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How to Bring an Entrepreneurial Mindset to Any Position

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Rebecca Minkoff

You don’t have to own your own business to think and act like an entrepreneur. Being entrepreneurial is a mind set and a skill set that can be applied to any position at any level.

Fashion mogul and social activist Rebecca Minkoff talks candidly about her journey and shares the top attributes most important to her success and in overcoming the challenges she faced along the way.

Whether you are starting a business or leading a corporate team, this episode will arm you with experience-based advice that allows you to take the driver’s seat of your career and life and unleash the fearless entrepreneur within.

Rebecca Minkoff

Rebecca Minkoff is a fashion designer and an industry leader in accessible luxury handbags, accessories, footwear, and apparel. Her modern bohemian designs are inspired by strong, confident, and powerful women who embody the effortless, free-spirited lifestyle. She is a global brand with a wide range of apparel, handbags, footwear, jewelry, timepieces, eyewear, and fragrance. In 2011, she won industry recognition when she was awarded the Breakthrough Designer Award from the Accessories Council. Her podcast, Superwomen with Rebecca Minkoff, is consistently in the top 100 of her categories and has launched the #superwomen tribe across the world. She also established the Female Founder Collective, a network of businesses led by women who invest in women’s financial power across a socio-economic spectrum by enabling and empowering female-owned businesses. This organization has grown to over 9,000 members and has supported women owned businesses by giving them access to education, networks and mentorship. @rebeccaminkoff

Celeste Headlee

Celeste HeadleeCeleste Headlee is a communication and human nature expert, and an award-winning journalist. She is a professional speaker, and also the author of Speaking of Race: Why Everybody Needs to Talk About Racism—and How to Do It,  Do Nothing, Heard Mentality, and We Need to Talk. In her twenty-year career in public radio, she has been the executive producer of On Second Thought at Georgia Public Radio, and anchored programs including Tell Me More, Talk of the Nation, All Things Considered, and Weekend Edition. She also served as cohost of the national morning news show The Takeaway from PRI and WNYC, and anchored presidential coverage in 2012 for PBS World Channel. Headlee’s TEDx talk sharing ten ways to have a better conversation has over twenty million total views to date. @CelesteHeadlee

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Episode Transcript

Celeste Headlee:

So Rebecca, I want to start with a question that I have been asking a lot lately, but I haven’t been throwing it away like I used to, which is how are you doing? I mean, I feel like most of us don’t really answer that question most of the time, but at this moment, coming out of a traumatic period, maybe the answer is different for a lot of us. How are you?

Rebecca Minkoff:

Well, you ask this question on an interesting day. My book came out and obviously, every author wants to become a best seller and I definitely became a bestseller, but I missed The Times list by 1100 books. And I’m really trying to think about the bigger picture and not get stuck on this, but I would be lying if I said it’s not clouding my day a little bit. If you want to know how I am overall, overall, I don’t have any complaints. I have healthy children, a great family. We moved to Florida during the second half of the pandemic, temporarily to have our kids go to school because they never shut down and I would commute. And so we were able to have as an unrestricted, I guess, life as we could.

Celeste Headlee:

What do you do when you are a manager, a boss and you reach a point where you feel overwhelmed, how do you handle that when maybe you can’t step away, but you physiologically and emotionally need to?

Rebecca Minkoff:

Usually, when I’m overwhelmed, it’s because there are many things happening all at once. And I think a good example, was like, we were launching a new product category at Rebecca Minkoff. My book was coming out. We have to think about Fashion Week and there’s a collaboration that’s happening in fourth quarter. And so when all vectors are occurring and then the kids are like, oh, I got to do their summer camp schedule as well and grocery shop and whatever, add to the list. That’s when I become overwhelmed. And for me it’s always been very helpful, I have these beautiful post-it notes that are my saviors with lines on them. And I literally just segment out, what do I need to do? And write it all down and of this, what is a priority? And it just helps get everything out of my head, swirling around like a tornado and onto a piece of paper where I can actually begin to tackle it in a very methodical way.

Rebecca Minkoff:

So that’s always been something that’s been helpful and tactical. I also sometimes will be like, all right, stop, what is most important I need to focus on right now what can I let go of? Because we can’t juggle it all. And so sometimes I’m just like, well that ball’s got to drop and I have to be okay with that. And so I think it’s also knowing when to just let something go. Even if you’re going to pick it up back later, that’s really been helpful to me too.

