Welcome to uploading the podcast, where we take you behind the wheel with the world's best creators, marketers, and professionals who have cracked the code on how to profit through content. You'll learn the ins and outs of content, strategy, creation, production, distribution, growth platforms, tools and more. If you haven't already, be sure to join Cas Magic, the all in one content workspace for professionals. We'll be sending out tips from our shows in our weekly newsletter, and we've also got a slack community of over a thousand creators, so make sure to drop in and say hello. And now get ready for the show. Welcome to today's episode of Uploading. Today we have the pleasure of being joined by Alyssa Cohn, who is a coach and works with startup CEO's, co founders, and other executives and board members all over the world. Alyssa has been named the number one startup coach by global Gurus and has worked with executives in Venmo, Etsy, Dell and the New York Times.

She's got a book called from startup to grown up, which is a guidebook for anyone who wants to grow as a leader. And she also has a podcast by the same name for startup to grown up, where she's interviewed multiple execs, coaches, everyone from the co founder of Loom to many other really successful leaders. In this episode, we're going to talk about how she became one of the top startup coaches in the world, how she's leveraged social media to grow her coaching business, and how she applies her coaching frameworks and content to her own life. So, Alyssa, I'm not sure if I covered everything, but I'll let you kick us off. Why don't you tell us a little bit more, you know, about your background and what got you started on the path to being such an amazing coach.

I love it. Thank you guys so much for having me. I'm so excited to be here. And I guess I would say that my epiphany around becoming a coach, it started with my epiphany about wanting to leave the corporate world. So I was in the corporate world. I was at Price Warner House Coopers, which is a fantastic firm and also not a good fit for me. So I thought to myself, I hope I get the flu so I don't have to go to work tomorrow. And indeed, I got the flu.

And so I was rushed to the emergency room and I just thought, this is not for me. I gotta figure out what it is and the reason, you know, I think it's important for all of us to sort of listen to ourselves because I think a lot of the Joseph Campbell quote, which is if you see your path all the way through to the end, you are following someone else's path. Your path only becomes clear moment by moment as each foot hits the ground. And that was definitely my career at PwC. I was like, I'm all set. This is going to be the thing. But, like, ultimately it just did not nourish me. So I set out down the path to figure out what nourishes me.

And I had to look at a lot of different things and it was really challenging. But ultimately I went to this conference as a volunteer, and then the people said, okay, now this coach is going to speak to the volunteers. And I'm like, do I have to be here for this? Like, what is this? And then it turns out that this coach spoke to the volunteers and I was completely mesmerized. I was like, what's that? I want to do that. It was like violence played and I could see that is the thing that I want to do. And then I followed her around the conference, and at some point she did this talk with 500 people and she said, who wants to stand up right now and get live coaching? And I thought, what's going to happen now? Someone stood up. She did live coaching for like 20 minutes with that person. And I thought, oh, my God, I could never do that.

But at the same time, I thought I could do that. I really saw myself in her and in coaching because fundamentally, coaching is about making a difference. And I really knew that the, my essence at my core, I wanted to make a difference and have an impact. And that's how coaching was sort of fit into the whole thing. And I just sort of said, okay, I'm going to get started on this path.

So what, what did it look like in the early days? Like, what was, so you have this experience, you realize you're like, this is something that resonates with me. Like, what came next? You still had a job, presumably, like, so what, what did that transition look like? What did the first, you're dipping your toes into the coaching world look like for the first time.

Yeah. So I still had a job. And also I was super young. So I'm thinking, how can I be the executive coach? So young? So I took coach trading, I hired my own coach, and actually I got a job in the startup world. So I was a CFO of one startup and then I was the head of strategy of another startup, and that was all in the two thousands. And meanwhile I was pursuing coach training and coaching all my friends for free. And, you know, the startup world imploded, as you may know, in those days. And then I thought, okay, great, I'm going to become a coach now.

