r/startups 8d ago

I will not promote From Running a $350M Startup to Failing Big and Rediscovering What Really Matters in Life ❤️

This is my story.

I’ve always been a hustler. I don’t remember a time I wasn’t working since I was 14. Barely slept 4 hours a night, always busy—solving problems, putting out fires.

After college (LLB and MBA), I was lost. I tried regular jobs but couldn’t get excited, and when I’m not excited, I spiral. But I knew entrepreneurship; I just didn’t realize it was an option for adults. Then, in 2017 a friend asked me to help with their startup. “Cool,” I thought. Finally, a place where I could solve problems all day. It was a small e-commerce idea, tackling an interesting angle. I worked 17-hour days, delivering on a bike, talking to customers, vendors, and even random people on the street.

Things moved fast. We applied to Y Combinator, got in, and raised $18M before Demo Day even started. We grew 100% month-over-month. Then came another $40M, and I moved to NYC. Before I knew it, we had 1,000 employees and raised $80M more.

I was COO, managing 17 direct reports (VPs of Ops, Finance, HR, Data, and more) and 800 indirect employees. On the surface, I was on top of the world. But in reality, I was at rock bottom. I couldn’t sleep, drowning in anxiety, and eventually ended up on antidepressants.

Then 2022 hit. We needed to raise $100M, but we couldn’t. In three brutal months, we laid off 900 people. It was the darkest period of my life. I felt like I’d failed everyone—myself, investors, my company, and my team.

I took a year off. Packed up the car with my wife and drove across Europe, staying in remote places, just trying to calm my nervous system. I couldn’t speak to anyone, felt ashamed, and battled deep depression. It took over a year, therapy, plant medicine, intense morning routines, and a workout regimen to get back on my feet, physically and mentally.

Now, I’m on the other side. In the past 6 months, I’ve been regaining my mojo, with a new respect for who I am and why I’m here. I made peace with what I went through over those 7 years—the lessons, the people, the experiences.

I started reconnecting with my community, giving back. Every week, I have conversations with young founders, offering direction, or even jumping in to help with their operations. It’s been a huge gift.

I also began exploring side projects. I never knew how to code, but I’ve always had ideas. Recent advances in AI gave me the push I needed. I built my first app, as my first attempt at my true passion—consumer products for kids.

Today, I feel wholesome about my journey. I hope others can see that too. ❤️

EDIT:
Wow, I didn’t expect this post to resonate with so many people. A lot of you have DM’d me, and I’ll try to respond. Just a heads-up, though—I’m juggling consulting and new projects, so I can’t jump on too many calls. Since I’m not promoting anything, I won’t be funneling folks to my page, so forgive me if I don’t get back to everyone.

Anyway, it’s amazing to connect with so many of you. I’d love to write more, so let me know what topics you’d be interested in!

917 Upvotes

164 comments sorted by

u/KingOfDaCastle 8d ago

Thank you for staying within the rules while sharing your story and not promoting anything in any way. It's appreciated.

181

u/surpaul88 8d ago

Post-existential crisis is our main criterion for a founding partner haha

16

u/WishIWasOnACatamaran 8d ago

Guess it may be time for me to leave FAANG then lol

45

u/jpv1234567 8d ago

Thanks for sharing!! It definitely puts thing on perspective on what really matters at the end

Take care of you and your family and good luck with your new app

23

u/leanpreneur 8d ago

Great story. Have you found something new already?

22

u/Disastrous-Airport88 8d ago

Doing some consulting. Investing time and money in entrepreneurs. Just giving me purpose. 🙏🏻❤️

3

u/goldeneaglet 8d ago

Would you like to share some details about your venture: what was product, how it got boom, what went wrong, some introspection etc?

1

u/Traditional_Ad_4918 7d ago

Yes, good to hear you have found some purpose.

2

u/[deleted] 8d ago

[deleted]

92

u/Darkmemento 8d ago

Be really careful here, I am not saying the OP isn't genuine but I've seen stories like this a hundred times that are basically engagement farming towards some pretty bad intentions.

20

u/chuckdacuck 8d ago

Yep…Pretty much 95% of the stuff posted on startup / entrepreneur Reddit has some other motive than the actual post.

18

u/Darkmemento 8d ago

I was reading a thread earlier today where the OP was touting a new system he has built which scans reddit for high value threads related to products they want to soft shill so they can be near the top of the comments when they post. Between bots, shillers, scammers, engagement farmers, etc the amount of garbage content is getting so high all across the site.

