Dylan Diamond (Founder, Saturn)

"I said I'm about to start senior year of high school. And they're like, ‘Woah, you're young!’”

Dylan Diamond was in the final stages of an interview with Tesla. Yeah - at 17! But wait, it gets even crazier…

Not only did Dylan become Tesla’s youngest intern in the WORLD, but by 24, he built an app that blew up, with millions of users. Here's how it all went down:

Q: What was the story behind Saturn and how did you get it to reach the top charts on the App Store?

It started as a schedule-sharing website.

There was a moment twice a year in homeroom where you would get your paper schedule for the upcoming semester. People would take a picture of it, post it on Facebook, and say, “Like, or comment if you have class with me.” 

This was a common ritual across every high school in the country. Even before Facebook, people were comparing notes about who they were sitting next to in class.

So, I built a web app that would auto-complete your courses and teachers. You'd input the period number, and it would match you with your classmates. This was a rudimentary calendar schedule sharing tool and friend finder for my community.

I posted a link to it in the school Facebook group, and every kid got on that web app.

Q: Around this time, you joined Tesla and became their youngest intern ever. How did that happen?

Around the same time that I was building this schedule sharing product, my parents had gotten a Model S. I thought of it more as a computer on wheels than a vehicle.

And I'm not a car buff, but I was a huge nerd. So it was really exciting for me to see this sexy vehicle with an API and an interface to the internet. 

I hooked it up to my Wi-Fi network and did a lot of reverse engineering.

At the time Tesla's app was pretty simple. No map, data, sharing or anything of the sort, but the API had all that data.

So I basically built Garmin for Tesla on the Apple Watch. You could track where you're going, share rides with friends, talk about energy consumption, max speed, and display fun stats.

At the time the community was really tight knit and everyone was sharing in an online forum called the Tesla Motors Club. So I hacked together this app called Tesla Toolbox and posted it in the Tesla Motors Club. It went viral - 20,000 people bought the app in the first month. 

Q: How did Tesla originally reach out to you? 

I think it was an email. I got on the phone with a recruiter and my age did not come up until the end when I said, “I'm about to start senior year of high school” and they were like, “Whoa, you're young!”

When I first got to Tesla, I was able to take a lot of their backhouse data software and build it into internal tools. So things like inputting your destination into the supercharger network and seeing the nearest charging stations along the way.

I had such free reign. If I had an idea they just let me run with it. You were able to build whatever you wanted.

We were expanding so quickly at the time: Tesla was launching Model 3, the supercharger network was doubling year over year, and it was a really exciting time to be at the company during hyper growth - especially when the entire world was betting against us.

We were building cars on the weekends trying to hit 5,000 vehicles a week. It was so scrappy and taught me a lot, but the people I worked with were incredible.

Q: What were the most important things you learned at Tesla that you took with you when starting your own company?

Tesla didn't have excess capital, so you had to really be scrappy and when Saturn started we decided to self fund it. Max and I learned to really be scrappy and focus on one problem at a time. 

Secondly, at Tesla, when I was building software, there was no designer. I was the designer. I was the tester. I was the user. It was a one man show for at least what I was building.

So I took a lot of that with me and was able to make sure that it’s a best in class product.

Teslas look really good, but they're also best in class engineering, and oftentimes you have one or the other. Working there taught me the marriage of those two values.

Q: How did you meet your co-founder, Max?

He pinged me on LinkedIn and said, “Hey, I'm the youngest Managing Director at Havas, a big marketing firm, and worked with brands like Coca Cola, Beats, T Mobile…”

He was also not in a frat and prioritized his work over school and thought we would bond.

So he invited me over and we just talked for hours, spitballing ideas back and forth, talking about each other's different careers, and we had a very complimentary skill set.

He was all marketing and I was very much an engineer. It was a good mix.

We didn't know right away what we were going to build, but eventually we started looking at the Google Analytics data for that scheduling product. He saw that step function of 50% daily active users over enrollment to about 90% and he said,“Dylan, you have to bring this to another school.” 

It took some convincing because I was doing the dual degree and working at Tesla.

But on the weekends we would build this and we decided to take it to my cousin's high school. We got a signal that we had something when half the school downloaded the app on the first day. 

Q: When did you decide to drop out of Penn and leave Tesla?

I was coding day and night, trying to keep up with school, Tesla, and what would eventually become Saturn. All of this was taking up increasingly more time and Max had started to talk to a lot of VCs.

We took a trip out to California, with no intention of raising capital, went to LA and then SF and just started pitching.

We made a deck before and worked on that in the hotel room late at night before we raised.

We were really fortunate to meet General Catalyst and Niko Bonatsos there. They invested Snapchat and were one of the really good consumer investors.

When we met him, we just had a good conversation. It didn't feel like a pitch meeting. And the next day, he gave us a term sheet. It was for $2.5 Million. And that was like “Wow! We did not expect that.”

When we got that term sheet, it became clear that we have a big opportunity and we thought that we couldn't hire a team around us if we weren't fully committed.

Q: What tactics did you leverage to scale to millions of users across the country?

We didn't really do any paid marketing for the first 2-3 years of the company.

We leveraged an ambassador network for both user acquisition and user research.

When we would go to a school in a new market we didn't empathize with the users as much as the northeast public schools where I grew up. So we would work with them, we would understand what is important about the product for them.

Then those students would plant the seeds and Saturn would grow year over year.

So that's why the schools grow year over year.

It took us some time to identify that growth model as part of our business, but we really leaned into it.

For Dylan Diamond’s full story you can listen to my interview with him on Apple Podcasts, Spotify, or by clicking the image below.

Bryan Clayton Thumbnail

Hey there! 👋

While everyone’s buzzing about the latest breakthroughs in AI, we have a story that goes back to the roots of entrepreneurship. Bryan started off mowing lawns as a kid. Today, he runs the Uber of lawn mowing, GreenPal, which is now a $30 million business. This is his story. As always, you can find the full podcast episode here at The Dealroom. Now, on to Bryan Clayton!

Note: This story has been edited for reading clarity

Founder, Bryan Clayton shares the story:

It all started when I got a Nintendo 64 with Super Mario Kart. My dad got pissed off because I was playing Nintendo all day long, and he talked to the neighbor one day, and the neighbor was like, ‘Hey, I'm looking for someone to mow my yard.’

He goes, ‘My son cuts grass.’

He came up to my bedroom and said, ‘I got a gig for you. You're going to go mow the neighbor's yard.’

I said, ‘I don't mow yards.’

He goes, ‘Well you do now.’

I got paid $20 for an hour of work, and from that day forward, I was hooked on entrepreneurship.

The first thing I did was start passing out flyers all over the neighborhood. Before I knew it, I had 10 or 20 customers. So, I stuck with that little lawn-mowing business throughout high school and college. Then, when I graduated college, I had to make a decision. Would I stick with this lawn mowing business that I had run in high school and college, or would I do something else in my life?

I didn't really want to be a blue-collar laborer for the rest of my life. But I could quickly envision what this business could become if I had 10 or 20 employees.

And I thought, ‘Well, I'm going to see how big I can grow this.’

I made a business plan and thought it would be worth it if I could get to a point where I had two or three crews going out every day and didn't have to personally do the work anymore. By year two, I had 20 employees. That business eventually reached $10 million in sales and was acquired.

Q: How old were you when, when you sold the business?

32 years old. I made the decision to sell it at age 30, and it took me two years to get it sold.

I tried to retire. I tried to just do real estate investing and it got really boring. Life didn't have meaning anymore. I didn't realize it, but my company was the reason why I got out of bed in the morning. So, I needed another mission. And that's where GreenPal started, the Uber of lawn mowing.

Q: How did you scale GreenPal into a $30 Million tech business without knowing how to code?

Well, it started with naivety. When I was running my landscaping company, I saw it was hard for consumers to quickly get pricing and discover which landscapers were reliable. And then, as a service provider, it's really hard running that kind of business because you don't have time to run sales, give estimates, or even answer the phone. You're literally cutting grass, and at night, you're mailing out invoices. It's just a grind.

I knew that somebody was going to build a platform that solved all those problems with a clean user experience. What I didn't have was the technical acumen.

I started attending tech meetups but had no luck finding technical people to start the business with.

I told two friends about the idea, and they said, ‘I'll quit my job tomorrow and do that with you.’

It was two guys that worked in sales at Dell. The three of us formed this company. We pulled our money together and sketched out what we thought the app would look like on a whiteboard.

We took pictures of those boxes and started talking to dev shops. We landed on one of the quotes that was $180,000, and we paid these guys to build what we thought the app should be. It took them 9-10 months. When we got it back, we quickly realized that this was a huge mistake. This thing barely worked; it was clunky and unintuitive, and there was no way we could do this if we couldn't go through iteration cycles quicker than 11 months.

At this point, we're all broke. I had taken all my proceeds from selling my business and locked them down in highly illiquid investments.

So, even though I had cash-flowing assets, I had little money in the bank. I was very cash-poor.

Q: What did you guys do from there?

I personally made the decision that no matter what, from that day forward, I was just going to work as hard as I could on the business. We have this terrible app; let's go door to door and talk to as many people as possible, pitching them on the idea of using it.

We did that until we got a hundred people, and they would always tell us everywhere the app sucked, but they never told us I don't need this. And one English lady said, ‘Oh, it would be divine if it did work.’

That stuck with me. Now we got to go find somebody to help us build this thing.

My co-founder is like, ‘Well, I found this thing called the Nashville software school. It's a boot camp for nine months, and it’s $12k.’

He put $12k on his credit card that he didn't have, and he started attending the Nashville software school 8 hours a day. Whatever he learned in a given week, he took and started rebuilding the platform from the back end.

We're like, ‘Word. Dev - check. Zach's going to become one.’

He's like, ‘Well, what you don't know is that it's going to take a lot longer than you think and somebody has got to build the front end of this.’

So I started going to YouTube University, looking up how to code HTML, CSS basics, and JavaScript tutorials, and I started taking every online class I could. After about three months, I became the world's worst front-end developer. But it was just enough where I could take what he was working with and connect to it and build the views.

We got to about 400-500 customers and then we got to a point where we could start just rinse and repeat.

People ask me if I will start another startup.

I will never do it again.

It's so much not fun, and your odds of success are so small.

Q: How did you scale the platform and get hundreds of thousands of users?

