Most people ask - is it possible?

Ajay asks - what would need to happen to make it possible?

Larger goals. Shorter timeframes.

Ajay calls it - compressing time.

It's what enabled him to:
- Buy, scale & sell a company in 4yrs
- Yake a sport from 72 to 156 countries
- Co-found a SleepTech company with Gary Brecka - one of the biggest names in longevity

Inside Ajay's playbook:
→ Questions that expand what your team thinks is possible
→ Why 90% of deals fail in diligence - and how to get through it
→ How to train AI to be your thinking partner

Full episode 👇️ 

👀 YouTube https://www.youtube.com/watch?v=Jyl41zw0g4Q 

👀 🎧 Spotify https://open.spotify.com/episode/2m2ighHdy6629rKH2S5ilo

🎧 Apple Podcasts https://podcasts.apple.com/us/podcast/how-to-buy-scale-and-sell-a-company-why-90-of-deals/id6792709388?i=1000782634982 

p.s. Since his exit, Ajay invested in 27 founders. Here’s what he checks for before investing, and it’s not what you think (30:36-32:10)

To healthy EBITDA,
Kate

Most people think you have to run a business full-time.

Justin Hoskins bought one that takes 15 hrs/week.

He lives in New York.

The business is in Florida.

He also travels a ton — not for work.

Welcome to the world of absentee businesses.

That you can buy.

On this episode of Deal Diaries - how Justin, an ER pediatrician, bought an absentee-owner marketing agency.

Inside Justin's playbook:

→ Why he passed on med spas
→ How to use your 401k to fund an acquisition
→ How to use AI to spot red flags in acquisition documents
→ Why a loan broker can save your deal

👉️ Watch on YouTube https://www.youtube.com/watch?v=MsgYDmkKDPY

It would mean the world if you could Subscribe on YouTube🫰 

👉️ Listen on Spotify https://open.spotify.com/episode/2BlD4WD9drbsquxa1QoIXE 

p.s. Apparently I wink at guests when nervous. Didn’t realize until post-production. Enjoy 😉 🫠 

Most people think you have to quit your job to buy a business.

Connor didn't.

Most people think printing is a dying industry.

Connor didn't.

Most people think that expecting a baby is no time to buy a business.

You guessed it — Connor didn't.

Connor kept his full-time role at Mars.

And bought a business within a few months of his search.

Had a baby.

Then bought another business.

Inside Connor's playbook:
→ How to run a part-time search
→ How he financed the deal without an SBA loan
→ How he got sellers' attention (bet you won't guess)
→ How to reverse-engineer a $100M business (with AI)

This is exactly the kind of conversation Deal Diaries exists for.

Real people.
Real numbers.
Real takeaways.

🎧 Listen on Spotify 👇️ https://open.spotify.com/episode/6Bg4S7WhrDmdieCTA5kjWJ?si=D7mJhCbHS96SpBbD55Tclg 

▶️ Watch on YouTube 👇️ 
https://www.youtube.com/watch?v=glOm7PjqS1c

p.s. The nerves of closing a deal are real. Listen to Connor talk about being "insanely nervous" — and what got him through (24:01).

To healthy EBITDA,
Kate

Joey walked away from a $300K salary at Wells Fargo.

Not because things were bad.

But because he discovered where banks quietly park most of their cash.

$19.3 billion.

No, not in real estate.

In cash value life insurance.

That one discovery changed everything.

He built a $30M valued life insurance agency.

How?

He co-founded his agency.

Grew organically.

Then acquired 2 more agencies.

Inside Joey's episode:

→ Acquire at 4x and sell at 15x
→ The 3 post-acquisition mistakes he'd never repeat
→ How he financed the deal without a bank
→ Investor DNA — how to find the right investment for your personality

🎧 Listen on Spotify 👇️ 
https://open.spotify.com/episode/3BB1pCL91xQ097Au40c3Nh?si=QuzHtLyoQ4eA6awWJQJCGw

From $300K Salary to $30M Valued Agency — How to Grow Through Acquisitions

Deal Diaries with Kate Chichi · Episode

Spotify

▶️ Watch on YouTube 👇️ 
https://www.youtube.com/watch?v=mUyuM_kpHvc 

p.s. Don’t look at the cringy plant in my background 🙈 

To healthy EBITDA, 
Kate Chichi

This is Founders Club - a supportive community for remarkable founders & CEOs focused on personal & business growth.

In today’s issue:

• Founders & Funders - A Delicious Evening with Hazelicious

• 1:1: Founder Coaching

Founders & Funders - A Delicious Evening with Hazelicious

​You've likely tried peanut butter, but have you tried Hazelnut butter?

Now you can!

👉️ RSVP: https://lu.ma/4gcu918g

Taste Hazelnut Butters & Milks in a Private Social Club

Presented by the founder of Hazelicious - a company reimagining hazelnuts to create delicious and sustainable products.

• ​Premium hazelnut butters and hazelnut milks

• ​Rich and creamy products made with a select variety of hazelnut

• ​Supporting small family farms and rain-fed agriculture

🗓️ Wed, Nov 6th, 7-9pm
📍 Private Social Club, Prospect Park, Brooklyn

Paired with ☕️ coffee & 🥐 baked goods.

