Seeking Advice: Startup Failed, Finances Ruined, Feeling Lost

[cindie]

Hi everyone.

For context, I’m a 25 y/o CEO & co-fo of a startup I’ve been building alongside my 2 technical co-fos. We’ve raised $300K+ total over the last 2 years and have been full-time since January 2022. In these 2 years I’ve taken a $35K annual salary.

We’ve recently come to the difficult decision to wind things down and have officially announced it to our network & stakeholders recently. Aside from running out of cash, we’re mentally and financially drained from the entire endeavor and are looking to move on. I’m having immense difficulties moving forward though.

Don’t get me wrong, running a startup has been incredible. We’ve seen and done things many don’t have the opportunity to do. But I can’t shake the feeling of deep regret and sadness that’s consumed me. I’ve become an intolerable and bitter person to everyone around me, limping around like a wounded animal.

The most saddening part has been my personal financials. In 2021 at age 22, I graduated college into an IT job that had me at $70K with incredible benefits and a great w/l balance. I got restless and suffered from “the grass is greener” with everyone telling me to quit my job after we received the accelerator offer to take things full-time. I wish I could go back and tell myself the grass truly isn’t greener. Since then, I’ve withdrawn the $5K in my 401K, liquidated $10K I had in market investments, and racked up $30K+ in CC debt so far in addition to $40K student loans and $20K car loan.

I have enough cash to take me until April of 2024, but after that I have no idea what I’ll do. I unfortunately don’t have a familial home to fallback on, so I’ll either have to continue going into debt to pay rent, couch surf, or rough it out in my car until I land a new job.

I can’t seem to get myself out of an emotional slump. All I can bring myself to do daily is play video games and eat junk food to try to suppress the pain. I’m struggling creating a resume as well since I haven’t gained any on-paper skills like certifications. I used to be technical (front-end & python) but since I haven’t programmed since 2021 I’ve lost all of my dev knowledge and replaced it with an assortment of other knowledge & skills. I guess my best shot is finding an entry project management role, but lacking proper Certs/accolades has made this difficult.

I’m sorry if this is just a long venting post, but I could really use some words of advice, kindness, and just a “you’ll be alright.” I know I’m young, and one day I’ll look back on this and say “I’m glad I tried.” But right now I’m struggling seeing the bigger picture. If you’ve gone through a similar experience, I’ve be grateful to hear your journey too.

Thanks everyone.

Edit: Just wanted to say thank you to everyone who commented or DM'd. I can't express how much I appreciate the kind words, tips, advice, and resources. It's going to take some time for me to grieve and process this whole thing, and all the support and thoughts are helping me tremendously. Thank you from the bottom of my heart, truly.

 

[613jono]

@cindie You. Are. So. Young.

You’ll be fine, friend. Really. There are tons of people your age who spent the past two years getting wasted. You’re still way ahead of almost all of your peers.

Sure, you probably know some ppl from school who took a more traditional career path and are doing quite well now, but (1) being behind them doesn’t make you a failure and (2) if you choose to pivot to that path there’s plenty of time to catch them.

What you need to do right now is get your head right. Your objective situation is not at all bad, it’s just that your subjective interpretation is negative bc you’ve suffered a painful failure.

Hang in there.

 

[cindie]

@613jono Damn, this is painfully true. Thank you for the last part. It feels like the world is ending, but you’re right. My objective situation is manageable and I can surely recover, it’s just been my negative mindset that’s been hindering my ability to do so.

Thank you, truly

 

[telldtruth]

@cindie I just came out from a hole I dug for myself after things turned bad career wise for me. First experience with failure in my career. Even though I knew I was alright objectively, I still felt like shit every day.

I never was an emotional person so what actually helped me was for the first time to identify and learn my own emotions, sadness, angriness etc. I realized it’s normal to feel these things even though it was new for me, and shifting the focus to getting to know yourself better is priceless in the long run because there will be more bumps.

 

[throwawayaccount1048576]

@613jono Such a good point. This is a leap year in salary for OP.

 

[bumbl3bee]

@613jono This is the right answer!

