#2: Zvi Band, Contactually

Welcome to From Startup to Grown up, the podcast. My name is Alyssa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number two and I'm so excited to have Zvi Band on the podcast today. Zvi is the co founder and CEO of Contactually, a customer relationship management tool which got acquired by Compass in 2019. As you'll hear, Zvi is a relationship guy. He wrote Success in youn Sphere, a book about nurturing relationships, and his new venture, Talk Social, is focused on bringing humanity back together. Zvi and I had a really juicy conversation about how he got onto the path of entrepreneurship and how he learned to see himself as the leader and the limits of transparency. Zvi and I also get into a real talk discussion about co founder Dynamics, Mental Health and his surprising advice to founders who are getting ready to sell their business. Please enjoy this conversation with ZV Band. Welcome to the show, Zvi.

Thanks so much for having me and especially being one of your first guests on the show. I'm honored.

Thank you for saying that. I'm so excited about this and I've been so excited to have you here because I know how important relationships are and actually I'd like to maybe I want to hear about your background for sure and then and take us through the journey and the story of that idea in Evernote. So maybe start off telling us about your background. Where were you born and were there early entrepreneurial kind of germs that we can sort of see?

Yeah, great question. The answer to that last part is no and I'll share more. So I was born in Boston, but bounced around the country. My father was an academic, so was in Berkeley, then San Diego, then two years in New Mexico before finally settling on the D.C. area where I still am now. Truth is, I was never the lemonade stand, newspaper hustler, et cetera. Like no real business acumen or interest at all until like post graduation. However, I was raised in a house where both parents pursue their passions at all costs.

Oh wow.

So I think it was innately in me. Like my mother left a job in HMO management to become a full time artist. My father was an astrophysicist and stayed in the academia. So it was definitely always like hardwired in me to very much like pursue what I was interested in. And I'm the kid that like my parents brought home Their first home computer when I was 10 years old. I'm like, yep, this is me. But it really wasn't until my first day at my first job post graduation where I was like, whoa, this is not what I was meant to do. And that to me was really the entrepreneurial spark that said, okay, I meant to build something that's.

Well, that's fascinating. Let's dig into that a little bit because I think there are a lot of people who get that call, like, wait, wait, wait, this is not what I meant for. What does that actually feel like for you?

Yeah, I remember very clearly, like sitting down at my desk or being sat down at my desk and said, hey, and this is the project you're working on up until that point. And this was for a government contractor. You know, it's great, it was a great place to work. But I was, I was told like, hey, this is the project you're working on. This is what you're going to be doing for the foreseeable future. And something clicked. I'm like, no, I'm not going to do this. I'm not supposed to do this. I'm supposed to do something else. I have ideas that I want to pursue, I have things I want to build, I want to make a difference. And I just didn't feel that was there. And that's really what set me out on my exploration of like, hey, what is this whole entrepreneur thing? What should I be doing? And there was another, I would say, catalyzing moment later on where I was already starting to read more about startups and what's going on. This is like again, 2006, 2007, definitely not really. Startups weren't really the rage. And I remember having a copy of an Inc magazine, funny enough, and my supervisor happened to like flip through it and he was like, yep, nope, no interest. I'm very happy working a 9 to 5 job and going home and not worrying about work. And I am so thankful for that moment because I was like, no, that's not me. Right? And so clearly I started to understand that some people are wired differently. Right? It's not like I just didn't like my job, so I wanted something different. It's that I wanted something that was more innately tied to my purpose on earth. Right? And I believe in work life integration, not like working nine to five and then not working from five to nine.

Mm, wow. That's a very powerful story. I love those catalyzing moments. So tell us about what happened. I'm so curious, like There was an idea in Evernote. Apparently it came from your head, it went to Evernote, and then it built into. Contextually tell us that founding story.

Yeah. And so there's obviously there are a few little hops in between. I left to become CTO of enterprise software startup that was acquired in 2009. I started my own, like, little consulting firm. And when I say started my own consulting firm, I basically was between jobs. And I emailed everyone I know saying, hey, I'm on the market. I can do your software development jobs or whatever. And very quickly I was working with the likes of Ford and CBS and Volkswagen, doing all these amazing projects. And despite being the kid who grew up, I'd say more introverted, not really, well, socially connected. I went to three different high schools, so clearly that had an impact on my social life. But I realized that, wow, all these amazing things were happening to me, not because what I did, not because what I knew, but from who I knew and more importantly, who knew me. And that was that kind of real key moment. I said, wow, my relationships are this important asset of mine, but at the same time, like most people, I sucked at it. I would meet someone for coffee and two weeks later, completely forget about who they were. Or I was so busy at the top of my inbox that a client project would end and I'd be so focused on what was next that I would never engage again. And so that's where I said, hey, I need to get better at this. I tried Salesforce and I tried Highrise, which was a CRM at the time, and nothing seemed to work. And so I had a practice of just capturing random ideas. I thought, you know, the shower thoughts in Evernote. And I remember May 15, 2011, I wrote down the idea for, like, wouldn't it be great if there was a proactive CRM that would help you with your relationships?

Yeah.

And so that was that moment again. It was just like an idea that I just wrote down and kind of kept going about my day, but it stuck with me. I kept coming back to it, and we end up building it in June and raising our first round of capital in October of that year.

Wow, that's a great story. So I'm actually going to skip to Tony, your co founder. How did you meet him? And I actually met Tony before I met you. So that's, you know, I have this sort of sense of the two of you very, very individually. But how did you meet him and how was that partnership in building the company?

