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Episodes (20)
Blog Posts (15)
Episodes
5x founder asked Ford for a contract so large—they acquired his company instead. | Amar Varma, Founder of Mantle
Oct. 23, 2025
Amar is a 5x founder who helped birth Tinder (it was the 10th project—after the first 9 failed), then sold his next company to Ford for putting a platform in every single vehicle they make. But the wildest part? He got Ford t...
Why you shouldn't chase unicorns; 3 Big VC Myths; and how to keep control of your startup
Jan. 22, 2024
$1B startups get all the hype. But for 99% of founders, it’s the wrong goal. You’re better off building a sustainable business with consistent growth. Raising big rounds won’t make your company big and staying lean won’t make...
Andrew McLeod, Founder of Certn ($100M+ Raised) | How to Find Product Market Fit
May 31, 2023
Before the pandemic, there were 24 employees at Certn (Or Certonians, as they're called). After the pandemic, there were 500. That's 20x growth in just two years. That only happens for one reason... insane product-market fit. This is the story of ho…
He fought Al Qaeda in Iraq, turned down $250K at McKinsey—& built a $150M+ ARR unicorn. Here’s how it happened: | Blake Hall, Founder of ID.me
July 1, 2024
"I was technically homeless at the time. I was sleeping on my buddy's couch. I had declined $250,000/ year at McKinsey... I had no idea what I was doing." Now, Blake has $150M in ARR, growing 30% per year, with 80% gross margins. He's raised $400M a…
He got kicked out of Harvard—then grew to $5M ARR in just 3 months. | Roy Lee, Co-Founder of Cluely
Aug. 4, 2025
Roy Lee went from getting kicked out of Harvard and Columbia to building Cluely, one of the fastest-growing AI startups ever—going from 0 to $5 million ARR in just 3 months. We go deep on Roy’s playbook for using controversy,...
He hit $40M ARR, exited for over $100M—& raised only $1.5M. Here's how | Ian MacKinnon, Co-Founder of Later.com
Nov. 25, 2024
In 2014, Ian launched a simple product: it let social media marketers buffer Instagram posts. It was originally a hackathon project. But it quickly gained users. So he and his co-founders went all in. They raised just one sma...
Adam Neumann Returns, SV Spies, AI Robots Rise | April Startup News w/ Jack Kuveke
May 8, 2025
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 DoorDas...
At 21 he made his 1st million. At 23, he grew his startup to $8M ARR in 6 months. | Matt Espinoza, Founder of Clover
Nov. 13, 2025
Matt sold his first company at 19 and made $100K. He sold his second at 21 and made $800K. A couple years later, he launched Clover and grew it to $8M ARR in 6 months. His secret? Insane distribution. His formula is to ignore...
He bootstrapped to $4M ARR in 2 years. Here's his LinkedIn playbook you can't ignore. | Noah Greenberg, Founder of Stacker
April 3, 2025
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 pl...
He raised $1.5M, hit $400K ARR in 9 months— but had to Exit Early. Here’s the top 3 lessons he learned | Rob Palumbo, Co-Founder of Outpoint
Nov. 14, 2024
Rob founded Outpoint in 2020 to help marketers optimize their ad spend. He was a growth marketer and his founder a data scientist. He had team-market fit, a solid thesis, and paying customers. But when the recession hit and a...
How Shopify & DollarShaveClub got more views than the Super Bowl for under $10K
Feb. 11, 2024
The Super Bowl is the best place to get in front of customers—if you have $10M to spend. Which means for virtually all startups, it’s 100% useless. So I decided to look into some of the best campaigns early-stage startups use...
TechCrunch called this YC founder a fraud at 18—then he built a $10M ARR fintech. | Sahil Phadnis, Founder of Affiniti
Sept. 8, 2025
Sahil was 18 when TechCrunch published a hit piece calling him a copycat. His co-founder Aaron was 16. They'd just raised $6 million from YC and top VCs for their crypto startup, then got subpoenaed by a state government and ...
$10M Raised, 500K Users, but she still failed—here’s what went wrong | Benedetta Lucini, Founder of Oval Money
June 26, 2025
This is the brutally honest startup story every founder needs to hear. Benedetta shares how she built a fintech app to half a million users and raised $10M—yet still failed. You’ll learn why chasing big partnerships can back...
1st time founder completely pivots after YC—then grows 30x in a year to $2.2M ARR. | Pablo Palafox, Founder of HappyRobot
Jan. 30, 2025
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...
