Running a startup is so damn hard. Dad warned me about it. Friends told me about it. Ben Horowitz wrote a book about it. Yet it was only by going through it myself that I truly got it.

Every step feels like an uphill battle - 100x the work, 1/100th the resources. The moment things feel manageable, a curveball makes you want to quit.

The image of running a startup is greatly skewed today. You hear all those glorified stories of startup successes, but you don’t hear about another 100 startups quietly closing shop. You see founders speak at events pitching their exciting products and sharing the rewarding journey that got them there, but you don’t hear the daily grind, the sacrifices they have to make, and the many moments they want to give up. In fact, they might be dealing with some shitty situations right when they’re speaking to you. You just don’t know.

No Down Days

Work-life balance is non-existent. Admittedly, for anyone ambitious enough to want to build a startup, they probably aren’t thinking about work-life balance to start with. Yet, even when they do, it’s hard to stop and rest because of the opportunity cost.

When you’re in a big company, taking a vacation just means some delayed email responses - your time away isn’t going to slow down the corporate machine in any meaningful way, and you’ll still get paid. But when you’re in a startup and when you are the business, taking a break often equals your business hitting pause.

So what ends up happening is that founders don’t choose when to rest but time their breaks based on opportunity cost, which often aligns with their clients’ schedules rather than their own preferences.

No Brand to Hide Behind

As a startup, the first thing you hear a potential client ask is why you. Why should we work with you? Why not Company X, who is much bigger with a much longer track record and much bigger client base? And the truth is, for some people, it’s indeed better to just work with bigger companies when those hard stats are the only things they care about.

So why you? I tend to think about every sales conversation as an investment conversation. Sure, a mature company can provide the customer with a working product and a much narrower range of potential outcomes that can be pre-defined and quantified with little risk, but they still might want to work with a startup because it doesn’t just solve your problem today, but will grow and solve your problems tomorrow.

That said, not everyone cares about the long term and making an investment for the future. So if you decide this is the angle you want to go with, much of the effort then goes towards finding the right person who speaks your language of innovation and growth and recognizes the value you can bring.

In fact, building an organized pipeline of sales leads is probably one of the most beneficial things a startup can do to develop a disciplined partnership practice. Yet it’s also extremely time-consuming: countless conversations including many going nowhere, endless showing-up in case something might lead somewhere, and shameless followups without easily taking no for an answer.

Even after that, you still have to make a connection with people and tell the right story. You should always start with their problem and customize your pitch. You need to stay engaged and think on your feet. There’s no letting loose because you, as a startup, come as a nobody and have to constantly justify your position and defend your worth.

Never Enough Time

I find my flow in deep thinking and deep work. But in a startup, there’s very little time for that. Things need to be done fast and soon. You don’t have the luxury to think through everything and experiment with different options. You strategize as much as you can and learn by doing.

And it doesn’t happen just once or twice - it happens almost every single week, as that’s the timeline we’re talking about for shipping new things in a startup setting. You’ll be thrown into unfamiliar terrain with new challenges constantly. You have to do many things for the first time to deliver the outcome. You’re forced to think from first principles without many examples to follow or guidance around you.

As you execute, you need to make quick decisions and move fast. You know you can do better if there were more time but have to ship it anyway. The moment you learn the ropes you’ll have to move on to the next thing, leaving an unsatiated taste of mastery.

2025 Lessons Learned

Unless you have a clear reason for why you want to build a startup, it’s much more comfortable to be in a more established company - despite the caveats. Statistically, you will make less money running your startup than joining a big company, while working longer hours and being more stressed. It only makes sense if your reward function includes novel experiences and accelerated learning or you’re obsessed with a certain vision that you cannot live without.

Building a startup dismantles your ego as you constantly hear people telling you no. However, you learn to be resilient. You make peace with feeling like an imposter and keep going despite feeling that you’re not enough. You find confidence in your ability to grow rather than who you are today.

You truly have to think from first principles. You won’t win unless you dare to challenge the assumptions, get down to the fundamentals to find creative and efficient paths to get over the hills.

People are the most important thing. It’s not about what you’re betting on, but who you’re betting on.