The UK startup world has always loved the myth of the first-time founder, the hungry newcomer
with a big idea and nothing to lose. But if you look at who is actually shaping the ecosystem
right now, it is often not the bright-eyed newcomers. It is the people doing it for the second or
even third time. They have been burned once, or they have succeeded and want to try again
with fewer mistakes. Either way, they approach things differently, and it shows.
Learning the Hard Way
Take Anne Boden. Before she launched Starling Bank in 2014, she had already tried to
introduce digital banking at Allied Irish Banks. It did not work out. But she learned exactly where
the obstacles were, from regulation to technology. When she went again with Starling, she knew
what to avoid and how to get it right. The bank now has millions of customers and, unlike many
of its rivals, is profitable. That would not have happened without the failed attempt that came
before.
Or Martha Lane Fox. Most people know her as co-founder of Lastminute.com in the late
nineties. The dotcom crash nearly destroyed the business, but it survived and eventually sold
for more than half a billion pounds. After that rollercoaster, Lane Fox did not disappear. She
went on to start other ventures, including Lucky Voice, and has become a prominent voice on
digital inclusion. The experience of the first big run, good and bad, gave her credibility and
resilience that younger founders often lack.
Why Investors Pay Attention
Investors are not blind to this. PitchBook data last year showed that second-time founders in
Europe were far more likely to raise Series A funding than first-timers. It makes sense. If you
have already been through the pain of hiring badly, scaling too fast, or negotiating term sheets
you did not understand, you are less likely to repeat those mistakes.
Sharmadean Reid is a good example. She built Wah Nails into a recognised fashion and
beauty brand before turning her attention to tech. Beautystack came first, and later The Stack
World, which focuses on women entrepreneurs. Backers followed her into the new ventures
because they knew she had executed before. It was not about whether her first company was in
a different sector; it was about trust in her ability to deliver.
Teams Follow Track Records
It is not just investors. Talented people are more willing to join a founder who has been around
the block once already. Joining a startup is a gamble for employees too, and track record
matters.
Look at Taavet Hinrikus, one of the co-founders of Wise. After stepping back from the
company, he co-founded Plural, a new venture platform designed by founders for founders. The
fact that he has done it before makes it much easier to attract both money and people. His
name alone signals stability.
Failure as a Badge
For a long time, failure in Britain carried a certain stigma. That is starting to change. More
founders now wear it as a badge, not in a Silicon Valley “fail fast” way, but in a pragmatic, “I
learned something the hard way” sense.
Alex Depledge sold her first company, Hassle, to Helpling in 2015. Her next startup, Resi, came
out of lessons she had learned earlier about scaling and customer trust. Investors backed her
again because they knew she had already been through the wringer once.
A Sign of a Maturing Ecosystem
Twenty years ago, the UK did not have many repeat founders. The ecosystem was too young.
That is no longer the case. There is now a generation of entrepreneurs who have done it once
and come back wiser. This is a sign of maturity. It also makes London, and increasingly
Manchester, Bristol, and Edinburgh, more attractive to overseas funds, who are often more
comfortable putting serious money behind someone with a history.
Looking Ahead
The UK will still celebrate the boldness of the first-timers. But in 2025 and beyond, it is the
repeat founders who may shape the companies that last. They are the ones with the credibility
to hire better teams, raise smarter capital, and build with resilience baked in.
Sometimes the most important ingredient in success is not originality or hustle, it is experience.
And in the UK startup scene, more founders than ever now have it.