Entrepreneur's Enigma
Entrepreneur's Enigma

Entrepreneur's Enigma

Seth Goldstein & Goldstein Media LLC

Overview
Episodes

Details

Welcome aboard to the captivating world of Entrepreneur’s Enigma, a podcast that dives deep into the thrilling and sometimes tumultuous journey of being an entrepreneur. Strap yourself in for an exhilarating ride through the highs and lows of the entrepreneurial landscape, as we bring you tales straight from the hearts and minds of some of the most innovative and determined individuals in the business world. Being an entrepreneur isn't just a career choice; it's a way of life that demands unwavering dedication, creativity, and resilience. The road to success is paved with challenges, victories, setbacks, and breakthroughs. Every week, we invite you to join us as we sit down with a diverse array of entrepreneurs, each with their own unique story to share. These remarkable individuals open up about their personal journeys, offering insights into their triumphs and tribulations, their moments of inspiration and frustration. While the entrepreneurial journey can often feel isolating, like navigating uncharted waters, Entrepreneur’s Enigma is here to remind you that you're not alone on this adventure. We understand that the rollercoaster of entrepreneurship can leave you exhilarated one moment and questioning your decisions the next. Our aim is to provide you with a sense of camaraderie and understanding by showcasing the human side of business. Through the stories of our guests, you'll find relatable experiences and valuable lessons that remind us all that success rarely comes without its fair share of hurdles. Our podcast episodes are your ticket to an engaging exploration of the entrepreneurial mindset. Whether you're a seasoned business owner, a budding entrepreneur, or someone curious about the world of startups and innovation, you're invited to join us on this audio journey of discovery. From tales of humble beginnings to accounts of turning bold ideas into reality, you'll find a treasure trove of wisdom and motivation to fuel your own ambitions. Mark your calendars, because we're here to brighten your Tuesdays. Set your alarms for 8 am Eastern, and let us be your companion during your morning routine, commute, or daily walk. As the sun rises, so does your chance to absorb the pearls of wisdom our guests generously share. With each episode, you'll gain new perspectives, strategies, and insights that can help you navigate your own entrepreneurial challenges. So, whether you're sipping your morning coffee, tackling your daily tasks, or simply seeking inspiration, remember that Entrepreneur’s Enigma is more than just a podcast. It's a community of like-minded individuals brought together by a shared passion for innovation, growth, and the unrelenting pursuit of dreams. Join us as we uncover the mysteries and wonders of entrepreneurship, one episode at a time. In this fast-paced world of business, it's easy to get lost in the noise. But with Entrepreneur’s Enigma, you'll have a reliable compass guiding you through the ever-changing landscape of entrepreneurship. Through the candid conversations, the genuine laughter, and the unfiltered discussions, you'll find solace in knowing that the challenges you face are all part of a journey that countless others have embarked upon before. So, get ready to embark on a journey filled with stories that will touch your heart, ignite your imagination, and invigorate your entrepreneurial spirit. Remember, you're not alone in this enigma called entrepreneurship – we're right here with you, every step of the way.

