Episodes
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In this episode of The Investor’s Guide to Joy, Paul Graham sits down with business strategist Jimmy Rios to unpack major SBA rule changes coming June 1, 2025, and what they mean for business owners looking to sell, scale, or bulletproof their companies. From equity injection requirements to seller financing shifts and rollover equity guarantees, they explore how to navigate these updates, avoid common pitfalls, and even rethink selling altogether. Whether you're planning an exit or eyeing growth, this episode offers practical insights to help you build a stronger, more sellable business.
Highlights of the Podcast
00:01 - Introduction
01:56 - Equity Injection & Business Structuring
03:35 - The Right Kind of CPA
05:42 - Misalignment Between Present Actions & Future Goals
07:28 - Seller Notes & New SBA Rules
09:14 - Retirement Planning for Sellers
11:29 - Rollover Equity & SBA Loan Guarantees
13:01 - Valuation Misconceptions & Reality Check
16:20 - Alternatives to Selling – Growth via Fractional Executives
19:11 - Closing Thoughts
#BusinessExitStrategy #SBAUpdates #ScaleYourBusiness
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In this episode of The Investor’s Guide to Joy, Paul Graham sits down with cost-reduction expert Shawn Stratton to uncover how business owners can save thousands without sacrificing service quality. From telecom audits to waste management, Shawn breaks down practical tips and reveals how his team identifies hidden savings through no-risk audits. If you’re running a seven or eight-figure business and think cost-cutting is just pennies on the dollar, this episode will change your perspective.
Highlights of the Podcast
00:00 – Opening Thoughts
01:24 – DIY Cost-Saving Tips for Business Owners
04:51 – Why Cost Reduction Is Often Overlooked
06:51 – Compensation Model & No-Risk Audit Process
08:38 – Detailed Walkthrough of the Cost Audit Process
12:53 – Long-Term Value & Why It Works
#BusinessSavings #CostReduction #SmartInvesting
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Missing episodes?
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In this episode of The Investor’s Guide to Joy, host Paul Graham sits down with Shawn Stratton of Schooley Mitchell to uncover how businesses can boost profitability by slashing hidden operating costs without sacrificing service. From waste removal to telecom and credit card fees, Shawn shares real-world strategies and case studies, including how one client saved 84% annually. Discover how expert audits, vendor data, and zero-risk implementation can turn overlooked expenses into major savings.
Highlights of the Podcast
00:01 - Introduction
02:14 - When and Why to Cut Costs
05:27 – Knowledge is Power: The Value of 30 Years of Data
07:52 – Same Service, Lower Cost - Guaranteed
10:27 – Real-World Win: 84% Cost Savings
13:47 – Small Changes, Big Impact
16:57 – Custom, Transparent Implementation
19:37 – We Sit on Hold for You
21:37 – Service Categories Schooley Mitchell Handles
23:37 – Industries and Ideal Clients
26:07 – Why You Need a Regular Expense Review
27:22 – Compensation Model: No Savings, No Fee
28:27 – Closing Thoughts
#BusinessSavings #CostOptimization #ProfitabilityTips
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In this episode of The Investor’s Guide to Joy, Paul Graham welcomes Trevor LaParl, to explore the power of the 1031 Exchange. Trevor breaks down how investors can legally defer capital gains taxes, shares real-life success stories, and explains how to avoid costly mistakes in real estate transactions. Whether you're a seasoned investor or just getting started, this episode is packed with essential strategies to help you build long-term wealth.
Highlights of the Podcast
00:01 – Introduction
01:45 – From Side Hustle to Real Estate Investing
04:20 – Discovering the Power of 1031 Exchanges
06:30 – Breaking Down 1031 Exchanges
10:15 – Limitations and Pitfalls of 1031s
12:40 – Introduction to Installment Sale Trusts
15:05 – Customizing Exit Strategies for Investors
18:20 – Real-Life Example: Using Installment Trusts Effectively
21:45 – Misconceptions Around Real Estate Tax Deferral
24:30 – Finding Joy Through Financial Education
27:10 – Final Takeaways and Resources
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In this episode of The Investor’s Guide to Joy, Matt Drouin shares how he broke away from the grind of chasing money to build a life and business rooted in purpose, community, and joy. Tune in to hear his journey from burnout to breakthrough and how redefining success can transform everything.
Higlights of the Podcast
00:00 – Introduction
01:45 – Matt’s Background
04:00 – First Investment & Lessons
06:15 – Mindset Shift
08:45 – Minimalist Lifestyle
10:30 – Redefining Success
13:00 – Authenticity & Joy
16:20 – The Trap of Comparison
18:50 – Advice for New Investors
21:15 – Joy as a Business Strategy
22:50 – Closing Remarks
#PurposeDrivenInvesting #RealEstateJourney #RedefineSuccess
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Discover how seven-figure entrepreneurs are cutting up to 50% in operational costs and scaling smarter with AI in this game-changing episode featuring Devan Dillard. From replacing entire departments with intelligent agents to optimizing workflows, marketing, and resource management, Devan shares practical insights on leveraging AI for exponential growth without the overhead. This is your essential guide to building a lean, future-proof business powered by automation and strategic innovation.
