A few weeks ago, I shared the big news that Meryl Johnston is now my co-founder here at TeamUp.

In my last email, you heard her story—how a startling diagnosis and surgery left her searching for her next great mission. Click here if you missed it.

While she was recovering and questioning everything, I was drowning in my own confusion. I'd stumbled onto something incredible, but had no idea what to do with it.

This is the story of how I nearly gave up while holding treasure in my hands.

Two people, half a world apart, each searching for answers we didn't know the other had.

Bangkok

Suddenly, the speaker on stage froze mid-sentence.

All eyes were on him.

Seconds passed. Had he forgotten what to say?

Then the hum of the ballroom faded and the lights dimmed.

Time slowed.

He turned and looked directly at me.

"You could have everything you want," he said, his voice echoing in the stillness.

What?

"But not if you hold on to it all."

I looked around.

Was everyone else seeing this?

I turned back to him.

"You must choose."

I tried to respond, but my mouth would only hang open.

His stare held me in place.

I blinked. The lights came back up and the audience erupted in applause.

What just happened?

I sat there, stunned.

Later, replaying those words in my mind, I thought I understood what he meant.

Choose one thing. Focus.

But his eyes held a burning certainty, like he could see what this choice would cost me -

and it filled me with quiet dread.

What would I have to let go of?

I would find out a few weeks later.

The real choice came in the form of an email.

Born For Adventure

I was born for adventure—not the outdoorsy kind, but the kind where I chart my own path.

I never wanted to live on someone else's terms.

That's what led me to ask my wife to quit to our jobs and chase this dream together.

But adventure always comes with risk.

And after years of chasing ideas, never quite finding success...

One question grew heavier on me:

How long can we keep going like this?

The Success That Wasn't Enough

The bookkeeping firm was working, at first.

It was everything my partner and I had hoped.

We helped eCommerce business owners understand their numbers, something I'd struggled with in my eCom days. Clients loved us, and our team excelled.

And for the first time since I left my job, with recurring revenue, I finally had a stable income. It wasn't much, not even adequate, but it was consistent and growing.

Then we hit the ceiling.

I'd built our entire client base from my network and simply ran out of prospects.

Worse, I learned that we needed much bigger clients than I knew how to find.

Business coaches say it's easier to sell to existing customers than find new ones.

So, instead of growing up, we grew out.

We added recruiting, then marketing services, trying to squeeze more value from my eCom experience.

But after a couple of years, none of it was working the way we needed it to.

I felt scattered. Each new project pulled me in a different direction.

I was confused and frustrated.

But one thing showed promise: recruiting.

The Fading Promise

My wife's job was getting harder.

The hours were longer, the stress intensifying. Weekends were spent in recovery.

Yet she never complained and never blamed me.

Financially, we were doing better as she kept earning more.

One day, she reminded me of my promise:

If we quit our jobs and moved in with my parents, I'd build a business that would free her to pursue her creative dreams.

Did I really say that?

I was now on my seventh business, and still no closer to keeping that promise.

I couldn’t even see a path forward.

However, I’m annoyingly, eternally optimistic. A failure hits, and within days I’m chasing the next idea like nothing ever happened.

Disappointment stings her more, so she'd grown less excited about my new ideas.

But even I have my moments.

How Much Longer?

Our financial talks usually happened on the couch, late at night.

My wife would finish paying the credit card bill and say:

"We spent too much this month."

But this night, after an especially stressful week at work, she asked:

“How much longer can you keep trying to make this work?"

"Will there ever be a point where you say, ‘I gave it my best,’ and go get a job?”

She didn’t say it with resentment. She said it with love and exhaustion.

A jolt shot down my spine before I could even think.

I didn’t have an answer.

How long could I keep asking her to carry this weight?

How long could I keep chasing my stupid dream while she held everything else together and put off her own dreams?

She deserved an answer, but I had nothing.

A Glimmer of Hope

The breakthrough came from an unexpected direction.

My partner was in an accounting community, and when word got around that we were helping businesses hire in the Philippines, firm owners started asking questions.

Accounting firms were entirely different.

For eCom companies, new hires were a nice-to-have.

But accountants were drowning in work and couldn't grow without more people.

I'll never forget my first discovery call with a firm owner.

She'd been unable to hire a quality American bookkeeper at nearly any price. She was working insane hours and her health was suffering.

At the end of that call, I sat back, completely dumbfounded.

It was such an easy problem to solve.

I'd already learned the hard lessons in hiring overseas, so sourcing great talent was no big deal now.

Then, when we started helping these accountants, they were thrilled and told their friends.

We’d stumbled onto something far bigger than I’d imagined.

Making A Difference

We were changing lives.

Overworked accountants could finally get the help they were desperate for.

Firms that had been stuck were growing again.

On the Philippines side, salaries were much higher than local rates, and they could work from home.

A mom with young kids could double her salary, and without the brutal commute, she could have five more hours with them every day.

For the first time, it felt like I was doing the work I was made for.

And maybe, just maybe, I could finally live up to my promise.

The Outsourcing Temptation

That's when I started looking at the outsourcing companies.

When I saw their pricing, I nearly fell out of my chair.

When these companies hired someone for $1,000 per month, they'd charge the firm $2,000, or sometimes even $3,000!

I saw dollar signs.

But why were firms willing to pay that huge markup, forever?

