How to Bootstrap a Company. OLark’s Start-up Story with Ben Congleton Tells All | Ep. 32: Business Podcast

How to Bootstrap a Company. OLark’s Start-up Story with Ben Congleton Tells All
How to Bootstrap a Company. OLark’s Start-up Story with Ben Congleton Tells All


Olark’s Ben Congleton tells the story of how he and his co-founders decided not to raise money and how they bootstrapped the company to success. We talk about how founders get caught up thinking they have to raise money, but really you don’t have to and in fact, not raising money might be your competitive advantage.

Ben shares things in this conversation he’s never told, you don’t want to miss this episode.

Remember, you’re just one business plan away from building the business of your dreams.

A full transcript of the episode is below

Brandon: (00:00)
Hi everyone and welcome to another episode of build a business. I am your host, Brandon C. White and today we’ve got a really special guest and friend of mine, Ben Congleton, the co founder and CEO of oligarch and if you’ve ever visited a website and seen a little icon in the right hand side that pops up that allows you to chat with either customer service or the owners of that website. Oh Lark was the first company to actually make that happen and they are celebrating their 10th anniversary this year, which is a huge accomplishment for any business and especially a sassy software as a service business that was bootstrapped. Ben and his co-founders went through a very famous accelerator here in Silicon Valley called Y Combinator and coming out of there traditionally a lot of the companies raise tons of money and you’ve probably read about that in either a tech crunch or one of the other tech publications if you follow that sort of news. 

Brandon: (01:06)
The difference is that Ben and his co-founder set out to raise some money and after a short period decided that they weren’t going to do it and have effectively bootstrapped their company. It’s a great story if you’re starting out in any sort of company, but even especially a software as a service business. Sometimes the media out there says, you’ve got to raise money, you’ve got to raise money, and here’s a great story of a company that effectively has raised no money. I’m going to let Ben tell you about that and gotten to over 30 employees, 10 years in business. Great accomplishment. Ben is a great guy. He and I met at a conference years ago, have stayed in touch and followed one another story and really even collaborated together on some stuff recently we joined a little mastermind group together every other Friday that meets in Palo Alto and had some fun with that. So you’re going to really enjoy this episode. You’re going to love this story because it is a story of how companies, many of them really find their way and how people come in and out of the story and ultimately what happens. So you’re going to love it. Without any further ado, let’s get to it.

Brandon: (02:31)
hi. Well Hey everybody. Welcome to another, another episode of build a business straight talk for entrepreneurs. We’re here with an, I’m going to get his last name wrong even though I’ve known him for like five years and [inaudible] is that right, Ben? I’ll take it. Alright, from a is the co founder and current CEO of OLark and if you don’t know Olark, you need to know, Olark, Olark was the first company to put that 

Brandon: (03:00)
little icon in the right hand side of a website so that you can talk to your customers and we’re going to talk about that. But what we’re really going to talk about, because Ben has a super interesting story. We’ve known each other, I don’t know, four or five years. We met at a cool, where did we meet? We met at a conference in Vegas in Vegas. Hold on by Paul, right? Yeah. Startup accelerator. Yeah. It was such a cool eclectic group of people. So everyone there was super interesting and that was, yeah, it was just a, it was a small small group. Small conference. That’s great. And for listeners, Ben and I started talking and Ben lives over in East Palo Alto. I live in Half Moon Bay and day Ben. Thanks. I live on the other end of the earth as well as everyone else, but we’re really not that far from one another. 

Brandon: (03:49)
And the crazy part is we just call it up in person. Well we’ve been meaning to do for four years but um, we see each other at the conference. But Ben, thank you so much. I know it’s, we’re doing it on Friday. This is just the way it works out. Thank you so much. Tell us your story and can you take us two when all the way back to where OLark started from. Yeah, and we were chatting about this beforehand so we’re going to go way, way back, way back, set the scene. It’s like pre 2001 right? We’re, we’re going way back there. So pre 2001 I started a web hosting company in high school, so 1998 and at this time there is, there was actually a couple of live chat providers but they’re all very enterprise focused. But there was one live chat provider called a human click. 

Ben: (04:46)
This was it in Israeli company, old school, that’s old school. And so we were using human click. It was super valuable for our business as a small business as like, you know, high schoolers with enough Oh number. We use chats, connects with our customers. And so we grew that business. My senior year we’re doing about $170,000 a year in revenue, which was wow. Pretty awesome. Like it was super fun. [inaudible] uh, but during that time human click ended up getting bought by live person and becoming a tech stack for live person. And so we had switched to other products that were more affordable. Cause when life person bought human click, they ramped up the pricing a ton and then focused on enterprise, which made it made a ton of sense. But for a small business they kind of screwed up. It’s over. So like imagine you have that idea in the back of your mind, right? You fast forward, uh, you know, you graduated from college, you finished high school, you graduated college, uh, during this time he still kept running that web hosting company kind of on the side. And he had some buddies who, your co founder, that one person meet with you and you’re kind of thinking about what’s next. And so I’ve gone off, I worked on a PhD at the university of Michigan. Uh, my two cofounders, that web hosting company, 

Ben: (05:58)
one of them had gone to LA to start a band. The other was sort of working in, uh, Southwestern Virginia or folk just doing like full time sort of consulting from deals that I would go fine. And so you’re making some extra money here, right. Um, I mean honestly we, we kind of were making, it was not, it was not making a lot of money, not a lucrative, this is like completely not lucrative. It was like we peaked senior year of high school in revenue and then we all went to undergrad and we had fun in college and use the help pay for our degrees and stuff like that. We weren’t bank money. I think we decided to like have fun in college, have like, like passive income is a fricking lie. But we had kind of like the climbing income. I like that cause I just did it sometimes telling her someone the other night I was like, I’m so sick and tired of all this online BS about passive income. 

Ben: (06:50)
I mean passive income just means to me that you’re not a service business. It means that it works when you’re not there, but it doesn’t mean you don’t work. Yeah. I mean there may be some magic out there somewhere but, but like this was not, this is not us. So anyway, so we had two guys basically whose livelihood was based on the consulting jobs. I could find. We had some income still coming in from the web hosting company. I was working on a PhD and we’re like, we started getting jobs from startups and so people were hiring us to go build stuff for them. And in my mind, man, these people are like, these are like the ideas. They’re still paying us a bunch of money. Why don’t we go do this ourselves? And they were like, try to like take it, have us like get past an options or equity or something that we’re just like, no, just give us cash. 

