How to Become the Top Startup Coach in the World Featuring Alisa Cohn

Being nervous, being anxious is normal. If you're going to take this difficult leap of going out on your own, it's helpful to figure out for yourself why.

From Smashing the Plateau I'm David Schreiner Khan with Going Solo. In this show, we discuss building your own successful business after a long career as an employed professional. Today, on episode 116 of Going Solo, I'm speaking with the startup CEO and coach, Alyssa Cohn. Alyssa Alyssa is known as the top startup coach in the world, but her notoriety didn't happen overnight. In this episode, Alyssa shares how she figured out how to build her coaching practice from zero to today. Stay with us to hear all the details. I believe everyone should have the opportunity to do what they love and get paid what they're worth. On my podcast, I've interviewed hundreds of successful entrepreneurs, many of whom run consulting or coaching businesses. We've created a free ebook with 49 actionable steps from 49 of our popular episodes to help you smash the plateau in your business and your life. It includes tips to help you with your mindset, relationships, business development and productivity. You can get your copy of 49 Tips to Smash youh Plateau at smashingtheplateau.com sltips that's smashingtheplateau.com tips. Now let's welcome Alyssa Cohen, named top Startup Coach in the World at the Thinkers50 Marshall Goldsmith Global Coaches Awards. Alyssa has coached startup founders into world class CEOs for 20 years. Rated the number one global guru of startups in 2021, she's worked with Venmo and Etsy DraftKings, Mack Weldon and Tory Burch. Alyssa, welcome to the show.

Thank you so much for having me. David. I'm excited to be here.

I'm so excited about our upcoming conversation. So I know you had a career before you became a coach. Let's start with a little bit of that and then we could transition into why you became self employed.

Absolutely. Well, so I left undergrad, I went to Boston University and I went to the nonprofit world. So I was the sort of a regional manager of working with international exchange students. And then I went to university in New England to become the chief of staff to the provost there. So you know, from there I sort of began to get a little bit of an awakening of what do I really want to do. And I decided I wanted to focus more on what help people get aligned inside of their organizations or sadly not. And so I went off to business school to look at that. I sort of got stumped on the way to business school And I went to the monitor group for a little while to strategy consulting. I went to Cornell for business school. And at Cornell we actually had an outstanding accounting faculty. It was like I was totally inspired by accounting and finance and strategy. And also you kind of get turned around in business school because there's a lot of status and sort of excitement focused on those topics. So I got all turned around. I ended up going to PricewaterhouseCoopers and their so called fast track program. Five years to partnership. And that seemed like a good idea until about two and a half years in I just thought this is not it, this is not for me. So I had to kind of figure out what is for me. And a couple of things happened. I met a coach and I was like, what is that? I want to do that. I met her at a conference and I thought that's what I want to do. And then the other thing that happened is I realized I wanted to make a difference. That was kind of the music in my head to make a difference. And I ended up joining the startup world. So I was a CFO of one startup, the head of strategy of another startup. And when that kind of all imploded, I had already taken coach training, I'd coached all my friends. So I decided, okay, I'm gonna become a coach right now.

So you were happy being a coach when you were in the startup world?

Well, I wasn't a coach in the startup world. I was the CFO in a startup.

Ah, okay.

And I was the head of strategy of another startup. But I had met a coach and I had this sort of coaching in the back of my mind and I'd taken coach training and I coached all my friends and so I was kind of preparing for being a coach.

Right, right. So you, you knew it was what you wanted to do at some point? Yes, Got it, got it. And tell me a little bit more about the implosion, the dot com implosion. Well, how it impacted you specifically.

Well, what happened was, you know, I'm thinking like I was at my second startup and we were co located in San Francisco and Boston. And so, you know, the startup was the startup world was melting down around me. Our company in particular was shutting down its Boston office. And they said to me, come out to San Francisco and we have, we'll have a job for you. And I thought about that because it's really hard to as you know, it's really hard to decide, well, I'm going to become self employed now. I'm just going to go for It. And in addition to thinking about whether or not I should go to San Francisco and do that job, I was, you know, I have my own coach at the time, and I was looking for another job, and I got offered another job in Boston. And my coach at the time said, that's the same job you keep getting offered. If you need ever need that job, you'll get offered that job again. You've been saying you want to start your own thing. The time is now. And I thought about it, and although I was sort of scared to death, I just realized she was right. And so I turned down both the offer to come to San Francisco and the job offer I got from a different company. And it was pretty much like on Friday, I said, okay, I'm going to become a coach now. And then on Monday, I became a coach.

Wow. And you had no clients at the beginning?

Zero clients.

Zero clients. Zero business.

Zero clients, zero business. Yes.

Yeah. That is scary.

It was terrifying. Yeah. I didn't draw a calm breath for like five years.

Wow.

Yeah.

