Building, Leading, and Paying It Forward - Ellen Rubin - Causely - Episode #53

We build relationships with customers and then we get them really engaged and excited about the company.

Welcome to Not Another CEO Podcast. I'm your host, David Politis. Every week we talk to inspiring leaders and get the true stories, the ups and downs, the lessons learned, and come away with actionable advice for our own journeys. Today's guest is a true pioneer in the world of cloud computing and enterprise technology. He's a multi time founder and CEO who has built and scaled companies that have transformed how businesses leverage technology. He co founded and was CEO of Cloud Switch, a groundbreaking tech company that enabled enterprises to securely move applications into the public cloud. That company was ultimately acquired by Verizon. After that, she co founded and was CEO of Clear Sky Data, an innovative hybrid cloud storage startup that raised over 60 million in funding and was later acquired by Amazon Web Services. Most recently, she was the founder and chief former CEO of Caudly. Today she serves as an operating partner at an early stage venture fund called glasswing Ventures, where she helps support the next generation of entrepreneurs. She's also a passionate advocate for the Boston technology community and for advancing opportunities for women in technology. Please welcome Ellen Rubin.

Hi there. So, so great to talk to you. Thanks for having me.

I'm excited, I'm excited that we're doing this. We've been trying to get this up a calendar for a while. So very excited for this conversation. Let's go straight into it. First question, what is the one thing you've done, big or small, at any of your companies that's had the biggest impact and you do again if you're CEO of another company in the future.

So I was thinking a lot about it since we talked and I was thinking about what really makes a startup get off the ground and be unique and powerful even though it's so small and there are so many things you don't know and you know, so many challenges. And of course in my head it's the team, it's the founding team and it's the early team and it makes a huge difference in terms of who those people are. And I was thinking about the fact that the people who have been involved with the companies that I have started and I've been fortunate enough to get to work with have certainly an intellectual curiosity that's part of it. But also they come to a startup, you know, like Cloud Switch or Clear sky because they see an opportunity not only to do something that's huge and might have a huge outcome and all of that, of course, you know, that's part of it, but A lot of them have said to me over time. I came here because I thought this was an opportunity for me to see how startups get built and what it takes to get a company off the ground and to grow and scale it. And that if I were staying in my very highly paid, very wonderful job that I already am in and, you know, have no reason to have to leave, I would never really learn. I'd never have an opportunity to see these things. And so a lot of the work that I did in, in past companies and would definitely do again is trying to expose people who are there to do a particular job, right? They're in, you know, they're developers, they're marketing, sales, they're, you know, finance, whatever it is. They're, they're doing the role that they're in, but to try to really give them a full picture as much as possible about what it takes to build a company, get it off the ground, and what the different areas of the company need to do to be successful together. And so, you know, for example, if you're somebody who is, you know, a BDR on the phone or you're somebody who is, you know, developing the, you know, initial, you know, product and code, you might not have a really good understanding and especially if you're earlier in your career, you might not really have a good understanding of what does it mean to raise funding, what does it mean to have to evangelize and be out there and, you know, in the world telling the world about this crazy idea that you have. You know, if you're, if you're not somebody who is technical, why is the product getting built the way it is getting built?

Right?

Like what? Why does it matter that the engineers are over there screaming about, you know, this philosophical debate or whatever? There, there's a reason. And of course, the other way, how, what does it mean to actually get an enterprise customer to want to buy something from you and what are the steps of that process? So in order to do that, there are a lot of things that you can do as the CEO and there are things that you can sort of enlist other people in the company to help you do to, to create that opportunity and that exposure. So, you know, obviously the all hands and you know, like regular conversations that you're having as a company, but, but even more informally, there are a lot of top times where having people kind of sit at a more of a lunch and learn, like, let's just have lunch or let's, you know, get on zoom during COVID or whatever and that somebody would present. Not just demoing like the latest version of the product, which is something we did, you know, as part of our Sprint process, but also sort of saying like, hey, we're running this marketing campaign and here's why we're doing it and here's what we're testing and some of, here are some of the tools that we're using and here are some of the early results that we're going to keep refining. Right, or right now we're raising funding. And so here's some things, you know, you can't share everything, but here are things about the way that process works and here's the different stages of a startup that go from this point to this next milestone to this next milestone. So definitely did that. And I think I mentioned to you in our previous call that, you know, I even had sometimes one of our board members or someone who was an advisor to the company come in and meet with people and just have a conversation, share their experience and you know, like the fact that they had built and funded and you know, themselves been entrepreneurs and stuff like that. And I think for people it's very encouraging and eye opening to sort of say, like, oh, if I were going to do something like this, I either want to be a founder or I want to at my next stage, I want to be in a more senior role and you know, in, in building a new company, what would it take and what do I need to understand and be part of? And I feel excited about it mostly because, you know, sort of wanting to foster that community in the ecosystem. It sort of helps people then go on to wherever they end up several years later, you know, to kind of take that with them.

Do you, I love this. How do you identify the people to bring on that are going to appreciate that? Like, because that I love it. And I actually think back to days where like, probably I think one of my highest rated all hands that we ever did was when I explained going from seed to A to B and like, what it meant. I think I was like, not, not company related, not like just explaining fund fundraising was like one of the best rated all hands we ever did. But there are some people who were on that all hands. I remember who said, I don't care.

Like, like why, why are we talking.

Why are we talking about this? So like, how do you find the people who would appreciate, you know, who want that?

Right?

And it's not a, like, oh, if you're not interested in all of the different topics, like, oh, that's bad.

Right.

You know, for some people, they're here to do the thing they love to do. They're passionate about it and they're excited. Sometimes I think it's a little bit, maybe more that for people who are. So I guess what I. To answer your question, the people who are like that, you just know them right away and they raise their hands and they tell you these things, right? Like, even in the interviews, I remember people saying, I'm coming here to sit with you and your co founder and learn and be part of this conversation. And you know, this is something that I'm excited and someday I want to do X. So then there, you know, there's no mystery in that case. In other situations, it's kind of a surprise, you know, like you have someone who's off, like, might be a little quiet or maybe a little more introverted, and somewhere along the way they come over and they kind of engage you in a conversation. Mostly when you're sitting casually somewhere, you know, like you're, you're, you're at a company, you know, get together, you're like in the kitchen or, you know, whatever, and they're just, or you know, you're sitting on zoom waiting for a meeting to start and they just start adding, asking a bunch of questions, right? Like the questions could be. And they're not about like the topic at hand. They're more like, oh, hey, I saw you talked about this on this podcast, you know, with, you know, with. Yeah, yeah, And I was really wondering why you said X.

Right?

And so then, you know, then, then, you know, then you know that they're there. And I think that even for people who aren't necessarily thinking of that as being, you know, critical or that they don't really want to know about the stages of funding or something like that, it's really great for alignment because whatever you do, and however small the team, still there's a little bit of like, okay, I don't get what that guy over there does. You know, like, you know, if someone's in a more experienced person in the startup world, then maybe they have more context. But even so, actually I have not necessarily found that to be the case where they're kind of like, oh, so and so is working on this. I don't really know why they're doing that. You're like, okay, well, let's talk about it. There's a reason. And by the way, what you're building over here or what you're selling over here is directly related. So, you know, we don't have time in a startup for people to be working on random things that don't connect to each other. So let's just make sure you really, really, or even maybe, hey, it's on me as the CEO to make sure that the communication is. Is in place, you know, for people who have questions to feel comfortable to ask those questions, like, why are we building this and not this, you know, is a totally fair and legitimate thing for people to. To want to know.

