#98 3-time founder Craig Walker — From Selling Door-to-Door to 3-time founder; Building Google Voice; and the Real Trade-offs of Entrepreneurship

And we had a board meeting and Mark Andreessen's on our board and he's like, yeah, you should buy them. I'm like, okay, let's. I'm on it. And so I called, we left that. This is amazing. Left that board meeting in San Francisco. I called Dan, the CEO, right? Texted him like, hey, where are you? He's at, he's at some restaurant in San Francisco. I'm like, I'll be right over. Go meet him. That night we have have a couple drinks, talk about it. And by the end of the night of that board Meeting, both the CEO of DialPad and the CEO of Tac IQ were now in agreement that this is a good idea. We just need to figure out the details. Like, it was amazing speed. And then the acquisition happened and it was, you know, like at the time we were less than 30 million of revenue and we bought them for 50 million and their revenue was like near zero. And so it was like, it was a really big spend.

Welcome back. This is from startup to grown up. My name is Alyssa Cohn and today I'm thrilled to welcome Craig Walker to the podcast. Craig is a three time founder and now the founder and CEO of Dialpad, one of the most advanced AI powered communications platforms on the planet. We had a fantastic conversation, starting with Craig's first job, which was going door to door in office buildings selling dictation machines. Craig talks about how these early cold calls shaped his respect for elite sales pros. After that, Craig did all the things business, business school, law school, M and A attorney, until he started his first company, which got acquired by Yahoo, and then started his second company, Grand Central, which is now Google Voice. He then walked away from his cushy Google job to start Dialpad and we talked about what gave him the impetus to do that. We discussed what it's like to start multiple companies and what he learned along the way, including about culture, about integrating the company they acquired, and a lot of surprising insights about hiring. Now, just as candidly, Craig described his personal side of the founder journey. Coding with his co founders in the backyard while his family ate dinner inside. Missing bedtime, but coaching the soccer team and learning to balance his relentless ambition with the relationships that matter the most. This is a fascinating real talk conversation. So please enjoy my great discussion with Craig Walker, founder of Dialpad.

Craig, welcome to the show. I'm so excited to have you.

Great to be here. Thanks for having me.

I'm super excited to talk to you. You're a renaissance man. If I will. You're a former M and A attorney, a venture capitalist, a three time founder, and now you are the currently the CEO and founder of Dialpad. But you started off as like a door to door salesman. Like you were selling dictation machines, right?

Yeah. So door to door dictation sales. Graduated from UC Berkeley, social studies major, loved the discipline, but really didn't prepare you for a whole lot of stuff. And worked in downtown San Francisco for a company called Lanier selling dictation equipment. And it was literally, this is the late 80s. You walked into the office downtown San Francisco, you had to be there by eight, they threw you out of the office by nine, you couldn't come back till five, and you literally just walked door to door in the financial district of San Francisco trying to sell dictation equipment.

It was, that's incredible.

Yeah, it was, it was a different time one. It was, yeah, it was pre 9, 11, obviously it was like 8 late 80s. So you could go into a high rise, like literally you'd hit the top button, go into every business on the top floor, go down a floor, go into every business. And by the way, you're in downtown San Francisco. So they're, these receptionists are very adept at getting rid of people like you. So there was a lot of, a lot of being, you know, politely shown, shown the door. And then like one time it was funny, this one time they have your little pitch of, hey, I'm here to see your managing director. Do you have an appointment? That's just what I'm here to see him about. And then, and then one, one time the guy happened to be walking by, he's like, hey, come with me, let's go talk. I'm like, I've never been here and now what do I do? But it was, it was definitely a tough grind. It was, it was about the hardest way to make a living I could ever imagine.

I mean, I can't. It's hard to imagine. What did you learn from that?

You know, it's interesting because I learned that one, this wasn't a career that I wanted to pursue for the rest of my life. And so I went back to business school. But the other thing I learned, which was interesting because I had buddies and people I worked with who stuck it out and ended up being successful and leveraged that into other better sales jobs and then just had great sales careers, moving up the ranks, selling more and more complicated, interesting stuff and making more and more money and being radically successful. And so kind of the big picture that I didn't See at the time is, hey, if you can figure out how to be successful in this very difficult thing, and if you can be ready with every conversation and when that break happens and someone's willing to talk to you that you're ready to go, close them there. There's a real, I mean there's a real art and skill to that. And so what I learned was massive respect for success, successful salespeople. And it is not easy and it's a grind. And sometimes it's hard to kind of see the future based on the day to day struggles you're having and the amount of negativity you face. But the people who can do it, man, hats off to them, they're, they're worth solid gold. And now on the other side, when you're building a sales team, do everything you can to find those types of people who've overcame those really tough, tough, challenging, you know, initial jobs and particularly initial sales jobs. But most importantly, I realized I needed to get into a, I need to up level a little bit.

Yeah, yeah. So you went to various. Actually, I wouldn't mind. I think it'd be helpful to maybe trace your career a little bit because you really did all these different things. You went to business school and when did you go to law school in all of this?

Yes, I went to Georget Business School, got out of there in 91 and came back to the Bay Area. Had grown up in Cupertino, so I'd always been kind of a Bay Area kid and worked at Apple Computer then in their customer success organization. And so that was great. I loved Apple. It was. Jobs had left, he had not come back yet. So it wasn't really the heyday of Apple, but it was. Apple was still probably the coolest company in the Bay Area and so loved that. And then they decided to move that entire organization to Austin, Texas. And this is, you know, and the big pitch for all of us was move to Austin. You know, you can't afford a house in the Bay Area, you'll be able to own a house there, et cetera. And I realized I didn't want to do that. Nothing against Austin, I absolutely love Austin and we have a big office in Austin. But I just like met the girl of my dreams. We were kind of like our lives were in the Bay Area. So I had dabbled with going back to law school and I had taken the LSAT and did pretty well on it. So I'm like, okay, this seems like a great, you know, fate is telling me to go back to law school and, you know, when the economy's not super hot and you're still young, I'm like, look, I can. I'll be much better off for investing this time in law school and going to do it. So went. Went back to Berkeley for law school and really just had this, like, passion for everything in the Bay Area. Business law, startup law. And I got an intern, summer, summer associate position at like, one of the top law firms in Palo Alto in the Silicon Valley, and working on super interesting things with. With really cool people and just realized I loved it. So glad I did it. And then, you know, after I graduated, I was like, right in the heart of Palo Alto working like, Cisco Systems was our client. I was on their M and A team. This is like the, you know, 1990, 95, and they were buying, I don't know, four, five, six companies a year. They were just growing like crazy. They were the hottest company in the Valley. So it was just. It was just a really, really cool experience.