If I had to distill it into one thing, it would be the marketplace's ability to generate demand. I knew that Google was going to be a channel for us, but I was hearing it so much, I was thinking, ‘Man, this may be the channel.’

We won't compete for these head terms, but we could compete for the long tail. So, we had five or ten service providers in Smyrna, Tennessee. We interviewed them and wrote content about them. It was unique, rich, organic content about these small business owners that didn't exist anywhere else. From that bottoms-up approach, we started noticing in Google Analytics that we were getting a little bit of traffic.

Q: How did it feel when you made your first $10 million off of that?

Scary.

I thought, ‘Man, I don't know that we can run this at $20 million. I’ve never ran a $20 million business.’

If you're feeling imposter syndrome, it's a good sign. You want to feel it at almost every step of the game because that means you're pushing it as far as you can.

We didn't celebrate it because we've never really felt successful or like we've made it. It's always felt like day one. And it's always been like, ‘Oh, look how far we've come! Yeah, but we've got to figure this thing out.’

For Bryan Clayton’s full story you can listen to my interview with him on Apple Podcasts, Spotify, or by clicking the image below.

Listen now

Have a productive week!

Shamus

Jacob Klug Thumbnail

Hey there! 👋

First, hope you had a BANGER July 4th! Weather here on the East Coast was beautiful, but not as beautiful as how much money this guy makes per month at just 20-years-old! As always, you can find the full podcast episode here at The Dealroom. Now, on to Jacob Klug!

Note: This story has been edited for reading clarity

Founder, Jacob Klug shares the story:

In high school, I was running a real estate marketing company. We mainly had realtors and some local businesses, but we realized a lot of them were trying to transition during COVID. Obviously, everything was digital, and a couple of out clients were looking to build a platform that integrates with Zoom and a lot of other community features.

I was like, ‘Well, this is super interesting. I’ve used Bubble.io and no code; maybe we can actually do this as a service.’

That's when the light bulb moment struck for me, and we took on our first client.

I woke up every day, and it never felt like a job. This was something I was doing over my weekends and now I do it during the week.

It’s really hard, though, because in the first 6-12 months, nothing happens. Yeah, we got a couple of clients, but they're small clients. It was one client here, and then a couple of months later, the next client and it would slowly trickle in. Unless you enjoy what you're doing, you're going to be like, ‘Well, it's not making money fast enough.’

I just kept doing it because it’s fun. Later, by the time you snap your fingers, you realize, ‘I actually have something. I have a real business here.’

Q: Did you graduate high school?

I was failing high school, and if I didn't do something about it, I would be held back.

So I had to make deals with all my teachers. I called all of them and told them, ‘Look, I cannot go to class on Zoom. I had other [sales] calls during them’

I explained to them what I was doing, and luckily enough, all the teachers of classes I needed to pass gave me flexibility for my assignments. They agreed that as long as I did the assignments, I didn't need to show up to class.

Q: What are the capabilities of no-code?

No-code is a new rise in tools that we've seen. There are different tiers of no-code. You have what I call tier one, which is like the OG at WordPress. They essentially created this new category because of the time coding just a basic website required. WordPress bridged the gap. 

The second tier includes tools like Notion that are made for you but can also be customized. You also have things like Webflow and Framer, which allow you to build cool, interactive, and custom websites. 

But where I hang out is, you could call it tier three or tier four, which is complex web apps, web applications, mobile apps, etc. There are tools such as Bubble.io, where you can essentially build pretty much any kind of web application using a drag-and-drop element for the front end that's completely custom.

All our apps you would not be able to know were no code. The tools we create range from building for startups to building internal tools for enterprises that are looking to automate their systems.

Q: How much did you start your business, Creme Digital, with?

Nothing. Agencies are great because they require no upfront capital. It's a positive cash flow cycle. When you think about it, you are selling and getting money in the door before actually delivering the service. 

It's not just agencies. There are other service businesses where you can implement this. But you have to get creative around ‘How do I get money in the door before I deliver? Even if it's like 50%.’ Which is what we did. We had clients and would take a 50% deposit. I'd then use that money to hire people to do the work, deliver the work, and then you get the other 50%. 

Q: What did you do to grow the business early on as a high school student?

One of the biggest things is always word of mouth, like referrals.

But the two main ways are:

1. Inbound 

2. Outbound

Inbound is Google ads, people intently searching, ‘I want to build a product.’ Outbound, which we're pushing out more now, is like cold emails. So, we experiment a lot with organic content, podcasts, socials, and Twitter just to get the message around.

Q: How did you get the YouTuber Airrack as a client?

Yeah, that was a funny one because his manager posted on Twitter that they were looking for bubble developers. My friend knew the manager and introduced us. They came to us, and they were like, ‘We need to launch this in three weeks, and we have half the platform ready. We need somebody to finish it off.’

So it was super pressing. We had 2-3 weeks to revamp this whole product before it went live to millions of people. We just grinded it out and dedicated the whole team to this one project. We really wanted to impress them, too, because we knew it would be kind of cool. When we showed them the app, they were blown away.

Q: How much does the business make today? 

Every month is different. We work on a subscription model, so we're an in-house fractionalized team for companies. We used to do fixed-scoped projects where you would come in, and we'd price it out, but we've transitioned to a purely monthly model.

It's good because our monthly revenue is more stable. It also gives the client a lot more flexibility around what they can do because they're not tied in. But on average, we're doing around $80,000-$120,000/month.

For Jacob Klug’s full story you can listen to my interview with him on Apple Podcasts, Spotify, or by clicking the image below.

Have a productive week!

Shamus

Gina Gotthilf Thumbnail

Hey! Shamus here, and welcome to another edition of The Dealroom, a newsletter (and podcast) sharing the stories of world-class entrepreneurs to inspire the next generation. Now, onto Duolingo!

Note: This story has been edited for reading clarity

Gina Gotthilf shares the story:

My original plan was to live and work on a farm, but I was quickly snatched back into the business world by an opportunity that fell into my lap. 

Q: How did you get that opportunity?

So, right before my visa expired, I thought, “Okay, there are a couple of people that I emailed who I thought were really interesting and I never got to meet. So I'm going to email them and say, ‘Hey, I have to leave the country; I would love to have coffee with you.’”

One of these people was Mark Coatney. Mark was leading media at Tumblr. They were small at the time, and I said, ‘Hey, if you guys help me do an awesome job for my client and make me look good, then you can use this as a case study for other big brands.’

We ended up working a little bit but over email. I met up with Mark once. We had a coffee, I told him a little bit about myself and that I’m from Brazil. When Tumblr decided to expand internationally, they were like, ‘Who do we know in Brazil? Oh, that girl!’

They contacted me, and I was like, ‘This sounds really nice, but I am no longer doing the career thing. I'm out.’

They were like, ‘Yeah, that's cute. But, let's explain to you why it would be good for you to work with us for at least one month.’

I accepted because it made a lot of sense. That month, I was just hustling to grow Tumblr and find the connections to put it in front of the media.

Q: What were some of the growth hacks that you employed to grow Tumblr?

Growth hacking didn't even exist as a concept. Of course, everyone was trying to make things grow through marketing, but the concept of growth that we know today didn't exist.

My mandate was, ‘Can you help us grow without any cash?’

I just thought, ‘How can I get this in front of as many people as possible, but for free?’

So, I ended up doing a lot of PR, but at the time, I didn't know it was PR.

I was like, ‘I bet that I can convince journalists that these New York people are special people worth talking to if I positioned them in a certain way.’ 

And so I just started finding all the journalist names that I could on Twitter, on LinkedIn, etc. I would literally go through the newspapers and magazines and write down the names of authors who I thought might be interested in something like Tumblr. Finding ways to interest these journalists and get them to talk to these guys worked out really well.

I also did things that led to PR. We brought some important comedians onto Tumblr, and that became a story. We started partnering with the government, and that became a story. We did their biggest-ever community meetup for 1,200 people, and that became a story. 

Those events in themselves didn't lead directly to growth, but then the story led to growth.

It's a playbook that I ended up reimplementing at Duolingo. 

Q: What do people most misunderstand about PR?

There is so much people misunderstand about PR. First of all, people often think of PR as like these like very strict stories that you want to tell.

And often, when it's a startup context, it's about fundraising. It's like, ‘We raised a round!’ Then people will come and say, ‘We did PR, and it didn't work with growth.’

A story about fundraising does not work for growth. It's a very different kind of story than the one that works for growth because the story about fundraising makes your company look really successful, and investors might be interested, but it doesn't make someone like you and me read and go, 'Wow, I really want to download that app.’

For Duolingo, we would find stories like someone who was able to double their salary because they learned English with Duolingo, and they're working at a mall in a restaurant. If I read that, I think, ‘I want to double my salary, too. If that guy did it, I definitely can do it too.’

Q: What are growth hacks that people are ignoring today that they shouldn't be?

I think that’s a million-dollar question. It's not about tactics. It's about understanding how things are evolving, where the opportunities are, and where you can jump in.

Over the past five years, people have all become their own little media brands. Everyone is on TikTok, has things to say, has a platform, and wants to be something. I don't think that has been leveraged to its full potential from the super micro influencer perspective because people make decisions based on what their friends tell them and what their families tell them.

That's the most important node that you can capture. When you have a social following of any sort, you have a smaller group of people who really trust you. Leveraging that—we haven't quite figured it out yet, but it can be huge.

For the full story of Duolingo, you can listen to my interview with Gina Gotthilf on Apple Podcasts, Spotify, or by clicking the image below.

Have a productive week!

Shamus

Hey! Shamus here, and welcome to another edition of The Dealroom, a newsletter (and podcast) sharing the stories of world-class entrepreneurs to inspire the next generation. Now, onto Chess.com!

Note: This story has been edited for reading clarity

Founder, Erik Allebest shares the story:

I needed a change, and my wife told me ‘You need to do something different.’ Our business was flat. I was playing too many video games, wasn't taking care of my health, and I needed a big reset. 

She’s said, ‘You’ve got to go to business school. I'm going to help you write your essays. I think this is your last chance to use that really lucky GMAT score you got coming out of college.’ 

I decided, ‘Alright, let's do it.’ 

But I will say I went there with a fair amount of ego. I'm a pretty different person than when I first got there because I didn't have a lot of other peers who were doing similar things as me. Most people were in entry-level jobs right out of college, and I was here running a business and making a lot of money. 

