Staring into the soul of Dominic McGregor
The Fearless Adventures founder has come a long way since he and his mate Steven Bartlett left Social Chain
Hello Rainmakers,
We all love a disruptor don’t we?
Meet Dominic McGregor from Fearless Adventures, and some of his investors and business partners.
Is it a venture capital fund? Kind of.
Is it a regulated investment vehicle? No.
Does it provide investment into businesses that want to scale up? Yes, but it claims to provide more than just the money.
So is it a marketing consultancy that takes equity stakes in its clients? Maybe.
But so what if it doesn’t fit into a box, isn’t that exactly what a disruptive entrepreneur like Dominic McGregor should be doing?
This isn’t a takedown, nor is it a puff piece. There’s also a few surprising new things about him. Read on…
Getting to know Dominic McGregor
I learnt something about Dominic McGregor and it wasn’t good news. Not for him, anyway. For a journalist like me it was explosive, and definitely worth following up.
But the founder of Fearless Adventures sparked a curiosity that required further enquiries where I got to know many more things about him.
At just 31 years of age he’s grown up in the business limelight, co-founding the social media agency Social Chain with business partner and former housemate Steven Bartlett, now a major media star.
Since 2021 his project has been Fearless, sometimes referred to as an “investment fund” which was co-founded by McGregor, with David Newns and Charlie Yates (below).
Pinning down what Fearless Adventures actually is though is part of the challenge. Is it a venture capital fund? Kind of. Is it a regulated investment vehicle? No. Does it provide investment into businesses that want to scale up? Yes, but it claims to provide more than just the money. So is it a marketing consultancy that takes equity stakes in its clients? Maybe.
But so what if it doesn’t fit into a box, isn’t that exactly what a disruptive tech sector entrepreneur like McGregor should be doing?
And even if you’re sceptical about the official Social Chain story - that McGregor helped Bartlett grow a US$300million turnover business with 750 staff, and that the pair “took the company public” in 2019 and exited in 2020 - it’s one which the telling of doesn’t lack audacity, something you can see being played out in the next chapters of both of their lives.
The Times newspaper has gone full sceptic on the claims. But as one entrepreneur told TheBusinessDesk.com in 2023: “Steven has very cleverly built his personal brand, there’s nothing wrong with that, but people have bought into the whole $600m myth.”
The reality lies somewhere in the small print, but even if the gain from chain wasn’t quite as portrayed, that’s still quite a story for a couple of young blokes in their
twenties. And cuts to the point as to why this is of genuine interest. McGregor also has a certain charisma, a magnetism and an energy that means he has a lot to give.
This is a story about what that is.
The starting point is to ask the question what is the best environment for a scale-up business looking to grow, learn and make it big?
It’s not an exam question, but it’s on the mind of investors and founders all the time.
The Fearless portfolio includes a six-figure capital investment in Pets Purest, as well as giving the business support for ecommerce, digital marketing and talent sourcing, Fearless has a minority stake in the company which chalked up £6m in revenue in 2020 selling health supplements for “dogs, cats, horses, ferrets and all other pets.”
They’ve also invested in Miniml cleaning products, a personal safety app WalkSafe, niche swimwear brand Swim Society, and Foudy’s, which makes women's football jerseys and fan apparel.
The founder of one investee company, Shipster, says she chose Fearless Adventures because of “their experience and expertise”. Hayley Cowburn, co-founder of Shipster, described Fearless as “different; they’re clear, honest, and have a genuine sense of excitement for our company’s future. The team is exactly what we need to grow.”
Sitting down with McGregor in his office in Wilmslow, you can only concur as he runs through the investment methodology, essentially putting a price on the skills the investee companies get access to, alongside the capital.
Not your typical VC
McGregor is not your typical venture capitalist. He says Fearless aims to be a true partner, offering hands-on support with marketing, recruitment, operations, and more.
"The idea with Fearless was that we wanted to invest in companies, but when we looked at what they were raising money for, it was mostly just for recruitment, marketing, and product development," explains McGregor. "So we thought, why don't we just help them with the marketing and recruitment side ourselves?"
