Alisa Cohn Startup & CEO Coach chats with Amit Somani, Managing Partner Prime Venture Partners.

Alisa Cohn has been coaching startup founders to grow into world-class CEOs for nearly 20 years. She is the author of From Start-Up to Grown-Up. A onetime startup CFO, strategy consultant, and current angel investor and advisor, she was named the number one “Global Guru” of startups in 2021, and has worked with startup companies such as Venmo, Etsy, DraftKings, The Wirecutter, Mack Weldon, and Tory Burch. She has also coached CEOs and C-Suite executives at enterprise clients such as Dell, Hitachi, Sony, IBM, Google, Microsoft, Bloomberg, The New York Times, and Calvin Klein.

Listen to the podcast to learn about

01:30 - Self-Evaluating as a Founder

05:00 - Blind Spots & 360 Degree Feedback

13:40 - When do You Need a Coach

19:40 - Imposter Syndrome & Journaling

27:00 - How to Use Positive feedback & Radical Candor

33:00 - Practicing self-care as a Founder

Read the complete transcript below

Amit Somani 01:38

Welcome to the Prime Venture Partners Podcast. Today I am delighted to have with us a very special guest as we come towards the end of 2021, Alisa Cohn, she’s been rated as one of the top startup coaches in the world, actually, number one. She is also an author. She’s recently published a book, which we’ll talk about from startup to grown up. And she has mentored and coached so many startup CEOs, founders, all the way to, CEOs of large publicly traded companies, and even some larger fortune 500 type companies. So welcome to the show, Alisa.

Alisa Cohn 02:13

Thanks, Amit. It’s so wonderful to be here with you.

Amit Somani 02:16

Yes, thanks. Thanks so much for taking the time, I’ve skimmed through your book, I can’t say I’ve read all of it. But it is just really a fascinating kind of read. And I’ll pick one thing right away from the book, a little excerpt, which is fascinating, which, as one CEO once told you, it’s eerie how the company looks more and more like me. Sometimes I have trouble delivering difficult news. And sometimes I’m indecisive. And then I watch people in the company having difficulty doing both of those things, meaning delivering difficult news and being indecisive. So if you haven’t done any self reflection, the company is going to look like you. So maybe we can use that as a segue to getting started about how you as a founder, just come to terms of how you are doing and how you need to do better?

Alisa Cohn 03:06

Yeah, it’s, thank you for bringing that up. I’m sort of smiling because I’m like, yes, it’s so true, it is so true. The thing is that no matter what you as an entrepreneur, and really, as any leader, you’re not always aware of how much the company and everyone around you mimics you and knows what you’re doing. When you’re the founder of an early stage company. In particular, it’s you and your co-founder, it’s you and eight people, maybe you’ve already known them from, college or whatnot, or from other experiences. But over time, when you’re successful, you turn to 20 people, 50 people, 100 people and 1000 people, and those little things that you’re not aware of the quirks that make up you, your personality, mirror themselves, they get kind of copied throughout the company, and then all the things that you’re great at, and all the ways that you’re amazing, are copied and all the issues that you have, and all the little quirks and difficulties that you have as a personality, they also get copied.

So the best thing anyone can do is to step back and do that self reflection to really see what I want to put out there, and to be the master of yourself to put out the right personality behaviors, so that people will copy the right behaviors.

Amit Somani 04:22

Absolutely. And sometimes they may even be blind spots. So you’re not even aware that you’re doing that, one of the first times I became a “senior manager” or a manager of managers, some one of my bosses told me that, once you’re in a leadership position, and this is even more pronounced for a startup founder, even a little whisper, becomes a loud scream, because you might have just said something in passing. So how do you figure out what image you are projecting? Or what values are you projecting? Any thoughts on that?

Alisa Cohn 04:50

Yes, actually, I’ll give you a little story. That’s also in my book, there’s a CEO I work with. And after that they had a holiday party, at a restaurant down the street. And afterwards, she said, kind of by the by Oh, that was so convenient, any more convenient would have been in the parking lot. And then little did she know, the next summer, people said, Do you want a tent in the parking lot for the holiday party? And she said, What? What are you talking about? Well, they took it as like, that was a mandate from her, a directive to move the holiday party to the parking lot. When you’re the leader, to your point of senior leaders, certainly a CEO. Your suggestions are orders, your whispers are orders, your brainstorms and your thought process are orders. And by the way, also your orders or orders.

