#7: Jennifer Dulski, Rising Team

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number 7. I'm thrilled to welcome Jennifer Delsky to the show. Jen is the CEO and founder of Rising Team. Prior to that, she founded Dealmap, which was acquired by Google in 2011. Jen has more than 15 years of experience at big brand internet companies, including Yahoo and Google. She's also on the board of WW, and she's the author of the Wall Street Journal bestselling book Purposeful. We had an incredible conversation. Jen is a seasoned leader and someone who is truly committed to the art of leadership. We cover a lot of ground, including her moving to Pittsburgh and founding a nonprofit when she was just 21 years old. We talked about how you can sometimes get fooled about having product market fit when you really don't, why it's so helpful for founders to spend time at large companies. And we also talk about Jen's perspective of life that she gained from having had a brain tumor. We also discuss the work-life mashup and her love of acronyms. You're gonna love this episode. Please enjoy my conversation with Jen Jennifer Dilski. Jen, welcome to the show.

Thanks so much for having me, Alisa Cohn.

I'm so excited. I'm so excited to have you. I've been so much looking forward to this conversation. And I want to start in what I think is the obvious place, Ted Lasso. You wrote an article showcasing, this is for LinkedIn, the leadership lessons from Ted Lasso, which of course is the, if you don't know what that is, it's the Apple TV runaway hit of the season. You call Ted a level 5 leader in the parlance of Jim Collins from Good to Great. So tell us what, in your words, is a level 5 leader and what specifically have you learned and brought to your work, which was inspired by Ted Lasso?

Yes. So for anyone who hasn't seen it yet, I highly recommend. I am a huge fan of Ted Lasso. I'm actually a huge fan in general of sports movies and television because I think they just always tell great stories of people overcoming obstacles and working together as a and that's what I spend most of my time thinking about and what I love. So, Level 5 leaders, if for people who haven't read Good to Great, are essentially people who put the team and the mission ahead of themselves. They wildly share praise for others when things go well, and they eagerly accept blame and responsibility when things don't go well. So, they are people who are modest and humble, and the team comes first, and that is Ted Lasso in a nutshell. He is kind, empathetic, and exactly the kind of leader you would want. And for Rising Team, it's actually pretty interesting because the premise, the whole premise of Rising Team is actually that great leaders are a lot like great coaches. And so, for this show to come out right at the same time we were building the company, there were so many parallels. I just, I had one of those moments where I just had to write it down. I couldn't help myself. And that's why I wrote that piece.

Yeah, I think that's lovely. Are you ever sort of challenged yourself? Because I love that ideal of empathy and being understanding and also treating— one thing that Ted Lasso does is he treats bad behavior with like— he meets a punch with a hug. And I'm curious, how do you— things aren't always perfect. What do you do when you realize that you're not being your best self in a certain moment? How do you pull yourself back into sort of kindness and empathy?

Yeah, well, one is making sure that you create an environment where people can tell you the truth and tell you— make— point out when you are not being your best self. Because sometimes I will say I, I may not notice. I mean, sometimes I notice myself and I can pull myself back, and sometimes it takes other people to say, hey Jen, you know, you seem frustrated right now, or something. And no, I don't— honest, my kids do this especially well when I get stressed. I have two college-age kids, so now they're exceptional at doing that. But so my team. And that's, you know, we haven't talked about Rising Team yet, but we— what we build is a product called the Leader Kit, which brings to life one leadership theme a month based on training and a team-building session that you do around that theme. And the very first month is about psychological safety, which is really the core to high-performing teams. And this is the notion that it is okay to speak up when things are going wrong, when you personally make a mistake, when you might not be at your best, when when someone else might not be at their best and speak up without fear of retribution. So we try to create an environment where that is okay. And the other point that's important here is empathy and kindness are key. It doesn't mean that you should just be super nice all the time and not tell the truth. So, you know, Kim Scott calls it radical candor. I like to say, I think of it as the two Cs. I call it clarity and compassion. You want to be compassionate to people and you also want to be clear about what you expect and when people aren't meeting expectations or when I myself am not at my best.

Yeah. Yeah. I think that's so beautiful. And I certainly agree that most people think that that kind of culture is like, "Oh, it's about being nice and I'm not being nice." No, it has to be sort of baked into a context of performance and also wanting, right, that clarity in expectation setting. So people also know what you want them to achieve.

