July 16, 2025
First Fair Success: Business Challenges and Family Memories
Resilient optimism isn't just a trendy concept—it's the beating heart of entrepreneurship. After exploring this powerful mindset last week, we immediately faced the perfect opportunity to put it into practice at our first fair of the season. The results? A much-needed victory that confirmed we're trending in the right direction after a challenging start to the year. Every single day of our four-day event outperformed its counterpart from last year, and our brand-new "Midnight Hammer" t...
Resilient optimism isn't just a trendy concept—it's the beating heart of entrepreneurship. After exploring this powerful mindset last week, we immediately faced the perfect opportunity to put it into practice at our first fair of the season.
The results? A much-needed victory that confirmed we're trending in the right direction after a challenging start to the year. Every single day of our four-day event outperformed its counterpart from last year, and our brand-new "Midnight Hammer" t-shirt design debuted with such success that people throughout the fairgrounds were stopping each other to ask where they got their shirts.
Behind this success lies the complicated reality all small business owners understand—the constant juggling of production demands, inventory management, and cash flow challenges. From the irony of needing credit card sales for next-day inventory purchases (and receiving only cash), to vehicle troubles appearing just before a major road trip, the obstacles never stop coming. What makes this journey sustainable isn't the absence of problems; it's the support system and mindset that helps us overcome them.
Perhaps the most profound aspect of this particular fair was the emotional journey it represented. Standing at the same fairgrounds where I spent my childhood watching my father and uncles race, now without them but with my own daughter experiencing it for the first time, created a powerful connection between past and present. There's something humbling about watching other families live out what was once your childhood, realizing that the people who were fixtures of that place are largely forgotten by the current generation.
Despite the challenges, we're expanding into new markets, taking risks on events outside our comfort zone, and seeing the results in growing sales figures. Most importantly, we received the best news possible—my daughter's clean bill of health from her neurologist after our frightening hospital stay months ago. This reminder of what truly matters puts all business challenges into perspective.
Want to support small businesses creating American-made products with purpose? Follow our journey, check out our designs, and remember that everyone struggles—the difference is whether you choose to go through it or grow through it.
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00:00 - Celebrating Fair Season Success
07:01 - Business Growth and New Designs
16:30 - Support Systems and Market Expansion
25:38 - Emotional Reflections at Childhood Fair
36:50 - Overcoming Obstacles and Looking Forward
41:31 - Family Health Victory and Closing
WEBVTT
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Last week on Share, the Struggle Podcast, we learned about resilient optimism.
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This week on the podcast we put that education to the test With our first fair of the season in the books and our next big challenge upon us.
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We recap it and see just how it all looks.
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Let me tell you something.
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Everybody struggles.
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The difference is some people choose to go through it and some choose to grow through it.
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The choice is completely yours.
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Which one you choose will have a very profound effect on the way you live your life.
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If you find strength in the struggle, then this podcast is for you.
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Do you have a relationship that is comfortable with uncomfortable conversations?
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Uncomfortable conversations challenge you, humble you and they build you.
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When you sprinkle a little time and distance on it, it all makes sense.
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Most disagreements, they stem from our own insecurities.
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You are right where you need to be Back on time.
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We need to back off.
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We all take on what we're behind.
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I'll take on what's behind.
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Ooh, ooh, ooh, ooh.
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What it do, what it hot Do-do-do-do.
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Good Lord, almighty, am I so excited to be back with you.
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Oh, it's true, it is damn true.
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Does my voice sound different y'all?
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Does it sound, I don't know, beat the hell in.
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In the words of a Mainer, it would sound something like this Does it sound all staved in?
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I think that's a word that I feel like we came up with here on the Northeast, staved in.
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Does that sound all staved in to you?
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Bubba?
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Tell you what I'm a dragon.
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I am dragging my clam in the sand.
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Okay, yeah, I might as well have a metal detector out here just looking for treasures and sand dollars, because I am just dragging my aetherion.
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He's just a happy little snail.
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I'm beat, all right, I'm tired as all get out, and yeah, that's about enough complaining, but I just wanted to give an explanation in case I sound a little rough to y'all, or for those of you that aren't from Maine and you're looking to learn some new words.
