Stéphan bootstrapped AODocs to $55M in revenue and 250 employees without taking a dime of VC money—while competing directly with venture-backed competitors. Starting as a services company in 2012, he spotted the cloud migration wave early and built document management for enterprises moving to Google Workspace. 

In this episode, Stéphan breaks down why doubling every two years beats hypergrowth, how to win enterprise deals with zero funding, and why touching business-critical documents means year-long sales cycles but 10-year retention. This is the anti-Silicon Valley playbook that actually works.

Why You Should Listen:

• Why the founder must personally close every single deal in 0 to 1
• How doubling every 2 years (not every year) creates a more stable business
• The brutal reality of enterprise POCs: doing it for free before getting paid
• Why you can't have both fast customer acquisition and high retention
• How being French/European became an advantage against US competitors 

Keywords

AODocs, bootstrapping, Stéphan Donzé, enterprise sales, document management, SaaS, Google Workspace, cloud migration, product market fit, B2B

00:00:00 Intro

00:01:12 Bootstrapping vs VC backed

00:03:44 From services to SaaS

00:19:08 Landing the first customer 

00:20:47 Why they turned down VC money

00:25:32 The 997 grind—four days on-site with customers every week

00:35:21 Why you can't have fast sales and high retention

00:40:33 Product-market fit

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Andrew bootstrapped Wrike and grew it from 0 to a $2.2B exit by doing the exact opposite of what every startup book tells you. No pivots. No talking to customers before launch. No narrow niche. Just 17 years of relentless focus on one problem while everyone else was pivoting every 18 months. 

In this episode, he breaks down exactly why bootstrapping saved his company (and why VC would have killed it), why he ignored customer development and just built in a bunker, and how manning the support phones himself became his secret product development weapon. 

Now building Zencoder (AI coding agents), he shares why the future isn't about replacing developers but making every human "superhuman" at their job. This is mandatory listening for any founder questioning conventional startup wisdom.

Why You Should Listen:

• Grew to $2.2B with no pivots for 17 years while competitors kept "failing fast"
• How he doubled revenue every year from $0 to $100M+ ARR
• Why manning support phones himself was better than any customer development process
• Why copycats helped Wrike grow faster
• The future of AI agents

Keywords:

Wrike, Andrew Filev, bootstrapping, 2 billion exit, product market fit, SaaS, Zencoder, AI coding agents, no pivot strategy, collaboration software

00:00:00 Intro

00:03:30 Moving to Silicon Valley from Russia to build for millions

00:10:06 Going all-in after previous side projects failed

00:11:27 Why he never pivoted once in 17 years

00:18:47 Launching without talking to customers first

00:24:12 Manning support phones and discovering the real roadmap

00:29:01 When Microsoft Project, Basecamp, and Jira were the competition

00:34:31 The only job definition—double the business every year

00:54:16 Why Developers won't be replaced, and become superhuman

01:01:57 The $2.2B exit and making employees' dreams come true

01:04:36 Finding product-market fit at Zencoder vs Wrike

01:06:55 Focus on people—everything traces back to them

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Peter Walker from Carta drops the hard data every founder needs. Based on actual cap table data from 1000s of startups, this Q2 update reveals the brutal new reality.

It takes 2+ years to go from seed to A (up from 1.6), you need 3X the revenue you used to, and if you're not AI, you're getting half the attention. 

But there's good news too—teams are finally getting leaner, exits are picking back up, and the worst of the funding winter might be behind us. 

If you're raising in 2025, this is your reality check.

Why You Should Listen:

• $3M ARR is the new Series A bar—& it takes 1 in 4 founders 3.5+ years to get there
• Half as many seed deals are getting done but at 20% higher valuations—you're either in the AI club or you're out
• Founders own just 56% after their first priced round and only 10% by Series D—every round costs more than you think

Keywords:

Carta data, Series A requirements, startup fundraising 2025, seed to Series A timeline, ARR benchmarks, AI startup valuations, bridge rounds, founder dilution, startup team size, venture capital trends

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Hedra CEO Michael Lingelbach breaks down how his generative video app went from zero to millions of users and an eight-figure run rate in months — then deliberately slowed down to rebuild a V2 that enterprises would pay for. We dig into the prosumer-to-pro upsell, why free users are a false signal, and how a creator-seeded launch can outpull ad spend. 

