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E60 | The Challenge of Scale with Ben Fletcher

Entrepreneurs are told time and again to embrace failure, to be proud of failure, to not be ashamed of failure. But failure is still something that is brushed under the carpet, something you shouldn’t be proud of. And so today’s guest, Ben Fletcher of Lead Bullets, is a breath of fresh air. 

Ben is a serial entrepreneur and the proud maker of multiple mistakes, many of which Dom talks to him about in this episode. Because at the heart of it, Ben’s mistakes are what drives him. In fact, when asked what he would go back and change in the past, knowing what he knows now, he replies: 

“I’ve learned so much from those mistakes, it’d be really hard to do anything that fundamentally changed the way my life worked out.”

And it’s those mistakes that have carved out his current role – the one that sees him help entrepreneurs and CEOs of fast growth companies not make some of the mistakes that he himself made. It doesn’t matter what the industry is, or the sector the business is involved in, a scaling business is a complex thing that trips people up time and again, and always in the same places. 

Dom and Ben talk about how to set objectives and why that’s important; about hiring good people; about not being on the edge and losing innovation and most importantly, not spending time with your problem children. 

This is a really fantastic conversation, one that we enjoyed hugely, so happy listening. 

On today’s podcast:

  • How Lead Bullets helps founders of businesses
  • How Ben ended up with an events business, by trying to get out of events
  • What they do differently to every other events company
  • Define your mission if you want to achieve success
  • Ben’s favourite mistakes
  • The importance of hiring the right people
  • Why raising money isn’t always the answer


Ben Fletcher is a hugely successful serial entrepreneur and the proud maker of multiple mistakes. Dom talks to him about a number of those mistakes, because at the heart of it, Ben’s mistakes are what drive him to success. 

Not that he knows quite what success looks like as he’s still working on that mission, but if he can help 1 million entrepreneurs run their businesses more effectively, he will feel his life’s work is done.

That’s quite an ambitious target for a guy who readily admits that he spent a lot of his early career floundering his way through in business and being successful largely by accident and happenstance. 

And that is what sets Ben apart from the vast majority of entrepreneurs. Entrepreneurs are told all the time to embrace failure, learn from it and allow it to help the business grow. But Ben is an entrepreneurial rarity, because he readily relishes his mistakes. 

When he’s asked what he wishes he knew way back when, that he knows now, that might help or change something he did in the past, he finds it hard to come up with an answer: 

“I’ve learned so much from those mistakes, it’d be really hard to do anything that fundamentally changed the way my life worked out.”

For that reason alone Ben is incredibly inspirational, not just for business leaders but for life in general. To go through life with such an optimistic outlook is truly an admirable quality. 

In his current incarnation of business, Fast Growth Icon and Velocity Squared, both of these are designed for companies with between 75 to 300 employees. The reason being because that’s the level at which you can’t, as the founder, be involved in all the key decisions anymore. You can do the key hires, just not all hires. You can be involved in some key meetings, but not all meetings about product strategy or not all meetings about marketing. And if you try to be that involved you become a bottleneck. So you have to create an organisation that can think and operate without you being involved. 

And that is the challenge of scale.

Ben’s Big Mistakes

Ben says that his early businesses weren’t wildly successful (well, they were successful, but accidentally, and not for the long term). 

“In the first iteration, the product was really good, generating loads of revenue that was pulling us into growth. And we had success. But it just camouflaged the fact that we were making lots of mistakes, because the business was growing because of the quality of the product… the second time we had this massive chunk of money, because we’d been really successful. So we were like, ‘oh, we’re investing in the future. It was just a future that never arrived.”

The importance of hiring the right people

Another of Ben’s mistakes was not hiring the right people. They thought to be successful they had to be bigger, three times the size they were. That ambition equalled growth. 

“We had tonnes of money because we were making loads of money, and we went out and we just hired loads of people. And it was a bit of a disaster, because I think what actually happened is we didn’t hire loads of really great people, we hired less good people, because we were in such in such a hurry to hire them. We had the wrong objectives.”

And the problem they quickly learned was that mediocre people follow the rules and aren’t big on innovation. So the company stopped innovating and had no flexibility, and they became just like all the other event companies.

Why raising money isn’t always the answer

Ben is proud of his accidental success because he learned the hard way that having lots of money doesn’t equal long term success. 

“Entrepreneurs are sold this idea that raising money is the key to success. And it’s not. It’s a very particular type of success.”

He warns:

“I think people fall for this mentality of ‘if I raised £10 million for my business, how can I not make a success of it?’ Well, lots of people raise £10 million and don’t make a success of their business. Having the money doesn’t make it all suddenly easy for you, it’s always hard.”

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