Jay Patel, a former Goldman Sachs investment banker, shares the operational and strategic advantages that his family office holds over traditional private equity. He details the creative, "street smart" tactics his family has used to build a generational empire of over 140 hotels, from flipping multi-million dollar hotel contracts to acquiring and revitalizing a national brand from Blackstone. Listeners will learn the specific deal structures, risk mitigation strategies, and core values that allow his family office to thrive in the competitive hospitality industry.Chapters:0:01 The Secret to Winning Isn't Hard Work1:08 Family Office vs. Private Equity: The Key Differences5:14 Investment Horizon, Capital Structure, and Risk Tolerance8:40 The Operational Edge of a Family Office10:25 The Dynamics of Working with Family13:09 Core Values: Hard Work and Education16:12 Jay's Story: From an Immigrant Family to Wall Street19:56 From "Wall Street" the Movie to a Career at GE25:21 Working 100-Hour Weeks at Goldman Sachs29:22 Competitive Edge: Why We Dominate the Hotel Market33:17 The Four-Story Interior Corridor Box: Our Ideal Investment38:37 The Immigrant Mentality in the Hotel Business42:05 How to Flip a Multi-Million Dollar Hotel Contract47:23 Street Smarts vs. Book Smarts in Business51:23 "Always Outsmart Someone, Never Screw Someone"53:56 How We Outsmarted Blackstone to Acquire a Hotel Brand1:00:52 Breakdown of a Creative Deal That Netted a $15M Profit
After handling over 500 deals worth billions, investment banker Peter Kubasek reveals how his father's heartbreaking business deal inspired his career. He breaks down how his team's 200-hour deep-dive analysis helped one client nearly double their company's valuation before an exit. Using a real-world example of a technology deal he orchestrated that now saves GE $1 billion a year, Peter shares how his faith is the secret foundation for navigating high-stakes deals and building a lasting legacy.01:25 His Father's Bad Deal03:37 The Sad Reality of the Sell Side in M&A05:55 The Simple Advice He Ignored07:40 The Four Pillars of a Perfect Exit09:07 Is Your Business Actually Working?10:55 Operate As If You're Exiting13:26 The #1 Thing Missing in Deals14:33 The World-Changing Tech Deal16:33 Hiring a CIA Operative to Do a Deal18:36 The Billion-Dollar Savings Proof20:13 Why Smart Buyers Pay More22:44 How To Change A Company's Culture26:26 Your Culture is What You DO27:23 The Hairdresser Confidentiality Test28:31 How They Almost Doubled Their Value31:45 The Root Of His Success33:42 Living Your Faith, Not Just Preaching37:54 The Daily Habit of a Billionaire Mentor40:47 The P&G Chairman's Kindness43:53 Where His Faith Began46:11 My "Faith-Filled" Bar Hop47:50 From Fire Escape to Lordship52:42 The Proverb That Changes Everything57:51 How He Wants To Be Remembered
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.
Does this mean the end for traditional private equity and venture capital firms?
Will this $124 Trillion Wealth Transfer be the one that means the end for Wall Street?
How are the most wealthy families in the world investing their money in 2025 and beyond?
In this interview, Ron Diamond breaks down how it all works.
