Boost Mobile’s Former CEO Reveals the Raw Truth About Startup Survival | Stephen Stokols

🎙 In this episode of the Doctor’s Investor Club Podcast, Stephen Stokols shares his journey from corporate executive to serial entrepreneur, angel investor, and founder of Tru Skye Ventures. From nearly going bankrupt with FreedomPop to securing a $30M lifeline, Stephen reveals the raw highs and lows of startup life, the power of face-to-face investor relationships, and why health tech is the next trillion-dollar frontier. As the former CEO of Boost Mobile and a veteran of over 30 angel investments, Stephen breaks down how physicians and dentists can invest like insiders even without deep tech experience.

🔑 What You’ll Learn:

• How Stephen raised hundreds of millions and scaled FreedomPop from scratch
• The emotional toll of entrepreneurship and how to survive near-bankruptcy
• Why authenticity is the most underrated leadership trait
• How Tru Skye Ventures is disrupting health & human performance
• The rise of nutrient-conscious consumer brands like Barcode
• How elite athlete tech is becoming accessible to everyday consumers
• Investment strategies for doctors: risk profiles, syndications, and deal access
• Why face-to-face investor meetings still matter in an AI-driven world

⏱ Timestamps:
 00:00 – Intro
 03:00 – Corporate roots and the leap into entrepreneurship
 05:00 – Accidental success: 10M users and a dating pivot
 07:00 – Leadership style: rebellious, authentic, and direct
 09:00 – The emotional rollercoaster of startup life
 11:00 – Near-bankruptcy and the $30M save
 13:00 – The power of personal investor relationships
 15:00 – Launching Tru Skye Ventures with Metta World Peace
 17:00 – Health-conscious investing: Barcode and beyond
 19:00 – Fluoride, cupping tech, and military-grade wellness tools
 22:00 – Syndication-style investing for physicians and dentists
 24:00 – Regional health culture: California vs. Mississippi
 26:00 – How elite performance tech is going mainstream

💥 About Stephen Stokols:
 Stephen Stokols is the founder of Tru Skye Ventures, former CEO of Boost Mobile, and a serial entrepreneur with deep roots in telecom, healthcare, and technology. He’s raised hundreds of millions in venture capital, led multiple exits, and now invests in disruptive health and wellness startups alongside NBA legend Metta World Peace.

📲 Connect with Stephen Stokols:
 Website: TruSkyeVentures.com
LinkedIn: Stephen Stokols
Instagram: Stephen Stokols

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