Season 2 of #VCHunting Complete!

Season 1 and 2! – A new Twitter banner!

[Want to see the roster for Season 1?]

Season 2 is wrapped up! It’s been a whirlwind of a time and I have thoroughly enjoyed speaking with an All-Star guest roster. My quest to build my very own venture fund is growing closer day-by-day, and I love that I have so many supporters who are rooting me on! I’m so very glad I’m documenting the journey, it’s going to be a wild 2020!

Season 2 Roster of #VCHunting

Each season gets better and better!


We are now two full seasons into my learning adventure into venture capital. While these interviews have been crucial to my learning regimen, I’ve had countless of in-person conversations with VCs that have been absolutely powerful as well (see below for more Twitter takes on whom I’ve met this season)!

Let’s get onto some learning from Season 2:

  • It’s clear to me that the first thesis of my venture fund was off. The idea was that there are huge holes in venture capital and that I am willing to take on these gaps and improve upon them. What I found is that this isn’t enough of a value proposition to build a fund. I can improve upon the dysfunctions of VC in how I execute, but I needed to have a better focus on what I find exciting, not merely trying to fix dysfunctions of the system like:
    • Venture capital is not a transparent industry
    • Venture capital has a clear incentive misalignment
    • Venture capital is driven by supply, not demand
    • Venture capital is lacking in diversity
  • I’ve gotten push-back from some VCs I’ve spoken to as they have found it incredulous that I would want to even entertain the idea of building a venture fund. I found this to be interesting as my assumption would be that other VCs would be excited and even encouraged that I would want to embark on such an endeavor. It seemed (to a few) that I was doing something that they felt wasn’t necessary. Maybe there are already too many venture funds out there? Either way, it was a little discouraging to find that some of my (future) colleagues would try to dissuade me from wanting to build a venture fund. I won’t be spending much time considering the nay-sayers. This is my goal and I’m going to achieve it!
  • Venture Capitalists are stuck between a rock and a hard place. While network-deals come easy for some, based on their time in the space, I never received any great suggestions on how to improve deal flow beyond the usual “tweet more / speak more / share more” mantra. I’m not convinced that this is the answer and I believe I’m uniquely positioned to be able to create a deal flow funnel that will be second to none. The gravitational pull I’m creating will (in time) be enviable.
  • I especially appreciated some of the VCs thesis and target markets that they are focusing on. The more I learn about other markets and why certain VCs focus on them tells me greater stories about who they are and what incentivizes them. It’s great to be able to see behind-the-curtain a bit and understand the motives of VCs to be in the space. Not surprisingly, I even had one person tell me that he’s simply here for the money and fame (not one of my interviewees).
  • I got some pretty solid feedback from a few VCs about my methods for attracting eyeballs and growing myself in this space. Being the fastest growing daily show in #venturemedia has been good to me, and it’s fascinating how there is such a lack of coverage of what’s going on from a human-standpoint. I still maintain that the venture media space is growing, however, not at the speed that other markets are growing. We still do not have a person or character that has really substantiated a niche within venture and video. While podcasting is on the rise, it’s really a half-baked attempt to be part of the wave of interest and staying relevant. We live now in a mobile-first video-first world where having video of founders, leaders, and company executives is still relatively absent, sans a few of the bigger players who are pushing content out. I’m building a model now of how VCs should address the public, daily, and be part of the overall conversation, daily. It’s something I’m seeing a few VCs begin to do, however, we’ll see how long they last in daily content. It’s hard to push content on multiple mediums, daily. Really hard.
  • I want to make venture capital something that is really accessible to the common man. Actually, in one of my journals, I wrote that “I want to make venture capital cool.” – I’m not exactly sure of how to do this, however, I’m going to be doing my best to be a cool VC in the future… I have ideas, however, it’s a matter of timing and execution that will reveal if those experiments are of any value.
  • Finally, I’ve been wrestling with the opportunity to join a venture fund (as an analyst or scout). I’ve been offered several positions this season and I’ve always answered “no.” The reason is that I’m convinced that while it’s probably a great idea to get in-the-trenches experience, I believe that the right partner or co-founder who understands what I’m trying to do will emerge in time. This isn’t to say that I won’t end up joining a venture fund, however, the terms of the opportunities weren’t good, and it would reduce my ability to focus on the larger plays that I have in store. I probably will struggle with this tension until the right timing comes, let’s hope that 2020 will be that year.

I am absolutely delighted to be in a position where I can bootstrap the early beginnings of the infrastructure of my own venture fund. Consulting with startups and companies in Agile is something that I’ve always been passionate about as Scrum and Agile changed my life!

I look forward to what 2020 Q2 brings. It’s amazing that so much has happened already in such little time. I’m telling you, with dedication, persistence, and assertiveness to the goal, all things can be achieved.

Thanks so much to all my supporters out there who are coming along on this journey with me. To infinity and Bitcoin!


I’ve been around! Click the pictures to retweet or drop a comment!

Hanging out with the Service Provider Capital LPs and GPs in downtown Atlanta!
Service Provider Capital’s other investments (like me)!
I also did my first live stream #AskaFounder – Was a good experiment!
Always teaching Agile and Scrum to startup companies! – This is up in Minnesota!
Spent some time with the guys to see how Agile for startups can help them grow quickly!
Hanging out with Daley Ervin of EngageVC!
Is this the first venture funded Radical SR3 race car? Me thinks so!

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