Acquiring Minds

Episode: How to Own 20% of Multiple SMBs

Host: Will Smith

Guest: Evan D. Leonardi

Date: February 12, 2026

Episode Overview

This episode explores Evan D. Leonardi’s unconventional journey in the world of small business acquisition. In a two-part discussion, Evan first shares the turbulent but ultimately successful purchase and turnaround of a rural commercial cleaning business, which he operates remotely while living a digital nomad lifestyle. In the second half, Evan details his innovative model: partnering with SBA searchers, using his expertise to help them buy businesses in exchange for ~20% equity—effectively building a diversified, passive, de-risked portfolio of SMB ownership without stacking personal guarantees. The host, Will Smith, probes both the hardships and the strategic insight behind Evan’s approach, highlighting lessons relevant for anyone interested in acquisition entrepreneurship.

1. Evan’s Background and Path to Acquisition (03:57–12:38)

• Career Start & Mindset

  • Evan began in healthcare and management consulting, quickly realizing the corporate path didn’t suit him due to his strong entrepreneurial itch. (03:57)
  • Early experiment: bought an Airbnb to gain entrepreneurial experience but sought a faster, bigger move into business ownership.

• Discovering ETA (Entrepreneurship Through Acquisition)

  • Exposed to acquisition entrepreneurship luminaries like Cody Sanchez and Walker Deibel via social media. Initially skeptical, but ultimately joined Ben Kelly’s “Acquisition Ace” community in October 2023 for mentorship and “to buy down my ignorance.” (06:20–06:46)
  • Credits structured community, education, and peer support with making his first deal less daunting:
    “A lot of the, the stuff you’re like, ‘I don’t know how this works, this seems risky.’ I got de-risked by being around people who are doing the same thing and having people who had done it before guiding me through it.” (06:46)

• Lifestyle Design

  • Digital nomadism is central—Evan is passionate about operating his businesses (and life) remotely, living in locations like Tulum, Mexico, for motivation, community, and lifestyle leverage. (09:48–12:38)
  • “My whole goal was always lifestyle first...I’m just trying to be myself...while also enjoying my life.” (09:48)

2. The Search and Acquisition: Commercial Cleaning Business (13:05–25:43)

• Buy Box & Search Criteria

  • Initially open to “any industry, anywhere in the country—just anything to get me out of my job.” Over time, preferred blue-collar, non-technical, and not excessively white-collar.
  • Core criteria: ability to manage remotely, recurring revenue, and not in highly competitive or low-margin industries like restaurants or retail. (13:05–15:37)

• The Deal

  • In late January 2024, got under contract on a commercial cleaning business in rural Ohio:
    • Purchase price: $1.6M (just over 3x SDE, business only)
    • SDE: ~$500K (revenue ~$2M, 25% margins)
    • Deal Structure: 90% SBA loan, 5% seller note (2-year standby), 5% buyer equity. No real estate included after environmental report complications. (20:13–24:32)
    • Remote management was a key consideration given Evan’s lifestyle.

3. The Transition: The “J Curve” After Acquisition (27:50–62:36)

• Immediate Challenges

  • Closing delayed six months due to SBA and seller tax complications. The seller checked out, lost key accounts, and masked operational issues.
    “I don’t think I’m totally out of the woods on yet, but...it was a scary J curve...” (29:27, 38:10)

• Inherited Organizational Dysfunction

  • Discovered deep-seated problems: key employees (seller’s family) underperforming or outright stealing, weak leadership, and a business run more like a “family piggy bank.”

  • Fired the GM (seller’s step-grandfather) and most family members. Resulted in legal threats, operational turmoil, and a near-collapse. (48:50–54:54, Quote below)

    “He overreacted very aggressively...he tried to delete all our files...he thought I was the bad guy, he was the victim. Very aggressive, threatening. The managers were scared of him...it was a very strenuous time as a new business owner.”
    – Evan, 51:42

• Survival and Turnaround

  • Evan and two loyal managers cleaned, managed, and recruited for months to right the ship.
  • Replaced management and gradually restored client confidence. Biggest account doubled its contract, stabilizing the business. (55:41–57:21)
  • EBITDA dropped about 20% amid the turmoil, but business quality, team capability, and processes all dramatically improved:
    “It wasn’t like the optimistic thing you put on the spreadsheet when you’re underwriting...but I think 2026 and beyond is going to be pretty solid is my hope.” (62:36, 66:02)

• Lessons Learned

  • Working Capital: Used line of credit instead of permanent working capital; paid it down aggressively before distributions. (68:00–71:47)
  • Remote Ownership: Built strong systems, trusted team, and process visibility to maintain performance remotely, but acknowledged the tradeoff—more challenging management and some employee feelings of abandonment during crises. (61:00)

4. Evolution: Becoming an SBA Buy-Side Advisor & Building a Diversified Equity Portfolio (72:11–113:20)

• Genesis of the Model

  • During the closing delay, Evan continued searching but couldn't acquire additional businesses personally because of his SBA PG commitment. Instead, he partnered with other aspiring operators/searchers—he would find and close deals for/with them in exchange for minority (typically 20%) equity. (72:37–74:57)

  • His value: Sourcing, negotiation, due diligence, deal leadership, transition mentorship—and then passive board-level involvement post-close.

