Episode 137: Charu Sharma

[vc_row][vc_column][vc_column_text delay=”0″]This weekend in San Francisco, Two-Brain held its first Tinker Meet-up.


Entrepreneurs who have complete financial and time freedom, and are seeking their next project, are called “Tinkers.” You can take the test to find out where you are in your entrepreneurial journey here.


One of our speakers was Charu Sharma, CEO of NextPlay. Charu has had an amazing life:

In 2003, Charu and her brother fought two goons in a train robbery, saving the lives of women on the train. She later represented India in South Korea, fighting in Taekwondo. Chapters of textbooks are dedicated to her in India.

When she moved to the U.S. for a four-year University program, she founded two start-ups out of her dorm room, lived at sea for a semester, and visited all seven continents on internships.

Now she has five National Awards, expeditions to all seven continents, over 600 stage shows, and three books published. Charu was enlisted as a “Power Woman” alongside such notables as Oprah Winfrey, Sonia Gandhi, and Melinda Gates by Youth Incorporated Magazine in March 2012.


Our mission at Two-Brain is to make 1,000,000 entrepreneurs wealthy. Charu has created Go Against the Flow to educate 1 million women to take risks and build their own businesses.

Charu has contributed to Huffington Post, Venture Beat, Business Insider, The Times of India and Youth Incorporated, among various publications. She organized TEDxRiverNorth in Chicago, and she has spoken at two TEDx conferences on risk-taking and entrepreneurship respectively.

Yeah, she’s kind of a big deal. And she’s still a few years away from turning 30.


In this episode, Charu is interviewed live by Jay Williams, a Bay Area Two-Brain Mentor. Her responses are both brilliant and sincere: No canned answers, lots of laughter, and some poignant quotes. Like these:


“I don’t want to just look good on paper.” Charu’s resume is amazing, but she actually goes out and DOES things. As an entrepreneur, that’s got to make your toes tingle.


“Instead of complaining about the rules, I want to get to the top and change the rules.”


“The best thing I can do for my company is to get lots of coffees with other entrepreneurs.”


“Mentors play a huge role for entrepreneurs, but also for your staff.”


“You need to create equal access to institutional knowledge.” – Meaning you can’t just project that your staff knows what you know.


On facing a tough challenge: “It made me test how much I wanted to do it.”


(I won’t give you more details – you’ll have to listen to the full story. WOW.)


 [/vc_column_text][vc_column_text delay=”0″][/vc_column_text][/vc_column][/vc_row][vc_row][vc_column width=”1/2″][vc_raw_html]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[/vc_raw_html][/vc_column][vc_column width=”1/2″][vc_raw_html]JTNDYSUyMGhyZWYlM0QlMjJodHRwJTNBJTJGJTJGd3d3LnN0aXRjaGVyLmNvbSUyRnMlM0ZmaWQlM0Q3NTYwMSUyNmFtcCUzQnJlZmlkJTNEc3RwciUyMiUzRSUzQ2ltZyUyMHNyYyUzRCUyMmh0dHAlM0ElMkYlMkZjbG91ZGZyb250LmFzc2V0cy5zdGl0Y2hlci5jb20lMkZwcm9tby5hc3NldHMlMkZzdGl0Y2hlci1iYW5uZXItMzAweDI1MC5qcGclMjIlMjBhbHQlM0QlMjJMaXN0ZW4lMjB0byUyMFN0aXRjaGVyJTIyJTIwd2lkdGglM0QlMjIzMDAlMjIlMjBoZWlnaHQlM0QlMjIyNTAlMjIlMjAlMkYlM0UlM0MlMkZhJTNF[/vc_raw_html][/vc_column][/vc_row][vc_row][vc_column][vc_column_text]Jay: 00:01 – All right. Our guest today is the CEO of Next Play, a company that uses AI to improve employee engagement by providing personalized mentorship and career planning. She’s been starting businesses since she was in her dorm room in college before joining LinkedIn. Along the way, she helped organize a Ted X conference, went on an Antarctic expedition, wrote a book, made a documentary, and started a movement called Go Against the Flow with a goal to support 1 million women to become entrepreneurs. Please join me in welcoming Charu Sharma. Doing research for this was really inspiring. You have done so many different things in your life. So I just want to.

Charu: 00:50 – You’re making me so red in my face since the first second I’ve known you.

Jay: 00:57 – Well, ask these guys, they know that that’s kind of what I do. So, I want to kind of start at the beginning and get to know your story from the beginning. So you grew up in India, yes?

Charu: 01:07 – Yes, I did.

Jay: 01:07 – So tell me a little bit about that. What was life like, you know, growing up—it was Mumbai or?

Charu: 01:14 – I mostly grew up in Mumbai, but I can tell a bit more about my context. But first of all, I’m so excited to be in this room because usually in tech in Silicon Valley when I’m in rooms, I don’t see women. So I’m just so happy to be here and I feel so warm and fuzzy and I love your energy and I’m really happy to be here. Also, FYI, most of you I think have been entrepreneurs for longer than I have. So, I would also—hopefully we’ll have time at the end to network, but I’d love to get to know you more personally and also hear you know how things have been for you.

Jay: 01:48 – Awesome. So OK, so growing up in India.