That's right. And in fact, when I say we built the company on the premise that great managers are like great coaches, I have another— you'll see I have a lot of Cs that I use. We'll talk about these, but we have 3 Cs that the company is based upon. Our philosophy is we call them Coach, Clarify, and Connect. And that's what great coaches do, right? They first— Coach means, do I understand each person, what they need, their potential? How do I best serve and support them? Clarify is, am I being clear about where our vision is? What does success look like? What are we here for? And who is doing what to get there? And the third is connect, right? Coach, clarify, and connect. You have to make your team feel like a team. And so, that's again, Ted Lasso does it, but we also try to do it because to your point, being kind in and of itself is not enough. People need to know what they're there for, be inspired by a vision, and then ideally be kind to each other in the process of getting there.

I definitely want to hear more about Rising Team, but before we get into that, I'd love to also talk about your past career experiences because you were the co-founder and CEO of Dealmap.

Was that your first startup? You know, interestingly, it was not my first startup. My first startup was a nonprofit that I founded right out of college. So I moved to a new city. I moved to Pittsburgh, Pennsylvania when I graduated college and I started the Pittsburgh site of a national nonprofit called Breakthrough. So my first founding experience was moving to a new place, having to raise all the money, hire all the people, get all the logistics started for this nonprofit. And, you know, I was only 21 when I did that. And I think back to those days and wonder like, you know, how did— how did I do that? And the truth is no one told me I couldn't, right? And at that age, you really believe that you can. And the truth is, I think most of us can if we just put ourselves out there. That's actually a little bit about what my book is about, that each of us can kind of start movements around the causes that matter to us. And so, yeah, I started that nonprofit in 1993. So it's been running now almost 30 years.

Oh, it's still running.

It's still running. And thousands— so it's about helping kids be the first in their families to go to college. And now thousands and thousands of kids have gone to college through this program.

What drove you to do that, to start that nonprofit?

You know, it was, it was based— it was modeled on a nonprofit that had started in San Francisco where I grew up. And the way the model works is it's a students teaching students model. So the The students that are preparing for college are middle school and high school students, and then the teachers are all older high school and college students. So I taught in the program when I was in college, and it just gave me so much inspiration because you see both what a difference people can make in each other's lives and also how much people are capable of when you give them the opportunity to do more than most people think they can. Right? So they take college students and say, "Sure, make your own curriculum, teach your own classes, etc." And so when they said, "We want to model this program in different cities. Does anyone want to move to a new city and start one?" I raised my hand right away. Huh.

That's amazing. Well, then I guess Dealmap was your second startup. And you sold that to Google in 2011. And I guess I would love to know from both of those experiences, What did you— what are kind of some of the takeaways from those experiences as a founder and a CEO? What went well and didn't go well that you bring into your leadership today?

Yeah, and I will say those two were very different. Founding a nonprofit and starting a venture-backed tech company are pretty different in nature. I think the nice thing about starting a nonprofit is is by definition, you sort of only raise the money, you know, you raise how much money you need to run the organization and then the next year you do the same thing and so forth. There isn't this notion of like being wildly unprofitable for a while, which happens in a lot of venture-backed startups. So in the Deal Map, I learned a lot of lessons around how to find product-market fit, what to do when things really aren't working, how to find a business model that works. The biggest takeaway I took there was just what's the difference between something that is working and not working. It's very easy when you're running these companies or working at them to think things are working because they're going pretty well. And oftentimes they're really not. Like when things— when you have true product market fit, things light up in a way where they grow naturally. People tell each other about them. And I— we didn't have that at Dealmap until our fourth try. At the company. We built 3 different products. We actually had 3 different names of the company before we hit on something that was successful. So I often called myself too stubborn to fail. It was right around— this was 2008 when we were in the sort of meltdown of the economy and the banks were all too big to fail. So I just said, I'm going to be too stubborn to fail and I'm going to keep going until I find a way to make this work.

Oh, I love that. Too stubborn to fail is something we should all take on board, actually. But when you say you— I think that's so interesting you say You think things are going right. So I coach a lot of founders, obviously, and in my book, From Startup to Grownup, I talk about the need to set goals. Otherwise, you're like, "We're making progress. It's so great." But you maybe should be making more progress. Maybe you're not making enough progress, but it's hard to really know that. How did you think about that?

Yeah. I compared it a little bit to being like surfing, although I'm not a surfer, but it's sort of what I imagine surfing might be. The first idea we came out of the gate with, it was like we went in the water on our surfboard and we didn't catch a wave at all. Like, it was pretty clear that it was not working. The second idea, we caught like a little wave and it was, ah, you know, we're surfing, but only we weren't really surfing. And the third idea was even a little bit bigger, but, you know, I would say in that sense, A good example there was we had some clients. They were— started paying us for what we were doing. And then I looked at the size of the market of people who might be interested in what we were doing, and it just wasn't big enough. You know, even if we got everybody who wanted what we were selling, it wasn't going to be big enough.

