Forever Employable Stories: Alisa Cohn, #1 Startup Coach in the World

Hey, folks, welcome back to another Forever Employable story. Super excited for my guest. This time around. I have executive coach, startup coach, and all around fascinating person, Alyssa Cohn joining me from very close to my former hometown in New Jersey. Alyssa, how are you today?

I'm fantastic. It's so great to be here with you today. Thank you for having me.

I'm thrilled. I'm thrilled to be here. We met a few months ago with Dorie Clark. You and Dorie were hosting a bit of a networking, kind of virtual drinks thing, which I was lucky enough to get an invitation to, and I thought that was kind of super on brand for her. Dorie wrote the forward for my new book, Forever Employable. And really, how do you. How do you maintain these networks in a world we're all socially distributed? Well, virtual drinks it was.

Yeah.

You and I met.

Yeah. And just to say, Jeff, we also wrote an article for two articles for HBR about how to do virtual networking during this time. So it's something that has a lot of passion and resonance for both of us. The idea of how do you add people to your network and then also continue to get to know people who you already know?

Yeah. And look, it's super important and super valuable, and we're here today because of that. We didn't know each other before that, and that was really nice. And I'm super thrilled that you've made the time to tell us your story, which I'm super excited about. So, look, you're an executive coach. You're the number one startup coach in the world, which is an amazing feat. But let's start off with executive coaching because I think that's really interesting. So what's an executive coach? What do they do?

Yep. So when I think about coaching, what I think about is this. It's helping people assess. Where are they, where are they going and how are they going to get there? Now, you can apply that to any aspect of life. Life coaches do life stuff, right? Weight loss coaches, weight stuff. I work with executives, specifically startup founders, to help them think about their leadership, to help them get coached inside of their leadership and help them grow as leaders. So coaching is really about partnering with someone to help them walk the path so they can be who they sort of. They can reach their full expression of leadership.

The startup founders that I've met and that I've worked for in the past, they all have some element of brilliance, Right. They got to that point by being smart, by being brilliant, by having this spark or whatever it is. The interesting thing Is I wonder what your experience is. How often. So a lot of the times it's technical brilliance, or it's product brilliance or it's design brilliance. Leadership is something that they typically have to kind of grow into if that brilliance sparks an idea that actually begins to grow. Can you teach that to somebody? Can you teach them leadership?

Yeah, it's a great question. It's the essential question, right? So can you teach that kind of leadership? The answer is absolutely yes. But to your point, a lot of founders, they start off with a technical expertise, even a sales expertise, product, and, and maybe they're tinkerers. And it's about how do you go from someone who's busy building a product to someone who's busy building a business? And that is a different thing altogether. So then it's about getting the right people, galvanizing them, motivating, figuring out what's going to motivate them, and putting together all the aspects that you need to along that way. So that requires inner growth. Inner growth. Like, I'm not sure if you remember, but in our cocktail event, I told you about the rap music video that I produced this summer, my summer Covid project, and it's called the work is in you. And that's what it takes for any founder to grow into a CEO or really anybody to grow. The work is in you. How do you grow yourself in order to kind of figure out what are the elements that you need to build to build a business and a thriving company?

So as you think about being a coach and you look at sort of the analogous coaches that people know, sports coaches, for example, things like that, gymnastics coaches, whatever it is, right. It feels like a lot of those folks did that thing first and then became coaches. So how does one become an executive coach? Don't you need to be an executive first?

You know, the answer is, it depends. I mean, from my point of view, as you know, I was at PwC and I was kind of on the fast track to partner there. So I had kind of that corporate expertise. I then joined the startup world and I was the CFO of one startup and the head of strategy of another startup. So I kind of got my own leadership chops at a young age. And I have found that actually I'm also a cpa, as we talked about before this, I have found all of those things enormously helpful when it comes to helping people scale, because I scale their leadership because I know what it is like to be in the trenches. Do you have to be have been an executive? I can't say. I think that you have to know the topics that executives deal with and had some experience of that kind of pressure that CEOs face every day, because without it, you don't quite have the empathy.

