What’s Next After Building a $2.5B Cybersecurity Company with Dean Sysman

What does it look like when a cybersecurity founder who built a $2.5 billion company decides to level up, again? Dean Sysman, co-founder of Axonius, sits down with Ron Eddings to pull back the curtain on what it really took to go from zero to $100M ARR in four and a half years, and what came next.

Dean breaks down the founder mindset, the emotional weight of tying your identity to your company, and why he stepped into the Executive Chairman role while simultaneously pursuing a PhD in AI systems at Columbia University. He gets into how boxing taught him what solo performance reveals about leadership, why vulnerability is a non-negotiable skill at scale, and what it means to care about something bigger than yourself. This one hits differently if you're building, leading, or figuring out what your next chapter looks like.

Impactful Moments

00:00 – Introduction
05:00 – Boxing for charity: raising $55K
08:00 – Competitive by nature, born to build
10:00 – Solo performance sharpens team leadership
13:00 – Axonius: zero to $100M ARR in 4.5 years
15:00 – Founder identity tied to company success
21:00 – Purpose bigger than yourself fuels resilience
25:00 – Self-awareness as the #1 growth tool
28:00 – Executive Chairman + Columbia PhD pursuit
33:00 – Ron's personal reflection on founder identity

Links

Connect with our guest, Dean Sysman, on LinkedIn: https://www.linkedin.com/in/deansysman/
Check out our upcoming events: https://www.hackervalley.com/livestreams
Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com
Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

Tämä jakso on lisätty Podme-palveluun avoimen RSS-syötteen kautta eikä se ole Podmen omaa tuotantoa. Siksi jakso saattaa sisältää mainontaa.

Jaksot(441)

Do You Know What Your Agent is Doing at 3AM? with Amir Ofek

Every AI agent in your environment inherits someone's permissions, and most teams have no idea what those agents are actually doing with them. Amir Ofek, CEO and co-founder of Aizome, shares how to ma...

16 Syys 38min

Cloud Broke My World Before AI Did with Dr. Jay Abdullah

Cybersecurity has survived cloud, mobile, and a dozen other "biggest disruptions of our lifetime," and each one felt unprecedented in the moment. In this episode, Ron sits down with Alyssa "Dr. Jay" A...

9 Syys 36min

The Dashboard Is Dead, Long Live the Harness with Myke Lyons

Security teams spent decades begging for more logs. Now the enterprise is generating petabytes a day, and the thing drowning in it isn't just the SOC anymore, it's your AI agents too. In this episode,...

1 Syys 35min

The AI Already Inside Your Company with Russell Spitler & Richard Penshorn

A year ago, the average employee held about 30 OAuth grants. Today that number has risen to 88, and it isn't slowing down. Ron sits down with Russell Spitler, co-founder and CEO of Nudge Security, and...

25 Elo 35min

Humans First: Adobe's Rule for Building AI Security Tools with John Gillis

Imagine how much investigation time your SOC could get back if the busywork just disappeared. Ron sits down with John Gillis, Staff Security AI Engineer at Adobe, who built an in-house AI investigatio...

19 Elo 34min

Let AI Do More Without Surrendering Your Judgment with Jen Easterly

Fresh off the showroom floor at Black Hat 2026, Ron brings back some hot takes from the crowd. Nearly every booth he visited, including the Exaforce booth, was pushing in the same direction. Trust in ...

14 Elo 23min

Post-Quantum Cryptography: What Every Organization Needs to Know with Michael Fasulo

What if the encrypted traffic flowing across the internet right now (emails, files, logins) is already being quietly collected and stored by someone waiting for the day they can finally crack it open?...

12 Elo 30min

Stop Defending the Edge: How to Rethink Your Mobile Security with Jared Shepard

What if the biggest risk to your organization isn't the device that gets lost, but the data that lives on it? Ron Eddings sits down with Jared Shepard, Founder and CEO of Hypori, whose path ran from h...

7 Elo 38min