Want to use your retirement funds to invest beyond the stock market? In this episode, Henry Yoshida, CFP®, shares how his fintech company empowers investors to use their IRAs and 401(k)s to invest in private assets, all while maintaining tax advantages. Learn how he modernized retirement investing and why today's investors must think beyond traditional markets to build true diversification and long-term wealth.

Key Takeaways To Listen For

• The story behind Honest Dollar
• Why big financial institutions resist alternative investments
• How self-directed IRAs empower investors to fund private real estate
• What true diversification means in investing
• Psychological advantages of investing through tax-advantaged retirement accounts

Resources/Links Mentioned In This Episode

• Honest Dollar
• Greenlights by Matthew McConaughey | Hardcover and Audiobook
• The Richest Man in Babylon by George S. Clason | Kindle and Paperback
• Rocket Dollar Knowledge Base

About Henry Yoshida, CFP®Henry Yoshida, CFP®, is the Co-Founder and CEO of Rocket Dollar, a platform that empowers individuals to unlock their retirement savings by investing through Self-Directed IRAs and Solo 401(k)s. A three-time entrepreneur in the retirement services industry, Henry previously founded Honest Dollar, which was acquired by Goldman Sachs, and served as a Vice President of Retirement Business at Merrill Lynch, where he managed over $2.5 billion in client assets. He has been recognized by InvestmentNews as one of the "Top 40 Under 40" financial professionals and is a nationally sought-after voice on retirement innovation, alternative investing, and fintech. Henry frequently appears in major media outlets, including CNBC, Bloomberg, Yahoo! Finance, and TechCrunch, where he shares insights on modern retirement planning and wealth-building strategies.

Connect with Henry

• Website: Rocket Dollar
• LinkedIn: Henry Yoshida, CFP®
• Phone: (855) 762-5383

Connect With UsIf you're looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

Follow Keith's social media pages

• LinkedIn: Keith Borie
• Investor Club: Secret Passive Cashflow Investors Club
• Facebook: Keith Borie
• X: @BoboLlc80554

Ready to make your money work for you, without becoming a landlord? Travis Watts breaks down how limited partners build wealth through multifamily syndications. He shares lessons from his journey from single-family "DIY investor" to full-time LP, explains how rising rates reshaped the market, and why 2025 may be the perfect time to "buy the dip." Tune in to learn what mindset shifts are needed to invest for freedom, not stress!

Key Takeaways To Listen For

• Single-family mistakes to becoming a full-time limited partner in multifamily deals
• What rising interest rates taught investors about risk, leverage, and timing
• How supply-chain issues and insurance spikes doubled renovation costs post-pandemic
• Why conservative leverage (60–65%) and fixed-rate debt are key to surviving cycles
• Rent-growth trends: Midwest stability, Sun Belt recovery, and value-add upside

Resources/Links Mentioned In This Episode

• Best Ever Conference
• Passive Investor Tips by Travis Watts | Paperback
• Rich Dad Poor Dad by Robert T. Kiyosaki | Paperback and Mass Market Paperback

About Travis WattsTravis Watts is a proven leader in the real estate industry, where he's been investing since 2009 in multi-family, single-family, and vacation rentals. He began investing with Ashcroft Capital several years ago and has taken part in more than 30% of the Ashcroft opportunities. After experiencing above-average communication, reporting, deal volume, and performance, Travis expressed interest in joining the Ashcroft Investor Relations Team. Travis also has a background in traditional Wall Street investing and obtained a Series 7 and Series 63 license while working at a major brokerage firm with more than 400 billion in assets. He now dedicates his time to educating others in the world of investing and has made it his mission to share passive investment strategies to help others achieve and maintain wealth in real estate.