5 months in, Snapchat had only 127 users. Here's how Evan Spiegel found product market fit w/ Jeremy Liew (Partner at Lightspeed and Seed Investor in Snapchat)
April 22, 2024
Snapchat got 0 downloads the day it launched. 5 months in, it had only 127 users. Today Snapchat is an $18B company with 400 million daily active users. Evan Spiegel noticed what even Zuck missed: daily communication is meant...
5 Steps to PMF with Rob
Jan. 8, 2024
We released The Five Steps to Product Market Fit a few weeks ago and received lots of questions on how to apply the steps. In this episode, Rob and I share more colour and more stories on each step to help you understand how ...
99% of founders SUCK at storytelling. Here's the pro who taught Slack & Salesforce how to do it. | Matthew Dicks, professional storyteller & bestselling author of Storyworthy.
July 25, 2024
There is no better storyteller in the world than Matthew Dicks. He tells stories for a living. He gets paid by the world's biggest brands to create stories for them. He's won Moth StorySLAM (a storytelling competition in NYC)...
ChatGPT just hit $3B in ARR—here’s why Sam Altman is a strategic genius.
June 13, 2024
Sam Altman is playing chess not checkers. He partnered with Microsoft. He partnered with Apple. He grew to $3B in ARR in 2 years. Hate him or love him, he's a strategic genius. You'll recognize a pattern: Sam has an idea, pos...
Each Google/OpenAI update kills more startups. Here’s how to make sure you're not next.
June 27, 2024
Every startup needs to compete with incumbents. But it's different with AI. AI startups need to create websites or apps from scratch and drive traffic. Incumbents can just add AI as a feature. They have distribution built in. AI is not like previous…
Forget Founder Mode— MrBeast Mode is Where it's At. | The top 7 highlights from MrBeast's leaked framework.
Sept. 19, 2024
MrBeast's 36-page framework leaked this week. It's how he built a $1B+ company and became the #1 YouTuber in the world. His channel is worth over $1B. For the first time ever, we get to see how MrBeast operates. We go through the 7 most important th…
Blog Posts
30 Years, 5 Exits: How Serial Founder Russ Fradin Pivoted Dynamic Signal From Influencer Marketing to $50M ARR
Nov. 25, 2025
Most founders get one shot at building a company. Maybe two if they're lucky.
Russ Fradin has been founding, exiting, and reinventing companies for thirty straight years—from Flycast Communications in 1996 through his current venture, Larridi…
From $0 to $8M ARR in 6 Months: How 23-Year-Old Matt Espinoza Hacked Distribution with 1,000 Videos Per Day
Nov. 25, 2025
Most 23-year-olds are figuring out their first job.
Matt Espinoza just scaled his latest company from zero to $8 million ARR in six months.
His secret? An almost insane obsession with one thing: volume negates luck.
Matt built his first software …
How to Compete with Billion-Dollar Incumbents: The 5x Founder's Playbook
Nov. 14, 2025
Five-time founder Amar Varma has a peculiar talent: he keeps finding himself at the exact intersection of emerging technology and massive market opportunity. In 2012, he was running Hatch Labs when the team launched their tenth experiment—a re…
10 Years to Build a $550M InsurTech: How Sure's Wayne Slavin Pivoted From Flight Insurance to Embedded Insurance for Tesla and Toyota
Nov. 25, 2025
In 2015, Wayne Slavin had a crazy idea on a flight to Vegas: sell life insurance to people freaking out during turbulence.
One weekend later, he built a prototype. No actual insurance product. Just a landing page, some Google ads, and a fake paymen…
From $20B Nutanix to AI Unicorn: How Dheeraj Pandey Built Two Generational Companies
Nov. 19, 2025
Picture this: You're the CEO of a multi-billion dollar public company. You've spent eleven years building one of the fastest-growing infrastructure companies in history. Then COVID hits, data centers lock down, and everything you predicted about clo…
From Amazon Logistics to a $2.1B Shopify Exit: The AI-Driven Startup Growth Framework
Nov. 21, 2025
Picture this: You're nine months into your startup. You've raised $7 million. You've signed exactly ten merchants. Your flat pricing model that seemed brilliant in theory? Merchants don't get it. The fast shipping promise you're so proud of? Custome…
How Axonius Hit $100M ARR in 4.5 Years: The Product Market Fit Blueprint Most Founders Miss
Nov. 13, 2025
Dean Sysman woke up in the cheapest hotel room on the Las Vegas Strip, dreading the call he was about to make.
