One Foot In Front Of The Other With Startup Coach Alisa Cohn

VCP 130 | Startup Coach

What do you do when your goal seems far off? Tony Martignetti’s guest today is Alisa Cohn, #1 Startup Coach by T50 Marshall Goldsmith Awards. Alisa shares with Tony how she had to go to the vendor fair and talk to strangers while it was snowing. It was the last thing she wanted to do. But she knew she had to place one foot in front of the other to become a coach. You need to start working to be where you want to go. Tune in and start working!


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One Foot In Front Of The Other With Startup Coach Alisa Cohn

It is my honor to introduce my guest, Alisa Cohn. She was named a top Startup Coach in the world at the Thinkers50, the Marshall Goldsmith Global Coaches Awards ceremony in London. Alisa has been coaching startup founders to grow into world-class CEOs for many years. She’s a one-time startup CFO, strategy consultant, Angel investor and advisor. She was named a Top 30 Global Guru and has worked with startups such as Venmo, Etsy, The Wirecutter, Mack Weldon and Tory Burch. She has also coached CEOs, C-Suite executives and enterprise clients such as Dell, Hitachi, Sony, IBM, Google and many more.

Alisa is a guest lecturer at Harvard, Cornell University, Henley Business School and the Naval War College. She's the Executive Coach for Runway, the incubator at Cornell NYC Tech that helps postdocs commercialize their technology and build companies. She serves on the Board of the Cornell Advisory Council. She has coached public and political figures including the former Supreme Court Chief Justice of Sri Lanka and the first female minister in the transitional government of Afghanistan.

VP 130 | Startup Coach

Her articles have appeared in HBR, Forbes, and Inc. She has been featured as an expert on Bloomberg TV, the BBC World News and in New York Times. A recovering CPA, she's also a Broadway investor in productions, which have won two Tony Awards and is prone to burst into song at the slightest provocation. She's about to publish her first book, From Start-Up to Grown-Up. I want to welcome you to the show, Alisa.

Thank you so much, Tony. I'm excited to be here with you.

Me, too. I'm honored to have you here, to be honest with you. I love all the stuff you put out there in the world. You have had such an impact on me. I love the work you do and the way that you have shown up in the world. It's powerful.

Thank you so much. It’s nice to hear.

We are at the campfire. It's all about creating this ambiance of sharing stories around the campfire. What we will do is we will tell your story to what we call Flashpoints. These are points in your story that have ignited your gifts into the world. As we are sharing your story, we are going to have you pause along the way and see what's showing up. You may have one Flashpoint or many and you can start wherever you like in your life. We will turn it over to you and let you take it away.

A lot of people ask me, “How did you become a coach?” because it's not a normal profession like a doctor, a lawyer and a teacher. Early on, when I was about fourteen years old and I was on a bus to this camp that I was going to, I was sitting next to my friend, Kim. We were talking about like, “What would you do when you get a job if you can do anything and not worry about money?” I said, “I would have intense conversations because that's what I like to do.” Show me the girl and I will show you the woman because what I do all day long is have intense conversations.

It's great when you can connect the dots to our childhood and say like, “That's who I want to be.” I'm willing to bet that it wasn't a direct path that you took from that child to the adult. Where were the pits and stops along the way?

Make a difference. The work that you do matters. 

When I moved through my life and I went off to college and I’ve got interested in education, I was the Chief of Staff to the Provost at Northeastern. We did strategic planning. At some point, he said, “You can't manage faculty because they have tenure.” I thought, “That can't be, the people will only do what you want them to do otherwise you would fire them.” I went off to business school to think about that and to think about why people do what they do in service of the organization and the mission or sadly, no.

In business school, I’ve got all turned around. Rather than focus on the people stuff, I’ve got focused on what everybody else is focused like status. I focused on finance, accounting and strategy. When I left business school, I went to PricewaterhouseCoopers and their so-called advanced development program, the fast track to the partner program. I thought, “This is it. I was a Journalism Major and I was a nonprofit kid but here I am. My ticket is made. I'm going to be a partner of PwC.”

First of all, I can relate to your story because I was a finance professional for many years. You think that your die has been cast and this is the path that you have chosen but how quickly you realize that it's not the end of the story and there's so much more to be had?

