PODCAST · business
O'Connor Bootstrap Podcast
by Isaiah O'Connor
Helping you achieve your entrepreneurship goals
Episodes
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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…
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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...
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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…
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Remastered Series Episode 32: What Is holding you back? Victimhood
In this remastered episode, I explore victimhood as one of the biggest mindset traps holding people back. Everyone faces tough breaks or unfair situations, but how you respond is what matters most. I share personal stories, including times I fell into victim thinking and how my wife handled being...
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Remastered Series Episode 31: Americas superpower
On this Fourth of July, I take you back to early 2020 when the COVID crisis was ramping up. While the situation was uncertain, what stood out to me was how quickly American factories retooled, entrepreneurs pivoted, and small businesses stepped up to fill urgent needs. This episode reminds us…
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A Conversation with Teresa Posada
In this new episode, I sit down with Teresa Posada to explore her path from architectural drafting and Home Depot to building multiple million-dollar businesses. Teresa shares how she used seller financing and her 401k to launch her first 18,000 square foot store, eventually expanding to three...
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Remastered Series Episode 30: What Is holding you back? Pride.
In this remastered episode, I dive into the dangers of pride in leadership and business. Drawing from Good to Great, The Go-Giver, and Adam Grant’s research, I show how destructive pride, an inflated focus on self, leads to arrogance, poor teamwork, and lost opportunities. I share real examples...
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An Update
In this update episode, I explain why my podcast output has slowed down recently. I’m moving back to the United States ahead of my wife and kids to prepare for our family’s big transition. Between sorting what to sell or ship, job hunting, and finding a new place to live, my time is limited....
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Remastered Episode 29: What’s Holding You Back? Ep 1 – Fear
In this remastered episode, I begin the Holding You Back series by tackling fear, the most powerful and common thing that stops people from moving forward with their business goals. Fear is not just about danger; it often hides as self-doubt, uncertainty, or worry about what others might think. I...
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Remastered Episode 28: The "What is holding you back?" series intro.
In this remastered episode, I introduce a new series called What Is Holding You Back? This series looks at the inner obstacles that can quietly sabotage your journey into entrepreneurship. Unlike physical challenges, these internal ones like fear, perfectionism, pride, or emotional paralysis are...
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Remastered Episode 27: Have you become institutionalized?
In this remastered episode I talk about how I jumped into my business with almost no plan. I thought I knew enough with my background and some balloon skills. I learned fast that’s not enough. Bootstrapping helped me keep risk low while figuring things out step by step. I kept a side job for a...
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Remastered Episode 26: Ready FIRE aim!
By Isaiah O’Connor In this remastered episode, I share how I jumped into my business with almost no plan. I thought I knew enough with my background and some balloon skills. I learned fast that’s not enough. Bootstrapping helped me keep risk low while figuring things out step by step. I kept a…
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Remastered Series Episode 25: Typecasting yourself
In this remastered episode, I talk about how we can typecast ourselves without even realizing it. I used to think typecasting was always a bad thing, but I have learned it depends on whether you can become passionate about that role. I share how this idea has shaped my career and how it might…
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Putting the Cart Before the Horse: Market First, Build Later?
We’ve all seen it. Products are rushed to market before they're ready. I break down two classic failures: Segway and Zune. Using the Go-Giver framework, I explore what happens when marketing runs ahead of real value. I walk through the good, the bad, and the ugly of launching too soon. I share...
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Remastered Episode: 24 Jack Of All Trades
In this remastered episode, we unpack the reality of being a solo entrepreneur. Juggling marketing, accounting, design, and everything else. Perfection isn’t required. Progress is. This episode will encourage you to embrace your learning curve, build the key skills needed to keep your business...
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Remastered Episode 23: Talentless
In this remastered episode, I explore the idea that talent isn't just something you are born with. It's something you can build. Drawing from the story of the Polgár sisters and their father's bold educational experiment, I show how passion, practice, and perseverance can outpace natural ability....
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Remastered Episode 22: Deconstructing Passion
In this remastered episode, Mike Rowe once said not to follow your passion, but to bring it with you. That challenged something I had written earlier: “What am I passionate about?” Or “What can I become passionate about?” — Isaiah O'Connor That second question—"what can I become passionate...
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Remastered Episode 21: Stop Marketing
In this remastered episode, I explain why you need to stop marketing your product or service and instead focus on marketing the emotion it creates. As Jim Klein from NASP explains, “People buy products or services based on emotional needs or wants, and then justify their purchase logically.”…
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Revisiting Required Secondary Powers: Discipline
In this episode, I’m revisiting the Required Secondary Powers series and focusing on discipline. It’s not the exciting part of business, but it’s what actually keeps you going. Whether you're building balloon art or coaching clients, showing up consistently matters more than talent alone. I’ll...
