How to Take Smart Risks at Early-Stage Startups with Sukhinder Singh Cassidy

Sukhinder Singh Cassidy, Founder & Chairman theBoardlist chats with Amit Somani, Managing Partner Prime Venture Partners.

Sukhinder is a Digital leader, Board member and Investor with 25+ years experience. She has held leadership roles at Stubhub, Google, theBoardlist, Yodlee, Polyvore, Joyus and Amazon. 

Listen to the podcast to learn about

01:00 - Risk-taking as an early-stage startup founder

06:50 – How to train your team to take risks

11:30 – Evaluating risk and reward when joining a startup

21:45 – How to rent the mind that you can’t afford to hire

27:30 – How should board members help founders

31:30 – Think Gut-Data-Gut NOT Gut Vs Data

36:00 - How to write a book about principles

Check out the book Choose Possibility by Sukhinder Singh Cassidy

Read the complete transcript below

Amit Somani 01:10

Welcome to the Prime Venture Partners Podcast. I’m your host, Amit Somani and I am delighted to have Sukhinder Singh Cassidy. An ex Googler, the president of StubHub, she’s just written a book which we’ll talk about on the podcast. And she’s also the co-founder and Chairman of theBoardlist. Welcome to the show Sukhinder.

Sukhinder Singh Cassidy 01:30

Thanks for having me.

Amit Somani 01:34

Sukhinder, so you had a fascinating journey, but I have to start with your book ‘Choose Possibility’. Because it talks about very many things, from managing your own career, to managing risk, to trading-off risk versus reward. And as you know, we at Prime and many of our listeners here are early-stage entrepreneurs. So, can you talk to us a little bit about some of the stories around risk-taking, as it pertains to early stage entrepreneurs or early stage startups. How would you define it? How would you take some of the frameworks in the book that you’ve got, building your risk-muscle and so forth? How would you help people think about cultivating those?

Sukhinder Singh Cassidy 02:10

Sure. Happy to, and again, thanks for having me. So, I think one of the things to note is there’s a self-fulfilling prophecy one might say, which is sort of, if you’ve started in an early-stage company, you probably already chose possibility at least once. To choose possibilities is sort of my framework for thinking about risk-taking. However, and I think this is one of the big frameworks in the book. If you think it’s about choosing once, between risk and reward, you’re in for a big surprise because often the path between risk and reward is fairly non-linear and it’s the result of many choices. Again, that may be obvious to an early stage entrepreneur, but when we are in it, literally in it and trying to find product market fit, the question for us really, right. And you know, this is the feedback loops we use to figure out, where the unlock might be.

So that, I would say is maybe the obvious thing from the book. I think for early-stage entrepreneurs though, often the question is what are smart risks to be taking and what are risks not worth taking? That’s one I see often. And I’ll talk about that in a moment. The other one I see is how do I train everybody else in my company to take some risks? Because I say to people in early-stage companies, the founder is doing it all, they’re taking all the risks and so forth, everybody looks to them and they take the risks. But every founder I know, and I’ve been a founder three times as you know, Yodlee, JOYUS and theBoardlist. I know that what I always wished was, well wait, how does everybody else around me take risks and act like owners? Am I the only one who’s supposed to be doing all this?

And I know many founders who are listening to this can relate to this feeling, when my company is going to scale, it can’t all be me, right? So, I think we also have to take other people to take risks. So, let me come back to the former, then I’ll go to the latter. I think while it’s obvious, as I said, to get into an iterative loop if you’re an early-stage founder. I think talking about the smart risks to take as the founder, the ones I think about most broadly and most importantly from the book are what I call “put the who over the what”. I think often founders want to hire people who let’s say have done it all before. I’ve seen this pattern. Somebody will walk in and has the resume for the exact job you want, right? But, when you think about prioritizing who you hire, I always say, think about two or three things.

Number one, if you want to take smart people risks in trying to unlock impact faster. The first and foremost is look for diverse skills to your own, not homogeneity. This is a really important one. I think most people want to hire somebody who looks like them, but then you end up with a company of engineers who all may get along fabulously, but you’re trying to find product/market fit. And there’s nobody who understands demand. And you wait too long to make that hire. Again, that’s a problem I’ve seen.

