Retired Founder

Been studying post-exit founder life for 4 years. Don’t have it solved, but know a few things for certain: Contentment is better than chasing more. Simple beats complex, especially with investments. Your habits don’t retire with you. Personal energy is your best guide. I am not alone. What did I miss?

For my post-exit founder friends. Anastasia is likely the leading expert on what happens after selling your business and how to navigate life beyond the finish line. Thanks @AnasKoroleva for your work here.

@rickfoe Thanks, Rick! Nice to see you here.

Jeff is a great follow. Very wise post-success guy.

@justingordon212 Thanks, Justin. I've enjoyed watching your progress!

@RetiredFounder Welcome back!

Reintroducing myself. Jeff Swearingen, a retired founder, exploring a post-exit world. Originally from Minnesota, school at UT Austin where I met my beautiful wife. Proud father of 3 adult kids. Salesman by trade, founder / entrepreneur since 1997. Founded SecureLink (an Austin based security software company) in 2003. CEO until I retired in 2018. Had a LOT of help from home, employees, advisors, etc. Worked hard and got lucky too. Sold majority to Vista Equity Partners in 2017, then another PE firm in 2020 and finally to a Thoma Bravo company in 2022. Weird thing happened a few years into retirement: found myself lost and confused, missing the structure, purpose and identity I had from work. Thought retiring young (49) with ample financial resources would be sunshine and roses every day, but it wasn’t. Embarrassing to admit that I was failing at success. Realized I wasn’t alone- started this account and posted my story a few places, which led to creating a men's group for other retired founders called Beyond The Finish Line. Thanks to all of my friends there that are helping me navigate the maze. Currently working on a few projects: managing the BTFL group, building a retreat center called Rancho Loco in Scottsdale, mentoring founders navigating an exit and slowly playing the top 100 golf courses in the US. I plan to post here on occasion, mostly about post-exit life, but maybe some golf content or other rants as well. Nice to be back, life is good.

@thesamparr “It is not the critic who counts.” You’re a stand up guy, Sam. Keep up the great work.

Alright. We turned that into something good. Whew. Good night everyone and thanks for the love!

@pxg @Top100Rick Love my other 13 PXG clubs in my bag too!

@RetiredFounder @Top100Rick Thanks for the reco 🙌

Guys, I’m thinking about buying a 7 wood. Anyone got one they recommend? Sometimes I like to get fit by a pro, but there is a great thrill to just picking one up off the rack. Like rolling the dice at the craps table.

Wife and I quit insurance 2 years ago. Kids are grown and on their own policies, so no concerns there. Our experience (yours may vary) is that things are less expensive paying out of pocket than we were paying with insurance “discounted rates” Hopefully will not need to test this with a major event, but if we were to have something catastrophic happen, I really don’t want the insurance company dictating care. This is not advice, do your own research, just sharing my experience.

Thinking of going naked on health insurance. Is this a bad idea? I have insurance, it costs me so much. And I still pay an ass ton out of pocket. Baring the low probability risk of disease; going no health insurance is a better deal. Just pay everything out of pocket.

@thesamparr Welcome to the last best place. Come see us in Big Sky next time.

In Montana for vacation. Holy hell. This place is wonderful.

@practicalgolf The quiet is the best part. Would love to live in a world without gas powered lawn equipment.

2 out of the last 3 golf courses I’ve played had robotic mowers. Perfectly mowed lines and it went around someone’s bag with impressive precision. 😳

70% of second businesses fail after an exit. Anastasia Koroleva studied post exit founders for 13 years and came on Moneywise to explain why. Her exit: -Built a bootstrap company to a "nine-digit" exit (over $100M) -Lost half her net worth through divorce and "stupid mistakes" -Now worth high eight figures -Started a second business that failed miserably Her money setup: -Spends $650K-$1M annually for family of 5 -No wealth manager (tried many, didn't like any) -Portfolio: 65% liquid assets, 25% private credit, 10% private equity -Owns homes in London and South France But after studying hundreds of post-exit founders, she found many follow the same psychological pattern. The common traps: -Starting too soon (using business to escape identity crisis) -Starting too late (skills atrophy, relationships fade) -Naive industry jumps (no competitive advantage -Misunderstanding your strengths (creator vs. operator) -Sudden Wealth Syndrome (irrational fear of losing money) Her biggest insight? "Most of us don't actually look at the big picture, and because of that, we fall into a very predictable trap." She believes it takes about 10 years to fully adjust after a big exit, and everyone struggles during this period. There's no escaping it. What she recommends: -give yourself 1-2 years to let things sllow down -Rebuild your basics (community, purpose, health), which is what your company likely gave you -Attack the next thing with clear motivation Full pod is live. Harry said it's the most important episode we've done. Agree?

@mikekarnj Seems logical that building product will be easier/faster/cheaper with AI. Also seems to follow that more products chasing the same number of prospect customers may make customer acquisition even harder than ever.

@mikekarnj Congrats! Did anything surprise you about your time on sabbatical?

Sonos upgrade- thoughts and prayers appreciated.

@rickfoe @vhmth Thanks for the excellent writing here, Rick. Have had lots of people sending me @vhmth recent post. Glad to help when / if he’s ready.

I'm interviewing people who are in a similar situation, as part of a series called The Other Side of Enough. They all have similar unexpected challenges... You might appreciate this one with @RetiredFounder. After 'Happily Ever After': newsletter.thewayofwork.com/p/after-happil…

I am rich and have no idea what to do with my life. Where I talk about leaving Loom, giving up $60m, larping as Elon, breaking up with my girlfriend, insecurities, a brief stint at DOGE, and how I'm now in Hawaii self-studying physics. vinay.sh/i-am-rich-and-…

@_jacksmith Woof.

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@SievaKozinsky Great model, you will do well. Good luck!

@SievaKozinsky Have you been successful buying these? I tried once with an Austin VC and was told they would rather let them go over a cliff than leave a messy skid mark. Just one data point.