Debi Kleiman is an award-winning marketer, teacher, startup advisor, mentor, and angel investor, with over fifteen years of experience working with and coaching startups of all kinds. She is managing partner of The Upside Angels, investing in early stage startups and providing strategic advisory services and coaching for founders. Prior to this, she spent 5 years as the Executive Director of the Arthur M. Blank Center for Entrepreneurship at Babson College, the #1 school in the nation for entrepreneurship. A marketer at heart, she previously spent a decade leading initiatives in brand development and innovation at Coca-Cola, Welch’s, and Procter & Gamble.

She wrote First Pitch, an Amazon best seller and #1 new release in startups and venture capital.Using easy-to-follow frameworks, stories, and best practices honed by analyzing thousands of pitches, Debi helps you build the relationship and communication strategies you need to get your new venture to the next level.


BRYAN WISH: What’s the One Away moment that you want to share with us today?

DEBI KLEIMAN: As I look back on my career, I feel my One Away moment was definitely the time that I realized you should never take a job for the money. That had a profound impact on what I was doing at that time and then what I went on to do after that. 

BRYAN WISH: You see a lot of early 20, mid-20 year olds play a short term game and regret it later. Where were you in your life when you took this higher paying job? What made you decide to do it? How did you feel during the experience when you realized it wasn’t a good fit at all?

DEBI KLEIMAN: Before I took this role, I was the president of a non-profit trade association in Boston that worked with tech startups and digital marketing and media companies and other types of players in the tech ecosystem that were really playing a role in the transformation of companies to a digital world. In that role, I got to be a part of an amazing community here in Boston of tech people, startup people, and innovation people that we’re really focused on bringing Boston forward as an innovation hub. That was work that I loved. I was really passionate about it. All the people I worked with, I really adored too because we were all so on the same page about where we wanted to take this and what we wanted to do for the Boston community.

Then I got offered an opportunity about five years into this to run a very large digital media agency in the Boston area and then also run the San Francisco office as well at the same time. It was a really incredible opportunity with a very well known agency that had great resources, great people, and really good clients. I saw it as an opportunity to flex some muscles that I had never flexed before in terms of running a very large organization, in terms of being on the agency side like that versus being on the client-side of a marketing job. It was a true executive leadership role on an executive leadership team that was really focused on growth and change. It seemed to be a lot of great energy and excitement around it. 

BRYAN WISH: You had a job you’re very fulfilled by. You’re working in tech. You were working in a sector that gave you a lot of fulfillment and joy and maybe purpose. Then your hard work, they clearly saw something in you and said, “Here’s this beautiful, big paying opportunity to come do X.” How did you evaluate the decision to stay versus go? 

DEBI KLEIMAN: They had mentioned, in the whole process that they were very interested in innovation and connecting with the startup community. That’s why my candidacy was so attractive to them. I had these networks. I had this experience of dipping into the startup world for great innovation. I thought it was going to be a great melding of the things that I loved around marketing, the digital world, and bringing startups to bigger companies and giving them an opportunity to shine and to grow their own businesses.

It excited me to play that kind of role where I was bringing people together who normally wouldn’t bump into each other. That is something I had been doing for many years in different roles. Bringing people together. Connecting people in an ecosystem. In this case, it was connecting big client companies to startups who could help them revolutionize their digital media, revolutionize their marketing, and really showcase them as leading edge.  

BRYAN WISH: With your job that was giving you a lot of the joy and fulfillment that you ultimately left, what were the criteria and the components of that job that made you come alive?

DEBI KLEIMAN: It was really a great job for my skill set. It was being a connector which is something I think I’m very good at. I love to connect people and make stuff happen. I love to find ways to introduce someone to a company or a person that can help them move forward in a way they might never have thought of. My whole role was really being a connector and a convener. We put on many large events, award shows, educational programs. It really encompassed all those things that I loved in terms of celebrating great work, educating people about innovation, and meeting new people to expand your network. That job really had all those pieces that I loved.

In the course of doing that job, part of my constituency was the tech startup community here in Boston. It happened to be a really exciting time here in Boston because it was a time when Techstars had just started in Boston. It was a time when MassChallenge had just started in Boston, another accelerator program. It was a time when the Boston city government was really recognizing that we needed to lead in tech innovation and had taken the steps to create an innovation district in Boston. All these forces were coming together to make my role, in being a convener and a connector, to be a great platform to make big things happen. That’s what I loved about it. Obviously the people is what makes all that go.