Number two, I hire, interestingly, if I want to hire people who can take risks in my own companies, I’m looking for people who have agility and who have a track record that demonstrates, usually at this stage small and maybe some large. And you say, well, why large companies? And it’s because actually at large companies… Once you already have product market fit, you tend to see A talent. You tend to know what A talent looks like. So, I like hiring people who’ve come out of large companies, but I want to see that they’ve done small companies too. I want to see that they’ve had both failures and successes.

And I think we often think that that risk-free hire is the person who’s done the job before. And the person who’s come from a track record of only success. And I would challenge that because I think if you want to hire people who have agility, and who can get into a feedback loop quickly without you needing to tell them, they know how to unlock and solve the next problem. You’re looking for people I think who’ve shown that agility in their own career, including failure. And I don’t think that’s an obvious, smart risk for people to take. They think that the smartest person to hire is the one who’s done it all before. And I can tell you that people who are only used to success may not have the agility that you’re used to. So that’s, I think, a really smart and important risk.

And then where I think it comes to teaching other people to take risks in your organization. I think one of the things I find very useful, and again, I have a lot of empathy for this because I’m a founder with strong opinions. I always say to people, “if you walk into a room with no vision, you’re going to leave with my vision.” And by the way, that makes me really happy because I get to say everything I have in my head. It’s not a particularly empowering or scalable way to sort of train other people to take risks.

So, I think as a founder I would say, you need to think about when you’re the author and most of the times as founders, who are always the author. And again, I understand that in early/product market fit, but for an early stage entrepreneur to even be able to get to the next level, you have to be able to hire smart people. And we talked about them, people who are agile. Guess what? People who are agile, they don’t necessarily want you telling them everything that needs to be done. You have to leave some space for them to author. And so when you think about authorship versus what I call being a publisher, one of the early and smart ways to help other people take risks is to literally, consciously think about when are you going to move your brain from author to publisher.

For somebody like me, it’s something as simple as like, hey, when we have a one-on-one, can you please bring in an agenda? Because I know that automatically shifts the onus to them. And you’re like, oh, an agenda’s bureaucratic. I’m like, an agenda is not bureaucratic. An agenda is a way for the person coming into the room. I don’t care if it’s on Google docs, I don’t care if it’s three bullet points. Organize your thoughts, come in with what you want to say, because when you come in and you’re just waiting for me to tell you what to say, guess what? We’ll have that conversation. And I don’t think founders realize how much the tactics they use really influence the ability of other people to author. We’re like, own, author, take a risk. You have to think about whether or not you’re creating space for people to take a risk.

Amit Somani 07:40

So, Sukhinder. I have a dozen follow-on questions, but I’ll try to limit it to maybe two or three. So how do you evaluate beyond obviously the resume and the pedigree. And you’ve talked a little bit about that in the book as well. The ability for people to take risks, right? How do you evaluate learning agility? Whatever is demonstrated, is demonstrated, and maybe you can do deep ref checks and so forth. Do you have a favorite interview question or two, or a part of the process that helps you evaluate risk-taking ability or agility?

Sukhinder Singh Cassidy 08:10

Sure. I have a few things. Number one, I always look at people whose resumes… When people have resumes that show two things, taking risks to learn, and what I call an ability to quantify their impact, I think I have my person. So, what do I mean by that? When people show me res… Oh, and there’s one third tell-tale sign in an interview, which I’ll give you. So let’s say I’m looking at somebody’s resume or their bio. What I’m looking for are people who might’ve taken a lateral move to learn something new. I’m looking in… By the way in the interview, you can ask this question, “tell me about a time you took a risk at your job”. And when people who have a perfect resume, it’s all big company, or it may be small company that had an outcome.

And then when you read the lines of what they did, they themselves find it hard to identify their learning or what I call their impact. They may be say something like, “part of a team that worked on ad sets”. I’m making it up and I’m like, okay, you didn’t really write your resume for what your impact was. And so you can look at these resumes and say, first of all, how do they write them? To your point, do they look small, big? Is there any evidence this person has tried something new in their past and taken a risk to learn, taken a non-obvious step. To me, I actually find it quite intriguing. And as I said, when people go small, large, they might have a failure and a success.

That’s one thing, but when you’re in the interview, I think asking people simple questions, what are risks? What are some of the smartest risks you’ve taken in your career? And if they can say things like, hey, “this risk I took to learn something, this time I took a non-obvious step, this failure I had” They’re quite easily able to identify when they took a risk to learn, to discover, to have impact. And then is follow-on question as I said, this is the tell-tale. One, I’m like tell me about your failures. Oh my God. The non-fail fails that I hear in an interview. I’m like, did you ever really take a risk?