And so you start off your career sort of the way we're all told to start off our career. We get a job, we move from one place to the next, we get a little bit more responsibility and. And then you decide to transition out. So I really have two questions and probably grow on top of that. Why? Why transition out of the corporate world? And then, and then how, how did you actually get out? Because breaking that cycle, particularly if you, if you're dependent on that paycheck every weeks, every month, whatever it is, is. It's really difficult, as I'm speaking from personal experience as well. So. So why break out of the corporate world? And then how did you do it? What was eas?

Yeah, it's as you said, it's very difficult. So from my experience, I was at PricewaterhouseCoopers and I was on this fast track to partner. I had sort of like, it's a 12 to 14 year journey to partnership. The program I was in was supposed to be a five year journey to partnership. So, you know, I had it all set in some ways, but I woke up at two and a half years in and I just thought, this is not for me. By the way, PwC is a fantastic firm. It's an amazing firm. And. And they treated me great the whole time, and they treated everybody great. And even as I was leaving, they were amazing to me. It just wasn't the right fit for me because it was just too big. And I just realized this is not for me and I had to go seek out what is for me. But how do you tell. Honestly, I got sick. I woke up one morning and I thought, I hope I get the flu so I don't have to go to work tomorrow. And then I got the flu like 18 hours later, rushed to the emergency room. So important pro tip, do not ask for the flu because it's really bad. So I was down for the count for two weeks. And every time I thought about going back to work, my fever would spike back up. And I just thought, this is not it. And I kept thinking in my head that it matters to me to make a difference, to make a difference, that the work of my hands matters. And PwC a great firm with all those people that did not feel like my calling. And so I had to seek out my calling. By the way, how do you do that? You kind of wander around and what. In my case, I went to this conference that I would never have gone to. It was called the Body and Soul Conference. And my boyfriend at the time was a yoga guy. So he's like, let's go volunteer this Body and Soul Conference. I'm like, seriously? But, you know, I had nothing else to do. Okay. So, you know, and I was sort of, again, I was in a seeking mode. And at this Body and Soul Conference, I was a volunteer and they said, okay, Cheryl Richardson is now going to speak to the volunteers. And I'm like, who's Cheryl Richardson? And can I go to stay for this? And then it turned out she was amazing and she's a coach, a very well known coach, it turns out. And she was amazing. And I followed her on that whole conference and I was like, that, that's, that's what I want to do. It was like violins played. And then Jeff, it's mechanics. So like, how do you go become a coach? So I asked Cheryl, how do you become a coach? And she said, you should get coach training. I'm like, ok, I got some coach training. And they said, you should coach everyone you meet. Okay. So I got my friends to let me coach them for free. In the meantime, I did leave my job at PwC. I joined the startup world. And that went on for a couple of years. And when things went south in 2000, I had already kind of gotten myself together to be a coach. I had taken coach training, I coached everyone I know. And then your next question, what do you do? You put one foot in front of the other. And so I began to figure out, how do I. You want a tactic, so I'm going to give you a tactic. My gym had this vendor fair that you could go down and you could like present, you know, like yourself. So I was like, I'm going to go to the vendor fair. And it was February and it was sleep. I was in Boston, it was sleeting, it was dark, it was five o'. Clock. I did not want to go, but I pulled myself together because I thought, this is what, you know, like, it's not like this sleet and this vendor fair is what I want. What I want is the life of my dreams. So if I want the life of my dreams, I'm going to walk through the sleet to go down and present myself with this vendor fair, which I did. And I had people sign up for complimentary sessions, which they did. Half of them did not show up for their complimentary session, but some did. And I coached them complimentary. And then one hired me after that call, and that was my first client, Rick Samuels. Thank you, Rick.

You still keep in touch?

No.

No. Okay.

I should track him down.

Yeah. Yeah.

Because that was my first paying client. And I will never forget, you know, the gratification of that. And things are hard, but if you want this vision of what you say you want, you have to do hard things to go get that.

Absolutely. Let me ask a clarifying question. So you say coaching, and, you know, specifically, you're an executive coach and a startup coach, but when you're starting out, you're saying, I met this woman and she was an amazing coach. And then she said, coach everyone you meet. Can you clarify what that means? So when you're saying, let me coach you, like what? Like how to shoot baskets, like, help me understand, like what. Like when you are. When you're offering that service. Because I want folks to really get a sense of how specific or how broad your pitch should be. If they're looking to break out of that cycle and they're looking at either make a significant shift like you did, or maybe even a subtle shift to take their expertise and do something just different with it, how specific or how broad do you need to be to make that pitch so that someone like Rick ends up hiring you for the first time?