Charu: 01:51 – Yeah, so growing up in India. So my college dorm room wasn’t that long ago. I came to the U.S. eight years ago, on a college scholarship. I went to a liberal arts school called Mount Holyoke. It was actually the first college in the U.S. that let women get college degrees. And I didn’t know that when I applied. But I grew up in a family where women are not allowed to work. So when I was growing up, we were middle class, we were comfortable, I felt very loved and warm and all that. But, it was very clear that, you know, it’s a very strongly patriarchal society and women don’t work. I was being raised to then become a housewife through an arranged marriage. And I think in that world people don’t feel oppressed. My mom is so happy. But I think I just wanted a little more and I wanted to have my own identity.

Charu: 02:44 – And so I just worked my butt off. And I came to the U.S. On the scholarship and I thought that—I was so young. I hadn’t seen a lot of the world. And so I thought, you know, I have these four years to live life and then I’ve got to go back and then a plan is waiting for me. And then I came here and a lot of the things you were talking, it was because I felt that I have these four years and I have to just take advantage of everything I can. And I did every study abroad I could. I did every internship. So I worked on Wall Street, I worked at start-ups, I went to all seven continents. And then before I knew it, I think hustling and identifying opportunities became a habit. And then I also realized that I think I just really like to create things, whether it’s product, whether it’s a team, but I wanted to be—what’s a nice way to say, but I wanted to call the shots and I wanted to be in the driver’s seat. And I think there’s nothing wrong about that. I think my strengths really align with this role. And I’m also very eager to hear how you all decided to start your own gyms and businesses. But yeah, so that’s been my journey.

Jay: 03:59 – Yeah. So it was like this four-year—you got this scholarship. And the idea is just do as much as you can during that four years. Cause I mean you had detailed, like you went to Antarctica, you were a semester at sea. Like was it just try everything or was there like a specific goal behind that?

Charu: 04:19 – So I think, cause this is getting a little personal, but when I was growing up, I just really saw my dad be very risk averse and he relied on his boss and he relied on his company he worked at to pull him ahead in his career. And I saw him being so frustrated and he’s one of the smartest, probably the smartest person I know. But I’m also a daddy’s girl. So, you have to meet him yourself. But I think I just—I think our childhood and upbringing affects so much of what drives us in our profession. And I just really decided that I will not rely on anyone else. I’m in the driver’s seat. I’m going to make things happen for me. And if I fail, it’s going to be because I was a slacker or you know, I missed out.

Charu: 05:05 – And so I mean, even now I think there are a lot of conversations about how female founders don’t get funded. And it’s true and I’ve had the hardest time with fundraising from VCs in Silicon Valley, but I think instead of saying, they don’t fund women, I think I try to read this as well, I don’t tell my story in a way that resonates with them. And I think this mentality is so important to really make a difference and especially to inspire your team and make sure they don’t have this victim mentality. But so anyways, so that’s how I think I just always wanted to be an entrepreneur. What was your question again?

Jay: 05:35 – So I mean it was like, just looking through it. You had a couple of semesters at sea, you went to oceanography for a while.

Charu: 05:41 – Was I intentional about it.

Jay: 05:41 – Yeah. Was there an intention or was it just like say yes to everything, I want to try everything.

Charu: 05:47 – Yeah. I think originally was that way. I just wanted to get out and see what the world is all about. And I was originally going to be an engineer, but then I realized why, I don’t even like it, you know? And so I wanted to do classes in politics and film studies and physics. And then I eventually ended up studying physics and economics because I think I’m very analytical and I was just really good at it. But I also did classes in world politics and Spanish and film studies like I wanted to. And I think most of my learning actually happened through the other things outside of my typical college education. So I think I joined 10 clubs in my first year, but then I also realized very quickly, no, I’m making a total mess. And so then I started really picking at any given time, two or three things that were my priorities. I think I’ve definitely learned the hard way, but I learned that quick. And I think since then I’ve been intentional. So if, I mean, I think there’s nothing wrong with just trying things to try things, but then also realizing my capacity, that I need to sleep, that I need to maybe, I don’t know, have some wind-down time and watch Netflix or, you know, whatever it is.

Jay: 06:59 – So one thing I found really interesting is, you know, it’s one thing to say, yeah, I’m interested in politics. It’s another thing to volunteer for a campaign. You know, it’s one thing to say like, you know, I really like oceanography. It’s another thing to go to Antarctica. Right? So like you kind of take these to you know, the next level and the next level. Is that just because your curiosity leads you there or or do you already have that vision in your head? Like, I’m going to do this?

Charu: 07:26 – I’ll give you a long-winded answer because you’ve said 90 minutes. It may not be that long, though. Think I grew up with a tiger mom, and everything was structured and things had to look great on paper because I had to get into certain colleges or whatever. And so, but when I was 17, I had five national awards and there was a chapter on me in the English textbook in India in ninth grade. It felt amazing because whenever it felt like my parents were so proud of me and I wanted to live up to those things. But then the reason I came to the U.S. was I didn’t want to be good on paper. I just wanted to know who am I. And I was 18 at the time. I didn’t do any of these things because they look good. I think it was natural curiosity, but I think also early on realized that I’m an experiential learner. And so, I mean, I can Google things and, you know, read about oceanography, but I came to the U.S. and I had this opportunity to live through these things. And I think that’s why,

Jay: 08:34 – Yeah. Was there any single experience that stood out as like life-changing? All of them?