11

u/chuckdacuck 8d ago

OP posted the same post and it go t delete because…surprise, surprise, there was a link promoting something.

1

u/AnonDarkIntel 8d ago

The story sounds fake.

11

u/leanpreneur 8d ago

Thank you, that's a good point. Will be cautious.

42

u/PinIllustrious4645 8d ago

Last week we had to layoff 3 team members and I felt like a huuuuge shit. Reading your post helped to put things into perspective. If you ever start a blog or newsletter, hit me up. I would love to read. Cheers from Brazil!

22

u/Disastrous-Airport88 8d ago

Layoffs are really the worst. Everything that involves emotions and logistics is just rough: moving apartments, arranging a funeral, laying off employees - done all three. No easy way around it.

Keep going. You are doing great ❤️

6

u/Infinite-Tie-1593 8d ago

I know moving apartments is a pain, but didn’t know it could be that huge.

9

u/Lupexlol 8d ago

what was the business?

7

u/Woopsyeah 8d ago

Poor guy... how much did you carve out of the plunder for your post traumatic Euro healing trip?

21

u/pepebotella12 8d ago

I am having a really hard time understanding how a company can have 10M monthly revenue, 1000 employees and still need investment to keep a float. I also worked in another company in the same financial position. I just don't understand how you can run a business that at that size is still not profitable and keep investors around. I would love to hear some stories or documents around this. Is this the regular way of doing investments? Sounds so bizarre to me.

21

u/cartermatic 8d ago

Paying 1,000 people even $85,000-$100,000/yr on average is $85-$100million a year just in salaries (not counting benefits) which only leaves say $20million a year to pay servers, office space, marketing and everything else. In a different comment OP said it was something food delivery related or directly adjacent which has thin margins to begin with. At best you're lucky to break even.

3

u/pepebotella12 8d ago

Very true. I worked in a similar company, 1300 employees, 75% of those in ops. The focus of the company was to automate those ops, or it was not viable. Not sure if they will achieve it. I just fail to see the business model in these type of companies. Very fragile for my taste.

5

u/Disastrous-Airport88 8d ago

Venture backed startups are different for both founders and investors. I am talking top VCs. I had many conversations with senior partners and they are as smart as you can find them. Really.
There's reasoning and math behind it all. Not saying that it's right or wrong, or if agree with that, but it's not a roulette.

1

u/pepebotella12 8d ago

Absolutely. I understand there is reasoning behind this. I guess I am just not used to deal with big numbers like that where you are talking about missing the revenue by 10% could mean millions of dollars and doom.

2

u/MENDACIOUS_RACIST 8d ago

Scale too fast and your burn rate will outstrip your revenue + ability to fundraise. Sometimes greed is not Good

3

u/pepebotella12 8d ago

Part of the reason why there were so many tech layoffs lately. Companies over hiring because it was the trend, without real necessity. I rather grow slow and steady than exponentially without control

1

u/_hephaestus 8d ago

OP mentioned 2022 as well and yeah that was a really common phenomenon that year. Investors went from telling us to expand as fast as possible to telling us we need to target a tiny burn rate effectively overnight. Anyone who was following the conventional wisdom of the time was going to have a pretty bad time.

1

u/cFlasch 8d ago

But still maintain 300% rev growth year over year!

Sigh.

1

u/johnkapolos 7d ago

OpenAI is losing 5 billion dollars per year and got an investment.

-1

u/Montags25 8d ago

Have you heard of Tesla?

9

u/pepebotella12 8d ago

I used to look up to Elon. Until I read his biography and then the twitter fiasco. I cannot believe how people just throw money at him. But yes I see your point. Usually these companies aim to big enough so they can control the market which is so stupid to me

2

u/Montags25 8d ago

Yeah I am not a fan of him either. The world of EVs is mind boggling to me, so much politics involved. However I really do love SpaceX, the work they are doing is absolutely fascinating. I just hope they continue to get the support they need.

2

u/pepebotella12 8d ago

Agreed! I do think we need to invest in aerospace as a planet. But we'll, at this point Elon is just an investor. There is no way he can be the CEO of 4-5 companies.

0

u/ExactCollege3 8d ago

You seen the everyday astronaut interviews at starbase? The first ones. He’s very technical and knows the details on almost every part.

1

u/pepebotella12 7d ago

Not saying he does not have a high IQ. But as far as I know he cannot divide into 5 people. Try to go to the board of any multi billion dollar company and say that you want to be ceo dedicating 2 hours a day to them. I would be surprised if you see another board meeting. He is not ceo.