Amit Somani 10:05

“I work too hard”. That’s what they tell me.

Sukhinder Singh Cassidy 10:10

I work too hard, I’m too ambitious, I’m ahead of the other person. I’m looking for the tell-tale signs that actually, you were willing to take risks, to try for something harder and willing to point to when it didn’t work out the way you thought, about what your learnings were. So, I’m looking for evidence of risks to learn, risks for discovery, risks to advanced skills, ability to talk relatively fluidly about real failures. Because real failures are the results of taking risks. And so, these are often the tell-tale signs that I look for.

And then my favorite non-interview question, when I… oh, and by the way, the one I talked about. I always say to people, what was your impact? If you can’t say, point to the place you were and the thing that would not have been learned or achieved, but for the fact that you were there helping push it along, if you can’t identify, and you don’t have to be a CEO to have impact. In your team, what was the role you had that…? And what was the impact you could point to that was accelerated because you were there, I’m looking for those types of answers.

And like I said, the other thing I use is I actually think interviews are fairly flawed because some people are good interviewers, some people are poor interviewers. I liked the back-channel reference, and I basically say to a back-channel reference, can you just let me know, is this person the top 1, 5, 10 or 25% of people you’ve ever worked with? Where would you stack rank them? By the way, if they can’t put them in the 1, 5, 10 or 25, I’m not sure I want to hire them. And then when they tell you, you can probe. So, those are some of the things I look at.

Amit Somani 11:40

Absolutely. Coming back to more of a career question for people. And then I want to go to the startup one in just a second, which is that, the line between risk and reward is not an instant feedback loop. Right. And it’s also a sine loop, right? I mean, you take lots of risks. You build muscle, maybe there’s some lateral or maybe even a step back to take two steps forward, etc. So, can you talk to us a little bit about…. And Steve jobs used to say this, right? “You can never connect the dots looking forward.” Right. “You can only connect them looking back.”

So, whether it’s Yodlee or Junglee for you, or Amazon, or Google or whatever it is, right. You can only look backwards. When somebody is evaluating whether to join a startup, right? Or to start a company or an exec from a larger company to come work for a smaller company, how should they think about that?

Sukhinder Singh Cassidy 12:30

Yeah, it’s interesting. So I always think, and I pointed to this earlier, so let me come back to it, and some actually key data. When you think about smart risks to take, I often say to people, there is a macro set of things to evaluate. And in the book I talk about headwinds and tailwinds, you know this. You’re looking to figure out where’s their momentum, or by the way, even in a headwind, we often get more responsibility. Somebody might be willing us to offer us a job that’s two degrees more responsibility than we have in a large company. And by the way, I’ll talk about why that’s a smart risk. But number one, you want to evaluate, so the macro-environment, and smart risk-takers know that actually success is not all about that. It’s about the situations in which you can mine or that can accelerate your success.

Number two, we talked a little about the who, we talked about from the perspective of a leader, but from the perspective of a joiner, we’re looking to find places that value our diverse skills and strengths and need them. When I went to Junglee, we talked about this. They wanted my biz dev and sales brain to be at work. And because it was very different from what the founders had, and that was what they needed, but values overlap. We do our best work when we’re in a tribe where we feel safe. Yet, we have diverse capabilities. Right?

Number three, I think one of the smarter risks to take, and you kind of identify this, is knowing ourselves inside of this equation what we value. Our passions matter, but often passions are actually changing. So, it’s sometimes hard to follow when somebody says, I follow my passions, my passions changed, but I think we definitely want to know our strengths and that’s key. And then I think this last notion of taking a smart risk is like, I think about my goal set in kind of three to five year increments. Some people want to paint the forward picture, but you and I both know, I could give you a hundred permutations to have landed me in the job running StubHub, literally from the start of my career. So even though I thought it was going to go one way, when I’m in a feedback loop, responding to what I’m doing well, and following kind of some of these principles, I may end up in a different role than the one I thought I did.

And so, when you put that all together, I always say to people, when you’re thinking about whether to join a startup or not, think about these macro questions of which startup, but then think about the reason you’re taking a risk and broaden your perspective. Is it to accelerate learning? By the way, that’s one of the best reasons to take a risk, because when somebody gives you the opportunity to learn something new and gives you more responsibility than you might be qualified for, those are times when accelerated learning happens. And by the way, learning is always… If you can learn at an accelerated rate, you also have the opportunity to have impact at an accelerated rate. So, often people want to jump to the job in which they know they’ll be successful. That’s not the job in which they necessarily get the most learning. Does that make sense?

