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Linda Rottenberg On Empowering High-Impact Entrepreneurs To Scale Up

Linda was named one of TIME’s “Innovators for the 21st century” and “the Entrepreneur Whisperer”.

Linda Rottenberg is an expert on entrepreneurship and leadership. For years she was known as “La Chica Loca” (the crazy girl) for insisting that high-impact entrepreneurs exist in emerging and developing markets. And in 2014, she published her best-selling book, Crazy is a Compliment.

As co-founder and CEO of Endeavor, Linda has led the global entrepreneurship movement for over two decades. With 60 offices spanning the world, Endeavor rigorously selects, mentors, and invests in high-impact entrepreneurs leading the fastest growing companies in underserved markets. Today, 1800 Endeavor Entrepreneurs generate over $15BN in annual revenuesand produce more than 2 million jobs.

We had a high-octane discussion about what it takes to scale up your business: from markets to talent to mentors to equity. Linda shared a number of powerful strategies that work for Endeavor entrepreneurs, from having a “start-up prenup” to executing “minivations” to leveraging economic downturns to stalking! And finally, we discussed what it means to be a great leader.

My favorite quotes included: “When economies turn down, entrepreneurs turn up”, and “Stalking is an under-rated start-up strategy”! And Linda made two book recommendations: “Blitzscaling” by Reid Hoffman and “Manhattan Beach” by Jennifer Egan.

If you would like to follow Linda, you can find her on Twitter or at You can also get her book Crazy is a Compliment, and listen to her episode on Masters of Scale.

Read the Transcript

Note: While When Women Win is produced as an audio recording, we are delighted to produce transcripts for those who are unable to hear. Kindly note that these are generated using a combination of speech recognition software and human transcribers, and may contain errors. Media is encouraged to check the corresponding audio before quoting in print.

Rana Nawas: (00:00)
Hello ladies and gentlemen, my guest on today’s show was named one of Times Innovators for the 21st century and the Entrepreneur Whisperer. Linda Rottenberg is an expert on entrepreneurship and leadership. For years she was known as “La Chica Loca”, “the crazy girl,” for insisting that high impact entrepreneurs exist in emerging and developing markets and in 2014 she published her bestselling book, “Crazy as a Compliment.” As co-founder and CEO of Endeavor, Linda has led the global entrepreneurship movement for over two decades. With 60 offices spanning the world, Endeavor rigorously selects, mentors, and invests in high impact entrepreneurs leading the fastest growing companies in underserved markets. Today, 1800 Endeavor Entrepreneurs generate over $15 billion in annual revenue and produce more than 2 million jobs. We had a high obtain discussion about what it takes to scale up your business from markets to talent to mentors to equity. Linda shared a number of powerful strategies that work for Endeavor Entrepreneurs from having a startup prenup, to executing mini-vations, to leveraging economic downturns and to stocking. And finally, we discussed what it means to be a great leader. So let’s get into it.

Rana Nawas: (01:30)
Linda, thank you so much for coming on When Women Win. It is such a delight to have this time with you.

Linda Rottenberg: (01:35)
I am thrilled to be here.

Rana Nawas: (01:37)
You’re one of the world’s biggest experts on entrepreneurship. You’re known as the ‘Entrepreneur Whisperer.” So let’s start there. Could you tell the listeners a bit about Endeavor, what you do, and why you founded it over 20 years ago?

Linda Rottenberg: (01:51)
Yes, I know. Endeavor is now 21 years old. We’ve officially came of age, I suppose. It’s hard to believe. It feels like our journey is really just getting going. But the story is that I was living in Argentina, going back and forth between Argentina, Brazil and Chilé for a variety of projects and then working with Bill Drayton at Ashoka for a while. And then I kept saying, well, wait a minute, where are all the business entrepreneurs and people? This was the mid 1990s, and in the US we were having Yahoo, Netscape and Steve Jobs coming back to apple computer and yet, no one I was meeting wanted to become an entrepreneur and I didn’t understand why. And so I learned a few things. Number one, there wasn’t even a word in Spanish or Portuguese for entrepreneur at the time. Number two, there was a perception that unless you had family in government connections, you couldn’t get the support, you couldn’t get the mentorship and you couldn’t get access to capital or access to market and I just thought, “wow, that’s insane! We need the next Microsoft not Microcredit down here and we need people to think big.” And so I went back and thought that it was a great idea to support entrepreneurs and Latin-Americans around the world and people introduced me to this other crazy kid named Peter Kellner who was talking similar jibberish and that’s really how Endeavor started. And so the idea was always that you had incredible talent, incredible ideas in emerging and growth and redeveloping markets around the world, but that there were missing piece that, in our view, if you could find role models, mentors and an ecosystem that supports the scale up of these great ideas, then you could generate growth and opportunity.