Right. So it's a really good question, and it's a very good question. And, like, it's a little bit how I kind of perfected for me, by mistake, the art of helping, like adding value in 20 minutes. So that's kind of what I think. When I'm meeting with somebody new, my goal is to add value in 20 minutes. And so to me, it was very simple. I would say, what do you want coaching on? Nobody said shooting baskets.

Nobody.

Not a single person, but everyone. As I said before, coaching is a domain. It is really about how do you think about where are you. Where are you going, and how are you going to get there? And you can apply that to anything in your life, because really, it is about sitting down with somebody for an hour. And what I would say to people is, if you had a secret weapon for three to six months that was totally devoted to you and your success, what would you want to work on? And they would answer me, and we'd start working on it right there and then. And it might be. It might be weight loss, and it might be relationship stuff, and it might be. I feel stuck in my career. Right. Because I've Always been the kind of person, I've always been the person that my friends come to to ask about careers. So that is not a surprise to me. But the truth is, if I may not be a relationship expert, but I'm an expert at asking great questions because I'm curious about people and if we sit down together for an hour repeatedly, you're going to have insight through my questions and through my asking you to really dig deep about what's going on with you. And that will unlock a number of things in a number of aspects of your life.

So I work with a business coach. I'm a company of one. You know, I have a part time assistant but generally speaking, you're looking at got Health Corp right now.

And it's your family members, right?

Well, yeah, I mean the children.

My.

Video production crew as we call them around here. And it's, it's. But at the urging of a friend, I ended up hiring a business coach and I've been working with her now for a year. And I found it to be fascinating because again, I feel like I'm an expert in my field. I feel like I know what I'm doing and I feel like I have really good perspective. And like you said, you sit down with somebody on a regular basis for an hour and you share what's happening, what your challenges are, where you're trying to get to. Right. And the objective external expert opinion that comes back opens up so many new ideas. I've found it infinitely valuable.

So what Jeff, what specifically have you gotten out of it? I'm so interested in that.

So this, I mean to be very clear, right. So this book and the reason why we're even having this interview is, came out of that because the idea for this book was sitting in my backlog for two years. And you know, my coach, she asked me kind of a similar question. Like what, what, what's kind of what's sitting around? What would you really want to work on? I said, well, I've got this thing in my backlog. It's been sitting there for, for two years. She's like, what's stopping you from doing it? I don't have any time, I'm really busy. This and that. She's like, well, do you want to do it? I said, yeah. And we talked about tactics to get it done. And through her and through that support we got it done. And now this is out there and it's, it's a significant amount of my focus at the moment as well. And I don't think I don't think it would be. I don't think it would be live right now if it wasn't for my coach.

So that's so yay you. Thank you for sharing that. That's fantastic. And tribute to her. But also notice how she wasn't an expert on publishing books.

She's not. No.

That's not what you got out of it. What you got of it was someone to sit down with you and really gently but firmly inquire into you, really what's going on with you. I mean, it comes down to that. Like, for me, it's always like, what's really going on with you. And when you can identify that for yourself and you're pretty capable person as you are, things just change. You just devote the time to it, or you just find the person to help you or whatever it is. I think that's very powerful.

Absolutely. So you transition out and you kind of literally walk through sleet to get your first gig. Right. And so you're getting out there and you're figuring this out. How long ago was that, roughly speaking?

Roughly speaking, that was about 20 years ago.

20 years ago. Okay, so then how do you start to then build your brand? How do you start to build your reputation when you're coming out of one world and transitioning into a new world where I'm guessing not that many people knew you in that space at that time? Right. How do you start to build that brand? How do you start to grow the awareness and your reputation so that you start attracting more business to you?

