Y-Combinator, a Two-Year-Old, and a Pregnant Wife

April 2014 was a momentous month. My wife became pregnant with our second child. On top of that, my startup, Payable, was accepted into Y-Combinator (YC S14).

I was excited. And terrified.

Doing a startup with a two-year-old is already a tall order. YC would kick it up a notch. A pregnant wife in her first trimester would kick it up yet again.

How could I make it work? How could I lead our startup? How could I be a great dad? A great husband?

Well, I’m here to tell you that I did. And I didn’t.

No one’s perfect. But, a guy can try. Here are my lessons from running a startup, being a dad, and going through YC.

Figure Out What Can Be Less than 100%

You want to give 110% to your startup...and your kid. That’s untenable. The guilt will overwhelm you. You’ll let your child down and you’ll let your team down.

The key is to realize that not all things are urgent. Not all things are equally important. And, it’s ok to be less than 100% some of the time.

When I worked at Intuit, CEO Brad Smith often talked about how he handled this very dynamic with his two girls. He looked at it as a task of juggling rubber and glass balls. Rubber balls, if dropped, bounce back. It’s not the end of the world. Glass ones, if dropped, shatter and can’t be put back together again.

You need to figure out what’s rubber and what’s glass -- what you can miss and what you can’t.

You need to prioritize.

For my family, this meant daycare pickups and dinner. My wife works full-time in tech. She takes our daughter in the morning so I can catch the early Caltrain from the Peninsula into San Francisco. I make sure to commute back in time to pick up my daughter before daycare closes.

That makes dinner the one time of the day we’re all together. So, we make it a priority. The only exception was for YC’s Tuesday Night Dinners. The dinners were a key part of the YC experience. Thankfully, the times were known in advance and could be planned around.

For Payable, this meant stepping away from product to focus on growing the business. Product is what I love. It’s where I get my energy. But, the rest of the team had that covered. My efforts were best spent on support, sales, marketing, legal, business development, and strategy -- all things that would break (or be neglected) without my involvement.

Create Protected Spaces

I find the hardest part of being a startup dad is managing my own psyche. Left unchecked, every hour can feel like a decision of “who do I let down now?”

That’s not healthy. It doesn’t lead to great parenting. And, it doesn’t lead to great leadership.I’ve found creating “protected spaces” a useful technique. You need to give yourself permission to not be responsible.

From 5:30 pm-8:30 pm, I’m not a startup CEO. I’m a dad.

That’s when my family is together for playtime, dinner and bedtime, so I do my best to be present. Plus, who wants to miss playing with Legos? Err...Duplos. The point is: I’m not responding to customers and emailing team members.

By creating that space, I get the mental freedom to be attentive to family matters. I’ve given myself permission to not respond to whatever issues are happening to the startup. I don’t feel like I need to be “on.”

Sometimes I lapse, but the vast majority of the time the startup issues are perfectly fine waiting until the next morning.

I also create a protected space for the team.

Once a week, I do a “Long Day” where I stay late in San Francisco with the team. That means I’m not seeing the little one that night. But, that’s ok because I make sure I’m there the other 6 nights a week.

Be OK with Missing the Scene

The Silicon Valley Tech Scene is full of happy hours, meetups, and parties. In addition to being fun, they’re a key source of networking and relationship building.

As a parent, it’s very difficult to make them.

If I go to that happy hour from 6-8pm, that means I’m not home until 9pm. My daughter goes to sleep at 8pm. So, the happy hour quickly becomes a choice of “do I see my kid today?”

I skip those happy hours.

I’m ok with that. At this point, I’ve probably missed an advantageous connection or two. I’ve definitely traded nights out for nights in. But, I’ve been around for more of the “little things” in my daughter’s life.


I’ve neglected to mention the most critical player in getting startup parenting to work -- your spouse. I would fail both my startup and my daughter without my wife’s support. To make it work, we talk...a lot.

One level is logistical. Who’s taking her to daycare? Who’s picking up? Do we have enough diapers? Are we out of milk? Every day is like coordinating trains out of a station, but it needs to get done.

Need proof? Here’s the text I received while at the YC Demo Day After Party.

A kid’s gotta drink

Yup...the quintessential “did you remember the milk?” request. After a 16-hour day, the biggest speech of my life, and talking to Joe Montana, I got brought right back down to earth.

And yes, I got the milk. A gallon of 2%.

Another level is emotional. Startups are a rollercoaster. Parenting is even more so. You go from dealing with the crap that comes with running a company only to come home and literally deal with crap. That makes for a long day.

Having your spouse as a sounding board is critical. Sometimes to vent. Sometimes for perspective. You need to release all the worries, fears, and guilt you have. Otherwise, they fester.

But, it’s not a one-way street. You need to reciprocate. Just because you’re dealing with a full load doesn’t mean you get to cop out. Your spouse needs an outlet, too.

The same rule applies to your co-founders and employees. You can’t expect them to know how you’re feeling. You can’t expect them to understand. You need to overcommunicate. Tell them how you feel. Let them know that you didn’t sleep last night. Not as an excuse for anything, but so that they understand the context you’re operating in.

Keep Iterating

As with anything else important, you need to keep adjusting and evolving. Your startup will change and grow. Your kid will too. Tactics that used to work will cease to do so. Cost-per-Click goes up. Cribs get too small. You’ll need to adapt.

Here are a few examples of things my wife and I have tried that are (currently) working:

• Give each other “me time” on the weekends. Go off and not be responsible for anyone but yourself for a little while. Find a way to disconnect.

• Get a babysitter. Time as a couple is even more important.

• Put car seats in both cars (if you both drive to work). That way the other spouse can pickup if something unexpected happens.

I’ll keep iterating when kid #2 comes around. It’ll be a thrill. More family. More startup. Less sleep.

I can’t guarantee I’ll do everything right. Or even most things, but...

...a guy can try.

Tad is the Co-Founder and CEO of Payable.

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