Rana Nawas: (03:45)
So how do you translate that into practical things that Endeavor does? What does Endeavor physically do?

Linda Rottenberg: (03:49)
Yeah, that was the theory. Now what? So, well 21 years later, here’s where we are. So this crazy idea that no one thought would work…I was known as “Chica Loca” throughout Latin America and in fact, in 2007, when I co-chaired the World Economic Forum Middle East gathering in the Dead Sea, and my good friend Fadi Ghandour was one of the co-leaders of that, he introduced me as “Chica Loca” to the Middle East.

Rana Nawas: (04:22)
That is so Fadi.

Linda Rottenberg: (04:22)
So all throughout MENA I’m also known as “Chica Loca,” which I love. But here’s where we are: Endeavor now operates in 33 markets around the world and we screened over 60,000 companies, not at the startup phase, but at that scale up phase. So generally speaking, half a million to a hundred million dollars in revenue. But people who really need to grow at least 10x that and need the support to get to the next level and as of this year, 1800 selected Endeavor entrepreneurs have generated $15 billion in revenues as of 2017 and created one and a half million jobs and what’s exciting is that two thirds of the jobs and three quarters of the revenues come after their association with Endeavor. So really what we do is first give that seal of approval to become an Endeavor Entrepreneur which takes about six months to a year. So suddenly people know that there’s been due diligence, which is important because a lot of our entrepreneurs are raising capital from both within and outside their regions and so people will say “oh, they’re an Endeavor Entrepreneur. There must be something worth taking an extra look at.” As of the market, it’s really, really important now. I think even if you’re a small and growing business, you need to think outside your borders and so a lot of what we’re doing is connecting people not only inside their own countries, cities and regions, but really globally because a lot of these ideas apply worldwide. And then access to talent – thinking about people’s roles as they change from the startup person to somebody who needs to build, scale and grow a team. And then lastly, it’s about a peer network. So a lot of what Endeavor is, I’ve always said, is that it’s of, by, and for entrepreneurs. So it’s entrepreneurs mentoring one another, giving one another support and tough love, and reinvesting in one another. So now through our Endeavor catalyst funds and through opportunities to really pay it forward, we believe that that’s where you get this multiplier effect, where entrepreneurs nominally worry about growing their own companies and scaling their own teams, but reinvesting to help others dream big too.

Rana Nawas: (06:31)
And you mentioned that you’re in 33 markets. Where are these markets? All continents?

Linda Rottenberg: (06:36)
Yeah, all throughout. We’re in seven markets in MENA, we’re throughout the Middle East, Latin America, Africa, Asia, Southeast Asia, Europe, and also the United States. We made a decision about five years ago that there were underserved markets in the US as well. So we’re now in five cities in the US along with countries globally.

Rana Nawas: (07:03)
Oh, wow. And so we were talking earlier about the UAE. You’ve been here obviously many times and you’ve been to Dubai, is that right?

Linda Rottenberg: (07:10)
Yeah. I love Dubai.

Rana Nawas: (07:11)
And how’s Endeavor UAE going?

Linda Rottenberg: (07:14)
I think the UAE is killing it in a great way. To be honest, for a long time we talked about Argentina and Brazil being places where Endeavor’s model really come to life, because the entrepreneurs are those who’d founded companies and really achieved great success and then were reinvesting as angel investors and mentors and you could just see the entire ecosystem blossom over time. And what’s super exciting is we’ve now been in the UAE long enough to start seeing that happen and seeing those same results. And I think the talent and the commitment we’re seeing in Dubai rivals any city in the world. The UAE, I couldn’t be prouder and it’s now become a model for every other new Endeavor country starting-up. We just started in Vietnam, Nigeria and Puerto Rico and I said, “look to the UAE and look at what’s happened in the last five or six years. It’s super exciting.” So I think that when you see companies like Fetchr, which have gone on to really grow in Saudi Arabia as well as in the UAEwhen you look at Careem obviously scaling throughout the Middle East…we’re talking about women. You look at, you know, Mona of Mumzworld, if you look at Suka Mall and you look at all these female led businesses, you look at Property Finder, I mean there’s just so much to be excited about and it really feels like the momentum. For a long time, there were Souk, there was Maktoob, and the question is, is that it? And the answer’s no. We’re just getting going but I am so proud that not only are there great companies and great entrepreneurs, but the heart of these entrepreneurs, the soul of these entrepreneurs is so inspiring. And I truly now think UAE, you know, in our view, rates among one of the top places in the world right now to be a scale up.