So the truth is that that is happening around you. And the way to uproot your blind spots really, is to get feedback from others. So I do, of course, a 360 feedback process for my clients to help them see their blind spots. And also, if you don’t have a coach, you can also ask people around you, what are some of the things that I’m not seeing? And if you can really convince them that you’re interested and listen to what they have to say and not get defensive, you will quickly unearth your own blind spots.

Amit Somani 06:10

Yeah, I’d like to dig into both of those. Well, I think those are both fantastic tools and systems as they were. So the 360, How do you run an effective 360? In fact, I think it’s probably one of the most underutilized tools in all of corporate life, and certainly in startups, because you’re like, oh, that’s for the corporate people, We know what’s going on.

Alisa Cohn 06:32

Totally. I mean, the other thing in the corporate world that can often be used as a weapon. And so then it gets a bad name, like I did a 360. And then I didn’t get a raise, or didn’t get promoted or whatever, that’s not very good. So when I think about 360, I think about this, you are the expert on your intention. Everybody around you is the expert on your impact, leadership growth, and effective leadership has to do with you marrying intention with impact. And the way to get at that is to talk to the experts, who are the consumers of your leadership, who are the folks who are impacted by your leadership, the people around you.

And if you ask them, usually, as a coach, I ask them, What do you think? What are this person’s strongest strengths? What are their development opportunities, weaknesses, obstacles and blind spots? How do they influence what environments bring out their best and their worst? And ultimately, what specific behavioral suggestions do you have for this person to help them be a better leader, a better CEO. And so if you get a lot of people weighing in on that, believe me, you’re going to get a roadmap for yourself about some areas that you could make some changes in.

Amit Somani 06:45

I love that, marrying intention to impact and then asking your customers or your stakeholders as they were, about how you’re doing. Why do you think is it so underutilized in the startup world, number one, the 360, in general? And then secondly I love the point you made, and I’d like you to expand on that, what are the behavioral insights or suggestions that you would recommend, as opposed to what are they good at? What could they do better in which is fairly typical?

Alisa Cohn 07:10

Well, the first question is, I think that these things are 360 and other tools are not always implemented. Number one, because we’re all busy, busy building the business, busy putting out fires, hard to take the time. Number two, I think, especially first time founders don’t understand how important it is for them to get on top of their own self development for them to understand how they’re coming across, and how much their leadership is so important to the stewardship of the business. So I think his lack of time and lack of understanding of the emphasis on it.

But I’ll tell you one great example that came out of 360 feedback that I think will answer your second question. I worked with this founder, his name was Lou and Lou’s fantastic, evolved and charismatic and caring and all these things. So I asked the folks around him what his development opportunities are, strengths and building opportunities. And one person said, He’s arrogant. I was like arrogant? I didn’t say this. But I thought, Wait, this is the nicest guy in the world, like, wow, what is it you’re seeing? So I did not say that I’m a coach. So I said, Oh, tell me more. What do you mean, arrogant? And she said, Well, he’s just so arrogant all the time. When he calls us into meetings, or whatever, you got to really probe Okay, tell me what behavior specifically he does. That makes you say he’s arrogant. And she said, he interrupts me all the time. Ah, he’s an interrupter.

So I go back to Lou. And I say, hey, somebody here said, You were arrogant. I’m not arrogant. I know. But somebody said that you interrupt people. I don’t interrupt people. And we talked, we talked for another minute. And within 20 seconds, yeah, he interrupted me three times. And I had never noticed it, by the way, because that’s another important distinction here. I’m the coach, my job is to get you to talk. If you interrupt me, that’s good. But if you interrupt your people, that’s bad. So he needed to really work on the behavioral element of interrupting, which was being read by other people as arrogant.

Amit Somani 10:20

Great. Let me jump to a slightly different topic. As you coach so many people and startup founders to later stage CEOs, what are some of your favorite questions you ask? And I know, it will depend on the context and what you’re coaching them for. But are there a working set of questions that you normally get into with them?

