Zach was burned out after a decade of working at top roles in Coinbase, Square and Brex. He quit with no startup idea-- and then, he went right back in. Given their background, Zach and his co-founder quickly raised an $8M seed round to build an NFT-related product in Web3.

One month later, they completely abandoned their idea. They realized it was never going to work. Then, the floor fell from underneath them. FTX went bankrupt. SVB fell apart. They took punches to the face for the first 6 months straight.

But, when everyone was paying attention to Gen AI in late 2022, Zach kept going deep in Web3. He noticed stablecoins were growing but there was no platform for developers to build with. So he built Bridge, a Stripe-like API for stablecoins.

The first months post-launch were underwhelming-- until they landed a fast-growing customer. From then on, the next year was exceptional 10x+ growth. Then Stripe noticed them.

In Oct 2024, they were acquired for $1.1B. Just 2.5 years after he started.

Here's the story of how it all happened.

Why you should listen:

• Why even $1B+ exits still feel like rollercoasters from the inside. 
• How to quickly abandon ideas and pivot to what truly matters.
• How they found a massive opportunity where no one else was looking.
• Why starting outside of the Bay Area was critical to their success.

Keywords
startup, billion-dollar exit, stablecoins, investor relations, crypto, fintech, market dynamics, entrepreneurship, pivot, challenges, stable coins, startup journey, acquisition, fintech, market resilience, product market fit, Pablo Srugo, Bridge, Stripe, entrepreneurship

Timestamps
(00:00:00) Intro
(00:2:46) Starting at the Worst Time
(00:8:56) The Emotions on Pivoting a Month After Raising
(00:11:44) Pivoting
(00:18:24) Leaving Brex
(00:20:36) Working on Something Out of Trend
(00:28:34) The Core Beliefs of Bridge
(00:32:56) Launching & First Customer
(00:38:57) Sometimes you Can't Think Too Much
(00:42:29) Series A
(00:44:24) The Acquisition
(00:49:05) The Feeling of Exiting for a Billion
(00:52:24) One Piece of Advice

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We took examples from the last 100 episodes and built a clear, 5 step path to finding product market fit:

1.Before Startup Mode, There’s Research Mode —> Become an expert to find problems worth solving.
 
2.Only the Insanely Focused Survive —> Focus all your resources to do more with less.
 
3.You have to be in the market to win the market —> Use niche markets to discover unique insights.
 
4.Forget Growth. Find Value. —> Optimize for value delivery and growth will follow.
 
5.Pivot Harder, Faster —> As soon as you realize you’re not solving a #1 problem, pivot.

Why you should listen:

• Why creating value by solving problems is the core of startups.
• Startups must avoid perfectionism and embrace learning.
• Research mode involves deeply understanding customer needs.
• Insane focus and hustle are essential for early-stage success.
• Validation comes from engaging with the market directly.
• Why growth should be a byproduct of delivering value.

Keywords
startups, product market fit, entrepreneurship, research mode, focus, hustle, validation, customer experience, growth, business strategy, Wattpad, user-generated content, agility, iteration, product market fit, startup growth, pivots, entrepreneurship, value creation, founder stories

Timestamps:
(00:00:00) Intro
(00:01:47) Who is Chris Saad?
(00:02:30) Pablo's Story
(00:05:53) The Core to Early Stage is PMF
(00:09:07) Step 1: Research Mode
(00:16:44) Step 2: Only the Insanely Focused Survive
(00:23:46) Step 3: Be in the Market to Win the Market
(00:32:57) Step 4: Forget Growth, Find Value
(00:37:59) Step 5: Pivot Harder and Faster
(00:45:45) Recap

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Gusto is a $9.5B startup that does $500M ARR. Josh built an absolute monster of a company-- and it all started with payroll software for SMBs. Not just that, he started by servicing only new tech startups that were based in California. It was exceptionally niche, and it worked.

After YC, he raised a $6M seed round from tier 1 angels, back when large seed rounds were not at all common. But, unlike others, he didn't spend the money. He kept his team small as they iterated on the product. By the time they raised their $20M Series A, they were  only 10-15 people. 

Here's the story of how they got started, gained initial traction, and took off.

Why you should listen:

• Why starting super small can lead to massive outcomes.
• Why you need a huge, no-brainer pain point to succeed.
• How to use early customer interviews to deeply understand your ICP. 
• Why small teams allow for faster decision-making and execution.
• Why deep passion about the problem set is so important.

Keywords
Gusto, Josh Reeves, entrepreneurship, startup, payroll, small business, Y Combinator, business model, innovation, technology, fundraising, startup, product-market fit, team building, customer satisfaction, growth strategy, small business, Gusto, entrepreneurship, SaaS

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We go through the top 5 product-market fit lessons I've learned from speaking to well over 100+ founders on this show over the last 3 years.

