The second act: fintech founders and their new startups

Founding one successful fintech is a hard enough feat, but for some entrepreneurs, once isn’t enough.

It is a select group of people who choose to leave their successful startups and then start the cycle all over again.

They aren’t starting from square one the second time around though, so keep reading to see where they are now, what they learned from their first startups, and the lessons they’re carrying through into their next chapters.

Daniel Hegarty

Habito → Communion

With a desire to fix the nation’s relationship with money, Daniel Hegarty left his first startup Habito to found Communion, a behaviour science-backed, community-focused savings app.

Aiming to make saving “feel as addictive as spending”, Hegarty told AltFi that though he has spent the last 15 years building and investing in businesses that, at their core, aim to make money easier for people, it was last year, amid a cost of living crisis and young people feeling more disconnected and disempowered than ever, that the penny finally dropped.

“The biggest challenge we face is ourselves: our psychology, our anxieties, our beliefs,” he said. 

“Building wealth and feeling good about money is far less about money than it is about deepening our relationship with it and understanding the behaviours we need to adopt to make it work for us.”

His advice to other founders — other than that you should always start a business from your kitchen table — is that culture is key, no matter the size of your team. 

Also, things take longer than you expect, so don’t delay. Money from the wrong people is worse than no money. And make sure you know the intention behind your vision.

“Define your 'why' — your purpose — early. It's your North Star,” he said.

“It will serve as your guide during the exploratory phases, it'll  help you define your roadmap and it'll help you stay focused when the rubber hits the road.”

Jessica Holzbach

Penta → Pile

Jessica Holzbach built leading European challenger bank Penta in 2016 to shake up business banking and help founders and small businesses. 

She was co-founder and chief customer officer, leading growth strategy, marketing and business development until she left in August 2021, just ahead of the bank’s acquisition by Qonto in 2022. 

Less than a year later she co-founded Penta, where she is now CEO. The Berlin-based fintech is a neo-treasury management platform describing itself as a “simple treasury account for high growth startups and VCs”. 

After many years in the fintech industry, Holzbach founded Pile alongside Balazs Deme, who previously founded and led blockchain platform Herdius, to help give more businesses the option to diversify their capital.

Callum Rimmer

By Miles → Swallow

Founder Callum Rimmer left By Miles after six years and raising more than £25m to launch financial planning startup Swallow, which recently raised $1m. 

Aside from the darts, Rimmer told AltFi that he misses the colleagues he had at By Miles, and that as a solo founder this time around he misses sharing both the achievements and the burdens. 

But he also said that not having a co-founder means decisions are not a compromise, “which means a greater clarity and execution of business vision”. 

He said he saw a significant problem space in pricing while he was at By Miles that he was excited to explore with his new venture, which offers companies a no-code Software-as-a-Service platform aiming to make managing, optimising and updating pricing models easier and faster for businesses. 

His advice for founders? “Commit quickly but don't be afraid to change your mind often. It is better to waste effort spent doing than waste time spent procrastinating. Keep building momentum until momentum takes over.”

Paul Anthony

Primer → Colossal

Paul Anthony co-founded Primer with Gabriel Le Roux in January 2020 after they had both held senior roles at Braintree, a US-founded mobile payments company. 

Anthony stepped down from his role as CEO in July, with his co-founder taking over as he stepped into the role of chair and strategic director. 

He recently shared news of his new startup, Colossal, building a next-generation monetisation platform for producers and music creators. 

In addition to being a “payments guy”, Anthony has also been a hobbyist producer and beat maker for 10 years, he said, and is channelling this passion into helping other creators. 

After running Primer as a global, remote-first company, he’s changing gears with Colossal, building out a creative space in London with an in-house production studio and “synth wonderland”.

Goncalo de Vasconcelos

SyndicateRoom → Rnwl

Eight years after founding his first startup, SyndicateRoom, in 2011, Goncalo de Vasconcelos embarked on his second venture with the launch of Rnwl. 

Pronounced “renewal”, the digital insurance wallet centralises a customer’s insurance policies. 

de Vasconcelos, who remains CEO of the company, came up with the idea soon after stepping down from the same role at SyndicateRoom, and receiving an auto-renewal car insurance letter in the post. 

According to Rnwl, de Vasconcelos thought to himself “Wouldn't it be great if there was a company online that would sort this out for me?”. 

There wasn’t, and so he came up with Rnwl, which now aims to be both the best insurance wallet and purchase experience in the world.

Christian Faes

LendInvest → Faes & Co

After 15 years with LendInvest, co-founder Christian Faes left the mortgage platform at the start of the year and went all the way to Santa Monica. 

Having transitioned from CEO to executive chair in 2020 and then to chairman this year, Faes headed to the US to set up both F2 Finance and Faes & Co. 

Faes & Co launched in May, as exclusively revealed by AltFi, and is a new fintech investment firm building and investing in technology-enabled direct lending business. “Fix and flip” lender F2 Finance is the first venture out of the firm. 

“When I arrived in the UK in 2008 and launched what would become LendInvest, it was a period of total market disruption, which turned out to be an opportune time to be starting out on that journey. In many respects, the current market has a similar feel to it, and I’m excited to be starting out on this journey now in the US,” Faes said.