I like that. You know, when I think back to some of the companies that like the lunch and learns. When you mentioned the lunch and learns, you know, and I think about some of when, when we had people speak about their function like a support person, we. I remember we had a support person come up and just explain what kind of tickets do we get? How do we respond? And there were a lot of people being like, whoa, that's. And I remember distinctly an engineer who said, oh, I can fix that problem.

Exactly, Exactly. They go away and they're like, that's ridiculous. Let's just make that problem.

Right.

Yeah. So I like that a lot. You know, so. So I mean, I think a theme in my introduction in every, in every conversation we've had so far is like, you definitely have a passion for helping the next generation of founders of entrepreneurs, clearly, because just even in this answer, and one of the things you've mentioned it a number of times to me is really helping women in technology. Specifically, can you talk about what that means to you? Because you mentioned it a couple times and I'm curious, how do you do that?

Right.

So it's. I'll describe it as a lifelong journey. And occasionally, you know, as I'm doing, I'll describe it as yet another panel, you know, about like, women in tech and women founders and stuff like that, I kind of feel good about some of the progress that I've seen. And also sometimes I feel like I'm still having the same conversations I was having, you know, 20 years ago. So it's, it's. It's mixed is how I would describe it. So I, because I chose to be involved in IT infrastructure, enterprise IT B2B infrastructure, like storage, networking, data warehouse, like data centers with, like blinky lights, you know, like, that's my thing. I dig it. I'm really into it. So because I chose that, you know, for my sins, I do actually find myself often being the only woman in the room. And there, in. I'm in an area where there are fewer women who have been founders, you know, not there. It's it's not none, but it's a smaller number. So I, like, like it or not, it became obvious to me that there was sort of a lack and a need, you know, to, to be personally involved in that as an issue. And so over the course of many, many years, I'm going to say decades at this point, I've tried to do things kind of in a few layers. So like, they're sort of like the, the macro sort of higher umbrella layer where you speak at events and you, you know, kind of are out on the circuit and you're constantly, you know, sort of evangelizing and talking and you're sort of saying, look, here's my journey. I was able to do it. I'm with a bunch of these other women who are, who also did it. And so first of all, it's possible, and second of all, we're here, you know, to, to be a network and support, you know, a group for people. But then there's a little bit more of like, the local stuff in Boston, which, you know, I think, you know, we'll talk a little bit more about Boston where you can kind of be a little more proactive.

Right.

Finally, there's like, at the most intimate and personal level where it's people in my own network, you know, people in my friends, you know, now kids of friends, you know, who are thinking and starting stuff like that. So I always, I have two daughters and I always have said to them that, like, I kind of have a formal policy in my head which is if a woman entrepreneur or a woman who is building a career in tech reaches out to me and, you know, anywhere on LinkedIn, you know, the show, you know, calls me up, whatever, I'll take the call and I'll get together with the person if I can and just sit down and talk with them and try to figure out, like, what are they wanting to do and what is it that they need. And sometimes what they need is just encouragement, but other times they need really practical stuff. They need an introduction to that guy, you know, Joe, Joe Schmo, or there who is going to help them to get to the next point in their funding journey or in their, you know, they need a co. Founder or something like that. And then other times they are stuck on issues of team building, right? In terms of like, what, what. Who should be in my founding team, who should be in my early team, what do I need now, what are the skills I need? And sometimes that's introductions that I can make, you know, and sometimes it's more just helping them think through it. So I've done a lot of, you know, mentoring, advising, kind of both informally and formally, but you kind of have to think of it as layers of energy that you need to put in, and it has to be sustained.

Right.

It can't just be like, oh, I feel like doing it this month, and then I'm busy.

The part you said something about showing people that it's possible, and in a number of these interviews that I've done now, I'd say at least 30, 40% of them, the CEO I'm interviewing has said something to the effect of this person, and they could name the person, showed me that it's possible, you know, and. And whether it was a family member or parent or mentor or just someone they watched, you know, at a. At saw at a conference. Hey, super. When you say it, it. Actually, I think there's some element that literally just knowing it's possible changes something in your, like, brain. Like, I could go do that. Why can't I go do that 100%?

And sometimes it's like, I want to do it, but I'm not ready to do it yet. And I'm trying to think about the steps I want to take in my career that will get me to a point where either I will become the founder and the CEO, or maybe that's not the aspiration. Maybe the aspiration is I want to be part of the founding team and I want to run this type of, you know, functional area, and therefore, I need to build skills. Either or.

Right.

I'm. I think, you know, I think it's important to pursue all directions there. But, you know, of course, in my heart of hearts, what I'm really like, is like, why wouldn't you want to be the founder CEO?

Right.

You know, so I'm. Sometimes I'm a little like, you can do it. You know, don't. Don't limit. If that's what you think you want to do. Don't be limited.

What were the challenges that you faced? I mean, I. You, you, like you said, I mean, you've been in, like, the hardcore infrastructure world, which is definitely. I mean, not consumer technology is not a dating app. I did is like, hardcore. Yes, you know, infrastructure. What were the challenges that you faced as you were starting your first companies?

So it's funny, I always think about it, and I think, like, was being a woman a limitation for me? And I'm sure on some level it was. I have no doubt that it was. But actually, at the time the way it felt to me was that I wasn't an engineer, I wasn't a technical person and in fact that seemed to be the bigger hurdle. So my background and expertise was more in. So I have an MBA and I, you know, my background and expertise was more on marketing and you know, business development, third party technology, relationships and stuff. And I had built an early career on that role. And it's, that's actually kind of a hard jump, right, you know, to go from there into. And then I'm going to build a company that's a heavily technical company and I'm going to be the founder, CEO and stuff like that. So part of the journey for me was realizing that I needed a technical co founder who I could really work well with and who was comfortable with me being the CEO. So that was, you know, part of the journey. And then part of the journey was just. I, all I can say is just like working my butt off to get smarter about the technologies that I was involved with and hands on with the products and like really sitting with the people, you know, with my co founder and other people who were the earliest engineers to really understand what are we talking about here. And in the end, you know I, I am who I am, right? You know, I'm still, I'm the, I'm the business, you know, I'm not, I'm not the technology. But you have to get closer and closer and closer so that you really have something to say about it or have intuition about like where is market going and what opportunities are there. So that to me at the time that seemed really hard and you know, I needed in some cases like, you know, a lot of support. So I didn't feel like I was just kind of making stuff up. You know, I memorized a whole bunch of stuff and now I could, you know, so like that to me those were like the really early concerns and challenges that I had. And you know, some of it is, you know, determination and desire to do it, but some of it is also having really great people around you who will work with you. I used to say like to one of the cloud switch founding engineers who like he and I used to hang out together a lot and I would say to him, you know, I only understand 50% of what you just said to me right now. And he'd go okay, which 50% unravel the whole thing and stuff like that. But at the end of it I understood more, right? And then that was really helpful for me to like relate that to the business decision that I needed to make.

