In this episode of Legacy Unscripted, entrepreneur Scott Baxter, founder and CEO of PlayYourCourt, shares the hard-earned lessons from his early fundraising journey and what every founder should know before giving up equity.
Scott reflects on raising his first $250,000 and giving away 38% ownership, all while learning the ropes of startup investment and valuation. He explains how raising only the minimal amount needed to validate your idea can protect your stake, attract smarter investors, and strengthen your long-term business strategy.
From his transition as a tennis coach turned entrepreneur to building PlayYourCourt into a recognized platform for connecting tennis players, Scott’s story is a candid look at the highs and lows of early-stage entrepreneurship.
Whether you’re a first-time founder, an investor, or simply curious about how to navigate the fundraising landscape, this conversation delivers clear, actionable insights.
🔥 Key Takeaways:
Why raising too much too soon can cost you control
How to prove your valuation before scaling investment
Common startup fundraising mistakes and how to avoid them
Why proof of concept is key to investor confidence
💬 Memorable Quotes:
“I gave up 38%.”
“I didn’t know how to raise money.”
“Raise the minimal amount you need to prove your valuation.”
🎧 Chapters:
00:00 From Tennis Pro to Entrepreneur: The Journey Begins
01:06 Funding Challenges and Lessons Learned
✨ Keywords: fundraising, investment, entrepreneurship, business strategy, valuation, startup mistakes
#Fundraising #Entrepreneurship #StartupLessons #InvestmentStrategy #BusinessValuation #StartupMistakes #PlayYourCourt #LegacyUnscripted

I hope you enjoy this episode!
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– Russ and the Legacy, Unscripted! podcast team

Connect with Russ on LinkedIn:https://www.linkedin.com/in/business-coach-florida/
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Get in touch with Russ: [email protected]

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Apple Podcasts: https://podcasts.apple.com/us/podcast/legacy-unscripted/id1793597573
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Legacy, Unscripted! hosted by Russ is a no-filter conversation about the legacies we’re building every day - whether we realize it or not. This podcast dives into how entrepreneurs, leaders, and everyday difference-makers live intentionally, overcome obstacles, and shape their impact on others. With raw stories, honest reflections, and practical insights, Legacy, Unscripted! invites you to reflect on your values, your purpose, and the mark you’re leaving on the world.