Do You Have What It Takes? The Traits Every Solopreneur Needs to Succeed

Watch the Episode on YouTube

What if the secret to success isn’t just about what you do—but how you think? In this episode, we sit down with Margot Machol Bisnow, author of Raising an Entrepreneur, to unpack the mindset that fuels solopreneurs and self-starters alike.

We’re diving into the grit, resilience, risk-taking, curiosity, and compassion that define entrepreneurial success—whether you're raising a future business owner or stepping into solopreneurship yourself. Margot shares wisdom from 99 entrepreneurs and their families, revealing the common threads that shaped their paths.

• Do you need to be fearless?

• What role does failure really play in success?

•  Can you raise an entrepreneur, or is it just in the DNA?

And, of course, we tackle one of the biggest myths in entrepreneurship—the idea that if you love what you do, you’ll never work a day in your life. (Spoiler: That’s not exactly how it works!)

This is a must-listen for anyone carving their own path in business—don’t miss it!

Like the show? We'd love it if you'd leave a 5-star review!

Connect with Margot Machol Bisnow

• Order Raising An Entrepreneur
• Visit https://raisinganentrepreneur.com/

Favorite Quote About Success:

"If you think you can, you can. If you think you can't, you can't." - Henry Ford

Being a solopreneur is awesome but it’s not easy. It's hard to get noticed. Most business advice is for bigger companies, and you're all alone...until now. LifeStarr's SoloSuite Intro gives you free education, community, and tools to build a thriving one-person business. 

So, if you are lacking direction, having a hard time generating leads, or are having trouble keeping up with everything you have to do, or even just lonely running a company of one, click here to check out SoloSuite Intro!

About Margot Machol Bisnow

Margot Machol Bisnow is an author, entrepreneur, and advocate for youth empowerment. She served as a Federal Trade Commissioner and held various leadership roles in government, but she is best known for her book Raising an Entrepreneur: 10 Rules for Nurturing Risk Takers, Problem Solvers, and Change Makers. Drawing from interviews with successful entrepreneurs and their parents—including her own son, Elliott Bisnow, founder of Summit—Margot explores how to raise children to be confident, resilient, and purpose-driven. Her work focuses on helping parents support their children in pursuing passions over traditional paths.

Episode Transcript

Carly Ries: What if the secret to raising a successful solopreneur starts at childhood? In this episode, we sit down with Margot Machol Bisnow, author of Raising an Entrepreneur, to uncover the key traits that shape entrepreneurial success, including grit, curiosity, resilience, and even compassion. So whether you're a solopreneur looking to strengthen your mindset or parent hoping to nurture an entrepreneurial spirit in your child, this conversation is packed with insights you won't wanna miss. You're listening to The Aspiring Solopreneur, the podcast for those just taking the bold step or even just thinking about taking that step into the world of solo entrepreneurship. My name is Carly Ries, and my cohost, Joe Rando, and I are your guides to navigating this crazy but awesome journey as a company of one.

We take pride in being part of LifeStarr, a digital hub dedicated to all aspects of solopreneurship that has empowered and educated countless solopreneurs looking to build a business that resonates with their life's ambitions. We help people work to live, not live to work. And if you're looking for a get rich quick scheme, this is not the show for you. So if you're eager to gain valuable insights from industry experts on running a business the right way the first time around or want to learn from the missteps of solopreneurs who've paved the way before you, then stick around. We've got your back because flying solo in business doesn't mean you're alone.

Oh, Margot, we are so thrilled to have you on the show today. I feel like there's so much that we can talk about, but you recently wrote a book called Raising an Entrepreneur, How to Help Your Children Achieve Their Dreams, 99 Stories from families who did. And you interviewed countless entrepreneurs about this, and I wanna be clear before we kick off some of our questions. we always target solopreneurs, but solopreneurs are also entrepreneurs just not with the intention of scaling with employees. What is, for the sake of this conversation, how do you define entrepreneur?

Margot Machol Bisnow: Oh, thank you because I love that question. For me an entrepreneur is anyone who starts anything. I consider artists, actors, musicians, people like that entrepreneurs. I consider people who start non profits entrepreneurs. I consider people who are activists, entrepreneurs.

I consider people who are solopreneurs to be entrepreneurs. And of course, people who go on and do the whole Silicon Valley thing where they end up having thousands of employees, they are too. But entrepreneurship is an attitude and it's a path.

Carly Ries: Absolutely. And you wrote this book for parents basically to help their kids become entrepreneurs if that's the path that they want. But everything that we're talking about today could also theoretically apply to aspiring solopreneurs because they need that direction. They need to know, where to go. So let's start at the beginning.