Celeste Headlee:

Let’s talk about your book because it’s interesting to me, the book is called Fearless and you just expressed an anxiety that you have, a little bit of fear that you have. Explain to me what you mean by Fearless, and is it supposed to be literally without fear?

Rebecca Minkoff:

It is definitely not supposed to be without fear. I called it Fearless because you are going to experience that emotion that’s been hardwired into us for longer than 10,000 years, let’s just say. And it’s there to protect you from life-threatening situations. But that emotion also enters into our personal and professional lives and holds us back. So my goal is that you’re going to recognize that fear, you’re going to use my rules to have stable guideposts with how to take a risk and how to think about risk from a business perspective. And then you go, you know what, I’m scared, but here I go, let’s do it.

Celeste Headlee:

Can you walk me through one of the rules, especially if it’s one that became crucial for you over the pandemic?

Rebecca Minkoff:

I think that the crucial rule that became my mantra during the pandemic is, well, there’s two really, one of them is that sometimes… Chapter 21 is called it’s endless, and success is being able to keep going. And if I look at my past in history, there was invitations not only to fail, but to give up so many more times than I like to admit. And instead of just being like, all right, I’m throwing in the towel, this is too hard, my co-founder and I just got back up. So I think that that’s something that throughout last year was a mantra of mine, of we just got to keep going. We might come out of this a different company, well, we are a lot smaller, but we kept going. Every day there was a reason why we should walk away.

Rebecca Minkoff:

I think the other is to take risk. Sometimes you win and sometimes you learn. And I think when you have failed, rather than going into a shame hole or berate yourself or tell yourself, you’re a piece of crap, it’s like, what did I learn here? And I think anytime you can learn something, you’ll be stronger and better for it. So when you reframe failure like that, I think it definitely can help you to bounce back sooner.

Celeste Headlee:

Is that tied into the advice that you also give on Unlocking Creativity? I mean, it seems to me like sometimes finding the upside or the learning opportunity in failure requires a creative mind. Does it not?

Rebecca Minkoff:

It definitely requires a creative mind, but some people will immediately look to creative minds and say, oh, I’m not an artist, but anyone in business or in corporate America, you have creativity because you’re solving problems. And that takes a lot of creativity and you’re painting, hopefully your purpose and path, and that is in itself is creative.

Celeste Headlee:

So can we talk a little bit about the idea of how to unlock that, not just accept that you can be creative regardless of your job, but also how you tap into the creative part of yourself.

Rebecca Minkoff:

If you look up the definition of creativity, it’s someone that is making something and we’re all making something, whether that is our life or child or a meal or an experience or a job or a company. So right there, it gives you a much broader canvas of what you’re creating. And then I think it’s really important to hone in on what makes you happy, what gives you purpose. And not everything that gives you purpose is going to make you rich or make you money, but how do you align your life to be more purposeful towards what does those things for you? And I think when you can start looking at that, and if you do want your purpose to make you money, maybe it’s not an immediate, overnight gratification, but how do you start to pivot your life to embrace that?

Rebecca Minkoff:

If you know you’re going to work at a job you hate forever, how do you make sure that you have a very rich life on the outside that fulfills your passions? And the creativity and the spin on it is up to each person, but I think discovering those things as the basics for that are the first steps to take.

Celeste Headlee:

Interesting. Each time I ask you about one of the three topics, your book title says, Unlocking Creativity, Courage, and Success. Every time I mention one of them, it leads us to the next, and that’s true here because we’re talking about creativity, but you’re also talking about how to define success. I mean, you’re saying that the definition of success is individual or unique to each person.

Rebecca Minkoff:

A hundred percent. I think, we’re all brainwashed to some degree of what we think success looks like. If you just take Mad Men, they did a good job advertising to us. Oh, you’re only a success if you’re rich and famous. And I think it’s up to us to reframe what does success look like for ourselves, each individual person and did the things that I’m doing feed me or not? And I think I ask myself that question every day. Am I just doing this because it’s what I have to do? What about it makes me excited? Okay. How could I focus more on that? For me, these days, the big risky things is what makes me excited. So that’s what I like to pour my energy into. And I think that can become what success feels like.