Yeah, it was great. So there so while I was running my consulting firm before starting contactually based here in Washington D.C. and at the time it's not that there was no startup community here, it's that people didn't realize there was a startup community here. And I was involved in a number of ventures. I founded a little brochure site called Proudly Made DC showcasing startups in DC that ended up making it to the New York Times. Then I started the DC Tech meetup which ended up being, being regarded as one of the largest meetups in the country with I think we still like 30,000 members. And through that just I didn't feel like it. But I became regarded as one of the people to meet in the D.C. area. Tony had worked worked for Microsoft previously and had followed a girl here to the D.C. area. And he just reached out to me cold saying, hey, I'm looking to meet people in the area. He and I had a few coffees and at one of those times I shared saying, hey, I'm playing around with this prototype of a relationship oriented CRM. And he offered to help out in his free time. Thought like, oh, you got some spare cycles, this seems interesting. Sure. So he started doing some customer development a couple days a week and then myself and our other co founder Jeff were working on the product and finally we actually received an offer from 500 Startups kind of out of the blue to focus full time and build the company. And that was kind of a burn the boats moment for all of us. And I think at that time when especially Tony and I said, hey, are we going to go in on this? You know, and we end up deciding to pursue it full time.

What made you take that leap? Why'd you think you could possibly get this right?

I'll be completely honest, I didn't like, I, I, I wouldn't necessarily say, you know, the, the general you think the startup story is, oh, I, you see a mountain summit somewhere and let's go pursue it, let's go start climbing the mountain like always aiming at the peak. It was actually not the case for us, or at least for me. I was like, I knew I wanted to start a startup. I knew I wanted to build a product and pursue something I was passionate about. I was running a really great consulting business previously, but, and this is what stuck with me even today is that I didn't want to get paid to build other people's dreams, I wanted to build one of my own. And so I knew I'm like, hey, I want to build this dream without having a clear vision of what the dream can manifest itself into. So to some extent, and this is. There were cases of this as we went forward too, but we just said, hey, let's build this. Let's pull on this thread and see where it goes. And if not, hey, we'll just go do something else.

Right. I love that. So you're willing to take the risk because you kind of thought, well, I want to build my own dream one way or the other, so now's good time as any to see how it works.

Yeah, absolutely. And for what it's worth, you know, I just. In full transparency, like my, you know, the 500 startups offer came with the string of saying, hey, for four months, we want you to move out to Mountain View to be with us and to work out of the 500 Startups offices and everything like that. And my two co founders, they're like, yeah, let's go do it. Absolutely. Like, you know, three matches on the floor, empty apartment, working 18 hours. Sure. Whoa, whoa, whoa. I just got engaged. I have a place and a dog and a fiance in dc. This doesn't really seem for me. Let's kind of try and make it work in dc. And it was them. And I'm very thankful. That said, like, no, let's go do this. And in hindsight, I'm thankful to have people who could throw me off the cliff when I wasn't fully ready.

I love the way you put that. So I'd love to keep talking about your relationship. I didn't realize you actually had two co founders. I thought you just had the one with Tony. Can you tell us, how did you decide how you guys decided to sort of divide up roles and responsibilities? How did you end up being the CEO? Like, how did those relationships kind of play out?

Yeah, absolutely. So our third co founder, Jeff, who we're still friends with, he left the company in 2016 to pursue. To pursue other interests. But it's very clear that he. He was happy. Heads down, in code, you know. So he became. He took the role of cto. I would say I had a little bit more. And by more, I mean like 15 minutes more. Like business acumen and experience. And it was my idea, after all. That was the catalyst for us coming together. So we decided that, okay, I would be CEO and Tony would be coo. But truly, and I think especially for Tony and I, like, there was. He and I co led the company together. At times we really like saying, hey, left brain, right brain. Partnering with each other very closely at times. We held each Other back. We definitely shifted roles amongst each other, but it's very clear that at least for the initial phase, I'd be focused on building the product and Tony, we focused on getting in front of users.

Okay. So it sort of felt like that naturally happened. So as the company grew, you two in particular had to probably navigate that relationship. Could you share some of the highlights of your relationship with Tony in particular and maybe one or two lowlights that you had to overcome?

Yeah, absolutely. So I think the highlights were, you know, I think throughout. And this is a. The ideal parts of a co founder relationship where you could tell and I could tell Tony, hey, you have this particular, you have this particular responsibility. Because you have this particular responsibility. I'm not thinking about it. So for example, especially it was initially like sales and marketing. You are focused on it. I'm not. Tony could say, say the same thing about product for me or fundraising at times. And that was always really helpful. Right. When we can very, very quickly divide it. I would say, like, and especially times where we were able to shuffle our roles, that was helpful. And I think this is one of the things, like, I wish we had done even sooner. Right. Because there was a period of time where I was focused more on product and Tony's focused more on sales. And then over time, we realized that I was becoming more of the external face of the company and we actually shifted and this ended up being just a rocket ship for the company where we said, hey, Zvi is focused on everything outside of the business and Tone is focused on everything inside of the business. And so it's something I take with me now of saying, constantly revisiting roles and responsibilities in a startup. I'd probably say, like the through line of where we had our lowest periods of time were when we weren't talking.

Frankly, you weren't talking because. Just too busy.

Yeah. We were too busy or too in the moment or frankly. And this is one of the things I, I really realize now is that we were afraid of talking. Right. We knew there was conflict between us.

Yeah.

And we'd rather just like our egos naturally try and do our egos avoid the mess in the corner. We're like, yeah, we probably don't agree with that, but let's just kind of keep going there. And oftentimes that resulted in us sometimes arguing in front of our team or a VP of sales would get one answer out of me and different answer out of Tony and ended up being like a really big problem for the company. I remember one of the jokes that, like, one sometimes our executive team would laugh at, would half jokingly say, like, why are mommy and daddy fighting? And we're like, okay, this is something we need to work on.

