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Invest Like the Best with Patrick O'Shaughnessy

Royce Yudkoff & Rick Ruback - Entrepreneurship Through Acquisition - [Invest Like the Best, EP.423]

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Investing, Business, Technology

4.82.4K Ratings

🗓️ 13 May 2025

⏱️ 90 minutes

🧾️ Download transcript

Summary

My guests today are Rick Ruback and Royce Yudkoff. Rick and Royce are Harvard Business School professors who teach their students how to search for, acquire, and run small business directly after graduation. It has been almost a decade since our first conversation, and unlike many past interviews that have become outdated due to technology or market changes, the core principles they shared about entrepreneurship through acquisition remain remarkably relevant today. They explore fascinating developments in the search-fund ecosystem, including the bifurcation between funded searchers targeting larger companies and self-funded entrepreneurs finding success with smaller businesses. Rick and Royce share their accumulated wisdom on what makes a company worth buying, why the "magic is in the multiples," and how their students consistently achieve impressive returns through patient, value-oriented business acquisition. Please enjoy my conversation with Rick Ruback and Royce Yudkoff. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ here.⁠ ----- This episode is brought to you by⁠ Ramp⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠ Ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. –  This episode is brought to you by⁠ AlphaSense⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠ Alpha-Sense.com/Invest⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠ Ridgeline⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠ ridgelineapps.com⁠ to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:23) Changes in the Small Firm Acquisition Space (00:06:52) The Impact of SBA Loans on Acquisition Entrepreneurship (00:08:55) The Evolution of Entrepreneurship Through Acquisition (00:10:09) Risk and Return in the Search Fund Model (00:13:38) The Role of Investors in Funded and Unfunded Searches (00:19:33) Criteria for a Good Acquisition Target (00:28:36) The Growing Popularity of Self-Funded Searches (00:43:21) Challenges and Red Flags in Small Firm Acquisitions (00:49:47) Exploring Margin Expansion and Growth (00:51:02) The Impact of Practical Teaching in Business Education (00:52:12) Keys to a Successful Business Class (00:53:30) The Role of Theory in Practical Business Education (00:55:29) Challenges and Rewards of Teaching Business (00:57:46) Capital Allocation in Small Businesses (01:00:50) Advice for Aspiring Business Searchers (01:03:45) Value Creation and Business Lifecycle (01:08:20) Deciding to Leave Private Equity (01:11:20) The Future of Higher Education in Business (01:16:06) Ongoing Relationships with Former Students (01:18:45) Favorite Business Cases to Teach (01:24:46) Encouraging More People to Pursue Business Ownership

Transcript

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0:00.0

Early in my career, I'd spend hours alone in the film room thinking I was being productive.

0:06.3

But the truth was, I had no idea what I was doing.

0:10.0

I was just going through the motions.

0:12.5

That's what finance leaders tell me.

0:14.8

They're frustrated because they waste hours manually tracking expenses and reconciling statements

0:20.5

when they should be focusing on

0:22.4

driving their business forward. Be honest with me, how much of your time is spent on high value

0:28.4

work? For many finance teams, it's less than 20%, but you can change that right now with

0:34.9

Ramp. Ramp is a free corporate card that handles all the tedious

0:39.0

financial operations automatically, so your finance team can focus on what actually moves the

0:45.1

needle. One CFO told me they cut their month and close from five days to one. It's no surprise

0:52.2

over 25,000 businesses trust Ramp, including Shopify, CBRE, and Boys

0:58.5

and Girls Club of America. Don't waste any more time going through the motions. Check out Ramp at

1:04.9

ramp.com slash G-G. And for glue guys listeners, Ramp is offering metal cards for the next 30 days. Just go to

1:13.6

RAMP.com slash GG. Cards issued by Sutton Bank member FDIC. Terms and conditions apply.

1:22.6

Hey everyone, Patrick Roshanasi here. If you've been thinking about the infrastructure behind AI,

1:26.9

what's powering it where capital is flowing and how to stay ahead of the curve,

1:30.0

you'll want to join me for a live webcast I'm hosting with AlphaSense.

1:33.1

It's called What's Next for AI and Data Centers?

1:35.8

And we're diving into the feature of cloud compute, data center investment,

1:39.4

and the cybersecurity landscape that's forming around it.

1:42.0

I'll be joined by Michelle Brophy from AlphaSense and Gary

...

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