Backing Contrarian Ideas & the story of Airbnb

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The Problem with Playing It Safe

I read a great piece recently by Matthew Roberts at Nodes Ventures. He framed European VC as a prisoner’s dilemma, and it got us thinking.

Every fund wants to do better deals at better prices. But no one wants to be the first to walk away from the overpriced “hot” deal. So what happens? Everyone waits. Everyone hedges. And everyone follows. And you end up with a sea of safe bets, all slightly different flavours of a similar thing.

But here’s the thing: this isn’t just about groupthink. It’s not just about being sheep. It’s about fear.

Investors don’t just follow because they’re lazy or slow. They follow because they’re scared of being wrong. Scared of looking stupid. Scared of backing something weird that no one else gets and having to explain it to their Investor committee, or worse, their LPs. Because when something is contrarian - when it looks odd, complex, or just hard to understand, the answer is often unclear. 

That’s the real fear. Not that the investment will fail, but that they’ll be alone when it does. So funds end up optimising for safety and back what everyone else is backing while passing on what no one else understands. Don’t risk being the outlier, unless someone else goes first.

This is how you end up with a market where every fund claims to be hunting outliers but behaves like they’re running a pension fund. And it’s why so many of the world’s most iconic startups were written off in the early days. Because they didn’t look “venture backable.” They just looked…weird.

Contrarian ≠ Crazy (But It Might Look Like It)

Let’s be clear: being contrarian isn’t about betting on every left-field idea you come across. It’s about backing something that most people don’t believe yet, but that you do. Deeply. Rationally. For reasons that mightn’t fit on a pitch deck slide.

The problem? Contrarian ideas rarely come gift-wrapped. They look awkward. Niche. Unscalable. Or just straight-up confusing.

Because anything truly new starts off unfamiliar. And our instinct, especially in finance, is to kill what we don’t immediately understand.

But unfamiliar ≠ wrong. Unfamiliar is just...early.

VCs say they’re looking for the next Airbnb or Uber or Stripe. But what they’re actually looking for is the current version of those companies. Polished, proven, de-risked.

The uncomfortable truth is that most iconic companies didn’t make sense at the start.

• Uber? Illegal taxis.

• Airbnb? Sleeping in a stranger’s apartment.

• Stripe? A payments API in a market already dominated by PayPal.

To believe in any of these early on required imagination and a tolerance for ambiguity.

But not all VCs are wired for that. They’re wired for pattern-matching. Does this founder look like the last successful founder? Does this deck remind me of something that worked before?

They want a benchmark, not a vision. And that’s the trap.

You don’t get outsized returns by picking what everyone already understands. You get them by backing the thing that feels weird, but turns out to be right.

The Airbnb Origin Story (The short version)

In 2007, Brian Chesky and Joe Gebbia were broke and about to miss rent. A major design conference was taking place in San Francisco, and all the hotels were fully booked. So they did something weird.

Knowing that a huge number of people would be coming to town for this conference, but with no hotel rooms available, they bought three air mattresses, laid them out on the floor of their apartment, created a basic website, and called it AirBed & Breakfast. They charged strangers $80 a night to sleep on their floor, and threw in breakfast.

That was the MVP (Minimum Viable Product)

And it worked. They made a little cash. And more importantly, they saw a new behaviour: people would pay to stay in someone else’s home. So they leaned in. 

They brought in a third co-founder, their former roommate, Nathan Blecharczyk, and tried to raise money. But the pitch was too weird. Too uncomfortable.

Letting strangers sleep in your house? No thank you.

They got rejected by basically every VC they spoke to. The reasons varied, but the underlying message was always the same:

“I don’t get it. And I don’t think anyone else will either.”

(You can read some of the real replies Brian Chesky received HERE)

But they didn’t quit. They scraped together money however they could. Their most famous hustle? Selling politically themed cereal during the 2008 U.S. election. 

As they were starting out in the summer of 2008, the founders needed a way to raise money. They bought a ton of cereal and designed special edition election-themed boxes, released that fall - Obama O’s and Cap’n McCain’s, which they sold at convention parties for $40 a box. They sold 500 boxes of each cereal, helping them to raise around $30k for Airbed & Breakfast.

Still, the site did not gain much traction initially, and the founders resorted to living off of leftover Cap’n McCain’s (the Obama O’s sold out). A time they refer to as a real “low point.”

Eventually, they got into Y Combinator after meeting Paul Graham the following Spring and from there were able to raise $600k from Sequoia and Y Ventures, getting them started on the journey to the giant they are today. 

Airbnb didn’t break through because it was obvious. It broke through because they refused to die. And now, they’re worth nearly $100 billion.

But the most interesting part isn’t what they’ve become.

It’s how close they came to never existing, simply because no one wanted to look stupid for backing them early.

Fred Wilson at Union Square Ventures, who notoriously rejected Airbnb, claimed in 2011 that Union Square kept a box of Obama O’s in their conference room to remind themselves not to make the same mistake again!

What Most People Miss About Outliers

The hardest truth in venture is this:

Many companies fail

That’s not a flaw in the model, that is the model. Venture is governed by power laws - one or two investments make the fund. 

It’s not about how many times you’re right, it’s about how right you are when you are.

And that changes everything. It means you don’t need to find 20 good companies. You need to find one monster. The one that returns 100x and pays for all the others.

But here’s the catch: those outliers rarely look obvious at seed stage. They look messy. Raw. Half-baked. The product is janky. The team is weird. The idea feels small, or way too big.

That’s why so many VCs miss them. They’re comfortable making safer bets. 

But outliers don’t fit in boxes. They show up like Airbnb - weird, uncomfortable, and easy to dismiss. That’s what makes them such great investments. Because if everyone could see it, the upside would already be priced in. So what most people miss is that outlier returns require outlier courage.

You have to be willing to look wrong and alone, for a while. And most investors aren’t. They’re optimising for not looking dumb. Not for finding the next Airbnb.

Shuttle’s POV And Why We Care 

This isn’t just a story we like telling. It’s a problem we’re actively building around.

Because the reality is, most retail investors will never get close to an Airbnb. Not because they aren’t smart enough, but because they’re locked out of the game. Closed networks, outdated accreditation rules, and tiny deal flow windows mean the odds are stacked from the start.

Even when access is possible, the risk is skewed. That’s why our approach at Shuttle is simple:

Don’t try to pick winners. Pick enough good shots.

We take an indexed approach to startup investing. Not in the passive, lazy sense, but in the intelligent, diversified sense.

We help investors build broad portfolios. Not by guessing, but by investing alongside leading VC funds and casting a wide net across sectors, stages, geographies, and time because that’s how you catch the outliers.

It’s not about predicting the next Airbnb. It’s about putting yourself in enough deals that if an Airbnb does show up, you’re already involved.

That’s the game most retail investors have been locked out of. And it’s the game we’re unlocking. Not by dumbing it down, but by raising the bar on access.

Because the future doesn’t belong to people who play it safe. It belongs to the ones willing to swing big, and swing often.

Final Take

Hindsight always makes everything look obvious, but the best companies rarely look like the best companies at the start. 

At Shuttle, we’re not here to chase what already makes sense. We’re here to give more people a shot at the ones that don’t…yet.

Our next Drop opens next week. See you there?

What we’ve been working on at Shuttle

• Drop No. 3 goes live on Monday July 14th 💪

• Getting started on building a new product 😏

• Working on scaling the team from 2 to 5 🤝

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