Lessons from a female entrepreneur | Victoria Montgomery Brown & Charles Duhigg | Big Think Edge

And gain the skills that they need to be on top of their game and their careers. They're going to need to keep learning soft skills: how to deal with human behavior and how to adjust to things that are changing in real time. That's an area that's very, very difficult for computers, but humans have a huge advantage. There's power in confidence.

I'm on the other side of the table now. I produce and I direct and I write. I can really feel the difference when someone comes into a room with confidence. I'm such an advocate for everyone to think like an entrepreneur. Think about how you would be doing your job if nobody showed you how to do it. Through the study of analytics, I knew exactly what was going to win, what was going to lose. Anybody can look at their craft, their profession, their passion, and become better. It's about finding that edge.

Hello and welcome everyone to Big Think Live. My name is Charles Duhigg. I'm a journalist at The New Yorker magazine and the author of the book The Power of Habit and Smarter, Faster, Better, and we're here today to talk about entrepreneurship. What does it take to get something going and to keep it going? Luckily, we're doing so with Victoria Montgomery Brown, who is our guest today. Victoria is actually the co-founder and CEO of Big Think. So this thing that you're watching, she made it. But more importantly, she's the author of a forthcoming book called Digital Goddess, which is being published by HarperCollins.

And I'd love to invite you to join our conversation today, particularly to ask questions. You can do so starting immediately by going into the comment section of whatever platform you're on and typing in your questions, your thoughts, or your suggestions. We will see them, we'll bring you into the conversation, and I'll talk with Victoria for about 40 minutes or so and then we'll start taking your questions.

So let me start by asking, first of all, Victoria, thank you for joining us today. This is a pleasure. Kids, we're actually business school classmates, and it's been so much fun to watch Big Think's success and now to read your book, which I absolutely loved. And before we jump in, let's take a step back and actually I want to ask you about this. So you started Big Think 13 years ago, is that right?

That is correct.

Okay, okay. And in the book, you start by telling the story of the week that you closed funding for Big Think. It was also the first week, or also the week that you first got arrested. Which, I gotta say, when we were at Harvard Business School, there was not a class on how to deal with getting arrested while closing your first big fund. Tell me what happened.

Gosh, I wish there were. And you know, it was an interesting story. I had been working at an organization for a couple of years and left and continued to do some work for them. I took car service and was charged with, well, basically charged with theft of car service, which was unbelievable to believe. I had to get a criminal defense attorney, and my criminal defense attorney thought it was a joke, like this nice young woman, and that one of his law school partners was just playing a trick on him. But it was actually serious, and it took a big chunk of my life in the first part of Big Think and was really, really stressful. I actually managed to get through it and totally fine, but yeah. It was actually about a month before we launched the public version of Big Think, and a big New York Times article was about to come out, and I was almost like, I don't want any press at the moment because I was so concerned about my legal issues at the moment. But managed to plow through it and here we are today.

Well, and you made this really interesting choice, and this is a theme that runs through the book, which is how does someone become an entrepreneur, how do you become an entrepreneur with ethics and with integrity? And particularly as a woman, I think there's different challenges that it sounds like you faced. You made this interesting choice, which is as soon as you got arrested on the craziest thing I've ever heard, like this ridiculous thing, you called your investors to tell them. Is that right?

That is right. I was actually incredibly nervous about it, and our lead investor is actually a classmate of yours and mine at business school, and he was the first person I called. I mean, these people had invested their faith in me and our organization, and I just felt like now is a moment where I could either be totally transparent or hide and pretend that it didn't happen. The temptation was obviously the latter, but I knew that the right thing to do was to call them. So I called in each and every one of them, except for my business partner called one of our initial high-profile investors because he had got him to invest.

And it was very difficult, but I am so pleased to say – and this is advice that I would give to anybody starting a business – no matter how uncomfortable the news is you have to deliver, if it's bad news you need to get it out there quickly and be as honest and transparent as fast as possible.

And in my case, anyway, in the long run, that has served me super well. I have extremely close relationships with all of our investors and because I was transparent from the get-go and continued to be so along the journey, even as we got new investors, that made them trust me even more because they knew that I would deliver them the hard truths with no blinders or bluffing. It was just straight, this is how it is.

Yeah, well, and that brings up kind of the book Digital Goddess, which is essentially a compendium. You know, Big Think has been this huge success. You guys have, I think, over a billion views at this point, and the book's an attempt to teach us what you've learned along the way. Who is this book for? Like when you were writing it, who was the reader that you had in mind?

Well, entrepreneurs for sure, but especially women entrepreneurs, because I don't think even today there is enough out there for women to basically learn about what it takes to be an entrepreneur and as a woman. And so that's really who the focus is for. But I hope that it's a book that any entrepreneur can learn from and an expose into essentially what it takes to be one, at least for me in my shoes.