His startup, Axonius, had just finished another proof-of-concept with a potential customer. Like the previous POCs, it had been plagued w…
How Instalily Hit $1M ARR in Months by Building AI That Actually Does the Work
Nov. 25, 2025
When Amit Shah left his role as president of 1-800-Flowers after eleven years of scaling the company from $500 million to over $2 billion, he wasn't looking for another comfortable executive position. He had spent two decades watching talented teams…
How Simon Eskildsen Built TurboPuffer, the Vector DB Powering Cursor and Notion
Nov. 15, 2025
Have you ever looked at your infrastructure costs and thought, "This can't be right"? That's exactly what happened when Simon Eskildsen discovered vector databases were so expensive that companies couldn't even launch features.
After spending nearl…
How to Build a Legal AI Company: The 10-Year Journey from Professor to $25M ARR
Nov. 13, 2025
At age 26, Ben Alaire became possibly the youngest tenure-track law professor in University of Toronto's history. Fresh from clerking at the Supreme Court of Canada, he had the academic dream—teaching tax law and co-authoring the 1,500-page te…
How to Build a Startup Moat: 3 Proven Strategies from a Microsoft Acquisition
Nov. 5, 2025
Do you ever feel like you're doing all the right things to build your startup, but competitors keep eating your lunch?
There's a strategy you may not have considered. It's not about moving faster or building more features—it's about building …
How to Pivot Your Startup to AI: From Nice-to-Have Terminal to $1M ARR Every 10 Days
Nov. 11, 2025
Every founder dreams of building something people can’t live without. But markets evolve faster than most startups can.
What separates companies that stall from those that scale is how they adapt—not with another feature, but with a new…
Product-User Fit vs Product-Buyer Fit: How Snyk Spent $4M to Learn the Difference
Nov. 14, 2025
Two years in, Guy Podjarny had burned through $4 million and built Snyk to just $100,000 ARR. Thousands of developers were using the product. They loved it. They recommended it to colleagues. They integrated it into their workflows. They just had on…
Startup Go to Market Strategy: How to Build a Category-Creating Company From Zero (Real Case Study)
Nov. 13, 2025
Most startup advice about go-to-market strategy is backwards.
They tell you to "find your ICP" and "build a sales funnel" before validating that anyone wants what you're building. According to CB Insights, 42% of startups fail because there is no m…
The Startup Acquisition Strategy That Built a $5B Parking Empire
Nov. 25, 2025
Alexander Israel sat in a Venice parking lot in 2018, staring at his phone. The first Stripe notification pinged. Someone had just paid for parking through Metropolis without tickets, credit cards, or any friction whatsoever. The technology was so s…
5x founder asked Ford for a contract so large—they acquired his company instead. | Amar Varma, Founder of Mantle
Oct. 23, 2025
Amar is a 5x founder who helped birth Tinder (it was the 10th project—after the first 9 failed), then sold his next company to Ford for putting a platform in every single vehicle they make. But the wildest part? He got Ford t...
Why you shouldn't chase unicorns; 3 Big VC Myths; and how to keep control of your startup
Jan. 22, 2024
$1B startups get all the hype. But for 99% of founders, it’s the wrong goal. You’re better off building a sustainable business with consistent growth. Raising big rounds won’t make your company big and staying lean won’t make...
Andrew McLeod, Founder of Certn ($100M+ Raised) | How to Find Product Market Fit
May 31, 2023
Before the pandemic, there were 24 employees at Certn (Or Certonians, as they're called). After the pandemic, there were 500. That's 20x growth in just two years. That only happens for one reason... insane product-market fit. This is the story of ho…
He fought Al Qaeda in Iraq, turned down $250K at McKinsey—& built a $150M+ ARR unicorn. Here’s how it happened: | Blake Hall, Founder of ID.me
July 1, 2024
"I was technically homeless at the time. I was sleeping on my buddy's couch. I had declined $250,000/ year at McKinsey... I had no idea what I was doing." Now, Blake has $150M in ARR, growing 30% per year, with 80% gross margins. He's raised $400M a…
He got kicked out of Harvard—then grew to $5M ARR in just 3 months. | Roy Lee, Co-Founder of Cluely
Aug. 4, 2025
Roy Lee went from getting kicked out of Harvard and Columbia to building Cluely, one of the fastest-growing AI startups ever—going from 0 to $5 million ARR in just 3 months. We go deep on Roy’s playbook for using controversy,...
He hit $40M ARR, exited for over $100M—& raised only $1.5M. Here's how | Ian MacKinnon, Co-Founder of Later.com
Nov. 25, 2024
In 2014, Ian launched a simple product: it let social media marketers buffer Instagram posts. It was originally a hackathon project. But it quickly gained users. So he and his co-founders went all in. They raised just one sma...
Adam Neumann Returns, SV Spies, AI Robots Rise | April Startup News w/ Jack Kuveke
May 8, 2025
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 DoorDas...