How did you get interested in this topic and where did it develop and how did it turn into this?

Margot Machol Bisnow: So before I answer that, the point of the book is not to tell parents to raise their children to become entrepreneurs. The point of the book is for parents to raise their children to become entrepreneurial and to have that mindset that you guys talk about all the time because whatever you do in life, it will help you. And we can go into all the different aspects of it later. Meaning having grit and resilience and fearlessness and all this kind of stuff. Even if you don't become an entrepreneur, I don't think parents can make their child an entrepreneur.

Parents can just raise entrepreneurial children and as you said, like all of those skills and traits are gonna help you in whatever you do in your life. And they're all the skills and traits that you want if you're going to be successful, whether you're running your own business or whether you have lots of employees or whether you're working for someone else but you just have an entrepreneurial, creative, risk taking mindset. I just think that's so important. An answer to your question or did you wanna comment before I answer your question?

Carly Ries: No, no, that makes perfect sense. Thank you so much for the clarification there.

Margot Machol Bisnow: So my older son, Elliot started an organization called Summit or Summit Series in 2008 which is get togethers and conferences of young entrepreneurs. And I

started going I guess in 2010 and have been going once a year, at least once a year ever since then. I just had never met a lot of young entrepreneurs back then, people who like the kind of people you work with all the time who just throw themselves into this thing they're building. And I was just so curious how they turned out the way they did and I asked all of them. And they all said I had someone who believed in me, someone who told me I could do anything I put my mind to and that they'd be there for me even if through inevitable setbacks because they knew eventually I'd be successful.

And usually it was a parent, not always. Sometimes it was somebody else along the way. I was just so struck by this and I just kept talking about it And the kids said, you have to write a book. I'm like, I can't write a book. And they're like, no, no, you have to write a book.

So they wore me down, I wrote a book and then I looked up five years later and they were all doing something else.

Joe Rando: That's being entrepreneurial, right?

what's the next thing I'm gonna do?

Margot Machol Bisnow: So I decided to do a second edition and kind of focus in more on what they were doing today and why they decided to change and everything.

Carly Ries: Well, so let me ask, you said that they all had somebody cheering them on and they had some support. Were there any other commonalities between all the entrepreneurs? I always have trouble saying that word for whatever reason.

Joe Rando: Because you wanna say solopreneur.

Carly Ries: Well, it's all hard. Were there any other commonalities between them that you discovered after interviewing all these people?

Margot Machol Bisnow: I mean, all entrepreneurs basically, they all have the same qualities, right? I mean, if they're gonna be successful, they all have grit, they all have resilience, they all have determination, they're all risk taking, I mean, we can go through all these different traits, they all have curiosity, they're all raised to look around and say, what can I do differently? How can I improve something? How can I change something? I'm sure this is how most of your solopreneurs start their business.

They're doing something, they're knowledgeable about something, they're experiencing something and they're like, wait a minute, there's this one thing about it that's not, I could make that better and then they start

Joe Rando: I wanna clarify though because I love that, I love that description, but it makes me wonder, what about somebody that, I don't know, opens a paint store. Right? So they sell house paint. Is that really I mean, you know, you say do something differently if you look at, you know, it's not really. I mean, there's other paint stores. are you saying do something differently in their life or do something differently in the world?

Margot Machol Bisnow: I mean, in the world because why else would somebody go to their paint store?

Like why open a new paint store when there are 10 paint stores in your town?

Joe Rando: Well maybe there isn't, maybe they have to go to the next town to go to the paint store

Margot Machol Bisnow: So it's a geographic My town needs a paint store but maybe there's something I can do to make my paint store different from every other paint store. Maybe I can have a place in the front where kids can take sample paints and do stuff or you know, something.

Joe Rando: Paint stores are so boring.

Carly Ries: Painting class, you could offer a painting class.

Margot Machol Bisnow: Right, right. Painting class while mom is shopping for paint, you know, the kids can be painting them on the walls or something.

Carly Ries: That's actually a really good idea.

I was like, let's jot this down. Well, you were saying we could dive into those qualities. Let's do that. So grit was one of them. Why is that important?

And how do you even get it?

Joe Rando: And what is it? Define it.

Margot Machol Bisnow: Grit is working really, really hard towards your goal and realizing that life is a marathon, not a sprint. Every entrepreneur I've talked to had a passion outside of school while they were growing up. And in every case eventually their parents supported that passion. And because the future entrepreneur chose the passion, they started working really hard at it. And because they worked really hard at it, they got really good at it and because they got really good at it, they developed the confidence that if they worked hard they could succeed.

