What is actually on my desk this summer, the mandates heading to market, and two deals I lost along the way.
In two days I leave for Sicily, joining my family between Palermo and Cefalù until the end of August. Still working; the out-of-office runs 24 to 31 July only. For months I have preached that the timing is now, so this issue is disclosure: what is keeping me busy, names removed, substance intact.
The first: a sell-side mandate for a leading platform in high-value remote payments, where an expensive purchase still begins as a conversation. Billions of euro in annualised volume, hundreds of enterprise accounts in ten-plus countries, transaction values ten times the e-commerce norm, margins above ninety per cent, retention in the high nineties. Embedded, vertical, sticky.
The second: banking infrastructure. Every bank and e-money institution in Europe must expose regulated open-banking connectivity; almost none want to build it. This business delivers it as a service, compliance-critical plumbing on multi-year contracts, and I have mapped more than 120 strategics and sponsors for it. Boring, mandatory and recurring is what this market pays up for.
The third: the sale of a crypto-payments firm for merchants in high-risk verticals, where card acquiring is expensive, restricted or unavailable. Its engine is stablecoin settlement: instant, global, indifferent to a sponsor bank's risk appetite. The networks have spent billions buying exactly this capability; the question is no longer whether it matters but who is left to acquire.
The fourth: a small-cap vertical payments-software situation in the UK and Europe, a buyside search and a capital raise in parallel. The acquirer: a platform consolidating vertical software. The targets: founder-owned systems running clubs, clinics, bookings and trades, deeply embedded, payments underexploited. The search: tens of thousands screened to a few hundred qualified, acquisition memos on well over a hundred. The raise funds the consolidation; the pipeline is built.
Behind those four: a payments valuation mandate, regtech M&A in KYC and AML, Eastern European banking infrastructure, and a high-risk stablecoin growth raise and two MGA M&A deals with post-merger-integration and knowledge management mapping. The breadth is the message; this is the window from the inside.
Honesty cuts both ways. I advised a buyside client this year, a listed serial acquirer valued at roughly $40 billion, with more than a thousand software businesses under its roof, twelve billion dollars of revenue and a playbook refined over decades, on the purchase of a payments business it knew thoroughly. The target: a two-decade-old, dual-licensed e-money institution, principal member of both major card schemes, direct on SWIFT, SEPA and Faster Payments, running accounts, issuing, acquiring and open banking under one roof, with a team more than a hundred strong across three European offices. The offer ran well into the nine figures, built on growth, margin quality, retention and integration value. The seller held out for half as much again, a premium no model I could construct would support. Months of work ended in a polite impasse, and the gap between those numbers bought the seller nothing but time. The market does not pay you what you think you are worth; it pays you what you can defend.
And I lost a mandate I wanted: the sale of a payments group at north of €100 million, a licensed e-money business regulated in two jurisdictions, whose wallet reaches more than seventy countries in eighteen currencies across eighty-plus payment methods, serving some of the most demanding corners of digital commerce. I was ready. The materials were as complete as anything I have produced, and I knew the asset and its buyers cold. Another bank won it anyway. I have replayed that pitch, and I still cannot point to the miss. Sometimes you lose without a clean reason, and the discipline is to accept that without inventing one. The consolation of a market this active: sellers become buyers, and I rather suspect our paths cross again, next time on the buyside.
Every one of these, won, lost or pending, reduces to the same conversation: a founder who spent a decade building, asked to make the largest financial decision of their life, once, with no rehearsal. Generational wealth is decided in a handful of meetings, and the hardest part is never the valuation; it is the timing. Sell too early and you wonder forever; hold too long and the window answers for you. My own view: the party winds down perhaps by the second quarter of next year, and nobody rings a bell at the top. The founders who transact well will be the ones who were ready before they had to be.
If you are weighing readiness, a raise or an exit, I am always open to a thoughtful conversation. Between 24 and 31 July, even bankers surrender to Sicily.
Tom C. Schapira
Founder and CEO
Imagine Capital Group
E: tom@imaginecapitalgroup.com
Website http://www.imaginecapitalgroup.com
