Entrepreneurship comes with a strange contradiction: from the outside it can look glamorous – the launches, the energy, the wins – but underneath it’s a swirl of risk, self-doubt, admin, people management, and blind optimism.
Across two WiiN sessions, four founders shared the truths they wished someone had told them earlier, from the first spark of an idea to the messy middle of hiring, funding, selling, and staying sane.
They came from different paths – corporate consulting, multi-exit founders, event organisers, association builders – but the themes overlapped in comforting (and sometimes painful) ways.
Founders don’t start with a master plan – they start with a spark
For Marie, the spark appeared only after she stopped rushing from one consultancy contract to another. She took two months off, travelled, painted her house, and gave herself space to think. Only then did ideas show up – a tutoring agency she could build with her husband’s network, and later a gift card business in Portugal, where she saw a clear gap.
Holly’s story began differently. She realised she was doing the same job for different employers and thought, “Why keep moving when I could just run my own thing?” She filed her paperwork, went to Money20/20 with a friend, and started telling people what she was doing – terrified, but moving.
Rocío’s start was more methodical. She calculated how much she’d need to survive a year without income, agreed it with her partner, and gave herself that timeframe to “try properly.”
Different journeys, same message: ideas don’t arrive fully formed. They reveal themselves once you step back, talk to people, and give yourself permission to explore.
Hiring and firing will grow you faster than any business book
Every founder touched on this – not in a “HR best practice” way, but in the “this is the part that keeps you awake” way.
Manon has learned to move fast:
She hires quickly and “fires even quicker” when it’s clear someone can’t thrive in a small, high-energy team.
She’s seen how people from large corporates struggle when suddenly nobody writes the deck for them — the founder is the sales team, the marketer, the engine. When someone can’t adapt, she acts. For her, carrying misalignment is more damaging than the awkwardness of letting someone go.
Holly has done both sides too, and says the emotional weight is real. Hiring the first person into a culture that previously existed only in your head is difficult; firing someone is worse when you’re the reason their mortgage gets paid. But she’s firm on one thing:
The only way to do it well is to treat people like adults – honestly and humanely. Marie tends to start with people she already trusts. It’s risky, she knows, but she values trust over everything when building something from scratch.
Across both sessions, it was clear: you learn who you are as a leader the day you build a team – and the day you let someone go.
Money anxiety never disappears – you just learn to work with it
No founder avoided the money conversation, because you can’t.
Rocío talked openly about the fear of leaving a stable salary:
She didn’t try to eliminate the fear; she tried to contain it. One year of savings. One year of opportunity. One year to go all in.
Manon, with a co-founder who has sold companies before, experiences it differently. Without external investors, they can shape Yesty without pressure for quick returns – but that freedom comes with the responsibility of pacing growth themselves.
Holly has done both bootstrapping and multimillion-dollar fundraising rounds. Her biggest lesson is that the source of money matters as much as the money itself:
There’s good money, and there’s bad money – and every pound comes with strings.
Knowing which strings you can live with is the real skill.
Marie echoed the importance of simplicity: her business case lived in an Excel sheet with rough estimates and common-sense assumptions. Her first investor didn’t need a 40-slide pitch; they needed conviction.
The thread across their stories:
financial courage isn’t about having no fear – it’s about moving anyway with a plan you can stomach.
Finding your niche is messy, and yes, you’ll get it wrong first
Every founder talked about early pivots.
Yesty started as a WhatsApp-based consumer gifting app. It didn’t land, so Manon and her co-founder tested B2B, then several buyer segments, before discovering the market research industry was hungry for their model.
Rocío described those early months as “going left and right” until she found the true value she brought.
Both made it clear:
most founders don’t find product–market fit – they stumble into it.
If you hide behind a screen, your business hides with you
Selling came up again and again. Not glossy selling – real selling, sweaty-palmed selling.
Holly shared her layered approach: social selling, thought leadership, curated SEO for an AI-driven search world, hosting panels, attending conferences, booking coffees, and – crucially – following up.
Marie is building her own visibility machine through LinkedIn, Apollo outreach, and Instagram reels for her tutoring brand.
Every founder agreed on one thing: you can’t grow a business if you aren’t visible. And visibility is uncomfortable for almost everyone at first.
Sanity, boundaries and self-belief: the real pillars of staying in business
Manon protects evenings fiercely, putting her phone away as soon as she’s home. Mixing work and parenting created more stress than momentum, so she split them cleanly.
Rocío doesn’t open her laptop at night, full stop. Work is hard, life is hard, rest has to be non-negotiable.
Marie used coaching to break overwhelming to-do lists into manageable steps.
Holly walks, spends time with her toddler, and is still learning how to switch off. Starting companies, she admits, has basically become her hobby.
They also acknowledged something many members whisper privately:
imposter syndrome doesn’t vanish – you just get better at answering it.
More than one founder admitted they sometimes wonder, “Why would anyone want to hear from me?” And yet, they show up anyway.
What to take forward
Here are the core lessons that surfaced repeatedly, across both panels:
- Hiring defines your culture. Firing tests your character.
- Know your financial threshold and build from there.
- Expect pivots. Expect confusion. Expect to be wrong before you’re right.
- Visibility isn’t optional – in-person connection still wins.
- Boundaries matter more than productivity.
- Your intuition is a strategic tool – use it with clients, investors, and timing.
- Courage isn’t loud; it’s consistent.