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The Investor's Guide To Joy

The Investor's Guide To Joy

By: Paul Graham
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About this listen

 “How do I create true freedom without trading time for money?” “What’s the playbook for passive income, tax-smart investing, and joyful living?” You're in the right room. Each week, you'll hear from elite investors, founders, and wealth strategists who’ve traded stress for stewardship—sharing practical moves to help you grow, give, and enjoy more. Hosted by Paul Graham—entrepreneur, capital raiser, and founder of Octane—who helps purpose-driven leaders scale to 7–9 figures with peace of mind, not pressure. Ready to build wealth that serves your life—not the other way around? Subscribe and start investing with clarity, conviction, and joy.Paul Graham Economics Leadership Management & Leadership
Episodes
  • Using AI to Audit and Avoid Extra Cloud Spend

    Using AI to Audit and Avoid Extra Cloud Spend
    Apr 16 2026

    In this episode, Max from CloudGo.ai explains how companies bleed millions in cloud spend.

    Discover how to audit your environment to ensure your tech stack is ready for VC due diligence or a single engineer becoming a point of expensive failure.


    • 00:25 – The scale of the bleed: Why companies lose millions in cloud spend.

    • 02:47 – The Tech Debt Trap: Why waiting until Series A is a mistake.

    • 07:16 – The Planning Gap: Why most companies fail at the start of the life cycle.

    • 09:26 – Instant ROI: Cutting costs by 20% in one hour.

    • 11:45 – The Human Bottleneck: Preventing single points of failure in your team.

    • 14:45 – VC Due Diligence: Why "vibe coding" kills funding rounds.

    • 20:33 – Free Audits: How to stress-test your infrastructure today.
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    27 mins
  • The Relaunch: Why I Paused the Podcast

    The Relaunch: Why I Paused the Podcast
    Apr 14 2026

    In this relaunch episode, I share why I paused the show for nine months to shift from "making noise" to creating real transformation. Discover how to grow your net worth without losing your identity or your family, as you transition from a moneymaker to a true money manager.


    Chapters

    • 00:00 The Struggle of Wealth Preservation

    • 06:29 Learning from Guests and Audience Impact

    • 11:56 Commitment and Consistency
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    16 mins
  • What Every Business Owner Must Know About the 10% Equity Rule Starting June 1st

    What Every Business Owner Must Know About the 10% Equity Rule Starting June 1st
    May 23 2025

    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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    20 mins
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