She'd been in the syndicate longer than I had, and she had no idea she was losing.
We were having coffee, the good kind, in one of those Edinburgh places that charges you for the privilege of sitting down. She’s younger than most of our members, sharp, does something clever in professional services that pays well. She’d written maybe a dozen small cheques over the years into companies the syndicate had brought to her. And somewhere between the flat white and the second cup, she said the thing that made me put my cup down.
“I don’t really do much before I invest. I just sort of go with what the group’s doing. It’s all a bit of a lottery anyway, isn’t it?”
It isn’t a lottery. That’s the whole point. It looks like a lottery, which is precisely why so many intelligent people play it as if it were one. But there is an invisible league table running underneath every angel syndicate in the country, and your position on it is decided long before any company exits. It’s decided by what you do in the weeks before you write the cheque, and, as we’ll see, by what the companies you back had already done before you arrived. And almost nobody can see the table they’re on.
I’m going to call her Kate, because that isn’t her name and she’d rather I didn’t use the real one. Kate is the reason for this piece. She becomes, later on, the happy ending. But first I need to explain the table she couldn’t see, and why the reason she couldn’t see it has everything to do with why other people invest at all.
This is a companion to our earlier article about the roughly £340,000 gap, the one built from Robert Wiltbank and Warren Boeker’s 2007 Kauffman Foundation study, “Returns to Angel Investors in Groups.” If you’ve not read it, the single sentence version is this. Angels who spent 20 or more hours on due diligence before investing saw an average return of 5.9 times their money. Angels who spent fewer than 20 hours saw 1.1 times. Same deals, roughly. Same market. The difference was the homework. We turned that into a worked example and it came to about £340,000 of foregone return on a modest portfolio. People found the number uncomfortable, which is the correct response to it.
This piece asks the question that sits underneath that one. If more diligence so obviously pays, why on earth do most angels do so little of it?
The answer is more interesting than laziness. The answer is that they’re often being perfectly rational, given what they actually want. And what they actually want is frequently not what they’d tell you at a drinks reception.
Five angels, five reasons
Let me introduce some people. They’re invented. I want to be completely clear about that, because the rest of this article leans on them and I’d rather you trusted me than caught me out. The following characters are fiction, composites stitched together from a decade of watching real syndicates and from the academic literature on why angels invest. Any resemblance to a specific person is your imagination doing what imaginations do. The research behind them, though, is real, and I’ll show my working at the end.
Meet four angels, and Kate makes five.
There’s Gordon, who is a management consultant. Gordon invests small, always small, five or ten thousand at a time, into companies that are raising a proper round. Gordon has noticed something that the rest of us pretend not to. A founder who has just taken your cheque, however small, is a founder who might also take your advice, at your day rate, which is considerable. Gordon’s investments are not really investments. They’re the cost of a warm introduction to a paying client. His diligence is light because light diligence is the correct amount of diligence for what Gordon is actually buying, which is access rather than equity.
There’s Marcus, who earns a great deal and hates his tax bill more than he likes anything. Marcus invests because SEIS gives him 50 per cent income tax relief on up to £200,000 a year, because EIS gives him 30 per cent on up to a million, because his capital gains can be sheltered, and because if the whole thing goes to zero he can claim loss relief against income at his marginal rate. Marcus has done the arithmetic and the arithmetic is genuinely lovely. By the time the tax reliefs have done their work, a total loss costs Marcus a fraction of the cheque. So Marcus, quite logically, doesn’t sweat the company. He’s betting on HMRC, and HMRC always pays out.
There’s Priya, who built something and sold it, and now has more money than she expected and a strange hole where the company used to be. Priya invests because she misses it. She wants to sit across a table from a nervous 29-year-old and see herself ten years ago. She gives real time, real contacts, real scar tissue. Her motivation is the one the academics call altruistic, though Priya would find that word embarrassing and would tell you she just likes the founders and wants them to win. She does more work than Gordon and Marcus combined. She hasn’t read Wiltbank. She doesn’t need to, because caring and diligence turn out to look almost identical from the outside.
And there’s Rupert, who is in the syndicate because the right people are in the syndicate. Rupert enjoys saying “one of my companies” at dinner. His diligence consists of finding out who else is in, and following them. Rupert is the purest example of a type the research is too polite to name properly, the investor whose real return is social, measured in standing rather than in sterling.
Then there’s Kate, who genuinely doesn’t know why she’s doing it, which makes her the most promising of the lot. Because Kate is the only one who can still change her mind.
