최고 Product Market Fit 팟캐스트 (2025)

1
WebSummit Panel w/ Founders of Glean ($5B) and Huntress ($2B): What it takes to hit $100M ARR 18:45

3d ago18:45

18:45

Two founders, two wildly different paths to $100M ARR: Arvind Jain, founder of Glean, walked away from a unicorn to start over—raising $15M without revenue and ignoring lean startup rules. Kyle Hanslovan, founder of Huntress, faced brutal rejection, slept in his car, maxed out credit cards, and still crushed it. This episode is packed with raw less…

1
How his $2B startup grew to $10M+ ARR with zero marketing. | Avery Pennarun, Founder of Tailscale 50:31

6d ago50:31

50:31

Avery Pennarun raised $160M for Tailscale—without even meaning to. What started as a small, simple project exploded into an unstoppable force in network connectivity and security. This episode reveals exactly how Avery turned a tiny seed round into millions of dollars in ARR, powered by nothing more than word-of-mouth and an obsession with solving …

1
May Startup News: Elizabeth Holmes Returns, Billion-Dollar Frauds, & the End of Tech Jobs w/ Jack Kuveke 28:43

10d ago28:43

28:43

Description: Jack Kuveke returns to unpack the wildest startup news this month: from billion-dollar frauds and crypto scams, to OpenAI’s secretive $6.5 billion gadget project with Apple’s design legend Jony Ive. We dig into why big-name investors keep missing red flags, and why AI might be crushing entry-level tech jobs faster than anyone expected.…

1
He hit $1M ARR in 10 months—after doing of a full, 180 pivot. | Merrill Lutsky, Founder of Graphite 56:30

13d ago56:30

56:30

After two pivots and nearly running out of runway, Merrill Lutsky found insane growth—scaling Graphite to tens of thousands of daily users and millions in ARR. He reveals exactly how Graphite landed its first massive enterprise customer, doubled revenue overnight by changing pricing, and turned user feedback into momentum. Merrill shares hard-earne…

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PMF Observations: Why passion is more important than you think 19:51

17d ago19:51

19:51

Most early-stage founders get trapped in the chaos of endless tasks, there's always too much to do and not enough time. We go through the last 4 episodes to see what how the best founders prioritize. We also see why you can raise millions without real traction but can’t fake product-market fit, how positioning yourself for luck is as important as h…

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He didn't raise VC for the first 7 years— then grew to $1B in ARR. | Dax Dasilva, Founder of Lightspeed 55:15

20d ago55:15

55:15

Dax built Lightspeed into a $1B ARR public company—even though he bootstrapped for the first 7 years. In this episode, he reveals exactly how he used a 4x pricing shift to create a global reseller machine that grew him to $10M ARR. He also breaks down why obsessing over design and deep customer empathy built the foundation for success.—and how step…

1
Q1 2025: The Seed to Series A Gap is Wider Than Ever. Here's what to do. | Peter Walker, Head of Insights at Carta 48:22

24d ago48:22

48:22

Carta just released their report for Q1 2025. Peter is Head of Insights at Carta, and the person who owns their data practice. We sit down to talk about the largest trends he saw across fundraising, industries, graduation rates and even hiring practices. Carta data shows that graduation rates from Seed to A are as low as they've ever been. Bridge r…

1
He went from 0 to a $210M exit in 3 years—without inventing anything new. | Kazi Ahmed, Founder of Carbon6 45:14

27d ago45:14

45:14

Kazi Ahmed took a small insight—seeing friends cash out from Amazon brands—and built Carbon6, a software roll-up startup, selling it for $210M just three years later. But behind the quick success was a frantic scramble to survive. Aggressive acquisitions nearly ran them out of cash, forcing a brutal pivot from burning $1M per month to profitability…

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Forecasts are overrated—great founders build one step at a time. | PMF Observations 18:06

1M ago18:06

18:06

I break down my top insights from recent conversations with four founders who won in unconventional ways. You’ll hear how Noah turned LinkedIn posts into his primary sales channel (without ever going viral), why Dan’s startup survived a brutal 95% downround but ended up at $400M ARR two years later, how Adam turned a stagnant $3M ARR business into …