BRYAN WISH: I really notice your deep appreciation for humanity. It seems that job would give you a true platform to be able to really build these skills to lead, convene, create community, and maybe a shared mission. Also, just maybe give you a greater appreciation for the city of Boston and what was there. I think it’s important to understand what you liked about something so when you go to something else, you start to sometimes see what was so great right in front of you. In this job that you ultimately left for, talk to me about those first few months. What was it about that opportunity where you realized you might have made a mistake?

DEBI KLEIMAN: Initially, I was blown away by the agency life and how exciting it was and how sexy it was. There was lots of travel and working on a global stage. Incredible dinners, events, and opportunities to meet some of the biggest tech publishers, digital publishers, and other agency heads that were really inspiring to me. Those first couple of months, all this stuff was coming at me that was really cool. That was also the time I was spending on my listening tour where I was trying to understand where our clients were at, what they needed. That kind of research and that kind of work, I love because it’s about talking to people and really understanding the insights that underly their business, the insights that they need to grow.

I was doing things that I was good at and that I enjoyed but it was on this much bigger stage. I had a huge team. It was exciting to me to think about all the possibilities that were ahead for our clients and for the team. We had just moved into a beautiful, brand new office, and I had the opportunity to launch us in that office. It was a historic building in Boston. There was a lot of attention on it. They had done a phenomenal job building it. There were all these new and sexy things that were happening with the job in the first few months. I did love it.

What triggered that it wasn’t going quite the way that I wanted it to or what I had expected was when we launched a very big client. It had been in trouble long before I had gotten there, but I was supposed to pick up the pieces and figure out what we were going to do now that the client was gone since that client was a big part of our revenue. How was I going to fill it in? What was I going to do with the people? What was I going to do with the lost revenue? How was I going to fix it? 

For me, it’s not a problem to do that stuff. I can fix problems like that. I’m operationally quite competent and I think I’m a good people manager and people developer. It was the way that it all went down that I sort of got this inkling that I was seeing behind the curtain a little bit. Everything wasn’t quite as glossy as I thought it was. Shortly after that, I had brought a Boston startup to a client to do something really innovative; a really innovative program that I thought they’d love. I got the client super excited about it and the client was totally gung-ho.

Then ultimately, somewhere, somehow, it was decided that we were not going to use a startup to fill this need. It was too risky to use a startup with this client and that we’d go with someone who had, what I thought, was an inferior offering but was more stable, had grown, and was a little safer bet. I thought to myself, “Geez, you guys brought me in here to bring the latest and greatest to you to show clients the next shiny thing and then when I do, it’s not really what you wanted.”

I guess it was those two moments where I started to see that maybe, at the time, they thought they wanted me for what I was bringing, but it didn’t turn out to be that way. For a long time, I worked and did it the way they wanted and stepped up and managed it and did all the things that I was supposed to do there, but I didn’t have joy in it. I felt that pretty quickly that the joy in that work wasn’t really for me. 

BRYAN WISH: I think sometimes we really have to learn the hard way. We get so bought into the allure of jobs, people, this, that. When we really have a minute when a few things happen, you can’t see all the layers until they’re shed. You’re like, “What the heck did I just bite into or get into?” 

DEBI KLEIMAN: I like to feel like I can get up every day and be creative, to make something. I wasn’t supposed to do that. 

BRYAN WISH: It’s like your core value, who you were was kind of knocked down. Where do you think your sense of innovation, creation comes from within? When did you develop that?

DEBI KLEIMAN: Even as a kid, I was always one to want to lead groups of people into battle or into change or into something that was unknown. Sort of creating something out of nothing had been part of my DNA. The way I think it sort of solidified was that I went into a very classical brand marketing career out of business school and I worked for companies like Proctor & Gamble and Coca-Cola, which are phenomenal training grounds for marketers. You learn competitive positioning, brand building market research, consumer insights; all these things, all those tools and abilities, they play out in pretty much any job you have after that. It’s the best training ever. I knew then that those were the skills I wanted to be using all the time. Those were the skills that excited me. A lot of what underlies those things is understanding people’s emotions, understanding what people buy and why, understanding the insights that cause trends to collide. Those were the things that excited me. Those are creation things. 

