, and guides to streamline your fundraising process.

• Active Investor List by Trace Cohen: a comprehensive list of self-identified investors, including their investment focus, typical check sizes, and contact information. Remember: you need to fill the form to get the entire list.

• The Ultimate List of 750+ Seed Funds by Matt Estes: an extensive directory of seed funds, detailing their investment stages, sectors, and contact details.

• Founder Toolkit: Non-Dilutive Funding Guide by Alex Macdonald: a curated guide highlighting over 35 non-dilutive funding options, including grants and revenue-based financing.

• Commonapp.VC by Confluence.VC: a unified application platform allowing startups to submit their pitch to multiple VCs simultaneously.

• Woman VCs Twitter List by Christoph Janz: a curated list of female venture capitalists active on Twitter, sharing insights and advice for founders.

Newsletters and Blogs to Source from

Curated insights from top startup minds to keep you sharp.

• Term Sheet (by Fortune): Startup deal news

• StrictlyVC: Insider VC updates

• The Generalist: Deep dives into startup trends

  • Newsletter

  • Podcast

  • Recommended:

    • Lessons from 20 Years of Venture Capital: Roelof Botha (Managing Partner at Sequoia Capital)

    • Timeless Lessons from Great Investors

• Not Boring by Packy McCormick: Story-driven startup analysis

• This Week in Startups: Hosted by Jason Calacanis.

  • Newsletter

  • Podcast

I know there are MANY resources we didn’t include today so please share with us your favorite ones in a reply to this email 😊 

In the past two years, we’ve published dozens of deep dives on world-class founders, sharing how they built their companies. These typically take 20-30 hours to research and write. The most recent ones are below:

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Premium subscribers get full access to this newsletter, exclusive events, event discounts, and more.

John Andrew Entwistle is the founder of Wander, a company rewriting the narrative of travel through elegance, technology, and intentional design.

He built his first company at the age of 13. And by the time he was 16, he built Coder.com—an idea born in high school, later backed by Silicon Valley's most storied venture firms.

At 23 he was already a CEO and had raised over 50 million dollars. But he got a different vision, something he was more passionate and excited about, and went all in to build Wander.

Now, at only 27, John Andrew is one of Forbes’ 30 under 30 and has grown Wander into one of the defining forces in the American travel landscape.

Listen to John Andrew’s interview on YouTube, Spotify, or Apple Podcasts.

Thank you to our sponsor:

• Rho - A business banking platform, purpose-built for startups.

Let’s dive in.

Rho is a business banking platform, purpose-built for startups and they work with everyone from two-person YC startups with world-changing ideas to publicly-traded enterprises.

With Rho, founders get:

• A single pane of glass they can use to run and scale their business from Day 1: Bank account, corporate cards to start running – and expense management, bill pay automation, and accounting to help you move fast as you scale.

• The big thing with Rho: Every customer has a "person" at Rho. 24/7 customer support - phone, text, email - they will be there at every critical milestone in your startup's journey.

To learn why startups choose Rho, visit www.rho.co today.

• Success in startups requires strategy, not just passion. John Andrew emphasizes that starting a company is a major life commitment, which inevitably comes with a high likelihood of failure. Founders must be deeply thoughtful, strategic, and deliberate in choosing their idea and executing on it. To wing it may be thrilling, but it isn't a reliable path to success.

• No one is coming to save you. Sounds ominous, but it’s actually a good thing. A recurring theme is radical responsibility: the mindset of "no one is coming to save us" instills a strong sense of agency, pushing founders to act decisively and build their company proactively without waiting for external help or validation.

• Work backwards. John Andrew created a "pre-mortem" document to anticipate failure points and systematically test Wander’s business model before building. He even tested real customer demand early by charging users for early access—generating hundreds of thousands in revenue pre-launch—highlighting the value of testing market fit before scaling.

• Start Unscalable to Validate the Vision. In the early days, John Andrew personally drove around to scout homes and oversaw cleaning, tech integration, and customer experience. This scrappy, hands-on approach let them validate that customers would actually pay for the product, even before scaling.

