SPOS #798 - Alisa Cohn On Startups, Leadership And Growth

Well, hey there and welcome to episode number 798 of Six Pixels of Separation. My name is Mitch Joel. It's Sunday, October 24, 2021. Let's get on with the.

Foreign.

So who are you and what do you do?

My name is Alyssa Cohn. I'm an executive coach and the author of From Startup to Grown Up.

Hey, how are you?

Fantastic.

Yeah, we.

How are you?

I'm doing great. I. I was thinking prior to getting ready for this conversation that as this pandemic unfolded, one of the saving graces I had was yourself and Dory pull together this small little group of people to just connect. And we wound up doing this on an app that. I don't even know if this app is working or not, but it's called Marco Polo. But it was really cool. It was like short little videos and we bounce each other messages and see and be helpful to one another. And it was a great way to connect and become better buddies, you know.

Thanks for saying that. And that was also a lovely experience for me in the pandemic and just getting to know all of you better and for us to be able to have a place where we can just swap ideas and help each other, but also just be connected during this very strange period. I. And it's been great getting to know you better, Mitch.

Yeah, it's fun. It was a. It was a good hang. Like we've had hangs before, but I feel like that, you know, we got. We got into each other's dirt, we figured out each other's businesses and helped each other out. And part of that journey was you deciding to get this book together called From Startup to Grownup. You have. You don't have a necessarily unique business model in the sense of you are a coach and you sell your time for X amount of dollars. I know because you work with startups, there's also probably invest investment opportunities. But. But doing a book when you have that business model can be very disruptive. It can be really disturbing because it takes some time to write a book and to sell a book. So I'm curious how you, like, what was going on? Like, what was the decision matrix for you to say, look, I have to put a lot of hours against this book, which is going to definitely impact the business and what you're doing. So you need this greater outcome at the end. And how did you process all this?

Well, listen, I have wanted to write a book for years, and first of all, I would say in my profession, it's important to have a book And I think even more fundamentally, I always felt like I had a lot to say. And I struggled over the years, not the months, the years, to sort of categorize and structure it and think about what the topics were. And so I guess I would say a couple things, that when the pandemic hit, I did an exercise with myself that I would invite everyone to do, which is to think of myself in my future state. So this pandemic is going to end. And at the time we thought, oh, two weeks, maybe couple months. As time went by, we thought, oh, a year, maybe two years, who knows? But at some point it's going to end. And I know that I'm going to want to be proud of my accomplishments during this period. And so what do I want to be able to say? And I knew if I don't write my book during this pandemic, I'm going to be upset. So that was one piece of the puzzle I would say. And I would just say that the book was gestating inside of me for a long time because I do work with startups and I'd walk into a situation and I would sort of say, gosh, I just wish there were a guidebook for y' all to help you prevent mistakes, right? You're gonna, you're, you're going to make mistakes. We all make mistakes. And there's gonna be some issues and confusion and it's going too fast. But there's some basic things that it would be great if you just knew in advance. And I wish there were a book that could talk about that. And I realized that was my mission, to write that book.

God, that's the best. When you, when you're looking for a book to answer a question and you realize that you have to write the book is probably the sweetest of sweet spots that you want in if you're thinking about writing a book.

That's probably true. I think that's true. And then it also, it animated me. So, you know, like, it can be a little hard, as you put it, and you put a lot of time against writing a book. So it was not a straight shot, like, oh, ta da, I've got the book. It was definitely a struggle and I had to think about how to structure myself and how to structure my time, how to structure the book. But what always animated me was my sense of purpose. Like, I'm gonna be so excited to be able to finally have this hand out to people to say, listen, here's how you can think about your meetings. Listen, here's how you can think about your own transformation as you go from founder to CEO or like, here's how to think about structure or here's how to think about your board. So I was excited to be able to have it. And so that really got me through some of the tough times. And the question, there are some tough times when you're writing a book.

So. And there were tough times also, just in the world in general, in particular, at the beginning of this chaos. And I'm wondering based off of the fact that you focus, I think, solely on startups, is it solely on startups or do you. Or once they get bigger than startups, you're still with them? How does it work?

Well, both. So I work with startups and then also I work with startups which have grown up and then I also work with large public companies. I've worked with Pfizer, with Microsoft, with IBM, you know, all sorts of companies like that. So I don't just limit myself to startups. I actually think it's really helpful because when you have insight into what makes a massive company, you can really help startups think about scale. And when I think about, when I have a lot of experience with startups, I can help companies, larger companies, be more entrepreneurial, think about organizing themselves differently, maybe take some experiments that the startups I'm working with are doing. So I like the back and forth, but I guess I would say my focus, especially now with the book is on, is on startups.

So how were like what was happening? Because to me, what it felt like, and I'd love your perspective, is there was this moment of we don't know what anything's going to be about and we're going to just pause a lot of things. There was this sentiment of because of this pandemic, people are working from home, they have more time to think, they're realizing they want to go out at loan. We're going to have this massive uptick in people starting up with businesses. K recovery. Some people do exceptionally well, some people did exceptionally poorly. What was your take in terms of, I guess, your clients and who you were dealing with? Was it scary business wise? Were you suddenly inundated with demands and needs? How did it look from your purview in terms of the startup community?

