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).

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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

---
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

Your story isn’t too messy, too boring, or too personal to share.
It’s the very thing that sets you apart.

And Holly Crawshaw Joyner has built her entire business helping leaders do exactly that.

Holly’s ghostwritten 120+ books and built a standout brand on LinkedIn by being raw, honest, and far from perfect. She knows what it takes to turn life experience into the kind of authority that makes people stop scrolling, and start listening.

In this episode, Holly joins Stacy to discuss:

• The behind-the-scenes lessons from ghostwriting 120+ books (and what actually makes a good one)
• How she built her business, The Story Spark, as a single mom during the pandemic
• The honesty-over-perfection strategy that made her brand stand out on LinkedIn
• Why LinkedIn is still the most underrated platform for introverts + thought leaders
• Smart AI hacks to turn posts, podcasts, and raw ideas into publishable content
• The real talk on self, hybrid, and traditional publishing (and how to know which path is right for you)

If you’ve ever thought about publishing a book, or finally leveraging LinkedIn to grow your business, this conversation will help you find the courage to get started.

More about Holly:

Holly Crawshaw Joyner is a New York Times-bestselling ghostwriter.

Since entering publishing in 2006, Holly has ghostwritten, edited, and coached well over 1,000 titles. In addition to the NYT Bestseller, other projects Holly has worked on have topped the most prestigious lists in the industry including Amazon Bestseller, Amazon Best New Release, and Amazon Top 100, among others.

She’s written books for all the major publishing houses, including HarperCollins, Penguin, Random House, Baker, and Hachette.

Since 2021, Holly has also been ghostwriting for and coaching clients on LinkedIn, teaching them how to build a brand and grow an engaged audience. In 2024 Holly was named the #1 U.S. LinkedIn creator for Audience Building and Brand Awareness. In 2025 she was listed as one of the Top 20 LinkedIn experts worldwide.

Holly is married to Drew. They live in Atlanta with her three daughters. She is a self-professed cat lady with an addiction to sour candy.

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

People matter more than performance. Yes, even in a numbers-obsessed industry.

Take it from Karl Heckenberg, founder of Constellation Wealth Capital, a $1B platform that takes minority, non-controlling stakes in large RIAs and wealth management firms.

Yes, he understands the numbers and mechanics behind investing. But what actually sets him (and his fund) apart is the fact that he builds real partnerships.

In this episode, he sits down with Stacy to talk about:

• His backstory: from investment banker to CEO, and how he built a $1B platform by betting on people
• Why founder-led firms outperform (and how Constellation supports them)
• What makes a capital partner “friendly” (and what doesn’t)
• Ownership and succession blind spots in wealth and asset management
• Lessons from 40+ deals that apply to any founder looking to grow
• The real ROI of relationships, connection, and shared values

More about Karl:
Karl serves as the President and Managing Partner of Constellation Wealth Capital. Before founding CWC, Karl was the CEO of Emigrant Partners and its affiliated company, Fiduciary Network. His career in the financial services has taken him to renowned institutions like Merrill Lynch, A.G. Edwards & Sons, Wells Fargo, and Charles Schwab. Karl has also contributed his expertise to several boards, including Sarasota Private Trust Company, New York Private Trust Company, and Cleveland Private Trust Company, and is currently on the board at Alternative Fund Advisors. He also held the position of Vice Chairman at Emigrant Bank and chairs the CWC Investment Committee.

A Washington, D.C. native, Karl is an alumnus of Saint Joseph’s University in Philadelphia.

Books Mentioned in This Episode:

• The Psychology of Money – Morgan Housel | https://a.co/d/j4ZWvk2
• Moneyball: The Art of Winning an Unfair Game — Michael Lewis | https://www.amazon.com/dp/0393324818
• The Big Short: Inside the Doomsday Machine — Michael Lewis | https://www.amazon.com/dp/0393338827
• The Undoing Project: A Friendship That Changed Our Minds — Michael Lewis | https://www.amazon.com/dp/0393354776
  
  

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

What if the most powerful thing a CEO can do… is show up?