00:00 Intro + Context
01:55 Family Offices Defined
03:20 The Rise of Family Offices
05:03 The $124 Trillion Wealth Transfer Crisis
06:37 Foundations vs. Families
08:10 Long-Term Capital
10:12 Mission Before Money
12:34 The Problem With Traditional PE
14:09 Why Patient Capital Always Wins
16:15 Ron’s Investment Rules
18:00 Avoiding Ego Deals
19:25 Generational Wealth Risk
21:03 Family Governance Breakdown
23:08 Why Families Fail
24:44 How to Structure a Family Office
26:12 Defining True Wealth
28:10 Why Family Offices Will Poach PE Talent
31:14 $1B Philanthropy Moves
33:00 Sergey Brin and his $1B Donation
35:04 PE vs. Family Capital
37:20 New Capital Mindset
39:48 Generational Thinking Gap
42:30 Fixing The Future
44:26 Closing Thoughts
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 flow with https://getdealflow.ai/00:00 - Intro: From Nothing to Millions 00:28 - Childhood + Early Setbacks 01:08 - NBA Dreams Cut Short 01:47 - First Investment Profits 02:07 - Marriage and Family Focus 02:31 - Why I Named It 316 Capital 03:12 - God Owns My Business 03:45 - How I Negotiate Deals 04:45 - Real Value Starts With the Bible 05:36 - Morning Routine for Wisdom 06:28 - How I Handle Loss and Failure 07:42 - Deal Breakdown: What Went Wrong 08:05 - Why God Let the Deal Fail 08:33 - God's Love in Hard Times 09:20 - Losing My Son 10:04 - Rushed to the Hospital 10:54 - Holding My Son, Worshiping Anyway 12:07 - Mourning and Grieving With God 13:29 - Yelling at God 14:08 - God's Response to My Pain 15:15 - Making Peace With Loss 16:12 - Don’t Make Your Kids an Idol 17:48 - What It Means to Abide 18:12 - Letting God Lead Strategy 19:17 - How I Got Saved 19:52 - Hearing My Father Hit My Mother 20:19 - Faith Became My Survival Tool 21:17 - Asking God to Show Himself 21:45 - Why I’m Still Sane Today 22:16 - Why I Need Daily Mercy 23:04 - Why Jesus’ Suffering Matters 23:44 - King First, Hustle Second 24:27 - Master and Student 25:14 - Why I Trust God’s Timing 25:55 - God Uses Pain to Teach 26:50 - Big Deal in Mississippi 27:12 - Crazy Seller, Long Deal 28:06 - No Cash, Still Closed 28:29 - 18 Free Lots Explained 29:01 - Deal Value: $2.5M 33:33 - What Value Really Means 34:24 - How I Structure Deals 35:55 - Helping Buyers Choose Offers 37:16 - Real Estate Exit Strategy 39:08 - Early Days: No Credit 40:21 - Making 3 Offers Always 42:20 - Listen Before You Talk 43:06 - Conflict Resolution Strategy 44:03 - Why Teams Beat Solo Hustle 44:38 - Avoiding Work-Life Burnout 45:30 - Ranking Life Priorities 46:55 - Hiring Based on Fruit 47:51 - Why I Train the Hungry 48:45 - What I Look for in Hires 49:54 - The Partner That Got Dangerous 52:13 - All Money Isn’t Good 53:13 - Breaking My Own Rules 55:38 - 3 Rules for Any Deal 56:08 - $15K Deal Walkthrough 57:06 - Flipped It for $85K 59:00 - Closing + Final Thoughts
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 ownership of your off market deal flow with https://getdealflow.ai/00:00:00 - A 4 Million Dollar Win00:00:25 - Top Three Business Principles00:02:28 - Growing Up Was Not Easy00:03:24 - Meeting His Wife, Ruthie00:05:07 - Advice To His Younger Self00:06:06 - Never Let Your Wife Sign a Loan00:06:55 - How He Built His Wealth00:08:42 - How He Started In Business011:42 - From Glass To Land Development00:13:33 - Toughest Time In Business (2008)00:15:22 - Suing The Bank Back00:17:45 - The Biggest Lesson He Learned00:18:52 - A Creative Hospital Land Deal00:22:12 - Always Leave Meat On Bone00:24:34 - His Land Development Business00:28:36 - What He Would Do Differently00:30:19 - His Legacy For His Family00:32:28 - Why His Grandson Went to College00:34:52 - Committing His Life To Christ
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 where the heavyweights of high finance share their off-market playbook: https://offmarketmemo.beehiiv.com/ 0:00 The road to the top0:47 KC has a stroke1:52 KC gets honored by Elliot3:35 KC explains the blue crab theory4:01 Lessons from business mistakes5:15 Why giving comes first6:44 How spiritual principles really work10:12 When chasing money goes wrong11:01 The story of Monica’s depression13:13 From pain to purpose14:06 The rise and fall of his first company15:27 The birth of LivingFuel16:46 KC’s divorce and darkest season18:02 Meeting Heidi18:55 The stroke that nearly killed him20:25 Heidi manages his ICU care22:13 Sneaking LivingFuel into the hospital23:07 The 7 pillars of real health26:08 Healing his son’s ear infections27:38 Why stress is more dangerous than diet28:00 Heidi sleeps in a chair for weeks29:01 The moment he knew she was the one30:13 The impossible 55-point list31:06 KC’s near-death vision32:36 God cares about the details33:26 The boy who drowned but lived35:17 The abundant life Jesus promised37:12 How to pray with faith39:01 What it means to speak to the mountain41:01 The power of Galatians 3:1342:57 KC marries Heidi43:21 The 7 things to rate in your life46:01 Why prayer actually works