👉️ RSVP: https://lu.ma/4gcu918g

Meet Accomplished Founders & Investors

​Founders:

• ​generating $1M+ in revenue

• ​raised $3M+

• ​exited founders working on their next venture

• founders looking to meet like-minded entrepreneurs

Investors:

​Investors in CPG & all other industries welcome!

• Angels

• ​Family Offices

• ​VCs

• ​PEs

👉️ RSVP: https://lu.ma/4gcu918g

Free Notion and Unlimited AI

Thousands of startups use Notion as a connected workspace to create and share docs, take notes, manage projects, and organize knowledge—all in one place. We’re offering 3 months of new Plus plans + unlimited AI (worth up to $3,000)! To redeem the Notion for Startups offer:

1. Submit an application using our custom link and select Beehiiv on the partner list.

2. Include our partner key, STARTUP4110P67801.

Learn More

Looking for support as a founder?

Unlock accountability, strategic business planning, scaling and fundraising support.

Whether you’re just starting or many years into your founder journey, 1:1 coaching tailored for you.

👉️👉️👉️ Book a FREE consult 

Coaching by entrepreneur & Family Office investor, previously VC, operations & product manager.

p.s. If the times don’t work for you, respond to this email with alternatives.

Enjoying this newsletter? Refer a friend!

Let’s discover Hazelnut butters together,
Kate

This is Founders Club - a supportive community for remarkable founders & CEOs focused on personal & business growth.

Expand into new markets, boost revenue, get new customers through acquisitions! 

Acquisitions of small boring businesses is an untapped strategy for startup growth - especially considering the ROI possibility:

• ​You can buy a company for $30-150k

• ​Add $70-300k in revenue to P&L

• ​Add millions to your cap table (x Multiple)

👉️ Register here: https://lu.ma/m33hdxw6 

🗓️ Wed, October 9th 5-5:45pm
📍 Online 
🎟️ FREE

Join the AMA and learn how to:

• ​Find a business to buy

• ​Vet the business

• ​Sort out the legal

• ​Pay for the acquisition

• ​Perform the merger

👉️ Register here: https://lu.ma/m33hdxw6 

Learn from an M&A-Experienced Founder!

​Petko, the founder of CHEFIN, expanded his Australian-based business into the US and Asian markets through acquisitions.

​Previously to starting CHEFIN, Petko worked on multiple M&As for WPP (British Multinational Comms Company), YouGov (London Stock Exchange listed company) and APD (Australian Stock Exchange listed company).

👉️ Register here: https://lu.ma/m33hdxw6 

p.s. AMAs are usually exclusive to Founders Club members, but we're opening it up for this one because we don't want to gatekeep this goldmine.

Enjoying this newsletter? Refer a friend!

See you at the AMA,
Kate 

This is Founders Club - a supportive community for remarkable founders & CEOs focused on personal & business growth.

Exclusive AMA: Selling 7+ Figure Deals

Are you a founder looking to get insights on B2B & Enterprise sales?

Join our Ask Me Anything (AMA) with Feargal O'Sullivan - CEO of USAM Group for over 10 years.

​Feargal specializes in closing 7+ figure deals.

​Learn about:

• transitioning from founder-led sales to hiring sales teams

• strategies & tips for sales outreach

• building relationships with potential customers

• closing 7+ figure sales

​Ask Feargal questions about sales specific to your business.

When & Where

🗓️ This Wednesday, July ​24th, 12-12:45pm
📍 Online (Zoom)

👉️ Register here: https://lu.ma/rx0rbcxg

Agenda

​🔥 12-12:20pm: Fireside chat with Feargal
🙋‍♀️ 12:20-12:40pm: AMA with Feargal
💭 12:40-12:45pm: Parting wisdom

Unique Opportunity

These AMAs are typically reserved for Founders Club members only, but we are giving a few spots to non-members.

Spots are limited.

Register before spots run out.

👉️ Register here: https://lu.ma/rx0rbcxg

Enjoying this newsletter? Refer a friend!

See you at the AMA,
Founders Club 

This is Founders Club - a supportive community for remarkable founders & CEOs focused on personal & business growth.

We also host Founders & Funders events 👇️ 

In today’s issue:

• Spinning @ Equinox with Pool

• Female Founders Online Support Group

🚴 Equinox Spinning for Founders & Funders

We had 600+ RSVPs to our last Equinox Spinning, so we’re bringing it back! ​

Join an energizing cycle session followed by a relaxing time in the steam room.

Did we mention that this Equinox has a pool?

Pool @ Equinox

🗓️ This Saturday, 10:30am EST - 2pm EST
📍 West Village

👉️👉️👉️ RSVP: lu.ma/iced8yn1 

Better business banking, from idea to IPO

Rho is the business banking platform with everything you need to manage your company cash and scale your business. Apply in minutes and enjoy 24/7 customer support plus enterprise-grade spend management – all with zero monthly, wire, or ACH fees.

Two business bank account options, one powerful platform.