Ben: (07:37)
You guys can make all the money. But like we just see the fair bills. So it would do, because we would build them out. Like let’s say we’re charging, we were stupid charging way too little money. Like let’s say we charged $75 an hour, we would pay ourselves $25 an hour. This is how dumb we were. So we pair us up $5 an hour and then four, two thirds of our time we’d spend working on cool projects like new ideas and stuff like that. So bill a client, I spend the rest of the time working on new ideas. And so, Oh, the first idea that we built with this team, like me, Kevin and Roland was somebody called [inaudible], which kind of tells you how much we suck at marketing, but it was a modular synthesis for garage band. It was fairly popular with, uh, like German techno artists. 

Ben: (08:25)
Hmm. But it was, it was because roll and Kevin were both into electronic music and so this sort of fat with fat fit with their interests. And I was like, Hey guys, like, you know, you know the market better than I do. Like if this thing can work, that’s great. Sure. That didn’t work very well. But it made, you know, made thousands of dollars but not tens of thousands or hundreds of thousands of dollars. And this was pre iPhone, how we released it as an iPhone app. Like who knows what the world would have been. Okay. But it was, it was pretty cool. [inaudible] after that kind of flop, we went back to the drawing board and looked at a couple other products because rolling has, uh, was actually an assigned ban out in LA. Yeah. This idea, Oh, it’s so hard to keep track of all our gigs. 

Ben: (09:07)
We have to update our MySpace, we have to update whatever other websites existed back in like 2007, 2006 to post your band gigs on maybe Facebook, probably geo cities set up that your tripod page had a log into your BVS like up anyway, like it’s always a pain. So I was like, Oh, let’s build this tool for bands so that you can post your gigs and people know, can follow you and stuff like that. And then we’re like, Oh, sudden insight bands have no money. They’re not going to build past. So we, we kind of specked it out and then decided not to build it. So then at this point we were sort of into this idea of thinking about products incubating products, trying out new ideas. And we were like, Oh, well what about, what about live chat? Like what’s happening with live chat in the last like 10 years. 

Ben: (09:57)
This is like 2000 we’ll call it 2007 something like that. Right? So like, I don’t know, eight years ago we’d first use live chat now we looked around and it was the same freaking guys in eight years. Like nothing had changed in the market. Like everyone was just copying live person and trying to build enterprise solutions and we’re like this is, this is ridiculous, right? Like there’s all these small businesses sewing online, there’s this growing like a movement from offline online commerce and there is no good communication technique for SMBs to talk to their customers on their website. Like people are spending all this money in ad words and there was no way to talk to them. And we know that this is valuable cause we used it back when we were getting started and now we were a lot more sophisticated. We know how to program and do a scale stuff. 

Ben: (10:43)
It’s more like, Oh, okay, well what if we just built the thing that we needed 10 years ago, three years ago, once we set out to build a chapter, just basically worked for us. It was super freaking easy to add to the website. We kept thinking like, what if you could drop one line of code on and it would just work. And the second part was, what if you didn’t have to change any of your habits? Were like, okay, like back in the day we all use pigeon or ADM. We were in there as I am clients all the time. What if like chatting with customers in your website was that easy? And so we actually built the original version and we hacked it in. So you could, uh, you could chat from, aim into the people on your website. You could chat from. I think we, we built MSN and you can do it via like I chat and Jabber. 

Ben: (11:27)
And so we built the thing basically that we would have loved eight years ago and it was very simple, pretty ugly. And the and anything has at that time we had to invent like all the tech because at that time was pretty innovative. Like there was no like X HTTP requests. There is no like, you know, you have to make it like [inaudible] compatible. Like it was, it was a fairly complicated technical challenge just to make the basic plumbing of this thing work. And then on the back end dealing cloud all these third party yet uh, it’s meshing protocol is like we were able to like hack stuff together. We were like writing C code. I mean it was, it was cool technical challenge to kind of get it running and then we sort of took that and again, like I was doing my PhD primary income was coming from consulting. 

Ben: (12:20)
We’re all in Silicon doing the band thing. Kevin was spending most of his time doing consulting work. So this was kind of like weird like fitting it in two thirds time. And I would, they actually dedicate every Sunday to this thing. Like every Sunday I would start working on it. It originally was called Abla, which means to talk in Spanish. We bought a cause I really liked short domain names. Yeah. And so that domain name was bought I think in 2007. So in 2007, we had a name, we hired a friend of mine from high school to do like all the initial design work. So you built like a brand and a nice website for us. And, and then we kinda started going around to forums and looking for people that were looking for widgets to put on their website to chat with other visitors. 

Ben: (13:09)
And that meant we were talking, there was a lot of librarians looking for stuff like this. There was uh, occasionally there is a, at this time there was a company called Meebo that at Agrium it was kind of like putting pigeon or ADM and putting it in the browser. Like that was our key value proposition as they had took that and put it into a browser. And they had this thing called Meebo me, which is like this little chat widget. And we were like, well their challenge is horrible. What if we can just like find all the people complaining about all limitations of their chat widget and just send them links to our stuff. Yes. Boards. Is this, uh, they, they had a no, they had a forum so, well yeah. I mean this isn’t like dial up. Yes. But you’re, you’re in there chatting, you’ve just read the reviews and then just, yeah, basically, well they, we’d make a lot of public posts but we would just like scour the internet like for these forums because this is like what probably pre Twitter and stuff like that too. 

Ben: (14:07)
So yeah, we scoured the internet for people who are having this complaint and we would be helpful and non spammy and be like, Hey we’re building this free thing to solve the problem that you’re having. Check it out. Like we built this for ourselves. What do you think of it? And so that’s how we got our initial customers are mostly libraries and a kind of a weird swash of people that have been using me by me. And so the interesting thing because of that, and this is interesting cause I don’t think I’ve actually told this story before. So you’re getting like some really like some fresh, really fresh express stuff. And so, all right, so this is 2000 so 2007 we had the product that launches free and 2008 so we had been at it for about, I don’t know, not quite a year, summer of 2008 we kind of worked more of the bugs out and it kind of work. 

Ben: (15:00)
Then people were using it and we had more users using it. And at this point I think Meebo had kind of caught onto us. We get a phone call from Meebo or an even if I was email or an email from me like Hey guys, we want to buy you. Okay. And or we’re like come on out to California and meet the team. Or like, okay well that sounds kind of cool. So we all flew out there. I think at that time Roland was living in Virginia. Kevin’s living in another part of Virginia and I was at Michigan working on my PhD, so we all flew out there like we should have realized we weren’t going to make any money when, uh, we got picked up by the super shuttle, the airport, but to the crappy hotel that they put us up in, I went down to Castro street in mountain view where their office was basically above one of the bars there. 

