Remastered Series Episode 34: What's holding you back? Comfort
In this remastered episode, I explore a risk most people don’t notice: the risk of being too comfortable. Comfort isn’t bad. It feels good and gives us a sense of stability, but it can easily lead to laziness and complacency. I discuss how being too comfortable in your career, business, or personal life can prevent growth and leave you unprepared for sudden changes.
I share personal stories, including my experience in volunteer work and running my business during challenging times like COVID-19. I talk about how hardship can push you to innovate and grow, why planning for the unexpected is crucial, and simple ways to step out of your comfort zone to stay productive, creative, and moving forward.
4 Aug 2025
Moving Chaos
In this episode, I give a quick update on why there hasn’t been an episode in the last couple of weeks. I was out of town and made the mistake of leaving my pre-recorded episode on the wrong hard drive.
Since getting back, it has been nothing but moving chaos. We are preparing to move back to the States, cleaning out the house, selling items at garage sales and flea markets, and temporarily staying with family. I share when I expect things to calm down and when regular uploads will resume.
18 Jul 2025
Remastered Series Episode 33: What’s Holding You Back – Entitlement
In this remastered episode, I talk about how a sense of entitlement can block you from the success you're capable of achieving. Whether it's feeling like you're owed something because of your background, your pain, or your family ties, this mindset can creep in and create mental roadblocks. I share the classic story of the grasshopper and the ants to show how this attitude plays out.
You'll also hear why real growth comes when you trade entitlement for gratitude and a giving mindset. I reference ideas from Good to Great and The Go-Giver to show how humility and generosity, not demands, unlock long-term success in both life and business.
Who has been a guest on O'Connor Bootstrap Podcast
Names identified in recent episode analyses. Showing up to five guests.
Teresa Posada
John David Mann
Diana Habovstak
Rabbi Daniel Lapin
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
555,317,277
Score snapshot 15 Sept 2025
Apple Podcasts (US)
5.0 / 5
3 ratings
Spotify
2.3 / 5
3 ratings
Podcast Authority Score: 69 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
90
Social presence
0
YouTube
93
Engagement
31
Contact O'Connor Bootstrap Podcast
Guest appearances
Does not typically book guests
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