Two Wrong Hires Almost Ruined My Company

Let me tell you a story I don’t talk about often.

My first CTO got poached by our own accelerator.

My second CTO?
He was secretly working full-time at a Fortune 100 company while also cashing my last $100,000.

And then my third CTO said the same thing the first two did:

“We need to rebuild from scratch.”

If you’ve ever built anything (company, team, product) you already know what happens next.

The first guy who said it left.
The second guy who said it stole from me.

So when the third guy said it… I should’ve walked away.

But I didn’t.

And if I hadn’t trusted him, Seamless wouldn’t exist today.

At the time, I was running on fumes.

My days looked like this:

• 5 a.m. to 9 a.m. — Seamless

• 9 a.m. to 5 p.m. — my full-time sales job

• 5 p.m. to midnight — Seamless again

My wife Danielle was a prosecutor, covering our mortgage while I poured every dollar into the business.

No backup plan.
No safety net.

Just belief, and pressure.

Eventually I took my first vacation in years. I flew to Colorado, and the day I landed, our time-tracking software flagged something weird.

My CTO was logging hours… but not for us.

He was working full-time at a Fortune 100 company.
Seamless was his side hustle.

And I had just funded it with my last $100,000.

So there I was:

No money left.
No CTO.
And a platform that still needed a full rebuild.

That’s the moment where entrepreneurship stops being “motivational” and becomes real.

Because it’s not testing your ideas.
It’s testing you.

Then I met Austin.

He looked at the codebase and said the sentence I never wanted to hear again:

“We need to rebuild it from scratch.”

I’d heard it twice.

But this time, he added something no one else did:

“Ninety days.”

Not “soon.”
Not “Q3.”
Not “we’ll see.”

Ninety days.

I said yes. Not because I felt confident.

I said yes because my back was against the wall.

And when your back is against the wall, your standards get sharp.

We had 1,000 paying customers at the time, and we couldn’t support them on the existing platform.

So I did something that sounds insane unless you’ve lived it:

I moved every single customer off the software and into a manual list-building agency.

Real humans. Building lists by hand.

For 90 days, we were a “software company….” with no software. Just to keep revenue alive.

That’s not strategy.
That’s survival.

Austin hit the 90-day deadline.

We rebuilt the platform.
We migrated every customer back.

And he’s still with Seamless today.

If he missed that timeline, Seamless never becomes Seamless.

No scale from $1,000 to $250M.
No thousands of jobs.
No millions of sales professionals served.

That moment could’ve ended everything.

Instead, it became the turning point.

So here’s the leadership lesson:

You will hire the wrong person.
You will trust someone who disappoints you.
You will get burned.

The question isn’t whether you make the mistake.

The question is: Did you survive it?

And when the right person finally shows up… do you have the courage to trust again?

Because after you’ve been burned twice, trusting the third time feels stupid.

Until it’s the decision that changes everything.

Sometimes the breakthrough isn’t avoiding failure.

It’s surviving long enough to meet the right person.

Want to learn more entrepreneurship lessons?

My new book Scale Your Sales is coming out this spring, and it’s the playbook I wish I had when I was in those 5 a.m. to midnight days.

It breaks down how to scale revenue, build a real team, and keep moving when it feels like everything is breaking.

Learn from my mistakes over the years so you don’t have to go through them, and follow my paths to success so you can 10x them.

Crush it,
Brandon Bornancin