And it was like on Friday decided to become a coach, and on Monday I became a coach. And the first thing I did, I'm not saying this is the right thing, but the first thing I did was create a vision board of my ideal life as a coach, because I knew that the going was going to be hard, which it was. And I wanted to have an understanding of what I was really shooting for, both in terms of making an impact, having autonomy in my day to day, and being able to explore a lot of things that interested me and sort of under the guise of work, and of course, being successful as a coach. So, like, creating that vision board was actually very helpful to me. I still have it to this day. And then it's like, what do you do? You have to go get clients. So I've been already coaching people for free. I now kind of upped the ante by coaching people for free and insisting they give me testimonials.

And then I went down to my gym, who was having a vendor fair, and I had people sign up for free sessions, which was really intimidating. And then they signed up for free sessions. And half people didn't even show up for their free sessions, but a few people did. And I got more practice coaching people. And one of those people from those first free sessions actually signed up and became my first paying client. Thank you, Rick Samuels, for paying me my first paying client. And then I just kept putting 1ft in front of the other. So I, you know, tried to.

I taught adult ed for a little while. I used. I'm a CPA. I was at pwc. I was a strategy consultant, but I also did my tax and audit hours, so I'm also a CPA. One of my colleagues knew that. She brought me in to teach the financial acumen program at this large company. And I knew that if I could start teaching that curriculum, I'd work my way into the leadership curriculum, and from there, I'd be able to get more of a reputation as being a coach.

That's exactly what happened.

Amazing. And one reason, Alyssa, that I'm excited for this conversation. I think there's so many things that we can get into. A, I want to talk about the coaching stuff, which we're definitely going to cover. B, I want to cover, you know, what you see in, like, amazing other leaders because you've had the pleasure of working with really high performing people and then c I want to cover content, right? Like, I think, you know, like we said, you've written a book, you're big on LinkedIn, you put out content all the time. So there's going to be a lot for us to cover and we can kind of jump around and keep things fun. But why don't we start with content, right? Like, how did you start getting into the content world? How did you start on LinkedIn with the book? Like, how did all of this sort of come together and what is your content strategy and how does that play.

Into you being important for coaches? There's really no way you're gonna be able to be successful if you don't have the ability to share your ideas. You call that content? Content is sharing your ideas. And I got started because I knew that I needed to have a few different channels. This is before social media, really was before social media. And so it's like, how do you get the word out to people so they know you're around? And in those days, the best way to do that, I realized, was an email newsletter. So I began to write a monthly email newsletter. I did that for years. Note that I never had twelve editions in a single year of my monthly newsletter.

And the reason I say that is because I did it quite imperfectly. So the way to do it is imperfect. For whatever reason, I was very nervous about I'd slave over writing articles. I'd be super uncomfortable and vulnerable again. In those days, you couldn't just like you had needed a tech guy to release your newsletter. Like, I did not do it by myself. It was before all the tools were around. So I had Barry launch my newsletter, as I told him, as I went and hid in the closet, which I literally would go do, and amazingly, people would write back to me and they'd give me really positive feedback about this newsletter.

And so that was very validating for me and super helpful. So I began to be a little more comfortable writing my newsletter. And because I then had my newsletter, I was able years later to use that as kind of like clips to then write for Worse magazine, the worst.com comma, like the online blog, because they used that as an understanding that I could write again. I really had to do, I would be very proactive in reaching out to them and having them not get back to me and continuing to follow up with them and ultimately write articles for them. And then I used that and plus my newsletters to be able to write for Forbes and then inc.com reached out to me to ask me to write for them. And that's really how I got started writing. And of course, then I started pitching the Harvard Business Review. And again, all of my background was able to get me to there.

