Eldon put a $150K line of credit on his house to start eSentire in 2001. No VCs would touch him—they didn't understand services businesses. He worked 12-hour days, 7 days a week for 7 years to hit $1M in revenue. His co-founder coded while he flew to New York on $99 JetBlue flights from Buffalo to save money.

Then something clicked: they brought in an experienced CEO who transformed their scrappy cybersecurity consulting into a managed service.

Revenue grew from $1M to $10M in just 3 years. They won 95% of competitive deals against Dell-backed SecureWorks by comparing themselves to a local burger joint versus McDonald's.

Today eSentire is worth over a billion dollars. This is the raw, unfiltered story of building a massive B2B company without following any of the Silicon Valley playbook—no YC, no venture capital for years, just pure survival mode.

Why You Should Listen:

• How to win head-to-head sales battles against bigger competitors with no marketing budget.
• Why taking a long time to hit $1M ARR doesn't mean failure.
• How bringing in an experienced CEO after 8 years saved the company.

Keywords (comma-separated):

Startup podcast, Startup podcast for founders, eSentire, Eldon Sprickerhoff, cybersecurity, bootstrapping, managed services, B2B sales, Canadian startup, MSSP, founder-led sales, pivot

00:00:00 Intro

00:01:00 Starting eSentire after 9/11

00:03:26 The dot-com crash reality

00:05:23 $150K home equity line to start

00:08:32 Landing first customer at ING

00:14:03 Making up the rules as they went

00:19:09 Bringing in an experienced CEO

00:22:44 The hamburger pitch that beat Dell

00:28:36 From $1M to $10M in 3 years

00:34:39 Common founder mistakes

00:40:39 Chief survival officer mindset

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Soham spent 6 months building AI that would auto-generate integrations between any software. He locked down Glean as an early customer because he had friends there. And it failed completely.

So he pivoted. This time, he refused to work with friendly customers who knew him. Instead, he did 10-20 calls per day with strangers who would tell him his product sucked. He posted on Discord communities at 3am, wrote technical blogs that went viral on Reddit, and created fake landing pages to see what integrations people actually wanted.

In one year, Composio grew to 100,000 developers and raised $30M from Lightspeed in just 3 weeks.

His contrarian take: in AI, asking users what they want will just get you faster horses. Built it instead, and watch their eyes light up.

Why You Should Listen:

• Why friendly customers will kill your startup.
• The 20 calls per day strategy that scaled Composio to 100,000 users.
• Why you can't validate AI products by asking.
• The exact Discord and SEO tactics that got their first thousand users without spending on ads

Keywords (comma-separated):

The PMF Show is a startup podcast. The Product Market Fit Show is a startup podcast. Startup Podcast, Composio, Soham Ganatra, AI agents, developer tools, pivot, Series A, Lightspeed, integrations, API, tool calling

00:00:00 Intro

00:06:44 Playing with GPT-2 before ChatGPT

00:12:37 Leaving his job to start Composio

00:21:16 Pivoting to integrations for AI agents

00:28:42 Why friendly customers are dangerous

00:31:01 Getting first users through viral content

00:36:01 Taking 10-20 customer calls per day

00:40:58 Scaling from 1,000 to 100,000 developers

00:43:58 MCP and the explosion of growth

00:48:59 Raising $30M from Lightspeed in 3 weeks

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Sahil was 18 when TechCrunch published a hit piece calling him a copycat. His co-founder Aaron was 16. They'd just raised $6 million from YC and top VCs for their crypto startup, then got subpoenaed by a state government and watched their business implode.

So they fired everyone, moved back to their parents' homes, and spent months cold-calling dentists and lawn care companies to find a real problem. What they discovered: 80% of SMBs still use community banks from 1995. Now Affiniti has 2,000 customers, $10M ARR run rate, and just raised $17M by partnering with trade associations to acquire customers at 25% the cost of traditional fintech.

This is the raw story of teenage founders who got punched in the face by Silicon Valley and came back swinging.

