How to Recover After a Failed Startup

Walter Guevara
Dec 14, 2020 · 6 min read
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Just as with any human relationship that comes to an abrupt end (or not so abrupt at times) certain events in our lives will require us to take a step back, heal our wounds, take some time and recover before we venture out again into the unknown.

Typically, when startup founders make the tough decision to not continue forward with their business, it’s because resources have been depleted and there is no clear sign of progress ahead. It’s a tough call to make, but an important one as going too long and too far without proper supplies typically does not boast well for anyone in the group.

In 2019, after 3 long years of engineering, planning and trial and error, my startup came to a sudden end. It didn’t hit a wall, there was just no more road left to walk on. Our financial resources were running low and, more importantly, my financial resources were non-existent. And the rest of the team was also having to make unwanted adjustments as we headed towards uncharted waters.

There is a fair amount of damage that comes with starting up your own company. Families can become fractured, friendships can end, finances can become depleted, careers suddenly halt and then once the roller coaster is over, you have to find your way back to normal life somehow. At least, whatever the current definition of normal is. Sometimes normal at 35 years of age is different than normal at 30.

It’s been over a year now since I handed over the keys to the office and things aren’t quite back to normal just yet, but they are getting better slowly and surely. Here’s what I’m doing currently to heal up and come back stronger for the potential next phase. Because it’s never quite “over” per say. It’s just “not right now”.

Don’t join another startup

You can imagine that after 3 years of doing it daily, I didn’t really know how to do anything else. All I wanted to do was to get to work on my next big idea. To put together another team and to take everything that I had just learned and not repeat mistakes. So I did.

I joined online co-founder communities and answered requests for tech leads and engineers. And within a few months, there I was at another pitch meeting as CTO of a game advertisement startup. And it was just as exciting as the first time around. We worked out of coffee shops and managed remote teams through Zoom. The typical startup workload was back.

The only difference was that I was pretty much broke at this point. And I had no office. And my energy levels were almost non-existent. I was running on sheer willpower and cheap coffee it seemed. To make matters worse, this new startup only had 2 members (myself included) and no budget. Needless to say, it didn’t take too long before the CEO decided that it wasn’t worth his time before he scrapped the project.

I jumped around a few startups after this and everyone pretty much suffered from the same fate. They did not have enough financial resources to last more than 2–3 months. Some companies didn’t even have an actual product. They only had very nice looking slides and presentations. In which case my role would be to build them their dream product.

At this point, I decided to change course and to really recover, financially and mentally and to leave the startup world behind, even if just temporarily. I dove into my part-time teaching job more and I started to spend more time on my coding blog (www.thatsoftwaredude.com). And slowly but surely, I eventually felt like I was able to breathe again. I still had my startup experience and knowledge. That didn’t magically vanish into the ether like I once feared.

I still take on monthly meetings and consult with early stage startups when possible. But this time around, I’m more patient with the process and I realize that everything has its season. Learning to slow down again is the biggest challenge I have found so far.

Talking about it

The truth is, you might not want to relive through the process of what you just went through. I know I didn’t. I left in the past and let bygones be bygones. There is no point in blaming anyone at this point I thought. But unless you confront what went wrong and what went right, you won’t learn anything from it. And you can only really do that by talking about it.

The more I opened up about the experience, mainly with family during morning coffee trips, the more appreciation I felt for the entire process. Stories that had become common to me, like flying across the country for startup competitions or driving for 10 hours for a 5 minute investor meeting sounded crazy to others. “Why would anyone do that?”

Why indeed. Well, because you have commitments and you should stay true to your word and not break them. That’s the response that inevitably comes out when asked, but that I never give myself the credit of thinking when alone. And it’s not until someone asks you “What do you think could have gone better?”, that you really get to dive in and reflect on what you learned. Because there’s alot there to unpack.

There’s also alot of information there that can help somebody else going through the same process. And it would be a shame to keep it bottled in thinking that it is wasted experience. Since that time, I have been able to guide several younger entrepreneurs through their own startup journeys and that has definitely been one of the more rewarding outcomes of this process.

So share the stories however you can. Share it in writing (like I am here), or by talking to those willing to lend an ear or to someone that could use the words to keep them going on their journey.

Plan ahead

But, if you are a true startup entrepreneur with big ideas and big dreams, then it would be a shame for you to become disheartened and to stop here at this juncture. Startup people are a rare breed despite what TV shows portray. Not many people would be willing to forego the safety and comfort of a standard lifestyle for a potentially chaotic and unknown venture.

So plan for your next business venture and plan it well. Don’t worry so much about timelines and legal docs and buying domains. Not just yet. But sketch out your idea. Write out your potential business plan. And come back to it whenever you have free time.

Slowly but surely, as your finances recover and you start to remember what it’s like to not be stressed daily, you will gain that confidence again and this time around you will be much more resilient and your chance of success will be that much more increased compared to the first time around.

There was a time after my startup that I believed that maybe this lifestyle wasn’t for me. That I should put those things aside and to focus my energy elsewhere. But just as quickly as that thought enters my mindscape, it is countered by that amazing idea that I sketched out years ago in an old notebook. And every time I look at that sketch, I smile and think to myself “I need to build this”.

Because as I said, it’s never quite “over”.

The Startup

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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

Medium's largest active publication, followed by +773K people. Follow to join our community.

Walter Guevara

Written by

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

The Startup

Medium's largest active publication, followed by +773K people. Follow to join our community.

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