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Hustle-Free Entrepreneur

Jese Gary
Automation
Event Industry
Artificial Intelligence
Leadership
Hospitality
Event Planning
Honeybook
Pricing
Burnout
Profit Margin
Tariffs
Corporate Events
Retirement Savings
Budgeting
Profitability
Profitability In Events
Hybrid Events
Hustle Culture
Delegation
Brazil

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, a... more

PublishesTwice monthlyEpisodes58Foundeda year ago
Number of ListenersCategories
EntrepreneurshipBusiness

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Artwork for Hustle-Free Entrepreneur

Latest Episodes

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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 ... more

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 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 Ca... more

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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 e... more

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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 even... more

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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, to... more

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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... more

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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 ... more

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 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 y... more

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Recent Guests

Tara Melvin
Wedding planner with Signature Concepts; founder of NSBWEP; organizer of the Signature CEO Conference
Signature Concepts; National Society of Black Wedding and Event Professionals (NSBWEP)
Episode: After 20 Years in Weddings, Here's What's Really Changing
Rosie Acosta
Guest, financial literacy advocate and coach featured on Life Over 40
Episode: I’m 40 With Nothing Saved — Where Do I Start? (Financial Reset for Beginners)
Esosa Ighodaro Johnson
Marketing and brand strategist who helps businesses design experiences that generate revenue
AcceleratorCon; Black Women Talk Tech
Episode: How to Host a Profitable Retreat or Conference (Without Burning Out)
Logan Clements
Freelance event producer and show caller
Logan Strategy Group
Episode: What Corporate Event Producers Do Differently (And Why Small Event Businesses Burn Out)
Melissa Fackler
Hospitality-leadership coach and consultant
One TEAM Partners
Episode: The Guide To Leadership To Reclaim Energy and Build Sustainable Habits
Benedicte Muya
Charcuterie cart entrepreneur; founder of Nibble and Nest
Nibble and Nest
Episode: How a Mobile Charcuterie Cart Owner Built a Premium Event Brand Outside the U.S.
Kaylon Beck
Founder of Beck and Call (corporate event agency)
Beck and Call Events / Beck and Call Hospitality
Episode: How to Get Corporate Clients in 2025: Event Pros Need This Strategy
Care Allen
Decor/venue entrepreneur and pricing expert
All-In Event Space, Care Monique Decor
Episode: Profitable Event Pricing vs. The Trap Most Planners Fall Into
Tiffany Green
Experienced event professional focused on brand and event marketing, with a background across multiple sectors.
Episode: How to Build a Successful Event Management Business

Host

Jesse
Host focused on systems and back-office strategies for event pros; often discusses automation, pricing, and profitability.

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Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)Hala Taha | Entrepreneurship, Sales, Marketing | YAP Media Network
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The Money MondaysDan Fleyshman
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The Code To WinningKagiso Dikane

Talking Points

Recent interactions between the hosts and their guests.

Why Women in Business Excel: Leadership Lessons from Dallas Lombardi
Q: How has the pandemic shifted leadership and work environments in hospitality?
The pandemic prompted a rethink of retention and culture; leaders realized the need for environments that attract and keep talent, reducing burnout, and valuing humane, sustainable practices over hyper-pressurized norms.
Why Women in Business Excel: Leadership Lessons from Dallas Lombardi
Q: How did Dallas realize the importance of leadership development early on, and what changed as she grew?
Dallas describes growing into leadership by starting young, learning to listen, and balancing compassion with accountability; she emphasizes authenticity, emotional intelligence, and setting boundaries to maintain authority while staying true to her style.
Why Women in Business Excel: Leadership Lessons from Dallas Lombardi
Q: What is one of the main routes to the experience of poor leadership in hospitality?
Leadership often suffers when leaders come in with rigid, ego-driven approaches and fail to understand the positions their teams hold; compassionate leadership rooted in empathy and understanding can prevent misalignment and improve outcomes.
The Hospitality Industry Is Broken—Here’s the Mindset Shift That Will Fix It
Q: What is the core shift leaders in hospitality need to make to address the current burnout and turnover trend?
Focus on human capital and culture first—invest in leadership development, empathy, and clear, transparent communication; create a workplace where people want to come to work, not just feel obligated to.
Balancing a 9–5 and Building a Sustainable Event Business
Q: What advice would you give to someone who's scared to even start their event business because they're feeling like they're too busy?
Acknowledge the feelings of being overwhelmed, but start small with a niche or a low-risk entry point (like dessert tables or a mobile lemonade stand) to gain experience, build credibility, and gradually connect with planners. Focus on getting a few consistent, manageable steps done each week, such as networking, refining a workflow, and delivering reliable service, which over time compounds into bigger opportunities.

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Frequently Asked Questions About Hustle-Free Entrepreneur

What is Hustle-Free Entrepreneur about and what kind of topics does it cover?

Episodes center on turning event-world hustle into sustainable systems, pricing discipline, and scalable back-office practices. Conversations span profitability, automation, pricing, and client management for event pros, with frequent emphasis on leveraging technology (CRM tools, data analytics, vendor management) to reduce burnout and improve margins. Guests typically bring hands-on expertise across weddings, corporate events, branding, signage, and experiential marketing, often sharing actionable frameworks for pricing, operational clarity, and new revenue streams like coaching, retreats, and licensing. A notable angle across episodes is leadership and business design—turning artisan or service-based skills into repeatable, scalable model... more

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Hustle-Free Entrepreneur launched a year ago and published 58 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Hustle-Free Entrepreneur?

Recent guests on Hustle-Free Entrepreneur include:

1. Tara Melvin
2. Rosie Acosta
3. Esosa Ighodaro Johnson
4. Logan Clements
5. Melissa Fackler
6. Benedicte Muya
7. Kaylon Beck
8. Care Allen

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