1
He took on Robinhood & built Public.com into a $1B company with $440M raised. | Jannick Malling, Founder of Public.com 55:12

1M ago55:12

55:12

Public co-founder Jannick Malling shares exactly how he grew his startup from a tiny beta to millions of users—and hundreds of millions raised. He reveals why fractional shares changed the game for user acquisition, how the company cleverly seized on the GameStop moment to explode growth, and why relentless product focus was critical to scaling qui…

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Adam Neumann Returns, SV Spies, AI Robots Rise | April Startup News w/ Jack Kuveke 39:53

1M ago39:53

39:53

Corporate spies stealing Slack messages. Adam Neumann raising another $100M (for WeWork 2.0?). AI startups hitting $34B valuations with zero revenue and ordering Ben & Jerry's ice cream over 15 payments with Klarna on DoorDash. April was wild, and Jack Kuveke joins the show to unpack the chaos, controversy, and insanity behind the biggest startup h…

1
1 year in he had just 3 customers—today he’s at $100M ARR. | Forrest Zeisler, Co-Founder of Jobber | Forrest Zeisler, Co-Founder of Jobber 53:13

1M ago53:13

53:13

Forrest Zeisler spent 6 months hearing “no” from every potential customer he spoke to. One year in, Jobber had just three customers—paying $29/month. Today, Jobber generates over $100M ARR, has raised $180M in VC, and employs nearly 1,000 people. In this episode, Forrest shares the brutally honest story behind Jobber’s early days: months of rejecti…

1
He lost 90% of his users overnight—then grew his consumer app to $10M ARR. | Koen Droste, Founder of Polarsteps 46:30

1M ago46:30

46:30

He turned a personal travel tracker into an app with 10 million users and $10 million in revenue, with almost no funding. He reveals how ignoring conventional startup advice—like launching early, chasing revenue, or partnering for growth—was key to their viral success. He realized everything growth was about word-of-mouth. So the key to success was…

1
He launched a “side-project”— now it’s used by 10% of all restaurants. | Jordan Boesch, Founder of 7Shifts 40:20

2M ago40:20

40:20

Jordan Boesch started 7shifts as a teenager helping his dad manage restaurant shifts. Today, his software runs scheduling for 50,000 restaurants. This episode dives into how Jordan bootstrapped early growth, why relentless focus on solving real customer pain mattered more than funding, and how tight partnerships supercharged his expansion. Jordan a…

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1st-time founder grows AI headshot app from $0 to $10M ARR in 2 years—with no funding. | Wesley Tian, Founder of Aragon 53:26

2M ago53:26

53:26

Wesley turned a simple AI headshot generator into a $10M ARR, profitable company—in just two years. He was fired from his job, broke in San Francisco, and, after getting rejected by 30 VCs, down to his last few thousand bucks. But Wesley saw a moment: generative AI was taking off, and no one was tackling AI headshots. Fast-forward two years, and he…

1
He raised $30M & failed. Then raised $0 & grew to $550M in revenue. Here's what he learned. | Mike Salguero, Founder of Butcherbox 54:56

2M ago54:56

54:56

Mike first raised $30M for a marketplace that never truly had product-market fit. Then he bet only $10K on ButcherBox. A few years later, he's doing $550M in revenue and he's profitable. The difference is in his first startup he was just catering to investors— in his second one only to customers. If you’re an early founder chasing growth, listen to…

1
He invested in 30 early-stage startups. Here's what he looks for in the founders he backs. | Gopi Rangan, Founder of Sure Ventures 35:57

2M ago35:57

35:57

Gopi Rangan has invested in 29 early-stage startups from scratch. He shares a simple but powerful approach to picking the right VCs, structuring your pitch (long-term vision + short-term plan + fuzzy mid-term path), and proving you are the sort of founder every pre-seed investor craves. If you’re raising a pre-seed or seed, Gopi’s tips will make yo…

1
He raised $300M to prevent heart attacks. Here's how he got his health tech startup off the ground. | Dr. Min, Founder of Cleerly 43:22