Totally. You know, as you know, I wrote a book called From Startup to Grown up. And in chapter nine, I address co founders. And my point in that whole chapter is when you have a co founder, you have a marriage. So when they talk about mommy and daddy, they like, they're experiencing your marriage.

Yeah, absolutely. And so for that reason, we've. Yeah. And I think it came in late as we became more mature and started realizing that it is just as important to work on our relationship as it is to be in the relationship.

Yeah.

But we started implementing different tactics, and now, you know, having started a new company, I'm able to take all those lessons learned and implement something again. Right.

That's amazing.

Yeah. And for me there, I was just.

Gonna ask, could you share what are some of the specific tools that you ended up using with Tony that you're now. Especially implementing now?

Yeah, I would say, like, one is importantly, just very much time.

Yeah. Spending time together.

Time is really, really important to. To spend. To just spend more and more time together. I. I truly appreciate that. Like, and time, not just like sitting in meetings, but like, so social time, making sure that, like, and again, we realize, like, and I think this is important to co founders. Co founders don't have to be friends.

Yeah.

They have to respect each other. And Tony and I, you know, I wouldn't necessarily say on a normal, you know, if he and I were to ever meet at bar, we'd be friends with each other, but we are very friendly and very respectful each other, even to this day. So establishing open communication and especially implementing tools for open communication.

Yeah. Like what? What tools?

So nowadays there's one tapestry so that I've implemented with, with my new co founder. I think we. We didn't take advantage of enough, but we had a few advisors and board members who are very good at not playing referee, but very clearly, like, stoking conflict, if that makes sense.

Oh, wow. So they would catalyze conflict so you couldn't ignore it.

Yeah. It's like, love that. I'm gonna bring you two together. You're saying this, you're saying this. Go. Right. I would say one of the tricks I picked up recently, which I. I wish I. I wish I had back in 2011, because it would have been transformational, but I asked from time to time is the very simple question, what are you not telling me? That you should.

Yes.

And that brings up all sorts of crazy answers. Right. That most of the time, you know, hit you like a Mack truck.

Yeah.

I didn't know you thought that.

Yeah. Like. Like what? Like, what have you learned? What is an example of something you've learned when you ask that question?

I would say, like, you know, one of the times, you know, with my co founder is, you know, I'm afraid of you. Oh, wow. This is very early on.

Yeah, yeah.

Right.

Yeah.

I'm like, whoa, why are you afraid of me? Right.

Yeah.

There was one time where with Tony, I made some kind of, like, off the cuff remark in a meeting. Right. And he took it to heart very personally. And I was like, whoa, again, words come out all the time. Sometimes I don't even know understand what I'm saying. Right. And to be able to hear that was really helpful.

Yeah.

So finding mechanisms to intentionally get out what you're not saying, I feel, is like, the root of most issues. And then, of course, we've hired coaches and people have worked with us, but just that can only amplify just the base level of communication between us.

Right. Wow, that's very powerful. Well, you know, on the topic of communication, what I find with founders is that when they address sort of difficult or delicate conversations, they kind of develop, like, go to scripts, I guess. I would ask you if you think about difficult conversations you've had with your employees or executives or Tony. Awkward conversations, delicate conversations. What kinds have been the most challenging and how have you approached them?

Yeah, absolutely. I would say, like, the. What kinds of issues have been most challenging are clearly when there's, you know, especially like, among an executive team, where there's very big disagreement with us. Right. And. Or, you know, with the whole company when you have, let's say, traumatic news to share. Right. Which can be, for us, related to, you know, you know, selling the company, which I'm sure we'll talk, we'll get to at some point.

Yeah.

It can be talking about, you know, it can be talking about letting go of a key employee or, you know, we had to do, you know, you know, a couple of layoffs, unfortunately, you know, throughout the course of the company. So addressing that, I've always found. And even if it's between Tony and I, it's always fine to like, just. And he's brought up, like, he brought up the term, like, rip the band aid off as quick as possible. Just get the information out. Don't try and barely just say, here's what's happening, and Then start to go into why or how we're going to resolve it. Even like amongst, when handling, like very severe conflict amongst my board, for example, or executive team trying to very clearly delineate what the level of disagreement is, like, what are we disagreeing about? And then saying, okay, let's come up with a solution. And so I think that was always really helpful for even on the board saying, hey, like, oftentimes, you know, people aren't necessarily sure what we're fighting about.

Yeah.

Are we fighting about cash? Are we fighting about sales strategy? Are we fighting about market opportunities? And oftentimes just getting everyone aligned around, like, what are we misaligned about?

Yeah.

Then you can say, okay, here are a few paths or here's what I'm hearing. So that's been one of the key tricks for me, is just trying to align around what, what are we all disagreeing about?

Yeah. How do you do that?

Do.

Are you the kind of person who's like, okay, I hear you saying this, you saying this, or do you sort of say, okay, everyone gets a minute to sort of say what they have on their mind. Like, how do you, how do you get it all on the table?