Rana Nawas: (09:14)
Wow. That’s huge. That makes me so proud, if I may say it then.

Linda Rottenberg: (09:19)
Me too.

Rana Nawas: (09:19)
Talking about scale up, what have you learned about taking an idea to scale, having done this now for over two decades?

Linda Rottenberg: (09:27)
Yeah. You know, I wrote a book “Crazy as a Compliment” because if you’re going to be Chica Loca, The Crazy Girl, you have to own it. So I’m like, hey, if people aren’t calling you crazy, then you have a problem because you’re not thinking big enough. But I wrote that book really to share some of the lessons in scaling and growing a business. I felt that so many entrepreneurship books focused on the startup, which is fine, but for me, that’s not where the most interesting things happen. Yes, you have to convince yourself to take that leap forward. So giving yourself permission to start your crazy idea is very hard and scary. But after that, in terms of product market fit, you have things like Kickstarter and Indiegogo and different ways to kind of test things, I think, more quickly than ever before. So for me that’s not where it gets interesting. Where it gets interesting is what happens when you grow a team to a hundred people from a band of people that are just using the adrenaline and the passion for the start up. What happens when you reach, you know, 3 million, 5 million, 10 million in revenues? It gets much harder to grow in the triple digits. How do you grow 10x from there, right? Going from 50,000 to 500,000 isn’t as hard, in my view, as going from 500,000 to 5 million or 5 million to 50 million. And I think at that point, so many people focus on the financials and on the products on the market. I focus a lot on the team. I think that culture and team are not only the most undervalued assets or detriments that companies have. But look at what’s happening now with Uber. Look at what’s happening now with Facebook. Look at what’s happening now with Tesla. I think culture and leadership come home to roost if you don’t get those right and I think that one of the things I’m so impressed with the founders of Careem is that Mudassir, Magnus and Abdullah are rethinking, they’re rethinking their roles and they came to us and said, “look, we know everybody is patting us on the back and saying how great we are to have gotten Careem this far. But if we really want to compete with Uber and Lyft, we’ve gotta scale from 1 million captains a year, and we’re growing 60,000 a month and we have our own internal team. If we don’t get culture right, if we don’t change our own roles, then we’re not going to be able to sustain that growth.” I thought that was remarkable. Remarkable. I remember talking to Jeff Weiner of Linkedin when he took over from Reid and so I asked “what did you do?” He said, well, I learned everything we did wrong at Yahoo and tried to apply the opposite to Linkedin because I realized how culture is so important and how changing my own role and just seeing Reid as a founder change his role was key.” So that’s my view; leadership, team, and culture.

Rana Nawas: (12:35)
I do want to go into that a little bit because it’s clear now, I think, that the traits and the skills of someone who starts a business are very different from the traits and skills of somebody who will manage people and pull them along, right? To me, it seems like a very different skillset. The awareness you’re talking about in Magnus and Mudassir is probably not that common. So how do you usually deal with that, with startups where really, you know, the starting team is a great starter team, but not a great managerial team?

Linda Rottenberg: (13:09)
That’s exactly right. And I think a couple of things. One is we’re giving our entrepreneurs more leadership training than ever before. We have programs at Harvard and Stanford Business School. We’re actually looking to take our women entrepreneurs to Wharton. I’ll get back to that. But I actually do think there are different challenges with the extraordinary female entrepreneurs we’ve seen, but they are slightly different challenges and we can get back to that. But I think an executive coaching is something we’re hearing more and more as something entrepreneurs want, which I think is very self-aware. I think that when we look at the cap tables and you look at the ownership, we used to at Endeavor be very distraught that entrepreneurs had given away too much of their business early on, right? And so that used to be the thing we were focusing on, “oh my God, how could it be that series A and the entrepreneurs only own, you know, 8% of their business? This is a disaster.” And that’s still an issue. But I’ll actually say that the capital’s getting slightly smarter, especially when you have now Wanda, you now have Samih of Makhtoob who’s now an entrepreneur who’s become the Founder to Funder Movement, right? You have some of our entrepreneurs paying it forward and investing. The capital is getting smarter. But here’s what we’re seeing now. Number one, do you have an employee stock ownership plan? Is all the equity concentrated in one or a few founders or are they really recruiting the talent at the C-suite to get professional CFOs, to get people to count talent and culture officers? To get the chief innovation or technology officer. Do those people have any equity? Do they have stakes? Do they have skin in the game? That is number one. Number two, the other kind of how you grow up is how do you have three co-founders? If you are all making decisions, if you are all at the same equity, who breaks the tie? And I think realizing that, even if you’re all best friends or family, you’ve got to think about a scenario where interests don’t align and plan. You know, going forward, I always say you need a start-up prenup, right?

