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EP 241: How Persistence and Risk-taking led to a Partner Role in Silicon Valley, with Anita Rehman

Anita rehman

Episode Description

Anita Rehman is a Partner at GSV in Silicon Valley who took a 2-year career break. Her experience encompasses roles as an entrepreneur, investor, and advisor to global companies in the Technology sector. Prior to GSV, Anita was an investment professional at Vantage Point Capital Partners where she invested in early to growth stage technology companies across the Consumer, Enterprise and Energy sectors. In addition, Anita is the founder of a vertically integrated plus size womenswear retail startup. Today's episode is part of our "Relaunching in Senior Roles" mini-series.

Read Transcript

Carol Fishman Cohen: Welcome to 3,2,1 iRelaunch, the podcast where we discuss return to work strategies, advice, and success stories. I'm Carol Fishman Cohen, CEO and co-founder of iRelaunch and your host. Today, we welcome Anita Rehman, a partner at GSV Asset Management, who took a two year career break. Her experience encompasses roles as an entrepreneur investor. And advisor to global companies in the technology sector.

Prior to GSV, Anita was an investment professional at Vantage Point Capital Partners, where she invested in early to growth stage technology companies across the consumer enterprise and energy sectors. In addition, Anita is the founder of a vertically integrated plus size women's wear retail startup.

Anita's a graduate of Manipal Institute of Technology, where she earned an undergraduate degree in electrical engineering. Following Manipal, she graduated from the master's in electrical engineering program at Stanford, and later earned an MBA from Wharton. This episode is part of our "Relaunchers in Senior Roles" miniseries, and we're going to be talking to Anita about her experience, not only relaunching, but reentering the workforce in a senior role.

Anita welcome to 3, 2, 1. iRelaunch.

Anita Rehman: Carol, thank you so much for having me. It's great to be here.

Carol Fishman Cohen: Thank you so much for speaking with us. Let's start by talking about your career path that led up to your career break, and what made you take the career break?

Anita Rehman: Sure. So I came to the United States to do a master's degree in electrical engineering. And I started my first job out of college was with a consulting firm, and I was fortunate enough to have tremendous mentors at that firm who encouraged me to go back and get an MBA. And so what happened is that, I applied to several MBA colleges and it just so happened that when I got a letter indicating that I had been admitted to Wharton for their full-time MBA program, I also found out on that same day through my pregnancy test that I was expecting a child. Oh. And so that threw me.

Carol Fishman Cohen: Yes, I can imagine.

Anita Rehman: That threw me into a loop and I just wasn't sure what to do. But I have a really supportive husband, which is a large reason why I've been able to come this far.

And, the suggestion, we put our heads together and decided that I should just go on this MBA journey, figure out if I could manage it. And then if I couldn't, I'd drop out and figure out what to do as the next step. So I just took one day at a time. And so I went to join my Wharton MBA in August of 2004, my daughter was born one day after my OPIM exam on December 23rd of 2004.

And then I went back to school on January 7th, 2005. Being in an MBA program actually gave me flexibility, and that is so critical for new moms. So I was able to muddle through my MBA. I was actually able to go through it. However, when the recruiting process started for us, I just found that there was no way that I could walk in, do all of the interviews, finish my coursework and take care of my one year old child.

And so I decided, just to keep my sanity, to drop one of those three things. And I decided to hold off on the recruiting process. . And as a result, I finished my MBA. I had this really hot and heavy degree in my hand. I had a beautiful baby in my hand, and then I came back to California to look for a job because, unintentionally, I decided to take a career break.

Carol Fishman Cohen: Thank you for walking us through that. That's a very unusual story. And I'm remembering now that we've known each other for a long time. And I think that we connected right at that stage where you were looking to get back in. Is that right?

Anita Rehman: That's absolutely right. All of it is a haze to me, but you absolutely, you stand out, I'm sure. I do remember cleaning out my Gmail inbox one day, and there was an email from me to you. I believe in the 2006 and 2007 timeframe, it's that, it's just such a difficult time and there's so much chaos and you're unhappy with the state that you are in. And I did reach out to you, and you were definitely a helping hand.

