Entrepreneur's Enigma: 20-Minute Entrepreneur & Founder Interviews

Seth Goldstein & Goldstein Media LLC

Details

Most business podcasts interview people who raised a round or sold a company. This one doesn't. Every Tuesday, Seth Goldstein spends twenty minutes or so with a founder or entrepreneur actually running a business. Translators, designers, coaches, agency owners. People who left a job and built something real. Seth was a journalist for six years, so he arrives with a question and gets out of the way.

Recent Episodes

SEP 22, 2026
Why Ignoring AI Could Make You Unemployable Long Term
Geoff Livingston helps organizations cut through AI hype and build systems that actually work. As founder of Generative Buzz, he has guided Fortune 500 marketing departments, major trade associations, and government agencies through AI transformation, from strategy and workforce development to measurable adoption. His clients typically see 10 or more hours of weekly productivity gains within 30 days. Geoff brings 30 years of technology, marketing, and crisis communications experience to this work, with clients including AT&T, Google, PayPal, Ford, and Verizon. He holds a master's degree from Georgetown University and is the author of Now Is Gone: Think Liquid to Navigate Never-ending Change and three social media books. He lives in Alexandria, Virginia with his family of humans and fur babies, where he writes The Buzz on Substack, takes pics, runs trails, and practices Buddhism (not in that order). Links Find Geoff on Linkedin: https://www.linkedin.com/in/geoffliving/ His Company: https://generativebuzz.ai/ His Substack: https://buzzbylivingston.substack.com/ Buy His Latest Book: https://bookshop.org/p/books/now-is-gone-think-liquid-to-navigate-neverending-change-livingston/fab724135ff6b6c1?ean=9798995577522&bkshp-astro=t His Podcast, AI Hope: https://open.spotify.com/show/033ysKUcHpyKqTyNPVR6vL https://podcasts.apple.com/us/podcast/ai-hope/id1896926627 If you’re enjoying ⁠Entrepreneur’s Enigma⁠, please give me a review on the podcast directory of your choice. The show is on all of them and these reviews really help others find the show. iTunes: ⁠https://gmwd.us/itunes⁠ Podchaser: ⁠https://gmwd.us/podchaser⁠ TrueFans: ⁠https://gmwd.us/truefans⁠ Also, if you’re getting value from the show and want to buy me a coffee, go to the show notes to get the link to get me a coffee to keep me awake, while I work on bringing you more great episodes to your ears. → ⁠https://ko-fi.com/entrepreneursenigma⁠ Support me on ⁠TrueFans.fm⁠ → ⁠https://gmwd.us/truefans⁠. Support The Show & Get Merch: ⁠https://shop.entrepreneursenigma.com⁠ Follow Seth Online: Instagram: ⁠https://instagram.com/s3th.me⁠ LinkedIn: ⁠https://www.linkedin.com/in/sethmgoldstein/⁠ Seth On Mastodon: ⁠https://indieweb.social/@phillycodehound⁠ The Marketing Junto Newsletter: ⁠https://MarketingJunto.com Host/Producer/Booker: Seth Goldstein of Goldstein Media LLC Podcast Network: Marketing Podcast Network AI Disclosure: The only thing that is AI generated is the intro voice guy and any long transcripts. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
17 MIN
SEP 15, 2026
What a Near-Death Experience Taught Him About Love and Purpose
Today’s guest is Gaylen Wilson, a heart transplant survivor, 20-years-sober former alcoholic, relationship author, erectile dysfunction advocate, Certified Thriving Relationship Coach, and co-founder of The Monument Method Institute with his wife, Heather. His life has been shaped by repeated reinvention—from farm and career failures to alcoholism, sobriety, financial hardship, and rebuilding professionally. In 2014, a virus left him in end-stage heart failure, forcing Gaylen and Heather to endure years of hospital stays, uncertainty, disability, financial pressure, and lost intimacy. On June 19, 2018, shortly after telling Heather he likely had only months to live, Gaylen received the call that a donor heart was available. After his transplant, Gaylen devoted himself to helping others make the most of the years they are given. For more than five years, he supported approximately 60,000 men and partners in two major erectile dysfunction communities, witnessing how ED can affect mental health, identity, intimacy, and relationships. Those experiences inspired The Monument Method, a relationship system focused on emotional safety, conflict repair, intimacy, accountability, and protecting the bond under pressure. Gaylen and Heather are also developing MVP—Monument Validated Person—a relationship-readiness dating platform designed to help people prepare for healthier