Hustle-Free Entrepreneur

Jese Gary
  • 5.0 (2)
  • Entrepreneurship

Welcome to The Hustle-Free Entrepreneur, the go-to podcast for event industry professionals and service-based business owners ready to ditch the hustle mindset and build sustainable, efficient businesses. Join us as we pull back the curtain on the unsexy side of entrepreneurship—think systems, processes, and back-office strategies that move the needle. Through expert interviews, actionable tips, and candid conversations, you’ll learn how to master running your business to focus on growth, profits, and living life on your terms. Whether you’re an event planner, venue owner, caterer, or solopreneur in any service-based field, this podcast is your ultimate resource for business success.Subscribe now to uncover strategies to help you scale smarter, not harder.

  1. 19h ago

    Why She Quit $12,000 Weddings on Purpose

    Send us Fan Mail Download the Complete Business System Stack for your event business: https://geasystemstudios.myflodesk.com/stack Stephanie built a wedding photography business over almost two decades, got to $8,000 to $12,000 a wedding, and then walked away from it on purpose. In this episode, she gets honest about the part nobody posts: being excellent at something you have stopped loving, watching the industry shift under you, and betting a multi-six-figure business on a photo booth she once told a friend "nobody would want." Jese and Stephanie get into the money, the jadedness, the ego check of corporate work, and why the seasons you want to skip are the ones building you. What you will hear: - The mentor who would not let her hold a camera for a full year, and why that made her better - How one bride's referral opened the door to corporate, and the ego check that came with it - The 2020 moment she watched 80% of her revenue disappear in a single week, and what kept the lights on - Why a photo booth is a second business, not an add-on, and what most photographers get wrong about it - The one thing she stopped doing that changed how the whole business feels Guest bio: Stephanie is a photographer and experience-maker who spent years shooting weddings under Sonju Photography before building Juju Booth, a photo and video experience company serving weddings, corporate events, and brand activations across multiple markets. She is in the Photo Booth Expo Hall of Fame. Originally rooted in South Florida, she now runs the business from North Carolina while her team stays close to home. About HFE: Hustle Free Entrepreneur is the real, behind-the-scenes conversation for event industry business owners who are successful on paper and quietly exhausted underneath it. Hosted by Jese Gary, HFE is where we talk about what running this business actually looks like, the money, the burnout, the pivots nobody shows online, without the hustle culture and without the motivational fluff. If you are running the version of your business that looks impressive from the outside and feels like survival on the inside, you are not alone, and you did not do anything wrong. Links: Connect with Stephanie: https://jujubooth.com/ 📌 Resources Mentioned: 🔗 Want a free business system audit? Let’s identify the gaps and opportunities in your event business   🔗 Work with GEA Systems Studio to build your systems + automations 🎙 Thanks for tuning in to the Hustle Free Entrepreneur Podcast! If you enjoyed this episode, don’t forget to:  ✅ Subscribe so you never miss an update  ✅ Leave a review—it helps us reach more entrepreneurs like you!  ✅ Share this episode with a fellow business owner who needs it 🚀 Ready to streamline your business and ditch the hustle? Grab my free resources at https://stan.store/greeneyedambition. 📲 Let’s Connect! 📌 Instagram: @greeneyedambition 📌 Website: greeneyedambition.com Until next time, keep building smarter—not harder!