Carol Fishman Cohen: Oh, thanks for saying that. I just think it's, it's amazing that I feel like here we are in 2021, having this conversation about your relaunch and your senior role, and that's part of what is, it's giving me chills right now, and it's just, it's such an exciting conversation. Anita, when you were in that mode when you contacted me, I'm guessing you were contacting a range of people. What were you thinking? What was your first thought? How did you approach a relaunch? Can you give us, bring us into your world at that time to just let us know how you went about it?

Anita Rehman: Sure. Yeah. And, so as most women, all of us when we have our child, it's just such an intense, it's beautiful, but also really intense period right after you have a baby, and especially your first child. And I had this fantastic degree in hand and I did come back feeling a little bit left behind or, I felt like I was not enough. Because everyone else in my MBA class was going off to Goldman Sachs or to Blackstone, or to some other really fancy firm. And they had a great title and a big fat paycheck, and I had nothing to come back to. But, I put one foot in front of the other.

I had figured out during Wharton that I wanted to focus in on the finance industry. And I decided to focus my job search on the venture capital industry, which was again, a very challenging industry to break into. But, I did what was, what came naturally to me, which was to reach out to everyone in my network, ask them for recommendations and then continue to reach out to other people.

And that was not easy to do, 'cause in some ways, as I said, there is some baggage, you know that you don't have a job and you're out there looking for something. Whereas, all of your peers have a job. In retrospect, it was just, it was unnecessary baggage. I just wish I had enjoyed that time more. But my strategy was exactly that, it was just to go out and say, okay, every week I'm going to set a commitment to talk to three people.

That's it. Three, it's not too much. I can handle a baby and three people. And I did that. And one introduction led to another, and it was really a random walk through which I was introduced to the partner at Vantage Point. Mind you that random walk took a year and a half. It was not an immediate random walk.

So it took a year and a half. And, and he, we interviewed, I was interviewed by him and we hit it off and I landed the job.

Carol Fishman Cohen: Wow. Alright, let me ask you a few details here. So when you said you assigned yourself, you're gonna talk to three people a week. Were you getting in touch then with people that you hadn't been in touch with for a long time or new people? And what did you actually say? Did you send them an email? What was on the subject line? What was in the email or what was in your first phone message to them?

Anita Rehman: I was, I reached out to people, so I had this brand new network from the Wharton database. And so that was a good leverage point for me.

But I didn't limit myself to just that. I started off with people that I was familiar with prior to actually going to get my MBA, because that's where I had a lot of trust and people knew me. They'd worked with me. They knew that I could deliver et cetera. And so I started out with my network and I said, Hey, I'm back in the bay area, I've had a baby. I'd love for you to meet her. And in addition, I'm looking for a role at a company, and this is what I'm interested in. Would you be available to have a cup of coffee with me? And that's basically what I said. And then, when I sat down with them to have a cup of coffee, I would ask if they knew of others that would be interested in speaking with me. And occasionally it wasn't all the time, but occasionally I would get one or two additional recommendations from my inner circle of friends.

I also sent out cold emails to people from my Wharton database. And that was incredibly valuable to have. When I emailed the people from Wharton, I just said that I'm from Wharton. I just graduated. And I'm back in the bay area. I'd love to connect with you as I'm looking for great opportunities. Carol, it sounds, you know, it was a really hard process.

Carol Fishman Cohen: Yeah.

Anita Rehman: And it entailed so many no's. But ultimately, you just have to put yourself out there. And I think this is just a general rule in life, in entrepreneurship, in getting out there. It is just that you have to go out and tell your story. You have to meet people and you just have to leave all of the judgment that you have of yourself and what you're capable of.

Because, most often, you can do anything you set your mind to.