relationships. His mission is to help people build relationships strong enough that no one has to face life alone. Links https://www.monumentmethodinstitute.com/ Monument Hearts Trailer on TikTok https://www.tiktok.com/t/ZP8GmXFnX/ Monument Method Trailer on TikTok https://www.tiktok.com/t/ZP8GmATNK/ ED Trilogy on TikTok https://www.tiktok.com/t/ZP8GWBKDj/ Timestamps [00:00] - Intro to Gaylen Wilson’s extraordinary reinvention story [02:02] - From farm life to stockbroker and the collapse that changed everything [03:39] - Alcoholism, emotional shock, and not having the tools to cope [04:14] - Finding sobriety through Rational Recovery [04:44] - Consulting work, 9/11, and another career setback [05:42] - Meeting Heather and rebuilding after divorce [06:10] - Traveling to all 48 contiguous states for field service work [06:48] - A virus, heart failure, and years of declining health [07:44] - Heather’s commitment through his illness [08:14] - The call for a donor heart and the race to the hospital [09:03] - Transplant day and the “Ferrari engine in an old Ford pickup” metaphor [09:34] - Why the transplant became a mission to help others [09:58] - Hold Me Tight, attachment theory, and the science behind conflict [11:36] - Creating the Monument Method as an emergency break for fights [12:36] - Why the relationship must matter more than ego [13:03] - Using touch and eye contact to reset fight or flight [14:12] - Marriage as a refuge, not another source of stress [15:32] - Parenting, attachment issues, and the need for real connection [16:36] - Why being an entrepreneur is easier with a soulmate partner [17:23] - Lessons from traveling in a Prius and learning to apologize fast [18:09] - What drives him now and what keeps him grounded [18:58] - The most important thing to carry with you in life [19:44] - What the transplant changed about his outlook on mortality and time If you’re enjoying Entrepreneur’s Enigma, please give me a review on the podcast directory of your choice. The show is on all of them and these reviews really help others find the show. iTunes: https://gmwd.us/itunes Podchaser: https://gmwd.us/podchaser TrueFans: https://gmwd.us/truefans Also, if you’re getting value from the show and want to buy me a coffee, go to the show notes to get the link to get me a coffee to keep me awake, while I work on bringing you more great episodes to your ears. → https://ko-fi.com/entrepreneursenigma Support me on TrueFans.fm → https://gmwd.us/truefans. Support The Show & Get Merch: https://shop.entrepreneursenigma.com Follow Seth Online: Instagram: https://instagram.com/s3th.me LinkedIn: https://www.linkedin.com/in/sethmgoldstein/ Seth On Mastodon: https://indieweb.social/@phillycodehound The Marketing Junto Newsletter: https://MarketingJunto.com
23 MIN
SEP 8, 2026
Stop Chasing Algorithms and Start Building Trust
Note: This episode is a longer one. But well worth a listen. Stephan Bajaio believes that success takes time and effort, and he emphasizes this lesson through what he calls the "four Ps." Drawing on his experience, Stephan shares practical advice with business owners: when evaluating a web page, especially a services page, he encourages them to look beyond surface-level details. He questions whether important points about a service are truly given the attention they deserve, suggesting that if something merits a bullet point, it likely deserves a full paragraph to provide essential context and value. Through this approach, Stephan helps businesses move from shallow descriptions to a more meaningful, engaging presentation of their work, ensuring their key offerings are conveyed with clarity and depth. More About Stephan: Stephan Bajaio is a CEO, Co-Founder, and CMO with 20+ years in SEO and digital marketing. He's helped brands like FedEx, Comcast, and Siemens win in search. Stephan co-founded VibeLogic to help businesses navigate the collision of AI and organic search. He helps marketers stop chasing algorithms and start building strategies that actually last. Links https://www.vibelogic.com/ https://www.stephanbajaio.com https://www.linkedin.com/in/stephanbajaio/ Start of interview: [01:40] Other Key Moments [04:07] Early interest in computers [07:33] Importance of Detailed Descriptions [11:53] Decision fatigue and modern anxiety [15:03] Building trust through valuable insights [19:04] Addressing therapy stigma [21:34] Balancing work and family time [26:33] Sharing Entrepreneurial Challenges [29:07] Hands-off management strategy [30:23] Finding passionate team members If you’re enjoying Entrepreneur’s Enigma, please give me a review on