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From Waiting Tables to Building a Global Media Empire to Re-Investing in the Travel Industry

In this episode of The Kirsh Connection, Andrew Kirsh sits down with Jon Skogmo, CEO of Way Capital and founder of Jukin Media, to discuss his journey from waiting tables in Hollywood to building Jukin Media into a global company and achieving a nine-figure exit. Jon also shares why he started over with Lost In, a travel media company focused on inspiring travelers through authentic storytelling—not telling you where to go, but why to go.

Episode Highlights:

  • Jon’s Hollywood story: moving to LA from Chicago and needing a headshot just to get a waiter job.
  • Building Jukin Media from his apartment into a 300-person global company.
  • The current state of the travel industry.
  • Why Jon launched Lost In and the growing demand for premium, experience-driven travel content.
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“We’ve built our agency in part by being faster, more attentive, and smarter than the competition. We can’t do that unless our partners are of the same caliber. The team at Sklar Kirsh has proven time and again that they are as hungry and committed as we are. The relationship with our agency and Sklar Kirsh could not be more cohesive. They have an expert understanding of our business and provide trustworthy advice – especially in difficult situations.”

— Marc Simons, Manager of Giant Spoon LLC
This testimonial does not constitute a guarantee, warranty, or prediction regarding the outcome of your legal matter.