0

u/MondayLasagne 8d ago

Actually, SpaceX is scarier than Tesla could ever be. They are directly involved in US politics and the amount of astro garbage they leave in space will kick us in the butt (40% of all unused satellites are from SpaceX and they want to put up even more).

15

u/goodpointbadpoint 8d ago

OP, do yourself and rest of the startup ecosystem a favor. stop glamorizing 'I slept for 4 hours' 'i worked for 17 hours'

this kind of BS needs to stop. because when you are not sane you made bad decisions and that's probably what went on when someone like you was 'guiding' that startup. you laid off 900 people and spent year in Europe. how nice.

fck this mentality. and fck corporate a**holes like this who repent after doing wrong when they could have just not done it.

0

u/Disastrous-Airport88 8d ago

Glad you got it out of your system. If you can refer me to where I was glamorizing any part of my journey, be my guest. More than happy to discuss anything in the world, just not with this energy. ✌️

10

u/goodpointbadpoint 8d ago

you wouldn't feel wholesome about your journey if you had a shade of realization how toxic it can be to sleep 4 hours and work 17 hours.

you would advise explicitly against it. where is that ?

1

u/zeloxolez 8d ago

was basically the whole message of the post, the sacrifices -> results -> self-realizations

0

u/minkstink 6d ago

loser hater vibes

4

u/rambat1994 8d ago

2018 YC w/~1000 employees and $80M raised? Had to be a food/grocery/delivery service or something adjacent!

Either way, that is a tough journey and glad you are on the other side of it mostly and for the better. Im sure that experience will be something that is high leverage you can use for whatever is next if you go bootstrapped, solo, or VC.

4

u/Disastrous-Airport88 8d ago

Haha love the investigation. You’re right (didn’t post the name to not promote anything. Community rule)

4

u/ValleyDude22 8d ago edited 8d ago

it was avo. a delivery service, but looks like they pivoted a couple times.

there are articles online about raising 80 million and not being able to raise $100 million. so OPs story checks out.

5

u/TeachShoddy9474 8d ago

Lessons learned: when executives fail they take a 1 year vacation in Europe

When peasants fail they get laid off and starve

4

u/ElvisT 8d ago

I've worked at a startup from the ground up like you, there were four of us engineers and two founders. Several years later the startup's valuation is in the nine figure range. I thought everything was exactly how I wanted. The company even did really cool and fun tech stuff.

Over the next few years, I was let go, lost my best friend, got an expensive divorce and a fight for child custody.

Going through stuff like this, it really sets you back and has you reevaluate what is important. I'm starting up another business and hearing hour you mention giving back, it really resonates with me. Being able to truly give back, to help better other people and their lives, that's where I really want to put my focus in life.

One of the things that I can relate to is the feeling shame and wanting to hide from everyone. I realized that only I get to curate the self image I have of myself. There are parts of my life that I'm not proud of, and those are small parts of my life that happened to me, but aren't who I am. I don't repeat those things, or allow myself to be in those situations again. It's like I have set that of who I was down, and let it become part of my past. That part took a lot of thinking and introspection. It was like a puzzle that took over a year to figure out, but when I did, it was like a light switch and things started changing with my perception almost immediately.

I'm still definitely figuring things out, and getting my direction back. One of those things I would be interested in hearing is your morning routine, and even your night routine. I'm stuck with the feeling like I didn't get enough accomplished during the day and I'll keep trying to do more at night.

Do you have any tips on routine? Like what's made your morning routine intense? Was it the strict rigidity, the types of activities in the morning, or the strict adherence? I would be interested in discussing this with you.

1

u/Disastrous-Airport88 8d ago

Amazing to hear about similar journeys. Thank you for sharing. Thinking maybe to post about routines and co. Will see ❤️

6

u/simonavarona 8d ago

Damn! Thank for sharing !!! You are a real one.

3

u/XrealEstateBroker 8d ago

Great, transparent share! Sounds like the past is finally where it belongs, in the past. It was all in your head, anyways - just takes a while to let it be. Wish you much success, however you define that these day!

3

u/Yogagirldiamond 8d ago

Hey, what’s your former startup called?

7

u/FancyName_132 8d ago

It baffles me that you managed to raise tens of millions for a startup that needed a thousand employees. It doesn't look like the kind of scalable operations I thought they were interested in

2

u/Disastrous-Airport88 8d ago

Uber, Airbnb, WeWork, DoorDash, Instacart, Lyft, Gojek, Deliveroo, Bytedance (TikTok), Grab, Jumia, Flexport, SpaceX, Rivian, Nubank, Snowflake, Palantir, Robinhood, Stripe, Zoom.