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We started off this week with a new word staved in that boy over there, he all staved in.
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Tell you what I'm a little tired.
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All for good reasons, though.
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All for good reasons, which we will celebrate.
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Last week, we talked about resilient optimism.
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Resilient optimism is a powerful mindset that acknowledges and accepts difficulties while maintaining a hopeful outlook and belief in one's ability to overcome challenges, the combination of optimism and resilience enabling individuals to adapt to change and recover from setbacks.
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We had an in-depth discussion about resilient optimism and how I thought I coined blind optimism as something super cool.
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But it already exists and it's actually not as cool as I thought it would be.
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But upon further research, we combined a couple of things that I really appreciate, and the first one is resiliency, and we use that to describe me, and I'm hoping we use that to describe me, and I'm hoping we use it to describe you, and I'm hoping last week's education was motivation for you, to encourage you to continue to have that positive outlook, to acknowledge and recognize setbacks and obstacles, but to continue to overcome them.
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Last week, we continued to overcome obstacles and we went to the first fair of our season and it was a success.
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Oh, look at this little baby.
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He's starting to learn how to win.
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Oh yeah, good job honey.
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Good job learning how to win.
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True story.
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True story last week's first fair of the season was exactly what the doctor ordered, we were up in sales.
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I would be willing to say that I think this is the first event of the year that we are actually up at the end of the event.
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I think everything leading up to this we've been down, but we've added new things.
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You can't really gauge the end of the event.
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I think everything leading up to this we've been down, but we've added new things.
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You can't really gauge the end result against anything else because we haven't done it before.
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But when you're talking about those events that we've continued to have in our schedule, as you get out there and start doing those, we are up for the first time this season, which is a tremendous victory for our season.
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Our net sales for the year are continuing to be up.
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It doesn't feel like it because we're taking more chances, we're investing more, we're doubling down more.
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So by doing that it might feel a little bit tighter, but I think we are approaching some real growth, I feel like.
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So I am hell-bent and determined that this season shall be our greatest sale season and we are trending in that direction.
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We are headed towards the best and all be-all results of our year, but I do think that a lot of that is because we continue to try new things to challenge us with bigger, bolder, more beautiful challenges yes, the beautiful.
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And we are on the cusp of another one of those, because tomorrow morning we will be leaving for Syracuse, new York, which we are so excited about.
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We've built this tremendous family in New York.
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Actually, little Paisley Rain's godparents live in New York.
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You guys have already heard that story so I shall not repeat all of it because you're probably tired of it.
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Yeah, we know this little guy.
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We heard it, we heard all about it, but you've heard all about it because we're excited.
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Okay, that's how this works.
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But you hear me here today sounding a little sluggish and a little tired because it's been a whirlwind and I'm recording this episode right now at about 6 AM and getting ready, waiting for a little piece of the rain to wake up, because it's daddy daughter day this morning, and then I'm going to get into full production mode and we're going to head out to Syracuse tomorrow after a quick AM appointment.
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So the weekend was a success, y'all.
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It felt good to get back into fair season and into something familiar that also comes with optimism.
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I've been doing things that are familiar that also come with some anxiety and, shall we say, a lack of respect.
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I've been doing things where I just don't feel as appreciated.
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So, rolling into the first fair of the season, being around a lot of them fair folks that we've come to know and love and appreciate some of those relationships that we've built over the years, being around all those folks enjoying ourselves with them, sharing those entrepreneur ourselves with them, sharing those entrepreneur conversations with them, and then being around all of our loving, dedicated patrons out there, those loyal, loving, loud, proud Americans swinging in having great conversations, supporting the brand and the cause and buying the product, talking podcasts, talking life, supporting family, all those things was a big just shot of optimism that we needed.
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It was that big victory on the road of failures.
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Right, it's just one of those weekends where you're like, okay, we're trending in the right direction here.
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Now what I'm going to say is this Three years ago at that fair, I had a tremendous number and I continued to grow going into that number.
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So I thought, hey, man, we are just off to new horizons here.
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And then the following year my number was cut by about 50% and then the next year it went up a little bit and we were going into this year so optimistic and feeling like you know what, we're going to crush it and I'm going to get back to that number of a few years ago.
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And I didn't get all the way back to that number.