1. Rho Business Checking Account:

   • Operate with stress-free banking, $0 ACH and wire fees.

2. Rho Business Savings Account:

   • Getup to $75M in FDIC deposit insurance to secure non-operating cash while earning yield.

Open a Rho account in minutes today.

Banking services provided and cards issued by Webster Bank, N.A., Member FDIC. International and foreign currency payments services provided by Wise US, Inc. Treasury Management services provided by American Deposit Management, LLC. All Rights reserved. © 2019-2024 Under Technologies, Inc. DBA Rho Technologies. Rho is a trademark of Under Technologies, Inc. Rho is a fintech company, not a bank. Rho partners with FDIC-insured banks to offer banking products and services.

Female Founders Online Support Group

Recurring, online, small-group cohort that acts as your personal board of directors & provides you with:

• 📈 Business feedback & advice

• 🛣️ Resources to overcome roadblocks

• 🎯 Goal setting & enhanced accountability

• 🧡 New friends & founder community

🗓️ 1 hour, every 2 weeks
🌎 Open to founders worldwide

Want to learn more?

Founders Online Support Group Interest Form

Fill in this form (takes 20 seconds)

tinyurl.com/ffgroup20

Hope to see you by the pool,
Kate

This is Founders Club - a supportive community for remarkable founders & CEOs focused on personal & business growth.

We also host Founders & Funders events 👇️ .

Warm welcome to the 323 new subscribers who joined since last week!

In today’s issue:

• Join Investors Group Chat

• Equinox Spinning for Founders & Funders

Are you an investor? Join the group chat

NYC TechWeek is in full swing!

Connect with investors for NYC TechWeek & beyond.

💬 Want to join?

👉️👉️👉️ Add your phone number here.

(Used exclusively for the group chat)

🚴 Equinox Spinning for Founders & Funders

​Join Founders & Funders for an energizing cycle session followed by a relaxing time in the steam room & lunch.

🗓️ This Saturday, 12pm EST - 3pm EST
📍 Around Madison Square Park

👉️👉️👉️ RSVP: lu.ma/equinox-spin

Come say hi if you see me at TechWeek events,
Kate Chichi

This is Founders Club - a supportive community for remarkable founders & CEOs focused on personal & business growth.

We host Founders & Funders events and share tools to overcome founder struggles.

Welcome to the 324 new subscribers who joined since last week!

In today’s issue:

• Join an Investors Group Chat

• Taste & Test with a16z Podcast Host

• NYC TechWeek Events 

Are you an investor? Join the group chat

NYC TechWeek is next week!

We’re connecting investors in a group chat for TechWeek and beyond.

💬 Want to join?

Respond to this email with your name & phone number.

Taste & Test with a16z podcast host

Come play with new tech & taste new foods and beverages.

Hosted with Steph Smith:

• a16z podcast host

• 147K+ followers on X

• Founder of Internet Pipes - leverage the internet to find good ideas, accelerate side projects and connect with fellow builders

Did we mention there will special guests?

🗓️ Wed, June 5th, 1-4PM
📍 Lumos House (Lower East Side, Manhattan)

👉️ RSVP: lu.ma/internet-pipes

Want to showcase your product at the event?

Respond to this email.

Join us at more NYC TechWeek Events!

🤑 AI in B2B Sales with Saad Bin Shafiq (Ai Synapse)
☕ NYC Tech Breakfast Club with Morgan Barrett (Optimal, Tech Breakfast Club)
🚴‍♂️ Equinox Spinning for Founders & Funders with Tem (Optemization)

Let’s test new products together,
Founders Club 

This is Founders Club - a supportive community for remarkable founders & CEOs focused on personal & business growth.

Each week, we give you tools to overcome common founder struggles and build founder resilience.

We also host Founders & Funders events.

Welcome to the 325 new subscribers who joined since last week!

In today’s issue:

• AirTag Winner

• 5 Truths to Embrace about Fear of Failure 

• NYC TechWeek Events not to miss

Referral Program Winner!

Congratulations to Heidi for winning an AirTag!

5 Truths to Embrace about Fear of Failure

We’ve written a lot on overcoming fear of failure and have gotten a ton of warm responses.

Thank you to everyone who let us know that the newsletter resonates and the tips were helpful! 🙏 

In case you missed them, check out previous newsletters on

Overcoming Fears of:

• Uncertainty & Decrease Self-Worth 

• “What will Other People Think”

• Disappointing Others 

• Letting People Down 

To conclude the series, we’re sharing 5 ultimate truths that you may not want to hear but should accept.

1. The only way is through

We hope that the exercises from previous posts help alleviate your fears.

However, you may still feel some fear. And that’s okay.

You have to act despite the fear.

When I was just starting everything was scary.

Sending an email, posting online, creating an event, calling a client…

So I made this my screensaver 👇️ 

After doing the thing I feared once or twice the fear went away.

The only way, is through.

p.s. If you know who deserves credit for this image, pls lmk, I’d like to personally thank them.

2. If you don’t try, you automatically fail

Give yourself a chance by trying. 

3. Don’t let your fear be a thief

You want to create something great but fear is stopping you?

