How to Find Meaning in Leadership

In partnership with

Without meaning, leadership becomes a weight you carry instead of a leg you stand on.

Sometimes you have to amputate the empty chase for more.

To elevate into purpose.

This week’s episode features Masami Sato, founder of B1G1, whose journey from Japan to building a global giving movement reframes what it means to lead with depth and purpose.

Why this Matters to Leadership Right Now

In high-stakes transitions, leaders often chase growth at all cost.

But the truth is, meaning not scale— is what sustains influence, inspires teams, and creates lasting impact.

Masami reminds us that prosperity comes from contribution, connection, and the courage to let go of judgment.

How 433 Investors Unlocked 400X Return Potential

Institutional investors back startups to unlock outsized returns. Regular investors have to wait. But not anymore. Thanks to regulatory updates, some companies are doing things differently.

Take Revolut. In 2016, 433 regular people invested an average of $2,730. Today? They got a 400X buyout offer from the company, as Revolut’s valuation increased 89,900% in the same timeframe.

No wonder 10K+ everyday people are taking the chance on Pacaso.

Founded by a former Zillow exec, Pacaso’s co-ownership tech reshapes the $1.3T vacation home market. They’ve earned $110M+ in gross profit to date, including 41% YoY growth in 2024 alone. They even reserved the Nasdaq ticker PCSO.

The same institutional investors behind Uber, Venmo, and eBay backed Pacaso. And you can join them. But not for long. Pacaso’s investment opportunity ends September 18.

Invest While You Still Can

_{Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.}

3 Executive Insights & Micro- Actions

Insight 1: Amputate Judgment

Judgment separates us from others and ourselves. Masami’s story reveals how letting go of judgment opens the door to authentic connections.

Insight 2: Embrace the Power of Small

Small, consistent actions create massive ripple effects. The big wins are built on small steps done faithfully.

Insight 3: Redefine Prosperity

Success without meaning is short-lived. Prosperity is found in gratitude, sustainability, and the contribution you make.

Summary Challenge

Choose one belief or habit that keeps you from experiencing meaning in your leadership.

Amputate it, and replace it with one purposeful action.

Registration Is Now open - Reserve your Seat Now

Saturday’s Sneak-Peak

Saturday’s ThinkLetter will be a “how-to breakdown” with Masami Sato, going even deeper into her frameworks for finding meaning in leadership.

That episode will sit behind the Skin in the Game wall, because transformation requires commitment.

I’ll also be in Chicago speaking for Hugh and Grace, sharing amputate to elevate strategies with their company leaders.

And next week, we sit down with Paul Gravley, CEO and President of Didlake — a leading nonprofit organization that creates opportunities and employment for people with disabilities, empowering them to lead more independent and fulfilling lives.

Go forth - Inspire your world