
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.
Latest episodes

Apr 10, 2025 • 35min
260 Anthony Vennare, Building a Fitness Media & Technology Company the Right Way
I love meeting people who beat the odds. Anthony Vennare was supposed to be a “dumb jock”. He wasn’t supposed to open a gym and find profitability within 2 months. He wasn’t supposed to raise millions of dollars to get more people working out. He wasn’t supposed to sign deals with massive healthcare companies and turn the world of digital content writing on its head. Luckily, no one told him. Today, Anthony is the co-founder and CEO of Fitt – a media and technology company that connects people to local health and fitness activities. They’ve got big plans for the future and anyone in the content & branding game needs to study what they’re doing. I got him for 40 minutes over the weekend and hustled to get this episode out ASAP because it got me so fired up. Hope you enjoy it. Attend my one-day conference January 27th in Pittsburgh. Learn more here. Anthony’s Challenge; Leave behind everything in your life that is stuck in the status quo. Write down a plan and execute on one step every month in the new direction. Resources Voice Dream

Mar 4, 2025 • 44min
577 Why China won’t Invade Taiwan
In this episode, Aaron Watson speaks with Dale Copeland about the likelihood of a Chinese invasion of Taiwan. Dale Copeland, a professor at the University of Virginia, specializes in trade, war, and economic interdependence. Known for his theory of trade expectations, he explores how future trade expectations shape war and peace, challenging conventional views in works like Economic Interdependence and War.Copeland argues the risk is lower than some believe, citing military, economic, and geopolitical constraints on Xi Jinping. We explore how trade dependencies shape global security and why China’s economic vulnerabilities serve as a key deterrent.Connect with Dale CopelandXUnderwritten by Piper CreativePiper Creative makes creating videos easy. How? Click here and Learn more.

Feb 26, 2025 • 48min
576 Understanding India's Role in Global Geopolitics
Akshar Patel is the founder of The Emissary, a media platform that explores India's history, politics, and societal dynamics. He aims to provide nuanced insights into topics like caste, Hindutva, and economic growth, highlighting India's conservative social fabric and rapid economic rise. Patel has been featured on various podcasts discussing India's evolving landscape.In this episode, we explore why India and the U.S. aren’t closer allies, who India’s primary adversary is, and how its global alignments are shifting. The discussion covers historical tensions, strategic relationships with Russia and China, Modi’s policies, economic reforms, and India’s growing digital influence. Tune in for a deep dive into India’s evolving role in the world and what it means for the future.Connect with Akshar PatelYoutubeXWebsiteInstagramUnderwritten by Piper CreativePiper Creative makes creating podcasts, vlogs, and videos easy. How? Click here and Learn more.We work with Fortune 500s, medium-sized companies, and entrepreneurs.Follow Piper as we growYouTubeSubscribe on iTunes | Stitcher | Overcast | Spotify

Jan 22, 2025 • 36min
575 Trump Pollster Henry Olsen on US Geopolitics
Henry Olsen is a senior fellow at the Ethics and Public Policy Center and a former opinion columnist for The Washington Post . His writing focuses on American politics, populism, foreign affairs, and conservative thought. He has authored The Working Class Republican and The Four Faces of the Republican Party.
In this episode, we discuss the future of U.S. foreign policy in light of Donald Trump’s re-election and examine J.D. Vance’s emergence as a significant political figure and his potential to shape the Republican Party’s future. Additionally, we analyze insights from recent polling data to identify key battleground states in upcoming elections. Tune in for an in-depth analysis of these critical issues.
Connect with Henry Olsen
Linkedin
Twitter
Watch this interview on our Youtube Channel

Jul 18, 2024 • 43min
574 Israel-US Relations, Turkey, and Geopolitical Analysis w/ Jacob Shapiro
Jacob Shapiro is a geopolitical analyst who helps investors and businesses navigate the complexities of a multipolar world. Jacob oversees geopolitical analysis at Cognitive Investments and hosts the Jacob Shapiro podcast.
In this episode, we question longstanding alliances, explore the intricate balance of power in the Middle East, and contemplate the future of U.S. foreign policy in the region.
We begin by tracing the historical roots of the U.S.-Israel alliance, primarily forged during the Cold War and heavily influenced by U.S. energy dependencies in the Middle East. Shapiro explains how the fall of the Soviet Union and the rise of American energy independence from the shale revolution have significantly altered these dynamics, making Israel less of a strategic asset today.
Connect with Jacob Shapiro
Linkedin
Website
Watch this interview on our YouTube Channel.

