300 episodes

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.

Going Deep with Aaron Watson Aaron Watson, Piper Creative

    • Careers
    • 5.0, 109 Ratings

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.

    441 Large Firms Need an Ethical Intruder to Test Cybersecurity w/ David Kane

    441 Large Firms Need an Ethical Intruder to Test Cybersecurity w/ David Kane

    Over a decade ago, David Kane realized that there was a painful gap in cybersecurity. He built Ethical Intruder to fill that gap. 
     
    Today, Ethical Intruder helps clients across financial services, DoD, healthcare, and nonprofits reproduce vulnerable paths a hacker may take, so they can shore up their defenses. David’s ethical hacker teams conduct simulated malicious breaches of a wide variety of business applications and web-accessible entry points.
     
    David has built his firm to be technology-agnostic, which comes with two benefits. First, they aren’t selling a specific solution regardless of its relevance. Second, they are accustomed to evaluating a dynamic collection of tools to identify the primary point of weakness.
     
    In this conversation, Aaron and David discuss how to seel cybersecurity to any firm, why nonprofits need to keep their data secure, and the 
     
    Sign up for a Weekly Email that will Expand Your Mind.
     
    David Kane’s Challenge; Find a way to build someone else up.
     
    Mentioned
    Csoonline.com
    Connect with David Kane Linkedin
    Facebook
    Ethical Intruder Website
    Email




    Underwritten by Piper Creative
    Piper Creative makes creating podcasts, vlogs, and videos easy. 
     
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    We work with Fortune 500s, medium-sized companies, and entrepreneurs.
     
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    • 33 min
    440 Brent Johnson explains Dollar Milkshake Theory for Entrepreneurs

    440 Brent Johnson explains Dollar Milkshake Theory for Entrepreneurs

    Brent Johnson is a wealth manager at Santiago Capital and a General Partner of the IceCap Strong Dollar Fund. Brent has had a multi-decade career in finance and has been responsible for managing billions of dollars.
     
    Brent is well-known for his Dollar Milkshake Theory, where he expects a rapidly appreciating US Dollar over the next few years, relative to other world currencies.
     
    Because the world is completely run by fiat currencies, cash whose value is not backed by some physical good such as gold or silver, Brent expects a massive devaluation of currencies across the board. Because of the U.S. is a relatively safer, stronger economy, he expects capital to flood into its domestic markets.
     
    There are a lot of implications to the theory.
     
    In this interview, Brent explains to Aaron what the Dollar Milkshake Theory is, how Brent’s career has unfolded, and the implications of a rising dollar for business owners and entrepreneurs.
     
    Sign up for a Weekly Email that will Expand Your Mind.
     
    Brent Johnson’s Challenge; Find someone you vehemently disagree with and have a conversation with them.
     
    Connect with Brent Johnson Twitter
    Santiago Capital Website
    brent@santiagocapital.com
     
    If you liked this interview, check out all of our past interviews with finance thinkers, investors, and advisors.
     
    Text Me What You Think of This Episode 412-278-7680




    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.
     
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    • 43 min
    439 Mortgage Master Dan Green is building HomeBuyer.Ai

    439 Mortgage Master Dan Green is building HomeBuyer.Ai

    Dan Green is the founder and CEO of HomeBuyer, a mortgage lender designed for first-time homebuyers. It’s his 3rd company he’s built in the mortgage industry.
     
    Dan previously founded the consumer-friendly mortgage education company "The Mortgage Reports", which was later acquired in 2014 by Full Beaker.
     
    Dan Green is a 17-year mortgage lending veteran and was a multi-year, number-one loan officer before starting HomeBuyer. His current company utilizes intelligent personalization to deliver timely and precise advice through specific moments of a home buyer's journey and fulfills the buyer's mortgage. 
     
    He was part of the Techstars accelerator in 2020.
     
    In this conversation, Aaron Watson and Dan Green discuss how he generated an enormous number of leads with a blog, why mortgage lenders don’t think long-term, and why private mortgage insurance is not the boogeyman.
     
    Sign up for a Weekly Email that will Expand Your Mind.
     
    Dan Green’s Challenge; If you think you will buy a house, reach out to a mortgage loan officer and get a preapproval.
    Connect with Dan Green Linkedin
    Twitter
    HomeBuyer AI Website
    dan@homebuyer.ai
     
    If you liked this interview, check out episode 361 with Jason Wolfe where we discuss starting multiple companies in the gift card space and building off of past successes.
     
    Text Me What You Think of This Episode 412-278-7680




    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.
     
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    • 56 min
    438 How to Build a Multi-Million Dollar Consultancy w/ Ben Wilson of Rivers Agile

    438 How to Build a Multi-Million Dollar Consultancy w/ Ben Wilson of Rivers Agile

    Ben Wilson founded Rivers Agile in 2008, in the eye of the Great Financial Crisis. The software consulting firm started focusing on advanced quality assurance and expanded to offer custom software development. 
     
    Now, Ben is leading his team through the pandemic, an office change, and a shifting marketplace for software solutions. He believes he’s poised to take advantage of a trend of onshoring and digital reinvention that the circumstances will demand.
     
    In this podcast, Ben and Aaron discuss building a team, what makes for good QA, and the markets that Rivers Agile sells into.
     