So that's how I started writing for, let's say, news publications, as well as my own personal blog. And I moved it all to LinkedIn over time, once I began to see that LinkedIn would help me reach a bigger audience, because ultimately, if I write a great article for HBR or if I write a great article for Forbes, that's fantastic. But nobody knows about it unless I have some sort of audience, unless I have some way to promote the content. So it was in building my LinkedIn presence, in sharing ideas on LinkedIn, and then sharing these articles on LinkedIn, that I began to be able to build my audience as well as people would begin to know about these articles. Honestly, what I then discovered on LinkedIn in particular is that when you just write little reflections on LinkedIn, little thoughts, short and somehow poetic, or even sometimes almost like aphorisms, people love it on LinkedIn. You could slave away over a long article, or you can just share a few thoughts, which I feel like are half formed, and people jump in and they want to respond to their own thoughts. So having a balance of those different pieces of content is actually very helpful. Watching what works is very helpful.

I trained myself to recognize, like, oh, interesting. People don't like, this is something that's so obvious to me. Like, whatever it is, it's maybe like, I don't know, even just like what I said to you about the Joseph Campbell quote, when you can see your path all the way through to the end, you're following someone else's path. Like, I would say that. And people would go, oh, wow. So then I would say, huh, people seem to really resonate with this. So then I might put something like that on LinkedIn, and I might write a few sentences about what that means to me or what that meant to a client of mine. And then people jump in and respond.

And that's how you begin to train yourself to realize about what are the things that you naturally think or say or do, which are actually noteworthy, and our content, you know, the idea of content for other people. And so my advice to everybody is to just be on the lookout for the things that resonate with people and then begin to try them on whatever social, you know, medium of your choice helps you to test out your ideas, because you have to be testing out your ideas and also getting feedback, which is this is not a good idea or this is a good idea in order to really see what's going to resonate with your audience.

Alisa, one thing that I'm very curious about is how did this impact your, your practice and your coaching to your clients? Because it seems like this is, this practice of building your personal brand on LinkedIn is allowing you to have faster feedback loops. And when you're a high ticket coach, you don't have as much data and as many fast feedback loops. So you're treating what you're seeing on the content as data. And so I'm curious how that translated into the services that you provide.

Yeah. So first of all, it just, ultimately, it really just profoundly builds your brand so more people know about you, which means they have the opportunities to reach out to you with opportunities. So, like, you know, they'll want me to be on their podcast, or they'll want me to join their committee or their board, or of course they'll want to hire me for their company or for themselves, either to speak or to coach. So of course that's important. When I was writing my book, there were times that I just wanted to sort of get some fresh thinking about what I was. Something I was thinking about. I put it out there on LinkedIn. People would respond to it.

It would help me refine even what I was thinking about. Excuse me. When I remember this, one very direct thing that happened is that I wrote an article for HBR, Harvard Business Review, and I put it on LinkedIn and got, for whatever reason, it got a lot of views. And then somebody from that emailed me directly and said, I must speak with you today. I was like, what's going on? Crazy people out there. So I was like, okay. So we spoke that night at 05:00 and he hired me on the spot. And that was a direct result of writing an article of hard business review and putting on LinkedIn and immediately getting a client.

So there's like a lot of different ways, large and small, that this content creation helps you. It helps build your brand, build your reputation, it helps you tangibly, it helps you think out ideas. It helps you build a tribe and an audience around your ideas. I think it also helps inspire other people, for sure.

It's the intangible roi, which, if you're coming at it trying to see how much money are you going to get back from the money you were investing into your content, you're probably positioning yourself, you know, at a place to fail because it is a long term investment in terms of building a brand. I'm curious, what was your content workflow? Did you even have one in the first place? You know, how would you allocate creating content throughout your day, aside from, you know, most coaches were starting out. I need to get. I need to get clients. I need to get better at my craft. I need to be on calls. I have my community that I'm probably coaching. How did you prioritize and allocate time for creating content?

Yeah, so one, I think, feature of myself as a solopreneur is that I am a hard worker, and I am really, like, focused on the hustle. Like, I would say for decades. Even now, I hustle every day, which means, yes, Ramon, I had to do all those things. I coached my clients, I looked for new clients, I went to networking events. Really, I was doing all of it because I had to run my own business. I was especially, the first five years, I was terrified. And I made time for content, whether it was weekends, whether it was, you know, I had an idea after getting off a coaching call, and I would just sort of write it down. I was not systematic.

