Cash Flow Conversations for Founders

Matt Love
  • 5.0 (8)
  • Business
  • Updated Weekly

Cash Flow Conversations with Matt Love. For family oriented entrepreneurs who want cash flow that serves their calling. Teacher mentor talks: story first, then the principle. Steady and educational. Not hype. Book a conversation: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK Community: https://www.skool.com/cash-flow-architects-5491 Book: https://www.amazon.com/Entrepreneurs-Asset-Family-Oriented-Greater-Themselves/dp/1964811902 Work with us: https://cashflowarchitects.com/ Educational only. Not personalized financial, tax, or legal advice.

  1. 4d ago

    51. How to Build Generational Wealth That Actually Lasts | Andrew Howell

    💰 WANT MORE CONTROL, LIQUIDITY & PURPOSE WITH YOUR MONEY? 👉 Book Your Strategy Call: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK 👥 Join the Cash Flow Architects Community: https://www.skool.com/cashflowarchitects/about 📖 Get Matt's Book — The Entrepreneur's Asset: https://www.amazon.com/Entrepreneurs-Asset-Family-Oriented-Greater-Themselves/dp/1964811902 🌐 Cash Flow Architects: https://cashflowarchitects.com --- What happens to the wealth you've spent your entire life building after you're gone? In this episode of Cash Flow Conversations, Matt Love sits down with estate and tax attorney Andrew Howell to discuss why creating wealth is only half the battle. The other half is building a family capable of preserving it. After 25 years practicing law, Andrew believes traditional estate planning often focuses too heavily on wills, trusts and transferring assets at death — without spending enough time on how wealth should function while you're alive or how the next generation will handle it when you're gone. Andrew and Matt discuss: ✔️ Why family wealth can disappear across generations ✔️ Estate planning beyond a simple will ✔️ Lifetime trusts and protecting inherited assets ✔️ Asset protection from creditors ✔️ Estate and tax planning ✔️ Raising children around wealth without destroying ambition ✔️ Identifying and passing down family values ✔️ Andrew's “family bank” approach ✔️ Why heirs should understand the estate plan ✔️ Business succession planning ✔️ Life insurance and estate liquidity ✔️ AI and the future of legal planning ✔️ Building a coordinated “family office” of advisors One of Andrew's most interesting approaches is what he calls his “family bank.” If one of his children finds an opportunity, they don't simply receive the money. They're expected to present the opportunity, create a plan, borrow from the family and remain accountable for paying it back. The idea is to give the next generation access to opportunity without removing the need to earn, build and make decisions for themselves. Because a lasting legacy isn't simply the amount of money your children inherit. It's the structure, values, education and opportunities you leave behind with it. 🎧 LISTEN TO CASH FLOW CONVERSATIONS: 🍎 Apple Podcasts: https://podcasts.apple.com/us/podcast/cash-flow-conversations-for-founders/id1632246139 🟢 Spotify: https://open.spotify.com/show/7em6d50zFLw9FY1GfJCYHB Podcast Management by @Azatrii ⚠️ This content is for educational and informational purposes only and does not constitute legal, tax, investment, accounting or insurance advice.

  2. Sep 25

    50. The Barbell Strategy — Why Balanced Portfolios Fail (and What Wealthy People Do Instead)

    Financial advisors love the "balanced portfolio" — but Matt Love and Glenn Yaney argue it's actually the riskiest place to put your money. Matt and Glenn break down the barbell strategy — inspired by Nassim Taleb's "The Black Swan" — and why it beats the standard 60/40 portfolio most advisors recommend. Instead of spreading money thin across stocks and bonds, the barbell approach puts most capital in safe, guaranteed assets and concentrates the rest into what you actually know and understand. Glenn shares how this played out in his own real estate journey, and Matt makes the case that true diversification isn't stocks and bonds — it's safe money paired with focused, high-conviction investing. 💡 Key Takeaways: ✅ What the barbell strategy is and why it beats a 60/40 portfolio✅ Why "diversified" portfolios may be more correlated than you think✅ Why Black Swan events expose the flaws in balanced portfolios✅ Why specialization builds wealth faster than diversification✅ The difference between a CPA and a true tax strategist 🎯 Who Should Listen?Anyone with a 401(k) or advisor-managed portfolio, real estate investors, and entrepreneurs rethinking risk. 👉 Book a free strategy call: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK ⚠️ Not tax, legal, or financial advice. Consult a licensed professional before making financial decisions.