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I really didn't get all that close to that number, but I did add a few hundred bucks over last year's event.
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So we are trending in the right direction, y'all, we are going in the right direction.
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We are going in the right direction.
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Friday night actually ended up being our best selling Friday in the history of us being at this event.
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There was not one day at the fair that I did not beat my day from the previous year.
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So Thursday, friday, saturday, sunday, we were up all four of those days and in the end of it it shakes out to being up a few bucks.
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So we'll take it.
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Y'all, we will take it.
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We're going to build off of that.
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We're going to celebrate all of that.
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But I'm also going to take a minute to really just acknowledge and appreciate all that was the weekend.
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We talk about some of the struggles and the obstacles that we go through, so I left you off last week having that discussion of being a small business owner sitting in a parking lot 90, 95 degrees, busting your ass all day, to then pack for two hours in the heat and realize you only made 40 freaking dollars at the end of the day.
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I went from that without dragging that failure to my next success Because, as we talk about, success is going from failure to failure without a loss of enthusiasm and I went into this weekend knowing we were going to do better than previous years.
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I went into this weekend knowing that this is exactly what we needed.
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So on Sunday, the wife and my mother and my father-in-law they went over and set the camper up.
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So on Sunday, the wife and my mother and my father-in-law they went over and set the camper up and I ended up going into full production mode.
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After returning from our last event and recording the podcast, I ended up just making as much stuff as I could.
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I ended up debuting a new design that I have not been able to announce online yet, and the reason why I haven't announced it online is because it was a tremendous success.
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I literally sold out of some sizings already.
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The only bummer is on my way to my next event I don't think I'm gonna have.
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Well, I there's no thinking about it.
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I know I won't have the opportunity to restock that shirt because I can't get the shipping here in time.
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So new design that I came out with it is Midnight Hammer, in honor of the B-2 mission over Iran.
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So on the front it says who says good things don't happen after midnight?
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With a big Midnight Hammer and a couple of bombs on the side of that bad boy, a couple of B-2s values.
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I've also got a nice BT bomber on the back with an American flag and the words peace through strength since 1776.
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It's on like a military coyote brown t-shirt.
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It's pretty sweet, man, I'm a big fan of it.
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It's soft, it's comfortable, it's beautiful and it's proudly made in the USA.
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Okay, and it's cool.
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I sold a bunch of those.
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Man, I had so many people come to my tent on Saturday and say, dude, I've seen more of your Midnight Hammered t-shirts out here today than like you just made that shirt, right?
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Is everybody coming in here and buying that and just putting it on?
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My wife was walking around with our One Nation shirt on and her dad and his girlfriend are walking around with Midnight Hammer shirts on and they were stopped by somebody saying they loved their shirts and Elliot was like, well, you can go buy them right over there, and he came in and bought one of each.
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So pretty, damn cool man.
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It was really cool to see people embrace the new design.
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Get out there, celebrate it, wear it.
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I will restock more of them.
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I do have enough to bring with me to Syracuse, but they're going to sell out they are going to sell out, they're going to be gone.
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Okay, this is like an infomercial right If you call and the lines are busy, just call back, all right.
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So if you're looking to buy it, we're going to redo it, we're going to bring it all back to you, but the truth is it's going to be gone, gone, gone.
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Oh, it's true, it's true, it's true.
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I don't know where that came from.
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Probably sleep deprivation is where that came from.
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So that's another little success there.
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We sent out a new T-shirt last week, a new design.
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It's selling.
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Sent out a new t-shirt last week and her design is selling tremendously this week, actually today, later today, after little Paisley Rain is with her Meemaw later on today, her Maemaw I'm going to get back into production and I'm dropping another new design.
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This one will be coming out for Syracuse, coming out for the racing crowd, the muscle car crowd.
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If you guys have been watching along, paying attention, you know that maybe a month or so ago we continued our sponsorship of KMR racing.
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We took their logo and our logo and designed them something really nice and I promised you that I would take that design and turn it into something for Loud Proud American.
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We make our own version of that design and it is here, it has arrived and it shall be done today.
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Well, that's the plan.
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That's the plan for it to be done today.
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As we talk about resilient optimism and going over obstacles and stuff, while I'm on this design discussion, I can outline another one for you that you just stick and move and overcome.
