March 31, 2026
How To Discover Your Perfect Business Idea, Validate It And Launch It This Year | Jason VanDevere Dream Driven
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The Undiscovered Entrepreneur | Jason VanDevere | Dream Driven & Goal Crazy Planner
Episode Summary
Jason VanDevere walked away from a fourth-generation car dealership empire to build something that actually lit a fire inside him. In this episode, Jason breaks down how he created the Goal Crazy Planner, built a real estate portfolio of 34 units, and wrote his book Dream Driven — all by choosing passion over a paycheck.
Timestamps
[00:00] — Introduction & Simon Simulation School check-in
[01:00] — Jason's background: fourth-generation car dealer in Akron, Ohio
[02:30] — Why Jason left the family business to pursue his dream
[05:00] — What stops most entrepreneurs from crossing the start line
[07:30] — The origin story of the Goal Crazy Planner
[12:00] — Why negative feedback from focus groups saved his business
[16:00] — Biggest pitfall Jason is most proud of
[19:00] — Pre-mortem strategy for entrepreneurs
[20:00] — Breaking bad habits using a daily scorecard
[23:30] — Dream Driven book breakdown: Easy Money vs Dream Driven approach
[28:00] — Advice for brand new entrepreneurs
[34:00] — Where to find Jason & free resources
[35:00] — Jason's 6-month goal: 100 lives changed
Key Takeaways
- Desire must be greater than the challenge or you will quit
- Negative feedback is a business-saving tool, not a setback
- Successful behaviors tracked daily lead to successful outcomes
- Find mentors already doing what you want — the shortest path is a straight line
- Money follows passion, passion doesn't follow money
- 📘 Dream Driven (Book) — Available on Amazon
- 📓 Goal Crazy Planner — goalcrazy.com & Amazon
- 🎙️ Goal Crazy Podcast — Search on all major platforms
- 🆓 Free Business Idea Course — goalcrazy.com/idea
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This is an Undiscovered Legacy Production and prod member of Pod Nation Media Network.
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If your desire is larger than the challenge that's in front of you, you're gonna push past and do it, right?
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But if the challenge is greater than the desire you have in your heart, then you're just probably gonna quit and try something different if the challenge arises.
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So yeah, it's like if all I was doing it was for the money, that would have been great until it got hard.
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And then I wouldn't have known what to do because I wouldn't have had the desire to push through the challenges that would have been required of me if the dealership ever got hard.
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So yeah, I think to get yourself across, you gotta find what's gonna light that fire for you.
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Are you ready to unlock your entrepreneur potential?
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Are you ready to break free from all the barriers holding you back?
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Then you've come to the right place.
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Welcome to the Undiscovered Entrepreneur, your first step in getting across the start line.
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Let's get across that start line together, right here, right now, on the Undiscovered Entrepreneur.
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So you should believeers, and we are here again with another amazing entrepreneur.
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We're here with Jason.
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Hey Jason, how you doing?
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I'm doing great.
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I'm excited today.
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All right, me too.
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I'm so excited to have this conversation with you, and thank you so much for taking the time out of your day to be on the Undiscovered Entrepreneur Get Across the Start Line.
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Yeah, yeah, looking forward to being here.
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All right.
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So before we start anything, I can have one uh kind of semi serious question to ask you.
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Okay, you ready?
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Yeah.
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All right, here we go.
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Are you a school believer?
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Absolutely.
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All right, Jason's a school believer.
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Woohoo! All right, thank you, Jason.
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I appreciate you.
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All right, so what I like to do here at the very beginning is just getting at it, get kind of an idea of who you are, what your entrepreneur adventure is, and how you got across the start line in your entrepreneur adventure.
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Yeah.
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So uh I grew up working for my family.
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So my dad is a car dealer in Akron, Ohio.
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If you ever come here, you'll see my last name, Vandeveer all over Akron, Vandevere, Kia, Cadillac, Chevy.
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They got five dealerships.
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So I was in line to be the fourth generation to own and manage these portfolio of car dealerships.
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Uh, so I grew up working in all the different departments.
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My dad wanted me to work in every department for a year, maybe even several years, so I could learn the whole business.
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And somewhere in there, I realized it wasn't a passion of mine.
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Uh, it's just not what I wanted to do with my life.
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And even though everyone told me it was a crazy idea to leave the family business uh to turn down that opportunity, I left with basically nothing.
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And I pursued a dream of mine.
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So random dream, but I wanted to design a planner.
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So I left my job.
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I spent months interviewing successful individuals, finding out how they set their goals, track their goals.
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I put together this design for the goal crazy planner.
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And for a few years, all I was doing was selling planners online, and then that turned into uh workshops and courses, a coaching program.
