Aug. 20, 2025
The Courage To Take One More Step
Ever feel like you're putting everything into your business only to fall short of expectations? That's exactly where I found myself at the Skowhegan Fair this year. After days of watching people walk past my booth, enduring stretches of 5-6 hours without a single sale, I had to make a critical mental shift that entrepreneurs rarely talk about: redefining what success looks like mid-journey. When my original sales goals became clearly unattainable, I set new targets that would still represent...
Ever feel like you're putting everything into your business only to fall short of expectations? That's exactly where I found myself at the Skowhegan Fair this year. After days of watching people walk past my booth, enduring stretches of 5-6 hours without a single sale, I had to make a critical mental shift that entrepreneurs rarely talk about: redefining what success looks like mid-journey.
When my original sales goals became clearly unattainable, I set new targets that would still represent meaningful progress rather than defeat. Fighting for every sale, I managed to hit my adjusted goal by exactly $50 in the final minutes of the fair's last day. This wasn't the triumph I'd initially imagined, but it taught me something profound about entrepreneurial resilience.
The most valuable outcome wasn't financial at all, but the people I met – particularly Isaiah, an 18-year-old with exceptional work ethic who approached business with remarkable discipline. "For every hour I spend having fun," he told me, "I'll do one thing I don't want to do to build my business." His perspective was exactly the inspiration I needed while navigating my own challenges.
As I prepare for the Windsor Fair and eventually Fryeburg (my season's biggest event), I'm facing serious inventory challenges and supplier delays. I've had to make tough decisions, including canceling a planned event to better position myself for success where it matters most. These choices reflect a maturing business perspective – understanding that courage isn't making one dramatic leap but taking consistent small steps forward despite fear and uncertainty.
If you're fighting for your own business dreams right now, remember that perseverance often looks less like heroic victories and more like quiet determination to simply take the next step. Check out our American-made products at loudproudamerican.com and share your own entrepreneurial journey with us on social media!
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00:00 - Return from Skowhegan Fair
08:19 - Sales Struggles and Competition
18:23 - Leading by Example
27:55 - Adjusting Expectations and Goals
35:24 - Meeting Isaiah: Unexpected Blessings
42:51 - Product Challenges and Tough Decisions
WEBVTT
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I am back home from the Skowhegan Fair, but it won't be long until I'm out of here again.
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But before we go, I got to let you know just how did everything go, and I want to go ahead and connect it to some inspirational advice that I heard from a friend that I'm eager to share with you.
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All.
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That and more, on today's episode of Share the Struggle Podcast.
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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 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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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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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.
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I'm leaving that world.
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The whole day gone.
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I'm running behind, I'm standing away To the back of the world.
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Good Lord, almighty, am I so excited to be with you?
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Oh, it's true, it is damn true.
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How you doing, baby boo, I missed you.
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You, I missed you.
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You know I missed you.
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Welcome back to this podcast, proudly named, precisely named, perfectly beautifully named.
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Share the struggle, because everybody struggles.
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As y'all already know, this podcast is brought to you by the fine folks over at Aloud Proud American already know this podcast is brought to you by the fine folks over the loud proud american, aka my mama and, uh, my, my baby mama and my baby and me.
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You know what I'm saying?
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Those would be the lib burr.
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T's the liberty family.
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That's right.
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We own and operate loud proud american, a lifestyle brand that produces only made in america goods for all y'all beautiful, loud, proud Americans out there.
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We know the mission at hand is to bring back American manufacturing.
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There is a great emphasis on bringing back American manufacturing and we are trying to lead the way.
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Think about that.
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Y'all Share the struggle.
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Everybody struggles.
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There's strength and truth in everybody's struggle, and the truth here, folks, is if you are willing to share the stuff that you go through, if you have the courage hint, hint, hint to share the things that you go through, that you grow through, then we all shall grow through those things together.
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Through that you grow through, then we all shall grow through those things together.
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There is strength and courage and wisdom and motivation in everybody's journey in life.
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Now, last week's show, things got emotional to end the show.
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I did not intend for them to get emotional, but they did All right, that's just the facts.
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That's just the way life is.
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We encounter things and we deliver things.
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We endure all things raw and in real time.
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Right, that's the truth about our show.
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It is a raw, real-time response to life.
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Last week I was painting the picture, a perfect little picture, of the Skowhegan Fair, loud Proud American on the road at yet another first-time event, yet another event for Loud Proud American that we have never done before Jumping into the bold waters of first-time events, getting off the old comfort couch and taking the leap of faith.