By not doing it you’re robbing people.

You’re robbing your customers, society, family and yourself. 

Don’t let your fear rob you of your dream.

4. Pain is temporary

Even the most extreme emotional pain will pass. 

Remember getting your heart broken for the first time? 

That sucked. A lot. 

Bet it felt like you’d never get over it. 

But you did. 

This too shall pass. 

5. It’s easier with others

When you’re at it alone, it can feel like you’re the only one who fails.

When you’re a part of a community, you see just how much other founders try and fail before creating something great.

Failure is a part of the journey.

It’s a refreshing shift in perspective.

This is why we created Founders Club - a supportive community for remarkable founders.

Join to get the support and perspective you need.

Applications due by May 30th.

Only 8 spots left.

Disclaimer: This newsletter is for informational purposes only, it is not written by a financial nor medical professional and does not provide financial nor medical advice nor help.

Enjoying this newsletter? Refer a friend!

Your Biz News Visualized

With Bay Area Times, you will get graphics like these, so you quickly understand the news without having to read through long and boring paragraphs.

Visual-based newsletter on business and tech

We explain the latest business, finance, and tech news with visuals and data. 📊

All in one free newsletter that takes < 5 minutes to read. 🗞

Save time and become more informed today.👇

Join us at NYC TechWeek!

Let’s hang IRL:

🤑 AI in B2B Sales with Saad Bin Shafiq (Ai Synapse)
☕ NYC Tech Breakfast Club with Morgan Barrett (Optimal, Tech Breakfast Club)
🕵‍♂️ Internet Pipes Meetup with Steph Smith (a16z)
🚴‍♂️ Equinox Spinning for Founders & Funders with Tem (Optemization)

Hope to see you at TechWeek,
Founders Club 

This is Founders Club - a supportive community for remarkable founders & CEOs focused on personal & business growth.

Each week, we give you tools to overcome common founder struggles and build founder resilience.

In today’s issue:

• 🎁 Win an AirTag! Ending soon!

• Fighting Fear of Letting People Down 

• Your Next Hire

• NEW NYC TechWeek Event

🎁 Apple AirTag give away! 

• To enter, share Founders Club newsletter using your referral link 👇️ 

• 1 successful referral = 1 entry ticket

• The more you refer, the higher your chances at winning!

• You can win even with 1 ticket

• Ends this Thu, May 16th 11:59pm EST

Fighting Fear of Letting People Down

Welcome back to our series on Fighting Fear of Failure.

In case you missed them, check out previous newsletters on

Overcoming Fears of:

• Uncertainty & Decrease Self-Worth 

• “What will Other People Think”

• Disappointing Others 

This week we’re focusing on Fighting Fear of Letting People Down.

Fear of Letting People Down is a fear of putting people who depend on us in worse circumstances or failing to deliver promised rewards.

Typically, this fear is associated with:

• family

• employees

• friends (who invested in your biz)

• investors

• clients

When we fear something, we often fear the worst case scenarios because it feels like there is no way out of them.

We are here to show you that even worst case scenarios can be solved for and are often not as scary as they might seem.

Let’s solve for these one by one:

Family

Worst case scenarios:

1. You won’t reach business revenue that enables you to provide for your family

2. Your successful business will go out of business and you will not be able to provide for your family any longer

Things to know & do:

1. You can get a part / full-time job

Most founders get a part or full-time job at least once while running their business.

If you’re not yet at a point where your business can support you or are experiencing unstable revenue, look into getting a job.

As a founder, you typically bring diverse and unique expertise highly valued by employers.

A job may enable you to:

• feel more safe and emotionally stable

• have freedom to think in longer terms

• make a more weighted decision about the future of your business

2. You can collect unemployment benefits

In case your business shuts down and you do not have another job lined up, you can rely on unemployment benefits to support your life.

3. Discuss your financial struggles with your partner / family

Founders tend to conceal financial struggles from their partner/family to reduce stress and shame.

As uncomfortable as it may be, it’s better to discuss financial struggles when you have months of runway rather than a day.

Discuss potential options:

• What business and personal expenses can you cut down on?

• Can you fundraise?

• Can your partner support you for some time?

• Can your family give you an interest-free loan?

• Can you borrow from your friends?

• Can you take a part/full time job?

• Can you sell any stocks?

• Can you max out your credit card?

• How much of your lifestyle could unemployment benefits support?

Depending on your answers to above devise a plan with a clear timeline to act upon if push comes to shove.

Employees

Employees can feel like a business family.

Founders often feel responsible both for the lives of our employees and the employees’ families.

That’s a heavy load to carry.

Worst case: You have to lay off people

It’s tough to let people go, especially when it’s due to the company’s financials and not the employees’ poor performance.

Things to know:

1. Your employees will get another job

2. You can help them find a job by making introductions to your network

You may even be able to get a referral fee.

3. Your employees likely have savings for this type of rainy day

4. Employees can collect unemployment benefits to support themselves while searching for another job 

Friends

Your friends likely gave you money because they love you and wanted to support you.

They also likely gave you a sum that they were comfortable never seeing again.

