Alex:
When people talk about fundraising, they always focus on the moment the deal closes. The announcement. The photos. The “we’re excited for the next chapter” LinkedIn post. But you’ve said before that for you, Matt, that was actually the moment things became harder.

Matt:
Yeah, massively. I think people assume the raise removes pressure, but honestly it just changes the type of pressure you’re under. Before the investment, you’re trying to survive. After the investment, you’re expected to scale.

Will:
And suddenly everyone’s watching.

Matt:
Exactly. Your investors are watching. The team’s watching. Customers suddenly take you more seriously. There’s this expectation that because you’ve raised money, you now have all the answers.

Alex:
Did it feel different internally straight away?

Matt:
Immediately. The day after the announcement we were already talking about hiring plans, growth targets, operational changes. We went from a small team figuring things out together to needing an actual structure almost overnight.

Will:
That’s the bit nobody really sees from the outside, right? Everyone sees the funding number but not the operational reality behind it.

Matt:
Completely. Raising money creates momentum, but it also exposes all the cracks in the business. If your hiring process is weak, you feel it faster. If communication isn’t good enough, you feel it faster. Everything speeds up.

Alex:
What was the hardest part for you personally?

Matt:
Hiring senior people, without question.

At seed stage, everyone’s just doing everything. But after the raise, you suddenly need leadership layers. Managers. Specialists. People who’ve “done it before.” And honestly, I think we underestimated how difficult that transition is.

Will:
Because on paper, you can hire incredible people…

Matt:
…who are completely wrong for the stage you’re at.

We made one hire that looked unbelievable on LinkedIn. Massive company background, scaled teams, investor-approved — the whole thing. But startups are chaos. You need people who can operate with ambiguity and build things from scratch.

And I think that’s where founders get caught out. They hire experience instead of adaptability.

Alex:
How much did that impact the business?

Matt:
A lot more than I expected. Probably set us back close to a year.

Not because they were bad — they genuinely weren’t. But culturally and operationally it just didn’t fit. And when you’re still relatively small, one senior hire changes the entire dynamic of the company.

Will:
Did you feel pressure from investors to scale quickly?

Matt:
Definitely. Not direct pressure in a negative way, but there’s an implied expectation once capital lands. You’ve raised because you’ve sold a vision of growth. So naturally everyone wants momentum quickly.

The challenge is balancing speed with stability.

Because bad hiring in a startup isn’t just expensive financially — it affects morale, culture, confidence… everything.

Alex:
I think people massively underestimate how emotional scaling becomes.

Matt:
100%.

Everyone talks about growth like it’s just numbers on a spreadsheet. Revenue targets, headcount, ARR. But scaling is emotional. You’re managing uncertainty every day while trying to keep the team confident.

There were definitely moments where I felt more stressed after the raise than before it.

Will:
Which sounds counterintuitive to most people listening.

Matt:
Totally. People think funding equals safety. But funding really just buys you time. What matters is what you do with it.

And suddenly there’s a clock running in the background all the time. Runway becomes a constant thought in your head.

Alex:
Did the culture change as the company grew?

Matt:
Yeah, and that surprised me as well. Early-stage culture happens naturally because everyone’s close together. But once you start hiring quickly, culture stops being accidental. You actually have to build it intentionally.

That was a huge learning curve for us.

Will:
What do you think founders get wrong most often after a raise?

Matt:
Trying to look bigger than they are.

I think a lot of founders feel pressure to act like a “proper scale-up” immediately. Bigger teams, more meetings, more layers, more process. But sometimes you lose the agility that made the company successful in the first place.

Alex:
That’s interesting because the outside world often celebrates growth at all costs.

Matt:
Yeah, but internally growth can feel messy. Some of the hardest periods for us happened during our fastest growth phases.

Because the business changes faster than people can adapt to it.

Will:
And founders rarely say that publicly.

Matt:
No, because everyone wants to project confidence. Especially after a raise.

But honestly, most founders are figuring things out in real time. There isn’t some secret playbook. You learn under pressure.

Alex:
That’s probably why conversations like this matter though.

Matt:
Exactly. Because the raise isn’t the finish line.

It’s just the point where the real work begins.