O'Connor Bootstrap Podcast
Isaiah O'Connor
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Recent Episodes
S2025E34 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…
S2025E15 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…
S2025E33 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…
S2025E32 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…
S2025E31 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,…
S2025E14 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…
S2025E30 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…
S2025E13 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…
S2025E29 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…
S2025E28 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…
S2025E27 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…
S2025E26 Remastered Episode 26: Ready FIRE aim!
By Isaiah O’ConnorIn 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…
S2025E25 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…
S2025E12 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…
S2025E24 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…
S2025E23 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…
S2025E22 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…
S2025E21 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…
S2025E11 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…
S2025E20 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…
Frequently Asked Questions
O'Connor Bootstrap Podcast has published 296 episodes since April 2020, covering topics in Business, Entrepreneurship.
O'Connor Bootstrap Podcast is currently dormant with new episodes weekly. Average episode length is 19m.
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