To Tech Startup or Not to Tech Startup

Above: HotTakes’ Team and milestones in 2025 thus far. We’re barely able to fit at one dining room table now!

Kevin Jing, Founder at HotTakes: Most founders face a familiar dilemma when deciding whether to take the leap: do you stick with the comfortable salary, the clear career ladder, the stability that everyone tells you to want — or do you gamble it all for the unknown reward (or punishment) of startup land?

And yet, so many people still choose the latter.

I was one of them. Along with my two best friends/co-founders.

At one point, I had a tidy 10-year career plan mapped out, complete with predictable promotions, mentorship, and all the security in the world, plus the comfortable salary. But walking away from that path forced me into a kind of mental tug-of-war. It wasn’t an impulsive move; it was a slow grind of late-night reflection, long conversations with other founders who had already jumped, and a lot of subconscious wrestling with what “success” actually meant to me.

On Living with Regrets

I think many founders suffer from the same very-human crippling weakness: FOMO. But not in the general sense of missing out on that fun party, or that exhilarating concert that *you just had to be there for. I’m talking about a deeper, more visceral kind of FOMO: the fear of not fulfilling your full potential.

It’s the gnawing thought that maybe you’re meant to build, to create, to push further than the safe path allows. And that if you don’t try, you’ll carry that regret with you forever.

The irony is that FOMO makes you act irrational. It pushes you to take risks that, on paper, make no sense. But, I’d argue that this irrationality is a well-needed step in every Founder’s journey. After all, there is nothing rational about leaving a surefire paycheque, a predictable career, and a comfortable 9-to-5 for…well, nothing tangible at first. Just an idea, and a fragile belief in yourself.

Yet, it’s that irrational leap that starts the journey. The one commonality in story behind every world-shaping unicorn today.

Small Wins

One of the biggest myths about startups is that they explode overnight. You read the TechCrunch headline — “$0 to $1M ARR in 9 months” — and start to believe that’s the norm. But in reality? It’s not even close.

The real journey isn’t a rocket ship. It’s a staircase. Step after step, small win after small win.

The first user who isn’t your roommate. \n The first investor who wires money instead of just “circling back.” \n The first time a stranger says, “Hey, I heard about your company.” For me, this happened at a houseplant store

None of those moments feel like unicorn milestones when you’re in them. They feel tiny. Almost laughably small compared to the “big wins” you thought you were chasing. But those are the things that keep you going.

The truth is: you can’t build a company by sitting around waiting for the massive win to drop out of the sky. Chasing that kind of hedonism can drive you insane in a way. Because there’s always bigger wins you hear about, another unicorn idea minted weekly, and it’s not you. But it doesn’t matter, and that’s the hardest pill to swallow.

That said, every once in a while, there are milestones that feel bigger than just another step on the staircase. For us, two stand out clearly:

• Paying ourselves for the first time. After months of working for nothing but belief, finally cutting ourselves a paycheck felt like crossing an invisible line between “dream” and “company.”

• Hiring talent we’d always admired. Nothing makes it feel more real than convincing people you respect to bet their careers on what you’re building.

  

To Startup or Not To Startup?

In the end, the choice isn’t as binary as people make it out to be. To startup, or not to startup, is less about chasing some glorified founder myth and more about asking yourself what kind of life you want to lead, and what risks you’re truly willing to carry. It’s an internal philosophical debate rather than a question of expertise, knowhow, or experience. Because at the end of the day, everyone has problems they face daily. And everyone has ideas on how things can be done better, even the most minute of things. Boom. That’s a business idea.

Because here’s the truth: your personal health, your well-being, your quality of life — they matter, and when they’re stripped you can’t be yourself. They’re not just “nice to have,” they directly fuel your output. If you’re sacrificing the basics of stability in rent, food, or mental health just to call yourself a founder, you might not be optimizing correctly. Startups are marathons, not sprints, and you need fuel in the tank to last.

And you also need to be brutally honest about the downside. You’re not risking a bad quarter or a missed promotion. You’re risking absolute failure. The kind that can cost you years of your career, your savings, and your peace of mind. And yet, if you do fail, the learnings are profound. You’ll come out the other side sharper, more resilient, and infinitely better prepared for whatever you choose to do next.

So the real question isn’t whether starting up is “worth it.” The real question is whether you can stomach the sacrifice, embrace the possibility of total failure, and still believe the upside is worth it to you.

If the answer is yes, then welcome to the irrational, exhausting, unforgettable journey of starting up.

Because in the end, the only thing riskier than starting up…is spending your life wondering if you should have.