Remember Facebook in its heyday? 

Scroll back far enough, and it’s a digital museum of bathroom-mirror selfies, cryptic relationship updates and someone reporting they’d “just had lunch” as if it was breaking news. 

Before long, it wasn’t just status updates. 

Facebook became a place to build a whole identity online - joining groups, messaging friends, organising events, arguing in comments, keeping tabs on exes and discovering brands we didn’t know we needed. 

It turned everyday life into a shared feed of opinions, photos and distractions and more importantly, fuel for targeted ads.

Meanwhile, Facebook’s founder - Mark Zuckerberg - was making an obscene amount of money from it all. Not directly from us (yes, I was a Facebook-er back in the day), but from what our habits proved: Facebook was addictive, scalable and full of monetisable attention. 

The perfect proof to raise on repeat.

Instead of cashing in with one giant round, Zuckerberg used that evidence strategically. 

From 2004 to 2017, Facebook raised small, consistent rounds every 12-18 months - using data, traction and results to secure better terms each time. 

For him, raising capital was a rhythm. A tactic. And when other founders seeking funding treat it that way, they negotiate from strength instead of panic.

You’re probably keen to dig up your old Facebook posts now, but hold that urge for a sec and keep reading this.

TL;DR:

A) Facebook kept lifting its valuation by raising in small, frequent steps; each round priced on results already proven.

B) Raising while there’s still runway keeps the power dynamic on your side: you choose investors rather than scrambling for whoever says yes.

C) A strong pitch is important, yes, but operational discipline gives investors confidence the business can scale without losing control.

D) Momentum compounds: each milestone increases confidence, which drives better terms, which fuels more momentum - the cycle behind Facebook’s rise.

Facebook’s timeline

Before it became our unofficial birthday calendar, Facebook was just a low-budget college website with a surprisingly strategic approach to money.

  • In 2004, the company raised $500K from Peter Thiel, who picked up roughly 10% of the business. But this wasn’t a grab-everything-while-we-can moment. It was small. Intentional. Enough to build momentum, not enough to get lazy.

  • Then came 2005, and rather than immediately chasing a giant VC cheque, they raised a modest $12.7M Series A. By then, Facebook had real data to show off: users were signing up, logging in, coming back, obsessing, tagging friends in photos - all the economic cues investors dream about.

  • Over the next seven years, the pattern continued. 21 rounds. $2.27B in total. But always in small, frequent bursts. Each round was backed by fresh proof - new growth, new engagement metrics, better monetisation signals.

  • Today, Meta (formerly Facebook) reaches over 3 billion users a month and brings in more than $160B a year. That scale wasn’t built on constant invention - it came from doing the basics exceptionally well: executing, monetising attention and acquiring what it couldn’t build fast enough.

The platform itself looks nothing like those early student-only days. Young people drifted off to TikTok and Instagram, and Facebook slowly turned into a place where middle-aged relatives share holiday snaps, argue about bin collections and tag each other in photos no one asked for. It’s not cool, but it is commercially powerful.

And that’s exactly the point. Older users have more money, click more ads and are easier to monetise - which makes Facebook’s “uncool” audience incredibly profitable. Meanwhile, Meta kept the younger crowd anyway by buying Instagram. 

In simple terms: Facebook now makes money from the people who stayed and the people who left. That’s the same strategy that started with small, disciplined raises: don’t chase hype - own behaviour, wherever it goes.

Now, back to the earlier raises

By raising little and often, Facebook grew like a company that always had something to prove. With no mountain of cash to hide behind, it stayed lean, aggressive and laser-focused on growth. 

Now, this is the important bit:

Every 12-18 months, Facebook went back to investors - not asking them to imagine a prosperous future, but showing them what was already happening:

  • millions of new users signing up

  • people checking the platform multiple times a day

  • users spending longer on the site

  • constant tagging, positing, scrolling and sharing

There was no denying it: people were spending a lot of time on Facebook. And when a platform has people’s time, it has something advertisers are happy to pay for.