Yeah. So actually, two separate questions. Because at first, I did not focus on building my brand. I didn't know to do that. I didn't have access to that language or those tools. I just hustled and I just talked to everybody I knew, everybody I could. I taught adult ed, which I guess was a way to build my brand without my quite realizing it. And I just kind of was. I built my network, maybe more. And I again, I really hustled and I really tried to figure out, how am I going to get clients? And because I'm pretty tenacious and also because I'm good at what I do, I got a bunch of clients. So that was very helpful as like proof of concept. And then the way I began to build my brand, you know, later than probably I would have wanted to, is. And I'll tell you what happened. I was working with this one company and it was going great, and they brought in a new head of leadership to this one company, and it was not going great anymore. And I was so upset. And I was like, I'm a runner. So I'd be running. Running and being so upset about this company and so upset by the time I got home, six miles later, it was always the same thing. Diversify your client base, Alyssa. You got to diversify your client base. And I'd be like, how do I do that? It's actually really not that hard. Write a newsletter. Okay. You know, so I was, like, really nervous about it. But about 14 years ago, 15 years ago, I began writing my monthly newsletter. So my monthly newsletter came out between eight to 10 times a year for as long as it was monthly. So just saying. Right. But I began to get used to. And by the way, I was terrified. Specifically, I wrote my first few, really for like a year. I wrote my additions. And then in those days, you'd have someone, like, launch it for you. So I would be done with it. I give it to him, to Barry. And then I would say, I'm going to go hide in my closet. And that is literally true. I was like, I go hide in my closet. I was so nervous about putting this out into the world. It was crazy. And so then I got more comfortable. And then I got the opportunity to write for Worth because I met the publisher at a dinner that I was at. So that was about networking. And I kind of got my courage up and to ask him if I could write for him. And by the way, he didn't. He said yes. And then I emailed him three times. Didn't get back to me. Then he got back, because that's because email overload, not because, you know, like, you have to be persistent with people. So that back to me put me off to the more junior person. We organized myself to write for Worth, which was great. And I used that to start writing for Forbes. And then I began to have a track record of content and building my brand and. And people began to hear about me, and they would come to me. And then INC found out about me, and INC asked me to write for them. So it's sort of Latin. And now I write for HBR again on the back of all of that content. So when you start building content and you have your network, as we know from our good friend Dori Clark, that's the way you become a recognized expert. And people began to reach out to me as a result of that. But it didn't happen in the first year.

Yeah.

So it takes a long time and.

Look, and that's really, really important because I talk about that in the book as well. And when I, when I tell my story as well. You know, I've been working on this for myself for 12 years. Right. And I don't. And it's an ongoing. It's ongoing work that's going to go on for a while. But I want to go back to something that you said. I want to connect the dots on something because it's. You said, how do I diversify my client base? Write a newsletter.

Yeah, I know.

Connect those dots.

I know.

How does writing a newsletter diversify your client base?

Right. Just to say that I read every time I went for a run and got that in my head, I rediscovered that every single time. And the reason is because what I knew without being an expert in this world, and I wish I had known then what I know now, but I just knew that having a regular cadence with reach out to people that was interesting and engaging to them would somehow come back to me in the form of clients. I didn't quite know how, but then it turned out, oh, people I used, who used to work with me rehired me or they'd forward it to a friend or they'd say, oh, I didn't know you were a coach. And then they would. Or oh, I forgot about you. Now I remember you. So as it happens, this person needs a coach or referring that way. So even just gathering the people you already know yields current business. Current business. But it also, again, it develops, you know, kind of a tribe so that people remember you because you're memorable. Yeah.

And so that, so that builds up over the years, starts to snowball into other writing gigs, which is terrific. I talk a lot about writing as a key skill. Clearly it's working for you. Give me a sense of in a typical, I don't know, in a month, roughly how much time do you invest in writing?

Definitely not typical because it goes up and down for me, depending on what else I'm doing. But let's say I interview one to three people in a month and then write up that interview. So that's an hour. I mean, I'm going to call that probably 10. If I'm, if I'm picturing like two or three people, that's 10 to 15 hours right there. Because it takes me a long time to write. Sure. And if I then add on doing like an ink article where I typically don't interview somebody, that's another probably three hours, maybe four hours. So whatever that is. Like, I mean, I think that in a month I probably spend a good 20 hours on writing.

