Amazon’s Culture of Experimentation and Learning; Big Bet Leadership with John Rossman

My Favorite Mistake: Business Lessons from Failures and Success

My guest for Episode #242 of the My Favorite Mistake podcast is John Rossman, a leadership and digital transformation expert. John is the author of three books on leadership and business innovation including the best seller The Amazon Way. He is an early Amazon executive who played a key role in launching the Amazon marketplace business in 2002.

His new book will be released on February 24, 2024: Big Bet Leadership: Your Playbook for Winning in the Hyper-Digital Era. You can pre-order it now.

Episode page with video, transcript, and more

Today, he is a leading keynote speaker on leadership for innovation, transformation and artificial intelligence and has given over 200 keynotes to worldwide audiences. John is an operator and builder whose love is diving into business problems and customer needs designing innovative solutions and business models, and creating durable enterprise value.

He served as senior innovation advisor at T-Mobile and senior technology advisor to the Gates Foundation. John was a managing director at Alvarez and Marsal for twelve years leading several business turn-around situations, serving as interim CIO at a restructuring client, and leading the development of several large clients, including Walmart, Nordstrom, and Microsoft.

John is the founder of Rossman Partners, a leadership development, coaching and advisor solutions company. He is often joined by his Frenchie, Bossman.

In this episode, we delve into the birth of Amazon's Marketplace, a venture that pushed limits and disrupted the e-commerce landscape. Rossman's role in pioneering this platform was marked by strategic risk-taking and innovation, lessons that emerging business leaders can take to heart. From edging out competition with unified checkouts to shaking the norm with new product categories, Rossman's story is a testament to the power of creativity and resilience. Understand his approach to the successful expansion of the Marketplace and discover how to nurture “small and tender” ideas into successful ventures.

Questions and Topics:

• Amazon Marketplace business - the 3rd iteration of a 3rd party selling platform
• Were you confident this was NOT a mistake, this new approach? What was different?
• What was the testing process?
• Auctions was an eBay competitor?
• What was the approach for evaluating the experiment? How long to give it? Not working or not working yet?
• Is the mistake thinking that a company like Amazon always gets it right the first time and that others need to do the same?
• Amazon is influential... Mistakes people make in trying to copy them too directly?
• Differences between Toyota Way & Amazon Way structure?
• What does “leaders are right - a lot” mean? Not “always”? 80% level
• What’s a hyper-digital era?

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