• Extreme Customer Experience First, Then Scale. Wander launched with a highly luxurious, tech-integrated offering (e.g., app-controlled homes, Teslas in garages, concierge services) to set a bold standard and validate demand. Over time, they refined and scaled back the experience while preserving customer delight and maintaining a high NPS.

• Branding as a Foundational Strategy. The Wander brand was designed deliberately to evoke emotion and aspiration. To John Andrew, a strong brand is a promise to the customer, and that everything from the name, logo, and even magical touches like moving backgrounds on the website should reflect that.

• Wander OS and Scaling with Software + AI. To scale such a capital and labor-intensive business, they built Wander OS—a software system to coordinate logistics like cleaning and guest communications. Now 100% of tasks are run through the system, with 60% handled autonomously via AI, enabling unusually high margins (70%+) and fast growth.

• Fundraising Is Milestone-Driven and Intensely Demanding. Each funding stage—pre-seed to Series C—requires founders to hit increasingly complex proof points, from product development and early revenue to scalable unit economics and growth. Wander is currently at Series B, which John Andrew describes as the most grueling, demanding both execution and speed, often at the cost of sleep and personal bandwidth.

• Scale Requires Growth, But Don’t Underestimate User Activation. John Andrew encourages founders to switch focus from just acquiring users to activating them, which is so much more powerful. Wander’s journey involved scaling its property supply through REITs and now turning attention to converting its large user base through personalized outreach and data-driven engagement, not just ads.

Listen to John Andrew’s interview on YouTube, Spotify, or Apple Podcasts.

00:00 What’s coming in the episode…

00:52 Introduction

02:49 John Andrew’s beginnings

04:08 Early lessons as a founder

08:19 The start of Wonder

16:35 The story behind Coder.com 

20:00 Wander’s early days

25:08 Building Wander’s brand

30:40 First customers and feedback

36:29 Locations and international expansion

42:03 John Andrew’s purpose

46:04 Funding Wander

50:51 Where is Wander today?

55:12 Focusing on user activation

1:02:41 What’s next for Wander?

I’m starting something new.

It’s a free local newsletter called The LA Grind.

It’ll include curated events and standout stories from LA’s founders, builders, and investors.

In the next week or two I’ll send out the first edition.

Sign up for free here if interested.

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders!

2025 Salary Report: Hire smarter, save big today.

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I think I’m in my new projects era.

I recently launched Newsletter Founder, a course and community for newsletter writers, and today I’m sharing a very early project, The LA Grind, a local newsletter with curated events and standout stories from LA’s founders, builders, and investors.

You can signup here or click the link below, but I may not have an edition coming out for a week or two, I just need to get this project out there because it’s been in my head for months and I can’t wait any longer.

beehiiv 🪄

magic.beehiiv.com/v1/da6a2feb-02d3-4aba-a8d0-f462fbee4fd1?email={{email}}

Also, I’m curious, have you listened to the Just Go Grind Podcast yet? Have you?? What’re you waiting for?!?!

We’re rolling with it now, 7 episodes into the re-launch, and have a great partner in Rho supporting the show.

It’s available on all the podcasting platforms:

• YouTube

• Spotify

• Apple Podcasts

• Overcast

Today we’ve got a deep dive on the $22B education giant, Duolingo, and there’s a lot to get into. Please let me know at the end what you thought of this piece, I’d really appreciate any feedback 🙂 

Let’s dive in!

Over 100 million people across the world use Duolingo month after month.

And if you speak more than one language, you probably have used it too.

In fact, there’s a pretty good chance that some of you reading this are simultaneously avoiding a snarky notification on your phone from the little green owl, urging you to complete today’s lesson (which you should, by the way).

Led by Luis von Ahn and Severin Hacker, Duolingo has put a spin on language learning under the belief that education is what truly changes people’s lives.

Almost 14 years later, it’s safe to safe to say, they have done just that.

Duolingo has reached nearly every corner of the world. But despite being of all different ages, races and nationalities, one thing about Duolingo users—they will do anything not to break their hard earned streak.