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So we end up going to the fair.
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Let's see what day is this.
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Wednesday morning.
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Wednesday morning I actually well, I printed t-shirts all evening.
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Tuesday night late into the night, close up, get a few hours sleep, come back over, get back into production.
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Wednesday morning making as much stuff as I possibly can, throwing the last few things in the bus.
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Me and my mom head out, go up to the fair, open the camper and then go over to our vendor spot, start building our display, reconnecting and catching up with everybody and putting all the new items in.
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Getting all that stuff done, I'm not sure what time we were done setting up, maybe 9 o'clock at night Somewhere around there.
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We had our display all finalized and then on Thursday we get up, go over to the fair, open things up and get things rocking and rolling.
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And we had a great Thursday, our first day of the fair Beat last year and it set us off into just that positive ball of energy, that positive ball just rolling down the hill right.
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We were just feeling, oh so nice.
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So I went into Thursday saying here's the deal I need some new stuff for Syracuse, I need to restock some things for Syracuse that are selling out, and so to do that, I need to sell some stuff.
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All right, so my philosophy was on Thursday I'm going to have a great Thursday, and usually you kind of have like a 50-50, 60-40 split where people are putting either making purchases with cash versus credit cards.
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So my assumption was I'm going to get enough credit card sales on Thursday that are going to automatically deposit overnight into my bank account that on Friday morning I can get up and, as long as I place my order before typically one o'clock, you turn on a two-day shipping scenario.
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That'll get my apparel that's in stock to me so I can restock and get things done for our next event.
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So here's the thing Thursday having a great day, super excited about the fact that I was getting a lot of cash and, as a small business owner, y'all love cash, okay, one of the biggest reasons for a small business owner to love cash is there's no processing fee on cash.
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Okay, one of the biggest reasons for a small business owner to love cash is there's no processing fee on cash.
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When I take credit cards, I'm going to lose, you know, roughly 3% in card processing fees and all those things.
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But for me, on the first day of the fair, what I needed was a little bit of credit card sales, because it would have automatically deposited into my account because I can't get to my account from where I'm at.
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So here's the thing, folks Of all the sales on our day, the day that beat the previous year, not one person paid with credit card.
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A lovely problem to have, unless you needed the money to get deposited into your account.
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You might be saying to yourself well, this is a small business owner, why is he depending on sales from one day to pay things the next day?
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He's a small business owner that is just treading water.
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Okay, times are tough.
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America Lay off of me, so I need a cash.
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It wasn't going in.
00:17:05.903 --> 00:17:08.011
I had it in my drawer but I couldn't get to the bank.
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That's when you suck up to the wife and ask her to put some funds in your bank account so you can place an order for some apparel, that when she shows up you can give her her cash back so she can put it back in the bank.
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That's one more thing that goes with owning a small business just that family commitment and sacrifice that has to be made.
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We talk about it week after week after week, but you really can't go into these things alone.
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You need a support group and thankfully, my wife and my mother have been tremendous for me to keep this rocking and rolling.
00:17:39.990 --> 00:18:01.833
So we placed an order so that I can get our new design out this week and then, ironically, on this same conversation, I go ahead and get the apparel order taken care of and then my graphics team messages me and says yeah, so your credit card declined, so we're going to hold onto your order until you get that cleared up.
00:18:01.833 --> 00:18:08.743
Well, they took my shipping charge from $16 to 60.
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And I didn't budget that on the account that I gave them, so I had to proceed to argue with them to then get that processed and put through the mail.
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So my designs arrived yesterday and my t-shirts, as luck should have it, are running late, so they should arrive today, while today just happens to be one of those days where I get up at five in the morning, I bring my mom to work.
00:18:32.883 --> 00:18:43.998
Well, today just happens to be one of those days where I get up at five in the morning, I bring my mom to work, I roll into the office, record the podcast, and then I sneak on over to the house as Paisley reigns waking up and we have breakfast, and then it's daddy-daughter time until my mama gets out of work.
00:18:43.998 --> 00:18:58.154
So my scenario for today is going to be trying to get Paisley to entertain herself long enough for me to do book work, paperwork and phone calls, which will not happen, I know that won't happen and then my mom's going to get out of work at two o'clock.
