How to Mix a Family and a Startup

We've all been there.

Sitting at our desk as this dark cloud of guilt begins to swirl — yet again — knowing that we're about to choose whether we're going to finish this one critical project at work or make it on time for dinner. Or a soccer game. Or any event that our families are counting on us for.

Do we fail the startup or do we fail the family? We're going to fail someone. Guilt is a constant, the only variable is the source of the guilt.

If this sounds familiar, it's because nearly every startup Founder wrestles with this problem on a daily basis.

We're not just working at jobs — we're trying to survive long enough to even get a paycheck. Everything we have is on the line, including the welfare of the very people we're running home to love on.

It's not a Choice — It's a Plan

Our challenge often begins when we think that the only option is making a sacrifice.

Yes, there are many cases where we simply can't be in two places at the same time. But managing the sacrifice between our startup and our family starts long before that. It starts with creating a foundation for understanding on both sides.

Where we get hung up the most is on how we approach this problem, which is good news, because that means we've got some ways to improve the balance.

The plan is a combination of how our families understand our startups, how our startups understand our families, and how we manage our time and "presence" to make absolutely sure we're all on the same page.

The Startup has to Understand Family

When I was starting my first company, we had grown pretty quickly in size, but our average age was still around 24 years old. I was so young I was bringing that average down.

There was this one guy who was "really old" (he was 30) and had kids. While the rest of us would be working well past midnight, he was clocking out at 5 p.m. We gave him a hard time about it, telling him it must be nice to work half days. We were kidding, but in retrospect, we never really understood what he was going through.

We didn't understand family. And it was incredibly regrettable.

Years later when we created Startups.com all of us were becoming parents for the first time. We all learned that every minute that burned through the night was another minute we weren't at the dinner table with our family, or reading to our kids, or tucking them in to make them feel safe for the night.

Now, not a single person is at their desk past 6 p.m. No one misses soccer games. We put family first as a culture since inception. There's no asshole like me mocking others for not putting the startup before their kids. Also, I'm now the oldest person in the company (oh, Karma...).

We've found that part of alleviating the "guilt" is creating an environment where family isn't a source of guilt to begin with. It's about making sure everyone — even those without kids — truly understands how important family is to us. We've grown by leaps and bounds all the while supporting families, not destroying them.

We're incredibly proud of that, by the way.

The Family has to Understand Startups

The balance of understanding doesn't solely rest on our startup, though.

We also have to educate our families on how our startup works in order to help achieve any sort of balance. This may be the hardest thing we do because the communication is so damn complicated.

Part of the challenge is that, to an outsider, this conversation basically makes no sense. Here's a rough transcript of my first conversation with my daughter years ago:

Me: "Daddy works at a startup company. It's like a regular company, except Daddy doesn't know if he's ever going to get paid."

Daughter: "Why would you do that? Why not just work at a company that pays you?"

Me: "Well, this is something that Daddy is really passionate about and if it works out well, could provide an even better life for us. But it requires a lot of hours."

Daughter: "So you have to work more and get paid less?"

Me: "Well, yeah."

Daughter: "That doesn't make any sense."

The problem with this conversation is that she's 100% right. It doesn't make any sense. And the less we explain, the less sense it makes. From the outside, what we're doing is risky, pays nothing, takes us away from our families, and sends us home frustrated and tired.

If we leave the conversation there, then all of those sacrifices and investments we make are for naught. It's our job to constantly remind our loved ones why we're doing what we're doing — not just the complaints about why it's so hard or we're so stressed.

If we don't invest those cycles into an explanation, we're only showing them strife (and typically no pay to go with it!)

My children are still very young, and they are just beginning to understand what I do. But what they hear from me the most — and I'm very deliberate about this — is every single good thing that happens that I'm passionate about. I know that these constant reminders provide the platform for understanding that is so critical to understanding the basis for my sacrifice.

A big reason I'm able to communicate so effectively with my kids is because my spouse is 100% up to speed and on board with our path.

I wrote about this extensively in another post "How to Prepare a Spouse for a Startup."

Collectively, we present a unified front about why we, as a family, are long on startups. It's incredibly hard to build this foundation, so nothing about this is suggested lightly, but absolutely critical in order to prepare the entire family for this journey.

We've Gotta Live in a (Time) Box

If we're not going to be able to work nights and weekends, we have to live in a time box. We have to set certain hours and we have to be so incredibly boxed into them.

We also don't have the luxury of wasted time — not even a little bit. That's because our wasted time has real cost. When we were young and single those moments had opportunity cost, which is also real. Now those moments cost us time with our family, which, let's face it, is a hell of a lot more real.

That means we have to organize our work days with absolute precision. We have to stuff twice as much productivity into the few hours we can dedicate to our startup as anyone else. If we can't get done what needs to get done in 9+ hours per day, the problem isn't enough time — it's enough organization.

It's 6:29 A.M. as I'm typing this. I have exactly 12 hours today to get everything done. That's more time than most people will ever spend at a job to begin with. But I need to be done by 6 P.M. with no exceptions. That's my time box. If I can't get something done by 6 the problem is me, not my startup.

How do I maintain that schedule?

Not by working more hours. I maintain it by cutting out as much bullshit in the middle of the day as possible. I schedule very few meetings. I check in on social media maybe once a week. I cleared any bookmark in my browser that isn't focused on productivity. I look at anything that's a distraction as a strike against my family.

I'm militant about time, and I'm so much happier for it.

Be 100% Present

If we were to rank the most important aspects of learning how to mix a family and a startup, I'd have to pick "be 100% present" as the most important, even though I'm getting to it last.

I say that because, despite everything I just shared, my guess is we're going to miss important events. We're going to have deadlines that absolutely crush us, because in our case if we don't meet them, we don't get paid.

Therefore, in the event we can't get all the time that we'd love to have, we have to make sure that the time we do have is 100% present. That's basically the last straw.

If I'm not present with my kids they can read me like a TSA scanner. They don't call me out — they don't need to — but their body language instantly changes. My wife is the one who will remind me where I'm supposed to be mentally at that moment and I'm very thankful for it.

So the phone gets put away. The laptop gets shut off. I unplug.

It's. So. Effing. Hard.

My startup brain wants to sprint at full speed. But I've learned that if I don't invest every bit of myself in those precious moments that I have, I won't have earned the right of understanding with my family.

In the same way, I've made commitments to everyone involved in my startup, I have to make good on the same commitments to my family — and then some.

There's not "being there" for an event, and then there's "not being there" standing right in front of your loved ones. If we can't be present, we're not really holding up our end of the bargain. And that bargain starts with being 100% present and focused on our loved ones.

Embrace Imbalance

If all of this sounds like a balancing act, it's because it is.

However, in this act, there is no balance. There's no perfect zen place where the craziness of a startup and family life just fall neatly into place.

It's gonna be hectic all the time.

We can't neatly manage every day and week into perfect order. That's not how either of our "startups" work. What we can do is embrace the imbalance. We can embrace the fact that some days or weeks are going to be heavy on family and others are going to be heavy on our startup.

What matters is how well we invest our time and presence in each when the time is right. This isn't about the quantity of our time, it's about the quality of our focus.