    “I can get smaller stakes of companies, but I can focus on the process I enjoy the most, which is...the buying of the businesses...and then find someone else who wants to operate them.” (74:57)

• The Model in Practice

  • Aims to cap personal equity at 20% in each deal to avoid multiple personal guarantees.

  • “If he pulls off five such partnerships, he’ll own the equivalent of 100% of a single small business. But he’ll be diversified, passive, and without a personal guarantee in any of them.” (00:00)

  • Terms are “market-driven”—some partners see huge value in time, access, and expert guidance; they’re willing to give up equity in return for a de-risked, higher-probability acquisition (77:38–80:19).

  • Quote:

    “Would you rather have 80%...of something good that’s been vetted by someone who’s done it...or would you rather have 100% of something that’s maybe not that great or you just never get anything?”
    – Evan, 78:00

• Risks and How It Works

  • No upfront fees; all “sweat equity” and time-risked. Operates in good faith—most legal protections ensure he isn’t cut out post-close, but picking the right partners is crucial. (81:28–84:08)
  • Focuses mainly on searchers with significant experience/background, seeking bigger deals ($1M+ SDE), and industries where he/partner has expertise. (84:29–85:46)

• Deal Flow & Scaling

  • Deals typically take 8–14 months to source, diligence, and close.

  • Has equity in four businesses; aims for 2–3 new partner deals per year (more possible with a team).

  • Began creating additional infrastructure (fund, network of recruiters, value-add post-close services) to scale, referencing similar models by Shareholder Ventures, Adam Markley, and others in the ecosystem. (103:18–108:27)

  • Quote:

    “So if I did this for five years with those conservative ish numbers...there’s a decent chance...I have a portfolio with $15 million in equity in my own name and $750k in cashflow, which I would consider set for life to some extent.”
    – Evan, 101:05

• Comparing the Model to Traditional ETA

  • Host and guest debate: Is this a slower or faster path to wealth than buying one business outright? Evan’s model may take longer initially, but scales far better, de-risks personal exposure via diversification and no PGs, and offers compounding equity and cashflow. (87:26–97:55)

• Why isn’t Everyone Doing This?

  • High barrier to entry—requires reputation, expertise, deal flow, and operator network.
  • Long game: Not “get rich quick” or easily Instagrammable, but yields compounding returns and lifestyle design for experienced searchers.
  • Concludes: This is professional investment—active but highly leveraged, earning equity “in kind” by delivering results for other operators instead of bringing capital.

5. Notable Quotes & Memorable Moments

On Lifestyle and Remote Ownership:

"I'm kind of a self-proclaimed workaholic... But I did want it to be so I could spend a couple hours a day on it, help grow it, but not be within 20 minutes of the business or in the office every day. So yeah, remote and absentee to me are very different things."
— Evan (15:53)

On Unmasking a Troubled Business:

"I found pretty quickly that the biggest customer had three family members working in the business as well, all making significantly more than the rest of the cleaners, all clocking in for hours that they evidently weren't working... the GM was hiding [complaints]... because they didn’t want to lose the family piggy bank."
— Evan (46:19)

The J Curve/Turnaround:

"He overreacted very aggressively... He tried to delete all our files... managers were scared... It was a very strenuous time as a new business owner." — Evan (51:42)

On Building the Equity Model:

"I can focus on the process that I enjoy the most, which is the searching and the buying of the businesses... and then find someone else who wants to operate them."
— Evan (74:57)

Napkin Math—The Vision:

“If I could do three a year...each business I buy then would effectively give me $50k in cash flow a year and $1 million in equity for when it eventually sells...If I did this for five years...$15 million in equity, and now...$750k in cash flow. So if I did this for five years...there’s a decent chance...I have a portfolio with $15 million in equity in my own name and $750k in cash flow.”
— Evan (100:02–101:05)

Host’s Closing Reflection:

“Owning 20% of five businesses seems better than owning 100% of one business.” — Will Smith (88:57)

6. Chapter Timestamps

• Evan’s Background & Search Beginnings: (03:57–12:38)
• Search & Acquisition Details: (13:05–25:43)
• Transition, J Curve, Turnaround: (27:50–62:36)
• Financing, Working Capital Lessons: (68:00–72:11)
• The Partner/Advisor Model Explained: (72:11–100:02)
• Model Comparison & Scaling Discussion: (100:02–108:27)
• Ecosystem Insights & Closing: (108:27–End)

7. Key Takeaways

• Acquisition isn’t “get rich quick”—expect a J curve of pain, learning, and adaptation, especially in small, fragile businesses.
• Strong systems, people, and lifestyle intent can enable location-independent business ownership, but there are real tradeoffs.
• Pooling expertise to help others buy businesses in exchange for minority equity can build a diversified, scalable, de-risked portfolio—IF you have deal flow, reputation, and choose your partners carefully.
• This evolving “buy-side advisor for equity” model is gaining momentum in ETA, especially among those with deep search, deal, and operational expertise.

For more, connect with Evan D. Leonardi on LinkedIn and find future episodes and summaries at acquiringminds.co.

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