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This week on the podcast, I feel super blessed to welcome Gabe Zichermann, author, entrepreneur, investor, and thinker.

Gabe has founded 6 companies and written 3 books on gamification, and Behavioral Design have set the standard in teaching how to build for engagement across many industries and countries.

After the collapse of his recent startup, Gabe embarked on a journey to understand the fear of failure and how it limits us personally and professionally.

This project, called Failosophy, distills the lessons of individuals and organizations that have learned to fail fast, fail better and fail more often to achieve success – and how we can too.

Gabe is a polyglot and frequent public storyteller with a culinary streak. He’s visited nearly 100 countries and counting and currently resides in Los Angeles with his partner and their dog, Gizmo.

In this episode we discuss failure and it’s benefits, how and why social entrepreneurship is harder than regular entrepreneurship, and how Gabe makes investment decisions.

Gabe’s beautiful heart and mind come through in this episode, please enjoy this conversation, it’s one of my favorites so far.


Follow Gabe on Twitter:

Check out Gabe’s new project about the power of failure:

Links from this episode:

Will on Gabe’s Failosophy Podcast: 



Show Notes:

00:41 Talking about how you two met in Founder Institute. 

02:00 How we got kicked out of the Founder Institute and how we got back in

04:52 What’s it like being an entrepreneur – the forgotten or ignored career path of the entrepreneur.

07:28 How do you differentiate retail entrepreneurship from tech entrepreneurship from social entrepreneurship? – Why not just start a cafe? what’s the difference between entrepreneurship that scales and that doesn’t scale? 

12:33 How do you think about social entrepreneurship? How his generation was taught that business was not a force for good and rise of social entrepreneurship over the last decade. 

17:16 Do you think it is harder to build a social impact company than it is to build any other company that is sustainable?

19:25 “If you feel like you need to give back, you’ve taken too much”. What does it mean?

23:00 How following your passion can illuminate our path through life. Why Gabe moved away from the Gamification conference he founded. 

24:00 How nothing we do can have a uniformly positive effect on the world. Being prepared for the fact of unintended consequences and side issues. The story of Onward, Gabe’s startup to help people with digital addictions. 

30:00 Digital addiction, how to solve it? would Gabe come back to this issue? 

31:00 Failosophy – how Gabe’s failures haven’t been getting easier and the question of getting good at failing. 

34:00 How to know what feedback to take and what feedback to throw out as an entrepreneur

34:59 A rubric for finding your soul’s calling – are you able to instinctually tell the difference between good feedback and bad feedback. 

38:01 Building a founding team that allows you to do the things you’re a rockstar at and not be encumbered by the things you aren’t a rockstar at. 

41:07 What’s your favourite social-impact tech company?

48:11 What can failure teach us?