
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 30, 2023 • 41min
569 Timeless Wisdom w/ Kevin Kelly
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 collect these thoughts after a recent birthday caused him to reflect on which lessons he could pass to his children.
In this episode, Aaron and Kevin talk about aphorisms, why it was important for him to write this book now, and the impact he hopes he has on his family.
Kevin Kelly’s Challenge; Think about how to be a good ancestor. Work on one good thing that you think your future generation will thank you for, or thank your great grandparents for something that they have done that you’re proud and thankful for.
Connect with Kevin Kelly
Twitter
Website
Excellent Advice for Living: Wisdom I Wish I'd Known Earlier
If you liked this interview, check out our episode about Four Huge Startup Exits w/ Jason Wolfe
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Apr 16, 2023 • 44min
568 Four Huge Startup Exits w/ Jason Wolfe
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 consider how he grew up. After growing up in the Milton Hershey School, an orphanage founded by Milton Hershey, Jason was living out of his car.
He taught himself how to code by using books at the local library and CompUSA's 'Building the Perfect Web'. This led to building the first coupon website and launching his first internet business. From 1995 to 2000, Jason built the business, raising $500k in VC from Jupiter Media and garnering >$1 million in annual sales and 20 million page views per month.
Today, he is building GiftYa, GiveInKind, and PerfectGift, which have the potential to be his biggest businesses yet.
Jason’s Challenge; Give more. Be Kind. Pull someone else up.
Connect with Jason Wolfe
Linkedin
Website
jason@wolfe.com
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Apr 9, 2023 • 44min
567 EOS and The Transformation of Digital Marketing Agency w/ Lyn Askin (Raxxar Digital Marketing)
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 the book Traction by Gino Wickman. His revenue triple, team size doubled, and profit 7xed in a short period of time.
Lyn was so impacted that he’s become a professional EOS implementer, helping business owners and leadership teams implement this powerful framework to improve their business processes, increase productivity, and drive growth.
In this episode Aaron and Lyn talk about his experience in the digital marketing industry, how he cracked the code in making his business much larger and more profitable, and how a personal health scare catalyzed change.
Lyn Askin’s Challenge; Sit with your leadership team, define and live your business’ Core Values.
Connect with Lyn Askin
Linkedin
Twitter
Website
If you liked this interview, check out our episode about the Million Dollar Agencies and Elite Mindsets w/ Jordan Ross (8 Figure Agency)
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Apr 2, 2023 • 38min
566 Million Dollar Agencies and Elite Mindsets w/ Jordan Ross (8 Figure Agency)
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 website design and development.
In this episode, Aaron and Jordan talk about how his consultancy helps marketing firms scale from 6 to 8 figures, the systems of success, what he learned from working at Amazon, and neuro linguistic programming.
Jordan Ross’ Challenge; Go all-in on yourself. Learn how to meditate and center yourself.
Connect with Jordan Ross
Linkedin
Website
If you liked this interview, check out our episode about Revenue in Year One Selling Saas Companies with Andrew Gazdecki
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Mar 27, 2023 • 38min
565 A Local Food Revolution w/ Simon Huntley (Harvie)
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 weekly or bi-weekly deliveries of fresh, locally grown produce and other farm products.
Harvie works by allowing farmers to create their own subscription services on the platform. Farmers can choose the products they want to offer, set their own prices, and customize the delivery schedule. Consumers can then sign up for the service and receive regular deliveries of fresh, locally grown produce and other farm products..
For farmers, Harvie provides a way to sell their products directly to consumers without having to go through middlemen like distributors or grocery stores. This allows farmers to earn a higher profit margin and build a stronger relationship with their customers. For consumers, Harvie provides access to fresh, locally grown produce and other farm products that are often of higher quality than what is available in grocery stores.
Simon Huntley and Harvie are making it easier for small farmers to succeed by connecting them with consumers in their communities. With Harvie's customizable subscription service, farmers can sell their products directly to consumers, which benefits both parties.
In this episode, Aaron and Simon talk about the decades of experience how he has grown his company, how they’re able to do it bootstrapped, and the lessons he learned building the logistics infrastructure to serve this function.
Simon Huntley’s Challenge; Cook a meal for yourself and think about the people that made it possible.