Yeah, I can imagine. And I just wanted to say I was. I was a coaching at EMC for quite a bit during that period, and also a very acquisitive company, and I helped them write their playbook for acquiring companies. So it's like the notion of when you do something over and over and over again, you kind of get good at it, hopefully. And I'm sure that you, as an M A attorney, really saw best practices and worst practices over overall.

Yeah. And it was, you know, and you saw acquisitions that went terribly. Like, there's a bunch of ones that, you know, examples where the cultures don't fit and. Or they just try to assimilate them into one immediately and then everyone leaves. Cisco was really great in that they would do an acquisition, but it was an acquisition for something they didn't have. Right. So by adding something you didn't have, it was really hard to say. Now you're just part of this existing team. They really let people and companies they acquired continue to do the things they were doing that made them so successful and that allowed their acquisitions to be really, really successful. And, you know, at Dialpad now we've done five acquisitions and we've done taking that exact same philosophy on all of them. Like, we're acquiring pieces of technology that we want to have in our one platform, but we don't. And so since they're the experts, they get to continue to kind of like, run their own teams and behave the way they behaved before. And it's not this jarring. We're Trying to force you into the way we do things immediately. And they've been all pretty successful. And I think I learned that from Cisco.

That's amazing. We're definitely going to dive into, like, more in depth examination of your acquisitions, but like, let's zoom out and talk about dial pads. So like, you got acquired, as you said, you got acquired by Yahoo. You did Grand Central, by the way. I was an early Grand Central user. Thank you very much.

Thank you for that.

I know. And then you got acquired by Google. Grand Central turned into Google Voice and you ran Voice for like three years, I think at Google.

Right.

And. And you know, just to say in those days now also Google's a cushy job also, it was a rocket ship. Certainly in those days. What was it that allowed you to say, take your cushy job. I'm going to leave and go start something else? That's a very challenging thing to do.

You know, it's interesting because you're, you're at a startup and you're kind of like you're working hard every day and you're making all your own decisions and you don't need people's approval. You just got to make the right decisions and hopefully everything works out and then you get acquired by a big company. And the first one we got acquired by Yahoo and Yahoo was the. It just felt like molasses. It was just like the biggest of big companies and like no one could do anything without everyone approving. And like trying to convince everyone to do anything just made it so tedious. So we, so Vincent and I literally left. I left after three months, he left after four months, and we just started Grand Central and we're like, look, we're never going to sell to a big company again because that sucked. And then Google came and we were out of every, any company in the world. The one you probably would say yes to would be Google. If you had a goal to never sell, you should put an asterisk on it that says other than to Google, because Google was by far the single coolest company on the planet. And when was that, 19 or 2006? Yes, that was like 2006. And so we got acquired by Google and Google was great. It was this chaotic, you know, startup. No one told you how to do things. You were just kind of left to your own devices to do things. And that was kind of like the honeymoon period of like, we bought you, now go figure out how to make this Google worthy. And so everyone kind of left you alone. And then, then we Relaunch the product, it starts to be really successful and once you do that, a lot more people want to be involved in your product and project and you have different groups fighting over it. And, and so yeah, you could have stayed, we, we all could have stayed there and had a very stress free life and, and tried to do good work. And I know, you know, I have friends who are still there from that time period and you know that that's, that's a totally fine path. It was a great company obviously, but after like three, three and a half years there it started to get like it was, it was like you were working at a big company. At the time it was 20, 25,000 people. I mean, I don't even know what it is now. 300,000 people, like it's much larger. Yeah, but 20,000 seems like a lot. And my days were filled with meetings with other manager layer people and not really accomplishing things and not really, you know, driving product decisions and not really being in the weeds and not being able to really do the things that I probably feel more comfortable or think I'm better at. Like I'm not. It's stifling to feel like you're just going to sit back and be a mid level manager at a great company that just didn't do it for me anymore. And then there was, there's this one morning where I woke up and I'm like, you know, this is the first time in my career I kind of dread going to work. Like this is going to be a long commute down a mountain view. I'm going to be in meetings all day. Probably not going to accomplish much more than going through a ton of meetings and then I'll come home and then you know, like, I'll do it again tomorrow. So it was kind of at that point where I'm like, okay, I think I, I think I got another startup in me. I think I can, I got an idea like how could we do the Google voice for enterprise communications and how could we make it so much better than anything that's out there already? That, God bless my wife. She supported me when I quit the law firm job, she supported me when I went to a venture fund, she supported me when I quit that to go to the struggling startup. And then kind of all the way through she finally got to a point where I didn't have to work very hard and we'd have been fine and set for life. And then I quit that one too. But it, like it's just the, it's the only way to live. You know, like it just the, the last 14 years running Dalpad have gone by in the blink of an eye. And I think it keeps you young, keeps you, keeps you motivated and you know, you only live once. So. Yeah, so it was worth it.

That is so powerful. I mean, there's so much to ask you about, but I'll, I'm just gonna sort of double click on it. Sounded like you have a feeling, you have a feeling inside of me, of, you know, that's like, I can't just be a mid level manager. I can't just be part of this kind of cog in the wheel. I have to have the ball and run the ball down the field myself. Like, is that just a part of you on your inside?