Ben: (15:49)
So like one of the perks of their office was there was a back stairwell that like one and two bar and you know, we thought that was kind of cool, but I went upstairs and it just kind of felt like a job interview or like this is kind of weird. Like we’re not really talking about the business. It seems like a kind of like a personal interview situation. And then the end of that, they’re like, Hey, uh, we want to do like an asset acquisition. We’ll give you like tens of thousands of dollars and we want to hire Kevin. And I was like, well, not going to sell the business for tens of thousands of dollars. But if you want to try to hire Kevin, go for it. And like, and so this was probably like, I don’t know, August, 2008 and so maybe July and then so basically Kevin initially said no to them. 

Ben: (16:37)
Right. It’s a very loyal friend and like you want to do this. And I think, I think I had, I had told Seth like basically no, but you can try to hire Kevin, you know, whatever. He’s my friend. But if he wants to leave, like, you know, I give you my blessing to go try to hire him because I’m working on my PhD. Like I don’t know where this thing’s going. It’s still side projects or projects. Yeah. Yeah. And so Kevin ended up and higher, uh, they were like flew out to Virginia. They like baked the cookies. They worked hard on, Kevin was a genius and is still in the penis. And so he, he ended up getting hired in and going and working Debo and that left me enrolling then. So I am like kind of cross business technical rolling’s a great designer. Really good, like [inaudible] really good clean creatively like growing product manager skills and stuff like that. 

Ben: (17:25)
So it was just us and I was like, man, I don’t want to be CTO. Like I don’t want to like run tech, I want to, I’m more interested in kind of the whole picture. And so we started this sort of search for, okay, well I think, I think what ended up happening was it me and Roland sat down, we’re like, man, how do we make this thing real? Either we need to kind of kill this off and move on with our lives and just focused on like I gotta focus on my rolling and talked about going to architecture design school or we got to like try to make this thing real. So it’s like, do we kill it or do we make it real? And I think role in kind of push and said like, Hey, maybe we should apply to Y Combinator. This wasn’t me rolling. 

Ben: (18:01)
And it’s like maybe we should play. And I was like, all right, let’s, let’s do it. So like Roland pushed us and like we fill up the app and applied the Y Combinator. Yeah, it’s you rolling in who at this point? Uh, it was me and Roland and it’s interesting I think on the YC application. That’s true. I think actually there’s one other person on the YC application. It was my friend George. It was like college buddy that I’ve added love this guy. Really good friends. I think we convinced them to be part of the the application and he was kind of excited about it. And you are studying, what is your PhD or studying? I was studying, uh, I was in the school of information so I had a master’s in computer science at uh, undergrad in business and computer science and information is kind of interdisciplinary degree. 

Ben: (18:51)
So it’s super freaking fun. Like I was, I was like taking anthropology courses. I was taking econ, I was taking design courses. It was basically like I understand people using all different methods, like anything from quantitative to qualitative to like the way economists approach rational thinking it anthropologists, opposed approach. I like just studying the way people make decisions. Awesome. Super fascinating. Even took a class in the business school and like conversation analysis. It was like the most fun ever. It was super fun. So you wrote in George this guy. Yeah, I can have a whole interview on George. George is amazing. But yeah, so we Combinator. Yeah. And but in parallel to that process, I was kind of like, all right, we need to find another tech co-founder. Like, like we need a technical cofounder for this and I can speak tech, I can talk to engineers. 

Ben: (19:48)
Like I love doing this stuff, but it’s not my passion. It’s not like this thing that like, I’m not like driven to like simplify and create good software engineering and like all the processes around that, like that those are weaknesses for me. And I want to find someone that loves doing that stuff. Uh, even though I can do it, I want somebody loves it. And so I started going to a lot of meetups and NRA where I was living in Arbor, Michigan at time, once, a lot of meetups trying to just meet people. One point I require, I, I convinced this guy, you got his name but either competing product to Abla and it was couple of library help. It was all written in Erling. He was like some uh, I want to say like kind of a technical guy at some astronomy lab and like North Carolina or something like that. 

Ben: (20:33)
And I was like, you know, clearly you love the technology side. I like the business side more. Do you want to work together? And so like we kind of do, did a little experiment and like he uh, helped me out like writing some code and her laying like, I was like, Oh, why don’t you try to reimplement the service we have in her leg and see how that feels and let’s try to work together and see if yeah, see if there’s a, if that relationship works at all. And like we went back and forth for a bit and he’s like, you know what, like I can’t do a startup right now. I’ve got too much going on in my life. It’s not a good fit. But like I built a connection. I talked to this guy, convinced him to give it a shot, you know, in the end it didn’t really work out for him. 

Ben: (21:06)
Not sure where he is today. Probably super happy. Right. It just wasn’t like the route where I rode for him and then like I, I met, Oh this guy Brandon through these meetups and a brand is pretty sharp and I dunno, it’s like there’s so many details of the story but like what was this like magically I met Brandon through meetup. There is like a friend had actually introduced me to Brandon because he had just been let go from his job and then uh, I was like, Hey, like I’m working on this thing. It’s going up. Awesome. Yeah, I see. Anything going on? Do you want to be my, you want to be my cofounder and like Brandon came over. So at this point it was me rolling. I think George is still involved this point and Brandon and I would say George probably wasn’t doing much. 

Ben: (21:50)
I was doing a lot role as in a lot brand was doing that and like we’re together, we’d kind of get together on Sundays and kind of jam on this. Cause Brandon that we’re local, we go like sit on his, so then it’s the couch like hack on stuff for it for a bit on Sundays, maybe a little bit during the week and stuff. And fast forward, it’s not like in December, 2008 Y Combinator said that we could interview with them, were accepted in the interview and, but because the market is so bad and we’re not sure if you’re gonna get funded, if you want to, you can defer. And we were like, all right, I’m in the middle of PhD program. Lost some flux. I don’t even know if he was very founding team. Let’s forget the first. And then in the meantime, let’s apply Techstars. 

Ben: (22:35)
Let’s apply to other accelerators. Let’s just like clean up our lives too and go focus on this thing. So like we got the, we got the interview, we said, all right, well put it off, we’ll interview for the next batch. And so from December two I would say June of that year. Yeah, so December of 2008 to June of, I don’t remember when the interview was. We’ll call it like may or something like that. March, I don’t remember. April may. It was probably in April. So, so in that interim time we applied to Techstars, we met people at Techstars, we ended up getting into Techstars for both Boulder and Boston. We are like giving talks like entrepreneurial events on like the stuff we were doing basically just living like we’re going to do it for real. Like we’re just like F Y Combinator, ethics accelerators. 