Yeah, oftentimes I'm the one who lays out, you know, and saying, hey, I sometimes pretend to be the dumbest guy in the room, usually because I am the dumbest person in the room. But yeah, just by mean that, like, because that gives you the license say, okay, just wait a second. Yeah, here's what I'm hearing over here, and here's what I'm hearing over here. Am I right? Am I right? Did I, did I mishear you? Am I misunderstanding it quite often like I am or other people are, So I get to be again, the dumb person in the room that, you know, people correct. And just to lay that out and say, okay, so therefore, this is the, this is the answer. How do we solve this? And oftentimes that allows other people to come in and address that. But I, I find that's helpful. Oftentimes, you know, we, you know, especially when it regards to, like, what to do with a very challenging customer situation, you don't need to make the decision right then. And especially if, like, emotions are elevated, just separating out, like, hey, here's the issue. Yeah, I'm going to assign someone to propose a solution. Let's talk about it tomorrow. That alone just separates it out because now it's no longer a emot, you know, like match between people, but it's rather just a situation that we Just have to problem solve our way out of.

Right. Oh, that's so well said. I mean, sometimes a pause also could just be very helpful. Like let's just stop and maybe kind of regroup a little bit.

Yeah, absolutely. And I learned this too late, but again, everyone is bringing in, you know, the meeting, the emotions from the meeting they had before or the fight with their kids this morning, or awkward drop off or you know, a discussion with their spouse or, you know, anything they didn't like the outcome of the football game last night. And so just trying to be very clear and saying, hey, let's, let's try and divorce emotion from this and really just understand the evidence here and understand like what is the decision that needs to be made and then very calmly work through a solution has been just immensely helpful to me.

Yeah. Oh, that's so great. Now Zvi, I know that you are obviously a relationship guy and I'm just wondering, are you also a culture guy? So, you know, contactually started out as a little bitty idea and then if I've heard of startups, you know, incubated company and then obviously into a company that got sold. How did you think about culture? If you did think about it and how did you think about sort of the culture changing as you got a little bit bigger?

Yeah, great question. Um, so yes, we did think about culture and I remember like go as a co founding team very early on when we're talking about culture, our root belief is like, hey, we want to build a company that we want to work for.

Ah, yeah, great.

And I think that really helped it. So we set values from the first company retreat.

Wow.

Yeah, I remember sitting down and proposing them and we, you know, tweak them and works with words with that, works with them, et cetera.

What were they? What were the values? Do you remember? I don't put you on the spot.

And actually there are a couple ones that like really became challenging. So we can address those three. One of them that was always there in different, different manifestations throughout was to be transparent. Like we really embrace transparency. The worst thing you could do at our companies, withhold information. And so we very much believe in radical transparency, which of course had its challenges later on.

Right.

We very much believed in being user centric, which is all. And we always noted every new hire, user centric and customer centric are very different things, especially when you're building enterprise software. And we always established that we were going to be user centric from very early on. We wanted to build a product that Users wanted to use because, remember, we were building a CRM company. Most CRMs people don't want to use, they have to use, otherwise they get fired. We wanted to build a product that users want to use, that end being a big advantage for us. Two ones that were very contentious, which changed over time, was progress over process. We always wanted to make sure that we were moving the company forward and we want weren't bringing on any hire that was just going to be following a process just because they were told to. We always said, hey, we want to make sure everyone here is thinking about moving our mission and our customers and our company forward. And another one, which you can imagine without me saying it or without me explaining it, had to change over time, was this was like 2013 and Facebook had really popularized this term. But move fast and break things.

Oh, yeah. Wow.

And we moved way too fast and we broke way too many things. And so you can imagine that was a value that shifted very quickly.

Yeah. Wow, that's awesome. First of all, I'm so impressed you can remember them, but then you're being really honest and saying, you know, we had to make some changes. So tell, tell us how you evolved those values. Tell us if you had like a moment of truth, like, okay, this is no longer good. This is not working for us. This is now counter effective. Or like, how did it happen that you evolved them?

Yeah, it's a great question. As I've reflected back on it, one of the unwritten values of the company that we exhibited but never really documented was introspection. Like, we were not a company. That was Moses coming down from the mountain with two tablets saying, hey, this is just what it is. It exhibited everywhere. I was, I'm a servant, leader, leader and still believe in servant leadership. At our company retreats and regularly we would ask our team, what would you think? How, how, how could we help this company? So one of our core values was ownership. And that meant ownership not over your particular area of responsibility, but ownership over the company. And so we would ask them, including every company retreat, which we did, you know, every April or so up until acquisition, was, hey, how, how can we make this company better? What should we start, stop or continue? How should our values change? And sure enough, every year at our retreat, we revisited, hey, what needs to change about our values? And we would rewrite them most years.

Wow, that's so that you talk about introspection. That's so we always think of values as things which are kind of long term. Right. They're supposed to be Durable, at least over a period of multiple years. But it sounds like you were just acknowledging we have to be flexible and iterate the values as we grow.

Yeah. And so the way I thought about the values, and I've since thought about values, is they were, they were lightning rods for what we believe in.

Yeah.

But they were always up for debate and discussion.

Yeah.

Right. So move fast and break things was something we intentionally talked about like a year or two later. And very quickly. Right. We were able to have that discussion. Like, that's a terrible value. Let's burn it down to the ground.

Worst value ever.

Yeah. Whereas progress over process became a very important thing. Right. Progress or process, when you have six salespeople starting or when you have 10 engineers. No, you. You need process in order to make progress. So it allowed us to have those intelligent level, level debates so we can very quickly discuss how do we interpret that. Whereas some we held near and dear. So ownership and transparency and being user centric were through lines that may have tweaked over time for sure, but they were through lines throughout the course of the company and not set in stone saying, oh, this is just the way we operate, period.

Yeah. Yeah. So then again, as you discuss them at your annual off site, I'm sure that you kind of enrolled your newer employees into the deeper sense of what that means. And also you began to even probably you talked to all the employees and everybody came to terms with the new maybe nuance of what these same values mean for us now at the company now, as opposed to five years ago.