Well, you know, as. As everybody knows, you know, there's sort of stages to this pandemic and I would say definitely in the first stage there was a sense of wait, are we still alive? And everybody was just managing a crisis and the crisis was both the sort of current situation, like, oh, everyone has to go work from home, we're shut things that we rely on like travel, you know, so people can't get to customers, people can't get to install things at client sites. And then also how do we now think about our own business when you think about like this unknown. So there was massive, I would say crisis management at first. You know that I wrote an article for Forbes at that period thinking about how do you plan for a future you can't plan for. Because all of the clients that I worked with, startups and, and others were, were going through that sort of, you know, I sort of think of that. I just think of that song, Head, shoulders, knees and toes. Like, okay, are we still here? Here my head, here's my shoulders. Like everyone was kind of feeling their way. Then it moved into the distinction of like, how did your business model adapt to that? So I had a number of clients who were working on in person events. It goes without saying that that was a massive disruption and some of them did not survive. But there were many that I worked with that had a business model that really worked for remote and they were more thinking about how do we navigate through the logistical problems of this because there's also supply chain problems, there's also just again, travel disruption, but how do we navigate through those to increase our ability to build our business? And you know, I worked with my clients to think about that as well. So I think there's all different stages. And I would add that a number of businesses have been started during this pandemic and I think that's also very interesting because people don't see everything as a massive problem. They definitely see this constraint and this sort of new normal, as we keep calling it, as an opportunity to rethink something or also to give them time to think, as you said, to step back and think about, well, what is a great opportunity right now for a startup.

So going back, you were originally an executive, you were CFO in your last position, correct?

Yes, that was a very long time ago. But I was, I was a CFO of a startup and then ultimately I was a GM of that same company.

So how does one become a coach? Why does one become a coach? And I think the bigger question that's always on my mind is what does a coach actually do? And I'm asking this in particular with startups, because startups are usually inundated with people who want to advise them, people who want to help them, people who maybe put in a small bit of Money. And the reason that the startup is taking that money is because of their knowledge and ability to guide them. So tell me a bit about why you decided to leave the corporate world, why you decided to become a coach, what, what you think a coach means in a world of the startup ecosystem.

Hmm. I. I became a coach because I was at. I was at a large professional services firm and I woke up one day and I just thought, this is not it. I really thought, I hope I get the flu so I don't have to go to work tomorrow. And 18 hours got rushed to the emergency room with the flu. So I kind of realized, like, hey, guess, I guess your. Your body is talking to you and you really can't ignore it. So it was a little bit of a. Not a little bit. It was a pretty depressing time in my life because I just was like flat on my back and thinking about, what am I going to do now? You know, like, washed up at 27, what am I going to do? And the only thing I could think in my mind's eye was to make a difference. For whatever reason, that phrase came to me, to make a difference, that the work of my hands mattered. And so I did a whole bunch of seeking. I've always been a seeker. And I got dragged to this conference and the conference was called Body and Soul. It was sort of a yoga type conference. And we ended up volunteering. I know, right? I know. It was not really me, but my boyfriend at the time was a yogi type. And so we volunteered at this conference. And at the end of the volunteer orientation, they said, now Shoah Richardson is going to speak to the volunteers. And I thought, can I leave? Is this mandatory? Can I leave for this? But it turned out Cheryl Richardson was this incredible coach and she was this incredible speaker. And as soon as she spoke, I thought, what's that? I want that. And it was like so clear to me that whatever she was about, I saw myself in that. And I followed her around at the conference. I saw her do live coaching, and I just thought, this is it. But I was pretty young, so that's when I entered the startup world. And I was head of strategy of one startup and I was the CFO of another startup and then ultimately the GM of the boss Boston office. Because again, I was thinking about to make a difference. I felt like, oh, inside of a startup, I'll be able to make a difference. And that's certainly true because it's such a small environment. Everything you do really matters. But ultimately that all imploded I had taken coach training, I had hired my own coach and that, you know, the startup scene as, you know, sort of imploded. And I thought, well, I'm going to become a coach now. And I put one foot in front of the other and I started coaching personally, you know, personal clients. And then I ultimately came into corporate, the corporate environment. EMC was my first sort of major corporate client. I coached there and did training there, facilitation there for about 14 years. And so that's how I built my career as a coach. And I would just say that in terms of startups, startups need all that advice. You know, you talked about the different people around them and there are plenty of investors who of course want to give their advice, some good advice, some bad advice. There are plenty of people in the ecosystem who've got a perspective. I think what as a coach, what I can do is I can help founders with that psychological journey that is so important that they have to go through as they manage their own psychology, through the ups and downs of growing a startup and then also adapt to the constantly changing and chaotic environment that they again, they have to adapt to as their startup becomes successful and ultimately grows.

And so now I'm thinking about just my world. And as you know, I used to run a marketing agency and one of the things that I like to do, I don't necessarily think it was reflected within the company is I did want to help startups build their first website, discover social mobile, whatever it might be. And on the business side, it wasn't really great. There wasn't a lot of money. They often didn't have, you know, they wouldn't. It was tough for them to even make the bills often. And we recognized early on, based off of our desire to scale, that we had to move away from those types of businesses. Unfortunately, we were good of heart, but it was difficult in terms of the pocket, and I'm wondering if that's been a struggle for you too, is finding not only the right startup but their ability to really work with you because they're pulled in, I mean, all startups are pulled in so many different directions.

