E22: Elliott Holland: A Guide to Achieving Wealth Through Small Business Acquisition
Planet Wealth: Fortunes of the Brave
Release Date: 08/11/2025
E36: Pamela Cytron: Wealth Isn’t Just for the Rich: How Fintech Is Changing Who Gets a Shot
Planet Wealth: Fortunes of the Brave
Pamela Cytron, founder of The Founders Arena WealthTech accelerator in Arlington, Texas, has spent more than three decades at the center of fintech, wealth management and enterprise sales. In this episode of Fortunes of the Brave, Pam and host Lance Woodson dig into how wealth is really created, who gets access to it, and why the current system leaves so many founders and everyday investors on the sidelines. They unpack the broken incentives inside venture capital, the realities of raising capital in fintech, and why sales is still a contact sport even in an AI driven world. Pam explains how...
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E35: Bridging the Wealth Gap: Founder and Investor Lessons from 2025
Planet Wealth: Fortunes of the Brave
2025 closes by revisiting the most practical lessons shared by founders, investors, and community builders across this year’s Fortunes of the Brave conversations. This recap threads together a single theme: better decisions happen when your mindset, strategy, and community support are aligned. First, we return to a mental framework for entrepreneurs and investors who feel the pressure of constant uncertainty. A five-step system called PEACE outlines how positive thinking, embracing challenge, appreciation, certainty, and empathy can reduce fear-based reactions and improve decision quality....
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E34: Michael Scarpati: Rethinking Retirement For The Rest Of Us
Planet Wealth: Fortunes of the Brave
For too long, retirement planning and independent fiduciary financial advice have felt reserved for the top 1 to 2 percent. In this episode of Fortunes of the Brave, Mary Kathryn Johnson sits down with Michael Scarpati, CEO and co founder of Retire.us, to unpack how technology and true fiduciary financial planning can finally open the doors for everyday Americans. Michael shares how his platform connects people with independent fiduciary financial advisors who focus on holistic retirement planning, not just selling products. They dig into the mindset barriers that keep people with 50,000 to...
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E33: Dan Egan: The Behavior That Builds Wealth
Planet Wealth: Fortunes of the Brave
Mary Katherine Johnson sits down with Dan Egan, VP of Behavioral Finance & Investing at Betterment, to decode how our habits, narratives, and timing drive financial outcomes more than hot tips ever will. Dan explains why success comes from matching risk to time horizon, building automatic systems that spare your willpower, using tax-aware prompts (hello, long- vs short-term gains), and reframing money from a scarce enemy to a tool you can wield responsibly, and often with your community. We dig into teachable moments that stick, how to design routines that “pay yourself first,” why...
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E32: Nick Malouin: From Chaos to Clarity: How Innovators Turn Uncertainty Into Action
Planet Wealth: Fortunes of the Brave
Mary Katherine Johnson welcomes Nick Malouin, Senior Strategy Director at Electric Innovation, to unpack how innovation strategy turns ambiguity into action. From Capgemini to Electric, Nick has spent a decade taking ideas from insight to in-market—bridging hard data with human truth so teams can build products people actually want. He breaks down why the best work starts with the consumer journey, not the org chart; how to separate signal from noise with out-of-category insights; and why “possible futures” beat single-line forecasts. If you care about product development, consumer...
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E31: Janice Shade: How Community Capital Moves Money from Wall Street to Main Street
Planet Wealth: Fortunes of the Brave
Community capital, crowdfunding, and local investing take center stage in this episode of Fortunes of the Brave. Systems entrepreneur and financial innovator Janice Shade, co-founder of Milk Money Vermont and founder of Capital Innovation Lab and Fundamenta, joins host Lance Woodson to unpack how everyday people can invest in the small businesses that define their hometowns. From her early days at Seventh Generation questioning the “green premium” to designing new models for Main Street investing, Janice shows why traditional capital markets leave most founders and communities...
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E30: Chad Hufford: Dare to Be Different: The Blueprint for Abundance
Planet Wealth: Fortunes of the Brave
Mary Katherine Johnson welcomes Chad Hufford, Founder & Financial Planner at Veritas Wealth Management, for a refreshingly human conversation about building wealth you’ll actually want to live with. Chad argues we’re wired for scarcity and crowd-following—great for survival, terrible for long-term freedom—so real progress starts with mindset, meaning, and management of the investor (not just the investments). You’ll hear how to define date-specific, dollar-specific goals (e.g., “₍future date₎ + net monthly income after tax”), then reverse-engineer the needed...
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E29: Rebecca McLean: Bridge the Gap: The Reg CF Revolution for Everyday Investors
Planet Wealth: Fortunes of the Brave
Mary sits down with Rebecca McLean to unpack how the JOBS Act and Regulation Crowdfunding (Reg CF) opened a new lane for everyday investors and community focused entrepreneurs to fund real estate; legally, transparently, and at scale. Rebecca traces National REIA’s 40-year mission to promote, protect, and educate the industry, including advocacy that helped unlock today’s crowdfunding rules. They dig into attainable housing, revitalizing blocks “one address at a time,” and why local collaboration + policy + partnerships matter just as much as capital. From accredited vs....
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E28: Matt Slepin: From Cowboys to Platforms: What’s Next in Real Estate
Planet Wealth: Fortunes of the Brave
Lance sits down with Matt Slepin, one of real estate’s best-known executive recruiters and storytellers, to trace the industry’s arc from the RTC era to today’s institutional, tech-enabled platforms—and what comes next. Matt explains how CMBS and REITs catalyzed a shift from “piles of assets” to true operating companies, why technology and capital markets now define competitive advantage, and how leaders must evolve from property whisperers to business builders with resilient balance sheets, systems, and succession. They get real about purpose and...
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E27: Kathy Fettke: Real Wealth, Real Returns: The Cash-Flow Playbook
Planet Wealth: Fortunes of the Brave
Mary Katherine Johnson sits down with Kathy Fettke, Co-Founder of Real Wealth, to unpack a practical roadmap to real estate investing that ordinary professionals can use to build durable wealth. After a family health scare wiped out her savings, Kathy discovered the power of rental income and house hacking, then turned a weekend radio show into a learning engine interviewing experts (including Robert Kiyosaki) and stress-testing everything with commonsense cash flow. In this episode, she explains how to leave bubble markets for fundamentals, why average-priced homes...
info_outlineThis week, Lance welcomes Elliott Holland, a Harvard MBA and expert in making small business acquisitions understandable and achievable. Elliott, who runs Guardian Due Diligence, has developed a proprietary system that helps professionals efficiently transition from corporate roles to multimillion-dollar business ownership. In this episode, he breaks down the key challenges, strategies, and mindsets required for successful acquisitions—highlighting common pitfalls like “analysis paralysis” and the psychological trap of "deal heat." He also introduces the concept of the “$250K salary trap,” where high earners end up living paycheck to paycheck due to lifestyle inflation.
Elliott underscores the value of mentorship, likening the right guide to a Sherpa who can lead you through the acquisition journey. He explains why buying a business often offers more advantages than launching a startup and debunks myths around passive income. Sharing personal stories, Elliott describes how business ownership has allowed him to live in Colombia and travel freely, offering a glimpse into the freedom and fulfillment that come with owning the right business.
Topics Include:
- Elliott’s Unique Journey After Harvard
- Common Challenges in Business Buying
- Developing Mindset Shifts for Success
- The Massive Importance of Mentorship
- Comparing Acquisitions vs. Startups
Resources Mentioned in This Episode:
Elliott’s Business Buying Masterclass
Connect with Elliott:
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Produced By: Social Chameleon