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I have a podcast of my own, the goal crazy podcast.
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Most recently, I just wrote a book, Dream Driven.
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Nice.
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Uh, and then somewhere on the side, I started investing in real estate.
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So I've got up to 34 apartments, and I would say that's like my highlight reel.
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Aside from that, I'm like most entrepreneurs, I'm just figuring it out as I'm going.
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And many of the things along the way that I did also did not work out.
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But uh, that's a little bit about me.
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That's awesome.
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Yeah, we're all kind of on that train of trying to figure out as we go along, kind of building the airplane on the way up, you know, off the cliff.
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So yeah, yep.
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But it's gotta be it had to have been difficult because you went from a fourth generation car dealer.
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I I used to be a car salesman, I think we I mentioned that earlier, so I kind of feel where you're coming from, and just kind of branched up from that must have been really difficult for you because it's kind of like, why am I doing this?
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Even though you're following a passion, I kind of understand that.
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It's gotta be kind of rough on the back of your mind.
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It was, it was, but when I was working at the dealership, if you ever go to one of the dealerships, you'll know if my dad is there because you'll hear him.
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He's loud, he's very excited, and you'll just be able to see that he has so much passion for the car business.
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He loves it.
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It's it's an extension of himself, this business that he's built.
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In growing up working there, it's like I knew I wanted that.
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Like I wanted a fire inside of me for my career, for what I was doing.
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And uh, when I worked there, I realized I wasn't gonna find it there at the dealership.
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And now, so I am lucky.
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My great-grandpa started it, my grandpa had it.
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Now my dad and my uncle co-own it, and my uncle has kids who are going into the business.
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So the business should not die.
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But uh I was not the path that I chose for myself.
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But it was a hard decision.
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I was afraid to tell them that I wanted to leave.
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Yeah, we really kind of got like, hey dad, uh I hate to tell you this, but yeah.
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But it's nice that you got over that hump that you got out of that comfort zone and actually be able to told them because you you probably would have miserable the rest of the time that you were there because it's not in your zone of genius or not the, you know, what you said, the fire inside of you.
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And that would have been really hard to take.
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Yeah, I would have been doing it just for the money, which is I think where most people are with their career is like they're doing it not because it gives them the freedom that they want, that it's not because they enjoy it or get the vacation time, or they probably maybe not even the income that they want, but they're just doing it for a paycheck.
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And it would have been a very nice paycheck that I would have been earning potentially if I did a good job running the dealerships, but uh I would have been just doing it for the money, and I I didn't want to do that.
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We gotta avoid that we're doing it just for the money.
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It's it's really tough because that money seems good, but it doesn't there's a big difference between abundance and money and abundance and passion.
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And and having that abundance and passion is really what's gonna drive you throughout throughout the rest of your life, more than likely.
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But just going for just the money, it's like it's very, very, very temporary to have that.
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Yeah, no, I I agree.
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Yeah.
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All right.
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So um what I'd like to do here is what do you think actually stops new entrepreneurs from getting across the start line?
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We have different types of problems and things that stop us from going.
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What do you think stops most entrepreneurs from getting across the start line in their entrepreneur adventures?
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Yeah, probably fear and they don't know where to start are probably the things there.
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And I know those are one of the one of them is one of your four hurdles there.
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That's what I think it comes down to you.
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Yeah, absolutely.
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Fear goes right here.
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First, false evidence appearing real.
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It's not nothing that's gonna, you know, it's not a saber-tooth tiger that's gonna bite us in the rear, and it's nothing that's really gonna hurt us, it's just something that it triggers a mechanism in our head, a very old mechanism in our head that tries to protect us.
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But sometimes it's actually, and I like making this point too, it's sometimes it points you in a direction.
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If you fear it, you need to go towards it instead of away from it.
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And that's I think what happened to you in in your uh in the car salesman and getting the dealership and tell yeah, I'm sure you're afraid as you said earlier, you're afraid to tell your dad, hey, I don't want to do this.
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But since you got over that fear, it wasn't something that wasn't gonna hurt you that bad.
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You actually came out really far ahead.
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Yeah.
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Yeah, absolutely.
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The fear, uh, I was afraid of him, but the I had a dream inside of me.
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And I think that's what really helped me get across the finish line is I figured out what I wanted to do with my life.
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And and it was I wanted to launch this planner business.
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And I think that's a really deep question.
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What do you want to do with your life?
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But I think once you can get clarity on that and you find this dream that's gonna light a fire inside of you, that's what's gonna give you the courage to go push through those challenges.
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Because you brought up earlier, right, we don't want to just be doing it for the money.