And what were you selling at that point?

So, yeah, this is maybe a little bit longer of a story than you want, but what we had done was we, we had technology that looked at millions of local reviews for businesses and analyzed it using natural language processing and pulled out the structured information. So this restaurant is romantic and the best dishes are A, B, and C, and here's what the service is like. It was sort of like an automated version of Zagat. And our original goal was to build a consumer product for this. And we built an awesome consumer mobile app, and I just couldn't get anyone to use it. And we had no business model, so I couldn't afford to pay for people to use it. And so what we ended up doing was taking all this amazing data we had and selling it to other local publishers who had no content. And they were really eager to buy it, and they started paying us, and it was great. And then I looked up and realized there are only so many local publishers. And it just was never going to be a venture-sized business. And so we had to take another hard look in the mirror and say, what do we do? And we went back to, to what do users really need? What do people want? And I said, okay, we have all this local data. What have we seen in all the local research that people really want? And there were only two things. One was events and the other was deals. And events was already being done by several other people. No one had really done, you know, deals and sales. And so that's what we did. We layered that on top. And as soon as we launched that, it was like night and day. All of a sudden we had 3 million users in the first year. We had people like Microsoft and MasterCard calling us because they wanted to work with us. And that's when I said, oh, this is what it looks like when it's actually working.

Right. Wow. That is, yeah, that's quite a journey. But then it's like, oh, that's how you know. Right?

When you know, you know. That's right. And actually, here, um, at Rising Team, you know, we launched— so I learned how to do, how to sort of take a slower start, right? So I was very lucky to be able to do, to kind of bootstrap it in the early stages, build a prototype, get some feedback, see what was working before we raised money. And now we've done several prototypes, so by the time we launch a product that is really out of beta and ready for the market. We were— we had done so much research about what people wanted that we ended up with something that's easy to explain, easy to share. And we have just incredible reactions to the product now. It's like 97% of all people who use it say, I learned something valuable, I feel more connected to my team. Like, all the things we want, um, that kind of like— is it, is it spreading? You know, yesterday I, I talked to someone about it, and today she sent me an email saying, I just recommended it to 3 other people. So that's the kind of sign that you want to be able to see.

Yeah. And you saw that from your experience at Dealmap where it wasn't that, wasn't that, wasn't that, wasn't that. Exactly. I love— yeah, that's the whole thing about serial founders, right? That they just know more the second time around, the third time around. And so I guess I'm also curious, what did you learn from your corporate experiences? You were at Yahoo during a growth period, you were at Google during a growth period. Then we didn't talk about change.org for a minute or two, but what did you learn from those experiences that, again, help you today with your leadership as a founder?

Yeah, so I think a few things come to mind there. And I guess first I should also say that even as a serial entrepreneur and a multiple-time founder, it doesn't mean that it's automatically easy. I don't want to give people the wrong impression that you wake up one day and everything becomes easy. It's still hard. There are still, I like to say, sunny days on the mountain and cloudy days on the mountain, even if you've done this probably hundreds of times. But when I— I actually think it's been really valuable for me to spend a lot of time at larger companies too. One is that you start to see what scale looks like. Like, what does it look like when you actually cannot do everything yourself, when you have to delegate to other people to get things done? How do you How do you hire well? How do you build a team that can carry forward the mission and the values in a way, even when you're not hiring every last individual person, et cetera. So, that's a big part of it. I will be honest that the network of people that I met at those places has been very valuable. So, there are people working now with us at Rising Team who, you know, came from Facebook. One came from Dealmap. There's one I worked with at Yahoo, like, you know, building your connections with people at companies of high caliber like that is really important. And the other thing that I learned is it's— at some point, it does become about prioritization and the ability to say no to things. Because as a startup, it can sometimes be easier. You're very limited in your resources. But as you get bigger and you say yes to more and more things, it then actually becomes much harder to say no and to say, "We're going to stop doing this." And I saw the pain of not saying no at some of those bigger companies. And so I think it gives me more discipline to do that now.

That is— well, I think that's very insightful. And I really appreciate your point about scale. I think the founders that I work with, when they haven't seen that before, they don't know what it's going to look like when it's bigger. But you've been kind of all around the map about seeing small, seeing big. So you have that perspective. So how does change.org fit into the picture? I mean, I can tell that you're a mission-driven person. I can tell that you care a lot about making a difference and to your point about being purposeful, but how did that all come about, joining change.org?

