8 months ago, one of my closest friends and I started our first company, Digital Press.

We started with two laptops and an idea. I remember sitting in his apartment living room on the couch, The Office playing on the TV in the background, while we threw around names and logo ideas. We opened a Google doc and started writing website copy. And all the while, we thought, "Will this even work?"

Just like every other entrepreneur out there, we had no idea whether our idea was a good one. All we knew was that we had about 2 months of runway in our savings accounts and had to try something.

From the moment we turned our website live, and I started using my own personal brand to amplify our unique approach to written content for founders and CEOs, we were profitable. (And if that's not the ROI of building a strong personal brand on the Internet, I'm not sure what is.)

In our first month of being in business, we hired our first full-time employee.

Month two, we hired our second.

And every month since, we've added another full-time team member--and with each hire, we've had to solve the challenges that come with every fast-growing startup.

For me, the past 8 months have taught me more about life, and specifically what it means to be a leader, than anything else I've ever been involved in. School couldn't have prepared me for this.

Whether you're a founder, or thinking about starting your own company, here are 8 lessons I've learned hiring a new person every month--for the past 8 months:

1. Hire yourself, then fire yourself.

Our growth rate as a startup has been borderline vertical. 

And at every step, I found myself repeating the same dance. I would step into the next logical role that needed to be filled. I would learn it, question it, master it. And then I would find someone who could do it better than me--and fire myself from that role, moving onto the next.

Jeff Seibert, founder of Crashlytics (which sold to Twitter and then later again to Google), sums this method of thinking up perfectly in his article, The Role of the Founder/CEO: You Have One Job.

2. Your culture is a reflection of YOU.

Nothing has been more humbling than the realization that, as a founder, the culture you create is a DIRECT reflection of the way you work, act, and treat others.

My co-founder and I have been friends for a decade. We met making music together in college--he played drums, and I played keyboard/piano. For 8 years, we collaborated on music, and in that process we learned how to respect each other's thought processes, perspectives, musical choices, and decisions. 

When we started a company, that same dynamic carried through.

I saw, pretty much immediately, how the way us two interacted gave our first, and second, and third hires a barometer for what we felt was an acceptable culture. We never yelled at each other. We never got passive aggressive. We listened, we joked around, and we cared about our work. 

Our most recent hire just came on board and said, "I've never worked at a company like this. It just feels different."

That's the point. And as a founder, you need to realize the culture you create is a reflection of YOU. So if you don't like the culture you've created, look nowhere else than in the mirror.

3. There's no reason to take money out of the company--and put it in your pocket.

So many aspiring entrepreneurs see "starting a company" as a way to put more money in their own personal pocket.

I'm going to let you in on a little secret: the moment you start building a successful, profitable business, and the moment you start hiring (a lot), and your payroll increases, and your overhead goes up, and expenses start mounting, all of a sudden taking money out of the company sounds like the dumbest thing you could possibly do.

There's no point. Leave it in the company. Grow. 

Grow your team. Grow the value of the company you own. Acquire competitors. Enter new verticals.

Build an empire.

4. Your stress is your stress. 

As a founder, you have to learn (very quickly) that your stress is your stress. It's your responsibility. It's yours to carry, yours to address, and yours to put aside when working with and supporting those around you.

The moment you start expecting your employees to assume the same day-to-day stresses should be the day you also make them full partners in the business. It's not fair to expect those around you to feel every nuance of the company when they were hired for one responsibility--not the hundreds you're juggling.

And honestly, as a founder, you should never take your stress out on anyone. It compromises your team. It worsens morale. It makes people feel unappreciated and encourages them to take their stress out on someone else--which is what ultimately creates a destructive culture.

Whoever says personal development isn't a key pillar of entrepreneurship lacks the self awareness required to lead. And that lack will only lead to the demise of the company.

5. People fail when they're not put in positions to succeed.

How often do you hear a friend, family member, or acquaintance say, "I hate my job."

But people only hate jobs for a few reasons:

As a Millennial, all I hear from older generations is how entitled Millennials are. How much we don't want to do the work. How we complain that people don't show us enough, and don't take the time to teach us.

And yet, during every single interview we've had with new hires, I've asked, "Why didn't you enjoy your previous job?"

Every single answer listed off one of the above three answers.

By being involved, by actively sharing the company vision, by taking the time to teach and empower the people we bring on, I have seen the opposite. I have never had more faith in the Millennial generation. Young people are capable--if you, you know, make the effort to treat them as an integral part of the team.

6. As a founder, your single greatest asset is head space.

The simple version of this is "time." Your time is your most valuable resource. 

But I would argue that head space, the quality of time, is even more important.

The whole purpose of hiring people isn't to add more noise, more overhead, more people. It's to reduce the amount of things you have to think about in a day.

The reason is because, as a leader, your primary job is to steer the whole ship. And in order to do that effectively, you need to be clear and calm. You can't be stressed. You need time to read, and think, and imagine. 

Founders often mistake this for kicking their feet up and watching everyone else work.

Trust me, if you're doing it right, it's calm--but it's certainly not easy.

7. Some decisions have to be made based on what you know you're going to do.

Every hire has to have a purpose.

Every decision has to have merit. Every choice should acknowledge both sides. Everything you do should be validated by both your head and your heart--it should make logical sense, and it should "feel" right.

However, there are some decisions where you're going to have to bet on what you believe you can make happen. Yes, they should be logically sound. Yes, they should "feel" right. But at the end of the day, doing things like preemptively hiring people will come down to the belief you hold in yourself and your team to make those hires worthwhile.

You have to know that even though you're taking a risk, you are confident in your ability to execute to the point where it's not really a risk at all. And the reason why you have to learn how to (responsibly) bet on yourself like this is because otherwise you'll start making decisions that mitigate fear--instead of confidently executing your way past it.

8. Principles are the only way to scale.

If the business is dependent upon your personal involvement, it's not scalable.

The moment we hired our first employee, I worked tirelessly to think of every possible scenario that could happen in that role, how I would handle it, and how I could build a process that would allow someone else to make the same kinds of decisions.

Once I replaced myself, I moved to the next role and did the same--as did my co-founder. 

I find most companies (agencies specifically) struggle to scale because the founders do the opposite. They start a company based on their own expertise, and refuse to pass those responsibilities to others. They want to be personally involved, in every decision, putting their own unique touch on each and every outcome. 

That's not scalable.

Like I said at the beginning of this article: hire yourself, then fire yourself.

Published on: Feb 28, 2018
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