2M ago43:22

43:22

Cardiologist Jim Min watched too many 50-year-olds die with no heart-attack warning. He co-founded Cleerly to automate detailed coronary scans—no invasive procedures, no endless manual work. Yet healthcare’s glacial pace, payers, and federal approvals all stand in his way. Hear how he’s testing AI across thousands of patients, fighting for universa…

1
He grew to $25M in ARR and $14M in annual profits—with no funding & no dilution. | Adam Robinson, Founder of Retention.com 52:10

2M ago52:10

52:10

Adam Robinson once struggled with a stagnant email SaaS stuck at $3M ARR, but he kept experimenting until he found how to solve a problem no one else was tackling—and everything changed. Suddenly, buyers were begging for his identity-based marketing tool—so he spun out Retention.com and grew it to $14M+ in annual profit with no outside funding. In …

1
He took a 97% downround—then grew to $400M ARR & a $575M valuation in 2 years. | Dan Park, CEO of Clutch 45:22

2M ago45:22

45:22

Dan Park joined Clutch when it was selling 20 cars a month. Then he grew it from $20M in 2019 to $200M in sales by 2022. He was one of Canada's fastest growing companies. Just as he was going to close a $100M round, the macro changed completely. Suddenly, he was left with only six weeks of cash. He was forced to go through a 97% down round at a $15…

1
He bootstrapped to $4M ARR in 2 years. Here's his LinkedIn playbook you can't ignore. | Noah Greenberg, Founder of Stacker 47:34

2M ago47:34

47:34

Noah Greenberg grew a content-distribution product from zero to $1M ARR in just one year (and to $4M in 2 years) by focusing on a single channel most founders underrate: LinkedIn. He posted insights daily, highlighted key players in his industry, and made it impossible for prospects not to notice him. In this episode, Noah reveals the exact step-by…

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He invested in 684 AI startups—& realized that quitters always win. | Jack Kuveke, Founder turned VC at Jabroni Capital 38:44

2M ago38:44

38:44

We break down the real startup playbook: fake users, fake traction, real secondaries. From starting a company with zero customers, to raising millions and launching a VC fund that's built to lose money, Jack shares the blueprint for getting rich (without working hard). Forget chasing product-market fit. Start chasing growth, money, and, most of all…

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The secrets to mastering product-led growth. | Wes Bush, Author of the #1 Bestselling Book on Product-Led Growth 40:58

3M ago40:58

40:58

Wes Bush wrote the original bestseller on Product-Led Growth—and then watched everyone try to copy Dropbox and Slack without truly getting it. Now, he’s here to break down exactly what goes wrong when early-stage founders jump into PLG, how to spot your product’s “million-dollar free problem,” and how to fix the three biggest onboarding gaps that s…

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He sold SkipTheDishes for $200M—then grew Neo Financial to a $1B valuation. | Jeff Adamson, Co-Founder of NeoFinancial & SkipTheDishes 1:01:06

3M ago1:01:06

1:01:06

Jeff Adamson co-founded SkipTheDishes, scaled it to 80% market share, and sold it for $200M—all before Uber Eats and DoorDash even got serious about Canada. He started with zero tech experience, got doors slammed in his face by restaurant owners, and had to personally place orders just to keep early partners engaged. Then, when Uber Eats launched i…

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How to tell if you have true product-market fit—& what to do if you don't. | Matt Watson, Host of Product Driven 27:31

3M ago27:31

27:31

One of the most common questions I get is 'How do I know if I have product market fit?" Especially when you're in that gray zone where things are kind of working but they're not really taking off yet, how do you know if you have product-market fit or not? That's exactly what we dive into here. Why you should listen: Why demo to close is an excellen…

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He got rejected by 40 VCs & had 6 months of runway—2 years later, he raised $100M from a16z. | Edo Liberty, Founder of Pinecone 1:02:14