And. And how public were you on that first Monday when you said, now I'm a coach, how public were you about your coaching business? Who are you? Who you were going to serve?

Yeah.

How much you would charge all those things.

Yeah, all those things. Well, I mean, many things to say about that, first of all. So I'm an executive coach. Nonetheless, A lot of coaching memes or coaching mindsets are similar, like personal coaching and life coaching and executive coaching. And in general, I like to make sure that everyone knows I'm an executive coach, not a life coach. However, on day one of becoming a coach, I did a very life coachy activity, which is that I got a bunch of magazines and I cut up all the magazines and I drew and I wrote. I sort of pasted a collage on a piece of poster board of my ideal life. So that was day one. And it was very inspiring, like it was in my vision board. And it was actually very inspiring. It was a lot like, you know, persistence and what gets you there and grit and how hard work is going to get you there. And also was about this one thing in particular, this picture of a woman who, it says, started her own business and made more money in her first year than she had in the past three years of her career. You know, I like, focused on that and a woman who was rock climbing, you know, going up the side of a mountain, and it was, like, about grit and persistence and about, you know, getting out there and trying and risking. So that was day one. As a coach. And then day two as a coach was, gosh, what am I going to do? What should I do now? I did have that vision board because you have to do a lot of hard things to start your business from scratch. And for me, I was working with a coach. So part of it was like to get my materials together, and then part of it was to find part of coach. So I asked everybody I knew if they had somebody that I could coach for free just to get the reps in about being a coach. And when you ask me, was I public about it at first, even, like, pricing and how I was going to do it and how I was going to serve, I didn't even know the answer to that question. Like, I was trying to figure it out. I didn't even know you should be thinking about who you're going to serve. I told you. I went to see a friend, and her parents asked me what I was doing, and I said, I'm gonna become a coach. I said, you know, what I'm really passionate about is helping people get a better handle on their money, maybe get out of debt, you know, sort of be more financially responsible, because after all, I was a cpa, right? So I. And also I had, like, an interest in this helping other people figure out their money stuff. And the father of my friend said, if they're bankrupt and in debt, how are they going to pay you? I thought, well, that's a very good point. I never thought about that. So, you know, I sort of had to spend some time figuring it out. I was introduced to the brother of close friends as maybe a potential client. And I. We talked, we had a good conversation. And at the end, he said, by the way, how do you describe coaching? And I don't know what I said, but my answer was so confused and chaotic and not understandable that he actually said to me, well, that was compelling, I. E. Sarcastically, I. E. It was not compelling. So, I mean, I had a lot to get through that first, like, year. And slowly, one foot in front of the other, I did begin to figure out who I could serve. So I realized I was very interested in helping people kind of sort out their career lives. And that's why I definitely wanted to become an executive coach, a business coach, somebody who helped people in the context of business. At first, that looked like individuals who needed help managing their careers and also getting new jobs, because I was kind of just good at that, naturally. And then over time, that became that. I was called into organizations and I'd get my foot in the door of companies. And then I would help executives inside of companies manage their careers and get promoted and be more effective. And then over time, I was also building my way into learning my way into figuring out the key tools of leadership, like influence. I got very interested in executive presence. So I really, you know, iterated, iterated, iterated over time on different areas of specialty until finally I ended up, you know, really focusing also in startups. That was a long time later.

Yeah. I'm really glad that you shared all these details, Alyssa, because I think it's really important for people to hear that, like you're a tremendous example of somebody who has set her mind on achieving something and you've been phenomenally successful, but it has not been in a day, in a week, in a month.

Right, right.

It takes time. There are a lot of steps along the way. It's like I like to say, a breakthrough is when somebody else has noticed the thousands of steps and pivots you've made.

Yeah, that's really true.

Right. So it's. This is not an overnight thing. This is, this is hard work that it's dealing with what you described as being terrifying, Dealing with it, figuring it out, being willing to put yourself forward and making all those, those tiny transformations along the way. So thank you for sharing that.

Well, thank you for saying that. I do want to say one thing in service of what you just said. There was a day that I walked into the gym and I was so overwhelmed and overcome by how nervous I was and upset I was and not sure I was, that I actually burst into tears. And you know, there I'm in the corner of the gym crying. And then for whatever reason, I got this image of my 90 year old self kind of looking down on me like my this grandmother, 90 year old self. And she was saying, what was she so upset about? You know, she had a couple of bucks in the bank. You know, she had parents who weren't going to let her starve. You know, she had health and like a sense of drive. What was she so upset about? And that really gave me a lot of comfort because as I spent the next five years really not taking a calm breath, really hustling every day, really being in driver mode. I would think, like from the perspective of that older self, I know this is gonna get me there. But that also really helped me when I had to do things I didn't feel like doing. And you know, my vision board, as much as I even myself kind of made fun of it was really helpful. Cause I Had to do a lot of things I didn't want to do and get uncomfort in a lot of ways I did not want to do. But I always knew it was in service of the things that I did want. And I appreciate that you say I'm successful now. I know I'm successful now. And let me tell you, that did not just happen. It really took work.