And they developed grit because they began to realize that when they worked hard they were successful and when they weren't working hard they weren't as successful. And so, I mean, I'm sure you see this with all the people you talk to that it's every single entrepreneur I've interviewed says, I work harder than anyone else I know. They all say, and because I love what I do I feel like I'm never working a day in my life. They all love what they do, they all work hard at it, they all have that sort of that grit and that focus and that determination And I think that's why they're successful.

Carly Ries: Yeah, so I think another one you're talking about curiosity, which I feel like those can kind of tie in hand in hand. But why is curiosity key?

Joe Rando: Can we pause for a sec? I want to back up because you know, I've been an entrepreneur since 1990. I've done solopreneurship. I've started enterprise software companies that we sold. I really take issue with the idea that you never work a day in your life if you love what you're doing.

Because I've never had that experience. Never. And I've been very successful. I developed a million square feet of retail real estate. I, co founded a software company that ended up selling to companies like, you know, the biggest companies in the Fortune 500.

And there were many days that felt like work in all of those things. And I just don't wanna mislead people to say, you know, it isn't all fun. I hated leasing. I loved having shopping centers and developing shopping centers, but negotiating leases was the low point of my life, and I had to do it all the time if I wanted to be in that business. And I couldn't hand it off because it was too important.

Because you live with these things for twenty five, thirty years. I just want to clarify that I can't abide by you never work a day in your life. At least I never had that experience.

Margot Machol Bisnow: And, but how about today? Aren't you having fun?

Joe Rando: I'm having fun right now. Absolutely.

Margot Machol Bisnow: You finally found the right career.

Joe Rando: Oh, but believe me, there's tomorrow. There is tomorrow. No, I do stuff here that I don't love. and that's just the nature of business to me. So again, it's one of those things where I don't wanna mislead people to think that if you have bad days where it feels like work, you're doing it wrong, because I don't believe that.

Margot Machol Bisnow: No, of course. I agree with you, but I mean, my husband was a lawyer, we know lots of lawyers. I don't know almost any lawyers who like their job.

Joe Rando: I am with you, I've worked with tons of lawyers over the year and every one of them would seem like they wanted to be doing something else except for one.

Margot Machol Bisnow: Yeah, think I know one also. So maybe you've made me clarify like, unlike being a liar where you just don't like your job, if you're an entrepreneur doing something you've chosen that you like, you'll like it the majority of the time.

Joe Rando: yes, yes, yes, absolutely. Okay, deal.

Carly Ries: And then you'll up with the stuff you don't like because you like it so much,

Joe Rando: Exactly. And if you don't like it and I've been there. You gotta leave. You gotta do something.

Margot Machol Bisnow: Move on.

Joe Rando: If it comes like being the lawyer and I'm sorry, lawyers. I know there are some of you out there that are passionate about your jobs and wonderful, and we're not trying to diss you. But it is a true experience for both Margot and myself that we haven't known many that really wanted to continue doing it for a long time. Anyway, disclaimer over.

Carly Ries: Fair enough. Okay, well I'm circling back, curiosity, why is that key?

Margot Machol Bisnow: I think people are successful, first of all, in starting their organization or their company because they've looked around and they've seen what can I do about this that's better? What could I do about this to make it that's different? How could I improve what's already being done? I mean, there's already something in every category. What is it you can bring to it to make it better, to improve it?

You have to be curious, you have to be thinking about that even to get started with your company. And then once you have your company, you can't just keep making the same product and selling it in the same way year after year after year. I'm sure all the people you talk to find this. You're constantly having to reinvent yourself, right? And adapt and change and do new things and new aspects and sell it in different ways and market it in different ways and package it in different ways and promote it in different ways.

And how are you gonna do this if you're not always thinking about what's going on in the world and asking questions?

Carly Ries: I mean, even if they wanna do like a social media strategy, they have to evolve that thinking every week. Oh my gosh, of course. That's always changing, and we all love it so much.

So okay. So you talked about grit, curiosity. You said it earlier that risk taking is also one of them. So how does that plan, how does the fear of failure play in? What are your thoughts there?

Margot Machol Bisnow: Yeah, so every entrepreneur that I've talked to, when they were raised, they weren't punished for failure. Their parents said, What did you learn from this? What will you do differently next time? How would you do it differently if you could go back and do it differently? But they never scolded them, They never criticized them for failing.

And as a consequence, they're not afraid to take risks. And if you're afraid to take risks, you're not gonna become an entrepreneur.

Joe Rando: Nor should you?

