Winning All the Time Creates Weak Acquirers
While boarding my flight to New York City for a Serial Acquirers conference, I got a call from my non-entrepreneurial friend, who asked how on earth I was willing to travel all the way from Europe just to stay a few days in the US... This got me thinking that there are a lot of smart people out there looking to build a company, or acquire traditional niche businesses. Take "boring" companies with EBITDA of $1-5 million. Although, I believe, there is one big problem… They have been doing too well their entire lives. (There hasn’t been enough pain, rejection, or overall hard moments…) They come from good families. All they have seen and experienced is victory. They have everything they want in life. They’ve got all the presents from Santa. They won at home, they won in kindergarten, they won in preschool, high school, and later in college. All they have done is win. They have rarely, if ever, made mistakes, and lost. Just look at the candidates for the top private equity and venture capital firms. Not much has gone wrong in their entire lives. But when it comes to building a firm, an investment firm, a serial acquirer type of company - again, let’s take a portfolio of traditional businesses. First, you need a pipeline of these $1-5 million EBITDA companies; for that you need to be talking to founders, introducing yourself to brokers, you need to talk to investors, raise funding - putting it all together to finally get the deal over the line. Later operate this same company or companies. What happens 99.98% of the time… lots can go wrong. Every week. You look or feel stupid. It's embarrassing. The problem with people who haven't lost or made mistakes before... they can't cognitively process that well. So what’s the reality then? Should they go do another job, back to the W2 world? I don't know whether management consulting has lots of failures, but those people seem really smart to me and seem to do well, maybe they should keep doing that job. They should go do things where if you work hard and are smart, you're going to either win a lot or win a little, but basically you're going to win every day. But a portfolio of traditional businesses should not be built unless they are prepared to experience a lot of mistakes and very, very hard days. The best deal makers, the best investors, the best serial acquirers, the best compounders, need to be able to tolerate the pain... because from time to time, they do.
AI-Driven Lettings Roll‑up Scales with $93M Fundraise
. @DanLifshits, co-founder of Dwelly, explains how he and his partners are building an AI-enabled roll-up in the UK lettings market by acquiring independent agencies and modernizing them with software. After completing 9 acquisitions in just 24 months, Dwelly recently announced...

More Tools Lead to Better Products and Stronger Business
Although this example of increasing competitiveness comes from the public markets... I believe the same principle applies just as strongly to investing in and building companies in the $1-15M EBITDA range. "With more tools you are better equipped to understand the world...
From Family Office Advisor to Founder: Raising $25M
An important reminder if you work for a family office or just a HNWI and you've done a wonderful job allocating their capital across various asset classes: fixed income, real estate, public equities, PE, venture capital, private credit, commodities, and traditional...
Specialized Expertise Thrives Regardless of Market Conditions
I keep seeing and hearing that, in today’s market, many of the most seasoned people in finance are avoiding fundraises and choosing to go deal by deal... That said... I had a brief 30-minute conversation with a gentleman who has raised...
Investors Prefer Repeat Sponsor Deals, Building Holding Companies
Important to mention that most of their deals are independent sponsor deals, and most sponsors are not doing their first deal. So far, they’ve done ten deals, and many investors on the platform are building holding companies themselves. (For example, one of...
Vetted $16M HVAC Roll‑Up Offers 30% IRR
"I strongly believe there are many high net worth people in finance (IB, hedge fund, PE, etc) who have a desire to allocate some money to LMM deals/roll-ups but don't feel like they have access to vetted deals." How about an...

Acquire Niche Market Leaders, Not Just Many Deals
One observation stood out from my notes on the Swedish event, where more than 35 serial acquirers shared their portfolio companies, capital allocation frameworks, and long-term acquisition strategies: The deepest edge in acquisition entrepreneurship is not buying a lot of companies. It...
Dominating Tiny Niches Yields Premium Valuation
This niche holding company is trading at roughly 65x earnings (2025 numbers: $234M in net sales and $38M in EBITA). It focuses exclusively on acquiring and developing industrial and service businesses in narrow market niches. Its acquisition criteria are highly disciplined... it...
Family Office Patience Fuels 100x Acquisition Asset Class
Lacey Wismer has been investing in ETA since 2010. She has backed 100+ entrepreneurs and completed over 65 acquisitions. Family office patience with A-player urgency. Search funds. Holdcos. Serial acquisition. Fundless sponsors... These used to be separate lanes. Now they're merging into...
What Makes Top 1% Search Fund Operators Thrive
We just released an episode with Lacey Wismer, who has made over 100 search fund investments. We discuss what separates a top 1% operators from the rest. She also shares stories from her early days, including investments that returned 35x and 100x...

Estimating Market Value for $1.5B
I’m sure there’s no desire, or rush, to go public anytime soon, clearly. But as a thought exercise, based on their current numbers: >$1.5b revenue >$250m adjusted EBITDA >10% organic ARR growth >ca$1.4T technology services TAM What do you think the public markets would pay for...
Choose a Career You'd Play for Free
I keep coming back to what Eric said about his job in private equity & running his fund. “I would do this job for free. I love it so much. I really enjoy the intellectual challenge of solving the problems that...
Network‑Driven M&A Fuels Rapid Growth for Young Operator
Just finished a conversation with a true operator. "Being boots on the ground. Getting punched in the face."- type of guy. (As he described himself...= He scaled his firm organically from zero to $20M in sales. Then sold it to a strategic,...
Slow Starts, Strong Balance Sheets Fuel Serial Acquirer Success
Serial Acquirers, Stockholm and The Story of 47 Acquisitions Per Year Why serial acquirers remain one of the most powerful business models in the world. The best of them have acquired as many as 275 companies and traded at valuations as high...
Deep
The newsletter is almost 1,800 words. We go deep with examples of sourcing and the way they use AI across their 160 portfolio companies. Lastly, we break down their real economic engine in detail: - M&A - Talent - Playbook It goes out in 4-5...