You know, Mitch, first of all, I'm just going to tell you a story from when I was a young coach. Like probably my first year of coaching, I was with my friend Kim and I was telling her father, yeah, I'm going to become a coach. And I was interested at the time because, you know, I'm a cpa, I have my mba, I was very interested in making a difference for people. And part of what I was interested in is helping people buy their first home or save enough to retire, whatever it was. So I was telling my friend's father, I want to help people who get out of debt. I want to help people save enough money to like send their kids to college. And he said, if you're going to help people get out of out of debt, how are they going to pay you?

I was like, oh, exactly right, brilliant.

I didn't think of that. So I mean, in the world of startups, the truth is that these days there's a lot of focus on coaching in startups. A lot of the investors recognize the importance of having a coach. Some of the funds that I've heard about, they set aside a certain amount of the money they invest to fund coaching and professional development for founders and for executives and CEOs of startups. And also, you know, I may not be able to work just financially, it may not work out that I can work with like the youngest seed stage startup. But I'm interested in making a difference. So I'm interested in contributing to the ecosystem. And over time startups do raise enough capital to be able to fund their own coach, hire me as a coach and do other professional development. And I would say the ROI on that is incredible because it's important for the CEO to be in her own professional development space to grow rapidly to prevent avoidable mistakes. So really it's a massive investment of her time and money, but it really pays off because it helps with a much smoother ride, so to speak, and more effective leadership and management.

So let's talk about what happens on the ground floor when you get in there. Because there are so many startups, there are so many great ideas, but ideas to execution or ideas to business model is not the same thing. And often the path to genius and great ideas isn't really anything to do with that, but rather is there a market fit? What is the actual business model here? How often are you dealing with that friction of this idea that ideas aren't business models and what does that look like for you?

Well, for me. So as a coach I have to say I am not the expert on any of my clients business models and a lot of them are in very technical areas. And I'm certainly not an expert on any aspect of technology or machine learning or kind of whatever they're working on. I would also say that most of my, if I'm picturing in my mind's eye like most of my clients have had some sort of either evolution or pivot. You know, we don't say pivot as much anymore, but like evolution or pivot or some change in their business model, I think that's normal. I think that as you grow, you begin to get more smart. To your point about business model, about refining your customer base, about refining what you're doing, you're also testing and figuring out, oh, that's actually not going to work that way. We have to go back to the drawing board and think about it differently. That's part of the normal evolution of startups. My job is not to advise them on that strategy or to advise them on that business model. My job is to help the CEO and other executives navigate in a changing environment. So when you pivot, how do you communicate to everybody around you? Hey, we've made a change. How do you make sure that the employees aren't using last week's playbook as opposed to this week's playbook? How do you make sure that everybody's on board with the changes that are going on? How do you make sure that your leaders are enabled themselves to be ambassadors for the change and also probably to maybe make some fine tuning in their workforce in who they're hiring to make sure they meet the demands of the new situation. That's what I do as a coach. I partner with the executives and with the founders and the CEO to help them organize that part of the business.

So do you find yourself being more of a third party to their business versus a telling them how they should operate? Because again, the other side of it is you're dealing with people who are obviously very intelligent, they're very driven, they have a vision. Those can sometimes be, I wouldn't say difficult to coach, but they may have a feeling of this is my path. What value do you bring? So you have to come in and say, well, I'm not just going to be like another shoulder for you. You're bringing in much more tangible things. So do you see yourself more as a third party partner to them? Are they often giving you great advice? Real kind of co coaching a little bit here.

Wouldn't that be great? Listen, I learned a lot from my clients. I learned a lot from my clients. From sure. For sure. I don't come in and weigh in on the business model. I, I might, let's say I might have a little point of view, but ultimately they're the experts on their business. If you think about when I meet, I'm just picturing some founders that I met kind of four years into their journey they spent two years thinking through what are they trying to do and researching. They are well deeper in the space than I will ever be. So that's not the role that I take on. And when I think about advice, the advice I do give, just coming back to my book, From Startup to Grown up, is here's the kind of meetings you need to have, here's what you should expect in your journey. As in, like, here are the difficult kinds of moments you're going to face, here's why self awareness is so important, here's how you think about hiring, right? So that is consistent in all kinds of companies. For me, I think the value I add often is, I wouldn't say shoulder to cry on, but I would say sounding board for sure. And also helping them get their sort of behaviors in the right way to make sure that they are speaking and communicating differently from 30 people to 100 people, to make sure that they're thinking about how they're managing their leadership team, to make sure that they're thinking about structure of the company before they really need to, like, before it's too late to think about how to manage their board. You know, relationships with co founders, which are a massive problem. Like when co founders have tension, that is one massive warning sign that this company is not going to make it. So those are the areas that I coach in. And I would say as a coach, a lot of what I do is help them take time out and reflect, recognize what they already know. As in, I know I should be having this difficult conversation with this person, or I know that I need to fire this person, or I know that I should be encouraging more systems around here, even though I myself don't like systems. So we spend the time on that and then help them act consistently with that inner voice that they have uncovered.