  2. Jun 9

    After 20 Years in Weddings, Here's What's Really Changing

    Send us Fan Mail Tara Melvin has been planning weddings in Washington, DC for over 20 years. She has watched this industry shift three or four times over. Pinterest. Instagram. COVID. Now AI. And in this conversation, she said something that should stop every event business owner in their tracks. The competition is no longer the planner down the street. The competition is AI. And the vendors who do not train AI about who they are and what they do are about to become invisible. This is the real, behind-the-scenes conversation with Tara Melvin, founder of Signature Concepts and founder of the National Society of Black Wedding and Event Professionals (NSBWEP). She shares what 20+ years in luxury weddings have actually taught her about adapting without losing your soul, what she would do completely differently if she were starting today, and the trends quietly reshaping how couples plan, spend, and celebrate. In this episode: What weddings looked like in 2004 versus what couples expect right nowWhy couples have become the influencers of their own wedding dayThe exact reason most wedding vendors are about to disappear from AI searchWhat Tara is telling her clients when they show up with AI-generated expectationsWhy multi-day, dress-coded, culture-infused weddings are the new normThe honest truth about boundaries when your clients are paying you six figuresWhat Tara would do completely differently if she started over in 2026The story behind NSBWEP and why community is the real legacyWhere the industry is heading by 2029 (and the trend most vendors are sleeping on) If you are an event business owner who has been quietly wondering if the way you have been running things still works, this conversation is for you. You are not alone in this. About Tara: Tara Melvin is the founder and principal planner of Signature Concepts, L.L.C. (formerly Perfect Planning Events), the founder and president of the National Society of Black Wedding and Event Professionals (NSBWEP), the founder of The Signature CEO Conference, and the creator of The Executive Mentor Program. She has been recognized as a BizBash Industry Innovator (2022) and one of BizBash's Top 500 Most Influential Event Professionals (2020 to 2021). Find Tara: Signature Concepts: signatureconceptsllc.com NSBWEP: nsbwep.com The Signature CEO Conference: thesignatureceo.com Instagram: @signatureconceptsllc | @nsbwep | @signatureceo About HFE: Hustle Free Entrepreneur is hosted by Jese Gary, founder of GEA Systems Studio and LuxeGiving. The real, behind-the-scenes conversation about running an event industry business. New episodes weekly. Free for you: If you are an event- or service-based business owner who needs the actual systems running behind the business you show on Instagram, grab The Complete Business System Stack at https://geasystemstudios.myflodesk.com/stack. It is the same map I walk paying clients through. 🎙 Thanks for tuning in to the Hustle Free Entrepreneur Podcast! If you enjoyed this episode, don’t forget to:  ✅ Subscribe so you never miss an update  ✅ Leave a review—it helps us reach more entrepreneurs like you!  ✅ Share this episode with a fellow business owner who needs it 🚀 Ready to streamline your business and ditch the hustle? Grab my free resources at https://stan.store/greeneyedambition. 📲 Let’s Connect! 📌 Instagram: @greeneyedambition 📌 Website: greeneyedambition.com Until next time, keep building smarter—not harder!

  3. May 13

    The Festival Staffing Problem Nobody's Saying Out Loud

    Send us Fan Mail  How to run festivals, community events, and event production successfully? Don't fall victim to running your business with a system held together by spreadsheets, QuickBooks, Google Forms, and a prayer. This week, I'm back with Cat McDevitt, from Eventeny, and we got into the festival operations conversation I've been wanting to have. Not the highlight reel. The real picture — the Frankenstein systems, the volunteer data that will shock you, the vendors who are quietly deciding you're a reputational risk, and what the festivals that are actually winning are doing differently. If you organize festivals, produce community events, or have ever thought about scaling into that space — this one is for you. ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ RESOURCES + LINKS ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ → Check out Eventeny (affiliate link): https://meetings.hubspot.com/cat-mcde... → Book a free demo with Eventeny: https://meetings.hubspot.com/cat-mcde... → Follow Eventeny on Instagram: @eventeny → Grab Jese's free After-Yes Checklist: https://chipper-creator-3415.kit.com/... ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ ABOUT CAT MCDEVITT ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Cat McDevitt is the CMO at Eventeny — an all-in-one event management platform built for festival and large-scale event organizers. She works daily with producers running community festivals, music festivals, fandom conventions, farmers markets, and more, and has a front-row seat to what's working (and what's quietly breaking) in the festival industry right now. 🔗 Want a free business system audit? Let’s identify the gaps and opportunities in your event business → https://businessconsultantcompany2491... 🔗 Work with GEA Systems Studio to build your systems + automations → https://businessconsultantcompany2491... 🔗 🎧 Listen to more episodes of the Hustle Free Entrepreneur Podcast →  🎙 Thanks for tuning in to the Hustle Free Entrepreneur Podcast! If you enjoyed this episode, don’t forget to:  ✅ Subscribe so you never miss an update  ✅ Leave a review—it helps us reach more entrepreneurs like you!  ✅ Share this episode with a fellow business owner who needs it 🚀 Ready to streamline your business and ditch the hustle? Grab my free resources at https://stan.store/greeneyedambition. 📲 Let’s Connect! 📌 Instagram: @greeneyedambition 📌 Website: greeneyedambition.com Until next time, keep building smarter—not harder!