KEY TAKEAWAYS FROM DUOLINGO

Don’t have time to read the whole piece?

Here’s what you need to know from the founding story of Duolingo, tying its lessons into ones we’ve previously learned from other founders we’ve covered:

• Make the broccoli taste like dessert. Duolingo turned the hardest part of learning into a game. Streaks, rewards, and guilt-based nudges keep users coming back every day. Founders building habit-forming products should prioritize motivation as much as content.

• Build a product so good people can’t help but share it. Duolingo reached 10 million downloads without any marketing spend. The app actually worked, felt fun, and delivered real value. If people love it, they will spread it.

• Treat growth like product. Duolingo ran hundreds of small experiments across notifications, branding, and content. They doubled down on whatever worked and cut what didn’t. This test-and-learn approach helped them scale both product and marketing in sync.

• Let your mascot carry the brand. Duo the Owl is a fully developed character that drives attention, emotion, and engagement. If you are building a consumer brand, consider how a mascot or consistent brand identity can drive growth across product and social.

• Align your business model with your mission. Duolingo kept education free by monetizing through a small set of paying users. This structure allows global impact while still building a massive business. Your business model should amplify your mission, not compromise it.

• Hire slowly and protect the culture. Duolingo waited years to fill key leadership roles because they refused to lower the bar. While it created early chaos, it paid off long term. Founders should hire for alignment and excellence, not speed.

Before founding Duolingo brought them together, Luis von Ahn and Severin Hacker lived very different lives in quite opposite places of the world.

Luis grew up in Guatemala. Though he came into the world under unique circumstances, he had a smooth upbringing as an only child, raised by his single mother in Guatemala City.

That is until his senior year in high school, when the kidnapping of his aunt forever scarred his teenage-hood. It was quite the turning point in his future, since it made the idea of leaving the country all the more possible.

But by then, another major event for Luis had taken place—he had decided to major in Math, which was no easy thing in Guatemala back in the late nineties. Backed by his strong academic record and his intuitive mother, he moved his entire life to the US to pursue his dream.

Luis grew up bilingual; though he already attended an American school back home, his mother made it a point to maintain a strong command of both Spanish and English in the household.

When he applied to college in the U.S., the TOEFL (Test of English as a Foreign Language) wasn’t as much of challenge because of his language level, but more so in terms of accessibility. Taking the exam cost several hundred dollars, and since all the spots in Guatemala were full, he had to fly to neighboring El Salvador just to sit for it. Altogether, the process cost over a thousand dollars—an expensive and frustrating hurdle before even knowing if he’d be accepted.

The memory of this whole experience would certainly not go unnoticed by Luis when the idea of Duolingo first sparked. They now offer the Duolingo English Test that is 100% remote, accepted by top institutions around the world and for only a fraction of the TOEFL cost.

But we’re getting ahead of ourselves here.

He got into Duke and, as planned, majored in Mathematics. He then got a PhD on Computer Science in Carnegie Mellon University, where he later started teaching his own class.

Once a professor, always a professor, though—it may not have been in the same traditional way, but that would not be his last time teaching. Duolingo was unquestionably built upon Luis’ years of experience in the field, and under the belief that education plays a main role in transforming people’s lives for the better.

While at Carnegie Mellon, Luis came up with a little thing called CAPTCHA. Yes, the same guy behind your daily language lessons is also the reason you’ve had to prove you're not a robot before visiting half the internet. And he did it at just 21 years old.

They gave -not sold- the idea out to Yahoo. Seven years later, along with a few of his students he built a 2.0 version of CAPTCHA, one that simultaneously worked on digitalizing books while you proved yourself as a human by typing a word. This new system was called reCAPTCHA and acquired by Google—only for tens of millions of dollars, this time.

Believe it or not, this was not even the most life-changing thing to come out of Luis’ time at Carnegie Mellon. He met Severin Hacker there, his co-founder at what would later be the world’s most popular educational app.

Severin grew up just outside of Zurich, in a little town called Zug, Switzerland.

His upbringing explains a lot of what his career turned out to be. For one, his interest in business was always in his blood.

