Ask HN: Advice for moving on from a failed startup?

69 points by throwaway9838 ↗ HN
Hello HN,

I am in a bit of dilemma. I started a enterprise software startup with a bunch of friends in college, we got a bit of funding and I dropped out. We did couple hundred k in revenue and raised a bit more but eventually we couldn't make it work. For past 2 years feels like I have been in a zombie startup and want to move on.

For people who have been in the same boat, what did you end up doing? As for getting ready to be in the job market again, what kind of positions did you end up applying for?

I am thinking either:

1) Join a seed/series a startup as a developer and grow with them. Pros of this are this is what I know how to do best and love working in small teams

2) Join a more established bigger co. Pros are a more stable position but not sure it will be an environment i will be able to do well in

52 comments

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I’ve been in this boat but it was a bit worse than what you’ve described.

Your next step will be extremely individual. I took some time to evaluate all my options and go with what I felt would give me the most joy.

Maybe my comment isn’t the most useful but I wish you so much success and happiness. Good luck!

Join a more established or successful startup in the same space.

Understand what separates the successful startup from the failed one you're in, was it the product, sales pipeline, marketing, org structure?

Essentially perform a diff between the two companies and root cause what you'd improve on and other structural things you'd change the next time around.

I'm sure you've acquired experience in the vertical that your startup was in, recoup of the time and energy investments made there.

Lastly all the best, this happens to many early employees and founders.

I don’t think you can do a diff as there so many factors that you can miss without having a complete bird-eye view of the business or the org.

But nevertheless, this is a great advice in that it still would give you a good example of a functional business/org and increase your chances of success significantly.

I think better to go for an earliest stage but established startup, like series A-B, where they just validated their product-market-distribution fit and are on track to scale, but you still can get a sense of how it feels to have this early PMD fit.

On the other hand, you still will miss on the 0-1 stage and if you want to learn how to do that too, may be worth joining a very experienced serial founder at a 0 stage. They usually have enough resources to iterate till they find one.

Edit: typos.

Spend some time to focus on yourself, your family, hobbies, self. Make sure you have a good foundation outside of your career and are working to live. If you take the time and allow yourself the time and space to do so the career stuff will just fall in place and the right choice will become obvious.
First thing I would do is take some time off. Even if it is just a week or two.

As far as a job goes, either one is fine. Working for a larger established company will teach you some stuff you probably haven't picked up. I would argue this is what you should do next.

This is a badge of honor that doesn't feel like one in the moment. I was in the same boat for 3 years before re-entering the job force, I felt isolated and demotivated in the 3rd year, when it was clear it was not working. Join a rocketship! Surround yourself with constructive minds. Try again in a few years, if you want. Life goes on.

Consider MainStreet! We are hiring like crazy :) https://jobs.lever.co/mainstreet

You got this next step!

MainStreet looks interesting. Does your interview process involve whiteboarding?
No whiteboarding, but there are questions on architecture and your standard set of coding problems. In lieu of the whiteboard, we encourage candidates to verbally walk us through their answers/solutions, and are free to use pseudo-code to illustrate.
Hey, also replied to the parent comment, but would also love feedback on if you'd like the interview process description changed at all for Mainstreet's listing here (I used your comment as the basis for the listings): https://nowhiteboard.org/
Thanks for the advice, joining a rocketship is what resonates the most with me to be honest.

Happiest I have been was when I was sleeping 5 hours a night maximum, always on the road visiting different customers' offices to work closely with them. Had an offer about a year ago to leave my current position and build out the data science team of a rocketship but didn't want to leave my team on their own.

Bit late on the reply, but I just featured your company on my website! Check it out here: https://nowhiteboard.org/ I'd also love feedback on if the interview process description needs to change at all for your company's listings
It’s probably important to know how close you were to finishing your degree, and if you have family or other support (financial aid?) to finish the degree.

It’s not the most important thing in the world, but if you were close it might make sense to pick up the necessary credits and get the diploma. In addition to having the degree (which can be useful if you’re applying to jobs where applicants are sorted by crude algorithms), you’ll also show that you are the type of person who sees something through.