Obviously, you should do your best to return the funds.

If you won’t be able to for some time, have a conversation with your friends to set realistic expectations.

Here are 2 most common outcomes of this convo:

1. Your friends tell you not to worry about it

They do not expect to get the money back.

 2. Repayment plan 

Make an agreement to repay the funds in chunks when you land on your feet again (e.g. 3 months after you land a job)

Investors

Worst case: Your company fails and is unable to return the funds to investors

Things to know:

1. Investors know the risks of investing

They understand that investing caries risk of losing all of the invested capital.

They wouldn’t invest if they didn’t have the risk tolerance for such an outcome.

2. Up to 90% of startups fail

While you should do your best to provide a return for your investors, many startups won’t be able to, it’s a fact of startup life.

3. VC investors are typically among the first to get remnants of your company

VCs tend to hold preferred stock and get repaid before common shareholders in case of liquidation.

VCs may have rights that entitle them to receive a fixed amount or a percentage of the liquidation proceeds before common shareholders.

As a founder, you tend to be the last on the list of distributions and sadly may not get anything at all.

Know that you are giving all that you can to everyone else, including investors, before taking anything for yourself.

Clients

If possible, try to complete the product / service your clients paid for.

Worst case: You are not able to deliver the product / service

Things to do:

1. Communicate with the client proactively

Apologize for the inability to deliver the work, explain the circumstances and propose a course of action to salvage the situation.

2. Reimburse if possible

If you’re able to, reimburse the client for the undelivered work.

3. Refer to your best competitor

It’s unlikely that you are the only company on the market providing your product / service.

By referring your client to a respected competitor you demonstrate that you care about the client’s needs being met, even if you can’t be the one to benefit.

The client will get their needs met, the client and the competitor will appreciate the referral and you might get a referral bonus.

Disclaimer: This newsletter is not written by a financial nor medical professional and does not provide financial nor medical advice. It is for informational purposes only and is not intended to substitute for professional financial, medical advice, diagnoses, or treatment.

😎 Your Next Hire

This a new section where we feature people & companies we personally stand behind and are proud to recommend to you.

Want to connect with Ventur-io?

• Respond to this email and we’ll put you in touch

• Or reach out directly and tell them Kate sent you

Want to be featured here? Respond to this email.

Join us at NYC TechWeek!

Let’s hang IRL:

🤑 [NEW EVENT] AI in B2B Sales with Saad Bin Shafiq (Ai Synapse)
☕ NYC Tech Breakfast Club with Morgan Barrett (Optimal, Tech Breakfast Club)
🕵‍♂️ Internet Pipes Meetup with Steph Smith (a16z)
🚴‍♂️ Equinox Spinning for Founders & Funders with Tem (Optemization)

Check out more awesome NYC TechWeek events: www.tech-week.com

Can’t wait to see you overcome your fears!
Founders Club

This is Founders Club - a supportive community for remarkable founders & CEOs focused on personal & business growth.

Each week, we give you tools to overcome common founder struggles.

In today’s issue:

• 🎁 Win an AirTag! New Referral Program

• Fighting Fear of Disappointing Others 

• [NEW SECTION] Your next hire 

• NYC TechWeek Events 

👭 Our New Referral Program!

🎁 Apple AirTag give away! 🎁 

• To enter, share Founders Club newsletter using your referral link 👇️ 

• 1 successful referral = 1 entry ticket

• The more you refer, the higher your chances at winning!

• You can win even with 1 ticket

• The give away ends on May 16th 11:59pm EST

Solving for Founder Fears

Disappointing others seems to be the 2nd most common fear among founders & CEOs.

Did you just feel the weight of this fear?

Let’s alleviate it together👇️ 

Welcome back to our series on Fighting Fear of Failure for Entrepreneurs, Founders & CEOs.

In case you missed them, check out previous newsletters on:

• Overcoming Fear of Uncertainty & Decrease Self-Worth 

• Overcoming Fear of “What will Other People Think”

Fighting Fear of Disappointing Others

After many conversations with entrepreneurs, we noticed that this fear is split into 2 categories:

1. Fear of Disappointing People - fear of loosing or never gaining the respect of people whose approval we seek.

   Typically associated with family members and people we look up to.

2. Fear of Letting People Down - fear of putting people who depend on us in worse circumstances or failing to deliver promised rewards.
   
   Typically associated with family, employees, clients, friends (who invested in your biz) and investors.

While you may experience both, solving for them is different so we’ll be addressing them separately.

This issue - Fighting Fear of Disappointing Others.

Next issue - Fear of Letting People Down.

Fear of Disappointing Others

We usually fear disappointing those whose approval we seek.

These people tend to be family members or people we look up to.

3 thing to do to alleviate this fear:

1.Have a candid conversation with the people you’re afraid to disappoint

Chances are, they are incredibly proud of you.

They likely understand that entrepreneurship is a hard, uncertain journey and not everyone has the guts to do it.

You do, and that’s something to be proud of.

They also likely understand that any company can fail.

If it does, they are not going to be disappointed, but rather proud that you tried.

