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When Simon Blakey made his first angel investment in 2000, the startup ecosystem looked radically different. There was no AngelList, no Seed Legals, and certainly no standardised term sheets. Finding deals meant subscribing to the "Venture Capital Report" — a physical, green-bound publication that featured just two or three opportunities with basic due diligence notes.
Fast-forward 25 years, and Blakey has completed over 100 funding rounds across 50-60 investments, ranging from robotics companies eventually acquired by GE Aviation to ticketing platforms processing over a billion in GMV. As Chair of the Investment Committee at Playfair Capital and a board member of Cambridge Angels, he's witnessed the entire evolution of early-stage investing.
His journey offers invaluable lessons for today's angel investors, particularly those making the transition from successful entrepreneurship to investing. Click the link below to listen to the full podcast.
Blakey's path to angel investing wasn't planned. Originally trained as a biochemist, he moved into management consulting via the Chartered Institute of Management Accountants. However, it was a profitable side hustle in West London property development during the 1990s that gave him both the capital and confidence to try something new.
"Around 98, 99, I was in my mid-twenties and recognised that being a partner at a consultancy firm was not my life goal," Blakey recalls. "It was the start of the dot-com boom, mark one, and angel investing was beginning to be talked about."
Acting on advice from Christopher Stone to either "do it full time or don't do it at all," Blakey set up a two-person office in Hammersmith and committed fully to learning the craft. He bought books on term sheets and corporate finance, but more importantly, he took his time despite the dot-com frenzy around him.
"I wanted to find what I call the unfashionable businesses with unfashionable valuations — those deep value opportunities," he explains.
Blakey's first five deals were remarkably successful, with one returning significant multiples in just 18 months. "I thought, 'Oh, this angel investing thing is easy,'" he admits. "I was wrong."
What followed was a sobering seven-year period where, in his words, "every single deal was utter shit." This "valley of death" in his portfolio taught him perhaps the most important lesson of his career: angel investing requires both patience and persistence.
"I'd had that initial success and quite serious returns at the early stage, so I thought, 'I've just got to keep working at this and things will come good in the end,'" he says. "And now I look at my portfolio and think, 'Yeah, I had this valley of death, but actually, in the end, it's all come good.'"
One of Blakey's most striking insights concerns the fundamental difference between angel and VC expectations around timing. While VCs face pressure to demonstrate portfolio appreciation to raise subsequent funds, angels can afford to be patient.
His portfolio includes companies he's held for over two decades. One robotics company from 2002 is still operating and has paid back multiples of the original investment. A logistics business, BuyBox, took 15-16 years to exit but generated a £120 million sale for angel-only investors.
"There's a fundamental difference between angel expectations and VC expectations," Blakey observes. "VCs need fast growth from the get-go because they need to raise their next fund. The best way to prove their prowess is to have an uptick in portfolio valuations."
This patience advantage creates interesting strategic opportunities. "Are there angel-funded businesses versus VC-funded businesses?" Blakey asks. "If you can have an angel-funded business that sells for £40-50 million but you got in at a £1-2 million valuation, as an angel, you're going to be very happy. But a £40-50 million exit for most VCs won't cut it at all."
Perhaps Blakey's most urgent message concerns the challenges facing new angel investors, particularly successful entrepreneurs fresh from exits. His recent LinkedIn post, "Why New Angels Can Crash and Burn," emerged from observing a recurring pattern.
"What tends to happen is they jump straight in," he explains. "They don't really know what good looks like from an investment standpoint so that they might invest a lot of money in two or three deals, not remember there's going to be follow-on requirements, and try to get really involved because they're successful entrepreneurs."
The inevitable result? Early failures (which always come before successes), unexpected follow-on requirements, and a rapid loss of enthusiasm for angel investing.
His advice for new angels is counterintuitive: Start small and take your time.
