If you’re building an early-stage startup, you have to take risks. You have to be willing to tear the band-aid off, go for it, and see what happens. You have to accept that failure isn’t something that might happen — it will happen. Repeatedly. Sometimes several times in a single day. Sometimes in small ways, sometimes in big ways, sometimes in the form of a complete rethink or pivot.
And if you’re not okay with that, early-stage startups are going to be deeply uncomfortable for you.
What I find interesting — and what I see over and over again — is how this changes as soon as a startup starts to feel even slightly established. A bit of funding. A bit of revenue. A couple of customers. Suddenly, behaviour shifts. People start acting like there’s something precious on the table that needs to be protected.
At that point, risk doesn’t disappear — it just gets handled badly.
Later-stage companies absolutely still take risks, but they manage them carefully. They isolate them. They make sure a bad decision doesn’t wipe out the baseline business. That’s sensible when you actually have a baseline business.
But early on, most startups don’t.
And this is where a lot of founders — especially those coming from corporate, or bringing corporate people in too early — get themselves into trouble.
Corporate teaches you to protect. Startups require you to expose yourself.
People coming out of corporate environments have been trained, for years, to protect what they’ve got. Protect revenue. Protect reputation. Protect customers. Protect internal political capital. That training is logical in a large organisation. It’s how companies survive.
But when you launch a startup, you don’t have those things.
You have an idea. Maybe a prototype. Maybe twenty or thirty thousand in the bank — often your own money plus a bit of angel capital. That’s it.
And yet, founders and early teams start behaving as if that £20–30k is something to preserve, rather than something to use. As if the MVP is something fragile that mustn’t be broken. As if early revenue is proof, rather than a signal that still needs testing.
It’s not.
Angels aren’t there to watch you carefully protect a small pile of cash. They’re there because they want you to use that money to springboard the company towards something that could be worth ten times more. That doesn’t come from playing safe. It comes from doing uncomfortable things, taking opportunities when they show up, and having the courage and tenacity to push into uncertainty.
That mindset shift is critical. And if it doesn’t happen, the founder — or the people advising them — can very quickly become the problem.
My first startup worked because we didn’t try to behave "sensibly"
Looking back at my first startup, one of the big reasons it worked was that neither my co-founder nor I tried to run it like a corporate.
Both of us came from long corporate careers. I’d spent around thirteen years in a large civil engineering firm. He’d spent close to twenty years in a law firm. But in both cases, we’d been outliers inside those organisations. We were the people who thought differently, did things differently, and were given unusual problems to solve because of it.
In my case, that meant being dropped into Southeast Asia and asked to grow and reshape an operation across six emerging market countries. It wasn’t neat or linear. It cut across highways, bridges, water, energy, advisory work — multiple disciplines, multiple services, multiple contexts. One of my bosses used to call me the “all-terrain vehicle” because I could move across very different terrain and was willing to jump off a cliff, so to speak, to make things work.
That willingness to jump was exactly what they wanted in that role.
My co-founder had done something similar, growing a business from scratch in Vietnam by combining legal and advisory services in a way that wasn’t traditional at all. It worked because he didn’t try to force it into an existing mould.
So when we came together to build our first startup, we didn’t bring corporate caution with us. We tore the band-aid off early. We took risks. We did things differently to how we’d done them in corporate. We moved fast, broke things, changed direction when needed, and didn’t get emotionally attached to early versions of the business.
Within about sixteen months, it worked.
Not because we were cleverer than anyone else, but because we didn’t waste time pretending there was something to protect when there wasn’t.
My second startup stalled because I did the opposite
The contrast with my second startup is pretty stark.
On the surface, it wasn’t that different. Similar type of work — management consulting, business consulting, infrastructure advisory. Familiar territory. But this time, I brought in more people from corporate backgrounds right from the start.
They were good people. Strong in a corporate context. Sensible. Reliable. But they weren’t startup-minded. The hunger was different. The tolerance for ambiguity was different. The risk appetite was much lower.
And the company felt it almost immediately.
For about nine months — which is a long time in startup terms — the business stuttered. Decisions dragged. Things felt heavier than they should have. There was a constant, unspoken sense that we needed to be careful with what we had.
But what we had wasn’t the thing.
Eventually, it reached a point where something had to change. Risk had to be embraced again. The way we operated had to shift. Only then did the company start to move properly.
The difference between those two startups wasn’t market conditions or intelligence or effort. It was mindset. Specifically, how early we started acting like there was something to lose.
When experience becomes a liability
I saw a different version of the same problem later on when I joined a tech company that had just raised a large round — north of thirty million.
The company was scaling quickly, from five people to around thirty. They hired a mix of startup operators and very senior people from corporate environments. Impressive CVs. Strong opinions. Deep experience in their domains.
The problem was simple but serious: the company hadn’t actually proven anything yet. There were no customers. No validated go-to-market. No baseline business.
The founder, who hadn’t yet scaled a company at that level, suddenly had to manage a group of very seasoned people — many of whom had done impressive things in corporate, but none of whom had scaled an early-stage startup themselves.
What followed was predictable in hindsight. Silos formed. Teams optimised locally rather than globally. People did what they thought was “right” based on their own experience, but there was no shared mental model of what stage the company was actually in.
Everyone was trying to do their best. And yet the organisation became disjointed, slow, and internally fragmented.
Again, the issue wasn’t bad intent or lack of talent. It was a mismatch between experience, mindset, and stage.
Early on, failure is part of the job
One of the biggest mistakes I see founders make is trying to eliminate failure early on.
That’s the wrong goal.
Early-stage startups should expect failure — small failures, frequent failures, sometimes multiple in a single day. That’s how you find out what works. That’s how you get out of the hamster wheel.
The real danger isn’t failing. It’s failing slowly. Dragging things out because you’re trying to protect an MVP, or a bit of revenue, or a narrative that says you’re “making progress”.
Time is the killer. A fast failure teaches you something. A slow one just exhausts you.
When this mindset needs to change
As companies mature, this way of operating absolutely has to change. Once you have steady customers and predictable revenue, risk needs to be managed properly. You don’t gamble the core business. You don’t casually blow things up. That’s why big companies feel slow and bureaucratic — it’s what keeps them alive.
There’s one important exception. If your entire business is already at risk — because a substitute product is coming, or the market is shifting under your feet — then sometimes the only option is to take a leap of faith and hope the thing you’re building can get you to a safer place.
But early-stage startups are not there yet.
They don’t need protection. They need to move.
The thing founders need to get right
What founders — particularly those coming from corporate — need to learn is how to shift their mindset based on where the company actually is.
Early on, acting like there’s something to protect will hold you back. Later on, not acting that way will kill you.
The problem is applying the wrong mindset at the wrong time.
Early-stage startups aren’t container ships. They’re speedboats. And if you treat them like they’re already fully loaded and crossing an ocean, they’ll never get going.