Give me an example of the challenges. Like what are some of the challenges that you confronted as a female entrepreneur that you think some of our male colleagues from Harvard Business School haven't had to grapple with?

Well, I think getting in front of people from in terms of investment is slightly more challenging for women. I think that's changing because there is a lot of idea that men want to invest in women, but there is bias, and there's no doubt about that and continues to be so. And I feel that women have to be a lot more savvy about who and how they approach for investment, and their idea has to be, I think, a lot more together than if a man were to just go into, say, a VC office or to a potential investor. I think there's a lot more trust that a guy can do it.

Now, I have a business partner, Peter Hopkins, and so it was not just me going after these investors, and he obviously helped enormously in that. But I do think that there is a specific challenge that women have to face. They really have to, I think, over deliver on what they are going to build and be very clear about it in a much more detailed way.

Yeah. And you mentioned in the book that only 2.2 percent of American venture capital goes to women-led firms right now, which is ridiculous, right? It's, it's – but I think you're right, and we know that the VC industry is a sort of monolithic insular industry; something like 80 percent of VCs went to either Harvard or Stanford. They're overwhelmingly male, overwhelmingly white, and that makes it challenging.

But of course, getting funding is only part of building a company and part of your journey. Let me ask you, when you look back at the last 13 years of building this company and taking it from an idea to something that so many people know about and rely on now, if you could go back in time, what is the thing that you would have told yourself 13 years ago that would have made that path either less bumpy or at least prepared you for it?

I think one of the things that I've experienced over the years is that every little thing to me has been a crisis. And I've lived that in a way that I don't think was necessary. Discussed, you know, some of the panic things that I went through, have gone through over the course of these 13 years. But what I would advise anybody starting a business is that there are going to be a lot of bumps and not to take each one of them as though it's going to be the end of the business.

And I really learned that the hard way and made a lot of the years and experiences of Big Think really difficult for me because I kind of was always in a catastrophic mindset. And while that has been useful in certain ways, because I'm always a step or two ahead of what I think might happen, it hasn't allowed me to enjoy the success of what we've built as much as I feel like I could have.

Give me an example. Like, paint a picture for me of one of the scenes from your life over the last 13 years where it just felt like everything was spinning out of control.

Well, I mean, as a startup we've always had financial issues. We've survived and thrived for 13 years, but that does not mean that there haven't been really dark days financially for us. And we are not a VC darling. We have individual investors primarily who are incredibly supportive, but it's difficult. It has been difficult for us to get investment, and so over the years, there have been countless times where I'm literally counting the money in our bank and thinking how many days do we have, etc. And instead of believing that something, because of the incredible business we've created and the audience we have, would come through, basically going to the worst-case scenario.

And I can give you an example of when I was doing that and how if I had just believed and been open to the possibility that things would work out and they did, that I would have enjoyed that process even more. So I think it was around 2013, so well into Big Think, and we’d been through ups and downs in the finances over the years. This one, we were really getting close to a big issue with, you know, potentially making payroll and things like that.

And this incredibly wonderful man, I won’t mention his name just in case he doesn’t want me to, heard about Big Think through another investor. He happened to be in New York from San Francisco, swung by the office, and we just chatted for a little bit. He and I went out for coffee, and literally at the end of the coffee, I didn’t ask for money. And this is a piece of advice I would give: if you ask for advice, you’re often given money, and if you ask for money, you’re often given advice.

Yeah, no expectation of him in any way wanting to participate in Big Think. And at the end of the coffee we’d been together for probably only about an hour, he said that he was going to invest $500,000, which was a lifesaver for us. He's obviously still an investor and along the way supported us even more. So just my, I guess, negative thinking has helped us in certain ways, but I think has harmed me in my emotional ways along the way that I didn't need to.

Yeah. And one of the things I love about the book Digital Goddess is that you're really open and honest about the toll that this company had on your mental health. You talk about having panic attacks, and you know it for someone who's watching this who's saying to themselves, "Look, I want to be an entrepreneur, but I have the same tendencies," right? It's really hard for me to deal with uncertainty, and it's hard for me to invest myself into something and not get totally wrapped up in it. What did you find worked for you to help create some buffer between Victoria having a life and Victoria the CEO?

Well, to be honest with people, I think if I were to talk about work-life balance for me, at least for the first 10 years, there was essentially no work-life balance. It was entirely about the business, and this was one of the things that probably contributed to my mental unwell-being at periods of time. But obviously, and even in those times, I relied on family and friends. And at a certain point when I was married to my then husband to get through these things, but my mind was a constant wheel of anxiety.

