Eps 669: Margot Bisnow on Raising Entrepreneurs

Episode 669

This week I’m sharing a conversation I had with Margot Bisnow, who interviewed more than 70 families raising wildly self-driven kids. She went looking for a formula and found something more ordinary. We get into how to tell a real passion from checking out, and what parents do in the moments after their kid fails. She also tells the story of biting her tongue when her son left college halfway through. If you’re white-knuckling your teen’s path, my friend, this one’s for you.

Guest bio

Margot Machol Bisnow is the author of Raising an Entrepreneur: How to Help Your Children Achieve Their Dreams, 99 Stories from Families Who Did, written after sitting down with more than 70 families whose kids grew into wildly self-driven adults. Before that she spent 20 years in government, including serving as an FTC commissioner and as staff director of the President’s Council of Economic Advisers. Her two grown sons found their own paths: Austin is a musician who founded the band Magic Giant and the folk duo Somewhere in Between, and Elliot founded the Summit conference series for young entrepreneurs and led the purchase and revival of Powder Mountain in Utah. When she isn’t talking about parenting, she’s traveling or with her family.

Community is everything!

Join our community Facebook groups:

Takeaways from the show

https://www.besproutable.com/wp-content/uploads/2026/08/TULUM_MISC_079-copy-scaled-e1787672851769.jpg
  • Watch your kid before you judge the passion
  • Finish what you signed up for, then quit
  • Pushing your passion onto your kid backfires
  • Attitude toward failure separates these kids from others
  • Skip both the blame and the excuses
  • “What would you do differently?” beats reassurance
  • Grades predicted nothing about future success
  • Find the environment where your kid thrives
  • Kids risk more when home stays open
  • Lead by following, wherever your child goes

“Having an opportunity to help your teenager discover their passion and pursue their passion, and have a happy and fulfilled and joyful life. It’s hard. It takes courage. But it is actually the most joyful thing we can do, is to raise joyful kids.” – Margot Bisnow

 

Resource list

Margot’s work

  • Raising an Entrepreneur: How to Help Your Children Achieve Their Dreams, 99 Stories from Families Who Did — second edition, the one with the photos, on Amazon
  • Website: Raising an Entrepreneur (articles, podcast appearances, book links)

Mentioned in the episode

  • Thomas Vu, lead producer on League of Legends
  • Benny Blanco, music producer
  • Blake Mycoskie, TOMS Shoes
  • Joel Holland, Harvest Hosts
  • Summit and Powder Mountain
  • Magic Giant and Somewhere in Between
  • Roger Federer’s 2024 Dartmouth commencement address
  • Angela Duckworth’s work on grit and parenting styles
  • Carol Dweck on effort and mindset

From Casey

  • Positive Discipline family meetings and co-created agreements
  • Back-to-School Checklist: bit.ly/teenchecklist
  • Living Joyful Courage Immersion Week, September 21–25
Subscribe to the Podcast

We are here for you

Join the email list

Join our email list! Joyful Courage is so much more than a podcast! Joyful Courage is the adolescent brand here at Sproutable. We bring support and community to parents of tweens and teens. Not a parent of a teen or tween? No worries, click on the button to sign up to the email list specifically cultivated for you: Preschool, school-aged, nannies, and teachers. We are here for everyone who loves and cares for children.

I'm in!

Classes & coaching

I know that you love listening every week AND I want to encourage you to dig deeper into the learning with me, INVEST in your parenting journey. Casey O'Roarty, the Joyful Courage podcast host, offers classes and private coaching. See our current offerings.