I thought, ‘Hey, I'm an entrepreneur. I know what I'm doing. I'm going to go to Stanford. I don't know what I'm going to learn there...’ 

It turns out I didn't know anything. 

Q: What do you think is the biggest thing you learned? 

Wow. That's a huge question.

I realized that building a company is bringing together an orchestration of so many different elements. You’re a conductor in an orchestra, and you're moving people around to create something. In order to do that, you have to put the best people in the right seats. There are a lot of different types of leaders from sales leaders, cultural leaders, product leaders, and technology founders. You have some people who have a ruthless mission and are jerks to work for, but they pay people a lot of money. But when I went to business school, my personal life philosophy was much different. 

I wanted to know, ‘How do you create an amazing culture that people want to be a part of and do great things together?’ That’s what I’ve learned. 

Q: What's the founding story behind Chess.com? How did you come up with the idea? And why did you decide to start the business? 

We started with wholesale chess, and when you searched on Google, there were two sections:

1. Ads
2. Search Results

We were constantly battling who was first for organic search results on Google, and there was immense competition between the top sites. We were nickel-and-diming each other down on price. Meanwhile, we were spending more and more money to get clicks to our site, and our margins were evaporating. I was like, ‘This is going to break and fail.’

That’s when I noticed this platform called MySpace, which at the time was very popular. I thought to myself, ‘Why don't we build a community for chess players?’

Then they'll come to play and learn about chess. Eventually, they'll buy the chess equipment, and we can have a better chess-selling business. 

While this was percolating, I got into Stanford Business School and realized I couldn't keep running this business. So, I sold the business but kept the domain name. 

While I was at the business school, I built all the wireframes and began work with my co-founder, Jay. He was on the technical side and two of us would do school during the day and work until 3 AM. I was staying up and building Chess.com with Jay. It was a grind. Also, I had two or three kids at the time. I was a pretty busy person, not taking care of myself. It was a period of investment. But when I graduated, I had some job offers at Facebook, Palantir, YouTube, Mint and other companies. 

Yet I decided to try this chess thing, and everyone was like, ‘You're crazy!’ 

I was like, ‘Maybe. I'll go get a job later, but I'm just going to see this out.’ 

And as I graduated, we started Chess.com using some money from having sold the other companies.

Q: How did you get your first thousand people in Chess.com’s community?

Through online communities and forums.

It was a simpler world. Social media was different back then. There used to be tiny pockets, like subreddits. One would be a place for talking about cars, then you'd go to Golf.com to talk about golf, etc.

Chess.com was where we had the community forum. Every single day, a thousand people would type chess into the browser, and Google would put a .com on it, and people would sign up. Eventually, Google Chrome stopped putting the .com on the end. So people would search chess, and we were already number one. There was a lot of natural growth from search engine optimization (SEO) and the virality of people sharing their experiences. 

Q: Why did every investor say “no” to you?

I met so many great people. When you're an investor, you have to be very careful in choosing businesses because your hit rate is so low. You have to choose businesses that can do outsized returns. 

So everyone looked at chess and thought, ‘Chess is tiny. It's insignificant. Why are you spending your time on this?’ 

And so it just wasn't big enough for anybody. I ended up funding it myself.

Q: What were the key inflection points that kind of led Chess.com to where it is today? 

So being excellent at SEO and being excellent at content.

People don't want ads; they want content. That's where they're putting their eyeballs. We knew very early on that instead of investing a ton of money into buying ads, we should invest in content because that's where people want to be. 

People are more inclined from short-form content and creator partnerships. All of it’s just content, and the community builds around the content.

There are a lot of people who do well using ads, but it just wasn't our strategy. Content and community have always been our strategy plus product excellence. 

For the full story of Chess.com, you can listen to my interview with Erik Allebest on Apple Podcasts, Spotify, or by clicking the image below.

Have a productive week!

Shamus

Hey there! Long time no see. I know that’s on me. Launching a new company takes a lot out of you, but we’re back and stronger than ever! 🚀 

This week, I sat down with Neil Parikh, who Co-Founded Casper into a $575M exit. Here’s how he did it.

Founder Neil Parikh shares the story:

I went to medical school at Brown, and I thought I was going to be a doctor. But the thing about medical school at that time was that they were not looking for innovative students. It’s mostly memorizing stuff, doing your homework, and taking a test. It's like the army. And that didn't resonate very well with me.

So I told my parents, ‘Hey, I'm going to take a year off. I'm going to move to New York City, and I'm going to figure something else out.’

First of all, they had a heart attack. My parents called me and turned blue in the face. They were very upset because they thought I might never go back to medical school. Which I didn't. So I moved to New York with some of my friends who had just graduated from undergrad. We ended up starting a series of companies, one of them being Consigned. And we were actually in an accelerator program in New York City at a coworking space where I happened to sit next to somebody who became my friend named Phillip. One day, I heard him talking about how he used to sell mattresses online from his dorm room.

And I'm like, ‘That's a dumb idea. Who's ever going to buy a mattress on the internet? Don't you have to try it before you buy it?’

But my dad was actually a sleep doctor. And I guess I've been thinking about the consumer applications of what could happen in healthcare and e-commerce. We realized together that there was a moment in time when all these industries could be disruptive. We saw Warby Parker and Harry's, and we said, ‘That's funny; mattresses are like a terrible industry. You have to negotiate the price.’

But when we go buy this water, you don't say, ‘No, I'm going to pay 80 cents for it.’ 

So we said, ‘What if we could totally improve the experience? But more importantly than that, what if we could build the Nike of sleep, where we could figure out how to create products, services, and other things that could help?’

Then, over time, we expanded into many other categories, and the co-founding journey evolved with that.

Q: You go to raise money from investors, but their reaction is not what you expected. What happened?

It's so funny because we were like, ‘This is a genius idea. Of course, it's going to work.’ 

Then we start pitching investors, and one by one, it's like dominoes falling, but in a bad way. Everybody's like, ‘Yeah, nobody's ever going to buy a mattress on the internet. The economics are never going to work.’ 

We probably had 50 meetings of all no's before we got to our first yes.

Q: Earlier, I saw this picture, which I think is pretty important from when you were trying to get investors. What story does that picture share?

Okay, so this is what happened. One of the investors we met was Ben Lerer (Managing Partner at Lerer Hippeau). Ben had actually been thinking about this category for a while and had tried starting this company in a different way, but it hadn't worked. So when we met, he was the first person who said, ‘I get it.’ 

So we're super excited. He's like, ‘I want to invest. And I'm going to write a $400,000 check.’ 

This was the biggest deal in the entire world. When we found out, I literally kissed the ground because we had no money essentially before this.

But Ben's one stipulation was, ‘Can I try the bed before I say yes because I want to make sure it's good?’

Now, here's the thing. We didn't really have a lot of production beds, but he's an investor. We’re like, ‘Yeah, of course.’ 

So we overnight a bed from our factory, we rent a U-Haul, put the mattress inside, drive to his house, and we go up into his Soho loft, and we see his wife there.

We're like, ‘Hey, we're here to install the mattress.’ And she thinks we’re the mattress delivery guys.

So she's like, ‘All right, cool. Yeah, it's in the back. You can go do it.’ 

So we go put the mattress in, and as I'm swinging the mattress around, we knock over one of his lamps.

I'm like, ‘This is a disaster!’ 

We finally installed the mattress. But what we didn't realize was that we didn't have a place to store it. So, basically, we threw away his old mattress. We prayed that he would like it because if he didn't and he wanted his old bed back, we had no other options. We kind of didn't sleep that night, hoping that he and his wife would have a good experience.

Luckily, the next day or two, we got an email that just said, ‘AMAZING!’ 

Then we knew the round was going to happen, but those were probably the most stressful few days of our lives.

Q: How did you sell $1 Million of mattresses in 30 days? What was that inflection point?

I think it was aggressively using earned media and then following up with paid media. Earned media is often about credibility, about figuring out how to get in front of people when they're not in the mindset to buy something. Paid media is often about finding people who are currently in the market.

Now, the thing about mattresses is not that many people wake up in the morning and go, ‘Oh yeah, today's a good day to buy a mattress.’ 

Usually, there's something happening in your life. You're moving into somebody's house, out of somebody's house, you're going to college, you're moving out of your parent’s house. There's usually some life event that's happening. So, a lot of what we spent our time on was thinking through how we could figure out how to tap into those life events and make sure that we're present right there when we need to.

Now, the amazing thing about having an expensive product (~$1,000) is you only have to sell a thousand beds.

Okay, ‘Are there a thousand people that we can find that could buy our product in a month?’

Now that I look back on it, it's not that impossible to think about, right? If I called up 50 people every day, could I sell a thousand in a month? Maybe. And so, I think actually it wasn't so implausible, but to be fair, a lot of things had to go right at the same time.

Q: What were some of the marketing strategies you used to tap into those life events?

So, over time, it was a lot of marketing partnerships, right? In our first year, we partnered with Uber. In New York City, there was a little Casper button, and you could call a Casper van that would show up at your house. Inside that van, we'd built a little bedroom where you could go try out the product. Instead of opening our own showrooms at the beginning, you could get a showroom on demand.

We also partnered with people who were delivering mailers to your house. We figured out that right when you're about to move, you change your address. That's probably a good time to message you because you're going to be in the market. We partnered with colleges and figured out how to get things to you.

I think a lot of marketing is about arbitrage. It's how you can figure out how to get your message to people whom other people are ignoring. So, in the early days, we'd advertise on these radio shows that nobody had ever heard of. What we realized is that these radio hosts, when they would talk about how amazing Casper was to their audience in Oregon or places that were outside of New York City, would crush it. Their sell-through rates would be incredible. And while a lot of our competitors were just advertising in the traditional New York and San Francisco, we realized there are so many people outside of the core demographic that you expect that could buy your product.

I think you have to be creative and figure out how to do things differently. I mean, look, how many marketing campaigns can the average person ever remember?

I bet it's less than one handful. What that means is that breaking through the noise is really hard. What we realized was that nobody was advertising on the New York City subways. And if you ride the subway back then, the only ads you would see are for these dermatologists who pop your pimples and really weird stuff. There were no cool brands advertising on the subways. So we met the person who does the advertising, and we said, ‘You know what, maybe this can be interesting.’ 