Exactly. And I'm sure there are more things we could have done better. Like, we didn't, when we were doing annual reviews or quarterly reviews, we didn't necessarily say, hey, how are you matching up versus the values? We didn't ever really get that far, but we were able to, as new people came on board, or as we had other experienced people, we were able to start having those other conversations around. Okay, what have you learned? What do you bring with from your other company? What's important here? And how do we. How do we shift it?

Yeah, yeah, that's great. So, Zvi, I want to turn to kind of like the ups and downs of startups, because startups are filled with ups and downs. I'm sure yours was no different.

I have no idea what we're talking about. No. This was a walk in the park for seven and a half years, straight.

Up and to the right. And I think one of the issues, you don't always know if you're Winning. So how have you dealt with, how did you deal with the bad moments in your day to day?

Yeah, I think there are two ways to phrase that. Right. One, let's talk about the company and then talk about myself as well. Company wise for us being what we built was a B2B SaaS business ARR and growth in ARR and all the attributes of annual recurring revenue. Like where were they were the key. And so we're able to very quickly look at like hey, how are we growing? What are our setbacks? And I do appreciate this about your, about my co founder is we were always very clear at saying here's what's working well and here's what's not.

Yeah, right.

We got in the habit of with our board and with our executive team having like red, yellow, green and very clearly being able to delineate what is going green. What is yellow that we're concerned about. What is red? Oh, we need to talk about this right right now. And we were so just being able to be transparent and being comfortable sharing with our team. Here's the bad, here's the ugly, here's the great. Let's celebrate the wins and let's talk about how we improved the things that aren't going so well. And then we're frankly we are very focus on just once we had that out in the open. Oftentimes we're able to problem solve with our team but we were able to say, hey, here's how we solve it. Right. If a client is two months behind on not on paying their invoice. Okay. It's not like the accountant team is going to hide that or the customer success team is going to say oh no, don't worry, everything's fine. The checks in the mail or anything like that, hey, this is a problem. Okay, how do we solve this? Right. And we're able to bring the full team on board to be able to address it. For me personally, yeah. I would say I was not prepared for the startup journey and to this day I still think that the seven and a half years of building contactually I spent in survival mode and I strive not to spend that. Yeah. One of the key tactics I developed was being able to separate the feelings of the moment or of the day from what I would actually do because oftentimes and I learned this about myself, that if I got overwhelmed or stressed or nervous or afraid, I would freeze up and stop. And I had to start realizing and developing the scale of saying no svi, you are feeling afraid or stressed or Angry right now. Do a quick, like logical check. No, everything seems to be fine. Or here's what's going well, here's what's not. Here's how much cash flow we have left in the bank. Here's the, here's the. In the Tim Ferriss, like, yo, Tim Ferriss language. Here's. Here's the worst that could happen and here's how we deal with it. Or here's how I deal with it and then put together my to do list and then just keep going at it.

So it sounds like you would be emotional, upset, overwhelmed, whatever, and you would kind of force yourself to look at the facts and then just deal with what had to be dealt with despite your feelings. Is that right?

Yeah, absolutely. And I think what became a company value of progress or process, really, I think came from me in that I've always tried to make sure that no matter what I wake up in the morning, I put together my to do list and I do my to do list. And that meant sometimes I had to shut off my brain, shut off the emotional side of me and say, hey, I'm just going to execute this to do list today and not think of it then. Great. Right. And I've since learned on how to better handle emotions, but that was the tool that I implemented at the time.

Right. Well, what did you learn about how better to handle emotions?

I feel. And this has been really, in the few years since acquisition, as I work to, for lack of a term, like do the work to prepare myself mentally, physically, emotionally for the next. For the next mountain to climb, it's to really embrace my emotions. Right. Not put in a box and just hide it or turn it off like as we joke about, but rather to just fully embrace it, saying, hey, why am I feeling angry? Let's understand that. Like, why am I feeling emotional? And how can I address it? And oftentimes I'm even just sitting in 10 minutes of meditation, I'm able to fully unpack those. Those feelings and come up with a solution for them. Right. Maybe I do need to have an honest conversation. My co founder. Right? Maybe sp you do. If you're afraid of your bank balance, just open your bank balance and understand it and figure out what to do about it.

Yeah. Wow. Now, you also said you were not prepared for what was going to happen in those seven years. In what ways do you. Do you see that you were not prepared? How. What would have prepared you? But how did you see you were not prepared is really the first question.

Yeah, great question. So I think as I mentioned early on, I, I didn't start with the summit and say, okay, I need to have like my gear in place. This is the team I'm going to need, this is the funding I'm going to need. Instead, it was like, you know, just a game of inches and just clawing our way forward, you know, month over month, quarter after quarter, year after year. One of the ones that I think sticks out with me the most is for the first few years of the company, I didn't feel like a leader. Like, the company was running, we were hiring people, we were executing a plan. But I both had like severe imposter syndrome. Like being CEO of the company, I was the CEO that kind of wanted to hide in the back of the room, right. And just like support everyone else. Like servant leadership, I think is a double edged sword because that also gives you the permission to stay out of the limelight. And it wasn't until I remember we hired a coach for me, you know, halfway through the journey and one of the most valuable things in my life was doing a 360 of all, you know, most of the people in the company. And it was very clear, like sv, they see you as a leader. So intrinsically I didn't feel like a leader. Extrinsically, they gave me the validation that said, spee, you are the leader of the company. You are acting like the leader of the company, so start acting like it. And that was a shift. I was like, oh, they need me to, they need me to help light a torch. They need me help light the way they, the customers need to see who the leader of the company is. Right. I can't just put the salespeople out there. Right. But I need to be at conferences. I need to be, you know, I need to have much more of a presence with my team and without versus just hiring people and saying, hey, what, what do, what do you need from me? Yeah, to do your job here.

