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Stress had already pushed her husband to Florida. She was still running the company in Missouri — and she would not list. A broker brought in Elliot Omanson, managing partner and CEO of Alphi, who spent about fifteen minutes roughing out income, lifestyle, and legacy after a sale. He even modeled the ugly case: she cleared only a quarter of what she hoped for, after fees.
When she saw she could still live the life she wanted and meet goals for her kids, she turned to the broker and said, “List my business.”
On Episode 316 of The Exit, host Steve McGarry presses Omanson on why that kind of certainty is the real unlock — and what owners and buyers get wrong on timing, tax structure, and diligence. Here is the playbook from the conversation.
1. Run the Quarter-Price Certainty Test
Owners freeze because the business is the income engine they understand — and a sale swaps it for a portfolio managed by someone new. Omanson leans on a Tony Robbins frame: people will not move unless there is a degree of certainty about the outcome. Fail to show that, and they stay on the sidelines.
His fix is deliberately crude and fast. Rough out post-sale cash flow, taxes, and legacy goals in minutes — then stress-test with a quarter-of-asking-price scenario after broker and legal fees. For the Missouri owner, that fifteen-minute model dissolved the fear. Closing still took two years, and that runway mattered: time to learn how income would arrive, how taxes work without a small-business P&L, and which tools replace the ones founders already know. That early modeling, he says, has been the single greatest value he has provided clients since.
Monday morning: Before you debate multiples, sketch a one-page post-sale plan — including a quarter-price case — and sit with an adviser until the numbers feel real enough to list.
“People are not willing to take action unless there’s a degree of certainty to the outcome.”
— Elliot Omanson
2. Sell When Comfort Hits — Before the Golden Goose Dies
Omanson is clearest on when it is not time to sell. Two owners he had met years earlier came back after unexpected drops in production and revenue — and had to take less. Comfort delayed the exit; the market punished the wait.
He names the trap a lifestyle business: less day-to-day involvement, still drawing cash you cannot recreate from traditional investments. His illustration (not a universal rule): a business that might sell for $3 million while the owner pulls $500,000 a year. Under a rough 4% rule, $3 million supports about $120,000 a year — not half a million. Taking that much out usually means under-investing; numbers drift; eventually that golden goose dies. Then the choice is scale back lifestyle or return to the grind.
His sell signal: when energy and drive are gone, when you are comfortable taking money out and not putting growth capital back in, have the hard conversation. That comfort is often peak value. A business rarely rises when the person running it is no longer fully engaged. Avoid selling into distress or a clear downward trend.
Monday morning: Pull trailing twelve-month owner benefits versus reinvestment. If distributions are high and growth spend is thin, treat that as a listing trigger — not a reason to wait.
3. Don’t Let the “Team of No” Lock in Your Tax Bill
Omanson’s views from the episode — not tax, legal, or financial advice. Talk to qualified advisers about your own situation.
His number-one pattern: owners treat taxes owed at sale as a fixed bill that simply must be paid as presented. Structuring can change what is owed — but only if founders look past what he calls the “team of no”: CFOs, CPAs, investment advisers, and attorneys who, in his experience, are not incentivized to learn unfamiliar tools or sign off on them.
He has seen tens of millions left on the table. The largest deal he mentions involvement with was on the order of a billion dollars, where only one partner was willing to learn how the sale might have been structured differently. Much of Title 26 (the U.S. tax code), in his telling, is about how to defer or minimize tax — 401(k)s, IRAs, annuities, certain insurance structures — not a catalog of ways to pay more.
Monday morning: Before you accept “you’ll just owe X,” ask which proven code sections your advisers considered for your deal — and who on the team is willing to learn something they do not already use.
4. Ban “Creative” Tax — Stick to Proven Code
When Steve raises charitable structures and inventive deal design, Omanson pushes back on one word: creative. To him, creativity in tax means inventing something unproven — the fast lane to audits and sleepless nights. Prefer tools already written into the code and clarified through case law, then tailor them to the individual.
He also separates mistake from fraud: getting a complex area wrong in good faith is different from forging documents or stuffing a structure with risk that clearly is not insurable. His firm, he says, stands behind clients if an audit challenges their work.
Monday morning: Kill any exit-tax idea pitched as brand-new or “never been done.” Demand the statute, the case history, and written accountability if the IRS challenges it.
“There’s nothing creative in the tax code. There doesn’t need to be. It’s literally all written down.”
— Elliot Omanson
5. When You Think Diligence Is Done, Do It Again
Half of Steve’s audience buys businesses. Omanson’s advice to his younger self after a painful first acquisition: when you think you have done enough diligence, do that same amount again.
Little went right on that buy — bank accounts cleaned out, obligations unmet, debt left behind. It nearly broke him. The lever is depth: quality of earnings, forensic accountants, and mapping how employee and client relationships formed — and whether they survive a new owner. Holdbacks often fail to pay out when diligence was thin. His rule of thumb: an hour of real diligence upfront can save a hundred hours of pain later.
Monday morning: Before you sign, rerun your diligence checklist at the same depth you already completed — especially QoE, relationship continuity, and holdback conditions.
Final Takeaways for Founders
- Model life after the exit early — including a quarter-of-asking-price scenario — so fear gives way to a concrete plan (and leave runway to learn the new tools).
- Comfort without reinvestment is often the sell signal; wait for the golden goose to fade and you may sell into a weaker multiple.
- Tax at sale is a structuring problem, not a fixed penalty — push past the “team of no” and use proven code and case law, not untested “creative” schemes.
- Buyers: double your diligence. QoE, forensics, and relationship continuity beat optimism every time.
Ready to Plan the Exit — or Check the Comps?
Omanson is building what he positions as a zero-fee wealth management model at Alphi, plus a forthcoming book, Keep What You’ve Earned, on tax strategy and what he thinks is broken in traditional wealth management. Find him at elliotomanson.com and through Alphi online.
Weighing an exit yourself? Browse open SDE listings and live comps on Flippa as a reality check — or list your business when the certainty model says it is time.
Episode 316 of The Exit podcast — guest Elliot Omanson, managing partner and CEO at Alphi.
