Mailbox Money Show

Bronson Hill
  • 5.0 (1)
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  • UPDATED WEEKLY

Are you looking for ways to grow your income without costing you more time? Many people think that to invest in real estate or other assets, you have to be involved on every level. In the Mailbox Money podcast, we explore new asset classes to invest in as well as tools that will make you a better passive investor. You won’t want to miss an episode because they’re packed full of life-changing wisdom from thought leaders. Hit subscribe and prepare to have your financial life changed! Bronson Hill is the host of the Mailbox Money podcast and the founder and CEO of Bronson Equity.

  1. Aleksey Chernobelskiy - Never Invest Blind Again

    3D AGO

    Aleksey Chernobelskiy - Never Invest Blind Again

    Get my new book: https://bronsonequity.com/fireyourself Download my new special report - How to Use Inflation to Your Advantage - www.bronsonequity.com/inflation Join Bronson Hill and co-host Nate Hambrick on the Mailbox Money Show with Aleksey Chernobelskiy for a practical discussion on how passive investors (LPs) can stop investing blindly. Aleksey shares how he built GP LP Match — a platform that connects LPs with quality GPs — and why most retail investors don’t have enough conversations or data to make strong decisions. The episode covers vetting operators, evaluating track records, avoiding common pitfalls, using better tools and information, and the power of seeing many deals to develop better judgment. Aleksey Chernobelskiy is the founder of GP LP Match, a platform designed to help limited partners discover and connect with general partners for real estate and alternative investments. He focuses on bringing transparency, better matching, and education to the LP/GP ecosystem. This episode is essential listening for any passive investor who wants to invest smarter and reduce risk through better information and connections. TIMESTAMPS 00:43 - Welcome to the Mailbox Money Show! 01:17 - Nate Hambrick on Market Sentiment & Emerging Opportunities 01:58 - Introducing Aleksey Chernobelskiy & GP LP Match Platform 03:15 - Why Aleksey Built GP LP Match to Connect LPs & GPs 04:43 - The Importance of Having More GP Conversations as an LP 06:40 - Looking at Hundreds of Deals to Develop Better Judgment 08:41 - Vetting Operators: Track Record, Experience & Gut Feeling 10:58 - Going Beyond Marketing Materials & Deck Aesthetics 13:15 - Deck Reviews, Data Queries & Platform Tools for LPs 16:25 - Three Pillars of Vetting Deals: Operator, Monitoring & Structure 18:38 - How AI Powers Deal Matching & Insights on the Platform 21:30 - Aleksey’s Personal Focus on Distressed & Creative Deals 23:24 - How to Connect with Aleksey & GP LP Match CONNECT WITH THE GUEST Website: gplpmatch.com Email: aleksey@gplpmatch.com #LPInvesting #RealEstateDeals #PassiveInvesting #GPMatching #DealVetting #InvestorEducation #AlternativeInvesting

    26 min
  2. Gary Lipsky - Is Multifamily Coming Back?

    MAY 11

    Gary Lipsky - Is Multifamily Coming Back?

    Get my new book: https://bronsonequity.com/fireyourself Download my new special report - How to Use Inflation to Your Advantage - www.bronsonequity.com/inflation Join Bronson Hill and co-host Nate Hambrick on the Mailbox Money Show with multifamily veteran Gary Lipsky as they discuss whether multifamily is poised for a comeback. Gary shares insights from years of experience on navigating high interest rates, declining valuations, shifting rent growth, and the importance of strong market knowledge, disciplined underwriting, and long-term holds. The conversation covers current cap rate opportunities, surviving challenging cycles, the power of cash flow, and why patience and operator expertise matter more than ever. Gary Lipsky is the President and CEO of Break of Day Capital, with over 1,400 multifamily units as GP. He is a two-time bestselling author and a seasoned operator focused on disciplined, long-term multifamily investing. This episode offers practical wisdom for both passive investors and operators on positioning for the next phase of the multifamily cycle. TIMESTAMPS 00:45 - Welcome to the Mailbox Money Show with Gary Lipsky 01:19 - Nate Hambrick on Current Multifamily Opportunities 02:06 - Gary Lipsky Introduction & "Survive Till 25" Mindset 02:48 - Cap Rate Expansion & 2021-2022 Valuation Losses 04:21 - Strategy Shift from Big Value-Add to Core-Plus Focus 05:38 - Advice for Investors Facing Challenges & Capital Calls 06:32 - Importance of Deep Market Knowledge & Off-Market Deals 09:12 - Changing Exit Strategies & Longer Hold Periods 10:34 - Investor Psychology, Herd Mentality & Unloved Assets 13:41 - Cash Flow Importance & Being a Free Agent Investor 14:41 - Multifamily Outlook for Next 12-24 Months 19:30 - Personal Portfolio Diversification & Liquidity Needs 23:12 - Connect with the Guest Connect with the Guest: Invest Smart Summit: http://investsmartsummit.com/ Website: http://breakofdaycapital.com/ #MultifamilyInvesting #RealEstateCycles #CashFlowInvesting #MarketTiming #InvestorPsychology #ValueAddStrategy #CapitalPreservation

