• He "kind of" had PMF for 8 years—until, after a rebuild, he grew 10x to $25M ARR. | Ben Alarie, Founder of Blue J
    Oct 20 2025

    Ben Alarie spent 8 years building Blue J with "partial product market fit"—real customers, real revenue, but no real market pull. Then he made a bet that would either kill the company or 10x it: he put the existing product in maintenance mode and gave his team 6 months to rebuild everything from scratch using a technology that barely worked.

    Two years later, Blue J went from $2M to $25M in ARR. They're adding 10 new customers every single day. NPS went from 20 to 84.

    This isn't a story about getting lucky. It's about a founder who knew—with absolute conviction—that the market would eventually arrive, and made sure he was ready when it did. But it's also about the danger of fooling yourself into thinking you have PMF when you only "kind of have PMF."

    Why You Should Listen:

    • Learn the brutal difference between fake and real PMF
    • Discover when to abandon millions in existing ARR to go all-in on something else
    • Why "time to value" might be the single most important metric for word-of-mouth.
    • See what it takes to survive until the market is ready.

    Keywords:

    startup podcast, startup podcast for founders, product market fit, founder journey, early stage startup, startup pivot, AI startup, SaaS growth, founder advice, hypergrowth startup

    Chapters:

    (00:02:00) Starting BlueJ
    (00:9:26) Introducing AI to Tax Research
    (00:12:44) Starting to Build
    (00:17:03) Not Having True PMF
    (00:19:44) Believing in Retrieval Augmented Generation
    (00:25:34) Updating to V2 of BlueJ
    (00:30:58) The Necessity of Time to Value
    (00:33:47) When You Knew You Have PMF
    (00:38:19) One Piece of Advice

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    41 mins
  • They failed every POC—then grew their cybersecurity platform to $100M ARR in 5 years. | Dean Sysman, co-founder of Axonius
    Oct 16 2025

    Dean thought he'd have to bootstrap Axonius because no investor would fund a solution to a problem that had existed for 20 years. He was wrong—they've raised $500M.

    The breakthrough came when a Fortune 500 company was actively being hacked by Chinese state actors. Their first customer almost said no—they had 20 bugs during the POC. But Dean's team fixed each one within 48 hours while their competitors took quarters to respond. That speed changed everything.

    They went from zero to $100M ARR in under 5 years, created an entirely new category (cyber asset management), and achieved an NPS score in the 80s—unheard of in cybersecurity.

    His framework for the three types of enterprise journeys will change how you think about positioning.

    Why You Should Listen:

    • Why responding to customer issues in hours changes everything.
    • How to turn a "dormant pain everyone accepts" into a $500M+ company.
    • Why speed beats everything.
    • The 3 types of enterprise software journeys and which one VCs won't fund.

    Keywords:

    startup podcast, startup podcast for founders, Axonius, Dean Sysman, cybersecurity startup, enterprise sales, Unit 8200, cyber asset management, B2B SaaS, YC alumni

    00:00:00 Intro

    00:02:25 From Hacker to CyberSecurity

    00:14:46 The three types of enterprise software journeys

    00:18:41 Why time to value beats everything

    00:29:33 Thought they'd bootstrap but VCs validated the problem

    00:35:14 Failed POCs and landing first customer with 20 bugs

    00:40:10 Zero to $100M ARR in under 5 years

    00:45:24 When to know you have product-market fit


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    49 mins
  • He tested his pitch on Uber drivers—then built a cybersecurity platform to $180M raised. | Casey Ellis, Founder of Bugcrowd
    Oct 13 2025

    Casey turned hackers into a marketplace and built Bugcrowd to $180M+ raised. But the real story isn't about cybersecurity—it's about how he validated a two-sided marketplace with almost no product, refined his pitch by literally testing it on Uber drivers until it clicked, and cracked the code on category creation when everyone thought hackers were the enemy.

    You'll learn about the exact moment he knew he had product-market fit, why he blew every pitch to top VCs until he reframed his vision, and how giving away 500 t-shirts did more for growth than any paid marketing.

    If you're building a marketplace, creating a category, or just trying to figure out how to explain what you do—this is required listening.