Alisa Cohn 10:55

Well that’s such a good question. Um, I work with one client, and I have now kind of trained them that I’m not going to answer the question initially, as in Alisa, what do you what should we do? And they know and they may make fun of me and mimic me that I’m going to say, what do you think you should do? And that’s not to be a jerk. And that’s also not to minimize my own expertise. Having been a coach for 20 years, I’ve seen a lot of things. But people instinctively go to, oh, I don’t know what to do. And so one of my favorite questions is, what would you do if you didn’t know what to do. Because people require you to pause and to really think, because at the end of the day, this is true for all founders and surely for all leaders, and really all people, if I weren’t here, you would do something. And you might ignore it. Okay, fine. If I weren’t here, what would you do? You might ignore it. Okay. But it’s very helpful.

I think that to your point about questions, questions are very powerful. Other questions I have are, what does success look like? What would be so problematic if you failed? What’s the worst case scenario here? What’s keeping you in the way? What’s in your way of what’s keeping you from taking action? Also, one question I really like is, what are you pretending not to know? Like, if someone’s dealing with a pattern of behavior over and over again, thinking it’s going to change, It’s not going to change. I’m like, wondering, what are you pretending not to know?

Amit Somani 12:20

I just love that last question. And I also know you sort of work with board members. And you also have got a chapter in the book on how to run effective boards, what are sometimes the board’s role in helping the CEO and the founding team grow. And what is it that the board pretends to not know, but they know.

Alisa Cohn 12:45

I love that, that is so true. I mean, we could run a whole other book on boards, there are some super functional boards, and who will work well together and do a great job for the entrepreneur. And there are some venture investors, and board members who I know personally, who are fantastic and so helpful to the CEOs I work with and the founders I work with. And then there’s everybody else. And I think that it’s a good question, what are board members pretending not to know sometimes? I have this part in the book where I talk about one board member who is like the general fighting the last war. And I regularly think that, somebody will come in with something that happened yesterday or two weeks ago with one of their other companies, and either went well, or went badly. And they’re taking that baggage and very vehemently, throwing it on to this founder. That’s like a very different experience.

So as a founder, your job is to figure out how to slice and dice the advice you’re getting. Sometimes good and sometimes should be ignored. And the other thing I would say is one example of that is I worked with a set of co founders, and they were inexperienced. And their investor, the VC who was on their board was pretty inexperienced, and he would make them go on fact finding missions, they were doing frontier technology, and he wanted them to have the predictable canes to the business, they were going fact finding missions all the time. And it was such a waste of time. And frankly, money, because then if they had to go off and do all these other things, and get other outside consultants, it was really not the right thing for the right stage.

So I think, as founders, and certainly, as any CEO, I know you know this, but recognize, you’re really the one who knows what’s going on around here, you’re really the one who’s running this business. People can give you advice, but they don’t really know what’s going on inside your company. So your job is to kind of separate out what’s valuable and what’s not valuable.

Amit Somani 14:55

Great. So let me ask a specific question. When does the founder or set of founders know that they are ready for coaching? And likewise, with the board, sometimes you as the board member observe, or the board observes that? Look, they’re doing great, the metrics are fine, but the company is scaling quite fast. And maybe they’re not going to cut it in certain ways, or they need to uplevel themselves. So when is a good time to get that going? And when do you become self aware that hey, I want it because you obviously can’t, shove it down somebody’s throat or you read the great book from Alisa or a book about Bill Campbell. And you’re like, Oh, now I want to get a coach, because it seems like that’s the thing to do.

Alisa Cohn 15:30

Well, that does happen. Actually. It definitely happens. Listen, my book is called from startup to grown up. And it’s divided into three sections, managing you, managing them and managing the company. And at some point, early or late, something’s going to happen. That’s going to be problematic. Whether it’s like, oh, we’re missing our numbers, we can’t hit our forecasts. We don’t know we don’t understand kind of where the state of the project says it’s managing the company. That’s a real problem. Maybe you need to have a coach to kind of help you sort out what is the problem in the way you’re running the company that’s giving rise to that issue. or managing them. You always have people problems. Most founders I work with, at some point, have a lot of trouble giving productive, difficult feedback. I I don’t mean saying you suck. Sometimes the founders I work with can be overly aggressive. I don’t suggest that you ever say that.

However, you want to be productive and helpful in trying to get this person to change. And people have a lot of trouble delivering difficult messages, or figuring out how to manage their team. So they go in the right direction, that’s a good moment to get a coach. And then certainly, if you’re having imposter syndrome, if you don’t know how to handle the ups and downs, you kind of realize your style isn’t working, you want to grow as a leader, that’s also a great time to, to hire a coach to look for a coach. And I guess I would, the last thing I would say is that some founders come to me and say, I’m a first time founder. I don’t know what I don’t know. And I recognise it’s gonna be helpful to have partnership on this journey.

