One startup, 50x. And you only needed one.

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 truth most investors don’t hear

You’ve probably been told to diversify. To buy index funds. To “play the long game.” And for the most part, that’s sound advice.

But here’s something public market investing rarely tells you: your upside is capped.

The best companies in the S&P 500 might 10x over a couple decades - and that’s if you timed it well, held through all the drawdowns, and ignored the noise. Most won’t even come close. Meanwhile, in venture capital, one winning investment can 50x and cover every other loser in your portfolio… and then some.

That’s not a fluke. It’s the model.

Venture capital isn't about being right all the time. It’s about being right once and having enough exposure to catch that one.

Most retail investors haven’t been taught to think this way. We’ve been trained for predictability, not power laws. But if you’re only playing in public markets, you’re playing a capped-return game in an uncapped world.

What “Asymmetric returns” really means

Imagine risking €1,000 and walking away with €1,000,000. That’s the kind of upside venture offers.

It’s called asymmetric returns: when the potential reward massively outweighs the risk. Your downside is capped at what you put in. But your upside? Uncapped. Infinite, theoretically. And in venture, that’s possible.

Take WhatsApp. A €250k seed round (let’s say at a €5m valuation) turned into a €19 billion acquisition. That’s a 76,000% return. One bet like that pays for every loser and then builds generational wealth.

Public market returns are symmetric. They grind upward over time, if you're lucky, at 7-10% a year. Venture is lumpy, erratic, and brutally unpredictable… until it isn’t.

In venture, returns follow the Power Law: a small number of breakout companies generate nearly all the gains. That’s why top-performing VC portfolios don’t look like mutual funds. They look like this: 1-2 massive winners, 5-10 moderate returns, and a long tail of zeroes.

Sounds risky? It is. But it's a calculated risk. And if you spread your bets smartly, the math works in your favour.

You don’t need to be a Genius, just in the game

Let’s kill the myth: venture success isn’t about spotting the next unicorn before anyone else. It’s about putting yourself in the path of opportunity.

The best investors don’t always know which startup will 100x. They just make sure they’re exposed to enough great companies that one or two eventually do. That’s the game. And it’s surprisingly accessible (if you play it right).

Think about it like this: investing in 50 early-stage startups doesn’t mean you’re making 50 high-risk bets. It means you’re increasing your odds of catching one massive outlier. AngelList data shows that with a portfolio of 50 startups, your chance of losing money drops to just 2.5%. Not because you’re picking perfectly. Because you’re diversified in a game where one hit pays for everything.

And you don’t need to write €50k cheques to play this way anymore. Thanks to platforms like Shuttle, you can now co-invest with top funds at much smaller ticket sizes, building a diversified venture portfolio without needing millions.

You’re not betting the house. You’re buying a lottery of calculated opportunities - with far better odds than the actual lottery.

Why now is different

Venture used to be a club. Invite-only. Old boys. Big cheques.

Unless you were a VC, a founder, or incredibly well-networked, you didn’t get access. The best deals? Gone before you even heard about them.

But the game’s changing.

Platforms like AngelList cracked open the door. Syndicates, solo GPs, secondaries - they all started chipping away at the velvet rope. And now, with tools like Shuttle, access isn’t a privilege. It’s a product.

Combine that with the rise of AI and community-led investing, and suddenly you’ve got everyday professionals building venture-style portfolios from their laptops. Discovery is faster. Diligence is smarter. Execution is simpler. The barriers are falling.

And retail investors aren’t just watching - they’re participating. Nearly half of Gen Z has already made their first investment. Many before they turned 18. This is a generation that expects to be in the room. And now, they can be.

For the first time in history, asymmetric upside isn’t locked behind closed doors. It’s just a click away.

So… should you go all-in on Venture?

No. That’s not how this works.

Venture isn’t about betting everything on a moonshot. It’s about smart exposure. It’s about putting a slice of your portfolio (maybe 5-10%) into a high-upside strategy that could transform your future.

The goal isn’t to swing wildly. It’s to tilt the odds. One 100x investment doesn’t just improve your returns - it reshapes them. That’s the power of asymmetry.

But here’s the reality: you won’t know which one it is until years later. So the move is to back multiple companies, consistently, with conviction. Focus on quality. Build a portfolio that gives you a real shot at catching an outlier. Then let time do the heavy lifting.

You don’t need to hit every winner. You just need one.

What we’ve been working on at Shuttle

• Inviting our initial users for our latest investment product 🧑‍💻 

• Planning our Product Hunt launch day for October 22nd 🚀 

• Building case studies for some of our recent investments 💼 

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