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 and Jimmy Rios dive into critical strategies for business owners facing financial challenges in 2025. From navigating SBA rule changes to transforming ugly balance sheets into profitable exits, they reveal how proactive planning, debt restructuring, and smart capital allocation can make or break a business. Whether you're scaling, refinancing, or just trying to stay afloat, this episode offers practical insights and real-world solutions every entrepreneur should hear.Highlights of the Podcast00:01 - The Long Game vs. Quick Wins01:07 - SBA Rule Changes Impacting Refinancing01:31 - Jimmy Rios’ Role and Approach03:32 - The Myth of More Funding as a Solution06:14 - SBA Refinancing: What's Changing and Why It Matters10:04 - Proactive Planning and Capital Strategy11:06 - Working Capital Justification Requirements14:04 - Honesty, Accountability & Hard Truths16:32 - Non-Recourse Funding as a Debt Solution18:08 - Final Thoughts & Takeaways#BusinessFunding #EntrepreneurshipTips #SBAChanges2025

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