BRYAN WISH: What a gift to be able to realize that. You were able to become aware of when those aspects of yourself weren’t being fulfilled, to also realize that you might have stepped into something that wasn’t as alluring as maybe it seemed on paper.

DEBI KLEIMAN: Yeah, it was a very sexy job. It paid extremely well. I was coming from running a non-profit and working in startups for a while. It wasn’t like I had this sort of glitzy, global platform. In my role, I was working internationally. I was working with real Titans of industry and that hadn’t been what I had done all that much up until that point.

I missed startups. I missed that early stage of that seed of an idea, that opportunity to help people shape something just at the beginning. I could viscerally feel that because when I did get the chance to do it, every once in a while at that point, I could feel my happiness rising. I could feel lighter. I could feel freer. I knew, at my core, that was going to be my life’s work. That was what I needed to do with my time. 

BRYAN WISH: Let’s talk about when you were in that moment realizing you were in the wrong shoes, so to speak. How did things unravel and unfold for you in leaving? 

DEBI KLEIMAN: I was there about 1 ½ years. Trying to make it work. Trying to find my way. I had a great team. I feel really fortunate that the people that I got to work with, I really adored. That allowed me to stay in a role that I didn’t love. Eventually, it became very clear that I wasn’t happy. My family was even telling me things at the time. My children were younger and they could even tell mom wasn’t happy going to work. One of my sons said to me at one point – we were having this conversation and I was like, “Oh, I don’t remember that happening.” He’s like, “Oh mom, that was the lost year. That was the year you weren’t really in it with us.” They picked up that I was not engaged in my life and I was so consumed with making this job work for me. That had never been something that I wanted for my life; that element of putting my career before my family.

That hit home pretty hard. I realized that I still had time before my boys were going to go to college and life would change. I really wanted to be the kind of parent that was around to go to Lacrosse games after school and to be involved in their lives. I didn’t want those years to be lost years for me. I was working against time. I had to do something or else I was going to miss that time with my kids.

It became rather urgent actually to pull the ripcord. I pulled the ripcord without a job. That was fine. My husband is so supportive. My family is so supportive that they were just like, “We want you back.” I was at a point where I was physically unhealthy. I was mentally unhealthy. I was unraveling personally and everybody saw it. Everybody that loved me knew it. I knew I had to go.

I actually took six months off and I didn’t even look for a job all that much. I really wanted to take the time to think deeply about who I was and what my life’s work was going to be. That is such a gift when you get to do something like that. It’s scary. It’s fun. You’re feeding your soul; so you know you’re doing a good thing but there’s also this, “Where’s my safety net? What’s going to happen if I don’t find the thing that makes me go?” 

I took a lot of long walks. I focused on my health. I lost 20 pounds and started exercising again. Everything started to clear. You start to get the blurriness to go away. You get so much clarity when you’re able to focus on yourself in such an intensive way. I spent a lot of time with my boys. It was great. 

BRYAN WISH: Your motivation and tenacity is incredible. It’s a beautiful drive. Sometimes under that drive is a driver. I’m curious if you had any drivers that were kind of pushing you to keep going, searching for more?

DEBI KLEIMAN: I had a mother who was incredibly successful with her career. She achieved a lot. She was a great leader. She ran big organizations. She was a much beloved community member in Boston. While she always told me I could be whatever I wanted and she’d be happy with that, I also kind of felt there was this element of I had to be as good as she was. I had to achieve the kind of status and recognition of helping people that she did. That pushed me a little bit in a certain direction to want to achieve at the same level. She was also someone who gave back a ton. She helped so many people. She was CEO of the Girl Scouts at one time. She did really innovative things with that organization. I wanted to be like her. That drove a lot of it. 

BRYAN WISH: Thanks for the vulnerability. Did you ever talk to her about that?

