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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A US$50M revenue restaurant POS backed by blue-chip investors falls on hard times. A fire sale ensues - to a software aggregator.   

Sound familiar? Don't worry, this is not another Bending Spoons article! But good guess, for Bending’s staggering success - after the recent IPO it’s valued at $24B including debt - has shifted the narrative from “How’s this sustainable?” - to “Why aren't more firms doing this?”.

We went away and did our research. There are more firms pursuing Bending-style chunky workouts. Two names that spring to mind are Constellation Software (CSU) and Deck2 Capital.  

That’s right: CSU is dabbling in distressed venture! Its operating group Harris is the new owner of TouchBistro, the company we referred to above. But not only that. Take-privates. Not shying away from issuing equity to fund deals.  

Our thesis is CSU’s capital allocation is decisively shifting towards larger, more adventurous deals, prompted by two factors: 

This week’s other story is a rather less-known outfit from Australia specialising in insurance distribution. We’re talking about Deck2 Capital, the Family Office investment arm of Chris Bayley, a co-founder of Cover Genius: the embedded insurance platform behind digital platforms like Klarna, Revolut, Booking.com, Uber, Amazon, Expedia, and others. 

Last Sunday in Zurich, I sat down with Chris for breakfast to hear about his latest idea: rolling up legacy online travel agencies (OTAs) and direct-to-consumer Managing General Agents (MGAs - i.e. insurance intermediaries). 

In this week’s issue:

Before we tuck in, a really important announcement: we’ve just launched ticket sales for the 24th September Serial Acquirer Summit in London. This will be our largest-ever event; a full-day affair. 

In the morning, hear from the continent’s best Technical Services Buy & Build teams including Lindbergh (Italy), Aspira Partners (Nordics), Iberian Ventures, SATEP (France), and many others. Access is limited to 100 people in the morning to enable better connections.

In the afternoon, learn from founders who’ve scaled rollups from 0 to $100M+ EBITDA, including Rodolfo Guarino from Hippocrates; Charles-Henry Beglin from Simago, and of course Ramsey Sahyoun from Evergreen Services Group. 

This feels like an opportune moment to announce our latest partners: XFOLIO (Summit Platinum Sponsor) and Builders Associés. 

XFOLIO is a modern treasury and wealth management platform built by serial acquirers, for serial acquirers (and the investors that back them). XFOLIO provides superior cash visibility compared to  legacy ERPs, which feeds into better forecasting, and ultimately higher ROIC. 

Builders is part Family Office (of the Simago fame!) and part Independent Sponsor, Builders helps acquisition entrepreneurs build scaled platforms. If your ambition is €30M+ EBITDA within 3-5 years, Builders is the right investor for you.  

Full event agenda and tickets available here. Can’t make it in person? A live feed will be made available to our premium subscribers.  

To an outsider, buying OTAs is a contrarian thesis given the travel industry’s hand-wringing over AI-related disruption. On the other hand, buying pure-play insurance MGAs (Managing General Agents i.e. intermediaries) via selloffs and carrier spinoffs sounds extremely tedious.

Not for Chris Bayley. Chris’ core thesis from his time at Cover Genius is that many insurance distributors are burdened by legacy systems, restrictive insurance partnerships, and a lack of focus on ancillary revenue - while under-investing in initiatives that drive new customer acquisition. 

For an idea of what's achievable, consider the US retail colossus Best Buy. 

In fiscal year 2026, Best Buy generated US$42B in revenue and US$1.4B in operating profit (source). Contrary to an urban myth, Best Buy does not generate half of its profits from warranty sales… but it’s not far off. Net commissions and profit-sharing from extended product warranties represent c.1% of Group revenue. Best Buy gets the upside but none of the insurance downside, which anyway is minimal for embedded insurance distributors. That’s US$400M dropping to the bottom line, around 30% of total profits. 

Deck2’s view is that embedded insurance should be more like 60% of profit and their first acquisition, announced in late 2025, is Auto Europe Group (AEG), a 70+ year old, US$0.5B TTV business whose origins lie in “renting VW Beetles to fellow Americans who visited their children stationed in Europe”. 

There are many more targets to go after. Not only OTAs, but also legacy e-commerce companies that can benefit from improved insurance attach rates and introducing subscriptions, in the vein of eDreams Prime. 

Cove, the operating arm of Deck2, is transforming the asset by: delivering better merchandising; overhauling customer support with AI; and improving supplier, vendor and agency partnerships. 

Bottom line, they are targeting 5x EBIT growth in 5 years. Sounds ambitious, but otherwise legit. We wish Chris and the rest of Deck2 good luck and move on to the next topic:  

Big flashy deals of the kind favoured by Bending Spoons are not commonly associated with Constellation’s business model. The Canadian aggregator’s bread-and-butter is firms like Akuiteo: a French ERP for services businesses which grew revenues and profits 3x and 7x, respectively, after the change in ownership (read our deep-dive on Akuiteo). 

Still, in absolute terms, Akuiteo is a minnow with revenues of €16M in 2025. And that poses a particular challenge for CSU. Over the last decade, its Invested Capital grew roughly 10-fold, from US$1B to US$10B (or US$15B if you include accumulated amortisation). Generating a healthy rate of return on a 10 billion capital stack is very different compared to a 1 billion capital stack. 

The answer is more, and bigger deals - and specifically two types of deals: