Want to build wealth without a one-size-fits-all plan? In this episode, Mike Milligan shares how personalized strategies and proactive tax planning can change the trajectory of your financial life. Plus, powerful stories behind his "one-of-a-kind" approach, lessons from family entrepreneurship, and why every dollar should have a purpose.

Key Takeaways To Listen For

• The #1 financial skill most people lack
• Why tax rates in retirement won't automatically be lower
• Tax diversification tools every investor should know
• End-of-life planning: why 80% of men die married, and 80% of women die single
• An expert advice on true legacy you need to hear

Resources/Links Mentioned In This Episode

• The One of a Kind Financial Plan by Mike Milligan | Kindle and Paperback
• Build: An Unorthodox Guide to Making Things Worth Making by Tony Fadell | Kindle and Hardcover

About Mike Milligan, CFP®
Mike Milligan, CFP®, is the Founder and Chief Financial Planner of One Oak Financial, where he helps families and business owners design simple, values-based financial plans that create clarity and long-term confidence. With more than 15 years of experience as a CERTIFIED FINANCIAL PLANNER™, Mike specializes in retirement planning, purposeful wealth-building, risk management, and personalized investment strategies. He is known for his relationship-driven approach and for helping clients navigate major life and career transitions with wisdom and financial stewardship. Mike also hosts educational workshops and community events focused on financial literacy and generational planning.

Connect with Mike

• Website: Mike Milligan
• LinkedIn: Mike Milligan, CFP®

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

How do you scale from flipping houses to managing over $1B in workforce housing? Today, Michael Pouliot, CFA, CAIAs, shares his journey from digging trenches to leading a vertically integrated private equity firm. He breaks down the shift from BRRRR to large-scale multifamily, the power of operational efficiency, and why workforce housing in the Southeast offers lasting opportunity, all while revealing how the right team fuels sustainable investor growth.

Key Takeaways To Listen For

• Why the BRRRR strategy still works and how it scales assets
• Lessons from buying a 36-unit property on Chicago's South Side
• The power of broker relationships and how 20% of brokers control 80% of multifamily deal flow
• How Carbon's approach adapts to shifting market cycles and distressed opportunities
• Survive till 2025: why now is one of the best times in a decade to buy workforce housing

Resources/Links Mentioned In This Episode

• Think and Grow Rich by Napoleon Hill | Audiobook and Paperback
• The Magic of Thinking Big by David J. Schwartz | Paperback, Hardcover, and Kindle
• Traction by Gino Wickman | Kindle, Audiobook and Paperback

About Michael Pouliot, CFA, CAIA
Michael Pouliot, CFA, CAIA, is the Chief Investment Officer at Carbon Real Estate Investments, where he oversees investment strategy, capital deployment, and portfolio performance across the firm's vertically integrated real estate platform. With deep experience in institutional acquisitions, asset management, and private equity, Michael has led transactions across multifamily, workforce housing, and value-add real estate throughout the Southeast and Sunbelt regions. Prior to joining Carbon, he held senior roles at real estate investment firms and advisory groups, specializing in underwriting, capital markets, and large-scale portfolio operations. Known for his data-driven approach and expertise in market-cycle strategy, Michael is a frequent speaker on real estate economics, financing structures, and operational efficiency. He holds both the Chartered Financial Analyst (CFA) and Chartered Alternative Investment Analyst (CAIA) designations.

Connect with Michael

• Website: Carbon® Real Estate Investments
• Podcast: Deal Flow Podcast | YouTube and Audacy
• LinkedIn: Michael Pouliot, CFA, CAIA

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

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 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

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 Watts
Travis 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 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

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 Seidensticker
Brian 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 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

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 Hilley
Jon 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: john@1031specialist.com

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

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 Haynie
Rob 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: rob@lisettlements.com

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