  4. Apr 29

    After 10 Years in Business, This Is What I'd Automate First

    Send us Fan Mail If you've been running your event business on sticky notes, mental checklists, and willpower — this episode is for you. In this solo episode of Hustle Free Entrepreneur, Jese Gary breaks down how to actually use automation in your event business without sounding like a robot or losing the personal touch your clients pay you for. This isn't a software pitch. It's an honest conversation about why so many event pros are stuck doing manual work that's quietly costing them clients, sleep, and revenue — and the simple, sustainable way to start automating one workflow at a time. In this episode, Jese covers: - The real reason your event business feels chaotic (and it's not because you need more clients) - How to identify the most time-consuming and error-prone tasks in your business - A strategic approach to choosing automation tools without wasting money on subscriptions - The 90-day rule for testing any new platform before you commit If you've been afraid that automating your business means losing the high-touch, white-glove experience your clients love, this conversation will change the way you think about technology in your business. CHAPTERS 00:00 Overcoming Business Stress and Mistakes 02:59 The Power of Automation in Business 07:30 Identifying Pain Points and Streamlining Processes 11:14 Embracing Technology for Efficiency 16:01 Implementing Automation Effectively 20:43 Learning and Adapting to New Tools 24:12 Creating a Better Client Experience ----------------------------------------------------- 🎁 GRAB THE FREE AFTER-YES CHECKLIST The exact post-booking checklist Jese uses to onboard new event clients without dropping the ball: https://chipper-creator-3415.kit.com/afteryes ----------------------------------------------------- 📲 CONNECT WITH JESE Website: www.greeneyedambition.com Instagram: gea_systems_studio TikTok: @greeneyedambition ----------------------------------------------------- 🎧 SUBSCRIBE TO HUSTLE FREE ENTREPRENEUR Apple Podcasts: https://www.buzzsprout.com/2449235 ----------------------------------------------------- ABOUT HUSTLE FREE ENTREPRENEUR Hustle Free Entrepreneur is the podcast for event-industry business owners who are making money but drowning in the manual work of running their businesses. Hosted by Jese Gary, CEO of GEA Systems Studio and LuxeGiving. HFE is where the real, honest, behind-the-scenes conversations happen about building a profitable event business without burning out. #HustleFreeEntrepreneur #EventIndustry #EventBusinessOwner #BusinessAutomation #ServiceBasedBusiness #WeddingPlanner #EventPlanner  🎙 Thanks for tuning in to the Hustle Free Entrepreneur Podcast! If you enjoyed this episode, don’t forget to:  ✅ Subscribe so you never miss an update  ✅ Leave a review—it helps us reach more entrepreneurs like you!  ✅ Share this episode with a fellow business owner who needs it 🚀 Ready to streamline your business and ditch the hustle? Grab my free resources at https://stan.store/greeneyedambition. 📲 Let’s Connect! 📌 Instagram: @greeneyedambition 📌 Website: greeneyedambition.com Until next time, keep building smarter—not harder!

