The Deal Flow Show

The Deal Flow Show

The Deal Flow Show is where private equity gets real. No scripted answers, no corporate fluff—just raw, unfiltered conversations with the top dealmakers in the game. We pull back the curtain on the industry, sharing the stories, strategies, and hard-earned lessons that you’d normally only hear behind closed doors. Whether you’re deep in the world of M&A or just starting to navigate private markets, this is where you get the insights, mentorship, and war stories that actually matter.

Episodes

August 7, 2025 65 mins

Today’s guest, Ron Diamond, founded and sold a successful hedge fund. Now he is running one of the largest family office syndications in the entire world.


He exposes how Family Offices now control over $10 trillion in capital, and why they’re quietly investing in solutions to problems the government can’t fix.


He explains how unlike Wall Street, the heirs of these families want to play the long game and invest with purpose.

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Real estate investor LaDale Buggs of 316 Capital shares how faith, pain, and smart deals helped him build a multi-million dollar real estate portfolio with no credit and no cash. This interview covers business strategy, real estate investing, faith in hard times, high-stakes negotiation, and long-term wealth building.If you are a PE firm, executing a roll up, or scaling rapidly with M&A, take ownership of your off market deal f...

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Real Estate Developer Bob Harrell shares his amazing story of surviving the 2008 crash and winning a lawsuit against a big bank. He covers advice on making money, real estate investing, and why your word must be your bond. His story covers overcoming personal struggles and finding faith, offering real business lessons for any entrepreneur.If you are in private equity, executing a roll up, or scaling rapidly with M&A, take owner...

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In this video, KC Craichy tells the true story of how stress almost ended his life despite being super healthy AND wealthy. He shares how his company LivingFuel was born from pain and how God helped him rebuild after divorce, collapse, and a near-death experience. You’ll learn how health, faith, and humility saved him. This video is full of powerful lessons on business, healing, and walking with purpose.Sign up to our newsletter wh...

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In this episode, Richard C. Wilson explains how he built the world’s largest family office network by focusing on value, positioning, and long-term niche domination. From owning FamilyOffices.com to interviewing 45 billionaires, he breaks down mental models, marketing strategy, and how to win exclusive deal flow. If you run a fund, raise capital, or want access to better deals, this episode shows what it takes to play at the highes...

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In this video, Herbert Drayton shows how he used AI to build a $25M business helping small companies get government contracts. He talks about growing one business from $900K to $6M and turning it into six startups. You’ll hear how he finds real problems, uses AI to fix them, and helps thousands of minority-owned businesses win deals. This is a story about government contracts, AI tools, startup growth, and making money by solving b...

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In this episode of the Deal Flow Show, we sit down with Ben Kelly, the founder of Acquisition Ace and one of the most respected voices in the small business acquisition space. Ben shares how he transitioned from Army Intelligence and JP Morgan to owning multiple cash-flowing businesses—all while prioritizing family, faith, and time over hustle culture.You’ll learn how Ben makes over $1M per year while working 20–25 hours a week, wh...

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In this episode, David Mandel unpacks how his underwriting background shaped his approach to venture capital — and why most AI startups today are just features pretending to be businesses. From 500+ angel investments to managing his own VC fund, David breaks down how he filters deals, why he avoids hype cycles, and what founders get wrong about raising capital. If you’re building or betting on B2B SaaS, this one’s essential listeni...

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In this video, Kevin Ramsier shares how he turned a tiny $200K business into a multi-state empire. He quit a finance job, bought a company in a diner, and built 12 businesses that now dominate their markets. Kevin breaks down how he scales fast, builds teams, and makes big exits with no fund, no bankers, and no fluff. If you care about real business, real deals, and building a $100M platform from scratch—watch this now.Sign up to o...

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In this episode, Carey Ransom breaks down what most startup founders get wrong — and how to actually build something worth scaling. From running a venture studio to building a fund that serves 100+ community banks, Carey shares his unique lens on early-stage startups, recruiting, product validation, and long-term thinking. If you're in the 0-to-1 stage or trying to understand the difference between building and optimizing, this...

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In this episode, Edoardo Maggini shares how he went from a 16-year-old Italian immigrant to building a $70M+ private equity roll-up in the coatings industry. He explains why he left the startup world behind, how his team is taking on giants like Sherwin-Williams, and what most entrepreneurs get wrong about building wealth. If you're thinking about buying businesses, building a portfolio, or competing with billion-dollar compani...

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In this video, high school drop out turned private equity firm owner Elliot Martinez breaks down why chasing money isn't the goal — having freedom is. He shares how mindset, clarity, and purpose shaped his journey from real estate to private equity. You'll hear the real reason successful people still chase growth. This conversation will shift how you think about success, wealth, and what truly matters.For more content like ...

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