Carol Fishman Cohen: You know, it's a really important message. It's interesting, you said that you wish you had enjoyed it, the process more now that you were looking back on it, but also you're acknowledging that day to day, and lots of rejections, or not even rejections, just non replies, just people not replying at all. That those can build on each other and that also can feel pretty, pretty negative. So I'm glad you're talking about that piece of it and that it took a year and a half. Did anyone say, you're dreaming, you're never gonna get into VC because this world is just too hard to break into.

Anita Rehman: Almost everyone said that to me, almost everyone. I'm not sure why I kept going because it is a really hard industry to break into. Almost everyone, I'd say about 99% of the people that I spoke to said that to me. One person, and I'll say, Sujit Banerjee, my friend from Wharton who graduated a few years before me, was in VC.

And his advice to me was that, Anita, the way you get into VC is by pounding the pavement. You network, you network, you network, they need to get to know you. They need to trust you. They need to trust your circle. And then it's again, VC is a cottage industry. You don't have HR functions, you don't have jobs opening up and job req's.

Someone suddenly leaves and they're scrambling to find someone to replace them. And I followed that to a T. I was like, okay, I'm going to pound this pavement really hard. And, as I said, I was really lucky to have the Wharton database, all of my friends, and I just kept continuing to network and put myself out.

Carol Fishman Cohen: Wow. Good messaging, and that was excellent advice, but it also required a tremendous amount of persistence on your part. So you had this conversation with the Vantage Point Capital Partners lead and started working there. And what happened? What did you start with, how did you progress, and what happened after that?

Anita Rehman: Yeah, Carol, it was incredible. I joined, the intellectual stimulation of working, finding the job that I wanted, getting it and getting into that role and actually delivering was fantastic. And I'm so glad I took the time to go down that path, because when you love what you do, everyone knows that, things just fall into place easily and it's not work.

And, and the other thing that I learned was that I could do everything that they threw my way I could handle a lot. I could deliver, I could over deliver. I could manage so many different things. We just learn those skills as women. And, the other thing that I realized was that, and I set up, I had lots of advice.

I had lots of women friends that I talked to who said, just make sure that your support system is solid before you go back to work. And so I ensured that I had enough help. I had someone to pick up my daughter from preschool. I had someone to bring her back. I had a fallback from that support, and I was really fortunate enough to be able to afford all of that.

And I thought it was important, that was, actually, I set aside enough money to make that happen first. And I gave up the other things that I couldn't do as an early associate, at a venture capital firm. So that was my priority. I budgeted for that. And, doing that helped me or gave me the flexibility and the time to move forward.

Carol Fishman Cohen: Yeah. I just wanna also comment that it's equally relevant for our stay at home dads, or other people in caregiving roles that are relaunching, exactly what you said about working to set up this network to support what's going on in your personal life so you can actually return to work.

Can you talk to us a little bit about level, compensation? I'm not asking you how much you were paid, but just how did you even figure out what level and what the pay should be, and in your first week, when you were sitting there, was it clear what you were supposed to be doing or did you have to figure that out?

Anita Rehman: Yeah, in terms of like level and compensation, it was clear. I did have, I did ping my network again and ask, what were the general rules. But it's a new industry, and so you see lots of different spreadsheets. And I think I did what most women do, which is to under negotiate and just take the first deal that came my way.

And I did that doubly so because I got into venture capital, I really wanted a foot in the door. In hindsight, two things I said, I wish I had enjoyed the time more and I wish I had pushed back cuz I would've surely gotten a little more and a higher level starting off, but it doesn't matter.

It got me on the right path and I was able to prove myself while there.

Carol Fishman Cohen: It's interesting, what year are we talking about now? The year that you went back?

Anita Rehman: 2008.

Carol Fishman Cohen: Okay. So you have been back. You're now in your 13th year, is that right? Yeah. so because we have, I actually wrote an article for Harvard Business Review where we caught up with relaunchers who had been back, 5, 10, 15 years and asked them to look back on when they first started, when they came in at a more junior level than what they had left actually, and what their advice was. And to a person, it was just what you're saying, it was get your foot in the door, focus on getting your foot on the door, and don't like, overthink the level or even comp piece of it. They even said that years later. And you're saying that too, like you're saying, okay, yep, maybe I made a mistake there. I should have negotiated more. Still the most important thing was to get in the door.