Celeste Headlee:

Is there a different strategy for taking a big risk than there is for going about your day to day job, getting through your daily works. Do you do something different when what you’re doing is risky, is as a gamble?

Rebecca Minkoff:

I like to weigh the risk as… I go extreme when I weigh risk, like, will I lose my livelihood? Will I damage my brand? Will I upset someone? And if I can say no to those things, and I’m sure there’s a couple more things on the box list, I should check off, then I’m like, okay, what do I have to lose? We’ve also become known as a brand that is willing to take risks and sometimes have failures. And so I think that we get a little bit of a free pass sometimes because we’re just like, you know what, if we mess up, we messed up. If that idea didn’t work, okay, it didn’t work. And so I think the more people can embrace that, the more understanding people will be like, well, at least they’re trying something, at least they’re innovating and not just staying still for concern of what people think about them.

Celeste Headlee:

I feel like this is something a lot of people are thinking about right now, or have been thinking about over the past year. There’s been a lot of job insecurity over the pandemic for business people like yourself or myself, it’s been volatile and very much like a roller coaster. And then for people who are working jobs for other companies, many of them have either had hours cut, they’ve been laid off. There’s just been a lot of change. And I wonder, how do you weigh your options when you’re deciding whether to become an entrepreneur, whether to start your own business or commodify something that you already do perhaps against the safety of a job and a salary?

Rebecca Minkoff:

I think that question is answered differently depending on how old you are and also what your responsibilities are. I would tell a 20 something with no kids, just their college tuition debt, full force go for it because they have nothing to lose. I would tell a woman who’s feeding her family and is more entrenched in a certain career path, do this more safely because you do have to provide for your family and you do have a role to fulfill, to be able to take care of them. So I think it’s hard to answer it specifically, but I think when you said, sorry, it’s like gambling, what can you afford to lose? And know that you can be… When I bought my first Bitcoin many years ago, the friend talking me into it was like, can you afford to lose $5,000? And I was like, it would really suck. I don’t want to lose five grand, but sure. Okay. You know what, let’s do it.

Rebecca Minkoff:

And so can you approach the risk that you’re taking of? Can you afford to lose whatever it is if you don’t make it? And if that’s the case, and again, you will have learned something if it fails, then I say, go for it. Because there’s so much regret or what happened or what could happen and you’ll never know until you try.

Celeste Headlee:

Well, how important is the right degree in that decision? I mean, you have talked about your pathway as being a little unorthodox. You didn’t follow what we think of as a traditional path. You didn’t go to university. For people who may be… Sometimes we go down these checklists to make it less of a gamble, is an advanced degree helpful in that regard?

Rebecca Minkoff:

I’m not going to ever be the person to dissuade someone from going to school and getting an advanced degree. I think we’re coming into an age where people are questioning, if that degree is going to get them where they want to go in life, or are they going to be saddled with so much debt that they can never take any risk? So I didn’t go to school, my co-founder didn’t go to school and here we are. And could we have made smarter decisions had we gotten our MBA at Wharton? Maybe. But what I really think is I probably would have met people there that would have accelerated what I was going to do anyways. I don’t know that I would’ve learned it sitting in a classroom. I think enough can be said about the learning takes place on the job. It takes place in the business. It’s not sitting on your butt.

Celeste Headlee:

There is this trend recently for articles in Business Insider or Forbes to say, here’s the habits that successful CEOs have, basically implying that if you do this thing, if you wake up at 5:30 every morning and do calisthenics for 15 minutes and make your bed every time and drink 20 ounces of water, then you’ll be successful too. I wonder what you make of that whole trend, of listing out what successful people do and encouraging other people to follow those habits.

Rebecca Minkoff:

I guess I’m impartial. I think if any of those habits sound fun to you try them, but you can’t recreate, molecule by molecule or habit by habit, whatever success someone else has. I started following this fitness instructor because everybody else did it and because he was the top guy. And guess what? I found a great change in my strength because of it. And I was like, cool, that’s a habit I’m going to keep, but not because I’m following the pack now, it’s actually because what he does work. So I say, try it if it works for you. Awesome. If it doesn’t, throw it away and develop your own habits.

Celeste Headlee:

I mean, is this the same kind of attitude you bring to business? How long do you wait before deciding that something isn’t working?

