Acquiring Minds – Episode Summary
Podcast: Acquiring Minds
Host: Will Smith
Guest: Greg Geronimus (formerly Co-CEO, Smart Tours; now Managing Partner, Footbridge Partners)
Episode: Buy Well, Exit Better: A $67m Win in 4 Years
Date: November 17, 2025
Overview
This episode of Acquiring Minds dives deep into the full acquisition lifecycle of a tour operator, Smart Tours, that Greg Geronimus and his partner acquired as young first-time “searchers,” scaled, de-risked, and ultimately exited for a 9x EBITDA multiple ($67.5m), returning over $62m to investors in just four years. Greg reflects candidly on each step: searching, structuring, operating—including high-stress crisis management—exit psychology, and the value of “buying well.” The episode is loaded with direct advice, hard-won lessons, and transparency on deal terms, making it invaluable for both novice and experienced acquisition entrepreneurs.
Key Discussion Points & Insights
1. Greg’s Background and the Appeal of Search Funds [04:14]
- Upbringing: Grew up observing his entrepreneurial father scaling a medical practice into a business and ultimately selling it.
- Career Path: Harvard undergrad → Private equity at Goldman Sachs → Harvard Business School (HBS) intending to find a startup idea but instead discovered search funds with his friend David Rosner.
- Early Days of Search Funds: Search funds were not widely known on HBS campus in 2011/2012. Greg and David catalyzed what became HBS’s celebrated “Entrepreneurship Through Acquisition” course.
- Search Capital: Their search was funded by a patchwork of mentors, ex-bosses, and HBS contacts; the investor landscape was less formal than today.
"For both of us, it was really love at first sight for the search fund path. In many ways a more attractive risk-reward than a pure startup." — Greg Geronimus [05:55]
2. The Search Process—Lessons from the Buy-Side [09:43]
- Geographic Focus: Limited to NY, NJ, CT, PA for family reasons.
- High-Volume Outreach: “Industry agnostic, high volume by design”—hundreds of emails, events, and local networking.
- Serendipity: The eventual deal came via a casual networking intro from a banker met at a BDO happy hour.
- Deal Origination: Old-fashioned, relational introductions (accountants, bankers) can trump cold outreach in deal outcomes.
"It does seem like people smirk at the irony...the business was a friend of a friend, right around the corner." — Will Smith [12:20]
3. Acquiring Smart Tours—Deal Structure & Off-Market Negotiation [19:46]
Business at a Glance
- ~$30m revenue, $5m EBITDA (but run by only 7 people, so true “owner-absent” EBITDA much lower)
- Classic “old-school” tour operator, highly cash-generative (customers pay up front, vendors paid later)
- Minimal team = high key person risk
The Deal [31:37]
- Structure (initial):
- 5x EBITDA
- 60% Seller Note at 4% interest
- 5% increase in price, 10% reduction in seller note in final structure (ended with 50% seller note)
- Final Structure:
- Purchase price: ~$29m
- 50% seller note
- $5m senior debt (SBIC)
- $10m investor equity
- Purchase price: ~$29m
"He starts sketching out...a 60% seller note at 4%. I had to restrain myself, not let on that I found it quite attractive." — Greg Geronimus [15:00]
- Why Off-Market Terms Make Sense: High key person risk meant a low multiple and big seller note were fair; such businesses “have no real market.”
Negotiating Tip
- Always Ask the Seller to Go First: Often, their “number” or structure can be more favorable than you’d dare suggest.
"There’s no way I would have put out the idea of a 50–60% seller note. I would have been too concerned about offending the seller...I would have done myself a significant disservice if I had, if I had gone first." — Greg Geronimus [47:25]
4. Operating the Business—De-risking, Not Just Growth [49:44]
- Steep Learning Curve: Both young, single-digit years of business experience, mostly finance background.
- Key Person Risk: Focused first on building out team/processes to “de-owner” the business.
- Philosophy: Conservative (risk-averse) owners; prioritized cashflow and debt paydown over aggressive, risky bets.
"We didn’t have to be heroic during the operating phase. If we could de-risk, professionalize, and build a real team, we’d be in a nice position to have a great outcome." — Greg Geronimus [50:25]
Value of De-Risking
- Massive equity value is created not just through growth but by converting a fragile, “all roads lead to owner” business into a robust, transferable operation.
"De-risking the business: You create value...with no EBITDA or revenue growth, but a much more robust infrastructure, it's a more valuable business." — Will Smith [39:06]
Cashflow Profile
- Negative working capital industry (collect up-front, pay later)
- Paid off ~$5m/year of debt, even with flat revenue, could return 40–50% ROE per year
5. Growth and Crisis: Marketing, Margin, and Macro Shocks [57:01]
- Year 1: Team-building and learning.