When you have the conversation, include:

• Why this business is important to you

• What makes this a great opportunity

• Your goals

• Timelines for the above goals

• What you’re going to do in case you can’t reach the above goals in the given timeline

Framing the conversation around goals, timelines and a back-up plan gives the listener assurance that you’ve thought it through and will be fine even if things don’t go as planned.

In the end your family just wants to know that you’ll be fine.

Story time: My conversation with my dad

As many daughters are, I was fearful of disappointing my dad.

I would never tell him when anything went wrong cause I thought he would sigh in disappointment.

One day, I braved up and told him that I was having a really hard time and wasn’t sure in which direction my business would go (and possibly into the ground).

I was expecting to hear that sigh of disappointment.

Instead, I heard:

(Ngl, tearing up just writing about this)

It was such a relief to hear this.

It also created the space for us to have more vulnerable conversations.

He now shares his struggles and we troubleshoot together.

Of course, people are different.

Sadly, not everyone will react in a supportive way.

For these cases see the next point.

2. Accept that some people choose to be disappointed no matter what

You can’t please everyone.

Some may default to disappointment regardless of what marvels you achieve.

This default disappointment is rooted in who they are as a person and has little to do with your actions.

If gaining someone’s respect is an impossible task, focus your attention on respecting your own efforts.

3. Do everything not to disappoint yourself

We often seek other people’s approval when we lack our own.

Focus on gaining your own self-respect.

Create a clear, time-based plan for your company.

Give it 110%.

Stay disciplined and consistent.

Make yourself proud!

If the business fails, you’ll know that you gave it your all. Having this assurance helps feel proud for trying, accept that the business wasn’t viable and move onto the next chapter of your life.

Hire Ava, The AI Sales Rep From $225/mo

Looking to generate B2B leads on autopilot? Ava’s your new best friend. 

Onboard Ava with a 10-minute conversation, and she’ll:

• Find relevant leads

• Do in-depth lead research

• Write hyper-personalized emails

• Contact 1000s of leads per month

• Get you qualified sales meetings

Ready to supercharge your outbound? Hire Ava today.

😎 Your Next Hire

This a new section where we feature people & companies we personally stand behind and are proud to recommend to you.

Want to connect with the candidate? Respond to this email with your company name and we’ll put you in touch.

Want to be featured here? Respond to this email.

Join us at NYC TechWeek!

Let’s hang:

☕ NYC Tech Breakfast Club with Morgan Barrett (Optimal, Tech Breakfast Club)
🕵‍♂️ Internet Pipes Meetup with Steph Smith (a16z)
🚴‍♂️ Equinox Spinning for Founders & Funders with Tem (Optemization)

Excited for you to win an AirTag!
Founders Club

This is Founders Club - a supportive community for remarkable founders & CEOs that nurtures wellness and meaningful connections.

Each week, we give you tools to overcome common founder struggles.

In today’s newsletter:

• Solving Fear of “What will Other People Think”

• 3 NYC TechWeek Events!

Welcome to the multi-part series on Solving Fear of Failure.

See Part 1 for Solving Fear of Uncertainty and Decreased Self-Worth.

Do you fear "What will other people think”?

This one’s for you 👇️ 

Overcoming Fear of “What will Other People Think?”

1. Mindset Shift: You can’t control what other people think

Have you ever done something well-intentioned, something that you know was the right thing to do and were still criticized or judged for your actions?

Welcome to planet Earth.

There will always be people who will judge no matter what you do.

Know that this has close to nothing to do with you and almost everything to do with their triggers, insecurities and fears.

You can’t control what other people think.

So why spend time on it?

Focus on doing your best and improving your own opinion of your actions, as that’s the only opinion in your control.

2. What if it works?

How exciting would that be!

Exercise: List all the amazing things that could happen if your idea works and really feel that success

Your list might look something like this:

• meet incredible people

• make new friends (who support me rather than judge me)

• grow my network

• introduce a new product/service to market

• help X amount of people/businesses

• feel independent and free

• feel in charge of my life

• become an expert in a particular industry

• be invited to speak at conferences

• raise $X

• generate $Y

• have company valued at $Z

• make more than I made at my full-time job

• sell company & retire or build the next thing I’m excited about

• be able to share my wealth with family and friends

• have the life I want

• feel really proud

• not regret never trying

Make this list your own. The more detail the better. Truly visualize it.

Now ask yourself: Wouldn’t it be a pity to forego all that just cause a few folks might judge you?

3. Past Success are Your Fuel

Exercise: Think of 1-2 instances when you feared being judged but did it anyway and got a lot of benefits.
Think back to these when this fear arises again.

Here is one that I think back to whenever I need to step over myself:

About a year ago I was terrified of posting on LinkedIn.

I’ve objectively done way scarier things in life, but something about LinkedIn was petrifying.

I knew that it could be beneficial but the fear of “what will other people think” paralyzed me.

Multiple coaching sessions and breathing exercises later, I finally committed to making 1 post.

I reread the text 23 times and pressed “Post”. 

My heart-beat went through the roof. 

“What will other ppl think” was racing through my mind.  

Turns out, nobody was there to judge.