Highlights of the Podcast
00:01 – Introduction & AI for 7-Figure Businesses
04:10 – Welcome Devan Dillard & AI Agents Overview
05:18 – Profit Margins and Hiring AI Over Staff
09:08 – Downsizing & Ethical Employee Transitions
10:14 – Hiring Developers for AI Buildouts
11:13 – Cost of AI Implementation
15:18 – Expense Reduction with AI
16:21 – When You're Ready for AI
18:21 – Competitive Advantage Through Cost Reduction
20:03 – Ongoing Optimization & AI Maintenance
22:11 – The 5 AI Executive Agents
24:47 – Where to Learn More
#AIAutomation #ScalableBusiness #EntrepreneurGrowth
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In this episode of The Investor's Guide to Joy, Paul Graham sits down with AI strategist Devan Dillard to explore how six-figure business owners can leverage AI to scale smarter, not harder. From automating content creation and lead nurturing to using AI agents for tasks like email management and branding, Devan shares actionable tips that help solopreneurs and small teams save time, reduce costs, and boost impact without hiring a full staff.
Highlights of the Podcast
00:01 – Introduction
02:06 – Meet Devan Dillard
04:01 – When to Start Integrating AI
06:03 – AI as an Aid: Content Creation
09:22 – AI for Visual Content & Branding
11:37 – Delegation with AI Agents
14:10 – Real-World Use: AI Email Assistant
15:24 – Educating Yourself & Getting Started
16:43 – Strategic Automation: Focus on Revenue
19:32 – Connect with Devan Dillard
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In this insightful episode of The Investor’s Guide to Joy, Jay Bourgana seasoned entrepreneur and GoBundance member, shares powerful strategies for buying and scaling service-based businesses. From fire extinguisher compliance services to niche landscaping specialties and military base contracts, Jay breaks down how to spot high-margin opportunities, leverage SBA financing, and create synergy through smart acquisitions. Whether you're a first-time buyer or a growth-focused operator, this conversation is packed with actionable advice and real-world examples that reveal how to build profitable, sustainable businesses.
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In this solo episode of The Investor's Guide to Joy, host Paul Graham unveils a powerful new direction for the podcast focusing on helping business owners scale without burnout, exit with clarity, and build lasting wealth. Drawing from his own journey through entrepreneurship, burnout, and breakthrough, Paul shares how his Octane growth group is empowering founders to break free from the grind and reclaim their freedom. If you're ready to stop surviving and start designing a business and life that truly work for you, this episode is your starting point.
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Paul Graham and Trevor LaParl of Q1031.com discuss how the 537 Installment Sale Trust (IST) can serve as a powerful alternative or backup to 1031 exchanges, which often fail, leading to unexpected tax bills. Trevor explains how the IST allows investors to legally defer capital gains taxes and offers more flexibility than traditional exchanges, enabling them to invest in stocks, annuities, or refinance trust-backed notes for better returns. They explore how this strategy can apply to real estate, business sales, and even primary homes, providing a pathway to preserve wealth while maintaining control of assets.
They also cover how living trusts and installment sale trusts can be combined for effective estate planning, allowing high-net-worth individuals to defer taxes and build multigenerational wealth. Trevor shares examples of clients utilizing these strategies to manage rental properties, sell assets, and structure their estates. The discussion further explores the role of third-party administrators (TPAs) in trust management and the flexibility of note structures, helping investors safeguard their wealth while optimizing income streams and tax deferral strategies.
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In this episode of the Investor's Guide to Joy, we dive into the wild, gritty world of land development with Greg Farricielli a real estate wizard who’s turned empty lots into over $100 million in sales. Picture this: a guy who looks at a patch of dirt and sees not just potential, but a paycheck. Greg, the mastermind behind the upcoming book Dirt to Millions: Mastering the Art of Land Development, sits down with us to spill the secrets that have made him a legend in the game.
It all kicks off with a crash course in land entitlements the magic moment where raw, untouched land becomes a builder’s dream. Greg walks us through the process step-by-step: securing legal rights, untangling title messes, and making sure water, power, and roads are ready to roll. By the time he’s done, that dirt’s practically begging to be turned into homes and builders are lining up to pay big for it.
Highlights of the Podcast
00:01 - Introduction
01:49 - What Greg Does with Land
02:45 - Four Primary Land Strategies
05:43 - What are Entitlements?
06:54 - Keeping Pads or Exiting Entirely?