Rebecca Minkoff:

In business, we react a lot quicker in terms of, the data is there, is there every day. So we know very quickly if something’s not working, but then you have other parts of the business, if you’re doing top of funnel activations, or you’re doing a campaign that can’t be measured, you have to know that it’s going to take time. It’s a slow build. I think a good example is about four years ago, we had a woman in the company that decided that we should no longer do any PR activities essentially, that PR wasn’t important, that being culturally relevant was, and she shut off that funnel and within three months we saw a huge decline in brand search and mentions and we switched and pivoted, but it took us six months to get back there. So I think that you can’t expect these things that you start to change overnight.

Celeste Headlee:

So, okay. You have now been an entrepreneur for two decades, almost two decades?

Rebecca Minkoff:

Yes. Almost two decades.

Celeste Headlee:

I mean, what would you think looking back at the woman who started out 20 years ago almost, what’s the guidance that might have helped you the most?

Rebecca Minkoff:

I think the guidance that helped me the most was… That’s a good question. The woman that sold my bags early on was very tough, sometimes to the point of just cruel, but she taught me the value of customer being first, of listening, of just being really damn good at what you do and striving to always become better. And I think that as much as I had fantasies of when we just get to X, I’ll be able to put my feet up and not be on the gas pedal. I quickly realized when we hit what I thought was that number, that I was like, oh, you actually just have to drive faster now, there’s no putting your feet up. And so I think knowing that demand of excellence is something that has to continue, there’s no sleeping.

Celeste Headlee:

How long do you plan to continue? Do you have a date scheduled for, all right this is the point when I actually do take my foot off the gas?

Rebecca Minkoff:

I have fantasies of when I’m going to take my foot off the gas, but I’m just not there yet. I mean, I think if we’re talking about business and you’re just doing the math, if I own X percent of my company, I need to hit Y before I can sell it and come away with something meaningful and have what happens normally when one sells a company. Where I could have my job and still be part of it, but the pressure isn’t only on me and my co-founder and our team, it’s on a whole new group that hopefully helps it grow. So I think that there’s a number in my head. I don’t ever want to do anything else, so it’s not like I would just quit either. Do you know what I mean?

Celeste Headlee:

Yeah. I totally understand what you mean. I mean, I find myself constantly coming up with numbers and then discarding them. It changes all the time for me, of when I think I’m going to start releasing the pressure. And I’m sure this is a different calculation for people who are not business owners or entrepreneurs. And I wonder what kind of advice do you have for our listeners who, I mean, the majority of our listeners are in traditional roles. They’re either salaried or they have a boss of some kind and a wage, and they’re working within, often a corporate environment. What advice might you have for them in terms of being successful in that role?

Rebecca Minkoff:

I would say that my advice for anyone who works for someone else’s, you can be an entrepreneur. You can think like one, you can act like one, you have this safety net that we don’t have of working for a larger company. And I think that people that succeeded and get raises and get promoted or thought leaders within companies are the ones that take risks. The ones that can lead, not only with conviction, but with vulnerability and who are great at taking others along with them. I think too often you hear these people at the top I, I, I, and I truly believe you might hear my voice today, but I’m only here because of the team that I have. And so how do you take the risk, bring the people with you, keep promoting others and do things that might sound crazy within a corporate structure, but that actually allows you to shine.

Celeste Headlee:

I mean, this is a question I think a lot of people have, again, the pandemic has changed a lot of things, and we are hearing a lot of stories about people who are creating new limits to what they will tolerate in their workplace. For example, many people are now saying, if my boss forces me to go back into the office, full-time rather than having at least a hybrid remote situation, I’ll quit. What kind of advice do you have for someone from making those kinds of decisions as successful as they can be, for making sure that they’re deciding their, I guess their walk away points in as productive away as possible?

Rebecca Minkoff:

I mean, I’m sure that each situation is so unique, but if you love what you do, and it’s more about the work-life balance that you want to have, everyone has to stick their neck out to some degree. So could your first opportunity be, instead of, I quit, if you force me to, it’s, hey, here’s a petition signed by X amount of people in the company, and this is how we want it to change. And this is how you can measure our success. I’m only giving women examples, but if you look at the right to vote or the right to our bodies, or what Susan Fowler did at Uber, all these women took extreme risk. They took societal cancellation. They went to jail, not Susan Fowler or [inaudible 00:22:37] on the bus, you think she was fucking comfortable sitting on that bus, not moving? Hell no.