For me, the moment of truth was when I woke up one day and I thought, “I hope I get the flu so I don't have to go to work tomorrow.” Sure enough, eighteen hours later, I was rushed to the emergency room with the flu. A strong mind and be careful what you wish for, I was down for the count. The truth is the firm was fantastic. I made a lot of great friends in the firm. I have a lot of appreciation for the firm. To be honest with you, as the years go by, I know for a fact more what I learned from that experience. Even when I told the firm I was leaving again, they were amazing to me.

It wasn't the right fit for me. It was too big and a feeling that I was one of many. I recognize that I wanted to make a difference. That was the voice going through my head. I was down for the count, on my couch with the flu, the voice in my head kept saying, “To make a difference. The work of my hands' matters.” That's what I went off to try to figure out. That's when I met a coach. When I met a coach at a conference, it was like violins played. I realized that's what I want to do.

What I love about this, too, is there's something about the experience you already had where you are working in PwC and realizing that it's not about throwing that all away either. There are a lot of beauty and learning that you take away from that experience. It's not all bad. It's how you frame that that makes a big difference and realizing that you are taking that and you are, in a sense, transcended and include. You include that pass and you transcend it into something that's now going to be the path forward and coaching being the path. Tell me what you did first. Did you just said, “I'm going to be a coach?”

It’s true. I was leaving PwC and I went to the startup world. I was the head of the strategy of one startup. I was the CFO and GM of another startup. That all imploded back in 2000. I had already taken coach training. I had already coached all my friends for free. When I imploded, I said, “I'm going to become a coach now.” There are two things about that, one is that I’ve got offered a lot of jobs after that. At the time, my coach said, “You have been wanting to be a coach for a long time. You are going to keep getting offered all those jobs. Those jobs keep coming into your life. If you want to be a coach and start your own business, the time is now. You will get those other job offers if it doesn't work out.” That was wise and helpful because it was nerve-wracking.

On Friday, you say, “I'm going to become a coach,” and then on Monday, you are a coach. How do you do it? I put one foot in front of the other. I made a ton of calls. I asked everybody I knew for referrals and people to talk to, to who I could pitch coaching. I would do a ton of free sessions. I went to my gym. My gym had a vendor fair. I was living in Boston at the time, in Brookline. It was February, I was going to go to the vendor fair. It’s the last thing that I wanted to do.

It was sleeting, snowing, dark and terrible. I printed out some copies of a little flyer, it was something about me. I trek down to the vendor fair and people signed up for free sessions. Even then I thought I don't want to go to this vendor fair. I don't want to talk to a whole bunch of strangers. I want to be a coach. I want a certain life. I know that what it's going to take to get what I want, to get that life that I wanted is the hard work of trekking down to the vendor fair when it’s sleeting and snowing even if you don't feel like it. It was clear to me that that's what it takes sometimes.

Hearing you say that has a visceral feeling in me. I feel that because there's an element of everyone has this picture in their mind of that thing, the vision that they set for, that future that they want to create. They then miss those steps that it takes to get there. It's almost like comparing yourself to someone else's middle and thinking, “I see that life. I want that life. How do I have that life?” When you realize that, that's advanced for you to see through that and say, “I know it's going to be a hard journey. I'm okay with putting myself in those uncomfortable situations to get there.” Many people die along the path is probably a bad term but they lose faith in that journey to getting to that thing that they want because they are afraid to do the work.


They don't feel like doing the work. It’s funny that you are talking about a vision in your head. I created a vision board. I'm a coach. What I always say to people is like, “On Friday, I’m going to become a coach. On Monday, I'm a coach. What's your first move?” They are like, “I don't know, make cold calls?” I'm like, “Don't. Make a vision board, which is what I did.” I had a vision board up on my wall showing me that's what I wanted. It was visceral and clear to me. I’m not saying I made cold calls but I reached out to people that were uncomfortable for me to do so. I was proactive, let's say, even maybe forceful about figuring out how I could get my first couple of clients, and then I did. I kept building on those experiences and successes. One foot in front of the other is how you get anywhere you are going.

As many times you can hear that we always get the reminder that it takes one foot in front of the other and then you get there. The whole premise of the show is about people getting to this place in life. There's a path that gets there. You don't just show up there one day and you are on stage. You have to start doing the work to get there. There's no fast pass.

Unfortunately, there are many detours but no shortcuts.

Tell me about the early days. It sounds like you had such great energy about this and you are willing to do the hard work. What were some of the setbacks and the challenges, especially around your mindset?

