Today, I want to talk about losing. As much as we celebrate wins, it’s the losses – the seemingly pointless, invisible, unfair ones – that really build resilience.
If you’re a founder or soon-to-be founder, maybe you’ll see yourself in some of these stories. I know I did.
Loss #1: Losing in Competitions
I’ve lost pitches. Many. Spent days polishing slides, rehearsing demos, tweaking every line of the product, just to come up short. Sometimes I’d lose to startups that barely had a real product. Others would win simply because they had huge funding rounds, or because they had more traction, or were simply “better” at selling themselves.
Why it stung:
- It felt unfair. After pouring hours, energy, hope, you expect at least some recognition.
- It shakes confidence. You start wondering: “If this effort I put in isn’t enough, what is?”
- Sometimes the feedback is vague or nonexistent. You leave with “thanks but no thanks” and that’s it. Hard to know why you lost.
What I learned:
- Preparation matters, but so does expecting to adapt. You think you know what judges care about – maybe product, maybe traction – but sometimes it’s narrative, or team, or connections.
- Feedback is gold. If you don’t get it, chase it. Always ask “can you tell me one thing I did well and one I should improve?”
- The loss often teaches more than the win. Better slides, clearer story, more honesty about risks – these come from seeing what others do better.
Loss #2: Clients Who Disappear
After competitions came a different kind of loss – clients who vanish. It’s one thing to lose in public, in competitions. But it’s another to have potential customers, people who seem genuinely interested, and then nothing. Silence.
My experience:
We had clients who told us they liked the product, who seemed ready. Then silence. No reply to emails, no calls returned. Sometimes we thought: was the product not working? The value unclear? Was pricing wrong? Or was it just internal in the client’s company and nothing we could control?
Why it’s painful:
- You invest time believing in the partnership. Building custom proposals, aligning expectations, sometimes even modifying the product. When they vanish, it feels like those hours didn’t exist.
- It makes you doubt your product, your messaging. If they liked things, why didn’t they commit? Was it me? Was it the pitch? Product-market fit?
- No feedback = no closure. Without understanding the “why,” you might repeat the same mistakes.
What I learned:
- Always try to build in feedback loops. After a meeting, after a demo: “What are your concerns?” “What would stop you from choosing us?”
- Be okay with asking. It might feel uncomfortable, but even if they say “no” and don’t want to explain, many will share if asked in the right way.
- Use disappearance as data. If several clients vanish at the same stage, that stage needs work – messaging, pricing, trust-building, etc.
Loss #3: Roadshow that Didn’t Turn Into Deals
Then there was our roadshow (in our second year) – a loss of a different scale. We pitched to multiple security companies / enterprises. We thought: this is the moment, this is where things shift. But despite all the meetings, despite all the hopes, we didn’t close deals. Very few follow-ups.
We sold “technology”, not value. And we learnt the hard way: being new in the market has its costs.
What made it hard:
- High expectations: you imagine this roadshow will open doors, get contracts, move fast. Reality is slower.
- Being new in the market means you lack credibility. Decision makers want proof. They ask: Do you have clients? Do you have scale? Case studies? Maybe references. If you don’t, you get politely dismissed.
- We didn’t have clarity on what “closing” looked like. After meetings, there was no structured follow-up. No clear next steps. We expected them to come to us.
What I learned:
- Value > Technology. It isn’t enough to show what tech does – you must show what it solves for the customer. Maybe even better: what it prevents. What cost (in money/time/risk) you remove.
- Structure the follow-up. Always leave a next action: “I will send you a proposal by X”, “Let’s schedule a technical deep dive on Y”, “Can you share your procurement timeline?”
- Build credibility early. If you can’t show big clients or scale, show early wins, small clients, pilot results. Use testimonials. Use whatever external validation you have.
Why Losing is a Founder’s Secret Weapon
By now you might be thinking: “Gonçalo, that’s a lot of losses.” And yes (and these are not all, not even close) – but losing isn’t just about the moment. It’s what comes after each loss.
Here’s why these moments matter more than they feel like at the time:
- Resilience grows muscle only under stress.
Each time thing’s doesn’t go your way, you adapt. You refine. You get better at dealing with rejection, uncertainty, discomfort. Those are daily parts of being a founder. - Clarity emerges.
What was vague becomes sharp. You see what customers care about. What messages resonate. What “close” really means. What your weak points are: sales, story, credibility, pricing (in the beginning, all of these were my weaknesses). - Humility & realism.
Losing teaches you to respect the unknowns. To prep for them. To keep ego in check. To recognize that good ideas are not enough – execution, clarity, persistence, feedback are everything. - Better decisions next time.
Losses force reflection. What would I do differently? Who should I have talked to earlier? What signals did I ignore? That reflection leads to more informed moves down the line.
The Dark Side of Losing
That said, not all losses are useful. If you mishandle them, they can drag you down.
- Emotional fatigue: If you constantly invest and get nothing, you can burn out.
- Imposter syndrome: Doubt builds. Sometimes it convinces you that you’re not good enough (even if you are, you just haven’t gotten the right breaks yet).
- Loss of momentum: If losses pile up one after another, momentum stalls. Team morale drops. Investors / partners worry.
- Paralysis by overthinking: You can start fearing every decision, avoiding risk, hesitating to act – which kills startups.
What I Do Now, To Turn Loss into Fuel
Because I believe losses are not just inevitable – they’re essential. Here are what I try to practice, so the bad ones become stepping stones:
- I ask for honest feedback.
- I set interim goals, not just outcome goals. For example: getting commitment to a next meeting, or getting feedback, or drafting a proposal – things I can control.
- I remind myself: you’re not alone. Every founder I admire has dozens of stories like mine. Most only share when there’s a win, but the losses were there.
My Final Thoughts
Losing is part of the founder story. It’s messy. It’s frustrating. It’s unfair. But, it’s also one of the richest teachers you’ll ever have.
If I were you reading this: when you lose next time, don’t just mourn it – mine it. Find the lessons. Adapt. Don’t be afraid to ask hard questions.
And remember: resilience isn’t bouncing back to where you were – it’s moving forward, wiser, less naive, more grounded.