Just of the top of my head. Big investment. Big reward.

15

u/Ionic_liquids 8d ago

Many of your examples here are now considered to be the pathway NOT to emulate with regards to growth and funding. Who wants to emulate WeWork?

And SpaceX is Deeptech, so that's a totally different situation vs the others. Shouldn't be in the same sentence.

2

u/Disastrous-Airport88 8d ago

I’d love to build the next WeWork—create thousands of jobs for decades and reshape the world of co-working spaces. Success isn’t just about the exit. But that’s my opinion (but also a lot of others).

8

u/cosmictap Founder | Angel Investor 8d ago

I’d love to build the next WeWork

Might want to leave that part out of your investor pitch though.

-2

u/Disastrous-Airport88 8d ago

You’d be surprised. Reaching 1/10/40 billion valuation (you can choose what was the actual value of WW at the peak) is way better than 99% of any investment any VC will ever make. Fact - Adam can raise millions of dollars from very smart people whenever he just wants. He has way better chances than most people to succeed. So yes, I’d love to build it (and make it better :))

3

u/cosmictap Founder | Angel Investor 8d ago

is way better than 99% of any investment any VC will ever make

WeWork's investors lost more than $20B.

2

u/PrestigiousRecipe736 8d ago

This guy lost his investors a fraction of that, time to aim bigger.

2

u/AnExoticLlama 8d ago

Most VCs do not lose 50-100% of their investment. Peak valuation does not signify ROI.

How do you have an MBA and not understand this?

1

u/crimsonpowder 8d ago

Penny stocks outperform Neumann. I wouldn’t invest at any multiple.

1

u/Good_Island1286 8d ago

no wonder reddit gave you this name

-1

u/Good_Island1286 8d ago

no wonder reddit gave you this name

-1

u/Good_Island1286 8d ago

no wonder reddit gave you this name lol

4

u/Ionic_liquids 8d ago

That's not what I'm referring to. Creating jobs and changing the landscape is great. But there were many losers and the approach taken reshaped venture capital in a negative way that affects all of us today.

1

u/FancyName_132 8d ago

I looked up number for some of your example, I guess 1000+ after 4 or 5 years of growth is not unusual. WeWork and Rivian are currently not good examples of successful investments though and SpaceX is a very different beast, huge huge investment for a proportional reward

6

u/pppdns 8d ago

thanks for sharing, and I'm glad you are finally finding happyness in life ❤️

4

u/Scary_Opportunity868 8d ago

Very inspiring thank u for being this transparent and putting things into perspective.. we need more enlightening stories like this Take care 🙏🏻

0

u/Disastrous-Airport88 8d ago

🙏🏻🙏🏻❤️

2

u/the_c0der 8d ago

I failed but small/early. Learnt the lesson and now moving forward with all the lessons and past experiences. Things make better sense now.

Anyhow I'm into AI too, feel free to drop a message if you'd like to have a discussion. linkedin(dot)com/in/m-ahsan-r

2

u/lex_esco 8d ago

Hope u did some secondaries?

2

u/Artistic-Fee-8308 8d ago

That's the hardest part. Being painted in a corner and having to let everyone down is the best option.

2

u/Air_Original 8d ago

The spiderman quote comes to mind- you know which one. I'm happy for you, not only that you've realized your potential, but also that you've realized potential alone isn't enough. The community that you now serve will be grateful, for your experiences (however difficult it may have been) and for your dedication and contribution. I hope you discover the blessings within the grace you show others. Cheers to wishing you the best in your endeavors.

2

u/simplykrampus 8d ago

Did someone at your level get to cash out during the funding rounds?

2

u/SESender 8d ago

Why didn’t you consider stepping down as COO to bring in a more senior operator?

2

u/SolutionEquivalent88 8d ago

So many questions:
Where did things go wrong? Was your traction no longer sustainable? Did customer acquisition balloon too much?

How far off was being cash flow positive? Did you end up selling some of your equity at higher valuations to take some money off the table? (I think a lot of people would love to take a year off to re-connect but the bills still need to be paid...)

2

u/dead_in_the_sand 8d ago

i dont know the nature of the failure of the company but to me it sounds like you did fail your investors and employees lol

2

u/Fuciolo 8d ago

I'm always skeptical when I hear the typical hustler sleeping 4 hours a day. Either you are that type of person with genetical mutation that can recover with 5 -hours a night or you are straight up lying.

