Seeking Advice: Startup Failed, Finances Ruined, Feeling Lost

@real_mayonnaise MSFT Renamed their PMs Product Managers like a year and a half ago because ppl were incredibly salty about the name inconsistency (and their friends making fun of them for being project managers).

Source: Ex-msft PM.
 
@cindie This Learn Hub has info about becoming a Product Manager. I know that PMs are being promoted to the C-suite more and more.

Good luck, OP. I've quit many things in my life, but always take important lessons away.

As a side note, I've written funding pitch decks for startups before. Have you considered another push for raising funds?
 
@cindie This is really a philosophy question, not a business one. You sound a lot like me when I was 25 though

Just washed out of my first business and didn’t know what to do with my life. I remember feeling so frustrated that I couldn’t make things work. On top of that, I had a stupid amount of debt that I ended up going bankrupt on.

Going through this at 25 is rough because it’s not about just the business failing, it’s the identity crisis that comes with it.

Personally, I spent a lot of time reflecting on what I actually wanted my life to look like. From there, instead of picking up the pieces I started rebuilding from the ground up from shit I loved. I started learning a new language, got better at programming, went back to school because it excited me, put more effort into my relationships and got engaged…

Start focusing on the journey again and forget about the destination. What can you do today that will set your soul on fire? Call up old friends you’ve been missing while you were grinding. Pick up a hobby. Go to work at Starbucks for a month or two to remember how much of a joke work used to be. For the next month or two your only concern should be how you make life something you’re excited about living again.

Don’t stress - everything is temporary and this too shall pass.
 
@flipflops82 Thank you for this comment. It resonates deeply with me, especially the identity crisis part. Everyone knows me as “the startup founder” and a large part of my depression about this is the embarrassment of losing that identity.

I really love “start focusing on the journey again and forget the destination.” I’ve been so focused on trying to see the bigger picture (and failing to do so) that the smaller picture is getting lost. My day-to-day, my hobbies I’ve dropped, etc.

Thank you for this comment. I appreciate it more than I can put into words.
 
@cindie People say life is short, but life is long. Very long. Just focus on living it such that you don’t want to kill yourself every day. And be kind to yourself. If your best friend was going through this you’d be kind and supportive to them - so do that kindness yourself too.

Chin up. Once you get through this not only will you be more experienced than your peers, you’ll be wiser too. I got faith in you.
 
@cindie I’ve been there. Many failed startups. Lost money. Lost life. I’ve also been on the other extreme and helped build 2 unicorns, scaled teams from 5 of us to 1000 people and made every single mistake in the book along the way. Bad engineering decisions. Bad leadership decisions. Bad Hiring Decisions. All mixed in with raising over $400MM across 2 companies.

Here’s my advice: look for your good points. I actually feel like I learned the most from the failed startups that I had. We really had to push hard. We tried out countless things. Success is weird. Sometimes you don’t even know precisely why you’re seeing success. Imposter syndrome becomes a real challenge. Whether failing or succeeding, I learned to start journaling my thoughts. Not complaining. Not running through intellectual puzzles. I started analyzing and encouraging myself. I wasn’t writing for anyone else. In fact, I would open a file in Vim, journal for 5 minutes at a times between meetings to collect my thoughts and then I’d erase the file and leave it blank for the next session. It has evolved over the years. Now, I go for an hour walk each night and talk to myself, to the universe, to the void - like I was talking to my best friend. I’m in the middle of getting my next venture off of the ground. Despite a higher net worth than 99.99999% of people in the world, no debt, nice cars, a nice house and healthy family, I still struggle immensely with impostor syndrome. I still have to talk to myself every night on my walk to not get overwhelmed with all of the moving pieces and doubt.

You are young, you’ve got an incredible amount of learning - anyone who has tried to start a company has immensely more experience than even some very senior leaders in large companies who have never dared stepping out on their own and taking a risk. Creativity is the loftiest of human ambitions and also the most difficult. There is no dishonor in going to get a job and building up saving. Go find a job with a Series A startup who is growing fast. I did after a startup failed and we turned it into a multi-billion dollar company. Because I had already tried starting my own companies, I had a lot of scar tissue. I was able to have a profound impact on the team and ended up leading the entire tech organization as we scaled the company up.

The future is going to be defined by people who have started taking the risk to be creative and step out of the crowd to try to build something. You are part of that crowd. You’ve inevitably already faced challenges that few people can even imagine and you’re still alive!! And, you built a foundation of experience for yourself that gives you a perspective that can be a super power for the future.