Charu: 08:39 – I think so. I think it’s mostly been the people who came in my life, whether someone I studied abroad with or a mentor or a teacher. I also realized that just generally life is so ill-defined, it’s really on you to figure out what’s the next move. You know, how I want to position myself, what network do I want to build, all these things. And when you’re young you just don’t know what you don’t know. And so I’m very aware that—and I don’t mean to just keep talking about, you know, being a woman again and again, but it was really some women who just took me under their wing and they gave me so much confidence when I was early in the workforce. And that’s the reason I do this company now because I realized people don’t have equal access to opportunity, whether it’s a company—I think in tech it’s exacerbated. But I think generally it’s ubiquitous. As business owners, I’m sure you feel this. But also, we were talking about just going ahead and being action oriented. I’m sure every one of you is that way. Otherwise you wouldn’t be in this room, because you’re business owners and you flew here from other parts of the world to be here and you didn’t need to. So I think we’re the same.

Jay: 10:00 – You started and participated in a lot of initiatives and activities along the way. At what point did you start your first business and what was it?

Charu: 10:10 – So I’m trying to think back. So the first real business was in college. So I serendipitously ended up at start-ups doing internships. I just wanted to be in New York City cause I hadn’t been there before. So I was looking for summer internships and I ended up doing two internships at start-ups consecutively and they brainwashed me and they made me realize, hey, I did it. You can do it. And I was like, OK, cool. And so when I went back to college, I think it was my junior year, I think, and I was seeing how all my peers are preparing for interviews to be at these investment bank or consulting firms. And that’s great. But they didn’t know why they were doing it, first of all, and they didn’t know how to prepare for it. And people are just not good at networking, especially at that age.

Charu: 11:08 – They don’t know what that entails and how to go about it. And I think that comes naturally to me. So I wanted to help my peers figure that out. And so I started this business. It’s weirdly spelled, it’s called and then you as Y O U . M E. I thought it was so funky, whatever, in my head. But it basically connected more senior, so junior and senior college students and recent graduates to their alums to learn more about their industry, do informational interviews, and also to prepare for job interviews. So it was pretty small, pretty specific. It’s something I knew and a problem that I knew I could solve. So it was a small start-up, didn’t become very big, but I think we helped over probably a couple thousand people. So it felt good. I think more than anything else it made me the confidence that if I have an idea—and I didn’t know how to code, I just figured it out because I met the right people somehow and so it gave me the confidence that even though I’m not an expert in something, I can go ahead and build it, and really it takes a village to do anything. So I think I also learned the skill set to source the right people and learn how to leverage their strengths and work together with them. So yeah, but the start-up didn’t go anywhere, but it was a great learning experience.

Jay: 12:29 – Yeah. When you say like the start-up didn’t go anywhere, I find that interesting. So like was there a specific goal and then you felt like you didn’t reach the goal or you fizzled out, I don’t want to do this anymore?

Charu: 12:42 – Good question. Yeah. So I find it odd, too, actually, I think I’ve just started using this word because I’m in this town. But I think a start-up to be successful means that someone acquires you for $100 million or you have a a deal here. But yeah, so I think we were impactful. We helped enough people. So maybe it was successful in that little sense.

Jay: 13:06 – Yeah. And so subsequently you started several others, so like there was a few different companies that you were involved in. Tell me a little bit about those.

Charu: 13:15 – Yeah. So if you go to my LinkedIn profile, you’ll see a lot of things. And I also want to preface, I wasn’t just hopping from thing to thing to thing. I was very intentional and—

Jay: 13:27 – It’s OK if you were, I would still hire you.

Charu: 13:30 – But so that start-up, for example, I think they are just more factors in life. So I’m not a U.S. citizen and I just could not figure out a way to keep working on that start-up. And I didn’t want to go back home and get married, so I took a job at LinkedIn, you know, so that happened. Yeah.

Jay: 13:47 – Yeah. And so like with those sorts of start-ups you get into this Silicon Valley or this start-up sort of culture, there is this idea like I’m going to build this giant thing and sell it for $100 million. Is that always the goal when you start or is that kind of the dream or is it just I’m going to try to solve this problem or is it a little bit of both?

Charu: 14:09 – So that’s a great question and I try to remind myself a lot why I started this company. So, excuse me. We’re not even two years old, so we’re very early. I just had a great breakfast burrito. Sorry. But I think early stage and specially for mission driven start-ups, frankly, it doesn’t matter. I just want something to come out of it. So it feels like there’s a pool table there are these balls, and I just want to move them. So that’s what I’m doing, right? My goal is how to get my next 30 customers. That’s it. And that being said, I do have to pitch to VCs who don’t often meet people like me who speak a different language, and who try to pattern match. Right? So then I think I do have to get myself very familiarized with how they perceive success, which are the things you mentioned.

Charu: 15:11 – And I also have to tell them that story so they feel like, OK, they know what they’re doing—and nobody knows what they’re doing—but they think that, OK, they know what they’re doing. I can give them whatever, $2 million, $10 million, whatever you’re raising. I think people here just throw money if you can convince them that you got them, you’re going to give them a great return. I really think it’s a very distorted world here. But I’ve met a lot of really successful women and they say, well, there’s nothing you can do about it, either you complain or you just first get to the top and then you change the rules.

Jay: 15:49 – Right. I love that. Yeah, I’m curious about the sort of fundraising piece. Like what is that like? So you have to, you know, go and pitch to a whole bunch of different investors, this idea and you have to kind of come up with what you think your company should be valued at and that kind of thing. Like how does that work?

Charu: 16:09 – Yeah. There are just so many things that you just possibly cannot know when you start. So I think something we did well was we were very intentional about making a list of those things we don’t know. And then getting lots of coffees with entrepreneurs, with VCs, before we ever needed to raise money from them. Right. Because then they can speak in this objective way where I’m not asking them for money. And I think mentors play such a huge role. I mean, that’s the mission of our company. And your company. But I think it takes a while. There is a learning curve and then we also did some accelerator programs, like 500 Start-Ups Mass Challenge. But they’re basically these cohorts similar to this. They bring together founders with some trainers and then they walk you through, what you don’t know, you don’t know.

