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E294 | Navigating Transformations in the Digital Age: Big Bet Leadership with John Rossman

Today we have a very special episode for you. It’s the first of our newly branded Mind Your F**king Business podcast.

If you are a leader struggling to steer your company through the complexities of transformation in the digital age, our guest this week will bring you the answers. John Rossman, former Amazon executive, and best-selling author, joined Dominic Monkhouse for a truly enlightening conversation.

Not just content with shaping Amazon’s strategies, John co-authored Big Bet Leadership, a crucial playbook for leaders navigating the uncharted waters of major transformations.

In a riveting conversation, John dismantles the intricacies of innovative leadership, discussing everything from the dangers of “zombie projects” to finding your company’s “fish hook in the eye.” With insights drawn from his extensive background and expertise, John maps out the terrain of high-stakes decision-making with the precision and acumen that only a seasoned expert can offer.

Whether you’re at the helm of an enterprise or simply intrigued by the mechanics of successful strategic changes, this episode will equip you with the insights to set your compass towards triumph in a hyper-digital landscape.

Download and listen today!

Watch it on YouTube

On today’s podcast: 

  • The key elements and complexities of a Big Bet
  • Finding your company’s ‘Killer Feature’
  • Dealing with Innovation
  • ‘zombie projects’
  • Looking to the future of business

Follow John:


Big Bet Leadership

The Amazon Way

Who is John Rossman

John Rossman is the author of four books on leadership and business innovation including the best seller The Amazon Way and Big Bet Leadership. He is an early Amazon executive who played a key role in launching the Amazon marketplace business in 2002. Today he is a leading keynote speaker on leadership for innovation and transformation. 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 has served as the senior technology advisor at the Gates Foundation and senior innovation advisor at T-Mobile.

His new book, Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era, is an actionable playbook for senior leaders to succeed at complex transformations.

John is the founder of Rossman Partners, a strategy & leadership solutions firm.

What you’ll learn from John Rossman

03:06 – Writing Big Bet Leadership 

04:30 – Thinking In ‘Memos’

06:20 – The ‘What Sucks Memo’ Or What Needs Fixing In Your Business

07:37 – Solving The Real Painful Problem of Your Customer?

09:47 – What Is A Big Bet?

11:37 – Innovation: Finding ‘The Killer Feature’ 

13:26 – Zombie Projects: ’Continue, Kill, Pivot or Confusion’

16:26 – The Complexities Of A Big Bet: Certainty vs Risk

21:38 – Why You Need To Adress Risks Earlier 

24:41 – The Cost Model Innovation

28:04 – The Importance of Portfolio Construction In Managing Bit Bets

30:16 – Leaders Commitment To Tomorrow’s Business

33:12 – DRI: Appointing The Right Person To Your Big Bet

36:07 – A Key To Become A Big Bet Legend: On-Point Repeated Communication

39:12 – Devil Is In The Details

41:22 – Elon Musk: Innovating By Simplicity

Elon Musk

How big things get done

Switch. How to change things when change is hard

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