"Don't feel you have to have done loads of deals to be valid," Blakey counsels. "Say you're taking your time, waiting to find the right deal, and building your network. Money for follow-on is crucial."
Blakey draws a compelling parallel between successful entrepreneurs becoming angels and professional athletes becoming coaches. Just as sporting greatness doesn't automatically translate to coaching excellence, entrepreneurial success doesn't guarantee investing acumen.
"The mindset you bring to angel investing has to be different from being an entrepreneur," he emphasises. "You are the sage, wise counsel sitting on the side. You're not the person doing or getting involved in operations."
This shift from decision-maker to advisor requires particular finesse since angels typically hold minority positions without legal enforcement rights. "What you have to do is gently give explanation and rationale rather than saying 'do this' and expecting it to get done."
Over 25 years, Blakey has developed several data-driven investment rules:
The Follow-On Limit: He now caps investments at two rounds, maximum three. "All my data shows that if I do more than two angel checks into a business, it's likely going to fail because it hasn't reached escape velocity. It's too easy to keep thinking 'it's just this bridge round.'"
Domain Expertise Over Everything: "I do a lot of my pre-seed investing based on the domain expertise of the founders. These were two academics who were well into the details and had that slight degree of stubbornness and obsession to run through walls to prove they have a viable business."
The Portfolio Approach: With roughly half his investments still active and the oldest dating to 2002, Blakey emphasises that angel investing is fundamentally a portfolio game requiring both patience and diversification.
Blakey identifies three challenging aspects of angel investing, with only one being enjoyable:
Deal sourcing: "You can go for months not seeing a deal that looks good. I remember 2007-2008, for 18 months, I wasn't doing any new deals. For every deal you find, you might see 50-100 that don't look good."
The time horizon: "It can take years to show success. I've got one IoT company where I invested two years ago, and it's taken that long just to get to commercial traction."
Post-deal support (the fun part): "Hopefully founders can show their full potential and you can help and advise them on that journey."
For the support element, Blakey has learned to avoid excessive board commitments (he was once on 13 boards simultaneously — "one of the worst times in my angel investing career") in favor of building trust-based relationships via WhatsApp and regular check-ins.
When asked about the best resource for angel investing, Blakey's answer is unequivocal: other angels.
"I didn't recognize at the beginning how isolating it can be being an angel. Join an angel syndicate. Reach out to other angels. Having people you can speak to about deals and do sense-checks on your thinking is really valuable."
This advice reflects a broader truth about angel investing: despite the individual decision-making, success often comes through community and shared learning.
At an age when he once planned to retire from angel investing, Blakey shows no signs of slowing down. His brother teases him about "doing more deals than ever," and Blakey acknowledges the irony while explaining his continued enthusiasm.
"I'm getting older and entrepreneurs are staying the same age. There's going to be a point where they really don't want to listen to a grumpy old man," he jokes. "So I think the market will decide when it's time for me to bow out."
Until then, he remains motivated by three factors: genuine enjoyment of the work, financial returns, and control over his schedule. "As long as I can do what I want when I want and still be involved with young, exciting companies and entrepreneurs trying to make a difference, I'll continue."
Simon Blakey's quarter-century journey through angel investing offers a masterclass in patience, persistence, and continuous learning. His experience spanning the dot-com boom, the 2008 financial crisis, and today's AI-driven startup ecosystem provides a unique perspective on what works — and what doesn't — in early-stage investing.
For new angels, particularly those transitioning from entrepreneurship, his message is clear: respect the craft, start small, build networks, and prepare for a longer journey than you expect. The rewards, both financial and personal, can be substantial — but only for those willing to learn from both successes and the inevitable failures along the way.
As Blakey puts it: "I've learned far more from my failures than my successes. The successes generally happen despite me, not because of me."
In an ecosystem often focused on quick wins and rapid scaling, that kind of humility, combined with 25 years of battle-tested experience, is invaluable guidance for anyone serious about angel investing.