That’s exactly what John Bowman is doing. As the new CEO of CAIA, he’s not sitting behind a desk or delegating from an ivory tower. He’s on a plane, in person, listening to the very people his organization serves.

In this episode, Stacy sits down with John to talk about the underrated power of founder-led sales (even when you’re leading a global organization), the ROI of empathy, and why success in finance is less about numbers and more about people than you think.

They dig into:

• John’s backstory: The leadership lesson he learned after getting laid off at 29 with three kids
• Why walking the “listening tour” isn’t just smart, it’s essential
• How storytelling shaped his career in this number-obsessed industry
• What CAIA’s member-first strategy can teach every founder and fund manager

Why he believes rejection is almost always redirection that’s either protecting you or leading you to where you’re meant to be

More About John:

John was appointed CEO for the CAIA Association in January 2025. He has devoted over 25 years to the asset management industry to recover the narrative of the value that the investment profession brings to society. He is a staunch public advocate for market integrity, long-termism, investor outcomes, diversity, human dignity and educational standards, as necessary ingredients to building a sustainable and healthy profession.

John previously served as Managing Director for the Americas for CFA Institute, a region comprised of 40+ countries from Canada, the U.S., Central America, South America and the Caribbean. Before that, John was a portfolio manager for non-US equity strategies at both Boston Company and SSgA for several years.

John is a prolific, speaker,writer and commentator, frequently keynoting industry conferences and appearing in investment and business publications such as the Wall Street Journal, The New York Times, Pension and Investments, Financial Advisor, The Independent, Wealthmanagement.com and CNBC. Bowman earned a BS in Business Administration from Mary Washington College and is a CFA charterholder.

Books Mentioned in This Episode:

• The Advantage – Patrick Lencioni | https://a.co/d/2msVUSw
• The 6 Types of Working Genius — Patrick M. Lencioni | https://a.co/d/15S3sKW
• Tribes: We Need You to Lead Us — Seth Godin | https://a.co/d/ajf88KP

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

You’ve got your pitch deck. Your talking points. Your “why us” slide.
But if you’re telling the wrong story in meetings, none of that matters.

In this episode, Stacy’s diving into the two MVPs of storytelling for fund managers: the job story and the brand story. Think of them like the hammer and wrench in your toolbox, you need both, but you’ve gotta know when to use each.

Inside this bite-sized episode, you’ll learn:
• What makes a job story different from a brand story (and why that mix-up matters)
• Why every fund or strategy deserves its own tailored story
• How constantly tweaking your brand story for the room can make your message… fuzzy

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

The impressively bold mindset that drove Chad Willardson to leave behind a million-dollar salary and a top 1% client base to build his own firm from scratch is the same mindset that grew his firm to $1.5B AUM and earned him the status of 5X bestselling author.

In fact, Chad’s story is proof that thinking like an entrepreneur can take you far in the fund world–and beyond. But can this mindset be learned and developed? Find out in today’s episode.

Plus, hear Chad’s full backstory and learn:

• Why advisors who think like entrepreneurs stand out to high-net-worth clients
• The hidden benefit of his LinkedIn presence: how he’s able to pass off sales meetings to his team almost entirely thanks to the strong trust he’s built on social
• His tips and tricks for balancing entrepreneurship and family life

About Chad Willardson:

Chad Willardson is the President and Founder of Platinum Elevated, an exclusive coaching program where he helps entrepreneurs enjoy increased lifestyle and financial freedom by removing their stress about money, increasing their cash flow, and freeing up a ton of their time.

In 2011, Chad founded Pacific Capital, a family office specializing in wealth management for high-net-worth entrepreneurs. Chad's currently responsible for investing $1.5 billion dollars as a fiduciary. Before founding Pacific Capital, he spent nine years at Merrill Lynch, ranking in the top 2% of over 16,000 advisors nationwide.

Chad is a 5X best-selling author and Co-Host of The Smart Money Parenting Show, a podcast ranking in at #2 Apple for Parenting, Kids & Family. He is a Certified Financial Fiduciary® and Accredited Wealth Manager who also writes for Entrepreneur and Forbes. Chad earned his degree in Economics from Brigham Young University.

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