Creating Magical Moments in the Post-Pandemic Transition with Executive Coach, Alisa Cohn, and Serial Entrepreneur, Jake Stein

Hi, I'm Erica Keswin. Welcome to Left to Our Own Devices, a show that explores how to bring our human to work and to life. Because left to our own devices, we're not connecting. Today we have two amazing guests that have their own working relationship. Alyssa Cohn is an executive coach who has coached startup founders into world class CEOs for over 20 years. Some of her clients include Etsy, Mack Weldon, Tory Burch, and Venmo. Alyssa was named the top startup coach in the world by Thinkers50 and rated the number one global guru of startups in 2021. Joining her is Jake Stein, one of the CEOs Alyssa has coached over the last number of years. Jake has founded and sold a number of companies including RJ Metrics and Stitch, and most recently founded a company called Common Paper. Before becoming a serial entrepreneur, Jake worked in vc, started a landscaping business in high school, and was the 44th ranked table tennis player under 21 in New Jersey. Now that is pretty cool. I know that you will enjoy this conversation and hearing some real time coaching between Alyssa and Jake.

Welcome, Alyssa and Jake. I am recording this live from my closet in Colorado. So thank you so much for being here.

Great to see you, Erica. So glad to be here.

So happy to virtually be in that closet with you.

Yeah, you can see behind me the belts and the. I did clean it. Luckily today.

The sweater's all stacked up.

The sweater's all stacked.

Very nice clothes.

Yeah, you're seeing my. I wish I had my own closet. You're seeing my husband's section. Okay, so let's dive right in. So, Alyssa, you and I have known each other for a number of years. I was so excited I reached out to you to have you on the podcast to talk about all things human, rituals and this return to office through the lens of an amazing executive coach. And I know you coach all different kinds of people and when we spoke, you said, you know what, let's also have Jake Stein on the call. He is one of the entrepreneurs who I've coached and he started and sold many companies and currently has a new company that we'll hear about. So this combo is something that I haven't done on the podcast. So I'm really excited. So before we dive into sort of that relationship, I know, Alyssa, I saw on your social media that you are literally, you're probably jet lagged, but you're just back from Israel for your first in person off site. So welcome back. And how was that?

Thank you. Wow. It was, first of all, just even Preparing for an off site, in person, there was so much more anticipation and excitement. Having been really starved for this kind of activity and sort of the way interaction obviously for like 15 months, but then getting to Israel, you know, remembering how to pack, remembering how to fly internationally, that was the whole thing. And then once we got there, I'll just, I'll say for myself and for the team, we had so much joy being in the same room together. Everybody has been working remotely, everybody has been making it work. And we all know there have actually been a lot of benefits to working remotely. But being in the same room, being able to have that human connection, that human contact was priceless. And I would just say that we really savored it because I think that we know that that could be taken away from us. And the other benefit, I would just say is that of course there's a lot of relationship juice, right, to build and then a lot of the side conversations that help real work get done. So it was a very interesting memory of what it was like to be in person together.

Yeah, it's interesting, right? We realize it's something that we lost and we do have more of. At least I know I do. A more of appreciation for that, for sure. So, Jake, you are in Philly as we speak and would love to hear what's going on with you. How is it there? And let's hear about your new venture, Common Paper.

Sure, yeah. Happy to tell you about it. So, yeah, I am in Philly and we are in the very, very early stages of the new company, Common Paper. Basically it came out of a challenge that I had at my previous companies and the acquirers just around the wrangling and negotiation and arguing over legal contracts when we were working with our customers. And the moral of the story was that at the time our relationship should have been the best. When we were jumping into doing business together and very excited about everything, we got into a fight and that's the worst time to get into a fight. And we think that there's a much better way where people are on the same page from the get go. And that's what we're trying to do. And yeah, we're just four people now. And the team was started during the pandemic. So there's all sorts of challenges and excitements and things like that. It's early days for us, but back on something big.

Oh, I love it. It's like you went into this knowing the problem that you wanted to solve, having been through it yourself.