Yeah, so it's true. I feel like I have spent my life in search of the ability to create impact at some kind of scale. The reason I started the Breakthrough site is because I did want to make the world better. And yet it was very linear in its growth. It was, you know, you could raise twice the money and you could serve twice the number of students. And so the reason I got into tech in the first place, this was the way to exponentially grow impact. And over the years then, I sort of veered away from direct impact to things that felt slightly less impactful. I mean, still impactful for the business, but less impactful for the world. I led shopping at both Yahoo and Google. I've done a lot of marketplace stuff. And it is— there are ways to say that that work is impactful, right? There are people's businesses, you grow the economy and all of that, but I just felt like I didn't want to wake up every day and do that for the rest of my life. And so I actually got called by a recruiter when I was working at Google about the change.org job. And I thought, you know, the chance to help grow an organization that's making this kind of positive impact in the world where everyday people are creating these amazing world-changing campaigns felt really like a great opportunity. I was able to get there at a critical juncture in the organization's history so that I was able to help them, you know, really massively scale their audience, but also find a business model that would work for them and scale the team. For me, this was my first truly global experience. Excuse me, experience. So I, we had teams that were spread across 18 countries and it was actually so so helpful. I did not know that later in my career I would face a global pandemic where everyone would work virtually, but as it turns out, I really knew how to work effectively virtually because we had people on so many time zones and so many locations. We just couldn't gather in person on a regular basis, and that ended up being a tremendously valuable lesson for the future.

Yeah, as it turns out. Yeah, here we are in a global pandemic. What did you learn? What do you do to, I think I would ask, create culture, keep everyone together, and also provide what you said earlier, psychological safety when everyone is remote?

Yeah. So I will say that in the change.org days, it wasn't that everyone was remote. It was more that we had people who were very distributed. So we created this very virtual culture, and there are some amazing traditions you can create to make people feel feel like they are more connected. So things like, we had even silly things like out-of-context quotes was something we used to do where people would say something funny and we had a Slack channel and, or we had this different funny traditions that you share across borders and you share virtually and in person that helped. In today's world, where so many offices are either fully remote or hybrid, I think it's even a harder task. It's a higher threshold because not only are people distributed, but people have the extra weight and anxiety of what's going on around them. It's just so much to handle. And so, it is, to be honest, one of the reasons we built Rising Team the way we did. We basically said, look, if you can consciously, proactively gather your team in a way that they all feel heard valued learning and do it just once a month. We call it HIIT for managers. It's like, yes, it takes some work, so does going to the gym, but it's short. We're gonna do like, you know, HIIT is, you know, your 7-minute workout every day. This is your couple hours a month. And if you dedicate a little bit of time to doing it, the investment just pays out so, so well. And we can see that in the kinds of responses responses that we get from, you know, people will say things like, I've been at this company for 2 years and this is the first time I've ever felt invested in. Or, you know, my team, we never have conversations like this. So, this is the first time I'm getting to know my team this way. And whether it's Rising Team or anything else, putting that conscious effort into thinking about the team as a unit and thinking about each individual and how you hear and understand them I just believe is more critical than ever.

Yeah. Oh, absolutely. And teaching your managers to do that, right?

So, it cascades throughout the organization. That's right. And I mean, that's why we started there. When you look at the data, actually, if you say employee engagement is the thing that's most highly correlated to company success, 70% of employee engagement is driven by the quality of individual managers according to Gallup. And most managers don't really feel equipped for their jobs. And so, You know, the question is, how do you help them become more equipped? When we were doing research on this, we found, you know, first it has to fit into their busy schedule. Like, they're just so overwhelmed. And then the other piece is, it's not enough anymore to just train the managers. You know, you can, you can send them to training or you can get them a coach, and those things are amazing. Right now, as you know, they're not generally accessible to everybody, but even when they are, Oftentimes, people then go back to their teams and think, "Okay, I learned a bunch, but how do I translate this into my day-to-day with my team?" And so, that's the last mile problem we're trying to solve.

I love the way you put that, last mile problem. Well, we have talked about Rising Team, but we haven't talked about Rising Team. What was the sort of the founding insight? Like, what's the founding story of Rising Team? How did you come to found it?