Transcription

[00:00:00] Casey O'Roarty: Welcome, welcome. Welcome to the Joyful Courage Podcast. This is a place where parents of tweens and teens come to find inspiration, information, and encouragement in the messy terrain of adolescence. This season of parenting is no joke, and while the details of what we're all moving through might be slightly different, we are indeed having a very collective experience.
[00:00:30] This is a space where we center building relationship, nurturing life skills, and leaning into our own personal growth, and man, the opportunities abound, right? My name is Casey O'Rourty. I am a parent coach, Positive Discipline lead trainer, and captain of the adolescent ship over at Sproutable. I'm also a speaker and a published author.
[00:00:53] I've been working with parents and families for over 20 years and continue to navigate my own experience of being a mom with my two young adult kids. I'm so honored that you're here and listening. Please give back to the podcast by sharing it with friends or on social media. Rate and review us on Apple or Spotify.
[00:01:13] Word of mouth is how we grow. Thank you so, so much. Enjoy the show.
[00:01:23] Hey, listeners. I am so glad that you are back for another show. So, you know, most of us carry around this quiet hope for our kiddos that, you know, someday they'll do something that's really theirs, something that lights them up from the inside, that makes a positive impact on the world. You know, we have these hopes, but we also have just a regular Tuesday afternoon where our teenagers are behind closed doors for what feels like hours, and the dishes are still in the sink, and maybe you're standing in the kitchen wondering whether you've raised a future anything, or if you're just kinda slowly losing your mind.
[00:02:05] My guest today is Margot Bisnow. She sat down with more than 70 families who raised wildly self-driven kids, and she went in expecting to find some kind of secret formula. What she found was a lot more ordinary than that, and honestly, kind of a relief because it's a lot of what we talk about here on the show.
[00:02:28] She found parents who believed their kids. They made them feel like they belonged, and at some point they loosened their grip, sounds familiar, on how it was all going to turn out, and started trusting the kid right in front of them. I love that. And, you know, she wrote this book called Raising an Entrepreneur: How to Help Your Children Achieve Their Dreams.
[00:02:51] Before all of that, she spent 20 years in government, including a stint as an FTC commissioner and staff director of the President's Council of Economic Advisers. Her two sons, who are grown now, so she's made it to the other side, one of which is Austin, started an alternative band, Magic Giant, and the folk duo Somewhere in Between, and her son Elliot founded Summit.
[00:03:16] The conference series for young entrepreneurs and led the purchase and revival of Utah's Powder Mountain. When she isn't talking about parenting, she's traveling and spending time with her family. I'm so excited to welcome her to the show. Hi, Margo. Thanks for being here.
[00:03:33] Margot Bisnow: So excited to talk to you and your, all your people.
[00:03:37] Casey O'Roarty: Yes. Yes, yes, yes. So I'm really excited to dig into your book. You talk about how, you know, in the book, every one of the kids had some passion outside of school, and I relate to this. I think back to my kids in the teen years, especially the ... I mean, they're both kind of fresh out, but you know, the years when they are at home in the house with us, and looking around and seeing them, you know, glued to video games or watching videos that are other people playing video games.
[00:04:09] It's crazy-making, and it just always read as such a waste of time. How do you help parents tell the difference between what's a real passion and what's just our kids kind of checking out, or even just taking an easy road? What would you say?
[00:04:27] Margot Bisnow: It, there's not an easy answer because you have to look at your kids.
[00:04:32] Mm-hmm. And you watch them, and you have to see. And you have to see if this is something they're passionate about or if it's just something that they just kind of seem to be, you know, zoned out and doing. And with video games, it can be one or the other. Um, one of the people in my book, Thomas Vu, always loved video games, uh, was a good student.
[00:04:54] His mom said as long as he got As and played, played a sport, she'd let him spend all the time he wanted on video games, but she really wanted him to grow up and be a doc- a doctor or something.
[00:05:07] Casey O'Roarty: Mm-hmm.
[00:05:07] Margot Bisnow: And one semester before he should have graduated from college studying some science something, he had a chance to talk to someone from Electronic Arts and told them about an idea he had.
[00:05:20] They, they, they'd come to his university, and, um, they invited him back, and he ended up dropping out of college and joining their first intern class at Electronic Arts and became one of the lead producers of League of Legends. And- Wow.
[00:05:36] Casey O'Roarty: Even I have heard of that, and I am not in the video game world at all.
[00:05:41] Margot Bisnow: And his family had, uh, emigrated from Vietnam, and just like the craziest story. You know, with their boat set upon by pirates, and I mean, uh, um, you know, arrived in the US with nothing. And, um, the first time he went back to Vietnam, it was to the town he'd come from to a football stadium with, like, 100,000 people watching his people play his video game.
[00:06:05] Casey O'Roarty: Mm. Wow. You never know. I can think back and remember my son was a basketball player, and he would talk his big game about his, you know, dreams about basketball. And yet what I knew about kids that really went for it is the basketball never left their hand And that was not Ian. Ian had all sorts of other things he liked to do too, and so while we absolutely offered, you know, to support with various teams, and we were ready to be there for him if that was really it, I could kind of see, well, this is something he likes to do, but he's not...
[00:06:44] This is not a kid who's going to the NBA or anything like that. And I wonder also about, you know, especially around sports, and maybe this is not necessarily inside of this conversation, but I do wonder about, uh, y- like, the level of push that parents do when they see that little spark. My daughter also had this really beautiful gift for music, and she started playing piano early on, and I got so excited about it, and we had flowcharts for her practice schedule, and, "You decide which three or four days a week you practice," and it became such a power struggle that she said, "I'm done.
[00:07:24] No more. I'm not gonna do it anymore," and she quit. So I- it feels like... You know, when I talk to parents too that see their kids doing well at something and are unsure around, like, when do we lean in and say, "Nope, you signed up, you finish," and when do we let go and say, "This is yours to do what you want with it"?
