The seven deadly sins of exits

Greed, pride, and an array of other human weaknesses can get in the way of a good exit. speaks to entrepreneurs about their triumphs and regrets in selling their businesses.

‘Entrepreneurs often believe that if they start a company and own it, they are skilled enough to sell it. That often isn’t the case.’

David Jackson, CEO of marketing research specialist Site Intelligence, has participated in three exits. He believes that selling a company requires skills and knowledge that will put most business owners ‘outside their comfort zone’.

Mark Barlow, a founding partner of marketing and communications group Hasgrove, agrees. ‘Successful business owners have all got egos – it’s part of their make-up. But it’s also true that they don’t know what they don’t know. It’s not until the exit that this becomes clear.’

Related: How to sell your business: Planning the exit strategy

Here, entrepreneurs who have earned their exit stripes offer a guide to making your exit a heavenly, as opposed to hellish, experience…

As Barlow observes, a know-it-all tendency is natural for people who have built winning businesses. The solution is to swallow your pride and ask for guidance, as he discovered when he sold his first consulting business, IT Counsel, to building and construction group Amey in 1999.

‘Everyone was delighted with our exit,’ he says. ‘But we could have got there faster, cleaner and in better shape from a valuation point of view if we’d had someone to help us.’

An experienced mentor would have pointed out that the contracts Barlow had with many of his government clients were, like all public sector contracts, non-transferable to an acquirer. Since nearly half of IT Counsel’s business was with the public sector, it was a critical oversight.


Most first-time business sellers underestimate the amount of time, effort and sheer hassle involved in a typical sale.

Barlow describes his exit of IT Counsel as ‘mind-blowingly onerous’. After eight months of negotiations, he and his acquirer travelled to Oxford with their respective legal teams to seal the deal.

‘I expected it to take a day. It took four days, and each one of them we were up until two or three in the morning. At some points we were on the point of saying, “Let’s just get a cab home and tell them where to go.”’

Unless you’re well prepared for it, this emotional and physical strain may cloud your judgement and affect the smooth running of the business at the most critical point.


Wanting to get the best valuation for the company you have slaved over is understandable. But asking for too much can be a turn-off for prospective buyers, according Tony Hayday, who sold his own direct mail business, DPS, before setting himself up as an investor.

‘Overvaluation is very, very common,’ he states. ‘If you’re a start-up and you pitch it too high (or too low, for that matter) people like me will just walk away.’

On the flip side, there’s a danger of being seduced by what might be an illusory gain. Jackson sold his first company, computer training business ScreenScience, to AIM-listed Adval Group in an all-share deal.

‘If you are selling purely for shares, your destiny has been handed to somebody else,’ he says. ‘Inevitably, there will be a lock-in period, so you can’t crystallise your gains for some time.

‘It doesn’t represent an exit – you have just exchanged one set of equity for another.’


Naturally, working out exactly where you are on the growth curve is easier said than done. And there are unforeseen events – like the dotcom crash or 9/11 – that can wipe millions off your company’s valuation through no fault of your own.

After Barlow had received several approaches for IT Counsel, he took his co-founder and two other partners to a golf club to discuss whether to sell.

‘I wanted to keep the company, but after we’d debated it, the other three voted to sell. I was the majority shareholder so I could have overruled them, but I decided to accept their views.’

Barlow has no regrets: ‘We sold in 1999, right in the middle of the Millenium Bug issue. The Millenium Bug was great for our business, but when the clock went past midnight on 1 January and the world didn’t end, a lot of IT consultants were laid off. So from a timing point of view it was perfect.’

Since then, Barlow has advised start-ups in his sector that ‘if someone wants to buy it, then sell it’. Jackson has a similar view: ‘You have to look at the risk of running it versus the reward you could get today. My feeling is, the minute you feel as though new competition is coming, or the market is changing, or when you’ve done really well and people see the value, that is the time to take some advice.’


Laziness may seem an unlikely failing in a hard-working business owner. Nevertheless, while all your effort is going into sales and marketing, less gripping areas of work may be neglected – such as bookkeeping.

Simon Campbell sold the Spanish arm of his web applications company, Conexia Multimedia, last year for a six-figure sum. He concedes that Conexia’s accounts were ill-prepared for the scrutiny of a potential acquirer. ‘I don’t come from a financial background, so I just got on with stuff and put money into the company to get it going,’ says Campbell, now MD of paper mail-via-web business ViaPost. ‘To put the books in order when you haven’t been keeping records properly is a real pain.’

That pain is intensified when due diligence begins. ‘[A potential acquirer] is going to dig into the numbers, the contracts, all the details,’ he says.

‘You might think it’s quite straightforward and easy for you to explain, but they haven’t lived and breathed the business for years, so you need to put it very clearly so they can understand it.’

While you may make a packet out of the sale of your business, it’s likely that not everyone in the company will be delighted by the prospect. In businesses where your main asset is your staff, it’s especially important to stave off the green-eyed monster.

Barlow notes: ‘In a people-based business, you have to take employees along with you. This means not just limiting rewards to the shareholders – I believe employee share option schemes are essential.’

Perhaps the most common failing of all is to assume your exit will happen naturally if your business is successful. ‘A lot of [Conexia] was based around me as a commercial driver of the business,’ he reveals. ‘When we were packaging up the business for sale, the real question was, what was the value of the company without me? That was why most of the business has ended up being closed down rather than sold on.’

Jackson of Site Intelligence points out that the nature of your business should dictate your financial strategy for an exit. ‘If you are a company that has been trading for some time, showing solid but not massive growth, almost inevitably your value will be based on bottom-line performance. You will want to optimise your profits but not in a way that distorts the figures.

‘If, on the other hand, you are a technology business with great strategic potential in the hands of the acquirer, your valuation will be about those factors the acquirer puts value on, such as fast sales growth and investment in technology. It is hard to achieve those things while optimising the bottom line.’

Whatever your business, the consensus is that you need to steer yourself away from operations towards strategic goals.

Barlow counsels: ‘Get the right people around you and get yourself away from the coalface. Stop going out to customers and being part of the delivery team, and have a clear and complete vision of when and how you are going to exit.’

Navigating the tax maze when exiting your business

Tax implications are a common concern when company owners decide to exit and realise the equity in a business. It can be difficult to navigate the maze and calculate exactly what your final tax bill is likely to be, but here are a few things to consider…

Let’s assume your company is an unquoted limited company and that the sale is to an unconnected third party. David Beer from Beer & Partners advises, ‘If you invested in 25 per cent of the shares four years ago and the company qualifies as a business asset (there are special rules for qualification and a review of the company activities is necessary), you may be able to claim business asset taper relief.’

He goes on to say that the final tax bill will depend on the amount of your initial investment, your other income in the tax year in which you make the gain, any other capital gains that you have made and any losses brought forward from previous years. ‘You should also be aware of your annual exemption for capital gains,’ he adds, ‘and the potential availability of tax relief for the acquisition of another business asset.’

For a gain of this size you should consult a tax adviser on the specific details because making the wrong assumptions might prove very costly.

Adam Wayland

Adam Wayland

Adam was Editor of from 2006 to 2008 and prior to that was staff writer on sister publication BusinessXL Magazine.

Related Topics

Business Exit Planning

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