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Remastered Episode 20: Endgame gamble or investment
n this remastered episode, I explore whether Marvel’s Avengers Endgame was a bold gamble or a smart investment. With over $2.7 billion earned at the box office, it’s easy to say it paid off—but that didn’t happen by luck. Marvel started small with Iron Man and built momentum over a decade, taking...
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Remastered Episode 19: Endgame And Story
In this episode, I break down how Marvel’s success with Avengers: Endgame is rooted in their mastery of storytelling. A solid narrative is essential, not just in films, but in business too. When you share a compelling story about your product or service, you create a bond with your audience that...
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Remastered Episode 18: Endgame and Value
In this remastered episode, I dive into how Marvel Studios created massive value over 11 years with Avengers: Endgame. By delivering consistent quality, building a loyal fanbase, and offering a long-term payoff, Marvel turned a series of movies into one of the most valuable franchises of all…
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Remastered Episode 17: The Struggle Of Pricing
In this remastered episode, I unpack one of the most common but challenging questions in small business: “How much should I charge?” I talk about the hidden dangers of underpricing, why just covering your costs isn’t enough, and how overhead and perceived value shape what customers are actually...
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Yet Another Required Secondary Power: Integrity
In this episode, I dive into the crucial role integrity plays in business and leadership. Using the Titan submersible disaster as a backdrop, I explore how small lapses in integrity can lead to catastrophic results. I share real-world stories, including lessons from RadioShack, and provide...
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Remastered Episode 16: Turning your hobby into a business
In this remastered episode, I unpack how you can take something you already love doing—your hobby—and turn it into a real business. Whether it's something you’ve always done for fun or a skill others admire, there’s a path forward if you treat it seriously. I walk through practical steps, mindset...
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Remastered Series Episode 15: Never Give Up
In this remastered episode, I tell the story of a man I call “Spencer”—someone born into privilege but marked by rejection, failure, and political disaster. What set him apart wasn’t perfection—it was persistence. He kept going, even when most thought he was finished. This episode is for every...
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Remastered Episode 14: Why Booostrapping
In this episode, I explore the concept of bootstrapping—building a business from scratch with minimal resources. I share my personal journey, how I started my business with just a website, a few balloons, and a lot of determination. From learning on the go to investing only earnings into growth…
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Remastered Episode 13: Is it wrong to desire wealth?
In this remastered episode, I address the important question: "Is it wrong to desire wealth?" Drawing on insights from Dave Ramsey and the Bible, I explore the nature of wealth and how it’s not the money itself, but the love of money that can lead to moral pitfalls. I discuss how wealth, when...
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Servant Leadership – What Is a Leader?
In this episode, I dive into what servant leadership really means. It’s not about holding power — it’s about serving others, earning trust, and leading with humility. I share stories from my own work life, including moments I’m proud of and mistakes I’ve learned from. Leadership isn’t about…
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Remastered Episode 12: Are You Dangerous?
Being dangerous isn’t a flaw — it’s a necessity. Like a sharp tool, entrepreneurs must be honed and ready to act with purpose, protecting what matters and pushing back against what threatens. 🎙 Thank You for Being Part of the Journey! Your support means the world to me. Join our Patreon…
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Remastered Episode 11: With Great Power Comes Great Responsibility
In this remastered episode, I explore the weight of success and the responsibility that comes with it. Inspired by Iron Man, I reflect on the influence entrepreneurs hold once they reach their goals. Whether you’re just starting or already thriving, the question is the same—how will you use your...
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Remastered Episode 10: Required Secondary Powers Discipline
In this remastered episode, I dive into the essential trait of discipline in entrepreneurship. I reflect on my experiences and share how discipline can be harder when you’re working for yourself, especially when you’re working from home. I also explore strategies for staying focused, setting...
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Remastered Episode 9: Required Secondary Powers A Teachable Spirit
In this remastered episode of my Required Secondary Powers series, I dive into the importance of having a teachable spirit. I discuss how being humble and actively pursuing knowledge—whether through books, podcasts, or conversations—helps entrepreneurs grow. Staying open to learning, even when we...
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Momentum Killers
In this episode, I dive into the hidden momentum killers that can quietly derail your progress, whether in business or life. From complacency and burnout to unexpected setbacks, I’ve experienced them all. I share my personal journey, the lessons I’ve learned, and how I’m rebuilding momentum with…
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Remastered Episode 8: Required Secondary Powers Determination
In this remastered episode of my Required Secondary Powers series, I delve into the critical role of determination in entrepreneurship. Drawing from personal experiences and historical inspiration, I discuss how making a daily choice to persist—especially during challenging times—can transform...
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Remastered Episode 7: Required Secondary Powers Intro
On today's episode, we revisit the concept of 'Required Secondary Powers,' a topic I first explored back in 2019. In this remastered version, I dive deeper into how these secondary powers are critical not only in superhero lore but also in business and personal success. For a more detailed...