Rana Nawas: (15:16)
Yeah, yeah.

Linda Rottenberg: (15:16)
Because no one wants a startup prenup because you know, it’s a signal that we won’t succeed and that the marriage will fail. But no, in fact, you have to plan for what’s going to go wrong.

Rana Nawas: (15:26)

Linda Rottenberg: (15:26)
On the women’s side, we’ve noticed a couple things. One is interestingly more women we’re seeing have 100% of the equity, which is kind of impressive that they haven’t given the companies away. Look at Sara Blakely of Spanx who built Spanx to a billion dollar business. She has 100% of the equity. Tory Burch, almost the same. And while that’s extraordinary, it’s kind of like, let go, you know? Share the wealth and that’s one thing, and don’t be afraid to lose control a little bit. I think that we women value perfectionism so much that we have to be willing to kind of have it be messy a little bit.

Rana Nawas: (16:08)
Linda also on this point, if women feel less confident about their own skills at valuing their company, and so maybe they don’t want to feel stupid, like: “oh my God, I did a bad job, so why don’t I just not do this at all?” Is that possible?

Linda Rottenberg: (16:23)
It’s so possible and in fact, the other thing I’ll say is we’ve had so many female founders who are extraordinary people. Mona aside, you know, I mean, she’s extraordinary, no one mess with Mona, but throughout the world, including our US female entrepreneurs who are terrified to go head to toe with the people who have the capital and are either foregoing rounds or are not negotiating the rounds or even with Endeavor Catalyst. It’s really interesting. We have to be allowed in by the entrepreneurs. They’re terrified. They’re terrified to do anything that’s going to put them in a weaker negotiating spot. And part of what we want to do is build up their confidence. We’re actually having negotiation lessons and capital raising just for women for exactly that reason that you said. We’re trying to dig in: “is it a control issue or is it, as you said, confidence?” I don’t know the answer, but it’s definitely now a pattern. We’ve seen it repeated enough times that we’re trying to take action so women out there have confidence. Also I will say the women have the perfect business plans. The man have half their business plans, didn’t work, they don’t care though, they’ll just wing it. We need to learn to wing it a little bit. For women, everything needs to be tied up in such a pretty little bow that I think we wait too long.

Rana Nawas: (17:41)
Yeah. I have seen studies though that say VCs and angel investors do respond differently to men and women, like they will require more detail from women. They will push harder on women. Have you seen that?

Linda Rottenberg: (17:54)
That’s just true. That’s just true. And I think that one of the other things I’m pushing on as the founder to funder, we’ve seen that model be very successful, I want more strong women to become the funders and angel invest as well. We actually have our new managing director for Saudi Arabia, Lateefa Alwaalan, who’s one of our amazing Endeavor Entrepreneurs and I’m very excited about that because she’s playing this leadership role. I definitely think the funders are still a problem. If you look in the United States, only 2% of venture capital in 2017 went to female founded companies. That is appalling.

Rana Nawas: (18:35)
What percent of startups are female founded?

Linda Rottenberg: (18:39)
I believe it is 18%. I know at Endeavor we’re over 20% female founded, which is great. I believe it’s 18% but only last year 2% funded.

Rana Nawas: (18:52)
Oh my God, that’s a huge discrepancy.

Linda Rottenberg: (18:55)
It’s a huge discrepancy. It’s really embarrassing and I think that we’ve seen this play out in the Time’s Up Movement in the US. I think #MeToo is more focused on the harassment side while Time’s Up is really focused on what’s going wrong in the workplace and how do we fix it. You look at the paltry number of female VCs and the problem that as you’re saying, if you’re a female founder, you actually are at a disadvantage so I think we’re not wrong to think we start out that way. I do think that that was a really relevant point.