Margot Machol Bisnow: No, you shouldn't.

Right, you have to be willing to take risks and you have to be not afraid to fail. Roger Federer gave the commencement address at Dartmouth last June, I don't know if you've listened to it or read it, it's phenomenal. And here's the greatest tennis player of our lifetimes pretty much. And he said, even though he won 80 of his matches, he lost 50% of the points he played in the matches. He said, if you're constantly focused on what you did wrong on your failures, if you're constantly looking back on how you screwed up, you're never gonna be successful.

You take it, you learn from it and you move on.

Carly Ries: Yeah, no, I mean, true. favorites.

Joe Rando: Yeah. Because you will wallow in all the failures if you let yourself do it for a little while and then look ahead.

Look out the horizon.

Carly Ries: I forget, Joe, we were talking to somebody where they're like, I give myself an hour to throw a pity party and then I move on.

Joe Rando: Yeah. I can't remember who that was, but that was good advice. pity party, then what what did I learn?

And then, okay, let's move on.

Carly Ries: Let's do this.

Yeah, absolutely. Okay. So risk taking. So will fail at some things as a solopreneur, as an entrepreneur, which means you need resilience. So let's talk about that factor.

Margot Machol Bisnow: I mean, nobody's gonna have it easy, right? Nothing's ever smooth, nothing's ever just straight up. And people who are discouraged by failure, they're not gonna be willing to take this path. And I think if you're a solopreneur, it's probably even tougher because you don't have anyone else to blame.

Carly Ries: Which can be so easy. It can be so easy to do when you're working with others. And even if it's not warranted in your brain, it's easier to pass it off.

Margot Machol Bisnow: Right, and so I just think it's really important. And back to sort of the whole upbringing thing, I mean, these people were not criticized for failure and these people all said to me when they

went off to start whatever it was they were gonna start, I knew if I failed I could go home. And having that confidence of something to fall back on gave me the courage to take risks, gave me the ability to be resilient. I didn't actually have to go home but I knew I had it there as a backstop. And every single person I've talked to nobody had it. Nobody said, Oh I've got this really great idea, good I'm gonna start it and then it's just gonna be easy and successful and it's just gonna be perfect all the way.

I mean, it's just not how life works. Right?

Joe Rando: That's what we all think.

We all think that. It's gonna be easy.

Carly Ries: Have you also found that, if you have that you can go home, it makes you not want to go home even more because you want to make this business for yourself? I don't know. I feel like if you have that safety net, you wanna be like, okay. But I don't need that. I wanna tell myself I have it, but let's prove that I don't need it. Have you found that?

Margot Machol Bisnow: I mean for some, some actually did go home, for a year, you know, they turned down, an opportunity to go to Wall Street or whatever and said to their parents, I'm moving home for a couple years to save money and start this idea I have in my head. You know, even though my friends are laughing at me for turning this down because I think I can do this thing. And other people said to me like, I mean John Chu, the movie director who did Wicked, he said to me, I always knew if I failed I could go home and that gave me the courage to take risks. And he said he never had to go home but he said having that gave him courage. So, I think it's different with different people.

Sometimes you need to go home and sometimes you just need to know you can go home.

Carly Ries: Joe, I didn't even tell her that she should mention Wicked in this episode. So that was even coming to me. I have a weird obsession right now that Joe has had to put up with, with Wicked.

Margot Machol Bisnow: Oh really?

Joe Rando: I still haven't seen it so.

Carly Ries: I know. Okay. So let's get to the last quality. And I love this one. And I think it's one that people don't really consider it as a quality that all solopreneurs, entrepreneurs share, or should have, but compassion.

So what does that mean as it relates to the entrepreneurial mindset?

Margot Machol Bisnow: I think it's one of the common misperceptions by people who aren't entrepreneurs that people become entrepreneurs to make money. And I don't think that's true. I think most people become entrepreneurs because they have this idea.

Joe Rando: That needs to be in the world, right? The idea that needs to be in the world, yep.

Margot Machol Bisnow: Yes, yes. They have this idea and they wanna do it. They wanna bring it to people. They think people's lives will be better if they have this product or this service or something that they think they can provide. And I don't think you have that unless you're raised with compassion to care about other people, what other people think and how your actions affect other people.

It's more than just being kind. I mean, kindness is so important But it's more than that. It's just being raised to think you know, how can you make the world a better place? How can you do something to improve people's lives?

Carly Ries: Absolutely. Margot, I just love this conversation. Joe and I actually have a quiz that we're about to put out that like, are you cut out to be a solopreneur? And it goes through all these questions. And I feel like everything we've covered today kind of walks through, do you have these qualities?

