Entrepreneurs: What Was Your One "What Was I Thinking?" Moment?

Episode 268 September 09, 2025 00:06:54
Entrepreneurs: What Was Your One "What Was I Thinking?" Moment?
Passage to Profit Show - Road to Entrepreneurship
Entrepreneurs: What Was Your One "What Was I Thinking?" Moment?

Sep 09 2025 | 00:06:54

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Show Notes

This segment of "Your New Business Journey" on the Passage to Profit Show dives into the hilarious, humbling, and oh-so-relatable “What Was I Thinking?” moments every entrepreneur faces. Our panel of business owners share their most surprising mistakes, from hiring mishaps to magic-bullet thinking to grand opening nightmares, and how those moments ultimately shaped them as better leaders. Whether you’re just starting your business journey or deep in the messy middle, this conversation reminds you that every misstep can be a stepping stone toward growth (and a good laugh along the way).

 

Richard Gearhart and Elizabeth Gearhart, co-hosts of Passage to Profit Show have this discussion with leadership and scaling coach Kenny Lange, Jen Rafferty from Empowered Educator and Whitney Dueñas Richardson from Global Sprouts. 

 

Whether you're a seasoned entrepreneur, a startup, an inventor, an innovator, a small business or just starting your entrepreneurial journey, tune into Passage to Profit Show for compelling discussions, real-life examples, and expert advice on entrepreneurship, intellectual property, trademarks and more. Visit https://passagetoprofitshow.com/ for the latest updates and episodes.

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Episode Transcript

[00:00:02] Speaker A: Ramping up your business. The time is near. You've given it hard, now get it in Gear. It's Passage to Profit with Richard and Elizabeth Gearhart. I'm Richard Gearhart, founder of Gearhart Law, a full service intellectual property law firm specializing in patents, trademarks and copyrights. [00:00:20] Speaker B: And I'm Elizabeth Gearhart, not an attorney, but I do marketing for Gearhart lot. And I am the founder of Gear Media Studios, a full service public podcast studio. [00:00:29] Speaker A: Welcome to Passage to Profit the Road to Entrepreneurship, where we talk with celebrities and entrepreneurs about their stories in the business world. But before we get into our interviews, it's time for your business journey. Two in five Americans want to start a business or are thinking about starting a business. And we want to ask our panel today, every entrepreneur has that one what was I thinking Moment. What was yours? Kenny Lang, welcome to the show. What was your what was I thinking. [00:00:59] Speaker C: Moment as we were talking before the show, I think most of the time I'm waking up and going, what was I thinking? But I think it was probably with my first company, I started to hire employees and was getting further away from the work. And I thought, well, I just wanted to like, pay my bills and not have people tell me what to do. And now I have clients tell me what to do. And apparently you need to lead employees well or they do bad work and will leave your company. So they also sort of needed to tell me what to do. And it made me wonder, what was I thinking? [00:01:35] Speaker A: Well, that's a pretty good one. Jen, what was your thinking moment? [00:01:39] Speaker D: I think the biggest what was I thinking Moment happens when I rely heavily on something or someone to be the magic bullet for what I'm looking for. Because the truth is, it's my company and there isn't anybody that's going to have the magic bullet. And often we look outside of ourselves to find the quick, easy answers or the quick fixes for some of these really big challenges that we have as entrepreneurs. And sometimes we just have to be comfortable in that messy middle and work through the work to get to the other side. Because what's true is there is no magic bullet. So what was I thinking? Happens once in a while when I rely too heavily on something outside of myself. [00:02:26] Speaker A: That's a great one. I'm guilty of that, too. Sometimes you just kind of want to share the responsibility of making a decision with somebody else. But when you're in business, you can share discussions, but ultimately the decisions are yours. And sometimes it's easy to kind of take a shortcut and Let somebody else do the thinking for you. But lots of times when you do that, it just doesn't work out. So point well taken. Whitney Duanes Richardson, what was your what was I thinking Moment? [00:02:57] Speaker E: I would also say, similar to Kenny, it would always be my first business. And I failed to do a background check on a contractor when I opened up my fitness studio. And she ended up getting in a lot of trouble for something. And my first thought was, what the heck was I thinking? Why did I not run a background check to eliminate this from being bad publicity? I was freshly 19, I needed some fitness instructors, and I was about to open, and I just hired who I thought was a great candidate, which ended up biting me. [00:03:31] Speaker A: That is a lesson learned. And I guess doing a background check is really important, no matter who you hire. Sometimes people just seem so great, and you get so caught up in the moment, and especially when you're starting out. I remember I was so grateful that somebody would even want to work for me, right, that it's easy to sort of cut corners if you're not careful. [00:03:56] Speaker B: Elizabeth My what was I thinking? Moment came when I thought to myself, why in the world I think it would be a good idea to open another brick and mortar business in this town because we had all our ducks in a row. We're gonna do our grand opening. Everything was set. We've been in this building for two decades, or no, 15 years. So my what was I thinking? Moment came when I realized not only I caught things in time, but it wasn't in time because the dealing with the town takes weeks and months. And anyway, we got through it, though, and the studio's running. [00:04:31] Speaker A: I remember those days. That was pretty exasperating. So it was rough, but we made it through. My what was I thinking? Moment was actually pretty embarrassing. I had hired a contractor to come and paint the second floor of our building here, and I didn't really look too closely at the thing that he wrote up. I hired him to do the job. I came upstairs, and the walls were painted, but none of the moldings or the doors or the baseboards or any of that were painting. So we painted the walls blue, but the baseboards were like this ugly brown color. And I said, well, why didn't you paint the baseboards? He said, well, you just said paint the walls. They paint the baseboards. So as an attorney, I feel like I should have done a better job with that. Fortunately, I do do a better job of reviewing client contracts, but I didn't do such a great job in that situation. And I guess the takeaway moment from this though is that obviously anybody who's running a business is going to have and what was I thinking moment. And in the same club as Kenny where I have those moments multiple times during the week. But fortunately, usually you can adjust and you can get on with your business. So Passage to Profit is a nationally syndicated radio show appearing in 38 markets across the United States. In addition, Passage to Profit has also been recently selected by Feedspot Podcasters Database as a top 10 entrepreneur interview podcast. Thank you to the P2P team, our producer Noah Fleishman and our program coordinator Alicia Morrissey, our studio assistant Risa Kat Bussari and our social media powerhouse Carolina Tabares. Look for our podcast tomorrow. Anywhere you get your podcasts, our podcast is ranked in the top 3% globally. You can also find us on Facebook, Instagram X and on our YouTube channel. And remember, while the information on this program is below believed to be correct, never take a legal step without checking with your legal professional first. Gearhart Law is here for your patent, trademark and copyright needs. You can find [email protected] and contact us for a free consultation. Take care everybody. Thanks for listening and we'll be back next week.

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