The founder hustle

Last night, while supporting the team through an important maintenance, I was reading through Twitter and saw the continuation of backlash towards this tweet:

When I first saw the tweet, I had no passionate reaction to it. To each their own, whatever. But the comments were magic. People of every walk of life, owners, employees, commented how wrong it is to have this mentality. Because, as they rightly pointed out, this is family time and we should hustle less. I wholeheartedly agree. 

Lots of founders (highly successful and very respected) chipped in to show their solidarity by sharing their holiday plans away from the office, which again is all good. The tone of these comments is where I have a problem. We aren’t being honest and we’re not sharing the full story.

I shared last night that I believe that as successful founders we need to remember and remind ourselves that we once did have to work longer hours. That it wasn’t always as freeing, mentally and physically, as it is today. Since there was some disagreement, and Twitter isn’t my forte, I’ll share here where I’m coming from.

The following will be our story. But I believe many (most?) others have a similar path.

Businesses have different life cycles

We’ve been running a business (my husband Chris and I) for seventeen years. We’ve had products for over 10 years. Our culture focuses first and foremost on peacefulness, focus, and calm for our entire team. And has been that way for years. We’re currently expermineting with 4-day (32 hour) work weeks for the ENTIRE TEAM. So, I get the importance of working less. And we have 2 kids that we see all the time.  

But it wasn’t always this way. Businesses are like people in that they have different phases of life. It might be a cliche analogy, but since we’re all focused on family over work, let’s run with it.

You don’t leave an infant unattended, and you don’t leave your business when it’s that young as well. When we started our company, our only job was to keep the damn thing alive. Make sure it doesn’t stop breathing in it’s sleep. You do that by waking up in the middle of the night, by thinking about it constantly, by being blurry-eyed and exhausted. But you know what, it’s invigorating and exciting and one of the coolest things you get to do in your life. 

Then you get through those first months/years. You start to grow. And growth is what gives founders the space to have space. Growing allows you to hire people to start wearing some of the many hats you were wearing when you started off. Growing allows you to charge more, if you’re on your own, or choose better clients. But growing is the only thing that opens the door to peacefulness. 

And growing takes a lot of fucking work. 

What is work?

Maybe where we’re all falling apart here, the DHH’s and the Gary V’s, and the rest of us, is how we define work. Is it being in the office? Is it being on your phone at the dinner table or at the recital for your daughter’s ballet performance? Is it not sleeping at night because you’re excited about what you’re going to ship? Is it obsessively checking and posting to Twitter the last week of the year? 

Maybe it’s all of those things? 

What makes us entrepreneurs is that we don’t stop working. At least, we don’t stop thinking about the hustle. We sit in a restaurant and observe how it is operationally and how we can apply that to our business. We read marketing material in that same ballet recitals program book and comment on how poorly worded the ads are. We are always ON, and that is totally ok! 

Our biggest challenge as entrepreurs is to find other outlets and other hobbies and passions so that we can think about work less. I have my kids. And my obsession with the team and how to keep pushing the boundaries. Chris has been racing cars. We like real estate. And we travel as much as we can. We are present, very present, for our kids and our families. But it takes tremendous work to get there. Discipline to put the phone on the table before walking in the door. Discipline to place it on silent, or to put the inbox aside. Not because we’re bad people, or because we don’t love our families. It’s because that’s our makeup. And the sooner we acknowledge it, the sooner we can use it to our advantage.  

Employees are a luxury

It’s easy to take time off when someone else is running the show. That’s the real, honest truth. When you run a SAAS business (or any business), and it’s just you, who does support? Who receives Pingdom alerts? You do. But you also have to think about growing, marketing, features, finances, and on and on and on. 

Hiring a team is what enables all of us to step away in some capacity. And that is a luxury we have to remember when we go yelling at new entrepreneurs to work less. Or to take a vacation without your laptop.

Entrepreneurs spend their lifetime figuring out what they own in the business and slowly handing it off to others as they grow. Some do it better than others and get things off their plate sooner. But we all have to do it. And the more you move off your plate, the more space you create in your head. 

Early on I did all of the support for Beanstalk (our first product). We could only afford to hire on the product side, so most of the triage and support was on me. There was a constant nagging of whether to check the queue. What if someone was stuck? What if something was broken and we didn't know? It was always in the back of my mind even if I didn’t open the computer or check my phone. When we hired Dana, our first person on support, it removed that nagging from my mind. Now I had space to think of other things. And the same story with all the things I’ve removed from my plate.

Today, I spend a lot of my days thinking. Because today my job is more strategic and less operational. But I only have space for that because I have an amazing team in place to cover for me. 

Working and growing are a choice

This is the most important wisdom we should be passing on to new entrepreneurs. That everything we are doing is a choice. Deciding to run a business is a choice. How long you work is a choice. And how big or how fast you grow is also a choice.

