Mastering the Art of Fundraising

Mastering the Art of Fundraising

Author: iHeartPodcasts April 2, 2026 Duration: 10:28

In this insightful clip of EYL, hosts Troy Millings and Rashad Bilal sit down with successful entrepreneur and mentor Ryan Breslow to discuss the intricacies of fundraising for startups. Ryan shares invaluable lessons and strategies that have helped him navigate the challenging world of venture capital and investment without falling into common pitfalls. 

Ryan dives deep into his personal journey, recounting initially unsuccessful attempts at raising capital and the crucial advice he received from mentors like Michael Carter of Playco. One of the key takeaways from this conversation is the importance of building relationships rather than simply requesting funds outright. Ryan explains why stating you're fundraising can put unnecessary pressure on both the entrepreneur and potential investors. Instead, creating a network of advocates who are genuinely excited about you and your project is more beneficial in the long run. 

Ryan also elaborates on the famed Silicon Valley adage: 'If you want money, ask for advice. If you want advice, ask for money.' This approach ensures that you not only gain valuable insights from seasoned professionals but also organically attract investors who believe in your vision and character. 

Troy and Rashad probe further, asking Ryan about the strategic targeting of potential mentors and investors, and how to avoid getting a 'no.' Ryan emphasizes the contagion effect of rejection in the investment community and advises playing the long game by impressing potential supporters gradually rather than rushing to secure funds. 

Throughout the episode, Ryan reflects on how critical it is to foster genuine connections within a network that can later be leveraged for intros and investments. His advice also covers the importance of not showing desperation to potential investors, as they are adept at detecting it to secure the best deals for themselves. 

For anyone looking to raise funds for their startup, this episode is a goldmine of practical wisdom and strategic advice. Whether you're in the early stages of your entrepreneurial journey or looking to refine your approach to fundraising, Ryan Breslow's experience and insights will equip you with the tools to succeed. 

Don't miss out on this episode packed with actionable advice and strategies for mastering the art of fundraising.

See omnystudio.com/listener for privacy information.


Hosted by Rashad Bilal and Troy Millings, Earn Your Leisure pulls back the curtain on the financial mechanics that power the worlds of sports and entertainment. This isn't just about headlines; it's a deep dive into the real stories of how money moves and how deals are made. You'll hear candid conversations that dissect business models and unpack the journeys of entrepreneurs, providing a street-smart education you won't find in a standard textbook. Each episode feels like a vital seminar, blending sharp analysis of current financial trends with the relatable context of pop culture. The Earn Your Leisure podcast, from iHeartPodcasts, operates on a simple premise: true financial freedom comes from understanding the game behind the game. It’s for anyone ready to look past the glamour and learn the practical strategies that build lasting wealth. Tune in for straightforward talk that makes complex business concepts accessible, always grounded in real-world examples from the industries that shape our culture.
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