3M ago1:02:14

1:02:14

Edo Liberty left a high-paying job at AWS—where he was building AI at the highest level—to start Pinecone, a company no one understood. He pitched 40+ VCs, got rejected by every single one, and nearly ran out of money. Then, he flipped the pitch, raised $10M, and built one of the most important infrastructure companies in AI. Then ChatGPT dropped. …

1
Post-YC, he split with his co-founder—then grew profitably to $2M ARR with just 5 people. | Jon Yoo, Founder of Suger 46:46

3M ago46:46

46:46

Jon Yoo’s startup wasn’t working. He pivoted mid-YC, spent five brutal weeks without signing a single customer, and then—right after raising his seed round—his co-founder left. Most startups die right there. Instead, Jon figured out how to land massive customers like FiveTran and Snowflake. He grew from $500K to $2M ARR in 6 months. Why you should …

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From mushroom-picking in Belarus to $200M/year. How he built Flo Health into a $1B health app. | Dmitry Gurski, Founder of Flo Health 1:13:34

3M ago1:13:34

1:13:34

This is one of the wildest founder journeys you’ll ever hear. Dmitry Gurski went from growing potatoes and picking mushrooms on a farm in Belarus to building Flo—a billion-dollar company with 75M monthly users that dominates the health and fitness category worldwide. He started Flo in a market already controlled by PayPal co-founder Max Levchin’s s…

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He started Groupon for SMBs, grew to $36M ARR—then exited for $170M. | Saurav Chopra, Founder of Perkbox 53:00

3M ago53:00

53:00

Saurav started a Groupon-like offering for SMBs in 2011. He quickly learned it wasn't going to work. He and his team pivoted and started driving leads to suppliers using Facebook ads. It worked and they generated revenue—but they were becoming a digital advertising agency. It wasn't at all what they wanted to build. So they pivoted again. They used…

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It took him 7 years to hit $1M ARR—now his $1B public company does $1M every day. | Noah Glass, Founder of Olo 1:10:28

3M ago1:10:28

1:10:28

In 2005 most people didn't even have cellphones yet. Those who did used flip phones. That's when Noah started Olo, a webapp to let people pre-order coffee from nearby shops. Users had to login on web, add a credit card, create pre-made orders and then send a text to a preset number when they wanted to pre-order. It was way, way ahead of its time. N…

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He interviewed users, built a waitlist & raised $1.1M—but it still didn't work. | Frankie Le Nguyen, Founder of Staging Labs 38:58

4M ago38:58

38:58

Frankie lost $10K in a crypto transaction—so he started Staging Labs to find a way to help others prevent crypto scams. He was head of an incubator called Entrepreneurship First and had seen dozens and dozens of founders build startups. He knew exactly what to do—and he did everything right. He found a co-founder, built an MVP, did customer discove…

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He got rejected by 50 VCs & had 4 months of runway—3 years later, he's at $150M ARR & profitable. | Hussein Fazal, Co-Founder of Super.com 1:02:07

4M ago1:02:07

1:02:07

Hussein's travel startup was doing $10s of millions when COVID hit. His revenue didn't just go to zero, it went negative. There were more customers asking for refunds than new sales. He was 4 months from running out of money. He ended up making a complete pivot, he changed the company's name from SnapTravel to Super.com. He went from travel to fint…

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Amplitude is now a $1.5B public company. Here's how they beat competitors with a 10x cheaper product. | Jeffrey Wang, Co-Founder of Amplitude 57:20

4M ago57:20

57:20

When Amplitude launched Mixpanel was the big game in town. They were first to market, had raised more money, and had a well-known brand. VCs passed on Amplitude because it seemed like just another Mixpanel. Today, Amplitude is a $1.5B public company—they're about 2x bigger than Mixpanel. Mixpanel's marketing spend helped educate the market. But bef…

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This 1st time founder raised a $38M Series A—after taking over 2 years to launch. | Chris Ellis, Founder of Thatch 55:54

4M ago55:54

55:54

This first time founder just raised a $38 million Series A. The crazy part is that for all of 2021, 2022, 2023, he had almost no revenue. He spent all that time building and pivoting. Finally he launched in 2024—and it blew up. I saw his LinkedIn post and his revenue chart doesn't look like a hockey stick... it looks like straight a vertical line. …

