In this empowering episode, Dennis McCurdy, Principal Owner of McCurdy & Andrew Investments, shares why going it alone as a solopreneur leads to the Valley of Dead Dreams and how accountability changes everything. If you’re grinding alone and watching your best ideas collect dust, you won’t want to miss it.
You will discover:
– What makes peer accountability more powerful than family or friends for growth
– Why you need a selective “gang” that will tell you the truth and push you forward
– How to choose accountability partners who show up and call you on your stuff
Episode Transcript
Scott Ritzheimer
Hello, hello, and welcome, welcome once again to the Start, Scale, and Succeed podcast-the only podcast that grows with you through all seven levels of your journey as a founder. I’m your host Scott Ritzheimer, and too many founders think that grinding alone is a necessary part of building a business or a nonprofit, especially those of you in the startup entrepreneur stage, trying to succeed as a solopreneur, the challenge though is without anyone watching, very few of us does our very best, especially over the long haul, which leaves so many of our best ideas to gather dust in what my guest calls the Valley of Dead Dreams. Doesn’t that sound wonderful? We’ll talk about what that is and how to avoid it here in just a bit. But my guest has built a system for himself and spent over a decade teaching others to do the same.
With us here today is Dennis McCurdy, who transformed his life from graduating near the bottom of his high school class and sleeping on an office couch to achieving seven-figure net worth. Following his military service, he built eight businesses, managed 29 properties, authored four books, and led mastermind groups for over a decade. He teaches that mindset, accountability, and strong relationships drive true achievement. He’s the author of the book “Unleash the Power of Connection, and he actively runs personal development workshops to help others reframe their failures into fuel for growth. He consistently proves that strong network connections and daily discipline directly accelerate personal transformation. Andy’s here with us today, Dennis. Welcome to the show. Glad you’re here. I love I love me a Harvard Business Review stat, and and you you give us one about a study. I’ll let you set this up for us. But what is it that that we can learn from this study, and how does it apply to that founder that’s that’s trying to succeed in that solopreneur stage?
Dennis McCurdy
We’re talking about the we all do better when someone’s watching. We are yes, which is true. I mean, I just was telling somebody the other day that it doesn’t even have to be somebody. Sometimes just a picture of somebody can, you know, can cause us to to focus more, to be more accountable. You know, the whole thing is, and I think that’s the big thing: is we’re not meant to do this alone. And we say that I say that in the book. You need to really reach out to people, be connected. Again, accountability is one of the most important things that we can have. I always tell people, I don’t like to be pushed, but I love the results, and and we you know we need that kind of thing. I mean, unfortunately, probably we all need a drill instructor in our life, but we don’t have one. And and I was raised by a drill instructor, so I know how that can go. But
Scott Ritzheimer
so it’s a fascinating dynamic because the folks who go out and start their own thing tend to be more comfortable with doing their own thing than a lot of people, and and the the flip side of that, maybe the negative for or for better or worse, I guess, is a tendency to do our own thing, our own way, at our own time, on our own terms, all by ourselves. How do how do you help folks? Because there’s a tension there of having that accountability, having folks that are in your corner and care about you, but how do we keep at bay that that resistance to push back, that that that rebel spirit that may serve us in other ways, but doesn’t necessarily serve us well here?
Dennis McCurdy
I think that we have to understand that you know basically it’s accepting it’s for your own good. You know, I mean, because you’re right, we’re very independent. I always tell people the best thing about being self-employed is being self-employed. The worst thing about being self-employed is being self-employed, because there’s just nobody to to push you. You know, except when you’re fire a customer fires you or something, which is the worst thing you want to have happen. So, you know, having you know, I’ve had a lot of mentors in my life. I’ve had accountability partners, and and coaches and consultants I’ve hired. I’m actually part of a national mastermind group now with about 50 other insurance agency owners, and it’s good to be able to have that and hear other people’s stories to be able to get out, get out of your own way. That’s our biggest our biggest problem for most people in the world. Just getting out of our own way, and and we can be stubborn. Plus, it’s nice, you know, being the boss sometimes.
Scott Ritzheimer
Yeah, yeah. So the way that we’re not going to go solve for this problem is to go get a boss somewhere else, right? That’s that’s that’s out of the equation, at least for these folks. Might be right for some folks, but let’s let’s just rule that out for the the sake of the conversation. So we’re not going to go get a boss from somebody somewhere else. Even if you hire an employee or two, you’re their boss, and so having someone there might help a little bit. But it’s not quite the same. We’re not necessarily talking about going and getting a business partner and giving up equity in your business. These are all like real complicated, can work in some situations, but that’s that’s not the solution that that you’ve proposed here in the book. What is?
