Leadership and Friendship in Business

Leading With Your Heart

After I finally reeled in a few successes and some hard-earned wins as a solopreneur, I realized I couldn’t do everything myself anymore. It was time to bring in some help.

You see, I never wanted to have employees. I never wanted to be a boss but I knew I couldn’t sustain working at that ridiculous level. So I hired…

… and with managing people came a whole host of complexities I wasn’t ready for.

One of the biggest challenges? Figuring out how to be both a leader and a friend. I thought I could easily make it work. You know the ole clock in, bust ass and then grab a beer to cap off the day.

Turns out, it’s not that simple. What started as good vibes quickly turned into a balancing act between having fun and authority.

You see everyone is Good when times are good, but when things start to slow down, or when the pressure is on, the true colors come out (on both sides). And things can get ugly quick.. and they did.

The Early Days: Feeding the Beast

In the beginning, I was obsessed with creating a laid-back, fun environment.

I didn’t want to be the stereotypical “boss” – I wanted to be the cool leader everyone liked, someone who was approachable and friendly.

Fridays were sacred. We’d crack open some beers, relax, and toast to our latest sales record pasted on a huge whiteboard. The atmosphere was a pure startup feel. We were celebrating success every month like we were on top of the world.

But behind all the bell rings and celebrations, I was quietly feeding a beast.

To keep that vibe alive, I had to keep pumping more and more cash into the system. The thing is, we were beating sales records every month, but our customer acquisition costs (CAC) were through the roof. It didn’t matter, though—on Friday afternoons, the beers were cold, the music was loud, and everyone was happy.

At some point I had to give up my own paycheck which was more of a reality check if anything. The bullshit about us “killing it” was starting to crumble. I kept the party going for as long as I could, but just like a drunk guy bumping into the DJ booth, the music and party stopped.

Losing the Locker Room

It wasn’t long before I realized that I wasn’t leading anymore – I was just another one of the guys and that wasn’t a sustainable model, that’s for sure.

I had to make some brutal calls which included firing and demotions. This was a tough time and I knew what needed to be done it just felt so wrong to do it.

I ended up recruiting a fractional COO to help guide me through these times to see if:

1. These team members were the right people for their jobs
2. Was I the right person for the job. Do I need to go?

His answer to #2 was, that I was about to find out. Its all in how I handled this moment right here. Right now. Fight or Flight time.

I chose to Fight!

Once I started to take control, and act like a damn owner/leader, we decided to pivot our product line and reinvent the company.

The Next 6 months would become a shit show with a ton of turnover but slowly we started to turn the ship around.

The Messy Reality of Leadership

Looking back, it’s easy to see how I let things slip. I was too focused on being liked, on creating that “fun” work environment, that I lost sight of the bigger picture. I thought if everyone was happy, the business could run itself into a huge success.

Turns out, you can’t keep the beers cold forever when the power is about to be cut off.

The hardest lesson learned, is that leadership isn’t about being everyone’s buddy—it’s about making the tough calls when it counts. It’s about realizing when the party’s over and it’s time to do the dirty work, even if it means pissing people off.

In my case, it meant stepping out of the friendly guy role and becoming the leader my company needed. And yeah, it meant some friendships were sacrificed along the way.

But here’s the thing: as much as I hated those moments, they’re the reason the business is as successful today. I had to swallow my pride.

If there’s one takeaway from all this, it’s that being “successfully confused” is kind of the whole point. You think you know what you’re doing, you think you’ve got it all figured out, and then business/life throws you curve balls. But in those moments that’s when you need to Lead. You need to adjust, you need to adapt because sure as shit, those times are coming.

So, if ever find yourself in a similar situation just remember: the beers can wait. The success of your company can’t.

If you’re like me, you’ll probably scratch the record a few times before you find the right beat. But that’s how you learn. And in the end, it’s all part of the ride.

Welcome to being “successfully confused.”