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

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

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

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

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

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