Getting Ready for the Next Life Chapter

Since selling Burner Rocket, I’ve been working on finding the Next Great Move. This could include starting another company, joining another early-stage startup, or go somewhere where I can make good money – save and pursue my own company later with seed funds. However, now, I’ll need to consider a big next phase in my life – marriage.

My last post was supposed to go out on Wednesday per usual, but instead, was published on Saturday – three days later. Why? Because I was proposing to my then-girlfriend on Wednesday up in New Hampshire in the snow. (!!!) Yup! I’m going to have to edit my timeline soon.

In any case, I’m looking at three primary categories for what I do next:

• Start another company. Pros: this is what I want to do. It’s what makes me the most excited. Cons: I do not have any clear interest in any one idea. Also, the SaaS market is highly saturated in marketing and sales, where I’ve spent my last two years. There is no clear wages here. (Danger given my upcoming nuptials and next-life-phase pieces like kids and new home.)
• Join an early-stage company. Pros: continue to down the entrepreneurial path with some exit potential. Able to be a part of an early leadership crew to grow a company. Build something great from nothing/ little. If funded, can mitigate wage concerns. Cons: I would not be the entrepreneur, only entrepreneurial. How much of wage concerns can be mitigated? Will there be an ownership stake that enables some financial freedom upon a potential exit? Product-market fit may not be achieved and depending on leadership, leading the company to this point can take a long time… or never.
• Join an organization that pays extremely well with learning upside. Pros: Can build up a cash stash to seed a future-startup. Will have less of the emotional roller coaster and be more even in stress-levels, likely. Can learn and network with vast resources and backing. Cons: Less entrepreneurial, if at all. Could be tied to golden handcuffs and never return to startups.

The point is to pursue one of these options early into 2019. Till then, I’ll continue filling my time with some consulting work to keep my mind sharp while learning and networking.

If you were taking a dive into another phase of your life, how are you evaluating your options? Why would you lean one way more than the other? What risks are you taking on?