Yeah, that's. So I just want to unpack that for a minute. Like, I think that servant leadership, of course, is such a beautiful, noble aspiration and modesty is a virtue. But I know that when I work with CEOs, the ones that I coach, they can be too modest. They'll say, it's not about me. And I'm like, actually, it is about you. Because all those people around your employees, you need to see you in the front of the room sometimes, need to see you at the conferences sometimes. And it sounds like that's what you got out of your Coaching process.

Absolutely. Yeah. And this relates to other things too, like including about company values. To me, one of the biggest gifts, which we don't really talk about enough, is the acquisition process. Because what happened is we were able to take the same team product, office space, mission, and airdrop it into a different company with a different culture. And I was able to see how a different leader exhibited their leadership. Yeah, I was able to see how small, subtle changes in values could have massive impacts on day to day. And so I was able to clearly see like, wow, it's not that I felt that someone was more or less of a leader than me, it's a question of what are, what are they actually doing to exhibit? Like, I'm still a software developer, I trade, so I still go into my mind to like, what do I give me the things I can do that will allow me to exhibit leadership and able to see that. So I started writing regular to regular regularly to my team. I. At company retreats, it was no longer about, you know, culture workshops and team gap through togetherness and strategy sessions. But I would stand up there and I would be honest about my, my passion for the company and the vision that we have and the challenges that we've seen and what we've achieved so far. I. Whenever there was a company celebration, I would always elevate it to like the highest company mission. Not just, you know, say, oh cool, we, we ship the product or we, or we, or we close the customer, but like always weaving in the larger story of contactually into it and it's just picking up those that end up being transformational for me as a leader.

Yeah. Oh, that's, oh, that's amazing. So I'd love to hear about the acquisition. So kind of tell us kind of the before, during and after, you know, how did it come about and what was that like? And you said there were some, maybe some, you know, some ups and downs even through the acquisition. So let's hear about that.

Yeah, absolutely. And obviously, like, you know, when you talk to any entrepreneur about an acquisition, there's always like, you know, their mouth half zipped by what they can or can't talk about.

Sure, sure.

But like, for us, like, we, you know, we were, we were hitting a key milestone. We were passing 10 million in annual recurring revenue, which for us SaaS business, you know, software as a startup is a very key milestone that many people regard. And so we knew we had something there. And for the board and myself and my co founders, we were starting to look, saying, hey, well, where do we go from here? Do we raise more money and keep investing in the business and move to other markets or keep moving up market and selling bigger customers? Do we keep going as is or do we look for, for an acquirer? And honestly, like, we, again, without having real like, foresight of like, this is what we want to achieve and let's go do this. We were really pursuing all of them at the time Compass was a acquisition, was not an acquisition target of ours, but rather they were a ideal customer of ours. We were selling at the, at one time, I think we had eight of the largest 20 brokerages in the country. And so we brought, we were able to bring on Compass as a customer. They had approached us a couple times by saying, hey, could we explore deeper strategic partnership, et cetera? And I would say that the right doors open just as we and the board were starting to say, hey, this is it. Right. We had started to explore options a year or two before and we had always received acquisition interest. But at the time, it's not that we said no to it, but we just, we weren't even ready to have the conversation as a board or even myself and Tony, we weren't having the conversation about us saying, hey, what do we want? But we started to. So, for example, and this was important for me, you know, I think Tony and I both realized that we were hitting the stage of the business where he and I had maxed out our learning, if that makes sense, and there would have to be some larger step change, function happen.

Yeah.

And I developed this internal mindset over the years that contractually that this was the best business education I could ever get that would happen to get paid for. And I felt like, hey, I've, I've maxed out my learnings here. What is going to be that next thing that will allow me to learn? And after exploring all the right, all the right avenues and having a number of, you know, interested parties, we end up joining forces with Compass in 2019. Who initiated that?

Did they initiate that discussion? Did you. For the actual acquisition, did you also meet with Rob? Did you guys have some discussions and meeting of the minds or like, what was that process like?

Yeah. So to no surprise you, given that we are a company around relationship building, it was a relationship I had. I had met Robert a number of times over the previous years and had worked with a number of Compass agents even before they started talking to us. I think 20% of Compass agents at one time were customers of ours. So we developed a relationship and my sales team and I were always trying to bring on Compass as a customer, but we were able to build up a strong enough relationship where I remember 9pm One Monday night, Robert called me out of the blue on my cell phone. I remember standing in my bedroom in D.C. and he said, hey, would you be interested in exploring a potential acquisition? And that started, I would say, a much deeper relationship. And to no surprise, there were fits and starts, but that was the beginning of the relationship that resulted in us being acquired. But I do truly credit the relationship that we had built with people in and around Compass over the years.

And so the acquisition went through, was that easy or hard to talk about where with your companies, with your employees?

So when we talked about the. This has ended up being one of the best lessons I've learned. For better, for worse. As I mentioned when we talked about our values, I really value extreme transparency. Right. We can't fix what we don't know about, so let's get everything out on the table and we try to exhibit that as much as possible. And there were times where we, you know, we hadn't remained more tight lipped about things, you know, cash situation or having to make larger, you know, exec or staff changes, et cetera. But unfortunately, when we weren't as transparent as we wanted to be around the acquisition, we weren't, we were too transparent.

Oh, yeah.

