The super honest questions of a startup founder and father of two

2015 was a crazy year: I left my cushy VC career and started spending all my life savings on building an uncertain product. I was living in a cramped downtown apartment with a baby who took over our one bedroom.

So there I was, sleeping on the floor of my living room every night with a 30-pound boot protecting my torn Achilles, barely getting five hours of sleep, hobbling between VC meetings, and trying to pitch my dream.

Just when I thought this crazy tale was going to be my defining startup story, the plot thickened. I eventually healed my way out of the boot, we moved to a bigger apartment uptown, and even raised the capital for Bizly, my startup. I was heading into the Christmas season with lots to be thankful for and feeling hopeful that the coast was clear to just focus on my startup and crush it through 2016.

That’s when my wife told me to check my Christmas stocking.

I reached in. I thought maybe it was a new watch, perhaps a cool gadget, or even a snack. Alas, it was a pregnancy test.

I saw one line (i.e., not pregnant), looked at my wife, and starting laughing, “Good one, babe.”

“No, look again.”

Faint as can be, there it was, the second line. Another baby.

Fast forward about seven months later, there I was, back in great shape after my Achilles recovery, getting some decent sleep, and polishing off a shiny new web app for Bizly to release to the world. With our son not due for another three weeks, I thought that was plenty of time to get everything sorted out.

But there were other plans for us. Sebastian was born six days after our launch. His birth was easy and blissful. It was a beautiful weekend. But I was back to work on Monday. Damn.

It’s now been about three months since he came around, and our daughter Kavi is now two and a half and starting school.

I still don’t have answers. I’m writing this article because I have questions. Lots and lots of questions. So here go the big ones:

1. How do you work out?

Let’s face it, I’m about four short of a six-pack; I am fighting for my dear life against “dad bod.” Between dropping my daughter to school in the mornings and rushing home to help for bedtime, how the hell do you work out? The daytime workout and shower is like an hour and twenty minutes, and you come back sweaty.

2. Sleep hacking?

3. Throwing shade

4. Dolla’, dolla’, bill ya’ll

5. Happy wife, happy life