I have become a. I've become, actually, I would say, much more systematic now. In the early days, I was not systematic. I just kind of did it and made time for it. And then over time, I think for all of us, like, you kind of realize, oh, if I had a system for this, it would be much better. So when I began to create a little bit more of a system, I tried to do batching some of my writing, thinking about the schedule of my LinkedIn posting. I'm on the other socials, but, like, LinkedIn is where I have 100,000 followers, and so that's kind of where I invest most of my time. And then when I was writing my book, I had no choice.

I had to really carve out specific time to make sure I was writing my book and also maintaining my presence on LinkedIn. Because, as you both know, that, like, writing a book is one thing. Launching a book is a whole other full time job that's unrelated to writing the book. And one of the things you need to do is find people who will write about you in the media. So that's, like, to your point, about long term investment building relationships with media, you know, and reporters for ten to 15 years, as well as building your audience on LinkedIn who are, or other socials who will then want to buy your book when it comes out and give you reviews and do all the things you need from books.

Alyssa let's talk about the book. Right. What was it like first? Like, what's it about for people who are listening, you know, from startup to grown up, what's the concept that you're covering? And then I also want to go into like, how you were able to formulate it and write it based off all your experiences.

Yeah. So my book is called from startup to grown up. And it's the journey, the personal growth journey it takes for founders to grow into leaders. But really it's about the personal growth journey that all leaders have to go through as they grow into leaders. It's divided into three sections, managing you, managing them, and managing the business, because those are the dimensions that you to be successful as a successful leader. And the back of the book and the appendix are 14 scripts to help you have delicate conversations, difficult conversations. Because I find that my clients having scripts and getting sort of their mouth around the words is very helpful for them to be able to do what they need to do to like, have difficult conversations. So I just want to say, like, super honest that it took me years to get over myself to write this book.

I was like, I have to write a book. I need to write a book. I'm not writing a book. It's so frustrating, and it's hard to write a book. And I'm not exactly sure what my inner block was. There was definitely some identity piece, which was like, I can't write a book. And then for better and for worse, there was a global pandemic. You may remember it.

And I thought, this is going to free up a whole bunch of my time traveling, right? I'm not going to have as much to do. If you don't write this book now, then you are just not a serious person. So I pulled myself together, I got my book contract, and I wrote my book during the pandemic. And, you know, figuring out the it was. I just want to say that I think a lot of creative pursuits are frustrating. They're trial and error. You sort of start off down one pathway and you realize it's not going to get you all the way there. But when I ties back to LinkedIn, when I talked about managing you, managing them and managing the business, sort of that structure, people really resonated with that structure.

And I was like, oh, that's the right structure for the book. And then there was something just around sitting down, finding a structure for the book itself, and then just sitting down and writing the writing every day, picturing my stories, clarifying my stories, recognizing where my stories might go and then figuring out how to create the narrative around that. I think there's a lot of trial and error to that, too. But then you get into a rhythm, and so then you can figure out, like, what's going to work for you. I should also say that I spoke to eleven entrepreneurs for my book about their personal growth journeys, and I took little pieces of the transcript out of my discussions with them, and that's how I started my podcast. I was like, I love these conversations. These are amazing. And they would say, oh, these are great questions that you're asking.

So I realized I wanted to continue having these conversations, and that's why I started my podcast, also called from startup to grown up, where I interview, as you said earlier, the founder of Loom, the founder of Kayak, Chip Conley, the founder of Jordan Beef Hotels, and other amazing founders. I just interviewed Gary Vaynerchuk today.

Oh, amazing. So I'd love some of the, like, what are some of the learnings? Right. You not only interviewed several of the highest performing people, but you have worked and coached, like, very successful executives, founders and all the like. So what are some of the learnings? What do you see across the board as a coach? You know, someone new comes in. What are some of those things that everyone can, like, really work on to improve?