You know, so another conversation and thing I mentioned in the introduction is you've been, you're also very passionate about Boston and, and, and you've built your businesses there. And, and you, you know, you're, you're, you're trying to help that community now. And you know, what, what is kind of the Boston ecosystem, what's that evolution kind of looked like over the years? I've spent some time there, but obviously I spent most of my time in New York and Atlanta. But Boston, I feel like, has kind of its own unique kind of kind of journey, if you will.

And last time we talked, you were like, I was like, oh, stab in the heart, like sharing some of the stats that are out there. And I go, Boston, number this and number that. I'm so. Okay, so I'll just get it out on the table. Like, I'm a huge, you know, Boston fan girl. So, like, there's, there's, there's no, you know, impartial thinking here at all. But what I would say to you is I built my career here and I have a whole group of people that I am connected to and, you know, involved with on an ongoing basis as, you know, fellow entrepreneurs, founders, investors, angels, you know, people who are in the academic world who kind of move back and forth and stuff like that. It is a vibrant and powerful ecosystem here. And, you know, there's definitely a desire among myself and my peers to keep that going and to keep enabling the health and the growth of that environment. Obviously, we benefit from having fantastic institutions and certainly in the world of AI, I mean, you know, Harvard, MIT and a bunch of other institutions here are at the forefront and there's all sorts of exciting stuff that comes out. The commercialization of it is very much based on people who are young and early founders believing that this is a good place to build a company and that they're going to have access to capital, to advisors, to mentors, you know, people who are powerful in their industry, who can help with, you know, introductions and stuff and ultimately acquirers if that becomes the relevant next step. So there's a lot of thinking that, you know, I do and, you know, been part of a lot of different organizations, most recently with the post exit founders that I, you know, I will talk about in a little bit, probably. But like, the goal is to really make sure that that ecosystem is strong. And I would say that, you know, if you look at it, obviously Boston has had a lot of success with companies like HubSpot and Wayfair and Klaviyo that have gone public. And then also like my early journey at Neteza in the data warehousing space, you know, went public, then, you know, got bought by IBM, product still in the market 20 years later, Kiva Systems that got bought by Amazon, as is now Amazon Robotics. So like companies that kind of became foundational companies and that are still doing that. And you know, the goal obviously is to continue that momentum and to also have some of those companies as anchor companies to help pull the next generation into the community and to stay here and to help build it and grow it. And that's what I'm doing right now. Honestly, you know, in my work at Glasswing, I would tell you that, you know, like there is, there's something with Boston where sort of like the stuff that's the hard technology problems, we're really great at that. You know, like when it. Sometimes it's been more sort of like application level or you know, stuff that's more, I don't know, consumer oriented. We've been less successful. And that's just true. So you know, that's, you know, just, you know, being more reflective on things. But there's enough here and enough critical mass for people to be able to say I can stay and I can build it. And what I have found is that the community is unbelievably supportive and collaborative. Like you don't come here and get lost.

Right.

It's small, it's, you know, much more intimate. And if you want to be part of things, you can be very quickly.

You know what's kind of interesting, I just thought about this actually as you've been talking because I've talked to a number of people about their local communities and it's kind of interesting because you think at least high level Covid happens. Everyone kind of works from home. All the companies started going remote. There's no more. But actually in a lot of ways the local piece matters so.

Right.

So much, you know, and I don't think you can actually build community and the support system virtually let fit. He felt like, I don't know, I just. As you're saying it, it's like, yeah, you need that critical mass. The school's help and the, the exited founders and the big companies and the, you know, all those things kind of. Even the folklore, the lore of the city and the companies. Like there's something interesting about that because so many people are like, we're all remote and everyone's all over the world in the country. But actually, at least for the Founder type communities and like, being local, there's, there's something very real about that.

Totally. You know, it's, it's. I guess what I would say is I've had a little bit of a shift in terms of I was at Amazon, you know, when Covid started, and I was there working remotely with people who were all over the place. And then I started Cosly also as a fully remote company, which I would never have done, you know, prior to Covid. And the answer is you can, you can do it. It's possible. Do I love it personally myself as a founder, I don't love it. And now that I'm sort of back downtown and spending time, you know, with other entrepreneurs, like, you know, sort of all the time.

Right.

You know, constantly, like, okay, yeah, let's just go grab coffee and stuff like that. I realized how much I missed it and how much it was missing from my experience. And, you know, we're like doing events, you know, all of Boston, you know, Glasswing for sure, but all of Boston, we're doing events all the time. And like hundreds of people are showing up, you know what I mean? Like just on a Tuesday. So clearly there is a desire and a, an interest in doing it. I think the answer is that people want to do it. They may just not want to do it five days a week. And I think that the balance of that was something that I, I didn't maybe understand as much in terms of that for some people just having a day or two where they didn't have to come into the office and that they could have some flexibility about it and that really was possible to do their jobs when they needed to remotely was pretty life saving. And so I don't think people are, are rushing to give that up, but you can still do it the rest of the time. And, and that love, I, I think.

I think that's the, I think that's going to be a competitive advantage for companies. The one that, that may have recently made that hard decision to say, we're going to do this in the office. We're this team locally, we're going to, you know, it's expensive, yes. Harder to find talent, maybe depending on what people are looking for. But even the stuff you were talking about before, you can't have that conversation where someone sits next to you and says, hey, I read this, I heard this. Because they're not going to ask for the CEO to get on a zoom to ask them up how many assessment podcasts, like, that's not going to that's not going to happen. You know, those conversations don't occur. The conversations between two people on different teams having lunch at the same time, like, those things don't ever occur.

It's much harder. Yeah, we were doing a lot of, you know, so I ended up, you know, certainly more recently at Amazon and at C doing many, many more one on ones with people, because I just, I had lost the connection. Right. You know, in terms of you could just wander by, you know, and see them in the hallway or something like that. And I didn't like that. And I wanted to have that type of connectivity. It is hard to do. And for some people, if they're more, you know, introverted or this is their first job, it's a little stressful to them to get on the phone with the CEO, kind of like, okay, what do I say? Listen. If you're sitting at a table and they're listening, and they might be more inclined to sort of sit or something like that. So I definitely think that, yeah, I think a lot about, like, the people who are, like, it's. It's early in their career and they need mentoring and they need models and they need also the social aspect of things. And I, I would not want to go back to a situation myself personally where there was none of that. And if you're doing things on a quarterly basis and stuff like that, okay, good, you know, you get people in and stuff, but, like, it's not the same. And so, you know, I'm, as I think about it, I do have to say though, that, like, you know, with the companies that have been really good at doing, like, fully remote, they got excellent at it, right. They had their practices and their policies and stuff like that. But for me personally, I, I'm missing part of what makes you want to be a founder.

I agree. You know, when you say that about the people earlier in their career, I kind of feel like it's whatever people's opinions are, you know, the set of children that kind of were in school in those really important years during those first couple of years of COVID and we don't really know what that impact is, that's right down the line. And my kids were very young and went through that. And I think there may be some social elements that weren't there because it was an important period of time. I actually think we could make the same argument for the people who came out of school and started working. We don't even know what, ten years from now. Those people don't have the networks they don't. I mean, just by definition, they don't have the networks and those close relationships and everything that they had. They don't have the person that they sat next to it and grinded it out for, you know, all the long hours. Like, even if you've got a great culture, at least in my opinion, like, that's the group. I don't think it's the people who are 20 years into their career that were Impact. It's like, it's those people who were first. This is their first job. That's how they experienced work.