So one of the things I love about startups and investing and advising and speaking to founders is I feel like everything is this weird paradox. And one of the weird paradoxes that I think is really true and challenging is that it's really never been easier than ever to start a business, but at the same time it's never been harder. And again, like the whole startup world is to me is filled with these challenges. But if I threw that statement out to you that it's easier than ever to start a business and it's never been harder to start a business, I'm curious what your reactions are and how you think about the deconstructing of that.

Well, I think it's much easier to your point, because Technology enables it also, it's more of a defined career path in a way. You know, there's been a sort of a mythology mythologizing for better and for worse about founders and startups. When you say it's never been harder, I think it's never been harder for anybody to gain traction about new ideas. It's a noisy, noisy world out there. It's increasingly noisy. I think attention is increasingly, you know, sort of just taken away. People's attention is kind of just taken away from everything because they're so bombarded with inputs. So from that point of view, I think it's hard to break through. But if you really have something special and you have this sort of earned secret of what it's about, and you're able to put together an early team and an early product and then do the right execution to then grow that into a middle and then later stage team and middle and later stage product or service. I think that it's a great time to build a startup and I think that those are the areas you need to focus on. How do you gain attention in a noisy world?

So when. And you've referenced it many times and a lot of it is the table of contents for the book. And I don't want to necessarily dive into the guts of all that because people should read it. It's a great book.

No, thank you.

It's a compliment. You can take it.

Thank you. I appreciate that. That means a lot to me.

Yeah, that's true. I'm curious about how you bring structure to it. Meaning do you find that there's a resistance when somebody is doing something new or they have a different vision? I always look at entrepreneurship in particular as this place where these founders are creating either entirely new markets or they're reinventing existing markets. And it's a very simplistic way. I self declare that. I know. But when you come in and you're bringing the rigor of what happens in a corporation, is there friction to that? Is there acceptance to it? You're talking about things like dashboards and having more fixed schedules and putting things in place, is there a lot of pushback against that? And I'm also curious if you feel that maybe by implementing those things, is it in some way forcing them back into why they're trying to disrupt the industry? Like, well, no, that's what the industry's been doing. We need to disrupt all those corporate things that you're trying to bring into place here as structure.

Yeah, yeah. So I, I try not to bring the Maladies of structure. The. The bad things. So it's.

Here are your silos.

Exactly. How come we don't get more siloed? How come we don't get more political?

I think we need more meetings here.

Right, Right, right. But I guess here's what I think. I don't try to talk people into anything. Or when I do, I recognize it's sor. It's. It's futile. What I try to do is come with data. So there's two things that. Two. Two stories that come to mind when you talk about that. First is about dashboards. I came into a company, and there was a project that was due in June. It slid till Aug. It was a big. It was like, the most important project they were working on. It was slipped till August, and then we're looking at the fall. And, you know, I'm sort of scratching my head. I came in the middle of this, and I said to the CEO, you know, what's going on with this project? That's like, super late. Oh, Alyssa, you have to be patient. So I'm thinking, like, you're kidding. I never. That's my line. A CEO has never told me before, ever. You have to be patient. But I'm in the environment. So as part of what I do with CEOs, I work with, I do 360 feedback. So I ask people around the organization about the strengths and development opportunities and blind spots of this person. They're the consumers of the CEO's leadership. So that means I'm kind of around. So part of my being around is I talked to the people, and what I found out was that the head of product was waiting for a whole bunch of insight and information from engineering. I found out that engineering thought that product had already what they needed. There was also a regulatory component, and the lawyer was trying to get in touch with the regulators, and someone was out sick, and someone was out sick, and week by week, they were out sick. So this was stopped not because there was, like, a lack of patience, but because it was actually stuck without a dashboard. I brought that all to the CEO. We had a meeting to sort of talk it all out, and we got back on track, but we lost six months in the process. Without a dashboard, for example, to use your example, there's no context to look at what's going on with this project and why is it. Why is it stuck? Or what's going on with our key business metrics? And why are we up here, which is fantastic, you know, green. And then why are we continuing to lag in what we say is an important business metric that leads to results, and results lead to success. So once CEOs see that, they become big advocates of dashboards, right? They don't think like, oh, this is IBM, like, we know, how can we do a dashboard? They become advocates. Then the second thing I would say is, just like I said, I do 360 feedback, so I like to bring data to the CEO. So on the one hand, everybody thinks you're an incredible visionary. That's great. Everybody thinks that you know your stuff, you know the space, and that you don't have a political bone in your body, which means that you focus exclusively on the goals of the company. And also you care about people. That's fantastic. And also what's missing inside of you and anybody else is a way to take that vision and translate it into action, which means people are confused and you don't always communicate what you're thinking, which means people are acting across purposes regularly. So that's not me convincing you that we should work on these things. That's your people coming back to you with a message of what about you is getting in the way of the business. So those kinds of things don't need convincing because once people see it, they're like, oh, that's kind of a problem. I want to work at that. I think my experience with founders is that they really like solving problems. So would you frame it as a problem? Like, here's something that you could. Here's a problem and here's the solution. They. They jump right in.

