The Most Attractive Market Isn’t Always the Fastest‑growing.
Just finished a conversation with a buyer who started building a rollup in a very specific industry back in 2020. They completed 40+ acquisitions and eventually sold the platform to a well-known PE firm. What stood out was the growth rate of the market they went after — they chose the one that was growing 5-7% and not the one that was growing 15% per year… When I asked why they didn’t chase the faster growing category, he said, “the most attractive market is not always the best market.” “And faster growth often brings more competition, more capital, higher seller expectations, and more ways for deals to go sideways.” The 5-7% CAGR market still had all the great credentials: a fragmented industry with sticky customers and high gross margins. Being under the radar seemed to be working well for them. They rolled some equity, so they’re still building but they also back new emerging founders from their small fund.
Start Small, Build Platforms, Then Acquire Luxury Giants
Imagine going from building a small and "boring" roll-up of timber companies to buying Gucci, Balenciaga and Yves Saint Laurent. True story. And the lesson in today's 5 Minutes in the Lower Middle Market is that the first business and acquisition...
Evergreen's HoldCo Drives 100+ Tech Acquisitions
For those curious about Evergreen’s operating groups, this is from their presentation at the serial acquirers conference in Stockholm: HoldCo level - 45 people focused on M&A, talent and finance LYRA - Technology MSP for SMBs Launched 2017 100+ acquisitions $1B+ revenue PINE - Could ERP...
Young Founders Drive 160+ Deals, $1.5B Sales
A firm started by a 25 and 27 year old. So far 160+ acquisitions $1.5B in sales and $250M in EBITDA Wildest part? 47 acquisitions in 2025 alone... A true masters at sourcing, deal execution, and everything else included.
Serial Entrepreneurs Thrive on Creation, Not Just Profit
Had a short in-person meeting with a true serial entrepreneur in his 50s. He had an early exit 20 years ago, and another one a few years ago. You can say the motive for profit and quality of life is...
Solo Search Funds Closing Gap, Delivering 5x+ Returns
Starting a search fund solo is a good idea. Keep reading... Solo searchers have returned an IRR of 27.4% compared to partnership returns of 40.3% in 2022. Partner search ROI was 3.8x compared to 2.9x for solo searchers in this 2022 study, an...
Mundane Businesses Can Become Multi‑billion Roll‑up Successes
Did you know that Chicago accountant Larry Gies bought his first company by maxing out 10 credit cards and borrowing $50,000 from a high school friend? He eventually built Madison Industries into a platform generating more than $5B in revenue by...
EOS Turns Chaos Into $77M, 15‑Company Portfolio
Sid is a strong believer in EOS and was one of the first people to recommend Traction by Gino Wickman to me. He has effectively integrated EOS across his business, helping him scale the firm into a portfolio of 15 companies...
Start Slow, Find Fit, Then Accelerate Acquisitions
When you study the serial acquirers model and those who’ve invested in this model for decades, you see that companies that completed 1-2 acquisitions per year in the early years tended to outperform those that pursued a faster pace, such...
EOS Drives Success: Right People, Real‑Time Scorecards
Seen EOS used by so many 7-, 8-, 9-figure holdco builders, including many former podcast guest. Finally started reading, 10 minutes in: 1. The right people in the right seats (are all of your people the right ones for their jobs?) 2....
Niche Strategy: 95 Deals Targeting $2‑10M Companies
Hyperfocus on one industry. Only acquire companies with $2-10 million in revenue. Repeat the playbook with 95 acquisitions. https://t.co/PXAPSDRwed
60% of Owners Limit Loan Talks to 2‑5 Lenders
Weekend data analysis after speaking with 250 small business owners over the past few months. Here is an interesting pattern around debt financing. One stood out immediately: Roughly 60% of owner-operators only speak with 2-3, max 5 lenders when evaluating financing options. I thought...
Profitable Businesses Rarely Lose Value, yet Competition Evolves
I hope today’s 5 Minutes in the Lower Middle Market really gets you thinking about capital allocation: 1. Why a true investment in a proven, profitable, growing, well-managed business should rarely, if ever, go to zero. 2. Buying a great...
Family Offices Favor Direct Deals, Trust Beats Size
5 Minutes in the Lower Middle Market 1. Family offices are shifting away from PE funds toward direct investing 2. Relationships and trust as a competitive advantage 3. How independent sponsors beat larger PE firms in deals 0:00 Steven Spielberg’s lesson...
From Island Roots to Building His Own Empire
Had a pre-call with a podcast guest. He comes from a very tiny island, worked for a private equity firm, then went to HBS and met his cofounder. So far they've done over 3 acquisitions. We record, hopefully in person, in early...