Amit Somani 17:10

Absolutely great. Maybe you talk a little bit about imposter syndrome. I think all of us have it at some level. But nonetheless, in the context of founders, because you’ve dealt with so many different scales, does it eventually go away? Or does it not? And if you haven’t, any tips and tricks to kind of deal with it?

Alisa Cohn 17:25

I talked to an extremely successful founder who grew a big company and now became an investor. And he said, I used to have imposter syndrome. And now I have worse imposter syndrome, because the stakes are higher. And so imposter syndrome doesn’t go away. I would say famously, Serena Williams has imposter syndrome, many famous people, and accomplished people have imposter syndrome.

So then what do you do about it? That’s the question, my best tool for everybody is to create a highlight reel. And a highlight reel is for you to actually physically write down your past accomplishments, your past successes, to remind you of your capabilities. And when you have that as a document, like seriously a document you can read every day, you can read before you do hard things, it gives you a fighting chance to remind yourself of your capabilities and your capacity, even in the face of severe self doubt, or imposter syndrome.

Amit Somani 18:25

That’s a wonderful tool, I always was reminding me of journaling, which is one of the things you talk about, and maybe sort of I’m going a little bit all over, but I’m loving the conversation here. Are there things you can recommend journaling for in terms of just the business and getting better, as a leader, as a CEO, as a founder and so forth?

Alisa Cohn 18:50

Yeah, journaling is really, really effective. First of all, journaling helps you get out of your own head and write down your thoughts. So very often we get almost paralysed by all the concerns, and all the doubts and all the contexts and all the things going on, when you write them down in a journal to sort of share your feelings to yourself and to give rise to them, they become more easy to manage, they become less kind of hidden secrets, and all jumbled up in your head and they become on the paper. So it helps you unpack them. The other thing is that it’s helpful for you to journal on the things, which are, patterns, like, oh, this always happens to me every day at three o’clock, maybe I should eat lunch, Or there always happens when I deal with this particular person.

I once worked with an entrepreneur founder, and he had a lot of issues with his CTO, and he kept telling me it was okay, it’s okay. This guy would be disruptive. This guy would, he would be constantly pushing him to make changes or whatever. And I kept saying, I think you should have a conversation. No, no, it’s okay. It’s okay. And then at some point, the CEO said to me, ask the leadership team, I stopped talking to the leadership team, I was like, What do you mean you stopped talking to the leadership team? What are you talking about? He said, we don’t have time . I said, I don’t think that’s really the right answer. He said, I can no longer stand being in the room with the CTO. Now that is significant. That’s important. So what that really means is you kind of journal and tell yourself the truth, it helps you tell yourself the truth, then you can make productive choices in the face of that truth.

Amit Somani 20:30

Yes, fascinating. Let me switch gears. There’s a lovely quote, it’s not from your book, but one that I’ve always sort of enjoyed, so it says, When the rate of pace of change outside is greater than the rate of pace of change inside, whether it’s in your company or yourself, something’s gotta give, So you need to sort of keep pace. And while many founders go on to be great CEOs of even large publicly traded companies and so forth, many others say, hey, look, this is not for me. I mean, famously, Reid Hoffman went and found somebody else. And there’s so many examples, Larry and Sergey. I worked at Google for many years, found Eric Schmidt and so forth.

So when is the right time to know both for one founder, as well as sometimes it’s awkward that if it’s like two or 3 person founding team, maybe one person is scaling but two others are not or two are scaling but one isn’t. So when is the right time, how do you do that assessment? How do you know that it’s not just a skill gap? But like, you really need to get some other people here going forward?

Alisa Cohn 21:30

I know there’s a very deep question, I love your quote, there’s a few things here. I’m going to address the topic just of the founders, because it is a thing that happens, where you’ve got a couple of, two or more co-founders. Usually it’s the CEO who is scaling, well that’s not always true. And the other co-founder may not be scaling. And I think it starts with the right co-founder relationship, where actually you talk about those things in advance . In my book, from startup to grown up, I have what’s called the co founder prenup that I decided is a thing. And what I asked co founders to do, no matter where they are, in their journey as co founders, is actually to ask themselves these questions, how do we handle conflict? What are our values? How do we see this business, and also what’s going to happen if one of us is not scaling.