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How did it go?
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Well, I gotta to let you know.
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It is, you know, depending on fairs and events and things like that, the wild rollercoaster ride that is optimism and pessimism, pessimism, pessimism, pessimism, pessimism Sounds really funny.
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It's not.
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Pessim Sounds really funny and it's not.
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It doesn't sound right, but it's really early on a Tuesday and I haven't slept very much, so we're gonna go with Pessimism.
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Look at you, little Pessimism.
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What's wrong with you, boy?
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Boy, I'm gonna take y'all back to the woodshed and whoop your ass into shape and get you straightened out, because you'll be losing it.
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Okay, what you was trying to say, like a man, fluff up your chest there, buttercup.
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What you were trying to say is I wanted to show you the highs and lows, how things ebbs and flow, how things come and go.
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You get all geared up, you get all fired up about how great things are going to be, and then they don't end up great and then the next morning you have to freaking, wash away and wipe away the tears and fight away the anxiety and tell yourself it's going to be a great day.
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And you go out there and you struggle some more.
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That is just the peak beneath the sheets.
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That's just how things work, and they get magnified when you do things for the first time.
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And y'all have heard this broken record all damn year.
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But the reason why you've heard this broken record all year is because we're being courageous enough to jump out of our comfort zone to try new things, to do new things, to take big, bold, beautiful chances.
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That's what we've been doing.
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So last week on the show, I talked to you about how things didn't really get to going the way they had hoped that we thought they would go, or the way that we hoped they would go, the way that we envisioned them to go.
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So I took you into the deep, dark hallways of my mind, from being super excited to being let down and frustrated, but building yourself back up to being excited again to go out there and to sell and do the best you can.
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Because, as you already know, if you've been listening to me, sales is a transfer of enthusiasm.
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If you're not excited about what you're selling and what you're doing, then nobody's going to be excited about the product that you're selling, so they're probably not going to buy it from you.
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With that being said, this year has been a lot more challenging because you have to get up and sell your things a little bit differently, and I think I mentioned it last week to you guys that we had some direct competition in the same area as us that has a great sales pitch.
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Their sales pitch is a great one because it benefits the military and they can sell all these things to you.
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As far as this is where some money's going, I don't know a hard percentage of where the funds go or where they're going through some of these causes.
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I'm not making any allegations but I don't know the numbers so I can't share them with you.
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But they do different bundles and things and they have their own sales pitch.
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Right, for me it's different.
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I'm trying to pitch you on American manufacturing.
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I'm trying to pitch you on the obvious benefits of buying American right, that's my pitch, that's my sales pitch, that's my spiel.
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I'm trying to fine tune some things to set us apart a little bit.
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But one of the things I talked to you guys about last week was a direct competition.
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Being right next to us and said direct competition, the person that was representing that brand.
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They were kind of, you know, I would say, staring us down, throwing some meat mug looks from time to time.
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We're kind of competing.
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We're both competitive, right, I'm willing to say that he's working.
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We're trying to be competitive and I get that.
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But I still think that we're different and that we can support each other and there's no reason for hostility there.
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But we didn't really speak very much throughout the week and, ironically, on the last day of the fair, the representative had come in and asked me for some contact info and saying you know, I'm not going to stay here the remainder of this fair, I'm going to get out of here early and I just don't know who to talk to about it.
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And I did some research and gave them some information.
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And then later in the day, he was packing up and came over to me and said, and um.
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And then, uh, later in the day, um, he was packing up and came over to me and said hey man, um, do you have a hammer?
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Like, I have these stakes stuck in my, um, my, in my tent, and I can't get them out.
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And I was like, yeah, I can run to my bus and get them.
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And, uh, it's over in the infield here.
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So I stopped what I was doing, stopped selling, went out of my way to go get the hammer, bring it to him, leave it for him.
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And then a few minutes later, he comes over and says hey, man, I don't know what I did, but I can't get these things out there, they're stuck.
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Any chance you could help me.
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I have a bad shoulder and I stopped what I was doing.
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I went out of my way to go over and to help him and get his tent freed up and the stakes pulled and everything.
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Obviously he thanked me and was super polite, but to me it felt right to stop what I was doing and help my direct competitor, to help my biggest competition, to help somebody that really didn't associate with me, acknowledge me or talk to me, because that's who I am.
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I try to lead by example.
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I try to be an example for my daughter, for my family, for my friends, for my brand, right.