Yeah, I think, you know, I read this quote, this Helen Keller quote of like life's either a daring adventure or it's nothing. Right? And so like it was, it was no longer a daring adventure. You know what I mean? It was, it just became like a path to, you know, comfort and a path to comfort, you know, like, is it, is it doesn't get you excited to get up in the morning? Or at least it doesn't get me excited. And by the way, like, I'm, I'm probably making this sound worse than it was. I, you know, the food was amazing, the shuttles were great, the people were awesome, you know, the products were insane. Everything about it, as far as a big company goes, was great. It's just you're, you're either wired to, you know, kind of move fast and do things and break things and try things, or you're not. And I'm just more wired that way.

That's right. That's why you're a three time entrepreneur. I get that. So you went off and founded Dialpad. And so tell us about that journey because I think that Google Ventures was involved with that. And what, what is explain to everybody what Dialpad is and why it's so significant.

Yeah, so, yeah, so what Dialpad is, is a modern business communication platform for any type of business communication that your company needs. And so we, we had Google Voice was a consumer, you know, voice communication tool where we gave you a phone number that rang you on all your phones and moved all your features and voicemail and texting to the cloud, which was really innovative at the time. When we, when we were at Google, thinking, okay, what's the next step here? We really wanted to do, okay, let's go take that and let's go build the world's greatest business communication platform. And every company in the world has a platform to speak to their customers. Every company in the world. There's something like, at the time there was something like almost 500 million desk phones on people's desks in the world. And our whole mindset was, that is crazy. You know, the cloud is here, software is going to eat hardware and you should be able to work effectively from anywhere on any device, including your own cell phone, and not have to go into the office to use your work phone. Like, I know this all sounds like super simple and obvious today, but at the time it was kind of revolutionary. And the idea was, you know, would a big company ever trust the Internet to carry their phones in these crucial conversations? You know, it has to be one of these old legacy Cisco or Avaya type systems. And our bet was that the network was going to get better. The need to be productive would overwhelm, you know, the need for complete, complete 1 zillion percent, you know, reliability and kind of the advent of the mobile phone had proven that, that hey, the quality wasn't as good as a landline, Calls would drop occasionally. But the value of being accessible at any time from anywhere on the planet more than outweighed those small differences. And so we want to do the same thing for business. So we were sitting there at Google Voice and realizing, look, we want to do this and let's build a Google Voice for enterprise. And kind of was working toward that to do it internally. And Google at the time got really obsessed with Facebook. And Google had this big initiative of like, okay, all you consumer apps at Google, you are now going to work on our new social network called Google. It was such a raging success. We all use Google all in our daily lives all, all the time today.

So some things don't work out, guys.

Yeah, so it just did. Like, apparently no one needed yet another social network. So what happened was we were like, look, we're not interested in that. We're hardcore communication zealots. We want to go innovate this massive trillion dollar market of just worldwide communications. So we're going to leave and go build outside of Google something very similar to what we wanted to build inside of Google. And so Google being the great company that it was, said, okay, hey, why don't you come over to our newly funded venture fund, Google Ventures, now called gv. And there were just great folks there. Wesley Chan, who is the product manager who led our acquisition in the first place. Rich Miner, who was the co founder of Android, was Over there. David Crane was a great guy over there. So there's this great group of, Bill Marist who ran the fund, which is great group of the four of them pretty much building, you know, really starting to stand up this venture fund. So they invited me in to go be an entrepreneur in residence, which basically meant you get paid to kind of think of ideas and come up with a business that they can fund. And, and I did that for, for a while and, you know, kind of knew what we wanted to do. And so it wasn't like this long period within, like, I don't know, like four months we had put the finishing touches on what we were going to do. They funded our Series A. I was able to hire, and Google was very supportive of allowing me to hire the engineers from Google who had built Google Voice as my co founders. And then we were off and running. So it was, it was about as kind and, you know, like amicable of a separation as you could ever have. And then Google, God bless them, through Google Ventures, gets to be a big investor in the company.

Yeah, I, that's an amazing story. And I would just say when you had the asterisk before, like, we're never going to sell to a big company. Ooh, asterisk, Google. I think that's certainly in the heyday of Google, probably still now. That's part of the value of Google, that they really, they really come from a DNA of innovators and they come from a DNA of entrepreneurs. And part of their whole Google Ventures thing and other ways that they handle things is like really enabling the next generation of entrepreneurs. It's kind of amazing.

It is amazing because you could see, like another company could have taken it a entirely different way and say, hang on, you're leaving. Well, no way are you, like, no way can you, we're going to sue you if you try to hire anyone, you know, from, from here and, oh, you want to go work on something similar to what you worked on here, no way we're going to sue you on IP stuff. And Google was the exact opposite. They were like, sounds awesome. Go do it. Understand, like, it's frustrating that you didn't get to do it internally. Knock yourself out and we're gonna fund you. And it was just like, you can't say enough about Google. They're just fantastic company.

Yeah, that's amazing. Now, what year was this that you started this style pet?

That was right at the beginning of 2011.

So what happened? So you, you, you built up, you know, sort of, you had the Business model in mind. You, you were the entrepreneur in residence during this period. So you were thinking it through, you were off and running. Walk everybody through what literally the first six months of a startup are like, like, you gotta find space, you've gotta like hire people. Like what is that? Like?

Yeah, it was crazy because I was the entrepreneur in resident, but the team that wanted to come with me were not right, like so, so they effectively, in the first place, they quit before I got funded. So I literally had my co founders working for free while I was still drawing a salary. And then the whole thing, it was like basically the pitch I made to them is, look, we're running the clock. When we raise money, we're going to back pay you, so you will be paid. But it's a leap. And they were younger than me and they had family.

That's a big leap.