Ben: (23:20)
We’re going to get in if we can. Like if we get in, we get in if we don’t like they’re missing out. Right. You’re building the company. And I had done this with my web hosting company. The weapon was in company initial funding. Initial outside investment was a hundred dollars from my uncle who will help us buy the domain name. We had friends that hooked us up with our initial like server hosting. We did a bunch of consulting work to like buyer for servers. Like, w we had done this before, like just, I was more familiar bootstrapping than any other format of building business. So like that’s all I know. All I knew, so, okay. So we were like, we’re going to do this for real. It’s South. I think at some point during this process, prior to March I’ve met this guy Matt and this other guy Andrew at kind of like a startup drinks event, Nan and Arbor, like just a networking event. 

Ben: (24:14)
There was a lot of like kind of watch printers at events and stuff like that in Ann Arbor. But so me being there and having an actual product just made like all the best people want to talk to me. Like the people who want to start us, we didn’t have an idea or stuff like that would come talk to me. And so I sort of had my pick of people to work with me back then because I was like, Oh, the guy actually doing it. I mean, he’s a PhD student, you know, like it was kind of cool. And, and what ended up happening was, uh, Brandon, I think it was about to get married and so he couldn’t like leave Michigan and he had just bought a house or something. Like he had a lot of like other constraints going in his life. And George was unwilling to leave, uh, Austin, Texas. 

Ben: (24:57)
Like he just, he also bought a condo, he’d worked at IBM and let a couple of companies down there and he was underwater and his mortgage and he loved Austin. And so like we had these like the two guys, right? We’re just in a situation where like financially it didn’t make a ton of sense for them and like just their stage in life then make a ton of sense for them. And so one of the happening is I think met Madison event and I was like, Matt, you can be a cofounder. Like if you go talk to George and like he’s cool with and he decides to leave and you replace it basically. And so he, he went down to South by Southwest. He was already going to and he met George and Austin talk to her George and George’s side, like, Hey, like Matt’s much better person. So like, yeah, some really good people. Just like good humans involved. Yeah. I only really work with goodies. 

Ben: (25:50)
I mean, you know, I’ve worked with people who aren’t good humans, but like it was like my direct network of like really close friends that I was doing this stuff with. They’re all just fantastic human beings. Right. And like I think, and I think that’s kind of what it takes. Like, you know, the people that you’re gonna like that you would even consider to be at like cofounder level. Like these are people that like, you know, they have your back, you know, that they’re thinking that they’re thinking of the team. They’re not thinking of themselves and like, they’re just like good people. So like, you know, like George, my friend from Austin, like just amazing good friend of mine and like, you know, like we’re still very close friends and you know, like yeah, it kinda sucked. He couldn’t leave Austin and go do this thing with me. 

Ben: (26:31)
But like anyone that you would elevates that level of like, Hey, we’re going to like work together for like 10 years. Like you better be like right, better really have a bond there because you’re going to go through tons of shit and sometimes you can get lucky, right. You can meet someone at a bar. Like I met Matt at a bar. Hmm. And like weird chatting and he’d just, I think because he had been friends with Brandon, like that existing network, make nice fuel, be more reputable in that situation. And Matt turned out to be an amazing human being. 

Brandon: (27:04)
And was there any that question cause a lot of listeners, was there any issue with equity at this point? I mean, was it all up in the air? Like George says, Matt’s a better person. Did you give George like a piece of the pie or George or you know, it was all business like, Hey, you can’t do it. We’re really sorry. We absolutely love you George. But 

Ben: (27:22)
well that time no one was full time and we’re all just trying to like, we’re all doing this part time aside side. And we weren’t even sure it was going to be real. Like real equity agreements that have been put in place at that time was we had like we had not back in those days man. Like we were just like inventing the shit. Just like so much resources now I think we just kind of invented kind of like best thing over time we’re just saying how should we divide this? Okay well we’ll like set a cap table, we’ll just pay ourselves and shares like all informally. Like we didn’t even, we hadn’t incorporated or anything like that. Like we were just kinda like we had a gentleman’s agreement cause we’re all like friends. No one was, I think everyone was just like reasonable human beings. And so for Kevin, cause he had like written so much of the code and really been in it, I think that the situation is a little bit different. And then the guide David who had actually done all the like website design stuff, I think we ended up just paying them for that because like he ended up why not being at a place to be a cofounder either. 

Brandon: (28:26)
Got ya. 

Ben: (28:27)
So like I think all in a neat thing is all this was happening part time on the side, which I think also made it a little bit easier too. Cause no one had like made giant sacrifices kind of doing it on the side, help out friends because they’re kind of excited about doing the startup and then the idea of like leaping and not getting paid any money. I think like 

Brandon: (28:48)
that changes things. 

Ben: (28:49)
Yeah. So, and I would say that in all the cases of all the people you met, for the most part, these are people that we had had like existing relationships with or like for friends that people deleted. And I had that network. The only exception of that rule would be like Andrew who kind of joined us as a, as a third cofounder when we are a fourth co-founder when we went until I CA I see. Because back then they would give you an extra five K if you 5k. Profounder right. Yeah. You know, Andrew is a smart guy, but I think like if w it was clear, like he was a junior, uh, like he, I haven’t been a, 

Brandon: (29:29)
yeah. Like he’s still needed to do his senior year of college. Oh, okay. So, but, but the four of you decided to go do Y Combinator at this point? 

Ben: (29:36)
Not yet, but more or less. Yeah. So we had to get into YC first, but I think shortly after, 

Ben: (29:42)
like George, uh, Matt subbing for George Andrew, yeah. Just kind of spent a lot of time working on me to let me kind of like let him join. And I like made him do a bunch of work, like go do a bunch of business case stuff, things like that. And he kinda like showed me that he worked hard and was willing to be like put in the time. And, and you know, I, I like smart young, ambitious people. Like I love working with ambitious people and Andrew’s definitely super hard working. And so like I, I admired that in him. And so I was like, yeah, sure man. Lil, we’ll make you a founder and you can come out and do it with us. So I think like I kind of sometimes a little trite about like, Oh yeah, we add away Andrew to be a co founder because, cause we asked for an extra five K but like in actuality like Andrew would prove themselves during that. 

Ben: (30:24)
There’s couple of months before a YC that he was just like, and it’s working hard. You had like, I mean he probably had the most sales experience with anyone on the team. You brought a lot to the table, but he was pretty young and an experience. There’s a lot to be said of ambition young and an experience. It provides a lot of value and a lot of energy. It’s a sausage factory, right? You guys are just figure it out. But you eventually get your rears to California. Yeah, I think we have finally at some point after March of 2009 we ended up with the team being like me, Matt roll in and Andrew and equal co-founders. No, we had done equity. We hadn’t discussed equity. We really finalized equity at that point. We weren’t like NYC, we hadn’t incorporated so it’s still a project. But you had customers. 