Yes, yes. I've felt the pain of it for a long time and tried a bunch of different solutions in different ways, different SOFTW solutions, different people solutions, different legal solutions, and found that none of them really attacked the root cause. So, yeah, we're taking a swing at it.

It seems like the best kind of company to start. So, Alyssa, so you work with Jake as an executive coach. You have other clients, all different kinds of companies, industries, sizes. What advice have you had for some of the people you've coached during the pandemic? I saw one of your articles you wrote about COVID coaching. I know each person's different and each company is different, but are there any common themes you can share?

Well, I think the common themes, if you think about the pandemic and how it ultimately played out, it was like the beginning, middle and end. Right? Hopefully we're at the end now. The beginning was, are we still here? Like, wait, are we still okay and alive? There was a lot. I did a lot of work with my clients at that time and I wrote an article about this, how to plan for a future that you can't plan for because there was so much uncertainty at that time. So how do you, as a leader deal with uncertainty? And the big constant was that every, all the employees had, of course, concerns and the CEOs I worked with were very concerned with their well being. So wellbeing was a very big topic. And then also creating clarity. How do you create clarity and give people a sense of we know what's going on around here, when you don't really know what's going on around here, but people would really ask, how long is this going to be? What's going to happen? You know, are we going to be okay? And as a CEO, certainly as a founder, CEO fighting for his or her life, it's like, of course we're going to be okay, but I don't quite know how we're going to get to that path in this unprecedented, unchartered waters. So it was a lot of work around those kinds of topics at the beginning. You know, of course, as we've moved through the pandemic, there's been other questions. And I know a topic that's of interest of you is like back to the office. So how do we now think about the office? Is the office the same as it once was? What have we experienced and enjoyed actually about remote work? And then what do we need to sort of fine tune as we figure out what our version of back to office looks like? That's a big topic right now.

Yeah. No, it's a huge topic. So Jake would love to get your take on that. Because when I think about startups and the stereotypical entrepreneur, maybe from what I've seen in the movies, you're in a room and everybody's all hands on deck and you're up late and eating pizza and it's a bonding experience. Experience. Especially in the beginning when you're really trying to grow the business. So what is your, you know, how do you think about this moving forward even with your new venture, with many people not even wanting to come back in the office? You know, do you think that's a prerequisite or, or, you know, what, what, what do you think?

Yeah. So you're, you're absolutely right that this is a big challenge and also just like a fascinating topic. And honestly, some of it, you know, predated the pandemic and it accelerated some things and made us question other things. And common paper is actually by design going to be distributed and remote first indefinitely. So for us, there will not be an office to go back to. However, I did just get together with the team and eat pizza yesterday evening. So pizza is key. That is still a common thread.

There's no if you don't have pizza, you don't have the startup.

Exactly.

And so the team right now, like I said, is just four people. And we're for people who've all worked together before. And so we have a base level of trust and rapport and understanding and we're trying to recruit more people. And one of the things that's most important to me is that how do we develop that rapport and trust and understanding in a context where there's not a kitchen to go talk at the water cooler or a Friday lunch for us to cater? And so I think we'll have to do different things. And it's something that we'll need to be really intentional about. And I don't candidly have all the answers. And I think there's. One of the important things is that now that we're all in Philadelphia together, we are getting together when we can. But one of our team members is about to move to Seattle for these new roles that we're hiring for. We're hiring all over the US So my expectation is that getting together for a pizza in my backyard is not going to be realistic. And so I'm confident that we will have on some frequency, we'll do an off site. There's no place to go offsite from but a get together. Maybe it's four Times a year, maybe it's twice a year. We'll figure that out. But I listened to the CEO of Automattic, Matt Mullenweg. He has a podcast all about distributed work, and he has a phrasing that I really like. Where at most companies they tell you where you have to be 50 weeks out of the year, and then you get to decide the two weeks when you're on vacation. And they just flip it where they tell you you have to be go somewhere two weeks out of the year for the off sites to get together. And then all the other times you can decide. And I think there's something really appealing about that model and stuff that we'll have to figure out, but I think that's the direction we want to go into.