He describes it as a “holistic model” that McGregor says he developed after reflecting on his own experiences at Social Chain; the cash flow crises, the struggle to build the right team, the operational headaches.
"I've been there, staring at a cash flow crisis in the face," he says. "I've had to deal with getting rid of people that you never feel ready for. So a lot of this is driven by not wanting people to be in the position I was in."
Rather than just writing a cheque and hoping for the best, he says Fearless takes a much more active role. They'll often appoint independent chairs to their portfolio companies, tapping into their network of experienced mentors like Music Magpie CEO Steve Oliver, Solly Solomou from Lad Bible and Simon Cooper, founder of On the Beach, to provide strategic guidance.
They'll also leverage their own in-house capabilities, whether it's the Fearless Academy training programme or the fulfilment services offered through their investment in Shipster, which helps ecommerce businesses integrate with logistics providers.
"The whole analogy of getting experience before you get experience, how do you solve that problem?" says McGregor. "What we wanted our course to be was that -experience before you get experience - show someone you're interested in the sector, you're humble enough to know you don't know everything."
It's that sense of untapped potential that fuels McGregor's mission. By breaking down the barriers to entry and providing hands-on support through their academy, Fearless is opening up new pathways for young, creative talent and making a real, tangible difference in people's lives, as well as building a solid investment proposition.
He says he wants to find pathways for 19-year-olds who have two years' experience in filming TikToks at home to access his world and break down the barriers they face.
It's also that willingness to be vulnerable and ask for help that also sets McGregor apart.
His LinkedIn posts invite you to look into his eyes and see his soul. In an industry often defined by bravado and ego, he's refreshingly, painfully, honest about his own struggles and shortcomings. It’s all laid bare in his 2024 book, I’m Never Drinking Again - How to stop drinking so much and change your relationship with alcohol.
He says that authenticity has endeared him to the entrepreneurs he works with and it certainly doesn’t leave anything out with his investors.
Getting the best out of him
But as important to the story of where Fearless and McGregor go next is Rachel McDonald, who has won the confidence of the investors to not only run the business effectively, but to get the best out of McGregor.
She joined in early 2022 after leaving advertising giant Dentsu where as chief executive of Dentsu North she managed seven offices in England and Scotland, overseeing at least 800 staff across agencies including Carat, iProspect and Amplifi.
At the time she spoke about finding the next big thing in the northern tech world, another THG or AO, but there’s a realisation that backing steady founders with a proven business model, but who need additional capital and strategic support to scale, is their sweet spot.
“The founders we work with often have a very clear vision for their future but need a little extra support in navigating the challenges that scaling a business can bring,” she says.
“In its simplest form I think the key difference is genuinely living up to our values and the purpose behind setting up Fearless in the first place. We promised ourselves we would back people we believed in and would make ourselves properly useful. Of course, we always act with integrity but we also wanted to create an adaptable platform that really focuses on helping each individual founder / business to thrive. We don’t insert ourselves into every decision or believe we know it all, we spend time listening and working out how our time and expertise can be most useful,” she adds.
“We genuinely see the services we offer being game changers for our portfolio giving them (for example) aligned access to a team of experienced marketeers, 100% aligned to impact on their business. The speed and ease in which we can deliver this creates real momentum and day one impact.”
For one Fearless investor, Simon Cooper, there’s an important point of difference between Fearless and a traditional venture investor. He says it provides a business with the equivalent of a marketing director, something businesses at this stage often can’t afford.
Cooper is the founder of online travel business On the Beach, a real success story which has come through private equity ownership and is seen as a bright light on the London stock exchange, and he also sees something of his younger self in the hive mind of Dominic McGregor.
“I was 35 when I sold to private equity, Dom isn’t even that old now.
“I’m 52 years of age, and I hope I’ve had some experiences worth sharing to businesses we back, but the team at Fearless are 20 years younger and very social media aware. So we have a diverse range of opinions to offer.”
He says many of the businesses don’t have an experienced marketing directors at their stage of development, so in order to get five years worth of growth in two or three years, they need a different approach.