Connect with Travis

• Website: Ashcroft Capital
• Instagram: @passiveinvestortips
• Facebook: Travis Watts
• LinkedIn: Travis Watts:

Connect With UsIf you're looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

Follow Keith's social media pages

• LinkedIn: Keith Borie
• Investor Club: Secret Passive Cashflow Investors Club
• Facebook: Keith Borie
• X: @BoboLlc80554

Want to earn 10–16% returns through real estate that others overlook? Brian Seidensticker breaks down how investors profit from tax liens, tax deeds, and untapped property opportunities nationwide. He shares his journey from aerospace engineer to leading a platform tracking 9,000+ auctions a year and managing $2.5B in assets, plus how accredited investors can earn quarterly payouts.

Key Takeaways To Listen For

• The U.S. tax-sale system explained: how liens and deeds really work
• Supreme Court's Tyler v. Hennepin decision and why it reshaped investor strategies
• How Tax Sale Resources helps investors research auctions nationwide
• Inside Mount North Capital's 16% annual returns and capital-partner model
• 2 main traits that built two successful companies

Resources/Links Mentioned In This Episode

• Mount North Capital
• Mindset by Carol H. Dweck | Kindle, Paperback, and Hardcover
• Outlive by Peter Attia MD, and Bill Gifford | Kindle, Hardcover, and Spiral-bound

About Brian SeidenstickerBrian Seidensticker is the CEO and Co-Founder of Tax Sale Resources and Mount North Capital, leading companies that provide data, analytics, and investment opportunities in the property tax lien and tax deed space. With over 20 years of experience in finance, real estate, and technology, Brian has been instrumental in building platforms that aggregate auction data from thousands of counties nationwide. Under his leadership, Tax Sale Resources has become the industry's go-to source for research and intelligence on the $20+ billion tax lien market. Through Mount North Capital, he oversees institutional and accredited investor funds that capitalize on tax lien and distressed real estate opportunities while helping municipalities recover revenue efficiently.

Connect with Brian

• Website: Tax Sale Resources
• LinkedIn: Brian Seidensticker
• Facebook: Brian Seidensticker

Connect With UsIf you're looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

Follow Keith's social media pages

• LinkedIn: Keith Borie
• Investor Club: Secret Passive Cashflow Investors Club
• Facebook: Keith Borie
• X: @BoboLlc80554

Keep more of your profits and build wealth tax-deferred as Jon Hilley reveals how the 1031 exchange helps investors legally defer taxes while compounding their wealth. He shares insights from the cannabis industry and explains how Delaware Statutory Trusts (DSTs) are changing the game for passive investors. Dial in as he breaks down complex tax strategies into simple, actionable steps for long-term financial growth.

Key Takeaways To Listen For

• Why betting on regulatory reform is risky
• The rise of Delaware Statutory Trusts
• How to defer up to 40% of your taxes legally
• Rules every investor must know to complete an exchange
• A generational wealth strategy: "Defer, defer, defer, die"

Resources/Links Mentioned In This Episode

• The Boy, the Mole, the Fox and the Horse by Charlie Mackesy | Kindle, Hardcover, and Spiral-bound

About Jon HilleyJon Hilley is the Founder of 1031 Specialists, a tech-forward qualified intermediary platform revolutionizing how investors complete 1031 exchanges. A former financial analyst at Goldman Sachs and hedge fund associate at H.I.G. Capital, Jon brings deep financial expertise to the real estate space. He has held executive roles at multiple startups, including Mile High Labs and Firefly Vapor, and currently contributes to ventures like Silver Horn Capital and Silver Horn Ranch. With a focus on innovation, integrity, and investor success, Jon is building a modern solution for tax-deferred wealth building through real estate.

Connect with Jon

• Website: 1031 Specialists
• LinkedIn: Jonathan Hilley
• Phone Number: 631-438-1031
• Email: [email protected]

Connect With UsIf you're looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

Follow Keith's social media pages

• LinkedIn: Keith Borie
• Investor Club: Secret Passive Cashflow Investors Club
• Facebook: Keith Borie
• X: @BoboLlc80554

Most people don't realize their life insurance policy is an asset they can sell. Rob Haynie explains how seniors and business owners can tap hidden value in term and whole life policies. From cash surrender options to retained death benefits, he shares insider knowledge on how life settlements work, the 90-day process, and why fiduciary duty and transparency matter.

