In this episode of The Pursuit of Purpose, Chris Kiefer sits down with Sean Wilkinson, co-founder of HostShare, to explore the intersection of real estate, tech, and entrepreneurship.Sean shares his journey from buying his first rental property as a teenager to building a 170-unit real estate portfolio—and eventually launching HostShare, a tech platform designed to unlock the massive amount of unused vacancy in short-term rentals. They dive into creative finance, lessons learned from early failures, and how real-world experience shaped Sean’s approach to business.The conversation also explores what it’s like transitioning from real estate into tech, the leverage and challenges of building a software company, and how AI is changing what’s possible for founders today. Sean opens up about focus, identity, and why choosing what to pursue matters just as much as how you pursue it—especially when balancing business, family, and travel.📢 Vacancy is wasted potential—unless you design systems that put it to work.🔑 Topics Covered:Creative finance & early real estate investingBuilding systems that scale without youShort-term rentals & hidden vacancyTransitioning from real estate to techNetwork effects & marketplace businessesAI tools for founders and operatorsFocus, identity, and long-term leverageFamily, travel, and intentional living👉 Watch now, hit LIKE, and FOLLOW for more conversations on purpose, business, and building leverage. Book Recommendations:How to Win Friends & Influence People by Dale Carnegie: Click hereRich Dad Poor Dad by Robert Kiyosaki: click here$100M Offers by Alex Hormozi: click hereThe Wealthy Gardener by John Soforic: click hereMovie / TV Recommendation:House of David: click here Connect with Sean Wilkinson:Email: sean@hostshare.coLinkedIn: click hereWebsite: click here

194 How Sean Wilkinson Built Wealth Before 30 Through Real Estate, Tech & AI