  3. Sep 11

    49. The Lifestyle Investor's Justin Donald on Using One Dollar Three Times

    He lost $160,000 walking away from a bad condo deal. Then he discovered a strategy that meant he'd never fully lose on a deal again. Justin Donald, Wall Street Journal bestselling author of "The Lifestyle Investor," joins Matt Love to break down the failed condo deal that shaped his investing philosophy, and how a whole life policy loan later funded a mobile home park deal that returned 36% cash-on-cash — while his policy kept growing untouched. They dig into "three uses of one dollar," income amplifiers like seller financing and equity kickers, why a top asset manager's own CIO privately ditched the 60/40 portfolio, and how the barbell strategy mirrors the playbook single-family offices use for billionaire wealth. 💡 Key Takeaways: ✅ How a $160K loss shaped his entire investing philosophy✅ How a policy loan funded a 36% cash-on-cash real estate deal✅ The "three uses of one dollar" concept✅ Why a top CIO doesn't run a 60/40 portfolio for his own money✅ How the barbell strategy mirrors the single-family office playbook 🎯 Who Should Listen?Real estate investors, business owners, and anyone curious about whole life insurance as an investing tool. 👉 Book a free strategy call: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK ⚠️ Not tax, legal, or financial advice. Consult a licensed professional before making financial decisions.

  4. Sep 6

    48. Building a Legacy That Lasts — Estate Attorney Andrew Howell on QSBS, Trusts & Family Wealth

    What if you could sell your company and legally pay zero federal income tax on up to $15 million? Estate attorney Andrew Howell, co-founder of York and Howell, joins Matt Love to break down QSBS (Section 1202) and why most business owners have never heard of it. They go beyond tax strategy into real legacy planning — building a "family constitution," avoiding "trustafarian" kids, and the asset protection playbook Andrew uses with high-net-worth families, from LLCs to offshore trusts. Andrew also shares his influence on Garrett Gunderson's book "What Would the Rockefellers Do?" and why he believes legacy is what you leave in someone, not just to them. 💡 Key Takeaways: ✅ How QSBS can eliminate tax on up to $15M+ per shareholder✅ Why C-Corps qualify for this break and S-Corps usually don't✅ The asset protection playbook — LLCs to offshore trusts✅ How to build a "family constitution" so wealth doesn't ruin the next generation✅ How the Rockefellers structure wealth to last generations 🎯 Who Should Listen?Business owners, real estate investors, and families thinking about estate or legacy planning. 👉 Book a free strategy call: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK ⚠️ Not tax, legal, or financial advice. Consult a licensed professional before making financial decisions.

  5. Aug 28

    47. Buy, Borrow, Die — The Right (and Wrong) Way to Leverage Volatile Assets

    "Buy, borrow, die" is one of the most talked-about wealth strategies out there — but done wrong, it can wipe you out completely. Matt Love and Glenn Yaney open with a true story of a client who turned an IPO windfall into $10 million, leveraged his stock as collateral, and lost it all when the market crashed and the bank called the loan. From there, they unpack what real diversification actually means, why IUL isn't the safe, uncorrelated asset most agents claim, and why whole life insurance can act as a true "bond replacement." They also discuss viewing every loan as an "investor," and why relying on a single W-2 income carries more risk than most people realize. 💡 Key Takeaways: ✅ Why leveraging volatile assets can go to zero fast✅ What real diversification actually means✅ Why IUL isn't as "safe" as it's marketed to be✅ How whole life insurance acts as a true bond replacement✅ Why every loan should be viewed as an "investor"✅ How much of your portfolio should stay guaranteed and liquid 🎯 Who Should Listen?Investors using leverage or "buy, borrow, die" strategies, business owners, and anyone rethinking diversification. 👉 Book a free strategy call: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK ⚠️ Not tax, legal, or financial advice. Consult a licensed professional before making financial decisions. If you want to talk through how this applies to your family, book an Initial Cash Flow Conversation: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK JOIN THE COMMUNITY https://www.skool.com/cash-flow-architects-5491 Get The Book — The Entrepreneur's Asset https://www.amazon.com/Entrepreneurs-Asset-Family-Oriented-Greater-Themselves/dp/1964811902 Work With Us https://cashflowarchitects.com/ This conversation is educational, not financial, tax, or legal advice.