But whether it’s a good idea or not depends on how far along you were when you dropped, the possible prestige/networking value of the degree, and your financial situation.

...and then they go back to a startup job where no one cares about the degree. But sure, if it's a tiny effort, might as well...
If OP wants to work abroad in the future - where I come from getting a skilled visa having a degree is an advantage. Not having a degree is not a problem either. But trying to get a visa having dropped out definitely counts against you.
Become a cog in the machine of a huge corporation. Get a position which is indifferent about whether you solve a problem today or on Monday. A regular paycheck that is predictable and impersonal is the way to put as much distance between this and your future.
Late stage startups are far more stable, and if the founder is still around, they still have the little startup DNA. Even a Series D unicorn will be looking at two digit monthly growth as opposed to an established co which is proud to hit two digit annual growth.
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Join a small tram that seems decent and does interesting things.

If you do good work there and are a good teammate, you can always get new jobs through referrals. Which is also a kind of stability.

After I decided to kill my startup that was not going anywhere I took a year break from startups and just spent time with my gf, friends and hobbies. I have got myself into fpv drones and planes as I find flying extremely relaxing. Now I am back at trying to build some of my ideas.

I do have a full-time as mobile dev job that is not too demanding so I have still time for my own projects.

That's tough if you're in a HCOL area and have to rent or are looking to purchase a home. Even if you're flush with cash landlords won't rent to you nor banks lend.
Lots of early stage startups are looking for founders. You've already learned all the $Expensive lessons, your experience is honestly valuable, it's difficult (not rare) to find so it's very valuable, especially at this stage. Good luck. If you really felt the need to post this, you need to expand your network, consider picking up a mentor or two to help guide you.
How does one pick up a mentor?:) I would love to have some kind of mentor, but I have no idea of even where to start looking.
Reach out to your boss and see if they have someone in their network. It's not uncommon to have 2-3 mentors you meet with once or twice a month for lunch etc.
The CTO and co-founder of the company left without notice 18 months after company creation/me joining. He burned out.

He's doing great from what I've seen and has recovered a couple of months after quitting. He went back to a company he worked at before co-founding the consulting company.

Not sure if this is relevant because there was no product when he was here, only consulting and projects that went nowhere and clients that he found difficult to work with. Now we have a product and work with great clients with projects going somewhere. More revenue per year with a third of the team. Almost zero churn for three and a half years.

Taking over and handling the aftermarth so the company does not die has been quite an education.

My last job was a failed startup. I felt like the view from its wreckage was a unique vantage point. From there I could see where we went wrong and I knew who was doing it right (because we were eyeballing the competition).

I was still interested in the space, so I just applied at one of the competitors that was excelling where we were failing. I put "if you can't beat 'em, join 'em" in my cover letter.

That was six months ago. So far, I'm happy with that way of moving on from a failure.

I regularly talk to founders who are going through the process of leaving their startup, and something that always gets tricky is what happens with your vested equity. Friendships are lost over this question.

I did a bunch of research and the most common thing that happens is this:

- the departing founder reduces their ownership to 5% or less (giving the shares back to the company, even if you've vested them)

- the departing founder receives at most $25000 (depending on financial circumstances of the company).

This is typical for companies that want to stay on the startup (rocketship track). This may not be the case for your company, but either way I'd try to ensure the company is structured for the success of those who are staying there.

Some founders ask for a lot more money or they want to keep ownership of the company - both cause a lot of trouble for the company and may lead to the company dissolving (in which they get nothing). They also destroy friendships and relationships, which are valuable in the long term in tech.

That's a gritty question!

First things first, I would think about the parts that went well, that you actually liked, then look for a role that incorporates those same elements to the extent feasible. Really dig into that one and isolate what you'd want to duplicate in a new role.

Regardless of the size of the company. There are exceptional and awful roles at any company size.

I would also be prepared for interviewers to expect a calm and candid explanation for why the company didn't get to where it wanted to go. Obviously, no finger-pointing or hyperbole in it.