[00:07:49] How do we differentiate?
[00:07:50] Margot Bisnow: So many questions.
[00:07:51] Casey O'Roarty: So many questions. There you go, Margo. Well, my- Solve it all.
[00:07:55] Margot Bisnow: My personal rule about when do you quit and when... was if I signed up for something, they had to finish that. Okay. So if it was, you know, a six-week camp or a semester's lessons or whatever, and then if they didn't like it, they never had to do it again.
[00:08:11] Um, I, I think it's a terrible mistake for parents to push their passion onto their kids. My older son was a, became a tennis player. We don't play tennis. And, and by the way, sort of in answer to the beginning of your question- ... more than 30% of the entrepreneurs I know, it was sports that they played at an elite level on into college, and I only know one person who became a professional.
[00:08:41] My older son, Elliot, had done every sport and f- sort of f- fell in love with tennis when he was about 12, and at that point, kids who end up top in the country are already doing regional tournaments. Mm. And I said, "I'm not taking you to a regional tournament until you've won a local tournament," not because I was trying to encourage him, but I just didn't see the point.
[00:09:04] And he just kept playing and kept losing, and he'd say, "I know what I did wrong. I'll beat him next time," and he fought his way up to 35 in the country.
[00:09:13] Casey O'Roarty: Wow.
[00:09:14] Margot Bisnow: And he was honored by the tennis center where he trained. And he said in his speech, he said, "Everything I am today is because of tennis."
[00:09:25] Casey O'Roarty: Hmm.
[00:09:26] Margot Bisnow: He said, "I didn't really like school.
[00:09:27] I didn't work hard at school. Tennis is where I learned grit, and focus, and determination, and resilience, and all the skills I needed to be successful in life." So I would say, you know, and, uh, we don't play tennis. I'd be the, like, the only parent when we started finally going to these tournaments with the top kids in the country who didn't know any of the rules.
[00:09:47] Casey O'Roarty: And- That's me with c- club volleyball. My daughter had a two-year experience with club volleyball, and I was the clueless mom.
[00:09:54] Margot Bisnow: Right. And I mean, I think that's good because it's something they chose.
[00:09:57] Casey O'Roarty: Yeah.
[00:09:58] Margot Bisnow: And, you know, the parents, the kids whose parents were tennis players, you could just see it, there was no joy.
[00:10:04] Casey O'Roarty: Yeah.
[00:10:05] Margot Bisnow: And so, I mean, back to what you were asking, Casey, I mean, it's like, does it give them joy? Is it what they love?
[00:10:12] Casey O'Roarty: Mm-hmm.
[00:10:12] Margot Bisnow: They love it, let them do it. And if, you know, after five years they don't wanna do it anymore, they wanna switch instruments or whatever, let them switch instruments. Let them switch sports.
[00:10:22] Who cares?
[00:10:23] Casey O'Roarty: Yeah. It doesn't matter. It's, it's funny, I hear from parents, clients, who will say something like, "Yeah, but I d- I don't want them to regret quitting." And my response is always, like, "Who doesn't have regrets?" Like, it's n- it's a part of life. And I mean, it's, it's not our job to create a world where our kids have no regrets, especially if everything, you know, that they're saying and doing is indicating that this has run its course-
[00:10:54] Margot Bisnow: Well-
[00:10:54] Casey O'Roarty: for now ...
[00:10:55] Margot Bisnow: in fact, I think it's the reverse. I think parents who want to prevent their kids from having regrets are doing their children- Yeah ... an enormous Disfavor Yeah I mean, because as you say, you have to be prepared for life. You have to be prepared to screw up. You have to be prepared to fail. You have to be prepared to get fired, to get be terminated, to be told you're not working out.
[00:11:22] You, you have to be prepared when things don't work out the way you had hoped, and you have to be resilient. Mm-hmm. And you have to be able to bounce back, and you have to have the confidence to know that you can bounce back.
[00:11:36] Casey O'Roarty: Yeah. Yeah
[00:11:37] Margot Bisnow: Confidence to know that you have failed, and you have picked yourself up, and you have started over, and you've done even better the next time.
[00:11:45] Casey O'Roarty: Yeah. I think that's such a great piece. I know, like especially in adolescence, early adolescence, and what I wanna talk about how powerful it is to lose and to fail and what we get to learn from that, and when it's the first time, how it can... I remember, same son, same sport, the first time he tried out for an elite basketball team and did not make it.
[00:12:08] I can bring up a crystal clear picture in my mind of how devastated he was, and reminding myself he's never had this kind of disappointment. And so of course, his ability to be with it has not really been developed quite yet. And, you know, the same thing with his first heartbreak. I remember thinking to myself, "Okay," c- calming myself down, right?
[00:12:39] Because it's not easy for us parents to be in the discomfort that our kids are moving through. But I remember thinking to myself, "Of course, he has no..." And it's helped me remind other parents too, they don't-- This is when they start to build that ability and the muscle memory of like, "Oh yeah, I've felt like this before, and I've made it, and it doesn't feel like this forever."
[00:13:02] Right? Right. So talk a little bit about how we can hel- In those moments as parents, and they're just really devastated by whatever the disappointment is, the fail or the loss Everybody. We're not here to fix it. We're not here to, like, dance around until they feel better. What actually helps our kids build something out of those disappointments instead of just leaving them, you know, feeling like a failure?
[00:13:32] What's helpful?
[00:13:33] Margot Bisnow: So I'm so glad you asked me that. Um, I think it's the major difference between kids who end up becoming entrepreneurial... And by the way, I don't, you don't have to become an entrepreneur, but just to have an entrepreneurial attitude toward life. Um, the major difference between those kids and other kids is the attitude toward failure.
[00:13:55] Casey O'Roarty: Mm.
[00:13:56] Margot Bisnow: And the main reason that they have this positive attitude toward failure is because when they failed, as you're asking, Casey, when they failed, their parents didn't punish them, their parents didn't blame them, their parents weren't angry and say, "It's your fault the team lost," or whatever. You know, you just...
[00:14:15] Whatever, something awful. And the parents also didn't do the other terrible thing that parents can do, which is say, "Oh, it wasn't your fault. You were cheated." You know. Right. No. It- You failed this time. It didn't work. What did you learn?
[00:14:30] Casey O'Roarty: Mm-hmm. What did you learn?
[00:14:32] Margot Bisnow: What, what did you do-- What would you do differently next time?