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 highest level.Sign up to our newsletter: https://offmarketmemo.beehiiv.com/ 00:00 Intro to Richard C. Wilson01:36 What FamilyOffices.com actually does03:18 How he discovered the family office world06:15 What problems family offices actually have08:50 Breaking down family offices like a 5th grader13:03 Dealing with ultra-wealthy while broke16:12 Why trust beats pitch decks18:45 The power of cognitive dissonance22:05 What truly drove him to build wealth25:32 The risk he took that changed everything28:44 How he made $35,000 in a single day30:40 Why he bought FamilyOffices.com33:21 How he used blogging and SEO to launch35:44 Marketing mentors and the choke point strategy39:18 Why finance people are terrible marketers41:32 How his AI tools help fix that44:40 Why family offices often have bad deal flow48:15 Positioning = better deal flow50:29 How media and distribution became his moat54:20 The deal structure tool that changes the game57:42 What the best family offices are doing differently59:41 Strategic acquisitions to remove bottlenecks01:02:40 The billionaires.com play and trifecta moat01:07:01 What billionaires do differently than millionaires01:10:35 How long-term niche focus compounds01:12:58 Don’t wait for permission — publish01:14:04 How far behind are PE and family offices, really?01:18:00 The biggest mistake family offices make01:21:20 His #1 quote from billionaire interviews01:24:06 Richard’s 10-year vision
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 boring problems.Sign up to our newsletter where the heavyweights of high finance share their off-market playbook: https://offmarketmemo.beehiiv.com/ 00:00 Meet Herbert02:20 Military to business journey04:40 Lessons from the Marines08:30 $900K to $6M growth11:00 Why he dropped Medicaid13:00 Started 6 software companies17:00 What is Nexus RFP?20:30 AI writes the proposals23:30 The $25M contract story27:10 When to sell a company31:30 His biggest mistakes35:00 Raising money the smart way41:00 Why minority founders struggle46:00 Picking real AI winners50:00 Fixing trauma before it starts54:00 His faith and morning prayer1:01:00 Why he keeps building1:06:00 How to connect with Herbert
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, why he refuses to overwork, and how he uses leverage, teams, and personal brand to scale smarter—not harder.Whether you're a private equity investor, solopreneur, or acquisition rookie, this episode is a masterclass in using acquisitions to buy back your life.Sign up to our newsletter where the heavyweights of high finance share their off-market playbook: https://offmarketmemo.beehiiv.com/ 00:00 - Intro: Meet Ben Kelly00:33 - Ben’s background: Army Intel → JP Morgan → Entrepreneurship01:30 - Teaching others to acquire businesses for $150K+ cash flow03:00 - Why people misunderstand what Ben teaches04:00 - The myth of “get rich quick” business buying05:00 - How Ben transitioned for time freedom06:30 - Why time—not money—is his #1 value07:30 - The $5K SaaS deal that became $180K/year08:30 - How Ben works 20–25 hours a week (with 4 kids)10:00 - The secret: Only buy businesses you don’t have to run11:00 - How Ben picks the right people before he buys12:00 - What he looks for in a general manager14:00 - How to “read the energy” of a business during due diligence16:30 - The role of faith in how Ben leads and hires19:00 - Why Ben’s values shape every business decision21:00 - Business can be dirty—why integrity pays long term23:00 - Ben’s upbringing and personal faith journey26:00 - Why some Christians chase billions and others chase family28:00 - Ben’s daily schedule: 5-hour workdays by design30:00 - The 4-filter system