Ex‑founders Crave Ownership: Buying Businesses to Build From Within
Every now and then, I get inbound from someone who - has built and sold a tech firm, or was the founder of a VC backed startup - and then took some time off (advisory, consultancy, or angel investing). Just to...
Durable Demand, Relationships, and Boring Cash‑generating Businesses Win
5 Minutes in the Lower Middle Market Today's takeaways: 1. Boring businesses that keep printing cash (@BoringBiz_) 2. The best networkers don’t feel like networkers 3. Why scripted private equity outreach fails (@PadraicMcC) 4. The old rules still win: - Own businesses with...
From Goldman Sachs to Hong Kong: Launching a New Venture
Not too many people are willing to quit their job at Goldman Sachs to start a business. But it gets even better… He decided to move from the US to Hong Kong. Very glad I got to talk Alex. It was great to...
Ex‑rental Owner Seeks Hands‑on Investor, Not Banker
Over the past 2-3 years, I’ve built a great relationship with this one traditional business owner. He used to run a heavy equipment rental company. Sub-$2M in EBITDA. This deal died for me at the last minute as the other...
Long‑term Acquisitions Gamble on Static Competition; Know when to Exit
The thinking exercise when it comes to buying a company and holding it for a long period of time... Doing that, you’re basically hoping that, over a generation time frame, the competitive environment doesn’t change, which, in a way, is a...
Educating Owners: Cutting Through Unrealistic Valuation Expectations
Not a week goes by without hearing about traditional business owners with valuation expectations that are completely detached from reality... I've seen and experienced that to be one of the real drawbacks of proprietary deal flow. When no broker or advisor has...
Dino Polska’s Capital Discipline Fuels 20‑30% Store Returns
Update: They opened 345 stores in 2025 (a total of 3,033). It's the weekend, so if you want to learn capital allocation 101… Dino Polska is a great example of how focused and robust financials and a carefully designed operating model can...
True Private Equity Deals Should Never Hit Zero Value
Value degradation in the space of business acquisitions and private equity... “Within any given portfolio in finance, you probably should expect one or two deals to go to zero...” Craig Dupper of Elan Growth Partners believes this is not the case at...
Say Yes to Your Idea, Reap Real Results
Coming back to this story of my university teacher a few times a year. During our last class before the exams, he asked each and every student where they’d want to work and what business they’d want to build. Having formal experience...
Great Ideas Surface During Walks and Workouts.
Having a slower day than usual. I can confirm that great ideas often “whisper” during non-work moments (walks, showers, between sets at the gym). It’s no surprise that daily walks and workouts are the favorite hobbies of great investors and capital allocators.
Patience and Networks Beat Brokers in Deal Hunting
Found myself reading the quarterly investor letter of Hayden Capital, a small hedge fund run by Fred Liu. "Avid investors. Lifelong learners." as they describe their team of professionals. In the Q4 2025 letter, he said: ' picking winners (and importantly,...
People, Not Paperwork, Drive Post‑Acquisition Success
You can spend months or years trying to buy a business, but once day one arrives, all of that effort disappears. Talked to 100+ investors? Many more company owners? Spend 6 figures on closing processes… all this does not matter. What matters now is...
Embrace Unqualified Risks to Own Your Future
"Don’t be afraid to try what you’re not qualified to do. If I only did what I was qualified to do, I’d be pushing a broom somewhere." -Sacca I received an email from someone who said they had just listened to this episode...
Personal Capital Fuels Growth in Undervalued Companies
I had an hour-long conversation with a former investment banker who now travels around the world to acquire and invest in companies that, let's say, don't fit neatly within traditional multi-company portfolio strategies... These are not necessarily distressed assets, but rather...
Industry Experts, Not Finance, Drive PE Rollup Success
Lessons from 137 acquisitions Robert Irving of Buffalo Growth Partners shares what he learned from building a fire protection business from zero to $20 million in revenue, selling it to private equity, rolling equity, and then helping execute a 137-company rollup. @aggieirving...
Deal Quality, Not Partners, Drives Rapid Acquisition Surge
Had a quick 30 minute conversation with a guy who has done six acquisitions and is working on another three right at that moment. "Finding operating partners has not been difficult. The issue is not finding people; the issue is finding...
Magazine Covers Lag; Direct Deals Become New ETA Norm
The magazine cover indicator? The old contrarian tell: by the time a trade is on the cover of Time or Forbes, it's already crowded. At least be aware of the signals... Last 48 hours on X: chatter out of an SMB conference...