Evergreen Secures 47 Acquisitions in One Year
Yes... the holding company that has acquired 160 companies in nine years is Evergreen. Ramsey, the co-founder in the middle next to Alex and me, spends his time speaking with business owners and leading Evergreen’s new platform and add-on acquisitions. He was...

Serial Acquirers Turn Cash Into Endless High‑Return Growth
One of the biggest reasons investors get excited about serial acquirers: They solve the reinvestment problem. In most businesses, good reinvestment opportunities are limited. You fund the core projects, maybe expand capacity, invest in product… and after that, the incremental dollar usually...
Acquisition‑Driven Holding Co. Hits $1.5B Revenue
There is a holding company acquiring technology services businesses. Since its founding in 2017, it has completed more than 150 acquisitions. Its highest annual acquisition volume has been as many as 47 companies in a single year. Today, the company generates $1.5...
Niche Holding Firm Commands 65x P/E via Dominant Acquisitions
There’s a niche holding company trading at roughly 65x earnings (2025 numbers: $234 million in net sales and $38 million in EBITA). The company focuses exclusively on acquiring and developing industrial and service businesses in narrow market niches. Its acquisition criteria are...
Operational Expertise Drives Speyside’s $1B Lower‑middle‑market Success
My conversation with Eric Wiklendt of Michigan based Speyside Equity. We discuss his journey and how the private equity firm has built a reputation as a highly operational lower-middle-market investor with close to $1B AUM, 38 total investments across 20 platforms,...

Serial Acquirer’s Playbook: 35 Deals in $50‑500M Manufacturing
Traveled to a Serial Acquirers conference in Stockholm, Sweden. The wifi at the hotel is slow, so it takes a little longer to upload the podcast episode with Eric Wiklendt of Speyside Equity, where he shares how they’ve acquired over 35...
Röko: Undervalued Serial Acquirer Poised for Growth
The holding company that almost no one talks about, yet it might be one of the most efficient compounding engines. RÖKO owns 29 niche, traditional businesses, runs at 21% margins, generates 14.5% returns on capital, and keeps acquiring new companies every...
Leverage Expertise, Not Assets, to Acquire Middle‑Market Firms
Speaking with a former hedge fund manager who started investing in and acquiring profitable lower middle market companies. There is a catch though.. The model often starts with advisory work, where clients are willing to pay substantial fees for judgment alone. There is...
First-Year CEO Playbook: Preserve, Learn, and Improve Quickly
Lessons from 60+ search fund deals and a few guiding principles for a new CEO’s first year at an acquired company (from seasoned search fund investor Tim Ludwig): 1. Do no harm. You (or the investors) bought a good business....
Talent‑First Strategy Powers Decades of Private‑Equity Returns
I started preparing for a research episode on a top private equity firm ($3B+ in AUM), and here are some of the notes I’ve taken so far: >Talent drives returns. >Their model is driven by the search for outlier investment talent. >Most of...
From Associate to GP: $95M Fund, 16 Niche Deals
1. Left an Associate role at a mid-market private equity firm 2. Raised $95 million over three years 3. Completed 16 acquisitions In this episode, I sit down with Kaido, who started his career at a PE fund in New...
Boring Success Gets 120 Views, Steak Grilling Gets Millions
There's an interview with a guy who quit his job and, with no prior experience, raised a $95 million to acquire 13+ "boring" niche businesses. Less than 120 views. Meanwhile, a gentleman grilling a wasabi-marinated A5 wagyu steak has over 7.5...
Flexibility to Invest Minority or Majority Drives Success
Talked to a small-cap private equity GP, and he said that from day one, they've always asked LPs for the flexibility to do both majority and minority investments... They’ve seen many great companies where the owners have clear reasons for not...
Elite Leaders Prove Focus, Long Hours Drive Success
Spent a long weekend with a group of folks in the mountains of Switzerland. All top people in their fields: a senior position in investment banking, CFO of a bank, serial acquirers, PE investors, etc. Some of the obvious observations: 1. Everyone’s busy,...

KKR Founders' First Capital and Early Investor Snapshot
A great one-page overview detailing the KKR founders’ initial capital contributions and the investors they raised from to finance their first leveraged buyouts. https://t.co/JQxW7mzQhZ
10 Cash‑
. @Travis_Jamison is sharing his story of doing 10 acquisitions in cash-flow-positive, profitable lower middle market businesses, with some deals projected to have an IRR of 25% or more. The best part: he is only getting started. These last 10 deals...

Sharing Your Deal Story Inspires New Acquirers
Important message for folks acquiring $2-15M EBITDA businesses, especially those who are willing to share their story and lessons down to the detail. Thanks to you, others are willing to take the leap. Just received a DM from a listener of the...
Buffett Chooses Companies with Durable, Layered Foundations
Vic Keller on Warren Buffett and Berkshire Hathaway acquiring three of his companies, and what he looked at in his companies: "Mr. Buffett acquired businesses that I was fortunate enough to be part of founding. I don't think anybody sells a...

KKR Co‑founder Relaxes Poolside, Scouting High‑debt Deals
A perfect weekend for George R. Roberts, the co-founder of KKR. > Sit by the pool > Read annual reports > Look for deals in the high-debt world https://t.co/MfCdQn4Ba1