You have a captive audience. They have to sit opposite this advertising for a meaningful amount of time. And maybe we can be a little bit controversial.

So we started launching puzzles, which we actually put on either word games or other puzzles that people could solve. And what happened?

They weren't really necessarily always about our product, but everybody would start talking about them because they'd go, ‘Oh man, did you solve that puzzle for that game?’ 

We turned an advertising unit, which was kind of bad, into one that was much cooler and ended up having a captive audience that then people would actually start talking about natively.

The extension was a lot further than we expected.

For the full story of Casper, you can listen to my full interview with Neil Parikh on Apple Podcasts, Spotify, or by clicking the image below.

Have a productive week!

Shamus

Founder of Dealroom Media

The other day, I was scrolling through LinkedIn when, all of a sudden, my eyes stopped dead in their tracks.

Sequoia just backed a new early-stage consumer company.

One of the only investments they made in a consumer business in YEARS!

What’s so special about this guy and his company? 

So, I did some digging and found that their founder, Sam Obletz is tackling a major problem.

He’s a Harvard graduate that’s building an app to replace Facebook Advertising forever.

Whoah, that’s one heck of a story!

So, I decided to have Sam on to learn exactly what he’s doing, how he’s raised over $8 Million, and the tactics his team is using to go viral.

Here’s the story behind Claim. 👇️ 

Note: This story has been edited for reading clarity

Q: Sam, what’s wrong with advertising today?

Oh boy, here we go. Let's attack this from both a consumer lens and an advertiser lens. Let's start with the merchant lens.

I actually think that most people don't realize how difficult it is to be a marketer. There are a few reasons for that.

1. It’s very difficult to make your P&L really pencil right now, given the cost of getting customers in the door for the first time.

2. Figuring out where a customer came from is more complex than ever.

We see billion-dollar industries developed around multi-touch attribution and assigning value to where a customer came in the door. Unfortunately, the process is becoming increasingly opaque, especially for the end user. It's kind of a fool's errand, in a way.

And so that's complicating the picture.

Lastly, the phasing out of cookies and Apple’s “Do Not Track,” have good intent, but they further complicate the ability of the marketer to say, ‘How do I find the right customers?’

They are being asked to grow gross margins, and they’re given a legacy set of tools to do so.

On the consumer side, attention is at an all-time low, which is again feeding into the vicious cycle of CPAs being at an all-time high.

We see advertising all day on our screens, creating desensitization to brands that try to grab our attention. We're not on Instagram to be sold things, and we're not walking down the street to be sold things. So it's a rude interruption in our day.

Q: What inspired you to build a company to solve this issue?

Yeah, I grew up with Facebook. At the end of college, I deleted it entirely because I felt two things.

1. The dopamine loop is real. I felt myself getting dragged more and more into Facebook and checking it at the expense of real-world relationships.

2. I got tired of the 4th or 5th direct-to-consumer company trying to reach me on Facebook when I was not there to be sold to.

We've built Claim to be the anti-Instagram.

The second aspect of starting Claim came from the feeling that a lot of our digital interactions are more transactional than ever right now. We wanted to bring back that emotional connection through authenticity.

Q: How do you bring back that emotional connection to brands?

Claim App UI

When you sign up, we'll add you to the activity feed. We spoke to the early folks at Venmo, and many people asked why Venmo had an activity feed.

Like, ‘Why do I need to see my friends paying each other rent or paying each other back for pizza?’

At the beginning and still today, that's to really drive home the point that activity is happening here. This thing is real. It’s credible. It's trustworthy.

In the same way, we drop you on the activity, and you can see the pace of interaction on the platform. If you open the app right now, you'll see hundreds of activities happening on the platform per minute.

What's cool about that is you're kind of immersed in this world.

We send a text to everyone at 11 AM EST on Thursdays. We say the drop is here, come grab your Claim (discount or reward to try a new brand). People look forward to that. I've had students tell me that the Claim is a bright spot in their week. They look forward to this.

It's not only an excuse to try a new brand but to go with a friend. That experience brings back that social experience of trying something new together. If you're going to try a new restaurant for the first time when you associate that with a social experience, you tend to value it higher, not to mention if you do work, you're going to value that experience higher.

It's the classic Ikea effect in consumer psychology.

For the full story, you can listen to my full interview with Sam Obletz on Apple Podcasts, Spotify, or by clicking the image below.

Have a productive week!

Shamus

Founder of Dealroom Media

Joe Lemay

Founder Joe Lemay shares the story:

I remember taking a flight to Seattle because [the company I was working for] partnered with Microsoft on a project. I felt I had to get in the room with a whiteboard with these other engineers. Doing it online wasn't going to cut it.

So, that's what I started to solve first. I worked on a project called Rocketboard, which was all about sharing an ordinary whiteboard with no electronics except your smartphone and turning that into something that feels like a Zoom experience.

After we listed it on Product Hunt it skyrocketed to #2 and got 20,000 email signups. But the problem was it didn't work very well in its first iteration. I was churning users and running out of money waiting for this thing to create product market fit.

And I was like, ‘How can I use this app I've built to make some money before I have to throw in the towel?’

After a few days of thinking, I literally just woke up with the idea of a notebook. One where you can erase everything in the pages by putting it in the microwave for a minute.

[Then Joe saw a tweet from Jason Calacanis that changed everything]

“Jason said, ‘I'm looking for stealth startups to launch on my stage. Tweet at me what you got.’ 

I had not really shown the idea of Rocketbook to anyone. There was no website.

I tweeted at him and said, ‘I'll have a video at you by the end of the weekend.’

Then, I just spent the weekend making a video of the notebook. I made it look like it was able to scan and erase by putting it in a microwave.

But it did not actually do anything.

He's like, ‘This is great. I love it. You're invited to San Francisco, and you have to be out here a couple weeks in advance in order to rehearse to make it on stage.’

When we get on stage, I show everyone how the notebook works. You put it in the microwave, and it all erases.

People are like, ‘Are you kidding me? This is crazy, right? It's just a paper and pen notebook, but it all erases in the microwave?’

And I ask everyone, ‘Now, who here wants a Rocketbook?’ 

People raise their hands.

I'm like, ‘Great! You can buy it now or pre-order yours now on Indiegogo.’

That day we got about $2,000 worth of pre orders. The next day, maybe another $3,000, and we're like, ‘Hey, that's pretty cool.’

When we woke up on Saturday our phones went berserk.

It was just ‘ding, ding, ding, ding, ding!’ We sold $99,000 worth of notebook pre-sales that day.

Q: How did you go from those 2,000 initial backers to raising $1 million in funding from that campaign?

A couple of things were instrumental.

One is we had a product that was really worthy of people talking about, and our conversion rate was really good. Our copy and our video were effective.

We didn't really have any marketing budget, right? So we had to be irreverent, stand out, and capture people in the first 10 seconds of the video. We thought a good way to do that would be two dudes in sunglasses and an astronaut outfit throwing notebooks around Staples.

Because all these notebooks have just been sitting here collecting dust while other products have been innovated. There are smart helmets, smart shoes, and smart everything. But the notebook industry had been asleep at the wheel, and we're making fun of them by pulling a [paper notebook] off of the shelf and saying, ‘Hey, what is this? The notebook that Hemingway wrote in. That's cool, I guess,’ and tossing it.

We did not have permission from Staples to do this, so we dressed in our orange astronaut outfits that we got from Amazon and decided to do it until we got kicked out of Staples, but it took a surprising long time to get kicked out.

Q: In November, 2015 things started to take a turn for the worst. What happened?

Yeah, so we launched this crowdfunding campaign in March and had given an estimated delivery day of November. We thought that would be plenty of time. But the major [issue] was getting the notebook itself to work reliably in various microwaves.

The problem was that if you took one of our prototypes and put it in a microwave for a minute, the heat-erase ink would make it clear, and everything would work great, but if you put the same notebook in my microwave, it might not erase completely after one minute. And if you put it in someone else's, it may burst into flames within a minute because microwaves have different power levels.

We ran into some problems fulfilling it and getting it manufactured, and then I owed one of our vendors over $400,000 before they released the next batch of books as well. So I was kind of stuck. And what were we going to do? Tell the rest of the backers that, ‘Sorry, we're bankrupt. We can't deliver your product.’

Q: How did backers respond to the delay?

Some were patient, some were like, ‘Cool, this happens in crowdfunding.’

Others were like, ‘I want my money back.’ And I said no to everybody if they wanted their money back. I'm like, ‘This is a crowdfunding campaign. I'm sorry if you're mad at us, but we're trying to use all the funds to get everything out for everybody.’ 

Some people got extremely angry about that…

They're like, ‘I can't believe this. This is outrageous. You clearly have a million dollars in your bank account, and you're taking off for Jamaica. I want to f**ing k*ll you. You suck.’

My emotional health was at a really low point where I was like taking Adderall during the day to like keep going. I was just terrified that we wouldn't make it through, and I would look like a loser and have to go get a real job, and suicidal thoughts came up. I'm not saying I was on the brink of suicide, but it was one of the few times in my life when these intrusive suicidal thoughts were in my head at times.

Between making the product, I didn't even have time to respond to all of the comments because I just decided I was going to focus on the product. If I have to spend 15-20 hours in a day working on something, it's going to be working on this emergency, which is the product.

That pressure actually got us to figure out the problem, deliver to backers [and build new products that would help us reach a $50 Million exit].

For the full story, you can listen to my conversation with Joe Lemay on Apple Podcasts, Spotify, or by clicking the image below.

Bobby Brannigan thumbnail

We did a thing…

I was up all night thinking about how to announce this, but f*ck it. Here I go. I’ve spent the last three years interviewing founders and sharing the stories of Warby Parker, Zillow, Rippling, Uber, etc.

7+ Million views and counting we’ve learned a thing or two about what makes a compelling story.

So, for the readers of this newsletter, I am offering a FREE 30-minute marketing strategy consultation for your business. You can redeem the offer here.

P.S. The link expires in 72 hours, so make sure you grab a time early; there are limited spots remaining.

Thank you for all of your support. I would not have been able to do any of this without you. Now, onto the story of ValoreBooks.