    27 min
  3. Feras Moussa - Why Multifamily Investors Are Buying Businesses

    MAY 4

    Feras Moussa - Why Multifamily Investors Are Buying Businesses

    Get my new book: https://bronsonequity.com/fireyourself Download my new special report - How to Use Inflation to Your Advantage - www.bronsonequity.com/inflation Join Bronson Hill and co-host Nate Hambrick on the Mailbox Money Show with Feras Moussa of Disrupt Equity. Feras shares how his team has scaled to over 7,000 multifamily units and $1B+ in real estate, then expanded into private equity through their M&A Launchpad — acquiring cash-flowing businesses that deliver significantly higher yields than traditional real estate. The conversation explores the transition from multifamily to buying businesses, the massive cash flow potential (often 3-5x multiples vs. real estate cap rates), working capital considerations, seller psychology, risk management, and creative deal structuring. Feras Moussa is the founder of Disrupt Equity, a real estate investment firm with over 7,000 units and $1B+ in transactions. He recently launched the M&A Launchpad to acquire and scale operating businesses alongside multifamily investments. TIMESTAMPS 0:47 - Welcome to the Mailbox Money Show with Feras Moussa 1:37 - Nate Hambrick’s Positive Experience Investing with Disrupt Equity 1:53 - Feras Moussa Background & Shift from Multifamily to Private Equity 3:17 - Why Higher Cash Flow Led to Buying Businesses 6:10 - Cap Rates vs. EBITDA Multiples Explained 7:48 - Operating Businesses is Harder Than Multifamily 9:49 - Ideal Business Size: $1M+ EBITDA Sweet Spot 11:44 - Challenges of Acquiring Businesses & Seller Emotions 14:31 - SBA Loans, Creative Structuring & Protecting Downside 16:26 - Risk-Adjusted Returns & Hedging in Business Acquisitions 20:02 - Working Capital Importance in Business Deals 23:10 - Roll-Up Strategy & Multiple Arbitrage Opportunities 25:10 - How to Connect with Feras Moussa & Disrupt Equity CONNECT WITH THE GUEST Email: feras@disruptequity.com LinkedIn: https://www.linkedin.com/in/feras-moussa-2072a1196/ Instagram: @feras.moussa #PrivateEquity #BuyingBusinesses #CashFlowInvesting #MultifamilyToMNA #InvestorMindset #EBITDAMultiples #DealSourcing

