For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 3.

Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks because he couldn't afford a hotel.

Finally, 3 years in he'd hit $1.5M ARR. So he pitched 60 VCs for a Series A—and got 60 'no's. He was forced to raise a small, $1M inside round.

But then things changed:

2018: $1.5M ARR
2019: $5M ARR
2020: $10M ARR
2021: $20M ARR
2022: $40M ARR
2023: $70M ARR
2024: $100M+ ARR

Huntress is valued at $2B.

The investors who backed his $1M bridge are up 140x.

Now every VC wants to invest—and Kyle's the one saying 'no'.

Why you should listen:

How to know whether you should keep going or quit.
What it takes to get through the first few years at a bootstrapped startup.
Why revenue expansion is a huge lever for fast-growth (Huntress has 140% net revenue retention).
How starting a startup can impact your personal life and relationships.
How to work with partners to sell to long tail SMB customers.
Keywords
entrepreneurship, cybersecurity, product market fit, startup journey, military experience, SMB market, funding challenges, automation, human expertise, business growth

Timestamps:
(00:00:00) Intro
(00:2:01) Working at the NSA
(00:6:14) A big win in counter cyber terrorism
(00:10:00) What gave way to Huntress
(00:14:22) Pitching to a startup accelerator
(00:16:29) Adopting curiosity
(00:21:04) Getting ahead of cyber criminals
(00:26:00) Starting to grow
(00:32:50) Cult or conviction
(00:35:00) It takes grit
(00:39:50) Learning from people's lessons
(00:42:20) Cockroaches and underdogs
(00:46:10) Three strikes, I'm out
(00:52:56) Having a military background
(00:56:17) One piece of advice

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They were building a Segment competitor. It was working—customers were paying. But every sales call, prospects kept asking about the backend tech instead of the product.

So they killed the roadmap and pivoted. It took them 18 months to hit $1M ARR. Then they started growing. And so far, they've raised $350M.

Viraj walks through exactly how he validated the pivot, landed the first 10 customers, and why being outside Silicon Valley forced him to show more traction than everyone else.

Why You Should Listen

• How to know when your side feature is actually your real product
• The exact question to ask prospects to validate willingness to pay
• Why getting to $1M ARR slowly can set you up to scale faster
• How to compete when you're not based in Silicon Valley
• What talking to your first customer 4x a day for 2 months teaches you

Keywords

startup podcast, startup podcast for founders, open source startup, B2B SaaS growth, pivot strategy, developer tools startup, finding product market fit, early stage fundraising, design partners, commercial open source

00:00:00 Intro

00:01:46 Getting caught at the Coldplay concert

00:14:29 Deciding to Pivot From a Working Product to Something New

00:17:27 Building a Business Around Open Source Technology

00:19:38 Selling Before You Build

00:27:37 Talking to the First Customer Four Times a Day

00:30:51 Landing the First Ten Customers

00:35:10 Fundraising Without Silicon Valley Pedigree

00:38:48 When He Knew He Had Product Market Fit

Retry

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For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 2.

Here are the key lessons from the past 60 episodes that we've released to date. Each of the 5 steps to Product Market Fit is based on actual case studies with real examples you can use. It's a recap of everything I've learned over the last two years- you don't want to miss it.


Chapters:
(00:00:45) Mistakes Are Unavoidable But Avoidable Mistakes Are Unaffordable
(00:04:41) 1. Before Startup Mode, There's Research Mode
(00:07:16) 2. Only The Insanely Focused Survive
(00:10:49) 3. You Have to be IN the Market to WIN the Market
(00:14:08) 4. Forget Growth. Find Value.
(00:18:05) 5. Pivot Harder & Faster
(00:23:50) Recap

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