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Questions that matter. If we can make the world more curious, could everything be better?
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Chase Jarvis with Shane Mac

askSep 18, 2019

Katelin Holloway with Mikel Ellcessor

Katelin Holloway with Mikel Ellcessor

Katelin is passionate about helping founders build scalable, diverse, and inclusive cultures. First introduced to the notion of intentional cultural development at Pixar Animation Studios, she studied alongside some of the most brilliant creative business minds of this generation. From there, she spent a decade building teams as a senior executive at some of the internet’s most influential startups, including Klout and Reddit. In early 2020, Katelin made the leap from operator to investor, supporting a new generation of leaders. Through the course of her career, the one common denominator remains: enabling people through belonging to create beautiful, innovative products that move the world.

Katelin is currently a Founding Partner at Alexis Ohanian’s venture capital firm Seven Seven Six, where she invests in people-first companies and manages the firm’s programs, including the 2% Growth & Caregiving Commitment and Operator in Residence Program. She is deeply committed to helping founders and the broader venture ecosystem evolve their diversity, equity, inclusion & belonging practices, creating new opportunities and access to wealth for people and products typically underrepresented in the tech industry. As an investor, she is passionate about supporting the companies that will shape the future of work, life, sustainability, and the delicate balance that enables us to thrive.

ask is made by @shanemac @mikelellcessor & Paul Chuffo at Joyride Media

Key Seven Seven Six Initiatives referenced in the show:

May 25, 202147:08
Chris Ruder with Shane Mac

Chris Ruder with Shane Mac

Spikeball CEO Chris Ruder is NOT the quick-hit, hockey stick growth guy. That said, Spikeball just crossed $100m in total revenue, so... In this episode of ask, Chris shares his thoughts about starting a business without risking it all. While building Spikeball, he kept his corporate job for over 5 years and we sit down to discuss the conversations with his wife and brother which led to him going full-time. It's a story of quiet confidence, patience, persistence, and is a powerful example of a less risky way to start a business.

Dec 20, 202040:52
Tina Essmaker With Mikel Ellcessor

Tina Essmaker With Mikel Ellcessor

✨Special Guest: Coach, writer (@99u, @WnotW), and speaker Tina Essmaker

🗣️Talking Points:

- How Tina reimagined her career path

- Coaching creatives to "the other side" of professional and personal transitions

- Giving permission to acknowledge our personal limits and avoiding burn-out

Follow Tina: @tinaessmaker

Mar 12, 202027:54
David Marquet with Shane Mac (Part Two)

David Marquet with Shane Mac (Part Two)

🎖️ Special Guest:  Former US Navy Captain @ldavidmarquet (Part Two) 

 🗣️ Talking Points:

 - David’s new book “Leadership is Language” (out TODAY) 

- Why leaders never say THEY and the WE/THEY boundary  

- Why THINKING is  >>> than doing things FAST

Follow David: @ldavidmarquet

Feb 04, 202027:22
David Marquet with Shane Mac (Part One)

David Marquet with Shane Mac (Part One)

🎖️ Special Guest:  Former US Navy Captain David Marquet (Part One)  

🗣️ Talking Points:

 - David’s path to the Navy 

- Internal versus external mindsets 

- Why REAL leadership means giving others control

Follow David: @ldavidmarquet

Jan 30, 202034:05
Nir Eyal with Shane Mac

Nir Eyal with Shane Mac

"The number one cause of distraction is not what is happening outside of us, but in fact what happens inside of us. The root cause of most distraction is not the external triggers, it's the internal triggers. So, I don't care what life hack or guru does your tells you to do with how to hack back your time. Fundamentally, if we don't first and foremost figure out what we are trying to escape from, what uncomfortable sensation prompts us to look for relief—to look for a psychological pacification from our devices, from television, from too much booze, too much work, too much, whatever—then that becomes a distraction. If we don't deal with that stuff and either fix it or learn methods to cope with it, we are always going to succumb to distraction."
Dec 12, 201945:34
Chase Jarvis with Shane Mac

Chase Jarvis with Shane Mac

"What's ultimately at play here is the loudest voice, the strongest cultural narrative. That's where culture orients around risk or reward or safety. The hope that I have is that (people are) looking around for a little bit, pressing pause and saying, wait a minute. The things that used to be couched as safe are arguably now riskier than ever before. That's true for employment, relationships, identity, so many things. The thing that's going to overpower that is inside us. It's not out there. And that's the part to get people to lean into."
Sep 18, 201901:03:56
Tanya Khakbaz with Shane Mac

Tanya Khakbaz with Shane Mac

In this interview with Tanya, we cover many topics from harnessing your passion to start a business, identifying “the magic” of your product that will lead to scale, and managing the work/life/parent balance, and the global shift towards a “skills-based” economy.
Jul 23, 201748:04
Ashley Wellington-Fahey with Shane Mac

Ashley Wellington-Fahey with Shane Mac

how do you change the sports industry and follow your dream?