Ppl left likes, positive comments and moved on. 

It was actually quite anticlimactic. 

The benefits, however, have been insane.

Posting on LinkedIn has literally changed my life:

• I met thousands of incredible entrepreneurs and investors. 

• Got DM’d and approached IRL by people I couldn’t dream of reaching out to before 

• Got sponsorships and opportunities I didn’t realize were possible 

What a pity it would have been to forego all of that just from worrying about “what will other ppl think.”

Ngl, I still feared a little what people might think when making my 2nd post.

3rd post onwards, it didn’t even cross my mind. 

4. Mindset Shift: People whose opinion you’re concerned about are NOT living the life you want

Can you list out specific people whose opinion you’re concerned about?

If you can, does each of these individuals have the exact life you want?

• do they have the business you want?

• do they have the family you want?

• do they have the partner you want?

• do they have the friends you want?

• do they have the lifestyle you want?

• do they have the freedom you want?

• do they have the $$ you want?

Likely not. They have NOT built the life you want. Then why do you care what they think?

p.s. Were you unable to list specific individuals?

Then trust me, the average human does NOT have the life you want.

Stop letting people you can’t even think of prevent you from building the future you want.

p.p.s. If a person is a founder, they are more likely to have supportive thoughts towards you because founders get the struggle.

We know that building a business requires doing cringey things, figuring out answers as you go, making mistakes and hard decisions.

Surround yourself with more supportive founders. Join community for remarkable founders.

Try these exercises and let us know what you think!

A Newsletter You’ll Love: Stay Ahead on the Business of AI

Need ONE newsletter to stay on top of everything?

Prompts daily has only the most important AI news, insights, tools and workflows.

The newsletter is known to:

• Make you more productive at work

• Introduce you to valuable and useful AI tools/workflows

• Help you look smarter in front of your friends (seriously!)

It’s also free to sign up!

In just ONE click, you can sign up to the FREE newsletter.

NY Tech Week is Back!

Excited to share events we’re hosting with phenomenal co-hosts:

☕ NYC Tech Breakfast Club with Morgan Barrett (Optimal, Tech Breakfast Club)
🕵‍♂️ Internet Pipes Meetup with Steph Smith (a16z)
🚴‍♂️ Equinox Spinning for Founders & Funders with Tem (Optemization)

Looking forward to seeing you there!

Rooting for you!
Founders Club 

A few weeks ago, we wrote about fear of failure and got a lot of requests to provide solutions to specific founder fears.

As always, at your service.

Read for how to solve for founder fears 👇️ 

Solving for Specific Founder Fears

I used to think that only early-stage founders experience fear of failure.

I was wrong.

I spoke to many founders who are generating millions, and they still feel fear of failure. 

Here’s a LinkedIn poll if you need more proof.

So what can help?

What do you fear?

For founders, fear of failure commonly means fear of one or more of the following:

1. Decreased self-worth & self-esteem 

2. Uncertainty 

3. “What will other people think” / shame / embarrassment

4. Disappointing people (family, friends, employees) 

Fear Specific Solutions

3 Mindset Shifts to Battle Fear of Decreased Self-Worth 

Mindset Shift 1: Your worth as a person is not tied to the performance of your business. 

Let me repeat that.

Your worth as a person is not tied to the performance of your business.

This is a tough one for many entrepreneurs to embrace, so we’ll do a separate issue on this topic in the future.

There are so many factors that determine the outcome of your business (market size, market conditions, customer segment, competition, financing etc.).

You are just one part of a massive equation. 

You would have to be almighty to believe that you alone are responsible for your business success and to tie your self-worth to it.

Exercise: Ask your friends why they value you. I promise that your business will be the last thing on the list (if on it at all).

Mindset Shift 2: Failing is not bad, it is essential.

Entrepreneurship is all about testing hypotheses.

An inevitable part of testing is getting negative results.

If someone doesn’t want to buy your product, it doesn’t make you a worthless person, it just means that the value proposition of your product does not resonate with the given customer at the given price.

Rethink your value prop. Find a different target customer. Change the price, not your self-worth.

Mindset Shift 3: Every failure makes you smarter.  

After failing, you know how not to do something.

You probably heard the famous Thomas Edison quote:

Getting something wrong is a learning opportunity.

It is not something to fear.

When you pick up a book or take a new course, do you fear that you’ll know more? Probably not.

Take the same approach towards failure.

Success is often reached through a series of progressive failures that lead to new information, skills, and strategies.  

3 Exercises to Reduce Fear of Uncertainty

Entrepreneurship is one big uncertain journey.

Below are 3 exercises to help you get more comfortable with uncertainty.

Exercise 1: What are the absolute worst things that can happen?

Truly, think of the absolute worst cases.

Then think about how you’ll solve for them. 

Below are the 3 most common worst case scenarios I hear from founders:

Yes, these are not ideal.

But, they are also not as big and scary as fear of failure can make them out to be.

Having an approximate plan for what you would do in the worst case scenario also helps reduce the fear. 

Exercise 2: Think about a time you failed a year or more ago

How did you feel in the moment?
Probably quite 💩 . 