Charu: 17:05 – They’re just so much to learn. And I think it’s also important to realize that you possibly can not know everything. Right? So I think I’ve also learned to prioritize. Fundraising is interesting because there are multiple ways to run your business. I forget the number, but a very minuscule minority of businesses actually get VC funding. So that’s not the only way to raise money as well. Right? I’m trying to, especially because I understand that this world is a bit biased. I’m trying to build a revenue-based model where if I solve the problem for my client, they pay me. Right? And they don’t care how old I am or what’s my accent or all of that.

Jay: 17:48 – Do you have a favorite failure over the years?

Charu: 17:50 – Favorite failure? So generally I think, and I’m sure it’s this way with you too, but we put ourselves outside of out comfort zone, right? On a daily basis. And so life is going to be like this, all the time. So I think, I’m just not affected by it anymore. So, yesterday I got some horrible, well, constructive feedback from a client and it seems like—we thought it’s going great and they’re like, it’s a shit show. And so I think I’ve just learned to not take it personally. It’s just we’re so young, you know, it’s this 80/20 rule, we spend 80% of our time focusing on 20% of things that are most important and the rest will not go well. And that’s OK. But then we listen to feedback and we act on it immediately.

Charu: 18:42 – So the breakfast burrito I got was with the person who does customer success at our company and so I got lots of advice. I mean, I took lots of notes. I have my backpack here and then later I’m going to go home, make a plan and send it to the client on Monday. Right. But favorite failure. So, I don’t think I have a favorite failure, but I think something that really—a couple things that really defined my learnings about what I want for the company as you were asking a few minutes ago is, well, there are two things. So one, at the beginning I just had this idea, I actually built a mentoring program for women at LinkedIn and I wanted to scale it. And I realize it’s not just a women’s issue. Everyone wants a mentor and there are so many untapped mentors who have so much to give, but they don’t know whom to give it to and how to really be a great mentor. So I wanted to build this, but I didn’t have obviously all the skills. And so first I needed an engineer. And I went through four technical co-founders. Somebody wanted—I think a VC was going to write us a check. And then 15 minutes before that they told me, hey, I want two thirds of the company. I’m like, what? And so that didn’t work out.

Jay: 19:53 – With your current company, you had four technical cofounders? They were actually at one point cofounders and you had to oust them.

Charu: 20:01 – Correct.

Jay: 20:02 – Wow.

Charu: 20:04 – But luckily it happened very quickly and I think that’s great practice because I realized that it’s really important to vet people. So now I have this rule. Anybody who works at our company, we do a month-long trial with them before. And we pay them for it. We don’t exploit their labor. But that’s how I met my current cofounders. So we did this trial for a month. I said, hey, help me build this MVP. I’ll pay you for it, a small stipend, because I’m poor right now, but I’ll pay you something and if we get along well, mutually we’ll agree to be cofounders. And then, you know, we just hit it off. I think there are other important things in addition to your skills or like work skills. He needed to be communicative. I need to trust him. You know, he needs to be a good-hearted person.

Charu: 20:48 – All those things. So I want to spend some time. So I think—but I had no clients. I had client orders, people in the sales pipeline who wanted to see a product before signing. I didn’t have my visa figured out. I had nothing and I didn’t have anyone to build a product. So it felt like, just felt like the end of the world. But I think it’s good because it made me test how much I wanted to do it. So I went to another person and they worked at Google and didn’t want to leave their cushiony job. So then I went to another person and they were just not skilled. So I went to another person, and so on.

Jay: 21:30 – That’s a lot of tough conversations. That’s amazing.

Charu: 21:34 – And we can talk later about retention as well. I know you wanted to touch upon that.

Jay: 21:38 – Yeah, yeah, yeah. I mean a lot of your companies and the stuff that you do is based on sort of helping people or improving some issue that you see in the world. Why not just create a product like, you know what I mean? Like it seems like it’s really driven on your beliefs and you almost go the hard route rather than just focusing on something that, you know, hey, I can create this cool video game or something like that. So the question is why not just create some sort of product or something if the goal is to have a successful start-up?

Charu: 22:23 – So we did that.

Jay: 22:24 – Oh, you did? OK.

Charu: 22:27 – Sorry. I think I’m not understanding.

Jay: 22:29 – Yeah. So, OK. Ignore the question. Let’s go to the next one. So, yeah, now you’re working at Next Play. Can you, I know you’ve kind of touched on this a little bit, but can you describe what Next Play does?

Charu: 22:42 – Yes. So exactly what you were just saying. I think, you know, I’ve had all these beliefs and I wanted to—then I got to a point where I was like, I want to scale it where wonderful people like yourself who are champions of the same value system and they wanted a mentoring programs for business owners or within companies for new managers, for specific underrepresented minorities, whatever. It’s important to help people develop and build the right—well I’m really grateful to the relationships I formed in my career early on. That’s the only reason anything ever happened from my first job to this business, to the client feeling comfortable letting me know that, hey, I know you’re going to do something about it, but here are all the things that are going wrong. Instead of just not saying and then just turning and not renewing.