Jan 12, 2024 • 37min
31 Alan C on retiring at 35
Alan C, retired at 35 by saving money, increasing income, and implementing sound investment strategies. He discusses going back to school, living in a low-cost city, and losing 100 lbs after retirement. Challenges listeners to reflect on expenses and recommends investing savings for compound interest. Shares tips on maintaining healthy weight, setting up savings, and expresses gratitude.

Oct 3, 2023 • 40min
573 The Key to Clear Thinking w/ Shane Parrish (Farnam Street)
Shane Parrish, founder of Farnam Street, discusses clear thinking, identifying blind spots, and making better decisions. They also explore the power of reading and the impact it can have on our lives.

Aug 20, 2023 • 49min
572 Former Bridgewater CEO’s American Dream w/ David McCormick
Former CEO of Bridgewater, David McCormick, discusses his winding career, his book Superpower In Peril, and his game plan to renew America. They talk about challenges and hope for renewing America, risks of social media, digital advancements in India, CEO's experience during the dot com bubble, and the impact of a successful company.

May 23, 2023 • 46min
571 Niche Strategy to $2 Billion Real Estate Portfolio w/ Chris Powers (Fort Capital)
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 gave him a $250,000 line of credit, and the plan was to keep flipping homes near TCU. Chris started buying foreclosed homes all over the Dallas Fort Worth area. From there, he started building high-end custom homes. He later got into land development and entitlement for several years, where he would assemble unentitled urban land and take the entitlement risk to develop from ground-up. He has since learned the value of focusing on a specific niche.In this episode, Aaron and Chris talk about how he's built his team, how he balances the identity of investor and entrepreneur, and how focusing on a specific niche of real estate has led to stratospheric growth.
Chris Powers’ Challenge; if you don't have a mentor, go find someone that you trust that will pass their wisdom on to you.
Connect with Chris Powers
Linkedin
Twitter
Website
If you liked this interview, check out our episode with Brent B. Shore. His firm, Permanent Equity, specializes in buying small businesses and has built their specialty and niche focus.
Underwritten by Piper Creative
Piper Creative makes creating podcasts, vlogs, and videos easy.
How? Click here and Learn more.
We work with Fortune 500s, medium-sized companies, and entrepreneurs.
Follow Piper as we grow
YouTube
Subscribe on iTunes | Stitcher | Overcast | Spotify

May 14, 2023 • 40min
570 Mergers & Acquisitions Advice w/ David Tobin
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 enterprise value and converting it into personal wealth. They offer consulting services to prepare companies for transactions, M&A services for acquisitions and sales to strategic buyers and private equity groups, and exit planning services such as management buy-out plans.
In this episode, Aaron and David talk about how these mergers and acquisition transactions occur, who the important parties are, what the most important terms are as a part of these deals, and a whole lot more.
David Tobin’s Challenge; Do vision planning, and make sure you have a mission that truly ties to this vision.
Connect with David Tobin
Linkedin
Website
If you liked this interview, check out our episode on How to Sell a Midsize Digital Agency w/ Amanda Dixon (Barney)
Underwritten by Piper Creative
Piper Creative makes creating podcasts, vlogs, and videos easy.
How? Click here and Learn more.
We work with Fortune 500s, medium-sized companies, and entrepreneurs.
Follow Piper as we grow
YouTubeSubscribe on iTunes | Stitcher | Overcast | Spotify
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