And I would advise people if they can, as an entrepreneur, to get help as soon as you start feeling those things because it's no way to live, no matter what you're building and how successful it is. Your well-being and mental health are paramount.

Yeah. No, absolutely. And of course, that the well-being and health of your employees, you know, you went from Harvard Business School to just spending some time in the television world and then starting this company. Had you spent a lot of time managing other people or being a boss before you started Big Think?

I had never managed anybody.

So…

Okay. And I really had never been an entrepreneur. So I had been at business school and worked for a couple of years in an organization. I mean, in that organization, I suppose I managed a few people, but it was so small that it was meaningless and the buck didn't stop with me. You know, the things that I mentioned in the book that are so trying is that the responsibility that you are responsible for people and their financial well-being. And that's one of the things that I think entrepreneurs should understand, that it's not just about building the business; it's taking care of the people who work with you and are contributing to the mission.

Yeah. And how did you mature as a manager? Let's talk about, you know, sometimes some employees, most of the time they do great, but sometimes we have to have hard conversations with them. How many employees does Big Think have right now?

At the moment, we have ten and about thirty or so freelancers.

Okay.

It's been, you know, different numbers over the years. We've had as many as 25 or 30, and it really just depends on essentially what our needs are for growing the business.

And as you can see behind this...

Oh, go ahead, sorry.

Or I was just going to ask what did you learn about managing those folks, like about communicating and setting goals and also giving the hard feedback when you need to?

Yeah. I'm not sure how much I've learned. I feel like I have grown, but it's obviously subject to interpretation by the people who work with me. Initially, I think that I was hesitant to have difficult conversations and would avoid them, and that only makes situations worse. So now I feel like I immediately have those conversations to mitigate the situation getting even worse. So that's, I think, the number one lesson is to confront situations head-on versus brushing them under the carpet. It may be difficult in the moment, but it will make you better, and it will also make your team better.

And even if that person isn't right for the organization, you have to have that conversation with them. Ultimately, it will be better for the organization and for the person as well.

And how do you make that decision? Because I know that there's this sort of, this nostrum in, you know, startup land which is that you should hire slowly and fire fast, by which people mean look for the employees who are going to contribute to your culture. And if you make a mistake, don't sort of get into this sunk cost policy where you try and make it work again and again. But at the same time, hiring is time-consuming and expensive. Oftentimes you need those people. When you fire them, it means that there's more work for you as a CEO to do.

How did you, when you were thinking about hiring and firing, how did you decide when someone was right for the organization and when it was time to let them go?

Well, I have made so many mistakes in hiring people; it's unbelievable. We've probably had over 100 or more people working at Big Think, and by and large, everybody's been excellent. But there have been a few people that have been detrimental to the culture of the organization and actually to the output of the organization.

And what I have learned about hiring and firing – and as tough as this sounds – if you have a bad feeling about a person for a prolonged period of time, that person should not be in your organization, no matter how much they contribute to the work or the bottom line.

Even life is short, and you want to be around people who are pleasant to work with, and if they are making an unpleasant environment for you or for any of the other people on your team, it's time to let them go. I have kept people on for so long that should not have been there just because, to your earlier point, I was so worried that letting them go would have really bad implications for the business, and that just never turns out to be true.

A business is, for sure, the people working at it are critical, but no one person should ever be critical to an organization, including the CEO or anything like that. If the organization can't stand on itself by the work and product that is being put out, that's a real issue. And no one person should really be completely necessary. I mean, in the moment, everybody is necessary, but there can be no one linchpin in a successful organization.

Yeah, and I think part of what you're talking about is culture, right? That if the culture works, then no one is essential because the culture is larger than the people who populate the company. Tell me, like, when you were starting Big Think, did you sit down and say, like, this is what I want the culture to be, or did it emerge more organically?

Gosh, I wish I had, you know, sat down and thought about that and written some manifesto about that, but really just when starting a business, it was like one foot in front of the other and thinking about what immediately needed to be done. Now I would advise people to think about the culture that they would want to be.

I absolutely did not do that. And had I thought about that in the early days, and maybe if Peter and I had thought about it together, we would certainly not have hired some of the people we did that ended up being really difficult to work with.

And how would you describe the culture today? Like, what have you learned about building culture and reinforcing that culture beyond hiring the right people?

Well, initially, I thought, you know, to use a military term, I hope, that command and control was kind of the way to be, that there was that I, as CEO, was responsible for the army, so to speak, below me, and it was important that they listened to what I said and did exactly that.

The culture today is way more loosey-goosey, and we have an incredible team of people who are responsible for themselves and that we have full faith that they will do what they need to do and grow the organization in ways that we need. And so, to my mind, hiring people that you can basically just trust will do what's best for the organization is the absolute way to go.