Yes, I totally agree. And I realized I forgot to say something earlier, which I should have said, which is one of the other things that I did in some of the earlier companies was also to try to bring customers in to the company physically, where possible. Which back at that point point, you know, I've been, in the past, I've been able to do. But certainly on, you know, on Zoom, and, And to. To do sessions where a customer who's an excited, happy customer who either, you know, recently purchased or is in the process of, you know, deploying and expanding, exposing the company as a whole to as much of that as possible and allowing them to ask questions and get a feeling of, like, the. The importance and the passion of it.

Right.

And so, you know, like, it's, again, it's easier to do those things when you're kind of gathering people together and you're having that kind of more of a group experience. It can be done on Zoom, you know. You know, it's. In some ways it's easier to do it on Zoom, but like, that feeling of, we built this product and it's for this guy or this woman, and here's why they bet on us and they made a decision about using our product that they didn't have to make. And here's why that matters.

Right?

Like, there's some of communicating that, like, I think for especially someone earlier in their career, you want them to understand that what they're doing has real impact on people's lives.

I love. I love that, you know, I want to go down that, like, tactically, I. Because I love that I actually didn't do it enough at any of the companies I was a part of. And when we did it again, you could see the impact that it had on the team.

Like, yes.

How often, for example, like, was that a regular thing that you would do at once, a quarter, once a year, once a month?

As. As much as we could make it happen?

Right.

You know, you needed the customers to be able to. They sometimes had to get approval from legal. You know, it was like a whole to do.

Right.

You enterprise.

Right.

But wherever possible, and especially if the companies were, you know, a little less regulated, you know, like, not the banking customer.

Right.

You know, not the healthcare customer. Although sometimes. But more like, you know, a company that might be a little more able to say yes, it's okay for you to just go ahead and speak. It's funny like how strict some of that was. But wherever I could get that to happen and I had someone who was a comfortable as a champion doing it. They love doing it. It was fun for them.

Right.

You know, it was like an opportunity to talk about, like. And also, of course, what did they do? They gave us that. Here are the next five roadmap things we really want, of course, have the engineers in front of them. So, you know, that was, that was good.

Did you moderate that? Did you like do kind of fireside chat? You moderated. Did someone on your team do it? Did they present? How did you structure that?

Sometimes I did it, but often it was like that the person who had, you know, if it was a salesperson who had actually built the relationship and done the, you know, kind of development of that, I'd have them sort of like do the introduction. Like, look here, you know, this is what we're doing here. You know, like again, like this is what we do. We build relationships with customers and then we get them really engaged and excited about the company.

Right.

Like that's.

I like that.

So that was very fun to do.

Right.

It didn't, it didn't have to be me all the time. You know, in fact, sometimes better, if not, you know, like that other people in the company are doing this kind of stuff.

I like that. Let's, let's talk a little bit about operating rhythm because we've talked about these all hands and we've talked about some of these things. Like how, how did you structure that? You know, was there, was there a, let's say how strict was the cadence? What was in that cadence? You know, can you talk me through that a little?

For sure, yeah. So, you know, it's evolved over time. Right. So like more recently, everything's on slack all the time.

Right.

So there's constant, you know, updating and you know, engagement and stuff in that context. And I would say that the, the all hands piece of it, especially where you're remote, is even more urgent in terms of stuff that you can do. If you're in an office, which I was, you know, in all my previous companies there were a lot of things that were, as I was describing, kind of like the more formal stuff, like all hands is sacred. We do the all hands. It's not a casual thing. We want to make sure people know that there's going to be an update and everybody's there.

How often would were the all hands?

Every week.

Every week?

Every week?

Yeah.

For how long?

You know, it sort of depended on what there was to talk about. And so there were times when they went longer and included more updates and comments. Sometimes they were relatively brief. Obviously we had the engineering structure right in terms of like the stand up and all that kind of stuff. So that was going on and some of the information was communicated there. But we tried to keep those tight. And we also used the opportunity of, you know, like the Sprint review and you know, the opportunity to kind of talk about what we accomplished, to tie back sometimes in terms of like, not every single time, but like more on a quarterly basis to say, remember, here's what we're building and here's the value to the customer and here's why this Sprint moved us forward to that. Because the customers that we've been working with or the design partners told us that they needed certain types of things and here's how these things relate and later on we're going to do it. So it wasn't like a full roadmap review, but it was sort of like you are here on the map of, you know, kind of connecting the dots a little bit. And then we did, you know, certainly at Clear sky, we did more of these lunch and learns and stuff like that. I tried to do those, you know, every couple of months where it was just a topic that seemed interesting to people or that I felt that people seem not to know about and that maybe it would be helpful for them, you know, or somebody asked me a question that I thought maybe it was good to share the answer. So those were things that we did regularly. And the way I feel about this stuff is you don't want it to be onerous and people are busy and nobody wants another meeting. But people, even in a relatively small company and gets much more challenging as you, as you've scaled and you have more like functional areas like they sort of just want to know what's going on and if you don't have a regular cadence of it, they will go look for the information or hear things that maybe aren't even the right information.

Right.

You know, like there's, there's no Upside to that. And so what you really want is even if there's not a huge amount to report the idea that you've sort of said to them, we're going to be as like insanely transparent as we can possibly be and you can ask whatever question you want and we're going to be really open about things. Some things, you know, we're not ready to share information yet because we're still in progress or they're, you know, it involves whatever somebody's personal issue or whatever. But the truth about it is, is like where we can, we're going to share the information and then that's it. And then you know what's going on, right. And then there's not like a little bit like oh I heard or so and so is thinking this and stuff like that. And I think that that's important for alignment but I also think it's important for people to feel like they understand what is happening with the company and what is the mission of the company.

I like that the connecting the dots term that you said before that I think that that at the core, right is such a value where people, if they know what they're working towards and why they're doing the work and why the company's doing like that just is so much, you get so much leverage on, on that. And I, I find that I talk to especially early, early stage founders, companies, 25 people or something like that, they feel like for them it's the bird to do the all hands, you know, and, and I tell people you don't actually the power to, of that all hands of the weekly cadence where people know they're going to get the information. Someone told me one time if you leave a gap in information, people are going to fill it with you know, what basically because you know, they, they, they, they don't know where else to go get that information. So it's like giving them that, you know. So I, I re. The connecting the dots actually is the, that's the power because when you get everyone aligned and everyone knows what we're working towards, they work harder usually.

Right?

Yeah, there's a lot of like mystery especially around the funding, the VC's valuations, like there's a lot of like, you know, whatever. And to the extent, you know, without sharing people's personal information, you sort of want to say look, this is how this works, right? I mean the truth is this information is all sitting out on the Internet. You can find it pretty straightforward but sometimes like where you sort of explain it to People, it's, it, it helps relieve some of the, you know, anxiety that people might have. And I did feel. It's funny, there were, you know, we can talk about Amazon, you know, probably, you know, over coffee sometime, whatever. But like, I learned, I did, I learned a lot there. And one thing that I learned was how seriously they took the recruiting and the onboarding of new employees. Like, like, it was really intense. Like, the, the interview process was super intense. And, you know, there was all this stuff about, you know, the leadership principles and applying them and everything and showing how you did stuff. But what it did was it kind of like leveled the bar for what are we screening for for this particular role at this level? And what kind of things do we want the person to know how to do and be able to do and to be able to culturally fit into this organization? And I, it was at least a model. Like, I don't know that all of it is applicable in a startup, but it like, it kind of demystified things that could be, for people confusing, right? Like, okay, we hired that guy. Why did we hire that guy? What are they doing? You know, that kind of stuff. Is he going to make more than me? You know, like, well, you like, remove a lot of that. It kind of allows people to focus on that they came to do exciting work and that's why they're at this company.