  6. Aug 21

    46. The Hidden Tax Lien in Your 401(k) — Glenn Yaney's Real Estate & Retirement Strategy

    Your 401(k) has a tax lien hidden inside it — and not even your CPA can tell you exactly how much it is. Real estate investor Glenn Yaney returns to Cash Flow Conversations to cover the origin story he skipped last time: the mortgage paydown mistake that nearly stalled his cash flow journey, why he cashed out roughly $300K from his 401(k)/QRP despite the penalty, and how cost segregation and accelerated depreciation changed the math. Matt and Glenn also break down why a 2.75% mortgage is an asset, not a liability, and how RMDs and inherited retirement accounts can leave your family with a tax bomb nobody warned you about. 💡 Key Takeaways: ✅ The mortgage paydown mistake that cost him more than it saved✅ Why he cashed out his 401(k)/QRP anyway✅ How cost segregation offsets capital gains outside a 1031 exchange✅ Why a low-rate mortgage is your best investor✅ The hidden tax lien inside every retirement account✅ How RMDs create a tax bomb for your kids 🎯 Who Should Listen?Real estate investors, business owners, and anyone rethinking their 401(k) or estate strategy. 👉 Book a free strategy call: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK ⚠️ Not tax, legal, or financial advice. Consult a licensed professional before making financial decisions. If you want to talk through how this applies to your family, book an Initial Cash Flow Conversation: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK JOIN THE COMMUNITY https://www.skool.com/cash-flow-architects-5491 Get The Book — The Entrepreneur's Asset https://www.amazon.com/Entrepreneurs-Asset-Family-Oriented-Greater-Themselves/dp/1964811902 Work With Us https://cashflowarchitects.com/ This conversation is educational, not financial, tax, or legal advice.

  7. Aug 14

    45. Redemptive Investing & Impact Real Estate — Deyl Kearin on Building a $5.5B Portfolio

    What if the most profitable real estate strategy wasn't about squeezing every dollar out of tenants — but investing in them? Deyl Kearin, a real estate investor and capital raiser for DLP Capital — a $5.5 billion real estate firm — joins Matt Love to break down "redemptive investing": a business model where treating tenants well directly improves returns, not just ethics. Deyl shares his path from flipping houses during the 2008 crash to building a $100M portfolio, stepping away to teach entrepreneurship, and eventually joining DLP's mission-driven approach to workforce housing. They dig into the hard numbers — tenants staying 2-3x longer than average, lower turnover and vacancy — plus how faith and purpose have shaped his career. 💡 Key Takeaways: ✅ How Deyl built a $100M portfolio after the 2008 crash✅ What "redemptive investing" actually means in practice✅ Why tenants stay 2-3x longer in DLP's communities — and what that does to returns✅ How thoughtful community design drives real estate value✅ Why impact and profitability aren't opposites 🎯 Who Should Listen?Real estate investors, multifamily operators, and anyone exploring impact or faith-driven investing. 👉 Book a free strategy call: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK ⚠️ Not tax, legal, or financial advice. Consult a licensed professional before making financial decisions. If you want to talk through how this applies to your family, book an Initial Cash Flow Conversation: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK JOIN THE COMMUNITY https://www.skool.com/cash-flow-architects-5491 Get The Book — The Entrepreneur's Asset https://www.amazon.com/Entrepreneurs-Asset-Family-Oriented-Greater-Themselves/dp/1964811902 Work With Us https://cashflowarchitects.com/ This conversation is educational, not financial, tax, or legal advice.