1. Pivot to Crypto. Doesn't matter what you make.

2. Raise VC funding. Super easy if you are making anything Crypto.

3. Launch coin.

4. Retire.

I was the lead engineer at a small, B2B startup. We got N millions in seed funding, but the product barely got any traction. Growth was slow. The last couple years there were definitely zombie-like, after most of the original team was laid off or left on their own.

I eventually moved on to be a cog-in-the-machine principal engineer at a larger company. To be honest, it's not very satisfying. I prefer earlier stage, even though it's generally lower pay for higher risk.

I'll probably do something else soon.

Advice definitely depends on more factors that you’ve shared. (I’m not asking you to share more, just stating the situation.) It depends on how your co-founders feel, it depends on your collective financial situation, on your equity agreements, outstanding contracts, it depends on what will happen to your customers, etc.

I started a company with a friend and when we ran out of money, energy to continue started petering out, even though our metrics were trending the right direction - surely, but slowly, too slowly. We were very lucky to get a buyer right before we were about to close the doors, someone who we knew, who cared, and who was able to get some funding and carry the torch and keep it growing. That took a lot of the worry out of having to stop working on it.

As for the next step - I think I found the best of both of your options in a small team inside a large company. It has helped refill the coffers a little after spending more than I should have trying to get a startup off the ground, and it has been exciting and fast paced in a startup kind of way.

It depends on your appetite for startup environments, but a couple of things I like about bigco right now are that I don’t have to do payroll or taxes or advertising or worry at all about where money is coming from. I get to go deep on technical subjects and spend time inventing rather than productizing.

After having done a startup, I would like to do another some day, but I have learned many lessons, and personally I want to wait for the right idea, the right funding, the right team, and not just jump into any ol’ startup at all.

> Join a seed/series a startup as a developer and grow with them. Pros of this are this is what I know how to do best and love working in small teams

Sounds like you already know what you want to do :) Trust your gut, if this is what it’s saying, go for it!

My suggestion is to join an early stage startup, founded by someone(s) with a good track record and with values that resonate with you.
I know your questions are practical, and you have not disclosed your emotional state, but I also know firsthand that shutting down a startup can be traumatic. Even as you address the practical issues, take care of yourself and do the inner work to process everything you have experienced.

I wrote a book titled "Eating Glass" specifically about the emotional journey through a failure like this [0] and put numerous chapters online for free [1]. My primary goal with the book is to help others, so I'd be happy to send you a free digital copy if that's of interest.

Good luck to you... you now possess valuable knowledge and wisdom to help you in your next venture and in life.

[0] https://www.amazon.com/Eating-Glass-Journey-Through-Failure-... [1] https://markdjacobsen.com/eating-glass/

I’d recommend fixing your startup. Take a look at it this way, you survived one of the weirdest economic times and we are on the precipice of a massive boom.

Your problems likely fall into one of three categories with known fixes:

1) You don’t have a recurring revenue model, I’m inferring this from we did a couple hundred k in rev but eventually it didn’t work.

Solution: figure out how to move to recurring rev.

2) Your product has a fundamental problem that you aren’t fixing to deliver value for your customers.

Solution: find out why they left. Fix it. Use those customers as testimonials / references for new customers.

3) Due to economics you were unable to acquire more customers.

Solution: reinvigorate your sales team.

If you’ve survived the last two years you can survive another two in the new economics. I would recommend taking a month to three months to get your head back in the game.

It’s virtually impossible that your product is so niche that you’ve exhausted the market after a couple hundred k in rev.

Mine failed too (cofounders dropped the ball), so I joined a seed startup (Lido) and both me and the company have grown really fast.

Having worked at larger Cos (Square, Two Sigma), company stability is way over valued. The SWE job market is so good that if one company fails, 10 more will be pining for you next day.

No idea. My buddy and I have a Phase I SBIR finishing on Friday and I think we’d need a Phase II to even get to the point of having a product. As much as I love being in the fight and taking risks, I don’t know that it’s worth working for peanuts for another two years.

The job market is hot and I have a nice project to show off. A month of studying and I could land a nice job, I feel.