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🎙 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:
⏱ 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
⚡ Like, Subscribe & Share
If this episode gave you insight into startup investing or health tech disruption, hit that subscribe button, share it with a fellow doctor, and drop a comment with your biggest takeaway.
🎟 Join the Movement
👉 DoctorsInvestorClub.com – Free to sign up. Get VIP membership when you refer 3 other doctors or dentists.
👉 LegacyRxConference.com – Join the confe
🌐 Connect with Dr. Kyle Stephenson on social media to stay updated on expert insights and strategies, and schedule your personalized consultation today to start building your path to financial freedom:
🔍 Instagram: @dr.kylestephenson
🔍 LinkedIn: Kyle Stephenson, D.O.
🔍 Facebook: Kyle Stephenson
🔍 Website: www.joinlegacyrx.com
🔍 Schedule a call & access resources: https://linktr.ee/kylestephenson
Network and Learn with Millionaires and Industry Leaders this October 24-25, 2025 → https://link.joinlegacyrx.com/widget/form/SZpeggmkXmXlDWnGtO9Ilink.joinlegacyrx.com
If you want to learn more about Infinite Banking Concept, click below: http://beyourownbank.com/ks
Don't miss out on the opportunity to transform your financial future. Subscribe now and start your journey towards financial wellness with Dr. Kyle Stephenson! 💼
By Kyle Stephenson, D.O.5
3636 ratings
🎙 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:
⏱ 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
⚡ Like, Subscribe & Share
If this episode gave you insight into startup investing or health tech disruption, hit that subscribe button, share it with a fellow doctor, and drop a comment with your biggest takeaway.
🎟 Join the Movement
👉 DoctorsInvestorClub.com – Free to sign up. Get VIP membership when you refer 3 other doctors or dentists.
👉 LegacyRxConference.com – Join the confe
🌐 Connect with Dr. Kyle Stephenson on social media to stay updated on expert insights and strategies, and schedule your personalized consultation today to start building your path to financial freedom:
🔍 Instagram: @dr.kylestephenson
🔍 LinkedIn: Kyle Stephenson, D.O.
🔍 Facebook: Kyle Stephenson
🔍 Website: www.joinlegacyrx.com
🔍 Schedule a call & access resources: https://linktr.ee/kylestephenson
Network and Learn with Millionaires and Industry Leaders this October 24-25, 2025 → https://link.joinlegacyrx.com/widget/form/SZpeggmkXmXlDWnGtO9Ilink.joinlegacyrx.com
If you want to learn more about Infinite Banking Concept, click below: http://beyourownbank.com/ks
Don't miss out on the opportunity to transform your financial future. Subscribe now and start your journey towards financial wellness with Dr. Kyle Stephenson! 💼

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