Tuesday Email: Each executed idea breeds new insights

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

I was staring at a bank account that read $0.00. Not $100. Not $1,000. Zero.

Two years earlier, I'd raised over $7 million. We had ten people on the team, fifty RIAs using our technology, and a vision to transform how advisors serve families. The kind of ambitious dream that keeps you up at night in the best way.

Now I was closing the doors.

Here's what surprised me: the moment we failed wasn't the moment I learned. The learning came three months later, in the silence that followed the noise. That's when I realized something our entire industry needs to hear.

We've confused thinking about doing with actual doing. In wealth management, we've built a culture that worships at the altar of analysis. We study, we model, we strategize. We attend conferences about innovation, but rarely innovate. We read case studies about transformation, but hesitate to transform.

Why? Because analysis feels safe. It looks productive. You can't fail while you're still planning.

But here's the truth I learned at $0: The insights that actually matter only reveal themselves through action. Consider how we actually become good at anything. Aristotle observed that "men become builders by building." Not by studying architecture. Not by analyzing blueprints for 10,000 hours. By picking up the hammer and making mistakes with real wood.

When I was running my startup, I spent months before launch perfecting our financial models and market analysis. Those models taught me almost nothing. You know what taught me everything? The first conversation with an RIA who said our pricing made no sense. The moment an integration broke at 2:00 AM, just before a demo. The day a competitor launched a feature, we'd dismissed as unimportant.

The messy, uncomfortable action revealed what six months of analysis had obscured.

But we avoid action because we've misidentified the enemy.

We tell ourselves we're afraid of failure. That's not quite right.

A child learning to ride a bike isn't afraid of falling—scraped knees heal in a week. They're afraid of their parents' disappointed faces. They're afraid the neighbor kid will see them crash. They're terrified of internalizing the story: "I'm the kid who can't ride a bike." The feeling of being a failure outlasts the act of failing by years.

In an industry obsessed with performance and quarterly results, this fear becomes paralyzing. We only want to perform when applause is guaranteed. We approach opportunities like actors at an audition, instead of a rehearsal—showing up only when success is certain, missing entirely that mastery develops backstage in the chaos.

This creates a cruel irony: The very professionalism we pride ourselves on becomes the barrier to progress.

So we've invented sophisticated ways to justify inaction.

We calculate the cost of what might go wrong with painful precision. We model the downside of every experiment. But we rarely calculate the cost of not experimenting at all.

It works like this: A homeowner discovers a small roof leak. Fixing it would cost $500, which feels expensive and uncertain—what if the leak is worse than it appears? So they monitor it instead. They analyze. Six months later, when mold has rotted the beams and a portion of the ceiling collapses, the $15,000 emergency replacement makes the $500 look like a gift. But by then, they've forgotten they ever had a choice.

The cost of inaction compounds silently while the cost of action announces itself loudly.

When I had fifty clients and ten employees, staying the course felt responsible. Pivoting felt reckless. The known ROI of our current approach beats the uncertain ROI of experimentation every time in our analysis.

But what we never calculated: the cost of not discovering that our pricing model was broken. The cost of not learning earlier was that our target market was too small. The cost of not finding out which features actually mattered until we'd built the ones that didn't.

Reactivity isn't cheaper than proactivity—it just sends the bill later with interest.

Here's the reframe that changes everything: Stop launching initiatives. Start running experiments.

The difference is profound. Initiatives demand ROI.

Experiments generate insights. When something is an initiative, failure feels personal. When it's an experiment, failure is just data.

A novelist who only writes sentences they know are brilliant ends up with a pristine blank page. The "worthless" paragraphs in a messy first draft teach you what your book is actually about. You can't think your way to that knowledge—you have to write your way there.

What if you approached that new client service model as an experiment with five clients instead of a firm-wide initiative?

What if you tested that technology integration with a single team for a month?

What if you ran that content strategy with ten prospects before committing to a year-long plan?

Small experiments compound into major insights. Each executed idea breeds new ideas. The doing creates a feedback loop that analysis can never replicate.

So here's the question:

-What's one thing you've been analyzing for months?

-What's the smallest version of that thing you could test this week?

Not perfect. Not proven. Just done.

Because the insight you need isn't hiding in another spreadsheet or waiting in the next planning session. It's out there in the action you keep postponing.

And unlike my bank account in that final moment, your opportunity to act isn't at zero yet.

But the meter's running.

The best is ahead!

-Matt