What we should be sharing is this: the people that are talking about taking the week off are the ones who are choosing to grow with intention. They, like us, are choosing to grow at a pace that is sustainable for themselves and for their team. We work less, which means we may grow slower. I’m ok with that because I’m choosing life WITH growth. And I can make that choice, because I have a profitable, growing business that can enable the benefits and shorter hours and salaries that I want for myself and my team. 

What we should be explaining is that to get here, we had to work hard. We had to learn the hard way. We had to have kids to realize the importance of family. We had to have space in our minds to realize the value of mindfulness. We weren’t born of these things, and they are not easily passed from one person to another.

Here’s how I learned.

An immigrant story

Natalie with her mom and sister

It’s the end of the year, so let’s share an immigrant story. I came to the US with my parents as Jewish refugees. That’s a story (maybe a book, Mom?) for another day. Both of my parents built huge businesses from nothing. It started with my mom when I was little. She worked her ass off building a mortgage business by working way more than 40 hours a week. She did it by working as long as necessary. My dad supported her and my sister and I have never felt neglected or distant from her. She instilled the fire under my ass and my sisters to be great. But she made tremendous effort to spend time with us when she could.

She had to work long hours because she had clients that called. And if she didn’t answer, they’d go to someone else. And I know what the naysayers will say, but I call bullshit. Maybe someone else could have been so savvy that they could fight that off, but my mom is my hero and pretty damn savvy and that was what she felt like she needed to do. We don’t know how spoiled we are in our SAAS businesses until you remember what traditional businesses take to grow.

But in addition to the fire my mom lit under my ass, my millennial-ness still shines through and I don’t want that way. I want to take unplugged vacations and be present in my kids’ lives all the time. I want to share experiences. So that combination is how Chris and I got here. Hard work and the insane desire to work less. Knowing that sometimes, you have to really put in the work. But that your purpose is to make those times shorter and less frequent as time goes on.

The early days

Natalie and Chris

When I met Chris, he already had a small consulting practice at Wildbit. I hung out at his house while he took client calls, then we’d have dinner, then he’d go back on his laptop. We didn’t count hours. We were happy. 

We spent time with family but because we had the luxury of being young and no kids, we didn’t really have to answer to much more than ourselves. When we felt burnt out, we’d take a break. 

Chris also missed my closest friends wedding last minute. We had a client emergnecy. He was in his suit on the couch trying to fight it fast enough to leave with me, but he ended up staying home. I didn't love that day, and he was pretty sad about it too. But it’s reality of being an entrepreneur. 

I don’t want to go back to those days, because we felt like we’ve paid our dues. Kind of like when you have your last kid out of diapers. But we don’t look back on those days with disdain. They’re so special. 

Real vacations?

We have always traveled together, and for a long time that included a laptop and we never put our phones on silent. We owned some important parts of the business for a long time. Specifically for a while Chris owned all the infrastructure for the business.

Chris hiking with Sophia in Costa Rica

My favorite story is of our big family trip to Costa Rica when our oldest was a one year old. We booked a huge house for our immediate families on both sides. We had very shitty internet reception (something about a satellite and only available when the tide came in?). It was ok because we had a team and the company could run without us. Except if there was an emergency.

Here we are on a hike to a waterfall when we got a call that Beanstalk’s storage infrastructure was completely down. We had to turn all of us around and hike back, through the same waterfall, while on the phone coaching someone through restarts of the server. This is real life of an entrepreneur on vacation sometimes. 

It gets better

Today we take unplugged vacations pretty regularly. I spend days reading books and not my inbox. We’re home at 5pm with the kids and get into work around 9:30am. I’m in the same camp as my colleagues that believe we should enjoy our lives and work less not more. It’s all true and it’s all important.

These businesses we’re building have cycles when they need us to hustle, and when they can afford for us to live a more peaceful existence. Even in a stable, successful business like ours, we have times where we have to give up more of our time away from work to get something out, to get ourselves out of a jam, or to support our team in the work that they’re doing. Just like when you have to jump in and help a grown kid, sometimes the business needs more from you. But the badge of honor is not on working long hours, it’s instead accepting that you’re available when it’s necessary, but fighting for those times to be exceptions and not rules. 

I want new entrepreneurs to not feel guilty or wrong for working hard at something they are crazy passionate about. Your business will pull you in and occupy your every brain cell. You will be excited about it, worried about it, passionate about it. Channel that towards getting to a better place. Find the important things to work on. Remember to find time for your health, mental and physical. Make some friends with founders who have been there before and see the other side. Maybe they can suggest a workaround or just trigger a gentle reminder to get outside. But don’t feel guilty about it. We’ve all been there and are only so dogmatic because we’ve seen the other side.

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