YouSaid · the spoken record

Sukhinder Singh Cassidy

lines on the record: 96
first: 2021-10-22
most recent: 2021-10-22
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“I would know today that I wish I knew that. I always say to people like, I think what I wish I knew then is that it doesn't need to be a mighty choice to enter these areas. You can enter in a small way. And like I said, I made what I would consider now a relatively small move. Yes, I quit my job, but I was like in my mid-20s and I moved to Silicon Valley. Like I would just say this idea that you don't have to have the big idea to get started. The big idea can come later. Just get close and start with something small. For me, that was a move to this area. For others, as I said, it might be tapping into a side hustle or opening an ET store. Like you can learn everything you need to know about these areas in small acts, not waiting for one big, perfect idea to show up and galvanize you.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“So that's possible. The other path is obviously a more traditional finance path through business school and classic financial training or consulting training.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“I would say on the entrepreneurship and technology side, I would say get proximate. And today, luckily for us, getting proximate doesn't mean you need to move to Silicon Valley. We all live in a hybrid world. But if you're contemplating moving to one of those areas and you don't know what it looks like, literally, maybe as simple as, you know, doing a couple informational interviews with people you find on LinkedIn. It may be tapping your close-in network and figuring out who's doing something entrepreneurial and going to shadow them. It may be like finding a side hustle where during your day you're at a large company in the evening, you're moonlighting. These are all ways to get proximate to what you know. And I'd say that's far more the case for entrepreneurship and technology because there are so many sort of gig economy hustles that you could do to learn before you ever make a bigger move. Venture capital is a much more kind of traditional path, I would say. You can get there from technology, but then they want to see that you've accomplished something inside of technology.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“And I wanted to know why, so I'm in the midst of reading it. And so far it lives up to its billing is just being refreshing, simple, surprisingly intuitive, yet we don't do it enough.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, one of my favorites, I'm like a very kind of geeky business person sometimes. I don't like to read all business books, but there's some I really love. One of my favorites is McKinsey's Growth Beyond the Hockey Stick. So if you're a leader or CEO who's always ever grappling with how to get your company to grow faster, and obviously it's DubHub, I was trying to accelerate growth. And just paradigms for what works. It's like the new good to great. I always love Jim Collins Good to Great, but great growth beyond the hockey stick is McKinsey's analysis of what makes top performing companies over a 30-year period. And it's just got lots of kind of anecdotes I love. So that's a favorite business one that I always recommend. And then right now I'm reading Atomic Habits. You know, Atomic Habits has long been on the bestseller list.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Because Rob pushed both of us. He pushed them to call me and need to consider it. And you know, when the situation went awry at Polyvore, the number one person I called was a guy named Becky Harry Narayan, one of those jungly founders and the one I was closest to who continue to know me and invest in all the companies I founded. And I just said, what do I do here? And he was the one who sort of gave me the like, look me straight in the eye, are these people you tried? Do they have your values advice and tell me to get the hell out? I really consider thinking probably the closest among that group, but all four have been very instrumental in my career.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, first of all, my dad, I always talk about the fact that he was a doctor, but he was also an entrepreneur, and he really loved working for himself. And I think he made the idea of entrepreneurship so accessible for me. Remember, he's also the guy who told me to take that train trip down to New York that led to the job with Merrill Lynch. Like if there was ever a champion of possibilities, even small ones all the time, it was my father. So he is my preeminent mentor for sure. And then I think the other group I'd point to is, you know, I've been lucky to have a lot of kind of great people I worked for. They often are my best mentors because they know me well and I know them well. All the tribe jungle, we talked about those four Indian entrepreneurs who started that company that I joined. I mean, my God, they became an angel investors in Yodeli, my next company. They introduced me that opportunity. One of them, Ramshiri Ram, was the first investor in Google. So when I made the decision to go to Google and they called me, it was”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure. Well, I probably have three that are at the top of my list these days. First of all, Ted Lasso. I know about you, but my family loves lasing Ted Lasso. Such a feel good, funny. Funny show. So well done. Season two, not so good as season one, but I will just say we still Ted lots of diehards on Amazon, a girlfriend of mine recommended McMafia, which is actually a pretty interesting, for those of you who like, I would say financial services and the mob, it's a fictional series on a British, Russian financier who gets involved with the wrong folks. That's a really niche one and an interesting one. It's been a great series to watch. Succession I'm waiting for, you know, season two. I mean, we all watched succession. And then I would say on the podcast side, right now, actually, I am listening to two separate podcasts about Elizabeth Holmes trial, one's the dropout from ABC and the other one is bad blood from John Careyu, who as you know is the original kind of journalist.