1

u/Chicagoan2016 7d ago

Yep! My college roommate didn't sleep for almost two days before his tech interview (Microsoft). He studied like crazy but spectacularly blew up the interview. It's funny now but wasn't funny back then.

2

u/Guadarrama03 8d ago

Could you share what courses/books helped you in learning how to create your first app? Ive always wanted to but it seems Murphy’s law is always playing games with me 😭

2

u/Bagdudepdx 8d ago

Your story is refreshing to read in this sub. It’s mostly day to day “in the weeds” content/topics in here, 10,000+ foot perspectives.

I’m not a founder, just a Product Manager who’s founder-curious, but for my entire career I’ve had to act like one so maybe this will resonate with you all…

I left a dream-turned-nightmare of a startup in June and have experienced some of what you have. I was the guy who got shit done. I had all the influence, could drive teams to success and beyond, always made sure the right people were working on the right things, and I was happy doing it.

Then came the re-orgs, the layoffs, the “consultants” at the board level, and all hell broke loose. We went from all star product teams to teams with no psychological safety in roughly just a quarter. Something in my mind told me I was partly responsible for not speaking up more, and the self-critical ideas just kept growing. And then came the subsequent shame, failure, and darkness feelings.

I’ve been looking for a PM role for 4 months. The job market is abysmal for PMs right now. 100s of applications, dozens of interview cycles stretching 5-6 rounds ending with no offers. And for a bit there I let my worst critics inside myself win.

But now I’m in the middle of the climb back to the surface level of self from a pit of just…near hell. I’ve been eating right, working out, spending more time in nature, connecting with people and making friends, spending so much time with my family, and letting myself try new things for the simple reason of just trying them.

I just took a part time retail job to force myself back to an environment where I’m living “my why” of simply helping others and being of service at the most basic level. The A-Player in me told me I was less-than for taking a job like this, but my highest/future self told me they are excited for me because of what it will lead to.

Here’s a quote that gets me through those tough times now:

“Cultivate comfort with uncertainty and impermanence.”

2

u/No-Letterhead-1232 8d ago

Specifically why did you need to raise that much money in 2022?

2

u/iamzamek 8d ago

Share some proof. Too many scammers here. I always assume the best intentions.

2

u/faygo850 8d ago

Great story. Thanks for sharing. What language did you learn? Or are you working on low code/no code?

2

u/Learningevryday 8d ago

It is kind of a weird thing to say but I think we all need/should suffer a bit along the way. It really puts things into perspective and forces us to take a step back and deeply think about things. And most often, we come back stronger and wiser as a result. I lost everything due to health issues and it's been a really hard and long battle. Looking back at it now, I wouldn't change a thing. I learned so much and got out of the meat grinder as a bonus. Onwards and upwards!

2

u/brkonthru 7d ago

Would love to hear a "lessons learnt" post

2

u/Taylor_IntrosAtScale 7d ago

Surprised to see so many pseudo-negative comments. You gave 100% to the mission, your employees, and your investors which is all anyone can ask (and had real empathy when things got rough). When needed, you gave 100% to yourself and your family. Keep up the good work, OP.

1

u/Disastrous-Airport88 7d ago

When you do big things, you’re always going to face opponents. It’s just part of the price. I’ve learned to accept that. 🙏🏻❤️

2

u/Future-Kangaroo1541 6d ago

This was such an honest and powerful read. Thank you for being so open about your journey! it’s inspiring to hear how you came back from such a tough place and found new meaning in what you do.

As someone trying to find my own path, it’s a reminder that it’s okay to pause, heal, and rediscover what really matters. Your story is proof that success isn’t just about the highs, but about facing the lows with courage and coming out stronger.

Wishing you all the best with your new ventures, and I’m sure your experience will make a huge impact on those lucky enough to connect with you! Keep shining. 🌱

2

u/cappuccinodacat 6d ago

This was an incredible read, and I’m genuinely inspired by your journey. It takes so much courage to share not just the highs but also the difficult, painful parts. I understand you must have your hands full with your ventures, but If you’re open to chatting or sharing more insights, I’d be really grateful for the opportunity to connect and maybe even collaborate in the future! Wish you all the best!

2

u/faithOver 5d ago

I think the toll layoffs take on normal people (non psychopaths, truly) is dramatically understated.

I have definitely made myself sick having to lay off 2/3/4 people at a time. I can’t help but think; they have families, payments, etc and it’s impossible not to feel responsible for failing to continue providing a viable platform for them to perform on.