Founder, Bobby Brannigan shares the story:

“It started at the end of my freshman year. I went to the bookstore to sell my books, as most students do, and they wouldn't buy half the books. So I asked the rep, ‘What do you want me to do with these books?’ She's like, ‘You can throw them in that pile over there.’

So I look at the pile, I'm like, ‘Wait a second, can I have the pile?’ She's like, ‘Sure.’ So my friend and I brought them back to my room, and within a week and a half, I sold them for like $5,000 on eBay. That was my ‘Oh sh*t’ moment.

When I came back the next semester, I was like, ‘Okay, game time; I got to get my hands on a lot more books.’

My first thought was, ‘Let me just put up posters around campus, in the dorm rooms, and the dorm bathrooms.’ I told the RAs and all over I would post these posters that I printed in the college library.

It said, ‘If you have books to sell, email me the ISBN numbers, and I'll give you a price. If you like it, I’ll pick them up, and you can give me cash.’”

Q: How successful were those posters in bringing in customers?

“Yeah, I think it was somewhere between like $500-800 a week in books I would buy, and I usually like double, triple, and quadruple my money. So, in the beginning, it was obviously pretty good.”

Q: How much did you bootstrap the company with?

“That's a good question.

The amounts fluctuated because what we were doing was flipping textbooks along the way and generating profit. We made $5-7 million in profit to fund the development of the [textbook] marketplace. But we also had to borrow money to do so, and we did so in very unconventional ways. We were able to amass, I think, $250k in credit card debt, and we actually had a person who managed a baseball card binder with all the credit cards in it.

Second, my father let me take out a home equity loan on his house.

[And third], we borrowed money from people, I'll call it, on the streets of Brooklyn, and if I didn't pay the people on the streets, I would have gotten my legs chopped off. So we were pretty extreme. I will say I was a very confident student. I didn't think anything could stop me. So, I took major risks.

[But it was extremely stressful] I remember driving on the highway in Buffalo, on I-90, and I remember blacking out while I was driving. I woke up on the side of the highway and was like, ‘What the hell is this?’ 

So, a few months later, I put my friend Scott in charge of the textbook marketplace while I took a month off.”

Q: How did you go from those few million in sales to that 85 million exit?

“What I ended up doing for the first time ever in the company. It's kind of crazy. I started talking to the customer, and our customer was the merchant. One of the most memorable was a guy named James Barnes who flew out to Little Rock, Arkansas and had a steak dinner with him and his whole team, which was like 10 of them.

I asked them, ‘What can I do to help them grow your business?’ They said, ‘Help us buy more books. We don't care about selling books. We sell with you because you de-risk us from depending on Amazon. We'll buy an unlimited amount.’

I immediately had an idea. I said, ‘Alright, would you want to bid on them? If you could bid on them, would you be okay with getting them in four months? And would you be able to give us a price four months in advance that we could power rentals with?’

That seems good. Let's do it. That was our moment where it's like, Oh my gosh, for seven years, I've been begging people to get in the marketplace. And now they're coming up like texting me, calling me, LinkedIn messaging me, ‘Can I be a part of this bid opportunity?’ So, that's what grew the company. It was purely innovation and asking the customer what they wanted.”

Q: What was the story of when you decided to sell the business? How did that go?

“Well, at that point, I had everything in the company. I wasn’t borrowing money from the scary people in Brooklyn anymore but I still had a home equity line at my parents’s house, and credit card debt, and like all these things. And all of my money was in the company, right? Like everything. So we're like, ‘What do we do?’

So, we started searching. We hired a banker. We talked to a bunch of people, and we found an unconventional opportunity. We ended up finding a company in Boston that was kind of like the kayak for student loans, and the founder of that company had a vision to partner. We ended up getting acquired by them, and they eventually got acquired by LendingTree.

But, it ended up being a great, great partnership because they had been in student loans for a long time, and they had other ways of getting traffic, and they had millions of customers, too.”

Q: How did it feel when you sold for tens of millions of dollars?

“It felt amazing. When that wire hit my account. I remember pumping in my headphones. I'm walking around Boston, blasting It Was All A Dream by Biggie Smalls on my headphones and just walking like I could have been floating.”

For the full story, you can listen to my full interview with Bobby Brannigan on Apple Podcasts, Spotify, or by clicking the image below.

Have a productive week!

Shamus

Founder of Dealroom Media

Lucie Basch thumbnail

Hey! Shamus here, and welcome to another edition of The Dealroom, a newsletter (and podcast) sharing the stories of world-class entrepreneurs to inspire the next generation. Now, onto the story of Too Good To Go!

Co-Founder Lucie Basch shares the story:

“When I was working in food factories, I discovered that the way we produce food today is the same as if we would produce fridges, electronics, or cars. We don't really think about what ingredients we put in that are going to have an impact on our environment.

When I realized that it's actually part of the production process to waste a lot of food by producing faster and making the cost cheaper, that’s when I found that my values were not aligned with what was what I was spending my time on.

I needed to change something.

I decided to put my energy and my time towards something that was really meaningful for me. And that was the fight against food waste. We throw away 40% of all the food we produce, and that's responsible for 10% of greenhouse gas emissions. I decided I didn't want to be part of the old food system anymore. I wanted to contribute to creating the new one.

That’s when the idea of Too Good To Go started to come to my mind.

I took a pen and paper and tried to put my ideas down. I literally drew out my idea for the app, but I couldn't code. So, I found someone better than me to do that.

One of the most important things I did at that time was to share the idea with as many people as possible. You often hear, ‘Protect your idea and make sure that no one steals it because they're going to do it faster than you.’ For me, I was so willing to reduce food waste and find a solution for it that, in a way, the more people knew, the merrier.

By sharing the idea with more and more people, I found some people who started to do the same thing I wanted to do. So, before I even started I had competitors who were working on a website and wanted to build an app.

So I called my ‘competitors’ who were in Denmark at that time. One of them was a developer, and that's how I found my co-founders.

The idea was if we convinced bakeries to join the platform, they would be able to sell excess food to the users of our app at the end of the day instead of throwing everything away.

[There was a problem, though. We had no users]

So, I went into the streets, knocking on all the bakery doors. I had never done sales in my life, and I didn't know what it was like to just take a door to your face. But it's all about being persistent and convincing, and because you're so convinced, you actually get to convince others.

[Since we were successful going door to door, we began hiring salespeople] Now we have more than 500 people sitting in 17 different countries doing all different types of sales jobs. We're lucky as well that now more stores hear about us from word of mouth, the internet, and also food waste has become more of a thing [compared to 10 years ago]. Leading to a lot of stores looking for solutions. And because Too Good To Go is the global leader, they come to us really quickly.

We now have more than 85 million users on our platform. 10% of them are in the US. It's also great for your brand because, on top of that, we send you back money at the end of each quarter for the bags you've saved.”

Q: How does your business make money?

“For every bag that is purchased on the platform, we take a commission. That's actually our main KPI, which is perfectly linked with our revenue because, for every bag saved, we take a fixed commission.”

For the full story of Too Good To Go, you can listen to my full interview with Lucie Basch on Apple Podcasts, Spotify, or by clicking the image below.

Have a productive week!

Shamus

Founder of Dealroom Media

Being an entrepreneur is f*cking hard. And nothing can truly prepare you for the journey of becoming one. But there are a few people who can help guide you along the journey. So, after hundreds of hours of listening to business podcasts, and building my own, these are the 10 best podcasts every entrepreneur should listen to in 2024.

1. My First Million

My First Million is hosted by Sam Parr and Shaan Puri, two friends who made millions selling their own companies. Sam is known for founding The Hustle, which sold to Hubspot for an undisclosed amount. Shaan sold two companies, one of which was Bebo, which exited for $25 Million to Twitch. Now, as co-hosts, they discuss new business ideas for entrepreneurs and interview those who have untraditional paths to success in the field.

One of my favorite episodes - How I Bought A Multi-Million Egg-Carton Business For $0

Summary:

• Host(s): Sam Parr and Shaan Puri

• Website: http://myfirstmillion.com

• Release of new episodes: Every week

• Average length of episodes: 60-90 minutes

• Topics covered: Entrepreneurship, exit strategies, business ideas, marketing, and more

2. MBIT: Business Success Uncovered

MBIT: Business Success Uncovered is hosted by Shamus Madan, an 18-year-old who interviews the brightest minds in business, such as Mark Cuban, Tim Draper, Spencer Rascoff, etc. Shamus frequently asks deep, thought-provoking questions to understand step-by-step how the guest built their company or career. He will take you inside the minds of some of the brightest people on the planet for 30-60 minutes every week. If you're an entrepreneur, CEO, or business strategist, this show is for you.

One of my favorite episodes - Noah Kagan: Revealing The Marketing Strategy I Used To Build A $100M Business

Summary:

• Host(s): Shamus Madan

• Website: https://spoti.fi/3SBH5gs

• Release of new episodes: Every week

• Average length of episodes: 30-60 minutes

• Topics covered: Entrepreneurship, exit strategies, marketing, and more

3. Invest Like The Best

Invest Like The Best is a weekly podcast hosted by Patrick O'Shaughnessy. Patrick currently serves as the CEO of O'Shaughnessy Asset Management and hosts conversations with the best investors and business leaders in the world. He explores their ideas, methods, and stories to help you better invest your time and money. Listen to the stock market and boardroom insights you can't find anywhere else.

One of my favorite episodes - Jack Altman & Miles Grimshaw - Building and Investing in Lattice

Summary:

• Host(s): Patrick O'Shaughnessy

• Website: investlikethebest.com

• Release of new episodes: Every week

• Average length of episodes: 30-60 minutes

• Topics covered: Entrepreneurship, exit strategies, marketing, and more

4. Founders by David Senra

Founders by David Senra hosts one of the most well-researched business podcasts on the planet. Every week, David Senra reads a biography of an entrepreneur or someone in history and finds parallels to how you can use their ideas in your work or business.

One of my favorite episodes - #298 I had lunch with Sam Zell

Summary:

• Host(s): David Senra

• Website: https://www.founderspodcast.com/

• Release of new episodes: Every week

• Average length of episodes: 60-90 minutes

• Topics covered: History, business strategies, management, and more

5. How I Built This

How I Built This is hosted by Guy Raz, who sits down with the world’s best-known entrepreneurs to learn how they built their brands. The show is a masterclass on innovation, creativity, leadership, and how to navigate the most challenging obstacles when building a business.