    Why You Should Listen:

    • Master the 30-second Uber pitch test—Casey's framework for refining your message until anyone gets it.
    • Learn why problem-solution fit without product-market fit is worthless
    • Validate your marketplace with $500 and no code
    • Why your network is your only real asset pre-Series A
    • The surprising ROI of early brand marketing

    Keywords: startup podcast, startup podcast for founders, marketplace startup, go-to-market strategy, product-market fit, category creation, B2B sales, early-stage fundraising, founder pitch, cybersecurity startup

    00:00:00 Intro

    00:01:36 From white label pen testing to the Bugcrowd idea

    00:18:58 Testing with MailChimp and 5000 hackers signed up

    00:21:46 Landing Google as customer in month four

    00:24:24 Blowing every pitch meeting in Silicon Valley

    00:33:21 The Uber pitch technique for simplifying the message

    00:36:57 Early go-to-market tactics and hitting $1M

    00:43:37 Open heart surgery and stepping back as CEO

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    49 mins
  • He quit Google & his 1st startup failed—but his 2nd grows at $1M ARR every 10 days. | Zach Llyod, Founder of Warp.dev
    Oct 9 2025

    Zach spent 8 years at Google leading engineering for Google Docs, then left to build a photo sharing app with zero go-to-market plan.

    Reality hit hard: "At Google, anything you launch gets millions of users. At a startup, the challenge isn't building—it's getting anyone to care." After writing a brutal postmortem documenting everything that went wrong, he started Warp with strict principles: only hire product-obsessed people, document every process, build pure software not services.

    For three years, Warp had hundreds of thousands of free users but no revenue. Then they pivoted to AI-powered development in 2024. Here's how they went from taking 300 days to hit their $1M to now adding $1M ARR every 10 days.

    Why You Should Listen:

    • Why working at Google can set you up to fail as a founder
    • How to know when to quit your own startup
    • Why you should write down every operating principle before starting
    • The shift he made to grow insanely fast
    • Why competing directly with fast-growing startups is actually smart

    Keywords:

    startup podcast, startup podcast for founders, Warp, Zach Lloyd, Google alumni, developer tools, AI coding, product-market fit, startup pivot, Series B

    00:00:00 Intro

    00:01:48 From law school to Google via Craigslist

    00:05:01 Why Google makes you a terrible startup founder

    00:10:36 Joining SelfMade as technical co-founder

    00:19:00 Writing a brutal post-mortem of the startup experience

    00:27:15 Building Warp and getting 10,000 signups day one

    00:38:08 Raising $50M Series B with zero revenue

    00:41:50 Pivoting to Agent Mode and AI development

    00:46:27 From 300 days to $1M to adding $1M every 10 days








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    49 mins
  • He tried to return $200K to investors 30 days in—then exited to Microsoft 5 years later. | Alex Sherman, Founder of Bluefish AI
    Oct 6 2025

    Alex had $2,000 in his checking account when Microsoft acquired his last company. For years, he paid himself $30K while his friends made six figures at corporate jobs. He had only 2 months of runway for 18 straight months.

    Then retail media exploded and everything changed—he went from grinding against the current to riding a wave.

    After selling to Microsoft, he took 6 months off, got bored, and started Bluefish AI with the same team. This time they called Fortune 500 CMOs before building anything.

    His #1 advice for early-stage founders: Get on the plane. And go meet your customers. You'll be shocked by how big a difference that makes.

    Why You Should Listen:

    • How to survive on 2 months of runway indefinitely
    • How to validate your next startup before writing any code
    • Why second-time founders often have more blind spots than first-timers

    Keywords:

    startup podcast, startup podcast for founders, PromoteIQ, Microsoft acquisition, Alex Bluefish, retail media, product-market fit, MarTech, enterprise sales, second-time founder

    00:00:00 Intro

    00:01:58 From management consulting dreams to startup world

    00:04:44 Trying to return $200K to investors after 30 days

    00:07:19 Pivoting through iterations to find retail media

    00:12:13 Finding product-market fit like a river reversing

    00:21:28 Microsoft acquisition with $2,000 in the bank

    00:24:30 Post-exit sabbatical and starting Bluefish

    00:35:08 Building for AI marketing with Fortune 500 design partners

    00:43:12 Always get on the plane

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    45 mins
  • A drug dealer threatened to kill him—then he grew 50x in 3 Years to $50M ARR. | Brett Carlson, Found of ServiceUp
    Oct 2 2025

    Brett had a drug dealer's car for 13 days. By day 11, the death threats started coming. This is the reality of building ServiceUp, the "DoorDash for auto repair."

    Brett literally stole DoorDash's entire playbook—city launches, three-sided marketplace, everything—but discovered even if he got 90% right, 10% of B2C customers can end you.