Then I remembered that discovery call. She had a problem she couldn't solve, so of course she would pay it.

In that moment, this felt like salvation.

I could continue helping people, but now with recurring revenue and even better margins!

I wasn’t dreaming about getting rich. I was dreaming of telling my wife we were okay.

So we thought we'd give it a try.

Still, I couldn’t shake the feeling: firms would eventually start asking what they were really paying for.

My partner said we should offer ongoing coaching to defend our value, but I was skeptical.

Once you're working well with someone, what coaching do you need?

We moved ahead anyway, adding contract clauses to prevent clients from hiring staff directly.

It felt wrong, like a trap our clients would resent.

After a few months, I couldn't believe the money we were making for basically doing nothing.

But something kept gnawing at me.

It was too easy. How could I keep skimming off the top without adding any real value?

Then I Found Something

With all this on my mind, I started digging deeper.

And I found something that, to this day, I still don't understand.

There were no companies specializing in direct-hire recruiting for accountants in the Philippines.

None.

Every single accounting-focused company was using the outsourcing model.

How was this possible?

Could I really be the first to bring this to accounting firms?

But that would mean walking away from the easy outsourcing money.

It would mean being a pioneer: choosing the hard road instead of following the crowd.

Lost In Confusion

I had found something truly incredible.

Yet in my profoundly scattered state, I had no idea what to do.

Every time I tried to focus on recruiting, I’d get pulled back into bookkeeping or our marketing service, which was struggling with fulfillment.

I was doing too many things, and none of them very well.

Recruiting was clearly the bright spot, but I couldn't give it the attention it deserved.

And my partner and I were starting to have disagreements.

I wanted to simplify things and focus on what was working, but he wanted to keep adding more complexity.

He was also adamant about sticking with the outsourcing model—not recruiting.

And all our accounting clients came from his network, so if he wanted to offer outsourcing, he would.

So, instead of celebrating my discovery, I was drowning in confusion.

The Cost of Adventure

That night on the couch, after my wife asked if I'd ever stop and get a job, I just sat there.

I couldn't answer.

"It's been eight years," she said.

Eight years since that reckless promise.

Eight years since I'd convinced her to quit the job she loved, sell our condo, and move in with my parents, all so I could chase this dream.

Eight years of, “That business didn’t work, but I have a new idea."

And then the comparison hit me.

In my first eight years of work, I was an architect.

I'd helped design neighborhoods across the country. An entire city in Guatemala. A stadium in Fort Worth. Amazing houses for the Washington, DC elite.

The guy she married had a career that people envied. He was building real places.

Now, after another eight years, I had started seven businesses and I was still just spinning.

What was I doing? Was I ever going to make it?

At this point, even I was starting to wonder if I had enough optimism left for yet another business if this one didn’t work out.

The Uncle

Then she said the last thing she'd ever need to say:

"I don't want you to become my uncle."

We both knew the story she was afraid of.

Her uncle was a good man who'd spent his life going from job to job, never able to hold onto one, always with a reason why it didn't work out.

The stress and financial strain followed him into his marriage, his kids' lives, social circles, everywhere.

What if I grew old and none of my businesses ever worked out? What if I never fulfilled my promise?

What if I became her uncle?

That was my greatest fear.

What Could I Do?

I didn’t have any answers, but maybe Bangkok would.

The annual Dynamite Circle conference in Bangkok, the one that had always given me direction when I needed it most, was coming up.

And I needed clarity more than ever.

The shadow of becoming her uncle crept closer every day.

I was 41 years old—if I didn't figure this out now, when would I?

She Was Searching Too

Half the world away, someone else was searching for answers.

She’d followed the path everyone celebrated—founder turned investor and advisor. But it didn’t quiet the ache inside.

She thought about the industry she loved and the accountants now facing the challenge that would define them.

She’d survived an outsourcing nightmare, and now she watched her friends walking into the same trap.

There had to be a way to help them.

That would be a mission worth taking on.

She wished she could join her friends in Bangkok, but she was still recovering from surgery.

The Person I Didn't Meet

In Bangkok, I was scheduled to lead a breakout session on what I'd learned about hiring in the Philippines.

Maybe someone would show me what to do.

What I didn’t know was that the person who could, was the very one who’d inspired me to start my bookkeeping firm in the first place.

If she had come, she could have walked into my session and joined in the discussion.

If she had come, we could have talked for hours about the industry's biggest problem.

If she had come, we could have realized we'd both been searching for the same thing.

If she had come, we could have discovered a rare alignment of vision, of timing. Purpose.

If only she'd come...

But she didn't.

So, I would have to find my answers somewhere else.

----

I knew a choice was waiting for me.

I just didn’t know how much I’d have to let go of.

So on that dreary Portland day in October, backpack over one shoulder—

I boarded the plane, carrying with me so much hope and dread, desperate for transformation but completely unprepared for what would happen next.

To Be Continued...

That's all for today.

Next week, we'll pick up in Bangkok—where I finally found the clarity I’d been searching for.

But that clarity came with a terrifying price:
a choice I couldn’t avoid.

I’ll tell you about my packed breakout session, the message that seemed to follow me everywhere, and the moment I finally understood what the speaker meant.

And I’ll share the email that arrived just after I got back,
with the words that changed everything:

"Hey Isaac..."

Thanks for coming on this journey with me.

Cheers!

Isaac
Co-founder
TeamUp

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