Yeah. And they're leaving a great job at Google where they were killer engineers working at Google. I mean like so it was, it was, it was a leap that they took. But then, yeah, then you, then you're looking for a space. And the great thing about Google Ventures is they actually had some dedicated space in one of their buildings in, in Mountain View. They called it Startup Lab. So we would work out of there occasionally, but mostly we'd work at my house and we'd have, you know, the four of us, I had this little pool house in my backyard and the four of us would be in the pool house working. And you know, you don't have whiteboards or anything. We had just like sticky pieces of giant 3M post it note things on the wall and writing ideas down and starting to, starting to code stuff. But the funny thing is you're in the early days of a startup and you're together like nonstop. You know, you're, you're in the same room, you're eating breakfast, lunch and dinner together pretty much. And then you work late. Like you work like 8, 9, 10 o' clock at night. And I'd be looking out of the window of my pool house and I'd see my wife and my three kids at the dinner table on the other side of the yard across the backyard. And I was like, man, that hurt. So I'd go back and forth a little bit more. But like in the, like this being my third startup, the first two, like I wouldn't get home until 10 or 11. Like I, I don't think I had dinner with my kids very often other than like the weekends, you know, because it's just kind of like, sorry, it's just like late hours. That's what it does. But, but I digress. But the start of the early days, like you're, you know, you're acquiring equipment and you're setting up servers. It's, it's easier now because there's all these cloud based solutions. Right. You don't need to go buy a bunch of servers and it, it's a lot easier just to get up and running. But it is, you know, then you gotta open bank accounts and you gotta find real estate, then you gotta get healthcare. Like there's just a lot of, there's just a lot of overheady type things you gotta deal with just to get started the details.

Yeah, I would just say that about like your family watching your family having dinner without you across the pool house. I mean like when you're off site, you don't see that, but then when you're on site, you're like, oh, that's actually my family right there.

Yeah.

You know, the people you're founding with your founding team are also experiencing that, although they can't see their family across.

Right.

I just think that's so important to acknowledge the sacrifices that entrepreneurs make. Like, let's just be realistic about that.

Totally, totally. And like, you know, like the days go super fast and you know, you, you stay up late, you get home. And I used to always like come home, hang out with the family as much as I could before they went to sleep. And like, I try not to work then, but once they'd be asleep and by like 10, 10:30, the house would be quiet, then you'd go back to work. Like it's, it's a weird, crazy, you know, unlimited amount of things to do, particularly in the early days. And you kind of like, you know, the years go by and you, you're like, wow, you know that, that they really did a lot without me during those time, during that time. But like I asked them about it, they, they, maybe they're just lying to me, but they say that they think I was a pretty good dad and hung out a lot. So who knows? Like, maybe I'm, maybe I'm making it sound worse than it was.

Well, I mean, how do you feel about it?

You know, I, the one thing that I did do, and this is, I learned this when I was like when I was a lawyer, the, the biggest, best law firm in all of Palo Alto or the Silicon Valley was and probably still is Wilson Sonsini. And so a name you've probably heard of. And the guy who Ran it was Larry Sonsini. Larry Sonsini. He had degraded like his family was from the Bay Area and my wife knew his sons and stuff like that. And I worked with his, you know, Lisa Sobratto, who married Matt Sonsini. Anyway, so, so we kind of knew the Sonsinis. And although he was running the most important law firm in the most important part of like the startup culture, he took time out to go be like his kid's soccer coach. And I remember like when I was a first year lawyer, I, I, I found that out. I'm like, okay, well I'm at least going to do stuff like that. Like whatever sacrifice it takes to do that, I'll do that. So I ended up coaching my daughter's soccer for like five years. I ended up coaching my son's baseball for seven years. And those just took more crazy sacrifices because like the other thing is like they're like your practice time is Tuesday at 3pm like it's made for, you know, like dads who and parents who are, you know, like real estate brokers and have a lot of free time or things like that. Or like. Yeah, I just couldn't believe it. I'm like, how can I get back to Danville by 3pm? I'm working in Mountain View. And so like you'd end up just having to do it. But it was great. Cause I think that gave us a ton of time together. And then you know, you just stay up later and put in the hours at other times. But that helped quite a bit. So I feel pretty good about it.

That's good. I think that's really interesting. Again, I think all professionals have to make these sort of trade offs. And like you already said, I was not the kind of guy that was going to sit around, have a cushy job and be like a middle manager. That wasn't your makeup. And so like in some ways you have to also, I think pick your spouse in a way that is going to respect and honor your nature.

Right, right. And I, yeah. And it's, you don't know. Right. So you meet your spouse, she was 21, I was like 25. And you know, who knows what a 21 year old will think when they're in their 30s with children and you know, and you know, looking for kind of a normal, stable life. But I think it was just kind of the deal like having gone, you know, having gone to undergrad, then go back to business school, then go back to law school. She could tell that I wasn't particularly single tracked or Radically stable to begin with. So I think she kind of knew what she was getting into.

Yeah, I hear it. So let's, let's Fast forward to 2018 because I think, and you tell me if I'm wrong, I think that this is when you started kind of really thinking about AI and putting AI into your business. And that was before anyone could even spell AI right. That was just a jingle in your, in your head, a glimmer in your head. And so not only were you really thinking about AI, but you bought this little company that we talked about, Talk iq. Walk us through how you found Talk iq, why you saw that as such an important acquisition and how that then kind of was able to fit into where you were at Dialpad.

