Starting over after business failure

Work a job as normal and boring as you can find. Boring is, boring. But boredom is a good way to build up energy for a future run at a startup.

Also, one thing you lose working in a startup for a long period of time is perspective on what "normal" problems are. Which is why so many startups look like they only target other startups. The best ideas come from working in an industry long enough to understand the specifics about a problem, how to solve it, and who would buy it.

What you are experiencing is absolutely normal. You worked on the best idea and you worked it hard. You even delivered revenue from customers and maybe you successfully raised some investor money. However, 4 years later, you're the end of the road. You are hungry for a new idea because you have built up a unique set of entrepreneurial skills that you want to keep using. You're a professional high-energy operator who builds and executes. However, you don't have anything as good as the last business because starting is hard. You know that a startup requires commitment and conviction. However, to get that fire again, for a new business, is a drag. Your startup left you out of commitment and conviction for your industry and with even less fight in your spirit for another run.

My advice: Go back to the scene of the crime and open up an investigation while the trail is still warm and you have some consulting gig to keep cash in your pocket.

Your startup worked for 4 years. I would recommend you go back to your industry and meditate on why you were convicted and why you were committed. Why did you succeed? What did you do better than the competition? Why did you stop succeeding? What about your customers you really loved? Which customers did you really hate? What was the magic of the business that others couldn't repeat as easily as you. In those answers may possibly lie the new startup that you want to launch that will CRUSH the COMPETITION. In a careful poring of the 4 years are the seeds for a new and possibly even more successful company. Take your time because looking at the failure will be painful.

Some people have given solid advice here on financial restrictions, so will focus on the 'fire for building' part.

Recently listened to a podcast of Tim Ferris, where he interviewed Tony Fadell - who built the iPod, iPhone and Nest. In it, he makes a serious case for getting bored. He explains how he uses it to drive new ideas, such as how it helped him get the clarity of mind to get the idea of Nest, and how afterwards he's done the research for his current problem - one of plastics.

"Get the time to get bored. Spend three, six months if you can, or at least two or three weeks outside of that. Get bored. Just put away all of your things. Maybe go clean up the garage or whatever it is. Right? Through that, you’re going to start to think differently. You’re going to act slightly differently and your mind might open up to other sources of inspiration, other problems, other things where you start to go, “Oh, now I see differently.” I’m not just going to go run to the competitor because I understand the space and run to the competitor and go work for them because they’re going to give me a better job. But I want to go do a whole different thing that I want to learn about that’s going to challenge me so I’m not just checking in every day and doing my work, but I’m actually growing through that."

Listen to it here: https://tim.blog/2019/12/23/tony-fadell/

After I exited my last business, it took me 3 years to finally get up to feeling ready again. I also went to a dark place for a while. My best advice is to keep your head up and think more about the present than the future, at least for a little while. Keep yourself busy and avoid things that feel too cumbersome or dreadful. Exercise and treat your body well.

In between battling depression and anxiety over the years, I started doodling things again. Those doodles turned into thought experiments, into reading research papers, into connecting into a new field. I'm feeling more energized these days about starting something new, and more excited about working on a startup again.

I wish there was some way I could have avoided falling into the emotional abyss and spending so many years there. Maybe I should have focused on building more friendships over the years instead of being a loner. You really start to take for granted such things until the isolation of failure sinks in. Hopefully this time I will find a co-founder willing to go to felt with me. I'm not sure I can endure another solo fail.

I've been through a handful of ventures in the past few years with ultimately no lasting success. Some made money in certain periods, but ultimately they failed, with the thousands of hours and many thousands of dollars invested in these ventures now "down the drain".

The only thing we can keep doing is pushing forward. Failure must be seen as a learning opportunity, not a failure of intellect or similar.

With that said, if you are experiencing emotional side-effects, which are completely normal from my POV (I've certainly had them), I urge you to consider your mental health, nonetheless your overall health. Success and money do not mean a thing if you cannot get out of your bed or house every day, or if you've frayed all relationships (whether familial, friendships, etc.) while working as hard as we're told to as entrepreneurs.

I failed a business after nearly three years. I thought that it was a great idea and invested $50,000 of my father's money. I got lucky in many ways because I started it in college and didn't have rent or family matters on the line. That said, closing it down really sucked. I feel like there are still some loose threads between myself and teammates — we never closed the loop on some things, so make sure you do that. Otherwise, it will bother you for a long time.

To bounce back, I focused on the opportunities that this experience has instead brought me. I realized that I got deeply involved with the entrepreneurship community on campus. I channeled all my energy to help others start companies and avoid the mistakes that I have done. This, in turn, led to more work opportunities at accelerators and organizations that support startups.

After working for about a year I gained new perspectives and experiences which pointed me to a new idea that I am currently pursuing. The "circle of startup" if you will :)

One of the best frameworks that starting my first company helped me develop is finding "problem/solution fit". Of course, that depends on your past business and experience. Personally, I became more sensitive to noticing problems and realizing that I could solve them with technology.

Serial fail-er here.

Start consulting with companies that have made it a little further down the road and learn from them.