[00:14:35] How are you gonna fix it? Do you wanna fix it? How, how are you gonna do that?
[00:14:40] Casey O'Roarty: Yeah. Do you have anything... 'Cause I'm-- Yes, I love that response, and I'm thinking about the m- uh, the, the moment, like, the timing of that conversation, right? Yeah. So the loss has happened, the fail has happened, the kid might be really in, really dysregulated.
[00:15:00] My guess is you're gonna say, you know, first and foremost, we get to wait for nervous systems to come back online, and then we get to start asking some, some, some, uh, critical questions, some curiosity. Yeah? Right.
[00:15:14] Margot Bisnow: I mean, I think it depends on each child. Each-- The parent wants to know their kid, and when their kid, if they wanna talk about it then or not till the next day or after dinner- Yeah
[00:15:23] or whatever. But, um, I think that's one reason that so many future entrepreneurs s- spend so much time in sports. Because with sports you lose all the-
[00:15:37] Casey O'Roarty: Mm-hmm ...
[00:15:39] Margot Bisnow: all the time. And if you're devastated by loss, you're never gonna be good in your sport. You have to ask yourself, "What would I do differently? How would I change?"
[00:15:50] You know? And, and, and, and I think being able to pivot, being able to change your approach, being able to try new things, it's just, it's so validating. Um, Roger Federer gave this great commencement re- address at Dartmouth a year ago, and he said... And he's, like, the greatest tennis player of, you know, our generation.
[00:16:13] And he said, "I won 80% of my matches. I lost 50% of my points I played. If you're always focused on the point you lost, you're never gonna be successful."
[00:16:25] Casey O'Roarty: Mm.
[00:16:25] Margot Bisnow: You just move on.
[00:16:26] Casey O'Roarty: Yeah.
[00:16:27] Margot Bisnow: And, you know, that's true in life.
[00:16:30] Casey O'Roarty: Yeah. And I think it's important to point out that that's not necessarily somebody's temperament, that's the way that somebody's been responded to, would you say?
[00:16:39] Like, nature or nurture? Or probably both, 'cause I think there's definitely more easygoing kids n- naturally, and maybe some kids that are more driven naturally. But I also think that there's so much we can create in the environment that is supportive of that, you know, what you're talking about, that resiliency, that bounce-back.
[00:17:01] Margot Bisnow: Right. And I mean, if they didn't get the part in the play, or they didn't make the basket that would have won the game, or whatever it is that, that the failure, not to say, "Oh my God, I can't believe you screwed up," and not to- Mm-hmm ... it wasn't your fault.
[00:17:17] Casey O'Roarty: Right.
[00:17:17] Margot Bisnow: But, but to say, like, "Hey," you know?
[00:17:20] Casey O'Roarty: Yeah. "
[00:17:21] Margot Bisnow: Nobody's perfect.
[00:17:21] But how would you fix it? What would you do differently?"
[00:17:33] Casey O'Roarty: So I'm a positive discipline trainer. That's the foundation that I stand on with my parent work, and we often will talk about, as far as parenting styles go, that there's this authoritarian style, and then there's this permissive style, and really the goal is to be in the both/and of the kind- Right ... and the firm.
[00:17:50] And that's really, when I hear you talk about being curious about... A- and mistakes are opportunities to learn is a huge pillar of positive discipline as well. Right. So this is so in line with what we talk about here. But it, yeah, really recognizing how we can be supportive without being kind of that waffley...
[00:18:12] Well, without being cruel, right? How could you do that? Let's, let's list off all your mistakes. Or being, you know, kind of doormaty, lawnmower parent of like, "I don't want you to feel bad, so I'm gonna do whatever it takes to convince you that it wasn't your fault." So I really am appreciating that.
[00:18:29] Margot Bisnow: After I wrote the first edition of the book, Angela Duckworth came out with something about parenting for grit.
[00:18:34] Yes. And she talked about the different parenting styles, the authoritarian and the permissive, and why these are so bad. And I s- And, and parenting for grit is exactly how every parent that I interviewed, how they raise their kids, which is Not authoritarian in terms of saying, "This is what you have to do."
[00:18:53] Casey O'Roarty: Right.
[00:18:53] Margot Bisnow: But authoritarian, but not loosey-goosey, like- Right ... like expectations, you come to dinner- Yeah ... you make your bed, you know, you're polite, that kind of thing.
[00:19:01] Casey O'Roarty: Absolutely. Yeah. And, and- It's a different leadership style, that authoritative, right?
[00:19:06] Margot Bisnow: But then in terms of permissive, quote, permissiveness, it's like, "Oh, you wanna go to Europe for the summer?"
[00:19:12] and, uh, "Okay." "Oh, you wanna change schools? Uh, okay." I mean, like, letting your kids have freedom to make big decisions about their life.
[00:19:21] Casey O'Roarty: Yeah. Yes, yes, yes. Yeah, that's e- absolutely. Yeah, giving them a voice, you know, valuing voice, valuing contribution and contribution of ideas, and then really using those contributions, right?
[00:19:35] 'Cause I think we can kind of give, you know, we can give this, "Oh yeah, you can have a voice, you can give your opinion, but at the end of the day, it's actually what I want that's gonna happen." You know? So it's such a beautiful gift to our kids when not only do they have an, a voice, not only is their opinion valued, but it also has worth.
[00:19:53] It also has power in, you know, not all the power. We're sharing power. This is a democ- I mean, to me it really feels like a democratic way of parenting. And we are still the leaders. Right. You know, the adults in the room are still the leaders, and, you know, the gift of good leadership is how we empower the people around us, right?
[00:20:14] So let's talk about grades. Let's talk about grades- Great ... 'cause I, I love this conversation. I come from a family who paid me for grades, and my car depended on my grades, whether or not I could drive it, and guess what? I got the bare minimum to keep the car, and- ... you know. So unfortunately my parents didn't know about Carol Dweck's work when, uh, they were raising me in the '80s.
[00:20:36] But one of your rules again is don't worry about the straight As, which is a hard sell for parents sometimes that believe that grades are everything, or the conversation is, "Well, it's about your effort," right? Like, I appreciate that, and the next breath is, "And you should be getting straight A's because you can.
[00:20:57] If you were putting in the effort, it would look like." So let's talk a little bit about this, 'cause I think it's a really juicy place.
[00:21:05] Margot Bisnow: So this was something that was very interesting to me. My father was a professor. I grew up in university towns. I grew up where academics were important. My husband and I both have advanced degrees from top schools, and we just thought that was how everything would work out.