  5. Apr 18

    When Your Business Model Stops Working (And What to Do)

    Send us Fan Mail The event industry is shifting — and if your business looks exactly the same as it did two years ago, that might not be stability. It might be a warning sign. In this solo episode, Jese breaks down what she's seeing across the event industry right now: changing client behavior, unpredictable booking cycles, tighter budgets, and a market that's rewarding different things than it used to. She walks through three strategic ways to pivot your business when you see the signs of change — without blowing everything up or starting from scratch. In this episode, you'll hear: The specific shifts happening in how event clients buy, book, and spendWhy pivoting your audience might be the most powerful (and most overlooked) move you can makeHow changing your positioning — not your service — can transform your inquiry rate overnightWhen it might be time to ask the hard question: is this even the right business model for where I'm going?The difference between a panic move and a strategic pivotThis one is for every event pro who's been feeling the shift but hasn't known what to do about it. About Hustle Free Entrepreneur: Real conversations for event industry business owners who are making money but want more freedom. Hosted by Jese Gary, CEO of GEA Systems Studio and LuxeGiving. New episodes every week. Links: Free After-Yes Checklist: https://chipper-creator-3415.kit.com/afteryes 🎙 Thanks for tuning in to the Hustle Free Entrepreneur Podcast! If you enjoyed this episode, don’t forget to:  ✅ Subscribe so you never miss an update  ✅ Leave a review—it helps us reach more entrepreneurs like you!  ✅ Share this episode with a fellow business owner who needs it 🚀 Ready to streamline your business and ditch the hustle? Grab my free resources at https://stan.store/greeneyedambition. 📲 Let’s Connect! 📌 Instagram: @greeneyedambition 📌 Website: greeneyedambition.com Until next time, keep building smarter—not harder!

  6. Apr 1

    I Almost Quit My Business… Here’s What I’m Doing Instead

    Send us Fan Mail Struggling with burnout or thinking about pivoting your business? Most entrepreneurs are secretly stuck in a business cycle they no longer love — and don’t even realize it. I open up about my raw, honest journey through burnout, tough decisions, and the redefinition of success in her 15-year event business.  In this episode, let's break down how to make smart, sustainable shifts without losing everything you’ve built. If you’ve been feeling overwhelmed, stuck, or questioning your next move as an entrepreneur, this episode is for you.  I share a real and honest look at the ups and downs of entrepreneurship—from navigating burnout to making tough decisions about pivoting your business. This isn’t about quitting… It’s about evolving with purpose. You’ll discover: How to recognize burnout before it breaks your businessWhen it’s time to pivot vs. push throughHow to build a more sustainable business modelThe role of self-awareness in leadership and growthPractical ways to implement new strategies without chaosThis isn’t just another “success story” — it’s a blueprint for redefining what sustainable entrepreneurship truly looks like.  You’ll hear how life changes, industry shifts, and personal growth all play a role in building a business that actually works for you—not one that drains you. If you’ve ever wondered how to step back, reassess your strategy, and move forward with clarity, this episode gives you the framework to do just that. 🎯 Ready to simplify and scale your business? → Need help setting up systems that support your next pivot? Learn more about GEA Systems Studio: https://stan.store/greeneyedambition 🛠 Tools to support your business: → HoneyBook (CRM + client management): http://share.honeybook.com/greeneyedambition → ConvertKit (email marketing): https://partners.convertkit.com/wlu5gufp2imm #EventBusiness #Entrepreneurship #BusinessGrowth #BurnoutRecovery #HustleFreeEntrepreneur #SmallBusinessTips #BusinessStrategy 🎙 Thanks for tuning in to the Hustle Free Entrepreneur Podcast! If you enjoyed this episode, don’t forget to:  ✅ Subscribe so you never miss an update  ✅ Leave a review—it helps us reach more entrepreneurs like you!  ✅ Share this episode with a fellow business owner who needs it 🚀 Ready to streamline your business and ditch the hustle? Grab my free resources at https://stan.store/greeneyedambition. 📲 Let’s Connect! 📌 Instagram: @greeneyedambition 📌 Website: greeneyedambition.com Until next time, keep building smarter—not harder!

