Acquiring Minds Podcast Summary
Episode Title: Why Choose Ownership Over Being a CEO
Host: Will Smith
Guests: Catherine Butler Dines & Rahul Desai, Owners of Women Travel Abroad
Date: November 10, 2025
Episode Overview
In this episode, Will Smith interviews Catherine Butler Dines and her husband, Rahul Desai, about their journey from high-powered careers in private equity and venture-backed startups to owning and operating Women Travel Abroad, a small but growing travel business focused on guided tours for women. The conversation explores the deep distinctions between being a CEO under the direction of others versus owning a business outright, the process of self-funded search, leveraging technology in traditional industries, and the rewards and tradeoffs of choosing autonomy and lifestyle over scale and prestige.
Key Discussion Points & Insights
1. Backgrounds & Early Career Trajectories
-
Catherine:
- Studied international relations and Arabic, originally aiming for diplomacy.
- Fell in love with business while working for a travel startup in Morocco.
- Post-COVID, shifted from consulting to an MBA at Duke, became involved in the ETA (Entrepreneurship Through Acquisition) world.
- Considered but ultimately bypassed traditional search in favor of a role as a PE-backed CEO, then moved to self-funded entrepreneurship.
- Timestamp: [04:42–05:57]
-
Rahul:
- Georgetown grad with early entrepreneurial efforts in machine learning.
- Moved from consulting to Silicon Valley, held roles at two high-growth startups in insurtech.
- Became jaded by the “lottery ticket” nature of startups: high equity dilution, small payouts for most employees.
- Supported Catherine’s search while keeping his PE job.
- Timestamp: [06:04–07:43]
Notable Quote:
“We’d rather own more of a smaller outcome than a very tiny fraction of a big outcome.”
— Rahul Desai [08:47]
2. Why Not Remain an Employee CEO? (Private Equity vs. Ownership)
- Catherine’s PE CEO Experience:
- Ran an IT services firm within Alpine Investor’s Evergreen Services Group.
- Realized lack of true authority as a portfolio company CEO; felt constricted in values-driven decision-making.
- Pivot Point: Board pushback over giving an essential offshore employee a small raise for family health reasons.
- Timestamp: [19:26–24:32]
Notable Quote:
“It didn’t sit very well that I was having to choose between treating an employee as a person… and it was only a conversation about profits. I realized I have a very specific value set…and the only way to mesh that with how I run a business is by owning at least 51%.”
— Catherine Butler Dines [23:38]
3. Decision to Pursue Self-Funded Search
- Both chose flexibility and control over structure and scale—kept day jobs, used nights and weekends for deal sourcing.
- Initially focused search on Cincinnati B2B services with standard ETA criteria; expanded to travel businesses after Rahul stepped back.
- Timestamp: [25:24–32:06]
Search Process Stats:
- 80 SIMs reviewed, 100+ businesses examined.
- Two deals nearly closed; learned costly diligence lessons when losing one at the wire due to seller’s personal tragedy.
- Timestamp: [26:40–31:13]
4. Acquiring Women Travel Abroad: Model & Strategy
- Looked for niche group tour operators with strong, repeat customer base and proprietary itineraries—not traditional travel agencies, not location-tied businesses.
- Timestamp: [32:06–35:57]
- Chose travel business despite industry cyclicality and lack of recurring revenue because:
- Catherine’s specific industry skills and background.
- Rahul’s ability to tech-enable and automate back office, reducing typical headcount-linked cost scaling.
Notable Quote:
“I was confident we could run at higher net income margins than the typical travel company because I had free labor [Rahul]…our secret sauce.”
— Catherine [39:41]
- Built a proprietary, no-code back office with heavy AI automation, effectively replacing expensive industry SaaS tools and further compressing costs.
- Timestamp: [43:15–45:55]
5. Deal Structure, Size, and Risk Profile
- Deal:
- Revenue at acquisition: ~$800,000
- SDE: ~$280,000
- Purchase Price: $500,000 (below 2x SDE)
- Funded with personal equity, family/friends capital, home equity line, and seller note. No bank or SBA debt: “prefer to sleep at night.”
- Seller worked minimal hours; transition was smooth.
- Timestamp: [52:29–57:19]
Notable Quotes:
“My benchmark was 51%. I wasn’t willing to give up any more ownership than that.”
— Catherine [58:21]
“If you cash flow $300k a year in Cincinnati, you can live a splendid life. If we return capital, own 100%, that’s a great outcome.”
— Rahul [66:01]
6. Operating & Scaling the Business
-
Focus on maintaining high margins (15–20%), rigorous financial discipline (automated treasury, strong accounting).
- Timestamp: [51:58–52:06], [73:00–73:54]
-
Manual and AI-driven marketing wins: SEO-powered inbound, 5x website traffic growth via AI-generated blogging.
- Timestamp: [73:00–74:00]
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Strategic vision: grow Women Travel Abroad to $4–5M in revenue; bolt on similar niche tour operators, all sharing back office “in a box.”
- Timestamp: [75:00–78:08]
Notable Quote:
“Our goal is, can we build the travel back office in a box and then deploy it to every company we buy?”
— Rahul [49:10]
7. Lifestyle Design and Long-Term Vision
- Both prioritize autonomy, flexibility, and lifestyle over ROI maximization or empire-building.
- Desire to move from “individual contributor” roles to true capital allocators and strategists as platform grows.
- Investors are friends/family/industry strategic partners with no fixed exit horizon.
Notable Quotes:
“Owning more of a smaller thing gave me flexibility and autonomy, rather than owning less of a bigger thing.”
— Catherine [68:43]
Memorable Moments & Quotes
-
On the Value of Ownership:
“As long as I had the vast majority of ownership, I felt okay. My benchmark was 51%… Owning the majority of it, I can decide to run the business however I want.”
— Catherine [58:21] -
On the Risk/Reward of Small Business Ownership:
“Buy as big as you can is conventional wisdom…but if you balance risk, structure, and lifestyle—it might make sense to go small, at least for your first business.”
— Paraphrased from Catherine & Rahul [62:45–66:01] -
On Negative Cash Conversion:
“Most deal structures are around the idea of AR; but if you have negative cash conversion, you have to negotiate differently. Cash conversion is an underappreciated aspect of deal structuring.”
— Catherine [83:27–83:46]
Key Timestamps
- [04:42–07:43] — Host and guests’ backgrounds
- [19:26–24:32] — Catherine’s turning point as a PE CEO
- [25:24–32:06] — Transition to self-funded search
- [32:06–35:57] — Why choose a travel business
- [43:15–45:55] — Tech enablement: building proprietary back office
- [52:29–57:19] — Deal structure, use of equity, seller note
- [66:01–67:17] — Discussing risk/reward and lifestyle payoff
- [73:00–74:00] — AI-powered marketing and margin discipline
- [75:00–78:08] — Scaling vision, future bolt-on acquisitions
- [83:27–83:46] — Lessons on negative cash conversion
Conclusion
This episode offers a candid, nuanced look into the psychological and financial calculus behind small business acquisition, the tradeoffs between CEO and owner mindsets, and the practicalities of buying, operating, and scaling a niche service business. Catherine and Rahul’s journey answers the question: “Why ownership?” by showing how the ability to align business with personal values, lifestyle, and autonomy can outweigh the lure of scale or prestige in the entrepreneurial path.
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