About @RetiredFounder

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From a loving, middle class home, I'm a public school B student from the Midwest. My wife and I  married in 1994, we have 3 great adult kids.

Not sure why, but I've always been chasing $. I was the kid delivering newspapers at 4 in the morning, I cut grass, shoveled snow, sold things door to door. In my teens, I was a grocery sacker, telemarketer, survey taker, electronics salesman, umpire and any other job that would pay me.

Today, I'm retired and am lucky to spend most days with my beautiful wife. We enjoy golf, hiking, skiing, SCUBA diving, cooking and playing backgammon.

We split our time between Texas, Montana and Arizona.

A salesman by trade, I worked in technology for 7 years out of college before starting my first company in 1998 during the dot com boom. Sold that end of 1999 in a spate of good luck and timing, netting close to $1m. This gave me enough chips to make several really bad investments before using my remaining stack to found my SaaS company in 2003.

Lots to write about that bootstrap journey, but suffice to say I had a great team, wonderful mentors and a supportive wife. Believe I made more good decisions than bad (plenty of both,) had more good luck than bad and stuck around long enough to hit the jackpot.

Always thought my financial "magic number" to be $10m. Partnered with an outstanding PE firm in 2017, took $21m in chips off the table and rolled a big chunk of equity. Sold $40m more in equity in 2020 and got one last delicious $27m bite of the apple in 2022.

Retirement wasn't everything I expected.

The first few years were isolating and frustrating. Thankfully, I hired a coach (Rick Eigenbrod) who helped me make sense of what happened.

Here's a year's worth of therapy in a 4 paragraphs:

I greatly underestimated the deep sense of loss I'd feel leaving my company. My structure, purpose and identity, the scaffolding of my life, all vaporized overnight.

The things the world expects you to do didn't work for me. Starting another company, investing in startups, working with non-profits and sitting on boards were all failures for me.

My brain was running well developed programs that helped me in my career and were killing me in retirement. Ceasing my habits to optimize, rush, accumulate, etc. have proven difficult to stop.

I was looking for the next big thing, rather than living my own beautiful "mosaic life." Trying to fill my picture with filled with special, meaningful tiles and remove the ones that no longer fit.

Today, I work to support founders any way that I can and have created a peer group for UHNWI founders called "Beyond The Finish Line."