Raw and Real Entrepreneurship®9 Jan 2025

Navigating Startup Growth and Challenges with Gregory Shepard, Founder of BOSS Capital Partners

In this inspiring episode of Raw and Real Entrepreneurship, host Susan Sly sits down with Gregory Shepard, founder of BOSS Capital Partners, serial entrepreneur, and author of The Startup Life Cycle. Gregory shares insights from his groundbreaking research, including interviews with 1,200 founders, and highlights the phases where startups are most vulnerable—and how founders can navigate these challenges to achieve the ultimate goal: a successful exit.

Susan and Gregory dive into the systemic biases faced by women and marginalized founders, the grit it takes to overcome these obstacles, and how celebrating small wins is crucial for entrepreneurial success. From marathon swimming and shark dives to Gregory’s ticket to space, they also explore what it means to push limits and embrace fearless leadership.

Gregory Shepard has built and sold 12 businesses in BioTech, TransitTech, AdTech and MarTech. He is a Forbes book author and contributor, and has been featured or quoted in publications like Fortune, Entrepreneur, The New York Observer, The DEAL, and Thrive Global. A recipient of four private equity awards for transactions between $250M to $1B, Greg has appeared on TV, radio, and popular podcasts, and been featured as a TEDx and keynote speaker at multiple universities and conferences worldwide.

Connect with Gregory:

Website: www.gregoryshepard.com

LinkedIn: @gregshepard/

Book: https://www.amazon.com/Startup-Lifecycle-Definitive-Guide-Building/dp/1637744323

Susan Sly is the maven behind Raw and Real Entrepreneurship. An award-winning AI entrepreneur and MIT Sloan alumna, Susan has carved out a niche at the forefront of the AI revolution, earning accolades as a top AI innovator in 2023 and a key figure in real-time AI advancements for 2024. With a storied career that blends rigorous academic insight with astute market strategies, Susan has emerged as a formidable founder, a discerning angel investor, a sought-after speaker, and a venerated voice in the business world. Her insights have graced platforms from CNN to CNBC and been quoted in leading publications like Forbes and MarketWatch. At the helm of the Raw and Real Entrepreneurship podcast, Susan delivers unvarnished wisdom and strategies, empowering aspiring entrepreneurs and seasoned business veterans alike to navigate the challenges of the entrepreneurial landscape with confidence.

Connect With Susan:

Website https://susansly.com

Website https://thepause.ai/

LinkedIn @susansly

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What if the anxiety, overworking, or self-doubt you feel as an entrepreneur isn’t just about your business, but the patterns you inherited?In this episode of Raw and Real Entrepreneurship®, Susan Sly ...

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