Yeah, I think one thing I would say is that you have to have self belief, and that may sound simple, but a lot of people are suffering with imposter syndrome or insecurity or lack of confidence, and then they don't even try. So one thing about high performers, and certainly founders, is they are triers. They will try and combined with that, they have the grit to overcome obstacles, because there are many, many, many obstacles on the way to success. So you have to kind of realize and not be daunted and afraid and upset by failure, setback obstacles along the way. So I think that mindset is super important. There's no substitute for elbow grease. You must have, you must be able to work hard and have stamina to work hard. And you've got to create a community around you.

As in, you've got to hire employees, you've got to find backers, whether it's investors or other professionals, to help you. You've got to build up a customer base. And the way to do that is to build community around you. And so there's got to be ways to do that. Social media is one way to do that, and another way to do that is just to be out there in the community helping other people and becoming, you know, someone recognized for their. For their contributions and for their wisdom and insight.

I'm curious, Elisa.

What?

And I definitely resonate with a lot of that. I'm sure Blaine does, too. You know, having. Having to go out there and face the barriers of, you know, having to raise in a market that isn't, like, the most frothy market, and you're like, oh, man, here we go. We have to go for it. And, you know, overcoming that imposter syndrome, having to do layoffs in a time that you don't really want to, and you might just want to keep going on the path you're in, because it's just easy to do that. But reality is you need to. You need to check yourself and you know what's right deep down, and you need to make those calls.

And these become very frequent. You have to. You know, the more familiar you get with them, the easier the future is going to be. But they're also. There's always going to be a bigger decision to be made and a bigger action to take. Um, so it's very unfamiliar territory. I'm curious, what have you. Can you talk about any, like, transformation from a client or any.

I would call this, like, your brag time. Like, what is it that you've seen a customer, a client, do that? You're like, wow, that even impressed me. Um, how they overcame that, and how did you help them through that?

Yeah, I mean, there's. So I would say I've had those kinds of moments with every single one of my clients, but one that comes to mind is that I worked with a founder who was really exceptional at raising money, which is like, yay, that's fantastic. So you can imagine, he was charismatic, he was persuasive, he was passionate, and weirdly, he was having trouble growing the company because he could not bring senior executives to the table. Like, that's so strange. Like, what is going on? And I would listen to him, and I kind of realized he just didn't have that passion and that drive on those discussions. So I kind of said, what's going on? Maybe they just weren't. They found a different opportunity, or they weren't the right person. And I'm like, no, seriously, what is going on? And we were able to tap into what was really going on with him.

His inner voice said, I don't want to pull them away from these safe jobs because I don't know what's going to happen with our company, which is a normal thought. And it was getting in the way of him really going for it to land these senior executives. So we talked through that, and I helped him bring evidence to that thought. Right. He was having this kind of unconscious, semi conscious thought, uh oh. I don't want to have them come away from their safe companies. Okay, so what is some evidence? What's some rationale that you can bring to that? Well, they know what they're getting themselves into. Maybe they find their safe jobs kind of boring.

They'll have a lot more opportunity and certainly a lot more upside at this company, this startup. If you're successful and do you think if you're not successful, you pull away from their safe jobs? It's like game over. They'll never be able to get a job again. Probably they'll be able to get to get a job again if that's ultimately what happens. In fact, they'll have even more experience in order to bring to the table. So with that in mind, he was able to completely transform his approach with these senior executives. He was able to bring them on board, and that was the key and the big unlock to massive scale of his company.

That's really cool. I wonder, have you ever, how do you overcome a client who, because what you're doing with them is uncovering blind spots, right? We all have blind spots. And so I'm curious, when you work with a client, are people initially in the beginning of the relationship with you, they might not be as open to admitting that that is a blind spot, be defensive, and you, you might already, this is an art for you. So you see this happening in real time where they're kind of rejecting it and they're slowly, well, say that again. Well, hey. And then they come back to you.

Hey.

I actually thought more of what you said. I think there's something to that. And eventually they fully come around.

