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Sometimes, a podcast episode takes you on a journey that is both enlightening and wildly entertaining. My conversation with Michael Todasco, MBA, MFA, was precisely that—an experience filled with insights, unexpected turns, and laughter. Mike is a Visiting Fellow at the James Silberrad Brown Center for Artificial Intelligence at San Diego State University in California.
I first connected with Mike through LinkedIn networking, and from our initial prep meeting, I knew this episode would be unique. It was clear from the start that Mike brought a wealth of innovation experience and a sharp wit that made every moment enjoyable. I found myself laughing more during that prep meeting than with any other guest before—and the actual recording of the episode did not disappoint.
The Path to Innovation: Mike’s Story
Mike’s journey into innovation was anything but conventional. He shared how his entrepreneurial instincts took root as a child in Chicago during the 1980s and 90s when he started collecting and selling baseball cards. What began as a childhood hobby became a serious business, allowing him to pay for college. This early exposure to buying, selling, and understanding market trends gave him a foundation in innovation before he realized what that word truly meant.
From there, his path was filled with trial and error. He went into finance but quickly realized it was not for him. He moved into private equity and did not find much more satisfaction there. A failed startup eventually led him to PayPal, where he spent 11 years—half of which was dedicated to running innovation within the company.
One of the standout moments of our conversation was when he described how he convinced PayPal to hire him. He strategically navigated through connections, leveraging a series of introductions to get his resume in front of the right person. Then, in his interview, he candidly shared how he had “failed” at his startup—lessons learned, mistakes made, and what he would do differently. His honesty and ability to extract value from failure ultimately landed him the job.
Building a Culture of Innovation at PayPal
At PayPal, Mike played a pivotal role in fostering a culture of innovation. He did not want innovation to be exclusive to a select few. Instead, he worked to ensure every employee, from engineers to attorneys, saw themselves as innovators.
One of his key strategies was creating an innovation tournament that engaged employees across the company. This grassroots initiative started as an intern’s idea and grew into a large-scale event where employees could submit ideas, form teams, and refine their concepts through multiple stages. Senior leaders, including the CEO, became involved, ultimately generating thousands of ideas.
Mike emphasized that innovation at PayPal was not about having a huge budget but finding creative ways to engage people and harness collective intelligence. His experience demonstrated that great ideas could come from anywhere and that building a culture of participation was more valuable than simply designating an “innovation team” to handle all creative thinking.
AI, the Future, and Embracing Change
When Mike left PayPal in 2022, he had no specific plan. He spent the summer experimenting with AI tools like GPT-3 and DALL-E. The more he explored, the more excited (and frustrated) he became because very few people were meaningfully talking about AI's potential.
He started writing about AI, and his insights quickly gained traction. His work eventually led him to San Diego State University, where he teaches and researches AI’s impact.
Our discussion on AI was particularly thought-provoking. Mike firmly believes that AI will be even more transformative than the internet. He highlighted how many people still have not fully explored generative AI. Yet, those who embrace it now will be at the forefront of a significant shift in how we work, create, and interact with technology.
We also touched on concerns about AI replacing jobs. While Mike acknowledged that AI would undoubtedly eliminate some roles, he also pointed out that technological shifts historically create new opportunities. The challenge will be adapting and redefining how we think about work, productivity, and purpose.
The Moment Mike Turned the Tables on Me
One of the most unexpected moments of our conversation was when Mike asked me how I define innovation.
It took me by surprise because, while I have spent my career immersed in innovation, I had never been directly asked to define it. After a pause, I shared that I see innovation as purposeful problem-solving—creating something that makes life better meaningfully. I emphasized that innovation should not exist just for being innovative; it should have an impact.
Mike, however, fascinatingly challenged that perspective. He pointed out that innovating for fun or experimentation is sometimes valuable because it can lead to unexpected breakthroughs. He referenced the idea of “unnecessary innovations”—quirky, playful ideas that may initially seem impractical but inspire creative thinking and open doors to more meaningful solutions.
His perspective reminded me that playfulness and curiosity are essential to innovation. As we age, we often lose that sense of exploration because of structured thinking or professional constraints. Mike’s insight made me reflect on how important it is to nurture creativity without always demanding immediate practicality.
A Conversation Worth Continuing
As our conversation wrapped up, I knew this would not be the last time I had Mike on the podcast. His insights, humor, and genuine enthusiasm for innovation made for a fantastic discussion. We covered everything from AI advancements to career advice to the future of work, and yet, it felt like we had barely scratched the surface.
Mike’s journey proves that innovation is not a linear path. It is about taking risks, learning from failure, and constantly staying curious. Whether he was convincing PayPal to hire him, building a culture of innovation, or exploring the future of AI, he approached every step with an openness to experimentation.
I left this conversation inspired, motivated, and, admittedly, still thinking about how I define innovation.
One thing is for sure—I am looking forward to having Michael Todasco back on the podcast again!
Keep innovating!
Eulanda
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