On the other hand, he recalls being one of the few families in his neighborhood to have Internet, so he spent good part of his childhood fascinated by computers; so much so, that he taught himself programming at the age of 12.

And yes, he's well aware of the irony in his name.

Naturally, he decided to major in Computer Science in ETH University in Zurich, but had his life truly turned upside down when he moved to Pittsburgh for an exchange in Carnegie Mellon.

Luis von Ahn was his professor, the youngest in Computer Science at the time, and Severin was eager to meet him.

Two years into the program, the idea for Duolingo was born.

It all started as a research project.

They got research funding while still in Carnegie Mellon and started working on an educational mobile app. In the early 2010’s, smartphones were taking over the market and everyone was in the lookout for the next big app.

They settled on one subject: foreign languages. Firstly, because there was a huge audience for it—about 2 billion people around the world are learning another language, in and outside of schools. But most importantly, because both Luis and Severin had lived firsthand the impact a second language can have in someone’s life, and they wanted to make that opportunity available to anyone through something as ordinary as a smartphone.

The project grew bigger and bigger though; they even got 8 other students involved. It grew a little too big, however, to the point where they had to be kicked out of Carnegie Mellon.

From then on, they began their journey into venture capital.

Duolingo didn’t have it tough raising their first round, since they had a lot of users guaranteed even before launch day—the waitlist for the private beta had over 300,000 people signed up. And within the first year, the app gathered 10 million downloads.

The secret? A truly good product.

With these crazy user numbers, they raised over $3.3M in Series A in October 2011. And through the years they kept raising millions, only it was not reflecting on revenue, not one bit—for the first five years, Duolingo made $0.

Most of their investors, according to Severin, believed Duolingo would eventually follow reCAPTCHA’s footsteps and be sold to Google. Yet both Luis and Severin had quite a different vision for Duolingo, and they were starting to see how it could someday become big; like, 2013-Apple’s-app-of-the-year kind of big.

They took their time to monetize, which Severin identifies as one of Duolingo’s biggest mistakes. But basically, they just had’t figured out how to monetize Duolingo in a way that felt true to its essence.

Duolingo was always after one mission—transforming education for good. But in order to do so, they knew they needed to reach people from across all ages, classes and nationalities.

Eventually, to maintain the promise of an open and accessible app, they developed a “freemium” model that combines ad-supported access for the free tier and an ad-free experience with some extra features for the paid “Super” tier.

However, all content is available for free. No lessons are gatekept—you can learn one, two or multiple languages in Duolingo without ever paying one cent, which is what most users are doing.

According to the 2024 shareholders letter, over 90% of the users use the free version, while roughly 8% of Duolingo users pay for a subscription and contribute to 80% of the company’s revenue, which was nearly $750M in total this past year.

It might have taken them some time to get here, but unlocking the “freemium” model was key to crack monetization while staying aligned with Duolingo’s mission.

THE MOST PUSHY APP ON EARTH

By 2014, only two years after launching, Duolingo had already reached 30 million downloads.

As it turned out, users were never lacking for Duolingo; they just kept coming and coming. But there was still something left to figure out—how to make them come back.

By having users compete against friends to receive all kinds of rewards, Duolingo has mastered the learn-but-make-it-fun genre. And what's made it all the more engaging are the two main traits of the app—the streak and the notifications.

To fight the fact that will-power is limited, Duolingo has taken a different route—straight-up guilt-tripping.

Completing only one lesson in Duolingo is enough to get you on a streak. You will easily complete the second, the third, and even all the way to the tenth might not be a hassle. But the further you get, the less you wanna break the streak, so you might as well do your lesson for one more day, right?

Some may call it manipulative; Luis and Severin call it effective.

Over 3 million daily active users have a streak longer than 365 days. And according to the Duolingo Hall of Fame, the longest streak on the platform is over 4300 days in a row, which is equivalent to nearly 12 years of uninterrupted learning.

