7MS #430: Interview with Dan DeCloss

7MS #430: Interview with Dan DeCloss

Today we're thrilled to have our friend and PlexTrac CEO Dan DeCloss back to the program! (P.S. PlexTrac is launching runbooks as a feature - and you should definitely check out PlexTrac's upcoming Webinar about runbooks on September 9!). We also did a PlexTrac 101 Webinar with them recently!

You may remember Dan from such podcasts as this one when we first talked to him in 2019. Dan and I have a lot in common in that we both started security companies about the same time, so I had a lot of questions for Dan around how business has been going since we last talked on the podcast. Today our topics/questions include:

  • What are the (good) warning signs that a passion project you have could be a viable business?

  • Why "having all the jobs there has ever been" is a great way to figure out it's time to start your own business :-)

  • At what point does a side project have to become what you do for your day job?

  • How do you safely prepare to quit a comfortable corporate life to life as a small biz owner? Do you go 100% on faith? Do you save your $ for a year so you can "float" your business for a while? Some combination of the two?

  • How important is it to have the support of your friends/family when starting a new biz?

  • Once you start a biz what are the best/worst things about wearing all the hats (engineering, sales, marketing, accounting, HR, etc.)?

  • When is it time to hire additional resources or raise additional money to support your growing business?

  • What marketing efforts are fruitful for a new security biz to spend time/money on?

  • How do you decide what bells/whistles to add to PlexTrac? Follow your own roadmap? Let the customers drive your direction? Some combo of both?

  • What new bells and whistles are coming to PlexTrac in the Webinar on September 9?! (Spoiler alert: RUNBOOKS!)

Jaksot(720)

7MS #720: Tales of Pentest Pwnage – Part 84

7MS #720: Tales of Pentest Pwnage – Part 84

Hey friends! Today's another Tales of Pentest Pwnage! Quick tangent first on a couple side projects: I've got a music thing at quack.house (like the duck noise, not the drug) and a podcast with my dan...

1 Touko 43min

7MS #719: Baby's First OpenClaw

7MS #719: Baby's First OpenClaw

Hey friends! This week's episode is "Baby's First OpenClaw" – basically me shouting into the void hoping a smart listener will DM me and explain why this thing is supposed to be life-changing. Because...

24 Huhti 28min

7MS #718: Fun Professional and Personal AI Project Ideas

7MS #718: Fun Professional and Personal AI Project Ideas

Hey friends! After last week's heavy episode about my wife's health scare in Punta Cana, today's is a lighter one. (Quick update: she's doing better – still recovering, but appetite's back and she's g...

17 Huhti 28min

7MS #717: I Gave Up My Wife's PHI (And I'd Do It Again)

7MS #717: I Gave Up My Wife's PHI (And I'd Do It Again)

Hello friends! Today's episode is a bit of a detour from our usual content — it's part vacation horror story, part security/privacy confession. My wife got seriously ill during our spring break trip t...

10 Huhti 48min

7MS #716: Tales of Pentest Pwnage – Part 83

7MS #716: Tales of Pentest Pwnage – Part 83

Today is my favorite pentest pwnage tale of 2026 – and maybe ever!  It centers around an ADCS abuse via an attack path I'd never seen before.  Tips include: Use Netexec to pull Powershell history Try...

3 Huhti 33min

7MS #715: Tales of Pentest Pwnage – Part 82

7MS #715: Tales of Pentest Pwnage – Part 82

Hola friends!  Today's another fun tale of pentest pwnage.  This time we started with no credentials and then set off on the bumpy journey from no-cred zero to domain admin hero!  One specific referen...

27 Maalis 20min

7MS #714: Tales of Pentest Pwnage – Part 81

7MS #714: Tales of Pentest Pwnage – Part 81

Hello friends!  We're back with a fun tale of internal network pentest pwnage.  This one highlights how AI can be used (with some guardrails!) to automate the boring stuff – and even help you pick par...

20 Maalis 22min

7MS #713: How to Secure Your Community – Part 3

7MS #713: How to Secure Your Community – Part 3

Hello friends, in today's edition of How to Secure Your Community, I give a brief recap of part 1 and part 2, and then dive into some cool phone shortcuts you can setup so that with a single tap, you ...

13 Maalis 31min

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