[00:21:23] So it was very interesting to me. Some of these entrepreneurs breezed through school, breezed through Ivys, got advanced degrees, and some of them didn't And it had no correlation to their future success. And again, you have to look at your kids. Mm. You have to pay attention. Are they not doing well in school because they don't care, because they're not trying?
[00:21:49] Or are they not doing well in school because, you know, they're just not good at trigonometry, but man, are they good at music.
[00:21:55] Casey O'Roarty: Mm-hmm.
[00:21:56] Margot Bisnow: You know? And so do we say, "Stop playing music and go study your trigonometry"? Why?
[00:22:02] Casey O'Roarty: Yeah. Why?
[00:22:04] Margot Bisnow: You know? Do they really need trigonometry if they don't wanna go into math or science?
[00:22:10] I mean, you may have a kid who loves science and who's a straight-A student and who wants to be a doctor. That's fantastic. You may have a kid who g- always gets good grades and is in the debate club and wants to be a lawyer and go to a great school. That's fantastic. You may not. You may have a very different kid.
[00:22:32] You have to pay attention.
[00:22:34] Casey O'Roarty: Mm-hmm. You
[00:22:35] Margot Bisnow: have a kid who's completely different and who could end up being hugely successful. I mean, one of my favorite in the book is this guy Benny Blanco, and I think a lot of people have heard of him recently 'cause he just married Selena Gomez.
[00:22:48] Casey O'Roarty: Oh, there you go. That's why it sounds familiar.
[00:22:50] Yeah. Yes. He's-
[00:22:51] Margot Bisnow: He's one of the country's top, um, music producers and music writers, and has something like 25 number one hits. I'm sure he's the most successful kid his high school has ever produced. And, uh, his mother said he... she got a call from his kindergarten teacher every week when he was little complaining that he wouldn't sit in the circle.
[00:23:12] And, um, Benny said all his teachers found him so annoying, and his, uh, his mom found a, a music teacher outside of school who said he was the most talented kid he'd ever worked with.
[00:23:24] Casey O'Roarty: Mm.
[00:23:25] Margot Bisnow: Which meant more to Benny than the fact that all his teachers thought he was an idiot. And his, his mom, starting in high school, let him w- he's from the DC area, let him, you know, take a bus to New York on weekends to work with music producers.
[00:23:38] And, you know, he's a star, and he, and he said, "I always knew I'd do well enough, you know, just to prove my teachers that just because I was annoying, you know, it was okay." But it just, you have to pay attention to your kid.
[00:23:50] Casey O'Roarty: Yeah. Yeah. I literally just had a coaching client earlier today, and we spend a lot of time talking about one of her kids on every call, and how, first of all, their temperaments are so drastically different, and so it's really challenging for the mom to keep her nervous system, you know, grounded as her daughter's just, like, wants to do all the things.
[00:24:12] And one of the things I said to her today was, "Hey, listen." You've got a kid that is gonna absolutely 100% create the life that she wants and nothing is gonna get in her way, and it's hard to parent. It's hard to parent that kid 'cause she's- this is her tr- you are her training ground, right? And I, I just, I love that story about Benny.
[00:24:33] I think there's so many kids and, you know, the system as it is is not a great system. It's a terrible system. And some kids can kinda roll with it. You know, my son could roll with it. My daughter could not, and ended up dropping out of high school, which again, coming from a family where you get paid for grades and everything matters and it's about your worth, it was very difficult for me to roll with that.
[00:25:00] And she's found her way on her own timeline to an educational path that includes her as a, my listeners are probably so tired of hearing me say this, but but she is studying biochemistry, wants to go to graduate school, wants to be a PhD, wants to work in a lab. Like she Found her way on her terms, and because of that, is thriving.
[00:25:30] Mm-hmm. Right? So there's all this traditional modeling and system that we feel like because that's how it's been, that's how it should be, and what I'm hearing you say again and again, we get to know our kids. We get to pay attention and see what it is that they need, and on a lot of levels, let them, let them take some of the lead.
[00:25:51] Margot Bisnow: And you have to put your kid in a situation where they're going to thrive.
[00:25:55] Casey O'Roarty: Yeah.
[00:25:56] Margot Bisnow: And I mean, a lot of kids in, that I talk to, a lot of these entrepreneurs, some of them were happy in big public schools, and some of them were miserable in big public schools. And some of them- Yeah ... were happy in small private schools, and some of them were miserable in small private schools.
[00:26:10] And you have to see that, so the parents with, who had miserable kids in small schools, let them go to big schools, and the parents who had- Yeah ... kids in big schools, let them go to small schools. And someone let their kid go across the country and live with an uncle and go to a completely different kind of school one year, and someone else let their kid go abroad and study for a year, and someone else let their kid take a year off.
[00:26:30] I mean, it, you have to see what works for your child. You have to- Yeah ... find where your child can thrive. And my younger son, Austin, who's an extraordinary musician, he wrote 300 songs in high school. I mean, they just like poured out of him. And when he was, he, and he knew he wanted to major in music composition in college, and we were looking at all these different schools.
[00:26:52] And I mean, he got in everywhere 'cause he, the stuff he had written in high school was just amazing. But like at first, we almost applied early admission to NYU, and we looked at the requirements, and it was like, you know, science and math and calculus and I don't know, sociology and-
[00:27:08] Casey O'Roarty: Yeah ...
[00:27:09] Margot Bisnow: psychology. And like we're like, ah, you know.
[00:27:12] And then he found the University of Colorado, which had like tons of requirements in the music school, and then it was like 20 credits outside the music school, anything you want.
[00:27:22] Casey O'Roarty: Oh,
[00:27:22] Margot Bisnow: great.
[00:27:22] Casey O'Roarty: And he's like, "
[00:27:23] Margot Bisnow: Yep, that's me." Yeah. And he took poetry and creative writing and acting and African dance and- Amazing
[00:27:32] you
[00:27:32] Casey O'Roarty: know,
[00:27:32] Margot Bisnow: things that are gonna help him in his music career.
[00:27:35] Casey O'Roarty: Yeah. You
[00:27:36] Margot Bisnow: know? Yeah. So we found, we found the school that was right for him. There's not like one right school. There's not one right way. There's your child, and you have to figure out what works for your child.
[00:27:49] Casey O'Roarty: Yeah. I love this through line. I love that we keep coming back to this, and I also am really curious what you think.