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Why new Carta data shows bridge rounds might be worse than you think. | Peter Walker, Head of Insights at Carta 31:17

4M ago31:17

31:17

Carta just released their report for Q4 2024. Peter is Head of Insights at Carta, and the person who owns their data practice. We sit down to talk about the largest trends he saw across fundraising, industries, graduation rates and even hiring practices. Carta data shows that graduation rates from Seed to A are much lower for companies that have ra…

1
He exited for $335M—& felt "emptiness". So he quit, gave up millions in earnout, & grew to $1M ARR in 6 months. | Alon Arvatz, Founder of IntSights & PointFive 51:43

4M ago51:43

51:43

Alon was a hacker for the Israeli Defence Forces' cyber department. There he saw the most advanced methods used in cyber warfare. So when he left, he started IntSights-- a company that helped enterprises defend themselves from cyber attacks. He was a first-time founder who didn't even know the word 'unicorn'. He made all the mistakes you could make…

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He raised $20M, hit $3.5M in revenue—& failed. Here are the top 3 lessons he learned. | Ned Phillips, Founder of Bambu 1:01:11

4M ago1:01:11

1:01:11

Ned had a chance to run Robinhood Asia but he turned it down. Instead, he launched a competitive product. He decided to go B2B and sell to banks and other financial institutions. He locked down a $400K revenue sale before writing a line of code. It seemed easy at first. Overtime, he grew to $3.5M in revenue, billions in assets under management and …

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He exited for hundreds of millions—then invested in 20+ founders. Here's what he looks for. | Jason Van Gaal, Founder of ROOT 48:02

4M ago48:02

48:02

Jason built a data center company in the 2013. When he exited in 2019, it was the third-largest exit in Canada that year. He'd sold his previous startup and invested 100% of his capital into ROOT. He grew to 10s of millions and exited for 100s of millions. Now he's invested in over 20 angel-stage startups. He shares the story of ROOT and what he lo…

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1st time founder completely pivots after YC—then grows 30x in a year to $2.2M ARR. | Pablo Palafox, Founder of HappyRobot 56:37

5M ago56:37

56:37

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 sh…

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He exited for $200M— then bootstrapped his next startup to $100M in revenue. | Alex Hawkinson, Founder of BrightAI 43:19

5M ago43:19

43:19

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 c…

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The early-stage fundraising playbook—here's how to raise your first few rounds. | Nathan Beckord, Host of How I Raised It 29:24

5M ago29:24

29:24

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 r…

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He lost his only 2 customers & was ready to quit—then he grew to $1.5M ARR in a year. | Josh Domingues, Founder of Flashfood 50:00

5M ago50:00

50:00

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 m…

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He raised $250K, had thousands of users, but failed— because he didn't pivot fast enough. | Darius Vaillancourt, Founder of Howdy 27:50

5M ago27:50

27:50

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 i…

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Stripe bought his startup for $1.1B—just 2.5 years after he quit his job. | Zach Abrams, Co-Founder of Bridge 55:25

5M ago55:25

55:25

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…

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The 5 Steps to Product-Market Fit w/ Chris Saad, ex-Head of Product at Uber, Host of The Startup Podcast 51:03

5M ago51:03

51:03

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…

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How Gusto’s $10B founder raised $6M, built a team of 5—& hit $5M ARR in just 2 years. | Josh Reeves, Founder of Gusto 56:33

5M ago56:33

56:33

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 larg…

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The top 5 early-stage startup lessons for 2025 12:02

5M ago12:02

12:02

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 o…

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He raised $1.3M, hit $100K ARR—but failed. Here's the lesson every founder needs to hear. | Tolga Ermis, Founder of PromiseQ 30:24

6M ago30:24

30:24

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 …

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24 ways to get your first customers—based on real examples from the last 100 episodes. 24:10

6M ago24:10

24:10

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…

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He bet on voice AI when no one else did. Now he has $1M+ customers & $100M raised. | Ankit Jain, Founder of Infinitus 39:44

6M ago39:44

39:44

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 raise…

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