So just being able to give rise to those conversations in advance, and throughout their journey together, that’s super helpful. But it also requires both co founders to build their communication skills and build a relationship. So when the going gets tough, they can have difficult conversations with each other, that is super critical. And then you can really have an honest conversation about what it is to not be scaling. By the way, there is no shame in that. It really is about like, maybe this isn’t, maybe we all have our basket of strengths and skills. So there’s one co-founder who I know who moved away from being so called, again, CTO, back to programmer, it was like, that’s what I always wanted to do. That’s why we’re always great at it, and there’s nothing wrong with that.

Now, when the CEO, either decides, to your point about Reid Hoffman, that they want to step away and then find the right new CEO, that’s fantastic. The issue is when the board or others, even the employees, and executives need something more for him or her, and they’re not delivering it. That is very painful. And I think it takes a lot of nuanced discussions with trusted advisors, to bring them along to the fact that they can be super successful without having to still be the CEO.

Amit Somani 23:50

Absolutely, it does take a lot of emotional maturity, and it is obviously your baby, and you have built it to this point. So it’s gonna be very, very hard to think about that, but it might be for the greater good, because the company could go on and do amazing things. Yeah, let’s talk a little bit about not just the founders, but building the organization. And what it takes to build a great organization, I’ll read a, I think a quote, or, an excerpt from the book, it says, at some point, you’re going to have to create a structure to get all these folks to work together.

So in this interesting, kind of mnemonics, like sports, tribes, guilds from Spotify, and pods from HubSpot, and so forth. And obviously, founders are very reticent. And especially the kind of founders, we deal with the early stage where you’re going from zero to one, one to ten, ten to maybe hundred. You’re like, no, no we just like, we all hang together. And everybody interviews everybody. And this is like one nice, happy family. And you’re like, No, that’s not gonna scale after maybe even 50 people or so. What do you think about just designing the org, building the org? Any thoughts on that?

Alisa Cohn 24:00

Yeah, I think it’s really important for you as the founder, CEO to realize at some point, you’re going to have to scale whatever you want to. You can experiment with decentralized leadership, you’re going to experiment with the holacracy matrix, whatever you want to do. And it’s super important for you to recognise it at some point, you can’t have all 50 people in the room making decisions. So getting your mind around that early is super important.

The second is that I think this is where the unsung hero comes in of management, you need to bring managers and employees want a home, they want to feel cared for, they want to feel seen, they want to feel understood, and that the person that does that is not necessarily you as you get to be bigger, not even, “the company”, it is the manager. So bringing in strong managers, training your managers, investing in your managers, helps any kind of structure you want to create, because it helps employees understand what’s going on and feel they have a communication channel to deliver feedback and ultimately, to feel seen and valued for the contribution.

Amit Somani 26:00

Yes, and one of the things that comes with that it’s a very interesting point that you make about management being unsung heroes, especially in a startup or more new age, company context, also you need to know how to let go and how to delegate effectively. I think a lot of founders struggle with that because they’re so good and so passionate about what they do. And of course, you talk a lot about this and I know you coach on this as well. So any thoughts on how to delegate effectively as you’re building the management team and the leadership team and the company.

Alisa Cohn 26:30

Yeah, it’s very difficult, it’s certainly difficult for the founders to delegate away their baby, they could delegate the stuff they don’t like. But delegating their baby is actually very difficult. Maybe it’s the product. Maybe it’s even, if they’re financially oriented to finances, but at some point, you’re going to have to delegate. So when I think about this, I think about it in sort of a few steps. Number one, recognize you have to delegate. Number two, make a list of all the things that you could delegate and figure out who you’re going to give them to. Number three, really assess that person, the person you’re going to give the task to, are they going to be great at this? Do they know how to do it? Or are they kind of new at it, that’s going to help you determine how much context you need to give them and how much supervision. I think a lot of managers will say, I’m not a micromanager, but if you’re giving something to a junior person, you’ve got to check in and supervise quite closely. It’s not about you, it’s about them and what they need.

And then the last step, I would say is that people forget to really acknowledge what does done look like, let’s look at each other and agree when this is complete, we’ll both know it, because it will be done. And done means this, this, this rare descriptor of what done is, and done includes a deadline. Just recently, someone said to me, this CEO said to me, ah, I didn’t get the thing. And I keep asking for it. And I haven’t gotten it. I said, Well, did you give her a deadline? And he said no. Like she should have just known people don’t know, people do not know, give a deadline. And then you can have something to grade against, like, well, hang on, I’ll give it something you didn’t make the deadline. That’s a conversation to have,this feeling of like, I thought you’re gonna get it to me. That’s a very difficult conversation to have.

