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What’s it like being a startup founder over 40?

What it’s like when you start a company — and actually have a reputation to lose

By Naomi Ackerman

Aforza cofounder Dominic Dinardo

Y Combinator cofounder Paul Graham once quipped that when it comes to first-time startup founders, “the cutoff [age] in investors’ heads is 32”. He was only partly joking: a perception endures that the best founders will be 19-year-old wunderkinds like Bill Gates and Mark Zuckerberg, or in their early 30s at the latest. 

Research suggests this attitude may be misguided. A 2020 report found that the most successful US startups — those in the top 0.1% in growth in their first five years — were launched by founders with an average age of 45. A 50-year-old entrepreneur is almost twice as likely to create a high-growth startup than a 30-year-old rival, researchers found.

Today, a swathe of founders in their forties and fifties are launching and running well-funded startups around Europe. Here we meet a few of them, learn why they pivoted in midlife and find out more about the advantages — and the drawbacks — of founding a tech startup after 40.

Midlife crises

There is a theme among over-40s founders. Most left a stable, well-paid job to launch a startup after facing up to the fact of their mortality, or questioning their legacy.

“You may say it was middle age, the point at which you need to do something else instead of buying a motorbike. I decided to try to cofound a startup,” says Sabrina Maniscalco, a Helsinki-based professor of quantum computing and the cofounder and CEO of software firm Algorithmiq. After over a decade in academia, Maniscalco launched the startup in 2020 aged 46. 

“On the one hand I was a little bit bored of the academic life, and on the other I was looking for new challenges,” she says. 

Algorithmiq CEO Sabrina Maniscalco
Algorithmiq CEO Sabrina Maniscalco

It was the sudden death of a colleague of a similar age that prompted Andy Yeoman to leave a $500k executive position at a California tech firm to be his own boss. 

“It brought into sharp focus for me that life takes sharp twists and turns,” says Yeoman, who was 47 at the time and now runs insurtech Concirrus. “When the email went out announcing the fact that he had passed away, in my head I almost did a ‘cut and paste’. I thought ‘if you change his name for my name, and that fact for my fact, that could be me’. I didn’t want that to be my story, so I then did one of those random things — I just walked in and said ‘I’m quitting’.” 

Dominic Dinardo had a similar reaction when his father passed away in 2008. The Scottish-born entrepreneur was at the time a well-paid executive at Marc Benioff’s software giant, Salesforce.

Dinardo’s father Tony had designed the church in which his own funeral service was conducted. Looking around during the eulogy, something clicked for his son. “I was thinking: ‘After we bury my dad, this church is still here. He’s actually somehow left a legacy behind’,” Dinardo says. “It does make you think: ‘What’s my legacy? What am I doing?”

It would be 11 years before Dinardo left corporate life at 48 to cofound consumer goods software startup Aforza. “It wasn’t a Road to Damascus, it wasn’t a flash, but it sparked something.”

A reputation (and money) to lose

Most 20-somethings have little to lose and everything to gain when attempting to launch their first tech company. But when former Virgin Money boss Jayne-Anne Gadhia launched fintech Snoop in 2020, the business world was watching. A well-known figure, Gadhia was 58 and had just left Salesforce after a short six-month stint at the helm. 

Founder of Snoop Jayne Anne Gadhia
Founder of Snoop Jayne Anne Gadhia

After investing her own cash and raising initial equity capital, Gadhia launched the money-saving app with cofounder friends from previous jobs.

“You’ve got a bit of a reputation to lose. So in a funny sort of way, it is slightly riskier,” she says. “Not that long ago this friend said to me: ‘I thought you were insane, after the career you’d had to set up on your own, start again from nothing’… I think it’s that in a sense. You think, I’ve done lots and lots of years, and do I want to bet it all on something that starts from scratch?”

Regret at not becoming a startup founder earlier — and battling (slightly) lower energy levels

Several over-40 founders concede that the relentless pace of being a startup founder can take its toll, while others say they regret not making the move sooner.

“Every conversation I have leads me back to ‘I wish I’d done it earlier’,” Gadhia says. “What we did for Virgin [Money] really was all the hard work, all of the entrepreneurship, but we didn’t reap the rewards — because that went to the people who put the money in.”

Maniscalco has only taken one or two days off since 2020, and has at times thought “this is horrible”. Yeoman also finds energy levels can flag: “I set the pace for the organisation, and that’s exhausting.” 

Experience and contacts

Midlife founders have decades of experience. They have an idea of who to bring in as CTO, and have faced down challenges before. As Dinardo says, “it must have counted for something”. 