Ben: (31:20)
No one was paying us at this point. Okay, awesome. It was to offer users and so we, it was still just kind of very much like a dream and a bunch of excitement and so I think probably like letting Andrew join kind of happened like last minute. I can’t remember. I don’t remember if he was at the YC interview or not. I think we might’ve added him between getting in and joining YC. But he might remember that better than idea. But like I was, it was, that was like over 10 years ago. I don’t remember that specific detail but blending. Why comment when we started YC, Andrew was there, he was a co founder. He had a lesser equity me, Matt and roll and didn’t do complete split. Like I took a little bit more than those guys cause I, it was kind of like the driving force for this thing, but for the most part it’s pretty even. 

Ben: (32:09)
Got ya. And that, that got us to California. I mean it all, it took me half an hour to get us to California, but I think that stories and threads is history. I think the important part is, is that people think, yeah, you just like, Hey Ben, come over for dinner and we whip out this idea and we go crank some code out and Oh my God, Oh, Clark Scott XYZ users and we’re making money and we’re drinking beer. Right. That’s not the way it happened. Nope. Nope. There’s nothing like that. I mean, I guess you want to, I’ll, I’ll get us to the end of YC and I’ll, I’ll accelerate a little bit. I just kinda wanted to focus on that part of the story. Sorry, I haven’t really told very much before. Well, it’s really important. I think also the lesson there is you’ve got to find, I mean, and people always ask, right? 

Ben: (33:05)
I mean, you know this a nontechnical co-founders, I think I need to find technical cofounder and I always say, well that’s the wrong, first of all, you’re asking the wrong question. The right question is I need to find the right co-founder because technical nontechnical, I don’t care. You’re married like in like you said you go through, it’s not a, you know the, the highest, when you win you win and you’re done. Good. But that’s not the test. You know the test is when, yeah, I mean you will deal with tons and tons of shit and it takes a long time. I think there is this like outside notion that like there’s a couple of stories, right? These companies that girl like super fast and like got successful very, very quickly. And I think people like to kind of hang on to those stories like sort of a like Instagram for like Facebook rapid success stories. 

Ben: (34:01)
But those are the exceptions. And I think that it’s important to, I’ll give you a context. There’s many success stories. It take I think a very long time and picked a lot of pivots and take like even those guys though Bennett, you know, I, I tell people like Facebook didn’t happen. Yes, they had rapid growth but it still wasn’t overnight. There were several years when they were doing colleges and I use under armor, right? Everyone’s like, Oh Kevin and those guys know Kevin was in Kips grandmothers basement making shirts at a pantyhose material for like four years. You know what I mean? But no one wants to talk. I think even Airbnb, those guys I think were, we’re a month away from going broke building the cereal boxes. So I think they had tried to do something else first and they had kind of like, yeah, there’s like a couple of different things they had tried during that process of actually figuring out what their company is even going to be. 

Ben: (34:55)
Well the point that I’m trying to make is even when you know, even once you know what your company is going to be, it takes time to, and there are a couple of guys that have gotten very, I would say loggy in terms of market timing. Yeah. Network and they’ve done really well. But I feel like you don’t really want to like base your philosophy or your approach on like getting lucky. You need to kind of build a process. It’s going to work. Yeah, like generates opportunity over time as opposed to just counting on opportunities, existing it for like one moment and just go grab it. Get rich quick scheme. It’s not going to work. Can you walk us through for the listeners, I mean not everybody, you know, we’re tech nerds now, everybody knows Y Combinator, but Y Combinator is really considered probably the defacto accelerator in the world. 

Ben: (35:46)
I mean there’s Techstars and there’s other really, really good accelerators. A Y Combinator is probably one of the first that really had the hits and put them on the map and has an engine that does it. I think the, what I’d love you to talk about is you go through Y Combinator and you get a little bit of money, but the expectation when you go through Y Combinator is this demo day and now you’re going to go raise money and there’s this thing here in the Valley that we live in that the badge of honor I, that’s what I call it. Or like the gold star for Ben is having raised money and I, aye [inaudible] you know, entrepreneurs asked me for advice like, Hey, the badge of honor is not raising money. The badge of honor is getting customers to build a business and actually never having to raise money. 

Ben: (36:32)
Now you have to re at times, yes it makes sense to raise money to accelerate your business. But, but that’s not the, that’s not what we’re shooting for. Like can we, can we go to these a bunch of, uh, places on Sandhill road or somewhere and convince them that our idea is good and then all is good in the world then? Oh it was good. Yeah. Yeah. So tell us about like your experience because yeah. How that worked and what your choice was. Cause you didn’t take that route, right? Yeah. So, okay, so we finished, we finished Y Combinator. It’s August, 2009. We do demo day. We’re not the hottest thing coming out of demo day. You know, like there’s a couple of guys talking to us. We don’t know anything about raising money. We don’t have like a lot of advice to lean on or networks and stuff like that. 

Ben: (37:17)
It’s really, yeah we’re going to raise money. And uh, you always start that process and we get like a couple of families, some friends give us a little bit of cash. I mean, I mean you and I were talking about the whole total raise I think was 60 K. I mean it sounds like a lot of money to maybe an entrepreneur hadn’t raised any money, but like in the realm of things that’s, well you can’t pay one person’s salary of 60 K so like that’s that. But like, but like in that process, right, we went and we talked to some VCs, we had a couple of guys who yeah, they were kind of interested in giving us money. Like there was a guy that built the live chat company before and he was like, yeah, I’ll do this if I, I’ll put in money if I can be chairman of the board. 

Ben: (38:03)
And then there was another guy who was like, or he wanted to kind of create the board composition like right then. And then there was another guy, a set of guys that were sort of, I would guess buddies with this guy who put in like maybe 400 cases. So he probably could have raised a bunch more money. At that stage is at least our perception, and this could have just been a negotiating point to be removed, but it seemed like this money is coming from a lot of strings. And for me, like part of the reason I’d wanted to build a company, and I wrote this blog before, 

Ben: (38:37)
kind of like freedom, like I built Oh Clark so that I could have a place where I wanted to be the CEO or the next hire or I could hang out with a bunch of my friends doing something great. And that was sort of like, that was like Ben of 2009 kind of wrote writing this blog post about why the sun was getting started. And like at that time just like this just doesn’t feel right. It’s not like I know how to do the route where you bootstrap, you grow it. And we got like, and the team has changed a little bit. We’d brought on another cofounder and yeah, before placing Andrew. So it was me, Matt rolling and stuff. Zack. Zach was a technical genius so we had like two. Okay. Geniuses Madden’s Zack. Zack was a technical genius of the backend. Matt was a technical genius of the front end is a fabric made of designer. 