So the other thing I've noticed in just speaking to other authors and speakers and thinkers in general is, and I'm painting a bit of a brush here, so excuse me while I do this, but there are some that really focus on the soft skills, and there's some that really focus on the hard skills. There are unicorns that can do both. And I'm starting to believe in this conversation that you are a bit of a unicorn. But I'm wondering in both the positioning of it when you're trying to get into that new startup or you're working with founders who have a perception of you. Do you think there is that perception? How do you think about hard skills versus soft skills in terms of both coaching and in terms of how startups need to think. Because within the data, there needs to be be a whole lot more on the soft skill side, in particular, if your team is small or you have a very short Runway.

Yes. Well, thank you for calling me unicorn. That's nice. That's nice to hear.

An angry, angry unicorn.

A purple unicorn. You know, there's a lot in that question. I would say that Regularly, founders, executives, CEOs, they dismiss the importance of soft skills until something bad happens. So something bad happens means one executive quits and then two executives quit and all of a sudden soft skills, quote unquote, become a real important mandate for them. It's easy to say, oh, all that matters is that people get their work done. They don't need to know the big picture until what happens is that, you know, marketing misses the ball, drops the ball because they didn't understand the bigger picture of what product actually needed and what the sales folks are actually needed. So I think there's an increasing attention being paid to the importance of soft skills. Also, everyone talks about eq, they may not know what that means, but at least they're talking about it. So I think that there's more of an appreciation for that. What I know to be true is that. But what will kill you is your inability to get people to work together, to execute. And so the way to get people to work together is to do what I call the unnatural act of leadership, which is give direct and compassionate feedback to people so that they are inspired and also they change their behavior. It's also to sometimes compliment and reassure someone who's the person who just did this massive screw up, right? That may not be natural to you, but sometimes that's what you need to do to continue to motivate people to fix the problem and then learn from it and move forward. So I think those soft skills are super important. And I guess the last thing I will say is that people do when I come into an environment before they meet me, they think like coaching is touchy feely.

Well, that's what I mean. It's like when even as an investor and someone who sat on funds, we talk privately on our calls about who within the organization needs coaching. And inevitably the follow up question is, are they coachable? And I'm always the one saying coachable for what? Like is it the soft skill thing where they'll feel this is like. Or is it that they need coaching in terms of their actual, you know, the hard skill sets, of what it means to either run the business or do whatever line they're directly involved with? And, and it's funny, most people, even at that level, senior people, often don't have an answer back for that.

Yeah, well, to your point though, really what coachability has to do with is, are they willing and able to change to meet the demands. So if that means to be more strategic or to be more of a. To be. Because that's what's needed now, that's very different from to do a better job of customer discovery. Right. Or whatever it is that, you know, sort of is the missing gap here. But I would also say this. People will say, oh, that person will never change, or that person's not coachable. I once met in a large company with a C suite executive, and I said, so, Chris, the point to you is you need the big. The big feedback to you, Chris, is you need to soften your style. And we were in person, he was a big, tall guy, and he looked down at me and said, alyssa, I have been told that I need to soften my style for 20 years. Don't you think that I would do that if I knew how? So we spent the next set of months. It took months, but it was very successful. Helping him literally get the tactics of how to soften his style. And by the end of the year, they were like, you know, people around him, to me were like, what drugs did you get, Div. Chris? What. What drugs did you give, Chris? And are you sharing? Ayahuasca had had a massive change because he finally understood the specific tools and tactics that will help him, quote, unquote, soften his style.

And so when you're thinking about that, when you're thinking about saying that to a leader, like, let's use this example, because I think it's. It's actually a Runway that we could. We could go down. When you're doing that, do you think, well, if Chris does that, in theory, it will fundamentally change the culture of the business. And I don't necessarily know the outcome of that. And again, that statement might be a good statement that if it does change the culture of the business, but it could be very detrimental. Do you think about that and, like, how do you. How do you do it? Because, again, we're not talking about businesses where there are thousands of employees and the CEO might, you know, shift through or move through another transitional role after five years. This is someone's baby, for lack of a better word. And they don't necessarily want it to be something other than how they see it.

Totally. That's a yes. Mitch. I could not say yes more emphatically. A good example for me is this, is that regularly I'll come into a situation, and it's a company with, I don't know, like, 50 people, 80 people, 100 people, something like that, that. And they'll say of the CEO and many, the HR person will say this and other people will say this too. He needs to learn to delegate more. He needs to trust his people. And I'm talking to everybody around and I think some of his people are fantastic and really are able to sort of take things and run with them. But there are some people in the organization who are really not equipped. And so if you, the CEO say I'm just going to trust them, I'm just going to trust him and let them run with it and they are not equipped, well, that's a disaster. Right? So really you've got to look situationally at your scenario and think, okay, I understand that the issue is that I'm probably too controlling. I get that. And also I recognize that there are some people I need to give more rope to. Okay, good. But what's happened here, what's happened here is I've hired people or somehow these executives or people have grown inside of the company and they're actually not equipped to be delegated to. So now that's a different question. Okay, so do we need to coach them? Do we need different people? Do they need more training? What needs to change for you to be able to do that? Delegation, as an example. And those can be painful discussions because ultimately it may be that one or two people are not up for it and then you've got to make some hard choices about those people. But I think what's very helpful is to recognize that you have to look at your situation and not just take regular management pablum. You've got to apply your own sort of insights and see what needs to change. Because when you get feedback like that, something needs to change. So I mean back to Chris and the soften his style. The impact was people felt uncomfortable coming to him and so he missed a lot of the important nuance what was going on. And also people would massage projects and not give him bad news. And so really that was detrimental to the business. Those are just some symptoms of the problem of him not being more accessible or softening his style.

