By Guy Rigby, Head of Entrepreneurs of Smith & Williamson

Guy Rigby, Head of Entrepreneurs at Smith & Williamson, asked six successful entrepreneurs about the biggest challenges they faced when setting up a business. Here’s what they had to say:

Alexander Anton – CEO, Legacy Portfolio:

I think that in the case of Legacy, the biggest challenge was convincing someone that the product existed and for people to believe that it could work. And in order to get that message across, you have to take a lot of rejection, have to be very stubborn, be able to sell, and you have to be a marketer.

Rob Hamilton- Founder, Instant Offices:

I think for me it was starting at 24 with no business experience and no management experience; I had never managed people, I had never run a profit and loss (P&L) before, I had never done marketing before. So all of the things you need to be able to do to run a business, I not only had to get the business working and make sure we had enough money to pay the bills. I had to learn all of those different disciplines.

Ed Bussey – Founder, iTrigga:

Start-ups are all-absorbing and inevitably you get drawn in because you love it, but also because you’re trying to do a hundred and one things and you just don’t have the time. So I personally find the biggest challenge for me is making sure I’m keeping that balance between time for my family, time to keep healthy and so on, versus a monumental workload, which inevitably goes with the start-up of a new venture.

James Lohan – CEO, Mr & Mrs Smith:

Probably my biggest challenge was getting turned down by publishers. We originally went to publishers to see if they would publish our idea, because we’re not publishers we didn’t know what to do. But we were turned down by all of them, which was a big challenge.

Then we decided we’d self-publish because it couldn’t be that difficult and looking at what other people had been publishing I thought we’d be OK. I was very comfortable with design and print and writing and things, so I figured if I pulled together a good team, we could publish our own guidebook. We got over that, but that was a big hurdle to get over, to be turned down by everyone to start with.

Alex Cheatle – Founder, Ten Group:

One of the biggest challenges was that even though we had a very clear vision that we wanted to become this very trusted agency and we were going to use knowledge management to sort things out for individuals, you never know what is going to occur. Of course, as an entrepreneur, you’re opportunistic and that opportunism runs in to being a strategic purist, so making the decisions where opportunism clashes with purity of strategy is really interesting.

Neal Gandhi – serial entrepreneur and investor:

One of the challenges I’ve faced throughout my career is that almost all of my companies have been a little bit ahead of their time. Sometimes way too far ahead of their time. And always in market defining mode, so always in a sector where beforehand people hadn’t realised the sector even existed.

For example, we set up one of the first internet consultancies (an ecommerce consultancy in 1996) when no-one knew that ecommerce was going to take-off. We knew it was but certainly no-one else figured that it was. And so I spent half my life educating the market on what was about to be, rather than necessarily just selling my products and services and growing the company off the back of the profits – you’re always market-making. That’s probably the hardest thing from my perspective.

For further information, to put forward candidates for an entrepreneur interview or to discuss any aspect of your business, call Guy Rigby, Head of Entrepreneurs, on 020 7131 8213 or email guy.rigby@smith.williamson.co.uk.


By necessity this briefing can only provide a short overview and it is essential to seek professional advice before applying the contents of this article. No responsibility can be taken for any loss arising from action taken or refrained from on the basis of this publication. Article correct at time of writing.

Smith & Williamson LLP

Regulated by the Institute of Chartered Accountants in England and Wales for a range of investment business activities.A member of Nexia International.

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