Ben: (39:27)
I’m like an okay business guy, shitty manager and like, uh, a reasonable backend engineer. Yeah. I kinda like do a lot of things poorly. But like, and so yeah, we basically had all the ingredients we needed to be successful. I think about that. So we have the right people, we have enough money to eat and we just needed a time. And so we, okay, we’re going to raise as much as we can in the next week. I think we next like whatever. At some point we’re like raise most we the next week, then we’re done. This is just a waste of time because we don’t need the money. And like at this point we launched, paid, we had a slowly increasing line in the shooter revenue. We’re like, you know, we just follow this line for awhile. That’ll be fun. And every day we’d get a graph that would be like, what is our MRR? 

Ben: (40:11)
And like the building over time, that’s a monthly recurring revenue for people. That is the key. One of the key metrics that you want to watch or a software, the service business. It’s a good metric. There’s probably some other metrics we should’ve been paying more attention to. It was like usage or chats. Sure. Well yeah, I mean I think actually those days all those messages were really great, but we were really just looking at, but the thing is we weren’t looking at them, they just happen to be great. It was just like we lucked out and they were great. So there are many things that like we did, we kind of just managed to get by doing it, but that MRR number for us. But wasn’t that really a signal at that point then for you that, I don’t hate to use this word, it’s so freaking overused, but you got product market fit instead of better way. 

Ben: (40:55)
You were just solving people’s problems. A true problem that they had that was a true pain point and they’re willing to pay you. I mean simplify. Yeah, that’s it. Yeah, no, it’s true. And the thing about it is we had figured out a way that it marketed itself well because every chatbox had a link back to us on it. And so in addition, so we had that going on for us and we had like really high word of mouth. Well we just, that was it. We did not do any paid ads, didn’t really know anything about marketing. I all arts history, we’ve never really done paid marketing, like just not something we’ve ever really understood how did do, but you did some good, I mean maybe you meant to, you and I talked about this a little bit in the past, but you, you also call it luck, call it whatever, but you got some luck with some organic SEO. 

Ben: (41:42)
I mean you had that viral component. Yeah, yeah. We did have SEO that helped us out a bit, but in the early days that wasn’t a factor at all. Well back then we didn’t have, I mean the domain authority is pretty low because we’re new and we didn’t have tons of links back to us at that point cause we’re just still getting started. But when did you change your name and why did you do that? Oh yeah, so that happened during Y Combinator. I mean people think of Paul Graham is like this like genius who has the answers for everything and all I can say is through our meetings with him, the main thing he was like being, it was telling us like don’t be like Dropbox like right. Get and it was just such a huge thing for them to buy like it was just a huge ordeal. 

Ben: (42:25)
It cost them tons of money and he’s like just like own whatever you’re going to be before you get big. So we were like, we looked at [inaudible] dot com and I think they wanted like 50 K for it or something. We didn’t have 50 K so we’re like okay, that’s not going to work. Plus we learned at some point that oblong means something kind of like asshole and Arabic or something. So then we also learn that no one in the freaking U S knows how to spell Abla. Yeah. Most people don’t know what it means. We were getting a few out of there, that’s the stupidest name ever. And we’re like, okay, like got it. We’ve got enough signals here. There’s nobody to hold onto this. Even though we were like, we were like into it. We loved it. Yeah. Internally we’re calling ourselves the door. 

Ben: (43:09)
It was a fun brand. So we had to come with a new brand and we just got putting this off and a bachelor’s was like, okay guys, today, this week we’re doing it. We’re gonna pick our new brands. So we just, no, there’s four of us. We sat down, generate a list of open domain names. We thought it could be our brand. Uh, there was names like [inaudible] that I ended up, well now if I, no [inaudible] was a favorite. Users see all these, like I don’t know, brands, his names and then we would kind of like vote on them and I think we’re kind of like, okay fine. Wouldn’t be like ping B I guess. And then we’d call up like Matt’s dad. Matt would have to describe to his dad like the name of the company and if he couldn’t like figure out what Matt was saying then like it was no-go. 

Ben: (43:55)
So like Matt called his dad about it can be and his dad had no idea what he’s saying. No. And any idea how to spell it? Yeah, like I’m done with this process. I’m just going to pick a name. We’re going to be that name for the week and if we don’t like it we’ll pick another name a week. So Roland had coming up, come up with the name [inaudible]. I don’t know where it came from at the time. He kind of disliked it when I picked it. I was like, that’s too bad. Rolling. You submitted it as a name. It’s short and it’s easy to spell and it’s basically unique internationally so that name can own the brand. 

Ben: (44:32)
We can create anything we want. There was no connotation to people’s heads. What’s this word? [inaudible] all art for a week. But then the week everyone’s still like being all Ark and then we never looked back. Awesome. Well that’s a good, it’s a, it’s a good story. It’s good for people to understand. Like do you and do you think, and today’s a date, today’s day and age, you actually need and we’re on zoom, zoom, Do you think that today it’s as important? Uh, I’m old school guys to like I don’t know. So the answer’s yes. Yeah. Yeah. I’m still, I’m old school, so there’s probably data that shows it’s not important, but I still think that for the average person, you say something to them, it just not tech people, but just kinda like, and you said I was like and you’re telling your dad your dad might add alright. 

Ben: (45:27)
It’s true. So that was what people were doing with Abla. It should everyone thought we just had like, I would say like average users, this thought you have to it. And I think for us it was for word of mouth, we’re just like, we want people to be able to tell someone else what the company is and what the brand is on ambiguously. It’s like when they say it, fair enough. So you get out, you don’t, you, you decide tongue in cheek here, I’m gonna raise money for a week. Whenever we get, we’re not going to do whatever money we get. Great. But then we’re not doing that raise money thing anymore. We’re going to go build the product. And at that point you start to, you get a good line of word of mouth effectively, whether you did design that into the product and knew it was going to work or not, but you have that link in the chat of every single one. 

Ben: (46:16)
And actually before you and I met, I knew you because of that. Yeah. You and I, we’re not that old, but you know, compared to some 20 year old were probably [inaudible] we come from three or four waves of the internet when we can remember BBS boards. But I remembered OLR because of that because it was viral. So at that point you guys are growing and did you just continue the, the trajectory? Ah, you know, that’s a really good question. I haven’t thought about the early day growth that much recently. There probably was kind of like various moments that kind of looked like a hockey stick. Like were you like and then like kind of plateau off and kind of true. There was never kind of like a hockey stick. Everything just goes and sure. I really have like a great explanation for what was happening. Like in our growth. I mean I think that in the early days we would have like PR hits every once in a while and those PR hits seemed to be like pretty, pretty helpful as time went on. Like we would try different things. Like, for example, we did a, uh, I think we might’ve done like a partnership with Shopify or like that, like pretty early 

Ben: (47:30)
on in that shot. Like way back when, you know, shop, I was tiny right now it’s pretty huge for us too. And so there’s a couple of these sort of little inflection points. We’re working with some other company that was, you know, not big yet but like pretty good at getting PR. Like that would be pretty helpful for us as early days. It’s like a pivotal moment. It added legitimacy to the brand. Yeah. Like when a shaft flower was going off trying to raise money, like we ended up being some of their case studies and so they would go and tell VCs like, Hey, like I look at our partner network and how like people are building real businesses on top of our, okay. Yeah, I knew Ali Tobi and all the, like all the people over at Shopify before back when Shopify was tiny. 