I had energy but I did not have great energy. I had anxious energy. I remember vividly, one day early on, I don't even know what exactly happened but I was trying to get something done and I couldn't get it done. I was trying to reach several people and they weren't getting back to me. I’ve got upset that I went onto my hardwood floor in the fetal position and was crying for an hour. It’s not for five minutes and not weeping. I then hopped to my couch, took a little stress nap, got back up and got back on the phone.

I have had mindset challenges my entire life. I have a critical voice in my head regularly, high achievement, high ambition. Part of what that comes with is critical voices. The critical voices for me and everybody will veer you off track. For me, it was about constantly coming back to the behavior as in, “What do you have to do to make this work?” I remember one time getting back in Boston, I worked with this one client pretty regularly. There was a regime shift. This fantastic client was wonderful and now it was a problem.

I'm a runner. I go out to run. At the beginning of my run every morning, I would be like, “I'm mad. It's not fair. I hate this. I’m upset.” By the time I’ve got to mile 3 or 4, I was like, “I have to diversify my client base. That's what this is about.” By the time I’ve got home, it always came back to one thing, “I’ve got to write my newsletter.” I would write a monthly newsletter. I’ve never got twelve episodes of my monthly newsletter out in a year. I was inconsistent, to say the least. I was like, “You have to do this.”

In the early days, I was a scaredy-cat. I was nervous. In those days it was like if you couldn't do it yourself, get yourself a web guy. Your web guy would hit send. I said, “Dear Barry, please hit send. I'm going to go hide in the closet.” It’s what I did. Slowly, I send my newsletter out and then people would respond. They would give me positive feedback or many times they would say, “I want to bring you into my organization and do this and the other.” I focused on diversifying my client base and building my brand early in those days, even though it was hard.

Putting one foot in front of the other is how you get anywhere. 

I have two questions about this that I'm dying to ask. First of all, I'm feeling into this element of your experience of where you are at this point. It’s the experience with all startup founders are feeling, that element of being the overachiever. You have these gremlins, these demons inside of you that are challenging you and poking at you. They want you to stop or they want you to do something different. Ultimately, you have to persevere. It sounds like you get the mindset of the startup. At this point, did you know you wanted to work with startups or you are working with startups?

Not exactly. I wanted to be a coach.

Whatever shows up at the door. You haven't found your niche yet at that point. The other question I had was about your writing. When you start to write, maybe even now, who are you thinking of when you are writing? That seems like a strange question. When I started writing my newsletter, I think about it like, “If it doesn't inspire me, then I need to stop writing it.” What do you think about when you write?

It changes over time. What I write on is what I know resonates with other people. Especially in the early days, it was a lot about resilience, bouncing back and mindset. That was a topic I was personally interested in but people also benefited from that. My first newsletter was about reframing and how you can reframe situations to build your resilience. That was a topic I was huge on the first years of my coaching. Personal growth has always been a passion of mine. It always resonated with people. Also, people came to me at an early age to get my advice on their careers. For whatever reason, I'm good at careers and I'm good at seeing what's going on. I also wrote about influence and career success because I know that would resonate with people.

You answered the question well in the sense that you write what you know, what you are interested in and what people want to hear. That's what I'm taking away from that, in a sense. That’s great advice. Let's continue on the journey. I want to see what else has shown up along your path to get to this place where you are working with the people you are working with now.

Another Flashpoint for me is when I was in Boston. I was running. I was coming up on a birthday and when I'm coming on my birthday, I'm like, “I'm having these intense conversations on my birthday.” I like to have intense conversations. Suddenly, it flashed into my head, “Ten years from now, you are going to be having the same intense conversations with the same people. What do you want to say?” I thought, “Not that I live here.” It popped into my head like, “I need to move to New York. Everything I want in my life is in New York.” That was in October of a certain year and I moved to New York in February of the following year.

People would say, “Why did you move to New York?” I said, “The question is, why did I stay in Boston for so long?” I like Boston and I grew up in Boston. I have a lot of friends in Boston. At some point, it was not the right fit for me. I felt like there was some way in which I was overly exuberant and enthusiastic for Boston. Whereas in New York, I'm demure. Context is everything. When I moved to New York, that's when I began to be involved in the startup community. In New York, at that time, we were building a tech ecosystem, a startup ecosystem. That was significant to be able to be part of that building.