Rebecca Minkoff:

So if you’re scared of your boss being upset with you, because you want to work from home because you’re more productive and happier, I’m sorry, but you got to stick your neck out. If you want to keep working there and you love it, except for that, so how do you galvanize and make change within your company and be the person that ushered that in versus the person that’s like, I’m effective this decision and I’m out? If you do want to leave, there’s so many great opportunities now for people, I think technology makes it so easy to start a website, become a brand. So many of the things that were hard before are easier, but that also means that you have to be better at cutting through the noise. So where are you going to turn to and how are you going to do that is a whole other, probably podcasts, but I’d say before you jump, make sure your eggs are in order.

Celeste Headlee:

So that’s one class of women. And then we have another class of women that had to leave their job because they didn’t have a choice, I mean, almost 2 million women left the workforce since February of last year, 2020. And so there’s a lot of women right now having to weigh how much they can work, how much they want to work and then how to get back in when we know that the job market is not always very forgiving to people who have gaps in their resume, any guidance for somebody who’s in that situation?

Rebecca Minkoff:

Yeah. I would say that I can only speak to the last recession, but out of that recession was a boom of incredible companies, whether it was Airbnb or Uber, companies that have fundamentally changed how we operate. And I think that rather than look at the horrific statistics of 2 million women leaving, could we say here’s 2 million potential entrepreneurs or here’s 2 million potential founders of companies that some will change the way we fundamentally live. And so my say to them is there’s companies like the Second Shift, which offer part-time work for women, where you basically get to filter out for your perfect job. There’s communities like mine, the Female Founder Collective, and our entire goal is to educate women on how they can start and succeed in launching their companies and make sure that the gaps that they have are filled with other women founders educating them.

Rebecca Minkoff:

And so if you are going to go that road, prepare for battle, because it’s not going to be an easy road, but you can do it. You just got to make sure that again, you are ready and stocked with your ammo to set out there. And I truly hope we see that, we’re already starting to see the numbers. I think I read in the news, it was like 2000 businesses a day are being started by women. So we know it’s not working and so now it’s up to us to figure out, okay, well, what does working look like for us?

Celeste Headlee:

What do you think it might look like? I mean, as we come out of this, what do you think we might see in the year or two into the future? What do you think will change?

Rebecca Minkoff:

Yeah. I mean, what I see within our collective already is it’s solo entrepreneurs or companies of two, they have a great product that they can market, not too expensively, it pays for their living. Are they going to be the next unicorn? Never, but I don’t think anyone should expect that they should be a unicorn. I think again, marketing and magazines have done a really good job of putting a lot of women on the cover and we all think we need to have billion dollar brands that IPO, when many or 99% of us won’t ever have that or should ever have that because it’s not what we’re doing. And so I think there’s opportunity again, because technology has made it so easy that if you have an idea, the path to launch is not hard. It’s getting an audience and sticking around that probably is more challenging.

Rebecca Minkoff:

So, I think again, do you want to work to live or do you want to live to work? And based on that, you can probably get the answer of… I know at my company pre pandemic, I was like, man, I could see that my life would be balanced if I could get to the office at 10:00, it would allow me to drop off the kids and go work out without feeling guilty or waking up at 6:00 AM. And we end our office hours at 4:00 or 5:00, so I could get home and make dinner, which I do enjoy and give back to my kids and not feel so rushed instead of getting home at 7:00. And at the time it just felt like, well, how are we going to do that if no one else is going to do that? And then we’ll be the company that falls behind because everyone’s working.

Rebecca Minkoff:

And now, we’re never going back to full time. I think we’re going to mandate two days a week, but if someone… My head of econ just worked remote from Europe for the last week and we didn’t care. So I think that from my company, I think ironically, in a time that’s been so horrific, found what balance could look like as we emerged, because it set a stage where everyone’s rethinking it. And so we’re going what’s right for us and the people that work here?

Celeste Headlee:

I mean, that sounds like an encouragement to everybody to stay flexible, I mean, to not draw lines in the sand, is that what you’re saying?