00:18:58.154 --> 00:19:05.295
I'm going to pick her up, come home and then by about three o'clock I ought to be in the office working until the sun comes up.
00:19:05.295 --> 00:19:09.039
That's pretty much how my time is going to be scheduled.
00:19:09.039 --> 00:19:12.064
Okay, that's just facts of life.
00:19:12.064 --> 00:19:13.945
That's how this is going to work.
00:19:15.451 --> 00:19:17.193
So back to the fair folks.
00:19:17.193 --> 00:19:19.740
Things went really good for us, man.
00:19:19.740 --> 00:19:21.002
We made it through.
00:19:21.002 --> 00:19:22.412
We had a successful weekend.
00:19:22.412 --> 00:19:25.240
It wasn't all that I hoped for, let's be honest.
00:19:25.240 --> 00:19:37.682
I set goals that I feel are attainable and then I set goals that I feel like are home runs and I came close to my bare minimum small goal improvement.
00:19:37.682 --> 00:19:38.343
You know what I'm saying.
00:19:38.343 --> 00:19:40.486
It was good, it was a gain, it was a win.
00:19:40.486 --> 00:19:46.420
It wasn't all that I hoped for, but I'm guessing it was all that I needed and deserved.
00:19:46.420 --> 00:19:48.316
Okay, so we made that happen.
00:19:48.316 --> 00:19:49.756
We dropped the new design.
00:19:49.756 --> 00:19:51.175
It was tremendously successful.
00:19:51.175 --> 00:19:53.718
It's got me encouraged about our next new design.
00:19:53.718 --> 00:19:54.541
It was tremendously successful.
00:19:54.541 --> 00:19:58.134
It's got me encouraged about our next new design because, as the events go, I'm trying to roll out new things.
00:19:58.855 --> 00:20:07.298
Every time I go to a new large event, I have all these designs and ideas in the pipeline and I'm trying to get them out as fast as I can afford them.
00:20:07.298 --> 00:20:09.756
So we're excited, man.
00:20:09.756 --> 00:20:11.361
Things are changing, things are moving.
00:20:11.361 --> 00:20:21.798
It's been a struggle to keep up with things, to maintain things, like I'm selling out of things and trying to reorder them in between events, and that's part of the struggle that we're talking about.
00:20:21.798 --> 00:20:26.902
Between last week, you know you're, you're running out of stuff, you're at an event and you can see it happening.
00:20:26.902 --> 00:20:33.948
You go ahead, place an order on Friday, um, and then it's going to arrive on Tuesday and you're going to leave on Wednesday.
00:20:33.948 --> 00:20:35.674
All these moving parts.
00:20:35.674 --> 00:20:38.424
That's just part of what I'm going through.
00:20:38.424 --> 00:20:39.990
That's part of what I'm growing through.
00:20:40.010 --> 00:20:46.674
We're in this growing season for the business and I know that we're off to bigger and bolder, more beautiful things.
00:20:46.674 --> 00:20:58.471
I just have to overcome these struggles and I know at the end of the season I'm going to be able to sit back and say dude, you did this, you built this, you've achieved some of the greatest year of success that you've achieved.
00:20:58.471 --> 00:21:06.894
And you had to work your ass off and do it in a whole different way and angle, but you made it and I know that's what's going to be for me.
00:21:06.894 --> 00:21:07.535
I can see it.
00:21:07.535 --> 00:21:08.395
I know it's coming.
00:21:08.395 --> 00:21:22.102
I'm just working as hard and fast as I can towards it and I get these little adrenaline boosters that kick in when you have a successful event, when you, you know, gain numbers over your previous year.
00:21:22.549 --> 00:21:28.063
You get another boost when you create a new design and it becomes super successful in your first event.
00:21:28.063 --> 00:21:35.230
You get another boost when you start reconnecting with just valued customers.
00:21:35.230 --> 00:22:05.596
When you reconnect with those loud, proud Americans that are becoming friends and family, when you get reconnected with your small business family that's on the road and you sit back and bounce ideas and stories off of each other, off of each other, you start to just build and manifest this adrenaline boost, this positive ball of optimism, and that is what really carries you into the next event, that allows you to overcome those obstacles.