Amit Somani 27:15

Yes, indeed, also, from this very cute quote/excerpt from the book, which says, there are many ways to motivate people but there’s one very trivial way to let you say it, that requires no special equipment, doesn’t cost anything and people don’t do it. Do you want to talk about what that secret weapon is?

Alisa Cohn 28:40

Yes, that is praise. That is positive feedback. People do not do that enough. And I do not know why. And I think it’s uncomfortable because people feel like it’s like, first of all, if you weren’t, if you didn’t grow up in a house, which gave a lot of praise. And if you didn’t grow up in a work environment, give a lot of praise, I get that you’re uncomfortable doing it. Also, it’s this feeling of it’s like the workplace version of I love you. And that’s uncomfortable for a lot of people who aren’t used to it. But what happens is if you don’t praise your employees proactively, you are the founder, and you’re very self motivated. You don’t need praise.

In fact, you’re not getting any praise, you’re getting a lot of headwinds, as we say, because you’re trying to do something that’s very difficult. Your employees are not founders, how do I know that because they’re working for you. So they need a different set of motivators, then you have and the problem in a startup is that you work long hours, it’s really hard. It’s an extreme work environment, you don’t always know if you’re making progress, you don’t always see the impact of your work. And meanwhile, people are definitely coming and telling you what you’re doing wrong. That’s definitely happening.

So the way to counteract all that is to actively proactively put into your day and week and month, times where you praise your employees and create a culture where your managers also praise their employees so that you have a fighting chance to counteract all the difficulty that comes with being a startup.

Amit Somani 30:00

So I completely agree with you. I couldn’t agree with you more. That feeling like hey, look, if that’s all we do, how do we do so called Radical candor. How do we give them more critical feedback? That’s not all fine and dandy and everything is great.

Alisa Cohn 30:15

I think that’s a great question. But the problem is that when you just give this so-called Radical candor, which I have something to say about, then you then you don’t, people aren’t happy. It’s like people sort of right weaponize this idea of radical candor. In terms of like, well, I had to tell him that he was a jerk or whatever. So first of all, radical candor is a fantastic book. It’s by Kim Scott, and everyone should go out and buy it for sure. And she has a grid about the way to think about so-called candor. And the truth is that her first step, and the first step with any kind of feedback you want to give or relationship you want to build, is to build that relationship, to care about this person to give the positive feedback to showcase what they’re doing well, then, and only then, have you earned the right to also help them grow their career and develop their career by giving them the more difficult the more constructive feedback, because otherwise, by the way on the other side of that, when I did, I worked with them.

A CFO when I had this conversation with him, he was averse to giving feedback to his employee, because, oh she’s gonna cry, and it’s gonna be upsetting and she’s not gonna want to hear it. So to me, what I said to him was, you’re being very stingy, because you see ways that she can improve and needs to improve. And could be more successful. And you’re not giving her that feedback, because you’re uncomfortable. So the asset and by the way, he did go give her the feedback. And she did cry. And she did get upset. And the next day, she came to him and said, I know that was hard feedback to give, thank you for giving me that feedback. I wish someone would have given me that feedback 15 years ago.

So she’s been running around for 15 years, wishing that she could be more successful. And so nobody was ever generous enough to give her that feedback. So that’s the way I see all the topics of feedback. But step one is to build a relationship, and make sure that people know what they’re doing right. And then make sure they understand that when you give them critical feedback, it is to help them get better, not make them feel bad.

Amit Somani 32:30

Absolutely. And I also love the point about defining what is done means and what are the constraints or the guardrails or timelines around it, and not just like judge other people by their actions, and myself by my intent. So that kind of thing. I just want to quickly crowdsource a couple of questions on Twitter and LinkedIn, and one came in that was really interesting. So it may not tie with the rest of the conversation here, but I’m going to bring it up. What are some of the best ways to keep surfacing and reminding how everybody’s job contributes to the larger purpose of the startup? And more broadly and expanded to how do you build culture more consciously and proactively?