09:38 - Should Land Be a Side Investment?
10:57 - Land Risk Spectrum
13:49 - The Importance of Reserves
18:01 - Creative Use: Covered Land Plays & Leasing
19:49 - Owner Financing Risks
23:44 - Investing With Land Developers
25:48 - Greg’s Investment Policy
29:26 - Over-Entitling Can Backfire
32:03 - Ideal Reader for the Book
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In this episode, we dive into the fascinating journey of Paul, uncovering pivotal moments that shaped his career and insights that inspire. From overcoming challenges to achieving success, Paul shares valuable lessons on perseverance, leadership, and growth. Tune in for an engaging conversation packed with wisdom and motivation!
Highlights of the Podcast
00:00 – Introduction and episode overview
02:15 – Paul’s background and early career journey
07:30 – Major challenges and how he overcame them
12:45 – Key turning points in his professional life
18:20 – Leadership insights and strategies for success
24:10 – Advice for aspiring professionals
29:50 – Closing thoughts and where to connect with Paul
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I’m sharing my raw journey through the 75 Hard Challenge—a mental fitness test that pushed me to grow into the best version of myself. In this video, I open up about the highs and lows, from pushing through grueling workouts and strict diets to overcoming moments of weakness on the road. I even share how traveling, life’s unexpected challenges, and yes, even a delicious fried treat almost made me lose focus. Join me as I reveal the personal lessons and mindset shifts that came from embracing hard challenges head-on, and discover if this journey might be the spark you need for your own transformation.
Highlights of the Podcast
00:01 - Introduction to 75 Hard
01:50 - Paul's Personal Experience with 75 Hard
03:43 - The Core Lesson of 75 Hard
05:49 - Paul's 150-Day Journey & Lessons Learned
08:04 - The Five Tasks of 75 Hard
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Ready to take control of your finances this year? In this video, I break down the 10 essential steps that transformed my financial life—from understanding my money to building passive income streams. Drawing from my own experiences of doubling my income in four years and bouncing back from going broke twice, I share practical strategies and mindset shifts to help you achieve financial freedom.
Discover how tracking my spending uncovered shocking habits (like the $3,000 I once spent on entertainment in a month!) and why I believe investing in yourself and others beats traditional stock-heavy advice. Whether you’re tackling debt, creating a budget that works, or building an emergency fund with a twist (hint: it’s more than just 3-6 months of cash), this video has you covered.
Highlights of the Podcast
00:01 - Understanding Your Money
01:16 - Developing an Abundance Mindset
02:51 - The Power of Unexpected Opportunities
04:38 - Budgeting for Success
06:16 - Building an Emergency Fund
10:00 - Paying Off High-Interest Debt
11:59 - Investing Wisely
13:32 - Becoming a Business Owner
14:57 - Seeking Financial Guidance
16:32 - Final Thoughts & Community Support
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From watching Shark Tank as a kid to co-authoring a book with Kevin Harrington, this is my unexpected journey in entrepreneurship. Discover how a childhood promise to my mom and a chance meeting at a family office event led to Start Up to Stand Out, a book sharing actionable insights on building success, brick by brick.
Highlights of the Podcast
00:00 - The Unexpected Journey to Co-Authoring a Book
01:33 - Introduction to Family Offices & Kevin Harrington
03:30 - Meeting Kevin Harrington & The Dinner Invite
05:38 - Becoming a Co-Author with Kevin Harrington
07:41 - The Lego Mindset – Paul’s Chapter in the Book
09:27 - The Final Book – From Startup to Standout
11:42 - The Entrepreneurial Mindset & Giving Back
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Every year, I take on a bold challenge to push my limits—this year, it's 100 YouTube videos in 100 days!
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In this episode of The Investor's Guide to Joy, host Paul Graham sits down with Bob Boeshaar to tackle the often-daunting topic of taxes. Bob shares invaluable insights on navigating tax challenges, including how to avoid common pitfalls like poor recordkeeping and hobby losses, and provides practical tips for business owners, investors, and individuals facing audits or back taxes. The discussion highlights strategies for staying compliant, leveraging tax laws, and understanding your options for resolving tax debt, ensuring you can focus on achieving financial success and joy.
Whether you're a seasoned investor, a small business owner, or someone simply looking to better understand the IRS, this episode delivers actionable advice and key takeaways. From managing payroll taxes to addressing liens on properties and businesses, Bob’s expert guidance empowers listeners to approach taxes with confidence and clarity. Don’t miss this opportunity to demystify taxes and learn how to turn them into a tool for financial growth.
