How to Grow from Startup Founder to World-Class CEO

Alisa Cohn left a partner track at PwC to find more hands-on impact, then trained as a coach after watching Cheryl Richardson work live. She went on to become a startup CFO and head of strategy, learning what separates first-time founders from world-class CEOs.
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In my opinion, the Founder Journey is the best personal development program out there. Can I get a hands up? If you agree, you have to dive into untapped territory you would never have explored without becoming a founder. Fortunately, our guest is here to help you grow from newly minted first time founder to a world class CEO. Stay tuned for the Startup Life Live show. Hello everyone and welcome to the Startup Life Live show. I'm your host, Andy Lyons, startup coach to first time founders. And after raising four businesses of my own, I now help newly minted business owners sleep through the night by giving them peace of mind. And for those of you watching live, thank you for carving out time to up your founder game. And those watching the replay, I am so thrilled that you're here and looking to improve your founder skill set and mindset. Please be sure to click the like button wherever you're watching. And those watching on the replay, be sure to not only like the video, but subscribe to my YouTube channel. So grateful. Now I have to tell you, our guest is the serious, unbelievable, amazing Alyssa Cohn. And I'm sorry, excited to tell you more about her. You know, she's been coaching startup founders into top notch CEOs for 20 years and was named the top startup coach in the world with and a top 30 global guru for startups in 2020. Now this is a one time startup CFO, a strategy consultant and current angel investor and advisor. And she has worked with startups such as Venmo, Etsy, the Wirecutter, Mack Weldon and Tory Burch. She has also coached CEOs and C suite executives at enterprise clients such as Dell, Hitachi, Sony, IBM, Google, Microsoft, Bloomberg, the New York Times, and Calvin Klein. Okay, so she knows what she's talking about and we're going to ring out every piece of advice that she has today. I'm so excited to introduce you to the one and only Alyssa Cohn. Welcome to the show, Alyssa Cohn.
Hi Andy. So nice of you to have me.
Thank you.
It's great to be here.
I love your energy. I am so grateful that you came on and joined us because we all need to continue to tap into our capability. And a lot of times folks, you know, you could have gone your whole life and not known what you're learning now as a founder. Right, Alyssa?
Yeah, that's really true. Prevent mistakes.
Exactly. So I want to let everybody know that we are live streaming on LinkedIn, YouTube, Twitter, Facebook, Twitch and Periscope. How, how cool is that? And I'd love for folks to pop into the comment threads where you're hailing from. I'm hailing from Boston. Alyssa, where are you hailing from today?
I'm from New York City.
All right, we'd love to know where you're hailing from. And if you are a founder of a business owner, which is why you've tuned in, please put the name of your company and the URL in the comment threads. I'm going to bring it right up here and we'll do a little spot spotlight on you. Let more of the world know what you're doing, your mission, your vision, and your beautiful business right up here on the screen. And, Alyssa, we're going to talk a little bit about networking later on, but I have found since the pandemic, these live shows are a terrific way for folks to network. You can meet people in the comment threads, whether it's a live stream show like this or a webinar or a zoom, put it out, grab your LinkedIn URL and share it with the folks and get theirs. And if they don't share, go look them up on LinkedIn and say, Hey, I saw you on the Startup Life Live show. Let's connect. Because you never know where your next collaboration is going to come from. So I just wanted to throw that out to everybody before Alyssa and I got started talking about her extraordinary background. Alyssa, you've been at this for nearly 20 years. I'd love to know, how did this idea to put your shingle out as a startup coach, how did it pop into your head? And of course, how did you find the courage to leave that paycheck behind and dive into entrepreneurship?
I know that's such a big question. Yes to all that. After business school, I went to PricewaterhouseCoopers and joined their so called fast track to partner program. Five years to partner. And. And in the middle of that, I just realized, this is not for me. PwC is a fantastic firm and it was a great place for me to learn a lot of skills. But ultimately for me, it just felt too big for me to really have an impact. And I had this idea in my head that was important to me that the work of my hands mattered. Like, where did that even come from?
I don't know.
But a voice in my head said to make a difference was my mission and calling and that it was important to me that the work of my hands mattered. So I left PwC and I thought about what do I want to do and how am I going to figure it out? I went to a conference as a volunteer and at some point that we went to this training, and then at some point somebody came in and they said, okay, now Cheryl Richardson is going to speak to the volunteers. And I thought, can I leave? And I was like, well, who. I don't know who this is. Is this mandatory? Can I leave? So Cheryl Richardson, my very first executive coach, is like a life coach. Spoke to the volunteers and music played. I thought, what is that? That's. That's what I want to do. Because I could tell she could make a difference. And I could tell that her kind of signature presence, her Persona was like mine in terms of the way people obviously gravitated her to help them solve their problems.
Oh, my gosh. Who knows Cheryl Richardson, she lives up the road, 20 minutes.
Oh, that's right. I forgot. She. She's a Boston girl.
Oh, my gosh. And her hus, Michael Gerrish. Oh, back probably about 20 years ago, had a book on when working out isn't working out. And my husband is chapter nine. Oh.
Oh, my God. That's amazing. Wow.
We are all fans of Cheryl Richardson in this area and throughout the world. I can't wait to tag her on this. Alyssa, please do.
I just want to say she really inspired me. And I was like, I'm going to become a coach because of seeing her. And specifically I saw her live coach in front of 500 people. She said, okay, does somebody want to stand up now and get live coaching? And I thought, what is going to happen now? And someone stood up and she live coached them for 20 minutes in front of 500 people. And I just thought, I want to do that. Like, I knew that I could do that. It was really intense. And then I joined the startup world. As you said, I was a CFO of one startup, the head of strategy of the startup. I took coach training and all that. The startup world kind of went kaplooey at a certain point. And I thought, now I'm going to become a coach and not just look for that same job that I keep getting. That's what I did.
I got to tell you, that is so much better than doing where you were with Pricewaterhouse. Bless their hearts. Your track folks, you basically have time to get your dry cleaning, and that's about it. You know, it is a hard track. And I just love the story of you seeing that serendipitous moment when you saw.
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