119:Toussaint Bailey, Exited Founder of a $2B RIA + Managing Partner of Uplifting Capital, on Differentiation, Values-Aligned Investing, and What Comes After a Big Exit

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?

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Ops shouldn’t be.
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