Key Takeaways To Listen For

• Why policy conversion before age 70 can create settlement opportunities
• The little-known option to convert term policies and then sell them
• How life settlements can turn policies from "expenses" into investments
• What the 90-day settlement process actually looks like, step by step
• Secondary vs. tertiary markets: how policies are valued, bundled, and resold

Resources/Links Mentioned In This Episode

• Abacus Life
• Coventry Direct
• The Art Of War by Sun Tzu | Paperback and Hardcover
• Book: The Confidence Game by Maria Konnikova | Kindle and Paperback

About Rob HaynieRob Haynie is the Managing Director of Life Insurance Settlements, Inc., one of the oldest and most established life settlement brokerage firms in the United States. With more than 20 years of experience in the life insurance secondary market, Rob has helped thousands of policyholders and financial professionals unlock the hidden value of life insurance policies through life settlements. He frequently speaks at industry conferences and has been featured in major financial publications for his expertise in providing policy owners with alternatives to lapsing or surrendering their policies.

Connect with Rob

• Website: Life Insurance Settlements
• LinkedIn: Rob Haynie
• Phone: 954-599-4433
• Email: [email protected]

Connect With UsIf you're looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

Follow Keith's social media pages

• LinkedIn: Keith Borie
• Investor Club: Secret Passive Cashflow Investors Club
• Facebook: Keith Borie
• X: @BoboLlc80554

Can you really build wealth from land nobody else wants? In this episode, Mark Podolsky, "The Land Geek," reveals how he turned burnout into over 6,000 land deals with returns of 300%–1,000%. Learn his system for finding sellers, flipping land, and creating passive income without tenants or toilets.

Key Takeaways To Listen For

• The "neighbor letter" method and how seller financing creates mailbox money
• Which states and markets offer the strongest demand for land buyers
• Bread-and-butter deal sizes and why terms beat cash sales for lasting income
• How land contracts protect investors and make foreclosures simple
• Why Mark began mentoring and how it creates ripple effects of freedom

Resources/Links Mentioned In This Episode

• Dirt Rich 2 by Mark Podolsky | Kindle and Paperback
• GeekPay
• The 12 Week Year by Brian P. Moran and Michael Lennington | Kindle, Paperback, and Hardcover
• The ONE Thing by Gary Keller and Jay Papasan | Kindle, Audiobook, and Paperback
• The Second Mountain by David Brooks | Kindle, Paperback, and Hardcover

Learn how to build passive income in real estate without renters, renovations, or rehabs with Mark Podolsky's book Dirt Rich. Grab your free copy now at https://www.thelandgeek.com/dirt-rich and explore The Land Geek's programs and coaching for even more guidance.

About Mark PodolskyMark Podolsky, known as The Land Geek, is one of the nation's leading authorities on raw land investing. Since 2001, he has completed over 6,000 land deals and built Frontier Equity Properties, LLC into a BBB A+ rated real estate company. Mark is the host of the Land Geek Podcast (formerly The Best Passive Income Model), where he shares strategies on creating wealth and time freedom through land investing. He also runs coaching programs and training communities that have helped thousands of investors learn how to generate passive income, achieve financial independence, and build businesses without renters, rehabs, or renovations.

Connect with Mark

• Website: The Land Geek
• Podcast: ‎The Art of Passive Income | Apple Podcasts and Spotify
• LinkedIn: Mark Podolsky
• Facebook: The Land Geek
• Instagram: @thelandgeek
• X: @TheLandGeek
• YouTube: The Land Geek

Connect With Us If you're looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

Follow Keith's social media pages

• LinkedIn: Keith Borie
• Investor Club: Secret Passive Cashflow Investors Club
• Facebook: Keith Borie
• X: @BoboLlc80554

What do you do when a business fails, a market collapses, or an entire strategy dries up? For serial entrepreneur Joe Downs, the answer has always been reinvention. From bars and restaurants to mortgages, tax liens, distressed second mortgages, and now self-storage, he shares how he built wealth by leaning into niches within niches.