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So I didn't mind doing that one bit and I had brought that up in conversation with some friends and with my wife there.
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And my wife said you know, I think her line which I thought was pretty great was we mend crowns around here.
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We're humble enough to fix up your crown If someone's going to walk around and pretend to be better than you but they fall down, we're not afraid to pick them back up.
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I'm not saying this person fell down, I'm not saying this person did anything wrong.
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I'm just saying I thought it was quite fitting for your biggest competition to come to you and ask for help and you stop everything you're doing to help when you.
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I think if you ask yourself how many people in that situation would have just dismissed their competition and said let's watch them struggle, not us, not the way we do business, not how we do things.
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So I thought that was kind of interesting and I only brought that up because I do believe last week we talked about you know the struggle of having your competition right there next to you and I don't want anybody thinking that you know, listening to last week, listening to this week, that we're somebody that doesn't want others to do well, that we're somebody that talks negative about a patriotic brand trying to help veterans.
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I stopped everything I was doing to help the same brand.
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So I just kind of wanted to put that out there.
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I don't want anybody thinking anything negative of us.
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But I also wanted it to be a little highlight for people out there Don't be afraid to stop what you're doing to help others, even if they're your competition.
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Lead by example, be the example, right.
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I thought it was kind of fitting to share that.
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But last week when we were talking about the event and how things were going, we really weren't getting off to the start that we had hoped for, that we had dreamed of.
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But we were trying to navigate those murky waters and I mentioned to you there were some days of five, six hours without sales.
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Those days continued Mostly every day that we were open.
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It was a hurdle a, it was a, it was a hurdle man.
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It was five hours, it was six hours before selling something.
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It was a real struggle but you oftentimes would um make up for it at night.
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You would um, you know just, your numbers would get better at night.
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I think when I recorded it was a Tuesday, monday we did like a hundred dollars.
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Tuesday we more than doubled it.
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So we were going in the right direction and sales kind of trickled upward for us throughout the week.
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I will say that on Friday we did pretty good, but our best day of the entire fair was the first Friday of the fair.
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Honestly, that's kind of strange for a fair.
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Traditionally Saturdays would be your best day in general and you would assume the last couple days of the fair, especially when it's a weekend scenario, would be the best parts of the fair right.
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So I was fully expecting Friday and Saturday to dominate the previous Friday and Saturday and they didn't.
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They really didn't come out and crush things.
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But I really spent a lot of time analyzing everything, kind of thinking about what are the reasons, what are the cause, what are the effects?
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What can I be doing differently?
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What is in my control?
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You can only control the things that you can control right, like you can't worry about the things that are out of your control.
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I cannot change the forecast.
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I could not dial down 90 degree temperatures to a beautiful 75.
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I can't do it.
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I can't put more money in other people's pockets.
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If I could, I put more money in my own pocket and we wouldn't have to be there in the first place.
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So it is what it is.
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You think about location, you think about temperature, you think about finances, all those things go into it and you stop and analyze everything and you really have to pivot right.
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I looked at it, got to a point in the week where I said there is no ever loving way.
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I'm going to do what I came here to do.
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I'm not going to attain the numbers that I really thought that I could or that I should.
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I'm going to put a goal in my mind that is a salvageable number, it's an attainable number and it's something that can salvage this week, put a respectable number in place that can help us to better position us for the next event and kind of set us up to be in the right spot.
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So what is a number that you can be happy with, that's respectable, that's attainable, that's not mailing it in.
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It's still something that's going to take a lot of effort and hard work to get to, but when you get to it you can still find a way to celebrate.
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Does that make sense to you guys?
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You go into something like I went into this fair thinking I had this huge number in mind that this is a home run.
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Here's a realistic number.
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I kind of have these ranges.
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Here's an absolute end, all be all.
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I have to do this type of number.
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I go into fairs like that.
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I had to recalibrate, renegotiate in my mind what was a feasible number and then strive for that number.
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I had two numbers in mind going into this to make the best of this fair.
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Like I said, I pivoted during the week and I said, okay, those numbers that you were looking to do, they're not going to come true.
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What are two numbers?
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That number one?
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You say, hey, I really feel like I pushed it and I got this done and this thing really broke well, and then next year this could be a tremendous fair.
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And then what's the next number?
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That's like, hey man, this is still going to be pretty damn hard to hit and if we hit this number, we should feel good about what we've done, considering the situation that we're in.
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And that second number it was on the last night of the fair.
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I was $50 away from that number, legitimately, $50 away from hitting that number, legitimately $50 away, um, from hitting that number.