Now here’s the thing the coffee conversation taught me. Every one of these people is behaving sensibly given their goal. If your goal is consulting work, light diligence is efficient. If your goal is tax relief, the company barely matters. If your goal is status, following the crowd is the entire strategy. The trouble is that four of these five people believe, when they check their statements, that they’re playing the returns game. They talk about multiples. They’re quietly disappointed when a company folds. They think they’re investing. They’re doing something else, and the something else has a cost they never see.
Keeping score in different currencies
One in forty: the diligence arithmetic
David S. Rose, who founded New York Angels and has probably seen more angel deals than almost anyone alive, puts it plainly. Writing for Columbia Business School, he says that “venture capital funds typically review up to 400 opportunities for each early-stage investment, professional angels are generally only able to look at 30 to 40 company presentations before writing a check.” In a Motley Fool interview the same year he said it even more baldly. Angels “typically invest in only two or three percent of the companies that they see, so that’s one out of 40 companies. You’ve got to be really tough.”
One in forty. Sit with that.
The Angel Capital Association’s own guidance, drawn from surveys of member groups, describes the same funnel from the inside. Only about one in four deals that reach pre-screening make it to screening, and only about one in three of those make it to due diligence. Compound that and you’re at roughly one in twelve reaching the diligence stage, before the final cull. In the UK, Angel Academe, one of the more rigorous networks, has reviewed over 5,000 opportunities since 2014 and backed 50-plus companies. That’s a funnel of about one per cent.
So here’s the honest arithmetic Kate had never done. Suppose you want to make three good investments a year, which is a sensible pace for a diversified angel building toward the 20-plus companies the data says you need. At Rose’s one-in-forty, you need to look hard at around 120 companies to find your three. If you’re doing the diligence the returns actually reward, Wiltbank’s 20 hours minimum, and a 2019 study by Forrester and colleagues put the mean at 60.6 hours per deal, then the numbers become absurd for a busy professional very quickly. You cannot do 20 hours of real work on 120 companies. That’s 2,400 hours. That’s more than a full-time job, on top of your actual full-time job.
Kate earns, let’s say for the sake of the sum, £100 an hour when she’s working. Twenty hours of diligence on a single company is £2,000 of her time. If she does it properly across even a fraction of the funnel, the cost of her own attention dwarfs the £5,000 or £10,000 she’s putting into any one deal. This is the trap. For a high-earning professional, doing angel diligence properly, alone, costs more in foregone earnings than the investment is worth. So she doesn’t do it. And because she doesn’t do it, she lives in the 1.1x world, not the 5.9x world, and she never knows, because the gap between those two worlds only reveals itself a decade later, by which time she’s blamed the market, or luck, or the founders, or “it’s all a bit of a lottery.”
The canteen: what a syndicate is for
But look what happens if you don’t do it alone.
This is the entire, unglamorous genius of the syndicate. When twenty angels share a syndicate, they don’t each do 20 hours. They pool it. The work is led by, and entrusted to, the members with the relevant scars, the ones who actually understand SaaS churn or clinical trials or supply chains, and the rest of the group rides on that expertise. Wiltbank found this too, in the UK, in his 2009 NESTA and BBAA study “Siding with the Angels.” The returns came from diligence and from investing inside your area of expertise. A group gives you both. You get the 20-plus hours of coverage without personally paying the opportunity cost on every deal, because the hours are divided and specialised. It’s the difference between everyone in the office cooking their own lunch and a canteen.
This is not a small effect. The UK Business Angels Association reports that 79 per cent of UK angel investments are made as part of a syndicate, and that the median initial cheque is £25,000 with a £7,500 follow-on. In Scotland it’s practically the default. Archangels, the Edinburgh syndicate, does its origination, due diligence, portfolio management and exit work on behalf of its 70-plus members, who invest as individuals but never have to be the expert on everything. In 2024 Archangels led £27.3 million of investment, £13.8 million of it directly from members. Over its life it has turned around £36 million invested into more than £100 million realised, taking, on average, about eight years to get there. That last number matters and I’ll come back to it.
Some canteens will poison you
The Angel Pyramid
- Layer 1, the base, about 60 per cent: the ad-hoc angels. Under 5 hours of diligence, investing on a pitch, a personality, a warm introduction, usually outside their own domain, holding a handful of companies. This is Wiltbank’s 1.1x band, where most cheques return less than the capital. Gordon lives here and Rupert lives here, and neither is failing, exactly, because Gordon’s return is a consulting fee and Rupert’s is a dinner-party anecdote. They’re at equilibrium. It’s everyone else on this layer, the ones who think they’re playing the returns game, who are paying for it.