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“The second thing is what I identified is like the inflicted pressure of performance as we start to see more kind of companies that don't look like the average valley company. And I don't just mean it's a woman or person of color. It could be a company that started in Canada. It could be a company that started in Kansas. It could be a company that started in India, like that doesn't fit the normal pattern. You know, dollars flow to where there's money. And so I think the other type of pressure is actually just performance pressure, as you see, you know, companies that don't come from your traditional background and founders either that.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I think there are two types of pressure that BC firms are under. First is from their LPs. So the first thing that needs to change and is changing is LPs. You know, the people who provide money to venture capitalists demanding to see staff on the rate at which they fund people of color and women, like i.e. how equality driven is their own funding profile. LPs have the ability to ask for that. And number two, what does the profile look like as a venture capital firm itself? Like what are their female partners? You know, what's their own pipeline for development? Because we know that when you're diverse, you fund more diversely as well, right? When you have more, you know, women as partners, more women get funded. So I think LP pressure is starting and it needs to continue. And LP is, I think, need transparency on how your dollars are distributed and need to ask for that in terms of pipeline versus deals that get closed. And then number two, pressure to keep these VC firms getting.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Unicorn several times over, I'm sure. And so there's lots of examples of women who are building really valuable companies. Oh, Canva. Canva just got funded at $40 billion. It's got Australian female founder. So I love seeing kind of these examples because I think it really, you know, A, it inspires a whole generation of other diverse leaders to feel like they can do it. But more importantly, for all of those BC dollars that had, you know, I would just say unconscious buys going out and like underfunded companies, there will be FOMO about the companies they missed. Maybe they need to look at their own funding practices and figure out like why they missed some of these great deals. And often it comes back to unconscious bias when these women and diverse leaders are early on looking for money.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Try and tackle this problem of equality. That's great. Number two, and I think this is important, people often say like, if you want to be it, you need to see it. The number and absolute levels of women who are founding companies compared to any prior period in my lifetime is kind of up into the right. People may say that percentages are still small, and that's true, but women are getting more venture capital. There's more pressure, obviously not just to put women on boards, but to provide funding sources for women and diverse people of color to start companies. And look at the number of female unicorns that exist, the female-founded unicorns that exist today. I was lucky enough to fund one of the first, Katrina Lake, a stitch fix. I was her early investor and she worked with me at Polybore. But since then, you have Whitney at Bubble, you have Rachel Carlson at Guild, you have the founder of Everly Well, everywhere you look, there are women starting not just great companies, but very valuable companies, Audi at House houses.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, first of all, I think there are two or three different ways to answer that question. Number one, there are lots of platforms now that try and solve bias and discrimination in everything from the hiring process to sourcing diverse talent. We're pretty unique in that we kind of are focused on the boardroom. But to sort of take away bias and discrimination from the hiring process, by the way, there's a whole other set of companies. I'm an investor in several that do things like help you confidentially report issues at the company in a productive way before it ends ever ends up in the press and gives companies the chance to arbitrate and to solve your problems, right? As an employee. So I think that we're seeing all sorts of platforms that run from bias and discrimination to anti-harassment to, you know, proactive consultation between companies and their employees to find solutions. So I'd say that is a positive to see that much technology kind of solutioning.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Public global companies. I think a few years ago when an activist put up a United Slate for the board, he used the board list entirely to put up an alternate slate for the board. And we didn't even know. We just gave us credit afterwards. He's like, oh, I use the board list. So that's great.