  8. Aug 7

    44. Debt: Why Wealthy People Borrow Differently — Glenn Yaney on Infinite Banking

    Debt is Matt Love's "second favorite four-letter word" — and he thinks it's one of the most misunderstood concepts in personal finance. In this episode of Cash Flow Conversations, Matt sits down with real estate investor and infinite banking practitioner Glenn Yaney to break down why wealthy people borrow money completely differently than everyone else. They dig into why "debt-free" isn't always the goal, the difference between good debt and bad debt, and why financing an appreciating, cash-flowing asset is a completely different game than financing a depreciating one like a car. Glenn shares how watching his parents over leverage themselves on non-productive assets shaped his own approach to debt, and Matt breaks down the concept of opportunity cost — why paying cash for a car can actually cost you more than financing it, once you factor in what that cash could have earned elsewhere. From there, the conversation shifts into infinite banking: how a properly structured life insurance policy lets you borrow against your own capital while it continues to grow, and why loan proceeds from a policy never even show up on your tax return. They close out talking about the risks of infinite banking, how to hold yourself accountable when reusing capital, and how both Matt and Glenn personally define financial freedom. 💡 Key Takeaways: ✅ Why "debt-free" isn't always the smartest financial goal✅ The difference between good debt and bad debt✅ Why paying cash for a car can cost you more than financing it✅ How infinite banking lets you access capital while it keeps growing✅ Why a policy loan never shows up on your tax return✅ The real risks of infinite banking — and when it doesn't make sense✅ How Matt and Glenn each define financial freedom 🎯 Who Should Listen? ✔️ Real estate investors✔️ Business owners and entrepreneurs✔️ Anyone who's been told "all debt is bad"✔️ Anyone curious about infinite banking or cash value life insurance✔️ Anyone looking to improve cash flow and build long-term wealth Want help designing your financial life with more purpose, cash flow, and control? 👉 Book your strategy call here: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK Connect with like-minded entrepreneurs and families who want more control, liquidity, and purpose with their money. 👉 Join Here: https://www.skool.com/cashflowarchitects/about Discover how family-oriented entrepreneurs can create greater control, liquidity, and legacy while investing in themselves and those they love. 👉 Order your copy here: https://www.amazon.com/Entrepreneurs-Asset-Family-Oriented-Greater-Themselves/dp/1964811902 🔗 Connect With Cash Flow Architects 🌐 https://cashflowarchitects.com📺 YouTube: https://youtube.com/@cashflowarchitects📸 Instagram: https://instagram.com/cashflowarchitects 🎙️ Subscribe to Cash Flow Conversations for more conversations on business, cash flow, retirement, taxes, investing, and legacy planning. ⚠️ Financial DisclaimerThe information discussed in this podcast is intended for educational and informational purposes only and should not be construed as investment, tax, legal, or accounting advice. Cash Flow Architects and Matt Love do not provide legal or tax advice. Any opinions expressed by guests are their own and do not necessarily reflect those of Cash Flow Architects. Before making financial decisions, consult with your own qualified financial, tax, and legal professionals. Guarantees are based on the claims-paying ability of the issuing insurance company. Book an Initial Cash Flow Conversation:https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCKJOIN THE COMMUNITY:https://www.skool.com/cash-flow-architects-5491Get The Book:https://www.amazon.com/Entrepreneurs-Asset-Family-Oriented-Greater-Themselves/dp/1964811902Work With Us:https://cashflowarchitects.com/Educational content only. This is not personalized financial, tax, or legal advice.

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Cash Flow Conversations with Matt Love. For family oriented entrepreneurs who want cash flow that serves their calling. Teacher mentor talks: story first, then the principle. Steady and educational. Not hype. Book a conversation: https://link.captivationhub.com/widget/booking/CefVjOwzLg0OAi7cgqCK Community: https://www.skool.com/cash-flow-architects-5491 Book: https://www.amazon.com/Entrepreneurs-Asset-Family-Oriented-Greater-Themselves/dp/1964811902 Work with us: https://cashflowarchitects.com/ Educational only. Not personalized financial, tax, or legal advice.

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