DEBI KLEIMAN: Oh yeah. We’ve had multiple conversations about that over time. When I first came out of college, I wanted to be a standup comedian. The idea I wasn’t going to go into a traditional career path, she was like “You’re absolutely not doing that” and I listened. I’m glad I did. I probably wasn’t a very good standup comedian. I think the thing that was hard for her was that she didn’t grow up knowing about startups. Startups were just becoming a thing then. Shark Tank wasn’t a thing. People didn’t aspire to be entrepreneurs the way they do today. In her mind, she’s like, “What’s this startup thing? What’s this entrepreneurship thing? Aren’t you just a small business owner? I don’t understand this.” She couldn’t grasp how I could make a career out of helping early stage founders. She was very nervous for me. She was nervous that I wouldn’t find what I wanted. Ultimately, all she wanted me to do is be happy. I think it was frustrating for her because she didn’t understand the world that I wanted to work in.  

BRYAN WISH: That’s so interesting. Let’s talk about that meaningful transition that you were able to make. During those six months when you were taking long walks, getting your health in order and being the mom you always wanted to be, how did you start thinking about the road ahead? What were the things that were coming to you that became important to you the second time around in finding work that really mattered to you?

DEBI KLEIMAN: I did another kind of listening tour. I had meetings with people who I had worked with before, people who knew me well, and people I had interacted with before. I said to them, “What am I good at? What do you think I’m good at?” I genuinely wanted to know. I didn’t want them to puff me up or anything. I just wanted to know what they saw in me that they thought was special, unique, or good. I wanted to hear it from their perspective and their words. I do a lot of that conversation. At the same time asking them, “What do you think I suck at?” What have you seen me do that you think is not a good idea for me to keep doing?” I’m a big believer in play into your strengths. I’m not a believer in, “Let’s work on your weaknesses and try to make them great.” I don’t think that’s the best way to go about life and to find joy. I think the best way is to find what your strengths are and lead hard into them and be great at that because it gives you joy. That’s not to say you shouldn’t be learning, but the idea of leaning into your strengths was something that I felt strongly about.

I wanted to understand what those strengths were from other people. I did a lot of that research. I was kind of doing research on my own product and I got a lot of really great feedback. People were super honest with me and gave me very specific examples. I was able to sort of tell when I was in a flow state versus not being in a flow state doing the work that I was doing. It came around that I missed the startup community in Boston. I missed all those people. I missed that work. I needed to find a way to find my way back to that. I was really fortunate because, at the same time, Babson College, which is in the town next to me, a phenomenal entrepreneurship school, was looking for an executive director to lead their entrepreneurship center. Holy cow. That was my dream job. It was like this confluence of timing was insane. I realized that was my path. That’s what I wanted to do. I wanted to teach. I wanted to mentor. I wanted to help early stage founders. I guess I’d always wanted to teach. That had always been in my career path, I think. I always wanted to be a college professor of some sort but I thought it was going to be much later. It was like the perfect job for where I wanted to be. 

BRYAN WISH: It’s funny how the universe kind of pops things up. Also, higher ed, from what I understand, it gives you that freedom to make your sons’ lacrosse games when you can and take those times. Take us with you on that joy ride to Babson. What was the experience like?

DEBI KLEIMAN: At the time I was at Babson, it was a time of great growth. It was a time of leaning into what we were great at which was teaching entrepreneurship. The college had been number one ranked in entrepreneurship for decades. It really was establishing itself at a time when entrepreneurship and teaching entrepreneurship was becoming such a big deal. All these colleges wanted to have it. They all wanted to know how Babson did it. At the same time, it was coming into Babson when we needed to do more if we were going to stay the leader. We needed to step up our game and do more. I was just the person to help them do that. It would allow me to create every day. They gave me so much freedom. I was held to budgets and so forth. I couldn’t go all crazy but they really allowed me to innovate and create every single day.

I felt I was going to work every day to build something. We were building something. We were taking this entrepreneurship center that was humming along and doing good things to something that was phenomenal, that was a student experience that everybody remembered, everybody talked about and had absolute, total impact on their lives, their trajectory. Whether or not they became an entrepreneur after school didn’t matter. It was just that they had an experience or did the project or met someone at the entrepreneurship center that changed their lives. That was my goal. I think we achieved it. 

BRYAN WISH: The people management skills that maybe you developed in your past career endeavors, you could really pour into these students and bring your skills, innovation, and creation to help them foster their ideas forward. You could really speak into their souls in a way that maybe no one ever had before or very few people had. 

