It was “really slow in the first couple of years...really, really slow.” GoHenry was an app and debit card for kids to help parents teach their kids about money. Dean started over a decade ago in 2012, when mobile was just truly taking off. And yet, it took multiple years to get off the ground. Once he found the right channels and repeatable growth…

Jaspar graduated YC & closed a $11.5M seed round this week. He launched Artisan just 8 months ago. And this is the first venture-backed startup he's ever ran. He started with product-led-growth but struggled. In May, he moved to a sales-first go-to-market & scaled from $200K ARR to $1.3M ARR by September. We go deep and tactical to figure out exact…

Cody started a ride-share business in 2017 with no capital. He focused exclusively on small towns (population <100K) where Uber/Lyft weren't available. I know as a VC I would've passed if he'd pitched me when he started—and I would've been dead wrong. So far he's raised only $2.1M, compared to Uber's $30B+ raised. And yet, he built a business doing…

I tried to pay my employees as little as possible. I thought I was being resourceful—& it seemed to work. Until it totally backfired. I learned my lesson the hard way. No founder wants to hire B-level or C-level talent. Everyone is looking for A-players. But most founders don't put in the work. And they end up with B-level teams. If you're serious …

Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks because he couldn't afford a hotel. Finally, 3 years in he'd hit $1.5M ARR. So he pitched 60 VCs for a Series A—and got 60 'no'…

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 things that startup founders can learn from MrBeast. From what maniacal obsession looks like, what it m…

Andres Bilboa is one of the co-founders of Rappi, the highest-valued app of LATAM ($5B valuation). Now he runs an incubator called Makers and has invested in dozens of startups. In this episode, he shares how Rappi started with no funding and no network. They added restaurants into their platform without permission and gave cash to couriers to buy …

Douglas has been in media and PR for over two decades. He’s the founder of Betakit Inc and has been running Betakit, Canada’s TechCrunch, for nearly 10 years. He understands what startups need to do to leverage PR, and how PR can help startups hire, fundraise and sell. On this episode, we get tactical and go deep on exactly when it makes sense to u…

In this episode, I sit down with Nick Frosst, Co-Founder of Cohere, the $5.5B AI startup that’s targeting the enterprise landscape. We go through the origin story of Cohere, the challenges of building foundational models, and why he believes large language models (LLMs) won’t lead to artificial general intelligence (AGI). We also explore the fierce…

Even if founders do everything right, they may still fail to find PMF. That's why even repeat founders have only 1.5% chance of building a unicorn. We talk about product-market fit constantly in this podcast. Hopefully, we learn from what others did and improve our chances of finding PMF. But there is only one way to guarantee that one day you will…

Don co-founded Vena & was CEO for 8 years. Last month, Vena became a Centaur crossing $100M in ARR. Don & his team launched Vena in a crowded market, where everyone else was trying to replace excel. So they built a budgeting and planning (FP&A) solution that instead leveraged excel. As Don says, they "disrupted the disruptors". Don knew the problem…

It's the first time I see a candidate BS his way through interviews with multiple people, impress each one of them, and ultimately end up being a complete fraud. But the biggest learning wasn't that you should watch out for fraud-- it was that you shouldn't trust interviews nearly as much as you'd think. While fake candidates are rare, candidates w…

Ashutosh is one of those rare founders who founded not just one, but two unicorns. He worked at Google for 4 years, left and started Bloomreach, which was last valued at $2.2B. Halfway through that journey, he left to do it all over again. He started Eightfold AI which is the one we're talking about today. In 2021, he raised $220M from Softbank at …

Carta is the backbone of most venture-backed startups. They have access to specific information about every single round, not just what's reported in TechCrunch. Today, Peter Walker, Carta's Head of Insights joins us to share the findings from Carta's Q2 reports. We go deep into data from pre-seed, seed and Series A rounds. We cover median valuatio…

Last quarter, Sanish raised a $50M Series D. His company has raised over $130M. They have enterprise customers across 14 countries including Dollar General, Aldo, and CircleK. It all started because Sanish was working out of coffee shops. He wasn't looking for a startup idea. But after a few casual conversations with employees, he noticed several p…

Sean Ellis created THE test for PMF. He led growth teams at Dropbox, Eventbrite and LogMeIn, which sold for $4.3B. He coined the term Growth Hacking and wrote the best-selling book Hacking Growth. Today we go deep and tactical with him. He takes us through how to use the Sean Ellis test to perfectly measure and understand product market fit. He tak…

Daniel's been building robots for 20 years. He's sold 100s of AI robots-as-a-service to Walmart, FedEx, & DHL amongst others. Last month, he raised a $40M round. 6 years ago, he realized why robots weren't getting massively adopted. Builders like him were trying to build perfect robots that always worked. But every situation has edge cases. What if…