- Layer 2, about 20 per cent: the tax-motivated cheque-writers. Marcus’s layer. SEIS and EIS relief is the reason for the deal, the downside is floored by the rebate, and so the diligence never gets done, because protecting the upside was never the point. Outcomes here run slightly ahead of Layer 1 after tax, and that’s the ceiling, because relief truncates losses without improving selection by a single hour.
- Layer 3, about 12 per cent: the passive syndicate members. Diligence nominally outsourced to a group, sometimes a good group, sometimes a fee machine, and never checked either way. This is where Kate sat for years. If the syndicate is poor, the fees and the thin deal flow eat the difference. If the syndicate is good, the member’s passivity wastes it. Either way, the pooled hours exist on paper and not in the member’s head.
- Layer 4, about 6 per cent: the active members of high-quality syndicates. Pooled 20-plus hour diligence genuinely done and genuinely read, entrusted to sector-expert gatekeepers with actual exits behind them, membership and admin fees only, no five-figure tolls billed to founders, and real engagement after the cheque. This is the 5.9x band the research describes. It’s where Kate is climbing to, and we’ll follow her there.
- Layer 5, the apex, about 2 per cent: the elite. Forty-plus hours led personally, in-domain, board seats, portfolios of 15 to 25 companies, and follow-on done selectively into winners rather than reflexively into casualties. Wiltbank’s 7.1x band. Priya’s layer, though she’d never call it that. Tiny, mostly invisible, quietly compounding.
Two leading indicators, one lagging truth
| Quarter | Priya | Gordon | Marcus | Rupert | Kate |
|---|---|---|---|---|---|
| Q1 | 35 | 4 | 3 | 5 | 2 |
| Q2 | 38 | 4 | 2 | 6 | 3 |
| Q3 | 40 | 5 | 3 | 5 | 9 |
| Q4 | 41 | 4 | 3 | 7 | 18 |
| Q5 | 42 | 5 | 2 | 6 | 24 |
| Q6 | 43 | 4 | 3 | 6 | 26 |
| Quarter | Priya | Gordon | Marcus | Rupert | Kate |
|---|---|---|---|---|---|
| Q1 | 25% | 0% | 10% | 0% | 0% |
| Q2 | 25% | 0% | 0% | 0% | 0% |
| Q3 | 30% | 0% | 10% | 0% | 50% |
| Q4 | 30% | 0% | 0% | 0% | 100% |
| Q5 | 35% | 5% | 10% | 0% | 100% |
| Q6 | 35% | 0% | 0% | 0% | 100% |
The league runs both ways
What Kate did next
So what exactly did she join, back in Q3?
Time to declare my interest plainly, since The Startup Race is our competition and I run it. But the mechanism is the point, not the branding. The old syndicate gave Kate pooled diligence, which was already a leap from doing it alone. The Startup Race goes a step further and moves most of the risky screening to before the investor ever arrives.
Here’s how. In a normal funnel, the angel or the group does the brutal work of examining forty companies to find one, and most of those forty are unproven ideas with a deck and a dream. In The Startup Race, fifty founders spend 52 weeks proving revenue in public, on a weekly league table of verified weekly revenue, drawn straight from their accounting systems. To even qualify, a founder has to be generating £5,000 of annual recurring revenue, which is about £96 a week. As we put it, rather bluntly, on the site: if you can’t convince strangers to pay you that much, you’re not ready to race. So the wishful thinking, the founders who can pitch but can’t sell, gets filtered out at the door, and then again every single week for a year, by the market itself rather than by Kate’s evenings. By the time she looks at the top of that league table, she isn’t looking at forty maybes. She’s looking at a handful of companies that have already survived a year of public, revenue-first natural selection, following the Four Sequential Problems method that has founders solve awareness, then fit, then traction, then scale, in that order. The funnel has been run for her, in daylight, using the one signal that can’t be faked. Real money from real customers. And on fees, the part that would have surprised the younger Kate most: no completion fee is billed to the founder, the model is membership and admin only with no carry or commission, and The Startup Race Ltd puts its own £10,000 into the winner on identical terms. None of Kate’s money walks back out of the door as somebody’s arrangement charge, and none of the founder’s runway does either, which is precisely why the founder scoreboard matters to her returns.
Now, the Race itself starts this summer, and the winner’s investment lands a year after that. So everything from here is the film run forward, the same trick the diligence table just played on you, the next twenty years told as Kate will remember them.
