My company is turning 16 and this is what I learned so far

This June Talk Shoppe turned 16 years old. Which means that if my company were a teenager living here in Los Angeles, it would be old enough to get its driver's permit.

I laughed when that thought first crossed my mind. But the more I sat with it, the more meaningful it became. 16 years feels both incredibly long and surprisingly short.

Long enough to have weathered recessions, market shifts, industry transformations, and more recently, an AI revolution that seems to redefine the future every few months. Short enough that I can still vividly remember the uncertainty, excitement, and ambition that existed when we first started.

Sixteen years later, I find myself reflecting not only on what we've built, but on what it actually means to own and lead a small business. Entrepreneurship is often discussed through the lens of growth, innovation, and success. But the day-to-day reality is far less glamorous and, in my opinion, far more interesting.

What people don't tell you about building a business

Number one with a bullet: getting paid will be one of the most excruciating business challenges, nay, life challenges you’ll ever face.

It's nerve-racking to start a new business, but I'm here to tell you that if you are decent at what you do the work will come. New business will show up. Dry spells will end. You will get projects done on time and on budget. But oh my god the getting paid part. The chasing of Accounts Payable people for money, the constant resending of invoices, the hounding, the not comprehending how companies worth billions of dollars can’t seem to pay a 4-figure invoice will be mind-blogging and it will SUCK. It does get better, I'm here to tell you that as well. But it can be so painful when you're just getting started.

Now that I got that off my chest, let’s start again and at the beginning: when people think about entrepreneurship, they often focus on the moments. The launch. The wins. The milestones. The awards. The big client announcements. What gets less attention is everything that happens in between.

The reality is that most small business owners spend their days navigating uncertainty. You are constantly balancing competing responsibilities. You are thinking about your clients, your employees, your partners, your finances, your growth plans, and your culture. All before lunch.

You are making decisions with incomplete information. You are solving problems no one anticipated. You are carrying responsibilities that very few people fully see. As founders, we often become the strategist, operator, salesperson, recruiter, mentor, and problem-solver all at once. It's rewarding work, but it can also be incredibly demanding. Oh, and did I mention the freakin’ getting paid part?!?!

The season I nearly walked away

There was a period several years ago when I seriously questioned whether I wanted to continue. Not because I had stopped believing in the business. In many ways, that was the problem.

The company was growing. Our clients were asking more of us. The team was expanding. Expectations were increasing. From the outside, things looked positive. From the inside, I was exhausted.

I found myself carrying the weight of every decision, every challenge, and every uncertainty. I remember thinking that perhaps entrepreneurship wasn't supposed to feel this hard.

Maybe it would be easier to step away. Maybe it would be easier to let someone else carry the responsibility. I suspect many founders have had some version of that conversation with themselves.

We don't talk about it often because entrepreneurship celebrates perseverance. But I think it is important to acknowledge that doubt is part of the journey. The longer you lead, the more you realize confidence and uncertainty are not opposites. They often coexist. The strongest leaders I know are not the ones who never question themselves. They are the ones who continue moving forward despite those questions.

What sixteen years have taught me

If I could go back and speak to the version of myself who started Talk Shoppe, there are a few things I would share. Here it goes:

Building a business is ultimately about people

Clients matter. Strategy matters. Growth matters. But businesses endure because of people. The relationships you build, the trust you earn, and the culture you create become your greatest assets over time. So be kind to those you work with. Be supportive and encouraging. It’s not only the decent thing to do, but you also don’t know where they’ll end up (spoiler: some become your clients down the road). 

Resilience is more valuable than certainty

I've spent years waiting for things to feel predictable. They never do, so you better get used to that idea from the very beginning. Markets change. Technologies evolve. Consumer behavior shifts (in our case that’s what makes work interesting). The goal is not to eliminate uncertainty. The goal is to build the capability to navigate it.

Growth creates new problems, not fewer problems

Early in my career, I assumed success would eventually mean fewer challenges. Instead, every stage of growth simply introduces a different set of decisions and responsibilities. That's not a flaw in the process. That's the process. Embrace it. 

Sustainability matters more than speed

Some of the most important decisions we've made were not about accelerating growth.They were about protecting culture, preserving quality, and building something that could endure. In hindsight, those decisions often mattered more. At least until now. 

Why I still love this work

After sixteen years, people occasionally ask whether I would do it all again.

The answer is 100% yes.

Not because every year has been easy or because every decision has worked out or because things became less challenging with experience. 

The answer is yes because I still believe in what small businesses represent. I believe in creating opportunities. I believe in building teams. I believe in helping clients solve meaningful problems. I believe in creating environments where talented people can do their best work.

Most importantly, I believe that building something with intention is one of the most rewarding experiences a person can have. Even with all the getting paid headaches.