Anita Rehman: Absolutely. Absolutely. Because once you're in the door, you deliver and people notice and then you can take your career so many different ways.

Carol Fishman Cohen: And you're there in your first couple of years. Did you have to catch up on technology? Were you looking at highly technical investments where you had to review? Like your background was in electrical engineering, was there any updating that had to happen there?

Anita Rehman: Yes and no. In VC, you always need to keep updating, and so it's just the nature of the job. So, specifically for me to go out and do upskilling and reskilling, I did not have to do that.

I had to learn on the fly though, just through my, through the people that worked at levels higher than me at the firm, we just had to, it's about taking a lot of initiative in VC. It's about going out and finding deals, understanding if their technology works, reading through patents. I read through hundreds of patents to understand how solar cells were made.

And thankfully for me, my electrical engineering degree came into play. I didn't know all of what was in that patent, but I could figure that out.

Carol Fishman Cohen: Interesting. So can you talk to us a little bit about your career progression and, and what led to where you are now?

Anita Rehman: Sure, absolutely. I worked at Vantage Point for about five, five and a half years.

And then at the end of that, as if it wasn't exciting enough to break into VC, I decided that I wanted to go off and start my own company, because I saw so many entrepreneurs jumping in so many people jumping into entrepreneurship and building all of these fantastic companies. And so I quit my job in VC and I went off on my own to start a direct to consumer plus size women's wear company.

I was passionate about it because it enabled me to serve the women's market. It enabled me to offer products where there was none. And, in some ways, offer confidence where there was none. I founded my startup in 2013. We raised a few rounds of funding and I ran my company for about five years. And towards the end of the five years, it was a really hard decision, but I had to merge my company into that of another plus size women's wear line. And the reason I had to do that was because I put my VC hat on and I was not able to scale the company fast enough to go out and get more venture capital. It was a fantastic experience.

Anyone that's been an entrepreneur knows that building a company is an all immersive experience. You know that, Carol, it absorbs every dimension of you in every which way. And so it was just a tremendous experience. It taught me to think in many different ways, and just put myself out there. But what I did, so after I merged my company into another line, I was pottering around again. It wasn't, again, a career break planned. But just out of the natural circumstance of not having my own company to go to, I was looking for something to do. And it took me about a year of doing a few projects here and a few projects there to figure out what to do again. And, I came back to GSV because I remembered that I loved investing.

And so I just started to try and get back into investing. I remembered what it took to break back into VC. This time, it was significantly higher and just so many more nos and so much more negativity because I was more senior. Typically partners come in from companies and from situations where they've taken Uber public, or they're the co-founder of Airbnb, they've achieved something really significant.

And I was going back to all of the firms saying, I'd love to come back in, but here's what I've done. I have a failed startup. I've done VC before that. I know exactly how it runs. I've run a startup for five years. I know exactly how that goes, so I can help you build, I know everything that can go wrong at a startup.

I can help your startups do well. I did not have a glamorous exit. I did not have a fancy corporate job that I was coming from. What I had was great years of venture capital experience, where I had jumped on every deal that I could jump on. I had built my own company, and so I knew exactly what it took or more so I knew what not to do when trying to launch and scale a company.

And I had that credibility to go off of. But, I was like, I know that this is the right path for me. I loved it when I was there the last time. And so I started to reach out again. I found my network. I made lists of people that I knew in venture capital, and I started to email them, do my coffees again.

Really embarrassed because now I'm going from like a failed company to reach out for another job, cetera. But, networking works in magical ways. And, there was a woman, I was part of the Wharton women's entrepreneurial network, and a partner who was in that network sent me a job posting that she found on Medium.