The command and control type leadership is, in my mind anyway, absolutely not right for entrepreneurs and startup organizations.

Yeah, and it's interesting. I think one of the things about the pandemic is that because we're distanced, we're working from home now because there's much less ability to see each other and monitor each other like that. That command and control is actually falling away much faster in all kinds of organizations, right? There's this need for everyone to kind of let go and be at peace with that because it can't be otherwise.

You know, I'm wondering, there's been a lot written about teams, about how to help teams bond together, how to make teams stronger than the sum of their parts. At Big Think, like, what are the culture hacks or the team hacks that you guys have found that make it easier for people to come together and get their work done and for those teams to be stronger than just a group of participants?

Well, I think one of the most important things – and no matter who the employee has been at Big Think – what has attracted them to the organization is our mission. So if it's a mission-driven organization, that is the thing that is most important to creating a positive culture.

You know, they understand what they’re there working to do. And I think reinforcing that in meetings and in the way that we speak to each other is really important as well. If it's just an organization designed to meet the bottom line or get the best possible revenue, I don't think that motivates anybody, really.

And what they want to do is be in an organization that they are proud to be working in and that they see that their contributions matter. And I think that creating a culture where people know that is very important.

Give me some examples of how the mission – like, what are choices you’ve faced as a CEO where you could have gone one way, but you went the other way because of the mission? Are there examples of that?

Yeah, absolutely. I mean, our mission is to help people get smarter faster, and that's a pretty easy thing to understand. But what it's not so easy to understand at times is that to do that requires making money.

And we've confronted situations where it would have been so easy for us to take a sponsorship or a client that was completely opposite of what the mission to Big Think was. For instance, we had early on a very large chemical company that wanted to be a big sponsor for us and put their brand around some of our experts’ content.

So imagine you’ve been on Big Think twice. How would you feel if suddenly before you spoke, there was a massive ad for a chemical company that it seemed to be that you were endorsing?

So we could have taken many of those types of opportunities, and for us, the people like you who really make Big Think what it is, smarter, faster, we just super respected that. It was critical for us, and destroying any type of relationship with the experts we have would have been terrible.

Short-term gain, potentially big short-term gain in terms of revenue, but very big long-term fail.

Yeah, you know, it's interesting you mentioned that in this interview, and you talked about a lot in the book that you started this company with your partner, Peter. And I know that relationships between founders are very complicated, right? They're in some ways like way more complicated than marriages because they go through these periods of being close and then of having differences. Tell me about, like, over the last 13 years, how has your relationship with Peter changed?

You know, I think it's become obviously a lot closer. We've been through serious ups and downs, personally, individually, professionally together, and we spend probably over the last 13 years, I've probably spent more time with Peter than anybody else in my life, including family, friends, etc.

And we have worked over the years sometimes as close to each other as like back to back in a little cubicle. And so I know Peter very, very intimately, and we've gone through some of the bad times. I think by distancing ourselves a little bit and also by candid and often very difficult and sometimes vitriolic conversations, but understanding that each of us wants the best for the company and ultimately for each other probably even more is how we've weathered many of the storms we've been through.

So give me an example of that. Like, give me one of the – give me an example of one of the toughest times that you and Peter went through and how you handled each other.

Yeah, so I mean, Peter is very open about this, and it's a chapter about our partnership in the book. At a certain point during Big Think's existence, Peter ended up becoming addicted to drugs, and that was not easy for us, for the organization, and then certainly not for Peter.

But the trust that he would emerge better than ever, which he did: he's now incredibly much more important to the organization obviously than he was during that time. But critical, no matter what, I think he took some time away from the business, which was necessary for the business and for him, and then came back stronger than ever.

And I think, at least in our partnership, it’s really important to give people the space to make mistakes and understand that they can come back. And in my instance, you know, Peter saw me struggling with anxiety and depression over a number of years, and he finally insisted that I go and get help for it, which I did.

And so that was a kind of intervention for him to me that was critical. And I didn't like to hear it at all, but he made it clear that it was that or I needed to leave. And so I did it obviously, and I'm really thankful for it.

But those two things, in the moment, seemed almost insurmountable. But really nothing is as long as you have trust in the other person and the belief that together you can make things better and also that together you're stronger.

I think it's a really good point that we have to have this space for people to make mistakes, right? And to believe that they can come back from those mistakes. I mean, I think one of the hard things particularly for startups is that oftentimes you're asking people to do jobs that they've never done before.

Very frequently, you hire them for one thing, and then you start giving them more responsibility simply because they're the only body that's in the room that has time to absorb that. And it's inevitable when someone is doing something new that they are going to make mistakes, right? That they're going to trip.