Generous Founder Secures 44 Investors for Australian Acquisitions
Great entrepreneurs and even better people. Having known Jason for a little longer, he's always been very generous. Sharing thoughts and feedback on content, looking at the few deals I wanted to close. Going as far as saying he'd be keen...
Acquiring Is Easy; Operating Demands Naïve Optimism
Here’s one thing I’ve learned after 160+ podcast conversations with people buying, operating, and scaling lower middle market businesses: It requires a lot of optimism and naivety. Describing these people... yes, they're all extremely capable, great at executing the skills needed to...
From Evening Firewood to 40s Entrepreneurial Success
Each April, we attend a small birthday gathering at a friend’s home. There is always this one guy whose entrepreneurial story I really like. Ten years ago, he was working a 9 to 5 job. During most evenings, he started cutting and...
Scaling $117M via 95 Acquisitions Inspired by Legends
Doing research and preparation for the podcast conversation with a gentleman who, since 2006, has completed 95 small acquisitions and been able to grow revenue to $117M while maintaining EBITDA of approximately $28M. He does it in a highly fragmented industry,...
Real Estate Often Outvalues the Underlying Small Business
The value of the land > the business itself I spoke with a family office that owns a portfolio of small businesses. One interesting point the son of the owner made was that, in several cases, the underlying real estate is...
Credibility Over Capital: BHC’s Blueprint for Middle‑Market M&A
Great find. I'd add here the research where I explore Bowles Hollowell Conner & Co., the quiet Charlotte-based advisory firm that shaped how lower middle market M&A gets done. Before private equity was institutionalized asset class, BHC figured out how to...
Cold Email Mastery Leads to $25M Venture
You can improve your life so much by mastering how to write an excellent cold email... That's exactly how Simon met his co-founder. He spent half a day writing it and had his wife proofread it. They then became business partners and bought...
Leaving Top PE for Independent Deals: High Risk, Higher Reward
How risky is it really to leave a top-paying PE firm to become an independent sponsor and buy a $2-10M EBITDA business yourself? (Think of people working at Warburg Pincus, Vista Equity, KKR, Bain, Carlyle, TPG, Hellman & Friedman, Apollo.) I read...
Gritty Maverick Built DLJ Into Wall Street Powerhouse
“I have to be busy, and I just love building things that make a difference.” In a 1986 Wall Street Journal article, Tony James was described as an up-and-coming M&A whiz kid. He transformed DLJ from a mid-sized brokerage into one of...
True Success Demands Genuine Passion, Not Fake Curiosity
You can’t fake curiosity and passion. Whether it’s building a portfolio of traditional businesses that generate cash flow... Or raising capital in venture, or running a B2B software company... You’re competing with people who live and breathe their craft, and if you don’t,...
Serial Home‑Service Founder Turns Pool Industry Into Scalable Brand
Here is @jeremyyamaguchi explaining his thesis on why he decided to acquire pool services businesses. So far, he has acquired 10 companies in a short 18 months. Jeremy has previously built, scaled, and exited three home services businesses: 1. Golden Shine (housekeeping)...
US HoldCos Leverage Aggressive Data Capture for Faster Value
Building a HoldCo in the US versus Europe Here is one specific example that shows how different it can be: I spoke with a European investor, entrepreneur, and now HoldCo builder who has experience operating in both markets. He said something that...
Build Trust Networks For
Why networks are one of the most underrated advantages in the lower middle market, and how to build them. We explore how trust, introductions, persistence, and long-term generosity can create better deal flow, stronger relationships, and a real competitive edge for...
True Learning Shows Up in Changed Behavior
Learning is a behavioral change. “If your behavior hasn’t changed, you haven’t learned.” – @alixpasquet
Ownership Shifts Analysis: Live With Your Decisions
A few days in New York City and an important message from a former partner at a lower middle market private eqity firm. Today, he runs his own firm. He has bought 8 companies, all legacy buyouts, with companies that have been...
Call Founders Directly to Master Niche Industries Quickly
I still think one of the best ways to understand traditional niche businesses and industries is by picking up the phone book and calling founders. With every founder you meet and every company you visit, you can soak in so much...
From Struggling Buyout to Global Fund Builder
My conversation with @PRamanathan on how he helped lead a management buyout of a struggling cathodic protection business in 2003 and turned it into Corrosion Technology Services. Himself local to Dubai, Ram's company, CTS, includes 10 companies operating across 8 countries...
Buyout Strategies Look Same; People Make the Difference
When talking to a lot of lower middle market firms, the buyout strategy is almost always the same. There is not a lot of differentiation. They are all kind of doing the same thing. What is different are the people and personalities...