Rob Woollen, founder of Sigma Computing, shares the unfiltered reality of going from 0 to $100M ARR. After spending seven years grinding without product-market fit, Sigma finally hit an inflection point—tripling revenue year over year. Rob dives deep into the pivots, setbacks, and critical decisions that turned early failure into a massive success. If you’re an early-stage founder feeling stuck, this episode will show you how patience, resilience, and radical product decisions can transform your...
Jun 30, 2025•56 min•Season 4Ep. 52
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 backfire spectacularly, how a seemingly successful startup can quietly fall apart, and how to set yourself up to avoid common but deadly fundraising mistakes. This isn’t just another success story; it’s a real guide on how not to fail. Why You Should Listen Discover why even rapi...
Jun 26, 2025•50 min•Season 4Ep. 51
How do you build a $100B business without hypergrowth or endless funding rounds? Hernan Kazah co-founded Mercado Libre, the Latin American ecommerce giant, at the peak of the dot-com bubble. But when the market crashed, funding disappeared, and competitors doubled down on spending, Mercado Libre focused relentlessly on building a rock-solid, profitable core product—ignoring pressure to chase faster growth. Hernan shares how they turned extreme constraints into a secret weapon, why getting profit...
Jun 23, 2025•57 min•Season 4Ep. 50
Four founders prove you don’t need Silicon Valley, a technical degree, or a massive seed round to build a massive company. We go through the key observations from the last 4 episodes: How Skip created a $200M business in a third tier city, Polarsteps’ NPS‑obsessed rise, Jobber’s decade‑long compounding engine, and why a small decision was key to Public.com’s huge success. You’ll learn when to ignore best practices, how to choose one north‑star metric, and why slow, relentless improvement beats s...
Jun 19, 2025•28 min•Season 4Ep. 49
Jordan Dearsley spent 3 years building a startup stuck at $500K in revenue—then he burned it all down and moved to San Francisco. A year later, he was at $10M ARR. This episode walks through Jordan’s decision to abandon a profitable business, why solving a painful customer problem was the key to explosive growth, and how finding product-market fit is as simple—and as brutally difficult—as discovering a 10/10 burning pain. If you’re a founder struggling to find breakout growth, this episode is yo...
Jun 16, 2025•51 min•Season 4Ep. 48
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 lessons on fundraising, product-market fit, and why relentless hustle alone won’t save you. If you’re a founder chasing growth, stop everything and listen...
Jun 12, 2025•19 min•Season 4Ep. 47
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 everyday developer headaches. Learn why your startup idea is probably wrong (and why that’s okay), how Tailscale found explosive product-market fit, a...
Jun 09, 2025•51 min•Season 4Ep. 46
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. Keywords startup scams, OpenAI Johnny Ive, Elizabeth Holmes, Builder AI scandal, tech IPO crash, AI job loss, crypto meme coin fraud, venture capital...
Jun 05, 2025•29 min•Season 4Ep. 53
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-earned lessons on recognizing true product-market fit, leveraging internal tools as a market wedge, and surviving the chaos every early-stage founder faces...
Jun 02, 2025•57 min•Season 4Ep. 44
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 having a plan, why slow initial growth might be your secret weapon, and how true passion gives you staying power. Why You Should Listen How to prioriti...
May 29, 2025•20 min•Season 4Ep. 43
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 stepping away from his comfort zone as an introverted developer was the key to scale. If you’re an early-stage founder trying to nail pricing, distributio...
May 26, 2025•55 min•Season 4Ep. 42
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 rounds make you even less likely to raise an A. And why seed-strapping might be an answer for many founders. VCs read and understand all this data. If ...
May 22, 2025•48 min•Season 4Ep. 41
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 and explosive organic growth. This episode dives deep into Kazi’s playbook: when to ignore customer interviews, how to pivot on a dime, and why getti...
May 19, 2025•45 min•Season 4Ep. 40
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 a $25M cash cow by solving one overlooked customer pain point. Plus, and how Cleerly used a 17 day-from- bankruptcy moment as its turning point. Why Y...
May 15, 2025•18 min•Season 4Ep. 37
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 quickly. He explains the mindset shift needed to nail product-market fit multiple times and why you should only tackle timeless problems if you want your...
May 12, 2025•55 min•Season 4Ep. 38
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 headlines. This is different than our normal episodes— definitely a much lighter twist, to be taken with a grain of salt. Let us know what you thin...
May 08, 2025•40 min•Season 4Ep. 37
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 rejection, maxing out credit cards, and nearly quitting. You’ll learn why there are rarely any “silver bullets”, how he handled relentless investor skepticis...
May 05, 2025•53 min•Season 4Ep. 36
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 obsessing over a single metric: NPS. If you’re an early-stage founder deciding where to focus, this is your must-listen episode. ___ Why You Should L...
May 01, 2025•47 min•Season 4Ep. 35
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 also shares hard-won lessons on managing burnout, dealing with near-failure, and creating a company culture that lasts. It’s packed with practical insi...
Apr 28, 2025•40 min•Season 4Ep. 34
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’s doing $10M in revenue, profitable, with just 10 employees. He shares every bold tactic—bundling random AI packs, hacking Google rankings, landing a...
Apr 24, 2025•53 min•Season 4Ep. 33
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 how Mike ditched vanity metrics, found sustainable traction, and grew ButcherBox past $500M in revenue—with no outside funding. ____ Why You Should L...
Apr 21, 2025•55 min•Season 4Ep. 32
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 your process faster, more targeted, and a lot less painful. ___ Why You Should Listen 1. The 2-minute test for "real" pre-seed investors – Spot VCs who ...
Apr 17, 2025•36 min•Season 4Ep. 31
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 universal insurance coverage, and coping with near-burnouts. If you’re a founder navigating hyper-regulated markets, Jim’s journey is the blueprint. ____ Why ...
Apr 14, 2025•43 min•Season 4Ep. 30
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 this episode, Adam reveals why he ignored “scalable hacks” until his product proved undeniable, the two keys that finally unleashed product-market fit...
Apr 10, 2025•52 min•Season 4Ep. 29
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 $15M valuation. Just two years later, he not only grew right back to a $575M valuation, he also doubled revenue from its previous peak to $400M. This ep...
Apr 07, 2025•45 min•Season 4Ep. 28
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-step playbook, including how to structure 3-month pilots for fast feedback, craft DMs that actually get replies, and pick the right content “waterin...
Apr 03, 2025•48 min•Season 4Ep. 27
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, hype. Why You Should Listen Why you need to spend most of your time fundraising. Learn exactly how to fake traction, drive FOMO and raise millions--...
Apr 01, 2025•39 min•Season 4Ep. 26
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 sabotage new users. He’ll show you why some sales-led companies die when they try freemium, how to carve out a simpler “first strike” moment, and the ...
Mar 27, 2025•41 min•Season 4Ep. 25
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 in Toronto, backed by billions in funding , he thought it was over. Instead, Skip became Canada’s dominant food delivery platform and got acquired...
Mar 24, 2025•1 hr 1 min•Season 4Ep. 24
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 excellent leading indicator of PMF. Why NPS is not as good as Sean Ellis test to measure product-market fit. Why retention is the best long-term metric, but t...
Mar 20, 2025•28 min•Season 4Ep. 23
