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. Since graduating, I’ve released 12 podcast episodes, written 27 Tailwinds editions, my 2019 Annual Letter, and gained a small following on Twitter.

Issue #26: My Changed Belief on Interviewing

One closing question I ask podcast guests is, “What’s a belief you used to hold strongly and have since changed your mind on?” I like this question because it shares some insight into how our views change with time and experience. Well, when it comes to the podcast, there’s a belief of my own that has shifted since starting the project.

Issue #22: Building Community

Cash Flow Cowboy, Tim Ludwig, Andrew Wilkinson, Ari Ozick, Michael Burry, Adam Keesling, Slate Star Codex, Oregon whales

Issue #18: Reading

Tim Ludwig, Dan McMurtrie, Greenhaven Road, Good Things Don’t Scale, Mikel Berger, Capital Camp

Think Like an Owner Newsletter: The Pilot

When I talk with owners and investors who are in the middle of starting their company or investing, I can hear and feel the emotional swings of their adventures. On some days they experience otherworldly highs; a new customer, closing a deal, an exciting new partnership. On other days they feel unfathomable lows; losing valuable employees, deaths and terminal illnesses in their work and personal life, divorcing with a business partner. These times are raw and felt stronger than at any other point in time.