There’s something about this shift that you create when you move to a new place. It allows you to have a fresh perspective on how you show up. You change your environment and your outlook on how things are. The people around you in Boston might say, “I know Alisa as this person.” They will always remember you as that person. You get a chance to have a new you, a new environment and then have new influences. There’s something about that, that is also an important part of a shift like that. Here you are in the big city. You can make it here and you can make it anywhere. I'm sure there were some challenges in making some connections because you are now in a new place. Did you have any people you knew in New York?


Yes. My mentor, Marshall Goldsmith, had already moved to New York. He was a role model. This was at the back of my mind for a little while, probably. I would spend some time making some contacts here in New York. At the end of the day, that was not a problem for me. Prior to that, I had wintered in San Diego for about three months. It was February, March and April. That's how I met Marshall Goldsmith, originally. That was in 2006.

When I was in business school, I came to New York for my summer business school and I'm like, “I’ve got thirteen weeks to create a life. Go.” When I moved to San Diego, I said, “I have three months to make a big life here. Go.” That's not that hard for me. I know the things it takes to make friends and to be involved in activities. I remember in San Diego, within three weeks, I was introducing people to each other who had lived there for ten years. They were like, “You already know everybody.” I'm like, “Yes, that's me.”

One of the things I always think about is if you want success, you have to create connections with people. Preparation is one part of the equation but it's the connections and the network you create that make a big difference. When those two things meet opportunity, that's where things start to come together. Tell me the next inflection point for you. Now you have connected the fact that you are working with startups and you have found that you enjoy this particular area. What has been the thing that you are connected with now?

I have this book coming out. It was a labor of love. I wanted to write this book. It was rattling around in my head for a little while. It took me a little while to gather my negative voices and to shift my mindset around, “I can write this book.” Once I’ve got out of that way and I’ve got a book contract, I had a very short time to write the book. I sat down and wrote the book. During the pandemic, I went on to this retreat center. For five weeks, I was in Baja, Mexico, which was stunningly beautiful. I’ve got my butt on the chair and I wrote the book.

In the middle of the book, I thought, “This is not going well,” but then I was like, “Alisa, this is your moment. This is the thing you have been thinking about for a long time. You want this to be great.” I doubled down on rewriting the whole thing. I'm excited about unleashing it on the world. A lot of founders are going to benefit from it and appreciate it. I'm excited about both founders and also new leaders to understand how I lead inside a fast-growing organization.

What’s remarkable about this though is that you have written more pieces for Forbes Inc and HBR, amazing articles and stuff for years. You probably have twenty books that you have written of content and yet here you are hung up around this one book, which I know is going to be fantastic. It's interesting how we can get in our way of creating that one book. Maybe part of it to an extent is because you feel pressured for it to be a perfect piece.

There's a whole stigma around writing a book. It's a good point. When I started my newsletter, it was not easy and then it got easier. When I started writing articles, it was not easy and then it got easier. It was also a warm-up in some ways. It’s like an exercise to get me where I want to go.

This is the first book and the next book, you would be like, “That's done.” When you look back on your path to getting where you are now, what would be the 2 to 3 things that you think about as the biggest lessons you have learned about yourself and about maybe people in general?

Get out of your way.

A lot. First of all, keep getting out of your own way. Negative voices, difficult thoughts, difficult moments, imposter syndrome, everyone suffers from it. You’ve got to keep getting out of your own way. That to me is the biggest one. The second is things have a way of working out. Especially if you are on your path and putting one foot in front of the other and doing the work, you have to be anxious about it. Also, you have to do the work. You can't visualize things. You have to do the work to get those things that you want.

We talked about there's no fast pass. There's also an element of seeing the mistakes that people have made and learning from them and then making your own mistakes along the way.

Find great mentors, network and build a great network around you of people who want you to be successful and who you can help succeed, too. That's important.

I look at the network around you and the people who I see around the community that we have here in general and it's amazing to see the support. One of my favorite quotes, I don't know where I’ve got this from initially, “Amateurs compete and professionals create.” I love it because it comes from the abundance mindset versus the scarcity mindset. If you are always out there saying, “I’ve got to beat the other person to the door,” you are going to end up being stressed. Is there anything else? What are lessons that you have learned along the way that you feel like people can learn from the challenges you have had?

The last thing I would say is that if you bring a growth mindset to the table, you have to recognize you can grow, you can change and you are not fixed with a set of traits. There are a lot of possibilities in the world. For me, personal development is my religion. I want everyone to realize that you can keep growing until the day you die.