Michael shares the GTM that signs enterprise contracts every few days with no outbound, the exact moment he killed feature churn to ship a real workflow, and what to hire (and fire) in the first 10 people. If you’re building AI or any early product, this is a must-listen blueprint on getting from hype to revenue.

• How Hedra hit an 8-figure run rate in months — with a prosumer → enterprise wedge
• The “free user” trap: why signups ≠ demand and how to price for pain
• When to pause growth to build V2 that actually sells (workflow > tech demo)
• A creator-led launch playbook that drives virality without paid influencers
• Hiring early: bring in a talent lead fast, staff for speed, survive co-founder changes

AI video, generative AI, product market fit, Hedra, Michael Lingelbach, creator tools, PLG, enterprise SaaS, go to market, startup growth

00:00:00 Intro

00:02:25 Why he built his own proprietary models

00:10:19 Target use cases faceless channels marketers podcasts

00:15:31 Early hiring lessons

00:38:00 Free vs paid

00:51:03 V2 launch and shift to enterprise 

00:53:46 Hitting eight figure run rate and scaling GTM

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Ross went from lawyer to self-taught engineer to CTO at a 1,600-person unicorn—then quit to build Wordsmith AI. 

In 18 months, he's raised $30M and grown to mid-single-digit millions in ARR by doing everything differently. He tested co-founders by starting fights. Built in Slack for 10 months before adding a web interface. Kept his team at 8 people while competitors hired dozens. 

This episode breaks down his exact playbook: how to test co-founders before committing, why attacking someone's core job kills your sales cycle, and how he accidentally created the hottest seed round by ghosting every VC. Plus the reality of building a rocket ship with a newborn at home.

Why You Should Listen:

• Why starting fights with co-founders can be a great way to test conflict.
• Why keeping your team at 8 people until PMF lets you move faster
• The accidental fundraising playbook that made VCs go crazy
• How having a baby forces you to be 10x more productive as a founder

Keywords:

Wordsmith AI, Ross McNairn, AI legal tech, product market fit, co-founder selection, Series A, Index Ventures, Slack integration, startup pivots, legal AI

00:00:00 - Intro

00:01:31 - From Lawyer to CTO

00:03:45 - Starting Wordsmith AI

00:06:41 - Testing Co-Founder Relationships

00:14:42 - Building the MVP

00:20:44 - First Product Iterations

00:26:39 - Finding Product Market Fit Through Slack

00:37:42 - Go-to-Market Using Webinars and Influencers

00:47:00 - Balancing Startup Life with a 10-Month-Old Baby

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Rick built Persona into a $100M+ ARR unicorn, but he never thought it would work. In fact, Rick started Persona believing it would probably fail, and that mindset might be exactly why it succeeded. 

In this episode, Rick reveals how a casual project with zero expectations turned into a billion-dollar business, why early-stage startups should avoid hyper-optimization, and the secrets he learned at Square about identity fraud that became his breakthrough. 

If you want to challenge the typical startup narrative, this one’s a must-listen.

Why You Should Listen

• How Rick Song took Persona from $0 to $100M ARR without believing in product-market fit.
• Why obsessing over optimization might be killing your startup.
• How to think differently about fundraising—Rick raised $2.4M without even trying.
• The real truth about what decisions actually matter in your early days.

Keywords

product market fit, startup advice, early-stage founders, fundraising, hyper-optimization, identity fraud, Persona, Rick Song, Square, founder mindset

00:00:00 Intro

00:08:07 Finding Persona’s First Customer

00:17:56 How to Quit a Successful Job for a Risky Startup

00:26:54 Early Product Strategy

00:37:40 Hiring the First Employees Without Selling the Dream

00:47:54 Fundraising Without Even Trying

00:56:55 Hyper-Optimization is Hurting Your Startup Decisions

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Neil Patel just flipped everything you know about startups upside down. He says product-market fit is overrated, giving away your software for free can make you rich, and the real secret to scaling isn’t charging customers—it’s monetizing the leads your free product generates. 

Neil breaks down his playbook on how startups can leverage free products to grow exponentially, why your churn doesn’t matter if you monetize correctly, and the reality about brand building that most founders completely miss. This episode challenges conventional startup wisdom and reveals a totally different way to think about building billion-dollar businesses.

Why You Should Listen

• Why Neil Patel thinks chasing product-market fit is a waste of your time.
• How offering your software for free can create a viral growth engine.
• How to monetize without charging for your product.
• Why branding matters, but why you’ll have to wait 10 years to feel it.