At 21 he made his 1st million. At 23, he grew his startup to $8M ARR in 6 months. | Matt Espinoza, Founder of Clover
Nov. 13, 2025
Matt sold his first company at 19 and made $100K. He sold his second at 21 and made $800K. A couple years later, he launched Clover and grew it to $8M ARR in 6 months. His secret? Insane distribution. His formula is to ignore...
He bootstrapped to $4M ARR in 2 years. Here's his LinkedIn playbook you can't ignore. | Noah Greenberg, Founder of Stacker
April 3, 2025
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 pl...
He raised $1.5M, hit $400K ARR in 9 months— but had to Exit Early. Here’s the top 3 lessons he learned | Rob Palumbo, Co-Founder of Outpoint
Nov. 14, 2024
Rob founded Outpoint in 2020 to help marketers optimize their ad spend. He was a growth marketer and his founder a data scientist. He had team-market fit, a solid thesis, and paying customers. But when the recession hit and a...
How Shopify & DollarShaveClub got more views than the Super Bowl for under $10K
Feb. 11, 2024
The Super Bowl is the best place to get in front of customers—if you have $10M to spend. Which means for virtually all startups, it’s 100% useless. So I decided to look into some of the best campaigns early-stage startups use...
TechCrunch called this YC founder a fraud at 18—then he built a $10M ARR fintech. | Sahil Phadnis, Founder of Affiniti
Sept. 8, 2025
Sahil was 18 when TechCrunch published a hit piece calling him a copycat. His co-founder Aaron was 16. They'd just raised $6 million from YC and top VCs for their crypto startup, then got subpoenaed by a state government and ...
$10M Raised, 500K Users, but she still failed—here’s what went wrong | Benedetta Lucini, Founder of Oval Money
June 26, 2025
This is the brutally honest startup story every founder needs to hear. Benedetta shares how she built a fintech app to half a million users and raised $10M—yet still failed. You’ll learn why chasing big partnerships can back...
1st time founder completely pivots after YC—then grows 30x in a year to $2.2M ARR. | Pablo Palafox, Founder of HappyRobot
Jan. 30, 2025
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...
5 months in, Snapchat had only 127 users. Here's how Evan Spiegel found product market fit w/ Jeremy Liew (Partner at Lightspeed and Seed Investor in Snapchat)
April 22, 2024
Snapchat got 0 downloads the day it launched. 5 months in, it had only 127 users. Today Snapchat is an $18B company with 400 million daily active users. Evan Spiegel noticed what even Zuck missed: daily communication is meant...
5 Steps to PMF with Rob
Jan. 8, 2024
We released The Five Steps to Product Market Fit a few weeks ago and received lots of questions on how to apply the steps. In this episode, Rob and I share more colour and more stories on each step to help you understand how ...
99% of founders SUCK at storytelling. Here's the pro who taught Slack & Salesforce how to do it. | Matthew Dicks, professional storyteller & bestselling author of Storyworthy.
July 25, 2024
There is no better storyteller in the world than Matthew Dicks. He tells stories for a living. He gets paid by the world's biggest brands to create stories for them. He's won Moth StorySLAM (a storytelling competition in NYC)...
ChatGPT just hit $3B in ARR—here’s why Sam Altman is a strategic genius.
June 13, 2024
Sam Altman is playing chess not checkers. He partnered with Microsoft. He partnered with Apple. He grew to $3B in ARR in 2 years. Hate him or love him, he's a strategic genius. You'll recognize a pattern: Sam has an idea, pos...
Each Google/OpenAI update kills more startups. Here’s how to make sure you're not next.
June 27, 2024
Every startup needs to compete with incumbents. But it's different with AI. AI startups need to create websites or apps from scratch and drive traffic. Incumbents can just add AI as a feature. They have distribution built in. AI is not like previous…
Forget Founder Mode— MrBeast Mode is Where it's At. | The top 7 highlights from MrBeast's leaked framework.
Sept. 19, 2024
MrBeast's 36-page framework leaked this week. It's how he built a $1B+ company and became the #1 YouTuber in the world. His channel is worth over $1B. For the first time ever, we get to see how MrBeast operates. We go through the 7 most important th…
30 Years, 5 Exits: How Serial Founder Russ Fradin Pivoted Dynamic Signal From Influencer Marketing to $50M ARR
Nov. 25, 2025
Most founders get one shot at building a company. Maybe two if they're lucky.
Russ Fradin has been founding, exiting, and reinventing companies for thirty straight years—from Flycast Communications in 1996 through his current venture, Larridi…
From $0 to $8M ARR in 6 Months: How 23-Year-Old Matt Espinoza Hacked Distribution with 1,000 Videos Per Day
Nov. 25, 2025
Most 23-year-olds are figuring out their first job.
