From lawn mowing to leading with entrepreneur Matt Shoup

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Show Notes:

Telling your brand story is more crucial than ever. It’s a surefire way to connect with your audience on a more human level and build ever-lasting trust. But where do you start? Our guest will tell you everything you need to know!

Meet Matt Shoup. Matt is an award-winning serial entrepreneur, book author, and keynote speaker. He discovered his passion for entrepreneurship very early on when he started a lawn-mowing business to earn $200 for a boombox. Over the years, he has founded six successful companies and grown them all from the ground up. Matt has been featured in publications such as INC Magazine, Entrepreneur Magazine, BBC, Fox Small Business, Huffington Post, etc. He also wrote two books, called ‘Become an Award-Winning Company’ and ‘Painted Baby.’ When he is not running his businesses, he enjoys spending lots of time with his family, traveling to Spain, and living life to the fullest.

Matt believes that brave and vulnerable storytelling is at the base of every successful business. According to him, it’s the true key to deep connections in both life and business.

In this episode of the Think Business with Tyler podcast, we talk about why your self-worth is not tied to your net worth, the importance of storytelling in sales, how to tell your brand story, and why you shouldn’t let go of your passion.

If you want to hear more about creating deep connections with your customers, tune into this episode to hear what Matt has to say.


💡 Name: Matt Shoup

💡 What he does: Matt is a serial entrepreneur, book author, keynote speaker, and podcast host.

💡 Noteworthy: He’s a two-time published book author, with his first book coming out in 2011 called ‘Become an Award-Winning Company’ and his second book from 2023, ‘Painted Baby.

💡 Key Quote: “Your self-worth is not tied to your net worth. And it’s not all about the profit.”

💡 Where to find Matt: LinkedIn

Key Insights

Your self-worth is more important than your net worth. It’s important to understand that your self-worth is not tied to how much money you make, but it’s more linked to your impact. This is especially true in business because running a business isn’t just about making a profit. It’s also about how you affect people in your journey through leadership, life, and business. Ultimately, that’s what you will be remembered by – how you made others feel.

Matt says, “Your self-worth is not tied to your net worth. And it’s not all about the profit. There are people involved in business, and all this money part of the business, you need to support your family, obviously. You need to invest. You need to be wise with money. You don’t get to take any of that with you. And the people that you journey with along the way in life and business and leadership, they’re going to remember how you impacted their life way more than the dollars that you made.”

Sell through storytelling. If you want to increase your sales and connect with your audience on a deeper level, you need to master the art of storytelling. Storytelling is as old as the time itself, and humans have connected through stories for centuries. But interestingly enough, telling stories is also an effective sales and marketing tactic.

Matt explains, “As we’re selling, as we’re connecting with others, ‘cause sales is just about connecting with another human, and you’re meeting their needs, and they trust you at a base level, but also a deep level. And you’re doing that not by informing, not by giving and spewing and throwing up information, but you’re pulling them in with a great story. Think of any recent story or movie, whatever kind of media you received. Something hooks you. There’s a storyline. There’s some kind of plight that’s involved where somebody or something is in danger of letting something or somebody down. And then there’s a moment where action happens, a resolution is made. So this is the process. And if you look at really good marketing and connecting, it’s through story, that’s how we’ve connected for years as humans.”

Tell your brand story. People don’t buy from businesses; they buy from people. So, if you want your audience to connect to your brand on a human level, you need to tell them your brand story. Make them feel like they’re part of your brand story. Make it feel personal.

Matt explains, ”I think any business owner, if you’re like, ‘Well, hey, I didn’t paint a baby. I didn’t almost kill a client’s kid. What’s the story I can tell?’ Origin story is so huge. So, how did you get to where you are? What were some of the struggles that you had to overcome to get there? And it connects with another person on a human level, and they see that you’ve worked hard to overcome something. So if you don’t have a big business blow-up, maybe there’s a personal one.”

Don’t let go of your passion. Your passion is your North Star. It’s your compass that’s guiding you through your entrepreneurial journey. So, if you want to be truly fulfilled in life, never let go of your passion.

Matt says, “When you have a purpose and when you have a passion and a calling, there’ll be a lot of things that push against that. So, what I tell business owners is if you feel like God or whatever you believe in, that’s bigger than you, is calling you to something, and you start to get a lot of pushback, I’ve given up a lot of times because of that in life, and I keep getting pulled back to the same thing. So when you’re getting a lot of that friction, a lot of that pushback, it means you’re probably onto something and keep exploring that and remember the greater purpose.”

Top Quotes

[21:47] “A lot of that anger came from a lot of just childhood bullying and getting pushed around, like any little kid, they need to know that they’re loved, that they’re good enough, that they’re accepted at a deep level. So I never got that. And so a lot of my business drive was like, ‘Screw you. I’m going to prove this to you.’ And my net worth and self-worth were very much tied together.”

[24:24] “It’s part of being a male. It’s you provide, you protect, you contribute. But when you talk about provision, it’s not always financial. It’s like, how are you emotionally providing to your kids, to your spouse? Provision is contribution. It’s filling a cup. It’s filling a bucket, and there’s a financial bucket, and in business guys, that bucket goes up and down. Sometimes it’s full. It’s overflowing. Sometimes it’s not as much. But when you’re only focused on that and you’re missing moments in your kid’s life or in your journey with your spouse, or just the little things. Your kids just want to know that they’re good enough and that they’re loved by you, by their father, and more money’s not going to fix if you’re missing all these other things, there’s lots of other buckets to fill.”

[25:15] “Write that down. What does my wife, what do my kids, what do the immediate people in my business need from me? There’s obviously a financial box. We just focus on that too much, and we can totally miss the spiritual, the emotional, just the time, the presence.”

[27:10] “I was not self-aware at all in my early twenties of business. I was crushing it in business, super pissed off, and just burning people out, burning bridges. Nobody wanted to stay and work with me.”

[29:34] “What I learned is you can stand firm. You can stand tall, you can stand rooted with a big smile on your face, and still love and be kind to people, so it is a balance. […] You can’t let people walk over you, but you can’t just be so steamrolling them that it almost turns into that they’re like, ‘You know what, I can’t wait to get away from this guy. I find another couple of bucks an hour. I’m out, or I find another project, I’m out.’ And that’s something that happens a lot too. You have to build a team where people know that you love them, that you trust them, and that you’re going to hold them accountable to things, but that you’re going to reward them, that you’re going to share in the profits that are created together.”

[40:35] “Spain, for me, gives perspective on how people do life. It always reaffirms and confirms with me, what we talked about before, it’s not always about the dollars and cents. It’s like, I’ve got amazing relationships with people and memories that I’ll have with them, with my kids, with my family for life. And I love bringing pieces of Spain back to the States. And then I always love bringing pieces of the States over to Spain.”

[45:27] “You’ve got to make money. That is an important thing. It fuels your life, your lifestyle, and everything, but there’s going to be way more important things that you leave behind for people than money, so always take that into account.”


Painted Baby by Matt Shoup

The 5 Love Languages: The Secret to Love that Lasts by Gary Chapman

Personal Website

Gentle Art of Leadership Podcast


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