Two Babies and a Startup: What Now?

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 5 hours of sleep, hobbling between VC meetings, 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. 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 Bizly 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 7 months. 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 6 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 started 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.

With the startup at full throttle, it feels nearly impossible to get out during the day. If someone has hacked this, let me know what you did. Pushups between calls? Jog to meetings? I’ll try anything.

2. SLEEP HACKING?

He’s a smart dude and I like a lot of his stuff, but on this topic, I just want to slap Tim Ferriss across the face. Optimize yourself at 4.5 hours of sleep? My ass.

I don’t care if I inject peanut butter in my left cheek while taking a dropper full of poppy seed extract and an IV of nitrogenated coffee. Entrepreneurs need sleep to perform. And with two babies, I want to find some ways to sneak in some sleep to recover from broken nights.

I think for every hour less of sleep that I get, I have about 8–10% less creative power for Bizly. But this isn’t Google — no sleep pods in our office. Ideas?

3. THROWING SHADE.

Back when I had one baby, my single friends thought it was so cute. It was a novelty, like a cuddly mascot that can hang out on our lap while we continue to drink and have fun. Have two kids and they treat you like you’re on a different planet, a planet of slobbering apple sauce, shleppy sweats and nightmarish tantrum-filled days.

Shit, I guess they are kind of spot on with that. But my question was about socializing. Am I doomed to try to find a dude in my kid’s school to hang out with? Is this like a bad real-life re-enactment of “I Love You, Man”? Has anyone figured this out?

4. DOLLA’, DOLLA’, BILL YA’LL.

I raised a nice round of seed capital for Bizly. But to benefit my team and make sure we have all the resources we need to get to the finish line, I take a base salary that is lower than my first job when I was 22 years old.

I dip into my savings every month to cover my mortgage, my kid’s school and diapers, on top of the already depleted savings from my self-funding at the start of this venture.

Believing in something takes all of yourself. I’m all in. As is everyone on my team, all of whom have taken a salary pay cut in exchange for equity and following this dream. Has anyone had any success going at this in a different way?

5. HAPPY WIFE, HAPPY LIFE.

If you’re an entrepreneur, your spouse never sees you, doesn’t have much of an extra hand with kids and also doesn’t have spare dough to go enjoy alone time. When you are around, you are probably stressing over some stuff related to your startup. Now this is a broken equation. The alone vacation ain’t happening, not now at least. You gotta put the phone away, focus on your spouse and get the quality time in. This is all much easier said than done. Anyone have good ideas on this one?

There are a lot more questions, but I’ll stop here (for now). On the positive, nothing is more motivating than the glaring eyes of two hungry kids. I wake up every morning like I’m ready to tear through walls to get to my goals. While I have such a clear vision for where I see things headed with Bizly and our industry, I’m still fairly lost on everything else. Thank God for my wife. Would love your feedback on these questions.

I hear babies crying so much, now I actually hear “phantom crying” even when they are asleep.

On that note, why am I still here? I need to go to bed.

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