How long were you at Amazon?

About a year and a half.

What else? I'm curious, what are like the other top that you won't talk about? The bad stuff, the good stuff. Like what. What are the top things you took away?

Other than that, I still believe in the prfaq process, which you may know of. So the idea that when you're developing a new product, before you write a line of code, you write a document that is the press release that will be released at the time that you launch the new feature or Service. And the FAQs of the, like, dozen questions, you know, there's like a half a dozen that are in all of them. And then, you know, there's some variation for the rest of them. But like, the key questions are, who's it for? Why do they need it? What are they doing today and what can't they do? And why is this going to uniquely solve their problem? Right, like this, the working backwards stuff, but like forcing you in a systematic way to go through that. And I think it's good for startups to do that too. You know, like, what do we imagine this product and this company to be? Do the Founders agree on what that would be.

Right.

You know, like, these are really important things. And I think that being forced to write it down as an actual document and not just PowerPoint with bullets, you'd be amazed how much harder that is.

Right.

Like, you know, like, does, does the argument hold together and explain it to somebody who doesn't know anything about this product? Like, could you write it in such a way that people would understand? And I think it's. I think it was great training.

You. You been through talking about Amazon, you've been through the M and A process a number of times through with your companies. How did those processes start? Were those you selling the company or were those people buying you? If that makes sense.

So I've had it many ways, many flavors, you know, and now at this point, I've also been on the other side of the table and, you know, sometimes I'm just like, whoa, this is, you know, like, every movie is different is how I would describe it. So, you know, I've kind of. I've seen in a lot of ways. So obviously it is more fun to get bought than it is to be selling.

Right.

That's, I think, a truism. And sometimes the decision is, you know, are we at a stage where we need to.

Right.

Because we're going to need to raise a lot more capital, and is that going to be accessible to us and stuff like that? You know, there's, there's some of that. Sometimes it's, wow, there's an opportunity here. What's their expression? There's an expression, local maximum. We're like, it's not to say that the company couldn't theoretically go on and do other things, but we're sort of at a local maximum where the founders feel like this would be a place that they want to go and that it could be a good outcome. The investors are supportive of it. And it feels like if we're part of this other thing, we could get to where we want to get to, better, faster, you know, in a more impactful way. Right. And so there, there are decisions to be made. And, you know, of course, best is where there's a bidding war and then people are fighting over you and stuff like that. That's always, you know, the, the, the desired outcome. But really, in the end, you have to say, like, I'm going to go devote my life and a bunch of the people, you know, like this, this team that I built, and they're going to spend a bunch of time in their lives at this company.

Right.

One Way or the other, you know, we're going to be there at least for a year or two and we're going to need to see how it goes and see, see if we're going to stick around and you know, like, is that, is that what we want to do now? Like, is that the next thing we want to do? And you know, like the answer, like certainly, you know, in terms of some of the experiences I had, you know, when we were talking about things that, you know, at Clouds, which we were like, well, we're pretty early and whatever and this is a growing market, but we were looking at the fact that hybrid cloud and the adoption of cloud computing by enterprise was clearly going to happen. But it might have taken and in fact did happen. And you know, I got to see it all the way through, you know, to like when I was at Amazon another 10 years, right. Like, because I started, I was so ridiculously early. I was back in 2008, you know, so it was kind of like, okay, as we get into 2015 and stuff, you know, it becomes just everybody's using the cloud. But it wasn't like that at the beginning. So like being part of the Verizon cloud platform made sense and seemed like a good bet for the company to do and. But you know, like as with all of these things, it's like, you know, it's your baby and how do you feel about it and you know, the emotion comes into it. But in the end you sort of have to sit down with your co founders and your investors and say like, is this, is this the right time for this company? And you know, I think, you know, I'll stand by those decisions.

Would you meet with those. A lot of people are getting calls from corp dad kind of all over. Like would you take those calls? You know, let's say when you're running the companies and some random person from some, you know, just reaches out cold. Hey, I read about you. Ellern would love to talk. Like would you take those meetings or you know, kind of put those at.

Arm'S length, you know, usually those happen after you've announced funding, you know, you know, you're kind of like, dude, I just raised funding.

Right?

Like, like go away, right? No, I think, I think it's always good to have like a quick intro conversation but early on where you're still building the product and you're still getting it, you know, into customers hands and you're showing the value it is and stuff like that, you know, there's really no point. And so at that point, I would feel more inclined to say, listen, we're not ready yet, but happy to talk with you. You know, six months from now, a year from now. Then when you're sort of at a point where you're kind of more in the scaling and growing phase, it's not a bad thing because some of those companies can be strategic investors, right? I've had strategic investors in pretty much all of the companies I've been part of. And it's. They can. They don't necessarily become your acquirers, but on the other hand, it's usually something that is additive to the other fundraising that you're doing and can be valuable. And also, sometimes it also is helpful with customers that they feel that you have, you know, like the relationship with a larger strategic partner and stuff like that. So those things can be helpful and good to do as just a, let's get to know each other, you know, let's engage a little bit. But the truth is, you don't want to spend a lot of time on that stuff before you're ready. And it's an incredible time sync. You know, like, I used to find. Oh, my God. I used to find with especially Cloud Switch again, as an example. Like, everybody wanted to talk about the cloud, so they were like, delighted for you to come and have a long conversation. And they put like 25 people on a call, right? Like, it was ridiculous. It was just ridiculous because they were like, trying to, like, I remember with VMware, like, they couldn't get enough of us, you know, like about, like, oh, what are you building? And, like, how much of it can we steal? And you know, like, no. And, you know, you're doing that little, like, dancing with the elephant thing, right? You know, you're like, going around trying not to get, you know, rolled. Rolled, you know, over.

So.

So it's not a good use of time. But I think in a, you know, like sort of surgical. A couple of people that you talk to seem like they're smart and they get it. And then it's worth kind of like if, hey, if you're going to be in town, let's have coffee, you know.

Like, keeping it light, you know, A couple things you said there. The dancing with the elephant is a good, good way. I've never heard that, but that's a good way of describing that. And I think over the years, I don't know how many big companies copied things that I showed them, you know, in the process. And I think now it's the AI companies, like, you in the early days of cloud, it's the AI startups that are getting calls from more the all the corp devs. I work with a bunch of them and they get these calls and they, oh, come in, we really interested, you know, and, and they show up with 20 people and just do give me a full, you know, break up.

Let's do an hour demo. Right, Exactly. You know, you could almost say like, look, we're happy to have a conversation, but we'd like to do it in person in our, you know, in downtown Boston and then just what happens, right? They're not going to bring 25 people to Boston.

I mean, that's good advice that, that's good refuse, Right.

Like I really want to talk to you and meet with you, but let's just get to know each other.

Right?

