Everyone in tech talks about raising. Almost no one talks about owning.

In this episode of Not Another Podcast, Brennan Pothetes sits down with Alex Matjanec, a serial founder who built and sold multiple companies without a dollar of venture funding, to unpack what it really takes to build wealth, freedom, and meaning in a world addicted to speed.

Alex built his first startup during the 2008 financial crisis, launched a top-ranked mobile agency during the App Store boom, and now runs Wysh, a fully licensed life-insurance carrier redefining what “financial protection” means.

They get brutally honest about:

• The trade-offs of raising vs. bootstrapping
• How to build a company while working full-time (without getting sued)
• What it actually costs (in time and sanity) to start an insurance company
• How AI is rewriting the creative and agency world
• The terrifying accuracy of actuarial math (yes, insurers really can predict when you’ll die)
• Why patience, timing, and ownership beat hype every time

If you’ve ever wondered how to build something real in a bubble full of noise — this episode is for you.

Timestamps

00:00 – Intro: Brennan on fatherhood and building

02:00 – Running a company while raising twins

06:00 – How fintech evolved from 2008 to now

09:00 – Crypto, smart contracts, and the insurance opportunity

13:00 – Life insurance as the most human business in finance

18:00 – AI’s role in predicting life & risk

24:00 – Building Wysh: redesigning insurance from scratch

33:00 – The next wave of applied AI and hardware

36:00 – Bootstrapping vs. raising capital in 2025

43:00 – The rise of the art-director era for creatives

46:00 – AGI, plows, and the next job revolution

50:00 – Longevity, fertility, and the future of insurance products

1:00:00 – How to actually start an insurance company (the truth)

1:16:00 – Wild stories: pandemics, fraud, and the Wimbledon policy

1:23:00 – The founder mindset: solving problems you can’t stop thinking about

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