Really tough question because I am still finding out the answer myself.
A lot happened in two years.
A couple of observations though:
- I spent 1.5 years after jumping ship exploring different audiences and problems i could solve. It might help if you have a rough idea before you jump ship because you're burning time and cash.
- Do plan for things going wrong. In these 1.5-2 years I had opportunities and partnerships. Some of these were with people I have worked with before and I thought we had really good synergy back then. Most went sideways and put me in a financial position worse than when I initially started. So plan for this eventuality but don't adopt a pessimistic outlook.
- Marketing is a huge part of the journey. I discovered that the hard way. I overestimated my PR and network which was too niche and wasn't as beneficial as I thought in my new focus area. As a 41 year old with 15+ years in consulting and , I found myself having to reintroduce myself to a market that knew nothing about me and I was as good as the guy who just graduated or spent only 1 year at a big brand firm. You don't survive on marketing alone but it's the number one driver of value perception.
- If you're under pressure, you'll make emotionally charged decisions and your emotions might blind your ability to reason through a decision. In general, the more pressure you're under when you're making the decision, the more you should increase your financial runway. So if in normal circumstances you'd make sure you had 12-16 months of runway, multiply that by a factor that represents the additional risk.
Do a personal cost benefit analysis or SWOT analysis. How does it look like? Is your tenure at Apple a + for your future network and vertical? is marketing the forte of one of your partners? What if things go wrong and the partnership breaks? Do you have enough financial runway? What if you burn too much cash too fast? Is there a side kick you can rely on to make extra money if you have to?
In no way is this comprehensive and I am still figuring things out.
Definitely made mistakes on the way but It's not always this bad. I started with a very disadvantaged position. I jumped ship because we lived through a local financial crisis as well. People took advantage of that. Make sure you have leverage on the negotiating table.
Hope it helps