The Anatomy of a round (and why they never go to plan)

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If you’ve ever wondered how a startup “raises a round,” you’re not alone. It’s one of those phrases people in tech throw around casually - like everyone was born understanding cap tables and term sheets.

The truth? Even inside the industry, the process is messy. Every round is its own little universe of ambition, pressure, and luck.

And since we’ve had to delay our 4th Drop this week - due to the deals still being in motion - we thought it’s the perfect time to show you how this really works - and why, in private markets, timing almost never behaves.

What’s an investment round, really?

At its core, an investment round is how startups raise capital to hit their next big milestone - building a product, hiring a team, expanding into new markets.

Investors put in money in exchange for equity - a slice of ownership in the business. That ownership grows in value if the company succeeds.

Rounds are usually defined by stage and size: Pre-Seed, Seed, Series A, Series B, and so on. Each step up the alphabet signals more progress, more capital, and more proof that the company’s onto something real.

Early rounds aren’t “guesswork.” They’re built on conviction. The data might still be thin, but the signals are real - the team’s track record, the product’s early pull, the clarity of the vision. Investors at this stage are betting on momentum and execution, not spreadsheets.

It’s part strategy | part storytelling - and when it works, it sets the foundation for everything that follows.

How rounds actually play out

On paper, fundraising looks structured. Set a target, talk to investors, close the round.

In reality, it’s more chaotic than that.

Rounds almost never move in straight lines. They can drag on for months… then suddenly close in 48 hours. One lead investor says yes, and suddenly everyone else wants in. Momentum flips the switch.

Founders are negotiating terms, managing due diligence, and juggling legal documents - all while still running the business day-to-day. It’s not glamorous; it’s exhausting.

Valuations get debated. Deadlines slip. Investors change their minds. Rounds can morph multiple times before they finally close.

And even the best founders (the ones with traction, hype, and confidence) still get blindsided. Deals fall apart at the last minute. Term sheets evaporate. Or a new investor appears out of nowhere and reshapes the whole thing.

That’s fundraising.

The public never sees the chaos - just the glossy “we’ve raised €5 million!” post once it’s all over. But behind that headline are months of late-night calls, near-deals, and spreadsheets full of maybes.

What this means for Shuttle (and for you)

At Shuttle, you only see the rounds once they’re fully formed and ready to go live - after months of behind-the-scenes work. Every deal we bring to the platform has gone through deep diligence, negotiation, and legal alignment between investors and founders.

Drop 4 was meant to launch this week but both upcoming deals are taking longer than expected. We can’t rush that process. These are real companies raising real money - not campaigns we can just schedule in advance.

And to make things trickier, rounds can open at the drop of a hat. One founder gets a term sheet, one lead investor moves, and the whole timeline shifts overnight.

We’re building a platform for a market that doesn’t run on schedules.

That unpredictability is part of what makes venture investing exciting - and part of why it’s hard to preempt. Access depends on timing, and timing, by nature, is unpredictable.

So when a Drop takes longer than planned, it’s not because things have gone wrong. It’s because we’re doing the work properly: sourcing credible deals, aligning with professional investors, and making sure that when you see a round on Shuttle, it’s one worth your attention.

Behind every opportunity on our platform is a founder trying to build something extraordinary - and an entire process that has to unfold before we can invite you in.

How we think about this

We’ll always be straight with you. No fluff, no filler Drops just to hit deadlines.

The nature of early-stage investing is patience and readiness. The best opportunities rarely arrive on schedule - but when they do, they move fast. Our job is to make sure you’re ready when that happens.

So if Drop No.4 takes a little longer, that’s okay. It means the work’s being done right.

Thanks for bearing with us. And if you’re new here, sign up to be first in line when Drop 4 goes live.

It’ll be worth the wait.

What we’ve been working on at Shuttle

• Ensuring everything is ready to launch Drop no.4 🚀 

• Submitted our application for FCA Authorisation 🇬🇧 

• Devising a new content marketing strategy 👀 

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