Do you have what it takes to have that entrepreneurial mindset as a solopreneur? And I just think it's gonna be so helpful helpful for so many people. So one, I just wanna thank you for coming on this show. But two,

Joe Rando: And I wanna say, one of the things that makes me crazy are these people that are basically encouraging people that they should start a business and kind of implying that if you don't, you're kind of a loser employee and I'm saying, dear god, no. There are so many people, number one, that are gonna be happier being an employee than being in their own business. And you know, it just depends on what your feed looks like on LinkedIn, right? But this is kind of things that I see a lot. And I'm like, that is not true.

number one, if we were all starting our own businesses, we'd probably all be either solopreneurs or small businesses, and we wouldn't have cars and cell phones and all these things we kinda like. But it's just that there are people that are built to work in companies and be employees and be part of a process you know, so thank you for making that very clear in what you're doing. Your work is basically outlining why some people are better off not doing this and that's great.

Margot Machol Bisnow: So I don't think you can make someone an entrepreneur. Of all the people I interviewed, five of them have a sibling who's an entrepreneur out of 75 and all of those who have a sibling who is an entrepreneur also have a sibling who's not an entrepreneur. As you say, you're taking on a lot of risk and you're working really hard and there's a lot of uncertainty and not everyone is cut out for it. But I would say to everyone who wants to consider it, go for it because whatever you were gonna do otherwise, it'll be there in a few years if this doesn't work out and the skills you had, you've gained and the experience you've gained will be invaluable and whatever else you wanna do. Nobody today gets a job and keeps it for forty years And if they do, they're probably miserable.

So try it, go for it. And if it doesn't work, go do something else.

Joe Rando: I'm really glad you didn't say thirty years because I have a property management company with somebody that's been there for thirty years and I think she's happy.

Carly Ries: Yeah. She cannot go anywhere. Well, that's great.

Margot Machol Bisnow: that's great. But how many people do you know are who are in the same job thirty years later?

Joe Rando: None. It's weird. It's great.

Carly Ries: It's also a generational thing. I think that's just the trend. I mean, my dad was in the same career for forty years. And when I first left my first job after college, he was so concerned. he's like, you don't wanna be a career jumper,

Margot Machol Bisnow: let your child do what gives them joy, let them pursue this path. So many parents and I talk to them and they're like, well, what if they can't make a living? And I'm like, okay your goal for your child is they should spend forty years doing something to make a living that they don't enjoy? That's what you think would be a good outcome for your child to spend forty years being unhappy eight hours a day? No, let them go, let them try it and it's gonna be fine and if after a few years it doesn't work and they wanna go work for a company, that's great, they can do that.

They'll have all this knowledge and experience and wisdom that they can apply in their new job.

Carly Ries: Have you guys seen that interview with the little kid where the reporter goes, what do you wanna be when you grow up? But the little boy goes, happy. But it's just like, oh, yes.

Margot Machol Bisnow: Apparently that's John Lennon also said that in school. Maybe he quoted it. They said, what do you wanna be when you grow up? And he said happy and they said, you didn't understand the assignment and he said you don't understand life.

Carly Ries: Oh, have never heard that. So maybe this kid was just quoting his parents or something, but it was cute in the interview. Well, Margot, we ask all of our guests this question. What is your favorite quote about success? Of your many.

Margot Machol Bisnow: Yeah, I was trying to think of all my favorite quotes so that I'd come up with something clever. And I have so many that I would love to share, but I think the one I'm gonna leave you with is Henry Ford who said, If you think you can, you can. And if you think you can't, you can't.

Carly Ries: Love it. One of my favorite quotes too.

Margot Machol Bisnow: I would encourage everyone that you talk to, every one of these people to think they can and to go for it.

Carly Ries: I love it. That is a great way to end the episode. If people want to learn more about you, find the book, where can they find you?

Margot Machol Bisnow: Yeah, so it's Raising an Entrepreneur, second edition on Amazon. I also have a website raisinganentrepreneur.com and I'm on Margotbisnow, I'm on Instagram and I'm LinkedIn and you name it, all the stuff.

Carly Ries: All the things. So we will include all of that in the show notes but thank you so much for working on the show today. Oh, it's my pleasure. And listeners as always, we love that five star review. We would love it if you'd subscribe on your favorite podcast platform, and we will see you next time on The Aspiring Solopreneur.

You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes, running a one person business and figuring it out as they go. So why not connect with them and learn from each other's successes and failures? At LifeStarr, we're creating a one person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com.