    37 min
  4. Troy Eckard - Oil and Gas Investing Explained

    APR 27

    Troy Eckard - Oil and Gas Investing Explained

    Get my new book: https://bronsonequity.com/fireyourself Download my new special report - How to Use Inflation to Your Advantage - www.bronsonequity.com/inflation Join Bronson Hill and co-host Nate Hambrick on the Mailbox Money Show for a clear, practical breakdown of oil and gas investing with industry veteran Troy Eckard. The conversation covers the massive tax advantages (up to 80-90% deductions in year one), strong cash flow potential, current supply disruptions driven by geopolitical events, and why oil prices are likely to remain elevated for the next 12–24 months. Troy shares his four decades of experience, explains the shift from risky vertical drilling to modern horizontal wells with high success rates, the importance of working with proven operators, and how to evaluate deals as a passive investor. Troy Eckard is the founder of Eckard Enterprises with over 40 years in the oil and gas industry. His firm has deployed more than $1.4 billion in capital across working interests, mineral rights, and infrastructure, including ownership of the second-largest natural gas pipeline in the Gulf of Mexico. TIMESTAMPS 0:47 - Welcome & Overview 1:40 - Nate Hambrick on Profit, Quick Payback & Tax Benefits 2:37 - Introducing Guest Troy Eckard & Eckard Enterprises 3:03 - Troy's 40 Years in Oil & Gas: From Old Rigs to Modern Technology 3:41 - Geopolitical Events (Iran/Straights of Hormuz) & Oil Price Impact 4:32 - Why Oil Should Be $150–$200/Barrel Given Current Disruptions 6:12 - Supply Shortages, Strategic Reserves & Delayed Drilling Response 10:03 - Physical Delivery Contracts vs. Futures & Near-Term Price Outlook 12:30 - Why Producers Are Laying Down Rigs Despite $100+ Oil 13:42 - Ancillary Opportunities & Risks in Oil & Gas Services 16:04 - Lessons from COVID-Era Negative Oil Prices & Captive Audience 18:26 - Building a Large Investor Base Through Education & Low-Pressure Model 20:38 - Risk Management: Focus on the "Who" (Operator Track Record) 22:05 - Modern Horizontal Drilling: Near-Zero Dry Hole Risk 23:10 - Technology Improvements & AI in Oil & Gas 23:48 - Connect with Troy Eckard CONNECT WITH THE GUEST Website: http://eckardenterprises.com/ App: Eckard Insight #OilAndGasInvesting #TaxAdvantages #EnergyInvesting #GeopoliticalRisk #PassiveIncome #InvestorEducation #CommodityInvesting

    28 min
  5. Paul Moore - THIS IS WHY INVESTORS LOSE MONEY

    APR 20

    Paul Moore - THIS IS WHY INVESTORS LOSE MONEY

    Get my new book: https://bronsonequity.com/fireyourself Download my new special report - How to Use Inflation to Your Advantage - www.bronsonequity.com/inflation Join Bronson Hill on the Mailbox Money Show as Paul Moore reveals why so many investors lose money—and how to avoid the common pitfalls. Paul shares his candid story of building millions after selling his staffing company, only to lose it all by 2008 through speculation rather than true investing. He explains the key lessons that shaped Wellings Capital’s disciplined approach: focusing on conservative structured deals (preferred equity and JV hybrid), strong operators, and durable assets in multifamily, self-storage, mobile home parks, and more. The conversation covers the risks of over-leverage and lofty projections, the power of base-hit returns, visionary-integrator dynamics, and why capital preservation beats chasing high IRRs. Paul Moore is the founder of Wellings Capital and author of The Perfect Investment and Storing Up Profits. He has interviewed hundreds of investors to uncover what creates lasting success in real estate. TIMESTAMPS 00:45 - Welcome to the Mailbox Money Show! 01:29 - Paul Moore's Journey: From Staffing Exit to Losing Millions by 2008 03:09 - Life Happens For Us: Learning from Failures 03:55 - Interviewing 238 People on "How to Lose Money" 04:25 - Discovering Traction & EOS – Finding Integrator Ben 06:37 - Visionary-Integrator Relationship in Business 07:36 - How Paul Hired & Promoted Ben to 50% Partner 10:43 - Shifting from Operator to Fund Model at Wellings Capital 12:49 - Preferred Equity & JV Hybrid Equity Structures 15:14 - Investor Demand for Cash Flow & Safer Deals 16:24 - 2022 Rate Hikes Exposed Market Problems 18:34 - Buffett & Munger Approach: Focus on Intrinsic Value 21:18 - Recommended Books & Resources for Investors 25:23 - Why 15% Risk-Adjusted Returns Are Strong in Today's Market 28:17 - Base Hits Philosophy: Don't Lose Money 30:43 - Closing Takeaways & How to Connect CONNECT WITH THE GUEST Website: wellingscapital.com Get Paul's Book: wellingscapital.com/resources #RealEstateInvesting #CapitalPreservation #PreferredEquity #InvestorMindset #MultifamilyInvesting #VisionaryIntegrator #WealthBuilding

    33 min
  6. Jack Hoss - AI Won’t Replace You. But Someone Using It Might.

    APR 13

    Jack Hoss - AI Won’t Replace You. But Someone Using It Might.

