Selling your company, circus shows, and the best of the internet

Executive overview

Exits are emotionally and psychologically complex, yet almost no resources address the human side of the process. Rob and Sherry Walling are writing a book to fill that gap, drawing on direct exit experience, founder coaching, and years of advising sellers at every stage.

Two personal stories frame the episode: an artist's graceful response to AI-generated art, and a 31-year-old track record broken by a teenager — both illustrating how the internet enables unexpected human connection.

The fullest exit guidance combines financial logic with psychological depth — and most founders go through it without either.

Best uses of the internet

• A local artist messaged Sherry about AI-generated show art — not as a rant, but as a collaborative offer to help
• She framed her concern as personal truth, not accusation, and proposed a solution rather than raising a problem
• Rob's 1993 high school hurdles record was broken after 31 years; a classmate messaged him out of nowhere
• Rob recorded a video for the kid: genuine respect, welcome to the club, and what athletics meant over 30 years
• The kid's father said the message landed in a way his own teaching hadn't — shared experience creates unique credibility
• Both stories show the internet enabling warm, unexpected human connection across time and distance

The circus show as entrepreneurial act

• Sherry wrote, produced, and performed in a 20-artist circus show with 400 attendees across three performances
• One show was a continuing education credit event for licensed psychologists and therapists — approved by state boards
• The goal: express psychological truths about human flourishing through movement rather than words
• Founders are cognitively overloaded; creative, physical, non-verbal experience rebalances the neural circuitry
• Sherry's reasoning: you can't advise founders to have passion projects if you won't pursue your own
• Personal loss reinforced her belief that art and movement are essential to wellbeing, not optional extras
• Creating the show lets her spotlight other artists — a "second half of life" priority

The exit book: why it's needed

• Rob and Sherry are co-writing a book on the psychology and mechanics of selling a company
• Rob's qualification: direct exit experience, plus advising 15–20 founders at various deal sizes in a compressed period
• Sherry's qualification: partner through Rob's exit, plus years of founder coaching on the mindset side
• Existing books (Andrews, Warlow) cover some ground; this book adds the psychological layer and full-lifecycle perspective
• Scope is not SaaS-only: applies to agencies, service businesses, and any sellable company
• Recurring patterns emerged from Rob's founder conversations — about 60–75% of the same issues came up repeatedly
• Even successful exits often leave founders feeling empty and lost — a reality rarely voiced or prepared for

Book structure and what it covers

• 16 chapters planned; 7 have first drafts; ~27,000 words written
• Chapter arc: why exits are hard → when to go → exit options → mechanics → mindset → deal-making → support team → collateral damage → managing the process
• Rob's voice: analytical, dense, decision-criteria-driven — treating the exit as a math problem or escape room
• Sherry's voice: narrative, story-driven, existential — treating the exit as a question of meaning and identity
• The two voices are intended to feel seamless and complementary, covering logic and emotion together

Upcoming books and projects

• The Exit Book: expected later this year (timeline uncertain)
• The SaaS Launchpad: early-stage SaaS book; video course through MicroConf coming first
• Entrepreneur's Guide to Keeping Your Sh** Together: major revision planned, targeting 30–40% new content, new audiobook recording
• The four books together cover the full SaaS founder lifecycle: start → build → exit → stay sane