Ben uses to say yes or no to ideas32:00 - ROI filter: Only doing what compounds his existing strengths34:30 - Why brand is now the centerpiece of his business model36:00 - How his newsletter and content drive deal flow passively38:00 - What social media does that cold calls can’t40:00 - The unfair advantage of brand: speed and reach42:00 - Ben’s superpower: thinking through people, not tasks44:00 - How Ben values his time in dollars before taking on new projects46:00 - How he customizes incentives to each person on his team48:00 - The biblical principle that fuels his generosity50:00 - Paying people more than they ask for (on purpose)51:00 - Crash course: How to find, fund, and integrate a deal54:00 - Why you should wait 90 days before changing anything55:00 - Where to find Ben online
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 listening.Sign up to our newsletter where the heavyweights of high finance share their off-market playbook: https://offmarketmemo.beehiiv.com/ 00:25 What Emerging Ventures actually invests in01:36 David’s story: from insurance CEO to full-time VC03:53 How early tech vendors pulled him into venture06:17 Why he exited everything to back founders08:38 Starting a fund after 500+ angel investments10:34 Operator vs. traditional VC: who makes better investors?12:36 “When in doubt, say no.”14:22 Why most startups shouldn’t raise venture capital16:15 What founders need before raising17:42 “It’s like dating, not banking.”19:50 His framework for evaluating traction22:15 The math behind hitting Series A24:14 Why he limits meetings and screens hard27:28 Red flags: hype, noise, and no differentiation29:25 The neobank bubble — and why it collapsed31:51 Why blockchain was misused34:41 One blockchain startup he actually liked36:10 “Every startup is now an AI startup.”38:09 Why most AI wrappers won’t survive40:53 Will AI kill B2B SaaS?43:04 Why big platforms will absorb all the tools44:28 Vertical SaaS vs. niche marketing47:22 Features vs. real products50:28 Can tech-enabled service firms become SaaS?53:24 Why some businesses aren’t VC-backable57:03 “I don’t bet on people. I wait for proof.”59:01 Why the conservative side of VC is overlooked01:04:20 How his fund is different from traditional VC01:08:05 Why unicorns and solid exits can’t coexist01:09:12 Where to find David and learn more
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 our newsletter where the heavyweights of high finance share their off-market playbook: https://offmarketmemo.beehiiv.com/ Timestamps:00:34 Who Kevin is01:53 Early life in Ohio02:45 From Invesco to business owner03:46 Bought a $200K business05:36 Grew it to 34 states07:33 How radon business worked09:30 Closed deal in a diner11:06 Why he chose buying over building13:35 How “Sier Capital” started15:25 His system for fixing companies17:27 Moving state to state18:03 His wife’s role20:36 How to choose a life partner24:28 Balancing business and family27:17 Hard conversations with employees29:26 What “violently aligned” means31:39 Creating open culture in PE33:13 Drywall interview test35:04 Why he gives equity36:03 From $10M to $50M38:00 How he fixes the P&L41:37 When to do add-ons43:46 Three ways to grow a business45:58 How to increase LTV47:25 The 48-hour guarantee49:35 Buying a piece of a sports team51:15 What pattern recognition does52:57 Breaking the rules to win56:08 Sales strategy and close58:37 Final takeaways59:53 Where to find Kevin
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 episode will shift your perspective.If you're thinking about buying businesses, building a portfolio, or competing with billion-dollar companies, this episode is a masterclass.Sign up to our newsletter where the heavyweights of high finance share their off-market playbook: https://offmarketmemo.beehiiv.com/Timestamps:01:35 Carey’s journey: startup builder to venture partner04:25 The #1 mistake founders make06:40 “Just because you can build it doesn’t mean you should”07:27 What makes a founder lovable09:51 Every startup is a snowflake13:03 Why he chose VC over private equity15:58 His take on frameworks vs. just starting17:07 Resist the urge to keep building18:46 The truth about “breakthrough ideas”19:40 The model behind BankTech Ventures22:50 How he de-risks product-market fit24:26 Applying PE-style thinking to early stage27:00 