So in each fundraising round, investors weren’t gambling on what Facebook might become; they were investing more because Facebook had already proved that the previous rounds had worked.

That steady proof kept investor relationships warm without desperate pitching. Facebook stayed front-of-mind because it always had clear results to show. It’s a compounding cycle:

Small raise → execution → data → higher valuation → repeat

These points triggered a great conversation on LinkedIn. Someone pointed out how this approach keeps founders sharp and investors genuinely engaged. They’re spot-on - and what’s interesting is that this discipline doesn’t just work at early stage. It scales. 

Klarna, for example, hasn’t relied on mega-round shock value; instead, they’ve built a $6B+ business by raising smaller strategic tranches that preserve agility, control and narrative power - even at global scale.

In other words: the rhythm still works, whether you’re scrappy, growing fast… or already a fintech giant.

Time to break down the mechanics

I love a big funding headline as much as the next person, but the real value is in how the result happened. If you’re thinking about taking out a business loan, here are five principles to bear in mind while doing so:

A) Think cadence, not cashpile

A big lump sum feels exciting… right up until it funds random hires, questionable ‘growth projects’ or an office no one asked for. Smaller, frequent raises do something smarter: they force focus. With limited cash, teams prioritise what actually moves the business forward.   

B) Build confidence between the rounds

Stay visible between raises with measurable wins: a margin improvement, a key hire that’s already paying off, retention that didn’t need heavy discounting. These are your trust deposits. Show progress before you ask for capital, and the ask sounds more like an opportunity rather than a rescue mission.

C) Let your numbers answer the hard questions

Relationships get you in the room. Metrics stop you being escorted out. When clean unit economics and scalable delivery do the talking, investors don’t waste time asking whether it works - they ask how big it can get. This is where you show them the numbers.

D) Let your decisions tell the story

A compelling founder narrative isn’t about a dramatic origin moment, but consistent decision-making. Why this product, not another? Why say no to a shiny opportunity others chase? Why prioritise one customer segment over the rest? Clear judgement is a signal of leadership. When your choices make sense, investors don’t just believe in the business - they believe in you running it.

E) Monetise on existing behavioural patterns

Meta’s real advantage is monetisation rather than reinvention. It watched how people behaved, then built revenue engines around those habits. People posted photos? Ads followed attention. People moved to visual-first content? Zuckerberg bought Instagram.

The lesson: don’t try to guess the future. Find entrenched customer behaviour and plug a business model into it. Obvious habits make the strongest growth engines.

The easiest way to annoy me is…

Ask me how I started my business, FundOnion

I know, it’s a bit ridiculous to let such a simple (and valid) question grate on me. But it usually comes with the expectation of a neat blueprint: do X, then Y, follow Z and voilà - business built. It doesn’t work that way. 

Take Jeff Bezos’ origin story. He worked at a hedge fund, quit at 30, drove to Seattle to start an online bookstore and ended up being a billionaire by 33. It’s hardly going to be useful to 99% of founders who don’t live inside a Silicon Valley fairytale. 

My point here is to not try to copy someone else’s circumstances, but extract the key principles. 

And if you really are curious about how I started my business, here’s how:  

I was a lawyer before I got into finance, and I hated it. That’s it. I realised I didn’t want to spend the rest of my life doing something that wasn’t fun or rewarding for me. So I jumped into starting a business completely unprepared. I was woefully ignorant at the time (still am, just less dangerously so), but I figured things out as I went.

It seems to have worked out well in the end, largely thanks to the brilliant people I work with.

Pet Peeves aside, let’s wrap up Facebook’s fundraising story

If there’s one theme running through all of this, it’s that progress is a better strategy than certainty. Facebook didn’t know exactly what it would become. Most founders who build something meaningful don’t start with a perfect plan - they start with movement, then make better decisions as the picture sharpens.

This makes the most reliable strategy surprisingly simple: keep making steps worth funding. And if you need that extra push to do so, lucky you - that happens to be my speciality. Reply to this email and I’ll help.

Till next time,

James

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