Should I Enter the Startup World?

A cousin of mine, who is a smart, well-accomplished, corporate lawyer at the top of his field asked me a question two days ago. Well, really a bunch of inquiries, but each was an input to his fundamental question: should I quit my job and found a start-up. He has a well-researched idea, potential backers, in a hot area, and in his area of expertise and passion.  Should he do it? Now? Should he find a technical co-founder? 

We're set to have a deeper conversation in the next few days. But here are five minutes worth of notes I sent him that reflect my own experience. I'd be interested if others who ventured into the magical world of start-ups feel the same:

1. I wish I had not gone it alone. Get a co-founder. Bunch of reasons behind this, but its really important.

2. I have not found a "right answer" or financial equation on whether to quit what you are doing or go do a start-up. It's like love or eating at White Castle. Makes no sense, you just get it. 

3. Notwithstanding the foregoing (remember, my cousin is a lawyer) be very careful to weigh all the risks and constraints of each decision. I thought about: How will I feel around change in income? Around any impact on my home life, retirement savings. Little things like "can we still afford get baby sitters whenever we want", or "if I want, can I still buy  a new completely unnecessary road bike." And:  how long can I continue to do all this without income? This helped me immensely. 

4. I wish I had taken time to build out my idea while I still had a job. Not just because of the income and safety of being able to think before you jump, but the minute you start building a start-up, people (investors, etc) will look at how long it takes to take off. Getting a head start in secret is awesome, if you can do it.

5. However hard you think the start-up will be, it will take more money and time than you think. People told me this, too. I thought: "bullshit, not me." Yes, you.  Your idea won't work, I promise. At least, not the way you think it will. If you are lucky, the next iteration or pivot will work better, but it will maybe the next one or the next one. Interesting fact: VC's don't bet on the details, they bet on the team, and the space. Because they know that the first iteration will not likely work, and they want a team that will figure it out, and do it quickly.

6. Nothing is a one way door.  This was important to me, and gave me the strength to take the plunge. You can always have a plan "B". I did. Of course, I also wonder: if an entrepreneur treats his or her decision to start a company as a one way door, perhaps they will fight harder. Fight to the death for their start-up. Fight longer than I did. 

7. My experience in founding a startup is that it has been a hugely rewarding experience.  Of course, not as rewarding as if my startup was successful, but the experience over 1.5 years is something I have brought with me to my current role and I'm sure I will draw on in the future.  I may have regrets over decisions I made along the way, but the decision to found a start-up is not one of them, by a long shot. 

8. When I made my decision to found a start-up, I had my table limit set. Mine was 18 months to get to velocity to raise an institutional round. I think it's important to be true to whatever your limit is.   But also make sure it is a reasonable limit given your idea (I made several mistakes in my start-up, but not getting this last one right was my biggest, I think).

9. I found that start-up advice is like going into 31 Flavors. Get some tastes, and pick the one that is right for you at the right time. If you try to take all of it, your systems will fail and you will shit yourself.  (Insert rocky road pun here.)

~fin~