Rana Nawas: (19:26)
And it’s interesting this week I released an episode that was with Victoria Tigipko who is a VC funder from the Ukraine. So she has a top four fund in Europe and she was telling me not only is there a similar picture of a very little VC funding and very few female VC funders, but also that female led startups outperform male led startups. Have you seen data to that effect?

Linda Rottenberg: (19:54)
Yeah, there’s definite data. There’s also data that if you have more than one woman on your board, you perform better. I mean the data is incontrovertible. Here is the other interesting note; I was looking at teams where it’s men and women and in many more than half the cases, I don’t know the exact number, but the women is the CEO, which I also found interesting. When we had a co dual male-female startup or scale up, the woman was more often than not, the CEO, which I found to be a great statistic. I really want to focus on this founder to funder issue though because I think it starts at the angel investing side. And I do think that entrepreneur driven capital is on average smarter capital. It started all the VCs out there. And so I want more of our great female fund founders to take that risk, mentor and reinvest as well.

Rana Nawas: (20:49)
Why not? I mean, I became an angel investor funder even without becoming a founder until…

Linda Rottenberg: (20:57)
I love that. I love that!

Rana Nawas: (20:58)
Then a year ago I became a Chica Loca too and started a podcast in a region that hadn’t heard of podcasts. But it’s going fine. So we’re okay.

Linda Rottenberg: (21:04)
I love that and I am so proud to be on your podcast!

Rana Nawas: (21:07)
Oh, that’s very kind.

Linda Rottenberg: (21:08)
I think in the region, by the way, we’re seeing great female entrepreneurs and more so than in other regions of the world. So I think that’s also very promising.

Rana Nawas: (21:21)
And I was curious to hear just now, I didn’t know there was Endeavor Saudi Arabia.

Linda Rottenberg: (21:25)
Oh yeah. Endeavors Saudi- we’re very excited about, particularly under the type of management we’ve seen in the last six months. You take a woman, you take an entrepreneur and everything, you know, ramps up. So I’m very excited about what’s going to happen going forward. We’re in the Middle East. We’re in the UAE, Jordan, Egypt, Lebanon, Turkey, Saudi Arabia, Morocco and Tunisia. As I said, I really think what’s happening in the UAE, because you also have great companies from Jordan and Lebanon where you have founders, you know, moving to Dubai, it’s just such a rich ecosystemand I really feel like we’ve just scratched the surface. I always get asked what regions in the world am I most excited about? And I tell people, you know, you’ve got to look at what’s happening in Dubai. And I was super excited about the property finder investment of General Atlantic partners, which was one of our first investments in the region recently, and it’s $120 million in property finder. Michael Ohana is an incredible entrepreneur that I was just really excited about because I feel like that’s just a sign of what’s to come.

Rana Nawas: (22:34)
Well, let’s bring it back to entrepreneurs in general. What are the most common mistakes that they make?

Linda Rottenberg: (22:40)
Well, I think that it’s interesting. We talked about the business plans and at some point I always say, you’ve got to stop planning and start doing. And I think that so much feedback about what customers want, what’s working and what’s not can only be done by trial and error and getting out. And I think if you get too theoretical and you don’t just put the plan down and start acting, that to me is, is a mistake. I also mentioned the startup prenup. I really think that not thinking about how roles change early enough, you get caught behind not thinking about culture and values early enough. As I said, the DNA, the heart and soul of a company gets set very early on and it’s very hard to change that. And when you’re scaling really rapidly, it’s too late at that point. So I feel like focusing on that culture is the other thing.

Rana Nawas: (23:36)
Thank you. And if I was going to ask the question a different way, what are your top three tips for budding entrepreneurs?

Linda Rottenberg: (23:42)
People talk about entrepreneurs as risk takers and risk maximizers. And I really don’t see it that way. I think the biggest risk is convincing yourself to take your idea out of the shower and off the Napkin and into the world. I always say the greatest ideas don’t die in the marketplace. They don’t die in a laboratory. They die in that shower where you don’t even get out and agree to go do it, you just like say, “oh, that’s too crazy”, and then you go on with your normal life. So you’ve got to take that initial leap of faith, and actually give yourself permission. I find that the best entrepreneurs are risk minimizers not risk maximizers and they just see ahead of the curve, right? And I think that’s the other thing, it’s about understanding that the best companies get founded in periods of downturn and chaos. And that’s when the big companies retreat. So it’s going forward when everyone is going backwards. I always say when economies turn down, entrepreneurs turn up. So, not getting the jitters by what’s happening around you, but actually looking for the open spaces that happen as a result of turmoil. Chaos is the entrepreneur’s friend.