  7. Mar 23

    I’m 40 With Nothing Saved — Where Do I Start? (Financial Reset for Beginners)

    Send us Fan Mail Struggling with saving for retirement at 40 with no savings? You’re not alone—and it’s not too late to start over. In this episode, we break down exactly where to start if you feel financially behind and want a fresh start after 40. If you’ve been asking yourself, “Did I miss my chance?” or “How do I even begin saving for retirement?”—this conversation with Rosie Acosta is for you. We talk about starting over after financial setbacks, letting go of shame, and creating a simple, realistic plan that actually works in midlife. You’ll learn how to build financial security step by step, even if you’re starting from zero. This episode is a reminder that you are not behind—you’re just getting started. Whether you’ve experienced divorce, career gaps, or inconsistent income, there is still time to create safety, stability, and peace with your money. Rosie shares practical strategies like the “three buckets” method (emergency, mid-term, retirement), how to shift out of scarcity thinking, and why paying yourself first is the key to long-term change. This isn’t about getting rich—it’s about finally feeling secure. ✨ You are not alone in this—and your next chapter can look different. 👇 Let’s talk about it: Comment below—where are you right now in your retirement savings journey? 📥 Ready to take your first step? Start tracking your money with this simple Etsy budget tool: https://creatorlink.shop/458XPSj 📚 Resources mentioned: Crema Financial I Will Teach You To Be Rich by Ramit Sethi 💛 Join a community of women redefining life after 40: Subscribe for more conversations on money, mindset, and starting over with confidence. 🎙 Thanks for tuning in to the Hustle Free Entrepreneur Podcast! If you enjoyed this episode, don’t forget to:  ✅ Subscribe so you never miss an update  ✅ Leave a review—it helps us reach more entrepreneurs like you!  ✅ Share this episode with a fellow business owner who needs it 🚀 Ready to streamline your business and ditch the hustle? Grab my free resources at https://stan.store/greeneyedambition. 📲 Let’s Connect! 📌 Instagram: @greeneyedambition 📌 Website: greeneyedambition.com Until next time, keep building smarter—not harder!

  8. Mar 18

    Event Planners: Are You Actually Profitable? The Numbers Most People Ignore

    Send us Fan Mail Struggling to figure out how profitable an event business really is? In this episode, we break down the real numbers behind running an event planning business—so you can stop being busy and start being profitable. Running an event business can look exciting from the outside, but many planners, venues, and event pros discover that revenue does not always equal profit. In this episode of the Hustle Free Entrepreneur Podcast, Jese Lewing Gary breaks down the financial side of the event industry and shares the real truth about profitability. If you've ever asked yourself questions like “Am I charging enough?”, “Where is my money actually going?”, or “Why am I so busy but not making the profit I expected?”—this episode will help you rethink how you price, track costs, and build a more sustainable event business. This conversation is especially helpful for event planners, venues, caterers, rental companies, and creative event professionals who want to build a business that generates real income, not just a full calendar. 🎙 Thanks for tuning in to the Hustle Free Entrepreneur Podcast! If you enjoyed this episode, don’t forget to:  ✅ Subscribe so you never miss an update  ✅ Leave a review—it helps us reach more entrepreneurs like you!  ✅ Share this episode with a fellow business owner who needs it 🚀 Ready to streamline your business and ditch the hustle? Grab my free resources at https://stan.store/greeneyedambition. 📲 Let’s Connect! 📌 Instagram: @greeneyedambition 📌 Website: greeneyedambition.com Until next time, keep building smarter—not harder!

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5
out of 5
2 Ratings

About

Welcome to The Hustle-Free Entrepreneur, the go-to podcast for event industry professionals and service-based business owners ready to ditch the hustle mindset and build sustainable, efficient businesses. Join us as we pull back the curtain on the unsexy side of entrepreneurship—think systems, processes, and back-office strategies that move the needle. Through expert interviews, actionable tips, and candid conversations, you’ll learn how to master running your business to focus on growth, profits, and living life on your terms. Whether you’re an event planner, venue owner, caterer, or solopreneur in any service-based field, this podcast is your ultimate resource for business success.Subscribe now to uncover strategies to help you scale smarter, not harder.

Information

  • Creator
    Jese Gary
  • Years Active
    2025 - 2026
  • Episodes
    59
  • Rating
    Clean
  • Copyright
    © 2026 Hustle-Free Entrepreneur
  • Show Website
    Hustle-Free Entrepreneur