Entrepreneur’s Enigma

Entrepreneur’s Enigma is a podcast about the ups and downs of being an entrepreneur. Being an entrepreneur is tough. It’s a rollercoaster.

Every week, host Seth Goldstein talks to different entrepreneurs about their journey… their successes and their failures.

Entrepreneurship can be a lonely game, but it doesn’t have to be. Come along for the ride.

Shows are released weekly on Tuesdays at 8 am Eastern.

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…

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The Power of Teamwork in Entrepreneurship: Lessons from Melanie Sikma

Melanie Sikma is the CEO and co-founder of her family’s tax firm One Stop Tax Strategists, where they helps high-income entrepreneurs bring peace to taxes and purpose to profits. Through strategic tax planning, top-notch accounting work and financial support, One Stop Tax Strategists uncovers an average of $70,000 in tax savings per client each year……

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Managing Music, Media, and Motivation: Allen Halas’ Unique Entrepreneurial Journey

Allen Halas is a music writer, radio host, and podcaster based in Milwaukee, WI. He currently works for OnMilwaukee, the largest digital media outlet in the city, and can be heard weekly on FM 102.1 in Milwaukee as the host of Love Local Radio. Allen is also the founder of Breaking And Entering, a music…

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Embracing Risk: Jake Wysocki’s Leap from Intrapreneur to Entrepreneur

Jake Wysocki trained hundreds in workshop facilitation at a Fortune 200 company, then left to bring that same methodology to the world of coaching. He now runs Intention Craft where he helps experts build Workshops their clients love attending and they love to deliver. Links Grab Jake’s free resources at workshopwhy.com – including a 45-minute…

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Delco Stories, Digital Marketing, and Becoming Your Own Boss with Josh Irons

Josh Irons is the CEO of River Avenue Digital, a digital-first marketing agency that helps small and mid-sized businesses take digital marketing off their to-do lists. He leads the agency’s people, strategy, and client work, with a focus on modern growth engines like AI-enabled marketing, performance analytics, and clear, conversion-driven storytelling. He recently expanded River…

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Balancing Podcasting, Business, and Parenthood: Insights from Tony Berardo

Tony Berardo is a multifaceted creator and entrepreneur whose work spans podcasting, digital content strategy, and brand development. He is the creator and host of Humanity & Hashtags, a podcast dedicated to exploring human connection, social trends, and modern-day challenges through meaningful, story-driven conversations. Tony is also the founder of Human Dad, a lifestyle apparel…

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Marketing and Leading Authentically Through Human Design with Stefanie Carlstedt

Stefanie Carlstedt is a Human Design Business Coach who helps entrepreneurs build businesses that actually fit who they are, not who the online world tells them to be. After building and losing a six-figure business by following one-size-fits-all strategies, Stef was forced to confront a hard truth: success with self abandonment isn’t sustainable. Through Human…

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The Ups and Downs of Tech Entrepreneurship: Bill Evans’ Tips for Success

Bill Evans is the CEO and Solutions Architect of Liberty Fox Technologies, a software consulting firm he founded after being laid off early in his career. A La Salle University graduate with dual degrees in Computer Science and Telecommunications, Bill turned a challenging job market into an opportunity to build a stable, fast-growing technology consultancy…

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From Radio DJ to Opera Singer to Tech Innovator: Alan Brunton’s Wild Entrepreneurial Journey

Alan Brunton is redefining the role of audio in human health, education, and performance. From pioneering restaurant ventures and media productions to groundbreaking audio technology, Alan’s journey reflects a rare blend of entrepreneurial drive, creative vision, and scientific innovation. His company, Cymatrax, stands at the forefront of a global movement to harness sound not only…

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From Camera-Shy to Content King: Ed Oyama on Embracing Imperfect Video for Business Growth

Ed Oyama used to hate being on camera. Twenty years ago, he had a blast editing videos for his church’s college group – but he couldn’t talk on camera to save his life! But one day he tried something different. He stopped chasing perfection and simply showed up – walking and talking with his phone,…

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