So if you look at my career, I followed learning a long way. I mean, I changed industries, I took a demotion to go to Google, I left my own startup as a founder and SVP at Yodlee, because I was there five years. There was no more learning to be had. I was not going to be the CEO. I had done every job. The company simply wasn’t growing fast enough for me to have new skills acquisition. And I went to Google and I took a two level demotion and I pivoted into local. Right. I followed what appeared to be like a high tailwind. I pivoted again at Google into running international. Again, I had no business running international business, but because I had taken the risk to learn and been able to have impact, I got rewarded by being offered something new to learn. So these things are not obvious, but I think I followed accelerated learning and challenge as a precursor to impact. And that has turned out to be a very good risk to take consistently.

Amit Somani 16:20

Yeah, no, I think I’ve done that a lot in my career as well. And I think you need to have a certain level of going inside and having kind of peace of mind, even security, right. And being somewhat self-secure to be able to do that. It’s nothing to do with finances. It’s just mindset, right.

One last quick question on risk, often in the startup world, and especially early, you have the sort of folklore or this adage of go big or go home. When you think about later stage startups or post IPO companies and so on, right. You could still have the social or what you’re calling asymmetric upside, right? The downside is not very much for them, whether it’s because of learning or whatever, but the upside is crazy. When you’re an early stage founder and a VC like me or a board member, like you says, guys, either we shut shop in the year or we are going to be the next, whatever Minicorn, Unicorn, whatever the next company that does a hundred million ARR from zero. So, how do you think about this, go big or go home notion, particularly at early stage, not once you’re established?

Sukhinder Singh Cassidy 17:20

Well, I think that you hit it earlier, often between any risk and any reward. This is the irony. This is why I call it choosing possibility. It isn’t a singular risk or the reward. It simply is not, it is a series of choices and it’s committing to the path of choice-making, looking for the impact, choice-making again. And I think it’s far more about your frequency than the size of the risks you’re taking, right? It can be many, many, many small. You and I can talk about how 301% moves, move you literally 360 or 360 moves, 180 incremental moves. It could be a move that moves you 10% and the move that moves you 1%. That kind of doesn’t matter. I think people are more obsessed with the idea that I need to make one perfect choice, sometimes even in a startup.

And you’re like, no, no, it is actually about your commitment to a number of moves and frequency. And so I think to your point in a startup, you’re taking a gigantic risk when you only have 500,000 in the bank. That might be actually the stupidest thing to do, because if you want to burn your cash to zero faster, knock yourself out. Most of us, obviously in the business of making incremental moves to figure out which is the unlock. And as you guys again know, it’s often the compounding benefit of many choices that will lead to product market fit. And you sort of have to follow where the path lead.

So, while this is all obvious, I think that the problem is the valley really celebrates. And this is one of the reasons I wrote the book. The ‘one big move”, ‘the one big bet’ and I’m like, people learn to become expert choice makers, but literally not expert as in one choice. Expert is in the consistently choosing, they’ve committed to the path. And therein is obviously, the key to unlocking reward. And in the case of an early stage startup, it is actually a lower risk way to manage your capital, which is limited by its very definition.

Amit Somani 19:10

Great. Let’s switch gears Sukhinder and talk about a different topic altogether, which is about board compositions, right? You’ve been a part of some amazing boards, right? From TripAdvisor to StitchFix, to Upstart, to, I don’t even know the full list. And of course you’re now running a company called theBoardlist, where you’re helping others kind of get board members from best, I could tell. So can you talk about what makes a great board and again, how should a founder think about the board composition. Right from hopefully day zero, but certainly day one, if not day zero, right?

Sukhinder Singh Cassidy 19:45

Yeah. This is the irony, right? We talk about some of the smartest risks to take if you’re building a team, is to find diverse skills, but values overlap, right? Value overlap means we feel we’re in an environment where our general sense of what’s just and fair in the world is aligned and allows us to do our best work. It doesn’t mean it’s a perfect environment, just means an environment where who we are, we feel we can show up authentically. So, often founders wait till too late to find people who… Find the one or two people who are necessary to unlock the things they don’t know. So we talked about this. You see many founding teams to start with, I understand. The two, three people they know, that’s awesome. The ceiling you hit is often not because you have many people in the company who are the same, it’s because you’re missing a skill that’s so critical.

