Bobby DeSimone is the Founder and CEO of Pomerium, the best way to authenticate, authorize, monitor, and secure user access to any application without a VPN.

Bobby explains why access control is so important, how it led to the biggest corporate hack ever, how its related to the day CrowdStrike took down the global economy, and how AI will change security.

Pomerium has a unique open source approach, and Bobby takes us inside the early days of building the product, how he got the first customers, lessons learning enterprise sales as a technical founder, and inside his funding rounds, including a recent Series A led by Eric Vishria at Benchmark.

Timestamps
(00:00) Intro
(02:02) Access Control: a sneaky large problem
(07:22) How an unsecure air conditioner led to the biggest credit card breach in history
(10:23) Google’s internal security software inspiring Pomerium
(16:41) Making his first money online selling a WoW bot
(19:24) How CrowdStrike took down the global economy in July, 2024
(22:29) Deep dive on access control and security
(29:39) How access controls impacted Google vs Uber’s self-driving lawsuit
(30:52) Why Zero Trust security is marketing bullshit
(32:09) Advice for building access control
(34:39) How open source built early trust with customers
(41:39) Missing a 7-figure deal because he didn’t use LinkedIn
(44:52) Everything he’s learned about sales as a technical founder
(50:06) Inside Pomerium’s Series A
(51:41) Advice on evaluating potential investors
(56:06) How AI will change security
(01:01:15) Getting in trouble at the first Pomerium board meeting
(01:02:15) How to hire good engineers
(01:04:00) When to scale back IC work as a founder
(01:06:56) Favorite new AI tools
(01:11:09) Why Meta’s open sourcing its AI models
(01:12:32) Life lessons from Charlie Munger
Referenced
Check out Pomerium: https://www.pomerium.com/
Crowdstrike outage post-mortem: https://www.crowdstrike.com/falcon-content-update-remediation-and-guidance-hub/
Pomerium on GitHub: https://github.com/pomerium/pomerium
Follow Bobby
Twitter: https://x.com/bdd_io
LinkedIn: https://www.linkedin.com/in/bobby-desimone/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/

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