Sometimes it’s not about will-power, though. Sometimes breaking your streak can be a genuine mistake—you’ve started a new job. You’re traveling. Life’s just gotten busy. But if that’s the case, then get ready to start receiving some ominous notifications on your phone.

Notifications play a huge role in your individual Duolingo experience, because they’re trained to work specifically for you.

The team developed a sophisticated AI system to make notifications just annoying enough to maximize the chances you'll come back.

Usually, you’ll get your reminder exactly 24 hours since you last used the app, so that it’s somewhat guaranteed that it’ll catch you on your free time. But as far as the actual message goes… it’s become a bit of a meme at this point. And it’s all thanks to Duo.

INTRODUCING DUO THE OWL

Luis knew it from the beginning—Duolingo needed a mascot. A colorful design and a pair of cute eyes never fail to draw people in.

They were between two final options: a little robot and a green owl. They decided to put it to a vote, and the whole team went with the robot; it was a software teaching you a language, after all.

They decided to ask outside people too, just to get a second opinion. Not that it could ever change their minds about the robot.

Except, it did. And that’s how Duo the owl was born.

Apple Developer

The thing with Duo is that however sweet his green feathers and big eyes may look, he’s actually got quite of an attitude. One thing about Duo and all other Duolingo characters—they will make you do your daily lesson, one way or another.

And people truly do love him—1 million people follow Duolingo on X, only to tune in to Duo’s unhinged tweets.

Twitter tweet

Twitter tweet

Another 5 million people follow Duolingo’s Instagram account to be fed some more weird posts.

Instagram post

And as if Duolingo’s bizarre content wasn’t enough already, nearly 17 million people follow their TikTok page.

@duolingo

congrats on your new bundle of joy!!! #duolingo

Just like in A24’s case, Duo’s online presence has only been perfected by dominating online pop culture, a now proven mechanism to organically and effectively reach out to the broadest of audiences—millennials and Gen Z.

In this state of things, don’t be surprised when you go on social media and see Duo somehow involved in whatever topic is trending, whether it’s a popular movie, an on-going TV show or a meme that’s just gone viral.

Twitter tweet

Instagram post

Twitter tweet

As of today, Duo’s reached celebrity status, believe it or not. A sassy green owl that teaches languages now rubs shoulders with charlieXCX, Olivia Rodrigo, and his namesake and bestie, Dua Lipa.

Through the years, Duo becoming an A-lister has only pushed Duolingo higher and higher in popularity—it’s now been over a decade since it first rose to the top of educational apps.

And it has simultaneously led to major promotional deals—last year, Duolingo partnered with one of Netflix’s most popular TV shows of all time, Squid Game, to launch ‘Learn Korean or else’.

The year prior, in an early April fools day prank, Duolingo partnered with Peacock to announce a new Love Island inspired reality TV show—Love Language. The show, sadly fake, had real business incentives:

The notifications, memes and deals, however, don’t even begin to explain the lengths Duolingo will get to make you learn a new language.

See, on February 11th, 2025, Duo the owl died.

Twitter tweet

The news shocked the world. Major brands like KitKat, Subway, BuzzFeed, Hilton, and T-Mobile jumped into the comments to pay their respects; even the World Health Organization came forward to make it clear that, at the very least, we didn't need to worry about it being smallpox.

The world’s most popular YouTuber, Mr. Beast, made his own TikTok about Duo’s death, that has now gathered over 100 million views. The Late Show with Stephen Colbert, weighed in as well. 

Official statements were made, condolences were sent and there was even a call to find a potential culprit. But there was still a huge question hanging in the air—how can a fictional mascot really die?

Well, it doesn't. Obviously.

As everyone expected, Duo was very much alive. He just wanted you to complete your daily lesson.

Twitter tweet

The stunt had an unthinkable reach of over 1.7 billion impressions across all social media platforms, and made Duo’s green feathers and absolute lunacy known to the whole world.

THE DUOLINGO FORMULA

Luis attributes Duolingo’s success to two key strategies: hiring the best and constantly experimenting.

Firstly, they took their time to hire senior leaders, which to Severin was one of their biggest mistakes because it made the office very chaotic. It was the first 20 employees’ first job, including Severin himself.

