Road To Carry is proudly supported by Reef Pass Investors
Reef Pass is a US based investment partnership that specializes in launching serial acquisition and HoldCo platforms (most often launched by ex-PE professionals).
Reef Pass brings decades of experience building acquisition platforms and flexible mandate across incubation and growth stages with a long-term capital base.
If you've ever thought seriously about launching your own acquisition platform, I'd love to hear your thesis!
Note: this partnership does not impact editorial independence.
Hi all - the 2026 Serial Acquirer Conference, co-hosted by Road To Carry and RollUpEurope, was a huge success! 🎉
Alex from RollUpEurope and Edwin from Road To Carry
Thank you to everyone who showed up. It was incredible to meet 160 of you in person.
I’m especially proud of the Roll Up Bootcamp participants who pitched investors during the private morning session. That’s a real step toward building something of your own.
We also heard unfiltered perspectives from an exceptional group of speakers
Bryan Rand (CEO of Rand & Co). On lessons learned from building a $400M revenue HoldCo
Cameron Perkins (Partner at Shore Search). On Shore Capital’s reimagination of search fund investing
Robert Brown & Dan Millen (Co-Founders of Reef Pass Investors). On lessons from public market’s 100-baggers applied to private market HoldCos
Rich Littlehale (Founder of Telos North) and Frankie Costa (CEO of Meridian Fleet Services). On life after Alpine-backed CEO role to pursue long-term HoldCo
Let’s dive into what Alex and I learned!
Session #1: Bryan Rand (CEO of Rand & Co). On lessons learned from building a $400M revenue HoldCo
Alex from RollUpEurope and Bryan Rand from Rand & Co
For those of you not familiar with Bryan, he’s the founder and CEO of Rand & Co Holdings - an Atlanta, Georgia, based HoldCo. 8 businesses with combined revenues of $400M. Sample investments: a commercial furniture; a fuel distributor; and a Mexican restaurant chain in the Chicago metro area.
The session’s title was “What It Really Takes to Build At Scale”. And in short… it takes a lot. Bryan did not mince his words:
“Many of the folks coming out of Private Equity have never made a decision… They’ve made recommendations, without having to own the outcome”.
Worse, PE-style “curated information” - high-quality QoE reports, management accounts etc. - often isn't available in lower mid market transactions.
Since everything looks easier in Excel than in real life, be humble and don't assume too many short-term wins. “When an SMB owner says they haven't invested in sales, there’s a reason for that. They’re not dumb, they’re generally not lazy.”
Next, we talked about shared services: a key value driver in PE-backed rollups, but challenging to deliver in a more makeshift setup. “[it is] not worth arguing with the PortCo CEO as to why the books didn't close… I can buy Accounting and IT Support much more cheaply than I can own them in-house”. Where Bryan has had traction, is on the Business Development front: “I have a bullpen of hungry folks who can make calls”. What else? Going to conferences. Updating the website. Setting up SEO.
AI adoption is one of the few areas of lower mid market where scale truly matters. Most smaller businesses, and their sponsors, are simply not resourced to “truly reward the iteration for the AI to really work”. Their AI efforts center on cost reduction and non-customer facing items.
We also discussed operator incentives. Bryan shared that: “Equity only really matters if it’s more than theoretical… Deleveraging is great but they don't take that currency at Kroger. You can't pay for your kids’ tuition with that”. Hence, offer the management a path to liquidity through dividends. It’s not as easy as it sounds. You’ll need a robust FP&A function to upstream cash in an expedient and tax-efficient manner. Also, lenders don't generally like dividends.
Bryan has a penchant for hiring executives in their 40s and 50s with unambiguous track records to run his Portcos. He is less dogmatic when it comes to operator compensation. “You can see their comp and where they are in their life, and you can back into what a meaningful outcome will be for them”. He’s tried everything: salary only; cash bonuses; co-investment; and equity / MIP.
Session #2: Cameron Perkins (Partner at Shore Search). On Shore Capital’s reimagination of search fund investing
Edwin from Road To Carry and Cameron Perkins from Shore Search Partners
Cameron’s career began as an emergency medicine and critical care provider in North Carolina. He co-founded FastMed Urgent Care in 2001, which eventually grew into a leading national urgent care platform with several successful recapitalizations.
Shore Search seeks to back acquisition entrepreneurs targeting $1-10M EBITDA businesses in industries with at least 500 targets. Their minimum check size is $5M, with a target equity commitment of $10-20M, including add-ons. A typical hold period is 5-8 years.
According to Cameron, Shore aims to “redefine excellence in Search”. Redefine how? By applying 3 pillars of excellence:
One, Mastering the fundamentals. “Not making first-time mistakes over and over again accelerates results”. Searchers have access to the parent firm’s playbooks, scorecards, and 100-day plans.
Two, Pattern recognition. Since inception, Shore Capital has founded 80+ platforms and made 1,300+ add-on acquisitions. That’s some serious institutional muscle memory
Three, Creating the compounding advantage through Board composition and network. As Cameron put it, “Federer had 5-7 people around him at all times, giving vantage points: hitting partners, physiotherapists, nutritionists, coaches”. Best boards help CEOs become better at prioritization and at decision making not by telling them what to do, but by continuously coaching them.