Key Takeaways To Listen For

• How business failures forced Joe to reinvent and ultimately led him into real estate
• Tax lien seminars to distressed second mortgages and 25% IRA yields
• The largest distressed second mortgage businesses in the U.S.
• Why mom-and-pop ownership creates massive opportunity
• A loan that lets investors acquire self-storage with as little as 10% down

Resources/Links Mentioned In This Episode

• Self Storage Academy
• Who Not How by Dan Sullivan and Benjamin Hardy | Kindle and Paperback
• The Road Less Stupid by Keith J. Cunningham | Kindle and Hardcover

About Joe DownsJoe Downs is a Managing Partner at Belrose Storage Group, where he focuses on acquiring and managing self-storage facilities across the United States. With more than 25 years of experience in real estate and private equity, Joe has overseen the acquisition, financing, and development of projects totaling over $1 billion. At Belrose, he leads strategy, capital raising, and investor relations, helping deliver strong returns through value-add and opportunistic self-storage investments. His background includes senior roles in finance, acquisitions, and development, giving him a broad perspective on creating value in alternative real estate assets.

Connect with Joe

• Website: Belrose Storage Group
• LinkedIn: Joe Downs
• Email: [email protected]

Connect With UsIf you're looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

Follow Keith's social media pages

• LinkedIn: Keith Borie
• Investor Club: Secret Passive Cashflow Investors Club
• Facebook: Keith Borie
• X: @BoboLlc80554

How can everyday investors access private equity, infrastructure, and private credit assets once reserved for institutions? Kimberly Flynn, CFA, to unpack how interval and closed-end funds are transforming access to alternatives. With over 25 years in finance and leadership experience, she shares insights on product innovation, performance fees, SEC regulations, and why private wealth is the new frontier for alternative investing.

Key Takeaways To Listen For

• XA Investments' origin story and mission to open private markets for individuals
• How mutual funds, ETFs, and closed-end funds differ in liquidity and structure
• Infrastructure investing: airports, toll roads, and built-in inflation hedges
• Why private credit is dominating 2025 fund flows, and how yield drives adoption
• A more resilient strategy than direct lending in volatile markets

Resources/Links Mentioned In This Episode

• Cliffwater Funds
• KKR and Capital Group Launch Public Private Investment Solutions
• Hamilton Lane
• Partners Group
• Murderland by Caroline Fraser | Kindle and Hardcover

About Kimberly FlynnKimberly Flynn, CFA, is the Managing Director of Alternative Investments at XA Investments. She leads product development, distribution, and investor education for interval funds and other alternative investment solutions. Before joining XA Investments, Kimberly was a Managing Director at Nuveen Investments, where she spent over a decade building and supporting alternative investment products. She is a recognized industry expert on closed-end funds and interval funds, frequently speaking at conferences and contributing to industry publications. Kimberly holds the Chartered Financial Analyst (CFA) designation and brings extensive experience in helping financial advisors and investors access institutional-quality alternative strategies.

Connect with Kimberly

• Website: XA Investments
• LinkedIn: Kimberly Ann Flynn, CFA

Connect With UsIf you're looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

Follow Keith's social media pages

• LinkedIn: Keith Borie
• Investor Club: Secret Passive Cashflow Investors Club
• Facebook: Keith Borie
• X: @BoboLlc80554

Grow predictably, protect your family, and give you lifetime access to cash, while also securing your retirement. Mark Willis, CFP®, shares how to think differently about money, maximize retirement income, and pay for college without going broke. Dial in and use tools like dividend-paying whole life insurance and annuities to build financial independence.

Key Takeaways To Listen For

• The first step to building a solid money plan
• Main difference between term insurance (renting) and whole life insurance (owning)
• Why whole life policies grow predictably and can still fund outside investments
• Annuities as the most efficient tool for guaranteed lifetime income
• Effective strategies that create lasting wealth and exit options

Resources/Links Mentioned In This Episode

• The Business Fortress by David Barnett and Mark Willis | Kindle and Paperback
• Debt by David Graeber | Paperback
• The Road Less Stupid by Keith J. Cunningham | Kindle and Hardcover

Check out The Business Fortress webinars, available through New Banking Solution, for powerful business and financial insights. Don't forget to sign up at https://newbankingsolution.com/.