Alisa Cohn 33:15

Right, so again, it comes back to starting with intention, to intend to build culture and to intend to have sort of an operating system inside of the company of the way we do things around here. So having that define for yourself, bring your employees into that, and then talking about it. And showcasing and rewarding those cultural elements. And overtime really comes down to communication, it’s you communicating to your executives, it’s your executives communicating to their leaders and managers, it’s leaders and managers communicating to the employee, what we expect around here, what the standard is, when to do, when more than more than ordinary is expected.

And then again, the way we do things, so the more you highlight that and communicate about that and reward for the behaviors you’re looking for, the more it’ll be comprehensive and cohesive both. I guess, I would say culture, but also operating systems of the company.

Amit Somani 34:10

Wonderful. One other question that I had in my mind is, how do you practice, self care and self love? Because it’s such a tough journey. I think you in your own podcast, which you run as well, talk about the hero’s journey. And we often tell our founders that out of 365 days, 360 days are sort of bumpy and a few days of glory if things are going well. So just like the highlights reel thing that you talked about which I love to tackle imposter syndrome, are there other things you recommend to keep mentally and emotionally healthy as you go through this really tough journey?

Alisa Cohn 34:50

Yes, so true. And you’re so right, that like most days are really awful and a few days of glory. Not only that, but as the founders will even say to me, I knew it’d be ups and downs, but I didn’t realize it’d be ups and downs, like in the same minute, like in the exact same way, close to each other. And that is the way it is. So it’s very emotional as a long term, you don’t always know if you’re making progress. And so the way I would say that is sit down and recognise, you have to pace yourself for the marathon. They call it a marathon, not a sprint, because it’s a marathon, not a sprint.

So you’ve got to make sure you pace yourself that you can find time to take some time off, and that you really make sure that it’s important, I think that people don’t do enough of basic practices, like getting enough sleep, like eating right, having the right nutrition, like working out on a regular basis to help you with stress relief, funding, other stress relief things, finding a group of people around you that can relate to what you’re talking about, like other CEOs, also having friends around you to remind you of the rest of your life. All of those tools help you stay in it for the long term.

Amit Somani 35:00

Absolutely. I think, sleep, exercise, meditation, nutrition, these are all very basic low hanging fruits that can be done. And that can reap great rewards. You write a lot, you write for the Wall Street Journal, you write for Forbes, you’ve of course got a book, from startup to grown up. What do you read? What is that you read?

Alisa Cohn 36:25

What do I read? Well, I read a lot of business books. Certainly I have a book right here called the long game by my good friend Dorie Clark. And I have read, looking right now at my bookshelf. My friend, Michael Bungay Stanier just wrote a book called “How to begin”. I was also inspired by Ben Horowitz like many people, “The hard thing about hard things”. Candidly, when I first read it, I was like, Oh, give me a break. It’s just like, so too much. However, all my founders loved it. It’s like, okay, so I read it again, actually listening to it was helpful.

And what I like about the book is that it really showcases the ups and downs and the real talk of what it means to be an entrepreneur growing into a CEO. And I thought it was a little too much sort of Ben Horowitz and my experience. And I wanted to write a book that was more broad from the point of view of showcasing a number of different experiences, because there’s a lot of ways and a lot of things you go through when you’re a founder.

Amit Somani 37:30

Absolutely. Are there other books that you recommend your founders read? Of course, I just saw the recommendation for the long game. I’ve just purchased it just before the podcast today. But are there other other books or typical ones that you recommend as people go through their sort of growth journey here?

Alisa Cohn 37:45

Yes, I think that “Radical candor” is a great book. I also think that “Crucial Conversations’’ is a great book. Certainly my mentor’s book, “What Got You Here Won’t Get You There” is a fantastic book. Also, I encourage people to read more spiritual literature, whatever practice you might have, like, you might have a Buddhist practice, or I guess I would say perspective taking about, how life really is and how, when you feel the walls coming in on you having some perspective. So there are podcasts also. I really enjoy Tara Brach’s podcast, which is a lot of Buddhist wisdom.

Amit Somani 38:30

Absolutely. Alisa, we could go on and on. But I really want to be respectful of your time, it has just been a delight speaking to you, and I hope that the founders that do tune in and listen to this podcast, it gives them some food for thought for self reflection, as they wind up the year and then get charged up for 2022. So I really appreciate you taking the time to be on the Prime Venture Partners podcast.

Alisa Cohn 38:55

Well it was my pleasure, and thank you so much for having me. I really enjoyed the conversation.

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