And through that job posting, I reached out, it was from GSV and I Googled Deborah Quazzo at GSV, and if you know, Deborah, she responded to me. I mean, I emailed her and within 15 minutes of emailing her, I got a response. Within one week of emailing Deborah, I interviewed with Michael Mo, I interviewed with a large part of the team, and I had my job offer.

So it was literally, it was just incredible.

Carol Fishman Cohen: That's unbelievable.

Anita Rehman: It is. It really is.

Carol Fishman Cohen: It's so interesting, the way you talked about it too, 'cause I'm trying to picture you saying that I had a failed entrepreneurial experience. And you said it was embarrassing. And so, having to have these conversations, I'm just wondering if people received that information differently than you thought they were going to, and whether they actually, at the end of the day, thought this is going to inform the way that you make investment decisions. And, in some ways made you even more valuable to the VC firm than before you had that entrepreneurial experience.

Anita Rehman: That's so true. That's so true. And I think it's all of these things that we say to ourselves and we assume for ourselves. Whereas when I went and spoke with Michael, that's exactly what he said to me.

I value the fact that you've tried something and you've tried taking risk and you went from your cushy venture capital job to actually build your own thing. And that's a large reason why we hit it off incredibly well. And when I joined GSV, I joined as Michael's chief of staff, because he was building up a part of his business. And I said, I'll again, I'm just gonna get my foot in the door. I'm gonna put myself in there. Chief of staff can mean a really junior analyst type position, or it can mean a COO I don't care. I'm gonna suck it up and I'm just gonna go in there.

And I made it the role that I wanted it to be. I gained his trust, and I just basically made it the role that I wanted it to be. And, I went from there, within a year, because Michael saw what I could do and how much I had learned. I was promoted to partner.

Carol Fishman Cohen: Wow. That's an incredible story, and so instructive for people. You said you sucked it up and you took a leap and you took this chief of staff role and you didn't really know where it was gonna lead, but you said you made it the role that you wanted it to be. I hope people are hearing that message. And then you became the role that you wanted you got the role that you wanted to have.

Anita Rehman: Exactly right. Yeah. I think once you have your foot in the door, Carol, I'm building the trust, building the relationship. It's all about trust and relationships. And, women tend to put so much of an index on the work you do. So for people who want to get into this field, really, it's about persistence. It's about networking. It's about pounding the pavement. And then it's getting in there and building the trust and building the relationships with the people at the firm.

Carol Fishman Cohen: Well, you have certainly demonstrated that. And do you feel when you were relaunching and it was a second relaunch, did you feel additional pressure because you were more senior or that you had to reach these goals quicker, or that people who might have seen it from the outside didn't understand where you were at what point, because you had taken career breaks. How did you handle that mentally? And did you have to correct any stereotypes or perceptions that you encountered along the way?

Anita Rehman: Absolutely. I felt so much more pressure because all of my friends, and these are all of my peers from Wharton, were vice presidents at Google, they were leading big organizations and big systems. And I remember talking to a girlfriend of mine, and I said, I feel bad 'cause I feel like I haven't done anything. Whereas, this friend of ours is a VP at Google, and that friend of ours is a VP at Airbnb.

And she said, hold on, step back. She's like, if you were at Google for 20 years, you'd probably be the CEO. Give yourself some credit. Step back and people have gone into these non-risky jobs and they've stayed at a company for 20 years. And, so I think, it's really important not to compare yourself to these situations, and to just really think through where you're at and map out your own career path.

Carol Fishman Cohen: That's so important. This whole concept of not caring what other people think, because sometimes you do care and you know what you think, and like you're saying, you might have felt embarrassed at different times. But, if you can filter out and tune out some of those external negatives, you're never gonna break into VC, kind of communications, it can ultimately help you rise above, but as you're saying, Anita, that's only if you pair it with persistence and you keep at it. Because some people might let that get to their heads and decide, you know what, I'm not gonna do this anymore and do something else.