Connect with Simon Huntley
Linkedin
Twitter
Website
If you liked this interview, check out our episode with Christian Simmons who’s Changing the Liquor Landscape in Pennsylvania
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Mar 20, 2023 • 47min
564 Bleeding Edge Robotics w/ Spencer Krause
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 and hardware to solve robotics, mechanical systems, electrical engineering, design and software development problems for their clients.
Spencer is also the host of Collaborative, where he interviews other leaders in the industry and discusses the interesting challenges of building robots.
In this episode, Aaron and Spencer talk about being hired to solve bleeding edge technology problems, good client relations, and the future of autonomous robots.
Spencer Krause’s Challenge; Allot 15 minutes of your day to think about ways to make your job more efficient.
Connect with Spencer Krause
Linkedin
Website
Youtube
If you liked this interview, check out our episode about Robot Pioneer Saving Lives & Improving Quality of Life w/ Jorgen Pedersen.
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Mar 12, 2023 • 30min
563 How Artificial Intelligence will Transform Meetings w/ Vowel’s Andy Berman
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 live for their users.
Andy is an experienced entrepreneur who previously founded Nanit, an industry-leading smart baby monitor.
In this episode, Aaron and Andy talk about competing with Zoom, the potential for AI to change the way we work, and how he thinks about building a compound start-up.
Andy Berman’s Challenge; Try Vowel and see if we can make your company more productive.
Connect with Andy Berman
Linkedin
Twitter
Website
If you liked this interview, check out our episode about How AI Changes Healthcare Forever w/ Dr. Shiv Rao (Abridge)
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Mar 6, 2023 • 45min
562 The Internet’s Top Sticker Brand w/ Sticker Mule founder Anthony Constantino
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.
Anthony oversees an operation that spans 16 countries in 4 continents with customers including Google, Facebook, Twitter and many of the world’s best brands.
Anthony is also the founder of the new social media platform Stimulus and has spent most of the past four years in Mexico City, one of boxing’s biggest hubs. He became a pro boxer at the age of 39.
In this episode, Aaron and Anthony talk about how he started his company, the constraints he faced operationally, and the marketing strategy that they deployed for more than 12 years that continues to work for them.
Anthony Constantino’s Challenge; Go try something new.
Connect with Anthony Constantino
Linkedin
Instagram
Website
Stimulus
If you liked this interview, check out our episode about 3 Generations of Family Business w/ Scott Heeter
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Feb 20, 2023 • 43min
561 $7 Million Annual Recurring Revenue 100% Bootstrapped w/ Adriane Schwager (Growth Assistant)
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 over $7 million in annual recurring revenue. More impressively, they’re completely bootstrapped..
They began offering companies digital marketing assistants and then graphic designers, but have expanded their offering to sales development, email marketing, business operations, and customer success.
In this episode, Aaron and Adriane talk about how she helps companies save money, how to be a more empathetic and clear-minded decision maker as the head of an organization, and how Jesse Puji laid the groundwork for her company to have enormous success after just 2 years in business.
Adriane Schwager’s Challenge: Write down every task you do for a day, put a check mark on the tasks you do more than once a week, then ask yourself which of the tasks you can document so you can delegate it and it’ll give you more time to focus on more high-level strategic work.
Connect with Adriane Schwager
Linkedin
Twitter
Website
Tiktok
If you liked this interview, check out our episode about Gateway X and TikTok Ads w/ Jesse Pujji
Underwritten by Piper Creative
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Feb 15, 2023 • 31min
560 Sustainability in Supply Chain with Daniela Osio (Kloopify)
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 with the data, analytics, and visibility into the environmental impact of all purchases.
In this episode, Aaron and Daniela talk about procurement, its desperate need for innovation, and how her platform helps companies implement sustainability goals in their procurement process.
Daniela’s Challenge: Take a look at where you’re spending your money. Do you spend your money on companies that align with your personal goals?
Connect with Daniela Osio
Linkedin
Website
If you liked this interview, check out our episode about the $2 Million to $80+ Million Family Business w/ Kristy Knichel
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.
Follow Piper as we grow
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Subscribe on iTunes | Stitcher | Overcast | Spotify
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