Because really what they wanted was the demo and the chance to kind of like suck your brain dry a little bit.

Exactly.

Don't give it to them. Right.

I like that. What is your view on AI? I mean, you've seen so many of kind of these, these technology cycles and rise of the Internet and rise of this, you know, rise of cloud. What, what is your view on AI?

So Rudina, who's the founder, managing partner along with Rick Grinnell at, at Glasswing, so they, they have a saying, okay, which is that AI is the overnight sensation 70 years in the making. That's their, that's their thing. And so I, I had to laugh when I heard them say that because I remember I started a company, I was living in Tel Aviv after business school and I started a company with some Israelis, like by accident, like a few of us in a room somewhere. And it happened to be a real time recommendation engine for E commerce, which was at that time kind of a big thing.

Right.

And it was like, you know, if you like this, you might also like this. And it was using Bayesian network algorithms at the time to figure out like, based on your demographics and your buying patterns and stuff like that, what would you like? And of course we had no idea what we were doing. It's like ridiculous story, but we were using the AI technology of that time, which I believe was sort of the second wave out of three waves of AI know where it's kind of like been the hottest thing and then it's kind of disappeared completely. So here we are, right. You know, in, in this latest phase. This one's going to stick, right? I think we can, we could agree that that's, you know, that's where we are at the moment where it's, it's like it gained so much traction and, and you know, buy in by people. The big thing this time that's different from my cloud computing experience is that enterprises started buying right away. So I'm seeing that, you know, in terms of the diligence that, you know, I do diligence on companies every day, you know, as part of glasswing and also in the companies that glasswing has funded, we're already at seed and even at pre seed they already at, you know, hundreds of thousands of dollars of ar sometimes, you know, like there's meaningful revenue that's being generated and it's very often at enterprise customers. So you have to say, who knows where this is going to go, right? This is, we're in a totally wild and you know, wild west moment. But what really excites me about it is that there is a desire to use the technology for actual problems in an actual industry context that solves a particular use case like right away. Not necessarily. We built this huge platform and somebody's going to figure out what to do with it and stuff like that. So like the term, the term we use at glasswing is intelligent verticals where it's kind of like augmenting of human, you know, labor and processes to do things that couldn't have been done before, SAS couldn't accomplish it. You know, just general automation couldn't have been done. But now because of AI, it's possible to do so, you know, I can take you, when we talk more about, you know, the, my background and stuff, I can tell you more about some of the examples of it, but like the idea that people have started to really apply the technology immediately in a way that has immediate benefit to the user and to the, to the enterprise customer is very exciting to me. And so I feel really good about that. You know, like the, as I was kind of mentioning that cloud switch, like there was like a long burn with the cloud computing adoption. Not because people weren't adopting it, of course they were, the developers were doing it like, you know, rogue on the side, you know, shadow it and all that kind of stuff. But until it became an, you know, a company standard and people felt like they had to use it. It took, it took many years.

Yeah, yeah, yeah, yeah, yeah. I mean, do you think that people will have to raise less money because of this? Do you think that people like what, what. Because it is. I, I kind of, I see what you're seeing, which is you build a product now and the speed to build the product and get it out in market is scary. To be clear to me, I find it scary because that means what's the moat for that, you know.

Right.

And, and I see a lot of people talking about could we raise, you know, venture is not the right thing. But, but then you see the companies that are being the most successful are raising still huge amounts of money. So it's like, it's very confusing. I don't know.

You know, it is, it is. So I'm, I guess I would have to say, like I'm old school enough that I think that even though it is actually possible. Okay, so let's, let's put a couple of facts down on the table. It is actually possible to build a product and get to revenue with fewer people. Now with AI doing a bunch of the work, it just is.

Right.

And there's, you know, a cap set of capabilities that didn't exist previously on the other hand, and we talked about this, I think on the previous call, like, just because that's true doesn't mean that the companies won't raise a lot of money. We know they are. They're raising a ton of money at in ridiculous valuations and that's that because the capital is available and wants to be deployed.

Right.

And because this is exciting and you know, a huge tsunami wave that people want to, you know, be part of. And I think it's an interesting question about like, okay, well, so you know, you don't have to spend on infrastructure anymore. We got rid of that because now, you know, you use the cloud, okay. Still you spend on infrastructure, you just spend in a different way. Fine. You don't have to hire as many people upfront. Okay, fine. But still you have to take the AI and make it work for you. And so the people that you hire need to have certain types of capabilities and skill sets and you still need to build a team. So presumably if you are raising $50 million or some crazy number, right, you know, which you see people doing at early stages, the argument is that you got to market faster and now you're going to scale faster. And at that point you're back to some of the same issues that you've been at previously, right? Which is it's fine that the AI is going to do a lot of the pipeline development and the sales productivity and the go to market and the customer success and the trouble ticketing and all the stuff that we're talking about, you know, incident management, all that stuff to happen. But still you've got to hold it together in Terms of what is this business and what is it that you're trying to accomplish. I personally don't think that two guys and a bunch of AIs is the answer to that problem. I still think you end up with teams that perhaps the ramp of the scale is a little slower but still ends up with, you know, you're still ending up with a hundred people. I know people disagree with me on this, but I think you get to a certain point where your engagement and your interaction with the market and with the customers will still require that and that we're not at a point where you just sort of say to the AIs, okay, go figure it out, take it forward. You know, I'll be over here planning strategy or something like that. So you know, prove me wrong. But I, that's, that's kind of my feeling.

I, I, I, I actually agree, I tend to agree with you. I think the challenge is that the stories that are being told and kind of sensationalized, I don't know, on LinkedIn and everywhere else is the, the three companies that got to, you know, this much revenue with 10 employees and it's like, but there have been no's in SaaS there. You know, it's like, it's, it's, and we, so I, I agree with you. I just think it's an interesting moment in time where it's like kind of crazy and people are feeling like, oh, this is the beginning of no employees.

Right, right, exactly. Like for sure did it. So of course we can do it. Like, because I'm also very focused on enterprise, I do believe that the relationship building with the enterprise still requires a laws of gravity and behavior and so that you're still going to want to do those things and that that will still matter and it's possible that we'll do a better and more efficient job at the way in which we build and sell products and you know, engage with customers and stuff like that. But still, fundamentally that arc of how you, how you do that is going to require time, energy and human relationships. And that's what I think, you know, and I, I'd be glad to do less like managing of spreadsheets and messing around in salesforce.com myself. Right. You know, I mean that's, that'll be just fine with me.

So talk to us a little bit about glasswing and your role as an operating partner there. You know, do you make investments? Do you just work with the existing founders? Do you like what, what does that role look like?

