5 Biggest Regrets With My First Startup

Walter Guevara
Oct 27, 2020 · 7 min read

Some people don’t believe in regrets. They regret nothing because it’s all useful in the grand scheme of things. Sure. Whatever makes you sleep better at night.

I personally think regrets are a great tool. When you answer the question “What do you regret?”, the list of things that inevitably come out are the things that you should be mindful of and never forget.

They are your guide posts in this thing we call life. So when I ran my first startup from 2017 to 2019, I made mistakes. Some of those mistakes were bigger than others, and those are the regrets that I use daily to fuel my work now.

Here are a few of those.

I took it too lightly

Startups sound fun from the outside looking in. You have a clever idea, you put a team together, you build it, play table tennis, and if the idea works then you will be financially free for a while, if it doesn’t oh well. At least there was table tennis.

That’s the mindset that I had from the very beginning anyway. And that caused one big problem. When things got serious, and they always do, I didn’t know how to react appropriately, thus leading to further mistakes down the chain.

There’s alot that goes into a startup that I avoided early on. Maybe I was nervous about the process or afraid that I had no idea what I was doing. Yeah. I’d say that’s about right.

I stayed out of the legal stuff as much as I could early on and told myself that I was right in doing so, because I’m engineering this whole thing. Then suddenly when I’m sitting in front of a room full of investors one day, things get real. And they get uncomfortable.

Questions about everything except for the code are flying at you and you do your best to maintain composure. It’s a humbling experience. And you do eventually get better at it, but it would have been better to get there much earlier.

So the regret? Don’t take it lightly and get into everything as quickly as you can. It’s the things that you don’t know that will eventually come back to get you.

Not getting user feedback

You might have a great product, but if nobody wants it, its a terrible idea. That has become my mantra.

You don’t want to spend months hashing out a product only to find out 6 months later that while pretty functional, there is no market for it.

In our case, we did do market research early to gauge interest in the product to really great success. People wanted our idea and they signed up to be notified about future updates. Thousands of people. It was a great start.

But the biggest challenge was building the actual product. We built something that was more catered to ourselves than to our audience. Of course we didn’t discover this until after we had our big launch.

The result? A very low conversion rate that took almost a year to fix. And really we didn’t start to nail the usability until we had more eyes on our product and until we could see real people using it.

The results are always shocking. The way that people use your product without any formal instructions is highly personal and varied from person to person. So building something that caters to everyone is the real big challenge.

Really you don’t want to find yourself developing things that you think are interesting and futuristic unless you know for a fact that this is something that will be used. Time is money and sometimes these ideas can get expensive.

So set up user panels with live people at least once a month and have them run through your interface and take meticulous notes on their interactions. If you want a faster route, you can also set up paid surveys online and do the exact same thing.

Know what people want and then build that.

Not focusing on design

Our particular SASS application was targeted towards hair stylists and salons looking to fill seats. The problem was that the overall design was made by, well, us. A group of programmer’s that had ‘some’ design experience. We weren’t terrible mind you as our product looked decent.

But we did not consider our target audience at all during the initial design process. Eventually we hired a professional designer to work with us and the first question they asked was one that we should have been asking as well.

After going over our user analytics and getting a better idea as to who exactly was visiting our website, they came up with 3 designs they thought would fit. I’ll say now, we disliked most of them. But that’s how we knew that we were on to something. Because again, the designs were not for us. Our audience definitely felt the impact much sooner as engagement went up almost immediately after we made the change.

This is something that really should be handled as early as you can as changing brand colors, logos and personality can be confusing after months of operation, particularly to any loyal users you may have that are high converting.

A clean logo and a eye-pleasing color palette can really make someone feel like they are a part of your product, and not just a user. This is why Google has a clean minimal design and why Amazon is orange. Because people remember design.

No team-building plan

A startup is only as good as its member. The problem is that there’s a good chance every member is pretty weak near the beginning. Particularly if this is everyone’s first time. And that is why team-building needs to be a part of the underlying ethos of your company.

I’ll say now. My startup had no initial form of team-building besides a weekly 3 hour meeting in a fancy coffee shop. And that actually worked pretty well for a while. It was a great opportunity to both de-stress from the outside life and to really go into detail about our company.

There were multiple times when certain members of the team (myself included) hit a wall and decided to make an exit out of frustration. It happens. We’re human and depending on the weather and sugar levels, we might act not appropriately. And it seemed like those situations almost always got resolved at the coffee shop.

While totally by accident, I now wish that we would have included more of these events into our company’s underlying business model.

Particularly because a new company is in it for the long haul. You have to realize most run without profit for years early on. That causes an underlying stressful foundation and if you don’t find a way to quell it, it will wreak havoc on you.

Recommendations? Sure. Take a company business trip with your team. A real one. Work towards building a network with other companies and then make a drive and rough it out.

We had to do this early on in our business as we were gaining traction, and it was rough. Having to drive across the state for 8 hours for a meeting and staying on friends couches along the way while taking turns driving isn’t ‘fun’. But it is rewarding.

We even considered doing monthly camping trips in order to built more trust. We considered it, but never got it off the ground. We probably didn’t trust each other enough to have each others backs during a wild bear attack.

Trust is the key.

Not being bold enough

Adaptation is mankind’s biggest asset. It’s the reason why humans have branched out to nearly every continent and managed to survive regardless of elevation, weather or food resources. You have to adapt and do so quickly.

That means not being afraid to throw ideas completely out and starting over from scratch. Sure, that might be your best code ever and you can’t believe it works. Add a comment stating the fact and then get rid of it if it isn’t helping you get to where you need to.

You would be shocked at how making a slight adjustment to one thing can change the entire game around. This could mean changing your pricing model to a completely free one and then looking for other avenues to profitability.

That’s a tough one, but you might find that your free model increases traffic by 10x. And now with that many more users, you might have more options that you never saw before. Probably much simpler means of becoming profitable at this point.

Really, you only get one shot at this. You have a product and you have a team, but not forever. So you have to try everything even those things that you have never done and are brand new and terrifying. You have to try those things. It’s the main reason why we can get packages delivered in 2 hours today and why we can hail a cab with 2 clicks on a piece of glass.

My regret lies in the list of things that I wrote down that never saw the light of day but that could have changed everything. The ideas on the whiteboard that in the moment were capable of changing the world.

Because always and forever, fortune favors the bold.

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Walter Guevara

Written by

Sr. Programmer. Coding blogger. Former startup CTO. Los Angeles native. Future sci-fi author. www.thatsoftwaredude.com

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +800K followers.

Walter Guevara

Written by

Sr. Programmer. Coding blogger. Former startup CTO. Los Angeles native. Future sci-fi author. www.thatsoftwaredude.com

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +800K followers.

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