Going Deep with Aaron Watson

Aaron Watson's show is a forum for having meaningful conversations about the passions, fears and problems of people from all walks of life. Guests talk about entrepreneurship, ultimate frisbee, finance and lifestyle design. Guests include Nathan Chan, Kevin Kelly, Bill Peduto, Morgan Housel, Noah Kagan, Tucker Max, and Barry Ritholtz.
RSS Feed Subscribe in Apple Podcasts
Going Deep with Aaron Watson



All Episodes
Now displaying: March, 2016
Mar 31, 2016

Jonathan Abrams is an award-winning journalist who has covered the NBA for ESPN’s Grantland, The New York Times and Los Angeles Times. He is a graduate of the University of Southern California.


His first book, Boys Among Men, chronicles the generation of NBA players that jumped directly to the pros from high school and the struggles they faced along the way.


Jonathan’s Challenge; Buy Shea Serrano’s book, The Rap Yearbook.


Check out Abrams’ book; Boys Among Men


Mar 30, 2016

Steve Patterson is a rationalist philosopher and author who works outside of the academic establishment. He believes the internet is revolutionizing every industry, including the world of ideas and that the future of intellectual progress belongs to independent scholars, not ivory tower professors.


He also believes truth can be discovered through a deep enough understanding of anything, as every pursuit ultimately points back to philosophy. He laments that the culture is stuck in an era of irrationalism, which glorifies blurry thinking and imprecise theories and his work is trying to change that.


Steve’s Challenge; Go out and try to break apart your worldview.


Steve’s Suggestion

Closer to Truth


If you liked this interview, check out episode 46 with Taylor Pearson where we discuss the decline of traditional jobs around the economy and rise of small entrepreneurs.

Mar 28, 2016

Neil’s site, Above Avalon, originated from a Tumblr blog about Apple in 2010. At the time, he was a Wall Street analyst focused on the financial sector, while all things related to Apple and technology were his evening and weekend projects. After being disappointed with the lack of relevant Apple analysis from both a financial and business point of view, he decided to begin building a new kind of Apple analysis site based on his financial background and critical thinking skills. By examining Apple from both a Wall Street and Silicon Valley perspective, he has positioned Above Avalon to provide unique insight into how Apple functions and its worldview.


Along with weekly Above Avalon posts and podcast episodes, Neil publishes exclusive daily updates for Above Avalon members. Members range from Wall Street experts to weekend hobbyists.


Neil’s Challenge; Try saying “No” to things that you can’t put your whole self into. No one has enough time to do everything.



If you liked this interview, check out episode 47 with Avi Geller where we discuss technology and the future of hearable tech.

Mar 25, 2016

Jessica Strong was engaged in the world of freelance work for years. She knew all about the never-ending to-do list of client requests, paperwork, social media updates, billing, tracking down receipts, fighting with WordPress plug-ins, and answering a million emails.

So she founded Whetstone Workgroup to help freelancers, consultants, and “mompreneurs” succeed in three specific ways. She created a physical space where freelancers can work more efficiently, with drop-in daycare available for attention-craving children. She also provides administrative services and software so Whetstone members can get through their monster to-do list more easily. And finally she offers consultations, trainings and workshops so her members can keep learning and growing as professionals.

Jessica’s Challenge; Create a cross section of things you are good at and things you enjoy doing. Execute on the things that qualify for both.

If you liked this interview, check out episode 28 with Emily and Kate from Propelle, where we discuss masterminds and the challenges mompreneurs face.

Mar 23, 2016

John Beck leads the development of TrueFit’s human-centered design methodology and his team’s design research, information design, product interaction, and user interface design. Through John’s leadership, Truefit helps clients create innovative web, mobile, social media and commercial software products that have positive practical impact.


John is part of Truefit's business development team and is skilled at helping clients understand the impact of good user experience and the best practices for success drawn from years of experience working with several of the world’s most distinguished health and technology brands including Samsung, Precor, Rolls-Royce, Kodak, and BodyMedia.


Prior to joining Truefit, John served as a Co-Founder and President of Gist Design, acquired by Truefit in 2013. John has also served as a Senior Interaction Designer at wearable body monitoring pioneer, BodyMedia, which was recently acquired by Jawbone.


John’s work has been cited in many industry and commercial publications including the Wall Street Journal, The New York Times, Wired Magazine, Business Week, and Engadget. John’s work has won numerous design and innovation awards including the IDEA Gold Medal sponsored by Businessweek and the Industrial Designers Society of America. He also serves as occasional lecturer and teacher.

John’s Challenge; Challenge yourself to practice design-thinking by carefully examining someone completing a task.

Mar 21, 2016

Scott is a business coach, trainer, and strategist who partners with small business owners and organizational leaders to help them uncover the things they cannot see, and build actionable strategies to help them live out their business on purpose.


His coaching business focuses on helping to teach the automation of small business processes to leverage organizational talent and to free the business owner up to work on his business versus working in his business. He also leads mastermind groups that allow business owners and organizational leaders to meet weekly and build an accountability practice.