Recent Episodes

The Surprising Power of Quizzes to Turn Cold Audiences into Hot Leads with Maiko Sakai
APR 7, 2026
The Surprising Power of Quizzes to Turn Cold Audiences into Hot Leads with Maiko Sakai
Maiko Sakai designs the front door of high-ticket businesses. After years in management consulting, she noticed a pattern: founders invested heavily in traffic and content but still relied on persuasion-heavy sales calls to close. The leak wasn't visibility—it was entry. Now she works with consultants, coaches, and service founders to build diagnostic entry systems (ie. Quizzes etc.) that let buyers self-identify before booking a call. Instead of pushing traffic toward webinars or lead magnets, she designs structured decision experiences that surface tension and accelerate clarity. Her work reframes quizzes from engagement tools into strategic infrastructure — reducing friction, shortening timelines, and attracting leads who already know why they're a fit. She believes marketing shouldn't convince. It should help buyers conclude. Maiko holds an MBA from Cornell, but her real expertise comes from studying how decisive buyers think—and designing entry points that respect their intelligence. Links https://maikosakai.com https://linkedin.com/in/maikosakai https://threads.net/maikosakaibiz https://instagram.com/maikosakaibiz https://x.com/maikosakaibiz 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/podcast-mastery-community-6116/about 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 Leave The Show A Voicemail: https://podcastfeedback.com/entrepreneursenigma Learn more about your ad choices. Visit megaphone.fm/adchoices
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26 MIN
Overcoming Failure and Finding Success with Dr. Danny Brassell
MAR 31, 2026
Overcoming Failure and Finding Success with Dr. Danny Brassell
A highly-sought after speaker, trainer and coach known as “Jim Carrey with a Ph.D.,” Dr. Danny Brassell (www.DannyBrassell.com) has spoken to over 3,500 audiences worldwide. He has authored 21 books, including Leadership Begins with Motivation and Misfits and Crackpots. The co-founder of WellCrafted Story™, Danny helps entrepreneurs, individuals and organizations leverage speaking on stages as a major client lead source that converts. Links https://www.YouTube.com/DannyBrassell https://www.twitter.com/DannyBrassell https://www.Facebook.com/DannyBrassell https://www.linkedin.com/in/dannybrassell/ https://www.instagram.com/realDannyBrassell 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/podcast-mastery-community-6116/about 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 Leave The Show A Voicemail: https://podcastfeedback.com/entrepreneursenigma Learn more about your ad choices. Visit megaphone.fm/adchoices
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18 MIN
From Cleaning Floors to Building Empires: The Entrepreneurial Journey of Guy Dunn
MAR 24, 2026
From Cleaning Floors to Building Empires: The Entrepreneurial Journey of Guy Dunn
Guy Dunn is a serial entrepreneur, technology innovator, and recognized networking expert based in the Philadelphia area. With over three decades of business experience, Guy has built his career on the fundamental principle that strong relationships are the foundation of business success. As the creator of RoofTrack360.com, a comprehensive platform revolutionizing customer acquisition systems for roofing companies, and TrustLooper.com , an innovative trust-building platform for businesses, Guy has proven his ability to identify market needs and develop technology solutions that solve real-world problems. His entrepreneurial journey includes scaling a multimillion-dollar franchise operation from 3 territories in 2006 to 9 territories across the Philadelphia Metro area, New York City metro area, and Central New Jersey by 2012. Guy's impressive career includes executive leadership roles as Chief Financial Officer of M. Davis and Company, Director of Business Development with Global Systems Technologies, Inc., and Chief Operating Officer with Glo-Chem International. His diverse experience across industries has given him a unique perspective on the universal principles of business growth: identifying target clients, attracting them, selling to them, and doing it profitably. A 1982 graduate of Morehouse College with a Bachelor's degree in accounting, Guy combines financial acumen with entrepreneurial vision. He is also the host of a business podcast where he shares insights on networking, technology, and business growth strategies with entrepreneurs and business leaders. As a sought-after speaker and consultant, Guy has presented his insights on networking and digital marketing to over 100 companies across New York, New Jersey, and Pennsylvania. He is the author of multiple books including ;Networking For Business; and Maybe You Can Fix It Yourself—Quick Computer Fixes For The Non-Geek. Guy credits his success to his self-proclaimed identity as a professional networker, his 2025 edition of Networking For Business represents the culmination of his decades of experience building meaningful business relationships in an increasingly digital world. Links https://www.linkedin.com/in/guydunn/ https://www.youtube.com/@TrustlooperIdeaGuy https://trustlooper.com https://rooftrack360.com 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/podcast-mastery-community-6116/about 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 Leave The Show A Voicemail: https://podcastfeedback.com/entrepreneursenigma Learn more about your ad choices. Visit megaphone.fm/adchoices
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17 MIN
From Side Hustler to Security Industry Disruptor: Taylor May's Entrepreneurial Journey
MAR 17, 2026
From Side Hustler to Security Industry Disruptor: Taylor May's Entrepreneurial Journey
Taylor May is the Founder & CEO of SecurityVIP (SVIP), a research firm dedicated to bridging the gap between manufacturers and end users in the security industry. With more than 12 years of experience in the security industry, Taylor specializes in emerging technologies and is recognized for building strong, lasting end user relationships. His leadership and impact have earned him recognition as an IFSEC Global Security Influencer, an Honored Listee in Marquis Who’s Who in America, and a Top 40 Global Thought Leader by the Life Safety Alliance. Taylor holds a B.S. in Business Administration from Oklahoma State University, where he also competed as a Defensive End on the 2011 Big 12 Championship Football Team. He later earned his MBA from the University of Dallas. Links https://www.linkedin.com/in/taylor-may-mba-55b40a84/ https://www.linkedin.com/company/svip-enterprises https://www.svip.news/ 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/podcast-mastery-community-6116/about 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 Leave The Show A Voicemail: https://podcastfeedback.com/entrepreneursenigma Learn more about your ad choices. Visit megaphone.fm/adchoices
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14 MIN
Rebuilding a Travel Business From Scratch With Ali Raymer: Surviving and Thriving After COVID
MAR 10, 2026
Rebuilding a Travel Business From Scratch With Ali Raymer: Surviving and Thriving After COVID
Ali Raymer is a Senior Travel Advisor and team leader at Picture This Travel who rebuilt her business from the ground up after COVID wiped out her income while she was navigating new motherhood. After briefly returning to teaching, she reinvented her business through personal branding, content, and systems—eventually scaling to a multi-million-dollar book of business. Today, Ali leads a high-performing team and speaks candidly about entrepreneurship, reinvention, and what it really takes to rebuild when plans fall apart. She brings a grounded, real-world perspective on growth, leadership, and resilience behind the highlight reel. Links Website: https://www.alipicturethistravel.com Instagram: https://www.instagram.com/alipicturethistravel LinkedIn: https://www.linkedin.com/in/alipicturethistravel/ Facebook: http://facebook.com/alipicturethistravel YouTube: https://www.youtube.com/@alipicturethistravel 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/podcast-mastery-community-6116/about 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 Leave The Show A Voicemail: https://podcastfeedback.com/entrepreneursenigma Learn more about your ad choices. Visit megaphone.fm/adchoices
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18 MIN