A lot of people build firms.
Very few sell them.
Even fewer?
Walk away from it all to start again.

But that’s exactly what Toussaint Bailey did.

After building and selling a $2B RIA, he’s back on the founder path, this time leading Uplifting Capital, a values-first platform rethinking what private market investing could look like.

In this episode, he sits down with Stacy to discuss:

• His backstory – How growing up in SoCal shaped his belief in “actionable faith in possibility”
• Why he left a law partnership to help build an RIA
• The cultural ethos that scaled Enso Wealth to $2B AUM and an eventual exit
• Why he launched Uplifting Capital and how it’s redefining access to values-aligned private markets
• A storytelling framework any fund manager can use to stand out (hint: it starts with “we’re not that.”)

About Toussaint Bailey:

Toussaint’s career has been built on a belief in the promise of possibility. As Founder and Managing Partner at Uplifting Capital, this belief manifests itself as investment in “Impact Alpha,” funds, and companies that produce compelling financial performance through gap-closing solutions in critical areas like education, healthcare, affordable housing, and renewable energy.

Prior to founding Uplifting Capital, he was CEO and Chairman of Enso Wealth Management, a private wealth firm with a mission to translate wealth into fulfillment for clients and advisors. Toussaint joined Enso shortly after its formation in 2017, overseeing the firm’s rapid growth to nearly $2 billion of assets under management and its eventual acquisition. Before financial services, Toussaint spent over a decade as a practicing attorney.

Toussaint has served in several advisory and board capacities, including Impact Investment Subcommittee of the Alternative & Direct Investment Securities Association; Investor Advisory Board of HBCU Founder Initiative; Advisory Board of Catalyst Housing Group; Advisory Board of SIY Global; and Board of Regents of Saint Mary’s College of California.

Resources Mentioned in This Episode:

Book: Finding Meaning by David Kessler (the “sixth stage” of grief: finding meaning).

Want More Help With Storytelling?

+ Subscribe to my newsletter to get a weekly email that helps you use your words to power your growth:https://www.stacyhavener.com/subscribe

- - -
Make The Boutique Investment Collective part of your Billion Dollar Backstory. Gain access to invaluable resources, expert coaches, and a supportive community of other boutique founders, fund managers, and investment pros. Join Havener Capital’s exclusive membership

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Running a fund is hard enough.
Ops shouldn’t be.
Meet the team that makes it easier. | billiondollarbackstory.com/ultimus

The finance and investment industry is a tough club. It’s known for being money-centric, number-focused, aggressive… even cutthroat.

And few places capture that intense energy quite like the trading floor of the NYSE, where today’s guest, Joe Greco, cut his teeth.

He started as a floor trader and media commentator, appearing on CNBC and guiding real-time market decisions.

Today, as Founder & President of PALIO, Joe coaches executives in wealth, finance, and investing, helping them make high-stakes decisions with clarity, speed, and trust.

In this episode, Joe sits down with Stacy to discuss:

• Why he left the chaos of Wall Street to coach the C-suite
• How being a husband and father of five reframed his definition of success
• What Wall Street taught him about leading with clarity and speed
• The future of AI in Finance

More about Joe:

Joseph Greco is the Founder & President of PALIO, where he coaches high-performing leaders and teams in finance and beyond. A former NYSE trader and media commentator, Joe blends financial acumen with behavioral insight to drive growth, alignment, and leadership transformation.

He’s also an active investor in commercial real estate and global sports teams, including Campobasso 1919, Ascoli FC, and Brooklyn FC.

Joe lives in Larchmont, NY with his wife and five daughters, and brings a spirit of faith, adventure, and continuous growth to everything he does.

Books Mentioned in This Episode:
Rerum Novarum: Encyclical Letter of Pope Leo XIII On Capital and Labour | https://a.co/d/dW1CdSU

Want More Help With Storytelling?

+ Subscribe to my newsletter to get a weekly email that helps you use your words to power your growth:https://www.stacyhavener.com/subscribe

- - -
Make The Boutique Investment Collective part of your Billion Dollar Backstory. Gain access to invaluable resources, expert coaches, and a supportive community of other boutique founders, fund managers, and investment pros. Join Havener Capital’s exclusive membership

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Running a fund is hard enough.
Ops shouldn’t be.
Meet the team that makes it easier. | billiondollarbackstory.com/ultimus

The chart you shared on LinkedIn isn’t flopping because people “don’t get it.”
It’s flopping because you made them work too hard to understand it.

That’s one of the most common content mistakes fund managers make:dropping data without enough context.

The good news? It’s an easy fix, and in this episode, Stacy shows you how.

She dives into:
• 3 quick rules to make your chart posts actually land
• A better way to use data to tell a story
• Why one great chart beats four cluttered ones every time

This is Story Snacks, a bite-sized, jam-packed series for fund managers who are ready to master strategic storytelling in under 20 minutes a week.

Want More Help With Storytelling?

+ Subscribe to my newsletter to get a weekly email that helps you use your words to power your growth:https://www.stacyhavener.com/subscribe

- - -
Make The Boutique Investment Collective part of your Billion Dollar Backstory. Gain access to invaluable resources, expert coaches, and a supportive community of other boutique founders, fund managers, and investment pros. Join Havener Capital’s exclusive membership

---
Running a fund is hard enough.
Ops shouldn’t be.
Meet the team that makes it easier. | billiondollarbackstory.com/ultimus