Yeah, I kind of I wanted to do something very specific and, you know, was very happy and fortunate to be able to do it with, with the glasswing team. So it's, it's kind of split between a few different things. So there's definitely working with the portfolio companies and being able to do some of the advising and mentoring and stuff that I have been doing all along and you know, in a more maybe sort of focused way, you know, with, with companies that you get to see them over a long period of time. So I love that. And then I'm part of all of the, you know, the regular partner meetings, the, the diligence calls. I help in terms of making introductions of companies that might be interested in getting funded by glasswing. And so I'm kind of in the mix of. It's almost like a fire hose of technology and company and founders coming at me all day long. And I love it and I love going downtown and hanging out with the team and meeting people downtown and just being again, part of that whole ecosystem. So that's, that's very exciting to me. And you know, like, kind of some of it is about the Boston community, but some of it is also in terms of like the glass wing approach to AI and the use of AI for enterprise and cyber and stuff like that I think is unique. So I think it's an opportunity to go like really deep on sort of the core technologies that are out there. But how are they getting applied? You know, such as applying it to these, you know, intelligent verticals and stuff like that. Looking at what makes a company have a protective moat beyond. Everybody's just buying some AI right now because they, you know, they feel like they should try stuff, right? And so like evolving that and understanding what to look for in that type of a situation is very, it's very cool and exciting to me. I'm used to being on the other side of the table right now. I'm like, ah, what you're saying, okay, and some of the things are things you would know. It's about the founder and it's about the, you know, like the, you know, the experience that they, you know, the founders have had and stuff. But some of it is also like a hardcore look at is AI being used in a way that could not be done previously with other technology and automation? And is it not just a wrapper around stuff for user experience or to, you know, make it look cool or something like that, but it is fundamental to what the problem that is being solved. And so, you know, being able to say, okay, well We've developed something that you know, takes advantage of a lot of the different techniques that are out there. But we've applied it in a very particular way and some of it is understanding the domain and the, you know, the background.

Right.

Like the data sources that are available and being able to apply them in a way that's unique based on the founder understanding the specific problem. So that's, you know, that's kind of where we are. So like, you know, like some of the companies, you know that are focused on inventory management for manufacturing. Verisit or Crane is a company that does looking at operational issues for the construction industry.

Right.

You know, so something like that or Lab Viva is for scientific materials and lab equipment, you know, so like, like had a lot of these processes for these types of markets, believe it or not, are still highly manual and a bunch of people with like in and out of different systems and spreadsheets and all this kind of stuff because they just, there were pieces that could not be automated and there was data that was not available to, to make the next step in the decision. So it's kind of like an end to end work workflow that is now being made possible.

And I love that the domain, the domain expertise is definitely to know where to apply AI right in these workflows. Not generic work.

Exactly. Like not any problem, but this particular set of problems.

Yeah, yeah, I see, I see that the companies that are getting the most other than like the cursors of the world. Like I think the ones I've seen that are getting that revenue quickly are those ones.

Yes.

Because it's just so, it's like hey, I worked at this industry before.

Yes.

I had to do the spreadsheets, I had to press the buttons, I had to move the stuff around.

Right.

And now literally it's all being done for you. Like those, I think those are the ones that are right now crushing it. Like those are the ones that are, you know, and getting enterprise adopted because the enterprise like sure. Like that's going to save me literally hundreds of thousands or millions of dollars.

Yeah. One of the, one of the Glasswing companies is Black Kite which is in the cyberspace and there it's not vertical specific but it is a very specific problem which I'm on the board of a public company called Allegiant, which is a manufacturing company and I, I understand these things now, you know, from the customer side more easily. Which is third party vendors. Right, third party. Not you, you're good but like you're all your supply chain and your third party vendors, like, how do we keep them up to the bar, right? We want to make sure that that is where it needs to be and all that kind of stuff. And so like, like technologies that are able to take this very often, like disparate and you know, unstructured data, data sitting around in all different places and put it together in ways that allow you to really make the decisions and help understand where, you know, where threats could be or how to improve a stat, you know, an operational process. It's very cool. So I'm really loving that and I'm enjoying, you know, seeing all of the technology and working with the founders and you know, for me too, it's kind of like, okay, you know, like, like if we're going to build stuff here, let's build real stuff, right? Like, like in industries that have real problems, that have not benefited maybe even as much as, you know, SaaS has benefited in other, you know, like companies that were like cloud native companies.

I want to transition a little bit to your background. Where, where did you know, like from a young age, did you know you wanted to be an entrepreneur? Do you know you wanted to be a leader? Did you, did you know that like at a young age?

No, I'm gonna describe it as like latent. So no. And my, my family sometimes. Laughs they're like, okay, did we know that you were gonna go do all these things that you ended up doing? Like we're gonna, where did we talk about that? No. So I, I didn't really know that I wanted to do it. And then when I got to college, and even more so when I was post college, I found myself gravitating towards some of the early startups that I got to see in the local Boston area and just, you know, that were around like, you know, that I bumped into through, you know, on campus or, you know, then when I was, was looking at jobs, actually I was a Goose Allen management consultant for a few years. And so we, you know, I had an opportunity to look at some of the things that were going on in the, you know, like in the educational software industry. And so I was looking at some of the things that were happening there that were more startupy. And I found that what kept happening was that I kept being like drawn to like the founders. Like, I just wanted to hang out with them and they just seemed the coolest people in the whole world to me. That's like, that's all I could think about was how cool they were. So after business school, Unlike pretty much 99.9% of my graduating business school class, I wanted to go to be. Be in startups. Like, at the time, that was not a thing that you did. And so I was telling you a little bit, I was in Tel Aviv and I started a company with some Israelis, brought it back to Boston, and then I pretty much been here since then. One of the things I would say and the reason that I think maybe it was latent, is my dad was an entrepreneur in the biotech world. And when I was growing up, he was building a company that, you know, went. Went public and, you know, whatever, and I really didn't pay any attention to it at all. I thought, but it must have been in there somewhere, you know, like, in terms of my having seen him do that kind of thing. And I didn't, you know, it was in a field I didn't understand in terms of the biotechnology and stuff. But the. The journey of it was something that he was really excited about. And, you know, obviously I get it now. It's much better. So that was very cool. And then the other thing that was very cool that I think is interesting is my mom was. She worked for IBM in the 1960s as a programmer. She was one of those, like, women they hired, good at math, and was like a programmer with punch cards. So I always think I've got, like, engineering and entrepreneurship in my blood.

Wow. What. What a bait. What have they thought, you know, or as you've kind of built these companies and. And been so successful, like, did. Did they care? I guess, you know, like your dad, like, me thinking about myself, like, if my kids went and started companies, I'd be so proud. You know, I'd be so, like, in that. Is that how it was? Or. They never really pushed you in that.

Like, they never pushed, but tremendously, tremendously supportive. And I, I believe, proud and excited. They, you know, got to see it. And, you know, of course, when you're the family of the person who's the founder, entrepreneur, you see the highs and the lows, right? And also you've experienced, in my dad's case, you've experienced them as well. So, you know, it's not like this, like, glamorous lifestyle at all. Like, it's just insane, right? You know, it's just so unbelievably intense. And, you know, highs are highs, lows or lows and stuff like that. So I think for them, they mostly were kind of like, okay, you know, like, it's really exciting that Ellen's doing this, and she probably could Use some support here, you know, which they were really great about.

Did you have a mentor at any point in your career? You know, especially as the first time CEO, it doesn't matter. But like did you have a mentor at any point?