Yeah. So, I feel like— this is the company I've been meant to build my whole life. I'm sure you've taught— you work with a lot of founders who feel that way. There's a few reasons for me. One is that, you know, my own personal passion has always been about empowering other people. Like, how do I help other people be their best? And I realized that, you know, that's what brought me into teaching in the first place. When I ran that nonprofit after college, I also taught high school for 4 years. Um, and now I teach at the Stanford Business School. But that idea of my ability to empower other people has been a big theme in my life. And to do this now through a tech product, which means it reaches so many more people, and to target managers in particular, which means if you help the manager, you also help the team, it seemed like the very exponential way to get at it. Also, I will say that, you know, they people talk about finding ways to get paid for doing what you love. And for me, when I, I used to joke that like, if people could pick their favorite day at work, like, what were you doing on your best day at work? My favorite day was always team offsite day. You know, it brought like the camp counselor in me got to come out. And so basically now I get to spend every day building team offsite day for every team on Earth. And so, it's pretty fun to actually spend time working on it. So, it's a way to kind of do what I love. And also, honestly, these are tools I wish I had had, you know, as a manager myself, as a manager of managers. I ended up building a bunch of things that sat in, like, Google Spreadsheets that literally have now been used by teams for decades but could never do the things I wanted. Like, I couldn't overlay the data or trend it over time. And by building it into an actual tech product, now I can, and I can give that to everyone else too.

Mm-hmm. Jen, I have to just tell you about doing the things you love. When I was 14, somebody said, "What would you do if you could do anything, didn't have to worry about money?" And I said, "Have intense conversations." Oh my God, I love it. So I became a coach and then I became a podcaster.

It's amazing. I mean, it's funny, my sister, I talk about this, a lot of times too because when she was— and you can see those talents coming out in people when they're younger. And my sister was kind of always the matchmaker, you know, like she would find the people who should be together and help them find each other. And, you know, now what she does, she works in executive search. And it is the perfect career for her. She gets to do what she loves every day.

Right. Show me the child, I'll show you the adult.

That's so great. Right, right.

But you've talked about these offsites and I think you have a 12-month monthly curriculum, sort of offsite set or toolkit for managers. What are— how would you describe maybe the stages that managers go through? How would you describe the different parts of the kit that you give people, that you give managers?

Yeah, so it is a monthly toolkit, as you mentioned, and it covers one key leadership theme each month. And then what's included in the package is what we call micro-training. So we basically have gone out and coalesced all the latest science and research down to 20 or 30 minutes that you can focus on. And then there's a team building session around each theme with an embedded activity or exercise to do with your, with your team. And we built them around the topics that are the most important things that managers need to learn to be great at their jobs. So it starts with psychological safety. It goes on to understanding and amplifying the talents of people on your team. You focus— you— there's a kit on cultivating appreciation because we know that people want to be valued. There's a kit on building resilience. The way we actually looked at how to build the curriculum is we looked at the Gallup Q12, which are the things that most highly correlate with employee engagement. So, if we said, if we want employees to be engaged, What things do they need? And the questions on that survey are things like, I get the chance to do what I do best every day, or I feel heard and valued, appreciated by someone on my team. And so, we basically built curriculum around each of those things. And the idea is that the manager can learn it and bring it to life without having to think about it a lot. Like, the way our guided sessions work is you just kind of hit go and then everything's in it already, the icebreakers, the discussion questions, the activities embedded, the data gets aggregated. We have a countdown timer all the way through that you can use. We build in the share-outs, how many minutes per person. There's reflections and action items. We put in some fun bonus items at the end that we always make sort of custom emojis that people can use to take the language forward. And so it's really like, how do you, again, like HIIT, you know, high-intensity interval training, you just sort of learn it, follow the instructions, and then your team comes along for the ride, which is I think what makes it more unique.

I can totally understand that that's very useful to managers and powerful for managers because as a coach, I regularly see that the things that we talk about in coaching don't naturally translate. So leaders and managers don't always think, oh, I could bring this to my team.

That's first of all.

And then second of all, even if they do, they don't always have the skills. So it sounds like you're giving really strong guardrails to people.

That's exactly right. And I had someone who works in talent development at one of the companies we're working with, he calls it leader-proof because the idea is anyone should be able to do it. We actually, in the tool, the team members and the team lead all see the same thing. So even if the team lead— you know, falters a little bit in running the session, any team member can actually step in and say, oh, it says we should be doing this now, or volunteer their own thoughts. And, you know, we test all these kits with real teams before we put them out because we want to make sure that they are going to work across a bunch of different types of teams. And what is so interesting is sometimes, yeah, people just do them not the way you might think. Like, I've seen teams do these with their cameras off the whole time, which is so surprising to me. In fact, so much so that we actually wrote into the product, you might want to keep your camera on. But some teams are very introverted and they really prefer not to keep their cameras on. And then when we get to the end of the session and we ask them what they thought of it, I thought, oh my God, this is going to be horrible. Like, they read silently to themselves, they kept their cameras off, and at the end they just say, They're like, "That was amazing. We never have conversations like that." Because, you know, the interesting thing is it doesn't really matter how you do it. Like, we're giving a lot of help and direction on the how, but it matters so much more that you do it than exactly how.

