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336: How to be a Trusted Advisor with Rick Chess

Management Blueprint · 2026-06-15 · 22 min

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Episode notes

Rick Chess , attorney, real estate strategist, capital-raising expert, and trusted advisor, is passionate about helping entrepreneurs, investors, and business owners navigate complex decisions that can dramatically impact enterprise value and long-term success. Throughout a career spanning more than five decades, Rick has raised over $100 million for multiple organizations, guided companies through acquisitions, governance challenges, and strategic growth, and helped owners prepare for successful exits. We explore The Capital Raising Framework - Focus on Individuals, Not “the Market”; Be Ready to Sell; Start With Who You Know; Connect on Emotion; and Find a Problem to Solve. Rick explains why raising capital is ultimately about understanding people, not pitching ideas, why investors care more about their needs than your opportunity, and how trust-based relationships create opportunities that compound over time. He also shares lessons from raising capital, building influential networks, serving on boards, and helping entrepreneurs avoid costly mistakes when pursuing funding, growth, and exit strategies. - How to be a Trusted Advisor with Rick Chess Good day, dear listeners.

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