Why startups are a long game - not a lottery ticket

Hello friends, and welcome to The Unsophisticated Investor! Brought to you by Scott & Rob, the founders of Shuttle!

If you want to invest alongside the VC funds who've backed breakout companies like Revolut, Asana, JustEat, Bolt, Lets Get Checked, Loom, Runna, Charlotte Tilbury, Deel, Aircall, AngelList, Carta, TransferWise and many more, regardless of your knowledge, network or net worth, join our limited waitlist now.

Now, let’s get into it 👇

The myth of the big win

When most people hear “angel investing,” they think of lottery tickets. You write one cheque. You hope it’s the next Stripe. And if it takes off, you’re set.

That story is seductive. And it’s everywhere; in media profiles, founder interviews, even platform ads. But here’s the truth most people don’t hear: real startup investing isn’t about picking winners. It’s about building a portfolio.

Yes, a single big win can carry your returns. But the path to that win isn’t random, and it definitely isn’t fast. Most successful angel investors don't have better luck. They have better discipline. They spread their bets, manage their risk, and give those bets time to mature.

Why the long game works

Startups don’t move at the pace of public markets. There are no quarterly earnings calls. No daily liquidity. Just years of building and sometimes years of nothing.

Most meaningful exits take 7–10+ years. Some take longer. That means the money you invest today is likely locked up for a while. But if you’re patient? That’s where asymmetric returns live.

Angel investing follows power law dynamics: in a well-built portfolio, 1 or 2 companies will return most of the value. The rest may break even, underperform, or fail entirely. That’s not a bug, it’s the design.

Which is why the long game isn’t just wise, it’s essential. The magic doesn’t happen in year two. It happens when one company compounds, survives, and breaks out, while the rest quietly fade.

What most first-time investors get wrong

Most angel investing mistakes don’t come from bad luck. They come from misunderstanding the game.

Here’s what typically happens: someone gets access to a startup deal, gets excited, and writes a cheque. Maybe two. But they treat it like a one-off opportunity, not part of a longer strategy.

The problem? A portfolio of one or two startups is almost guaranteed to disappoint. Even pros expect a chunk of their investments to go to zero. But that’s fine, because they spread their risk over 20, 30, sometimes 50+ companies.

Other mistakes? Chasing hype. Overvaluing “the idea” instead of the team. Underestimating how long it takes to see any return. Angel investing isn't about catching trends, it’s about backing execution.

The best investors don’t chase winners. They build a repeatable approach and stay in the game long enough for the odds to shift in their favour.

The hardest part: doing nothing for years

Writing the cheque is easy. Waiting is hard.

Most of us are wired for feedback; we check our portfolio, track performance, tweak as we go. But startup investing flips that on its head. There are no charts to watch. No quarterly earnings. Sometimes, no news at all.

You might go years without hearing much from a company you’ve backed. And when updates do come, they’re often vague or full of jargon; “runway extended,” “pivoting GTM,” “hiring a COO.”

That silence makes people second-guess. Am I losing money? Should I have sold? Is this thing even alive?

But here’s the paradox: the best outcomes often come from the investors who do the least. Who stay diversified, stay patient, and resist the urge to micromanage something they were never meant to control.

If you can sit with that discomfort (and zoom out) you give yourself a shot at the kind of asymmetric outcomes that make the wait worth it.

What smart investors do

Smart investors don’t try to predict the next unicorn. They focus on stacking the odds in their favour.

That means:

• Diversifying across at least 20 startups, ideally over a few years

• Expecting losses and designing their portfolio knowing some bets will fail

• Backing founders, not just ideas, because the best startups evolve constantly

• Investing with a clear thesis: what stage, sector, or business model they understand well

• Staying patient, knowing real outcomes can take a decade

They also look for ways to improve their exposure: co-investing alongside experienced VCs, accessing dealflow through trusted platforms, or sticking to sectors they know deeply.

But most importantly? They treat startup investing as a strategy, not a side hustle. A long-term move that complements the rest of their portfolio, not a moonshot that makes or breaks it.

Play the game the way it’s meant to be played

Startup investing isn’t about finding the golden ticket. It’s about understanding the rules of a different kind of game - one where time, patience, and pattern recognition matter far more than hype.

It’s not for everyone. But for those willing to play the long game - to diversify, stay curious, and think in decades - it can unlock a kind of upside you simply don’t get in public markets.

The key is knowing what you’re getting into and having the tools to do it well.

What we’ve been working on at Shuttle

• Closing in on the next two investment opportunities for drop #4 💧 

• Building out our first ad campaign for LinkedIn 📺️ 

• Counting down to our first Product Hunt Launch 🚀 

The Unsophisticated Investor is brought to you by Scott & Rob, the founders of Shuttle. We’re both sick of private markets being a playground exclusive to the ultra-wealthy so we started a company to challenge the status-quo. Shuttle’s singular focus is to unlock private markets for Millennial and Gen Z tech professionals and help them build wealth through the highest performing private market opportunities.

Scott & Rob
Shuttle Co-Founders