Yeah, totally. That's very inspiring. And what I love about that is you throw it out to the users and then you're like, "Oh, I did not expect you to do that." And you keep iterating. There you go. We're saying, "Okay, camera's off.

That's fine." Every time, every time we test one, I'm like, "Oh, we should change that." But that's the fun thing about building products is you learn from the people who use them.

Right. You know, Jen, I'm so struck. You have so much fantastic leadership experience. You're such a mission-driven person. Like, you care about making a difference. Now you're a leader running a company to enable leaders. So I'm like, "Jen, you're like perfect. Have you ever experienced any setbacks in your own leadership, your own leadership journey?" Oh, I mean, of course I have.

I mean, setbacks in every direction. This is why I use the analogy of the mountain. I say like some days it feels like it's sunny and you brought a picnic lunch and you can see the top. And other days it feels like the biggest storm is coming and you're way at the bottom. And that happens all the time, even sometimes on the same day. You can go back and forth. When I think about some of the big setbacks, I mean, let's be honest, Dealmap, although it has a good ending, we built 4 different things before anything worked. That was years of work with nothing to show for it. And how do you keep a team motivated during that time when things really aren't going well? You know, on any given day, you can You can win a deal, you can lose a deal. Those things happen all the time. Even, I think about when we were about to sell Dealmap to Google and we had had to make that hard decision of do we sell the company or do we take more funding and keep going independently? We had both options. We decided to sell and 36 hours before the deal was closing, my whole team packed up in boxes and everything. We got a call that says, "We found something in your diligence and we're not I'm not sure we can do this deal. And those, I mean, those moments are just crushing. And we did find a way through that path. You know, we, we changed the structure of the deal. We made it work. It took 3 weeks longer. But, you know, those are— there are some really difficult moments that you face along the way, not to mention personal life things that, that get in the way. I mean, I Early in my career at Yahoo, I was diagnosed with a brain tumor. At work, I found that out. So, you know, yes, everybody has— actually, one of my favorite books is Robin Roberts' book, and she says, "Everybody's got something." And so the question, it's interesting, we're actually— we have one of the kits in Rising Team is about building resilience, and we talk about how everybody has their own kind of unique resilience superpowers. We all have kind of slightly different styles about how we go after it, but we all do have the ability to bounce back.

Yeah. Yeah. Well, that totally— and certainly you can learn that as a founder. I guess you can also learn that when you realize you have a brain tumor. It sounds like you're okay now.

I am. It was— I know, I am very grateful. It's benign brain tumor. But I had— yeah, I had just started at Yahoo. It was about a month or two after I started. I was still in my 20s and I had to leave work and have brain surgery. And, you know, life throws you unexpected things. And I still, at the end of the day, I am so grateful because, A, those kind of moments give you a lot of perspective, and B, so many people deal with so much worse.

What kinds of perspective did it give you?

You know, that, and I will say I have 2 kids and And each one of them has had one fairly bad accident, which I'm again so grateful that they are both okay. Those moments though just have taught me that, A, life is short and we should really try to make the most of it. And for me, that has been about trying to point my life in a direction that I feel has some meaning. And also though, appreciating that little things, you know, just like all— or even in the pandemic, like, I'm so appreciative to live in a neighborhood where I could take calls on walks and things like that. And those little things matter a lot. Um, and then the other thing is just, yeah, the people in our lives who mean a lot to us, we should tell them and spend time with them. And that's what I've done. I, I feel like it does make me live with both more appreciation and a little bit more anxiety too, that things could go wrong at any moment. But right, because you try to keep more in the appreciation side and less than the anxiety side.

Yeah.

Well, that may give more context for your phrase.

I'm gonna— or it's not a phrase, it's an abbreviation. Jen, it's pronounced iktidah.

Iktidah. Iktidah.

Oh, she corrects me. Iktidah. Excuse me.

Can't you correct that? Can't you pronounce that? Can't you read that?

Just kidding.

It's a horrible— yeah.

Tell us what that is.

