🔑 How to build a HoldCo into $20 billion+
Welcome to The Business Buying Academy with Sieva Kozinsky. Here's what we have in store for you today:
- Want to get your business in front of my audience?
- Buying a $127 million stake in a failing bank
- Want to build a $400 million/year HoldCo?
🔑 Market your business to Sieva's Business Business Academy audience
We began testing with our first advertisers last year, and it turns out this community is incredibly engaged. With 70,000 operators, investors, and "acquisition curious" reading this letter each week, we drove customers for advertisers ranging from Vesto (treasury management platform) to Mainshares (sourcing investors for SMB acquisitions).
We are looking for a couple new advertisers to partner with this year as we launch a few new products.
Interested in marketing your business to this audience? Just respond to this newsletter and say hi.
🔑 A Unique HoldCo Model: How to Spot Undervalued Businesses
I love to study holding companies.
Lately, I've been scouring books and articles to find interesting HoldCo operators.
One I found a while ago is Portland Holdings, the creation of billionaire Michael Lee-Chin.
While many know the big-name HoldCos, this story is one you probably haven't heard.
It's a masterclass in building a HoldCo through targeted acquisitions in underserved markets like the Caribbean.
We'll explore Michael's buy-and-build playbook, the intricate HoldCo structure that supports it, key deals, and expanded actionable lessons for running your own holding company. Let's get into it.
How Portland Holdings Started
Michael Lee-Chin was born in 1951 in Port Antonio, Jamaica, to a modest family. His mother worked as a bookkeeper, while his stepfather ran a grocery store.
As a teen, he hustled jobs like landscaping at a hotel and cleaning cruise ship engines.
In 1970, he immigrated to Canada on a scholarship to study civil engineering at McMaster University, graduating in 1974. After a brief stint as a road engineer back in Jamaica, he returned to Canada, working as a bouncer before entering finance as a financial advisor at Investors Group in 1979.
Then his business career started.
In 1983 when he borrowed $500,000 (in Canadian dollars) to buy shares in a Canadian investment firm called Mackenzie Financial.
His stake appreciated to $3.5 million by 1987.
With that capital, he acquired a small investment firm, Advantage Investment Council (AIC Limited), for $200,000.
Under his leadership, AIC grew from $800,000 in assets to nearly $15 billion at its peak decades later, focusing on a "buy, hold, and prosper" strategy inspired by Warren Buffett and Benjamin Graham.
In the meantime, he started Portland Holdings in the late 80s as he grew AIC.
“Most people make decisions and act on their decisions based on: ‘Ready, aim, aim, aim, aim, aim…,” Lee-Chin said in an interview. “What I do, is I ready, aim, and if I’m in the vicinity, I fire.”- Michael Lee-Chin on his investment philosophy
Today, it's a privately held HoldCo influencing about $20 billion in assets across financial services, insurance, tourism, agriculture, real estate, energy, and biotech, with operations in over 20 countries but a heavy emphasis on the Caribbean and Latin America.
Portland's structure is classic HoldCo:
A top-level entity that holds controlling stakes in subsidiaries, allowing centralized strategic oversight while granting operational autonomy to each business.
This setup minimizes risk through diversification, optimizes tax efficiencies via Canadian-Caribbean treaties, and enables efficient capital allocation across borders.
The Caribbean Buy-and-Build Machine
Chin's genius lies in spotting undervalued opportunities in emerging markets, particularly his native Caribbean.
He noticed large inefficiencies in Caribbean markets that many American investors didn't care to pursue.
In short, this was his strategy:
Acquire controlling stakes, build synergies, and hold for long-term value creation.
He avoids diversification for its own sake, instead owning a few high-quality businesses in growth sectors.
Plus he has a few other rules. Every acquisition must:
- Every acquisition must exhibit solid returns on equity
- Be in a long-term growth industry
- Have entrepreneurial management
- Possess global leadership potential
- Have a competitive advantages (like brands or licenses).
Let's take a look at once specific deal and see how it went.
In 2002, Portland Holdings acquired 75% of National Commercial Bank Jamaica (NCB) for US$127M
At the time, NCB was Jamaica's third-largest bank, but it had been severely impacted by the country's 1990s financial crisis, during which high interest rates, currency devaluation, and widespread bank failures led to government intervention via the Financial Sector Adjustment Company (FINSAC). FINSAC had bailed out and restructured several institutions, including NCB, before putting it up for privatization
- Portland Holdings Website
The Jamaican banking sector in the late 1990s and early 2000s was plagued by systemic inefficiencies.
High inflation, interest rates exceeding 50%, and a debt-to-GDP ratio over 150% led to widespread non-performing loans (NPLs), bank insolvencies, and a loss of public confidence.
NCB itself suffered from demoralized staff, dejected customers and outdated manual processes.
Chin and his investors made a bet that Jamaica's financial system would recover.
It paid off.
They grew the bank from $6 million in profits to about $85 million in just a few years.
Cumulative profits reached US$1.45 billion from 2004 to 2017 as NCB became the largest bank in the country.
NCB is just one of dozens of success stories for Portland Holdings.
But the lessons from most of them boil down to the following:
- Bet on Underdogs in Underserved Markets: Invest where others overlook. Inefficiencies = opportunity. Jamaica's 1990s financial crisis was Lee-Chin's entry for NCB, turning it into a HoldCo cornerstone.
- Apply Strict Acquisition Criteria: Chin sticks to his strict rules for buying companies, and knows exactly what he's looking for. He can hit home runs repeatedly because he's only looking for a very specific type of business he knows exactly what to do with.
- Buy-and-Hold with Discipline: Own a few high-quality businesses you understand deeply. Finance optimally with tolerable debt, reinvest cash flows, and hold long-term. In a HoldCo, this builds compounding without constant churn.
🔑 He Does $400 Million a Year in Revenue
Want to understand how to buy and operate businesses like a pro?
Then you need to listen to this conversation.
I spoke with Bryan Rand, CEO of Rand & Co, who owns 9 platform businesses with $400 million in total revenue.
Bryan told me how he buys businesses, the wild story of how he started a fuel delivery business, and how he teaches his kids entrepreneurship and investing.
This is a fascinating conversation. Watch it if you want to build a holding company
Have a great day,
Sieva
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