When you were dealing with employees or reflecting on yourself, and those mistakes occurred, how did you help coach people through them? Because I think there is this tension between when does someone not going to work out in a position and they need to be replaced for some responsibility to be taken away versus when someone makes a mistake but we think maybe they can do better next time.

How did, like, is there an example that you confronted where you were faced with that, having to decide whether to let someone go or demote someone versus coach them to the next level?

Yeah, absolutely. And I'm not sure that I'm a good coach at all, but I think what I am is a compassionate and empathetic person. I mean, years ago we had a big sponsorship that required us to travel to Paris and have really high-level people in a room that we needed to video.

And essentially, the entire sponsorship was about capturing this video. The whole thing went really, really badly. And then to begin with, while we were there supposed to be filming these individuals, these experts live, our videographer forgot to turn on one of the cameras. And that, it was the main camera; essentially, the only thing we had were the outtakes of their sides of their faces and stuff like that.

And this was a wonderful, wonderful person and super talented, and that's a moment where Peter and I could have been like this, you know, we're letting that person go; she screwed up, etc. But there was no intention of her doing that. And you could imagine how she felt after that: like, oh my god, holy, I have super messed up.

And instead of us riding her and berating her, we just were like, you know, these things happen. I've made mistakes as bad. Everybody in the world has made mistakes as bad. And to understand that her intention was not to have that happen and move on.

And I think that the way that I think about keeping people is if their intention is good and they've made a mistake, it's not a problem. It's if they are really making an effort to screw up that you take a look.

Yeah, no, I think that's a really good point. I think about a friend of mine who I was living in Costa Rica last year, and he and his family came down, and his wife left, put her purse on the beach to go play with him and the kids. And unsurprisingly when she came back, her purse was gone.

And it's one of those things where my friend could have said, "How could you think to leave your purse on a beach?" But he knew that she was beating herself up over this, right? Nothing he could say was going to make her feel worse than she already felt.

And of course, she had learned the lesson: you don't leave your purse on a beach in a foreign country. And so I think that having that presence of mind to say, "No, no, the person is actually already punishing them." Anything I can say to this person, they're already saying to themselves.

That's a really important step to be able to take, and it helps you distinguish who you ought to keep around and who won't learn from those mistakes. And by the way, I have certainly made many mistakes in not being kind in the moment. That's just an example, a positive example for me and for Peter where we didn't react badly, but I can't really think of any, but I know there have been multiple, multiple times where I have reacted really badly to somebody making a mistake, and later on I've beat myself up about it and been really disappointed and ashamed of myself.

Yeah, let me ask. You know, it's an interesting time to be talking about women in business because, you know, obviously Me Too occurred and really changed the conversation. There was also this period of, you know, like the boss, right? These books by women entrepreneurs, many of which were fantastic, that I think in some respects were sort of liberating for certainly in some of the women I spoke to who read them to sort of say, "Look, like this is how a woman doesn't have to pretend to be a man in this business space; they can cut their own path."

But then there's also been a lot of negative backlash to that. There have been a number of articles about companies that are women-run where female employees criticize the CEO and say, "I don't feel like this has been as nurturing for women as I hoped it would be." There's the Nest, no, the Wing, sorry, the Wing and the Away, the luggage company where some of the folks who are watching the stories come out of these companies say they think it's unfair because they are questioning if women are being held to a different standard as CEOs than men are.

I mean, what is your take on this? Because it is a complicated time right now to be talking about gender and leadership and to parse out what's appropriate criticisms and what aren't. Do you have any thoughts on that?

I do. I mean, I truly like to think of leadership as something that is done well if you're a man or a woman, and there shouldn't be a difference. So yes, women CEOs are potentially held to a different standard, but that doesn't mean in my mind that they should be behaving differently. Good leadership is good leadership, and being an empathetic leader is the same no matter if you're a man or a woman.

Yes, there often is backlash from particularly female employees in organizations sometimes if there's a female CEO, but I don't think that women should really reflect on that. They should be the best leader, entrepreneur, CEO, whatever it is, their position can be, and not think about their gender in those moments.

And you actually – you write in the book that women can use femininity to their advantage in business, not in nefarious ways, obviously, or sexualized ways, but what do you mean by that?

Well, I think that one of the advantages I have had, certainly being a female entrepreneur and CEO, is that men at this moment in time really do, by and large, want to encourage female leadership and business leadership.

And so I think, at least we started Big Think in 2007, I think many of the meetings with investors and potentially clients we got in some part because they were interested in nurturing a female business leader. And so I don't think that – I even write this in the book – that sexual dynamics should necessarily be taken out of the workplace.