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Remastered Episode 6: Bottlenecks
Have you ever been stuck in a traffic jam? A big one, like on a major highway that runs through a large city? You know, the good ones where you're parked on the highway next to the speed limit sign that mocks you with a limit of 70 miles per hour. If you make progress at all, it's only inches, or...
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Remastered Episode 5: A Giving Spirit
In today’s episode, I explore the question of who is more likely to succeed: the hard-driving individual who doesn’t mind stepping on others, or the nice guy who helps those around them? I dive into research by Professor Adam Grant, who studied this very topic and found that, while nice guys do...
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Plan Now, Panic Never: Facing Tariffs and Uncertainty
In this follow-up to my tariff episode, I break down the latest developments—including the 90-day pause on most tariffs (except China’s)—and what they mean for your business. I share how market reactions, supply chain shifts, and rising costs might affect you, and give practical, experience-based...
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Remastered Episode 4: A Life Lesson From Stan Lee
What do Stan Lee, Grandma Moses, Colonel Sanders, and Samuel L. Jackson all have in common? They didn't find their biggest success until later in life. In this episode, I’m sharing a powerful reminder that it’s never too late to change your story. Whether you're stuck in a dead-end job or feeling...
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Remastered Series 3: My Origin Story
Why call it an "Origin Story" instead of "Getting to Know Isaiah"? With this being my third episode, I felt it was the right time to share more about who I am and where I come from, but that’s not the main point. A good origin story explains the why behind the who. Welcome to another episode of…
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Remastered Episode 2: DCEU, the MCU, and Your Career
In this episode, I compare the Marvel Cinematic Universe (MCU) and the DC Extended Universe (DCEU) to highlight a powerful lesson about choosing your career. DC had the advantages, but Marvel succeeded because they followed their passion—not just the money. I’ve found the same to be true in...
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Remastered Episode 1: My Introduction
Welcome to another episode of the O’Connor Bootstrap Podcast! If you enjoyed the content, drop a comment, and don't forget to give us a 5-star rating on your preferred platform. A massive thank you to Wintergatan for providing our incredible intro/outro music at no cost. Check out their amazing...
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Tarrifs, The Good, The Bad, and The Ugly
In today’s episode, I break down the new tariffs that started this spring—taxes on goods from Canada, Mexico, and China—meant to boost U.S. industry and jobs while trimming our trade gap. I look at what happened with steel tariffs a few years back: prices spiked, then dropped, and some American...
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Creative Compensation
Compensation isn’t just wages—it’s the full package of pay, perks, and growth. In this episode, I break down creative ways small businesses can reward employees without breaking the bank. Learn from my experience running a lean, high-reward team that thrived without government mandates. Welcome…
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A Living Wage part 3 Ripple Effects
In this episode, I dive into the economic ripple effects of wage policies, examining how increased wages can impact everything from consumer prices to local economies. I also highlight the importance of market-driven wages with a deep look at how Chick-fil-A's competitive pay and employee…
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A Living Wage part 2 Other Considerations
In todays episode I dive into the often-overlooked factors that influence the concept of a living wage. I discuss how benefits, career progression, and local cost-of-living differences impact financial security beyond hourly rates. I also examine how entry-level jobs foster valuable skills and...
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A living Wage Part 1: Misconceptions
In this episode, we tackle the complex debate surrounding the living wage, shedding light on common misconceptions and revealing the realities behind wage policies. We’ll discuss California’s recent decision to set a $20 minimum wage for fast food workers, which has resulted in widespread job...
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Assertiveness: The Final Required Secondary Power (For Now)
Welcome to another episode of the O’Connor Bootstrap Podcast! If you enjoyed the content, drop a comment, and don't forget to give us a 5-star rating on your preferred platform. A massive thank you to Wintergatan for providing our incredible intro/outro music at no cost. Check out their amazing...
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Another New Secondary Power: A Giving Spirit
Welcome to another episode of the O’Connor Bootstrap Podcast! If you enjoyed the content, drop a comment, and don't forget to give us a 5-star rating on your preferred platform. A massive thank you to Wintergatan for providing our incredible intro/outro music at no cost. Check out their amazing...
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ABOUT THIS SHOW
Helping you achieve your entrepreneurship goals
HOSTED BY
Isaiah O'Connor
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Frequently Asked Questions
How many episodes does O'Connor Bootstrap Podcast have?
O'Connor Bootstrap Podcast currently has 300 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is O'Connor Bootstrap Podcast about?
Helping you achieve your entrepreneurship goals
How often does O'Connor Bootstrap Podcast release new episodes?
O'Connor Bootstrap Podcast publishes regularly with 300 episodes available. Check the episode list for the typical release schedule.
Where can I listen to O'Connor Bootstrap Podcast?
You can listen to O'Connor Bootstrap Podcast on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts O'Connor Bootstrap Podcast?
O'Connor Bootstrap Podcast is created and hosted by Isaiah O'Connor.
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