- Year 2: Tech and process overhaul—moved from pen-and-paper to real software.
- Marketing Surprises: Digital channels underwhelmed; direct mail (yes, retro!) was the growth unlock, especially for older demographic travelers. Word-of-mouth still king.
"We invested a lot in paid search, social...the results were pretty underwhelming. The big game changer? Classic direct mail." — Greg Geronimus [71:18]
- B2B2C Channel: Selling through universities, churches, community orgs delivered sizable group sales.
Crises Managed:
- Ebola, war in Ukraine, Zika, terrorism—numerous black swan disruptions; growth suffered, but didn’t break the business due to diversification.
"It was exhausting. Didn't have a tremendous business impact...but it did absolutely take a toll. A lot to navigate through as leaders." — Greg Geronimus [61:11]
6. Decision to Exit and Execution [75:20]
- Held for 4 years; doubled sales to nearly $50m, $7.5m EBITDA with larger, professionalized team.
- Received compelling unsolicited offers; sought board advice.
- Chose to run a competitive process with Fidus Partners; 78 NDAs, 37 IOIs, 12 management meetings, multiple LOIs.
- Key was being transparent: wanted to exit as operator, not continue for PE buyers.
"As much as we had transitioned away from the key person risk we inherited, we did create some with ourselves—but not nearly to the same degree." — Greg Geronimus [82:00]
7. Final Numbers and What Happened Next [87:20]
- Exit Price: 9x EBITDA = $67.5m, with $7.5m EBITDA on exit.
- Paid down ~$15m in debt, distributed ~$4m to investors during hold, net proceeds to investors $62.5m.
- Buyer (Summit Park, PE) struggled post-close due to COVID; ultimately shut Smart Tours down in 2022 after several years of restructuring.
"Good people, good plan, got hit by a Mack truck during COVID...with a leveraged capital structure and revenue going to zero, it was too tough a hole to climb out of." — Greg Geronimus [90:28]
8. Lessons and Life After Exit [88:21]
- Buy Well, Exit Better: Entry price/structure matters as much or more than post-close heroics.
- De-risking = Value: Just making a business less fragile can create outstanding returns.
- Don’t Get Greedy: Sometimes, the right time to sell is when things are hot, even if there's “more upside."
- Greg and David now run Footbridge Partners—search fund investors, highly hands-on, focused on backing a few traditional searchers per year (including more tour operator deals).
"You can create a lot of value on the way in. You can play it safe and still generate an excellent return. Don’t get too greedy." — Greg Geronimus [88:21]
Notable Quotes & Memorable Moments
- On Deal Origin:
- "I unknowingly emailed my cousin three times about buying his business...the first two were funny, the third he was annoyed." — Greg [10:22]
- On Direct Mail Unlock:
- "The silver bullet for tour operators is direct mail...not digital." — Industry advisor [72:28]
- On Pressure of Tour Operators:
- "It’s a command performance...you get blamed unless the experience is 10 out of 10." — Greg [66:12]
- On Exit Psychology and Boards:
- "Our board member said he’s never experienced seller’s remorse despite lots of exits. I think we took that to heart." — Greg [75:57]
Timestamps for Important Segments
- Background, Discovery of Search Funds: 04:14–08:39
- Designing the Search (Geography, Volume): 09:43–11:24
- Deal Origination and Structure: 13:04–15:42, 31:37–36:30
- Discussion of Entry Multiple, Seller Note: 35:41–39:06
- Operating Philosophy & De-risking: 49:44–54:20
- Crisis Management (Ebola, Ukraine, Zika): 57:01–61:11
- Direct Mail and B2B2C Unlocks: 71:34–74:57
- Exit Process, Auction, Board Influence: 75:20–81:35
- Final Economics of Exit: 87:20–88:21
- Post-Exit—Smart Tours Fate & Footbridge: 90:26–91:54
Tone and Language
Greg’s narrative is candid, self-effacing, and highly tactical. Will Smith brings a conversational but probing tone, unafraid to ask “dumb” questions and drawing out deeper lessons and specifics throughout.
Key Takeaways
- Sometimes the best deals aren’t found through volume but relationships.
- Pushing the seller to go first in negotiations may yield unexpectedly favorable terms.
- “De-risking” a business—building out team and process—can be as lucrative as growth.
- Tour operators are cyclical but have excellent cashflow and recurring business through customer experience.
- Aggressive digital marketing isn’t always a panacea; know your customer’s channel.
- Exit timing can matter as much as exit multiple; sometimes luck (and macro shocks) play a decisive role.
- “Buying well” gives tremendous optionality to owners: growth, cashflow, and exit—all with lower stress.
For More
- Acquiring Minds on YouTube
- Subscribe for Summaries, Upcoming Webinars
- Connect with Greg Geronimus [LinkedIn – see show notes]