Charu: 23:30 – So we did that. So now we’ve got this mobile app named Ellen, and it chats with people. It understands their goals, their blind spots using AI. And I can talk more about that too. And then it connects them to the right mentor, mentee or both within their cohort. So we don’t have a community of mentors, rather we’re a system that you can just plug into any ecosystem that has both sides of the equation. And so it does matching. It also trains them on being effective mentors and mentees. So what is expected of you? How do you show to a meeting? How do you prepare the agenda? At the end of every meeting, the app pops up on your phone and will say, hey, Charu, how was your meeting with Jay? Give them real-time feedback. These three, four optional multiple-choice questions.

Charu: 24:19 – And in that you record your action items that are shared on a system. And so you’re accountable, but you get a lot of just-in-time reminders, meeting reminders, and then you can track your ROI. You as the program manager. So for example, we wrapped up a case study with Lyft recently and they saw that their employees after six months, had 218% increase in their clarity towards that career path. So that’s huge, especially for early career professionals because we don’t know what we’re doing. Right. They saw that people felt twice as self-confident in six months. More employees recommend their company. So especially, I mean, if I want to build a revenue-based model, I have to be very cognizant of the business case to, so we pay very much attention to the data that’s being recorded.

Jay: 25:07 – So a company will say, OK, we’re going to do an engagement with you. And then it will be like a subset of employees that would go and fill out a profile or something like that. Would there also be—would that set of employees include both the people that potentially are going to be mentors and the mentees as well?

Charu: 25:27 – Yes, exactly. So everyone just fills out a quick form, it takes them less than three minutes to talk with Ellen. And how we came up with the name was, we talked to I think over 50 people asking what are one- or two-syllable names you trust? And a lot of people kept talking about—can you guess? Yes. So I you make some decisions trivially and you move fast. So that’s how Ellen happened.

Jay: 25:50 – How does the AI work?

Charu: 25:52 – So two pieces. One is the matching. So we can do basic if-then loops, you know, so if I want a promotion, match to someone senior, but it’s not that simple because people are more multifaceted and mentorship and their goals are very personal. So we have this machine learning model that can basically relevantly match people for, you know, for a company that has literally a 100,000 employees. So that’s really cool that we can scale something like that. A second is working with blind spots of people. So if you tell me that, you know, your goal is to hire 10 people, OK, I’ll work with you on that. But what if that’s not the right goal for you? Right? So the AI, it needs some data off the user. So over time, but relatively quickly, it understands what your blind spots may be. And sure that’s your perceived goal to hire 10 people, but what is your real goal? So that’s pretty cool. And I think that’s how we’re able to attract this very strong technical talent who want to work on these complex technical problems.

Jay: 26:59 – Right. Wow. All right. I think we did that in one of—in my speech at the last summit. And maybe I can just use AI to replace my speech. And tell me a little bit more, you touched on this as well, about how you feel mentoring plays a part in people’s career development.

Charu: 27:19 – As I was saying before, actually, forget about young people, for everyone. I’m sure Obama doesn’t know, you know, what he was doing. I think our time on this planet is so limited. It’s so important to use this time well, and it’s so important to have a person who is not emotionally in that situation who can help you think through your goals, your priorities. And I also think, I’m a big believer that there isn’t just one mentor. I think you need to have a sort of this board of mentors and you go to one person because you want to understand how to be a good manager, right? You go to another person because you want to work through your financial statements. But different people play different roles. Oh, thank you so much. Oh, you weren’t kidding about the water. Thank you, Heidi.

Charu: 28:15 – And I think different mentorship relationships look different. So maybe I meet with you every month to talk about being a good manager, but then maybe I meet with you just once to walk you through how I hired my first 10 people. And I think it’s not necessary to call it mentorship because generally people think it’s a very huge commitment. It seems like heavy lifting and I am a big fan of whenever you ask someone to be a mentor, and also this is not answering your question, please feel free to direct me.

Jay: 28:50 – Oh no, it’s fine. This is great.

Charu: 28:50 – OK. If you ask someone to be your mentor, I think it’s really important to, instead of that, say, hey, this is my specific goal. This is why I think you can help me with the goal. So my goal, why you and then what is my specific ask.

Charu: 29:09 – So this person I just met, I said, hey, I actually need to very quickly learn about customer success. That’s account management. I think some buzzwords are just used here in a lot of tech companies. But it’s basically making sure that, you know, the pilot has rolled out, project management, all that stuff. And could you please meet with me for the next three months once a month? I’ll buy you coffee, I need just one hour of your time every time. I’ll present a situation. If you can role play with me, that would be really helpful. And so even though they’re so busy, they’re happy to help. But if I would say, hey Sue, will you be my mentor, you know, it’s like, what does that even mean?

Jay: 29:45 – OK. Yeah. That was my next question is actually how do you approach it with your business or just for yourself? Is it just like you said, you’re saying, hey, let’s have coffee for the next three months and work through this problem?

Charu: 29:59 – Yes, largely speaking. Yeah, I think—so because I also manage a team, it’s also my responsibility to make sure that they have the right mentors, right? And because I have a certain limited network, I try to share that for my mentorship and for their mentorship. And I think for my mentorship there is my own mentorship as a founder or as a salesperson or whatever I’m doing. But then there is the company mentorship that hey, can you guide me on how a start-up is run? You know? So I think it’s important to, for example—and I’m sure you have a lot of activities planned for this weekend, so I’m sure you’re going to do it anyway, but generally it’s important to, you know, box what’s important to you. Actually this is something we do with our users. So for example, to the mentees, we ask them to rank five things on a scale of one to five. Maybe we can do it now very quickly. And not everything will apply to you because you are business owners. But first, how clearly do you know your next career step on a scale of one to five? So you can think about just how clearly do you know your 90-day plan, right? So that’s the clarity. The next thing is your skill set. So to achieve those goals, do you have the right skills? And then can you write down what—

Audience member: 31:17 – Can you slow down a little bit?

