Retired Founder

Chasing energy and experience.

Retired from chasing money and things.

[Retired Founder @RetiredFounder]

If I had put my Tesla Roadster deposit into SpaceX stock, I could afford my own Falcon Heavy.

[Retired Founder @RetiredFounder]

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?

[Retired Founder @RetiredFounder]

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.

[Anastasia Koroleva @AnasKoroleva]

I recently joined Alex Macdonald in conversation for his new platform Sequel Originals.

Being invited onto something he’s creating felt truly meaningful.

Watch our full conversation here: https://t.co/qstU8VLMsr

Credit: @alexfmac x @joinsequel

#Sequeloriginals #ExitParadox #Entrepreneur #PersonalGrowth #Founder #PostExit

[Retired Founder @RetiredFounder]

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

[Retired Founder @RetiredFounder]

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

[Retired Founder @RetiredFounder]

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.

[Retired Founder @RetiredFounder]

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

[Retired Founder @RetiredFounder]

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

[Retired Founder @RetiredFounder]

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.

[Retired Founder @RetiredFounder]

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

[Retired Founder @RetiredFounder]

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

[Sam Parr @thesamparr]

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?

[Retired Founder @RetiredFounder]

@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.

[Retired Founder @RetiredFounder]

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

[Retired Founder @RetiredFounder]

Sonos upgrade- thoughts and prayers appreciated.

[Retired Founder @RetiredFounder]

@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.

[Rick Foerster @rickfoe]

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':
https://t.co/C0w97Z0GYD

[Retired Founder @RetiredFounder]

@_jacksmith Woof.

[Retired Founder @RetiredFounder]

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