Keywords

Neil Patel, product market fit, SaaS growth, freemium model, lead generation, churn reduction, monetization strategy, startup branding, digital marketing, SaaS startups

00:00:00 Intro

00:07:05 The Secret Math Behind Giving Software Away for Free

00:21:32 How Free Software Can Disrupt Billion-Dollar Industries

00:26:26 The Truth About Branding (and Why It Takes 10 Years)

00:29:59 Neil’s Final Advice to Early-Stage Founders

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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, virality, and content to get millions of views—and millions in ARR. You’ll learn why Roy intentionally designs content to spark outrage, how he leveraged Twitter to raise millions from top VCs within 24 hours, and his tactical advice for mastering the short-form algorithms that dominate attention today.

 If you want an unfair advantage to scale your startup, this is a must-listen.

Why You Should Listen

• How Roy Lee mastered viral marketing to scale from 0 to $5M ARR in 3 months.
• Why controversy and shock value are the ultimate distribution hacks.
• Exactly how Roy raised $5M in 24 hours by leveraging Twitter virality.
• Why short-form content is the most underrated growth channel for startups today.
• The secret to X/Twitter's algorithm.

Keywords

Roy Lee, Cluely, viral marketing, startup growth, product market fit, AI startup, raising venture capital, short-form content, going viral, Twitter strategy

00:00:00 Intro

00:02:20 Getting Kicked Out of Harvard and Columbia

00:10:31 How Roy Engineered His Viral Moment

00:17:23 Launching Cluely and Hitting $5M ARR in 3 Months

00:20:49 Secrets to Mastering the Twitter Algorithm

00:28:21 The Formula Behind Virality

00:38:31 Leveraging TikTok, Instagram, and an Army of Creators

00:44:06 Retention Challenges and Future Product Vision

00:50:50 Roy’s Advice for Early-Stage Founders

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Mary Beth Snodgrass shares the raw and real story behind Healthiby—an innovative healthcare startup that succeeded in delivering measurable health outcomes but ultimately failed commercially. Hear firsthand what went wrong, from unclear payer dynamics and sales friction, to macroeconomic shifts and storytelling gaps. This episode pulls back the curtain on why having a working product isn’t enough and why mastering the market dynamics is crucial to your startup’s survival.

Why You Should Listen

• Learn why even successful products can fail if the payer isn’t clearly defined.
• Understand the hidden hurdles in long sales cycles.
• Discover why storytelling and personal founder journeys are key.
• See how market timing and macro changes can dramatically impact your startup’s trajectory.
• Avoid the pitfalls of focusing solely on solving problems without a robust go-to-market strategy.

Keywords

product market fit, healthcare startups, startup failure, go-to-market strategy, founder advice, chronic conditions, startup storytelling, B2B sales, health tech, behavior change

00:00:00 Intro

00:03:04 Pivoting Fast

00:06:16 Finding Initial Users

00:08:53 Building a Behavior Change Product

00:13:55 Why We Failed

00:17:48 Navigating Complex Sales Models

00:19:56 Key Lessons

00:22:45 Final Advice for Early Stage Founders

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Tanay started coding at 10, built a product with millions of users by 11, and never stopped. In this episode, he shares how he created Wispr Flow—one of the fastest growing AI startups today. He's built the world's best voice to text app. I use it myself every single day. And he just raised a $30M Series A from Menlo Ventures 

This is a must-listen for any founder obsessed with building something users can’t live without.

Why You Should Listen

• How Tanay built one of the world’s first voice assistants at 11—and what it taught him about startups.
• Why most founders get product-market fit wrong 
• The critical mistake that almost killed Wispr AI
• The one thing Tanay wishes he’d known about building a startup team five years ago.

Keywords
product market fit, AI startup, Wispr Flow, Tanay Kothari, founder stories, startup pivot, voice interface, building teams, hyper-growth startup, deep tech startup

00:00:00 Intro

00:07:22 Learning to Code in Secret

00:13:27 From New Delhi to Stanford and Silicon Valley

00:17:34 Feather X—Tanay’s First Big Startup Exit

00:24:33 The Original Moonshot Vision of Wispr AI

00:31:19 Why Wispr AI Had to Pivot

00:38:32 The Power of Incremental Change Over Radical Shifts

00:43:00 Achieving Explosive Growth and True Product-Market Fit

00:49:01 The Most Important Lesson—Building the Right Team

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