5 Lessons Learned After a Decade of Entrepreneurship

My first business was a lemonade stand, except instead of lemonade I sold my Mom’s mint iced tea; I saw it as a competitive advantage (even though it was my Mom’s idea).

Then in college I ran a franchise for College Pro Painters, painting 42 houses in the Lower Merion area during the summer of 2002.

During my sophomore year at College, while I was interning at Morgan Stanley, I started doing some independent contract work under the moniker Nick Eubanks Solutions.

Then in 2008, I launched my first, actual Company called atomni, with 2 Partners.

So even though I’ve been an entrepreneur since I was 8 – this post is going to reflect on my past 10 years since creating my first legal business.

There are countless articles about what it takes to be an entrepreneur, covering all the lessons from shining moments to dumpster fires – my goal with this post is to be different, and try to add something new to the conversation.

I want to run through some of the lessons I’ve learned that you maybe haven’t read about (I know I didn’t).

It’s not going to be pretty, but in reality being an entrepreneur is pretty ugly, and more people need to talk about that.

So here we go…

1. This is way harder than anything else you’ve ever done

You see the pictures of fancy cars and nice houses, and I’ll admit I’m guilty of following a few vanity accounts on instagram too – but what people don’t show you is the high credit card bills, the near empty bank accounts, and the nights spent wondering wtf you’re going to do the next day.

While the idea of a job seems safe, and for the most part it is; there’s nothing safe about starting a company. Sure you can’t get fired in the traditional sense of the word, but you can still get fired; whether by your clients, your partners, or the board – you don’t have the control you think you do.

There really should be some sort of course or material to prepare you for the mental toll this is going to take on every aspect of your life; your relationships, money, health – everything.

To crystalize this, think back to a time where you were really frustrated with your boss. Remember feeling a lack of control and likely thinking about how you would do things differently if you were in charge?

Now imagine being in that same head-space, except there’s no one to blame but yourself. The feeling of inadequacy and impostor syndrome sets in quickly, and believe you me, it’s terrifying.

2. You’re not going to hang out with the same people

That may sound obvious, but I’m talking about friends you’ve had since college, high school, and possibly even childhood.

Building a business and pouring all of your time and attention into something, changes you.

I’m not saying it’s bad, but you will begin to feel isolated from your peers because, well, they won’t really be your peers anymore – and you’ll seek out people that are.

Especially as you begin to grow, and your business crosses key milestones like your first hundred grand, your first employee, your first million dollars, and so on – you will naturally seek out people that are in the same place in life that you are, if for nothing else than to commiserate.

It’s not even necessarily intentional, it just sort of happens, because being an entrepreneur is a mindset.

And.. it’s contagious, well, infectious – it will infect all aspects of your life. You’ll likely start reading blog posts about things you never cared about before; finance, hiring, cashflow statements, and so on. Which will quickly evolves into reading business books, listening to podcasts, going to events…

It consumes your life and so you end up only spending time with people in the same phase of their entrepreneurial journey as you.

3. You’re never going to have time

This comes back to mindset, but things you put off will simply never get done.

The only way to combat this is to accept it, and reframe how you think about it – and the trick for doing that is to understand it’s about priorities.

The shift needs to go from “I don’t have time” to “it’s not a priority right now.”

This was big for me, and it really stemmed from things in my personal life like drinks with friends, concerts, and even family events.

It’s unfortunate to admit, but it’s the truth.

You will hit a point where you either burn out, or you’ll learn to meticulously manage your calendar – and trust me when I say it’s a surprisingly acute skill.

One tip I can offer is setting specific blocks of time that you’re available for meetings, and either 1) opening up your calendar to be shared and editable by your team (whether PM’s, AM’s, or Managers), or 2) hiring a dedicated assistant, whether a VA or an in-house EA.

Which leads me to my next point;

4. You’re not that important

I know it’s harsh, but this is an important byproduct to be aware of.

In the beginning, you are the company, every bit of it. But as the company grows and you begin to hire, you will become less and less important up until a point…

Then it will happen, and it may come slowly enough that you don’t notice, but one day your business will run without you (at least it should).

Congratulations, you can now take a vacation.

The nuance here is that if you haven’t removed yourself as the critical linchpin required to run your business, you don’t have a company; you have a job.

Being an owner is a relatively thankless job, unless you’re able to retire in your business – this means that you can participate on the highest value items but the day to day operations and fulfillment is run by your people.

Finding the best talent and then building compensation packages to attract and retain that talent will become your new day to day.

When things are at their best you’ll likely be spending 70-80% of your day trying to hire for key roles or making executive decisions.

For a while your decisions will be critical in setting the Company’s path; how fast you grow, how profitable you are, and the strategic moves to ensure your future.

Start thinking about replacing yourself years before you plan to do so – this is something I’m still learning. Hat tip to Richard Baxter for some very solid advice here;

You really need someone to take over who is 100% behind the business, and from the business.

I have a solid 20 years of work left ahead of me – I just love what I do too much to stop doing it, but knowing that when the time comes I need to prepare well in advance to ensure the stability of the company, is invaluable.

5. Delegating is an art form

I’m sure you’ve heard delegating is important, you may have even heard it’s hard, but it’s more than that…

It’s an art form akin to painting or yoga; it takes time and practice – and a lot of it.

What’s more is you have to learn how to delegate, because it’s not as simple as just telling people what to do.

You need to develop the ability to design processes that enable delegation, and then mapping people to those processes.

You also need to be willing to accept that there will be a decline in quality (whether real or just perceived by you) and that’s OK, it’s part of the learning that must happen.

Let your team make mistakes, and do things differently than you would, otherwise you’ll never be able to scale.

More times than not eventually the student surpasses the teacher – so you’ll ultimately end up with better work than you were capable of in the first place.

In Closing

It’s not all doom and gloom, it’s just some gut checks that I’ve personally had to deal with and I thought were worth sharing.

Plus, it helps me to write about them to further accept and reflect on them.

What do you think? Did I miss anything?