Cherry Hill Private Wealth at Harbourfront Wealth Management

Had lunch with a founder recently who'd just launched a new company. Exciting product, real opportunity, the kind of energy that only comes at the beginning of something you genuinely believe in.

But underneath the excitement was the weight of a lot of decisions — corporate structure, cross-border complexity, investor readiness, personal financial planning — all happening at the same time as just trying to build something great.

The early days of a venture are all-consuming. The planning pieces feel like they can wait. The problem is they're not neutral while you're waiting. The structure you set up on day one shapes everything that comes after it.

Wrote about it in this week's From the Ridgeline — fromtheridgeline.com

A founder reached out to me a while back. He'd closed an exit, was already deep into his next venture, and had seven figures sitting in a bank account earning essentially nothing.
Not because he didn't know better. Because he was head down building and never stopped long enough to deal with it.

Two years went by. The new business found its footing without needing that capital. But by the time we sat down, the money had been sitting idle the entire time.
This is more common than most founders talk about. You're exceptional at deploying capital into what you're building. But liquid capital outside the business? It gets neglected because there's always something more pressing.

Wrote about it in this week's From the Ridgeline — fromtheridgeline.com

I was catching up with a founder friend over a glass of wine. He was telling me about some restructuring he's doing across his businesses — smart, proactive moves.

Then he paused mid-sentence.

He started listing all the professionals involved. Private banker, two accountants, two lawyers, insurance advisor, investment person. All good at what they do. None of them coordinating with each other.

And the person making sure it all came together? Him.

He looked at me and said: "I'm basically the CFO of my own personal life."

It's one of the most common things I hear from founders — not because their advisors aren't good, but because nobody is looking at the whole picture at the same time.

Worth asking yourself: who is actually quarterbacking your financial life right now? And is that the best use of your time?

I write about exactly this in From the Ridgeline — a short letter for founders and business owners. If someone you know would find it useful, feel free to share this post or pass along the newsletter.

Last ski season I was skinning into a backcountry bowl with a few guys. Fresh snow, good crew, solid plan.

We still missed where we were trying to go.

We had all the information we needed — we just couldn't see the terrain properly from where we were standing. It wasn't until we got to higher ground that the right line became obvious.

I find myself thinking about that a lot with the founders and business owners I work with.

Everyone has a lawyer, an accountant, an investment person. Everyone is doing their job. But when nobody is looking at the whole picture — the business structure, the personal finances, the tax exposure, the estate — things get missed. Not because anyone did anything wrong. Just because good work in isolation isn't the same as good work coordinated.

Worth asking yourself: who is actually coordinating your financial life right now?

Hosted a small group to learn more about secondary private markets with Simon Oak from and . Great content, great company, and great food!