DEBI KLEIMAN: I mentored hundreds of them. The mentorship part, I loved because that’s about teaching and coaching and all that stuff I did developing people in other roles and loved to do. There was probably 25% of the ones that I worked with that I really dug in with and really knew well. I think what you’d find them saying about me was I just cared so much. They could call me day or night, weekend or not, anytime. It wasn’t like I ever turned it off. I wanted to help them build their companies. I wanted to help them create a confidence and a toolbox that they felt they could do anything. Babson is a much busier place than most institutes of higher education. It takes entrepreneurship very seriously. We were all expected to be entrepreneurs in our roles. It wasn’t that I wasn’t working weekends and nights anymore. It was that I was tuning in in a more flexible way and in the terms I wanted to.

BRYAN WISH: You could still have the needs that you had wanted personally and with your family which is so important. You could still be super stimulated. You had the best of both worlds. We spoke right when I got to Denver, 30-40 days ago. You were up to some really interesting projects. I’d love to give you the floor to speak to what you’re working on right now and how it’s building on everything you’ve done in the past. 

DEBI KLEIMAN: I like to say I’m living the portfolio life, which is a term that a friend of mine uses to describe a life with lots of different projects and interests that you pull in and out of each and every day. Every week is different. I sort of have a couple buckets of things that I’m doing that I left Babson. It’s all around entrepreneurship. It’s all around startups. I haven’t left that world in the slightest. I moved into angel investing which has been so much fun. I did a little angel investing when I was at Babson, but I wasn’t allowed to invest in the startups that I worked with there. That was a college policy.

Now that I wasn’t there and I got to know so many great entrepreneurs there, there was this chance now to actually support them with money as well as my time and my energy and to dig in with them a different way. I still spend a lot of time with early stage founders. Most of them are raising seed money or pre-seed money. I’m helping them plan their pitch.

I wrote a book last year about pitching that did really well. I got great feedback on it. I feel it helped a lot of people get some concrete advice and next steps. It took them through a process. I use the work from my book. The book is called First Pitch. Buy it. It’s on Amazon. I still work with my book a lot. I speak to other college student groups. I speak to accelerator groups. I did a mini-book tour. I’m still doing that work and I love it. It’s a great basis for my angel investing because I’m also meeting some cool startups that I probably wouldn’t have met otherwise in doing those talks and workshops.

I’m loving the angel investing. It’s really fun. I’m learning a lot too because it is a different way to look at startups than I was previously. I assembled a great group of people together who want to invest together. I’m also a part of another angel network that is really wonderful called TBD Angels. My firm is called Upside Angels. It’s cool because it brings together everything that I love. I’m getting to work with friends and colleagues from other past lives and past jobs that I adore. That makes it even better.

BRYAN WISH: It’s so cool. It’s like you brought everything under one roof. The book probably supports deal flow. The deal flow probably supports the book. I’m sure projects and consulting and things are all interconnected. What a beautiful world. 

DEBI KLEIMAN: It is. I built an accelerator also. A VC firm brought me in to run an accelerator for professional athlete founders. All the founders of these startups are professional, elite athletes. We took them through a 10-week program working with these early stage startups that they had. I knew how to do that from Babson. I was really good at it. I love that work. Seeing them on demo day, how far they’ve come. You feel like you’re launching your babies into the world. Staying with them as they continue to grow. You see their businesses change so much. They change as people too. It’s very rewarding work. 

BRYAN WISH: You’re a mother to kids, mother to startups. 

DEBI KLEIMAN: That’s funny you say that. So many of my students will call me their Babson mom. I can’t help but mother people, I suppose.

BRYAN WISH: This has been such a joy, such a treat to do this with you. You’re such an authentic light. I’m glad we were able to reconnect. Where can people find you? The book?

DEBI KLEIMAN: I’m on LinkedIn a lot. I’m on Twitter a lot. My Twitter handle is @drkleiman. I have a website for the book. It’s I have a website for my angel group. That’s called On that site, there’s also a page about speaking in workshops if someone wants to bring me in to do some work with a group or do some training. 

BRYAN WISH: Debi, thanks for showing up today as yourself. It was great. 

DEBI KLEIMAN: This was great. I feel like I’ve been through a little bit of therapy now. It was good.