    Pittsburgh’s best conference to Expand your Mind & Fill your Heart happens once a year.
     
    Ben Wilson’s Challenge; Challenge your vendors to find better deals.
     
    Connect with Ben Wilson
    Linkedin
    Twitter
    Instagram
    Rivers Agile website
    ben@riversagile.com
     
    If you liked this interview, check out our collection of interviews with Pittsburgh’s top entrepreneurs and leaders.
     
    Text Me What You Think of This Episode 412-278-7680




    Underwritten by Piper Creative
    Piper Creative creates podcasts, vlogs, and videos for companies. 
     
    Our clients become better storytellers. 
     
    How? Click here and Learn more.
     
    We work with Fortune 500s, medium-sized companies, and entrepreneurs.
     
    Follow Piper as we grow
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    • 39 min
    437 First Generation High School Grad to Top Financial Advisor, The Mindset of Tyrone Ross

    437 First Generation High School Grad to Top Financial Advisor, The Mindset of Tyrone Ross

    Tyrone Ross is a financial consultant, community builder, and entrepreneur.
     
    He has been named to Investment News 40 under 40 (2019) and a top ten advisor set to change the industry by WealthManagement.com.
     
    Tyrone has focused on pushing a conservative, stodgy industry forward by focusing on young professionals, embracing financial technology startups, and acknowledging the role crypto assets play in a portfolio.
     
    Aaron and Tyrone talk about fighting financial jargon, why advisors fear crypto, and how Tyrone has never taken a vacation.
     
    Pittsburgh’s best conference to Expand your Mind & Fill your Heart happens once a year.
     
    Tyrone Ross’s Challenge; Find our leaders. Mold the next generation of young minds. 
     
    Connect with Tyrone Ross
    Linkedin
    Twitter
    Website
     
    If you liked this interview, check out our back catalog of finance-focused podcast interviews.
     
    Text Me What You Think of This Episode 412-278-7680




    Underwritten by Piper Creative
    Piper Creative creates podcasts, vlogs, and videos for companies. 
     
    Our clients become better storytellers. 
     
    How? Click here and Learn more.
     
    We work with Fortune 500s, medium-sized companies, and entrepreneurs.
     
    Follow Piper as we grow
    YouTube
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    Subscribe on iTunes | Stitcher | Overcast | Spotify 

    • 39 min
    436 Deploying $750 Million into Established Businesses w/ Stephen Gurgovits of Tecum Capital

    436 Deploying $750 Million into Established Businesses w/ Stephen Gurgovits of Tecum Capital

    Stephen Gurgovits is the Managing Partner and co-founder of Tecum Capital, a $750+ million private investment firm based in Pittsburgh, PA. Tecum’s committed capital is deployed as mezzanine debt, subordinated notes, and private equity into lower middle market businesses across the US.
     
    During his career, Stephen has been directly involved in over $1 billion of aggregate financial transactions, both public and private.
     
    Prior to spinning Tecum Capital out of First National Bank, he was President and CEO of F.N.B. Capital Corporation, a wholly-owned merchant banking subsidiary of FNB.
     
    Stephen currently serves on the board of directors for Western Allegheny Capital, Gibraltar Cable Barriers, Uncle Charley’s Sausage Company, Auburn Gear, Inc., Oberg Industries, and the Pittsburgh Chapter of the Association of Corporate Growth.
     
    In this podcast, Aaron and Stephen discuss launching the firm, how they allocate debt and equity investments, and Stephen’s interpretation of current market dynamics.
     
    Pittsburgh’s best conference to Expand your Mind & Fill your Heart happens once a year.
     
    Stephen Gurgovits’s Challenge; Make your bed and read the Wall Street Journal every day.
     
    Connect with Stephen Gurgovits
    Linkedin
    Tecum Capital Website
     
    If you liked this interview, check out episode 269 with Brent Beshore where we discuss private equity investing in the lower middle market.
     
    Text Me What You Think of This Episode 412-278-7680




    Underwritten by Piper Creative
    Piper Creative creates podcasts, vlogs, and videos for companies. 
     
    Our clients become better storytellers. 
     
    How? Click here and Learn more.
     
    We work with Fortune 500s, medium-sized companies, and entrepreneurs.
     
    Follow Piper as we grow
    YouTube
    TikTok
    Instagram


    Subscribe on iTunes | Stitcher | Overcast | Spotify

    • 38 min

Customer Reviews

5.0 out of 5
109 Ratings

109 Ratings

H-man2011 ,

Fantastic listen and guests

Aaron has been a stalwart craftsman in the Pittsburgh podcasting scene for some time now, completely unabshed in his humility and dedication to bringing the best guests and interviews day in and day out. Highly recommended.

Barry Rabkin ,

Everything I love!

Aaron covers everything I love. Pittsburgh, startups, ultimate frisbee, social impact and productivity hacks. He gathers unique movers and shakers from every walk of life for highly engaged conversations. I learn something new every time I listen.

ErikBison ,

Great show, highly recommend!

Aaron and his guests share inspiring and actionable lessons on how to live your best life personally and professionally. Highly recommend listening and subscribing if you want the knowledge AND mindsets to work towards and achieve all your goals in business and life!

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