These are the top 5 things you should keep top of mind going into 2025.

Why you should listen:

• Small teams outperform larger ones in early stages.
• Paying employees well is needed to build A+ teams.
• Go all-in on fundraising to do it faster. 
• Mind your burn rate to maintain flexibility.
• Creating undeniable value is essential for growth.

Keywords
product market fit, startup strategies, fundraising, small teams, value creation, entrepreneurship, founder insights, business growth, early stage startups, team dynamics

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Tolga stumbled upon a problem in the security monitoring space. Motion cameras generated way too many false alerts. So he decided to solve it using AI. He raised over a million dollars and got several customers.

But he always felt he was pushing a boulder up a hill. At one point, one of his large customers churned and went with a competitor. Tolga pivoted, but it was too late.

Now, thinking back, he realizes that one of the main issues is he may never have been solving an important-enough problem. And in my experience that's the reason that 95%+ of startups fail.

You learn a lot from the massive successes— but you can only really know what drives success if you pay attention to the failures as well. So here it is, back by popular demand.

Why you should listen:

• Why learning from failures is as important as celebrating successes.
• Why you need to deeply validate the problem with customers before building. 
• How to tell if your product isn't a top priority based on sales cycles.
• Why you probably need to pivot sooner than you think.

Keywords
startup failure, founder stories, learning from mistakes, customer validation, market dynamics, business pivot, entrepreneurship, PromiseQ, AI technology, security solutions

Timestamps:
(00:00:00) Intro
(00:02:50) What is PromiseQ
(00:11:06) Working on a Non-Priority Pain Point
(00:16:10) Realizing the Different Costumer Profiles too Late
(00:18:23) The Business Model
(00:20:52) Why you need to pivot fast
(00:28:32) If Things Went Differently

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There are a few things harder when building startups than getting your first few customers. When you're on a standstill, getting momentum is incredibly hard. Going from zero to one takes an incredible amount of effort—you have absolutely no credibility, no proof points.

So to help you out I went through 24 ways of getting your first customers using 24 different examples from this show.

Why you should listen:

• Figure out how to land your first few customers. You are guaranteed to find at least one example that works for you.

Keywords
customer acquisition, startup strategies, community building, persistence, experimentation, free services

Timestamps
(00:00:00) Intro
(00:01:35) Stay22 - Pay your Customers
(00:02:25) Reddit - Creating your Community
(00:02:58) Rappi - Seeding Supply
(00:04:04) Wattpad - Seeding Demand
(00:05:05) Cameo - Finding Someone With an Audience
(00:05:43) Noibu - Showcasing the Value of the Platform
(00:06:41) Bridgit - Showing up in Person
(00:07:24) Rewind - Attaching to an Ecosystem
(00:08:36) Clio - Adding Friction to the Funnel
(00:09:06) Wealthsimple - Lunch & Learn
(00:09:29) Athennian - Classic Customer Discovery
(00:10:00) Carbon Robotics - Presales from Customer Discovery
(00:10:34) StackAdapt - Creating Custom Software
(00:11:21) ApplyBoard - Identifying Power Users
(00:12:27) Forma AI - Sheer Force of Will
(00:15:01) Blockthrough - Starting with an Obvious Problem
(00:16:25) GoBolt - Finding Problems Close to You
(00:17:08) Shopify - Building a Waitlist & Showcasing the Product
(00:17:43) Fullscript - Cold Emailing
(00:18:30) Spellbook - Running Experiments Exceptionally Quickly
(00:19:27) Legion - Finding a Design Partner
(00:20:18) Knak - Consulting
(00:20:54) Dabble - Building Distrobution
(00:21:55) Zeffy - Making the Product Free

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Ankit left his job as a VC to launch a Voice AI platform—back in 2018! It wasn't the voice AI of today. The first demo sounded like a robot. But still, he convinced large enterprise customers in the healthcare space to try it out. He found a highly manual, call intensive workflow in the back office and autoamted it using AI.

Years later, he's raised $102M and has dozens of large $1M+ enterprise customers using the product. He talks about how he started it, how he saw the AI opportunity so early on, and how he found a way to lock in champions that pushed his product inside large enterprises.

Why you should listen:

• Why the search for product-market fit never stops.
• How to build trust with enterprise customers.
• How to get champions to fight battles for you and win enterprise deals.
• Why even successful startups are never straight lines up and to the right.

