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.

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Last week we were in Greenland, learning how the Inuit survive on barren rock and ice. Did you know that the Inuit arrived 200 years after the Norse. Unlike the Inuit though, the Norse were wiped out sometime in the 15th century. 

Shame, because the Norse settlement bears all hallmarks of a Venture Capitalist experiment. A charismatic founder with “scar tissue”. A contrarian strategy to unlock a huge TAM. I'm talking about Erik the Red of course - a Viking outlaw who discovered Greenland while in exile. Upon return to Iceland, Erik convinced enough people to fill 25 ships to join him in settling the aptly named “Green Land” (only 14 ships made it through).  

Erik would have no trouble building rapport with modern Venture Capitalists whose romanticised ideas of Holding Companies bear uncanny resemblance to his Greenland pitch  - a contrarian bet sold on the promise of outsized returns. Traditional HoldCo investors - Family Offices, dedicated funds like Reef Pass, the Will Thorndike tribe etc. - therefore, need not worry. Further reading: Hold It - Don't Drop It - Don't Stop It! Why Long Term Hold is this decade’s hottest investment trend. The two tribes are hardly competing for the same resources. Most VCs are uninterested in equity efficient, patient compounders. They want to be backing Founders That Buy Boomer Businesses At Scale And Change Them With AI.  

Fear not, there’s enough supply for everyone, and not only in America:    

Italy is calling - for real this time! Two days in Milan mapping Europe’s hottest (quite literally) succession market

We spent a week among management consultants chasing Germany’s blue-collar succession dream. 3 things we learnt

Meet NGTG: the Danaher of Japan riding the SMB succession bonanza

But be careful - the seas might be stormy. This week, we take a fresh look at Teamshares - a flag-bearer of the HoldCo hype and, since last month, a publicly listed company (via a SPAC with Live Oak Acquisition Corp. V):

Teamshares knows a thing or two about survival and adaptation. Read on to find out:

If you’re new to the Teamshares story, check out the first two instalments of our series:

Teamshares wants to dominate America’s SMB succession game - but do the numbers add up? 5 observations after digging through the SPAC docs (published in 2025)

Admired, copied, misunderstood: the incredible story of Teamshares (published in 2024)

Before we tuck in, a shoutout to our sponsor TechCredit Partners… THE debt advisor to rollups, HoldCos and Independent Sponsors. If you’re looking for $5M-$100M in debt capital, TechCredit Partners will help you close the optimal deal. 

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Teamshares’ impressive statistics - nearly $500M in revenue, 90-plus portfolio companies, international ambitions - belie a tumultuous past. The original equity story revolved not so much around owning companies, as harvesting their cash flows for as-yet-to-be-developed fintech products. Back in 2023, the Teamshares CEO Michael Brown cheerfully declared: “We built a neobank, we’re soon to launch credit cards, and we’re building an insurance business as well, so there’s a secondary layer of financial products that will basically replace the vendors that the companies used to use”. 

To paraphrase, Michael’s strategy was:

Teamshares run-rate revenue surged from $10M in January 2021 to $400M in August 2023 (source). Breakneck growth requires tradeoffs, which explains why Teamshares ended up with dozens of $500K EBITDA gift shops and pizza parlours:

In retrospect, it’s easy (and risk-free) to poke holes in Michael’s thesis… But what if we told you that this very thesis was underwritten by Vinod Khosla, a Silicon Valley éminence grise? Did you know that the guy who has just agreed to shell out $9.6B for the Seattle Seahawks is Teamshares’ second largest shareholder with a 10% stake (via Khosla Ventures; source)? 

Back to our Norse vignette for a minute. The colony persisted for 400+ years, before winding down due to a combination of the Little Ice Age; Black Death-related trade disruption; and, above all, a rigid social hierarchy that stifled adaptation. The Norse clung on to stationary cattle farming for too long even as their Inuit neighbours showed the way by zipping around in kayaks assembled from Siberian driftwood - and hunting everything. 

Teamshares’ own Little Ice Age proceeded as follows:

There was a point last year where Teamshares came close to a Norse-style wipeout - but instead, pulled off a $175M equity raise (but only $74M in net proceeds) in conjunction with going public. Judging by the market’s reaction, it’s not out of the woods yet. With the stock trading around $6 (as at 22 July 2026), the SPAC / PIPE investors are 35-40% underwater, compared to 65% for Series E investors.   

The Teamshares of 2026 is a leaner, more resilient operation. Gross debt is down. Breakeven is tantalisingly close after years in the red. Cash flows from operations were -$42M in 2024, -$38M in 2025 and -$3M in Q1 2026 (source). Operationally, the biggest lift was pulling the plug on 13 PortCos in 2 years, or 1 in 7 (source: S-4). 

Particularly affected was the Food & Beverage segment, formerly the Group’s largest with c.30% of revenue (according to this LinkedIn profile). We know what happened: some eateries pulled back and some shuttered altogether. But why?