As to the common pitfalls in Search, Cameron singled out post-merger integration. Two major failure points being: 1) financial processes built too slowly (Shore pushes to get visibility within the first 90 days to 6 months); and 2) overestimating management team bandwidth post-close. Solution? Hosting a “pre-close Board meeting”.
This article is also sponsored by TechCredit Partners: your trusted debt advisor. It’s 2026: don't DIY debt. Focus on what you’re really good at. And let Linus take care of the debt raise.
Session #3: Robert Brown & Dan Millen (Co-Founders of Reef Pass Investors). On lessons from public market’s 100-baggers applied to private market HoldCos
Dan Millen (left) and Robert Brown (right)
Those attendees that do want to go on for as long as possible were rewarded with a presentation by Reef Pass Investors, an investment partnership that specializes in launching serial acquisition platforms, particularly as a long-term holdco model.
Robert and Dan began their careers in public markets, investing through what they call a “long-term private equity approach” (e.g., Danaher, Constellation Software, TransDigm, etc.)
Today, the team is busy hunting the next generation of 100-baggers in private markets. Here are some of their core principles for assessing new platforms:
The team should be launched at a founding level + must have deep experience in private equity, go-to-market, and high-velocity M&A
Top compounders are akin to top athletes: they exhibit discipline and ability to perform under pressure. “Surprises come up every week in HoldCo”. Are you able to set long-term goals and work towards them daily?
They also shared some balanced perspectives:
On the downside, some things have gotten much harder. Increased transparency equates increased competition for the best assets. Attractive niches fill up fast. And yet, as the next panel showed, specialist HoldCo investors can still win founders’ minds - and deals - against private equity.
On the plus side, we’re in the midst of a major SMB owner retirement wave, with lots of quality businesses coming to the market. Technological advances - remote work, offshoring, the rise of AI - enable HoldCo builders “to stay lean for a long time”. And importantly, it’s far easier to find, and debt fund acquisition targets.
Session #4: Rich Littlehale (Founder of Telos North) and Frankie Costa (CEO of Meridian Fleet Services). On life after Alpine-backed CEO role to pursue long-term HoldCo
Edwin (Left), Frankie (Center), Rich (Right)
Telos North “backs courageous founders with permanent capital, operational freedom, and a community of peers required to build companies that last”.
As for Frankie, he cut his teeth as the CEO of Helios, an Alpine Investors-backed light mechanical and commercial HVAC. Helios launched in 2020 by acquiring a 25-person shop in Oklahoma City. From there, Frankie scaled the franchise nationwide and into new business lines, eventually entering light commercial mechanical work - servicing clients like Dollar Tree and 7-Eleven.
When Frankie was ready to move on, he had no shortage of investor inbounds. However, he was otherwise oblivious to the HoldCo structure. A friend connected Frankie with Rich, who duly indoctrinated him about the model.
Caveat: Rich didn't need to sell Frankie on the concept of compounding. Frankie quoted Graham Weaver, the founder of Alpine Investors, lamenting about selling too early. A 5x MOIC isn't bad, but watching the next owner also print a 5x makes you realise you could've ended with a 25x - if only you had the structure to hold on.
Rich and Frankie introduced the concept of “Asymmetric warfare” to outcompete PE-backed aggregators. The explosion of interest in blue-collar services means that business owners in “hot” categories like HVAC or fleet management are inundated by buyer inbound. You can’t necessarily out-resource PE - but you can out-hustle.
Two examples to illustrate the point:
Example #1: meet owners on their terms. Fly / drive out wherever they’re based. Show up at 5am and hop in the truck. Make friends…or per Alex, maybe even grow a bushy beard like Frankie!
Example #2: it is reputationally advantageous to be structured as a company and not a fund vehicle. “Winning followership in the first weeks is existential”.
Road To Carry Interview Series
One of the most interesting themes emerging in the serial acquisition ecosystem today is the rise of AI-enabled roll-ups.
We’re continuing the RTC Interview series with Ilya Drozdov, co-founder and CEO of Dwelly. Dwelly is an AI-powered property management rollup platform in the UK. Dwelly recently raised $93 million, led by General Catalyst and Trinity Capital. With 10+ acquisitions in less than two years, the company is scaling aggressively.
We’ll talked about:
How AI is actually improving operations and margins
Scaling an AI-powered roll up platform
Convergence of VC and PE with AI and roll-ups
Register below.
Looking Ahead
This was our first event in NYC and we can’t thank you all enough for the support.
Over the last year writing the Road To Carry newsletter, I’ve met so many talented individuals across investing and operating roles who all wanted to build an acquisition platform of their own—just like I did.
With this conference, and many more to come, my goal with Road To Carry is to build a community where people who are serious about this path can find the right partners, learn from each other, and take real steps toward entrepreneurship.
I really hope that you will continue to be a part of this community we are building.
You can stay up to date on upcoming events by subscribing to Road To Carry’s event calendar and RollUpEurope’s event calendar.
Disclaimer: Unless noted otherwise, views and analysis expressed here are the author's own and based on public sources. The article is intended for informational and entertainment purposes only. This is not financial advice. Please consult a professional for investment decisions.