Keywords
product-market fit, AI in healthcare, automation, conversational AI, startup challenges, scaling, founder advice, technology evolution, compliance, trust in AI

Timestamps
(00:00:00) Intro
(00:02:01) How it all started
(00:06:29) Automating Insurance Calls
(00:16:37) Landing the first customers
(00:22:02) Giving your persona phone number to early users
(00:27:43) Landing large enterprise customers
(00:33:45) Getting Early Adopters to Believe
(00:36:34) Finding Product Market Fit
(00:38:04) One Piece of Advice

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Marty and his co-founders lived full-time in their office for several months. They worked on their startup 24/7. To come up with the idea, they messaged 120 potential customers every day for 3 months.

Originally, when they pitched YC they were told their idea would never work. YC said they'd seen it several times and it was destined to fail. So in 2 weeks Marty landed a customer and built a product-- and YC let him in. He went on to raise a $3M seed round from General Catalyst in 6 days and later a $17M Series A from a16z in 14 days.

We go deep into how to come up with massive ideas, how to get to product-market fit, and how to quickly fundraise from tier 1 VCs.

Why you should listen

• Why all 3 founders living in the office was the best decision they ever made. 
• How to raise a seed round in 6 days and a Series A in 14-- all from tier 1 VCs. 
• How to leverage LinkedIn to get exposure and lots of leads. 
• How to get more mindshare from your employees.
• Why Pylon has almost no meetings.
• How to come up with an idea using both top-down and bottoms-up processes.

Keywords
founders, startup, customer support, Pylon, co-founders, omnichannel, B2B, venture capital, product market fit, entrepreneurship, startup, Y Combinator, fundraising, product development, market trends, customer support, AI integration, team dynamics, venture capital, entrepreneurship

Timestamps

(00:00:00) Intro
(00:01:35) Why he chose to sleep in the office
(00:07:11) Project Management instead of People Management
(00:11:24) How it all started
(00:23:33) Cold Messaging Potential customers
(00:28:02) Finding the Trend
(00:35:49) Building V1
(00:38:32) Getting into YC as ChatGPT Comes Out
(00:42:37) Why fundraising is a "social game"
(01:01:21) Raising Series A from A16

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I interviewed Martin on the keynote stage at the SaaS North conference. Here is the audio version. Martin built Applyboard into a $4B unicorn doing $100M+ in ARR. He left and started a new startup called Passage— and raised a $40M seed round.

He talks about 100-hour weeks, hiring exceptional talent, why smaller teams can outperform—and why he decided to start all over again.

Why you should listen:

• Why great founders thrive in high-stress situations-- on "the edge of failure" as Martin calls it.
• How to make your first hire. 
• Why you need to go all-in and work crazy hours to build a unicorn.
• Why Martin thinks it's key to never give up, even in tough times, as cliche as it might sound.
• The importance of creating a positive environment to attract good people.

Keywords
entrepreneurship, education, immigration, impact, startup, Passage, ApplyBoard, perseverance, business model, founder journey

Timestamps
(00:00:00) Intro
(00:03:54) Getting Into Coding
(00:06:48) Accidentally Making Applyboard
(00:10:41) Starting startup #2
(00:17:19) Raising the Biggest Seed in Canada with Only 20 Employees
(00:20:07) If You Can't Outsmart Them, Outwork Them
(00:23:21) Getting the First Software Developer
(00:25:48) One Piece of Advice

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Jon started a sports betting app 4 years ago-- now he does $150M in revenue and $1B in betting volume. AND he's profitable. In his first year alone , he did $10 million in revenue.

He took a year to build the app and as soon as he launched it, it took off. He did $10M in revenue in his first year.

Honestly, it sounds too easy. But the reason it worked is because, as he shares on the episode, he'd spent 7 years in research mode. He'd spent years building a marketing agency in the sports betting space. He not only understand the market, the customers and the product, he'd also built a distribution machine and knew exactly how to get in front of users.

Here's how it happened.

Why you should listen
- Why distribution is the difference between success and failure
- How spending a long time in research mode can make go-to-market much faster
- Why simple product difference can lead to huge differences in outcomes

Keywords
sports betting, Dabble, entrepreneurship, product-market fit, startup journey, social betting, technology, marketing, revenue growth, challenges

Timestamps

(00:00:00) Intro
(00:01:49) Getting Into Sports Betting
(00:04:22) Before Dabble
(00:08:08) Starting Dabble & First Steps
(00:10:55) The Initial Vision
(00:17:55) How Sports Betting Works
(00:24:26) Nearly Going Bankrupt
(00:27:53) Building the App
(00:31:23) Launching
(00:35:47) Revenue Timeline
(00:38:28) Finding Product Market Fit
(00:41:48) One Piece of Advice

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