Thank you for sharing that. By the way, do you still have that vision board?

I do. I was like thinking, should I go and get it right now? I have it right in my other bedroom. And by the way, I left Boston, I'm in New York now, and I left a lot of things behind in Boston and I have not quite figured out where to put that vision board. Like, it's. It's not on my wall, but I still have it because it's really meaningful to me.

Yeah.

Yeah.

How long have you been known as the startup coach?

Probably well known as a startup coach. Probably like five years. But I've been working a lot with startups for like 14 years. I moved to New York about 14 years ago and that coincided with a massive kind of tech movement, startup movement in New York. And I like to be part of building and I like to be part of communities. So. So for me, I was excited to be part of this thing we were building in New York. And also I had been in the startup world. I had these two executive roles inside the startups and I had the startup bug. So it made sense for me to be part of the sort of startup ecosystem here in New York. And then I definitely got hooked and got, you know, interested in what does it take for founders to grow into CEOs. And then I just began, you know, I began to, as we all do, I became an expert in it. I learned and learned and learned. I mean, that's what my book is about now. From Startup to Grownup is about that journey from founder to CEO, from somebody who's building a product to somebody who's building a business. Because I walked into companies all the time and I would say things like, well, so where's your leadership team? And they'd say, well, what's a leadership team? But I didn't ask that. The first day I walked in with startup, it was like five startups in 10 startups in. I was like, oh, they need a leadership team or oh, they need to have an off site. And as you get good at something, you then again get more and more called to do that thing.

Tell me a little bit about your Process for becoming good at something. Like one of the issues that I see with, and you've kind of described this, one of the issues for somebody who becomes a consultant or becomes a coach, particularly after a long career as an employed professional, is as an employed professional, especially, you know, a high achieving one who's been in the work working world for a long time, you get well paid for dealing with complexity and solving complex problems and typically not solving something that's, that's so repeatable. And when you're in your own business, it's actually your marketing is better when you become known for something very specific. It's easier to attract your ideal clients. And frankly, it's a lot more profitable as a business owner when you're dealing with the same kind of problem over and over again.

Yes.

So the question is, can you talk a little bit about your process for kind of narrowing in on a particular niche and then becoming more and more expert within that niche?

Yeah, it was hard for me to narrow in on a niche because I fell prey to a concern that many people have, which is, oh, no, but then what if other people don't want to hire me because I'm too niched or whatever? So that was already a problem for me. And then also I'm very interested in a lot of different things and I think I can help everybody. So, you know, I really didn't want to say, oh, no, only this and not this. But luckily the niche began to come to me. Initially, I got very interested in influence because I must have read a few books by Robert Cialdini and I saw how important it was in the workplace. Like I really, one thing that I was focused on is I want to be an executive coach. I want to work at high levels of the organization so I can have more impact. Because I, you know, going back to why I became a coach, I wanted to make a difference and I wanted that the work of my hands mattered. And in a company, if you can help a senior executive, first of all, people live most of their lives in the workplace. They just do. So I knew that if I could help make workplaces better, I'd be making people's lives better. And when you can impact an executive, that means you have a lot more scope to impact a whole bunch of other people. So, okay, what do I need as a coach? What skills do I need to offer to be excellent at working with executives? Well, definitely influence. And also I was interested in that. And also I heard this phrase one time, executive presence, and I thought, oh, that's what's that? I want that. I didn't even know what it was. But I also saw like other people needed that. So I began to test out this idea with other people that I was an expert in executive presence, power, influence on charisma, corporate politics and decision making. And I would say that to people in order to pretend I had a niche also because those are things I was interested in. But most people could find something for themselves inside of a company and especially a large company inside of that. I like the word charisma, so I like to throw that in because oh, what's charisma? And I like the word corporate politics. People shy away from corporate politics. So I began to like test that out and that was very successful. So then I would start when I started working with startups, that's not so much. Those topics are not as relevant for startups. So I began to almost, I would say to people I'm, I have a barbell, you know, I have sort of two sides to my practice. One is I work in those areas with executives and large established companies and then I also work with startups, founders, co founders, executives to help them grow their startup. So when you have kind of two niches that I think feels comfortable to people. And I began to be able to articulate it with a lot of confidence. And then to your point about how do you learn that, hey, if you decide that you're an expert in influence, you better go out and read a whole bunch of books and you better talk to a lot of people about influence and you better test out what works and what doesn't work. And that's what I did. Same with executive presence, same with decision making. And I think it's really important to become an expert in the areas that you love because if you don't love them, you're not going to do the extra time and energy, reading, practicing, talking about them. I really believe in practice exhibition games and you're sort of doing things over and over, especially in low stakes moments that will help you with higher stakes. I believe in helping my clients experiment with different tools and techniques. I absolutely believe in being up to speed on the literature. I work a lot with my mentor, Marshall Goldsmith and the other members of the Marshall goes 100 coaches and to learn what they're learning. So I guess I would say I'm very much like passionate about self study.