Ben: (48:13)
So, and I think that it’s just like interesting kind of being in that environment and like have being an, uh, an ecosystem where people are just helping each other out. And so, but I don’t know, I don’t really think there’s like pivotal, pivotal like, like moments where like it’s like, Oh this thing happened and made a major impact. I just think it was like a series of like hustling, like trying to meet other partners and your ecosystem. Like understanding all the people there, like actually knowing them as human beings. And occasionally these people would help. We’d help each other out. Like we’d promote them, they promote us. Right. I think that really caring about our customers. So in the early days we all did rotations on support just to make sure that we would stay like very close to the user. And especially when you’re just getting off the ground and you’re four or five, six, seven, eight people like that, that time is just critical to making sure that you’re not out there just like building random shit. 

Ben: (49:08)
Like you’re completely solving, they’re your customer. Cause I feel like it’s very easy. Oh, wouldn’t it be cool if when people are all like, Hey, like just make free message delivery work better. You know, like it’s, it’s so easy. I think it’s the light. Put a support person in front of your customers and I get like a summary and then like just like and building stuff that’s like not really that important for customers at that stage. No, it’s really important to it. Listen to the customer. I think that rotation is, I mean, you know, even if you just start listening in all the calls and not even doing it, that you’re, you learn a ton. So Ben, the other thing that’s really interesting is, and I love you did this, cause I haven’t raised some money. I got beat up from it. Some investors in the past, you have a completely remote team, right? Yeah, completely remote. We stopped paying off Lisa’s entirely. I don’t know, maybe like it wasn’t even that long ago. I think we still, at least in Ann Arbor, Michigan, like last year in March or something. But no, haven’t actually, once I had been going thought office for a year, it was just kind of like after you build it empty, empty floor of a building. And how many people do you have? You have over 30 right? Yeah, I think we got like 

Ben: (50:28)
the number is always like a little bit more in my mind, but it’s probably like around 33 somewhere, somewhere. Give or take two I think around 33 is what we have right now. And you guys use just for those out there who w thinking about remote team zoom, do stand ups with your team and then you do, I only see some pictures. Can I hear you talk about it? You do, which maybe you would invite some outsiders occasionally. Probably be cool. Okay. To your, what do you do to get together once or twice a year? Yeah. That’s interesting. So we get together entirely as a company for a week, once a year, and every year prior to this year we’d fly people’s spouses ESOS out if they won to come and we fly their kids out if they want to come. This year we tried something a little bit different. 

Ben: (51:15)
We just are flying just the old lockers out. And I think part of the reason we did that was because we’re realizing that by putting the option there, like yes, sometimes people felt a little more obligated to bring their family with them because it was like more or less free, right? When there’s actually a lot of value in being able to take time away from family to focus on Olaf because we’re so embedded into your kind of like, we’re so flexible, like day to day, like you didn’t take time off to go deal with something or like pick up a kid or whatever. It’s just so easy. That’s for our flexible work. It’s a blend with that. It’s nice to have some time when you can just kind of step away from that focus on the company and focus on each other and your relationships with your coworkers and stuff like that. 

Ben: (51:59)
But it’s, yeah, I think it’s a really powerful way to, to create some of those human connections. It’s kind of amazing. It’s sort of like like a big family reunion. It’s just so special and I’m not sure exactly how we managed to do this, but, well probably because of you Ben, because I mean if you can comment, one of the things about Ben for everybody is, and this is the saying that you can elaborate. When I first met Ben he was like, listen man, it’s not about the money. Yes you want to make money, you’re in business, but it’s about solving a problem and hanging out with people that you enjoy working with. Being a little bit humble here saying, I don’t know how it happened but it happened because your leadership really drove that. 

Ben: (52:41)
Sure. I’ll, I’ll step that back a little bit. I think what we ended up doing is we early on when I started this company, my philosophy of like I want to be the next hire or I want to be a CEO, like that’s been in my head like something’s getting and then I think Matt, my co founder is incredibly good about just like caring about culture. Like he cares about culture. Like, I care about culture a lot, but Matt is just like me 10 X or something like that. Like Matt is thinking about the way that people uh, kind of will, the way we communicate to the team, the way that we like come back to our values and work values and the things I feel like Matt has like a super power there. And I think that the combination of me and Matt in those leadership positions and the early days 

Ben: (53:26)
of having this four founders living together, the house where we are all, yeah, it’s clear family. The like work through any issue lived in a work from the same house for like the first two years of the company. And so I think like having that experience, like as we brought more people into this family, I think we just sort of kept that, that mentality. And I would also think that like without BC money trying to like [inaudible] I think, yeah, the, that’s it. [inaudible] awesome. Like [inaudible]. Okay. The whole, that allowed us to allocate a little bit more time towards building values and building culture and building processes within our organization. To keep those things alive. Whenever you show up to a retreat and like everyone is hugging each other and this is like the first time they’ve met, it’s just like, so it’s like very special. I mean people tell me, Oh, it’s like very California, but it’s like, it’s very special. 

Ben: (54:22)
Uh, having not worked at a bunch of other places, what would have been kind of like interact with like other coworkers or friends outside of a Lark? It was a rare phenomenon for something like that to happen. I think you’ve got it. I mean everything that I know and I hear and uh, when we talk and share ideas that that’s what you guys have been really good at. I think that is why you’ve been able to grow, be successful. Well, I think there’s another factor too. And I think like not only have we grown and been successful and I would say we’ve been through hard times and like there are many challenges we run through. But I think it was the thing is that as a leader when you have a team that like really cares about you and about each other, like it’s just so much easier to deal with tough times and to deal with shit because you were like, Hey, like helping out these guys. 