There is a difference between men and women, and I think that, you know, as you said earlier, men behaving or women behaving as men is just not how things should be. There are benefits to both, and I've embraced those, and I think it's been rewarding to me to do so.

How have you said – how would you say that your leadership style has changed over the years?

I think that I am a lot softer than I was from the get-go. You know, as I mentioned earlier, my thinking was that I had to be – know the answer to everything, not ask questions, seem completely resilient. And now I think I lead much more openly, and I'm open about not all, but some of my emotions and the state of the business, etc.

Early on, I felt like the hardships we might have been going through needed to be hidden from our team or from others or from our investors or whatever. In some way we never did, but that was my thinking. And now I just really understand that, you know, being soft is not a bad thing; it's actually a positive thing as a leader, at least for me.

And I think that’s what's changed. I think I was initially quite hard, and now I'm much softer than I was.

Is there an example of a conversation you've had recently that you think when you started Big Think you would not have had that conversation?

I don't know particularly. Do you mean with an employee or really anyone?

I mean like, what’s an example of how you’ve become more soft?

Well, I think over the years, people might have been early on afraid to come and talk with me about what they were experiencing, what they wanted in life, etc. And certainly in the last few years, many of our employees have gone on to do different things, which I'm delighted about. I want everybody to be as happy in what they're doing and successful as possible.

But I know for sure early on, people would not have told me that they were thinking of going back to school or thinking of a different field or wanted to change their position inside Big Think for fear of upsetting me. And now I can literally say every person who works at Big Think or has worked at Big Think has the comfort to come to me and know that I will be supportive, you know, barring it be something ridiculous and will help them transition into whatever it is they want to do.

So I think that's the way I've changed.

Yeah, well let's move to some audience questions. And again, if you're watching this, we would love to have your questions. You can enter them into the comments in whatever platform you're using. We will definitely see them, and here’s one that came in. It's from someone who's watching, and they say, "I'm moving from a solid 20-year career in chemistry to becoming an entrepreneur. I tend to live with rose-colored glasses, confident that success lies ahead. Is this a dangerous outlook?"

I think optimism as an entrepreneur is essential. I don't really know any entrepreneur that is not optimistic about what it is that they believe they can build or eventually do build. So optimism is fundamental.

I would also say that while I was way too negative and fearful at the start of Big Think, you do have to plan and visualize what could go wrong and try to mitigate that, but with a sense of optimism that you'll work through it all the time. So rose-colored glasses, I think, are necessary, but you better have a bit of, I don't know, just sunglasses or something like that in them because there will be tough times. But optimism, to my mind, is essential.

Yeah, no, I think that's exactly right, and it's a hard balance, right? I think for the 20-year career in chemistry, becoming an entrepreneur, I think you have to believe in yourself; you have to believe it's going to work. But at the same time, when you say that you have to be realistic, does that mean having a backup plan or a plan B? Does it mean what does it mean?

I think absolutely not. As I write in the book, I think having a backup plan is really dangerous because then you have a way out. At least for me, going all in was fundamental to it. So leaving a job, etc., not having income, and being forced to figure out how to make Big Think work was critical to me.

So I think backup plans are actually dangerous, and if you're seeking investment, I've learned that investors don't want to see that you have a job or something to fall back on. They need to see that you're hungry and that this is critical to achieve so that you will focus entirely on it.

Yeah, here’s another question from Jason Olsen. Thanks for sending this in, Jason. He says, "What advice would you give to young people when it comes to balancing feelings of entitlement with not being taken advantage of?" And this is a great question because I find this very frequently that, for instance, when I'm hiring assistants, some assistants say, "Hey, you offered me this salary. I'd like a bigger salary. I think I deserve more," at which point I have to say, "Look, the salary is the salary, and this isn't personal. This is about what I think the market will bear for finding the person that I need."

And I think for some people, there is a sense of entitlement because there's this question in the back of your head: am I being taken advantage of, or is this person being fair with me? How do you navigate those?

Well, I try to impart to people not to go into a conversation with even the notion of being taken advantage of, to think that the person actually has your interests in heart at heart.

So I would advise people to not even go into job interviews with that concept. I mean, it will come across very clearly if the person is trying to lowball you or whatever, but to your point, the job is the job. And oftentimes, I feel young people today, millennials or what have you, go into positions thinking that they can skip steps, and I think that's dangerous for them and dangerous for the organization.

There are reasons people accelerate through companies; it’s because they're contributing more as they learn more. And so this notion of entering a job with the feeling that you might be taking advantage of, I don't think is good for the person and certainly not for the organization. I would be wary of hiring a person like that.