Now in an early stage startup, I always say to people, I remember I wanted to hire the best talent in the world. Guess what? The best talent in the world is not coming to your early stage startup, when it’s in working for you and leaving Google or whatever, when it’s high, high risk. Some people simply won’t come before product market fit is achieved. And even when it’s achieved, they want to see a series B, C company, but if you have a boardroom, which quite frankly lacks any diverse thinking. And I find it ironic, I’m like, well, what if I told you, you could rent the mind but you cannot afford to hire? Let’s just think about that for a moment. You’re an engineering driven company, you know nothing about SaaS go-to-market. Wouldn’t you want to give yourself a double insurance point, insurance policy by putting that expertise, not just in the company, but on the board? Couldn’t that be an accelerant if you’re not having to recreate the wheel.

And by the way, again, you may not be any position to hire a VP of sales. You simply can’t, you’re hiring your first salesperson. Well guess what? On the board you could put a VP of sales. I think that people think that boards are for later and they’re for governance, unlike they’re for skill renting, when you’re early. And getting that diverse, great mind who maybe doesn’t think the way you do, but maybe is the unlock you need in the next chapter of the company. And the other benefit of building board diversity early is that, private boards, you can define the board term. Nobody’s saying that this is a person you have to take for 10 years. You can say, Hey, this board term is two years, it’s between now, then we’ll both really decide in the next series, because the needs of your board may change or be similar. So, I would say, think about renting the mind on the board, who would come for some equity and who is fascinated, but maybe your board represents the experience they don’t have.

On the other side, I say, if you’re a large corporate executive, do you really… I understand it seems very cool to join a public board, but if you’re wondering what a startup is like, and you’re too afraid to go, wouldn’t a great risk to take be to go sit on some of these boards? And you can learn it. I mean, these are all right, smart moves. They have very low risk for people’s time and energy, yet can have an outsized reward on either side. Yet, I think we think of the boardroom is something to be sort of not touched. And a founder thinks that highest risk move they can put do is give somebody an independent board seat. I’m like, no, that person’s not going to control your boardroom. It’s controlled by you and the VCs and the people put the money in. I think of that it as a rather smart move to put somebody independent on your board early and independents who have the industry functional expertise that you need for the company that you lack.

Amit Somani 23:05

I completely agree with you. I think it’s highly underused, not just at early stages, but ironically, certainly in a lot of the Indian startups. I would even say in sort of mid to later stages, right. Until you finally finally wake up and you’re like, oh, wait a second, we need to do this. And I love that term of skill renting, I have not heard that before. I think it’s phenomenal because I think it’s expertise, it’s network, it’s somebody to be the sounding board. If you’re getting somebody who’s great on sales, on your board and an independent board member, they can even help you hire the VP sales or figure out how the comp structure should work or whatever, which you may have no experience or expertise as a founder.

Sukhinder Singh Cassidy 23:40

I totally agree. And I think people are penny-wise, pound-foolish. Of course when I was in a startup, I thought my equity was worth the most, and I didn’t want to give it away lightly. And I’m not suggesting you should. But, if you think about the quality of the person you’re trying to attract, I would say, if you’re worried about the equity, give then make it a shorter board term, you can re-evaluate in two years, not four, right.

But, it’s sort of like hiring. That means, well, did I give them too much equity? I’m like, well, if you gave them too much equity, you’re going to wake up two years from now and be like, or even now you forget two years, six months from now and be like, wow, I can’t imagine what I was doing without this person. Or you’re going to both figure out it’s not a fit and they’re not going to be here four years anyway. So, we often obsess so much about the percentage or what have you. And I’m like, look, get going. You’re either going to be enthused or not. And there are ways to control how much equity you give away by simply things like board term and then be able to re-evaluate more quickly.

Amit Somani 24:35

Great. Since you worked with many founders, you’ve worked on both sides of the table, right? Being founder, as well as being a board member. Talk to us about some of the best practices of how the founders leveraged the board the most, or maybe some innovative ways in which they do so, beyond skill renting. And vice versa, if you’re a board member, what is the best way for you to add value? Because like we said earlier, you don’t want to be kind of stepping all over the founders and sort of…

Because you’re not doing this vicariously, right? You may be seeing it vicariously, but the founders that are running the company. So maybe on both sides of the table, what’s a way to be a great board member that you’ve found to be useful? And for a founder or a set of founders, if you can even name them, how are they able to use the board very successfully?