Well, it's great. And you started this company during the pandemic, so you're able to create that structure from the get go. So two things that you said really resonated with me, and then we'll have a little bit of a live coaching session and have Alyssa react to that. But the two things that resonated with me, you know, one is I heard the, the CEO of Google talk recently and say many of us are living off the relationship capital that we built when we were in person. So when you share that these four people that you're working with now, you know, you don't have to worry about that as much. And so, and Alyssa, maybe you can, when I turn it to you also comment on, you know, what happens when you don't have those initial people because you're going to be expanding. So that was the first thing that really resonated. The second thing is that, you know, I'll put my coaching hat on as well, which is, you know, you, right now, you're all in Philly, so you're going to have people all over. I would say to you, one of the things you're going to have to think about and others who are listening is you want to make sure that you're not getting together in the backyard and everybody else is feeling left out. And so it's gonna, it comes out to being, you know, really intentional about, about going forward. So, Alyssa, what do you think?

Well, I'd love to hear first what Jake, sort of how Jake kind of responds to those thoughts.

Yeah, I completely agree with that. And I completely agree with the, like, the problem and the constraint. And I don't, I'm not totally sure on the solution because I, in my last company, we were all in Philly in One office and occasionally a fantastic person for a personal reason would need to relocate. And we had this discussion every time like, well, we're not really set up for remote, but this person's so great, so why don't we try to make it work? And almost invariably it wouldn't work. And then six months later they were getting another job and it was just like, oh, gosh. And then we got acquired by a company based in California and I was flying back and forth all the time, or I was the one person in the Zoom where there were 14 other people in California in a conference room. And it's not great. And so I don't want there to be, oh, there's the Philly crew and then there's other people that are remote from main hq. And yeah, I think we need to have something else which is the. This is how we get together virtually, or this is how we develop that relationship capital, as you said. And it used to just kind of happen by accident. And I did some things to try to make it happen as well. But I think we, as you said, need to be very intentional about it and really conscious that we're not playing favorites formally or informally.

Yeah. And when you say be intentional about it, it's so true. And I would say we have to invent something which does not exist right now, because right now it's normal, oh, we're in the same office. Let's go into the conference room together, and the folks who aren't should show up on video. But what we see now in going back to office, like, I don't know much, but I do know that's not working. Everybody who's on video, can't hear, is not able to participate, feels left out. That is just the fact. So certainly, like an upgrade of technology would be helpful. Right. Just so we can hear you. But then also the intentionality may be, you know, if we have one person on video or more than one person on video, we're all going to be on video. Because one thing about remote work was that we're all on video. It was the great equalizer. Right. That nobody had sort of an advantage at the same time. It's like, how do you intentionally create the building of relationships when you're not in the same spot? So I think that has to probably start more one on one with people rather than just in large groups or even in small groups. Because again, I'll just go back to the most recent experience of the office that I had. There were a number of people who joined this company who joined during the pandemic, people had not met them in person. People had an experience of them as work colleagues, which was mixed, let's say. And that changed when they could meet them in person. What that says to me, obviously, if you can meet them in person, you should. When you take the time to gather once or two or three times a year, that's important. But I think what didn't happen, which needs to be more intentional about happening, is that you have to meet your colleagues who you interact with by video, informally, like for lunch, for coffee, whatever that is. Otherwise you're not creating that, you know, to the point of the social capital account, the relationship bank account.

Yep.

Yeah.

I mean, and I see.

I see Jay taking notes, because I'm a note.

Yeah, look at.

We're all.

We're all getting a coaching session here. And right when you said creating something that hasn't. Hasn't existed before, as you were saying, speaking. Alyssa, I couldn't help but think about rituals and either creating new rituals in this new world of some people in Philly, some distributed all over the world. This is a new company. So you have this opportunity to create some rituals based on your organizational values and all of that and other organizations that have been established. And you can think about this, Jake, through the lens of your former companies that you sold and, you know, what were rituals that you could have sort of maintained in this new world. So would love to get your take on that, Jake. You know, does thinking about organizational rituals, you know, does that resonate? And I was sharing for the listeners before we hopped on that. And some of you follow my podcast, have heard this. But the question that I often ask entrepreneurs, leaders to figure out what some of their rituals are. When do employees at Common Paper, when do employees at Stitch feel most Stitchy React to that, Jake, and let me know if you think that that would be an interesting place to start as you move forward.