Yeah, so by 2018 we had, we had, we had built this super scalable cloud based platform for communications and we had done. And our whole, our whole thesis was if you build the right platform, you can do anything on it. So, so we used it for our conference calling and our video conferencing and our business phone system and our contact center solution and it did messaging and texting and it was just this one beautiful app. How we used to describe it and the way you won was to have higher quality, more delightful user interface reliability, stability and you know, and great design. But that's it. Right? Like, and I, and I think we were the best at that. But then we, I got a demo and I, Brian Peterson, my co founder, who was the engineer who ran Google Voice at, at Google, Brian told me, hey, there's this company called Talk iq. They do real time AI, whatever that means. And the CEO is a friend of mine from Google, this guy Dan o'. Connell. We used to work together at Doodle at Google in the early days. We're pretty good friends. So I'm like, okay, just out of friendship to you and to your friendship of Dan, we'll meet with them and we go and we meet with them and they had a demo, a sales call and they, they showed their little rudimentary client on the screen of during the sales call. Here are four questions they want the sales rep to ask. And ask the sales rep ask those four questions like hey, so what's your budget? You know, what's your timing? What's why, what's your need? Why are you thinking of making this change and who's making the decisions here? So it's basically the Bant qualification Budget authority need timing. It would check it off in real time, meaning it understood what was being said while it was being said, and I left that meeting, like, legitimately, like, okay, we're going to partner with those guys immediately. That. Because that's a whole different layer versus just availability, design, uptime, you know, feature completeness, things like that. That was a whole new unlock. If you can understand what's being said, when it's being said, and by whom, you can do some really interesting, like, the sky's the limit. So we came out of that medium. And this is, again, the beauty of being at the CEO of a small startup. You're like, okay, that's what we're doing. We're going to go partner with these guys. Let's get our engineers together. And so they were all excited about them because they were this even a smaller startup. And we had our engineers work together, and our engineers are like, look, these guys are great. They built it the right way. We would have built it the same way. We're making all this progress just in a short amount of time as partners. And then we're like, okay, well, if it's working that well and the platforms are that compatible, we should literally buy them. And we had a board meeting, and Mark Andreessen's on our board, and he's like, yeah, you should buy them. I'm like, okay, let's. I'm on it. And so I called. We left that. This is amazing. Left that board meeting in San Francisco. I called Dan, the CEO, right? Texted him, like, hey, where are you? He said he's at some restaurant in San Francisco. I'm like, I'll be right over. I go meet him that night. We have. Have a couple drinks, talk about it. And by the end of the night of that board Meeting, both the CEO of DialPad and the CEO of Takaiq were now in agreement that this is a good idea. We just need to figure out the details. Like, it was amazing speed. And then the acquisition happened, and it was, you know, like, at the time, we were less than 30 million of revenue, and we bought them for 50 million, and their revenue was, like, near zero. And so it was like, it was a really big spend.

That is a big spend.

But it was. It was one of those things of, like, clearly the world's. This just makes too much sense. Just kind of like the whole thing of, like, one beautiful app in the cloud that lets you work from anywhere makes too much sense. Understanding a conversation, real time makes too much sense. And so that gave us the opportunity to then build that into our platform and be able to really start getting ahead of the world on AI and Understanding what happens on business conversations and how to coach and how to let people build playbooks and do all sorts of interesting things. So it was like an epiphany and it was almost like a little bit of a bet the farm epiphany. But end of the day it was, it just made a ton of sense. And you know, obviously super thrilled we did it. And now we have, now we have a full time AI team of over a hundred people, probably, you know, a couple dozen PhDs, and we've been able to, you know, really do things uniquely that other people haven't been able to do just because we had that, all that learning and the skills and the talents around the table to do it.

So that was kind of the seed corn that gave you the head start.

Yeah, absolutely. And by the way, like we were able to put it into the product back in 2018 versus everyone else. You know, like gen AI hits and they're like, oh my God, we're a Gen AI company. Yeah, we, it, it really kind of like separated the wheat from the chaff. And when we talk, it's, it's sometimes challenging. When you talk to analysts, particularly like banking analysts or buy side analysts, they're like, well, everyone says the same thing. I'm like, yeah, everyone says the same thing. It's really easy to say the same thing. But when you look under the hood and look at the platform and look at the actual history and are you just taking recording and sending it off to GPT and calling that your AI, or are you actually doing something more than that? It starts to be pretty differentiated.

That's amazing. Do you feel like because you were an M and a lawyer and because you had the experience of Cisco, you were able to come to conviction more quickly on this acquisition?

Totally. And that was the first acquisition we ever did. So I'd say absolutely. And by the way, that was the biggest, you know, like we've done, we've done four or five other kind of tuck in acquisitions, but that was the big bet. And it was, it's. I don't even know. It was one of those things you're like, oh my God, I can't believe I'm lucky enough to have found this. You know what I mean? Like, yeah, like if I don't jump on this, someone else will figure it out type of a thing. So yeah, I, I was, I was super convicted that that was the right way to go.

And what? Talk a little bit about how. Because something you also said was like, what you learned from Cisco is It's like you bought them and Cisco used to buy their companies where there was nobody else doing it. So talk more about how you were able to get the integration going and how, how smoothly that made, how that went, but also, did you make mistakes that you kind of learned from?

Yeah, so. So first and foremost, we wanted to keep everyone on the team because that's the best way to keep them feeling good about it. Right? So we, we effectively kept everyone. And then we said, look, you are now the AI team. So your, your co founder and CTO is now our chief AI officer, and he still is to this day. And you're that AI team. You're those experts. We had already been working toward partnering and making the two work well together. Now we just took that a little further and built it into the core of what we were doing. But that was. Everyone had a role. It was, it worked really, really well. What could we have done differently? I will say like a, in an effort to try to keep everyone and make everyone happy in this big kumbaya world. You do. Like, they didn't. They had some folks who probably, you know, like, at an early startup, you take a lot of risks on some hires, and they're like, guess what, you're the head of sales. And like, that person may not necessarily be the head of sales at a more mature startup. And so you. We had a little bit of growing pains, you know, like a year or two in of like, okay, now how do we fit these. Slot these people into the bigger thing? But as far as the core of IT in the engineering and the tech and the team, which is really what we bought it for, like, that, that was. That all effectively has stayed together. And I think that's a credit to, you know, to keeping their leadership in place. And by the way, their leadership deserves to be in place. Like, they're, they're really, really good at this. And so, so that made it really easy. I think what we do in all of our acquisitions that makes it really higher likelihood of success is to spend a lot of time in looking how they built stuff. If they built it the right way, that means the engineers probably think the same way. That means they're going to integrate really well together and have kind of the same view of how to get things done. And there have been other ones where we love the company, we love the product, we love the founders, we loved everything. And then you get the tech teams together and it's like they're talking two different languages and you're like, that, that'll never work, you know, just never work.