But all in all, they truly prioritize hiring smart. They just don’t want to settle, so much so that they went two years without a CFO simply because they couldn’t find the right person. Their first CMO, Cammie Dunoway, was also difficult to find, and she wasn’t hired until 2018.

It paid off big time, however. They carefully curated their team and made sure everyone in Duolingo was up to its mission’s standards: the current Head of Engineering came straight from Google, and their CMO had prior experience in Yahoo and Nintendo.

Cammie was also crucial to the Duolingo formula, since it was the first time they had a multi-millionaire budget to spend on marketing after seven years of only focusing on PR.

Dunoway set up a team of youngsters and Luis and Severin gave them free will to test out strategies to their liking, as long as it didn’t compromise the product.

Throughout this whole process, they’ve perfected their marketing strategy—influencers work in certain countries, and performance marketing in some others. But for a market as wide and competitive as the American, they figured out that Duo the owl with his obnoxious antics on socials were the way to go.

Lastly, Duolingo’s co-founders believe in always taking the long view.

Notifications, for example. They could easily go harder on notifications and try to draw more people and attention in. But once it gets too spammy, it’s done—the user is prone to never get back to the app, and rightfully so.

The same goes for Duo the owl’s content. There’s a fine line between edgy and straight-up raunchy. They could easily cross it once or twice to gain more traction every now and then; but they rather not do things impulsively only to later find themselves in need of damage control.

It goes hand in hand with hiring slow—Duolingo is a mission-driven company: making education accessible for everyone, everywhere. And in order to keep walking towards that goal, every decision matters.

Ever since launch day, Duolingo has consistently and exponentially grown in every possible aspect—downloads, subscribers, daily and monthly users, valuation and revenue.

They’ve managed to stay on top of the educational category in both the App Store and Google Play.

Despite all of this, of one thing Luis and Severin are certain—Duolingo’s only at 1% of what they can achieve as a company.

With over 40 languages and more than 100 courses now available, Duolingo is ready to branch out into new and exciting learning territory.

In 2023 they launched their Music Learning Program. Furthermore, they’re looking to deep their toes into math courses.

The Duolingo learning method —learning by doing and through a phone— has been proved effective for more than a decade now: according to Luis von Ahn, users who complete half a course on Duolingo learn as much as students taking four university semesters of language education.

Math and music, therefore, were at the top of their picks, because the learning method lends itself well to these subjects. But after that, there are no plans to stop.

In terms of geographic expansion, there’s also plenty of potential.

They have offices in New York, Seattle, Beijing, and Berlin, but they’re looking into Japan, Korea, China and India to increase their presence in Asian markets.

In just over a decade, Duolingo has come to dominate language learning. By all accounts, there’s little doubt it will slowly but surely find a way to dominate all other fields.

If accessible, universal education is the goal, then the sky’s the limit for Duolingo.

“Reduce, Automate, Delegate”:

On focusing on the product:

On Duolingo’s social impact:

In the past two years, we’ve published dozens of deep dives on world-class founders, sharing how they built their companies. These typically take 20-30 hours to research and write. The most recent ones are below:

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna

Hey, Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Premium subscribers get full access to this newsletter, exclusive events, event discounts, and more.

Nick Huber had an early start in entrepreneurship as only the author of The Sweaty Startup could have.

Back in his hometown, Tell City, Indiana, Nick had his first ever job as lawn mower and didn’t ever stop until founding his first company, Storage Squad, in college.

After growing that business into 12 different states and $2M in annual revenue, it was sold in 2021. From then on, he has skyrocketed his presence online and has built The Sweaty Startup’s brand, including a thriving newsletter and podcast and over 300k followers on Twitter.

Nick’s also the owner of Somewhere, Bolt Storage, and RE Cost Seg and considers himself an opportunist; the so called ‘boring’ and ‘old-fashioned’ businesses are what fuel him, both spiritually and financially speaking, considering they’re jointly making more than $30M in revenue.

Listen to Nick’s interview on YouTube, Spotify, or Apple Podcasts.