Sukhinder Singh Cassidy 25:20

Sure. Well, look, I think that as we talked about… First of all, you can change the composition of the board over time, particularly if you’re private, right? You can set clear board terms. And just like I said, think about what you will need at each stage and keep people on if they’re great and if not have flexibility. So that’s one of the smart ways to use a board, is just to think about the composition of skills and also term as a way to sort of keep maybe new people coming to the board, if you want, or some people, they just love the stability of having the same board from start to Series D or what have you.

But I think the other smart things that I’ve seen done in the boardroom is look, there’s founders who send you this…. and a lot do it. They’ll give you a 40 page deck, 50, 60, you know, everybody has dumped their slides into it. And the board meeting is simply an update for what’s happening with the company. I’m not sure that’s the best way to use the skills of the boardroom. I think it’s about creating an expectation and also a very efficient 30, 90, 120, whatever it’s going to be. And obviously, we know in early stage startups, you also go to a board member often outside of a board room to ask them a question. But to leverage that person’s time, I think you’ve got to send the deck ahead of time. Even if it’s the night before, your board members are ADD, not just you, they really don’t want to sit through a 50 page update. Now you’ll say, well, I sent them the deck and they never read it.

Be clear on your expectations. Be like, I am sending the deck now, tonight or I’m going to send it an hour before. And I expect people to read it. And I think you need to say, “what are the three questions you want answered in this board meeting?” So come with the three discussion items you want to lead on and extract the value, because if you do an update, you’ll get a bunch of listeners. If you lead a discussion, that’s informed by whatever you sent ahead of time, right? If you want to use the slides as backup and lead a 10 minute update, but not go through the slides, these are all great. But it’s about structuring the time and sending the materials ahead of time. By the way, we’ve also all been in board meetings, myself included where nobody’s read the deck.

It’s okay to literally say, “if you haven’t read the deck and you didn’t have time, it’s okay, we’re going to take the first 10 minutes. Can everybody read the deck?” I can assure you, your board members are smart enough to read your deck in 10 or 15 minutes and then be like, “and then I’d like to have the discussion”. So you can even do that inside the confines of the board meeting if people have it. And I many boards where no matter what people say, they did not read the deck. When they got to the room. A lot of VCs don’t read the deck always before they got to the room. You see many people winging it and if I was a founder, I’d be frustrated. But I think you just have to realize the boardroom is another group of people who aren’t together often, they’re like another team to manage.

You’re like the coach of another team. So if you want to get the most out of it, you have to put some amount of effort into coaching those folks along. Not because they’re not smart, but because you have to point them and give them a framework. But the framework is not, “let’s just go through the slides and then I’ve given you a company update. And I think my board is rather useless because they didn’t give me any feedback.” You have to guide the discussion and be in, and use the time for discussion in a framework.

Amit Somani 28:20

Great. And how would the inverse, when you’re a board member, what is the way for you to be very effective, but yet not “overbearing? “

Sukhinder Singh Cassidy 28:30

Yeah. Well, first and foremost, I think that A, it can be helping to solicit that cadence. If you’re not getting it from the CEO, you can suggest it. You can say, hey, it’d be great if you send this the night before and what are your three questions? So we don’t overtake the conversation, because that happens. I know many founders who are frustrated that a board member takes… goes off on some tangent and it’s hard to wrangle them and come back. So, I think your job as a good board members to try and solicit, what is it you want to get out of this interaction and then to try and at least honor that format as best you can. I think another thing to being an effective board, if you have a question that you want to take off cycle, you have to check yourself to some degree and be like, is this useful to this discussion and what we need to get out of it. Or can I simply say “I’d love to follow up after?” So, I think board members understanding their own capacity.

Number three, I think effective boards give their CEOs regular feedback. I never see this happen. Ever. Founders never get a review. Your board loves you until they don’t. You never know what they think of you, by the way, a board should be doing a 360 for you because none of your direct reports are ever going to tell you due to your face, what you do well and what you do poorly. So I think that generally speaking, boards are very poor at doing any kind of review. But if you want to be an effective board member, one of your jobs is to understand, from a holistic perspective, not just what you see in the boardroom, how is the CEO doing? What are they great at? What are they not? Everybody’s not great at everything and how do you give them feedback? But you have to lead a process that does that.