Yeah, so it's funny, I grew up in a family where we used acronyms all the time. Even like before texting, we had this whole set of acronyms that we put on the fridge, and they were things like FHB, which was family hold back. Like when too many people would come over for dinner and we didn't have quite enough food, we'd be FHB so nobody would take too much. Um, So I developed this acronym. Yeah, actually, believe it or not, I developed this when I was in high school because I remember so distinctly I went to this— my parents sent me to a camp for delinquent children. I'm not sure why, but I know I went. So I went to this like camp where you had to learn how to like be tough and obey rules and things like that. But one of the things that we did was this big ropes course. And there was a zipline off of the top of a very, very big cliff. And I was just terrified of this thing. I was at the top of the cliff and I was the last one to go and everyone was at the bottom and they were all like chanting at me to come down. And I just was like, I can't do it. I was so afraid. And then I had this like inner dialogue with myself. Do I— like, because I thought I could just turn around, like I could walk back the way I came. And I had this inner dialogue of, do I want to be the kind of person who turns around? And then I said, I really don't, but I'm still really afraid. And so I had this discussion with myself where I said, well, if I can do this, then I can do anything after this, because this thing seems so, so scary right now. And that's where "ik tikta" came from. If I can do this, I can do anything. And I did jump off the cliff. And ever since then, I have had this habit of just trying to do things that I find really to be very frightening because I find that they make other things a lot less scary in comparison.

Mm-hmm. What I love, I love so many things about that story, including that you were talking to yourself as a kid on the mountain, right? And you were inspiring yourself. And also, you know, we have these moments of truth that we are able to tune into or not, or we miss the moment. And you tuned into that moment of truth in terms of like, who am I? You know, like, am I the kind of person who? And then I love how you actually jumped off the literal cliff.

Metaphorical cliff.

Literal cliff. Yeah.

And I totally hated every moment of that, by the way. But it wasn't that long. And that's the thing, most scary— most things we're scared of aren't actually that big. Um, you know, I think it's easy to be scared of so many things and just not to try a lot of things. Now, there's a difference. Like, some things are really genuine— genuinely super risky and you know, put your life at risk. And I don't, I don't take those kind of risks, but there's plenty of things that are not life-threatening that still scare me that I think are worth doing. I, I once went up in a glider plane— that's a plane with no engine— um, again, just like it was right before I graduated college and I was about to go start this new program by myself, and I thought, that's really scary. What else could I do that like makes that seem easier. So it's a weird strategy, but—

Well, it works for you.

Yeah.

I mean, I, so I ask all the founders that I talk to on this program, I ask about imposter syndrome or self-doubt. So what's funny is that I guess I'm really interested now, like, given this philosophy and these experiences you've had and putting yourself in these difficult moments on purpose, things that scare you on purpose, Have you had self-doubt and imposter syndrome?

Yeah, it's, it's actually pretty funny. I had one of the, the women who's actually a partner of someone I used to work with, she— we were talking one night, and this was many years ago now, and she said, uh, imposter syndrome. And I said, what's imposter syndrome? And she said, of course you don't know what imposter syndrome is. So I think there is perspective that somehow I don't have it. And that's definitely not true, even though I wasn't familiar with the term at the time. But I'd say there have been some moments in my life where that's been stronger than others. And the time when it's been the highest in my life is actually fundraising for tech startups, right? Like, and I hate to admit this, for a long time I didn't admit it. It because I thought it just showed so much weakness to admit that I think it's hard to raise money, especially as a woman. When I was trying to raise money for Dealmap, it was 2008, 2009, maybe, you know, not a lot of women founders or CEOs. And I would go up and down Sand Hill Road and I would have meetings sometimes, you know, late afternoon meetings. And I would go to the restroom and all the toilet seats would still be up like they had just been cleaned and no one had used them all day. And I just thought to myself, "God, this would be easier if I were a man." And then I would get so angry. I would have one of those internal dialogues with myself and say, "How can you even admit that? And how can you? And maybe it's not true and maybe it's just you," and so forth. And so, yes, those are the moments that I've had a lot of self-doubt. And even this time, we've just raised a seed round for Rising Team in February. It was great. Our lead investor is Female Founders Fund. But is it a coincidence that the lead investor is a fund that funds only women founders? Probably not. And if you talk to Anu, who's incredible, who's the founder of Female Founders Fund, she will tell you in her first bat at raising her first fund for them, I can't remember, it was like hundreds of meetings to raise, you know, so it was a small, small fund. And so the— I think sometimes we do have to say the system is not— it's not even, it's not even in a lot of ways. And I know, again, I still have a lot of extra privilege for many, many reasons. Um, and some places we each have a lot extra privilege and some places we don't. And Yeah, those are the moments that I find myself thinking, "Oh, God, is it me? Like, why is this not working?" And what I think gets me through is, you know, having belief in myself, having a community of people that I can go to for help and encouragement, and then just sheer determination. You know, it is the too stubborn to fail thing that comes back. And, yeah, if you try enough, you likely will succeed. So it's about not giving up in those moments.