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And um, I had about 10 minutes or so, like, literally, it's, it's past 11 o'clock, we closed the fair at 11 o'clock and um, or it's almost 11 o'clock anyways, and it's pretty bare.
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Most vendors are gone.
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There's not many left standing that have not closed their shop or not started packing everything up and leaving.
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And I'm telling everybody hey man, I got to get another 50 bucks here.
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And, lo and behold, one more customer came in and we spent some time talking and they bought one hooded sweatshirt that retails for $50.
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I did it.
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I broke that number $50.
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I did it, I broke that number.
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I hit the number that I told myself you can celebrate, you can make a difference in your business with this number.
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It's not great, it's not tremendous, but if you're going to reconfigure and reevaluate your week, you have a number that can help you get ready for the next event.
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It's not going to pay off a bunch of debt.
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It's not going to put you in a perfect position, but it can help and you can justify the time that you've invested by the result that you made, because it wasn't a lost cause, right, you didn't go there and you didn't lose money.
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So I hit that number.
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There was some celebrating that has to come in play in your mind with that by saying, wow, I really, really, really had to fight for this.
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I had to earn every single cent of this to get to this number and that was a good feeling.
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It was a good feeling to get there.
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I'm encouraged by that and I really truly feel like I'll be back next year.
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I'm going to push for a better location next year and do things a little bit differently, but I do feel like it can work for me and that it could be a good fit for me.
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But man, one hell of a challenge for me this year, and I actually had a really good friend of mine share with me that there was another vendor that was at this fair.
00:17:54.667 --> 00:17:57.888
I'm not going to get into the details, but they sell apparel.
00:17:57.888 --> 00:18:02.412
They spent three days at the fair and they sold one t-shirt and they packed up and headed out of there.
00:18:03.342 --> 00:18:04.747
I hear stories like that.
00:18:04.747 --> 00:18:09.289
I look at my competition, who I perceive to be doing better than me.
00:18:09.289 --> 00:18:13.026
For most of the week you start beating yourself up.
00:18:13.026 --> 00:18:26.342
But when you hear the stories of others that didn't achieve nearly what you achieved, it has to be a feather in your cap to keep going, to keep pressing forward, to continue to have the courage to do the things that you're afraid to do.
00:18:26.342 --> 00:18:29.645
And that's a testament to us.
00:18:29.645 --> 00:18:37.415
That's a testament to the brand and the motivation that we have to continue to fight, fight, fight for this brand.
00:18:38.279 --> 00:18:57.182
Now, with all that said, I mentioned to you guys last week that we have made some new connections, we have met some new friends, we've added to the family, and I talked to you guys about being super encouraged by some of the youth that's in this country.
00:18:57.182 --> 00:19:01.330
It's not all a lack of work, ethic and complete disappointment.
00:19:01.330 --> 00:19:04.285
It's not all binkies and litter boxes.
00:19:04.285 --> 00:19:11.708
There's still some hardworking Americans out there that can change the future of this country, and I was excited to spend some time with them.
00:19:11.708 --> 00:19:29.673
And I mentioned to you Isaiah, an 18-year-old young man, isaiah with an amazing work ethic and an amazing personality, and I spent just about every day of the fair with Isaiah and his friend Caden, who's also a great kid.
00:19:29.673 --> 00:19:35.972
He also is motivated and wants to work and he started his own business.
00:19:35.972 --> 00:19:45.344
So he's working a few jobs, but he has his own LLC that he's doing for landscaping and overall just home improvement.
00:19:45.344 --> 00:19:49.192
And we were in the tent and all of a sudden he just pulls his phone out.
00:19:49.192 --> 00:19:58.269
Somebody on the other end answers and he says I'm going to be very direct with you, and then he just bangs out his sales pitch Now as somebody.
00:19:58.470 --> 00:20:01.906
If you guys have listened to the show, you already know if you're a day one, get your ones up.
00:20:01.906 --> 00:20:02.608
I acknowledge you.
00:20:02.608 --> 00:20:03.111
I love you.
00:20:03.111 --> 00:20:04.741
You've been here for over five freaking years.
00:20:04.741 --> 00:20:05.282
I love you.
00:20:05.282 --> 00:20:05.784
I thank you.
00:20:05.903 --> 00:20:09.549
Okay, day ones, y'all already know I'm a sales guy.
00:20:09.549 --> 00:20:18.910
I'm a sales trainer at heart, right, and I spent years in a call center doing sales for a Fortune 500 company on a military base.