And this is one of the things I learned too. I learned to, I learned too late that as good intentions, you want to be around transparency. Radical transparency and total transparency are very different things. And especially when you're talking about, you know, a move that people would be concerned about, would affect their livelihood without them fully understanding all the ins and outs of it, that it's a very scary thing. And now in hindsight, putting myself in their shoes, right? You know, telling a salesperson, hey, you know, I need you to go on the road, but who knows, this company may, you know, may not be around in, you know, in three months or, you know, telling someone who's, you know, just about to get married, hey, yeah, you probably will have a job still, like 95% sure. But still that 5%, maybe not, right?

Ouch. Yeah.

Yeah. So as as much as we fought for our team and made sure that everyone ended up in really good place, you know, in hindsight, we, and I counsel this to other entrepreneurs too, you know, founders, hey, there are things that you really just have to keep yourself and your board and that's it. Not exec, team, not like, you know, advisors, not even all of your investors. And so it was, it was up and down, like for sure. Like I would say, you know, having spoken, worked with other founders have gone through this too. You know, you have to pretend to pretend like everything is going normal outside of an exec meet or outside of the conversation and then jump in and have a completely different mindset. So bouncing between those two mindsets was a real challenge, especially when you add it in. Our team started to find out and you know, hear, started hearing things so we'd get questions either way. But yeah, it was a very intense six month period.

Oh, I can imagine, I can imagine. So you join Compass, at least for how long were you at Compass then? Did you stay, how long did you stay at Compass?

Just under two years.

Just two years. When you first got there, you and the team, however many people you could bring with you and I guess Tony also. Is that right? What was that like, what was the integration period? How, where was the match and the great fit and where were the sort of points of like, oh, I didn't know this was going to happen. Like what was surprising?

Yeah, no, I would say the, the, the great, the really great thing about it is they needed us. Right. Like that we, and we already had a bit of relationship, we already had them as customers. There was absolutely no question in our mind that everything that we had built and learned about contractually, about operating taxually, customer success and training and design and UI UX et cetera was oh yes, the faster you can implement this for our customers, the better. Right. And so actually now like, you know, if you speak to anyone, Compass, you just saw just over the two years post acquisition, just a complete polarity shift in the, the technology they had built out the biggest challenge. And I still am not sure how we could have built around this. But as an executive team and as a founding team and as a board, you know, we were so focused on both sprinting towards the moment of acquisition and also trying to be, trying to carry on as business as usual. Yeah, that the moment the acquisition closed and the team knew and our customers knew everything, everything contractually previously ground to a halt. Right. Sales and customer success with like wait, are we selling? No, we're not actively selling anymore. How do we support our customers on the product side? Like wait, like we're now we're not building contaction anymore, we're building encompass CRM. Like what is our roadmap? So and we tried to spend time focusing on the, you know, focusing on the, you know, first hundred days post acquisition. I remember we started having meetings. Yeah, but for various reasons, you know, as is actually quite obvious, we, we were so focused on the transaction itself.

Yeah.

And so I'm still not sure how we could have dealt around that. But it definitely took time to restart our engines, a couple weeks there of getting our engineers on board into the new ecosystem, etc.

Yeah.

One of the biggest lessons is that I, that I personally learned, and I think this in hindsight is obvious, is that, you know, we were a 70 person pirate ship.

Yeah.

And now when you're joining a larger company, you're joining the Navy. Right. And then pirates versus navigation Navy, you know, metaphor or something. And I learned, you know, too late. Yeah. And in hindsight I, I didn't prepare myself for operating like part of the Navy. Like I was way too much of a pirate. I was like, hey, let's just go build this feature. Or we don't need approval for this. We'll just send off an email and.

Let them know whatever progress over process. Right.

Yeah. And not prepared, not even prepared for the cultural shift. Right. Of hey, how do you, how do you, how do I as a leader operate now when there's multiple levels of management above me? And so it definitely took some time, but overall, I mean, again, I consider contaction to be business school. I learned a whole lot through those two years.

Yeah. That's amazing. You know, I spoke to Matt Blumberg, who's the CEO, the founder and former CEO of Return Path. They also got acquired. But before they got acquired, and they almost got acquired, as he told me, they got very close to being acquired and then it fell through. And to your point, their business had grown, had had ground to a halt. Their business had to be restarted and they didn't have the acquisition on the other end. I think it's a very difficult thing when you're prepping for acquisition and you think it's going to happen to then somehow keep with your left hand, keep the business moving. So it's like seamless. That's like a very, very difficult problem.

Absolutely. And I think there's also, and I've spoken to other founders about this. There's also the thing we don't address often enough, like the mental side of what's happening to you as a founder.

Yeah.

You and I know many founders post acquisition who for various reasons go into deep depression.

That's true.

I didn't. But in part because I remember surrounding myself with other entrepreneurs who had sold their company and I'd seen the, seen the warning signs of what to look for. And so I Started doing even six months before started doing the mental work to. And sounds weird but like to mentally let go of my baby.

Yes.

Right. That by the time the acquisition closed, as much as I love and bled for contractually, it was time for it to move on.

Right.

And. Or move on from me.

Right, Right. What was that mental work? How did you do that?

Yeah, to me, I think it's because the. The startup can be, you know, can be such a key part of identity. I had to do a lot of work to identify like, wait, who was I? Right. I. I wasn't just vban CEO of contractually. I was banned Entrepreneur. Entrepreneur of multiple ventures over time. Not just contactually. Right. That I'm a father, that I'm a husband, that I'm an investor, that I care about these things. Right. And that my identity is not wrapped up and my life is not wrapped up based on what I do for contractually and how can tax is going because sure enough over the years as contractually went to the as you know, like the worst screwed it's over moments. You know, I felt that moment my life was spiraling down the drain when hindsight it took my wife and others to pull me back and say, sweet, everything's fine. You're just having some problems at work. Right.