Rana Nawas: (24:51)
Nice. Maybe that’s why we’re thriving in the Middle East!

Linda Rottenberg: (24:57)
Yeah! We pride stability in the US and get freaked out. Yeah, exactly. You need a little bit of turbulence; we’ll always be entrepreneurs. And the last one I would say, I found this at Endeavor, is you’ve got to think earlier on than you would have thought about broader markets. I really think that sometimes people don’t think big enough and you have to test really small. But even if you’re testing small, you’ve got to think big. And then how do you go from point A to point B to point C? But if you don’t have a big enough dream, then you’re really never going to go very far. So, that’s the other thing; don’t limit your dreams even if you take small actions to move on.

Rana Nawas: (25:43)
Yeah. That was my Instagram post today, actually. It was “dream big.”

Linda Rottenberg: (25:45)

Rana Nawas: (25:45)

Linda Rottenberg: (25:47)
Yeah, exactly! Execute small. But dream big.

Rana Nawas: (25:51)
I love it. So do you believe that some people are born to be entrepreneurs and others are not?

Linda Rottenberg: (25:58)
Even though I say entrepreneurs are risk minimizers, the perception of risk is very different for people. And I think that people, if you’re going to get a stomachache by telling people that they’re fired or they’re not going to get their bonuses, you know, then maybe this was not the right role for you. It’s a very lonely job. If you don’t feel comfortable getting 10 doors shut in your face and then going to the 11th…because you’ve got to be that persistent. I always say stocking is an underrated startup strategy. So, I do think that there are some people for whom stability, the constant paycheck, that security is just really important. And I always say it’s a gut check but what I don’t believe is that you have to be a male engineer in a black hoodie in silicon valley to be an entrepreneur, right? So I think some people psych themselves out because they think “oh, I don’t look like an entrepreneur” or “I don’t have an idea that’s as big enough as Facebook or Tesla or Twitter so it doesn’t count.” I always said that mini-vations, mini-innvoations, are often where the best companies are built and regardless of whether it’s an adaptation of existing models just to a new location and understanding the local market, incremental changes can have exponential results if well executed. So, I think that that’s what I would say; don’t assume that you can’t be an entrepreneur because you haven’t seen someone who looks like you or has your type of idea before you. But if you really don’t have a tolerance for the uncertainty and chaos then maybe, you know, this isn’t the right role.

Rana Nawas: (27:43)
Yeah. The reality is though that over 90% of entrepreneurial ventures will fail within the first two years. I don’t know what the stat is exactly. So, the vast majority will not succeed. How do you know when to draw the line? Because then there’s people out there saying, “you’ve got to try, you’ve got to struggle, you’ve got to keep going. Gotta do this, you gotta do that. Don’t worry about failure and all of this.” And then these poor entrepreneurs are out there pushing and pushing and you know, well maybe I’m one of those 90%.

Linda Rottenberg: (28:12)
I love that everyone talks about entrepreneurship as “failure’s great!” and Reid Hoffman, my friend and fellow Board Member, Founder of Linkedin is like “let’s not get ahead of ourselves. We don’t love failure in Silicon Valley. Okay. To be honest, we tolerate some degree of going out of business, but you know, we don’t prize failure, nor should you.” But I think that’s the other misconception people have; that people go all in from day one. I always tell the story of Phil Knight of Nike who was an accountant and selling the shoes in the back of the van, which is this great “rags to riches” story. The guy was an accountant until it was clear that Nike had broken $1 million in revenue, then he went all in, right? Sara Blakely, I mentioned, of Spanx; she was a machine operator, she had a day job and it was only when Oprah put the Spanx stockings on as part of her favorite thing for Christmas, she was like, “oh, if Oprah is doing this, maybe I can go all in and full time.” And I think now you know where we have this gig economy, where we have demand jobs, where we have side hustles, even if you’re part of…a friend of mine was The Chief Marketing Office until recently and the chair of GE, and she said that by the end, everyone at GE had side hustles, right?

Rana Nawas: (29:33)
That’s Beth Comstock!

Linda Rottenberg: (29:37)
She’s the best!

Rana Nawas: (29:37)
That was the first episode on season two!

