I usually do a few interviews (podcasts?) at the beginning of the year. I avoid all of the end of the prior year “what do you predict for next year” stuff and find that several long-form interviews at the beginning of the year allow me to get out of my head what’s going on from my frame of reference.

If you know me, you know that I learn by doing, writing, reading, and thinking out loud. I find these interviews to be a good way for me to think out loud to solidify my transition into the new year.

I did two interviews right after the new year. One with Andrew Keen …

The Tech Community Needs To Be Humble to Survive What Will Be a Challenging 2023

… and one with Jason Calacanis.

(0: 00 ) Jason Kicks off the show
(2:49 ) Brad Feld, Co-founder of Foundry, talks about starting out in investing
(13:30 ) LinkedIn Jobs – Post your first job for free at https://linkedin.com/twist  
(14:56 ) Brad’s thesis for whom he’ll get in the “trenches” with  
(20:48 ) MasterClass – Get 15% off an annual membership at https://masterclass.com/startups
(22:22 ) Fighting to the end + Investing through the dot-com bubble
(38:13 ) Microsoft for Startups Founders Hub – Apply in 5 minutes, no funding required, sign up at http://aka.ms/thisweekinstartups
(39:43 ) Surviving the GFC
(44:23 ) Brad’s perspective on the investor/CEO dynamic + being a leader in a down market
(1:00:02 ) Reflecting on the speculative asset bubble
(1:16:44 ) Looking forward into 2023

They are both great interviewers willing to let me ramble when prompted vs. tie me into a structured interview.

So, if you like hearing me think out loud, I encourage both of them. Jason’s show notes include links to specific segments (listed above) if something specific catches your attention.

A few weeks ago I did a long interview with Jason Calacanis on This Week In Startups . I got a bunch of positive feedback on it and thought it was one of the better long form interviews I’ve done in a while.

The other day Jason released an interview that he recently did with David Cohen, the CEO of TechStars . I listened to it earlier today – it was also excellent. I highly recommend it if you are interested in TechStars, accelerators, early stage investing, ramping your startup, and how David thinks about angel investing from his fund Bullet Time Ventures.

I always enjoy hanging out with Jason Calacanis. We first met in the mid-1990s when Jason was hanging out in NY doing Silicon Alley Reporter. I can’t remember who initially introduced us – it was probably Fred Wilson .

We covered a lot in the hour+ interview for This Week In Startups . Things like why I didn’t retire at age 30, what Amy’s ring tone is, Startup Communities, Boulder, what motivates me, the different between mentors and advisors, my biggest failures in the Internet bubble, the Foundry Group investment strategy, my angel investment strategy, why Fred Wilson and USV has been so successful, why the objective of a VC is a straightforward and how to define success as a VC, why the answer to “how is a VC fund doing” is “check back in a decade”, hiring for culture fit vs. competence., why entrepreneurs get to – and should – define their culture, why you can’t change people (and how my first marriage blew up), why investors are like D&D characters, examples of bad behavior of VCs and entrepreneurs, more stuff about VC and entrepreneur interactions, what the best board meetings are, a reminder that people lie, Lance Armstrong and ego, CEO coaches, the first person I ever fired, and a bunch of other stuff.

Enjoy!

Jason – you are the Internet’s Charlie Rose. Well done.