He knows it’s a tough summit to scale, and the proof of concept will come from a successful exit, which they are obviously working towards.
Likewise, Steve Oliver, entrepreneur and founder of MusicMagpie, which was recently sold to AO, got to know McGregor better during lockdown after initially meeting as a Social Chain client. They would walk around different trails near their homes in Cheshire getting to know each other better and pondering how the world might change.
Oliver says he invested in Fearless in late 2021 and was “excited” by “the more holistic and ‘wrap-around’ investment support model they were offering to the fantastic and exciting businesses they were investing in.”
He says he’s typical of investors who want to give something to the businesses they invest in beyond the financial commitment, but only to a point.
“I simply don’t have the time to source, explore, run due diligence and ultimately decide upon investing in too many young and ambitious companies myself – let alone then both administer the deal itself and then most crucially offer the ongoing support to a number of investee companies, so it is fantastic to do so as part of such an exciting LLP alongside such an exciting, experienced and successful bunch of North-West based entrepreneurs who can all add value to the portfolio.”
In the investment world there’s undoubted scepticism.
Some bristle at the self identifying as a VC. “Probably his attraction is his social media expertise. But it’s not a VC though,” says one. “They have some money but are doing tiny cheques (really angel size) to invest in ecommerce and related businesses that would make use of their stable of mini agencies around marketing, social, logistics.”
Another says McGregor seems “a bit stretched personally” against the reputation he’s trying to give himself.
And yet both detractors offering honest critiques both say they like him.
And so to the thing I discovered.
It wasn’t a LinkedIn post about giving discount rail cards to entrepreneurs, or that the Conservative party wanted him to be an election candidate, or even having a rant at an online bank over a payments issue. Nor was it that he’d hit 30,000 followers on Instagram (though they are all true).
In November HMRC filed a bankruptcy petition against McGregor in the High Court. My initial enquiries were met with an unconvincing response from his representative that this was an error.
“During a standard investigation, HMRC unearthed historic tax errors. Dominic immediately sought to resolve these issues. The recent filing was made in error due to communication errors, and the matter is now resolved.”
The statement also came with a plea around his personal circumstances.
In the course of events it meant that in November 2024 McGregor had to formally resign from the LLP, which isn’t a great look, but he was supported by the other partners.
When we meet I ask him about it and he explains. But he also asks me to stop recording and so we go “off the record” for his explanation. He assured me the issue was being sorted out. I believed him. Suffice to say a week after our conversation the petition was withdrawn and the matter has been settled.
You might wonder why I’ve even mentioned it. But having also now spoken to his business partners, and read his powerful book - reminder, “I’m Never Drinking Again - How to stop drinking so much and change your relationship with alcohol” - it’s actually just one of those bumps in the road which people price in to working with him. It’s not likely to be a mistake he’ll repeat, however.
In the book he tells harrowing stories of his own destructive behaviour that he acknowledges had “ruined my reputation” and did terrible damage to what he describes as his invisible PR - “what people say when you aren’t there”.
He tells vivid stories of his own business innocence, having HMRC turn up to raid the offices of Social Chain because they hadn’t paid £100,000 in PAYE contributions because, says McGregor, “no-one told us that after paying wages you have to pay HMRC”.
He admits to constantly lying to get himself out of scrapes. But chapter seven of the book is even called, ‘Breakdowns lead to breakthroughs’, that even when he hit his own personal rock bottom it gave him the clarity and courage to drive on.
You can’t read the book, spend time with him, or hear the genuine and heartfelt warmth and confidence expressed towards him by his backers and partners and think this lad is a wrong un. He isn’t, clearly. His ideas and his energy, and his empathetic approach to supporting people who’ve walked the path he has, is impressive.
The moments in our meeting when he is most animated come when he talks about the academy to help young people develop skills to get on in this world.
As he embarks on the next stage of life - fatherhood and family life - and as the business matures, those around him will be hoping he’s learnt enough by now that he can carry on achieving the highs without the lows.
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