[00:27:56] There is also this piece, and I think it's a human thing, and it's not only in our relationship with our teenagers, I think it's also happens in other significant relationships of our life, which is thinking that we know what's right. And being able to let go of the unfortunate popular opinion of, oh, teenagers, they don't know what they want, right?
[00:28:22] Or teenagers, you know, they don't, they don't have a clue. It, it makes me so sad that that is such a common quick comment to be made about adolescents How do we let go of the idea that what we believe to be the right path for our kid might not, we might not know?
[00:28:45] Margot Bisnow: Right. So I think this is a great question, Casey.
[00:28:49] Parents want their kids to be successful and happy. Yeah. And so they think if they follow the path that worked for them, it's going to work. And it's a different world, and so they don't need that path. I can give you a couple stories. Um- Please do ... I just gave a talk to a whole group of entrepreneurs up on Powder Mountain, and afterwards a dad came up to me and he said, "You know, can I talk to you?
[00:29:12] I'm just so distraught. I haven't talked to my son in three weeks. He started this stupid little company in his dorm room at college, and I think it's the stupidest company I ever heard of, and he just announced he's dropping out of college and he wants to move home and work on his little company. And I think he's ruining his life."
[00:29:27] And I called over this- Oh, I'm
[00:29:29] Casey O'Roarty: so glad he was there to see you speak, Margo ...
[00:29:32] Margot Bisnow: I called over this guy who I know had dropped out of college and I know had made a small fortune, a large fortune. And, um, I said, um, "Craig, let me ask you a question. You have a choice of hiring two kids. One of them quits college, moved home, worked on his little widget company for a couple years, ultimately decided that it really wasn't going anywhere and he wanted to work in a real company and kind of see how that works.
[00:30:01] The other kid stayed in school, wasn't inspired by anything, didn't get particularly good grades, but somehow graduated. Which kid do you want?" And without blinking, he said, "The first kid," and so did the other 300 entrepreneurs in this room. And the dad was just like, "Wow, thank you." Mm-hmm. Like it just hadn't occurred to him.
[00:30:22] Yeah. He thought his
[00:30:25] Casey O'Roarty: kid was ruining
[00:30:26] Margot Bisnow: his life. Yeah. And if I can just give you one more example. So I, I said, like my dad was a professor. I grew up in university towns. It didn't occur to me that I could have a kid who wouldn't graduate from college. It was just like a given. And, um, Elliot, my oldest son, called up two and a half years, halfway through his junior year and announced he was taking a semester off.
[00:30:45] And of course I was horrified, but I like bit my tongue, you know?
[00:30:51] Casey O'Roarty: My dad would've said, "That's not a thing."
[00:30:54] Margot Bisnow: So I said, "Okay, well, you know, well, let's see how it goes." Um, and, um, but anyhow, and my husband had just started his company and Elliot had worked for him over the summer and was selling ads, you know, from his dorm room, and want, just wanted to do it full time.
[00:31:10] The, the, the cl- the classes he had to take to graduate just no longer interested him, and he was working with my husband. He really, really wanted to be an entrepreneur, and he didn't think he was cool enough that, you know, young entrepreneurs would talk to him, and he wanted to know how young entrepreneurs had done it.
[00:31:26] And so he cold called 18 young entrepreneurs under the age of 30 and invited them for a ski weekend in Utah in April 2008 and it was gonna be a one-off and people came like Blake Mycoskie from Toms Shoes and Sam Altman from ChatGPT OpenAI. Wow. Yeah. It was like really amazing. I mean, they, they hadn't done anything yet.
[00:31:50] You know, they were all just getting started in their companies. They were all, like, 25 years old, and they'd never met anybody like themselves before, and they all said, "You have to do this again, and I wanna bring six friends." Okay. And that's how Summit got started, and the... It wasn't until I wrote the book that it hit me That this event took place a month before he would've graduated, staying in school, not studying classes that didn't interest him.
[00:32:17] And if he had stayed in school another year and a half, and then gone to work for my husband, you know, for a year and a half, the moment would've passed him by. Someone else would've done it. This became a huge deal, a huge deal, because it was the first time entrepreneurs under the age of 30 had ever gathered together.
[00:32:33] Yeah. So I learned something. I mean, I thought it was a terrible decision. Mm-hmm. It was the- the- that changed his life and enabled him to be successful. Yeah. So I mean, it's a good thing I let him. I mean, it was torture for me.
[00:32:48] Casey O'Roarty: Yeah. I'm familiar with that torture. I mean, and we just, we don't know. We think we know.
[00:32:54] Listeners, you think you know how things will turn out. Like bad idea, good idea. You don't know. You don't know. There's... And there's best case scenario, worst case scenario, and then a billion scenarios in between those two as well, and I just, again, God, the gift of- of- of believing in our kids and knowing our kids and trusting that they're gonna grow through whatever moves they make, especially once they become older adolescents, young adults, like this is their time, and beyond, to stand on their own two feet, right?
[00:33:32] And to take some risks. We want them to take risks, but we're like, "Well, don't take that risk." Take risks, don't take that risk. So it's time to, you know, let go and see. And within, like even as, you can't see me 'cause, you know, listeners, I'm not on camera, but my face is like open and my eyes are big and it's a- an enthusiastic, "Let's see," versus, "Well, let's see."
[00:33:55] You know? So I think that's such a gift to our kids when we can really show up that way for them. It sends so many messages about- A hundred percent ... what we believe. Yeah.
[00:34:05] Margot Bisnow: A hundred percent. And almost all of them said to me, "I always knew I could take risks, 'cause I always knew if I failed, I could go home again."
[00:34:13] Casey O'Roarty: Yeah.
[00:34:13] Margot Bisnow: And generally, they didn't have to go home.
[00:34:15] Casey O'Roarty: Yeah.
[00:34:16] Margot Bisnow: But they always knew they had, they could've if they needed to, and that they wouldn't be blamed. And- I love that ... like
[00:34:22] Casey O'Roarty: that,
[00:34:22] Margot Bisnow: you, who's another, um, person that I interviewed who, um, you know, he did, uh, Wicked, the movie director. He... Okay. He did. And- and he said, "I always...
[00:34:33] I- I- I had the courage to take risks because I always knew if I failed, uh, I could go home again." And he never had to, but he said it gave him the courage to take risks i- in his movie making.