Dennis McCurdy
Having your own gang? We talked about that earlier. I mean, I’m a big believer in mastermind groups. Again, I think as an entrepreneur, solopreneur, you have to understand and be open to these things if you really want to grow and accelerate. I mean, just everybody. We’re not all one thing. We can’t do all. Everybody has our quirks and their quirks. Everybody has their strengths and their weaknesses. So I remember once when I was talking to one of my buddies in a group, we were saying he was saying, write all the things down on the left side of a piece of paper that you’re good at. Write all the things on the right side that you’re not good at. You don’t like. You should tear it in half and put an ad in the paper for that part, because again, we’re not perfect. So having someone who you know again, why I like the gang concept, having which means goal achieving nudging group. It’s having people around you that are not afraid to call you on your stuff, because we all have stuff. I mean, if you think you don’t have stuff, you’re in denial, right? And so, being vulnerable enough to accept that and and accept the. I want to say I don’t want to say criticism, but accept the pushes because, in fact, it was James Allen said in his book As a Man Thinketh a person who doesn’t shrink from self-criticism can always achieve their goals, and so having people that will give you that loving kick in the butt when you need it is really important because
Scott Ritzheimer
yeah, this is this is this is at least the first and may end up being the last. I don’t know. We’ll see. But episode where we talk about this question, I don’t know that I’ll ever ask this of anyone else. What’s the difference between a good and a bad gang member.
Dennis McCurdy
A good and a bad gang. Well, a a good gang member shows up for you, and you show up for them. A good gang member will tell you the truth. You know whether you want to hear it or not. You know to say, hey, wait a second, you know, let’s get off this. You’ve been on this too long. You’re making these excuses. You’re not. You’re you’re lying to yourself. That’s what you want. I mean, you don’t want to punt to people who just say yes, yes, you’re great, you’re wonderful. That that doesn’t get you anywhere. I mean, nobody’s perfect, and so we’re all trying to improve, you know, a little bit every day. And so, and it’s easy to deny, you know, hey, I’m, I’m, I’m, this, I’m okay, I’m doing this, it’s right, and somebody else will go, wait a second here, you know, you’re a little off track, or you’re, or you’re letting some of your maybe negative patterns, you know, filter in your sabotaging behaviors, which we all have. I always liked that cartoon way back in the day by this little guy called Pogo, and he said, “We’ve met the enemy, and it’s us. And so we have to realize and be open enough to accept that.
Scott Ritzheimer
What is your take on who to invite into your gang? Is it family members? Is it friends? Is it other business owners? What are some of the mistakes you see folks make there? I guess I would set up and say I think most people have a gang, whether they want to or not. Right, it’s more that they haven’t been selective in who that gang is. Would you agree?
Dennis McCurdy
I agree. I totally agree, and that’s really important. I mean, sometimes it just happens through osmosis. They just, you know, and people just in our our natural life. But having people in your family can create a whole. It’s a whole nother dynamic there. So in fact, I remember talking to a woman who it was a husband, two daughters, and the wife in a very successful restaurant. But there were always there was always this stuff going on. In fact, one of them said, “Well, I want to leave here and I want to go to New York City, and I want to get a good job and I want to make this kind of money. And I said, “Wait a second! You get six weeks off at this job. You drive two miles to work, and you’re the boss. What are you talking about? So I had said to them, “You know, hire a coach for the family. Hire a psychologist if you have whatever you have to do, because this is a gold mine and you’re going to kill it. And they actually did, so they ended up selling it and being miserable.
Scott Ritzheimer
Oh, that’s awesome. So
Dennis McCurdy
Yeah, having that’s important. Go ahead.
Scott Ritzheimer 9:58
What are some of the best places to find your gang?
Dennis McCurdy
That’s a tough one. It you have to just be very. I mean, sometimes you can find them online through things like LinkedIn. Sometimes through business groups, people you know, even maybe even through customers who might know people. It’s there are some online mastermind groups now, which can be helpful because you have facilitators who actually pay and they facilitate the meetings and things, so that can be helpful. It’s it’s a process, and and some and sometimes I know in the book I talk about my friend Margot Chevers, and she and I had decided to have a mastermind group, and so we started meeting once a month, and other people said, “Well, I want to come. I want to join party, be part of your group. And they would come, and they would they would they would show up. Maybe they come twice, and then they say, “Oh, I’m just too busy on this. I said, “Well, we’re busy, but we show up every month. We commit to our goals, and we get them done. So you’re too busy to do that. And Margot and I met every month for seven years.
Scott Ritzheimer
Wow!
Dennis McCurdy
And so we used to. I know. I know if you read it in the book, but we used to write a check to each other after each meeting for 500 bucks, post dated 30 days, and if you didn’t do your goals, the other person got to cash the check.
Scott Ritzheimer
Yes. Yes. I love that. I love that, and and I I think what that taps into is how you’re saying ahead of time is like these are people who are advocating for you, and and when when you look to some of the more common places, a a spouse, a parent, a friend of yours, they either like a friend cares but doesn’t necessarily understand. A family member is probably afraid and understands, right? But when you can find other people that you can, to some extent, go shoulder to shoulder with, like the two of you did, I think that goes back to what you opened with of the power of peer groups. Where did you find that? How did you discover that?