Gadhia says: “I remember a number of my colleagues and I saying: ‘Gosh, if you were a couple of people without business experience setting up a big new startup in a garage or something, how do you know what to do?’ There are so many things that we were fortunate to understand, and contacts that we were fortunate to have had through those years of experience.”

Peter Briffett cofounded London-based employee finance app Wagestream in 2018 aged 45. A serial entrepreneur, he had previously launched and sold several startups, including Living Social and YPlan. “Unless you’ve killed all your relationships and no one ever wants to work with you again, it is easier to build an initial team [in your 40s],” he says. “There’s got to be some benefit to getting old, and some of it must be you’ve got more contacts and can put a team together quickly.” 

Self-confidence as a startup founder over 40

Over-40s founders also report having a self-confidence and level of self-knowledge they just didn’t possess in their earlier years — assets many believe have helped them make better decisions as founders.

“If I were younger I would be nervous and unsure of myself,” Maniscalco says. “Especially for a young woman [founder] it’s more difficult, because a lot of young women self-doubt more than men.” 

👉 Read: Get Market Fit CEO Vicky Brock: On lonely startup life and suicidal thoughts

Briffett says that the belief he had at 25 “that I could do everything” has disappeared. Later in life “you don’t pretend you can do everything”. He gives an example: Wagestream has focused on the hospitality, retail and healthcare sectors. “I think if I was 25 I would probably have tried to sell Wagestream to everyone, from manufacturing to logistics,” he says. But he knew from experience that “you can try and be too much to too many, and ultimately not get traction in any [sectors]”.  

Barney Wragg, who founded “robot chef” startup Karakuri in 2018 at the age of 45, says it’s a huge asset to now know “when to work until 2am, and when to stop” — unlike in his 20s. 

Investor bias goes both ways

For some first-time 40-something founders with established contacts at the pinnacle of the startup ecosystem, it really is as simple as sending a single email and receiving $1m. 

“I wrote to one former leader, a very important person in my development,” Dinardo says. “I said: ‘I’m thinking of building on this technology, what do you think? Will you bless this idea?’ And the person wrote back saying: ‘How much money do you want?’… It actually took me 24 hours to think of what the right answer was to that question — all I had done was produce a couple of slides. The answer was a million dollars.”

But a few older founders speak of encountering preconceptions from some VCs when fundraising, particularly younger analysts. 

“I would say there’s probably a negative age bias in a lot of investors,” says Wragg, who was an early employee at chip-maker ARM and had not attempted to raise cash for a seed-stage startup since the 1990s. 

Wragg says he found re-entering that pool “hard in my 40s”. While “historical tech funds were staffed by founders”, many now have “quite young analysts with limited or no experience inside the startup community making investment decisions”, he says. 

Wagestream’s Briffett agrees that sometimes VCs require over-40 founders to hammer home their commitment. 

“I’m older than most investors now, but like Madonna I’ll keep singing at 49,” he says. “I think VC money should flow to all ages. If you’re an articulate 20-year-old with a great vision, why can’t that be funded? I just think that should work both ways. The older you get the more it’s like: ‘Why do you still want to do this? Have you got the energy to do this?’ 

“Any VC funding a growth company knows that it is a high-energy thing, it’s not like you can have another life. So you have to be able to convince them that you’re all in.”

Just the start?

Has their whirlwind experience left founders with a yearning for more?

Gadhia “definitely” has plans for further ventures, and is “currently having some conversations with a different group of friends about launching a different startup”. “I think it’s because there is nothing that’s as good as setting up your own business and seeing it thrive,” she says. 

Maniscalco is focusing on Algorithmiq for now, but wants her experience to inspire other women in their 40s to found a startup.

“It’s less usual for women to really make a drastic change after they’re 40. You have a family, you think you’re settled,” she says. “I would love to see more women my age take risks. In many cases life is unpredictable, today the job market is unpredictable, so if you’re passionate about something there shouldn’t be fear of change.”

Naomi Ackerman is a freelance business writer and tweets from @nomiackerman

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Greg
Greg

A very interesting article. A real issue for older founders in the US is the incredibly high cost of individual health insurance, which might explain why there are more in Europe. While a single 20 year old can run the risk of not having health insurance, that is not an option for someone with a family. Premiums of more than $2500 per month quickly eat into savings and shorten the runway for the business. This is just one of many expenses that an older executive used to a large income has to maintain unless their family has agreed to a… Read more »

James
James

In Europe all medical care is free regardless if you pay insurance or social security.
However if you want a pension at retirement age you will need to pay a fee to SS.