The Investor's Guide To Joy

In this episode, Jason Pond shares how his Momentum Community helps ISP and tech business owners overcome the post-conference slump by turning inspiration into action. He explains how the group supports companies earning $750K–$3M annually with accountability, structure, and tactical guidance to scale beyond the "swamp" of early growth. Whether it’s refining customer experience, automating operations, or staying focused on that “one big thing,” Jason’s approach turns conference ideas into business momentum.Highlights of the Podcast00:01 – Introduction01:37 – What is the Momentum Community?02:12 – Who Jason Serves03:49 – Early Stages of the Community05:02 – Shifting Industry Needs06:27 – Marketing, Automation & Customer Experience07:39 – Ideal Community Members08:58 – Graduation from the Community10:39 – Readiness Over Revenue12:32 – Why Members Join14:11 – AI & Momentum Case Study15:30 – Curiosity vs. Commitment17:00 – Guiding Momentum with Direction18:04 – Tailored Accountability19:56 – Not a Mastermind, But a Growth Community#BusinessMomentum #TechEntrepreneurs #ScalingSuccess

In this episode, Jason Pond shares how he scaled his broadband business from a small-town ISP to a $5 million exit. He breaks down key lessons on co-founding, building a strong company culture, strategic planning beyond the $1M mark, and preparing a business for sale, even when you don’t plan to sell. Whether you're a solo entrepreneur or growing a team, Jason’s insights on leadership, growth, and staying battle-tested through challenges are invaluable.Highlights of the Podcast00:01 - Introduction and Episode Overview02:38 - Founder vs. Co-founder Dynamics04:48 - Company Building Journey07:49 - Company Culture and Strategic Planning10:00 - The Inflection Point at $1M Revenue13:50 - Remote vs. In-Office Teams15:56 - Caution on Outsourced Strategy and Consultants18:08 - Value of Industry Networking20:37 - Structuring a Business for Exit25:28 - Final Advice on Entrepreneurship#EntrepreneurshipJourney #BusinessGrowth #StartupExit

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 Podcast00:01 - Introduction01:56 - Equity Injection & Business Structuring03:35 - The Right Kind of CPA05:42 - Misalignment Between Present Actions & Future Goals07:28 - Seller Notes & New SBA Rules09:14 - Retirement Planning for Sellers11:29 - Rollover Equity & SBA Loan Guarantees13:01 - Valuation Misconceptions & Reality Check16:20 - Alternatives to Selling – Growth via Fractional Executives19:11 - Closing Thoughts#BusinessExitStrategy #SBAUpdates #ScaleYourBusiness

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 Podcast00:00 – Opening Thoughts01:24 – DIY Cost-Saving Tips for Business Owners04:51 – Why Cost Reduction Is Often Overlooked06:51 – Compensation Model & No-Risk Audit Process08:38 – Detailed Walkthrough of the Cost Audit Process12:53 – Long-Term Value & Why It Works#BusinessSavings #CostReduction #SmartInvesting

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 Podcast00:01 - Introduction02:14 - When and Why to Cut Costs05:27 – Knowledge is Power: The Value of 30 Years of Data07:52 – Same Service, Lower Cost - Guaranteed10:27 – Real-World Win: 84% Cost Savings13:47 – Small Changes, Big Impact16:57 – Custom, Transparent Implementation19:37 – We Sit on Hold for You21:37 – Service Categories Schooley Mitchell Handles23:37 – Industries and Ideal Clients26:07 – Why You Need a Regular Expense Review27:22 – Compensation Model: No Savings, No Fee28:27 – Closing Thoughts#BusinessSavings #CostOptimization #ProfitabilityTips

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 Podcast00:01 – Introduction01:45 – From Side Hustle to Real Estate Investing04:20 – Discovering the Power of 1031 Exchanges06:30 – Breaking Down 1031 Exchanges10:15 – Limitations and Pitfalls of 1031s12:40 – Introduction to Installment Sale Trusts15:05 – Customizing Exit Strategies for Investors18:20 – Real-Life Example: Using Installment Trusts Effectively21:45 – Misconceptions Around Real Estate Tax Deferral24:30 – Finding Joy Through Financial Education27:10 – Final Takeaways and Resources