[00:34:46] Casey O'Roarty: Mm. And- Yeah ...
[00:34:47] Margot Bisnow: you know, many of them told me stories like this, like-
[00:34:50] Casey O'Roarty: Yeah ...
[00:34:51] Margot Bisnow: you know. And a couple of them did, you know.
[00:34:53] They- they tried something, it failed, they came home. Yeah. They spent a year working on something else, and then they went off and tried something else
[00:35:00] Casey O'Roarty: I mean, that's it, right? We get to provide a soft landing, right? W- and, and that's what I'm... That's the words that, those are the words that are coming up for me is being that strong and soft space to come back to, regroup, learn, you know, con- reflect, and go again. Again, again, right? Let's try it again. I love the idea of this isn't your kid not getting their shit together, right?
[00:35:36] This is your kid out there really going for it, and that support of knowing at the end of the day, should this fall apart, I know there's a place where I'm unconditionally loved and accepted and celebrated regardless of how this plays out.
[00:35:52] Margot Bisnow: 100%.
[00:36:03] Casey O'Roarty: Something you have written about is tying entrepreneurship to compassion, and that a lot of the founders that you talk to are driven by something bigger than just, you know, making the money. So why does that bigger sense of purpose matter so much? And what do you notice?
[00:36:19] Margot Bisnow: I think it's so funny because people who don't really know entrepreneurs think that entrepreneurs become entrepreneurs to make money.
[00:36:28] Pe- people who wanna make money go to Wall Street People become entrepreneurs because they have an idea of how to make a better product or how to make a better service or how to deliver something better, how to write a better song, how, how to, how to, how to, how to, how to make a better movie, h- how to, how to do something that's gonna make people's lives better, that's gonna give people something that they should have.
[00:36:53] A better face product, you know, a better, a better article of clothing. It's something that's gonna wash better, that's gonna wear better, that's gonna last better. I mean, whatever. It's something like, "Wow, I can do this and it's gonna be better." And I mean, I think if all of them were raised to be compassionate, to realize that they're not just put on this earth to make money and to look out for themselves, but they're here to try to make a difference in the world and try to make the world a better place and try to contribute, and I think their entrepreneurship is part of that.
[00:37:25] And I mean, I can just give you example after example. It, it's like a better software that's gonna, you know, save you time. It's a better laundry detergent that's doesn't have all those chemicals. It's a better, you know, clothing line that's more comfortable. I mean, whatever it is.
[00:37:40] Casey O'Roarty: Do you find that, like, what...
[00:37:42] Did you find any common themes in the family systems, the households, that kind of promoted this sense of wanting to make impact like that?
[00:37:53] Margot Bisnow: Yeah, I mean, I think they were all raised, you know, not just to care about themselves, but to care about others. Yeah. I think they were raised to be compassionate. A lot of them did a lot of volunteer work.
[00:38:04] A lot of them had to contribute in various ways to other people. They were all-- They were raised to be curious, and they were raised to ask, like, "How can I make it better?"
[00:38:15] Casey O'Roarty: Mm-hmm. Yeah. "
[00:38:16] Margot Bisnow: How could I improve it?"
[00:38:18] Casey O'Roarty: Yeah. "
[00:38:18] Margot Bisnow: Does it have to be this way? Really, this is so annoying. Could I make it better?"
[00:38:23] Casey O'Roarty: Yeah.
[00:38:24] Margot Bisnow: And, and so many of them, not all of them, but most of them ended up becoming an entrepreneur because they had gotten really good at something and really knowledgeable about something, and then they realized, "You know, there's this thing that I could do better-
[00:38:40] Casey O'Roarty: Mm-hmm
[00:38:40] Margot Bisnow: that I could improve, that would make this work better, that would make this go faster, that would make this go smoother, that would make this a more pleasant experience, that would, that would make..." Something, like, that you could improve. Yeah. And I mean, I... You know? And I mean, I think that's where most companies get started.
[00:38:55] Casey O'Roarty: Yeah. So we have two things that are promoted a lot in the positive discipline philosophy. One is regular family meetings- And the other one is co-creating agreements. And as I listen to you, I'm thinking about what we tell parents, which is sitting down with their kiddo, exploring what the ch- whatever challenge is, whether it's how we're contributing to chores, or screen limits, or curfews, or whatever.
[00:39:24] And we invite our kids into brainstorming, what are some ideas that you have about how we can create a win-win over whatever the situation is? And then in the end is a list of things that both parent and teen is okay with, and then the teen gets to pick what they're gonna try for a week. And then a week later, we come back and say, "How did that work out?
[00:39:47] What could we do to make it better?" And so I'm, like, really lit up by listening to you talk about this because you guys, listeners, like, if you're following the PD, the positive discipline model, this is baked in. We're constantly trying to, like, okay, how can we tweak this? How can we... Let's talk about what we're noticing, right?
[00:40:10] What's getting in the way? So it's, it's really not a drastic, anything drastic that we need to do. It's simply holding space for curiosity, and I like to talk a lot about critical thinking and developing critical thinking. And I can see the, the bridge between those little daily, like, eh, chores or laundry or whatever, into then, oh, I've got this thing, it's working okay.
[00:40:38] Could it work better? How could it work better? What are some things I could try? I'm gonna try it, and then I'm gonna reassess it. And so that, that's exciting to me, Margot.
[00:40:47] Margot Bisnow: No, I love that. And I mean, so many of these companies ended up getting started exactly that way. I mean, Blake Mycoskie was in Argentina.
[00:40:55] He went to play po- learn how to play polo. It was, like, after he'd ended up one company, and he saw all these kids barefoot, and he thought, "Oh, this is so sad. I, I wish I could get them some shoes." And I mean, 99.9% of the people in the world would say, "Yeah, that was too bad," and then they'd go back and go on with their life.
[00:41:14] But he was just like, "Gee, I wonder if there was something I could do," 'cause he was raised to be a compassionate-
[00:41:20] Casey O'Roarty: Mm-hmm ...
[00:41:20] Margot Bisnow: you know, person who tried to get things done. And then he thought, "You know, I could raise money and try to, you know, maybe start a non-profit to get them shoes." And then he thought, "How about if I just design a shoe that every time you buy one, one is given away?"