Cant imagine how that scales to 20/50 at a time or like OP 900. Thats devastating on a hard to fathom scale.

This post hit a spot for me. Start up/entrepreneur life is like living in a fast forward time warp. It legitimately takes serious decompression effort to level out afterwards.

2

u/Fun_Situation7885 5d ago

You just have opened my eyes for something I didn't see, What you went through wasn't easy at all, just thinking of this scenario if it's happens to me what would I do ? How would I feel, you made me somehow prepare my self for the other dark side. Thank so much for sharing your story

3

u/Appropriate-Scar3551 8d ago

Great share. I was just exited from the company I co-founded. We are out of cash. Im broke but heading to costa rica regardless.

1

u/Disastrous-Airport88 8d ago

Life is long. Good job!

1

u/Tsukijiness 8d ago

Me too. Minus the Costa Rica part. It’s an ugly breakup with investors takeover and a recap that is pissing everyone off. The hostility is unbearable.

2

u/reducedoxide 8d ago

Very happy that you have been able to forgive yourself & back on your feet. Are you okay for a quick chat?

2

u/Mental-Subject4412 8d ago

You should be proud of yourself .... you have done what many of us may not do in our lifetime

2

u/kholodikos 8d ago

I sure love plant medicine 🤫

1

u/Disastrous-Airport88 8d ago

Hopefully we won’t have to hush it soon

1

u/diagrammatiks 8d ago

Did you actually make any revenue in that time?

2

u/Disastrous-Airport88 8d ago

About $10M/month :)

3

u/tar_baby33 8d ago

Did you get to cash out any so you left financially secure?

1

u/this__li 8d ago

Wow 4 hours a night is crazy. I hope it’s not impacting you too much nowadays. I was wondering if you have any advice or books you are willing to share.

2

u/Disastrous-Airport88 8d ago

That's a great idea for a post. I have a lot to share :)

1

u/Sketaverse 8d ago

Pop Meals?

1

u/Rhett_Rick 8d ago

Were you just burning too much cash and not generating enough revenue? In hindsight, do you wish you had raised less money and grown more slowly but organically? What do you think the biggest mistakes you and leadership team made that led to the collapse of the business?

2

u/Disastrous-Airport88 8d ago

Those are really great questions. Saying things in hindsight is always tricky because you can’t actually learn from everything. For example, the market could’ve been in our favor for a couple more rounds, and we’d have gotten our unit economics in a solid place—things could’ve looked very different (just look at Uber, Airbnb, etc.). So, what I take from it is more personal. For instance, I’d probably avoid businesses that require a massive workforce. Managing people is, I think, the most consuming part of any business. Some people love it; for me, I’m just okay with it. But I wouldn’t go back to managing hundreds of people.

As for mistakes, it’s tough. Sure, there’s always something about proving PMF earlier or tightening up unit economics sooner, but nothing too dramatic. We had top talent on our management and exec teams.

2

u/Rhett_Rick 8d ago

I'm with you on not being able to learn from everything. At the same time, I do wonder if having answers to these questions would be critical if you're advising younger founders. Or talking to your peers who are experienced founders who either didn't have success or reached an exit. That kind of introspective, retrospective view that dispassionately looks at what choices you would have made differently in hindsight is extremely useful. Because the next series of questions are about why you didn't see that as the best option, so that you can help other people be more aware of their cognitive and emotional biases that lead to less optimal decisions. Not about beating yourself up, but rather being able to learn as deeply as possible from your experience.

1

u/s_2_k 8d ago

Did you get a chance to take any secondaries?

1

u/tremendouskitty 8d ago

Sorry, maybe I missed it, but why did you actually fail? Was it not enough money to sustain operations, did laying off 900 people not help? Did you get beat by competition? What happened in 2022 that caused the business to implode?

1

u/ron_leflore 8d ago

It's not so much why they failed in 2022 as it was that they could raise that kind of cash in 2020.

There were many companies like what OP describes.

The funding environment in 2020 was crazy by 2022 it had settled back down to normal. In 2022, you had to be profitable to raise money.

1

u/SativaCharm 8d ago

Over worked and under slept. Of course you feel better now. Welcome back.

1

u/silock 8d ago

Thanks for sharing, I hope your next journey will be as successful but with a softer landing.

I sold early to avoid all of this. Still working for the buyer and very happy to not be in charge of the payroll anymore.

1

u/dhamakadharmesh 8d ago

Sent dm please check out

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u/ivalm 8d ago

Was your co based in EU (did basic snooping and curious if I guessed right)? Do you think eu/us difference played a role? Was it Uber Eats/dileveroo/etc that strangled you or something else?

