Hustle-Free Entrepreneur

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 d...

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 re...

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...

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...

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 shi...

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...

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 epis...

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 Ighod...

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...

Send us Fan Mail Feeling burned out as a business owner or event professional? In this episode, we break down how leadership, boundaries, and sustainable habits help entrepreneurs reclaim energy without walking away from their businesses. Melissa Fackler , Small Business Operations Coach and Event Specialist at One TEAM Partners , unpacks why so many leaders in hospitality and the event industry a...

Send us Fan Mail Want to start a mobile charcuterie cart business? Did you know opportunities exist outside of the U.S. event industry? This episode will challenge how you think about mobile food businesses, branding, and standing out in an oversaturated market—by looking beyond borders. In this global conversation, I sit down with Benedicte Muya , founder of Nibble and Nest , a mobile charcuterie...

Send us Fan Mail Struggling to turn your creative talent into real profit in the event industry? In this episode, we break down how custom signage evolved into a high-value luxury service—and how event pros can use it to grow smarter, not harder. In this conversation, Jese Lewing Gary sits down with Tracey Levette Fowlkes , a custom signage expert who transformed her creative passion into a profit...

Send us Fan Mail Struggling to turn your event planning expertise into real, scalable income? We break down how event planners turn their skills into high-paying coaching and consulting without starting from scratch. In this episode of Hustle Free Entrepreneur, Jese Gary sits down with Jasmine Ruff to unpack how event professionals can monetize their expertise, step into coaching or consulting, an...

Send us Fan Mail   Struggling to keep up with inquiries, onboarding, payments, and follow-ups in your event business? In this episode, I break down the 5 automations I use to save 10+ hours every single week—without losing the personal touch your clients expect. Running an event business doesn’t mean you have to be glued to your inbox or manually chasing clients for every step. Automation isn’t ab...

Send us Fan Mail Struggling to break into corporate event planning? In this episode, we break down how event pros can land corporate clients in 2025 —without feeling overwhelmed, underqualified, or stuck in the wedding-only lane.  Corporate events can feel intimidating if you’ve built your business around weddings or social events—but they don’t have to be. In this episode of the Hustle Free Entre...

Send us Fan Mail Many event planners enter the industry fueled by passion and creativity—but without formal business training, pricing often becomes the biggest obstacle to profitability. In this conversation, host Jese Lewing Gary sits down with Care Allen, CEO of The Care Monique Design Studio and The All-En Event Space, to unpack the real reasons event pros underprice their services and how to...

Send us Fan Mail  Struggling to scale your event business without burning out? In this episode, you’ll learn the framework 6-figure event pros use to grow with systems, not stress. In this powerful conversation, Jese Gary breaks down one of the biggest lies in the event industry — that nonstop hustle equals success. Spoiler alert: it doesn’t. Being “booked and busy” can actually mask deeper issues...

Send us Fan Mail Is the hospitality industry overdue for a mindset overhaul? In this episode, we break down why resilience, adaptability, and personal growth are becoming non-negotiable for true leadership in hospitality. In this powerful conversation, Jese Lewing Gary sits down with Chef Franck Desplechin to talk about the mindset shifts that today’s hospitality leaders must embrace to thrive. Fr...

Send us Fan Mail  Struggling to keep up with the rapid changes in the event industry? In this episode, we’re breaking down the key event industry trends for 2026 and beyond—and what you need to do now to stay relevant, profitable, and ahead of your competition. ✨ What You’ll Learn: As the event industry evolves faster than ever, adaptability is the new advantage. Jese Lewing Gary unpacks the data...

Send us Fan Mail Want to know how to scale your event planning business without burning out? In this episode of the Hustle Free Entrepreneur Podcast, I share the exact systems and strategies you need to stop hustling and start scaling. Running an event business can feel overwhelming when you’re stuck doing everything manually — from chasing clients to managing endless admin. But here’s the truth:...

Send us Fan Mail Thinking about starting or growing your event management business? In this episode, we dive deep into the skills, strategies, and niches that can help you succeed in the dynamic world of event management. The event industry is so much more than weddings. In this conversation, Jese Gary and Tiffany Green explore the multifaceted world of event planning, covering everything from cer...

Send us Fan Mail Being a leader is more than managing tasks — it’s about empowering people, creating culture, and leading with compassion.  In this episode of the Hustle Free Entrepreneur Podcast, Jessie sits down with Dallas Lombardi, a powerhouse in the hospitality industry, to discuss what it truly takes to be a leader in today’s business world. From the unique challenges women in leadership fa...

Send us Fan Mail Revenue doesn’t tell the full story of your business. In this episode of the Hustle Free Entrepreneur Podcast , Jese reveals the 5 essential KPIs for business growth that every entrepreneur should track. These key performance indicators go beyond vanity metrics to show you how healthy your business really is. If you’ve been stuck in hustle culture, constantly chasing revenue witho...

Send us Fan Mail  The event industry is changing fast — and AI is leading the charge. In this episode of Hustle Free Entrepreneur, Jessie dives into how event professionals can harness the power of AI to streamline operations, wow clients, and boost profits without the stress. From AI-driven CRMs to content tools like ChatGPT, Jasper, and Canva, discover how technology is shaping the future of eve...

Send us Fan Mail In this week’s Hustle Free Headlines , host Jessie Gary breaks down the headlines every event and service industry business owner should be watching. From the skyrocketing price of coffee caused by climate change and global unrest, to the ripple effects on restaurants, cafes, and catering businesses, we’re talking real-world impacts—and how to adapt.  Discover how technology and c...