And I see very few boards that commit to it. Now I see very few founders that know to ask or quite frankly some don’t want it. And I’m like, okay, well, if you want to be the person who’s surprised by what somebody has to say about you, including your board, who you fear secretly might fire you one day. Well, that’s a pretty stupid risk to take coming back to the world of risk-taking. The smartest risk is to understand how you’re doing, demystify that, stop worrying about what somebody could say about you in the future. Understand what they’re saying about you now and and be in a conversation with your board about how to be a better board member.

By the way, nobody in your board has offered to give you a review, go ask them. I remember when I was the CEO JOYUS at Series B, I said to Michael Dearing and my independent, I was like, “well, you guys I’d like a review.” And they’re like, “what?” I’m like, “yeah”. “Go ahead, go do a 360 with my team”. “I expect you to give me a review.” I’m not interested in being in the dark. And I’m also not interested in having some mystery around what I’m doing well or poorly, but I tasked my board for it.

Amit Somani 31:05

Great. So as we come towards sort of the end of the podcast here, I want to sort of bring it together. So there are two very interesting kind of metaphors that I found in the book. One was, how do you get ready to make bigger leaps? And there’s this notion of headwinds and tailwinds. And then I think you have the metaphor around subways and coconuts. I think it’ll be very intriguing to talk a little bit about that. And the other one was the gut-data-gut principle because there’s a lot of decision-making that happens with very incomplete amount of data or ambiguity in the situation. So, I’d love for you to talk about both of those and really from the point of view of bringing this together in terms of how do you choose possibility for the bigger leap?

Sukhinder Singh Cassidy 31:45

Yeah, sure. So, in the book I talk about Gut, Data, Gut, which is people are always like, how do I make a decision? Do I listen to my gut? Or do I listen to my data? I’m like, you want to be in just a cycle. So often, particularly when we have more experience, we’re not necessarily old, but maybe have a few experiences under our belt. We might be leaning into something and say, “my gut is telling me, this is an intriguing area.” And then, you guys know this, your gut maybe tell you this might be an intriguing feature. And then you want to go off and do focus groups, and do A/B testing, and do landing page testing and optimization. That’s all makes sense. But then you may come back and the data may be telling you one thing yet, something in you was feeling uncomfortable and has a sense that it belies the data.

I always say to people, okay, well then the way to honor your gut is to try and look for… you typically, gut is some subconscious pattern recognition that is going on. When I have a gut that somebody may not be a great hire, despite the fact that they’d done great in an interview panel and everybody thinks they’re wonderful. It’s because, if I just push hard enough, I can maybe identify the thing that’s giving me pause about them, that may relate to something I’ve seen before. So, often our gut is a way of honoring intuition, but even intuition is… It may be pattern recognition. So, I will say to people, don’t avoid your gut, but you want to be in a dynamic between your gut and the data.

And let’s say the data offers something and you want to go a different way because of your gut, it’s fine to say, “I’m going to take a risk and do something different than what the data’s saying.” Acknowledge it’s a risk, acknowledge you’re honoring your gut. At least that gives you the freedom to come back. Right. And say, I was wrong. I was right. My mind changed. I mean, all of those things are possible. So I don’t think it’s one or the other, it’s one and the other.

And then I think with regard to this other question of subways and coconuts, what I say to people is, I am no longer president of StubHub because we sold the company right before COVID for 4 billion. And then unfortunately, I’ll come to the coconut event in a moment. I was still holding the reigns of the company when we went from over a billion dollars a quarter in GMV, to virtually zero during COVID over the span of 10 days. But for the two years I was running StubHub for eBay. I came in, it was a division of eBay, independent subsidiary, and I was running it. I spent all of my time trying to teach a team that was once a startup to remember how to be entrepreneurial again. I was trying to teach agility. I was like, yeah guys, less time and planning, simpler OKRs. We’re going to take some set of resources and incubate it. If we want to fund growth, we’ve got to fund it ourselves because eBay’s not giving me more money. I’ve got to cut costs here in order to be.

So, I was trying to re-stimulate growth and agile thinking. And it was pretty hard. I mean, I love the team, but it was like, they would’ve been indoctrinated inside of the eBay culture for a long time and then COVID happened. And inside of a week I saw people be far more agile. I saw 2000 people get into motion and make new and scary choices. The choice to change our customer policy call on the fly. Otherwise, we could have gone bankrupt. All of these things, the decision on who we were going to cut and how quickly, we furloughed within two weeks. I mean, that process would have taken us three months of debating the who and the whatever. And then what we call a coconut event happens. And you say, “what are subways and coconuts?” In the book, we talk about things that have known volatility. The subway may arrive at 7:08 or it may arrive at 7:15. There’s known volatility. You can plan for that kind of risk. A coconut is an event you can never plan for, something drops out of the sky, hits your head, kills you. A coconut. Literally.

