Let’s say it’s 2012. And you're graduating Stanford with a comp sci degree. You could go to Google, Facebook or any of a number of well-paying emerging juggernauts. If you’re Frank Wang, you move across the coast and do your PhD in cybersecurity at MIT.

Now you’re doing your PhD. And you make pals with a local VC. So naturally, you start a cybersecurity incubator as an academic (Cybersecurity Factory) which churns out companies such as Huntress Labs.

Your PhD is in the bag now and you're ready to start making money. Time to apply all of that theory from academia in a company, right? Wrong. If you’re Frank Wang, you become a VC at Dell Capital.
It’s the middle of the Covid pandemic and VC is going bonkers. Massive amounts of capital being allocated in a frenzy unlike anything we’ve seen in decades. If ever. Rather than joining in the party, Frank sees it as a clear signal that it’s time to move on and becomes a security engineering leader at modern data stack company DBT.

Now that you’ve got a comfortable job at a high flying tech company, it’s time to take your foot off the gas pedal, right? Do your part and ride it out through a lucrative exit. Frank saw this as the time to step up his side hustle instead and start the popular blog and newsletter, Frankly Speaking.

The conversation is a little over an hour of Dave exploring the career arc of Frank to date and what he’s learned while blazing his own, unconventional trail through cybersecurity. The unique road he has traveled lends him perspective for those who want to better understand VCs, running a side business, or simply what happens when you ignore conventional wisdom and have the courage to make your own path.