So I'm working on something new, new project. We'll call it a startup. It's, it's still very stealthy and I look at my to do list and it's all really important. It's all really all over the place. It's everything from like an email copy to legal contracts. Like it's all over the place.

Right.

And I'm one who has muscle memory on this. I've done this before I have systems in place. I get it. But focus is something really, really different. When I look at the list and I go, what needs to be focused on? Or where does the focus come from? And I think it ties in good to the last topic of soft skills versus hard skills. How do you help find the focus? And how do you coach in a place where, no matter what you're saying and as much focus as you want them to have when they're working with you at the same time, they are founders, they have 16 million things going on from 16 million different parts of the business to deal with. And I know you talk about in the book, but even some tactics would be great. How do you. How do you focus on focus?

How do you focus on focus? Well, what I say is that most important thing is to keep the most important thing, the most important thing. So I hope that helps you, Mitch.

Not at all. But okay.

I think that there are some, you know, basic time. The problem is that nobody teaches you time management. Not really. And so you kind of get. Get thrown into this world to your point where you have everything, you have to do everything by yourself. And also it's at the level of like strategy and abstraction and also the level of writing this copy for this email and then also contracts like you're saying. So I think what's really helpful is to. These are kind of the basic tools. Plan your week. So recognize on Sunday or on Friday, the week before, the most important things you really want to get done in the week that comes and really focus on getting those done as much as possible early in the week or early in the day or take a big bite out of those things. So you picture that you're making progress. The truth is that you can't do everything at once. So you do have to sequence yourself and put your sort of most creative time and creative energy into the things that really matter. And also the things that have a long lead time. And then the truth is that you have to forgive yourself for not being able to complete everything. And you're constantly triaging because, you know, Mitch, what you just said is you have this list of things. So true. And also you have a whole bunch of stuff that's gonna just happen to you. You, right, you don't even sort of see it coming. It's going to just happen. So you need to carve out the right time to take strategic action, to do deep thinking. So it's like a couple hours a day, allocate your most sort of fresh energy whenever that is to those most important things. And then I think it's actually very helpful. I used to be a fan of when founders would start their company and they'd only have very small, you know, like tiny company, like 10 people or 20 people I would think. No, no, of course you shouldn't waste your money on an ea. And now I think, you know what, it's actually really helpful to have an EA who helps you follow up on things, who helps you stay on top of your schedule, who can sometimes be another set of hands, for example Mitch in your case, to draft the copy even if it's not good, it might be starting from, might be better than starting from a total blank page. So finding the ways to delegate and to help to get help in a competent way is actually a massive time saving technique.

So I wanted to talk about this idea because building teams is a huge topic in the startup world and I'm sure it's a huge topic that you're constantly grappling and dealing with. And I even find myself in the place where people will call me and ask that question of I think I need someone to run our marketing. And my gut reaction is what are you talking about? Somebody to lead a team of people who are going to do some marketing. Are you talking about hiring someone to actually like do that email, right, do that ad copy like and when they say I don't know I find that genuinely my answer back is I well, I don't know either and, and I'm wondering how, how you think about it when you are really forget 10 people, when you're two, when you're three, when you're really the founders and you're doing a lot and you're managing and I'll get back to today's and timing because I have some thoughts around questions around that too. But who do you hire? Do you hire doers out of the gate or do you hire people who can lead, people who can do right.

I think that the stages in startups are really helpful to guide that answer. Early days of a startup, what you're typically doing is hiring people who are useful, who like utility players, can do a bunch of different stuff and probably can learn it. So they may not be the person who wrote the email copy at their past jobs, but they might be able to take a couple hours or a couple days and get enough training to write enough good email copy. Early days or you know, if you're looking for the person who can do it, who the sort of the expert you bring in, someone who has an Expertise just in that. But I think in the early stages of startups you do want to find doers. You want to find people who are comfortable with change and comfortable expanding very quickly and comfortable learning new things, sort of diving in a very proactive, you know, can do way as the startup matures. You definitely want to look for leaders and builders, not the person who's going to write the email copy, not the person even who's going to sort of tell other people to write the email copy. It's more like the person who's going to say, whoa, I've run a marketing department and really it's about thinking about this process of messaging and how we write the copy and who does what and sort of the definition of roles inside of that. Now that's a builder and a leader who is now going to run the team of the marketers that you have there. And that is no question a very different skill set. And also it's someone who's probably done that job before. And I would add that it's also important that the person's a people leader and a people manager because you're going to want them to, you know, sort of caretake the people that you've entrusted to them, like the marketing team so they can help develop their careers and also help make them better marketers over time.