Several and still do and some of them I'm still in touch with, you know, even here as I'm sort of in this next phase of, you know, being on the, you know, in the operating partner role I did from very early on and I, I, the advice I give to newer entrepreneurs is you need those people, those people are critical for you. And it isn't necessarily just one person, right? It's sometimes this person is really powerful and exciting and a great mentor and inspiring to you in this particular set of issues and somebody else might be for, for you, for something else or as you evolve in your journey. Like you need different kinds of mentors and supporters. But like, so I was part of the original team at Neteza in the data warehousing space and so Jit Saxena was the founder CEO and he was, is and still will be a mentor to me like forever. You know, like we're like, it's like 20 years gone by. So he's maybe one of the, the early ones where you know, he challenged me and pushed me and you know, I was working for him as an employee but when I was ready to go be a founder myself, he was like, I'm going to help you. And he did, you know, he made sure that the venture people that he had relationships with, you know, worked with me and took me on, you know, to kind of, you know, engage with me as a, you know, an, an entrepreneur residence and all that kind of stuff. You put money into the company, you know, like, so like stuff that really matters, you know, at that early moment. And then there have been other people along the way who have just been like, when you need the, you know, like you're stuck on something and they're the people you call. You're like, I'm like I, I, I, I'm, I'm, I'm almost done with this funding and we ran into a snag. What do I do?

Right?

Or I'm really having problems with this person on my team and I just cannot figure out what to do to make this be productive.

Right?

Can, can you just sit down and talk through it with me and stuff? And you know that they've lived the journey, right? You know that they're going to give you, they're not going to give you bullshit advice. They're Going to give you real advice.

Someone, one of the episodes they talked about kind of like a personal board of advisors.

Yes.

You know, and I thought that was a good way of describing this because it is hard to go at this alone. I mean, basic, I mean, not impossible, but very difficult to go at it alone. I, I don't think I've met a single, I can't think of a single successful founder that I've met that said, I just did it on my spot.

Myself, you know, and, and I'm using AI and it's just me and there's nothing.

Exactly, exactly.

Sure.

But I think, yeah, that's, that's really. Yeah. And I think that those, those people, you know, they, something that I, I found when I was younger is that I, I, you worry like, oh, could I reach out to that person? Because I don't know where they get in there in your case. They, they, he was your CEO, you know. But like, I, and I always tell people, like, you know, you, if you reach out to most people, most people have been through the journey, most really want to pay it back, like they really want to. So I always tell people, just, just reach out. You'd be surprised. I would say it's like a 90% hit rate.

Totally agree.

Right?

Totally agree. If somebody said, I'm building a company and I'm really interested in the fact that you had this experience or you did this thing or whatever, or you're a. And you know, found CEO, whatever, can I just have a short call with you?

Right?

Or if I'm local, can, can I, can I, can I buy you coffee or something like that? Why would I not say yes If I could do it right? If I'm able to do it, I would do it. You know, it's like kind of. And even if it's like, oh, I'm running all over the world, I'm traveling and stuff like that, you can take a 10 minute call.

Right.

I mean, so I do feel that that's really important. And luckily for me, I've had people who were those people. And you know, in the end, like, you know, you look back and you think like, those people, not only did they get it, but they also, like, they did it in a way that wasn't like, oh, I'm just doing it to be nice. Like, it wasn't about that. It was that like, they were like, they see that you're serious and that you really want to do something exciting and you want to build a company and stuff like that. And so they Feel very motivated, you know, to. To help you. And I feel that way for sure.

You mentioned your two daughters. Do you. Do they see you building these businesses? Have they kind of been exposed the way you were to your fathers, maybe through osmosis, made you more intentionally? Like, how have you handled that?

I think they've seen more because I used to, like, bring them into the office and they would come to company parties and, like, they knew the people and the team and the stories and stuff like that. And so, you know, for better and for worse, because they definitely, you know, they. They were there for the ride. I don't know that it's necessarily made them think, like, oh, I want to be an entrepreneur. Like, I can't say that I know that that's true. It's possible, you know, maybe at some future point. But I think that. I think they have an understanding of what that whole life is like in that experience in a way that, you know, I hope it will be helpful to them in their profession in some way. But on the other hand, it also makes me feel close to that, right? Like, that they, you know, they really have been part of the conversation. And, you know, they. They have really good ideas, those girls, you know, so sometimes I'll say, hey, what do you think about this? You know, like, they're. They're adults. They're in their 20s, and. And they. They have some good insight.

I like that. I. That's how I grew up with my father taking me to meetings, taking me to things and asking me, even at the age of, you know, 11, 12, like, what's my thought on this meeting that we just came out of? What's like, you know, and I've tried to do the same with, like, which. With my kids, which has been, you know, really, really interesting because even at. I mean, I took them at, like, five, six to the office, and as soon as they could write, you know, I was like, just write down what you're hearing, you know? And at the end of the meeting, they would come to me, what does churn mean? You know, like what? And they would draw the graphs, like, actually draw, like, the charts they saw on the slides.

That's great.

And, you know, I think. I think, well, you don't even know.

What, you know, what's sticking.

You don't know. You don't know what's actually happening.

Yeah.

You know, I think, you know, a lot of people I've interviewed have had similar stories, but in, not necessarily big companies, but entrepreneurial kind of parents. And I think there's also something about work ethic that you kind of see, right? Because you, you understand what it actually takes to be successful. And, and I think, I think if nothing else, even if they're not entrepreneurs or I, I think there's some, some osmosis of like, wow, look at what my parent had to do.

Right?

Yeah. And you know, as it happens, I have two daughters, right. So there's an aspect too of like, seriously, you can do it, whatever it is, go do it. You know, like, so they're in the, in the DNA as well, I hope. And you know, and then also finding the balance of life that they want.

Right.

Like, there's no answer here, right. In terms of like, you have to work this hard, you have to do this many things, whatever, it's just not true. So like, where, where is the balance for them individually and, you know, hoping that that's like a, an open conversation that that can be had.

Knowing everything, you know, today, all the experiences you've had in your career. If you could go back and give yourself one piece of advice at the very beginning of your career, maybe before you started Booz Allen, like, what would that one piece of advice be?

Be so intellectually curious. Just want to know like, about what's happening around you, want to meet people, be open to experiences. I think it took me a while to come to that, you know, like, I kind of somehow thought of myself on more of a track, you know, coming out of school, out of, you know, at Booz Allen, there were projects, you know, with structures to them and stuff. And just like this, the, the, that element of serendipity that is part of entrepreneurship, you know, of like you had lunch with that person and then by chance you started talking about this topic and then suddenly you're building a company together, right? Like, there are things like that, that, that happen or why does, you know, why does some particular person invest in your company or not? You know, like the, the, the, the, the things that you can do that are structured and that you have control over and then a certain amount of just being open to connections, experiences, learning about new things, you just never know. And so I, you know, I, I, I highly encourage that and I also wish I had done it earlier.

Alan, thank you for doing this with me. I, I have enjoyed this. We could probably talk for like four hours, but I, I really, I, I really appreciate you taking the time and just sharing all, all this. I think there's so much good stuff in here. We got tactical, we, we talked kind of high level we talked future facing. So anyway, thank you very much.

My pleasure. And shout out to Barack Kaufman for introducing us.

Yes, yes. Yeah, Barak. We didn't talk too much about the PDF group, but we met through pf, which is post Exit Founders, and it's a group that Barack Kaufman created and has, I don't know, thousands of people now exit as founders. It's amazing. So thank you, Barack, for making the introduction. And yeah, I hope everyone enjoyed. If you did, please share with your networks. That's a wrap for this week's episode of Not Another CEO Podcast. Thanks for joining. For show notes and more, please Visit not another CEOPodcast.com we'll see you next week.