What building a 20+ person company actually cost me

Everyone’s posting their 2025 wins right now.

So I wanted to share the real version — the wins, the losses, and the responsibility that comes with building something from nothing.

That cake I posted on LinkedIn wasn’t just a birthday thing.
It represented the hardest year of my life.

In January, Creator Match 🧩 was a team of 5.
By December, somehow… we were 20+.

That growth didn’t happen cleanly. Or comfortably.

Year one, I paid myself $0

I walked away from a $130,000 management consulting job and paid myself exactly $0.

Not because it was brave or romantic — but because every dollar needed to go toward hiring and building something real.

I ate sh*t so the company could survive.
Couch surfed.
Traveled like a broke college student.
Sacrificed sleep, stability, and honestly… some relationships.

At the same time, other people were making scary decisions too.

They weren’t just taking new jobs.
They were leaving stable paychecks and predictable paths to bet on something new.

And when someone does that for your mission, everything changes.

You stop thinking in quarters.
You start thinking in people.

The wins (that took way longer than LinkedIn makes it look)

• Partnered with 30+ brands, including our first 7-figure deal

• Barely survived year one of running my own business

• Hosted brand trips at Formula 1 Austin and Vegas

• Hit our first $1M payout month to B2B creators

• Grew Creator Match from 6 to 7 figures

• Built a team from 6 to 20+ incredible humans

• Finally started paying myself a salary

Today, our team spans 5 countries and 10 U.S. states.

Different time zones.
Different backgrounds.
Different perspectives.

But aligned on the same mission.

We’ve got:
→ Agency vets
→ Paid ads nerds
→ Social operators
→ Creator economy natives
→ Influencer marketing experts
→ Dedicated YouTube strategists

And yeah — let me be honest about the growing pains.

There were weeks where our systems completely broke because we hired faster than we could onboard.
Nights where I stared at the ceiling wondering if we were moving too fast, too soon.

Your mission has to be bigger than a paycheck.

People will push through chaos for something they believe in — but they won’t stay for something hollow, no matter how good the comp looks.

The part no one glamorizes

I’ve never been more stressed and anxious — and excited — at the same time.

The doubt is constant.
The pressure never really shuts off.
And the stress grows as the business grows.

Which brings me to something else I shared recently…

Why I worked for free (and why that mattered)

People ask how I get paid to speak and travel now.

What they don’t see is the unglamorous beginning.

I spoke for free.
Tiny panels.
Webinars no one remembers.
Podcasts with small audiences.

Sometimes I even paid for my own travel just to get the reps and the content.

Speaking (and honestly, most creator careers) works in levels:

1. Build reps

2. Build a portfolio

3. Get invited back

4. Travel gets covered

5. Payment shows up

If you’re early, don’t wait for permission.
Create the reps. The rest comes later.

And because wins without losses aren’t real…

Here are my 10 biggest losses of the year:

• Lost $11K when a brand went under (still paid the creators)

• Sold a $50K campaign, then the client got laid off post go-live

• Blew a spreadsheet formula and overbudgeted by $10K

• Lost a major client due to misaligned expectations

• Lost a team member due to poor onboarding

• Lost more sleep than I can count

• Sitting on $200K+ in accounts receivable (brands pay late)

• Had to pivot after LinkedIn video reach tanked

• Messed up an agency fee and lost margin

• Refunded a 5-figure campaign when sourcing turned into a nightmare

Fast forward to today

We’re employing people.
We’re changing lives.
We’re paying out millions to B2B creators.

If you ask me what the real secret sauce of Creator Match is — it’s the people.

This year, we promoted two incredible leaders — Tara Knight 🧩 and Naek Mejia.
We also brought on an HR manager (Jennifer), not just to recruit, but to invest in the people already here.

We’re intentional about who we hire.

In every interview, I ask one question:
Do you want to be great?

If it’s not a hell yes, it’s a hell no.

Looking at this team now, I’m proud of the growth.
But more than that, I’m proud of the responsibility.

At some point, building a company stops being about betting on yourself.
It becomes about honoring the people who bet on you.

Early on, I wondered if this would work.
Today, 20+ people decided it was worth betting on.

I’ll never take that lightly.

Thank you.
Let’s build.

— AJ

P.S. If you’re in a season where things feel heavier than they look from the outside — reply to this. I read every message.