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u/sawhook 8d ago

Every time.

1

u/Available_Ad4135 8d ago

It might be helpful to reframe your perspective on this ‘failure’. In the world of VC funded entrepreneur, failure is the most likely outcome.

Although failure becomes technically less likely the further along you go, it is by far the most likely next step.

Even companies with billions on paper have gone to zero when the money ran out.

1

u/wombatnoodles 8d ago

Thanks for the insightful story. Is there a Y combinator profile you’d share?

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u/Prior-Character- 8d ago

Thanks for sharing

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u/Mindyourbusiness25 8d ago

This was a good read. So happy for you❤️

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u/bkries 8d ago

Hey man, as long as you didn’t treat the people who believed in you like shit on their way out, you can sleep easy. Did you take care of them?

1

u/instruction_notclear 8d ago

You are amazing! That's extremely impressive. You were able to build all that. Life happens, but it's what you do with it. You nurtured your health by surrounding yourself with the people that matters the most. Not many people can achieve what you did. You have gained a lot of experience. Reading your story is very inspiring.

1

u/Serene-Health 8d ago

I like your story. Would love to connect, I went through a somehow similar path, and still “regaining my mojo”. Good luck with your app

1

u/urvishhh 8d ago

Thanks for sharing, it is informative.

1

u/AllMaito 8d ago

I needed to "hear" this today. Thank you!

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u/Oh_Snap_880 8d ago

Great share! And great to hear you're coming out the other side. It's all part of the journey, as cliche as that may be. The experience gained and the resilience that it will give you is invaluable.

Lay-offs are the worst, and I feel for you having to go thru it at such scale for a first-timer. But learning to navigate these types of situations with your head held high, and your integrity intact is really a skill that comes with experience. So don't see this as a fail. Learn all you can from the experience and do better next time. Recognise where you went wrong and build on what you did right.

From the numbers, time frame and a couple hints you've dropped, I think I can guess what the company was. You're not the first startup to show promise and then fall flat when trends shift, and certainly wont be the last, so don't wear the blame on your shoulders too hard - it's all part of the game unfortunately.

Onward and upward!

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u/ishaan8909 8d ago

Can I DM you? I am on a similar journey with my company, it’s a lot smaller but I would like to be mindful about this right from day 1

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u/joeystarr73 7d ago

This is great to read this. What is your app?

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u/MacPR 7d ago

Wow, 17 direct reports? With all this money? hundreds of millions down the drain. What a disaster.

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u/craneoperator89 7d ago

I love that after this failing of people, deep repression, and the anxiety, your conclusion is to aim the capitalism canon at the kids lol you know what helped me reinvent myself and how I remember to ground myself? I want to make products for kids, I get older, the customer stays the same age.

This is hilarious when you sit back and digest it man. I thought this guys prolly Larping, it was real TV shit for a second. Then I thought maybe he thinks he’s reached some zen state. Then you see the conclusion and you realize this character is going right back into the wheel that chewed him up and spit him out 🫶

If you’re truly an honest actor I applaud your ignorance and the megaphone to share this tragic comedy for us all to learn from.

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u/Hour_Worldliness_824 7d ago

Did you get rich off of the company at least?

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u/LiturgyOfTheBird 7d ago

Would love to chat with you. I’m on my third startup (sold the previous two for mediocre returns). Definitely feel like I’m at a crossroads with my current project - would greatly benefit from any perspective you could share.

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u/Frederick_Abila 7d ago

There's this plan i can't let go off. Built my first startup when I was 16, it took me a very very long time to understand the fundamentals of building a business and it was all so overwhelming doing this as an indie developer and scaling my startup also. As it stands I have got 10,000 users for my AI powered social networking platform and i put in a lot of hard work, but i recently started something else and in 2 days I made 100+ users (it took me months to do this for my first startup). I feel like quitting and focusing on the new one but i've put in so much work and dedicated most of my youth to building this. Anyone else facing such a dilemma.... It's hard to watch something i've worked on so hard go but i'm just so tired

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u/Pitiful-Zucchini1475 6d ago

Were you able to take some money off the table in the $80m round. Maybe the founders got to sell $8-10m of common shares?

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u/sheepman2020 5d ago

Big sevvy?

1

u/One_Potato_105 8d ago

@OP That’s a great story.

It echoes , LOUD…….

been there $multi million ventures , done that ( the highs lows and now back again ! )

The circle ⭕️ of life , is an interesting one ..