Charu: 31:24 – Yes. Sure. Cool. Your clarity towards your next career step. So for you it could be your clarity towards generally what I’m going to do in my next 90 days. The second thing is your skill set. And so more specifically in our context, it’s about I want to go from, I usually would say, hey, I want to go from, I don’t know, from engineering to being a product manager. Right? So the first thing means well do you know that you actually want that thing? Do you know what the next thing is going to be? Is it product management or do you just think that? Second is the skill set. Right. Actually second is the plan. Do you know how to get there? Third is the skill set. Fourth is the self-confidence. Rank your self-confidence on a scale of one to five. And then fifth is your networks. So do you know the right people? In our context it’s within the company. But I think for you it’s just general. Do you know the right people you need to know to be successful?

Jay: 32:40 – So these are questions that the app will actually ask?

Charu: 32:42 – Yes.

Jay: 32:42 – Right. OK. And so if you—will it make suggestions based on whether you score yourself low on one or the other? Like you know, self-confidence.

Charu: 32:53 – It does. So we actually use that in our matching algorithm, too. But I wanted to expand on that a little and say you cannot do all five things, obviously, because you’re talking about prioritization and mentorship. So we recommend that you figure out which two things do you want to focus on over the next say six months. And then understand that the other things may not improve because you’re not intentionally working on it, but that’s OK. So you really have to prioritize.

Jay: 33:23 – That’s amazing. So your company is relatively small, right? And you as the CEO of the company are in some ways a mentor to the folks that are working for you, but you also suggest that they find outside mentors for their area of expertise. So, do you think that would work for like a service business? Like we have, I mean, we have, you know, for not all of us, but we have a gym where there’s a gym owner and then there’s, you know, coaches, maybe sometimes there’s a head coach, maybe there’s an admin. Like, do you feel like that structure would work the same way and how would you approach that?

Charu: 34:01 – So I have a clarification question just because I don’t know anything about running a gym. Generally or does this group actually have experience in those specific roles?

Jay: 34:15 – Generally? Not everybody, but generally we’ll have started at the bottom and kind of work our way to that. So we will have done all of those things. And if we’re smart, we’re not doing them now.

Charu: 34:28 – Yeah, that’s really helpful. So I would say two things. So one I think it’s just really important that your employees have an outlet to express their concerns openly without the fear of being fired or in any way being penalized for feeling bad. So that’s just really important and not everyone has an outlet in their life. So I think that’s also a role that mentors play. So that I think that in and of itself is really useful that they have some sounding board that is not you because there is always a certain line between a manager and the report, right? It could be someone else within your company. That’s OK, but it needs to be somebody they don’t report to. They should not be in that line. Second, this is more specific to me and maybe some of those people who haven’t done those roles.

Charu: 35:17 – But I’m not an expert in anything. I’m a jack of all trades right now and so I cannot mentor anybody on my team on the thing they’re doing, frankly. So my job is right now is to make sure, but that’s just what works for me, is hire really smart people who are coachable and I think skill mentorship and coaching are different things. Coachable as in I’ll give them feedback. They want to understand the larger business, work with, you know, the bigger picture, all of that. So I just hire smart people and then get out of their way. And my job is to make sure that there are no roadblocks in their way. But I cannot tell my engineer that, hey, your code should have this thing. I just don’t know.

Jay: 36:00 – Right, right. Yeah, that was my next question is, you know, are there specific things you’re doing on the front end when you’re hiring or before you hire to sort of facilitate that process?

Charu: 36:10 – So while I don’t know the details of a code, I actually went to a programming boot camp to understand the basics, to know how to communicate with them and how to do a little bit of, you know, vetting people, assigning goals with them for them. So I definitely familiarize myself in everything before I hire someone for that role. But as we grow as a team and as our network grows, now that are some, you know, mentors/friends/champions in my network who are experts in those things. So I’ll ask them to do the third round of interview. They’re happy to make, you know, an hour for two 30-minute conversations, especially because I’ve already screened those people. But yes, vetting is very important. And I don’t know if this would apply to the sort of roles you would probably manage, but I always give people homework, because I want to see are they the sort of people who, excuse me, go above and beyond on a task that’s given. Because I think generally a lot of people just look good on paper and then when you work with them, you realize, I don’t know, we shouldn’t have done that.

Jay: 37:26 – Yeah, yeah. Yeah. This is great. I have tons more questions, but I want to open it up a little bit for the audience. Anyone have any questions for Charu? Raise your hand.

Audience member: 37:36 – So getting into the mentor business, and hiring people in the mentor business, how do you mentor people when nobody comes up with mentor experience? So where do you develop the skill set to mentor people in such a bag way for software and AI and all these different things when everybody’s coming in and saying, well, I’m a programmer—different departments and funnel that into the key thing that you do.

Charu: 38:15 – Do you mean at my company what I do or do you mean how a mentor would handle—

Audience member: 38:20 – More in your company, you created this whole entire concept where you didn’t hire mentors, you hired people to do specific jobs to build this thing that eventually is mentoring.

Charu: 38:35 – So great question. I also think we need to hire people who are experts in this when we’re ready. But at this stage I needed to be the expert. So like I said, I have no other skills, so at least I need to be the domain expert. And I wasn’t at the beginning, but I developed it. So I’ve thought about mentorship for more hours than most people on the planet. And we built our product iteratively. So we made this embarrassing unfinished, MVP, minimum viable product. We went to a conference, it was so embarrassing and we knew people would poop on our idea, but we just went for it. And of course people complained. It was confusing as hell. But we got feedback and then we learned what do people expect, right? And then first we corrected that and then we built the next thing.

