Issue #27: First Year Out of College

In May last year I graduated from University of Portland and last month passed without my realizing the significance. All last year I was excited to graduate. During the final spring semester, by which point I had started the podcast, I wanted to spend all my free time learning about acquiring small companies. But homework took up nearly all my free time and it was frustrating. I was ready to finish.

The feeling of not having homework, classes, and living in an apartment without roommates has been incredible. Additionally, I’ve had more time to work on Think Like an Owner and connect with fascinating people. Since graduating, I’ve released 12 podcast episodes, written 27 Tailwinds editions, my 2019 Annual Letter, and gained a small following on Twitter. I do miss seeing my friends everyday, but the end of college didn’t end all those friendships as I feared it might. If anything, those friendships are stronger than ever.

With over a year and a half under my belt with the podcast, I feel I’ve hit a groove. At first I was afraid the small company investing world would be too small to support a podcast. Today I think I could upgrade to a weekly episode cadence. The space is huge and there are hundreds of smart and thoughtful investors out there, all approaching investing in their own unique ways. The more I explore and the more folks I talk with, the more I realize how much there is yet to be explored.

I have to credit most of this progress to you, my readers and listeners, who reach out to talk about the space, share your learnings, and introduce me to the most interesting professionals you know. Your willingness to share is what’s propelled this project forward and will grow it faster than ever. There is no way I could have grown the project to what it is today just through cold emails, calls, and messages on Twitter and LinkedIn. This has truly been, and will continue to be, a team effort and I want you all to know how much it means to me.

On the more personal side, I’ll be getting married on August 29th with a much smaller wedding than originally planned. Michelle and I originally invited 130 people but as coronavirus unfolded we cut back to 25 of our closest friends and family. We briefly considered postponing it, but marriage is more than a ceremony and we didn’t want to wait any longer. My former roommate and one of my closest friends will officiate, we’ll have fantastic Italian food, Great Notion beer, and a long-time family friend will play live guitar music for us. We’re beyond excited.

Thank you for being a part of this project. I have big plans for the podcast and every conversation, email, intro, and phone call from you builds on this project in no small way. I’m very glad to have you all along for the ride!


Thank you to Traction Capital Partners for supporting the podcast and making it easier than ever to create new episodes. Traction acquires companies in the Pacific Northwest with between $1-5m in EBITDA and has acquired two companies to date. Visit their website or contact one of the partners, Justin Turner, directly to learn more.


Capital Notes

  • This Twitter thread about the inverse relationship between quality of a company’s CIM and returns was fascinating, I loved watching all these expert investors go back and forth. Highly recommend reading this.

  • Tim Ludwig talks about the first 100 days after an acquisition in this Twitter thread.

  • I listened to this Invest Like the Best episode with Rishi Ganti about esoteric assets that trade without markets. I couldn’t help but pull parallels to micro PE from it and I hope you pick up the same notes that I did. Credit to Alex Mears for the recommendation.

  • Polina Marinova left her job to work on The Profile full time and wrote about her experience so far being an entrepreneur and the excitement and fear it brings.

  • This thread about lessons learned from writing online from Patrick McKenzie and David Perell is really interesting to think about, even if you don’t have the desire to write.

If you found an interesting article, podcast, or interview that I missed, please let me know, I’m always looking for interesting stuff.

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I’m always looking to connect with folks interested in this space, don’t hesitate to reach out.