Built to Sell Radio

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Ep 527 How to Avoid an Earn-Out (Even in a Service Business) Jan 02, 2026

Show notes

Most business owners hit a fork in the road.

Stay "on the tools" and keep making great money. Or start feathering back your personal involvement so the business can grow beyond you.

In this episode of Built to Sell Radio, Dr. Michael Filosi walks through how he made that shift in a dental practice, without jeopardizing cash flow. He didn't rip the band-aid off. He reduced his patient days one day at a time while the practice added clinicians and transitioned patients carefully. Over a few years, his billings went from roughly 43% of revenue to single digits, and he only went to zero once the business was already producing most of his take-home income.

In this episode, you discover how to

Spot the "capped upside" moment when your time becomes the constraint
Feather back from four days on the tools to three, then two, then zero
Time each reduction using numbers, not hope
Transition customers off the owner without breaking trust
Remove key-person risk by ensuring no one producer dominates revenue
Keep cash flow steady while you trade personal production for enterprise value

The result: Filosi sold his practice and collected 100% of his cash at closing, which is almost unheard of in dentistry.

Ep 526 Best of 2025: 4 Moments That Change How You Exit Dec 26, 2025

Show notes

Built to Sell Radio just dropped a year-end special that pulls the strongest moments from 2025 into one episode.

Across four formats (Exit Story, Inside the Mind of an Acquirer, Mastering the Deal, and After the Deal), you discover how to

Choose exit value over lifestyle income before comfort caps valuation
Spot the "founder-dependent" trap that scares off serious buyers
See how buyers price risk, not just revenue and EBITDA
Use imperfections as leverage instead of liabilities
Build leverage before a first offer quietly sets your ceiling
Create real alternatives so negotiations stop feeling one-sided
Prepare for the identity shift that hits after the wire clears

Ep 525 How to Know When to Get Out: What to do when Shopify threatens, Selling vs. hiring a CEO. A controlled process instead of massive auction and getting your cash up front. Dec 19, 2025

Show notes

If you're feeling a little queasy about the pace of change, you're not alone. AI is accelerating competition in almost every market, and it's making some business models feel irrelevant almost overnight.

In this episode of Built to Sell Radio, John Warrillow talks with Ryan O'Leary, who saw a similar wave coming in payments when Shopify started bundling merchant processing into its plans. O'Leary chose to sell before the shift crushed margins, structuring a deal that put most of his cash in hand up front. In this episode, you discover how to

• Decide whether to raise capital, hire a CEO, roll equity, or sell • Spot the early signals that a platform is about to "bundle" you into irrelevance • Run a tight sale process with a short target list and still generate multiple LOIs fast • Negotiate for deal structure that protects you, not just a higher multiple • Limit earnout risk by keeping the earnout short and the rules hard to game • Separate emotion from the numbers so you can negotiate clean • Keep your team aligned through the transition by sharing upside, including the earnout

Ep 524 3 Non-Negotiables to Walk Away Clean, Turn Your Expertise into Recurring Revenue, and Avoiding a Deal-Killing Clause. Dec 12, 2025

Show notes

Most experts who start a practice or studio end up trapped by their own success. The schedule is packed, the waitlist is long, but every dollar still depends on them showing up.

In this week's episode of Built to Sell Radio, John talks to a physical therapist who turned a fully booked, owner-dependent practice into a boutique fitness business with recurring revenue, a second-in-command, and a clean exit on her terms. After a first deal collapsed on closing day thanks to a last-minute bank clause, she went back to market with three non-negotiables and still got a seven-figure outcome.

Ep 523 15 x EBITDA for a Service Firm Dec 05, 2025

Show notes

In this episode of Built to Sell Radio, John Warrillow sits down with Ujwal Arkalgud, who built the same company twice. Chapter one was a classic problem: a profitable, founder-heavy services firm with impressive EBITDA but a ceiling on valuation. Chapter two began when he turned that service into a productized offering, transformed how customers bought his work, and ultimately sold for more than 15x EBITDA — roughly three times the offer he received as a simple service provider.

Ep 522 The difference between 4x vs.8x EBITDA, Customer Concentration Discounts, PE Re-trades with Eric Wiklendt on this special edition of Inside the Mind of an Acquirer Nov 28, 2025

Show notes

For many owners, private equity feels like a black box: a buyer shows up with a multiple, some debt, and a term sheet, and it is hard to tell whether you are getting a fair shake or being set up for a painful re-trade later.

In this Inside the Mind of an Acquirer episode of Built to Sell Radio, John Warrillow sits down with Speyside Equity managing director Eric Wiklendt.

Ep 521 10x Outcome Selling Tiny to Private Equity and how to make the 'Cruise vs Double Down' Decision Nov 21, 2025

Show notes

Andrew Roberts spent two decades turning a bootstrapped family company from Brisbane into one of the most widely used text editors on the web, then faced the hardest call of his career: keep a comfortable, profitable business or push for a bigger exit with venture capital and private equity in the mix.

Ep 520 How Chris Hutchins convinced Google to buy Milk—and Wealthfront to acquire Grove—despite not generating much revenue (and no EBITDA) Nov 14, 2025

Show notes

A strategic acquirer is a company buying to advance its own roadmap, distribution, or capabilities—unlike financial buyers (private equity, family offices) who buy primarily for cash flow. To a strategic, value may sit in what you've built, not what you've earned.

Chris Hutchins' story makes the point. He co-founded Milk, acquired by Google, and later founded Grove, acquired by Wealthfront. Both saw assets they could plug in—product, team, IP—even when revenue and EBITDA weren't impressive.

If you want a strategic acquirer to pay for what you've built rather than how much money you make, this episode of Built to Sell Radio is for you. You'll discover how to:

• Define and prioritize the assets a strategic may value now (team, product, customer list, roadmap, even your lease) • Reframe your pitch so a distribution-rich buyer may see an immediate lift from your assets • Run a fast, momentum-led process that invites quick noes and surfaces real interest • Split assets across buyers when it improves the overall outcome • Protect employees and customers while you move quickly toward a decision

If a strategic exit is on your radar, this playbook helps you create options when EBITDA won't carry the deal.

Ep 519 How to Avoid the Unforced Errors That Can Wipe Out Your Equity Nov 07, 2025

Show notes

Spencer Dennis was an elite golfer whose playing career ended with spine surgery in his teens. He became a tour-level coach, running high-performance programs for juniors, college players, and pros. Managing parents, trainers, and recruiters through texts and email was chaos, so he built CoachNow to guide athletes between sessions.

CoachNow caught on quickly with busy coaches. Then a run of decisions—turning off revenue under "grow fast" advice, stacking convertibles and preferences, and accepting stock-for-stock deals—left Spencer with little to show for a product customers loved. This is a cautionary tale for any owner negotiating with "sophisticated" investors.

Ep 518 Growth Equity, Control, and When Rolling Equity Fails — John Ruffolo (Inside the Mind of an Acquirer) Oct 31, 2025

Show notes

If you're considering your endgame, you're probably looking at private equity. Most PE firms use a familiar formula: buy a majority stake and ask the owner to "roll equity"—re-invest part of the proceeds—into the newco they're building. The downside: you become a minority shareholder in a business you no longer control.

There's another path: growth equity, which lets you take chips off the table via a secondary while maintaining control. That's the business John Ruffolo is in as Founder & Managing Partner at Maverix Private Equity (he also founded OMERS Ventures).

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