One of my favorite episodes - Calendly: Tope Awotona (2020)

Summary:

• Host(s): Guy Raz

• Website: https://www.npr.org/series/490248027/how-i-built-this

• Release of new episodes: Every week

• Average length of episodes: 60-90 minutes

• Topics covered: Marketing, creativity, innovation, and more

6. The Game w/ Alex Hormozi

The Game w/ Alex Hormozi is one of the most concise business podcasts on the planet. The level of value Hormozi packs into a 15-20 minute episode is astronomical for founders. He often draws on his own experiences, sharing real-world examples of successes and failures, making the show relatable for entrepreneurs at a variety of stages of their journey.

One of my favorite episodes - 8 Lessons I Learned From My Hero

Summary:

• Host(s): Alex Hormozi

• Website: https://spoti.fi/47YKVVo

• Release of new episodes: Daily

• Average length of episodes: 15-30 minutes

• Topics covered: Business strategy, sales, marketing

7. We Study Billionaires

We Study Billionaires is hosted by Stig Brodersen, Preston Pysh, William Green, Clay Finck, and Kyle Grieve. Three times per week, they share lessons from famous financial billionaires, including Warren Buffett, Ray Dalio, and Howard Marks, and teach you how to apply their investment strategies. This goes far beyond mere numbers on a balance sheet; it's a masterclass in decision-making, navigating uncertainties, and a primer on effective risk management.

One of my favorite episodes - Multi-billionaire Masterclass w/ Ray Dalio

Summary:

• Host(s): Stig Brodersen, Preston Pysh, William Green, Clay Finck, and Kyle Grieve

• Website: https://www.theinvestorspodcast.com/we-study-billionaires/

• Release of new episodes: Daily

• Average length of episodes: 15-30 minutes

• Topics covered: Business strategy, sales, marketing, etc.

8. The Diary of A CEO with Steven Bartlett

The Diary of A CEO is hosted by Steven Bartlett. When Steven was 18, he was a broke college dropout. At 22, he founded Social Chain, a social media agency in the UK, and took the company public in 2010. Now he is Dragon on Dragon’s Den, Founder of Flight Story, and a host of this podcast. The show is a living diary documenting the experiences of entrepreneurs, athletes, marketers, doctors, and more to provide listeners with raw, unfiltered insights into their success.

One of my favorite episodes - Airbnb CEO: “Airbnb Was Worth $100 BILLION & I Was Lonely & Deeply Sad!”

Summary:

• Host(s): Steven Bartlett

• Website: https://stevenbartlett.com/the-diary-of-a-ceo-podcast/

• Release of new episodes: Semiweekly

• Average length of episodes: 90-120 minutes

• Topics covered: Health, wellness, business, etc.

9. Business Wars

Business Wars is hosted by David Brown, who delves into the many battles in business over the years that, whether we realize it or not, have created the world we live in today. Ever wonder what goes on behind the scenes when massive businesses are at war? Well, this podcast gives you a look behind the curtain.

“Netflix vs. HBO. Nike vs. Adidas. Business is war. Sometimes, the prize is your wallet or your attention. Sometimes, it’s just the fun of beating the other guy. The outcome of these battles shapes what we buy and how we live.” - Business Wars

One of my favorite episodes - CVS vs. Walgreens | Powerful Medicine | 1

Summary:

• Host(s): David Brown

• Website: https://wondery.com/shows/business-wars/

• Release of new episodes: Weekly

• Average length of episodes: 30-40 minutes

• Topics covered:

10. a16z Podcast

The a16z Podcast is hosted by Steph Smith, who was the former Director of Marketing for Hubspot and now runs a16z’s podcast and marketing efforts. The show features industry experts, business leaders, and other deep thinkers to understand how the world of technology is evolving and what our future may look like.

One of my favorite episodes - AI Hardware, Explained. 

Summary:

• Host(s): Steph Smith

• Website: https://a16z.com/podcasts/a16z-podcast/

• Release of new episodes: Biweekly

• Average length of episodes: 30-40 minutes

• Topics covered: Tech, culture, business news, trends, etc.

Podcasts can be one of the best ways to hear unfiltered conversations in business, enabling you to truly understand what goes on behind the scenes that can make a company a slam dunk or a flop.

If you prefer to read these entrepreneurial stories, check out The Dealroom: Business Success Uncovered, where we send you a concise entrepreneurship story delivered straight to your inbox every week.

Noah Kagan thumbnail

You might recognize Noah Kagan from his YouTube Channel, but behind the scenes, he also runs a $100M software company. And he’s built it using the exact same marketing strategy for 18 years. WTFFF.

Founder Noah Kagan shares the story:

“One day, Dave McClure came up to me and was like, ‘Hey, there's this guy who literally locked himself in a room for six months and built a [finance app] called MyMint. He's looking to hire someone in marketing. Why don't you come by and meet this guy?’

And so I meet this guy. He's very arrogant and cocky, but I think he was actually just very confident. He showed me MyMint, and I was like, ‘Holy sh*t, this is going to change the world.’ 

MyMint website from 2008

So I said, ‘Aaron, all right, cool. I'll be your director of marketing.’ 

He's like, ‘Dude, hell no. You don't even know how to do marketing.’

And I said, ‘Well, let me do this. Let me go put together what I would do for marketing. I'll bring it back in a week, and if you like it, you can pay me, and I'll execute the plan I proposed to you. If not, it's fine. There's no cost to you. How does that sound?’

He said, ‘Great!’

So, I spent 60-80 hours locked in a room putting together this plan. You can see this plan online: The Mint Marketing Plan.

I presented it to him, and he was like, ‘Damn, this is good. Go do it.’

Q: How did you get the first 100,000 users without even having a product site launched?

“It's literally chapter eight in this book, which is the exact same marketing stuff I've done over and over with YouTube, now 1 million subscribers, with the email list at noahkagan.com, with AppSumo, with TidyCal, it’s the same stuff over and over and really what you're trying to do in marketing is first think about the problem you're solving.

I call it the 3W’s. What's the problem? Who's the customer? Where are they online? So, for Mint.com, our customer is actually a techie who just got a job or someone who's super into personal finance.

The two ways that we were able to really get 100,000 users super cheap was #1 is sponsoring pre-influencers. So we sponsored Paul Stamatiou, Jim from Blogineering, and Neville Medhora, all these guys who were blogging about personal finance, like no one was really sponsoring them.

So I thought, let me just email all these people and give them like $500 [for an ad slot]. That made it so cheap to sponsor them at the time. So when you're trying to do marketing, if you go to markets, you pay market price. If you go to things that haven't been fully tapped, like blogging at that time, it is a great opportunity.

The same thing is still happening today. Like at AppSumo.com, we're still doing the same thing. We're sponsoring up-and-coming video creators who are talking about tech and personal finance, and we're sponsoring for a lot cheaper than they are because they don't have the full information yet.

When they will, they're going to charge a lot, and then we'll move on to someone else or maybe scale with them. For example, we sponsored Tim Ferriss before he was big. We were paying $5,000/month for all the ad traffic on his site. That guy [now] charges $50,000 per ad slot on his podcast. We were paying $5,000 for all of it for maybe 3-4 years.

And then #2 was blogging. We decided there's not a lot of blogging out there around personal finance, so I hired this guy named Viet from a blog called stopbuyingcrap.com

And I was like, ‘Viet, I just need you to blog. Do whatever the heck you want to do. Just go write a lot of stuff.’ 

Obviously, we created structure, but he ended up creating the blog, which went on to be super big for Mint in customer acquisition.

And I'm still doing that with my personal stuff on Twitter, LinkedIn, and social media. So you do have to follow somewhat of a framework where you can find the thing that works, and then when you find the thing that works, go crazy on that.”

You can listen to my full interview with Noah Kagan on Apple Podcasts, Spotify, or by clicking the image below.

Have a productive week!

Shamus

Founder & Host of MBIT

Ben Van Leeuwen Thumbnail

Hey! Shamus here, and welcome to another edition of MBIT, a newsletter (and podcast) sharing the stories of world-class entrepreneurs to inspire the next generation. Now, onto Van Leeuwen!

Founder Ben Van Leeuwen shares the story:

“My first summer job in college was driving a Good Humor ice cream truck. My brother Peter and I did that for three summers. The first was in Connecticut after my senior year of high school. We rented an old Chevrolet Stepvan that broke down constantly, bought the ice cream, marked it up, and sold it on the streets of Manhattan. We did really well. By the second summer, I managed to save about $30,000 from running the ice cream truck.

Ben Van Leeuwen standing next to ice cream truck

But then it came time to go back to college. 

I did not want to go back to college. I love learning, but I didn’t want to sit in the same place for four years and learn. But again, because of where I grew up, the normal thing to do is go to college. I ended up not going back to college, though.

I took a year off and traveled around Southeast Asia and Europe with the money I saved from the ice cream truck. In those travels, I found that when you go to Italy, Vietnam, Thailand, Europe, and Asia, people care about food. They care about ingredients. And I was so excited by that.

Eventually, I go back and finish college. My GPA was 2.9. I wanted a really good job. A really fancy corporate job where I could make a good living. I was scared. I wanted to survive in life. Not only did I not get a job, I didn't even get any interviews.

But one day during the spring break of my senior year of college, I was walking around Bryant Park, New York, and I saw a Mr. Softee truck, an ice cream truck, and that was the moment when I had the idea to make my own ice cream. It was a really simple idea, right? Ice cream trucks work. People like ice cream. Why not make premium, even higher-quality ice cream on the trucks?

So, we started the business with $60,000 from friends and family.

We used heavier cream, egg yolks, and no stabilizers. We make ice cream in the way that a really good, classic, three-Michelin star French pastry chef would make traditional French ice cream.

Then, to make it special, we source pistachios from Bronte, Sicily, chocolate from small farms in Ecuador, whole bourbon, and Tahitian vanilla beans.

But at that time, a new ice cream truck would cost $70,000 for the truck and then another $50,000 to turn into an ice cream truck.

So how did we do all of that with $60,000?

We actually built two trucks. I bought used post office trucks on eBay. They were 1988 P30 Chevrolet step vans. We paid $7,500 for both of them, and we found somebody who could turn those into ice cream trucks, which entailed cutting holes in the sides and putting aluminum framed windows and chest freezers in.

