Article
September 10, 2025
Last time, I shared how Meryl and I finally met, and how it felt like we'd found the answers we'd been searching for.
The vision was clear, the timing was right.
It seemed like a perfect fit.
But it couldn't be that simple... could it?
Today I'll tell you what happened next.
If you missed the last one, you can click here to get caught up.
For a moment, it seemed inevitable.
In those first few calls with Meryl, everything clicked into place.
It was uncanny, like we’d each been carrying the missing piece to the other’s puzzle without knowing it.
A perfect match of experience, knowledge, and mission.
I’d admired her work for years. Now here she was, and she wanted to work with me.
It felt… unreal.
All we had to do was start.
But reality wouldn't be that simple.
I already had a business, a partner, and I was tangled up in bookkeeping, content marketing, recruiting, and outsourcing.
How was I supposed to bring Meryl in without blowing up everything else?
This is different, she thought.
Meryl was more excited about this than anything else she was looking at:
Accounting apps, service providers, web3 experiments… all interesting, sure.
But this could move the entire industry.
She’d spent the past year trying to figure out what her next chapter would look like.
After everything she’d been through: cancer, recovery, identity upheaval...
She’d done well with Bean Ninjas, but deep down, she still felt like she was meant for more.
And here was a model she understood instinctively.
The recruiting approach was clean, transparent, and scalable, exactly the thing she’d wished existed when she built her team.
She felt a familiar drive to jump in and make it happen.
But Meryl was an investor now.
That was the role she’d committed to after stepping down as CEO.
So she held back.
She’d provide capital, connections, and give advice.
But she wouldn't get her hands dirty.
Instead of walking away from my existing business, I tried to channel the energy I’d brought back from Bangkok into what I’d already built.
My partner agreed to let me lead the team-building arm and stay out of our other services.
With Meryl in the picture, it felt like we had the chance to build something special.
But how would that work… with three of us?
After a few rounds of discussion, I started drafting a partnership agreement.
On paper, it looked like progress.
I typed out the roles:
Meryl: advisor, industry connections, brand credibility.
Me: recruiting fulfillment, sales & marketing.
My partner: CFO, business & entity structure.
--
Meryl was eager to understand how this partnership would work in practice.
She knew Isaac's role. That part was obvious.
But Isaac's partner's role wasn’t as clear.
So, she decided to get on a call with him.
If the roles were clear, and the vision stayed sharp, maybe they really could build something great.
--
My stomach tightened as I typed the letters “CFO.”
I paused. Why does a startup like this need a CFO partner?
I tried to move forward, but the thought wouldn’t leave me alone.
Oh no. I'm doing it again...
--
On the call, Isaac's partner was friendly, easy to talk to.
But when she asked about his responsibilities in the new partnership, his answers got… fuzzy.
“I’ll be CFO, managing finance and cash planning, and be in charge of entity structure,” he said.
When she pressed for specifics — what exactly that meant and how he’d do it, he gave vague responses.
He reminded her of people she’d worked with who sounded competent but avoided clarity.
She'd never been able to work well with them.
Feeling a little uneasy, but still excited about the business, she sent Isaac a message.
--
Meryl told me about the challenges she saw:
"He seems like a lovely guy, but I haven't worked well with people like him in the past.
I’m still happy to be involved, but if we do this, I’d prefer to coordinate through you.”
So it's not just me.
I’d had doubts about this three-way partnership from the beginning, but I kept telling myself I could make it work.
If I just kept the peace… maybe I wouldn’t have to choose.
I'd always felt conflicted about giving my partner a piece of the recruiting business.
Back when we launched the bookkeeping business together, we had grand visions of helping eCommerce businesses with everything —
bookkeeping, marketing, recruiting, and more.
We fooled ourselves into thinking we were great visionaries, believing we could do it all.
So, when I decided to start an online course on how to build teams, I didn't know what to do.
The course came from my experience and I did all the work.
My wife warned me repeatedly:
“It doesn't make any sense for this to be part of a bookkeeping business. You should just start a new business on your own.”
But I ignored her.
Partly because I didn’t want the conflict.
Partly because I'd kind of agreed that anything eCommerce-related would be included in the partnership.
Over time, the course evolved into the recruiting service, which I ran.
Eventually, through my partner's network, we discovered accountants needed recruiting help too.
And, that's what turned into the opportunity I now had.
So, while I’d been conflicted in the beginning, keeping it in the partnership seemed to work out.
But did that mean I now owed him a third of a future business that might not need him?
Sitting there drafting this new agreement, I could feel the weight of that old decision pressing down on me.
I was about to give away another part of what I’d built…
just to keep the peace.
There was another difference between us.
My partner still insisted on the outsourcing model.
But Meryl and I were aligned on recruiting.
And I kept telling myself we could do both.
I’d focus on recruiting. He would handle outsourcing.
It sounded reasonable enough, but my heart I knew it was naïve.
The two models came from opposing philosophies.
Recruiting felt fair: firms hired the talent, paid them directly, built their own teams.
With outsourcing, someone was always in the middle siphoning value, adding little if anything.
