So far it has been challenging to find time and energy to explore ideas and do costumer development after 10 hours at work and spending a couple of hours with family.
Thank you for sharing your story! Have a couple of questions, if you don’t mind sharing a bit more:
1. How are you supporting yourself financially? Are you consulting or living off you savings?
2. Based on your friend’s story, do you have any tips on what not to do when trying to moonlight?
1. I am primarily living off my savings. However, I haven’t had to sell any investments for expenses during this period and they have likely grown ( as per Mint.com ) I don’t actively track my investments ( I have vested stock from the fruit company + use robo investing ) so I am mentally free to enjoy other things without worrying about market volatility … I think my average monthly expense ranges from $1500 - $2500 depending on the country. A lot cheaper than a Bay Area down payment + plus so much time to do anything. Also unmarried and no kids.
2. My friend ( at Fruit Inc ) was working with a undergrad friend from the East coast on a side project. The other friend posted a Craigslist ad needing help on the project and mentioned my friends credentials on the posting. Somehow a recruiter found out about it and so my friends VP called him … that he can’t do so and so, and that the fruit company owes everything and he needs to turn it all to them, and he can be terminated etc. And even after termination they will come after him. Long story short, he stopped working on the project and he was NOT terminated but he did eventually leave to a different company. (For context: the project my friend was moonlighting on was not some cutting edge secret or some hard problem )
Bottom line: If no one knows about your project you are fine. And if you decide to leave the company and work on your idea … might make sense to ensure that the start date of the code etc looks a little after your resignation.
If you remember Flipboard, Evan Doll was in the iOS team and also taught the CS183 at Stanford. As per his LinkedIn as soon as he left, the same month he cofounded Flipboard although the app was released 1 year later.
I have a few coworkers from my team that cofounded companies and they too have 1-2 month gap after they quit and they all got funding :)
I don’t think the policy changed as per se. It’s just they found proof of him trying to hire a part time help.
I had a co-worker around 2013 ish who just wanted to blog and put personal projects code to GitHub. It was not recommended and needed VP permission … basically a hassle.
Thank you for sharing this! Appreciate your advice.
Even though AI is hot, I think, raising a 2M+ seed round in the current market still requires having a prototype and some paying customers (or LOI), especially for the first time founders.
At the end of the day, the goal is to build a strong business so your earlier point about having a clear vision of the initial product before jumping ship makes sense.
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.