20 hours writing, right. So that's at least, at least half a week. If you distribute that, it's roughly five hours a week, at least done writing. And clearly that's not only diversifying but growing your client base as well. And it's tremendously valuable, especially now that you've, now that you've got sort of regular outlets and a relatively diverse set of outlets as well, that starts to broaden it out as well. Are there other ways that you generate business that drive leads? Like how else can you, if you're stepping out, you're going to build this career based on your expertise and this thing that you'd like to do. Your writing clearly very powerful. How else do you generate business? What else drives leads into your business?

Well, I used to really, I really made a point of asking for referrals and I think people like get uncomfortable asking for referrals. I mean, I really think that I've helped a lot of people and I know that our process is helpful for them and I just think like, don't you want to show other people? And so I'm comfortable asking for referrals. But at this point I would say people without my asking, I just today just got another referral, even two today actually. People find me through my website or they just email me and say, oh, I know somebody who's looking for a coach. Can I refer you? So track record and existing network also, you know, I was just on the BBC even just last week and that generated the BBC and the New York Times. Whenever I'm in them, they're like, oh, I saw you. People have never, like I met 12 years ago or like, oh, I saw you in the New York Times, I saw you in the BBC. So that's cool. And it keeps me on people's radar screens. You know, there's an alchemy of how you get business and you should not always clear what's the one thing that's going to lead to business. I know that somebody hired me after meeting me eight years ago, right?

Yeah.

So it's sort of, it just, you just have to have a sense of the long term nature of the game.

I saw this illustration, it was about COVID and it was about how it was like the Swiss cheese strategy for managing Covid and it was basically a slice of a bunch of slices of Swiss cheese where the holes didn't line up right and every slice was like wearing a mask, social distancing, small groups being outside, well ventilated, that type of thing. And so like some virus passes through every slice, but less passes through multiple slices. And so by the time you get to the end, right. There is very, very little that gets through. And I think, I think. And the reason why I bring that.

Up, I was going to say, why is that relevant to our going with this?

I just really like Swiss cheese. That's really it.

He's like, I'm obsessed with COVID and cheese.

Right, right. These two things that are like, you should see my fridge, it's just full of Swiss cheese. Emmental or no, it's really amazing. But the idea is that there is no one strategy that is a silver bullet for driving leads to your business, to yourself, to these opportunities. It's all of these things together, right. That some leads are gonna pass through and others are gonna get blocked. So it's writing, it's giving, networking, it's doing stuff like this that we're doing right now. It's networking, it's these happy hours media, etc. And eventually that starts to build, right? This kind of these consistent leads that come from these various sources. And sometimes, like you said, those sales cycles will be years long.

Yes.

You'll just wake somebody up. This happened to me. In fact, I've been teaching a class for the last month with, with one of the big hardware stores in the United States. You might recognize them. And, and the guy who hired me for that is a guy I worked with 14 years ago.

Yes.

And I really just lost touch with him. And then he just kind of pops up. He's like, hey, I've been reading your books and I've been following along and now I'm ready. Right now I'm ready to h. And it's amazing to me.

And you didn't even know you were waiting for him?

No, I had no idea.

Oh, now you're ready.

I'm thrilled that you're here though. Fantastic. But let me ask you one more clarifying question. So I've got two more questions for you. One more clarifying questions about question about this. And then sort of one more kind of bigger closing question. So media you talked about the BBC, you talked about New York Times, you talked about Inc. And these other Forge, et cetera, all these different places. How do you choose which media to do? Is it paid work?

Typically?

Do you ever say no to certain publications? Like where? How does that decision making process work for you?

Well, it's pretty organic. I mean, if I've heard a couple of a publication then like I'm pretty sure other people have heard of them. And so I think that's probably a good use of my time. I think being nice to reporters is a good use of your time. I just, I just recorded an audio course for Knowable called Learn to Love Networking. So Knowable is a new startup that's doing audio courses. It's called Learn to Love Networking. Feel free to check it out. And in that I say it never hurts to have context in the media.

Right.