Oh, definitely. Yeah. And I'd say that at least at Stitch, there's a very clear answer jumps out to me, which was like, I held office hours every Friday afternoon in the kitchen, and I would often. Basically, at one point, I started trying to do my work in the kitchen just so that I was trying to get interrupted. And if someone had something for me, I would just be there typing away, and I'd wave to them as they got a coffee or a snack. And it was just a natural thing. And then it kind of morphed into I would just put out a message in our Slack channel saying, my office Hours are starting. Here's three suggested conversation topics. If you have nothing to talk about. And it would always be two things very work related, something off my calendar or something about competition or whatever. And then one completely goofy personal thing like I'm trying to buy a plant this weekend. Does anybody have tips and sort of the optimal strategies for buying a ficus or something? And it was obviously not mandatory, but whoever wanted to could stop by and you can come for five minutes, you can come for the whole hour. And it was Friday afternoon, so a lot of times people would bring beer. And it was eventually a very informal thing where the conversations were wide ranging. And I think it was a lot of putting capital into that relationship bank. And then once the pandemic happened, I tried to keep it going and it was really nowhere near as good. Where I tried to just do a copy and paste of, okay, same time slot, I'm going to send the same slack message. Same people can show up or not show up, same rules. And it just was like, really, I was grinding it out and I did it. And I think people appreciated it and it was better than not doing it. But one of the lessons I took away from it was that you really can't just necessarily copy and paste. I mean, it's worth trying. And I may do something like that. But I think you really need to start from first principles, thinking, what am I trying to appreciate? What am I trying to accomplish? And then also, what are the pros and the cons of the mediums that are available to me? Because sitting around a table drinking beer is not in my toolkit right now. But we have this instantaneous worldwide communication. We have some people are in beautiful sunny locations, some people might be somewhere else. There's other things that we can do. There's dogs in the background, there's other tools in our toolbox. And so thinking about how to leverage that. So right now, comp paper is only four people. I don't think I have a lot of great things. The one thing I decided to do which I know won't work forever, is I have a one on one with everybody every day. And so that is like, to Alyssa's point, it's like there's not enough work stuff for us to fill that time. So we end up talking about, what'd you do this weekend? Oh, how's your. Is your daughter better from wherever? And like, we're trying to. We're getting into some informal stuff as well. But it's something where I don't have like a keystone Anchor to the week, where everyone is doing that one thing and we know, okay, this will diffuse us. This will be a good place to talk. So. Something I'm still trying to figure out.

It's interesting. I mean, I think you're right. For the time being. My gut tells me that, you know, rituals from a scientific perspective give us a sense of psychological safety and belonging. So even though those office hours during the pandemic were not ideal, my guess is if you were to ask the employees from Stitch, they would say, you know what? It made us feel safe. It made us feel connected. We wish we could be around the table, but I think it's also really smart to say, well, okay, maybe going forward, there will be something that looks like that. But at least you're starting from, you know, what worked, what didn't work, and you'll have to report back as you grow.

Yeah.

Alyssa, what do you.

What do you think?

Erica, Can I. Can I add one thing to that?

Yeah, please.

That's so beautiful, Jake, what you just shared. And there's something that was organic about the process in person, but didn't quite translate. So I. You know, as I write in my book From Startup to Grown Up, a lot of my clients were working on rituals in the pandemic. And one of them, before the pandemic, had Wednesdays are for Wednesdays. And it was about every afternoon. Every Wednesday afternoons, they would go around the room and they would talk about their win and somebody else's win, which is, like, wonderful and beautiful. There's a lot of clapping, and it was so great. And pandemic hit. Actually, that translated incredibly well to zoom. That was actually super easy to do because it was just to get up you. Now you. And in fact, it was kind of fun because there's an order. And then, Jake, to your point, it's like, look out my window as part of that experience. So I think it's very interesting to think about what does translate, like, back to first principles. Like, you said things which are, now you go. Now you go. Now you go can translate to video, but the organic human connection has to be probably rethought.

