I'm Jeff Swearingen, a retired software founder. I have nothing to sell you — no coaching, no subscriptions, no agenda. Just honest perspective from someone who's been through it.
This site exists to help two kinds of people:
Planning an exit?Chances are you have bankers, lawyers, investors, employees, co-founders and others in your ear. If you want honest and objective advice, contact me. No agenda, no cost of any kind, just experienced advice from someone that's been through it.
Already crossed the finish line?Are you post-exit, post-economic, yet wondering what happened to your sense of purpose and identity? I run a free men's group called Beyond The Finish Line where post-wealth founders help one another live their best lives.
About @RetiredFounder
Life so far
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 are based in Scottsdale, Arizona and spend time in Big Sky, Montana and Pebble Beach, California.
Career
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.
This gave me enough chips to make several really bad investments before using my remaining stack to found my SaaS security company, SecureLink, 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.
Partnered with Vista Equity Partners in 2017 and sold the company across multiple transactions from 2017-2022.
Retirement
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 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.
Communities I'm aware of, work with or support somehow
Beyond The Finish Line (BTFL) - my free peer group for post-exit, post-economic founders. Members share the common trait of having the perfect amount of money: "enough."
Hampton - a highly vetted private network for high-growth founders and CEOs, founded by Sam Parr. Small peer groups of 8 meet monthly with a facilitator to work through business and life challenges.
PEF (Post Exit Founders) - a global community of 5,000+ post-exit founders supporting each other in finding purpose, fulfillment and what's next after selling their company. Founded by Barak Kaufman and Shlomo Dalezman.
Long Angle - a free, vetted peer community of 6,000+ high-net-worth individuals across 45+ countries. Founded by post-exit entrepreneurs, focused on wealth management, peer connections and private market opportunities. No membership fees.
Tiger 21 - the premier peer advisory network for ultra-high-net-worth entrepreneurs, investors and executives. Founded in 1999, members meet in small groups with a dedicated chair to navigate wealth preservation, family, legacy and philanthropy.
EO - the entrepreneurs organization. Paid peer-to-peer entrepreneur group. I was a member a long time ago and met some great people.
What Happens When You Get What You Want? by Rick Eigenbrod - explores why we are far better prepared to pursue success than to have it, and why achievement can also bring loss and disruption
The Psychology of Money by Morgan Housel - timeless lessons on wealth, greed, and happiness, exploring the strange ways people think about money
The Second Mountain by David Brooks - a look at what happens after you summit the first mountain of career success, and the deeper commitments to family, vocation, philosophy, and community that define a meaningful life
From Strength to Strength by Arthur C. Brooks - a practical roadmap for finding purpose, happiness, and success in the second half of life, from Harvard's happiness columnist
Rancho Loco is a personal project — a dedicated space in Scottsdale, Arizona, built to enable the kind of in-person, authentic conversations that just don't happen on Zoom. I love hosting people, but having too many guests at the house for too long isn't great for anyone. Can accommodate 8 guests with their own bedroom and bathroom.
Rancho Loco is available at no cost to interesting groups of friends and founders, both working and retired. It's not a party house, it's a place to connect with peers, have real conversations, and remember what life is like when you don't have your phone in your face all day. Bring your A game — there will be an arcade with pinball, video games, ping pong and golf simulator.
Beyond The Finish Line (BTFL) is a free peer group for post-exit, post-economic founders. Our members have sold their businesses and share the common trait of having the perfect amount of money: "enough."
BTFL exists because the journey after an exit can be unexpectedly difficult. The loss of structure, purpose and identity that comes with leaving your company is real, and most founders aren't prepared for it. Our group provides a private, trusted circle of peers who understand what you're going through — because they've been there too.
BTFL is not an investment group, not a networking club and not a for-profit venture. It's a place where founders support each other in building meaningful lives beyond the finish line.
No. I do not make any traditional investments in companies. I am here to give, not invest. If you need help, guidance, someone to talk with, I'm here. But, please don't ask me to invest in your company or refer you to any of my friends for an investment.
Can I pick your brain?
Yes, if you're considering selling / exiting your business, I'd be glad to help guide you with no agenda or fees. Please contact me.
Yes, if you've sold your business and are feeling a bit lost. This is my main project for those Beyond The Finish Line. Please contact me.
Please read the notes!
Please see notes to the right before hitting send!
I love founders, but only have bandwidth and knowledge to be useful to some.
If you're thinking of selling your business or planning your exit, please tell me a little about your situation before hitting send.
If you've sold your business and are trying to figure out life beyond the finish line, please write a bit about your situation before hitting send.
If you are thinking of starting a business or are in the early stages, I'm cheering you on but there are many better resources than me.