It gave this soft, friendly 1950-60s look a little bit different than our aesthetic now.

It was really hard work, though. The credit cards were maxed out. There was no production facility built. We had no money for that. So we co-manufactured for the first two years, then we pivoted to do our own manufacturing, which we still do a lot of in Brooklyn.”

What were some of the components that it took to get customers to be loyal repeat buyers?

“So, craveability is the key. For example, make a really good vanilla that people don't want to try once but want to eat for the rest of their lives.

Second, the most challenging part of innovation in the ice cream business is making new flavors that are hits. And to determine that, we don’t ask people, ‘What do you think of these flavors?’ We just see what gets eaten, and that is almost always going to correlate with how quickly it will sell.

Then, one of the most important parts is service, and service is actually harder to execute than product…”

You can listen to my full interview with Ben Van Leeuwen on Apple Podcasts, Spotify, or YouTube below.

Have a productive week!

Shamus

Founder & Host of MBIT

Hey! Shamus here, and welcome to another edition of MBIT, a newsletter (and podcast) sharing the stories of world-class entrepreneurs to inspire the next generation. Now, onto Aquasition.io!

NEW: We Are Launching On Video 🚀

We're beyond thrilled to announce the launch of MBIT Podcast — now in video! 📹 Dive into the insights of founders, entrepreneurs, and operators, where each episode is a visual journey for a more immersive experience.

Grab your seat below where every frame is a step forward in your entrepreneurial journey. 💻

Stay curious, and, as always — keep grinding!

Founder Matthew Chan shares the story:

“I was working part-time at AirUp for almost two years and it was coming time for me to either move into a full-time role there or get a new job.

By the end of November, I had to make a decision. Would I pursue a full-time role in AirUp or leave and go full-time on my lead-generation business? At the time, there wasn’t really any role at AirUp that fit my skill set. They had a couple of HR positions and an accounting role, which I wasn’t interested in.

So, I quit, and my parents wanted me to start interviewing for full-time roles.

At first, they were like, ‘Dude, just take the job. Are you are you stupid? You can do both at the same time.’

And I was like, ‘I can't do both at the same time. This is why.’ 

But ultimately, as always, I'm really stubborn, and they know they can't change my mind. So I wagered. I said, ‘If I can't get my agency to be self sustaining within six months, I would sell my car.’ 

My dad was like, ‘Give it a year. You're going to come back and end up getting a job. But have fun, and go experiment with this, and we'll see what you can make out of it.’

Not long after, I signed my first client over Zoom.

It was October 21st last year. I remember it as clear as day.

I literally cold-called this guy from a list of names on Google. I said, ‘Hey, I'm gonna be completely honest with you here: this is a cold call; if you want, you can hang up now, or you can give me 30 seconds, and you can decide.’ 

And he heard me out. At the end of the call, I booked a Zoom meeting. Then, I had to scramble to create a pitch deck.

For this agency, I worked with automotive detailers who were restyling shops and window tint shops, and I would bring them people who wanted their cars detailed.

So, I pitched him the deck on the Zoom call. I would sell them on $1,500 monthly retainers plus $1,000 ad spend per month and hope and pray that they would get enough cars into their shops to cover that and profit with a 3-4x return on ad spend.

After my pitch, he was like, ‘Yeah, let's do it.’ 

He paid on call. I sent him the invoice and the contract, which I got off ChatGPT, and the Stripe payment cleared. It was the best feeling ever. That was the ‘Oh sh*t, this is a real model. This isn't just some internet scam.’

Over time, the sales appointments weren’t hard to get because I wasn't afraid to dial people. So I just had to create a script that took people's guards down and allowed them to hear me out for 60 seconds.

We have since pivoted to generating leads for pool builders. In our first month we did $40k in revenue. And then this month, we have been focused on hiring, so we did take a bit of a revenue hit. I think this month we’re going to do like $30k. But since we have these processes in place, I have enough appointment flow for my team to be closing 20-25 clients per month.

So, hopefully, by January, we can ramp up to the six-figure run rate mark, which I think is very feasible.”

You can listen to my full interview with Matthew Chan on Apple Podcasts, Spotify, or YouTube below.

Have a productive week!

Shamus

Founder & Host of MBIT

Henry Shi, Stephen Curry, and Hussein Fazal

Hey! Shamus here, and welcome to another edition of MBIT, a newsletter (and podcast) sharing the stories of world-class entrepreneurs to inspire the next generation. Now, onto Super.com!

NEW: We Are Launching On Video 🚀

We're beyond thrilled to announce the launch of MBIT Podcast — now in video! 📹 Dive into the insights of founders, entrepreneurs, and operators, where each episode is a visual journey for a more immersive experience.

Grab your seat below where every frame is a step forward in your entrepreneurial journey. 💻

Stay curious, and, as always — keep grinding!

Founder Hussein Fazal shares the story:

My co-founder, Henry, and I started SnapTravel in 2016, and instead of updating our LinkedIn and telling our network we started a new company, we just started doing stuff.

There is this book called Running Lean by Ash Maurya, which tells you how to test business ideas. The very basic concept is if you have a B2C idea, you build a website, you drive traffic to it, and you see what people do. If you have a B2B idea, you start talking to customers, see what their problems are, and how you can help solve them.

We approached it by actually iterating on business ideas every 2-3 weeks and just trying different things with the market to see if they worked.

With SnapTravel, we hypothesized that people wanted a travel agent over text. So we built a simple website, drove ads to it, and people would call and say, ‘I want to book a hotel.’ 

SnapTravel text

Henry and I would pick up our cell phones, manually respond to people, and say, ‘Yeah, I got a great hotel deal for you.’ 

We would then go look it up on the web and book the hotel for them.

That’s how we got our first 100 customers without even really telling anyone what we were doing. When we saw that there was traction, that's when we started to rebrand, change the name to Super.com, and develop our app, which allows people to save not only on hotels but also on travel, gas, insurance, and pharmaceuticals.

Q: Why did you decide to raise capital for the business?

Compared to my last company, which we bootstrapped to $100 Million in revenue, this time around, we've actually raised over $150 Million from VCs. The additional capital allows us to invest faster and more aggressively in where we know there's going to be success.

There are certain areas that take a very long time and a lot of money to build, and we are confident that it's going to be a big revenue driver for the business.

But without the VC dollars, you just can't do that.

So, as an example, one of the things we built into Super.com is the Pay Card.

Super.com app

The Pay Card is effectively a card that allows a customer who typically couldn't get access to a credit card, a Mastercard. That enables them to start using the money they already have to build their credit score and earn rewards from their everyday spending.

Now, building that out took a lot of time. Almost a year to get the product the right way we wanted it to work. But imagine you were completely bootstrapped. It'd be a lot harder to go and do that, but with the fundraising, we're able to execute quickly. And with supportive investors, it can really help accelerate your product development to the point where we are now already doing $100 Million in yearly revenue.

You can listen to my full interview with Hussein Fazal on Apple Podcasts or Spotify below.

Have a productive week!

Shamus

Founder & Host of MBIT

Oscar Höglund

The year was 2009. The internet was just starting to take off when Oscar Höglund decided to take advantage of the opportunity. 15 years later, that dream became a $1.4B company enabling artists to sell their music on the internet. Here’s how he did it.

Founder Oscar Högund shares the story:

“Prior to going into TV production, I was very much a numbers guy. I worked at BBC as a management consultant and was everything but creative. But when I looked at my boss I realized that I didn't want to have their life. So, I quit and went on a soul-searching excursion. I met with tons of companies and eventually met with this TV production company called Zodiac. I always loved storytelling, so I thought, ‘Why not join?’

Little did I know that that would be one of the best decisions in my entire career.

I found myself different from everyone else in the room. I was the numbers guy in the creative industry, which was super rare.

I went from enjoying working to absolutely falling in love with my work making TV shows and doing video production.

But we found a problem.

It was really difficult finding music, adding music, paying for it, and licensing it. There were no tools. As a result, people were using less music rather than more.

That was the starting point, where [my co-founders and I] came to the insight that we wanted to soundtrack the internet.”

How did that lead to the development of Epidemic Sound?

“It was a multi-step process. First, it came down to trust because the traditional music industry hinged around representation. What that means is as a songwriter or as an artist, you would create a piece of content, and you wouldn't be willing to sell that to anyone. Instead, you would have a record label, a publisher, a neighboring rights organization, and a manager, and everyone would hold shares of the revenue.

That would then generate royalties years down the line, assuming that all the forms had been filled out correctly.

This is where we had our first big challenge. We placed this massive contrarian bet because we reached out to music creators and said, ‘Hey, we have a better way of distributing your content. If we were allowed to acquire all of the rights to your music, we could invest hundreds and millions of dollars to build out the cultural infrastructure needed to soundtrack the internet.’

All of these commercial entities are terrified of using music because if you don’t have all the rights, you can get sued. And thousands of companies have been and gone under as a result.

So, in the early days, it was a lot about explaining who we were and what we stood for.

Unlike others, we had no publishers, and there were no middlemen to feed. So we could take all the revenue and share it 50/50.”

How were partnerships so essential to building out the Epidemic platform?

“You're absolutely absolutely right, Shamus. It's been part of our playbook from day one, and it's basically how we've done everything. Before deciding to try and soundtrack the internet, we said, ‘We need to start somewhere.’ 

That starting point was broadcasters because they were super dominant at the time and were very prolific storytellers.

We thought, ‘If we build a product good enough for them, the impact we can have when we release that music across the entire internet is going to be surreal. So let's start there.’

There were basically 50 prolific production companies that made all the hit shows. When we dug down even further into the value chain, we saw on top of them were five prolific broadcasters who commissioned all of the shows from the 50 production companies who, in turn, hired 5,000 producers.

And we went, ‘Ah! What if we partner with the broadcasters? It's much better for them from a commercial perspective and from a creative perspective.’

And so we did. We partnered with the broadcasters. They encouraged all the production companies to start using Epidemic Sound, which is how we got our first 5,000 beta testers for our product, and off we went.”

You can listen to my full interview with Oscar Höglund on Apple Podcasts or Spotify below.

Have a productive week!

Shamus

Founder & Host of MBIT

Matt Maloney and Mike Evans

Founder Mike Evans shares the story:

“Well, I was sitting in my bedroom, and I wanted to order a pizza. The problem was to get one, you had to go through the Yellow Pages, which are not organized in any meaningful way.