Ashley is the CEO of The Relish, a new media sports company for female fans. She has an inspiring story and shares her love for sports, women in business and serving an underserved market: women sport's fans.

Hope you enjoy.
Mar 10, 201701:27:38
Tammy McSimov with Shane Mac

Tammy McSimov with Shane Mac

how do you love your work, be happy, and take care of yourself first?

A conversation with my mom, Tammy. We discuss everything from work before computers, being a great leader, how to make sure you are happy before anything else and more.

I hope you enjoy.
Mar 05, 201744:54
David Marquet with Shane Mac

David Marquet with Shane Mac

David's bio:
Former captain of a nuclear submarine.

Captain Marquet retired from the Navy in 2009 and is now the author of Turn the Ship Around! A
True Story of Turning Followers Into Leaders. Fortune magazine called the book the “best howto
manual anywhere for managers on delegating, training, and driving flawless execution.”
Captain Marquet’s Intent-Based Leadership model is turning around all types of organizations—
from big manufacturers to start-ups and sport teams to government.
He helps leaders build environments where people contribute and feel valued —where
everyone is a leader.
Nov 09, 201538:32
Jason Fried with Shane Mac

Jason Fried with Shane Mac

why drink tea?

Jason's bio:
Jason Fried thinks deeply about collaboration, productivity and the nature of work. He's the co-founder of 37signals, makers of Basecamp and other web-based collaboration tools, and co-author of "Rework."
Nov 09, 201505:41
Simon Sinek with Shane Mac

Simon Sinek with Shane Mac

why start with the why?

Simon's bio:
Simon Sinek is an optimist. He believes in a bright future and our ability to build it together.

Described as “a visionary thinker with a rare intellect,” Sinek teaches leaders and organizations how to inspire people. With a bold goal to help build a world in which the vast majority of people go home everyday feeling fulfilled by their work, Sinek is leading a movement to inspire people to do the things that inspire them.

A trained ethnographer and author of Start With Why: How Great Leaders Inspire Everyone to Take Action, Sinek has held a life-long curiosity for why people and organizations do the things they do. Fascinated by the leaders and companies that make the greatest impact in the world, those with the capacity to inspire, he has discovered some remarkable patterns of how they think, act and communicate. He has devoted his life to sharing his thinking in order to help other leaders and organizations inspire action.
Nov 09, 201520:49
Ryan Carson with Shane Mac

Ryan Carson with Shane Mac

why's culture matter?

Ryan's bio:
Ryan is the CEO and Co-Founder of Treehouse an online technology school that teaches you how to make Apps.
Previously Ryan founded Carsonified (acquired 2011) and DropSend (acquired 2008).
You can see interviews of Ryan on
The New York Times
Foundation with Kevin Rose
This Week in Startups with Jason Calacanis
Founders Talk
Ryan was born in 1977 in Colorado Springs, Colorado. He graduated from Colorado State University in 2000 with a degree in Computer Science. He then moved to the United Kingdom to pursue a bit of adventure and fun and ended up meeting Gillian, getting married and having two wonderful boys. He and his family now live in Portland Oregon.
Feel free to follow him at @ryancarson.
Nov 09, 201517:02
Jonathan Fields with Shane Mac

Jonathan Fields with Shane Mac

conventional wisdom?

Question everything. Asking questions to world leaders in art, business, music, and technology.

Jonathan's Bio:
Jonathan Fields is a New York City dad, husband and lawyer turned award-winning author, media-producer and entrepreneur. His last book, Uncertainty: Turning Fear and Doubt Into Fuel For Brilliance was named the top personal development book in 2011 by 800-CEO-READ.

It’s important to note that Jonathan’s mom does not, in fact, own 800-CEO-READ, though she may have inadvertently coded a script that hacked their system during the selection process. #Hearsay. #NotAdmissibleInCourt.

Jonathan’s current focus, Good Life Project, is a global movement that inspires, educates, connects and supports mission-driven individuals in the quest to live better, more engaged, connected and aligned lives. #WakeUpPeople.

Fueling this quest is a rapidly-expanding digital media, community-building and education venture that produces a top-rated podcast, a broadcast-quality web-series seen in more than 150 countries and educational programs for mission-driven leaders, entrepreneurs, and makers. #HeSleepsReallyHeDoes

Jonathan also speaks globally on aligned entrepreneurship, movement-dynamics, mindful innovation and living a good life. #AndNapsButThoseTalksPayLess.

