2 Years In: 22 Raw Lessons From The Messy Middle

2 years ago, I quit my corporate job.

I was sleeping on couches. No revenue. No team. No idea what I was doing (still don’t lol).

Today, Creator Match not only turned 2 years old, but we hit a major company milestone having sent $1M in creator offers in a single week.

Most founder advice is complete BS. But we're still here. Still growing. Still figuring it out. Here are 22 raw lessons from someone who's still building in the messy middle.

THE ORIGIN STORY

I started Creator Match betting on something everyone said was too niche: B2B creator marketing on LinkedIn.

May 21, 2024: I announced I quit my corporate job. Nobody knew what was coming.

June 20, 2024: I launched Creator Match publicly. Same day Tara Knight commented on the post. She didn't even work here yet. Six months later she'd shut down her own agency to become our COO.

Year 1: I went all in. September 2024: sleeping on couches with friends while building. Convincing Tara to go all in with me. We hit $1M in creator payouts in 12 months. I didn't pay myself a dollar. I can’t express enough how SMALL the budgets were back then. Imagine me in the dumpster hunting for crumbs (think $2k TOTAL budgets that include 5 creators AND our agency fee lol).

Year 2: We went from 5 people to 40. Built a global team. Flew everyone out for our first offsite (two villas, three bonfire parties). Helped build an entire industry for B2B. First agency to pay $1M to LinkedIn creators. Then we did it again in a single month.

Year 3 (now): We just sent $1M in creator offers in one week.

But here's what matters: we didn't stop at LinkedIn.

Creator Match builds full-stack creator programs for the fastest growing tech brands in the world. 

We support brands through:

• Short form channels (LinkedIn, Instagram, TikTok, YT shorts, Twitter/X)

• Long form channels (YouTube & newsletter)

• Paid media (to boost the influencer content)

• Creator gifting

• Brand trips & IRL events

40 people on the team. Billion-dollar tech clients. Paying millions to Creators. And doing so much more than just one channel now.

It's real now. Still can't believe it. And we’re just getting started.

THE LESSONS

22 - Stop building a life you need a break from.
You won't be burnt out if you are building something you're passionate about. Treat business like a video game - enjoy every level.

21 - Befriend your competitors.
You have way more in common than you think - stop playing a zero sum game.

20 - Pick one: lifestyle business or scale business.
Knowing the direction you're going will help in the long run especially how you build.

19 - If you can't commit a decade, don't bother.
Stop chasing get rich quick. Most ppl quit too early. Good things take time and compound.

18 - Riding every high and low will kill your company.
Ride the middle. Boring consistency beats passionate chaos.

17 - Your ADHD is not an excuse. Focus or fail.
I have ADHD as a Founder. It's not easy but do fewer things better than more bad.

16 - "Work-life balance" in year one is a red flag.
Find work you'd give your weekends to. Become obsessed.

15 - The graveyard is full of businesses nobody started.
The hardest line to cross is the start line.

14 - Own a swim lane, not a swimming pool.
Be known for one thing completely before you scale. For CM it was linkedin creator marketing and B2B.

13 - Rework your calendar around your energy, not the clock.
Protect your peak hours. I do creative work in the AM, calls in the PM.

12 - Surround yourself with other Founders.
I moved in with one lol. Proximity is a cheat code. Thx for keeping me sane Brandon Pourmorady.

11 - You can only pick 3: success, health, sleep, relationships.
Stop pretending you can do it all. Especially in year 1, you will need to sacrifice. For me, it’s been sleep.

10 - Post it ugly or stay invisible.
The messy middle is the moat. Document > create. And let your team POST!!!

9 - Quit the red ocean. Go find a blue one.
I bet on what people said was too niche (B2B). There was zero competition.

8 - Your best hires matters more than your biggest client.
Like hosting your first ever team offsite in Austin during SXSW, and building it all in public. You should genuinely enjoy the ppl you are building in the trenches with.

7 - Don't sell. Just solve.
People buy when they hear their problem repeated back. Listen, don't sell.

6 - Chasing the sexy niche is why you're broke.
Boring has bigger budgets. Riches in the niches.

5 - Do things that don't scale.
Especially with AI - make the handwritten cards. IRL dinners. Human touch.

4 - Bulletproof your mind by chasing hard things.
I ran 3 marathons in the first year of biz (1 ultra).

3 - Year 1 is not the year for balance.
Someone hungrier is outworking you right now. Get ready for long hrs and sacrifice. Go all in.

2 - If you hate sales you will fail as a founder.
You're selling clients, talent, investors.

1 - The scariest thing isn't leaving. It's staying.
I jumped from my comfortable corporate 9-5 to launch a startup.

🤝 In Partnership with Creator Economy Live (CEL) East

I haven’t been home in 2 months. Drinking more cups of coffee than the number of hours of sleep im getting.

Biggest learning building Creator Match: Motion builds momentum, and that compounds into wins. You need to show up. And now I have a 40+ person team that counts on me... plus brands and creators.

Tomorrow, I emcee Creator Economy Live with TikTok, LinkedIn, Chicago Bulls, NFL, Disney, AG1, and 500+ creators and marketers.

The "messy middle" is brutal. But it's also the phase where you outwork everyone else. The phase where you win.

If you're serious about building in the creator economy, you need to be in the room where it happens. Like Creator Economy Live tomorrow. I'll drop a discount code for you in the comments!

^{Use code CREATORMATCH20 for 20% off all passes.}

WHAT’S NEXT?

40 people. $1M offers in a week. Billion-dollar clients. Speaking at Cannes. Hosting brand trips around the world (from Formula 1 to the SF Giants). Getting invited to give a TED talk. Emceeing the largest creator conference in the world (1 Billion Follower Summit in Dubai).

But here's the thing: we're hungrier than ever. Still learning. Still building in public. Still figuring it out day by day.

Year 2 is proof that boring, consistent, patient work compounds. Not get-rich-quick. Not luck. Create your own luck. And show up.

What's your "never did I think"? What's the thing you quit for that everyone said was too niche?

Keep going anyway. Your "never did I think" list is already being written.

You just can't see it yet.

— AJ

P.S. If you want to work with Creator Match (as a brand or a creator) — start here.