Going Deep with Aaron Watson

Going Deep with Aaron Watson

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.


October 3, 2023 39 mins

Shane Parrish is the founder, curator and wisdom seeker behind Farnam Street. He is also  a bestselling author and entrepreneur known for his popular podcast The Knowledge Project and Brain Food newsletter.

Originally a personal blog where Shane could explore the discoveries made by others about decision-making, purposeful living, and the mechanics of the world, it swiftly transformed into a leading website for personal development...

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David McCormick is the former CEO of Bridgewater Associates, one of the world’s largest hedge funds. He has also previously worked in the Bush White House and as President of FreeMarkets, a Pittsburgh-based startup from the early 2000s.

He accomplished the sale of FreeMarkets to Ariba in 2004 for an estimated sum of $500 million and ensured that his team retained their jobs after the acquisition.

McCormick ran in the GOP primaries ...

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Chris Powers is the Founder & Executive Chairman of Fort Capital. Fort Capital is a Fort Worth, Texas-based Real Estate Private Equity firm. 

In 2016, Chris made the decision to focus on Class B Industrial full time and that is where the firm has dedicated the majority of its resources since.

After graduating in 2008, Chris started a leasing and property management business and flipped houses on the side. Wells Fargo ...

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David Tobin is the Founder and Managing Partner of TobinLeff, where they help clients convert business value into family wealth. 

David is a serial entrepreneur who has founded, grown, and sold four companies. David has worked with over 100 businesses to build value, retain key employees, and achieve profitable exits.

TobinLeff is an M&A advisory and exit planning firm that assists business owners in maximizing enterp...

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April 30, 2023 41 mins

Kevin Kelly co-founded Wired magazine in 1993, served as its Executive Editor for its first seven years, and was a pioneer from the early days of the internet. He is an author of several bestselling books and is a return guest on this podcast.


Kevin’s book Excellent Advice for Living is a small book of wisdom, in a pocketable format with 450 tweetable bits of advice that he wished he had known earlier. Kevin was prompted to colle...

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Jason Wolfe is the definition of a serial entrepreneur. He sold MyCoupons.com for roughly $23 million in 2000, shortly before the DotCom bubble burst.

Jason rolled over his proceeds into successive wins with his companies Direct Response Technologies (acquired by Digital River for $22 million), Jambo Media (for $15 million) and Giftcards.com (by Blackhawk Network for $120 million).

Pretty impressive. Even more so when you...

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Lyn Askin is the founder and CEO of Raxxar Digital Marketing, a leading digital marketing agency based in Louisiana. Lyn has over 20 years of experience in digital marketing and has expertise in SEO, PPC, social media, and content marketing to create comprehensive campaigns that drive results.

Recently, Lyn’s agency has hit a new level, thanks in large part to implementing the Entrepreneur Operating System (EOS) outlined in th...

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Jordan Ross is the founder and CEO of 8 Figure Agency. He is a systems expert with over 15 years of experience advising startups, mid-sized companies, and Fortune 500 organizations.

8 Figure Agency is a consultancy specializing in helping agencies scale their revenue and profitability. He and his team help agencies specializing in search engine optimization (SEO), pay-per-click (PPC) advertising, social media marketing, and we...

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Simon Huntley is a farmer and entrepreneur who is passionate about helping small farmers succeed. He is the founder and CEO of Harvie, a company that helps farmers sell their products directly to consumers through a customizable subscription service.

Harvie is a software platform that connects small farmers with consumers in their communities. The platform allows farmers to create customizable subscription services that offer ...

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Spencer Krause is founder & Director of Product Development for SKA Custom Robots and Machines. With over twenty years of experience in executing electrical and mechanical projects, Spencer has worked on some of the hardest problems in the world of technology and led teams tackling novel and thrilling projects. 

SKA Custom Robots & Machines is a contract-engineering firm that utilizes their expertise in mechatronics an...

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Andy Berman is the co-founder of Vowel, a software that allows dynamic remote teams to inject artificial intelligence into their calls. In 2021, Vowel secured a venture round of $13.5 Million to pursue the goal of making meetings more useful.

Their virtual meeting platform has an embedded set of tools that aid in the planning, preparation, execution, and follow-up of meetings. Smart summaries, transcriptions, and search are already...

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Anthony Constantino is the co-founder of Sticker Mule, one of the most popular custom sticker websites in the United States and Europe.

Sticker Mule was founded after Anthony was asked by his 72-year-old friend, his cofounder, how to use the internet. More than a decade later, Sticker Mule is one of the most popular custom sticker websites with over 100 employees world-wide and printing operations in the United States and Europe.


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Adriane Schwager is the co-founder and CEO of GrowthAssistant, a global talent solution helping marketing teams focus on brand, strategy and results. They help startups and direct-to-consumer brands accelerate the growth of their businesses by offering full-time offshore employees to handle the manual tasks of marketing campaign management, design and reporting.

GrowthAssistant was founded in February 2021 and has already scaled to...

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Daniela Osio is the Founder and CEO of the procurement-focused start-up Kloopify. Daniela is a former supply chain specialist for DuPont and was a CPIM certified and ISM 30 under 30 rising corporate start.

Today, she uses her expertise in logistics procurement, supply chain management, and risk management to run Kloopify, a data platform aimed at the global supply chain.

Kloopify introduces sustainability to the procurement process...

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February 7, 2023 55 secs

Steve Jobs was deeply influenced by Edwin Land, the founder of Polaroid. He took many of the top strategies that Land employed and used it to build Apple.

If you're interested in this video essay, watch the full video by clicking on the link provided:  https://youtu.be/1byJCn3sPhc

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John Jonas is the Founder of OnlineJobs.Ph. His company has helped more than 100,000 companies successfully hire Filipino talent by simplifying the outsourcing experience.

John was extremely early to the trends of remote work, international hiring, and niche job boards. His reward has been more than 15 years in business and a day-to-day in the present that is low stress and highly impactful.

In this episode, Aaron and John talk abo...

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Kevin Gibbon is the CEO and cofounder of Airhouse, an end-to-end operations and logistics platform for modern e-commerce companies.

Airhouse works with companies to make distribution of their consumer goods products easy. They use a platform that is an all-in-one, cloud-based warehouse that maintains itself, helping direct-to-consumer companies get orders from factory to front-door.

This company is informed by Kevin’s previous expe...

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Tucker Brown is the 6th generation rancher of the R.A. Brown Ranch. He has grown his followers on TikTok to 199k+, and garnered 3.7 million likes on his videos. He went viral overnight by sharing a video on TikTok of him lassoing a cow. Since then, he’s been constantly sharing tidbits of their ranch operations content in the said platform that help grow his business.

R.A. Brown Ranch is a progressive family ranching business that h...

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Shawn Allen is the co-founder of M@C Discount. Previously, he was President and GM of Asset Auctions, COO of AssetNation and Senior Product Manager of Giftcards.com which were all successful internet marketplace businesses.

M@C Discount stands for Merchandise at Cost. The company buys truckloads of closeouts merchandise and customer returns from major retailers. They receive "New"​ and "Used"​ items that are sold individually at ag...

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Justin Welsh is a solopreneur that has made more than $3 million running from a collection of digital products. He has leveraged a large boutique advisory firm for entrepreneurs and creates digital products for creators.

He has a  decade of experience building two $50M+ ARR businesses, teams of 150+, and helping raise over $300M in capital from VC firms like HLM Ventures, Leerink Transformation Partners, Vivo Capital, Toba Cap...

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