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 startup.

Why You Should Listen

• How Sigma went from $0 to $100M ARR—but spent 7 years figuring it out.
• The pivot that turned years of failure into explosive growth.
• Why obsessing over speed to product-market fit is the wrong game.
• How to handle the psychological toll of startup uncertainty.
• The hidden power of building features your customers never ask for.

Keywords

product-market fit, Sigma Computing, pivot, startup growth, business intelligence, Snowflake, early-stage startup, SaaS growth, cloud analytics, founder stories

00:00:00 Intro

00:02:49 Debating speed to product–market fit

00:10:14 Quitting Salesforce and the EIR leap

00:23:12 Two years of prototypes that went nowhere

00:36:53 The Snowflake meeting and spreadsheet pivot

00:45:41 Dealing with Investors

00:52:30 Tripling three years straight to $100M ARR

00:54:46 Why most people shouldn’t start a company

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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 rapid growth and millions raised might not save you.
• Find out the hidden dangers of relying on corporate VCs.
• Learn why equal founder equity splits might not be a good idea.
• Hear the biggest fundraising mistakes early-stage founders make (and how to avoid them).
• Get practical advice on how to truly validate your startup before building tech.

Keywords

startup failure, fundraising mistakes, fintech startup, founder lessons, corporate VC, startup partnerships, product validation, founder equity split, early-stage fundraising, startup growth challenges

00:00:00 Early Days at Uber and Moving into Fintech

00:07:00 Launching a Consumer Fintech App in Europe

00:13:37 Validating Without Tech Building an MVP by Hand

00:19:22 Why US Startup Models Don’t Work in Europe

00:23:07 Raising Money Quickly—and the Hidden Costs

00:28:56 Running Out of Cash When COVID Hit

00:32:15 Tough Decisions Layoffs, Sales, and Shutdown

00:37:53 How Big Partnerships Can Sink Your Startup

00:43:41 Staying Optimistic Even When Everything Falls Apart

00:46:38 Crucial Fundraising Advice for Early-Stage Founders

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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 profitable early was a game-changer, and why the biggest businesses are built by doing fewer things, better.

Why You Should Listen

• How Mercado Libre survived going bankrupt by pivoting overnight.
• Why most startups die chasing growth—and what to do instead.
• How to build unstoppable momentum by nailing one thing first.
• The simple test to know if your startup has real product-market fit.
• The one thing all $100B companies do differently.

Keywords

Mercado Libre, product market fit, Hernan Kazah, startup advice, ecommerce growth, marketplace strategy, profitability, venture capital, early-stage startups, Latin America startups

00:00:00 Intro

00:04:07 Why We Chose the eBay Model

00:08:56 The Early Hack That Got Us Our First Users

00:14:23 Raising Money at the Worst Possible Time

00:21:37 Becoming Profitable and Going Public

00:26:34 How Mercado Libre Stayed Patient While Competitors Chased Growth

00:34:05 Why We Expanded Across Latin America From Day One

00:45:11 Our Secret to Winning Against Better-Funded Competitors

00:50:04 The Most Important Advice for Early-Stage Founders

00:52:16 Why AI is Different From the Internet and Mobile Revolutions

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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 silver‑bullet fantasies. Perfect fuel for scrappy founders hunting product–market fit.

Why You Should Listen

• The single‑metric focus that took a travel app to $10M ARR through Covid
• Turning six months of “no’s” into $100M ARR: the slow‑burn playbook
• Why mastering your craft first can unlock your next billion‑dollar idea
• Picking the rules to break: using “unconventional” as an unfair advantage

00:00:00 Intro

00:01:30 Why location odds matter less than you think

00:02:50 Skip the Dishes proves huge wins can start in tiny markets

00:05:30 Polarsteps shows what happens when one metric rules them all

00:09:00 Jobber’s decade‑long slow burn to compounding growth

00:14:40 Public.com and the power of diving deep into your craft

00:21:40 The real skill: knowing when to ignore conventional wisdom

00:24:30 Key takeaways and next steps for your own playbook

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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 your blueprint.

Why You Should Listen

• How to pivot from a dead-end idea to $10M ARR in one year.
• The power of solving a 10/10 burning pain.
• When customer anger becomes your biggest growth signal.
• Why chasing local maxima can trap your startup.
• How true conviction unlocks explosive growth.

Keywords

product-market fit, startup pivot, explosive growth, voice AI, founder stories, SaaS startups, early-stage startups, customer pain points, San Francisco startups, developer tools

00:00:00 Intro

00:02:35 Stuck at $500K ARR & Burning the Boats

00:07:15 Knowing When It’s Time to Quit

00:08:49 The Side Project that Became Vapi

00:16:28 Early Growth and Finding First Customers

00:23:32 The Product Hunt Launch that 3X’d Growth

00:27:57 Surviving Explosive Growth

00:35:17 Competing Against OpenAI and Big Tech

00:41:26 How to Identify a True 10/10 Pain

00:48:53 The Moment of Real Product-Market Fit

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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.

Why You Should Listen

• Learn exactly what top founders did to get from zero to $100M ARR
• Why chasing perfection won't work (and how to stop)
• The secret to surviving brutal fundraising rejections (over 60 VCs said no to Kyle)
• Why hustle culture isn’t enough—here’s what matters more

Keywords

product-market fit, startup fundraising, unicorn startups, founder hustle, lean startup method, scaling startups, early-stage growth, AI startups, SaaS growth, venture capital advice

Chapters

(00:00:00) Intro

(00:02:05) Quitting a Unicorn to Start Again

(00:05:09) From NSA Hacker to Startup Founder

(00:09:18) Ignoring the Lean Startup

(00:12:59) Knowing When to Launch

(00:16:32) Finding Product Market Fit

(00:18:01) Final Advice for Founders

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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, and why the biggest opportunities are hiding in the “smallest” problems. If you’re an early-stage founder looking for practical insights, game-changing growth hacks, and lessons from someone who’s been through it all, this is the episode you can’t miss.

Why You Should Listen

• Learn how Avery grew Tailscale from zero to millions in revenue purely through word-of-mouth.
• Discover why chasing enterprise deals too early might actually slow you down.
• Find out why solving “small, simple” problems can lead to billion-dollar outcomes.
• Hear the counterintuitive reason why your product failing early users is actually a huge advantage.
• Understand how Tailscale turned COVID lockdown into an explosive growth opportunity.
  
  

Podcast Keywords
product market fit, startup growth, product-led growth, Tailscale, word-of-mouth growth, startup fundraising, developer tools, network security, B2B SaaS, early-stage founder advice

(00:00:00) How Tailscale Raised $160M Without Chasing Investors

(00:01:48) Building a Billion-Dollar Idea From Scratch

(00:05:18) How to Find Real Problems Worth Solving

(00:13:14) Landing the Critical First Customer

(00:22:25) Why Great Founders Start Small, Not Big

(00:28:33) Turning Bottom-Up Adoption into Enterprise Deals

(00:36:55) Growing from Zero to $1M+ ARR Through Word-of-Mouth

(00:46:16) When Avery Knew Tailscale Had Product Market Fit

(00:48:27) Avery’s Most Important Advice for Early-Stage Founders

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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 news, tech layoffs, Theranos lessons

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