So you think tech is the key? Like you didn't really mention culture. Everyone talks about culture and how important that is.

I think I, well, I think tech's the key and the tech is kind of a harbinger of culture if, because like we build everything the way Google engineers would build everything and if you build everything the way like someone five years before using you know, like some.net framework or something like that's totally no longer in vogue, that tells you the culture is probably different. And I think like most startups that get funded by venture capitalists, like I just, there's just kind of like a similarity of culture. Probably more homogeneous than you think. But yeah, no, if they're a bunch of jerks or if someone like, like we've, we've had some before where, where we were all in the tech was great, the teams liked each other and then, then like there were like just games being played during the negotiations and during. And I'm like, look, I'm looking for a win win. I'm not, I'm not here to jam you. I'm here to make the best product. And like this is one plus one equals three. And if you're optimizing for like this is the end of the line. I need to get every last penny because like I'm selling my company, it just means we're not aligned. So, so we've, we've walked away from some where stuff like that has happened too. So that's where you find culture. But most of it like, you know, I think I'd say most particularly most Silicon Valley companies, it's pretty open environment. We love to share information with our, with our employees. We want them to be totally bought in on the mission. We want them to all be owners and to have a vested interest in the success of the company and all the acquisitions we've done, their founders felt the same way and did the same with their company. So that always worked pretty well.

Yeah. So that match was there. Craig, you have been going from entrepreneur to operator to entrepreneur to operator. Little bit of student detours into being a student. Right, for like 30 years, 40 years, whatever it is. And, and so I'm curious, what do you think it takes to go from being an entrepreneur, scrappy startup, figuring out healthcare, like working till 10 o' clock at night in the pool house with everybody all together to an operator? Your company has like what, 1200 people now, is that right?

About 1500?

Yeah, 1500 people. Okay, so like now you're operating and you've been doing this for what, 13, 14 years. What do you think it takes to grow from being an scrappy entrepreneur to a mature operator?

I think it's a great question because, because like I struggle with it myself of like I want to spend more time like a scrappy entrepreneur. Like I, I feel like I spend too much time as an operator these days. You know what I mean? Like, like I can, I can run meetings and I can do check ins and I can have one on ones and I can set direction and I can, I can review okrs and I can you know, like do stuff like that. But I don't think that's my greatest value. I think my, my best value is like being more strategic or more in the weeds. Spending more time with the product team, really trying to, you know, spending time with partners. Like we have great partners. Google's a great partner. T mobile's a great partner. SoftBank's a great partner. Spending like putting things like that together, that takes a lot of time. You're on the road a lot. You're constantly evangelizing the thing. You're talking to customers, you're seeing how they're using it. You're bringing that feedback back. I would way rather do that than be really buttoned up on. You know, like we said we'd get our okrs in on the 15th. You know, let's get them in on the 15th. So I struggle with it because I kind of have to do both. And, and as the company matures or has been maturing, I've done a better job of hiring better lieutenants. So my, my E staff, they're better operators than I am and I think they know that. So, so I'm, I'm happy to delegate a lot of the operation stuff that'll free me to go dive into the things that I think are the biggest, you know, biggest, most important things we need to focus on.

Mm. So it sounds like what you've done is you've kind of learned the skills also recognize it's not your highest and best use. And so your key to success is hiring great people around you who love to do that and are good at it.

Right, right. And there's, and the other thing is finding within the organization, even if they're not naturally their title isn't like COO or you know, chief of staff, but there's, there's just those certain people who are really good at cross functional stuff and being really organized and making sure it all happens and no matter where they are in the company giving them more of that to do. And I've, I've been lucky to find folks like that. I'm like, hey, look, I understand you're on the marketing team, but I need you to work on this thing. And they're like, yeah, happy to do it. And so like there's, that's been, that also has been a leverage. I've never hired a chief operating officer. I think about it frequently when I get frustrated that I'm spending too much time doing operations stuff. But I don't think I necessarily need to just because I think the folks around me are really good.

Yep, you have certainly in your companies, you've had experience hiring experienced executives. What has that experience been like, what's said of the good of that and the bad of that?

You know, there's, I saw, I saw a blog post that Mark Anderson wrote on this and he was talking about, you know, hiring individual contributors. If you do really, really well, you'll have like a 70% success rate and hiring executives. If you do really well, it's more like 50%.

That's so optimistic.