Advice is free—actioning bad advice isn't. Early-stage founders are bombarded with advice. A lot of it from investors who have never operated a business, never ran marketing, never led sales. And yet, many founders take VCs' advice as sacrosanct. And many VCs feel like they can and should opine on everything. If many people treat you like an expert…

Alex got the co-founder of a public company to join him and raised $6M out of the gate—but it took him 3 years to make his first sale. But after he shifted from selling to SMBs to selling to MSPs (Managed Service Providers i.e., outsourced IT), things took off: April 2015 - $1K MRR August 2015 - $10K MRR June 2016 - $100K MRR Nov 2018 - $1M MRR ($1…

When an employee unexpectedly quits, an investor backs out, or a big customer churns— fear of failure takes over. When you close a new round, land a big customer, or make a big hire— you feel pure excitement. Every founder is on a fear-excitement spectrum. There's no way to prevent yourself from feeling the two extremes. But I've seen great founder…

Pierce launched a consulting business that grew to millions in revenue and dozens of employees. But he noticed his customers kept asking for the same solution. So he launched Knak, an email marketing and landing page builder that integrates to Marketo. Unlike most founders, he didn’t go all-in. He kept working on his consulting business full-time u…

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) a record 59 times. Every founder knows storytelling is a critical skill. But 99% of founders I meet are terrible storyteller…

5 years ago, Shubham had just graduated college and had no network. He bootstrapped to $3M in ARR, then raised $200M & grew to $85M ARR. But he started trying to sell AI for marketing to enterprises with no network. So for 2 months, he'd go to the lobby of a bank and sit there for an hour. He'd wait for the CMO to walk by, just so he could say hi. …

Google is in talks to buy cybersecurity startup Wiz for $23B (a 40x revenue multiple). Wiz is the company that in 2021 announced it grew from $0 to $100M ARR in just 18 months. How did this cybersecurity company grow so fast in a crowded space? How does it get a 40x revenue multiple when FAANG stocks trade at 5-15x? Who are the exceptional founders…

Paul built a startup that was acquired for $2.2B. He worked on AI at Uber and Oculus. But when a farmer told him about some of the problems he was facing, he quit and went all-in on farming. He built a robot that attaches to the back of tractors, uses computer vision to identify weeds and lasers to shoot and kill them. He sells each robot for $1.5M…

Elon Musk single-handedly took on the entire automotive industry. No one, including me, thought he would succeed. But he's built an $800B company. Whether sales are slowing down misses the mark: the punchline is it took well capitalized, professional automakers 15 years to catch up to a single founder. Sure, Elon Musk is special. But this goes beyo…

Last month, Ashby raised a $30M Series C. Ashby is used by customers like Notion, Ramp and Sequoia. Benji built Ashby as an end-to-end Applicant Tracking System (ATS) that would replace several point solutions. He had to build heads down for 18 months and couldn't launch a simple MVP. Surprisingly, even though he raised $3.5M at seed, he didn't gro…

AI startups don’t necessarily have to beat incumbents. Some will start entirely new markets instead. Like Canva to Photoshop, Shopify to Amazon or Pickleball to Tennis, many of these won’t even have to compete. They create 10x easier to use products and through that open up an entirely new space. They solve problems people didn’t even know they had…

"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 and his startup ID.me is worth over $1B. This is the story of how pivoted for a Groupon-like model to …

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 tech revolutions. Unlike mobile, the internet, or the PC revolution, AI is not a new distribution ch…

Andrew spoke with 120+ VCs to raise a $1.5M pre-seed round. He closed $2.7M and had demand for many millions more. He devoted 90% of his time to fundraising, but only took weeks from the first meetings to close. 99% of founders I meet do not fundraise at this level. It takes them longer to close, they have fewer choices and raise less. This is a sp…

Zoom was THE work-from-home stock. It's down 90% from peak. The same hype that fuelled work-from-home stocks is now fuelling AI. What happened to Zoom will happen to many AI companies. AI startups today need to carefully position against foundational models and incumbents. Here's how to think through it. Why you should listen: Learn why what happen…

Chris shares the story of how he grew Refine Labs to $22M ARR, what he did to grow so fast, and also why he regrets spending so much on growth instead of focusing on profitability. He goes exceptionally deep on sales and marketing and provides tactical advice you can steal. Chris is the founder of Refine Labs & Passetto. He's also a LinkedIn Top Vo…

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, positions correctly, lets the bets play out, and goes all-in on what works. Rinse, repeat, rinse, repeat, rinse, repeat. In unde…

