Can’t Objectively Tell Whether to Push Forward or End Things.

2x entrepreneur.

First venture = small. Good learning experience. Bootstrapped. About broke even. Wound it down but not a big deal. Only myself involved. No other co-founders

Second (current venture). Brought on a junior co-founder. Decided to raise money + build team, but wanted to bootstrap for a bit of time to get traction and help with the fundraise. Hit huge initial traction (revenue) out of the gate and decided to delay fundraising b/c we could. Then everything went to hell.

• tons of production problems (stressful, but expected, so no biggie)
• a former contractor brought a lawsuit on the company. i thought / still think the lawsuit is BS, so decided to aggressively fight it hoping it would settle or go away quickly. but didn’t happen. well into the six-digits of cost now.
• decided to put fundraising on hold until the lawsuit was resolved. thought most investors would be scared off unless there was a clear path to resolution for the lawsuit.
• have also put team building on hold b/c wanted an end in sight to the lawsuit before really went down that path.
• junior co-founder is a great person, but just not the right fit. more of an employee than an equal.
• i haven’t been taking a salary for the benefit of the company. and just can’t do that anymore.

and yet, despite all that, still think there is a promising business here. we’re still selling product and customers are happy. just not sure if i have the energy to do it. i feel stressed, defeated, and like a failure. “how did i screw things up so much to get ot this point”. i am now on anti-depressants, and some days it’s hard to get out of bed. i have a wife and a new baby and i feel like a failure for not supporting in a responsible way.

for the business to be go forward:

• lawsuit has to be resolved
• need to replace junior co-founder and bring on a team quckly
• raise money
• stabilize a shaky supply chain and get things back on track.

i’m worried that I’m just too tired at this point, too stressed, too burnt out. I need a break. And I’m worried that even if I solved the first two problems above, I shouldn’t raise money unless I’m all-in…to do otherwise would be a huge mistake. and I’m not sure i’m “all-in” because of everything that happened.

And yet becuase there is still promise here, I think if I were to shut things down I’d be forever regretful and wouldn’t have enought grit. I think the investors i’ve spoken to in casual chats would view me as a failure and this would be my lsat realistic chance to start a company. I’m in my mid-30s now. I love doing this, but my wife doesn’t want this life anymore. and I can’t blame her. If this startup doesn’t work out, I’m not sure I would ge tthe chance to do another. and I’ scared i’d have no idea I would know what to do if i weren’t running a company.

i just want a do-over…but such is life.

how do i make a decision on what to do?