Trust me, today feels very long but in another 10 years you’ll look back and feel like it flew by. Go find a fast growing rocket ship and reap the benefits of a good salary and the experience of scaling up a company and build a financial and experiential foundation for your next venture, if that is what you decide to do.
 
@richboat Wow. Thank you tremendously for sharing your journey, it’s inspiring to hear how the downs positively contributed to the ups. I deeply appreciate the encouraging and kind words too. It’s hard giving myself credit for the accomplishments since things didn’t end up quite how we planned, but putting it all into perspective really helps me realize how incredible it is that we made it as far as we did while doing great things along the way.

I love the idea of finding a medium for getting those thoughts out, so thank you for the brainstorming on that. I’ll have to tinker with journaling or just talking to the void. So many thoughts flood my mind so I imagine getting them out one way or another would be very beneficial.

I’ve been looking to get back into corporate, but a chunk of my network has been echoing that sentiment for me to look at joining a Series A/B startup since they’ll much better understand how valuable my knowledge is as a founder with a good salary to match. Definitely going to do more research on A’s that are hiring.

Best of luck on your next venture, and thank you for this comment. I really appreciate it.
 
@cindie Also, credit card debt is better than being homeless. Only use it if absolutely necessary, but make sure you have sufficient available credit to get you through many months of unemployment or lower-paid employment. The time to seek credit is well before you actually need it, not when you're suddenly out of cash.
 
@cindie Impressive progress, my friend! At 25, you've demonstrated remarkable determination and effort. Comparatively, at your age, I was still navigating the waters of uncertainty, a bit of a mummy daddy boy. With a decade on you, it's clear you're leaps and bounds ahead. Life is a journey of highs and lows, and it's crucial to focus on sustaining those highs without dwelling on the past lows.

You've got a substantial runway ahead to carve out the best version of your life. Should you need any assistance, please don't hesitate to reach out. As a FAANG software engineer, I'm more than willing to lend a hand, helping you navigate the ever-evolving landscape of technology and tools. The best is yet to come, and I'm here to support your journey forward.
 
@wolfdylan I really appreciate it, thank you tons for the kind words and advice.

I tell people all the time that I truly miss programming. My CTO is a legitimate genius in Python and every time he shows me code, I always say “holy shit I wish I knew how to do that.” and really regret that I stopped doing it.

I suck at self-learning i.e YouTube tuts, online sources, etc, in terms of learning fundamentals. Once I learned Python and JS fundamentals in the classroom, I was then able to take off running on my own. It’s all evolved so much that it feels overwhelming to start back up essentially from scratch though. Any tips on how to get back into it would be very much appreciated :)
 
@cindie There is nothing wrong with taking a knee and making sure you have a roof over your head. Remember maslows hierarchy of needs? Try to get any job you can ASAP and wait for inspiration to hit again. I’m sure there’s a few things you’d do different, so keep that in mind when you start anew
 
@cindie You've embarked on a new entrepreneurial journey. Embrace the challenges, knowing that this phase, like everything else, is transient. Persevere, keep progressing, and fearlessly navigate your path. Don't hesitate to simply be present in the moment; adapt to the circumstances. Taking a moment to gain some humility.
 
@cindie I felt like this for a bit. Had a startup, failed. Went to big tech. Life is wayyyy easier here; with that said, now looking to get back into small business stuff.Getting a job, although it feels shitty, can help you recuperate, put some cash in your pocket, and get you ready for the next thing if you so choose.

What sort of work do you want to do? Can you share resume?
 
@tubescreamer Spot on. We’ve been running an AI x Game Dev startup. The game dev space is very turbulent with awful job security so I think I’ll pivot out of games industry, but I really enjoyed Automation in my IT job out of college. I was essentially an automation analyst who found ways to automate processes within the organization (I worked within IT org of a large power manufacturing company.) Very fulfilling and fun work overall, so looking for something similar or adjacent. Could share resume once I update it - it’s been awhile
 
@cindie
haven’t gained any on-paper skills

lol you're 25 and ran a start-up for 2 years and you don't have any marketable skills? You and I both know that's false.

The video games and porn aren't going to make the pain go away. Take the advice of "fail faster" to heart. Go spend a few days looking at start-ups that are hiring c-level roles. Go talk to them, let them know you're looking for a new project to get involved with, understand their businesses, ask them what other projects they know about that are starting up, and find one you can get involved with.

No one hits it big on their first time out. You "fail faster" to push through the line of shit so you can get to the successful idea quicker.

Good luck.
 
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