So I'm curious, Ramon, to me, that's called. Yeah, that's called Tuesday, you know, every day. That's so true, because people, especially founders, and you guys, may relate to this yourself. You think, you know, you have this idea, you pretty sure you know what you're doing, and you have strong personalities, and in the best way, you've got conviction. So it's hard to listen to other people sort of tell you that there might be something else you're not seeing. One place that really shows up is 360 feedback. So in case you don't know what 360 feedback is, everybody. It is where I talk to the folks around the executive and I say, what's working? What's not working? What is this person great at? What is this person to get better at, and what are specific suggestions you have for this person? So I compile all of that.

I talk to eight or ten executives around the CEO or the founder I'm working with, and then I present them. Here's the data, here's what they say. Now, normal people will say, no, I didn't mean that, or no, it's not like that. Well, okay, but I got ten people who say it is like that. So what do you think? Because you're the expert on your intention, but everybody around you is the expert on your impact, and so it's really important to be able to marry that intention with that impact. Human beings are normally defensive or in denial, and it takes them a while to digest the situation. But I would say that most of my, not most, the founders I work with also, the counterbalancing point is they want to be successful, but they want to win. So they're willing to, after a little while, they're willing to look at the truth and then deal with the reality of what's going on.

A lot of that's ego, too, right? Like being able to manage your ego and be open to hearing things that maybe you don't want to hear in the hope or because it's going to make you a better person. Um, Alyssa, one thing, one last thing I want to cover is, um, the idea of how all of this applies to coaching, right? Because we talked about it from, like, you know, standard executives operating a company, solopreneurs. And these are general practices you can apply to your job. But, like, if you were a coach starting out, like a, what are the lessons? I mean, probably all of them, but what are some of the lessons that can be specifically applied to coaches who are looking to, like, scale up their business? And then b, you know, what advice do you have for coaches who are somewhere along this journey and that are aspiring to get to kind of where you are, where you're on Tim Ferriss's podcast and you have your book out and your coaching top execs, what advice do you have for them to become a top level coach?

Yeah. So step one, get great at your craft. So you need to have reps, you need to have clients, whether it's for free, whether it's only not a lot of payment, like not a high fee, you don't have to, like, the first step is to get clients one way or the other in order to get reps and to get practice at your craft, to get better at your craft, find a mentor, find your own coach to really help you have that confidence of being great. And then I certainly think in the age of social media, you've got to find a way to get, to get attention by sharing your ideas. So you could build your own community, you could join another community, you could post on social media. I think you should figure out what channel is going to work for you and find ways to share your ideas on social media and begin immediately. Something I did not do, I encourage everybody to do begin immediately to try to figure out what's my book? If your book is ten years away, that's okay. What's your book? Think about it now.

The things that you're noticing that you think you bring to the table, your frameworks and models which are working as you get more and more reps, that will sort of be the basis and the foundation of your body of work. So I would say get great at your craft. Definitely find various different ways to build your brand, pull a community together, and you've got to be fearless. You've got to just try again. You've got to be comfortable failing. You've got to be comfortable trying to get new clients and having it not work and then debriefing what didn't work. We're talking about defensiveness and ego. You've got to get over your own defensiveness and ego to just recognize that's okay.

I'm going to just keep trying and keep taking shots on goal in order to recognize that you will get better and better at even the business side of it. Because the business side of it, the sales side of it, the getting new client side of it, is just important as the coaching side of it.

Yeah, absolutely. Alyssa, want to thank you for coming on today. We covered a ton. Was super informative for our listeners who might want to find more about the book, connect with you, follow along your content on LinkedIn. Where can we find you? Why don't you shout out your socials and where we can connect?

Yeah, totally. So you can find me on LinkedIn and follow me there and all the other socials. And in every case, if you just google or search Alyssa cone, you'll find me. That's a l I S a n a c o h n. Also, come to my website. On my website, I have five additional scripts to help you with delicate conversations and one to make your life better. And that's alysacone.com scripts.

Thanks so much, Alyssa.

Thank you, guys.

Thank you.