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“The track record is quite good. Now, I would characterize the track record two ways. Remember, we're not a search firm. We're a discovery platform, which means our core metric is like how many people come to the board list and search and then ultimately find a board member. Whether it's through us or whether we were just part of their journey. And to date, we've helped over 2,000 women, 2,000 companies from early stage to public have come to the board list searching for board members. And as I said, the way I think about the board list is sometimes we are the accelerator of the journey. Sometimes you find the exact person you want on our platform. We are, you know, we consider our role to be a source of talent and to make sure that that board seat gets successfully filled. So yeah, and the companies run from Series A all the way to public.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“That point, they were like, oh, oh, like, yeah, you're right. But they didn't do anything about it. So when I started the board list, I basically crowdsourced. 600 names from 30 executives and entrepreneurs in the valley. And I said, would you give me the names of women?”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure. Well, if you recall, I wrote that open letter Tech Women Choose Possibility. And you said what was the reception? I said, it was very positive. And people kept saying to me, What are you going to do next? And of course, I thought I was just writing a letter, right? I was like, well, didn't I just do it? I put out this opinion. And, you know, but it became clear to me that maybe there was something more to be done. And I had been kicking around the idea, actually, with a number of DCs of them starting to put more women on tech boards. You know, they would come to me and say, I kinder, what should we do about women in tech? And they'd have all these solutions for putting girls in STEM, to which I respond. You can do that, but that will take generations. You realize that there meant plenty of amazing women leaders in the valley. I know them. I see them every day. Like, why don't you just put them on your boards? Because you have all these early stage companies that could really benefit from this experience. And ironically, you know,”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I don't know. Most leaders I know would know that that's really not a choice. I mean, once you're there, you're there, but I appreciate your saying it. Mostly, as I said, I'm super proud of the team because this is what I will say about risk, right? Risks come upon us that we never can anticipate versus ones that we can. And in those moments, you see people's agility. And let me tell you, the subhub team, like that is a team of people who share my values. And I was very proud to be leading a team that really made hard choices in a rapid period, including choices that affected each of them. Think about that. Like people making choices about their own job, you know, to try and make sure sub hub survives. And like, you know, as a leader, like a very painful period, but also one of the most rewarding to be with that group of people.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“I can't share any confidential numbers, but you know, back to company. No, no, I'm proud of the fact that the company survived, right? I mean, it looked dire for everybody.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“I got from people. I mean, I understand that customers were very upset. We had to change policies on refunds. On fly, yeah. I didn't have the money. On the fly. I didn't have hundreds of millions of dollars to give everybody their money back. The best I could do was give people credit. Like, I mean, like literally, I was like, I'm trying to choose between the company not going under. In which case, you'll get nothing. You'll get right. Literally, which was, yeah, how do you explain that to people? I did my best. I wrote a transparent note to our customers. I got tons of hatred. And it's fine. Like people were very frustrated. You remember the levels of everyone's frustration. It's people's money. So anyway, very intense, but I'm very proud of the team. We structured in a 60 day span. And only once we'd finished the restructuring did I depart because I knew that StepHub could survive for an indefinite period until live events started to come back. And so, you know, turns out the indefinite period has been over a year. Obviously,”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Not 100% case. No way. And by the end of the week, every sports league has suspended its season, like literally something like 20,000 events canceled in like a week span. I mean, when I say you go from sort of, you know, having a record sale to like an existential crisis, that was us. Because we were no longer owned by eBay. We didn't have eBay's balance sheet. We were owned by another private company who itself had to manage its cash because guess what? ISIN ticketing too, right? So IST being affected internationally. We're being affected internationally and more importantly in the US, which is the majority of our business. And so we went from, you know, record sale to cash crunch. And it was on my watch. And so you can imagine, I feel responsibility for our business. I feel responsible for our employees. I feel responsibility that we do not go bankrupt. And we rapidly restructured the company over 60 days. I will say to people, if you want to know what that period was like, just look at my Twitter feed. The amount of”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“And I do not expect to still be in the sea on March 13th. Well, I think I'll be there, but it will be part of my transition. And on March 13th, COVID hits the US sports and entertainment industry in a massive way. At the beginning of the week, we are forecasting that, you know, we need to start to plan for closures. And I remember saying to our finance schema, we're forecasting to be 50% down. Maybe we need to have 25% down. Maybe we should need to have a 50% case. This is what we're trying to think about how to. But not 100% case.