Yeah, no, I think that makes a lot of sense. There's a question from Jana who asked, "In your book,excuse me, in your book you have a chapter called 'Grow a Pair.' Can you tell us why this is good advice for female entrepreneurs?" And we should specify, as we say in my household, when it's time to get serious about something, you got to "ovary up" on it.

But like that, yeah, you don't say whether you should grow a pair of might be, you know, any kinds of organs, but it was something that usually is kind of an aggressive masculine thing to say. So I think Jana's asking, like, what should women take from that?

Well, I think that women are often portrayed as being, especially in business, meek, etc. And to my mind, while I know some people may have issues with this, it is like grow a pair of balls. And that just means not necessarily actually growing them but be willing to do the tough things that men are often associated with doing.

You know, having the difficult conversations, being tough when you need to be and not being afraid. And that's really what it means to me: it's just not being afraid and behaving in a way that men are typically associated with in business, like jumping all in and confronting the difficult things.

Yeah, no, I think that makes a lot of sense. Soham sent in a question saying, "Can you give a few suggestions for a teenager who's watching this right now in terms of wanting to start a business?" I guess, and just in life.

Yeah, let's say let's start with business, but then also, I don't know, like, you know, we're in our 40s now. I have two kids. One of them is on the brink of being a teenager, and I do sometimes wonder, like, what do I wish someone had told me when I was 13 or 14 years old? What is that for you?

For me, I think it's find something that you really enjoy doing and are passionate about, and believe that it can be catalyzed into a career. You know, when I was a teenager, I had this notion that I should do things like study math and finance and things like that because that was ultimately the path to a job.

And so my advice for teenagers today is really try to figure out what it is that you like doing and not worry about what you think the steps should be to get you to a job because that will sort itself out if you figure out what it is you like to do.

I agree. And you know, something that I think about a lot because I get a lot of emails from readers who say, "Do you have advice?" And the advice I've given to both teenagers and to adults is there are a lot of studies that show that we don't take enough risks in our lives, right? We know this across the board.

That people don't tend to take enough financial risks in how they come up with their stock portfolios; they don't take enough risks at work and take on new jobs. That oftentimes in life, the reward for taking risks is actually bigger than we think it will be, and the risks tend to be less risky than we think they will be.

As humans, we’re bad at being risk calculators. But what's interesting is that then it brings up this other question, which is a lot of people who hear that say, "Well, does that mean I should go, like, you know, jump off cliffs or, like, use drugs, or that I should just invest in my cousin's crazy business scheme?" And the answer is no because there are different kinds of risks in this world.

When people say that you should take on more risks, what they often mean is you should take on more risks that involve hard work. So if a risk does not involve hard work, then it's probably just a risk.

But if it's a risk like starting a new company or going after a promotion or applying for a job that you think is scary to do or trying something socially, if it's something that feels like work, that's, I think, an indication that that's a risk that you should think about taking. That's a risk that might pay off for you because it's going to end up paying off.

So Soham, I think I think you should work, don't worry about the job you're going to get, as Victoria put it. Look for what you love and be open to taking on risks as long as those risks seem like hard work.

I would say again, and rewarding.

And rewarding. Exactly, exactly.

So Sabrine Priestley, who's on YouTube, sends in this note: "Any words for a 55-year-old first-time female entrepreneur? She's building a spiritual course with coaching, and as an engineer and author, this is a totally new game for her."

So I just think, you know, honestly, it's no matter the age of the entrepreneur. It's figuring out is this something that is differentiated? I mean, this goes back to some of our business school training. Are you uniquely able to take it on, and is there a market for it?

So those are the three things that I would think about as an entrepreneur, no matter what the age or gender. Are those things critical? And also, again, going back to the optimism thing: be optimistic that you can make it happen and then invest the hard work to making sure that it does.

So Winsome asks, "You've had a lot of experts talk about things on Big Think that they've never spoken about publicly elsewhere, right? You spend this – you know, having been on Big Think myself, one of the nice things is that you have this time to really talk to the camera. And as a result, a lot of people end up saying things that they haven't said anywhere else. What are some of your favorite interviews and content that you guys have ended up putting up on Big Think that you're really proud of?"

Oh my gosh, there are so many of them. I'm trying to remember one of the first interviews we did when we needed to get content before the launch of Big Think. We went to the Aspen Ideas Festival and interviewed, I guess, around 35 or 40 people because all these thought leaders congregated there.

And I quite honestly had never really heard of him before, but one of our people, Brett Dobbs, who used to work with us years ago, booked Billy Connolly. And by the way, by booking, I mean he was walking around just grabbing people. And he was the former poet laureate of the United States, and his interview is still up on Big Think.