Charu: 39:35 – We went to another conference in two weeks, but this had to happen really fast. And so we built the whole product iteratively. There’s nothing in the app that somebody else didn’t tell us to do. I mean, we also had to understand why they’re asking. We just didn’t blindly build what they were saying, but we had to invest resources, energy, time and money sometimes to build that domain expertise. And also if you think about it, if I’m going to raise money, I have so many things working against me, how I show up and I don’t just, you know, sit like this, you know, when I’m going and fetching, I sit like this and I want to be that kind of a person. But all that is working against me and so I need to really prove that I know more about mentorship than anyone they can fund. I don’t think that answered your question.

Jay: 40:41 – So, sorry, I’m just gonna repeat the question for people listening. So how many things have you had to become the expert for and how many more things do you feel like you’re going to become the expert for?

Charu: 40:52 – Yes. I think that’s a great question. So to some extent, I don’t know. And to some extent, what I do and what I need to do is just focus on the next six months. So at this stage if my biggest goal is to get my next 30 customers, what do I need to get an expert in? And so sales processes, lead generation, you know, setting up referrals, so people who have these networks of clients already, you know, send us people, et cetera. But my answer will completely change in three months. You know, like yesterday, now I have to become an expert in customer success, you know, and then maybe in a week from now I’m going to a conference to pitch and maybe in a week I’ll realize, no, no, no, no, I need to be an expert in product. So these things happen, too. But I try to stay with my priorities for at least three to six months. Knowing that, yeah, people will complain about other things like I was saying earlier, but it’s OK. I’ll come to it in three to six months from now.

Jay: 42:05 – Other questions?

Charu: 42:08 – Also, could you all please also introduce yourself? I like your shirt.

Jay: 42:14 – What was the need for the product?

Charu: 42:29 – I think mentorship is not anything novel. I’m not inventing anything at all. People have sought mentorship. People have been amazing mentors. The problem is these relationships from very organically and informally, and hence not everyone gets equal access to opportunity. That was my personal problem with it. It’s important to have systems in place, whether for entrepreneurs or for employees at a company that create equal access to institutional knowledge, to opportunities, to mentorship. So our vision is really to create this central node. Mentorship is step one, but our vision is that the app will be the central node that understands an employee’s aspirations and goals or blind spots or whatever, but then it matches them to the right thing that they need. Right now we’re starting with mentorship because that’s what I am right now, the expert on.

Charu: 43:39 – Right. But in future we plan to connect them to, hey Charu you’re in sales. Have you thought about customer success? Here is an open role. So career pathing, maybe helping you understand how you cultivate your passion, especially if you’re new to a field. And frankly, most users, they’re goals are career pivoting. Most people hate their jobs. Right? And maybe it’s just a matter of having a mentor sitting down, understanding, well, maybe I just don’t like my team, but I actually really love sales maybe. Right. So I think it’s just so important to have these systems in place and that’s what we’re trying to build and that’s the need I see.

Jay: 44:28 – So the question was, did you notice that people were uncomfortable asking for help?

Charu: 44:35 – Yeah. So I built two start-ups from my college dorm, then I got recruited at LinkedIn, and I got recruited by their global head of sales. So I was so excited. I wasn’t looking for a company job. I just wanted to go learn from him and work with him. And he’s an amazing public speaker. And I was just completely charged and I was like, I want to work with Mike. And so I took a job at LinkedIn and then I realized, actually I’m in an entry-level sales job and it really sucks. And I think the right people loved that job. I just had a mismatch of expectations for myself. I thought I would be his protege and I built these start-ups, they wanted me to—I had in my head, I thought, you know, like young naivety that oh, they think I have some amazing ideas and we’re going to change LinkedIn and of course not. And so I joined the company. I had an amazing manager and I had this executive sponsor. How many of you have heard that term before?

Charu: 45:42 – So a mentor versus sponsor. Quick digression, I’ll come back to this real quick. A mentor is somebody who can give you advice, who can talk through issues, and a sponsor is an advocate who opens doors for you. So I may not meet them every month or every three months. I just know them and they know me, but they open doors for me. So the global head of sales wasn’t going to sit down with me to mentor me on sales, but he kept me in mind when opportunity showed up or he vouched for me when and if, you know, it needed to be done. But I realized I don’t like this job. And I also realized, even though I thought I was so confident, I realized actually I have huge imposter syndrome and it showed up in a certain situation. I would not ask for help.

Charu: 46:28 – I felt like I didn’t fit in. Yeah, I just felt completely out of place and I felt lonely and my parents would call me, ask hey, so you were going to come back. What happened? And it was cold in Chicago. I was in Chicago and I grew up in Mumbai. It was cold and just all these things just didn’t feel good at all. And so I didn’t do anything. Somehow this woman found me and she started mentoring me. She used to be at LinkedIn in a San Francisco office. And so I was hinting at it earlier in the conversation, but she just gave me so much validation and confidence as a young woman, and she made me realize there’s nothing wrong with me. I’m very competent. The problem is I’m not in the right role, but when you’re in the situation it’s hard to know these things and it really helps to have that external sounding board to tell you what’s going on, you know, from several feet away.