Matt Espinoza just scaled his latest company from zero to $8 million ARR in six months.
His secret? An almost insane obsession with one thing: volume negates luck.
Matt built his first software …
How to Compete with Billion-Dollar Incumbents: The 5x Founder's Playbook
Nov. 14, 2025
Five-time founder Amar Varma has a peculiar talent: he keeps finding himself at the exact intersection of emerging technology and massive market opportunity. In 2012, he was running Hatch Labs when the team launched their tenth experiment—a re…
10 Years to Build a $550M InsurTech: How Sure's Wayne Slavin Pivoted From Flight Insurance to Embedded Insurance for Tesla and Toyota
Nov. 25, 2025
In 2015, Wayne Slavin had a crazy idea on a flight to Vegas: sell life insurance to people freaking out during turbulence.
One weekend later, he built a prototype. No actual insurance product. Just a landing page, some Google ads, and a fake paymen…
From $20B Nutanix to AI Unicorn: How Dheeraj Pandey Built Two Generational Companies
Nov. 19, 2025
Picture this: You're the CEO of a multi-billion dollar public company. You've spent eleven years building one of the fastest-growing infrastructure companies in history. Then COVID hits, data centers lock down, and everything you predicted about clo…
From Amazon Logistics to a $2.1B Shopify Exit: The AI-Driven Startup Growth Framework
Nov. 21, 2025
Picture this: You're nine months into your startup. You've raised $7 million. You've signed exactly ten merchants. Your flat pricing model that seemed brilliant in theory? Merchants don't get it. The fast shipping promise you're so proud of? Custome…
How Axonius Hit $100M ARR in 4.5 Years: The Product Market Fit Blueprint Most Founders Miss
Nov. 13, 2025
Dean Sysman woke up in the cheapest hotel room on the Las Vegas Strip, dreading the call he was about to make.
His startup, Axonius, had just finished another proof-of-concept with a potential customer. Like the previous POCs, it had been plagued w…
How Instalily Hit $1M ARR in Months by Building AI That Actually Does the Work
Nov. 25, 2025
When Amit Shah left his role as president of 1-800-Flowers after eleven years of scaling the company from $500 million to over $2 billion, he wasn't looking for another comfortable executive position. He had spent two decades watching talented teams…
How Simon Eskildsen Built TurboPuffer, the Vector DB Powering Cursor and Notion
Nov. 15, 2025
Have you ever looked at your infrastructure costs and thought, "This can't be right"? That's exactly what happened when Simon Eskildsen discovered vector databases were so expensive that companies couldn't even launch features.
After spending nearl…
How to Build a Legal AI Company: The 10-Year Journey from Professor to $25M ARR
Nov. 13, 2025
At age 26, Ben Alaire became possibly the youngest tenure-track law professor in University of Toronto's history. Fresh from clerking at the Supreme Court of Canada, he had the academic dream—teaching tax law and co-authoring the 1,500-page te…
How to Build a Startup Moat: 3 Proven Strategies from a Microsoft Acquisition
Nov. 5, 2025
Do you ever feel like you're doing all the right things to build your startup, but competitors keep eating your lunch?
There's a strategy you may not have considered. It's not about moving faster or building more features—it's about building …
How to Pivot Your Startup to AI: From Nice-to-Have Terminal to $1M ARR Every 10 Days
Nov. 11, 2025
Every founder dreams of building something people can’t live without. But markets evolve faster than most startups can.
What separates companies that stall from those that scale is how they adapt—not with another feature, but with a new…
Product-User Fit vs Product-Buyer Fit: How Snyk Spent $4M to Learn the Difference
Nov. 14, 2025
Two years in, Guy Podjarny had burned through $4 million and built Snyk to just $100,000 ARR. Thousands of developers were using the product. They loved it. They recommended it to colleagues. They integrated it into their workflows. They just had on…
Startup Go to Market Strategy: How to Build a Category-Creating Company From Zero (Real Case Study)
Nov. 13, 2025
Most startup advice about go-to-market strategy is backwards.
They tell you to "find your ICP" and "build a sales funnel" before validating that anyone wants what you're building. According to CB Insights, 42% of startups fail because there is no m…
The Startup Acquisition Strategy That Built a $5B Parking Empire
Nov. 25, 2025
Alexander Israel sat in a Venice parking lot in 2018, staring at his phone. The first Stripe notification pinged. Someone had just paid for parking through Metropolis without tickets, credit cards, or any friction whatsoever. The technology was so s…