In terms of who you're thinking about adding to your network. And so I follow my own advice on that. And do I turn anything down? Yeah, I turn things down. Especially, you know, when I think about, I turn down a lot of like virtual summits or why they are time consuming and there's a lot of people doing virtual summits. And so I'm not so sure if I'm going to get a lot of reach from those virtual summits. Now. I don't, I do do like May Bush does a virtual summit in January. She's super well known. She's a good friend of mine. Of course I do her virtual summit. Marshall Goldsmith is doing a virtual summit. Of course I'm gonna be involved in his virtual summit. So it's more like people I've never heard of. Maybe. But none of it's paid, to answer your question. None of it's paid.

Yeah, it's interesting, right? I mean the pay comes from the leads in the network. Right. And the audience that you're building. And that's part of the hustle. It's part of the work, I think that a lot of folks don't realize, you know, like, oh, you're doing another conference, you're doing another version so much you're doing another piece. Yeah, it's the work. This is the sales part of the work itself.

Yeah, definitely.

Okay, I got one more question for you and then, and then we'll wrap this up. So this one's really interesting and I'd love to get your take on this and maybe I'm getting a little free coaching out of this. We'll see out of the process.

Warning, warning for coaching.

Apologies if I'm asking for coaching, but here's what I'm seeing. So in my world, one of the sort of competitive advantages that people have who do what I do for a living is geography. So for example, someone is the best or best known agile coach in Amsterdam. Someone is the best product management trainer in New York City. Right. Covid has killed that. The idea of a geography based moat is gone. Everybody's teaching in the same Place. Online.

Online.

Online. Which means that I, and people like me and everybody else is now competing with literally every single other person in the world who does anything remotely close to what I do for a living, which can be really, really intimidating. For example. Right. I. I'm expensive. There are people who do exactly what I do for a lot less money than me, and I never really had to compete with them because we never taught at the same place at the same time. And I would fly, and maybe they wouldn't fly, or something along those lines. I would go somewhere, they wouldn't go somewhere. That type of thing. That's gone now. All of us are playing in the same space. Anybody can. As long as you're willing to adjust for a time zone.

Mm.

Right. Anybody can play in any space at any time. I can sell classes. Like, literally today, I, you know, I spoke at a conference in Scotland. I worked with my client in India.

Right.

And I did work with my business partner in New York.

Mm. Right.

That's today.

Yep. And now you're conducting an interview with somebody who's in Montclair, New Jersey.

Exactly. My favorite state in the whole world. And so how do you stay relevant, in demand, when that. With this new added level of competition and the competitive advantage of geography completely gone, how do you maintain your edge in this world?

Yeah. So I love this question, and I am going to definitely give you some coaching because I think you need to reframe your attitude. Right. So I am known as the top startup coach in the entire world. Okay. I'm not playing in the Newark, New Jersey area. And I would invite you just today, by the way, I spoke to somebody who's. He's based in Belgium, and I said the same thing to him, which is that now is the time to do just what you said, which is not have to travel. So you've leveled. You've democratized and leveled the playing field, which means you have 100% access to build your brand. And building your brand commands higher fees, more notoriety, more people coming outreach to you versus you, outreach to them. And all of those things together are totally playing in your favor. And I would say to you, don't think of it as a competition. Think of it as what do you need to do to be top of everybody's radar, both in terms of kind of brand excitement as well as just knowledge, like, top of mind as well as knowing so many people, they come to you first. If all those things are working together for you, then geography in this time becomes your friend, because you just did all those different things. I know that I myself just did a keynote in India for 300 Indian CEOs over India and Asia. CEOs. Like, they would not have flown me in to do that. That would have not been so easy to do. Right. So there's so many virtues of this time. That's how I invite you to think about it.

Right. So it's. You're saying, hey, it's not actually a competitive disadvantage, it's a competitive advantage because now you've got the whole world and new opportunities and the ability to work in three different countries in one day.

Exactly.

Whereas before, it would have just crushed your soul to be on that many airplanes.

Right, Right. And you wouldn't have had the time. You literally wouldn't have the time. You cannot do three events in a day in three different locations. But on video, you can.

That's right. It's pretty amazing. Alyssa, thank you so much for sharing your expertise and spending the time with me telling us your forever employable story. It was a ton of fun, and I wish you nothing but the best and success in the future.

Thanks, Jeff. Likewise. And thanks so much for having me. E.