5 Minutes in the Lower Middle Market
5 Minutes in the Lower Middle Market is a short daily podcast on the best ideas, lessons, and signals in the world of small business acquisitions, holdcos, private equity, and operating companies. In five minutes or less, it helps buyers, operators, and investors get sharper on what actually matters in the lower middle market.
Episodes
18 episodes
Why Every Business Owner Should Study This AI Example
In this episode of 5 Minutes in the Lower Middle Market, we explore one of the most eye-opening AI use cases I've seen in a traditional business.A roofing company in South Florida recently ran a blind test on a $6.5 million commercial e...
The Best-Performing Stock in S&P 500 History (621,000%)
In this episode of 5 Minutes in the Lower Middle Market, we study one of the greatest business builders of the last 50 years: Ken Langone.Most people know Langone as the co-founder of The Home Depot. Fewer know the story of how it all s...
482 Acquisitions in 16 Years: The John Malone Playbook
In this episode of 5 Minutes in the Lower Middle Market, we study one of the greatest capital allocators in history: John Malone.Most people know Malone as the architect behind cable giant TCI, where he reportedly completed 482 acquisit...
Why Thrive Holdings Is Spending $1 Billion on These Roll-Ups
In this episode of 5 Minutes in the Lower Middle Market, we explore a trend that would have sounded strange just a few years ago: venture-backed companies pivoting into roll-ups.For years, investors chased pure software businesses. Toda...
The Billionaires Behind Monaco's Superyachts (And the Businesses They Bought)
In this episode of 5 Minutes in the Lower Middle Market, we explore an unlikely place to study wealth creation: the harbor of Monaco during Formula 1 weekend.Many people assume the yachts belong to tech founders, celebrities, or hedge f...
How a Funeral Home Company Sold for $1 Billion
In today's 5 Minutes in the Lower Middle Market, we break down the story of Tribute Technology.What began as a simple website business serving funeral homes evolved into a comprehensive software platform used by thousands of customers a...
From $100k to $10B in Assets: The Lower-Middle-Market Playbook Behind Leon Capital Partners
In this 5 Minutes in the Lower Middle Market episode, we break down the story of Fernando De Leon and Leon Capital Group — one of the most fascinating lower middle market compounding stories most people have never heard about.Starting w...
The $2.2B Aerospace Roll-Up Nobody Talks About | Bryan Perkins and Novaria Group
In this 5 Minutes in the Lower Middle Market episode, we explore Novaria Group, which has completed 27 acquisitions since 2011 across niche aerospace and defense manufacturing.The broader lesson has little to do with aerospace itself. I...
This is The Most Overlooked Deal Sourcing Channel
In this episode of 5 Minutes in the Lower Middle Market, we explore one of the biggest competitive advantages in dealmaking: creative sourcing.The best opportunities often exist where others are not looking, where large institutions can...
The New Edge in Private Equity and the Lower Middle Market
In this episode of 5 Minutes in the Lower Middle Market, we explore how AI is starting to automate some of the most expensive cognitive work in finance — and why that matters for private equity, search funds and traditional small businesses.
From Small Timber Deals to Owning Gucci and Balenciaga
In this episode of 5 Minutes in the Lower Middle Market, we break down the story of François Pinault — the entrepreneur who started with a small timber trading company and eventually built Kering, the luxury empire behind Gucci, Balenciaga, Sai...
The $727B Market Behind Small Business Acquisitions
In this episode of 5 Minutes in the Lower Middle Market, we look at SBA lending through the SBA Loan Intelligence Database from MA Labs.The big takeaway: SBA lending is not a niche corner of small business finance. With 2.1 million loan...
The Swiss Cheese Model for Picking Great CEOs
In this episode of 5 Minutes in the Lower Middle Market, we explore a simple idea: great operators are often the people who have already passed through many hard filters.The lesson: when hiring a GM, backing a CEO, or evaluating managem...
Solo Search vs. Partnered Search: What the Data Says
In this episode of 5 Minutes in the Lower Middle Market, we look at the data behind solo searchers versus partnered search funds and why partnerships have historically outperformed on average.0:00 Patience as an investor, impatience as ...
The Quiet $20B Empire Built on HVAC, Filtration, and Safety | Larry Gies of Madison Industries
In this episode of 5 Minutes in the Lower Middle Market, we look at Larry Gies and Madison Industries, one of the best examples of how boring, unglamorous businesses can create enormous value.The lesson: you do not need a glamorous busi...
Great Businesses Aren’t Always Forever Holds
In this episode of 5 Minutes in the Lower Middle Market, we explore why good lower middle market deals should not go to zero and why great businesses are not always automatic forever holds.The lesson: great investing is not just about c...
The Hidden Advantage Small Buyers Have Over PE Firms
In this episode of 5 Minutes in the Lower Middle Market:- Why the best investment theses can be explained in just a few sentences- Why family offices are shifting away from traditional private equity funds toward direct investing
Everyone’s Heavy on AI But Boring Businesses Still Pay the Bills
In a world obsessed with what’s new, some of the biggest opportunities in the lower middle market still come from very old principles: durable demand, real relationships, consistency, and curiosity.In this episode of 5 Minutes in the Lo...