Linda Rottenberg: (29:41)
Oh really? She just did an amazing book. I love that. Yeah, exactly. So, we’ll talk about how they had to re-orient GE, one of the oldest standing companies in the US, you know Thomas Edison, because people had side hustles. So that’s what I would say; you can test out your idea whether it’s on Kickstarter or whether it’s at the farmer’s market or whether it’s tweaking your tap in your beta test before you have to make a decision to max out your credit cards and you know, mortgage your house and become full time. That’s the other great thing about today; I think that there’s more flexibility.

Rana Nawas: (30:21)
You are also known as a Mentor Capitalist, right? So if we could talk a bit about mentorship. I’m 17 years in the corporate world and I always had mentors and programs shoved down my throat and all of this, you know? And now for a year I’ve been an entrepreneur and it seems a lot harder for me to find that right person. What advice do you have for entrepreneurs on finding the right mentor?

Linda Rottenberg: (30:48)
For starters, I’d go plural. I always say save monogamy for your love life, but you want to be poly mentorish! So I think about it as a circle of mentors. I think we used to think about that corporate ladder where you’d have one grey-haired mentor pulling you up the ladder and looking out for you. That world is dead. So, I think looking at it as this circle of mentors because I found that model really stressful, especially since I didn’t enter the corporate world, I was like,” oh my God, I need to find a spouse and a mentor? Like this is too stressful.” By the way, when you have mentors, sometimes they’re no longer right and then it’s like you have to break up with your mentors. That’s really hard.

Rana Nawas: (31:33)
And very awkward…

Linda Rottenberg: (31:33)
Very, very awkward. Sometimes you have to cut the cord and say “thank you very much. This was wonderful. I’ve taken up enough of your time, but it’s really time for us to move on,” which is a hard conversation, but it’s often a relief to both parties because your world changes. And so that’s why I say get someone who’s older than you. Get someone who’s younger than you. Get someone who’s up there. Get someone who’s a friend. In the book, I tell the story of Larry Page when he went back to Google. He had been the co-founder of Google and then he stepped down as CEO so that Eric Schmidt could take over. Then he went back into becoming a CEO. Who does he go to for advice? His biggest frenemy, Steve Jobs. Why? Because as much as Google and Apple were completely at odds, fighting, they had lawsuits going, Steve Jobs had done the same thing. He had been kicked out as founder and gone back and Larry Page knew that Steve Jobs was the only one who could understand him. So, oftentimes we see entrepreneurs that are in the same field and you’d think they wouldn’t talk, but actually they understand one another better than anybody else. So what I would say is; what’s really nice about having a circle of mentors is it takes the pressure off. You can say, “look, I just want a cup of coffee like every two months.” It’s not somebody who’s going to call you up every week, which is kind of a burden, right? So I feel like if you get different people and then see where the chemistry is at different stages of your life. You know, I have a YPO Forum, we’ve been around for 12 years, but everyone’s needs kind of change over time. So don’t think of only one mentor and don’t think of people being lifelong mentors. Do it for a few years and then maybe switch out.

Rana Nawas: (33:23)
Well, let’s talk about leadership for a second. We talked a lot about the entrepreneurs and entrepreneurial skills and you mentioned what Endeavor does to help sort of create that next skill set of leadership. What makes a successful leader, in your view?

Linda Rottenberg: (33:39)
Well, I think knowing your strengths and weaknesses and knowing that the culture is going to reflect the leader, no matter what, so trying to be someone you’re not is not going to result in authentic leadership. And there’s no one right style, but you’ve got to understand your gaps or be told them. You know, in my own case, I think that for a long time I was like, “oh, I’m a crazy founder and I like chaos. I’m going to try to be a manager.” You know, I was not a very good manager and people told me that. And I was like,” okay, I have to learn.” You know, my husband always told me that I wanted everyone to end a conversation liking me and so every conversation took 45 minutes and after I had kids I was like “oh, I do not have that time.” And so I had to learn to actually do more with less time and it was refreshing for people. Then the next time that happened, my husband got cancer and we went through a year where he was going through a very tough chemotherapy and ended up having this 16 hours surgery to remove his entire femur. And I had always thought that as a female leader, I had to present added strength to give my team confidence and not appear too vulnerable because I thought it would make them feel uncomfortable, like I was weak but I was so wrong. And I came back and I just had to be honest about what I was going through when people ask. And instead of turning people away, people told me that it drew them closer. And so that was a real lesson. And I realized that it’s okay if you’re authentic and if you’re vulnerable, people will respect that. And just trying to be the vision of the perfect leader really results in bad outcomes. I had always thought we had to be superhuman and my lesson was, you know what? Be less super and more human.