Dennis McCurdy
Where did I find the power-the power of a group? You mean, or yeah, many, many, many years ago, I was invited to a men’s group that was more of a not a business group, but it was just basically men building intimacy with men, communicating, and I discovered all of the different opinions and variety you can get from that, and that’s when I decided to start my own mastermind group. And then also, I when I was teaching my workshops back in the day, I was concerned that they would they would leave the workshop, and that would be it. So I said to them, anybody who attends the workshop can come to a free mastermind group. We meet every month. We had here’s the location. This is what we’re going to do. And you know, of the hundreds of people that came, only maybe about a half a dozen actually did it consistently, and eventually we disbanded. But you know, it was like you need to have that constant accountability. Every human being needs that; otherwise, we’d all be perfect, right?
Scott Ritzheimer
For sure, for sure. Dennis, there’s there’s so many different questions I could ask, and in so many ways that you could go with this. But there, I want to make time for a question that I ask all my guests. I’m interested to see what you have to say, and the the question is this: What would you say is the biggest secret that you wish wasn’t a secret at all? What’s that one thing you wish every founder watching or listening today knew?
Dennis McCurdy
You don’t have to do it alone. It’s it’s that simple. You can, and if you’re, if you don’t want to involve, like say, a gang kind of person, get yourself a coach or consultant, someone that you trust enough and you have enough, like enough, where you’re willing to open yourself up to take that advice again, because nobody’s good at everything, nobody’s perfect at everything, and so we need to really recognize that. Because if you if you can capitalize and move past your weaknesses, almost anything’s impossible. Impossible. It’s just a matter of doing that and being humble enough. I think. Sometimes, which is harder when, as you get more successful, sometimes.
Scott Ritzheimer
Yeah, yeah, it really is. It can become more and more isolating. There’s some folks listening that they’re they’re ready to start a gang, or or they’re they’re just interested in learning more and how they can not do this alone. Tell us a little bit about the book. Remind us of the name and where we can get a copy of it, and then how folks can connect with you and learn more.
Dennis McCurdy
Sure. So the name of the book is “Unleash the Power of Connection”, and it can be bought on Amazon or Barnes and Noble or Digital Chalk or any of those any of those platforms, and they can reach me at just. McCurdy.com. If they want to reach out, be happy to chat with them, give them some ideas. I’ve been involved in a lot of mastermind groups and a lot of coaching and consulting from from both sides, both giving and receiving. So I’m very open to. Yeah, I think you have to be open to learning and being. You know, realize you’re not perfect.
Scott Ritzheimer
Yeah, yeah. So true. So true. Recommend it, especially those of you who have that feeling of being alone, because you’re the only one in your business. That’s a very real thing, but it doesn’t have to be that way. And Dennis, I love the idea, love the approach. Really enjoyed the book, and really enjoyed this conversation. Thanks for being on. It was really a privilege having you here, and for those of you watching and listening, you know your time and attention mean the world to us. I hope you got as much out of this conversation as I know I did, and I cannot wait to see you next time. Take care.
Dennis McCurdy
Thanks, Scott.
Scott Ritzheimer
Hey, everyone. Scott Ritzheimer here. Thank you so much for listening to the Start Scale and Succeed podcast. I hope this episode gave you exactly what you need for the level you’re in right now. If you want to discover what level you’re in, take our 10 question Founders Evolution Quiz for free at foundersquiz.com. That’s foundersquiz.com. It’ll pinpoint exactly where you are, and give you tailored tips to move forward and reach that next level in your journey as a founder. If you got something out of today’s episode, don’t forget to subscribe, rate, or review. It helps us reach more founders like you, and let’s be honest, it means a ton to me, my team, and all our incredible guests. So keep starting, scaling, and succeeding, and I’ll see you in the next episode.
Contact Dennis McCurdy
Dennis McCurdy transformed his life from graduating near the bottom of his high school class and sleeping on an office couch to achieving a seven-figure net worth. Following his military service, he built eight businesses, managed 29 properties, authored four books, and led mastermind groups for over a decade. He teaches that mindset, accountability, and strong relationships drive true achievement. He is the author of the book Unleash the Power of Connection. He actively runs personal development workshops to help others reframe their failures into fuel for growth. He consistently proves that strong network connections and daily discipline directly accelerate personal transformation.
Want to learn more about Dennis McCurdy’s work at McCurdy & Andrew Investments? Check out his website at https://www.mccurdyinvestments.com/
Connect with Dennis through his LinkedIn at https://www.linkedin.com/in/dennis-mccurdy-cfp-465a1bb/
Check out Dennis McCurdy’s personal website at https://dennismccurdy.com/
Get a copy of Dennis McCurdy’s book Unleash the Power of Connection at https://www.amazon.com/Unleash-Power-Connection-accountability-procrastinating/dp/097988635X