Yes.

You guys can see I'm sort of chuckling right now because you said Wednesday, and I thought you said wince Wednesday. And I was like, Jake thought that, too. And I'm like, oh.

I was like, yeah, it's like a dodgeball sort of thing.

Talk about why we're wincing wins. Oh, my God. That's really, really fun. Really funny. All right, Alyssa, one more question for You. You wrote an article that I saw which said, you know, the lockdown was hard on our psyche, but reopening may be worse. Why do you think that? What did you mean by that? Can you share some thoughts?

Well, this came because three or four clients in a single week said to me as we were emerging from the pandemic, it was like, oh, I have my first shot. I'm getting to my second shot. In New York, we got our act together fairly quickly in getting the vaccines out, and they were looking into the future, and suddenly they realized, I haven't really taken care of this health thing. I've been putting it off. I haven't been thinking deep thoughts or complicated thoughts about my career. I've been putting it off. Even my relationship. Right. And so I've been putting that time off. And in the meantime, I've established this, like, beautiful cocoon of routines with my family, spending so much time with my family, understanding that the constraints have been so peaceful. I'll speak for myself. The absence of FOMO was such a joy and a relief of not having to worry about missing other things that were going on or being double booked. And so suddenly, as the world emerges, first of all, things you put off because, like, oh, this chair doesn't count, suddenly count again. And suddenly you've got to address. They did not go away. You have to address them again. And then also you've got to kind of take your, like, crack open the seal of that new routine, which for some people had been very comforting, and reemerge into this new world. The post pandemic world being itself kind of, on the one hand, normal, on the other hand, not. So. I think it just was a very fast shift for people. And the anticipation of that was actually more surprisingly, psychically painful than they had anticipated.

Yeah, there's a lot of stress right now. I mean, gearing up to post Labor Day. I mean, I talked to somebody today. They said, September 7th, everybody's coming back. And even just saying that, you can see the stress just trickle down. Jake, what are you hearing in your world?

Yeah, And I could say both what I'm hearing and what I'm feeling, which is that I am one of those people that really enjoys a routine and feels very comfortable having my walls around me. And there are definitely some things where it has been presented. Oh, yeah, this is in person. And I'm like, oh, man, do I have to do that again? And I'm reminded, actually of something that Alyssa helped me with in one of our coaching sessions where I was Having a challenge with a person. And I think I had been operating within my guardrails and I was writing excellent documents and sending very well composed emails, and the problem was not getting better. And it's so obvious in hindsight where Alyssa was like, okay, have you taken them out to lunch? What is this person's kids names? And that was shocking to me. And in hindsight, again, totally obvious that that's a good way to resolve a problem. And now I'm realizing, oh, crap, I got to start doing that stuff again, where I have to start thinking outside my little, Let me write an excellent email, let me sit in my very comfortable home. And so just thinking, oh, I don't have an excuse anymore to put that stuff out, so I know it's worth it and I know I'll be happy I did it once I do. But it's something that is a little stressful, right?

I'm pretty extroverted. And even the extroverts I'm talking to are like, okay, you're gearing up. We haven't done this in a while. And I also, Jake, think about what you said earlier, which is we also need to keep considering all of the mediums that are available to us because on the one hand, yeah, I mean, yes, who doesn't, you know, lunch is great, but it's thinking about, well, the other person might not want a lunch. And you know, maybe we talk about these range of mediums and you know, I, yeah, it's going to be, Alyssa, to your point of this article. It's going to be interesting and, and hard, but I think an opportunity for a reset and to bring some really great and new and exciting things out of this. So I want to ask you both one question that everybody gets on the podcast and it shifts a little bit more to the personal. And so the question is, what do you each do in your lives that make you feel most like you?

If you want me to go first, I have an immediate answer.

Sure, go for it.