I do think you need to ask yourself this question, "Why did I fail?". If you don't extract that knowledge from this attempt, then you'll like pay the same fee for those lessons again.

 

[z71517]

@cindie Better to try and fail than to not try.

Go find any job just to get out of your rut and avoid further debt. Study up on the latest in programming and I'm sure you'll have great opportunities ahead.

Well over 90% of tech start-ups fail, and this is a brutal time. You have a lot of company and nothing to be ashamed of. Good luck.

 

[michaeldinunzio]

@z71517 I would say - don't get a job. He is an entrepreneur.

 

[z71517]

@michaeldinunzio How does that pay the bills?

 

[michaeldinunzio]

@z71517 Saved money.
Loans.
Friends, family, fools.

 

[jomary]

@michaeldinunzio What is wrong with you?

No, I’m seriously asking. What could possibly make you think that further draining their savings, taking out loans, or relying on their family & friends is a better idea than getting a job?

 

[michaeldinunzio]

@jomary If you don't have a plan B you will make it I believe.

 

[jomary]

@michaeldinunzio That doesn’t answer my question.

Is your problem just abject stupidity and naivety? Or…?

 

[jomary]

@michaeldinunzio My last reply was mean, especially if your problem actually is abject stupidity.

So I’ll spell this out for you.

If your plan A is winning the lottery, so you liquidate everything you have and pour every red cent into Powerball tickets, the odds won’t suddenly be in your favor just because you have no Plan B.

A tightrope walker without a net may be more careful, but they aren’t suddenly in no danger of falling.

Luck is a huge part of successful entrepreneurship.

Not having a backup plan might, like the tightrope walker without a net, give you more motivation to get everything right, but in entrepreneurship, doing everything right still doesn’t guarantee success.

I know a sub full of people who were successful enough to have internet access, internet connected devices, and time to spend on an internet community like this may not illustrate that, but it’s true.

Simply trying, even trying your hardest because your life literally depends on it, isn’t enough to make it.

So going out on that tightrope without a net, when one is freely available, is just naive and stupid.

 

[ladywalsh]

@cindie First, thank you very much for baring your soul to the group with this gut-wrenching result. I'm decades older than you and in the first year of my second startup. My first failed because of a change made by Google that they reversed years later. My model was adopted by my leading competitor and they exited handsomely.

The measure of your life will not be where your successes lie. It will come from what you attempted, adapted, and learned. The further you get from the experience, the more perspective you will gain. The regret of failure can always be soothed with another attempt, our growth from the experience that blooms in another. The regret of the cowardice that defeat brings stings for the rest of your life.

You took your shot, and seemingly played it straight with investors. For that alone, you should be proud.

 

[cindie]

@ladywalsh Thank you for this perspective, and for the kind words. Deep in my mind beyond the negative thoughts, I know that these words ring true.

Best of luck and good wishes to your current startup journey, I hope all works out in your favor

 

[real_mayonnaise]

@cindie You should position yourself as a product manager - in demand, hard to find, and hard to define. Startup ceo founders often do this and can probably adapt to the roll in a company that they find vaguely interesting.

 

[cindie]

@real_mayonnaise It seems like my current skillset & experience align well with those of a pm so I’ll have to begin searching for pm roles. Thanks a ton for the tip, I’ve been struggling to figure out what role titles to look for aside from proj manager.

 

[real_mayonnaise]

@cindie Product manager is a way more interesting (and much better comp) than project manager. I’d go read those job descriptions at the faangs.

At Microsoft this role is called program manager and a product manager there is more like a product marketing manager everywhere else.

You might also consider product marketing manager as a path if you are more marketing oriented but dev experience is more valuable for prod mgmt since the job is basically making sure the devs make the right things.

 

[cindie]

@real_mayonnaise Funny enough, I had scheduled a chat recently with a mentor who works at MSFT and asked him about a role I was thinking about applying to (Account Technology Strategist) and he ran me through the role definitions and such at MSFT which was a tremendous help but also put me in a whirlwind lol. Program Manager def seems like the way to go at MSFT since I enjoy being the bridge between biz & dev teams.

Once I’m in the right mindset, definitely going to revisit and see what offerings they have open. Thank you!!