Hey all,

I have two options in front of me, and I'd love to hear the thoughts from the founder community here, particularly those who raised money from investors to run a high-growth startup.

Path 1 - I have sourced a small software business that is willing to sell to me. It's an old, legacy product that has been run as a lifestyle business by the current owner. He wants to retire (is late 60s) and he didn't think he could sell his business with such low revenue. Has about $900k in revenue across 350 customers in the b2b compliance space, so the product is a need-to-have. I have some investors who want to give me money to buy the company, rebuild the product into a modern solution, and pay for a year's worth of sales/marketing. This incredibly de-risks it for me, however, they want 55-60% of the equity and the expectation would be that I'd turn this into a high-growth startup (TAM is $9b+).

Path 2 - I have a technical master's from a Stanford/Harvard/Cal and am in the interview round up to be a PM at a startup with expected comp around $200-225k, which would be AWESOME.

Context:

I've done some entrepreneurial stuff before - cofounded a startup that is still running in SF (was a part of it when it was pre-revenue), helped my buddy file IP for novel technology and we were going to raise money to turn the IP into a product/company but an established brand wanted to license our IP so we took that route. I also bootstrapped a small eCommerce biz on the side and sold it (~5 figures). I've always been entrepreneurial.

Most recently, I was at a Fortune 1000 company doing PM work and really didn't like it. I didn't like the politics and impediments to execute, so I left earlier this year to look for a small business to buy.

However, I'm 33 y/o, < $500k NW, single, and really want to find someone to settle down with and have a family. This part really makes me want to stabilize my life.

So, I have an option to pursue the path I've always wanted (my own startup), but I also realize that I'm getting to the age where I need to start stacking skills and experience for a FAANG. I don't want to be 38 after a failed startup and be applying to individual contributor roles at a FAANG. I also think if I play it right with a role at FAANG or a few high growth startups, I should be in the position to retire early. And lastly, going the FAANG/employee route would stabilize my life and perhaps be more apt to find someone to settle down with.

Has anyone who been in a similar position? Looking for thoughts to help me think through this. Thanks All!