How do you feel about it now?
You probably completely forgot about it or it feels quite minor and unimportant.

The same thing will happen with whatever failure you’re fearing now.

p.s. Were you unable to think of a time you failed? Then what are you doing fearing failure now?

Exercise 3:  What can you control right now? 

Typically you can control your:

• strategy

• resources (daily time & effort and $ investment)

• timeline

Focus on those and do your absolute best for a set period of time.

There is no point stressing about things out of your control.

Hopefully it works.

If it doesn’t, you’ll know you tried your hardest and that it wasn’t your lack of work that led to failure but rather external factors. 

Have a plan B - what will you do if it doesn’t work?
Try a different value prop / different customer acquisition strategy / go for a different problem space / get a job etc.

Similarly to Exercise 1 above, knowing what you could do next helps put your mind at ease.

How are you feeling after these exercise?

Respond to this email and let us know!

Feel free to share your current fears or anything that helped you with fears in the past. Your info is always confidential.

Stay tuned for Part 2: Solutions for fearing “What will other people think” and disappointing people.

Warmly,

Founders Club

Every time I host IRL events I get asked to create an online space for founders to connect.

Introducing 🥁 🥁 🥁 

Curated Community for Remarkable Founders, CEOs & Prominent Individuals

Our members are founders and CEOs whose businesses are generating over $1M+ or raised $3M+, exited founders and prominent individuals.

Some members are generating $14M+ and raised $25M+.

Grow Yourself, Your Startup & Your Friend Circle

Member benefits include:

• Online community - access to remarkable founders at the tip of your fingers

• Peer support groups - overcome your personal & business challenges in a trusted group of founders, led by a professional coach

• Exclusive access to events - masterminds on key topics to grow your business and IRL community events to make new friends

• Perks - up-to 30% off SaaS tools

Want to join?
Apply👇️ (1 min)

Only 30 spots left. Applications are due by Friday, April 26th.

Looking forward to welcoming new members!

Founders Club

This is Founders Club - wellness events for Founders & Funders.

Welcome to the 257 new subscribers who joined since last time!

Was this forwarded to you?

⚡ Electric Cycle Beats Session

​Join Founders & Funders for an energizing cycle session with the legendary Brandon Green - one of the most popular spin instructors at Equinox!

🧖‍♀️ Steam Room After

Follow up the workout with a relaxing time in the steam room.

​All fitness levels welcome.
No Equinox membership required.
Free.

🗓️ Sat, March 23, 12-3pm
📍 Equinox, Flatiron, NYC

👉👉👉 RSVP https://lu.ma/ff-equinox

Spots are limited!

​​After the spin class, you'll have access to the Equinox facilities until closing time.

Looking forward to spinning together!

Founders Club

Join THE BEST WORKOUT IN THE WORLD

​What to expect

• ​50% High intensity cardio on the treadmill

• ​50% Strength training on the floor

• 50 min class

FREE Class

You're getting a ~$50 workout for FREE

Ready to Find Your Strength?

🗓️ Monday, March 4th @ 7pm-9pm
📍 Manhattan, NOHO, NYC

👉 RSVP here: lu.ma/ff-barry

​What to wear 👟

• ​Workout clothes & running shoes

• ​The studio has changing rooms with lockers

Let’s sweat together,

Founders Club

This is Founders Club - a supportive founder community that nurtures wellness and meaningful connections.

Do you experience fear of failure?

This one’s for you.

As founders, we tend to feel alone in our struggles.

You’re not alone.

Each week, we take a question from our Online Support Groups, gather and share wisdom from coaches, founders, and VCs.

Let’s conquer founder challenges together!

In the entrepreneurial journey, the fear of failure is a common companion, but it doesn't have to be a roadblock.

10 Tips to Conquer the Fear of Failure on Your Entrepreneurial Journey

Embrace Failure as a Learning Opportunity

1. Shift Your Mindset: Failure is not the end but a stepping stone to success.

2. Analyze failures: Break down what went wrong, extract lessons, and apply them to future endeavors.

Focus on What You Can Control

3. Identify controllables: Concentrate on aspects within your control, like effort and strategy.

4. Let go of the rest: Accept that not everything is under your control, and that's okay.

Set Realistic Goals and a Failure Contingency Plan

5. Break it down: Set achievable short-term goals to build confidence and momentum.

6. Plan for setbacks: Anticipate potential challenges and have contingency plans in place.

Celebrate Efforts and Milestones

7. Acknowledge effort: Recognize the hard work you put in, regardless of the outcome.

8. Celebrate milestones: Acknowledge and celebrate small wins along the way.

Surround Yourself with a Supportive Network

9. Join a founder group: Connect with fellow entrepreneurs who understand the challenges and can provide valuable insights.
   
   Want to join a Founder Support Group? Learn more here.

   
   

10. Find mentors: Learn from experienced individuals who have faced similar fears and triumphed.

And remember, success is a journey, not a destination—keep pushing forward, and the rewards will follow.

Have a question?

Submit it here, anonymously.

Let us know what you’re fearful of and how these tips work out for you.

Warmly,

Founders Club