00:20:18.910 --> 00:20:22.278
I've also been a sales manager.
00:20:22.278 --> 00:20:33.247
Multiple locations, multiple trainings, my last, when I say previous life, running a Harley-Davidson dealership, working my way up to owning a Harley Davidson dealership, sales, sales, sales.
00:20:33.247 --> 00:20:36.972
I was constantly training, learning and educating people on sales.
00:20:36.972 --> 00:20:45.423
You're piquing my interest here, young man, and for him to literally open the call with.
00:20:45.423 --> 00:20:46.827
You know I'm going to be very direct here and go into his clothes.
00:20:46.847 --> 00:20:57.855
I was proud of the kid and he got everything he needed to out of the conversation, set up his appointments, and after the conversation he was talking to me and said listen, I'm doing fun things today.
00:20:57.855 --> 00:21:03.752
So for every hour I spend having fun, I'm going to do one thing I don't want to do.
00:21:03.752 --> 00:21:11.534
For every hour that I'm having fun, I'm going to stop for a minute, pick up my phone and I'm going to code, call somebody and try to make some money.
00:21:11.534 --> 00:21:23.115
I'm going to try to build my business and I thought, man, look at the perspective on an 18-year-old young lad to say, hey, I'm enjoying myself today.
00:21:23.115 --> 00:21:28.132
For every hour of enjoyment I'm going to add one moment of discomfort.
00:21:28.132 --> 00:21:29.455
I'm going to do something I don't want to do.
00:21:29.455 --> 00:21:30.480
I'm going to make a phone call.
00:21:30.480 --> 00:21:35.882
For every hour that I'm enjoying myself, I'm going to do one thing to better myself.
00:21:35.981 --> 00:21:36.912
Think about that, guys.
00:21:36.912 --> 00:21:38.855
Can we adopt that?
00:21:38.855 --> 00:21:40.398
Can we apply that?
00:21:40.398 --> 00:21:43.154
Think about it All the days that you're sitting around.
00:21:43.154 --> 00:21:53.119
Maybe you're at the lake doing something, maybe you're on vacation doing something, maybe you're on the couch, doom scrolling when you look at the clock and realize you've been doing an hour of nothing.
00:21:53.119 --> 00:21:59.742
Can we implement two minutes of something to change our direction, to cause and affect our day?
00:21:59.742 --> 00:22:07.692
To put things in a positive way, I learned a lesson from an 18-year-old young fella over the week and I'm proud of him.
00:22:08.674 --> 00:22:15.515
But to get back to my point, also on Isaiah, I spent some time with the young fella and he's just a great kid man.
00:22:15.515 --> 00:22:19.123
He's the type of guy that leaves a good impression on you.
00:22:19.123 --> 00:22:25.642
It was very cool to see my wife and baby arrive and them all take to each other.
00:22:25.642 --> 00:22:45.323
Paisley really loved him, and what was kind of cool is when Allie and Paisley arrived which was a surprise to me as to when they were arriving and I had to run to the gate to let them in and Isaiah stepped up and took over the tent and when I came back he was all pumped up and said hey, man, I sold something, I sold something.
00:22:45.323 --> 00:22:48.289
And he, he never asked for training.
00:22:48.289 --> 00:23:11.440
I never showed him, um, how to cash people out, I never showed him how the computer works or anything, but he just stepped up, filled in, took care of it, sold some stuff and then the rest of the weekend, whenever opportunity allowed, he wanted to be behind the computer making sales and talking to people, and everything about that just made me proud.
00:23:11.440 --> 00:23:16.535
Everything about that just encouraged me, right.
00:23:17.096 --> 00:23:32.020
I was encouraged that, like I've said, last week, there is a population out there of young individuals in this country that still want to work for things, that still believe in things, that still, um, are willing to do hard things.
00:23:32.020 --> 00:23:42.272
And then also to know that I built a brand, that this young man was drawn to enough to work his full-time job and to come hang out and spend time with us.
00:23:42.272 --> 00:23:48.284
He also took a a liking to Kyle and Julia with Underdog Metal and was helping them out.
00:23:48.284 --> 00:24:17.616
And all of us had talked after the fair and said, man, if we were all in different positions, if we were in better positions, if we were just a little bit further ahead in our businesses, we would hire Isaiah, we would take him on the road, we would do everything we could to help propel him to the next level in life, and he is just a tremendous asset for any business out there that is looking for someone to grow with them and their business.
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