I have. Well, I have a few things, but one of the things that I do that makes me feel like me is my kettlebell workout. Because I have become really associated with kettlebells, both because my journey of fitness has been so nourishing for me over my life, because about five or six years ago, I developed osteoarthritis in my right knee because I was overusing my running. And so kettlebells in many ways so I could build strength and balance out my workout. And oh, by the way, my doctor said I'd never run again. And I was able to get so strong that now I still run, but I'm more balanced in all my fitness. And my fitness has been a journey of exploration, like self exploration and re identification with myself as someone who's like, I lift heavy weights and like fun. And I work out with my kettlebell coach, and he's taught me a lot about coaching. So there's a lot of juice in that. Over the pandemic, I was posting videos on Facebook and Instagram called Kettlebell Quarantine where I would show one little kettlebell move. And I did it just for fun. I don't know why I did it, but actually I got a lot of feedback that people looked forward to it. They cheered me on. I love that. And also a lot of people said, oh, it's so inspiring. And that was very gratifying for me. So I would say it's kind of reinforced my identification with my strength training and specifically kettlebells.

Well, I love it. And it sounds like it really became and is a ritual for you, right? We know it's a ritual. If a week would go by and you didn't work out, you know, I know you bring them when you bring them when you travel or get them when you travel.

I shipped them to Mexico when I was there for five weeks during the pandemic, I shipped kettlebells. I posed for a picture for your book launch with my kettlebells and your hat because that was like my ritual.

Yeah, well, and I will say your ritual became a ritual, like every Sunday. I knew that I would see your post with the kettlebell. So I love that. I really do. Jake, what about you? What makes you feel most like you?

Yeah, I'd say it's also an exercise thing. And for me, it's running. And I get a lot of different things from running. I probably like first and foremost. It's like my main form of anxiety and stress release is just. And I have a routine where I know which days I'm going to run. I always do it first thing in the morning. I have a route that I like to go, and it's something where I love just observing the city and the construction that's going. And every time I go, they've made a little bit of progress. And it's something where I really look forward to it. And when I can't do it, it's definitely something that I miss it. And the great thing is that unless there's ice on the ground, I can do it. And if it's really cold or if it's raining really hard, it might stink, but I can do it. And if I'm on vacation, as long as I have my sneakers, I can do it. And so it's something that's a practice that has been with me for now, yeah. More than a decade. And yeah, I'm hoping if I start to have problems with my knee, you know where I'm going to get some advice on this. So far, so good.

Well, I hope it doesn't happen. But yes, I could be supportive.

And my guess is, you know that that ritual probably gave you a lot of comfort during the pandemic. It was something you were able to do and time to connect with yourself, with others, with the city of Philadelphia. I mean, I had a woman share with me that she started running during the pandemic and she always tried to run right before seven, when all the healthcare workers were banging the. I mean, there were people were banging the pots and pans to cheer on the healthcare workers. So my guess is that was a real comfort.

Oh, absolutely. Yeah. And in the beginning when we didn't know that being outside was relatively safe, when I couldn't do it, it was especially tough. But once we learned that that was a responsible thing to do, that was a huge unlock for me and definitely made navigating the rest of it much more tolerable.

Yeah, no, I'm sure. Well, thank you all so much for being here. I'm really excited to follow Jake your journey for Common Paper as you're solving this problem and see about your growth and hear how you think about these issues from a cultural perspective. And Alyssa, can't wait to get my hands on your book From Startup to Grown up, which comes out on October 26th. Is it?

Yes. Perfect. Thanks.

All right, coming to Amazon and a Barnes and Noble near you and Jake.

Anyone who's anyone has already pre ordered it.

Yes, pre order it. And Jake, I'm sure we'll both be at the book launch, so I look forward to meeting you and seeing you in person. And I wish you both a great rest of the summer.

Thank you so much.

Thanks, Erica. You too.

Bye, guys. Thank you for tuning in to Let youh Own Devices. If you enjoyed what you heard, please rate and review the show on Apple Podcasts. If you want to receive my monthly ish update on all things human at work or just want to say hello, email me@ericaericakeswin.com stay safe, stay connected and I'll see you soon.