We interview Chris Slow the CTO and Founding Engineer at Reddit. Reddit is now a ~$10B company, with nearly $1B in revenue. Their 1B+ monthly active users are so powerful they can move markets. This is the story of how it all began. On this episode, we interview Chris Slowe, Reddit's current CTO and Founding Engineer. Chris was in YC's first-ever b…

Wardah was a PhD graduate working at a biomedical imaging startup. But all it took was two different dentists giving her two totally different diagnoses for her to quit her full-time job. She was unemployed with no idea what to build. All she knew was that something was broken—and she had to fix it. Her startup Overjet is now the #1 dental AI platf…

Dane was the CEO of Squarespace from 2007 to 2011. He grew the company from ~$2M in revenue to ~$15M. He's a multi-time founder with multiple exits. His current startup, Odeko, raised $227M. He takes us through his long journey as a founder of multiple companies and shares the key startup lessons he's learned. Why you should listen: - Why 7-day tri…

His first startup was a cool idea: Uber for Valet Parking. Investors loved it. But the unit economics didn't work out. So he had to pivot. He ended up selling it, but decided to do things differently the second time around. “It’s the boring stuff that makes money. Sometimes the sexy, interesting things are really great ideas, fun to use, but aren’t…

His travel startup crashed 90% overnight. Here’s how he used AI to grow past $2M/year—to $2M a month: For a while, Andrew was crushing it. Accelerator -> $750K pre-seed -> $2M ARR -> $2.5M seed round. Then COVID hit. He was selling to events like CES, SXSW, etc. Revenue dropped from $160K/month to under $10K... overnight. Investors from his seed ro…

Poojan is a multi-time successful founder. He raised $60M for his first startup and exited. He just raised a $75M Series D at his current startup. But it wasn't always easy. - In his first startup, he had to hover beside conference booths for hours to land his first customer. - He gave his product away for free to the first several customers. - It …

Arvind founded 2 billion-dollar startups—by doing everything lean startup tells you not to do. - He didn’t focus on launching an MVP. - He ignored early market feedback. - He didn’t charge beta users anything— for 2 years. And it worked. He went from $0 to $3M in revenue the year he launched publicly. He tripled to about $9M the year after. And tri…

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 to be ephemeral, not recorded for all time. In this episode, we dive deep into how Snapchat went from idea to product-market…

If you feel like the ‘unicorn or bust’ playbook isn’t for you, then this episode definitely will be. Rand Fishkin is a multi-time founder and published author of Lost and Founder. He founded Moz, raised $29M in VC, grew to $50M in revenue and exited for $70M. But he ultimately realized that the VC-backed life wasn’t for him. So he went on to start …

While Voice AI is all the rage now, it wasn't a hot sector in 2017. After Dylan graduated from YC, VCs rejected him. He couldn't raise a round. They all assumed Google would do it. So he raised what he could from angels and made it work for the next 3 years. He's now built the world's most accurate Speech AI model. He's grown to 5,000 customers and…

Andrew is the founder/CEO of Enable. And he is riding a rocket ship: 2020: $17M Series A 2021: $45M Series B 2022: $94M Series C A few months ago he raised $120M at a $1B valuation. But it took him five years from the time he started Enable in 2015 until he was able to raise his first round in 2020. Andrew was running a profitable development shop …

Alex started Apt2B in 2010. He sold couches online before IKEA did. It took him over 3 years to make as much money as he used to as a furniture salesperson. But it paid off. After growing the business to $6M in revenue, he sold the company. Post-acquisition he grew the company to $40M in sales. In this episode, we dive deep into what Alex did to ge…

Every founder wants to build the next $1B+ company. So it’s normal to get inspired by what companies like Apple, Shopify and Microsoft do. But it’s also a huge mistake. In this episode, we look at what Shopfiy, Fullscript and Spellbook did to find product-market fit. In many ways, it’s the opposite of what they do now, as big succesful companies. B…

Spellbook is ChatGPT for lawyers. They've raised $30M in the last 6 months. They now have over 2,000 law firms as customers. But it wasn't a straight line-- it took Scott 6 years to get here. For the first 5 years, Scott worked on a legal tech platform called Rally. During that time, Scott along with his co-founders and their small team ran hundred…

Kyle Braatz is the founder of Fullscript, a $900M revenue company that started by helping health practitioners recommend supplements to their patients. It's like the Shopify for doctors, nurses and nutritionists Even though he captured 50% of the Canadian market in one year, early-stage VCs didn't see the opportunity. So he bootstrapped his way to …

Aydin Senkut is the Founder and Managing Partner at Felicis. He invested in Shopify's Series A in 2010 at a $25M valuation. He joins us to tell the story of how Shopify found product market fit. Shopify is now a $100B company. But as Founder & CEO Tobi Lutke said, in the early days, his goal was "to build a 20-person company". Shopify is not a stor…