Kate’s first cheque wasn’t written to a pitch deck. It was written to a scoreboard.
She had three ways in, and she used all of them over time. She backed the winner of the £100k Race, the founder who’d topped the Premier League after twelve months of published weekly revenue. She went pro-rata alongside one of the Golden Buzzer investors, borrowing the conviction of someone who’d done the deep work so she didn’t have to repeat it. And when the competition finished, she invested alongside the observing investors, the ones who’d spent a year watching the field before committing a pound.
Notice what she never did. She never sat through a pitch evening.
Then the £1M Race changed her arithmetic entirely. Ten investees of £100k each, plus the wider field of race-proven companies around them, meant she could build the twenty-company portfolio the research recommends in two years rather than the decade it takes a conventional angel collecting deals one dinner at a time. Her Premier League returns, on the model’s own numbers, arrive in eight.
Now run her forward, because she’s 30, and the decades are the whole point. Suppose she invests £50,000 a year for ten years. On paper that’s £500,000 deployed, but SEIS relief at 50 per cent and EIS at 30 per cent mean HMRC hands £20,000 to £25,000 of it back each January, so her real outlay is nearer £300,000. Each yearly vintage compounds at the rate implied by the model’s own worked example, £100,000 becoming £500,000 or more over a decade, which sits comfortably below the multiples Wiltbank recorded for the high-diligence cohort, so it’s a Premier League assumption rather than a fantasy one. By 40 her portfolio’s paper value is around £1.35 million, with the first exits just landing. By 50, all ten vintages matured, she’s realised roughly £2.5 million. Every pound of gain free of capital gains tax, which at today’s rates is about £480,000 the Treasury never collects. The taxman was her co-investor on the way in and her silent partner on the way out.
The usual objection is the power law, and it’s a fair one. Some of her companies will return nothing, and two poor vintages would dent those numbers meaningfully. But this is where the model earns its keep at the bottom of the distribution as well as the top. Wiltbank found roughly half of conventional angel investments return less than the capital put in. Kate’s companies had all banked twelve months of verified weekly revenue before she ever saw them, and our own data from the earlier, smaller races, a small sample, honestly declared as such, shows even the bottom tenth of participants averaging £50,000 in annual revenue, several times the UK startup norm. She isn’t funding experiments. She’s funding businesses that have already survived the period in which most startups quietly die. The model raises her ceiling through diligence and raises her floor through selection, and the floor is the part nobody puts on a poster. And where a company does fail, SEIS loss relief means a failed pound costs an additional-rate taxpayer about 27 and a half pence, so even her zeros aren’t quite zeros.
Will she make it? I can’t tell you that, and I won’t, and you should distrust anyone who does. This is a projection, an illustration of a direction, and it comes with no guarantee attached, because none would be honest. Angel investing is high risk. Most individual angel investments lose money. Wiltbank’s UK data found that 56 per cent of exits failed to return even the capital put in. Capital is genuinely at risk, the returns take the better part of a decade, and the power law means most of Kate’s companies will disappoint her while she waits, quietly, for the ones that don’t.
But I know which layer of the pyramid she’s now standing on, and I know both of her columns are moving. The old way, the following-the-crowd way, the light-touch way that four out of my five characters practise for four out of five perfectly good reasons, keeps most angels on the bottom layers for life, held there by sunk cost and by the comfortable gravity of their own social group. The new way, the one the research has been quietly pointing at since 1996, is available to anyone willing to admit which game they’re actually playing, and then to play it in a structure built for people who have day jobs.
Kate finished her coffee. She asked how to join. That, more or less, is the whole story.
The league table was always there. She just needed someone to show her she was on it. There turned out to be two of them, and she’s climbing both.
A last thing, since Kate’s question will occur to some of you. The next Race runs for 52 weeks with the league table published weekly, and there’s a seat for people who just want to watch: no commitment, no cheque, the same verified revenue Kate saw, live. If you’d like to see the table for yourself before deciding whether you’re on it, take the Race Observer seat at join.thestartuprace.com/observer. And if your next question is whether you’d qualify to invest at all, the the four routes to sophisticated investor certification, including the two considered crowdfunding investments that solve the chicken-and-egg problem of needing to be in the game before you’re allowed in
Appendix: verified sources
This article is for information, not investment advice. Angel investing is a high-risk asset class. Your capital is at risk and you could lose all of it. Tax reliefs depend on individual circumstances and may change. Characters are fictional composites; projections are illustrations of direction, not promises. Past research findings are not a promise of future returns.