How could I make a strong argument for recruiting if my company was offering outsourcing?
Even with questions hanging in the air, Meryl was still excited.
But if she was going to invest, they’d need a new entity.
Isaac’s partner took the lead.
He seemed confident, said he had experience, and Isaac deferred to him.
“We should create entities in the U.S., Canada, and Australia, all owned by a Singapore corporation. It’ll be the most tax-efficient structure,” he said.
Bean Ninjas was registered in multiple countries, so Meryl knew how complex international business could get.
She wasn’t sure a Singapore entity was necessary, but she was open to it.
Let’s see what he puts together, she thought.
He said he'd come back with a plan.
Meryl was eager, but patient.
A week went by.
She asked Isaac an update, and Isaac replied that his partner said he was working on it.
Meryl was an action-taker.
She liked speed and momentum, which was how she’d grown Bean Ninjas.
But now that she was an investor, she had to be more passive.
It was irritating.
A week later Isaac relayed another message:
“Still researching. A lot to figure out.”
She waited yet another week, much longer than she wanted to.
Meryl didn’t want to push too hard, but after weeks of waiting she couldn't stand it any longer.
So she emailed Isaac’s partner:
"Just checking in. Any progress on the structure?"
His reply came three days later.
One line, a plain URL.
No plan, no explanation.
Just a link.
--
When I opened my partner's email, it took a moment to register, then my face went hot.
I clicked, hoping I was missing something.
It was a Singapore government website, an FAQ...
Something anyone could find with a 10-second search.
--
Meryl sat back in her chair, confused at first, then frustrated.
This was really disappointing.
It wasn’t the link, but what it meant.
She waited weeks and weeks for this?
If the three of them couldn’t take this first step together with conviction, how would they ever build a great business?
--
Why would he do that?
I was mortified.
Here was someone I admired, who to my great surprise and delight, wanted to work with me.
And I was blowing it.
With weeks lost and momentum slipping, I wondered if the three of us should do this together at all.
I thought about those first calls with Meryl — the alignment we’d found, the sense that we saw the world the same way.
We both liked to move fast, to act with purpose, to make things happen.
And between the two of us, we had everything we needed.
What if just she and I built this together?
I closed my eyes and pictured it.
Our recruiting business would disrupt the outsourcing industry.
We would change lives, the perception of global talent, and how teams are built.
I saw a client base hungrier than I’d ever experienced. We had thrilling traction and acceleration.
After all those years of hardship and failure, something would finally work. Beyond my wildest dreams, even.
My wife would get tired of hearing me say, “I can’t believe this is happening.”
Sitting at our kitchen table, with annoyance in her eyes, she would say for the hundredth time:
“Well, you know, it has been ten years. It was bound to work eventually.”
I sat on the couch with my laptop, the partnership doc on the screen.
I thought of Meryl's first email to me, the one that started it all.
My journal lay open beside me.
At the top of a blank page, I’d written:
"What do I want?"
My wife came over to say goodnight. She was tired.
This wasn’t what I’d promised her.
--
Meryl could see it so clearly.
This could be the mission I've been looking for.
It could actually change the industry.
But she could also see Isaac — hesitant, cautious, holding back.
She sensed he didn’t yet grasp the magnitude of what he'd found.
Should I tell him what this really is? Should I push him?
Watching him on those video calls, she saw fragility beneath his talk of adventure.
Something was keeping him from making the obvious move.
If she pushed and they failed, she'd be the one who broke him.
Besides, he'd want more from her then.
And she was an investor now, not a founder.
So she waited.
--
This was the calling I was born for.
Together, Meryl and I could build something incredible.
It was right there… and still, I froze.
What if I was wrong again?
What if business number eight failed too?
How could I answer my wife's question about getting a job then?
Would I be the uncle?
I thought about Bangkok.
The speaker on stage had made it so simple.
“You must choose.”
In the stillness of night, I stared at my open journal, the empty page.
I couldn’t move.
So I chose to stay.
We knew what we should have done.
I was born for adventure.
I should have gone all in and built a recruiting company that would change the industry.
But I was terrified of giving up the stability that had taken me eight years to build.
Meryl was meant for more.
She should have embraced who she really was, a founder, and taken on the mission with me.
But she was afraid to give up the comfort of her new identity as founder-turned-investor.
Besides, we'd figure this agreement out.
Maybe we wouldn’t achieve that bigger vision —
but surely we would make something happen.
Something decent.
Eventually.
…wouldn’t we?
Ultimately, I didn't want to turn my life upside down again.
And she wasn’t ready to risk becoming a founder again.
--
So, at the end of 2022, a year that was supposed to be transformative for both of us -
Though everything inside screamed at us to leap...
Meryl and I did nothing.
Our budding partnership ground to a halt.
She didn't want to push me.
I didn't want to rock the boat.
She would stay the unfulfilled investor.
I would remain scattered and frustrated.
The firms and talented people in the Philippines who needed our help would have to wait.
We were just too afraid to bet on ourselves.
--
The dreams we had would remain just that—dreams, with both of us unwilling to chase them.
Maybe that's all we were meant for anyway.
Isaac
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