Yeah. Thank you for sharing all this. And now let's talk a little bit about your actual expertise. So what kinds of problems do you solve?

I solve a problem Sometimes that where an executive has a problem and they don't know what the problem is. So I do two things. I help people, executives, CEOs, founders, identify what's the problem. And I do that by asking a whole bunch of questions like, well, tell me more about that. What do you mean by that? How would you categorize the situations where that comes up? Give me an example of a situation. Give me another example of that situation. So in doing so, I actually help people mind the problem themselves, which they find very valuable. And then the other piece of what I do is I help people actually as a coach. I help people solve their own problems by helping them identify where they are, where they're going and how they're going to get there. By helping them think through differently on frameworks, being more rigorous with their own language and the way they're thinking about something, helping them with mindset shifts and also being a sounding board so they can talk out their issues and problems and through that come to their own solutions.

That's great. How do you share information about yourself and your ideas and your methodology?

Well, I do that through writing. So I write for hbr, for Forbes and for Inc. I'm on a lot of podcasts, not unlike the amazing going solo podcast right here, right now.

You're very kind.

It's an important way to share my information and I think you know. Well, I've also just written a book, right, called From Startup to Grown up, which is 10 chapters of sharing information, both about the journey of going from founder to CEO, but it's really about the journey of going anywhere you want to go, which is it's divided into three sections, so self managing yourself, managing others, and managing the company. So if you're a solo practitioner, you first have to start with managing your own psychology, as I did myself, as everybody has to managing the ups and downs on your own, managing times, the loneliness, managing having this sort of self discipline to do the things you need to do and then managing them. In the case of a solo professional is managing clients, managing vendors, managing your other stakeholders, and then managing the business is that I think that people forget this is a business you're running. So how do you think about the metrics of your own business? Which is something that I think about certainly as well in terms of revenue, in terms of how I spend my time, really what I measure is how I spend my time and how effective it is in terms of either my marketing activities, my sales activities, or my client work activities.

That's great. Alyssa, is there anything that I haven't asked you, that you would really like to share before we close out.

What I want to share with everybody is that being nervous, being anxious is normal. And I think it's extremely helpful to have in your mind's eye if you're going to take this difficult leap of going out on your own, it's helpful to figure out for yourself why. For some people, it's purpose and meaning, especially, you know, sort of later in life. For some people, it's to have independence, financial independence, and also just purpose, personal autonomy. I know for myself, I felt like it was about wanting to activate all of my powers, not just the powers the company would let me have. So I wanted to really express my full self and to make sure that even as you get nervous and even as you get distracted and have all the ups and downs, that if you keep your North Star in mind and put one foot in front of the other, you will get there.

That is great. Alyssa, I want to thank you so much for taking the time to come on the show and be so forthcoming with your story and sharing all of the trials and tribulations that have led to where you are now. If someone wants to go deeper with anything we've discussed or access any of the resources that you may have or get a copy of your book, where would be the best place for them to go?

Well, you can definitely come to my website, alyssacon.com and I have two. Well, certainly you can find the book from there. The book is called From Startup to Grownup. It's available on Amazon as of October 4th, and also so on my website I have a number of free resources. Right now I have. Well, actually by the time this comes out, I will have a set of scripts to use. So what I love to do is give my clients scripts to have difficult or delicate conversations. And I'm offering them to folks who come to my website and subscribe to my newsletters because people find them very valuable to have. Just get your mouth around the words. So come and join me on my website, follow me on LinkedIn and Twitter and say hi.

Sounds great. My guest today has been Startup CEO and coach Alyssa Cohn. Thank you again, Alyssa, for joining us.

Thank you, David. It was so fun.

When you visit the goingsolo website, you'll find a summary of each episode along with the links we mention on the show today, we learned how Alyssa Cohen became the top Startup coach and much more. I believe everyone should have the opportunity to do what they love and get paid what they're worth. On my podcast, I've interviewed hundreds of successful entrepreneurs, many of whom run consulting or coaching businesses, and we've created a free ebook with 49 actionable steps from 49 of our popular episodes to help you smash the plateau in your business and your life. It includes tips to help you with your mindset, relationships, business development, and productivity. You can get your copy of 49 Tips to Smash youh Plateau at smashingtheplateau.com tips that's smashingtheplateau.com tips. Thank you for taking the time to listen to our show. I'll see you on our next episode.