Like all good 80’s kids, Drew Stern loves a good Choose Your Own Adventure story. In fact, it’s this approach that has led this former musical theater actor turned award-winning technology CEO to such great success. With three high-growth tech exits in the last decade, Drew's innovative spirit and passion for creative success have made him a trailblazer in the world of technology and the performing arts.

Discover how Drew embraced chance and combined his two passions—performing and tech—to create Stageyo AI, the world's 1st digital marketplace and AI engine connecting stage performers with their supporters. Learn how he envisions using technology responsibly to foster authentic connections between performers, their art, and their patrons. Don't miss this inspiring story of intentional risk-taking and leadership that has earned Drew recognition as an influential CEO and celebrated entrepreneur.

Connect with Drew and Stageyo AI on Instagram and on the web.

• Make sure to follow this podcast everywhere you find podcasts, leave a rating and a review, and slip into our Instagram DMs at @wasitchance.
• More about Heather via @heather_vickeryandco on Instagram and Threads, @Braveheather on TikTok, and listen to The Brave Files
• More about Alan via @theatre_podcast on Instagram and listen to The Theatre Podcast with Alan Seales

EPISODE TAKEAWAYS:

• Drew’s career had two phases. He grew up the youngest of 5 and everyone performed constantly. Tech was unexpected.
• Tech was a chance Drew embraced.
• If you want to be a great leader, go put on a play - this creates trust, creativity, team player, and being a great listener.
• No entrepreneur can do anything on their own. It has to always be a team effort.
• Getting venture capital investment is like auditioning, frustrating, scary, difficult and most of them don’t book.
• You need to be able to see the future, then make it happen (manifest it), and then move on. Sometimes you have to close a great show.
• Growth is a combo of intentionality and embracing chance.
• You have to have the confidence to take the chance.
• Drew created his own Machine Learning AI platform well before AI was a household name.
• Stageyo was born from a desire to build things more emotionally aligned for Drew and allowed him to blend his two passions: Performing and Tech.
• Stageyo is about creatine agency, equity, and access around performing arts.
• It answers a need for authentic connection between performers, their art, and their patrons.
• Technology is the great equalizer between agency, equity, and access.
• Envision, trust, and know your capabilities.
• Past successes allow Drew to play, test things out and really explore possibilities.
• There are two sides to the AI coin. There are great challenges to using it responsibly.
• How can you use technology to enable people to enjoy things in real life - this is one of Drew’s goals.