It's kind of sad, but true. And I think, I think it's, it's a real challenge. It's a real challenge when for me, every day that I come to work, this company is the largest company I've ever run. Right. Like, it's not like I've taken a company public and you know, tens of billions of valuation and thousands and thousands of employees and then I have all these learnings that I can then apply to this. Like, you know, we were, we were a smaller company when we got bought by Yahoo, we were a smaller company, we got bought by Google and now we're 1500 people. And so it's new to me every day. So along that journey, there's people that you think are the right people may have been the right people for that phase of the journey, but aren't the right people for the next phase of the journey. And recognizing that is hard to do because you really love them and they went through some stuff with you and you fought battles but, but like that next step may not. And by the way, it's kind of like when I couldn't, I didn't see myself long term at a 20,000 person Google. You know, there's a lot of people who are like series A, series B, series C type, you know, marketing and sales folks, which is a different game than, you know, being a high growth or a later stage growth company. And so it's A real challenge. And having not gone through that before, you're learning it on the fly. And, and so, so it's, it's always a challenge when you bring in an executive from outside because they'll have their own biases, they'll have their own opinions, they'll have their own experiences. Secondly, it's really hard to evaluate how, because, like, everyone will still come to you with this great resume of like, I was, I was the C Blanco at this company and we took it from 10 million of revenue to a billion. And like I was there every step of the way and it was all, you know, I was responsible for all of it. And a lot of people like naturally human nature, they're gonna, they're gonna make their story sound as good as possible. And, and of course you were the person responsible for that incredible growth. But a lot of times you realize that growth came because it was an incredible product market fit. There's a product, incredible partnership someone else did, or incredible something else. So trying to figure out just how responsible you actually were during that stuff and then how will you fit in and work with the rest of the company? So the one of the worries of ever bringing in like a senior person is will they be super disruptive to the rest of the company and to the rest of your team that you really like? And so we've been fortunate. Like, I just hired our chief marketing officer a year ago, but her name's Jen Grant. I worked with her at Google. She then went to Box and ran marketing, then she went to Elastic, then she went to Looker. And I've been trying to hire her for a decade. And we put her on the board of directors six years ago. So. So like she was a known entity like this. She knew everything about us, we knew everything about her. So it was a, it was almost like hiring from within. Similarly, we hired a chief customer officer. The guy who ran was chief customer officer at Genesis and spent 22 years at Genesis, which is a big competitor of ours in the contact center space. We didn't know him from Adam. He was out of Boston, spent 22 years at this big company that we kind of want to take down and think is a little slow moving and stuff like that. And. But he seemed great. I really liked him. Met him in person a bunch of times and what we decided. And he was awesome about the suit. He's like, he wasn't sure he wanted to come work for us, so we're like, how about this? Why don't you just work? Let's Go six months. You be, you be, you know, consulting as basically doing the job, but just as a consultant. You can walk away anytime, we can walk away anytime. And after, you know, four months of that, it's like everyone loved this guy. He's obviously a great culture fit, obviously has all this experience and knowledge and is going to be a success here. But those are two pretty extreme examples. Usually it's much more of a, all right, this guy looks good, or you hire a headhunter and you have three or four really good candidates and you try to do all your reference checks and you try to try to understand. But coming back to Mark Anderson's thing, it is a little bit of a coin toss and when you get it wrong, it sucks because they'll come in, they'll potentially change all your methodologies, they'll get rid of your people, they'll bring in their people. And if they don't work out, you've just set yourself back a year, 18 months. Then you gotta go find another person to redo that whole thing. Then you start over again. It's tough. So I would say for just any advice of like being able to keep continuity as much as possible and coach rather than replace is so much better than the rip and replace model because again, you're likely going to get it wrong half the time and when you do, it's super disruptive.

I mean, that's such good advice and thank you for sharing that experience with us. Craig. I would just also add that it sounds to me in this whole conversation what I'm clear about is that you're really into long term relationships, that you want to build loyal, trust based long term relationships and that, you know, they pay off in their own say kind of, but like they literally pay off where 20 years later you could finally hire this person.

Right, right.

Well, I look at, some of you already know.

I look at my like my chief product officer and I, Vincent Becket, we've worked together since 2001. So that's 23 years, 24 years now. And he was my co founder at Grand Central. Then he left Google Voice to join me here. My CTO and co founder, Brian Peterson, we've worked together since 2007. So what's that? That's 18 years. Like it's, it's, it's good. My general counsel was our product counsel at Google. So I've known him since 2007. Jen, I've known since Google. It's just, it just makes life. Our head of HR has been working here for eight years someone I even knew before that. So it just makes it so much easier to not. You know, it's like you don't have to worry about their motivation, you don't need to worry about their values, you don't need to worry about how they think of the world and what Dialpad's place in the world is. You just. That you. That's just, that's. You take that for granted and it just makes life so much easier. And, you know, you can lean on them and you can argue and you can get. You get in disagreements and no one's going to feel personally harmed by it. Like, it's just. It just makes it so much better.

Yeah, totally. Craig, you are such a positive and energetic person. I have to say that when I met you in Vancouver, I felt that way, and I feel that way now. I mean, this startup journey is like a grind. And I'm just curious, throughout all this, have you ever had your own moment of truth or this feeling of, like, this really sucks?

