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. 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!

    47 min

  2. 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!

    27 min

  3. 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!

    22 min

  4. 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!

    22 min

  5. 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!

    48 min

  6. 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!

    39 min

  7. FEB 24

    How to Host a Profitable Retreat or Conference (Without Burning Out)

    Send us Fan Mail  Struggling to host events that actually make money? In this episode, we break down how to host retreats, conferences, and business events that turn a real profit—without burnout.  If you’ve ever wondered how to host an event for your business and actually walk away profitable, this conversation is for you.  In this episode of Hustle Free Entrepreneur, I sit down with Esosa Ighodaro, event strategist and profitability expert, to unpack the real numbers behind hosting successful events. We talk about how to host retreats, how to host conferences, and how to throw an event that supports your long-term business goals—not just your ego.  Too many event organizers measure success by applause instead of profitability. Esosa explains why understanding your true costs, revenue streams, and client education is critical to building a sustainable event-based business.  ✨ About Esosa Ighodaro Esosa Ighodaro is an event strategist who helps business owners design impactful, profitable events. She specializes in coaching entrepreneurs on financial clarity, revenue strategy, and aligning event experiences with measurable business goals. Her approach blends strategic thinking, client education, and practical financial management to help hosts increase revenue without increasing chaos.  Learn about her bootcamp where she'll walk through: ✨ Clarifying your event concept + audience ✨ Structuring it so it makes money (not just noise) ✨ Pricing, positioning, and execution without burnout ✨ How to build an event that can grow beyond a one-time moment If you’ve been sitting on an idea—or feeling stuck in execution—sign up so we can learn more about your new idea and help you shape it the right way. Register here  ✨ What You’ll Learn:  Why client satisfaction ≠ profitabilityCommon money mistakes event hosts makeHow to coach clients and set better expectationsSales strategies event organizers should focus on dailyHow to track finances to avoid burnoutRevenue streams that increase event profitThe mindset shift needed to grow as an event CEO If you’re searching for how to host your events strategically, this episode will challenge you to think bigger and smarter. Need help setting up HoneyBook, automations, or building systems that support profitable events? Explore GEA Systems Studio services: https://businessconsultantcompany24914.hbportal.co/public/HBcreation   💻 Tools We Love: HoneyBook (Client Management) – http://share.honeybook.com/greeneyedambition  🎙 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!

    1h 11m

  8. FEB 17

    What Corporate Event Producers Do Differently (And Why Small Event Businesses Burn Out)

    Send us Fan Mail  Want to learn why being corporate event producer is different? This conversation will shift how you think about event management, production, and scaling your role. If you’ve ever wondered how corporate events run so smoothly (while your calendar feels chaotic), this is the perfect episode for you.  Logan Clements, freelance event producer and show caller, pulls back the curtain on the technical side of corporate events. We talk about the difference between event management and event production, why understanding AV and run-of-show logistics is critical, and how corporate teams avoid burnout by narrowing their focus. Logan also shares how networking, volunteering, and even pursuing international events can expand your career faster than paid ads ever will. We dive into post-pandemic shifts in corporate event strategy, the role of AI in event production, and why the human element still wins every time. ✨ What You’ll Learn: The real difference between event production vs. event managementWhy corporate event producers don’t try to “do it all”How understanding AV protects your profit and reputationHow to niche down inside the event industryWhere international opportunities exist in corporate eventsWhy AI won’t replace producers—but producers who use AI will winIf you’re an event planner, venue owner, or creative feeling stretched thin—this episode will help you rethink your structure. Ready to build smarter systems in your event business? Book a strategy session to map out your operations and stop running your business in survival mode: https://businessconsultantcompany24914.hbportal.co/public/strategy Need help with HoneyBook setup, automations, or backend systems? Learn more about GEA Systems Studio here: https://businessconsultantcompany24914.hbportal.co/public/HBcreation   🎙 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!

    1h 1m
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Ratings & Reviews

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
    57
  • Rating
    Explicit
  • Copyright
    © 2026 Hustle-Free Entrepreneur
  • Show Website
    Hustle-Free Entrepreneur