Episode Details
December 24, 2025
20 minutes
In Episode 43 of the Never in Reverse Podcast, host Jeremy Axel and co-host Douglas Cox candidly discuss the hidden struggles entrepreneurs face during the holiday season.
They explore the pressure to always be available, the guilt of missing family moments, and the loneliness that can come with being a provider.
The conversation highlights the challenge of balancing business demands with personal well-being and family time. Both hosts share personal stories, emphasize the importance of setting boundaries, and encourage listeners to prioritize meaningful moments with loved ones.
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Episode Transcript And Overview
Timeline Notes
The Hidden Struggles of Entrepreneurs During the Holidays Discussing the unseen challenges, guilt, and loneliness that business owners face while others enjoy holiday festivities.
The Holiday Grind and Always Being "On." Exploring the difficulty of unplugging from work and the habitual nature of always being available.
Pressure to Respond and FOMO in Business Examining the pressure to respond quickly to customers and the fear of missing out on opportunities.
Work-Life Balance and Cultural Expectations Debating the reality of work-life balance, societal pressures, and the need to unplug for mental health.
The Pendulum of Priorities and Entrepreneurial Expectations Discussing shifting priorities between work and family, and the myth of entrepreneurial freedom.
Self-Imposed Pressures and the Founder’s Trap Addressing internal and external expectations, as well as the emotional traps founders often encounter.
The Importance of Presence and Family Moments Sharing personal stories about choosing family time over work, and the value of being present.
Setting Boundaries and Personal Time Emphasizing the need for boundaries, personal time, and self-care to avoid burnout.
he Provider Mentality and Loneliness Exploring the loneliness and sacrifices of being a provider, and the importance of keeping something for oneself.
Holiday Pressures and Family Dynamics Discussing financial and emotional pressures during the holidays and the complexities of family relationships.
Final Thoughts and Advice for the Holidays Encouraging listeners to set boundaries, breathe, and accept the imperfect nature of the holiday season.
Notable Guests
Bill Fairman
Fund Manager, Private Lender
Bill Fairman
Fund Manager, Private Lender
A best-selling author, national speaker, and serial entrepreneur with 30+ years of experience in mortgage banking.
Over the years, Bill has worked closely with hundreds of high-net-worth individuals, helping them strategically grow wealth as a Fund Manager for more than 13 years.
He’s also a trusted voice in the industry, serving on the Government Relations Committee of the American Association of Private Lenders.
Nick Kiridzic
Founder and CEO
Nick Kiridzic
Founder and CEO
I'm the founder of StaffHero, where we help growing businesses scale without the chaos connecting them with skilled remote assistants and automation systems that save time and cut costs.Before this, I spent over ten years in healthcare and business development, constantly spotting the same problem: amazing teams burning out under the weight of busywork. That’s what pushed me to build StaffHero.
Now, I focus on helping business owners get their time back and build systems that let them grow with freedom and focus.
Paul Glover
The No B.S. Executive Coach
Paul Glover
The No B.S. Executive Coach
Paul Glover is No B.S. Executive Coach, whose mission is to Challenge the Best to Become Better.
He is also:
• An Ex- White-Collar Felon.
• A “Recovering” Federal Trial Lawyer.
• A Subject Mater Expert on failing and recovery.
• Who is a TEDx speaker, Vintage Speaker, Forbes contributor, and an author whose book, WorkQuake™, is endorsed by Marshall Goldsmith, a Top 10 Business Thinker.
• An Executive Coach With 30 years of experience who advises and coaches executives in organizations with up to $1 billion in annual revenue.
• A Starbucks addict, and
• A Chicago Bears fanatic.
Adi Klevit
Founder | CEO
Adi Klevit
Founder | CEO
Adi Klevit is the Founder of Business Success Consulting Group and the host of the Systems Simplified podcast. With nearly three decades of experience as an industrial engineer and process consultant, she has helped hundreds of growth-focused companies systematize their operations to scale successfully.
Known as “The Process Guru,” Adi specializes in designing and implementing turnkey systems that reduce dependence on the owner, empower teams, and increase profitability. Her clients range from fast-growing trades businesses to multi-location professional service firms, and she is a trusted advisor to CEOs across the U.S.
Joe Dillon
Divorce Mediator & Founder
Joe Dillon
Divorce Mediator & Founder
Joe is a pioneer in divorce mediation who has been helping couples navigate the end of their marriages with dignity and financial wisdom for over 17 years. As co-founder of Equitable Mediation Services, Joe combines his MBA in Finance with specialized training from Harvard, MIT, and Northwestern University to guide couples toward agreements that protect both their emotional wellbeing and financial futures.
Joe pioneered virtual divorce mediation in 2011, nearly a decade before others adopted online practices during the pandemic. His results speak for themselves: Equitable Mediation Services maintains a 98% case resolution rate, significantly higher than the industry average of 70%.