Rana Nawas: (35:41)
Yeah. Okay. It’s time for the rapid fire round. What is a book you’ve recently gifted someone?

Linda Rottenberg: (35:47)
Well, I recently gifted people “Blitzscaling” by Reid Hoffman. Two answers. One is that I think it’s really the best book about scaling up that I’ve read. As I’ve said, so many entrepreneurial books are about the startup phase, but this is about not only his work at Greylock and in silicon valley investing, but about his Stanford course and one of his podcast episodes “Masters of Scale.” .

Rana Nawas: (36:16)
I love that show!

Linda Rottenberg: (36:18)
Awesome. That was great! I think it was episode 10. You can go back and listen. So “Blitzscaling” is one. The other is a book by my friend Jenny Egan who won the Pulitzer Prize here in the US. She’s a masterful writer and the book is called “Manhattan Beach.” It’s about a young girl in the 1930s, becoming the first deep sea diver for the Navy, nnd it takes place in the Brooklyn Naval Yards, which is just 10 minutes from my house in Brooklyn. And it is a gorgeous book. I loved the book and so if you want fiction, read “Manhattan Beach.”

Rana Nawas: (36:57)
It’s so funny. Today I was on the phone with a friend saying, “I’ve got to read more fiction. I read far too much nonfiction.”

Linda Rottenberg: (37:03)
I only read fiction.

Rana Nawas: (37:10)
Good for you. And I look forward to my signed copy of “Crazy as a Compliment.” You can give that to me. Who is a woman who’s influenced you greatly?

Linda Rottenberg: (37:21)
Oh wow! What a great question. God, I just have so many people. But I would say that one of our first Endeavor Entrepreneurs, Leila Valez of Beleza Natural, who I just saw. She expanded her hair care company into Harlem in New York. And this is a woman who grew up in the favelas, in the slums of Rio, and got a job at Mcdonald’s. Then she decided to build, with her sister-in-law Zika, a hairdresser of a franchising salon that would cater to the Afro- Brazilian population with curly hair. And what inspires me about her story is that she was not going to stop. People thought, “oh, what a nice little story. Micro-credit.” I was like, “no, no, no. There’s nothing micro about delays in Natural and it’s over a hundred million dollar company. It employs over 6,000 people and she is not done. As I said, she just expanded to Harlem from Brazil a month ago and she’s going to take on L’Oreal.” And what inspires me about that story is that she continues to get a lifelong learning. She went to Endeavors program at Harvard for Leadership. She secured $30 million from the toughest private equity firm in Brazil. She is always pushing herself and yet she is the most beautiful, elegant, soft spoken woman. And I just love that because it’s not our traditional view of a leader and yet I never underestimate her because as quiet, gentle and lovely as she is, she has that killer instinct. So that’s what I would say.

Rana Nawas: (39:09)
I love that as a closing thought that; there are many styles of leadership.

Linda Rottenberg: (39:13)
Yes. I have identical twin daughters who are 13 and a half, you know, they’re a little shy, but I didn’t want them to think of themselves just as introverts. I didn’t want to lock them in. And luckily, nothing is binary anymore, right? With these millennials, or centennials, my kids are centennial, so everything’s beyond the binary. So they came to me the other day, their names are Tidy and Eden, and Tidy said, “we figured out that Eden is an extroverted ambivert and I’m an introverted ambivert.” I love this. What are the models for leadership? You don’t have to be extroverted or introverted. You can be extroverted ambivert or an introverted ambivert. Love it!

Rana Nawas: (39:59)
Oh My God, that’s amazing! Linda, where can listeners find you?

Linda Rottenberg: (40:04)
They can find me on Twitter as @LindaRottenberg, on and You can order “Crazy as a Compliment,” go to the Masters of Scale episode on Endeavor, come visit us at Endeavor in New York or Endeavor UAE. By the way, Happy Birthday, Endeavor UAE. I know there’s a celebration tonight, so I love that I’m on this podcast the night of our local celebration.

Rana Nawas: (40:30)
Thank you so much, Linda. It’s been an utter pleasure having you on the show.

Linda Rottenberg: (40:34)
Oh, real pleasure’s mine.

Rana Nawas: (40:36)
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