I love what you said because there's also this element of some people feeling like, “I’m further on my career. I can't make a shift into something else.” We need to challenge that. There's always something that can be done differently. Maybe not all things are possible but there's always something that can be done. That's great when you can open people's minds to seeing new possibilities. It’s our job as coaches. Before we get too far along, I want to ask one last question. What are 1 or 2 books that have an impact on you and why?

There are many answers to that question. I'm going to give you a few books. The first is not a book. I want to say Tools of Titans, which is by Tim Ferriss but even more importantly, The Tim Ferriss Show podcast has been meaningful to me because it helps expose me to people who have different mindsets, understand challenges and who show up on that show. Tim has an incredible way of opening people up. The people he gets have so much to teach. I want to put that into the mix.

Another book is from my childhood, which is A Wrinkle in Time by Madeleine L'Engle. I have a client and he's got a daughter. I brought him the set of Madeline L'Engle books for his daughter. A Wrinkle in Time exposed me to the world like, “Curiosity. A whole other world.” It's sci-fi but not quite sci-fi. It's about a little girl like you exploring the world, learning about the world, and being freaked out about what she finds. It's beautifully written. I will never forget the visceral impact it had on me.

I want to react to both of them because it's such a great share, Tools of Titans and Tim Ferriss in general. I love that you shared that because there's something about the eclectic nature of bringing different minds together and learning from them. When you think about the startup world, it's great when you see people coming from different disciplines, they share ideas, they are crossbreeding, creating new things and innovations. It's great that he has that forum for people to bring that all together. He has magic about that podcast.

A Wrinkle in Time is great because a book like that hits you at the right time, at the right age. I had someone talking about The Catcher in the Rye. Reading that as a child and then reading it again as an adult, you are getting a perspective. I remember that book and how it hit me as a child. Now I can see it differently as an adult. I can't tell you how excited I am about your new book. You shared a little bit of what it's about already. Is there anything else that you wanted to bring on from the book?

My book is called From Start-Up to Grown-up. It's about how do you go from someone who's building a product to someone who's building a sustainable business. It's also for leaders who have been focused on their area who now have to expand themselves to become broader leaders. It's divided into three sections, managing you, managing them and managing the business. There's a trajectory where it starts with you.

I am an amateur rap artist. I do have a little rap out there on YouTube. It's about executive coaching and it's called The Work is in You because the work is in you. My book starts with you and how you manage yourself. You can think about how you deal with people. It's about self-awareness, self-care and self-nourishment. It's about dealing with people as individuals. It's about how do you hire and how do you fire. It's about how do you measure what you are doing in the business.

Alisa, this has been fantastic. I can't thank you enough for coming to the show and sharing your brilliance. Hearing your stories and your insights continues to reinforce in me the path that I'm on, that other people are on and what we need to overcome those obstacles along the way of creating what we want to create. Thank you so much for coming on.

Thank you so much for having me, Tony. I appreciate it. I love talking to you.

Thank you. Before we let you go, I want to make sure I give people a place where they can find you. What's the best place to reach out to you?

Come and find me at You can download my Questions to Spark Conversation and that helps us all deepen our conversations. You can join my newsletter list, which is exciting and fun. Hopefully, it will give you some ideas to spark your own conversations.

That is needed. We are all getting back together and creating some more conversations. People are going to enjoy that. I'm sure people are going to be going out there and checking things out. Thank you so much again. Thanks to the readers for coming on the journey with us. This has been amazing.

Thank you so much. It has been great to talk to you.

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About Alisa Cohn

Alisa Cohn

I was named the #1 Startup Coach in the world at the Thinkers50 Marshall Goldsmith Leading Coaches Awards in London. I was also named one of the Top 30 Global Gurus for Startups. Based in NYC, I coach startup CEOs, co-founders, other startup executives and board members all over the world. I also coach senior and emerging leaders from Fortune 500 companies. My clients include Venmo, Foursquare, InVision, Etsy, The Wirecutter (sold to The New York Times), Pfizer, Novartis, Dell, Hitachi, IBM, Calvin Klein, Tory Burch, The New York Times. I also speak at Cornell, Harvard, The Naval War College and am the executive coach for the Runway Program at Cornell Tech.

I write for Inc and Forbes and Harvard Business Review. I have been featured in BBC, Bloomberg, New York Times, Wall Street Journal, and other regional publications.

My specialties include executive presence, power, influence & charisma, corporate politics, personal mastery, strategic decision-making, developing a strong personal brand, and building social capital. Additionally, I design workshops and give talks for executives, remote teams, managers and employees on similar topics.


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