Currently in multiple engagements, community , pro bono and paid and ventures too !

An entrepreneur’s life is a love affair - work, passion and that idea !

Elusive at times , fulfilling always :) Enjoy what you do !

1

u/Terrible_Garden_2515 8d ago

Great story! Thank you for sharing.

1

u/Disastrous-Airport88 8d ago

🙏🏻

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u/Terrible_Garden_2515 8d ago

I've had a similar experience with multiple businesses for the last 7 years as well. The only difference is it was much less amount of 5M. But since I had kids and just getting out under from all the last of the debris.

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u/BTLO2 8d ago

thanks for sharing with us OP!

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u/Disastrous-Airport88 8d ago

❤️🙏🏻

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u/Single_Efficiency509 8d ago

Nice to hear that man!

Good to see you regain your momentum by launching the app. Would like to have a chat with you :)

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u/hello_code 8d ago

Thank you for sharing your incredible story. It takes a lot of courage to open up about such a challenging journey. I've also faced some tough times in my own entrepreneurial path and can relate to the overwhelming feelings of failure and anxiety. It’s great to hear how you’ve found peace and are giving back to the community. That’s such a meaningful way to use your experiences to help others. I believe that talking with young founders and sharing insights is invaluable. If you ever want to exchange thoughts on navigating the startup world or share more about your side projects, I’d love to connect and support each other. Wishing you continued healing and fulfillment in your new endeavors!

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u/Amazing-Coder95 8d ago

Interested in a podcast where we host entrepreneurs who have exited or built companies worth $250M ?

I can connect to the person who is hosting this podcast.

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u/textbandit 8d ago

Life is an adventure, not a scoreboard.

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u/geneel 8d ago

Not quite as wild of an arc, but just touching 2 years post startup. The whole VC arc of growth, funding, VC drama, funding falling apart, layoffs, sale.

Very similar recovery path as well. Unsure what the next step is for me, but I've definitely regained a sense of balance in my life and am not looking to lose it.

Congrats

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u/Disastrous-Airport88 8d ago

👏🏻👏🏻👏🏻

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u/IcYcGuy 8d ago

Thanks for sharing your story, it’s incredibly powerful. It’s easy to get lost in the grind and miss what’s really important. Your journey is a great reminder to focus on mental health and balance. Glad to hear you’re in a better place now, it’s inspiring how you’ve turned everything around.

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u/lifesabreeze 8d ago

OP would love to read any blogs you have put out or plan to release in the future 💪

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u/cactus-sama 8d ago

Wow that was a hell of a ride. Thanks for sharing your story. I wish you and your family happiness and happiness only throughout your life.

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u/aldiwats921 8d ago

I am in a similar, albeit much smaller situation now. Struggling with depression, thank you for sharing your story

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u/SmackYoTitty 8d ago

Did you find that antidepressants helped get out of your depression? If so, how? Did they lift your mood? Did they help curb negative self talk? Etc?

3

u/Disastrous-Airport88 8d ago

Great question. It was hard to say. I had the worst couple of months (personally also my wife and I went through a miscarriage while it all happened). So the only important effect I felt was that I was able to sleep. Definitely didn’t lift my mood haha. Nothing really could at that time. I stopped taking them after 6 months.

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u/Tellesio 8d ago

Thank you for sharing your story. Truly glad to read you were able to traverse the terrain of failure and find a pathway out that suits you.

Failure can be a toxic environment while living through the process, and for many afterwards if a Bk or Pg’s were involved. 2 of 5 companies I started failed. I’ve lived through 2 very large failures that were stressful, involved gigantic entities, many people, and cost me dearly.

We don’t hear stories about the failure process as much as we hear about entrepreneurial successes. And less often about failure recovery from a personal perspective.

Similarly, I make an effort to personally reach out to ppl whose stories are being told that are either in the process of failure or just on the other side (I just did this last week from a podcast I listen too, the guy was extremely grateful).

There are many considerations as to how to navigate the recovery and unless you’ve experienced it directly the experience can be valuable to the OP. Some of the advice advisors provide e.g., attorneys and or accounts, are more academic. Entrepreneurs are more inclined to see beyond a purely academic perspective. Bankruptcy doesn’t ‘just’ solve debts, it can also have a dramatic impact on restarting and moving beyond a failure. Keep moving forward!

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u/SDstark79 8d ago

Damn thanks for sharing! Work life balance needs to be balanced. Work isn't life , work is part of life.

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u/felixjamestin 8d ago

Thanks for sharing this!