Now, in his new role as an executive member of the board of the European Business Angel Network (Eban), Gray will be heading even further afield, with Kazakhstan and New Zealand among the far-flung exotic locations on his itinerary.
“I’m always nervous of any country with a ‘stan’ on the end of it, but I could not have been more wrong about Kazakhstan,” says Gray, fresh from his travels to the massive former Soviet central Asian state.
“It’s a big country – about the size of Europe – with a relatively small population, comparable with that of France, and a huge amount of money. They have a clear determination that they don’t just want to be dependant on their oil and gas, they want to develop entrepreneurship on a wider scale.”
Gray was invited to Kazakhstan to help with the early-stage development of a business angel network, but highlighted a number of steps the country needs to take before investors can start developing syndicates.
“One of the major obstacles is the legal system, which contains many throwbacks to the Soviet era,” Gray says. “For example, there is no legal protection for minority shareholders, which initially pretty much rules out angel investing.”
But he notes that there is an appetite for change in Kazakhstan and expects it won’t be too long before angels begin investing.
He found that the changing face of the former Soviet state also comes through in other areas too, saying: “Although they have vast oil and gas resources, they’re already interesting in renewable energy, which I think is quite enlightened.”
Gray’s next sojourn will take him to New Zealand, a country he is already familiar with, and one where the business angel scene is in some ways quite similar to Scotland. But some of the destinations being lined up for Gray could prove to be even more interesting – Eban has been approached to discuss the possibility of helping to set up business angel syndicates in North Africa.
“It may sound corny, but spreading prosperity is a good way of spreading peace and Europe has an interest in developing links with North Africa, which, after all, is just on our doorstep,” Gray says.
Sitting on Eban’s board also gives Scotland a seat at the top table when it comes to discussions about the future of regulating investments.
“While there’s no suggestion that there are changes on the way at the moment, regulations can sometimes change quickly and can have unintended consequences and so it’s good to be involved at this level.
“On the flip side, Linc Scotland is the oldest angel organisation in the world, having been founded in 1992, and other European countries are keen to learn from how our angels have formed syndicates and how those syndicates come together to make larger investments.”
With members of Eban spread across 23 countries from Finland to Turkey, there is certainly plenty of opportunity to learn lessons from how other nations run syndicates.
Closer to home, Gray believes Scotland’s angel scene is flourishing, with a number of syndicates in the process of being set up. Some of the ideas developed north of the Border – including Scottish Enterprise’s co-investment fund, which now forms part of the Scottish Investment Bank – are being copied in England and Northern Ireland.
Gray became a business angel in 1996 after selling his family’s debt collection firm. He made his fortune using specially-written computer software to connect 350 staff across 12 offices in the pre-internet days.
While his first investment was a “disaster”, his second – in eye scanner maker Optos – proved to be a huge success, generating him a return that was 12 times the size of his initial stake. Investing in Optos – and using his skills as a chartered accountant to work with the firm during its early days – also cemented Gray’s reputation as a technology investor, although his involvement has spanned many different sectors.
Now, when he’s not involved in international duties with Linc Scotland or Eban, Gray is looking to return to the front line and is on the hunt for companies in which he can “sink his teeth” as a consultant or non-executive director.
He says: “A lot of the work I’m focusing on at the moment is about giving entrepreneurs a choice – do they want to sell their companies or do they want to carry on building them to a later stage, when they could potentially reach a higher sales price.
“It’s all about giving entrepreneurs those choices and helping them to sit down with the investors who can help them make those decisions.”
The Seed Enterprise Investment Scheme (EIS) is another hot topic that is occupying Gray’s mind. The tax-break – to encourage wealthy individuals to invest cash in earlier-stage companies – was introduced by Chancellor George Osborne in March’s Budget, building on the success of the existing EIS for larger firms.
However, Gray is concerned the Seed EIS could encourage some investors into the market who just see it as a tax break and aren’t prepared to engage with companies in the same way as business angel syndicates, which tend to offer managers advice on routes to market or bring other expertise to the table.
Crowd-funding – through which members of the public can buy shares in companies for anything upwards from just a few pounds – also raises questions for Gray.
Although the method has its place – with Gray seeing it as an extension of the “friends and family” funding that many start-up companies use before going to business angels – he is worried that it could complicate the share structure of some fledgling companies.
“Some business angels could be put off if they are faced with 1,000 or more shareholders to buy-out when they come to invest in a company,” he warns.
Education: Something new from every deal done, especially the unsuccessful ones
First job: Cleaning the showers in a sports club – paid in threepenny bits so it looked like more cash
Ambition while at school: To get out of school (which seemed to perfectly match the ambition of my teachers, as it happens)
Car: Many more thrills to be had from investing than from a super car
Kindle or book? Both – books still better for maps, pictures and reverences
What makes you angry: Desk warriors who have never taken a risk in their lives complaining about supposed lack of ambition in those who have had the courage to actually start a company
Can’t live without: A spellcheck
Music: Still prefer the Rolling Stones to The Beatles
Favourite place: Wherever my next exit completion meeting is going to be