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And I think it's like if your desire is larger than the challenge that's in front of you, you're gonna push past and do it, right?
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But if the challenge is greater than the desire you have in your heart, then you're just probably gonna quit and try something different if the challenge arises.
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So, yeah, it's like if all I was doing it was for the money, that would have been great until it got hard.
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And then I wouldn't have known what to do because I wouldn't have had the desire to push through the challenges that would have been required of me if the dealership ever got hard.
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So yeah, I think to get yourself across, you gotta find what's gonna light that fire for you.
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Exactly.
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Do me a favor, what uh what inspired you to do this?
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I mean, you said you wanted to do the planner, I get that, but what actually inspired you to do the planner?
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I'm I'm really curious about that.
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Yeah.
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So when I was working in those different departments at the dealership, I I got very obsessed with planners.
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And lots of that was because of the nature of the role.
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I would show up, I'd go into a new department, I was only gonna be there for a few months or a little over a year, and I needed to figure out all right, what are the goals of this department?
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What are the habits I need to have every day so I can succeed?
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There was a maybe a pressure inside of me to I needed to perform well, right?
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My one, my name is on the building.
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I'm potentially gonna be the all these people's boss one day.
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Like I want them to earn their respect by how I perform here.
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So I was using all these planners because I just needed to keep myself on track to these goals.
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And I was ordering all these different planners, they all had the right promises and keywords when I was buying them, but I feel like when I would order them, they just wouldn't deliver on what I was looking for.
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And I was reading a lot of self-help books, I was attending lots of conferences, and I feel like that I was learning these principles that successful people were operating under.
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And I just wanted it all together in a planner.
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I wanted this planner where it's like, I know if I put my goals into this planner and follow the process, I'm gonna reach my goals.
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And I just wanted to find that template.
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And now I believe I've made it after a lot of hard work.
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But uh that's that's what initially put it on my mind in this desire.
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One, I wanted it for myself, and I also wanted it for other people because I at least was on a track at the dealership to I was on a very successful path that many people might not have the same opportunity.
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But I wanted to give them the confidence, like if they had the right method to accomplish their goals, they could still go have success, even if their family doesn't own a large dealership.
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And I would say that still was a desire of mine when I was leaving the dealership.
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I feel like growing up, my friends would kind of tease me about like Jason's got the golden ticket, right?
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Like, all he has to do is keep his same last name, smile his way through working for his family, and he'll go be successful.
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And that saddened me away because I truly believe it's like everyone has the same opportunity to be successful as I did.
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They would just, they're just gonna have to work for it.
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And I would still have to work at my family's dealership.
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It might have been a very straight path.
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But uh, I wanted to prove to other people look, you don't being successful, it doesn't just come from you having the right parents who own a big business, it comes from you having the courage to go out and do something, do something that's gonna serve others and accomplish your goals.
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So hopefully the planner would then give them the framework to make that happen.
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You hit some very good points there.
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And the one I'd really like to kind of reiterate on too is being able to help others.
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And I think being able to help others is its own reward, too.
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I mean, because I mean there's a difference between having a dollar and then having that warm fuzz of healing in your chest that you know is going to stay with you because you know you helped somebody achieve a goal, or you got a promise that was kept that made a big difference in their lives, and you had something to do with that.
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Oh, yeah.
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Yeah, it's it's a lot more rewarding.
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One of the main goals I track for myself is lives changed.
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And maybe those are like clients that sign me on, or maybe it's someone that it like I met at our church and they a piece of advice I gave them, they went and did something with it.
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Like if I helped them make a change in their life, I track it for myself.
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And it's just so rewarding because that's what that's what lights the fire inside of me more than just chasing the money.
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And there's a part of that too, that you're a world that you're also a part of that we changed lives too, and that's in podcasting and and teaching others that listen to us the what we've learned in changing their lives too.
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That's a little harder to track, but it does happen.
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Yeah, yeah, yeah.
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Oh, absolutely.
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And I'm sure you've gotten people though reach out when they hear an episode and they tell you, like, hey, I really needed that, or that was phenomenal.
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Or I implemented what that one guest said, and it's yeah, I would draw, I've got like a little barometer thing here in my office where I track lives change for the month, and I would color it in because it's just one more person.
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I'm gonna give myself credit for it.
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There you go.
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And and you fill that in, it makes you feel good when you're able to fill that in.
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Yeah.
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And I like the fact too that you you take the best of everything that you've learned from all these other places, whether it be webinars that you've gone to or conferences or even books that you've read and combine them into yourself to make one final product.
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And that's what I try to do too.
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But the end product's always going to be different for everybody because our experiences and our lives are different.
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But being able to get that one final product from all the learnings and teachings that you've had to one place is really what makes a difference.