In 2013, Forbes named this website one of the top 100 websites in the world for entrepreneurs, and it named Jonathan one of 25 entrepreneurs to follow on twitter, along with Richard Branson, Mark Cuban and Randi Zuckerberg, an accolade he had inked on his lower-back to impress the hipsters at Brooklyn power yoga. #ItDidn’t

He has been featured widely in mainstream and online media, including The New York Times, Wall Street Journal, BusinessWeek, FastCompany, Inc., Entrepreneur, USA Today, Real Simple, HOW, O Magazine, Self, Outside, Slate, Vogue, CNBC, Fox News, PBS Nightly Business Report and thousands of other places that sound cool, but don’t impress his daughter all that much. #UmLikeWhatsTVDad?
Nov 09, 201506:45
Brad Feld with Shane Mac

Brad Feld with Shane Mac

how to not pitch a VC? Question everything. Asking questions to world leaders in art, business, music, and technology. Brad's bio: Brad Feld has been an early stage investor and entrepreneur for over 20 years. He lives in Boulder, Colorado and Homer, Alaska with his wife and is on a quest to run a marathon in every state in the US. Brad has been an early stage investor and entrepreneur since 1987. Prior to co-founding Foundry Group, he co-founded Mobius Venture Capital and, prior to that, founded Intensity Ventures. Brad is also a co-founder of Techstars. In addition to his investing efforts, Brad has been active with several non-profit organizations and currently is chair of the National Center for Women & Information Technology and co-chair of Startup Colorado. Brad is a nationally recognized speaker on the topics of venture capital investing and entrepreneurship and writes the widely read blogs Feld Thoughts, Startup Revolution, and Ask the VC. Brad holds Bachelor of Science and Master of Science degrees in Management Science from the Massachusetts Institute of Technology. Brad is also an avid art collector and long-distance runner. He has completed 23 marathons as part of his mission to finish a marathon in each of the 50 states.
Nov 09, 201507:06
Lewis Howes with Shane Mac

Lewis Howes with Shane Mac

what is your passion?

Question everything. Asking questions to world leaders in art, business, music, and technology.

Lewis's bio:
Hi there. My name is Lewis and I want to get real with you for a minute.

I’ve always dreamed big, strived for greatness and deeply cared about people.

My dream growing up was to be a professional athlete and be an Olympian. After getting injured while playing professional football, I immediately thought about how to achieve the next dream.

Broken, broke, and clueless on how to make money or get a career, my obsession for learning about business, marketing, and adding value to influential people (when I had no value to give) began. Since then it’s been a powerful journey for me – becoming a New York Times Bestseller, building up a multi-million dollar online media company, speaking all over the world, advising for billion dollar brands, receiving media praise from places like Details Magazine, being one of “5 Internet Gurus Who Can Make You Rich” and much more.

I’m a firm believer that how you feel every moment is more important than what you do or what you have. I got a taste of being a pro athlete for a short amount of time. Knowing what is possible in life when I commit to my vision and pursue it with 100% passion… anything is possible.

Living my ideal lifestyle is important to me instead of working to survive life.

It’s hard to think that without having any business experience I went from sleeping on my sister’s couch to running a seven figure business in a couple years. Hustle comes to mind when people ask me how I did it. Lot’s of hustle, passion, focus, and consistent vision.
Nov 09, 201505:54
T.A. McCann with Shane Mac

T.A. McCann with Shane Mac

what past experiences led to your success?

Question everything. Asking questions to world leaders in art, business, music, and technology.

T.A.'s bio:
I am a founder of Rival IQ - the best way to analyze and monitor your competitive landscape. Focused on active online marketers who want to get ahead, Rival IQ saves you time and delivers key insights about your competitors across their key marketing channels (web, search, social…). Try a sample “landscape” here for major car brands.
I was previously VP of Product Strategy at Blackberry (formally Research in Motion), focused on BBM (Blackberry Messenger), social applications (Facebook, LinkedIn, Twitter, Foursquare…) as well as the native Contacts apps after Blackberry bought my last company, Gist.
I was the founder of, a social address book sold to Blackberry in February 2011, as well as Jump2Go and 3 other web based companies. I am on the board of Full Contact and Guidant. I am an active advisor to startup companies including Creative Live, Zooppa and EveryMove. I also spent 4 years at Microsoft in various roles on Exchange and Mobile Service Delivery Platforms. I like B2B and mobile stuff!
I am a new, but active angel investor and have made investments in Creative Live, Inside Social, Everpath, Heapsylon, Skedadle as well as Founders Co-op, FG Angels and SKV. I am looking to do more so connect with me here.
I like sharing my experience and ideas, so I spend lots of time at Startup Weekend (on the board) and Techstars (active mentor), Buerk Center for Entrepreneurship at the University of Washington (on the board) as well as Lake Washington Girls Middle School. I learn by mentoring, coaching and teaching.
Prior to my startup activity, I was a professional sailor and competed in 2 America’s Cups (won one, lost one) and the Whitbread Round the World race (now called the Volvo Ocean Race). I am married to Teresa, a wonderful and creative woman and father of Ray, a smart, caring and active daughter! When I am not working, I like to run and bike long distances and swim at 1/2 the pace I did in college.
Nov 09, 201546:45
Robert Stephens with Shane Mac

Robert Stephens with Shane Mac

where's offline going?

Question everything. Asking questions to world leaders in art, business, music, and technology.

Robert's bio:
Founded GeekSquad, CTO of Best Buy.
Nov 09, 201523:30