    Get my new book: https://bronsonequity.com/fireyourself Download my new special report - How to Use Inflation to Your Advantage - www.bronsonequity.com/inflation Join Bronson Hill on the Mailbox Money Show for another insightful conversation with Jack Hoss on how AI is transforming real estate investing, business operations, and personal productivity. In this episode, Jack shares practical ways investors and operators can leverage AI tools today—from AI agents handling lead response and property management to streamlining deal analysis, tenant communications, and operations—while emphasizing the importance of staying ahead of rapid technological change. Jack discusses building systems that amplify human strengths rather than replacing them, the massive efficiency gains available (including potential seven-figure savings on SaaS tools), current limitations and risks like token costs, security, and prompt injection, and why the winners in the coming years will be those actively using AI rather than fearing it. About Jack Hoss: Jack Hoss is a real estate investor and operator who has flipped and wholesaled hundreds of properties. He is the host of the RealDealChat podcast and helps investors scale their businesses through smarter operations and cutting-edge tools, including AI. TIMESTAMPS 00:44 - Welcome to the Mailbox Money Show 01:36 - Guest Intro: Jack Hoss & RealDealChat Podcast 02:17 - Jack's Journey from Microsoft Corporate Job to Real Estate Investing 03:27 - Historical Technological Shifts & Current AI Disruption 04:14 - AI Tools for Massive Efficiency Gains & SaaS Cost Savings 05:19 - Replacing SaaS Stack with AI in Real Estate Operations 06:59 - Hiring & Vetting AI Talent / Certifications & Experiments 08:34 - Bill Gates Story & Deliberate Practice with AI Tools 09:22 - OpenClaw / Agentic AI Experience, Costs & Security Risks 10:54 - Future of AI, Rapid Model Releases & Energy Consumption Challenges 12:41 - Nuclear Energy as a Solution to AI Power Demands 14:56 - Practical AI Applications: Speed to Lead & Property Management Agents 16:47 - Maintaining Authenticity & Human Oversight with AI 19:23 - Training Custom AI on Personal Data for Authentic Voice 21:34 - Low-Hanging Fruit: AI for Deal Follow-Up, Buy Box Guardrails & Operations 23:52 - Recommended Time Investment & Subscriptions for AI Learning 27:14 - Using Projects in ChatGPT for Persistent Context & Memory 30:14 - How to Connect with Jack Hoss CONNECT WITH THE GUEST Website: realdealcrew.com | assessment.realdealcrew.com #AIinRealEstate #RealEstateTech #ArtificialIntelligence #InvestorMindset #BusinessEfficiency #FutureOfInvesting #DealSourcing

    33 min
  7. Andrew Cushman - 4,576 Calls Before His First Deal

    APR 6

    Andrew Cushman - 4,576 Calls Before His First Deal

    Get my new book: https://bronsonequity.com/fireyourself Download my new special report - How to Use Inflation to Your Advantage - www.bronsonequity.com/inflation Join us for another inspiring conversation with Andrew Cushman, who turned relentless persistence into multifamily success. Andrew shares how he made 4,576 calls on a flip phone before closing his first deal, the mindset that powered his transition from engineering to full-time real estate, and key lessons from surviving the recent multifamily correction. The episode explores supply & demand fundamentals, why the Midwest offers steadier cash flow, conservative underwriting in higher-rate environments, and practical advice for passive investors on reframing setbacks and capitalizing on current opportunities. Andrew Cushman is a seasoned multifamily investor and operator who has acquired and managed thousands of apartment units. With an engineering background, he transitioned into real estate by flipping homes before scaling into multifamily. Known for his disciplined, long-term approach and zero-loss track record in a volatile market, Andrew emphasizes operational excellence, market selection, and building sustainable wealth through real estate. TIMESTAMPS 0:47 - Welcome to the Mailbox Money Show 1:32 - Andrew Cushman Introduction & Lifestyle by Design 2:42 - 4,576 Calls to First Flip Deal 3:58 - Brutal Daily Schedule & Phone Persistence 4:46 - Mindset: Believing in the System & R&D (Rip Off & Duplicate) 7:10 - Quitting Engineering Job After First Flip Success 9:06 - Motivation to Leave W2 & Risk of Regret 11:22 - Current Hunger vs Early Grinding Phase 13:17 - Multifamily Journey & Market Shift from Boom to Correction 13:53 - Probabilistic Underwriting & Fixing Debt in 2021 16:34 - Managing Downside Risk & Avoiding Deal Blowups 19:09 - Projection Realism vs Actual Performance 20:06 - Selling C-Class Assets & Portfolio Strategy at Market Peak 22:38 - Patience in Deal Sourcing & No-Deal-Better-Than-Bad-Deal Mindset 24:05 - Inch Wide Mile Deep Focus Strategy 25:30 - Other Asset Classes & Operator Dependence 26:48 - Current Buying Environment & Distress Opportunities 29:32 - How to Connect with Andrew Connecting with the Guest: LinkedIn: linkedin.com/in/andrewcushmanvpa Website: vpacq.com #MultifamilyInvesting #RealEstateMindset #PersistenceInBusiness #MarketCycles #PassiveIncome #ValueAddRealEstate #InvestorEducation

