The Biggest Lessons Learned Running a Startup

5 min readNov 9, 2020

I’ve said it before and it is worth repeating, startups are hard. If you truly want a successful business model that can scale well and that large numbers of people actually want to use, it’s going to be hard.

I ran a startup for 3 years, almost to the date, and many things went right in the process, but equally as many things went wrong.

If you are in the early stages of your startup, or considering going all in on your business venture, here are a few lessons that I personally learned during that process that might help you out on yours.

Your initial implementation is going to be bad

It just is. There’s no going around it. Nobody has used your product on day 1. Nobody. But you went out of your way to build something that you think everybody wants. That is not a recipe for success.

But it’s a start. It’s definitely better than not having anything. When my company first launched, we had a very complex sign up process. It must have been a 10 step approach. Truthfully, we might have seen it implemented online and figured it would work well with our product.

It made sense, if you were already familiar with said product. But if you were presented with this wizard on day 1, there’s a good chance you would drop off quickly. And people did. But it took us a while to realize this. We spent more money on ads and marketing and while the numbers went up in terms of traffic, our actual conversion rate was pretty low.

Slowly we transitioned into an anonymous, non member model and then people started to sign up like magic. They got an immediate and free look into our platform and then they decided to continue with the sign up process.

There was a fair amount of code that went into that initial model mind you, also referred to as technical debt. And while this is common for pretty much every business, the level of debt can greatly be reduced by being more aware of how your users are interacting with your product.

Whatever your version 1.0 is, don’t get too attached to it longer than you need to. Get feedback quickly and iterate.

Investors are interested in your team more than your product

And there’s a simple reason for this. Odds are that your product, at least early on, still has quite a bit of work required to really turn it into a valid and profitable idea. And you and your team (if you have one) are the ones that are going to be spending the time doing so.

This could take 6 months or it could take 6 years. Investors are looking for a good idea with potentially high return on investment, yes. But they know that this isn’t possible without the gears turning and a group of people making it happen on the other end.

My startup met with many investors in the first year, particularly shortly after launch and mainly after participating in the TechCrunch Battlefield competition. Almost every meeting involved a deep look into the team. How we met, who we are, what we are looking to get out of this. And it took some time before we stopped talking about how great our product was during those meetings and changed it over to a more honest and personal narrative.

It turns out we had interesting backgrounds. We were all from different parts of the world, we were close friends and coworkers, we all had families we were taking care of and we were all technologists looking to build something valuable. These meetings went much better than the more artificially hyped ones early on.

An investment firm might not fully buy into your idea on year 1. But, as with the case with us, they follow up and keep tabs. A year later they might want to see how much progress you have made and how your team is holding up.

Good teams aren’t found, they are built. They are built through struggle and through friendship, through thick and thin. And it’s the only way, because giving up that much effort and time requires trust more than anything.

Be easy with it

There’s alot that can go wrong when you mix 3 to 4 people, one tiny office and 3 years. The biggest lesson that I learned personally, is to be easy with the whole process. Depending on the idea, the season, the month, the year, it can go in many directions.

Sometimes it isn’t working and it might not be anyone’s fault. Or sometimes it is someone’s fault, in which case bring it up and figure out a solution. After a year or so in my startup, some people were burnt out and wanted to throw in the towel. For sure, they are allowed. We’re all human and time is finite.

You can’t force anyone to expend their energy where they don’t want to, and in that same light, people can’t force you to not expend that energy. On a long enough journey, not everyone is going to make it to the end. It’s just a part of the journey.

I think the idea of grinding and hustling and being relentless is good in theory, but it fails often in practice. That was my mentality throughout the course of my startup. When my personal bank account hit zero, I kept going. And it worked out as we got our first big investment shortly after. When the investment ran out a year later, I kept going and sold everything I owned to continue on. Other’s didn’t follow suit and decided to make an exit.

I don’t personally regret sticking it out until the end, as it was a real test on my mental fortitude and there was a good chance that this might of been the only time I would go through this. But I think if I had just taken it a bit more easy with the whole thing, we might have been able to find that much sought after success at year 4 or 5, instead of year 3.

It’s always better to flow with the current, than to backpedal through harsh waters and damage your vessel.

The Biggest Lessons Learned Running a Startup

Your initial implementation is going to be bad

Investors are interested in your team more than your product

Be easy with it

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Written by jibon das

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