Charu: 47:24 – So that was immensely helpful. So A, she just made me feel so confident. I became pretty good at what I did. Because I realized OK, it’s temporary. Career is like that. Life is like this. I didn’t have to stay in this for too long. Let me just prove myself and get out of this and find another role at LinkedIn. And she helped me do that. So I did what I was hired to do really well. Just the way I would carry myself completely transformed, she helped me identify what I could do at LinkedIn. So what are the roles open and then how do you connect with them? What are they looking for? How to position myself. So then I stayed at the company for three years and then in my new role I started realizing, wait, everybody on the team, or most people on the team, are where I was and they didn’t know what to do.

Charu: 48:16 – And people keep saying that, you know, there are these fireside chats or whatever and they’ll say, manage your career. What does that mean? Can you please tell me? You know? And so people just didn’t know what to do, what is a mentor, how to find one, what to do with them, et cetera, et cetera. So to pay it forward, I built a mentorship program at LinkedIn. Nothing official. It was just a fun side project I had. But also on the other side, from my conversations with my own mentor, I realized that people like them who are senior, they want to give back so much and right now they’re giving back to people who ask, like you were saying, you know, how easy or difficult it is to ask for help. And then the people who are confident, who think they deserve to be mentored by the senior-most VP, they ask and most people don’t. So again, coming back to I wanted to put those systems in place, so I felt the need to really achieve scalability. And so hence we use technology and hence we use AI to scale this.

Jay: 49:15 – The technology makes it a little bit easier for that sort of ask.

Charu: 49:18 – Absolutely.

Jay: 49:18 – So I’m going to just do one more question for the podcast and then we’ll wrap that portion up. If you have other questions, you can obviously ask Charu before she goes. So one more question.

Charu: 49:41 – That my goal is to do good in the world as opposed to making a lot of money for myself. No, they’re not. But it changes how we make decisions. Right. Sure. Let me really quickly think of something.

Jay: 50:09 – So the question was, you know, we talked about the difference, what is a mission-driven start-up and you know, how is that different and is it mutually exclusive to make money with a mission driven start-up?

Charu: 50:28 – OK. So it works in every, sorry—no I think you’re fine. I can see him now. It works in all facets. It’s like your values, what is driving you? So from the people we hire to how we hire them, to how we really invest in mentoring them and eating our own dog food, to the way we sell. I’m not going to push this on everyone because I have to hit my sales quota. You know, things like that. So it really surfaces in everything you do. Did that answer your question? OK.

Jay: 51:18 – OK. So I have two more questions. The first one is there anything that you’re doing that you think makes you successful that when you look around, not necessarily this room, but you look around, that nobody else is doing?

Charu: 51:41 – I would say two things and I don’t think it’s anything inherent. I think anyone can do it. And it’s also integrating what we’ve been talking about. So one, surrounding yourself with the right people who can help open doors for you, who can make you aware of your blind spots, et cetera, et cetera. But it’s really on you. So it’s on me to do this. Second thing, I’m very action-oriented and I mean, like I said earlier, everybody in this group has got to be because you’re sitting here. But like yesterday, I got this feedback and I was surprised and I almost wanted to cry because it just felt bad. Because we thought we were doing amazing, you know? And so it was a difficult conversation. And then I could have come home and I could have cried and I could have just said, oh, she’s a bitch.

Charu: 52:33 – And she’s so, you know, whatever. But, I think the right attitude is to solve it. And I had to see that I don’t get to play the start-up card all the time. Sure, we’re lean, but they’re my customer and she’s right in expecting what she is expecting and these are the things I need to work on. Now we’re almost two years old. I have to go from this level of service to this level of service. So I think a combination of being objective and really appreciating the feedback you’re getting, but what I really mean to say is acting on it. So I think bias to action, I think I do that really well.

Jay: 53:14 – Yeah. Awesome. And then the last question is, what is the best advice you’ve ever received?

Charu: 53:19 – This is so hard because like I said, I have so many mentors,

Jay: 53:24 – So just maybe pick two or three, then.

Charu: 53:28 – It’s like asking, you know, if you’ve traveled so much, what’s the favorite country you’ve been to.

Jay: 53:33 – Well, you can list all the countries that you’ve been to. So just some of the best advice that you’ve ever received.

Charu: 53:38 – This is something that doesn’t necessarily apply to what we’re doing. And it’s so basic. But someone who I just met one time, she doesn’t really have, you know, this place in my life. I just met her for coffee and she said something so simple that has just stuck with me and she just said, that’s it. Always follow your impulses. That’s it. But it’s been so helpful because, and it may not sound like a big deal, but just to me personally in my journey, it has meant a lot because that also makes me action-oriented. Of course I’m not being rash, but if I think I have an idea, I’ll go build it or you know, hire people to help build it. And if I know in my heart that a certain thing is right, you know, whether, OK, sure, if this company has all these negative signals then just stop wasting your time on it. Or this person, maybe does not have experience in sales, but they have this vibe. So I know there are a lot of negative connotations that could happen from somebody making decisions off of their intuition. And that’s how discrimination happens, too. But I mean to say it in a more positive context, which is follow your heart and it’s so generic and cliche, but I think it’s great advice to follow.

Jay: 55:03 – Yeah. That’s great. Where can people find out more about you and what you do?

Charu: 55:08 – is our website.

Jay: 55:15 – Thank you so much for taking the time to chat with us today. It was really inspiring and you know, we got to learn about something that maybe is a little different than what we’re doing on a daily basis, but all the lessons apply to what we do. So please join me in a round of applause for Charu.

Charu: 55:34 – Thank you. I really enjoyed being here.



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