Okay, now I want to go back to. You were talking about scheduling and putting in the time. It's, it seems to me like that is a path towards potential burnout stress. I have never not spoken to a founder and maybe I speak to the wrong founders that hasn't had some sort of mental health crisis. I've, I've seen founders have like, like the left side of their face froze for a month and it was all stress based. They're managing their time and they're good at it. The problem is at the end of the day there's only so many hours in a day and things that they quote, unquote, feel they have to get to, but essentially have to get to because let's face it, a lot of these founders are taking a lot of money very early and the pressure is even augmented when that happens. So what's the balance between. Yeah, you know, put the time and focus on when you have like it all sounds great, but when you're in the foxhole and the first bomb goes off it, you're running and you're looking at your day going, I'm, I'm not going to be able to get to anything or you're burning yourself out.

Yeah. So first of all, I really agree with you that the mental health is a massive problem with entrepreneurs. In fact, founders, entrepreneurs are 30% more likely to have issues with the depression and anxiety and to your point, burnout than their counterparts. And that's a real problem. You know, it's, it's a real problem. And, and like, the truth is that it's not clear if the personality of the founder is what's causing that or the stress of the extreme work environment is what's causing that. But one way or the other, it's a massive problem. I think that you have to do the best you can to manage your time. You have to do the best you can to recognize that these are the top priorities. And I'm going to let other fires burn. You know, I remember hearing about Peter Thiel and the whole squad at PayPal sitting together thinking about what fires are we going to let burn? And I think that's really important for a founder to realize that actually you can have a lot of burning fires and still be successful. I think investors these days are a lot more compassionate about founder depression and founder anxiety. But at the same time, there's a lot of pressure. And I think that in some ways you're buying yourself that kind of environment. And the last thing I would say is that as I talk about in the book, you do the best you can to do self care. So it's really important to be on the right fitness regimen. It's really important to have the right stress reduction techniques, whether it's meditation or inspirational reading or again, fitness. It's really important to eat nutritiously, it's important to get enough sleep because those are the things that will take care of your physical body, which will help you may not solve, but it will help you take care of your mental health. You have to have a friend group around you that will help you. Obviously finding a therapist, certainly having a coach. These are all things that also can support your mental well being. But I'm not going to pretend it's a solution. The truth is that you have to figure out how you can kind of live inside of this pressure cooker and this extreme work environment for years. It can last years. The sort of, the difficult nature of it.

Yeah, I mean, that's the other myth about this. We hear these stories and see these acquisitions and think you have an idea and a year later you sell it. But the truth is, most of these businesses, before you see anything is five years. And before there's anything really material, it's usually a decade. I mean, that is the real trajectory. And even that is fast for many.

Oh yeah, that's fast. And also it's still true that most startups fail. It's still true that most small businesses fail. And so I agree. I think that the mythologizing of startups has done a disservice to people because I think they think like I'm a failure if it's five years in and we're not gaining the right traction or if, you know, if it does fail the business or if they don't get a great outcome if they sell. And I think it's important to recognize that it's actually the exceptions that have these big outcomes.

Yeah, we highlight the exceptions. We don't highlight the rules because the rules would be boring if we did that. I'm curious about the new reality and the new reality I see in the startup world is one is there's a tremendous amount of dry powder that is looking to be invested into these companies. We're talking trillions of dollars and by the way, a lot of it unfortunately not really going to places like female driven startups or those from diverse cultures. There's a real issue with that and we've seen seen even because of COVID an even worse result in that. But maybe a topic if you want to weave it in. I'd love to hear your thoughts on that. But just dry powder in general and what's leading, what pushes that is then insane valuations. I mean, I'm literally seeing offers of money to companies with very little due diligence, market capitalizations that are completely misaligned with anything related to any reasonable market because there's so much dry powder and people wanted to just put as many chips on that roulette table as possible. So hearing that, you would think, wow, that's amazing. We're going to really inspire innovation and see this new culture of startups and diverse founders, but we're not necessarily seeing that and that could be caused to create more tension for these founders. And I'm wondering your thoughts on again, this strange paradox that we find ourselves in.

Yeah, it is strange. You say dry powder and I agree with you. And also there's been over the past few years especially super inflated funds being or rounds being raised. As you said, it's sort of very shocking valuations. I think in some ways that puts pressure on the investors actually, because they're trying to figure out, you know, there's almost a bidding war in a sense for startups. I certainly think it Puts pressure on startup founders because they recognize like, you know, the enormity of like, oh, we have a lot of money now, what are we going to do? And it also puts pressure on them to spend the money and that may not always be the right answer for them at their stage. Sometimes too, too much money too early can actually not. Can be not a good thing for them. So, you know, I think this, you know, the topic you raise about money coming to underrepresented people like minorities, like women, it is, it's a real, it's, it's just a real concern.

Well, it's surprisingly brutal that it got worse. You would have thought after me too, Black Lives Matter, where the world is at, that we would see it moving in a positive direction. But it seems from what I've seen in terms of the research and is that it's not going in that direction.

No, I think we need to continue to change the landscape of who people see. Like literally the people who are involved with venture and also who are involved with startups. And I think we need to continue to just change that picture. And until we do, I think that it's still going to be the same groups of people giving money to the same groups of people.