So I had a list of all these restaurants, but many of them didn't deliver to me. That was a terrible way to discover who delivered to my address.

My original plan was to build a website that just listed the restaurants that delivered to my zip code, not even my address. When my business partner Matt received a $140 check from signing on the first restaurant, I quit my job two weeks later to go full-time on the business. At the time, the goal was for it to pay off my college debt. But for the first 3-4 weeks, I couldn't sell the restaurants to join GrubHub. What I had was a dinky website that was a delivery guide, and I wanted restaurants to advertise on the website.

I tried everything. Printouts, pitching the idea to restaurants, advertising, and none of it worked.

What actually ended up working was a relationship pitch. I pitched them on this idea like, ‘Hey, I'm an entrepreneur. You're an entrepreneur. Take a chance on me.’ It's not too dissimilar from how you pitched me on being on this podcast. It turned out that sales is all about relationships first.”

From those first steps, how did you get GrubHub to be profitable?

“I started the business out of my apartment. There was no outside investment involved. This idea of friends and family money, I didn't have that. So, I just started writing the software myself.

Partly because of that and the relationships we developed, the business was profitable up until we took the first round of financing.

From there, we grew into four more cities, and we were profitable again. We took a second financing, and that's the same thing happened. We kept going through this process until, eventually, we went public on the stock market. One of the reasons we won was because of a key factor. The service was different from everything else out there.

How?

The food was just better.

We didn't cook the food. We didn't even deliver the food at the time.

It sounds crazy, but we made sure through statistical analysis that we understood how the experience went for customers and that the best restaurants were the ones delivering the food.

Because of that, we had customers who continued to order with us again and again and again. They would order twice a day all year long, a hundred orders per year. And when that's how we were profitable, we didn't have to keep spending money to acquire customers. We had loyal, frequent customers. That's not true for any of the large players right now.”

Listen to Mike Evans’ full story on Apple Podcasts below.

Have a productive week!

Shamus

Brian Smith speaking

Founder, Brian Smith shares the story:

“At the time, one in two Australians owned a pair of sheepskin boots, but in America, that wasn’t the same story. I looked at my buddy Doug and said, ‘Hey, we have to go into business.’ So we went back to my house, where I found a surfer magazine where I'd seen the ad for these sheepskin boots. I called up the company Country Leather, and we ended up sending him $500 for six pairs of samples.

Since I was terrified of sales, my buddy Doug went on the road as a salesman. He came back after a few weeks and after handing out 150 business cards to every shoe retailer, we had no orders. They told us, ‘We're crazy trying to sell cheap skin in California. It's too hot.’

But I knew that wasn't the reason because Australia's climate is exactly like California.

So we said, ‘Okay, let's go try the surf shops.’ Doug took one area of Los Angeles. I took the beach cities. I remember walking into the first retailer really scared because I was terrified of getting rejected. I opened up my little bag of samples, and he just went, ‘UGG boots? What are you doing with those?’

I said, well, we're thinking of importing them. And he’s like, ‘Oh man, you're gonna make a fortune!’ So that happened all the way down the coast from Malibu down to Mexico. Doug was also getting the same reaction in the Valley.

We were on fire. We thought we were going to be instant millionaires! But we didn't think to ask for any orders because we didn't have any inventory. That backfired on us big time because we ended up raising about $20,000, which in today's money is about $70,000.

We bought 500 pairs from Australia, and when they finally arrived, we went back on the road with a huge duffle bag full of boots and an order pad. I went back to the same store that told me it was gonna be a fortune, and he goes, ‘Well done, Brian. But we couldn't sell them in our store because we just sell surfboards, trunks, and flip-flops.’ 

The next store said the same thing, and the next one. After a couple of weeks, when Doug and I regrouped, we realized that our sales for the year were 29 pairs. It happened to be exactly a thousand dollars.

That was horribly disappointing because Americans just didn't understand sheepskin.”

Q: What kept you from not shutting down the business after all of the failures?

“Well, right after that first delivery at Christmas, which was our first-year sales, I used to go up to Malibu with my Dodge van full of product. I ended up selling about $6,000 worth of boots out of the back of the van in January, February, and March.

The thing that made me never give up ultimately was that every one in two Australians owns a pair of these things, and they think they're the best in the world. So it wasn't the product that was wrong. It must be me.

I had a couple of years where we were advertising with these models on the beach with perfect clothes, hair, and sunset, and the boots were the main feature of the ad. But, I had a beer with one of my good surf shop retailers in San Diego, and he called out the back to these little 12, 13-year-old kids who leave their surfboards in the store and said, ‘What do you guys think of UGG?’

Every one of them just went, ‘Oh man, UGGs, they're so fake. Have you seen those ads? Those models can't surf.’ 

Instantly, I realized I was sending the wrong message to my target market. When I looked at the ads again through their eyes, I was embarrassed at how bad they were.

So, I caught up with a buddy who was running a national scholastic surf association in Orange County. I said, ‘Hey Pete, do you have any young kids who are gonna turn pro real soon? I've got no money, but I can pay them in UGG boots.’

He introduced me to two kids, Mike Parsons and Ted Robinson.

And, instead of posing for photos, we just went surfing. When we ran those ads in October, November, and December, and the sales went to $220,000. It was a night and day difference. That's when I discovered the art of advertising and marketing. Your brand is not your logo, and your brand is not the product. The brand is how consumers think of you.”

Kat Cole

Kat Cole shares her story:

“When I was nine, my mother, siblings, and I left my alcoholic dad and went out on our own. [My mother] worked multiple jobs to make ends meet, feeding us on a food budget of $10/week for three years.

My mom was really an example to me. She was courageous, gritty, resourceful, entrepreneurial, and could do a lot with a dime. So, that colored my beliefs and made me want to work at a very young age.

From waitressing at Hooters, working in the mall, and cleaning gym equipment, work was a way out of that situation. It was freedom. And in that early work journey, I was often either elected to leadership positions or asked to take on leadership positions. It felt quite natural because I had been in a leadership role with my sisters for many years.”

Q: Later, when you were admitted into college, you dropped out to work at Hooters. Why?

“So I started at Hooters in high school when I was a junior. I was the first person in my family to get into college, majoring in electrical engineering and computer science. My plan was to get that degree and then go to law school.

Hooters was a way for me to pay for my education. I was a hostess, waitress, bartender, and trainer, where I taught new employees. This is all in my first two years there. So, even though I was going to college, I was making the most, working in the restaurant.

I dropped out because Hooters had asked me to be a part of international training teams, travel around the world, and open franchises. At 19, I was in Australia, Central America, and different states in the US, traveling, being elevated professionally, and taking on a ton of responsibility.

But that meant I was also never in school, so I was failing, and through my actions, I had already made my choice. This is where I'm spending my time. These are the opportunities right in front of me that feel more unique and more important than going to class.

So I meet with my counselor, and she says, ‘There is a way to make up your classes, but you're not only going to have to stop traveling, you won't even be able to work as much.’

I could not financially afford to stop working. So, I dropped out and took a corporate job at Hooters. I just believed there would be more opportunity. I moved to Atlanta and started working in the corporate office. As the company grew, I grew. Every 18 to 24 months, I was promoted to a new management role. By the time I was 26, I was one of the vice presidents of the company, doing around $800 million in revenue. I didn't know anyone in my network who was my age, whether they had been to college or not.

However, I did realize there were things I missed: the language of finance, the language of business and accounting, and the mentorship of business people who were outside of the restaurant industry. So I went back to get my MBA without a bachelor's degree.”

Q: How did you get your MBA without a bachelor's degree?

“I had a mentor who took a great interest in me. She was a recruiter and still is a dear friend today. She's like, ‘Look, if you want to stay in the restaurant industry, you're going to have no problem getting any job you want. But if you ever want to go anywhere else, you are not going to get past their HR filter. You're a child of a single parent, alcoholic father, college dropout who's worked at Hooters her whole life.’

I didn't like the idea of doors being shut. She said, ‘I know someone who's a CEO who got their masters without a bachelor’s. It's not easy, and it's rare, but it's possible.’

And that's all I needed to hear that it was possible. I started calling all the business schools that had executive MBA programs with locations in Atlanta and was accepted into multiple MBA programs. They told me I had to take the GMAT very quickly. So I took the GMAT and had to get a higher-than-typical passing score, which I did, and that was it.

I started at Georgia State University, Robinson College of Business in 2008 and graduated in December of 2010. Two months after I had started as president of Cinnabon.”

To listen to the full interview, click the link below.

Have a productive week!

Shamus

Mike Salguero (Source: Forbes)

Mike Salguero shares the story:

"In 2015, my wife was diagnosed with a thyroid condition. We found that grass-fed beef is part of an anti-inflammation diet and can help alleviate some of the symptoms. Whereas corn-fed or grain-fed beef can leave your body inflamed. We were reading these blogs that said, ‘eat grass-fed beef,’ but we didn’t know where to go.

I ended up finding a farmer who raised cows on grass and bought what's called a cow share, where you can buy half of a cow or a whole cow. When I got all of this meat, I didn't have enough room for it in my freezer, so I started giving it out to my friends.

One of my friends was like, ‘This would be so much better if it was delivered to my house!’ And I thought, ‘That's an interesting idea…’

At the time, I really wanted to run a subscription business again. I was not looking to start a big company and didn't think that this was going to be my big company. This was intended to be a hobby, and then I was going to figure out what's next.

When we started to expand the business, a key strategy we used for hiring was the barbell strategy. We paired super young people with those at the tail end of their careers. My original group was 3-4 who were directly out of college. Then I pulled one guy, who was a meat buyer and 70 years old, out of retirement.

What I saw is young people are really coachable, and older people are really just looking to have a fun problem to work on. We found that type of employee is like really great and often overlooked. Oftentimes, people are looking for somebody who's in their mid-forties as a senior executive. And the difference between someone in their mid-forties and somebody who's 70 is an additional 25 years of experience.

That's the barbell strategy. So you've got like weights on one side and the other. Together, they lean in the middle. I think that's a great way to operate a company, and certainly, what we did early on to help scale to $600M in revenue.”

To listen to the full interview, click the link below

Have a productive week!

Shamus

Founder & Host of MBIT