    33 min
  8. Kent Ritter - What the Multifamily Crash Revealed

    MAR 30

    Kent Ritter - What the Multifamily Crash Revealed

    Get my new book: https://bronsonequity.com/fireyourself Download my new special report - How to Use Inflation to Your Advantage - www.bronsonequity.com/inflation Join Bronson Hill on the Mailbox Money Show for another packed conversation with multifamily operator Kent Ritter on what the recent market correction truly revealed about investing in apartments. Kent shares hard-won lessons from the post-2022 downturn, why many new sponsors struggled, and why disciplined operators in strong, supply-constrained Midwest markets are now positioned for attractive opportunities. The discussion covers supply/demand fundamentals, the importance of operational excellence, conservative underwriting in a higher-rate environment, and how passive investors can reframe past challenges to capitalize on the current cycle. Kent Ritter is the CEO and founder of Hudson Investing, a multifamily private equity firm focused on the Midwest. With a background in business ownership and deep experience in real estate, Kent specializes in acquiring and operating apartments in stable, job-growing markets like Indianapolis and Cincinnati. He also hosts the Ritter on Real Estate podcast, where he interviews top operators and shares practical insights for investors. TIMESTAMPS 0:35 - Welcome to the Mailbox Money Show 1:27 - Multifamily Market from 2010–2022: Easy Wins & Cap Rate Compression 3:04 - The 2022 Shift: Rising Rates, Inflation, and Market Correction 4:56 - False Sense of Expertise During the Boom 7:03 - Lessons from Early Crowdfunded Deals and Due Diligence Failures 8:15 - Why Good Operators Are Surviving While Others Struggle 10:04 - Psychology of Investing After Losses: Reframing Fear 11:57 - Why Real Estate (and Multifamily) Remains a Core Long-Term Strategy 13:43 - Supply & Demand Fundamentals in Housing 15:40 - Current Opportunities: Depressed Valuations and 2016-Level Pricing 19:29 - Key Criteria for Buying Multifamily Today: Market Growth, Jobs, Landlord-Friendly Areas 21:56 - Newer Class A/B+ vs Older C-Class Properties: Bifurcation in Performance 24:48 - Long-Term Inflation Hedge and Rent Growth in Multifamily 26:01 - Outlook for Multifamily: 3–5 Year Cycle and Capital Deployment 29:28 - How to Connect with Kent Ritter and Hudson Investing CONNECT WITH THE GUEST Website: https://hudsoninvesting.com/ Podcast: Ritter on Real Estate #MultifamilyInvesting #RealEstateCycle #PassiveIncome #MarketCorrection #MidwestRealEstate #ValueAddStrategy #InvestorMindset

    32 min
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Ratings & Reviews

About

Are you looking for ways to grow your income without costing you more time? Many people think that to invest in real estate or other assets, you have to be involved on every level. In the Mailbox Money podcast, we explore new asset classes to invest in as well as tools that will make you a better passive investor. You won’t want to miss an episode because they’re packed full of life-changing wisdom from thought leaders. Hit subscribe and prepare to have your financial life changed! Bronson Hill is the host of the Mailbox Money podcast and the founder and CEO of Bronson Equity.

Information

  • Creator
    Bronson Hill
  • Years Active
    2021 - 2026
  • Episodes
    255
  • Rating
    Clean
  • Copyright
    © Bronson Hill
  • Show Website
    Mailbox Money Show

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