Cody started a ride-share business in 2017 with no capital. He focused exclusively on small towns (<100K) where Uber/Lyft weren't available. I would 100% have passed if he pitched me years ago—and I would've been dead wrong.

So far he's raised only $2.1M, compared to Uber's $30B+ raised. And yet, he build a business doing $20M+ in annual revenue that is live in a dozen markets and multiple countries.

Besides competing with massive companies, he was also weeks away from bankruptcy when ride-share froze during the early days of COVID. He goes through exactly what he did to survive—and to grow well beyond where he was pre-COVID just a year after.

If you're bootstrapping or competing with better funded players, check this episode out.

Why you should listen:

• Why even massive competitors often don't mean you can't build a business.
• How to hack your way to millions in revenue with no budget.
• Why customer service and success are the keys to unlock word-of-mouth.
• How to survive 3 weeks of cash and near-bankruptcy.

Keywords
Uride, rideshare, entrepreneurship, bankruptcy, business growth, startup challenges, market expansion


Timestamps:
(00:00:00) Intro
(00:01:48) Thunder Bay Ridesharing
(00:03:49) A Problem that Shouldn't Exist
(00:06:44) The Launch
(00:08:15) Growing and Outgrowing
(00:10:50) A Bylaw Loophole
(00:13:27) Expanding to Other Communities
(00:17:05) Three Phases
(00:21:54) Surviving
(00:29:18) The Demand Curse of Ride Sharing
(00:34:09) Unride Focus
(00:39:46) Long Ways to Go

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I tried to pay my employees as little as possible. I thought I was being resourceful—& it seemed to work. Until it totally backfired. I learned my lesson the hard way.

No founder wants to hire B-level or C-level talent. Everyone is looking for A-players. They know that startups are all about the people. But most founders don't put in the work. And they end up with B-level teams.

If you're serious about getting and keeping A-players there's only one way to do it. You need to have a coherent strategy, you need to be intentional, and you need to make it priority number one. Here's how.

Takeaways

• Why paying employees less than they're worth incentivizes the wrong behaviour
• Why you need to have a system for regular performance reviews and salary adjustments.
• How to attract and retain A players
• How great junior talent can outperform B-level experienced talent.

Keywords
founders, compensation, hiring, A players, salary strategy, employee retention, startup culture, leadership, team building, performance reviews

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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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