“In the hiring process, I’d look for stories of trauma.”
A second-time founder told me this as we co-worked side by side a few months ago. He’s already exited once, raised $3.7 million for his seed round with the same cofounder, his older brother, and has the kind of track record that makes other founders lean in when he speaks.
Me? I’m also a second-time founder, but he’s made a lot more progress than I have. So when he shared his hiring philosophy, I listened.
He told me he couldn’t hire someone who was only after a salary. He was looking for people whose hardships and traumas had shaped them into who they are.
“I need to know what drives them.”
You might be surprised, but this mindset isn’t unusual in the startup world, especially when it comes to evaluating a founder’s profile. It’s something I never would have guessed.
Growing up in Hong Kong, the default was always to put on a polished front. You didn’t air dirty laundry, and you certainly didn’t talk about family trauma in public. The one thing you didn’t want was to bring shame to the family.
When I was looking for a cofounder, I started noticing patterns in how different incubators thought about talent. Entrepreneurs First, for example, seemed to favor PhD students. At one point, I even wondered if a PhD was the secret marker of a great founder. So I asked a Y Combinator alum, now a VC founder, what he thought.
He advised me to ignore whether someone had an Imperial PhD, but to:
“Find someone who’s hungry.”
Funny enough, I later joined an EF bootcamp, where I had a proper chat with a PhD graduate from École Normale Supérieure, one of Europe’s top science schools. I asked him the same question. His answer was simple:
“Find someone who has something to prove.”
Some tech founders are probably laughing at me right now. In a world where university dropouts are celebrated, or even university kick-outs if you think about Cluley, there I was, asking PhDs for advice.
I realized this isn’t just a hiring question for startups. Even a tech policy expert once told me:
“I’d rather hire a working-class kid.”
Shark Tank’s Barbara Corcoran had a further explanation:
“Rich kids know all about business as an observer, but they don’t know business as a player. Whereas poor kids tend to have had hardships. They’ve had to be a player earlier. They’ve had to contribute to the family, they’ve seen their parents struggle, they know the power of a buck.”
At a Techstars event in London, I overheard program managers telling founders how some VCs famously dig into childhood. The first question they might ask is:
“What’s the most traumatic experience in your life?”
Isn’t it strange that business is dressed up as rational and logical, yet it’s full of emotion?
And stranger still, Marc Andreessen, general partner at Andreessen Horowitz, has linked drive to “guilt,” the kind that comes from family pressure.
Guilt is a strong emotion.
A few months ago, I spoke with a founder who had just joined the Antler accelerator. He’d spent a decade in the gaming industry, and he told me how much he wanted to solve a problem he felt responsible for, how much “guilt” he carried. At first, I had no idea what he meant. Then he explained: the games he helped build were addictive for teenagers, and he couldn’t shake the guilt of it.
Guilt.
Guilt is that blurry weight in your head that says you’re never doing enough. It argues that you deserve a harsher test, that ordinary suffering isn’t sufficient. Guilt is like refusing painkillers when you’re in agony, a shame-made anaesthetic you force upon yourself.
You tell yourself you deserve it, even when you can’t explain why.
Maybe it’s the sacrifices your family made so you could stand where you are today. Maybe it’s your parents, who never had the chances you’ve enjoyed. Maybe it’s an apology you never managed to say, and now it’s too late. Maybe it’s the words “I love you” that went unsaid. Or maybe it’s the love you couldn’t give yourself when you needed it most.
Sometimes I wonder if we’re just trying to make sense of our pain. Maybe the pain is simply there, a circumstance, the outcome of chance, a low-probability event landing on us, and nothing more. Yet we keep reaching for meaning. We want to be the hero of the story. We want our pain to count for something, to prove that it shaped us, even if we’re not sure pain was ever meant to carry meaning at all.
What if it doesn’t?
What if pain is just pain, and the meaning comes only from the story we tell ourselves so we can keep going, so we can make sense of who we are?
Guilt > resentment.
For a long time, I wrestled with it, the guilt of being far from home, of not repaying the people who raised me, of not showing up when they needed me.
But I also knew that if I lived only to meet other people’s expectations, I’d end up with something worse: resentment.
Asian students once came up to me asking how they could convince their parents to let them pursue entrepreneurship instead of a corporate job.
I gave them some practical advice, but the truth is, I battle with guilt every single day.
My first startup began as a project to help people with anxiety. In truth, it felt like giving myself permission to pause, to read, to look inward, to try to understand myself. As British psychotherapist Philippa Perry wrote in The Book You Want Everyone You Love to Read:
“Sometimes being authentic means we’re not as kind as we would wish to be. If this makes you feel guilty, remember that guilt is better than resentment.”
As a venture capitalist recently told me, even trading decisions, supposedly the most logical of all, are driven by emotion. So it’s no surprise that hiring is too. Alexandr Wang, founder of Scale AI, said it best:
“Hire someone who gives a shit about the company and about their work.”
Maybe our superpower isn’t numbing the pain, but feeling it.
I totally agree with this. But the reality is that most start ups, tech companies, and banks, hire hardly any people from working class backgrounds — or anything close to that. Usually start up employees tend to be someone who went to private school, then Oxford or Cambridge or LSE etc., then maybe a year or two working in Investment Banking on consulting. There is a certain polish that is sought after. There's an unwritten code and boxes to be ticked before someone will even be considered for most roles in the start up world. Not sure how this ever changes in the UK especially with the cost of living — especially rent — so high in London.