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 Podcast00:00 – Introduction01:45 – Matt’s Background04:00 – First Investment & Lessons06:15 – Mindset Shift08:45 – Minimalist Lifestyle10:30 – Redefining Success13:00 – Authenticity & Joy16:20 – The Trap of Comparison18:50 – Advice for New Investors21:15 – Joy as a Business Strategy22:50 – Closing Remarks#PurposeDrivenInvesting #RealEstateJourney #RedefineSuccess

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 Podcast00:01 – Introduction & AI for 7-Figure Businesses04:10 – Welcome Devan Dillard & AI Agents Overview05:18 – Profit Margins and Hiring AI Over Staff09:08 – Downsizing & Ethical Employee Transitions10:14 – Hiring Developers for AI Buildouts11:13 – Cost of AI Implementation15:18 – Expense Reduction with AI16:21 – When You're Ready for AI18:21 – Competitive Advantage Through Cost Reduction20:03 – Ongoing Optimization & AI Maintenance22:11 – The 5 AI Executive Agents24:47 – Where to Learn More#AIAutomation #ScalableBusiness #EntrepreneurGrowth

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 Podcast00:01 – Introduction02:06 – Meet Devan Dillard04:01 – When to Start Integrating AI06:03 – AI as an Aid: Content Creation09:22 – AI for Visual Content & Branding11:37 – Delegation with AI Agents14:10 – Real-World Use: AI Email Assistant15:24 – Educating Yourself & Getting Started16:43 – Strategic Automation: Focus on Revenue19:32 – Connect with Devan Dillard

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.

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.

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.

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 Podcast00:01 - Introduction01:49 - What Greg Does with Land02:45 - Four Primary Land Strategies05:43 - What are Entitlements?06:54 - Keeping Pads or Exiting Entirely?09:38 - Should Land Be a Side Investment?10:57 - Land Risk Spectrum13:49 - The Importance of Reserves18:01 - Creative Use: Covered Land Plays & Leasing19:49 - Owner Financing Risks23:44 - Investing With Land Developers25:48 - Greg’s Investment Policy29:26 - Over-Entitling Can Backfire32:03 - Ideal Reader for the Book

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 Podcast00:00 – Introduction and episode overview02:15 – Paul’s background and early career journey07:30 – Major challenges and how he overcame them12:45 – Key turning points in his professional life18:20 – Leadership insights and strategies for success24:10 – Advice for aspiring professionals29:50 – Closing thoughts and where to connect with Paul

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 Podcast00:01 - Introduction to 75 Hard01:50 - Paul's Personal Experience with 75 Hard03:43 - The Core Lesson of 75 Hard05:49 - Paul's 150-Day Journey & Lessons Learned08:04 - The Five Tasks of 75 Hard

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 Podcast00:01 - Understanding Your Money01:16 - Developing an Abundance Mindset02:51 - The Power of Unexpected Opportunities04:38 - Budgeting for Success06:16 - Building an Emergency Fund10:00 - Paying Off High-Interest Debt11:59 - Investing Wisely13:32 - Becoming a Business Owner14:57 - Seeking Financial Guidance16:32 - Final Thoughts & Community Support

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 Podcast00:00 - The Unexpected Journey to Co-Authoring a Book01:33 - Introduction to Family Offices & Kevin Harrington03:30 - Meeting Kevin Harrington & The Dinner Invite05:38 - Becoming a Co-Author with Kevin Harrington07:41 - The Lego Mindset – Paul’s Chapter in the Book09:27 - The Final Book – From Startup to Standout11:42 - The Entrepreneurial Mindset & Giving Back

Every year, I take on a bold challenge to push my limits—this year, it's 100 YouTube videos in 100 days!

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 Podcast00:07 - Introduction to Taxes and Joy03:03 - Meet Bob Boeshaar04:07 - Why People Don't Pay Taxes07:59 - Audits and Recordkeeping09:19 - Hobby Losses vs. Business Losses18:35 - Types of Audits27:12 - Liens and Asset Management34:06 - Options for Tax Debt Resolution37:03 - Key Takeaways for Investors39:31 - Final Thoughts

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 Podcast00:08 - Introduction02:40 - Business Owners' vs. Individuals' Tax Strategies04:14 - Challenges for Smaller Businesses07:50 - Success Story: Tax Savings in Acquisitions09:50 - Advice for Business Owners12:59 - Real Estate Partnerships and Common Mistakes15:10 - Working with a Tax Professional22:26 - Timeline for tax planning23:50 - Choosing the right tax professional25:17 - Tino’s real estate investment journey30:05 - Due diligence and market risks32:40 - Mindset for investors