the podcast directory of your choice. The show is on all of them and these reviews really help others find the show. iTunes: https://gmwd.us/itunes Podchaser: https://gmwd.us/podchaser TrueFans: https://gmwd.us/truefans Also, if you’re getting value from the show and want to buy me a coffee, go to the show notes to get the link to get me a coffee to keep me awake, while I work on bringing you more great episodes to your ears. → https://ko-fi.com/entrepreneursenigma Support me on TrueFans.fm → https://gmwd.us/truefans. Support The Show & Get Merch: https://shop.entrepreneursenigma.com Follow Seth Online: Instagram: https://instagram.com/s3th.me LinkedIn: https://www.linkedin.com/in/sethmgoldstein/ Seth On Mastodon: https://indieweb.social/@phillycodehound The Marketing Junto Newsletter: https://MarketingJunto.com
40 MIN
SEP 1, 2026
Why AI Won’t Replace Great Marketers—It Will Augment Them
Adrienne Wilkerson is the co-founder and CEO of Beacon Media + Marketing, a national digital marketing agency specializing in mental and behavioral health organizations. She started her first business in 2001, is an Inc. 5000 winner for three consecutive years, a published author, and the host of The Beacon Way podcast. Adrienne helps founders and leaders stop second-guessing their marketing and start showing up in a way that actually reflects the mission they built their business around, because when the connection is right, the growth follows. Links https://www.beaconmm.com/the-beacon-way/ https://open.spotify.com/show/3BDBxY9jDasCTJtRkX7EJ2 https://podcasts.apple.com/us/podcast/the-beacon-way/id1593107821 https://www.youtube.com/@BeaconWayPodcast Her book: https://a.co/d/fBo6sBg Her Author Page: https://www.amazon.com/author/adrienne.wilkerson https://www.linkedin.com/in/adriennewilkerson/ If you’re enjoying Entrepreneur’s Enigma, please give me a review on the podcast directory of your choice. The show is on all of them and these reviews really help others find the show. iTunes: https://gmwd.us/itunes Podchaser: https://gmwd.us/podchaser TrueFans: https://gmwd.us/truefans Also, if you’re getting value from the show and want to buy me a coffee, go to the show notes to get the link to get me a coffee to keep me awake, while I work on bringing you more great episodes to your ears. → https://ko-fi.com/entrepreneursenigma Support me on TrueFans.fm → https://gmwd.us/truefans. Support The Show & Get Merch: https://shop.entrepreneursenigma.com Follow Seth Online: Instagram: https://instagram.com/s3th.me LinkedIn: https://www.linkedin.com/in/sethmgoldstein/ Seth On Mastodon: https://indieweb.social/@phillycodehound The Marketing Junto Newsletter: https://MarketingJunto.com
33 MIN
AUG 25, 2026
From Poopy Pipelines to Predictable Growth
Lindsay Rios is a Fractional CRO & owner of GTM Done Right, helping B2B companies turn accidental growth into intentional growth. Many of the businesses she works with have built revenue growth through referrals, word of mouth and organic inbound. But eventually those channels stop producing the same results, growth becomes less predictable, and leadership realizes they need a more intentional go-to-market strategy. This is where Lindsay comes in to identify the real causes of stalled growth, whether it's a misaligned ICP, a disconnected revenue strategy or what she famously calls a "poopy pipeline." Lindsay also partners alongside Mandy McEwen, where they help business with their revenue growth by integrating social selling into their GTM strategy. Links https://www.lindsayrios.com https://yourfuturebiz.com https://nextwave.golumi.io If you’re enjoying Entrepreneur’s Enigma, please give me a review on the podcast directory of your choice. The show is on all of them and these reviews really help others find the show. iTunes: https://gmwd.us/itunes Podchaser: https://gmwd.us/podchaser TrueFans: https://gmwd.us/truefans Also, if you’re getting value from the show and want to buy me a coffee, go to the show notes to get the link to get me a coffee to keep me awake, while I work on bringing you more great episodes to your ears. → https://ko-fi.com/entrepreneursenigma Support me on TrueFans.fm → https://gmwd.us/truefans. Support The Show & Get Merch: https://shop.entrepreneursenigma.com Want to learn from a 15 year veteran? Check out the Podcast Mastery Community:https://www.skool.com/podcasting Follow Seth Online: Instagram: https://instagram.com/s3th.me LinkedIn: https://www.linkedin.com/in/sethmgoldstein/ Seth On Mastodon: https://indieweb.social/@phillycodehound The Marketing Junto Newsletter: https://MarketingJunto.com
31 MIN