I’m on my way to Kansas City for the day to spend time with the Kauffman Foundation at the 1 Million Cups annual meeting, talking about Give First: The Power of Mentorship . My drive to the airport started off with an intimate conversation with a close friend who recently got a cancer diagnosis that compounds another serious health issue he’s been battling. Consequently, I’m in a pensive and reflective mode right now. ...

I’m on my way to Chicago for the day to give several talks on Give First: The Power of Mentorship and spend time with my long-time friend, Troy Henikoff. I enjoy Chicago and its startup community, which has produced some great companies over the last 20 years. I think my first investment in Chicago was during the late 1990s in StartSampling (which I inherited from a Mobius partner.) It lived for a long time based on the tireless work of Larry Burns and his team, but ultimately didn’t make it. My next experience was with FeedBurner, which resulted in a positive outcome and fostered lasting friendships with the founders (Dick Costolo, Matt Shobe, Eric Lunt, and Steve Olechowski), as well as several executives, including Don Loeb, Rick Klau, and Brent Hill. ...

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I’ve been enjoying doing podcasts again on the Techstars Give First Podcast . When I went into hibernation two years ago, David carried the weight of the podcast and kept it going. But, … I’m back (for what it’s worth), at least for a little while until I turn into a pumpkin. I had a delightful conversation with Seth Godin . We’ve been friends for 30 years through an initial connection from Charley Lax as part of a diligence project that introduced me to Jerry Colonna and Fred Wilson around an investment that Jerry, Fred, and SoftBank subsequently made in Seth’s company, Yoyodyne (which was acquired a few years later by Yahoo!) ...

I am an enormous Andy Weir fan – I think a long dinner 1:1 with him would be epicly fun. While I usually run naked (I don’t listen to anything), I’ll occasionally add an audiobook during a marathon training period. During the summer training for the StVrain75Hygiene36 Berlin Proxy Marathon 2021 (a marathon I ran locally at the same time that my partners Seth and Ryan ran the Berlin marathon), I listened to Project Hail Mary. ...

As I wander around Seattle for a few days, including a fun event with JP Morgan in the morning and PSL at the end of the day, I’ve been pondering the evolution of startup communities. I first started coming to Seattle in 1990 and wrote a post seven years ago about it – Hanging Out In Pioneer Square . Last night, while sitting with Greg and Shannon Gottesman, overlooking Lake Washington, I relaxed into a wonderful feeling of topophilia . ...

I decided to ask Claude (Opus 4), Gemini (2.5 Pro), and ChatGPT a few personal questions. I’m tired of the excessive anthropomorphizing of “AI software”, so I thought I’d see what some of the different AIs had to say about … themselves. I warmed up each conversation with a few personal questions. My questions are in italics. Claude When were you born? I was created by Anthropic, though I don’t have a specific “birth date” in the traditional sense. I’m Claude Opus 4 from the Claude 4 model family, which was released in May 2025. Rather than being born, I came into existence through a training process where I learned from text data to understand and communicate in natural language. ...

I spent two days in Toronto (hosted by Matt Golden at Golden Ventures) and a day in Upstate New York (hosted by Martin Babinec ) this week as part of the launch of Give First: The Power of Mentorship . Many others were involved in making this a fantastic trip that touched over a thousand people. Extra special thanks to Julia Baird and Olivia Goldstein for the awesome support. ...

Give First: The Power of Mentorship is now available in both physical and Kindle formats. BradTheBookSalesman says, “Don’t wait, buy it today!” And yes, someday it will be available as an audiobook. As a bonus, my long-time friend Andy Sack’s book AI First: The Playbook for a Future-Proof Business and Brand is also launching today. BradTheBookSalesman says, “Buy Andy’s book also! Make it a two-fer.” ...

As I gear up for the official launch of Give First: The Power of Mentorship this week, I spent the weekend reading, playing with my 7GL, running, celebrating my 32nd wedding anniversary with Amy, and hanging out with some friends who were in town. Ben Wiener’s book Fever Pitch: A Novel About Selling Your Vision, Raising Venture Capital, and Launching Your Startup was delightful! Ben is a partner at Jumpspeed , based in Jerusalem, Israel. We are email friends, and he has been key in helping develop and lead the Jerusalem startup community. I don’t know his portfolio well, but I do know he was an investor in BreezoMeter, an app I obsessively used during a fire season in Boulder one summer. ...