Rebecca Minkoff:

I think you shouldn’t draw lines in the sand and I think that people are listening. I don’t know why, it went from, everyone’s losing their job to everyone’s quitting very quickly. And I’m like, are we being manipulated here? But I think that employers are listening and watching, because I think they’re all scared they’re going to lose their staff after reading about this rash of resignations.

Celeste Headlee:

Do you give thought to retention and how you might keep staff members?

Rebecca Minkoff:

I definitely do. Our particular issue has always been that another company comes in and offers a huge wad of cash to someone, that we can’t compete with. And so I think we’re trying to figure out, what can we offer to someone if it’s not a $25,000 raise? What are some perks that they get to have? And we ironically just had a situation with one woman who was offered, I think even more than that to leave. And we said, “Listen, we know we can’t compete on price, on salary, but if you stay with us for one to two more years, you’ll be able to command probably double, triple that because of the perception we have as a brand with our innovation and our risk-taking and longevity, whereas this brand can pay you a lot of money, but no one cares about them. So you’ll probably get there and be potentially make incremental raises, but maybe not the jump you eventually want to have.”

Rebecca Minkoff:

And she could see if she looked out two more years, that we were right and she decided to stay. So I think each individual person is so different and retention is definitely top of mind. And I think now more than ever, we’re trying to make sure that people feel happy and valued, even though it’s an environment where it’s not like, oh, we can just give out tons of raises and bonuses after the last year we had. So we’re trying to make them feel better in other ways, until we’re a little bit more back on our feet.

Celeste Headlee:

I mean, I know you shortened your work hours, but are you also working remotely more now?

Rebecca Minkoff:

Yeah, so we’ve only asked that people come in one to two days a week and to sign in when they do and we’re not making… We’re going to do that through the summer and then we’ll see what happens in the fall. But again, I don’t think anyone’s planning to do more than three days a week in the office ever again.

Celeste Headlee:

Ever, like forever? That this is just your work style now, three days at the most in the office?

Rebecca Minkoff:

I don’t want to say forever, hold on, I can only say for now, but there’s definitely times where it is every day, if it’s at Fashion Week. My design team, they love coming to the office. They’ve been there every day, since May of last year. They didn’t want to stay home and they couldn’t design over Zoom. So they made the back of my office, it looks like someone’s apartment and they love it. And they play music and they got their plants growing. And so I’m not telling them, oh, you can only be here three days a week, they want to be there five days a week and no one’s forcing them to. So I think we’re leaving it flexible, but to my head of accounting who lives in New Jersey and has a two hour commute each day, she never needs to come in. And that’s fine.

Celeste Headlee:

So before we wrap up here, I wanted to bring this back around to your book, Fearless, because I love the way that you set it out as rules, which are like guidelines. And I wonder in light of all we’ve been talking about, over what’s changed in the past year and what may or may not, never go back to the way it was. Can you give us a rule that might help us with this kind of, I don’t want to say uncertainty, but it’s a new landscape and that can be unsettling to people.

Rebecca Minkoff:

I think it’s a new landscape, but I made this really… I’m really proud of this example that I gave to my son, but he’s nine and sometimes I feel like he can be a little bit short-sighted. And I said to him, I was like, “Your great grandfather who spoke Russian was sent here on a boat without his family to Sheboygan Wisconsin, and had to somehow find, I don’t even know how people met up those days. The boat arrived, you’re just supposed to be like, I think you’re my uncle, I don’t know. I just like to look at history because I’m like, what we’re complaining about is nothing. If you look at the last pandemic, what? 20 million people died or the Great Depression were red lines wrapped around the streets. So for me, I think always going to problems of comparable magnitude or history makes me go, all right, I can do this. What am I complaining about? Not being on a bestseller list yet? Okay, fine. Get over it.

Rebecca Minkoff:

So I think change is scary. There has been an over proliferation of fear-mongering, especially around this year. And so it is very scary and you can’t negate that emotion, but you can’t let it stop you. You have to find a way that you’re going to go forward anyways and not let it be that that part of your brain controls you. Because that would be a terrible thing to say, I’m the effect of a secretion in my brain.

Celeste Headlee:

Rebecca Minkoff, Thank you so much.

Rebecca Minkoff:

Thank you for having me.





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