Season 3 – Episode 04

Excelling at Tech, Entrepreneurship, and the Art of Not-Knowing

with Sequoia Blodgett

Photography by Gregory Berg

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Corporate culture perpetuates the idea that we need to fake it ‘til we make it, pretending to have all the answers and projecting confidence in our abilities—whether we feel it or not.

But what if there are advantages to not knowing?

What if living rich, creative entrepreneurial lives requires that we let go of what we think we know, step into new territory and expand our mental map of the world?

Today, Jeffrey considers the benefit of naïveté in creativity and entrepreneurship with Sequoia Blodgett, former music video director and founder of Commas, a tech platform designed to help founders build sustainable businesses. Sequoia shares her journey from directing music videos to the tech world, explaining what she did to secure VC funding for her first company and how the failure of that venture led to the creation of Commas. She addresses the vast disparity of women of color in tech, discussing the unconscious bias prevalent on both sides of private equity and her mission to even the playing field for multicultural entrepreneurs. Listen in to understand how travel enhances creativity and learn how to navigate your own knowledge gaps in the pursuit of an excellent life.

Our Guest

Sequoia Blodgett

Sequoia Blodgett is a “creative technologist,” speaker, content creator, and the founder of Commas, a product and service engine for growing entrepreneurs that offers exclusive access to top tech and creative resources. Commas also offers a virtual school on entrepreneurship dedicated to helping founders build sustainable startups. Sequoia’s entrepreneurial journey from film to music to tech has been a winding road, but on this journey Sequoia has learned much about finding purpose, pursuing excellence, and falling down only to get back up stronger for it.

» Sequoia’s Website

Key Takeaways

[0:02] How naïveté can work to our advantage

  • ‘Fake it ‘til you make it’ = destructive business advice
  • Wide-eyed not-knowing benefits pursuit of creative life
  • Let go of what think know as step into new territory

[4:44] How Sequoia’s creative genius expressed itself early on

  • Organize ideas + people in form of magazine, film
  • Exposed to father’s creative work at Pixar
  • Studied TV, dance and film at Loyola University

[11:47] Sequoia’s frustration with the business of making music videos

  • Can’t just create what you want (write hundreds of treatments)
  • Must prove yourself over and over again
  • Politics means work may never be released

[17:43] What inspired Sequoia to step into the tech world

  • Learned about VC working at tech camp for girls
  • Crowdfunding to attend Draper University
  • Tim Draper invested in first tech company 7AM

[29:59] How the failure of 7AM informed the creation of Commas

  • Didn’t understand business, burned through capital

[34:46] The navigation of knowledge gaps in pursuit of excellence

  • Access to much info, yet rapid change renders us ignorant
  • Learn to recover from failure savvier but not jaded

[39:10] Sequoia’s mindset shift around what it means to fail

  • Mentor explained that failure necessary for learning
  • Freed from weight of having to be right

[40:04] The vast disparity of women of color in tech

  • Issue on both sides (i.e.: unconscious bias, pattern matching)
  • Mission to even playing field for multicultural founders

[46:01] Sequoia’s insight around trying to do it all yourself

  • Scale with systems when small, leverage automation
  • Tech to build cashflow business and then hire team

[48:06] What Sequoia is doing to foster a strong inner life

  • Hire coaches to make sure Commas is successful
  • Support with business and self-development

[51:20] Sequoia’s take on the necessity of wonder

  • Travel to experience other perspectives
  • Creativity improves when embrace other cultures

[57:27] What Sequoia is learning to say NO to

  • Reject opportunities not necessary for growth
  • Left Black Enterprise to say YES to other opportunities

[1:02:22] How to expand your mental map of the world

  • Know what you don’t know + create support pack
  • Create nurture pack to foster inner awareness
  • Learn from people your brand elevates
  • Get outside yourself to shake up perspective

Season 3: Gregory Berg

Gregory Berg is a veteran photographer, multimedia storyteller, and the host & producer of Life on Purpose, a podcast that explores how to lead a more intentional life. Since he began his career as a professional photographer in 2004, Gregory has traveled the world seeking to capture the light and beauty that connects us all.

Gregory’s quest has led him to visit breathtaking destinations and photograph amazing humans, including world champion skateboarder Tony Hawk and distinguished entrepreneurs at Camp GoodLifeProject, a summer camp for adults where he has served as a photographer for the past five years.

After realizing the power of mindfulness and intention to infuse creative expression with transformational power, Gregory has developed projects (coming soon) to share this revelation with others. In the meantime, he posts stunning iPhone photography with his reflections on the world around him each day on Instagram.

For a brief primer on mindful photography, see his post written for Digital Photo Mentor. To see more of Greg’s photography, visit his website:

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Each week brings you in-depth conversations with leaders, stories from change-makers, and provocative ideas from artists and scientists – all designed to inspire you to shape your best work with more possibility, impact, and – yes – wonder.