His background in these roles includes direct and B2B sales, designing and implementing an organizational strategy, training and development, marketing and fundraising, along with teaching and speaking.


Scott’s Challenge; Create a document and write a step by step instruction for one thing that you want to delegate. Get it delegated within the next three weeks.



If you liked this interview, check out episode 59 with Aaron Walker where we discuss living a life of significance and coaching business owners.

Mar 16, 2016

Mike Dariano is a writer, an educator, and a creator. He writes about productivity and better work at Productivityist and edits the site which features good things to read, watch, and use. He also writes at The Waiter’s Pad – a blog that shares in depth notes from podcast interviews around the web.


He has written a few books including; My Meditations: What a Roman Emperor Taught me About Parenting, Read More Books: Hijack your Habits, Tame your Time, and Find Better Tools for Reading More Books, and Children’s Poems for the Couch on a Sunday Afternoon.


Mike’s Challenge; Read more books.


Mentioned Media

Helsinki Bus Station Theory

Gary Vaynerchuk on Rich Roll podcast

Venkatesh Rao on the Tropical MBA podcast


Check out Mike’s Book; 28 Lessons from Startups that Failed



If you liked this interview, check out episode 46 with Taylor Pearson where we discuss entrepreneurship and the future of the economy.


Mar 9, 2016

Robert P. Seawright is the Chief Investment & Information Officer for Madison Avenue Securities, a boutique broker-dealer and investment advisory firm headquartered in San Diego, California. At Madison, Bob’s role is a thought leader for the firm’s independent advisors, providing counsel and guidance with respect to the latest industry trends, research and best practices. In September of 2014, The Wall Street Journal published a list of fifteen smart people for investors to follow that included Bob, along with Warren Buffett, Howard Marks, William Bernstein and the CFA Institute.


Bob is a columnist for Research magazine, a Contributing Editor at Portfolioist as well as a contributor to the Financial Times, The Big Picture, The Wall Street Journal’s MarketWatch, Pragmatic Capitalism, and ThinkAdvisor. Bob’s blog, Above the Market, has received “best of” recognition from a wide variety of sources, including The Wall Street Journal, Financial Planning, the CFA Institute, Insider Monkey, Financial Social Media, and Investment News. He also speaks regularly to a variety of audiences on topics related to finance, investing and the markets.


Bob’s Challenge; Sit down and think of a few examples of mistakes you are making.


If you liked this interview, check out episode 55 with Morgan Housel, where we discuss finance writing and cognitive biases.

Mar 8, 2016

Michael Port has written six books, including Book Yourself Solid and Steal the Show, the latter which—according to the former President of Starbucks—“might be the most unique and practical book ever written on the topic of public speaking.” He's been called an “uncommonly honest author" by the Boston Globe, a "marketing guru" by The Wall Street Journal, a “sales guru” by the Financial Times, “a public speaking phenom” by Jonathan Fields and “the best public speaking coach in the world” by Lewis Howes.


The founder of MastermindTalks, Jayson Gaignard, declared, "Michael Port is the best speaker I've ever seen." His books have been on the bestseller lists of the NY Times, Wall Street Journal, USA Today and Publisher's Weekly.


He was once a professional actor, having received his MFA from NYU's Graduate Acting Program, guest starring on shows like Sex & The City and Law & Order, and in films like The Pelican Brief and Down to Earth. These days, Michael can be seen on MSNBC, CNBC, and PBS as an on air expert in communication and business development and as the host of the most popular podcast on public speaking and performance, Steal the Show with Michael Port.


Michael’s Challenge; Save money. Even if it is just a little bit, start investing now. Check out Jack Bogle’s book The Little Book of Common Sense Investing.


Connect with Michael



Mar 2, 2016

Colin is a professional author and international speaker, and co-founded a publishing company. He travels full-time, moving to a new country every four months or so, with the country being determined by the votes of readers of his blog.


In the six years since starting his blog, Colin has lived in New Zealand, Thailand, Iceland, India, Romania, and Czech Republic, visited the 48 contiguous US states twice, road tripped through South America, rode the rails through Southeast Asia, and visited about 30 other countries.


Since hitting the road, he has pivoted from building brands for other companies, to consulting on branding, to building brands for himself. He has run nearly a dozen medium- and small-scale endeavors, in industries ranging from sustainable product design to subscription-based publishing technologies. He currently makes a living by publishing books through a publishing company called Asymmetrical Press, which he also co-founded with two fellow authors, Josh and Ryan from The Minimalists.


He also periodically teaches classes, gives talks at schools, conferences, and events, and runs workshops all over the world.


Colin’s Challenge; 20 minutes per day away from technology and other people to allow your mind to free associate and be creative.


Colin’s Writing

On Failing Gracefully


If you liked this interview, check out episode 23 with Nathan Chan. We discuss publishing and brand-building.