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Yeah.
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Yeah.
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Cause when I quit my job, I spent months interviewing successful individuals.
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And having a family with connections did help with that.
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I was able to get in contact with a lot of business owners and ask them how they accomplished things.
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But probably what was really helpful then is after I made this design, one of them recommended I host focus groups.
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Uh he was like, you got to host a focus group, take people through this design.
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And I thought that was a silly idea to host a focus group.
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But out of respect to him, I did it.
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And that was so powerful for me.
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One, that meeting was scheduled to go an hour.
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I had six people go through this design, and the meeting ended up going over three hours long.
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We didn't even make it through the whole design.
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And really, it was painful.
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People were telling me all negative feedback, like this is confusing.
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I don't get what I'm supposed to do here.
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This is too much writing.
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This seems repetitive.
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And when I left that meeting, I felt crushed.
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What have I done?
00:15:07.789 --> 00:15:08.990
I've spent months now.
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I turned down a great opportunity.
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I've told the world I'm making this planner, and it's I feel embarrassed that I even showed it to other people.
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But then I had this clear list of things that I needed to fix.
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It was like, all right, I'd rather get all the this information up front, but when I can change it, rather than after I've launched the product and get bad reviews.
00:15:27.949 --> 00:15:35.709
And there was just like trying to figure out the right way to take so much beautiful, great information and strategies I learned from these people.
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But then how do I put it in an easy, straightforward process that's not too much, that's not too, that's not too little that somebody could actually get results from.
00:15:44.990 --> 00:15:52.909
And I ended up hosting seven of those focus groups because I just kept going until eventually the last two of them, it was like we went through it.
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Maybe they noticed a few typos, small things, but they would try it out, it would work, and they're getting results.
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And finally I was like, all right, it's ready to get this actually started.
00:16:05.469 --> 00:16:08.269
Negative feedback is not always a bad thing.
00:16:08.429 --> 00:16:13.389
Some of us want the negative feedback so we know what we need to work on, just like you did.
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I mean, and get going getting it out from other people that don't know exactly who you are is probably the best.
00:16:20.350 --> 00:16:26.029
Because like you can go to a family member or a friend or something like that, and they'll go through like, oh, this is great.
00:16:26.189 --> 00:16:28.990
I was like, no, that's not what I want to hear.
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I want to hear what's bad about it so I can fix it.
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But you know, they're gonna want to save your feelings or whatever.
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So being able to I turn around behind to the guy behind you and say, Hey, what do you think of this?
00:16:40.110 --> 00:16:41.949
I did that with my podcast cover.
00:16:42.029 --> 00:16:50.669
I I was at a coffee shop and the the woman behind me was you know was in line and I bought her coffee and turned around and said, What do you think of this podcast cover?
00:16:51.549 --> 00:16:51.870
Yeah.
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Oh, that's great.
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Yeah, and and it was it was great.
00:16:55.149 --> 00:16:56.189
It's great information.
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Don't take it so hard that you're getting negative feedback because then eventually after you make these fixes, after you make these these solve these problems that you've had with the negative things, it starts to work itself out.
00:17:08.910 --> 00:17:16.670
And those last two focus groups were the the the kind of final things like, okay, I finally fixed everything that needs to fix, I have a viable product that I could put out there.
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Yeah, yeah, they were powerful.
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And silly but not silly.
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That's what I call it.
00:17:22.910 --> 00:17:23.549
Yes, it's silly.
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I'm a silly guy, so what can I say?
00:17:25.950 --> 00:17:37.230
But even though it seemed silly to you at first, getting over that that thought of it being silly and actually holding these focus groups again and again and again to get to the where it need to be.
00:17:37.470 --> 00:17:41.470
If you did if you thought it was so silly that you didn't do it, it never would have happened.
00:17:42.350 --> 00:17:46.190
Oh yeah, my business would have absolutely failed if I did not host those focus groups.
00:17:46.350 --> 00:17:46.990
Yeah.
00:17:47.789 --> 00:17:48.190
All right.
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That's awesome.
00:17:49.150 --> 00:17:49.789
Thank you so much.
00:17:50.029 --> 00:17:53.150
Okay, so I have a question I like to ask all my guests.
00:17:53.470 --> 00:17:56.269
Now you've been on a few podcasts, and you have a podcast too.
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So you always hear like, oh, what's your biggest pitfall?
00:17:59.470 --> 00:18:00.509
What's your biggest problem?
00:18:00.670 --> 00:18:01.710
Blah, blah, blah, blah.
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So I like to put a little bit of a spin on that.
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And I like to ask, what was your biggest pitfall that you're most proud of?
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