My Friend’s Startup Is Thriving and Mine Is Falling Apart

Money Dilemmas is where we talk about the tricky stuff - the conversations about money that live in the grey area between love, power, fairness, and everything in between.

Each story starts with a real member dilemma, the kind many of us have quietly wrestled with but rarely said out loud.

Because money isn’t simply transactional; it’s about what we value, what we tolerate, and what we’re taught to accept.

And at the end of every story, one of our co-founders weighs in — offering her two cents and best advice on how to navigate the dilemma.

The Dilemma:

Six years ago, I met one of my closest friends at a networking event for founders.

We were both new to the whole thing - wide-eyed, terrified, and slightly obsessed with the companies we were building.

No one in my life really understood that obsession. My friends would ask how work was, and I’d find myself trying to explain why my startup wasn’t just a job.

It was my identity. My everything.

She got it. Finally, someone got it.

We became each other’s person. We’d text constantly, celebrate every tiny win, and drink too much wine after every rejection or bad launch.

I remember sitting on the floor of her apartment the night one of her investors pulled out, both of us crying and swearing that one day, it would all be worth it.

For a long time, our journeys ran in parallel.

There were ups and downs for both of us, but we were side by side - two women trying to build something in a world that rarely takes women seriously.

Then, somewhere in the last year, things shifted.

Her company started to take off, really take off.

Her revenue has exploded, she’s getting nonstop press, investors are chasing her now, and people speak about her with this almost cult-like admiration.

Meanwhile, mine has quietly started to fall apart.

Sales have tanked, we’re running out of cash, and I don’t even have the energy to raise another round.

I feel like I’ve been sprinting for years and my legs just gave out. I keep telling people I’m “re-evaluating,” but really, I think I’m giving up.

I want to be happy for her - truly, I do. I know firsthand how much she’s worked for this.

But every time someone mentions her, or when I see yet another glowing article about her company, something inside me twists.

It’s like I’m being forced to watch the version of my life that I dreamed of, the one that didn’t happen for me, play out right in front of me.

She’s so busy now that we barely talk. When we do, I feel myself holding back.

Pretending to be fine. I tell myself she deserves this and she does.

But it also feels so unfair. I’ve worked just as hard, maybe harder, and yet my story is ending in a slow fade while hers is turning into a movie.

I hate this feeling. The jealousy, the bitterness, the shame.

But I can’t seem to shake it.

How do you keep loving someone when their success is the mirror of your own failure?

Camilla’s Take

What you’re describing is very honest. There’s a kind of heartbreak that comes from seeing someone else live out the version of your dream that didn’t happen for you.

It’s not jealousy in the way people throw that word around. It’s something quieter, heavier. Part grief, part fatigue, part disbelief that all those years of effort might not lead where you hoped.

You’ve spent years building something that became the centre of your life, your identity, your sense of purpose, your proof that all the sacrifice meant something.

When that starts slipping through your fingers, it’s not just a company collapsing.

It’s the story you’ve been telling yourself about who you are.

So of course it hurts to watch someone else’s story soar at the exact moment yours is faltering. It would hurt anyone who cared as deeply as you do.

I also want to say this: the fact that you can name these feelings, rather than bury them, says something powerful about your character.

Most people don’t talk about what happens when ambition collides with exhaustion, or when success becomes a mirror that reflects back everything we’ve lost.

You’re already doing the hardest part, staying honest while it stings.

Try to separate what belongs to her from what belongs to you. Her rise isn’t proof that you failed. Her story just took a different shape.

Yours might be entering a new chapter that doesn’t look like the one you planned, but that doesn’t make it smaller.

It might even make it freer.

If you need distance for a while, take it.

You don’t owe anyone the performance of being endlessly happy for them when you’re grieving your own dream.

Give yourself space to rebuild your confidence before you try to rebuild the friendship.

When you do reconnect, it’ll be from a truer place — one that isn’t fuelled by comparison or guilt.

And please don’t mistake this season for failure.

What you’ve built, endured, and learned still stands, even if the company doesn’t. Some stories don’t end with an exit or a headline. Some end quietly but they still mattered.

What do you think?

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