Right. So just. I want to just double click a little bit more on that. The identity piece and the ways you did. Did you journal? Did you talk to somebody? Did you meditate on it? Like what specific practices did you do to work on that identity piece?

Yeah. So prior to acquisition, I started journaling a lot more.

Yeah.

I started talking to other entrepreneurs who had in the prior nine months has sold their business and that ended up being really helpful. Like, hey, what did you go through Issues. So one of the things that I'm very thankful for was I started learning and reading so much about founder depression post acquisition.

Yeah.

Which it sounds like such a first one world problem. Like, oh, come on, you sold your business for millions of dollars. You know, all this money's in your account. You get this accolade, you level up in life and sure, you're found, you're faced with depression, but really like it is. It is a legitimate mental issue that I've seen people go through.

Yeah.

And so that was really helpful to be able to be aware that this wave was coming for me and therefore I could prepare myself by journaling, by talking to people, et cetera. And then frankly like starting to very quickly dive into doing the work and picking up meditation and losing weight. And everything like that right after the acquisition.

Yep. Yep. That's great, Zvi. So just a few more questions here. What, what do you wish you had known earlier on your journey?

Yeah, great question. To me, communication with your team, your co founders, and also yourself is penultimate.

Yep.

And I do also the self communication to be important. What do you mean by that?

When you say self communication, what do you mean? Like self talk?

Like, what am I really feeling? What's happening in my head? What is logically breaking it down around what I could be doing or doing different? I think we've touched on this a couple of times before, but transparency is not, not all or nothing. As much as we push for radical transparency, we push too hard. And I look back at numerous situations over the period of time, and if I were to go back and do something again, it's that the speed and clarity of decision making can be a true weapon for the business. Right. And also weapon against you when you're lacking it.

That's so great. And so is there one or two pieces of advice you have for other founders as they embark on their journeys?

So get your mental health in order. Right. And I know we, we, we sacrifice so much for our company, for our companies, but I now see a therapist twice a week. Yeah, we'll be, you know, I do so many other things to make sure I'm taking care of myself, mentally, physically, spiritually, emotionally, and to be honest, seek help. People love entrepreneurs and entrepreneurs love entrepreneurs. Right. And I find again, going back to communication, there's something really powerful about, you know, getting on the phone with someone, another entrepreneur, an investor or something like that. And you know, when the usual pleasantries come up of saying, hey, how you doing? Instead of saying, oh, yeah, I'm doing fine, you can say, you know, Honestly, I'm a 6 out of 10 right now, and here's why.

Right.

And that can just transform yourself and the conversation in a moment's notice. And you will walk out a better person for that.

Yeah. Oh, that's so great. I love that. What's great advice. And you know, and I, whenever I ask founders, what's your advice for other founders, you know, for, for people just starting their journey, they always go to the self care. They always go to like, take care of yourself. And I just really appreciate that. It's so, so important.

Important because we're so good at, we're so good at ignoring other people's advice, including our own.

That's true. That's actually really true. So sweet. What are you working on? Now tell us all about it.

Yeah, absolutely. So, you know, as I dug deep down to understand why I'm here on Earth and looking at all the projects I've been passionate about and frankly, asking myself, like, what could I spend? What problem could I spend the next 10 years of my life working on? Empowering human connection is at the center. Right. I think it's clear to all of us that we're in a valley of loneliness. Right. And we're just seeing tectonic shifts in how we relate to each other as human beings. Like the way my grandparents found their sense of belonging and community. Each other is going to be completely different than how my two young kids will. Right?

Yeah.

And we're stuck in the middle, like, lonely and fragmented and burning down each other's houses, et cetera. And I truly believe, like, our mental health crisis is social health crisis. And so what I'm focused on is that we humans build community through conversation. So that's why I'm focusing most of my time on. Right. Helping people gather their communities for deep, intentional conversation, the likes of which you can rarely experience without a trusted facilitator. And we're truly understanding that great conversation is like an art form. And we want to help people have the deep conversations that lead to a life well lived. So that's what we're building with Talk Social.

Love it. I love it. So juicy. I can't wait to see the journey of you and Talk Social Media. Is there anything else that you'd like to say?

Yeah, it's great question. As I think about my personal mantra, I maybe have been guilty of this in going back, talking about my journey and saying, oh, I wish I'd done this. I wish I'd done this. I think one of my fundamental operating principles, which I try and share with as many people as possible, is to live life with no regrets. And so that's why I don't live in the past as much, saying, I wish I did this or I wish I did this. It's that, oh, I learned this in the past. And therefore, this is what I want to exhibit going in the future. And that's a very big mental shift. And truly now the reason why I'm pursuing Talk Social versus another, let's say, more achievable venture idea is because I want to make sure that I'm able to wake up every day pursuing something that I truly believe is my calling and I will regret anything else otherwise.

Yeah.

And I have to remind myself. And so to me, the thing I counsel entrepreneurs and even my kids now is saying hey, what is the decision that you will regret the least and just make that decision.

Yeah, that's great. Sweet. Thank you, thank you, thank you. What a joyous, joyous conversation. Thank you so much for your honesty and your genuineness and it was just great to have you on the show.

Likewise. It's great to spend time with you, you know, look forward again. You and I still have yet to meet in person, I know. Hopefully sometime soon.

Hopefully someday.

But very thankful for your time and your questions today.

Good. Awesome. Okay, good. Thanks everybody for joining in.

Bye.

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