And they happen far more often than we think. So COVID was a coconut. And I would just say, what we’ve all learned in this moment about our own agility and the agility of our teams is ironically, they will take more risks to avoid harm, then they will take little risks for upside. So, what I say to people is, remember COVID has taught you something about your agility in the worst of situations to avoid harm, you literally took risks. So, let’s remember that agility because it should put in perspective for you the little opportunities to take risks every day that you bite your tongue on. That quite frankly have only the upside in and are often two way doors, where you can figure out what you do next, if it doesn’t work. And let’s use this as a teaching moment, because we all just found our own agility and the biggest coconut of all time. As CEOs, as family members, as mothers, as fathers, as friends, I mean in every way imaginable. People learn their own capacity to pivot.

Amit Somani 36:05

Yeah. I think that Daniel Kanheman talks about this a lot in this book, right. Which is that, we tend to have a lot of loss aversion. So, we have much more agile than we think, because we’re trying to avoid loss as opposed to the level of risk you need to take to get upside, to get a big leap. One last question from me, Sukhinder here. What did you learn about yourself and the process of writing a lovely book, such as this, right? Because it’s quite arduous to sit and write. The process of becoming a published author in a different way than what’s in the book, right. Actually writing a lovely book.

Sukhinder Singh Cassidy 36:45

Right. Thank you. Well, first of all, thank the Lord I’m somebody who, I guess believes in a framework for risk taking, because writing a book is a risk, right? You write it, by the way, it’s a fairly opaque. And if you go with a traditional publisher, traditional process, there’s no data. You’re talking about the absence of data, nobody wants you showing the book to anyone, there’s no A/B testing. I could put out a survey on risk-taking and I did, but no one’s going to tell you whether your book… It’s like a consumer product that has literally very limited amounts of data you’re allowed to bring to the table, when you were kind of manufacturing the product and you want response. So, I would say it is a risk, but to your point, it’s a risk worth taking in order to have upside, an impact.

So, I wrote the book because I wanted to take a risk of impact. I’ve largely in my career focused on trying to take risks that create impact for others and for me, but starting with others, I don’t really know a world where you can be successful, where your only impact is yourself. And then probably leads to one of the surprising things in the book. I really did not want to write anything that even looks like a memoir because a memoir to me means you have some life that’s so extraordinary it’s worth celebrating. I don’t think my life is so extraordinary, it’s worth celebrating. I think I wanted to use examples from my life to demystify what many people from the outside-in is presumed as some perfect career, in order to sort of just help the ideas and principles become accessible to everyone, because I think they are.

I would say that maybe, what I learned writing the book is I was very uncomfortable, I didn’t want to write a memoir. Yet, the book flows most easily. It was most difficult to write a book that was all principles because it’s a rather dry book. And so I was going to go principal first, my story second. And interestingly, I struggled for over a month to just get that flow. And the minute that I pivoted and sort of accepted that I was going to write the book as an arc of my own risk-taking learnings. And the book is roughly divided, as you know, to get going, get smarter, get rewarded. The minute I reversed it and said, okay, just let go of this idea, forget whether people think it’s a memoir or not, you’re trying to congratulate yourself or not. Just accept that maybe the best way to tell the stories is through the lens of your own career. And you can still put in the frameworks, the book then flows very easily.

And so, it’s like anything, right? When we make it personal, you make yourself far more vulnerable, but in some ways then it sort of poured out. And so, while it is arduous, it was a lot easier to write the book. When I just went back into my own emotions and what I was going through at that time, than trying to write it from let’s say a storied place where I was like, well, here’s the big idea and the big lesson and then let me tuck my story underneath it. It sounds like a far more academic book and perhaps it is. Everybody wants to be a Thought Leader, but in some ways the more personal the book, the more the frameworks could flow. So, that was a surprise to me.

Amit Somani 39:30

Absolutely. Thank you so much Sukhinder. It’s been a delight to have you and I not only enjoyed the book, but our conversation as well. So thank you for being on the Prime Venture Partners Podcast.

Sukhinder Singh Cassidy 39:45

Thanks for having me.

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