    He raised from Tiger just as the firm exploded. The DoorDash partnership that seemed like salvation turned into their worst nightmare. But then they pivoted to B2B and saw their average order value grow 5x overnight.

    "Work-life balance is BS. If you can work seven days a week, you'll fail faster, fix faster, and find product-market fit faster."

    Why You Should Listen:

    • Why just 10% of your customers can destroy your business
    • How to close funding in the middle of a macro crisis
    • Why work-life balance is BS if you want to build something big
    • How stealing another startup's playbook can lead to 5000% growth
    • Why your worst customers might actually show you your best pivot

    Keywords:

    startup podcast, startup podcast for founders, ServiceUp, Brett Carlson, marketplace startup, B2B pivot, Tiger Global, auto repair tech, fleet management, startup growth

    00:00:00 Intro

    00:01:40 Failed auto shop becomes ServiceUp idea

    00:03:27 Pulling co-founder out of retirement

    00:09:30 Raising $2M seed from angels

    00:13:23 Building the MVP in Puerto Rico

    00:15:01 Early Bay Area operations and getting shops

    00:17:50 The drug dealer death threat incident

    00:21:17 Tiger Global loses $8B during Series A

    00:26:57 DoorDash partnership disaster

    00:28:36 Pivoting from B2C to B2B fleets

    00:30:00 Finding product-market fit

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    33 mins
  • He pitched 100 VC and spent 3 years building— then grew to $7B AUM. | Doug Scott, Founder of Ethic
    Sep 29 2025

    Doug spent 3 years building technology before landing real customers. While other startups were growing fast, Ethic was stuck at $5M AUM after two years. Until he found a way to help his customers help them WIN new clients they couldn't land before.

    That single shift took them to $250M AUM in one year. He reveals why he left investment banking in Australia, sold everything, and moved to the Bay Area within three weeks with no idea what company to start.

    He pitched over 100 investors to raise early rounds, survived years of building with no traction, and discovered the enterprise sales playbook that unlocked distribution in wealth management. Today Ethic manages $7B and has raised.

    "If I knew how difficult it would be, maybe I wouldn't have done it." This is the reality of building a decade-long overnight success.

    Why You Should Listen:

    • Why helping customers win new business is the killer ROI
    • How to survive a 3-year build phase when everyone else is growing fast
    • Why you should pitch 100+ investors even if only 5 will say yes
    • How to figure out distribution and go-to-market
    • Why the best value-add investors never pitch their value-add

    Keywords:

    startup podcast, startup podcast for founders, Ethic, Douglas Scott, wealth management, ESG investing, fintech, B2B2C, Series A, distribution strategy

    00:00:00 Intro

    00:01:47 What Ethic does

    00:08:15 Leaving Australia for Bay Area with no plan

    00:17:06 The breakthrough for 5x YoY growth

    00:29:42 Three years building with no traction

    00:38:36 Distribution partnerships unlock growth

    00:42:44 Finding product-market fit

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    45 mins
  • PMF Observations: Speed is the only startup moat—& why most founders lose it.
    Sep 25 2025

    Arnold Schwarzenegger mastered three completely different fields—bodybuilding, acting, and politics—with one simple philosophy: reps, reps, reps. This solo episode reveals why speed of execution is the only real moat for early-stage founders.

    One founder takes an idea from conception to signed customers in three weeks. Another takes six months. They both had equally good ideas, but one got 100 reps in a year while the other got 10. Even Twitter, an established app, became top 5 in the App Store not through one or two big changes but 300 small iterations.

    Teams naturally slow down over time. You used to ship in days, now it takes months. You have more engineers but move slower. This episode breaks down why this happens and how to maintain that day-one velocity even at $10M ARR.

    Why You Should Listen:

    • Why speed is the only moat early-stage founders actually have
    • How to get 100 reps while your competitor gets 10
    • Why MVPs shouldn't stop after you have a product in market
    • How Twitter went top 5 in the App Store with 300 tiny changes
    • Why teams naturally slow down and how to fight it

    Keywords:

    startup podcast, startup podcast for founders, startup speed, MVP strategy, iteration cycles, product development, founder mode, execution velocity, startup growth, early-stage strategy

    00:00:00 Intro

    00:00:32 Arnold Schwarzenegger and reps, reps, reps

    00:02:18 Speed as the only moat for early-stage founders

    00:03:48 Why founders lose MVP mentality after launch

    00:09:22 How to stay in Jeff Bezos' day one








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    11 mins