Money Talks, Fundraising Walks - My Rollercoaster of Startup Wins and Losses

Startup Life: Trials, Triumphs, and Tough Lessons
- Money Talks, Fundraising Walks - My Rollercoaster of Startup Wins and Losses

If you’ve ever seen a headline about a startup raising millions in funding, you might think fundraising is just about pitching the right investor, shaking hands on a deal, and popping champagne. Spoiler alert: it’s not. Not usually anyway.

Fundraising is a rollercoaster, and not the fun kind. It’s a grind of emails that go unanswered, pitches that go nowhere, rejections that sting, negotiations that make you question everything, and shushing the whiny “why not me” inside your head. It’s also the thing that can take your startup from an idea to a thriving business — if you can survive the process.

So, let’s talk about the real story behind securing funding. The wins, the losses, the lessons, and the moments that made me want to flip a table (and the ones that made it all worth it).

Win: The First Check That Proved This Was Real

There’s something surreal about the moment when someone outside of your own bank account invests in your business. It’s not just about the money — it’s about validation. It’s proof that someone else believes in what you’re building.

For us, that first financial boost didn’t come from VC money — it came from grants, bootstrapping, and good old-fashioned scrappiness. We patched together funding from government programs, innovation accelerators, and strategic debt to raise $415K so far. Not bad for a startup built without a mountain of VC cash.

Lesson? There’s more than one way to fund a startup. And sometimes, the slow-and-steady route is what keeps you in control.

Loss: The Investors Who Ghosted Us

Oh, the ghosting. It’s real. You have a great meeting, they seem excited, and then… radio silence.

I’ve had investors:
🚀 Love our concept but disappear before the second meeting.
🚀 Drag out conversations for months, only to pass.
🚀 Get caught up in decision paralysis, leaving us in limbo.

At first, I took it a little personally. But here’s what I’ve learned: “No” is rarely all about you. Investors have their own timelines, pressures, and priorities. If someone drags their feet too long for your timeline, just move on. The right investors don’t need convincing — they see the opportunity and the timing is a fit for them.

Win: Learning to Play the Long Game

Fundraising isn’t a single moment — it’s a long game of building relationships, proving traction, and showing that you’re a business worth betting on.

Some of our biggest funding wins have come after months (or years) of conversations. Investors want to see traction — not just a great pitch, but real results. And to be honest, as a Founder, so do I, lol.

What worked for us?
✅ Showing consistent growth and evolution. Even small wins prove momentum.
✅ Being transparent. Not just about what’s working, but what isn’t.
✅ Building relationships before we needed the money. Investors don’t like desperation.

The best funding partners aren’t just writing cheques — they’re backing the people behind the business.

Loss: Realizing That Some Money Comes With Strings

Not all funding is good funding.

Some deals look great on paper — until you realize they come with control clauses, unrealistic expectations, or investor pressure that could take your business in the wrong direction.

I’ve learned that protecting your vision is just as important as securing funding. Because at the end of the day, money means nothing if it forces you to build a business you don’t believe in.

Final Round: Where We Go From Here

Fundraising isn’t about one big win — it’s a series of wins and losses that shape how you build your company.

Would I love a giant, game-changing investment tomorrow? Sure. But what I care about more is sustainable growth, the right partners, and a funding path that lets us build Roamlii the right way.

So if you’re in the middle of the fundraising grind — keep going. The “no’s” will come. The ghosting will happen. But if you stay in the game, adapt, and stay true to your vision, you’ll get to the yes that actually matters.

And maybe — just maybe — you’ll get to pop some champagne after all. 🍾

Yours in tourism, innovation and startups,

Founder & CEO
Roamlii