Yep. Yep. And putting one foot in front of the other and keep going.

Yes.

Yes.

Absolutely.

Yes.

I have a sign in my— that I used to have in my office that says, "Keep moving forward." It's from another one of my favorite movies called Meet the Robinsons. It's a Disney animated movie about a little kid inventor. But the idea is like failure is part of the process. Process. Yeah, it is about keeping moving forward. Just in fact, there's one great scene in it where he invents a peanut butter and jelly gun that explodes all over everyone, and then the whole family explodes into, "You failed!

You failed!

It was so great!" You know, they celebrate the failure a lot, which is—

that is awesome. That's amazing. Well, just a couple more questions. I guess I'm so struck by your whole story, I could talk to you for hours, but The summation, what do you wish you had known earlier in your journey?

Yeah, I think in terms of what I wish I had known earlier, the thing that comes to mind here is about life and work and how they fit together. I've actually written about this topic a fair amount because I hate the term work-life balance. I find that it's ridiculous to think that these two things can be perfectly balanced. And so I call it the work-life mashup. And for me, it's funny because I've been calling this for a decade, but now, of course, in the pandemic, everybody truly had their work and lives mashed up together in a way that was unexpected and somewhat extreme. But I think, you know, for me, as I look back on my earlier career when my kids were younger, you know, I had— I sometimes would feel sort of guilty that I wasn't, you know, I either wasn't as good a mom or I wasn't being as good at work as I could. And the thing that I've learned with more perspective is that guilt doesn't actually make me better. At either of those things. And so I was able to sort of set aside the feeling of guilty— guilt, guiltiness, guilt— and just say, I'm just gonna do the best I can at both of these things. And for me, they are mixed together. I say, like, I'm still a mom when I walk into work. Like, the call I had before this, I was on with someone and my daughter called about some call it, you know, she's in college, she still called about a class registration question she had. And I still said, hold on, let me take this call quickly. Because when your kid calls, you don't know if it's an emergency or not. And then I say, you know, I'm still a CEO when I'm at home. And that means sometimes if urgent things happen, you know, I had one where our site was being hacked at change.org and I was in the middle of, you know, some family event. And yeah, I had to step out. And so I have the perspective that's come with time is just, it's not productive to feel guilty about those things. I'm going to do my best and that's the best I can do. And so far that's working out fine.

Mm-hmm. Mm-hmm. That's great. And last question, what specific advice do you have for other founders as they embark on their journey to grow into leaders?

Yeah, I think, I mean, the interesting thing is, you know, the advice I might have given 2 years ago I think would be even dramatically different than today because the truth is we are just living through such an unusual and challenging time. And the rules are changing in everything we do. It's, you know, everything we thought was going to work a certain way is being completely upended. And so I think that I think for managers and leaders and founders, the key thing is how do you take this moment and help the people around you get through it? And, you know, that's why we built Rising Team to help people get through it. I'd say, you know, I now summarize my book into what I also call the 3 Cs. It's 3 different Cs, but for me— All Cs. I know. See, but for me, those are courage, community, and commitment. And so this is like, if I were to give any advice, like this— the people who are successful at starting movements, at starting companies, at leading teams, they have these three traits. The first is courage. They are willing to just get out there on the cliff and jump off, and oftentimes those things are not big, they're small. When you start a company, like the first thing you might do is just talk to some people about an idea, or you might, you know, file a little bit of paperwork. Like the first instinct to start something, anything, can be often quite small. The second piece is community. It's just so critical right now, again, to build community around us. And that means I think every leader can and should be investing in that with their teams right now. But also, we need to have people around us who can support us when we're feeling lonely or sad or anxious. And the third is commitment, which is just keep climbing the mountain, you know? Left foot, right foot, breathe, as Pat Summitt says. And find people you want to climb it with and something at the top of the mountain that you're looking forward to getting to.

Amazing. Jenn, thank you so much. What a fantastic, inspiring conversation. And I just appreciate what you're doing in the world. And so thank you so much for joining me and for sharing all this, all your wisdom with everybody.

Well, thank you, Alisa. It's been great talking to you. And I, yeah, I'd love to hear more of your thoughts on these topics too.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.