A Product Market Fit Show | Startup Podcast for Founders

Pablo is the first guest that has the same name as me-- so you KNOW this episode will be great. Pablo hustled for months just to get to $70K in ARR. He got rejected from YC, re-applied, and finally got in.

But after months in YC, he realized his first product was not going to work. He had some traction, but not nearly enough customer pull. So he shut it down. He went back to square one. He did customer discovery in a totally different space and leveraged the latest in Gen AI. He then built AI agents that automate calls in the logistics space.

Just a year after shutting down his first product, he'd grown to $2.2M in ARR. In December, he raised $15.6M from a16z.

Here's how it happened.

Why you should listen: 

• Why you should be careful of "free" money from grants.
• Why YC changed the trajectory of Pablo's startup.
• How a big pivot is often necessary-- even when you have customer traction. 
• Why the key is to find a true, no-brainer pain point.
• Meeting customers where they are can lead to smoother adoption of new technologies.
• How to build a product that provides clear ROI is essential for customer buy-in.
• Continuous exploration and adaptation are key to finding the right market fit.

Keywords

Happy Robot, startup journey, product market fit, early stage funding, co-founders, computer vision, YC, venture capital, entrepreneurship, business development, funding, European founders, Y Combinator, customer acquisition, pivoting, logistics, AI agents, startup growth, Series A, market research

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Alex sold his last IoT startup for over $200M to Samsung. He felt the needed to build something much bigger, so he started BrightAI. The goal was to use AI and IoT to solve big problems for enterprises.

A few years later, he bootstrapped to $100M in revenue across just 7 customers.  Last quarter, he raised $15M in venture funding. He shares how he closed million-dollar enterprise projects before building a product, why he refuses to go after just one vertical, and some of the biggest lessons he's learned after years building startups.

Why you should listen:

• Why impact is the biggest driver for starting startups. 
• How to find champions and get enterprise design partners.
• How AI and IoT can combine  to solve real-world issues.
• How to make sure you don't get stuck in a niche forever.
• How to tell if you're on to something in less than 18 months since launching. 

Keywords
SmartThings, Bright, IoT, critical infrastructure, pest control, AI, technology, innovation, entrepreneurship, product development, AI, pest control, multimodal AI, revenue streams, platform scaling, product-market fit, early-stage founders, entrepreneurship, sustainability, critical infrastructure

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Nathan has interviewed 100s of founders on how they raised their first few rounds. In this interview, we go through some of the most compelling stories he's heard. We go through step-by-step what you should do to raise a round, how to get meetings, how to tell stories, and every other piece of the fundraising puzzle.

If you're planning to raise a round anytime this year-- check this episode out.

Why you should listen:

• Why you need to look for believers in the early days.
• Why you need to meet way more investors than you might want to.
• How to create momentum for your round.
• Why spending more time planning will mean spending less time raising. 

Keywords
fundraising, startup, venture capital, investor relations, fundraising process, founder stories, capital raising, startup funding, investor introductions, fundraising strategies

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A few years into building Flashfood, Josh was $35K in debt with no money in his account. Just a few months earlier, he'd lost both the pilot customers he'd worked so hard to lock in. He'd worked for months to land them and had delivered what he promised.

But both retailers told him the problem he was solving was not important enough.

And then, he met Loblaws-- one of Canada's largest retailers. They loved the case studies he had. They tested it out and quickly launched it across 100% of their locations.

"I was going to shut down the company." That's how close it came to failing completely. Instead, a year after meeting Loblaws he was doing $1.5M ARR and had raised a $3M seed round. Now, he does 10s of millions in revenue and will soon be profitable.

Here's the story.   

Why you should listen:

• Why startups often drive founder to near bankruptcy.
• Why you need to keep testing your startup until you hear 'no'.
• Why sometimes large customers might be easier to close than small ones.
• How to get champions to close enterprise deals. 
• Why you might be a top priority for some customer sets and not others.

Keywords
food waste, grocery stores, app development, early stage founders, product market fit, sustainability, entrepreneurship, discount food, consumer behavior, environmental impact, enterprise sales, customer priorities, stakeholder buy-in, corporate culture, product-market fit, revenue growth, grocery industry, startup challenges, business strategy, environmental impact

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Darius started an EdTech startup to help users of online courses collaborate with each other. It blew up during COVID when everyone felt isolated. It gained thousands of users. They were engaged. They came back to use the platform. And, most importantly, they dramatically improved completion rates for online courses.

Darius thought he had it. But it turned out universities didn't want to pay. What users cared about was not what universities (the buyers) cared about.

His biggest lessons is that he should've pivoted much sooner. Here's why.

Why you should listen:

• Why success and failure are often not that far apart.
• Why engagement and usage don't always lead to revenue.
• How to figure out the KPI that matters for your buyer.
• Why users and buyers are not one and the same.
• Why you need to pivot much sooner than you might think-- or like.

Keywords
startup challenges, entrepreneurship, online learning, EdTech, market dynamics, product development, business strategy, lessons learned, networking, pivoting

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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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