Why You Should Listen:

• How getting destroyed on TechCrunch at 18 and subpoenaed by the government led to a $3M revenue pivot in 12 months
• Why going back to square 0 is often the best move
• The trade association go-to-market strategy that worked for SMB.
• Why 200 VC rejections and raising $6M in peak 2021 couldn't save their first startup—but taught them everything they needed to know.
• Get comfortable with bad days—stoicism is the only way to survive.

Keywords:

Affiniti, Sahil Phadnis, SMB fintech, startup pivot, Y Combinator, teenage founders, Series A, B2B payments, startup failure, trade associations

00:00:00 Intro

00:01:50 COVID existential crisis at 16

00:08:36 Building websites for restaurants

00:11:11 Meeting Aaron on Instagram

00:15:17 200 VC rejections then raising $6M

00:23:03 Getting called a fraud on TechCrunch

00:29:15 Firing everyone and moving home

00:31:16 Faking toothaches to research SMBs

00:40:50 Launching Affiniti

00:47:00 The trade association growth hack

00:55:03 Raising Series A in 3 weeks

00:58:30 Stoicism and bad days

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Jon spent 3 years building Gamma with barely any traction—just a few hundred users after burning millions. Then ChatGPT dropped. In desperation, he pivoted to AI-powered presentations in March 2023 with one year of runway left. What happened next was insane: Paul Graham publicly mocked their launch tweet calling it worthless—then it went viral.

They went from 2,000 signups a day to 60,000. Their servers crashed for three days, but when they came back online, panicked users threw $50K at them thinking they needed to pay to make it work. Within two months of launching payments, they hit $1M ARR and became cashflow positive.

This is the raw story of how a dying startup caught the AI lightning and never looked back.

Why You Should Listen:

• How to survive 3 years with no traction.
• Why 80% hype and 20% value can still build a real business
• The exact onboarding flow that turned 5% activation into viral growth
• How negative viral engagement can still drive massive revenue
• The difference between 10x better and 50% better

Keywords:
Gamma, Jon Noronha, AI presentations, product market fit, pivot to AI, viral growth, Paul Graham, ChatGPT, cashflow positive, productivity startup

00:00:00 Intro

00:02:15 Why presentations haven't changed in 40 years

00:11:55 User research reveals the real problem

00:26:26 The market crashes and runway shrinks

00:34:32 ChatGPT drops and everything changes

00:43:19 Paul Graham trashes the launch tweet

00:48:59 Going viral by accident

00:51:33 60,000 signups a day breaks everything

00:55:07 Hitting $1M ARR in 2 months

00:58:47 Endurance is everything

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Soham co-founded Rubrik by taking what he learned from building Google's data center tech to enterprises desperate for cloud migration. Two quarters later, he hit $1M ARR. And a few years later, a $16B IPO.

Soham breaks down why paid pilots beat free trials, how to sell enterprise hardware before it works, and why early customers become your biggest champions when you solve real pain.

Now building WisdomAI after watching the ChatGPT moment unfold, he shares what's different about competing in AI's gold rush versus owning an ignored category.

Why You Should Listen:

• Why early customers endure broken products
• How he hit $1M ARR in 2 quarters selling enterprise hardware
• Why you should always charge for pilots
• Customer feedback is the only PMF signal that matters

Keywords:

Rubrik, Soham Mazumdar, enterprise sales, data backup, IPO, product market fit, B2B SaaS, cloud migration, WisdomAI, data centers

00:00:00 Intro

00:04:26 Leaving Google to start a company

00:11:00 Building the founding team

00:14:27 Landing the first customer in Australia

00:22:30 Hitting $1M ARR in two quarters

00:25:42 Go-to-market strategy and the DeLorean stunt

00:30:30 When Arvind left to start Glean

00:34:10 Starting WisdomAI after the ChatGPT moment

00:51:22 Advice for early stage founders

Retry

Claude can make mistakes.
Please double-check responses.

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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

Send me a message to let me know what you think!