Thank you to our sponsor:

• Rho - A business banking platform, purpose-built for startups.

Let’s dive in.

Rho is a business banking platform, purpose-built for startups and they work with everyone from two-person YC startups with world-changing ideas to publicly-traded enterprises.

With Rho, founders get:

• A single pane of glass they can use to run and scale their business from Day 1: Bank account, corporate cards to start running – and expense management, bill pay automation, and accounting to help you move fast as you scale.

• The big thing with Rho: Every customer has a "person" at Rho. 24/7 customer support - phone, text, email - they will be there at every critical milestone in your startup's journey.

To learn why startups choose Rho, visit www.rho.co today.

• When it comes to growing a business, Nick embraces being scrappy and frugal. Along with giving out flyers under students’ doors, the entire marketing plan for Storage Squad was one simple sentence: “Need storage? StorageSquad.com, $29.99 per box all summer”. Nick himself wrote this same 8 words in chalk in over 5000 Boston sidewalks. Chalk and flyers did the trick—they grew to over $2M annual revenue.

• “Nobody’s ever going to give you permission. You have to give yourself permission”. When raising capital, Nick’s been rejected more times than he can count. But if it was all about the experience, the resumés and the ‘pedigree’, nobody would ever do anything. He willed himself to still go forward with expanding Storage Squad into a self storage business and prove himself to investors instead of patiently waiting for external approval.

• Social media had an unthinkable impact on Bolt Storage. With no barriers, he started sharing on @sweatystartup on Twitter what entrepreneur life looked like—the good, the bad and the ugly. Transparency at its core. By early 2021 they had gathered 750 investors, raised $20M and gone from 8 to 25 employees. All this only one year after Nick’s Twitter account first blew up.

• Your startup’s have it rough to compete with all the already established companies in the market; that’s just what it is. But to Nick, your startup does have two very important advantages you can’t squander: you can move faster, for one. Decisions can be made from one day to the next if you say so. Secondly, you can -and should- hire international talent to grow your company at a lower cost.

• Though Nick’s realized that building businesses is truly his driving force, The Sweaty Startup as the media aspect of his brand has been crucial in his entrepreneurial journey. First, because a strong social media presence makes for a great platform to actually grow the business. But also because by becoming a good communicator, Nick has become a better founder and leader as a result.

• Nick encourages all founders to stop seeing their first company as their ultimate cash cow. Your first company should be all about acquiring skills, connections and mainly capital. You’ve got the rest of your life to aim higher and take bigger risks.

Listen to Nick’s interview on YouTube, Spotify, or Apple Podcasts.

00:00 What’s coming in the episode…

00:54 Introduction

02:21 Nick’s background

05:53 Growth strategies

07:58 From college storage to self storage

11:00 Raising capital

13:17 Partnering with Dan Hagberg

17:21 Selling Storage Squad

19:31 Nick’s presence on Twitter

24:37 Acquiring Somewhere

33:01 Starting RE Cost Seg

37:30 Writing “The Sweaty Startup”

43:04 A business empire vs a media empire

47:23 What’s next?

49:16 Where’s the opportunity now?

56:34 Nick’s ideal business partners

58:07 Reach out to Nick

Links to Nick’s companies and socials:

www.sweatystartup.com

www.nickhuber.com

www.sweatystartupbook.com

www.somewhere.com

www.boltstorage.com

www.recostseg.com

www.adrhino.com

www.spidexx.com

www.boldseo.com

www.titanrisk.com

www.x.com/sweatystartup

www.instagram.com/sweatystartup

www.linkedin.com/in/sweatystartup

www.youtube.com/sweatystartup

www.tiktok.com/sweatystartup

www.threads.net/@sweatystartup.com

https://podcasts.apple.com/us/podcast/the-nick-huber-show/id1576120606

https://podcasts.apple.com/us/podcast/the-sweaty-startup/id1445260221

Link to buy Nick’s book on Amazon: https://amzn.to/4bLazjW

Best,
Justin

Founder of Just Go Grind

P.S. Hiring? Check out the team at Athyna