Yeah, it's, it has to change. And we're seeing the people out there, the ability to support them, incubate, push it forward. It shocks me that there hasn't been a higher level of equalization there at all. It's strange. Last area I'm curious about is just work in general. Right now we're hearing tons of thoughts on what the future of work and the office will be. Clearly there's a lot of the ideas and, or businesses being driven out of the startup community. I keep vacillating on how I feel about what it's going to be like in terms of remote work from home, home, all that, that whole world. I'm wondering what, what your thoughts are in a world where again, there's, there's many sides to this story. There's a recent Microsoft report that came out that talked about creativity, innovation. Collaboration has completely fallen off the charts that people are working in more silos than ever before. You know, when I look at the greater result of the pandemic, I don't think people are not going to concerts because they got used to streaming. I don't think people are not going to restaurants because they got used to Uber eats. It seems to me that we are maybe overplaying a hand here, that the only thing that will really change is the fact that, nope, we're just going to work, you know, we're going to go to work three days a week and work remotely. I'm not sure I'm buying into that as much anymore. And based off of the leaders I've spoken to, it seems like those who are choosing that route are not necessarily getting the same results of those who are, quote, unquote, showing up in the physical space, which is, again, it's a human, human. It's a natural human instinct. And a lot of the thinking came from a world where we were all remote. Like, I keep people like, we're going to be only remote in three days a week. I'm like, easy to say that when everyone is remote, because you have to be different when 30, 40, 50, 60% of the team is there physically and others are making a choice or the company's allowing it. I do think you're going to have a different result. And you're. Again, we were speaking about women earlier. They're saying it's going to affect women probably the most or whoever else it might, because that's just the nature of how this thing unfortunately always plays out. So when you're speaking to founders and startup, just the startup community, do you see them thinking differently about work? Now that we're in this phase, do you think it's going to go back to the way it was? Do you think it's going to be totally different?

So, first of all, I would say the founders I speak to are definitely thinking about it. They're thinking about it quite a bit and they're trying to figure out what's the right answer for us. And since we do, they don't really know. They're really betting on a bunch of experiments. So one of the companies I work with is saying, we're hybrid, we're going to reinvent hybrid, and specifically we're going to have an office, and we're going to have the office to be a gathering place where we only gather when we have a team meeting or we want to gather in person for something specific. But mostly people will be remote. If they are remote and they need to have a place away from home because they don't have a big enough house or apartment here in New York or they have kids at home, they can go off and find like a wework location, you know, a remote location to work from. So that's one way to handle this. I think your point about when some people are all in the room together having a meeting and some people are remote, it's actually a terrible experience. So if you're going to do that, you need to think about what kinds of technology upgrades do you need to do to make sure that it's going to be a better experience? Or you need to say, and this sounds weird to everybody, you need to take that zoom meeting from your desk or from, you know, so everybody's on zoom together now. People don't like that either. So I think there's a lot of experimentation going on. I think the people who find it the simplest, it may not be the best structure, but the simplest is what companies have been doing long before the pandemic, which is to go remote first or remote only. So the companies that are doing that have a pretty well trod playbook already to pull from. And then the question question is how often can they safely meet in person? Because one of the secrets of remote work is to have periodic in person meetings to drive that collaboration, that creativity. And also just the social capital that greases the skids of getting work done.

Yeah, I think we're overplaying a lot of hands and placing bets that we really don't know much about. And I also think we are undervaluing human nature in general. Like I really, really do. Just the, the more people who are going back to the office feel that it's an all or nothing situation and that while there are nuances of course and it's not again, painting the brush in general, it's like this is what worked for us and this is what's going to work for us. And yeah, it's, I think it's going to be depressing to people who think work is going to be completely the only thing that really changed as a result of co. But that's probably a conversation for another day. Yes, we should let people know that your brand new awesome book is called From Startup to Grown Up. Let people know where they can best connect to you. Find out more about whether it's your coaching services, your book, whatever you want to let people know about.

Well, you could definitely come to my website, alyssacon.com and you can download my five scripts to help you be a better leader. It's about really getting your mouth around the words of some delicate and difficult conversations you have to have as a leader. And you can always send me an email. I'd love to to hear from everybody and I always love to hear what people have taken away from this discussion. So Alyssa lissacon.com is my email. Feel free to reach out to tell me what you learned today in our Discussion and what you're going to use.

No pressure. Alyssa, thank you. Yeah. Thank you so much for your time.

Thank you, Mitch. This was a great conversation. I really appreciate you.

Smells on the air see there it's crushing the final impression Stains on the paper where words felt like water Unearth all the changes that never didn't matter. I think it's beginning to freeze here. Caught in the rage and the fire of things all the brightness that burns me I fumble in through like a child in the dark when the nakedness comes I am shocked by the color the glorious way your skin comes alive And I never thought we make it back so soon Might be nice but I knew you'd be your own destroyer come the time and I never thought I'd make it up to you. Here please forgive me. How could we escape all the bitterness powder bomb bitterness held in the face of the things that I don't understand Intellectual lies over and over this helplessness suits us funny how quiet has slipped to our corners Worn all our edges away you were watching are breathing and bathing wanting and warming and cautiously waiting for some simple signal to creep cross your conscience uncover redemption and oh, did I mention I carried you down to the St. Lawrence River? The bank's running dirty the water's beginning to freeze here solid by morning.

And.

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