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“That's unbelievable. Yeah, unbelievable. I know. People say unbelievable timing. One thing to note is, you know, everybody who was bidding to buy us in the strategic category was smarter than Stubhub because, you know, we were the largest player in C2C ticketing, right? Ticketmaster is the other big player and much bigger than us, but not the same category. So ironically, all of the people bidding the bias were people that honestly I would have wanted to buy, but they were all smaller than us, but with big checks and often PE dollars behind them. So look, successful outside for StubHub and then, you know, I think I'm going to sail off into the sunset after, you know, a reasonable but short transition period.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes, I know. People give us a lot of credit in hindsight for that sale period. And I think for eBay, just a tremendous outcome. Because to your point, we announced the sale in the fall of 19 and the transaction closed, like money in the bank for eBay on February 13th of 20. Wow.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Part eg Yeah, you got it. So, and by the way, and in this case, look, completely professional, like you have a founder who's been out of the company for 20 years and has nothing to do with near 15 years. He had started a competitive ticketing company, and now you want to come back. And by the way, he had been pushed out of the company. So if there was an ego involved here, it's that the original founders pushed him out of the company in 2005. And so, yeah, there's a lot involved in winding up being able to come back and buy the company that you were once pushed out of. So anyway, I had nothing to do with that dynamic. I just want to be clear.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Event with COVID. And, you know, ironically, StubHub sold for a record sum, you know, $4 billion. We led a process that led to a successful transaction that closed on February 13, 2020. And I thought, as much as I was personally disappointed, you know, I recognize it was a very successful business outcome. And I was going to go have to find a new job because very rarely does the acquired company, you know, get to have its CEO run the combined company. And I certainly was not getting that job. The original founder of StubHub bought back the company and he wanted to run the combined company.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“In 2020, yeah, no, no, in 19. My goodness. In January of 2019, and put pressure on the CEO, the then CEO, to sell that hub, as opposed to hold it. So midway, I was only a year into my tenure when an activist joined eBay board and quickly became apparent that we were going to end up selling the company and I was going to be leading a sale process, which is not necessarily what I personally wanted. So that I could have anticipated in the sense that eBay had had an activist once before. And certainly when I took the StubHub job, it did occur to me that that would be one potential risk that eBay itself might parent company would face pressure. I expected more sort of earnings pressure, you know, pressure to deliver our numbers every quarter. There was an outside possibility of an activist, but that came to pass and that led to the sale of the company to sub-hub sale. The other unexpected”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“I feel like that's the leading question. Just a touch. Just a touch, but I'm happy to share. I ran Stubhub from 2018 to 2020 in that time. There's a lot of surprises. Some I could have anticipated and some I couldn't. First of all, just a phenomenal and fun experience if you've ever been in a business of live experiences and giving that gift to people of live, there's just really nothing like it. And I'm also happy to be a big sports entertainment fan. So that doesn't hurt. But when I think about the things that were surprises, number one, StubHub, if you know the history, was bought by eBay over 10 years ago. And so was an eBay subsidiary. And I could have anticipated that eBay would continue to face shareholder pressure because it wasn't growing at the same rate as Amazon and its margins were declining. And in fact, that shareholder pressure came to pass and an activist Elliot, two activists joined the board, Starboard and Elliot.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“You've got the reward you want. They are. But we often only focus on the end gold when really I think what we should be focusing on is creating impact. Every time we create impact, we create an indelible result or outcome that is the result of our own efforts and learning and agility. And that's really like the reward for risk taking. Because I can't tell you if you're going to get the original reward. I can't tell you if you're going to get the original success you imagined or something different. But I can tell you if you pursue impact in every choice that between you and that big reward you're going to create a lot of outcomes and those outcomes will become the basis for your reputation, your confidence, your skills, and any future success you acquire. That is the reward for risk-taking. And that's why I say don't focus on success, focus on impact.