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Ask HN: A 31yr old's dilemma

5 points by process-exit 8y ago

Hi HN, First, some background. I'm 31, technical, and working at a Prestigious Tech Company (PTC). Live in NYC. An engineer most of my career, and in the last few years, some BD too. I've started companies before : once when I was 24 (solo) and once when I was 27 (cofounder). Both profitable, and the latter growing fast w/ a recently closed series B. I left that company very early because of a life tragedy, but have regretted it ever since. Last ~4 years at Prestigious Tech Company (PTC) have been mixed. Great to have stability, to travel and to work with smart people. But near impossible to get truly motivated. For much of the past year I've been quietly building, and have a new MVP that I have very strong conviction in. Felt motivated again. Believe the business is decently validated via talking to and onboarding some early users. I'd like to raise some funding and run with this, BUT: a) PTC may IPO in ~2020 which makes staying almost certainly the safer financial decision. b) The 'society' at PTC is awesome. Having a place to go / big group of smart and ethical people to hang out with. I recall some of the loneliness/unhappiness of my first solo business. c) Most importantly: I don't have a non-technical cofounder. I'm under-networked. Used to see that as a positive attribute (ha) - now it's just frustrating. Despite being mildly tech-twitter-famous I don't have many real connections w/ cofounder types in my life. Worried that when it comes to raise my inability to have attracted a cofounder will be a negative signal. Founding with a relative stranger may also be a relatively negative signal / bad idea. HN: What would you do in my shoes? Is my failure to have built this network over the years a sign that I shouldn't pursue this? At 31, am I past-the-post to some extent? PS: Since I'm seeking a cofounder - if you'd like to learn more, please reach me at fathomsdeep@protonmail.com

emddudley 8y ago
Only on HN... Can I be honest with you? This reads like a humble brag. You're already very successful. No one here can make this decision for you. You sound like a capable person that is over thinking things. Assess your risk tolerance and trust your gut.
- process-exit 8y ago
  I can see how I've given you that impression, but why would I create an anonymous throw-away account to humbly brag? If there's any ulterior motive here, it's cofounder sourcing.
epc 8y ago
Go to NYTM and maybe other meetups in your "space"…there's always people looking to get in on the ground floor on something. See if you can found a company while working for PTC without compromising your job/equity in PTC (hire one or more kids to do the day to day grunt work operating your MVP).
- process-exit 8y ago
  That's a great idea.
outericky 8y ago
31 is still very young. We started at 36 and that was still young. Plenty of time. That said, if it's truly 2020, then i'd say wait for the IPO. Some financial security will make it much easier to jump and do your thing later. If money isn't a concern now, then go for it. Counter point, the market is looking to become more unstable and there is a good chance 2020 IPO won't happen, so raising funding now might be your best and get after your own thing. Hopefully you've vested something at PTC so you have something to gain in the IPO.
- process-exit 8y ago
  Thanks and I appreciate the balanced view there. Congrats on launching something at 36 as well!
mindcrime 8y ago
At 31, am I past-the-post to some extent? ROFLMFAO. No, you have barely even made it to the starting line. Do whatever you think best, but don't use age as an excuse one way or the other. You're not too old, you're not too young, you're just you. Wherever you are, start there. Regarding the PTC and the IPO... ask yourself how confident you are that they are really going to IPO. It's not unheard of for companies to use the carrot of a pending IPO - that somehow, mysteriously, is always "just a few more months" away - to keep employees from jumping ship. This works right up to the point that they admit they're broke and lay everybody off... And even if the IPO happens in 2020, make sure you understand just how much you stand to benefit. Of course you can't predict exactly what price the stock would open at, but you can probably use historical data to get a ballpark idea. Figure out how much stock you own, or have options on, how much purchasing any options would cost, etc., and see if there are weird provisions around vesting / selling your stock, that would lock you in there for X more years, etc., etc. All of that should factor in to deciding if staying at PTC is really in your best interest or not.
- process-exit 8y ago
  Thank you!

5 points by process-exit 8y ago

emddudley 8y ago

Only on HN... Can I be honest with you? This reads like a humble brag. You're already very successful. No one here can make this decision for you. You sound like a capable person that is over thinking things. Assess your risk tolerance and trust your gut.

process-exit 8y ago
I can see how I've given you that impression, but why would I create an anonymous throw-away account to humbly brag? If there's any ulterior motive here, it's cofounder sourcing.

epc 8y ago

Go to NYTM and maybe other meetups in your "space"…there's always people looking to get in on the ground floor on something. See if you can found a company while working for PTC without compromising your job/equity in PTC (hire one or more kids to do the day to day grunt work operating your MVP).

process-exit 8y ago
That's a great idea.

outericky 8y ago

31 is still very young. We started at 36 and that was still young. Plenty of time. That said, if it's truly 2020, then i'd say wait for the IPO. Some financial security will make it much easier to jump and do your thing later. If money isn't a concern now, then go for it. Counter point, the market is looking to become more unstable and there is a good chance 2020 IPO won't happen, so raising funding now might be your best and get after your own thing. Hopefully you've vested something at PTC so you have something to gain in the IPO.

process-exit 8y ago
Thanks and I appreciate the balanced view there. Congrats on launching something at 36 as well!

mindcrime 8y ago

At 31, am I past-the-post to some extent? ROFLMFAO. No, you have barely even made it to the starting line. Do whatever you think best, but don't use age as an excuse one way or the other. You're not too old, you're not too young, you're just you. Wherever you are, start there. Regarding the PTC and the IPO... ask yourself how confident you are that they are really going to IPO. It's not unheard of for companies to use the carrot of a pending IPO - that somehow, mysteriously, is always "just a few more months" away - to keep employees from jumping ship. This works right up to the point that they admit they're broke and lay everybody off... And even if the IPO happens in 2020, make sure you understand just how much you stand to benefit. Of course you can't predict exactly what price the stock would open at, but you can probably use historical data to get a ballpark idea. Figure out how much stock you own, or have options on, how much purchasing any options would cost, etc., and see if there are weird provisions around vesting / selling your stock, that would lock you in there for X more years, etc., etc. All of that should factor in to deciding if staying at PTC is really in your best interest or not.

process-exit 8y ago
Thank you!