Shooting Straight: Built a $3.6 Million Business (and Still Has Doubts)
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How did Waylon transition from a lineman to building a trade school?
Waylon Hastie left a career as a lineman to build a school that prepares the next generation for the trade. Today, his business is thriving, but he still wrestles with the same self-doubt that shows up for many business owners. On this episode, Entrez Leadership's head coach, John Falcons, joins Waylon at the shooting range for an honest conversation about imposter syndrome, hiring the right people, and leading through the challenges that come with a growing business. Let's get to it.
Pull. Pull. How long have you been in business? Seven years. Pull. You moved that target! Yep. Pull. All right, I'm gonna make the questions harder on you, because I missed. What was your revenue last year? Oh gosh, 3.6 million. Pull. Pull. What made you start your business? The desire to serve and help. I didn't say pull! Pull! Would you rather make more money or have more free time? Free time. Pull! Pull! What's your biggest goal for the year? More free time. That's your biggest goal? For 100%. For your whole team or just for yourself? For myself. What about for your team and your business? Processes and systems. What's that going to do for you? Repeatable,
right? It'll allow the opportunity to scale. More insight and vision for the future. Love it. Pull. Good shot.
Pull. Pull. One word do you think your team uses to describe you?
What does Waylon say about dealing with imposter syndrome as a business owner?
Bold. What about on your bad days? It's probably not the best choice of word, but a turd. A turd. Yeah. Pearl! Ah, I got him!
Pearl!
All right, Waylon, you got me on that one, but we're going to the next range and we're gonna kick it up a notch. Let's do it. All right, Waylon, we got five different targets with five different topics. And we've got three different questions. We've got green questions, the easy ones. Those are worth one point.
When and why did Waylon decide to raise his prices?
Then we got yellow questions, those are worth two points. And then we've got the hard questions, the red ones, and those are worth three points. For each round, we're both gonna shoot. I'm gonna shoot first to pick the target and the topic, and then you're gonna shoot. If you hit the bullseye, you get to pick which question you're gonna answer. But if you miss, you automatically are gonna have to answer the red question and you're gonna get no points. Make sense? Let's do it. All right, let's do it. Money. Money. Let's see what you got. You're in trouble. Bullseye, pick which one you want. Red, yellow, or green? Let's go yellow. All right, let's see what we got. When did you know it was time to raise your prices?
I would say within the
last probably 2023, is is the first season of business where we had enough financial data and enough understanding really was support you know we hired some help to uh to to kind of review that because i would i would be honest i i don't i don't really as a business owner i didn't know how to do that i didn't even know where to begin to look right but when we hired a controller as a third party and we began to look at that and we were able to hire a fractional CFO and I started learning about margins and gross margins and net margins and I didn't know about it then. However, I trusted those people that I hired enough to know it's time for a price increase. How'd you set them to begin with? Just what other people were doing or?
Yeah, just basically some Googling market research, you know? Okay. And we started out really low just to kind of get going. So we, each year we'd raise our price, but I didn't know enough to know about why. The goal was to get started, get traction, and then stick with the market for what I knew.
Yeah.
How did it feel? Like when it came time to do it, did you have some reservations? Were you a little worried about how it was going to go? Yeah,
of course. I mean, with imposter syndrome for me, it was, you know, I didn't know how to handle the concept of a customer giving us that money. And I don't take that lightly, right? So in that, it's like, where's the fine line of what I know now as a net bottom line in order that I serve well on the team and the business, right? So it was really hard when we got in a position to say, all right, it's time to go up because the fear that goes with that is how high is too high?
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Chapters
8 chapters
1
How did Waylon transition from a lineman to building a trade school?
0:05–2:03
2
What does Waylon say about dealing with imposter syndrome as a business owner?
2:03–2:34
3
When and why did Waylon decide to raise his prices?
2:34–7:19
4
What gut‑feelings and non‑negotiables does Waylon use when hiring new team members?
7:19–9:25
5
How does Waylon’s team approach off‑site strategic planning and accountability?
9:25–17:46
6
Why does Waylon compare executive coaching to hiring a personal trainer?
17:46–31:30
7
What impact does Waylon’s school have on breaking family cycles for students?
31:30–39:29
8
What final advice does Waylon share about leadership, money myths, and moving forward?
39:29–41:55