[00:41:36] Casey O'Roarty: Brilliant.
[00:41:37] Margot Bisnow: You know, and like another guy, Joel Holland, he sold his first company, he got an RV, he's traveling around America, and he's like, "You know, there's so many cool places that I pass, wineries, and breweries, and farms, and all these cool places, and I'm stuck staying in these horrible RV parks. There has to be a better way."
[00:41:59] And he s- you know, found this thing called Harvest Hosts that someone had just started, and he said, "Can I buy it from you? I w- I have an idea of how to take it to the next level," 'cause that's what he does. And, you know, now it's, like, huge and, and, you know, you pay, like, $80 a year, and you can stay in, like, 100 cool wineries or farms all around the country.
[00:42:20] Um-
[00:42:20] Casey O'Roarty: What's the name of that company? That sounds really cool.
[00:42:23] Margot Bisnow: Harvest Hosts.
[00:42:25] Casey O'Roarty: Harvest Hosts. Okay, love it. Yes.
[00:42:27] Margot Bisnow: No, but I mean, it's just like, you know, you're raised to think, like, "How can I make it better? How could I improve- Yeah ... how could I improve people's lives?" All these people, they're RV-ing. They don't wanna spend the night in this stupid RV park.
[00:42:38] Yeah. You know? And also, like, as you're traveling along, I mean, the, the reason it's so successful is, like, the farmers, and the wineries, and the breweries, whatever, all these people, they love it because the people come, and they park there, and they're like, "Oh, what are you selling?"
[00:42:52] Casey O'Roarty: Yeah. "
[00:42:53] Margot Bisnow: Oh, can I buy one of those?"
[00:42:55] You know? Yeah,
[00:42:55] Casey O'Roarty: yeah.
[00:42:56] Margot Bisnow: So it helps the local people also.
[00:42:59] Casey O'Roarty: Yeah, yeah. I love that. I love that. Ah, well, your last rule that you talk about is lead by following and backing your kid without steering the whole thing yourself. So after sitting with 70-some families that you, that you sat with, and those entrepreneurs that you've gotten to know over time, if there's one mindset that you want every parent to walk away from this, um, podcast interview with, what is it?
[00:43:28] Margot Bisnow: Um, yeah, it, it was something that really surprised me, and I, I, I'm just gonna read you what the paragraph that I-
[00:43:36] Casey O'Roarty: Sure ... I,
[00:43:36] Margot Bisnow: I was looking at this before. Um, "It's the toughest part for parents. If you want to incubate an entrepreneur, you need to lead by following, regardless of where your child wants to go.
[00:43:48] It's one of the hardest things for most parents to do. Knowing what your kids' strengths are, understanding what path would be good for them, and judging when and how to support that path. Many of the moms I talked with did this naturally. All of them did it eventually."
[00:44:03] Casey O'Roarty: Hmm. I love that little bit at the end.
[00:44:07] Many did it naturally. All of them did it eventually. So there's hope for all of us. Even if you're listening to this show and you're like, "Oh, God, this is not how I've been showing up," it's, the time is now. The time is now. The time is now. Yeah. So my show is called Joyful Courage, and I always end my episodes asking my guests this question: What does joyful courage mean to you, Margot?
[00:44:31] Margot Bisnow: So, uh, such a great question, and I was thinking about how I would answer it. I think that having an opportunity to help your teenager discover their passion and pursue their passion- And, and have a happy and fulfilled and joyful life. It's hard. It takes courage. Yeah. But it is actually the most joyful thing we can do, is to raise joyful kids.
[00:44:58] Casey O'Roarty: Mm-hmm.
[00:44:59] Margot Bisnow: And, and, and to see them being happy and, and, and not just happy, but filled with joy because they know that, that they're doing something that they want to do and that gives them joy. And I just wanna say that it's not just to become an entrepreneur, which means, like, starting a business and working, you know, 100 hours a week and taking on all sorts of risk.
[00:45:22] It's, it's being more entrepreneurial in the way that you raise your kids. And if I can just read this one little thing-
[00:45:29] Casey O'Roarty: Yep ...
[00:45:29] Margot Bisnow: I think is so important for parents. "Even if your child doesn't want to be an entrepreneur, encouraging them to become more entrepreneurial by promoting certain attitudes can only be a good thing.
[00:45:42] All children thrive if they learn to believe in themselves, to pursue their true passions, to find new ways to solve old problems, to see opportunity where others see the status quo, to be willing to take on a challenge without proper credentials, to work with single-minded determination to achieve a goal, to take on risk if the project is worth trying, to learn that building something wonderful is its own reward regardless of how much money you make, to view failure as feedback and setbacks as learning experiences, and to dream big dreams."
[00:46:22] And I know it takes courage to do that, but I think if you do that, you will be filled with joy and your children will be filled with joy.
[00:46:29] Casey O'Roarty: And boy, doesn't the world need kiddos that are growing in to, into their adulthood with all of those, or at least the majority, some? As many as possible of those skills.
[00:46:41] Ah, thank you so much for that. Where can people find your book and follow your work?
[00:46:46] Margot Bisnow: So it's, the name of the book again, and make sure it's the second edition 'cause it's the one with all the photos. Okay. Raising an Entrepreneur: How to Help Your Children Achieve Their Dreams, 99 Stories from Families who Did, and it's on Amazon.
[00:47:00] And I also have a website called Raising an Entrepreneur, and that has links to all the articles I've written and all the podcasts I've done, and also links to the book.
[00:47:08] Casey O'Roarty: Beautiful. Okay, I'll make sure all those links are in the show notes. Margo, thank you so much for spending time with me today.
[00:47:15] Margot Bisnow: Thank you.
[00:47:15] It was really fun, Casey. I really appreciated the conversation.
[00:47:22] Casey O'Roarty: Thank you so much for listening. Thank you to my Sproutable partners, Julietta and Alana. Thank you, Danielle, for supporting with the show notes, as well as Chris Mann and the team at Podshaper for all the support with getting this show out there and making it sound good. As I mentioned, sharing is caring.
[00:47:39] If you're willing to pass on this episode to others or take a few minutes to rate and review the show on Apple Podcasts or Spotify, it helps other parents find this useful content. Be sure to check out what we have going on for parents of kids of all ages, and sign up for our newsletter to stay connected at besproutable.com.
[00:48:00] I see you doing all the things. I believe in you. See you next time.

See more