Highlights of the Podcast
00:07 - Introduction to Taxes and Joy
03:03 - Meet Bob Boeshaar
04:07 - Why People Don't Pay Taxes
07:59 - Audits and Recordkeeping
09:19 - Hobby Losses vs. Business Losses
18:35 - Types of Audits
27:12 - Liens and Asset Management
34:06 - Options for Tax Debt Resolution
37:03 - Key Takeaways for Investors
39:31 - Final Thoughts
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In this episode of The Investor's Guide to Joy, Tino Madyara, a seasoned tax professional and real estate investor, shares expert advice on tax strategies for business owners and investors. He highlights the importance of aligning personal and business tax plans to maximize savings, avoid surprises, and navigate complex tax structures. Tino also offers a success story where proactive tax planning saved a business $500,000 during an acquisition, demonstrating the power of strategic decisions in tax management.
Tino Madyara discusses common pitfalls in real estate partnerships, particularly around tax structures and depreciation, and stresses the need for business owners to work closely with a tax professional. Reflecting on his own real estate journey, he encourages investors to find a strategy that aligns with their personal values and long-term goals. This episode provides actionable insights into tax planning, real estate investing, and making informed decisions for financial success.
Highlights of the Podcast
00:08 - Introduction
02:40 - Business Owners' vs. Individuals' Tax Strategies
04:14 - Challenges for Smaller Businesses
07:50 - Success Story: Tax Savings in Acquisitions
09:50 - Advice for Business Owners
12:59 - Real Estate Partnerships and Common Mistakes
15:10 - Working with a Tax Professional
22:26 - Timeline for tax planning
23:50 - Choosing the right tax professional
25:17 - Tino’s real estate investment journey
30:05 - Due diligence and market risks
32:40 - Mindset for investors
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In this episode of The Investor's Guide to Joy, Paul Graham and Christion Sadler dive into the secondary real estate market, exploring how it provides investors with the opportunity to unlock equity before the typical 3-5 year lockup period. Christion explains how the Pre-iShare platform facilitates these transactions, offering a marketplace where buyers and sellers can connect. He shares insights into why liquidity is important for investors, whether due to life events or portfolio adjustments, and discusses the challenges of pricing and due diligence in secondary market transactions.
The conversation also delves into the creative possibilities within the secondary market, including structuring deals and negotiating terms, as well as the importance of being an accredited investor. Christion emphasizes the need for transparency, thorough communication, and understanding the risks and opportunities involved. With a focus on secondary market investments, he offers valuable advice on how investors can navigate this evolving space to unlock potential upside and achieve long-term success.
Highlights of the Podcast
00:07 - Introduction
02:32 - Christion's Role & Investor Profiles
04:25 - Investor Situations & Liquidity Needs
07:38 - The Need for a Secondary Market in Real Estate
12:24 - Due Diligence & Market Confidence
13:45 - Valuation & Pricing of Secondary Market Shares
15:44 - Process, Timeline, and Costs for Secondary Sales
18:30 - Buying and Selling Secondary Market Shares
19:16 - Due Diligence in Secondary Market Investing
22:39 - Benefits of Vintage Investing
25:27 - Types of Real Estate on the Platform
27:55 - Negotiating Secondary Market Transactions
32:43 - Accredited vs. Non-Accredited Investors
34:08 - Accredited Investor Status
35:41 - Secondary Market Benefits
39:08 - Preacher Liquidity Fund
41:45 - Operational Risks
45:18 - Personal Investment Advice
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In this episode of The Investor's Guide to Joy, host Paul Graham and Stacy Calvin dive into essential financial strategies for business owners and high-income earners. They explore the benefits of diversifying investments through syndications, optimizing entity structures for tax efficiency, and leveraging income-shifting techniques. Stacy also shares actionable insights on liability protection, proactive financial planning, and the importance of aligning financial decisions with long-term goals.
The value of working with a knowledgeable CPA and provides tips for choosing the right one based on experience, qualifications, and strategic approach. Stacy debunks common myths about tax preparation and highlights how proactive planning can maximize deductions, reduce liabilities, and enhance financial outcomes. Packed with practical advice, this episode is a valuable resource for anyone seeking to optimize their finances and elevate their success.
Highlights of the Podcast
00:08 - Introduction
01:59 - Guest Introduction
02:58 - Investing Personally vs. Through a Business
07:28 - Top Strategies for Larger Businesses
11:58 - Finding the Right CPA
14:21 - Debunking Tax Myths
15:36 - Tax Strategies for Business Owners
17:32 - Real Estate Rules and Myths
20:06 - Trusts and Tax Misconceptions
23:34 - The Importance of Year-End Planning
27:04 - Best Practices for Six-Figure Earners
30:17 - Tailored Strategies for Seven-Figure Earners
31:31 - Diversifying Lifestyle Investments
32:41 - Tax Strategies for High-Income Earners
35:05 - Choosing the Right CPA
38:56 - CPA Fees: Value vs. Cost
44:47 - Mindset Shift: "Knowledge is Power"
45:34 - Closing Remarks
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