How to Bootstrap From Real Estate Agent to $80M+ Tech Exit | Tyler Smith - SkySlope Founder & HealthTech Pioneer

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Tyler Smith got a $330,000 loan at 19 and built SkySlope into a company managing two-thirds of all North American real estate transactions—without raising a dime of outside capital. After selling for $80M+ to Fidelity, a biological age test showing 47 when he was 39 (his dad died at 47) sparked his next mission. Now he's building Hundred Health to democratize personalized healthcare for $499/year. From "competing with paper" to revolutionizing proptech, Tyler reveals how product-market fit trumps everything, why bootstrap beats venture capital, and his vision for AI-powered daily health guidance that knows exactly what you should eat and how you should exercise before you even wake up.

➡️ Show Links

LinkedIn: https://www.linkedin.com/in/tylersmith/
Company: Hundred Health - https://hundred.com/
Previous Company: SkySlope (acquired by Fidelity)

➡️ Timestamps

0:00 Intro: Meet Tyler Smith, SkySlope Founder
0:43 SkySlope’s Impact on Real Estate Tech
1:11 Friendship That Sparked Innovation
2:07 Tyler’s Real Estate Beginnings at 19
4:34 Building SkySlope: From Paper to Cloud
9:01 Bootstrapping to $80M Fidelity Exit
17:05 Health Tech Pivot: Mayo Clinic Insights
23:59 Hundred Health: Affordable Doctor in Your Pocket
33:22 Future of AI-Powered Personalized Healthcare
36:24 Closing: Tyler’s Mission to Transform Lives

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