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, on your way to your larger ambition, every day you're making choices and producing outcomes, you know, in this, and you're just doing that cyclically. Between you and that big reward is a dozen, 10, 100 more choices. And every time you make a choice, you're trying to produce a success, a learning, but some kind of outcome. So let's say that you don't achieve that ultimate success. You don't get the promotion. But along the way, you built a great division. You doubled revenues. You launched new services. I call all of those outcomes. By the way, you built a team that, you know, gave you a high satisfaction rating as a leader. All of those outcomes are still positive. There's still what I call your career capital. And in that process of just continuing to pursue results and impact, you've not only accumulated career capital, you've likely become more agile and more confident. So aren't those all things that are going to contribute to your future success, whether or not”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure. Well, what I always say to people is when we make a big choice, particularly a big career choice. You know, most big choices unfold to sort of a meaningful reward and call it three to five years. It's hard to think about a work ambition that you could just that is big enough to be exciting, yet so small that you can achieve it in six months, right? It almost doesn't happen. So let's presume you make a big choice and you're like, hey, I want to ascend to this level. I want to be a CEO in the next three to five years. Or I want to get at my current company or I want to be the head of this division, whatever it might be. At the end of the day, we make a big choice and we're not done, right? Like once we've made a big choice, we're like, oh yeah, now I need to execute my way for that reward. I didn't just choose it. Now I need to execute my way to that reward. And so through the process of execution, every day we're making littler choices to find success. We'd say like, okay, now we need to build the revenues of this, you know, of this division. Oh my God, we need to restructure. Oh my God, we need to find new ways to grow.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Absolutely, absolutely true. You can't just research away all the inherent risk in the situation. You just make the best choice you can. And then you need to have confidence in your ability to respond.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Painful and like, and honestly, like a waste of my time and their time because nothing transpired that was positive, right? We just, I just exited. So I considered a failure. But I also consider it a success in the decision to join e-commerce, you know, to leave Google and become a CEO. I got to run my own company. I got to run Stubhub. I began a journey. I got to become an e-commerce investor, an e-commerce board member. Like I have loved being in the business of e-commerce for the last 10 years. And that would only have been possible because of my decision to join Polymore, however painful. So anyway, I think it was a personal failure, but I think in many ways, you know, the choices I made, some of them stuck and those ones, you know, not all of them, but several of them were successful.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, well, by the way, I would say to people it depends over what time frame you characterize that decision. On a six month timeframe or your timeframe, that was a failed decision. And I call it a failure because I failed to have impact. You know, it's different than joyous, right? We talked about why joyous did or did not reach its culmination as a video platform. But I can look back on those six years and see every innovation we achieved, see everything we built, see the team we assembled and what they've gone on to do, see the fact that like we were the pioneer. And I can feel very proud because I know I had impact. Polygora, I had no impact. I was just six months. You know, it was.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“That you want to tie yourself to going forward. And I said, You're right. And so I actually didn't fight for it. I was like, okay, he wants it. He can have it back. I'm out. You're right. This is not the right place for me, which was against every instinct I have as like somebody who wants to drive and control, right? Just to give up and be like, yeah, you're right. And I look back on that situation and say my mentors were right.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Working for or with most closely, right? In our experience, working with them. Do we share the same values? Do we have different strengths? Do we have complementary strengths? And I think I ended up in the boat with somebody who at the end of the day didn't share my values. Like we really wanted to run the company, not just, I wouldn't even say it was different ideas of how we could get there. It was like, we wanted to run the company differently. What we valued in leadership was different. And so when that, you know, when that situation transpired, I went to my mentors and I said, oh my God, like the founder wants the company back. Should I fight for it? And the very first thing my mentor said was no. They said, why would you ever want to fight for a company that's 10 people big where quite frankly what you're telling me about this story and what's transpired? And by the way, I'm not going into nitty-gritty of how it transpired, which was maybe not in keeping with my values. They're like, from all of the behaviors that have gone on, like what makes you think that this would be a group of people?”