About Mark Willis, CFP®Mark Willis, CFP®, is a Certified Financial Planner™, best-selling author, and the owner of Lake Growth Financial Services, a Chicago-based firm helping clients take control of their finances with safe and predictable strategies. He co-hosts the Not Your Average Financial Podcast™, where he teaches how to pay for college without debt, invest in real estate, and create tax-free retirement income that can't be outlived. Mark has been recognized as a three-time #1 Best-Selling Author and is on a mission to help people think differently about money, become their own source of financing, and build lasting financial freedom.

Connect with Mark

• Website: New Banking Solution | Lake Growth
• Podcast: Not Your Average Financial Podcast™ | Apple Podcasts and Spotify
• LinkedIn: Mark Willis, ​CFP®
• Facebook: Lake Growth Financial Services
• Instagram: @notyouraveragefinancial
• YouTube: Not Your Average Financial Podcast™

Connect With UsIf you're looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

Follow Keith's social media pages

• LinkedIn: Keith Borie
• Investor Club: Secret Passive Cashflow Investors Club
• Facebook: Keith Borie
• X: @BoboLlc80554

Discover how to cut taxes, secure a second passport, and grow wealth internationally. Mikkel Thorup, one of the world's leading expat consultants with 25 years of nonstop travel, investments in 10+ countries, and a global family life. He reveals how to structure offshore wealth, gain residencies and citizenships, and build cash-flowing real estate portfolios abroad from beachfront property in Brazil to frontier plays in Paraguay.

Key Takeaways To Listen For

• How Mikkel turned a dyslexia diagnosis into a worldwide investment journey
• Why Brazil's northeast offers cash-flowing beachfront real estate under $100K
• The hidden tax advantages of Panama and why structure matters more than location
• Residencies that open doors to global mobility and tax benefits
• Unexpected opportunities in frontier markets

Resources/Links Mentioned In This Episode

• Brazil Beachfront Newsletter
• Paraguay Potential Newsletter
• Expat Secrets: How To Pay Zero Taxes, Live Overseas & Make Giant Piles of Money By Mikkel Thorup | Kindle and Paperback
• Mindset by Carol H. Dweck | Kindle, Paperback, and Hardcover

Stay ahead in the expat world with the Expat Money Newsletter! Get insider strategies, offshore tools, and global investment insights delivered straight to your inbox. Sign up now at https://expatmoney.com/newsletter.

About Mikkel ThorupMikkel Thorup is the world's most sought-after expat consultant and the Founder & CEO of Expat Money™, a private consultancy helping high-net-worth individuals legally reduce tax burdens, secure second residencies and citizenships, and build international investment portfolios that include real estate, agricultural land, and hard assets. He hosts The Expat Money Show podcast and authored the #1 best-selling book Expat Secrets – How To Pay Zero Taxes, Live Overseas And Make Giant Piles Of Money. Mikkel also co-founded the Expat International School of Freedom & Entrepreneurship, serves as Free Cities Ambassador with the Free Cities Foundation, and sits on several boards related to construction, development, and philanthropy, including 10 Eighteen Uganda, which supports teen mothers in Uganda's Namuwongo slums.

Connect with Mikkel

• Website: Expat Money® | Mikkel Thorup
• Podcast: The Expat Money Show | Apple Podcasts and Spotify
• LinkedIn: Mikkel Thorup
• Facebook: Expat Money
• Instagram: @expatmoneyshow
• X: @ThorupMikkel

Connect With UsIf you're looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

Follow Keith's social media pages

• LinkedIn: Keith Borie
• Investor Club: Secret Passive Cashflow Investors Club
• Facebook: Keith Borie
• X: @BoboLlc80554