00:22:05.596 --> 00:22:09.131
And that's exactly what I needed and that's exactly what this fair was about.
00:22:09.131 --> 00:22:19.314
I love going back to a fair that I grew up at and just kind of regrounding myself and getting ready for the season.
00:22:19.314 --> 00:22:23.702
So, as I was saying, number wise, great success.
00:22:23.702 --> 00:22:51.011
Connecting with customers and friends and family another great success, right, and exactly what we needed when we needed it the benefit of having a day and then sitting down with businesses that you trust and look up to, like Ledgeway Farm, and having these conversations about just how they get to where they are, what their philosophy is and where they're going.
00:22:51.112 --> 00:22:57.263
Motivation for us, brainstorming angles and events and opportunities and avenues to grow.
00:22:57.263 --> 00:23:05.564
We also uncovered another new potential event that I will be making phone calls on today to get into.
00:23:05.564 --> 00:23:20.723
Matt brought up an event to me and then he ended up working on getting me some contact info and introduced me to somebody and we're working on maybe doing something different, adding something else to the schedule this year.
00:23:20.723 --> 00:23:25.882
So hopefully next week's show, I can recap Syracuse and announce to you something new.
00:23:25.882 --> 00:23:28.376
Yet another new event for us to go to.
00:23:29.138 --> 00:23:32.779
This year that's a part of the challenges of this year.
00:23:32.779 --> 00:23:40.077
This year, that's a part of the challenges of this year we jumped just head over heels out of our comfort zone and we went to Daytona.
00:23:40.077 --> 00:23:45.392
We did Daytona Bike Week, a bucket list item and opportunity and event for our business.
00:23:45.392 --> 00:23:45.932
We did it.
00:23:45.932 --> 00:23:47.575
We went out there and did it.
00:23:47.575 --> 00:23:51.440
We are about to go to Syracuse, new York.
00:23:51.440 --> 00:24:00.539
We are leaving tomorrow for another tremendous event Out of our comfort zone, out of our wheelhouse.
00:24:00.539 --> 00:24:09.498
I am still working on being a vendor in the Catskill Mountains of New York for another motorcycle rally in September.
00:24:09.498 --> 00:24:15.459
We're also looking at another event that I just mentioned to you that will take me into a new area that I have not done.
00:24:15.459 --> 00:24:17.342
That's actually in my state.
00:24:17.342 --> 00:24:27.565
We're talking about a handful of events that are all new, that are all outside of the range in which we typically operate.
00:24:27.565 --> 00:24:52.622
Those challenges, those efforts, those risks are all part of the reason why we are having the best sale season we have ever had and it's all part of the reason why next year I'm going to remove things from my schedule that I've been doing for five years because they are not growing our business and we're going to continue to apply ourselves to new, bigger challenges to grow our business.
00:24:52.622 --> 00:24:55.090
And we're going to continue to apply ourselves to new, bigger challenges to grow our business.
00:24:56.834 --> 00:25:07.459
I have begun to learn that I need to make decisions that are right for my business, not decisions because I have friends and connections right.
00:25:07.459 --> 00:25:12.095
We often do things in life because we're just being nice.
00:25:12.095 --> 00:25:19.239
We do things in life because we don't want to disappoint, we don't want to upset, we don't want to offend people that are close to us.
00:25:19.239 --> 00:25:29.903
Oftentimes we continue to do things that don't really service us any longer, that don't benefit us any longer, because we are afraid to upset somebody close to us.
00:25:29.903 --> 00:25:33.980
We are worried we're going to ruin a relationship.
00:25:33.980 --> 00:25:49.252
Well, the truth is, the moment that you feel like you are jeopardizing a relationship because you're bettering yourself and your family and your business, then it's not a relationship worth having and that's where I've gotten to in my life.
00:25:49.252 --> 00:25:59.680
If I'm going to upset you by doing what's right for my business, my family and myself, then you are only in it for you and that's okay.
00:25:59.680 --> 00:26:04.176
But I don't need to continue to do things just to appease you.
00:26:04.176 --> 00:26:14.900
So, with that said, all these new obstacles and challenges and risks that we're taking is motivating for me to continue down this path next year and I'm excited about it.
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