The quality is not as good as today's because we used different equipment back then, but that still stands out to me as one of my favorite interviews. And he was so open in a way that I think that he hadn't been in other platforms, and he ended up reading two poems for us. The lanyard was one of them, and I can't remember the other, but that to me was one of the most joyful interviews I’ve had.

The other thing is that a lot of business people come on and are constantly asked about things like what's going on in the economy or what is going on specifically in their business. When we have economists and business people on, we're asking them much more personal things about leadership, etc.

And so another great interview that we've had, I didn't conduct this one, but was Larry Summers, the former Treasury Secretary, on how to make difficult decisions. Now he's on all the time talking about the economy, etc., but I found that that interview with him riveting and much more personal than things on other platforms that I've seen.

That's interesting. What did Larry say about making difficult decisions?

Well, basically, there's a process to it. And he walks us through the stages of it, but you kind of have to evaluate the outcome, the good and the bad and walk clearly through both before you make the decision. I mean, it's a lot more complicated than that, but that's sort of the gist of it.

Gotcha. And again, just to anyone who's watching, feel free to submit your questions into the comments section of whatever platform you're watching on. We have time for a couple more.

Here's a question from Lena Stroth, who wrote in from Facebook. And she says, "Fellow female CEO and founder here! My business, which is an online staffing platform for media professionals, is starting to gain traction. That said, I still struggle with selling myself in the business. Is this something you encountered as well? If so, how did you combat that?"

Yeah, selling oneself is difficult, that's for sure, but the way that I approached it is that it's not truly about selling myself. It's about selling the business, you know, convincing people that what we are offering is going to be helpful to them.

And so it's much easier in the same way that I think I've been a pretty good agent. I'm good at pushing people and, you know, pep talking them much more than I am about myself. So putting myself in the mindset that I'm pitching Big Think and trying to make it grow, whether that be through investment or sales, is much easier than thinking about this is an outcome I'm looking for for myself.

So distancing yourself in a certain way from your own ego and just think about the business is how I would go about it.

Okay, and Sakura, who's watching on Big Think Edge, says, "Can you speak to habits in your life that have made you successful? For instance, designated planning time or wellness checks or reading?"

I would say neuroses and overwhelming anxiety have been the driving force in my success. I do write books and things, but it's just really what has driven me is a great anxiety about not achieving things.

So that's the honest truth. And that actually brings us to a great question from Peter Hopkins, who I think you know, who says, "What do you do to manage your stress? What are your practices to help you lower the stress temperature when it feels like it's going to boil over?"

Well, I mean, in the book, I discussed it was, was it a year or two ago? I guess it was two years ago. I actually thought I was having a stroke and had to go to Mount Sinai, where I probably made a total fool of myself. But Peter came and saw me there, and so in those moments, I started to meditate, and it hasn't been a hundred percent successful, but it has worked some of the time.

I need to get back on it because I go on fits and starts. But then also, I guess about four years ago when Peter initially confirmed me about my anxiety and depression, I actually went to a psychiatrist and got put on medication.

Now, I hope I don't stay on it for the rest of my life, but I'm not embarrassed about it, and so I took that matter into my own hands and actually addressed it head-on.

Thanks, actually. So maybe he addressed it head-on, and that actually is like a good segue into our last question, which is from Monica Platt, who's watching on YouTube.

You know, we've talked a lot during this conversation about successes and about overcoming things, but also a lot about anxiety and about dealing with the hard parts of this. And I think for a lot of people, when they're thinking about becoming an entrepreneur or they look at a path like yours, it's very inspiring, but it's also scary, right? There are all these unknowns.

And so what Monica asked was, "How do you become less fearful? What advice do you have for people who say, 'I want to do this thing, but I am scared' to help them overcome that?"

I don't know that you can overcome the fear. I still feel fear oftentimes. I think it's just literally plowing through. If you're focused and actually doing things, the fear kind of dissipates. It won't go away, but actually taking action is how I would encourage people to move through the fear. Literally move through it. It won't go away, but the more you're doing, the less you'll be able to feel the fear.

Yeah, I think it's good advice for all parts of life.

Well thank you so much, Victoria, for having this conversation with me. It's so interesting. And thank you to all of you who tuned in for your questions and for joining us. And you should absolutely look for Victoria's new book Digital Goddess, which is coming out everywhere the books are sold on October 6th, and you can pre-order right now if you want to.

And please join Big Think next week for a sponsored webinar with Matthew Pullman, who is the CEO and co-founder of Nanotronics, and he's going to be discussing radical innovation, unlocking the future of human invention. That's next Tuesday at 1 at August 11th at 10 a.m. with a live Q&A.

And in the meantime, thank you, Victoria, and thanks viewers for coming and joining us.