Can money buy happiness?
"When you have money, you're not allowed to be sad."
Hi, it’s Melissa, and welcome (back) to “your founder next door”, a weekly publication with stories and tidbits of my human journey bootstrapping eWebinar to $5m ARR. No BS, just straight-up truth bombs on what it’s like to build a company without an abundance of resources or friends in high places.
The question that always breaks the internet 🤼♀️
I grew up in a very materialistic culture in Hong Kong, where money was everything. My dad used to tell me that people will judge you by the watch you wear, the clothes you have on, the car you drive, and the place you live. For a long time, I believed that was the only measure of success. I wrote about this in detail in how much is enough to stop working.
I’ve since come to know better. There’s more to life than financial success. Of course I still like nice things. I like to travel and eat well. I’m not lavish, but there are very few experiences I withhold myself from.
Yet, when I hear about someone else’s number, I still catch myself thinking if I had that, I’d be happier. My troubles would go away.
Don’t we all do this? We look at people with money and we project a whole life onto them. Those people must be living their best life. They must be so happy.
Which brings me to the question that always breaks the internet: can money buy happiness?
How I met Simon Swords 👋
Simon found me. He commented on one of the bootstrapped founder stories I wrote a while back, then sent me a private message. He said he loved the story, that he was also bootstrapped, in his early 40s, and had just sold his company for 8-figures.
I was in the middle of planning Season 3 of ProfitLed, themed around the intersection of Passion, Profit, and Purpose and how those shift as founders come into financial success. So I invited him on the show to learn his story.
Simon bootstrapped Fundipedia for nearly 20 years before selling to FE fundinfo in May 2025. He started in a garden shed with an Ethernet cable and a VoIP phone. He eventually landed clients like HSBC and Barclays. There was no breakthrough moment, no overnight success, no hockey-stick growth from zero to a hundred million in 12 months. He just worked really hard, for a really long time, and built something extraordinarily valuable for someone else.
I love these stories because they’re not lotteries. Simon doesn’t write on LinkedIn. Nobody wrote about him. Most people have never heard of him. Yet his story is the one that gives the rest of us hope, because it’s a story about what’s possible as a “founder next door”.
My conversation with Simon on ProfitLed 🎙️
While our journeys are very different, I recognized a lot of my own struggles in his. The hustle. The sleepless nights. The anxiety of not knowing where it’s all headed. The chip on my shoulder, wanting to prove my worth through external achievements, and slowly realizing none of that actually matters.
Simon opened the conversation by telling me what drove him. It wasn’t for the money. It was to prove people wrong. He carried a lot of pain from his childhood. Bullies. A head brace he forgot to take off when he answered the door, sending his friends recoiling. Debilitating hay fever. Parents who hated each other. A house he’d come home to, empty most nights.
He told me about the time he thought he was having a heart attack on an HSBC onboarding call and decided to finish the call before going to the hospital. He said he would have rather died than given up.
In my last company Spacio, I had a chip on my shoulder too. I wanted to show people I could do it, including my parents who wanted me to become a lawyer, a doctor, or a banker. Lack, pain, and desperation fueled my ambition. I thought it was a requirement for success, so I embraced it and honored it. I was never happy and always frustrated.
Once, my very wise founder friend Ben Huh (the inventor of LOLcat back in the day) told me I could never feel the success of Spacio because there was too much suffering associated with that company. He said “one day, you’re going to build a company from love and abundance, and it will be a completely different experience.” I didn’t fully understand it then. But he was right. eWebinar is that company.
When Simon’s deal closed, he had what he called “a big old cry.” He told me it wasn’t relief. It was 25 years, maybe 42 years, of pain, self loathing, and overthinking everything finally letting go.
The money landed, but the anxiety didn’t leave.
Simon’s pain was familiar to me. But there was something else in his voice I hadn’t expected. It wasn’t just “this was really hard, I built this for 20 years.” I felt a sadness underneath.
He joked that once you have money, you’re not allowed to be sad. “I have money. I’m sad.” He said, in a cheeky tone. I wasn’t sure if that was fully a joke…
We dug into the first part of it. He said people assume that if you have money, what could you possibly have to complain about? Your friends are still working hard. You’re not allowed to express it. You have to be sensitive to everyone around you who has less than you do. So you smile and nod, and you keep it to yourself.
I had planned to ask Simon the question: Do you think money can buy happiness? But after we’d been talking for a while, I didn’t. I already knew what he would say.
That stuck with me. Because the truth is, we are human. Sometimes we’re sad. But we have this tendency to look at someone who has a lot and think what are they sad about? They have everything. How ungrateful of them.
I’ve always been on the side that money can buy happiness. It buys freedom. It affords you the luxury to work or not work, or to work on your own schedule, the way I do. It lets you say yes to the things you want and no to the things you don’t. Financial freedom doesn’t mean having all the money in the world. It means making decisions free from the constraint of money. Most of us are closer to that than we think, because it doesn’t actually cost that much to live a good life nowadays especially with the sharing economy.
Talking to Simon was the first time I could put something into words I’d been circling for years.
Even if money can buy you things that make you happy, it can’t make you not sad.
Those are two completely different things.
The things that make us truly happy aren’t things. It’s not a supercar, a mega yacht, or a first-class trip to the Maldives. It’s who you experience those things with. The people who love you. The people you love in return. Most importantly, your relationship with yourself.
We all have this idea that once we get to the destination, everything will be great. Once we have $10m in the bank, our troubles are over.
Happiness isn’t an asset you can buy. It’s a learned skill. It might be the hardest one to acquire, because it changes shape as we grow. The work doesn’t end.
I’m only learning this now, in my early 40s. You can have everything you want, and there can still be something buried inside you that prevents you from being truly happy.
Last week I went to a retreat in Portugal, and the thing I uncovered about myself is this: while I seem to have everything, there are two voids in my life I haven’t fully reckoned with. I don’t have a relationship with my mother. I don’t have a relationship with my brother. To fill the space they left, I’ve built an incredible community full of amazing friends I travel with and have fun with all year round. But no matter how full my life is, there’s still something missing. The two most important relationships in my life are broken. And no amount of money will fix that.
So, can money buy happiness?
It’s not a yes or no. It’s yes and no. Happiness isn’t a binary thing. Money can buy many things that give us moments of joy. But it certainly can’t make you not sad.
That is something we have to work on ourselves. The only way to undo it is to find the source of the pain and address it.
After we stopped recording, Simon and I got to talk about the two retreats I went to last year where I found my own happiness unlock. A year ago today, I was at my worst. I didn’t think I was coming back. I considered calling it and doing something else. Today, I’ve never felt better, I’m having more fun than I ever have, and I’m producing some of the best work of my life. I’ve written about that journey in the importance of self-love in entrepreneurship and losing delusional self belief.
It turned out Simon had already heard of The Hoffman Process, the 7-day self-development retreat that started my own journey. I just put it back on his radar. He’s open to it, and I’m so excited about that. Here’s a guy who seemingly “has everything”, but there’s something holding him back from fully experiencing the fruits of his labor. If he can crack this, it could be the next huge unlock in his life.
What Simon built in 20 years, fully bootstrapped, is admirable. But his story doesn’t end with the exit. The biggest thing I learned from our conversation is that the exit is not the finish line. It’s a different starting line for a new kind of adventure.
To hear our full conversation, tune into this episode of ProfitLed here: Apple, Spotify, YouTube
Till next time,
— Melissa, your founder next door ✌️
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Money can take a lot of pressure off.
Being at peace with yourself and the world around you probably matters more than people admit.