How Operate and BankTech work together30:11 His unique vantage point between two worlds31:02 Why he cares so much about community banks33:45 His family’s legacy in banking35:21 Banks as the foundation of real communities37:10 “Everyone can teach me something”39:51 Advice to his younger self as a founder41:59 Why he became obsessed with recruiting44:46 The mindset shift that unlocked scale46:39 How he retains talent long term48:13 The #1 trait he hires for49:40 Why startup athletes are better than resumes51:25 How to match talent to company stage54:56 “I’m not building to get somewhere. I just love doing this.”57:57 Why 50% qualified is the sweet spot59:32 Carey’s definition of adventure in business
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 companies, this episode is a masterclass.For more content like this and an inside look into the world of the largest dealmakers in the world, subscribe to The Off Market Memo https://offmarketmemo.beehiiv.com/ Are you in Private Equity, VC, or a Family Office? Become a guest on the Deal Flow Show herehttps://guestlist.dealflowshow.ai/Timestamps:01:06 How Edoardo broke into ETA03:40 What StarStep Capital actually does05:27 Why they picked the coatings industry07:46 His immigration story + first business10:08 How he exited a startup in 3 years14:51 Advice he’d give his younger self15:55 Why “start from scratch” is overrated18:18 What most small business owners get wrong20:05 His step-by-step process for doing deals21:35 Why focusing on one industry matters22:26 How he thinks about building his team25:30 How his team splits roles without titles28:03 Why solo entrepreneurship doesn’t scale29:54 The hardest part after buying a company31:15 Why he loves keeping sellers' kids in place33:45 How they structure branding + integrations34:59 What long-term value creation looks like36:54 Their current size and 10-year goal38:47 How his Machiavelli mindset gives him an edge41:07 How he developed a big vision early43:21 “I don’t feel big… I feel like I’m just starting”44:42 Where he gets advice and mentorship47:24 The closest thing to a “bad deal” they’ve done48:45 Why proprietary deal flow is key50:26 Why bigger deals are actually easier53:22 What affects multiples in this space55:02 How they consistently win competitive bids57:57 Their long-term model vs. traditional PE59:26 Biggest lesson from 2025 (so far)
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 this and an inside look into the world of the largest dealmakers in the world, subscribe to The Off Market Memo https://offmarketmemo.beehiiv.com/ Are you in Private Equity, VC, or a Family Office? Become a guest on the Deal Flow Show herehttps://guestlist.dealflowshow.ai/The Deal Flow Show Episode 1 ft Elliot Martinez Timestamps:01:25 Why most of your worries are fake02:14 The deeper reason behind wanting money03:13 The basketball game that changed his motive05:42 A 30-second exercise to kill regret07:43 Writing your own obituary11:03 How faith shaped his business13:20 Millionaires chase lifestyle, billionaires chase purpose15:33 Warren Buffett’s 25-5 rule19:10 Energy audit: Who drains vs. fills you20:35 The power of intentional relationship building26:16 How to talk to billionaires29:57 How to get a callback from high-level people33:14 The business model explained simply36:46 How a mentor saved him millions39:32 Red flags when buying a company42:59 Why character beats profit47:35 Intuition vs. numbers in dealmaking50:10 How it feels managing investor money53:11 Getting the right people on the team58:19 Building the team before raising capital01:04:35 The one skill that beats AI01:08:51 A week-by-week relationship routine01:13:17 How to find your zone of genius01:16:38 Hire out what drains you01:17:45 The biggest mistake in private equityThe Deal Flow Show is where real conversations happen with real capital behind them. Hosted by Ivan Acuna and DJ Panfili, this is not another surface-level business podcast. We sit down with investors, operators, and elite dealmakers to unpack how 8- and 9-figure deals actually get done — from private equity roll-ups to mindset shifts, from war stories to wealth strategy.No fluff. No guru talk. Just raw insight, big plays, and the people pulling the strings behind today’s biggest moves in private equity, VC, and Family Offices.