I think every, every startup person, particularly like the founder, CEO, if you have very lonely moments where it's like, man, like you're like the decision, every decision's on you. Like, you know, you may have a bad quarter and you might get pissed about something not going right, but it doesn't matter. Like, you're. It's on you, you know, and then you gotta make decisions and figure things out. And it's like. And it, and it's, it gets me much more of a hunch of like, hey, maybe we're moving too fast right now. You know, like, things are. Things feel like they're getting a little loose. Maybe we should slow down to speed up later and maybe we should, you know, or, or like, look, this whole, like in our space, the whole agentech AI, so we had, we have this whole, you know, like, foundation of AI and then generative AI and then all this stuff, but now we're like, hey, agentic AI man. That, that just created a. Jumped on the scene recently. And so we overnight, and this was about three months ago, I said, we're starting inside of Dalpad, we're starting our own startup. And this guy, we're putting this guy in charge of it and he's picking his team and his mission is to go build our echetic solution. And you are not encumbered by the rest of Dialpad. Go do whatever you want and execute as fast as possible. And thank God we did that because now we're like, we're like rolling out features and we have Voice bots and we have, you know, we have agentic via chat and we can actually do things and really have this incredible agentic solution. Like a whole nother startup that now works and lives inside a dial pad. But like that was just lying in bed at night of like, man, the world's changing fast. I gotta come out like, we've got to do something bold. And I do think there's, there's, there's plenty of lonely nights, man, there's plenty of lonely nights and there's plenty of like high stakes days. Like there was a day, man, there was a day when we were gonna, we were gonna close on a financing and we were gonna close on a partnership with T Mobile. And then we were going to, then T Mobile maybe was going to join the financing and we simultaneously we were acquiring a company. And all four of those things came to a point on it on the same day. And the problem was like, it was great. Everything was coalescing to this, like this, you know, this point of singularity. But had one of them not happened, the whole, all four of them wouldn't have happened. You know, they all became dependent upon each other and that was like the most high stake stress night and day of my life. And it all came down to, you know, this T Mobile partnership. Are they in for the partnership and are they in for the investment? And if they were in for the investment, then the whole round would close. And if the whole round closes, then we're going to be able to buy this company. But it literally all had to happen that way. And like that when I was talking to this great guy at T Mobile, Jason Young, he's like, okay, I'm going in, I'll let you know. And then you're just sitting there for like 90 minutes, then you get a phone call and it's Jason. And you see it on your phone, you're like, okay, I'm going to answer this and my life's going to change one way or the other depending on what this guy says. And luckily, and fortunately they came back and said, yeah, they approved the whole thing, we're partners, we're going to invest, blah, blah, blah. And then everything just, everything else happened, right, but had that not happened, man, there was, that was gonna be, that's gonna be a gut punch. And there was, there were gonna be like a lot of bad consequences coming from that as well. So, so there's a bunch of terrible highs and lows, but at the end of the day, like I'd way rather be in control of it myself, you know what I mean? Like, I, I think I can figure anything out and if there's like, I just need to know what I'm up against, you know what I mean? Like, hey, if, when you've done these things for this long, I've been through the financial crisis, I've been through the dot com crash, I've been through Covid. I've been through the last couple years of IPO markets being closed and the economy being weak and all these. And now we have AI coming and no one knows what the future is going to hold. Those are all unsettling and difficult times, but I'd way rather be the one navigating them than sitting back and hoping someone else is doing it right. Like that would feel. That would feel like a little helpless of like, God dang, I hope, I hope we get this right. So, yeah, I'm optimistic. Ever the optimist. And by the way, again, you know, life should be fun. You should enjoy what you do. You should work with people you like being around and you should work on stuff that interests you so you can't stop thinking about it.

I love it. So great. Craig, just a couple more questions. What do you wish you had known earlier on your journey?

Good question. I mean, just more like tactically tactical stuff. Like when you asked the question about being a good operator, like, it was a long time into my journey before I even like really ever thought about results. You know, like I was always just focused on the mission of like, let's go build this, let's go build that. Like, this will be great, let's do this, let's do that. And then results just kind of happened. I never like, and I remember when we hired the CMO long time ago, he's like, yeah, you know, like if we miss our number, I'm like, what? Like I've never, I've never once, like I never up to that point, I'd never stressed over it. I think about it quite a bit more now, obviously, as the company is much more mature. But, but I think that, I don't know, I think that naivete and not knowing makes it a lot easier to do stuff. And, and you know, like you read things like, you know, Brian Chesky at Airbnb or Jack Dorsey at Square, like they had no experience in the hospitality industry or in the payments industry. And I remember reading something that Dorsey said that, you know, had I known how screwed up this industry was, I would have never gotten into it. You know, like, you almost need that outsider naivete to come in and try things differently. And so I don't. There's not like some secret. I wish I knew. I kind of like, I kind of like the discovery part of the journey too.

That's so great. I had Jim McKelvey, who's Jack Dorsey's co founder, on my podcast and it's the same thing. It's like, yeah, we had no idea. In fact, he said, you know, I looked into payments and I stopped counting after I realized we were about to violate like 17 different regulations. It's just like, okay, here we go.

Well, and that's.

But not knowing is a blessing.

Well, yeah, because the people who knew that stayed out of it. They're like, this is impossible.

Exactly, exactly. And Craig, what advice do you have for other founders as they embark on their journey to grow into leaders?

Well, there's probably never been a better time to be a founder, you know what I mean? Like just there, there's so much opportunity and like no one's really, no one truly understands what AI is going to do and how it does it. And you know, I remember I was at, I was at some dinner at some investment banking conference in San Francisco and they were talking about, you know, there's going to be a hundred million dollar revenue companies with like eight people on the team. You know what I mean? Like there's, there's your marketing guy and he can do everything because he has all the AI capabilities to understand demand gen, build websites, you know, create content, put social and PR and all this stuff. And there's, you know, similarly way more efficient engineering and way more efficient everything else. So it's super unique times. And I think the best time to be an entrepreneur is when there's like total disruption. Right? Like, cause like it's a, it's a jump ball. Like this is great. No one has a 10 year head start on you on how to be a great CEO or founder in an AI centric world, at most someone has a year on you, you know what I mean? And that year, things have changed so much and so quickly that that doesn't even give you much of an advantage other than just kind of a feel. So, so I'd say go do it. It doesn't take a ton of money. All these things are accessible and now like it's, it's kind of the world of ideas and execution and it's just going to be a really like, I think about it from kind of like, because I have kids graduating college or graduated college, I'm like, you know, What's. What's their future hold? You know, like, if companies don't need as many people. Yeah. Isn't that going to be bad for humanity? And yes and no, because I think there'll be twice as many. Like, you may need half as many employees, but there'll be twice as many companies because there's just so many opportunities to create something special.

And.

And I think we'll get. I don't know, like, it'll get more specialized. Like, I will be the single best, you know, AI bot for this particular industry and this particular role, and then everyone will chase all these millions of different slivers and get really good at it. Then ultimately companies will be like, look, I can't manage all these slivers. I want them all into one. And then there'll be this consolidation and then big companies will emerge. But it's going to be a wild ride and it's going to be a fun time to see how it shakes out. So if you're thinking about doing it, now's the time to do it.

Love it. Now's the time. Craig, thank you so much. What a great conversation. I really appreciate your time.

Yeah, appreciate you. That was awesome.

Really awesome. 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.