Anita Rehman: I think you're absolutely right. Carol, you pair it with persistence, and then you also build a really strong core support system around you. And you have your supporters and people who just stand by you and encourage you along the way and say, I they're behind you, whether it's a fail startup or a great VC job or anything else that you're doing, if you can form that circle of trust and that circle of support, that is so critical in pushing you forward. I cannot tell you, when I was looking for a job when I was more senior to get back into VC just now, so many people looked at my background and said, oh yeah, for sure you were an analyst and an associate. Yeah, that's great. So many analysts and associates are basically graduated out of firms.

And I was like, no, I left to go start my own. I found myself justifying all these people and I found myself coming back and ruminating and thinking through it. And it's incredibly hard to do. But I'd say if there was one solution to this, I'd say, keep moving forward, send those emails out, meet those five people a week or three people a week. Just keep moving.

Carol Fishman Cohen: So you are getting right to where I wanted to ask you this question about, that we ask all of our podcast guests, which is what is the best piece of advice for our relauncher audience, even if it's something that we've already talked about today, and I'm hearing you say this right. Do you wanna repeat what you, your advice that you just gave or is there anything else that you wanna add to it?

Anita Rehman: I think there's two things. One is that relationships are so important. And nurture your relationships, don't let them go. And the second one is, absolutely. I think life is a marathon.

It's not a sprint. Don't get caught up in what everyone else can do in 10 years when they're 30 or 40. It really doesn't matter. You and I know Deborah Quazzo, she's shattered the glass ceiling every stage of the way. And don't let age be a factor. Don't let other people's opinions be a factor. Just keep moving forward. It's a little bit like that line from Rocky, where it's not about how many times you get hit, it's about how many times you can get up and keep moving forward.

Carol Fishman Cohen: Wow. That's a powerful way to end. And I'm, I have been through our whole conversation feeling this concept from you, take it one day at a time, put one foot in front of the other, keep going.

That's coming through really strongly and dovetails perfectly with this advice. So Anita, before we close, is there anything that you'd like to share with our audience about the work that you're doing?

Anita Rehman: Actually there is, Carol, thank you so much. We run a program at GSV called the GSV Startup Bootcamp.

It's a seven week program that opens up the world of entrepreneurship to anyone that wants to attend. It's free, people are not selected for it. We have really high caliber speakers that come to it. For example, we had John Chambers, we had the CEO of Nike, John Donahoe come to it. And then in addition to those main speakers, we run small group programs where people can learn from others who built successful companies or from VCs, as to how to launch a startup, launch a business, or they can just come and meet in our community of entrepreneurs. And so the website for this program is And, I would encourage anyone that's interested to come and sign up for it.

Carol Fishman Cohen: That's amazing. Let me just make sure I have this right. So anyone can register to attend this.

Anita Rehman: That's absolutely right. It's our way of opening up the curtains of Silicon Valley to teach anyone that's interested in launching a business, how to build one.

Carol Fishman Cohen: And does it run virtually or does like, can anyone from any anywhere sign up for it?

Anita Rehman: It's a global program. It runs on zoom, it's virtual. And you will get your zoom links as soon as you sign up for it, we'll send you an agenda and a schedule, and you just choose to join which sessions you want to.

Carol Fishman Cohen: Wow. What a great opportunity and resource. How often do you run it?

Anita Rehman: We run it twice a year. And so next year our program is going to launch in February and it'll run for seven weeks, and then again in September of next year.

Carol Fishman Cohen: All right. Very good to know, Anita, thank you so much for joining us today.

Anita Rehman: Of course. Thank you, Carol. And I so appreciate what you did for me 13 years ago. Thank you so much for being a lifeline at that point.

Carol Fishman Cohen: Oh, and I just, again, the idea that we're having this conversation right now and where you are, is it just, so inspiring for our relaunchers and for our employers, for them to know what's possible.

Thanks, Anita. And thanks for listening to 3,2,1 iRelaunch, the podcast where we discuss return to work strategies, advice, and success stories. I'm Carol Fishman Cohen, the CEO and co-founder of iRelaunch, and your host. For more information on iRelaunch conferences and events, to sign up for our Job Board and access our return to work tools and resources, go to

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