Charles Delingpole’s evolution: From fintech CEO to influential angel investor

While some may have anticipated Charles Delingpole's departure as CEO of ComplyAdvantage last year, few could have predicted his new direction.

ComplyAdvantage was already Delingpole's third business, having founded The Student Room in 2002 while at university and having co-founded Kriya (formerly MarketFinance) in 2010 following a stint at JP Morgan.

In both cases the serial entrepreneur and judge of the upcoming AltFi Awards 2023 eventually handed over day-to-day operations and moved on to his next big thing.

But this time is different. In fact, what’s most surprising is that as of today, Delingpole has yet to launch his next startup or announce a new venture.

“I’ve got no plans to start anything new,” is his straightforward answer to my question.

That’s not to say Delingpole is taking it easy, he isn’t even going on holiday this Summer, “far too busy adding value here in London” he laughs.

“I think it was too hot in Q3 to actually go away, right?”

From Founder, To Executive Chair

Part of the ‘value’ that Delingpole references is his new role as ComplyAdvantage’s executive chair, a transition he says has been “fairly smooth” and came at the right time.

It’s a strategic shift that some founders might struggle with, handing over day-to-day control of the company they started, however Delingpole says he’s been “happy with the dynamics” with new CEO Vatsa Narasimha.

“I think if I vehemently disagreed with any particular decision, then I'd articulate that… but I think largely we are of the same opinion or on the same page, and I’ve got to trust his judgement as well.”

“There’s a lot of people who have done the same thing,” says Delingpole, pointing to Carwow founder James Hind and Paddle founder Christian Owens, both who spent over a decade building their respective businesses before shifting into executive chair roles this year.

“I think a lot of people who've been [CEO] as long as I have—doing the same thing basically for nearly 10 years—have found it a good move.”

The other part of the value Delingpole refers to is his discreet role as one of London’s most prolific and successful angel investors.

Angel Investor Extraordinaire

So far this year alone Delingpole has reviewed over 160 pitch decks, invested in eight new startups and seen at least one exit with the sale of British insurtech Anorak to German insurance broker Clark.

Last year two of his portfolio companies were acquired. Fund establishment platform Vauban was snapped up by San Francisco’s Carta, and Credit Kudos was bought in a high-profile deal by tech giant Apple.

“The companies that I [invested in] over the past eight years, a lot of them are getting towards breakeven, they've grown and now they’re at a good scale,” the investor says, hinting that more good news is on the horizon.

This year however Delingpole has noticed a marked decline in new fintechs looking to raise—which he attributes in-part to fewer companies getting licensed by the financial regulators—and a sharp increase in those companies proclaiming to harness ‘artificial intelligence’.

“A ton of new companies are just LLM [large language model] wrappers basically. That’s maybe 20 per cent of the companies I’ve seen, which are doing something with OpenAI or GPT-3.”

That said, even the best investors don’t always get it right.

Just this week Delingpole saw his investment in Koyo Loans wiped out, after the consumer lender failed to raise additional capital, a story first reported by AltFi.

“It actually didn't work out, but I think most companies are still doing fairly well.”

Charting A New Path

With the backdrop of his impressive portfolio and having been awarded AltFi’s Special Industry Contribution award in 2022, Delingpole this year is joining the AltFi Awards 2023 panel of judges, casting his eye over the nominations later this summer.

“I guess the areas that I'm most excited about are infrastructure and the more complex, less obvious architectural areas of fintech, rather than the B2C branding companies,” he says.

“At the same time, some B2C fintechs are doing amazing revenues and amazing profits, but then again, maybe those guys don't need an award, their real award is making money.”

While the trajectory of Charles Delingpole's journey may have shifted from founding startups to influencing them from the sidelines, his passion for fintech clearly remains unwavering. 

Whether guiding ComplyAdvantage as executive chair or placing strategic bets on budding fintech companies, Delingpole's mark on the industry continues to be indelible. 

Nominations for the AltFi Awards 2023 are free and close at midnight 29 September 2023.