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“This is going to go one of two ways. Either my partner and I kind of share the same values and want this to work, or there's a possibility that this person feels very threatened by me voicing my own opinions. And I think the latter ended up happening. And at month six, you know, the founder basically said, I want the company back. It's either Sukinder or me. And the board chose him. And it was an incredibly painful experience. And so what did I learn from it? I think I learned one seminal lesson, which is you can do all the studying you want. You know, whenever you make a new choice, like the who that you're partnering with, the who of the equation is even more important than the what. I always say that to people like we make new choices based on the industry, based on the company, based on the company's track record, based on our passions. Yet intrinsically, when we enter any new situation at work, we are, you know, inextricably tied to whoever we're”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“On the one hand, you have a founder who has been used to running a company and obviously has control over it, including financially through equity ownership. And then you have a CEO who sort of theoretically bought in to sort of be the adult. So my point overall is that when you think about any startup founder, CEO journey, you're like pairing somebody who has financial ownership of a company that's pretty large and moral authority with somebody who theoretically has professional management skills, but also wants to set vision. And that's what I entered into Polybor. And I think if I were to characterize it in a nutshell why it didn't work out, I think that, you know, the first three months, I was listening to sort of what the founder had to say and didn't really want to disrupt the Apple cart. I really want to listen and be a thoughtful partner. And month three to six, I started to sort of voice some of what I believed we should do with the company. And by the way, I said to the board,”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure. Well, first of all, I always say to people, you can take smart risks or try to take smarter risks, but you don't never eliminate risk entirely, right? You can do all the studying you want and set yourself up well and still fail. I mean, that is why it's called risk after all. And certainly in Polyvor, I've made a very studied choice. I entered the e-commerce arena very knowingly. I wanted to be a CEO. And the company, I mean, I'd known the company for three years. So I felt like I really had done my homework. Yet when I arrived at Polybore, I had a game plan that said, look, I'm taking over from a founder. You know, Silicon Valley is littered with founders, CEO, pairings that don't work, that crumble. It's like a marriage, right? I mean, at best, your odds are 50% on a marriage. And like, I'd say they might be even slightly less on a founder, CEO relationship, because you have two people who have authority over a company, right?”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“To, I would say apprentice under masters. People are really good at it. And those people attract new opportunity all the time. So those are the reasons, I think, that proximity, getting close to what you want, even before you know it exactly has far more value than planning in the abstract.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“To environments or people that even roughly approximate the thing you think you want, the thing you think you want. And cheap things happen. Number one, you learn a lot more by being proximate than planning from afar. Like if you say, hey, I want to be a chef and I'm currently a financial analyst. Like what say, well, how do you get yourself in circumstances where you're in and around chefs and restaurants, you know, before you ever make a mighty leap to go to culinary school? Because you can learn by being proximate whether or not that thing is even what you want, right? So getting close helps you identify the thing you think you want is what you really want. Number two, you get knowledge on how to achieve it because you're, you know, you're proximate to people who've already done what you want to do. And simply by studying them or being around them, you're going to learn. And the third thing is, well, if you really know what you already want, when you get proximate, you know, you really get the opportunity to, you know.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“It's interesting. I think one of the reasons people fear risk is they just don't like uncertainty. In fact, there's research that suggests that often people choose something, not because they convince it's the best path, but because it simply reduces uncertainty. So uncertainty creates a lot of anxiety for people. So what's the antidote to that? Well, for many people, it's planning. Well, I'm going to do this, but first I'm going to create a plan. So they start planning for the thing they don't know and they plan from afar, right? So you can create this perfect plan of what you imagine the thing is that you want to go after. And you can add more and more detail to that plan. But the problem is like you're pretty far away from understanding what that new reality looks like. And so while you're creating a plan, it's not like it's sort of a plan in your head with more and more detail that makes you feel, you know, less uncertain, but it's not getting you any closer to the action. So often I say to people, like if you know what you want, or even if you don't, get proxy.