Remember that not everyone has solved the same set of problems.

Find companies that have problems that you already solved with your business, and help that company by applying what you've learned.

They'll benefit from your experience and fresh approach, and you'll see what you can do with a different set of tools (more capital, better product, better team, etc.)

After working with a few companies for a few quarters, you might have a fresh outlook on whether to solve a new problem or join an established company.

I went through this recently and have come out the other side with a successful new venture. It took some self reflection, humility and creativity to get here.

What did it for me was putting aside my ego and realizing that maybe my ideas weren’t the pinnacle of human thought. Up until this point I had been building what I wanted, believing that as an engineer I knew better than everyone else and therefore what they needed and should want. I think Silicon Valley and VCs have this problem in general and this is why most of them fail.

It wasn’t until I immersed myself into searching, networking and communicating, that I finally understood that there is a huge divide between what people need and what engineers think they need.

With that said, my suggestion would be to network with people outside of your normal circle and find someone or a business that is doing remarkably well without engineering or automation. Figure out how to pitch the bigger picture to them and co-opt them into a new venture. Their idea is already working with manual, redundant workflows. Imagine what you could do together to make the business scalable.

It depends on your financial situation. If you can afford it, take some time off and forget about the whole thing. If you need money, I would either get a steady job or a contracting position to reestablish a stable financial situation. It’s hard to think straight while being broke.

This was me a few years ago. My end goal was to build up savings in the 3-5 year time frame.

My off-ramp was to:

1) Take on consulting clients

This allowed for a shift in day to day/finding an alternate source of income asap. Depending on opportunities available, you might want to skip this step.

2) Identify interesting startups in the area + get a software dev job.

This allowed me to hone up my rustier coding skills and make good money without needing to worry about clients/big picture deliverables.

3) After 1 year, move to FANG.

I needed a year to get back into the IC mindset and skillset at a level where I could be hired as a senior/principle level at FANG.

A penny saved is a penny earned.

Instead of focusing on making more money, focus on spending less. This reduces pressure, increases health and time to think and be creative. In my adult life I have spent years in low expense scenarios learning and creating. Forget the herd, do what you want to do. Move to a cheap place (avoid anywhere with a 'digital nomad' community) and go swimming, surfing, rock-climbing or cycling every day. Even if you have zero savings one remote gig or an occasional bout of local work will keep you going.

I’ve just pulled the plug on my business, and now I’m moving sideways - back to regular employment but in a role that’s pretty different from what I’ve done for the last 15 years. Hopefully that will recharge my batteries, and then in a couple of years I might be ready to try again.

I took a job at a small startup for a year. It was healthy for a number of reasons -stable pay, rebuild savings -catching up on new tech I had missed while being heads down -larger teams, more socialization I had missed -time and space to decompress and process what I have learned

I wish I took some time off in between startups. I’d suggest taking some time off to clear your mind and rejuvenate. If you have the ability, traveling can help (although this is tough now with the virus outbreak).

Just work a regular full time job for a while. No shame in it. And if you absolutely can’t get past the idea of being employed for a steady paycheck, then just think of it as a way to raise cash for your next venture when you get a good idea.

Don’t jump into startups right away. Find a company to work for, preferably one which is interesting and positive (not just any stable BigCo but not someone else’s 4 people startup either). Do that without imposing any time limit - when you’re mentally ready, the startup bug will bite. That time you’ll be better all around.

Go work for a big company. The work is slower and you can take a break.

Big companies also mean big opportunities. And you don’t get to see what these opportunities are unless you’re on the inside. You will find some inspiration there for a great B2B company and you can leverage the connections you make there to make it happen.

Let new ventures find you instead.

Take some time to refresh your mind. After grinding your idea for four years you most likely lost some experience in other fields.

Have fun, read fiction books. When you'll find a new idea, you most likely neglect this parts of the life again for several yers. Good luck!

I took a job in the same space as my startup. My startup was bootstrapped, so having built a product and learned the market was interesting experience to my new employer. The work in the job seems much easier once you've been grinding for the same problem on your own. I've continued to deepen my network.

You can still solve the problem you were trying to solve with the startup, although you'll be doing it at a company. Maybe approaching it from a different angle will shed new value on your ideas and creativity, and you won't feel as depleted.

It took me 4 years to recover from burnout post business failing. I moved to the mountains, did a lot of meditating and snowboarding and was able to start a now-successful company after that 4 years.

Wow, I've just woken up to a bunch of new comments. Thanks everyone!

I’ve been there. It was incredibly stressful and tiring, especially towards the end. I could not focus on anything for weeks after, let alone think about starting something new.

Give yourself some time. Eat, sleep, work out, live - chances are you might not have done much of that lately. I would suggest travel, but maybe not right now :)

Look after yourself first, allow yourself to be bored again, the creativity and the itch will come back. But you can’t force it if you’re running on empty.

Take a break, take care of yourself. Be careful with energy levels and then you will know when is the right time and what you want to do.

I've been there. If you want to chat (and maybe even work on something together), mail me.

Partner up with somebody :)