The Going Deep with Aaron Watson podcast is a forum for having meaningful, deep conversations about the passions, fears and problems of people from all walks of life. Guests talk about entrepreneurship, sports, finance, comedy and lifestyle design.


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238 Going Deep Summit

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237 Mark Heckman, Google Adwords, Local Business, and Shitty Job Boards

Mark joined WebKite in the summer of 2016 out of his excitement for the advertising technology space and the powerful products WebKite has developed to date. Machine learning and language …

236 Barry Rabkin, Selling Drones, Building Brands, and Setting Progress Goals

Barry Rabkin has over a decade of success founding, growing, and selling technology companies. An operational and strategic business leader, Barry’s experience ranges from high growth, venture backed startups to …

235 Kim Scott, Upgrading Leadership & Relationships with Radical Candor

Today’s episode is a conversation about Truth and Love. Both are often missing from our daily interactions, and Kim Scott wants to fix that.   Here NYT and WSJ bestselling …

Going Deep With Aaron | 234 Aaron Klein, Managing Risk, Common Investing Mistakes & the Future of Financial Advising

Risk is a word with numerous definitions. Riskalyze helps investors negotiate the risks they face.   Aaron Klein is the quintessential entrepreneur, spending his entire career working with entrepreneurial businesses …

Going Deep With Aaron | 233 Ka Sundance, Traveling the World with 6 Kids!?!

Ka Sundance is a location independent father of 6, YouTuber, and CEO of a $1 million heart-centered online business. Together with his wife Katie, he works to show aspiring business …

232 Christian Simmons, Changing the Liquor Landscape in Pennsylvania

Christian Simmons is a hustler and a visionary.   His company, Pennsylvania Libations, connects distillers, small businesses, and individuals, to one another with the intent of growing, experiencing, and preserving …

Going Deep With Aaron #231 | Andy Rachleff, Wealthfront CEO is Revolutionizing Financial Planning with Software

Andy Rachleff is Wealthfront’s co-founder, President, and Chief Executive Officer. He serves as a member of the board of trustees and vice chairman of the endowment investment committee for the …

Going Deep With Aaron | 230 Fantasy Education Scenario

This post is inspired by Scott Young’s The Essential Education: If You Had Ten Years to Learn Anything, What Would You Do? In his post, Scott outlines his Ideal Ten-Year …

Going Deep With Aaron | 229 Bryce Conway, How to Save $27,000 on International Trips through Travel Hacking

In the fall of 2013, Bryce Conway started a website teaching people how to save money while traveling the world. He learned the ins and outs of the credit card …

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