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Small big, small, small, small, medium, small, small, small, small, and they just keep pivoting in small ways until they realize the reward they imagined are a different one. So we have boiled the hero's journey down to a single choice when really rewards getting is about a system of unlocking multiple choices. And it's never just one choice. It's about committing to the process of continually choosing your way and your path.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, you know, and not just for entrepreneurs, for people at larger companies too. We have this idea, you know, when we look at the heroes journey, what we see and remember is this like one mighty choice the hero made that could either lead to sort of abject failure or glorious success. And by the way, we see that story not just in popular media, but even in the media that relates the journeys of successful entrepreneurs. Like we're all watching what happens when Richard Branson goes to space. Is this going to be ethically successful or something disastrous going to happen? Like there's all of these binary stories we see about people's like big singular choices. And I think, and I call that the myth of the single choice in the book, the reality is that most people who are taking risks, it's not one risk that led them to the reward. It is a multitude of risks. And by the way, they're not even all big. They may be small, small.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“It's about how you become a calculated risk taker, right? If we're asking you to lean forward and take more risk in your career, the question is, you want to do it smartly. And then the last, of course, really chapter really kind of talks to how many of these choices really unfold over time. So organized it roughly in the order in which it happened in my lifetime, which is also the sort of order, broadly speaking, which I learned these lessons.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure. So obviously it's probably obvious from this conversation that I've taken a decent amount of risk in my career. And I wrote the book because I think people have a very unrealistic sense of what risk and reward looks like compared to how it really unfolds. And so I structured the book in a way that really I didn't want it to be a memoir, but I structured in a way that goes from sort of basic lessons on risk-taking to sort of maybe more complex, not ideas, but kind of philosophies. And it really mirrors maybe the way I learned to take risks. You know, for me, it was really simple in the beginning. And, you know, we talked about those early moves. I made five or six moves in the span of seven years, right? So whether they worked out or not, I took a fair amount of risk, you know, and made a number of sequential choices. And then I think the middle is about being a smart risk taker. Nobody says, I don't say certainly that this book is about just taking risk willingness.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Uber had its Me Too moment about a year later. And in fact, many companies did. And you started to see some of the very, very bad behavior far beyond the microaggressions that many women talk about that, you know, people of color and women experience, unfortunately, to a far greater degree than any of us think. So the letter predated it, but I think Me Too really exposed some of the more flagrant and honestly awful things people go through at work.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Building at larger companies. I really didn't try and use my voice actively on any broad topic. So for me, it was a risk to even write the letter, right? I'm like, what will people think of me? Well, they think I, like, you know, I'm putting myself out there for the first time as a female first and a leader second, which is the exact opposite of how I ran my own career, right? I never wanted to be seen as sort of like for my gender. I wanted to be seen as my capabilities. So I think the letter was very well received. I think people just said, well, hey, thanks for acknowledging the reality, but also being solution-oriented. Like, you know, it was just a counter to the narrative that it's also terrible. And really until all of our daughters become engineers, nothing can be solved. I mean, so I think it was maybe the first time I'd use my voice in any kind of way that offered maybe a personal perspective. And I found a little risky to do it. And I think I was validated in sort of trying to.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“Overwhelmingly positive, a lot more than I second. Keep in mind, you know, we talk about risks we take in our career like many other people. I spent the majority of my career heads down building my own companies.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source
“I was too aggressive for the secretaries. And I'm now startup entrepreneur and I hear firsthand stories from other amazing female entrepreneurs and how terrible their experience is, fundraising and just the biased experience. So I wrote the op-ed by surveying 100 women in tech from CEOs to entrepreneurs asking for their opinions on being an entrepreneur and then their experience of bias and discrimination. And in fact, what the survey shows, which is why I write the letter, is what you'd expect, which is, you know, they, you know, I think a majority had said we have directly experienced bias and discrimination. Yet like 80s. Did it lead to the letter or the book? A little bit, the title is what I mostly took from it, but I think the notion that it's a dual path, like there can be risk and reward and still danger or harm.”
2021-10-22 · Masters in Business · Sukhinder Singh Cassidy on Entrepreneurship (Podcast) · IDENTIFIED FROM THE TRANSCRIPT · source