Ben: (55:11)
Like we’re in this together, we’re trying to get to the same place together. Like we may disagree, we may face challenges like we may argue but like on a psychological safety level, it’s there. Like, you know, you tell me like people know that like if something didn’t happen because like their kid was sick or because like they, you know, just been dealing with a lot of stuff in their personal life. Like, like they know that like my reaction is not going to be like, Hey, like what the fuck is more like it’s going to be more like, Oh my gosh, like, you know, are you taking the time to like take care of that problem? Like, you know, we can, what can we delegate? Like what? Like, what can we take off your plate so that you can like be present in that moment and like what you need to deal with outside of work. And I think that uh, for me it’s like a long game because if people know that like they’ll bring their whole selves to work cause they know that you got them when they need it. Yeah, I think that’s it. You’ve done awesome. I want to just say a few things. If you have a website out there and you need chat, you need to get Omar, these guys. Yeah. Hello. Been there since the beginning. They’ve got, they care as you’ve heard in customer service. So it’s now I, everybody really wants 

Ben: (56:24)
to talk about the business. I’m just going to say Ben and you can sum it up, but Oh, aren’t you doing really well? I want to talk about rev. You do a lot of revenue. You guys, you know, you gotta feed and clothe and put everyone’s kids through college for 31 people so people can do the math out there. You guys are all making, you know, a good healthy living and you’re having fun. And I think that that’s important. So now that he is a, I think your shirt that you have on 10 year anniversary, right it his 10 year anniversary shirt, that’s the cool thing when you reach 10 years is these shirts will just appear and you will have nothing to do with them. Like that’s, that’s like, I dunno. I dunno. Just little things like that make me feel so happy. Right. Like just our retreat was organized by our team. It was so co-created. It was, it’s amazing. It’s amazing what you can do when you empower people. So you got 10 years into it, you have kids. What does a day look like for the CEO now of Oh Lark. I feel like a day especially, I don’t know. I know you kind of like prompted me like we’re going to talk about a day. 

Ben: (57:30)
Yeah, sure. I’ll give you kind of like high level, right? Because like what I’m doing on a database. Yeah. And it varies more like on the, on the place in the quarter or like than it does by data week or anything. So a typical day for me and I’ll just give you like my day, I dunno today because that’s like a reasonable example. So today is a Friday, it’s the end of the week. I try to have a little bit more chill Fridays so I got up whenever. All right. And I’m single parenting. My, my wife is like on the East coast helping out her. Uh, her mom was in a bike accident with our other daughter. So me and Nora are kind of like holding the Fort down or it’s two years old and I would do this for 10 days. So my wife got back. 

Ben: (58:17)
I’m excited, but like, so I get up whenever Nora gets up, which you know, could be like, I dunno, seven o’clock could be seven 30. Then I go and uh, we have a diabetic cat, so I have to give our diabetic cat shot, I have to feed our cat, then I have to give her, give it a shot. I have to go feed their dogs chicken. So I do like this like mad dash. So basically be as efficient as I can to kind of deal with the stuff. My daughter is two so I’ve made change a diaper for something like that. If she’s kinda like active, well normally I’ll kind of like leave her inside while dashing around dealing with all the animals and keeping them alive. And I then I come back inside and normally, uh, our nanny come come at eight and then I will, it’s like in that gap between an Oregon stuff and eight, normally I’ll slate, I don’t know, hang out and play people or something like that. 

Ben: (59:09)
Normally we have a game we like to do or build powers, which is pretty fun. So then Workday starts eight, eight o’clock. He’s caught me. Like Fridays I normally try to keep a little more chill. So, uh, you know, I spent like the first like, I don’t know, hour and a half, like just really sitting down and trying to plan because we have new quarter coming up. But I just like this to sit back and like reflect on our milestones, reflect on our vision and like make sure that all the conversations need to happen to sort of set that up or being thought about. I think I also was doing some reflection on my own OKR cause again quarter like we have offset quarters in our quarter. This is like the last three of our quarters. So like the last day of the last week, my quarter is normally trying to be pretty chill. 

Ben: (59:52)
Like I don’t like mad dashing around the end of that time. So it’s time to reflect. Is it time to think about like would have been doing, it’s not really a time to like act as much on a on the last day. So I had a, I’ve been doing a lot of customer interviews so one of my items was I spent some time writing up customer interviews and sharing with the team. So I typically do that on Fridays. So I have this quarter I did alright. That’s like over over 30 calls with customers. Each call was at least half an hour. Longest was maybe like an hour and a half and I just kind of like let the customer talk and I make the time and space for them. So I got and I try to like make like very real like have like very real conversations and they’re targeted, right? 

Ben: (01:00:36)
Like my, yeah, Ellis was like I want to talk to definitely I want to focus in on a top 30 by revenue but I also want us to kind of spread that out. Like I looked at top 500 by revenue. It was like a main, I kind of batch I was focusing on. Then I also looked at the bottom 500 by revenue because I wanted to get like a split perception of like the big guys and small guys and just like have a good sense. And so you know like an hour and a half call with someone, one of our bigger customers and for the first half of that call we’re talking about how like they’d gone to amuse concert and they had like slipped in the bath tub of the hotel, like mess up their leg. And it was like not the night they were expecting and now they’re like being taken care of that they’re like working from home and they’re like daughters taking care of them. 

Ben: (01:01:19)
Like just kind of some real fricking context about what’s going on in the lives of our customers because this stuff actually I think it’s important to understand that like as much as I think, I don’t know like the term human resources is the humanizing. Like at the end of the day, like every person there is a human, they have like challenges in their job role they have. Uh, so I asked you like what are the biggest challenges in their job role? Not even related to Alek. Like I just want to understand like what’s going on in their life. Like what, like what are your challenges? No, I asked her like what’s going on? Oh Clark. Like what’s challenging goal arc and no I tried to get like much context about life. How does that work? [inaudible] and then you know, the end, I kind of asked like what do you like about Laura? 

Ben: (01:02:01)
Cause that’s always fun to cheer for the team. But for me like I’m trying to like pull in context to sort of feed my intuition and my pattern matching around like our customer base is how to reach these people, how to innovate and how to like, you know, make their lives better. So like today day was spent kinda like reading through some notes, these trying to type them up. I try to for the hype these up to the team and then I use these relationships for things like, Oh like someone wants the marketing, let’s do a case study. Well now I can introduce you. Or like, Hey, uh, you know, we just hear about this bug happening. I’ll be like, well actually I have a recording of a call that I talked to a customer, they’re complaining about the exact same thing and you can kind of understand where it fits into their workflow and why this is important to them. 

Ben: (01:02:41)
And it’s nice, I feel like as CEO to be able to kind of provide that top down. Like, Hey, we really freaking care about customers. And did you know that like Laura was running into this issue? Like just try to like kind of with a customer base of like overall 11,000 customers sometimes. Like it’s hard to, for the individual people that work at Olaroz to seem more than the customer service requests. And so that’s something I’m trying to champion. So I spent spent some time doing that today. I ran a meeting. How between product and marketing too, discuss how we’re going to prioritize product channel fit for like products like mingle. They’re just like for everyone to just be aligned going forward. Like who’s responsible for what, what’s going to happen next quarter? What’s gonna happen to quarters out a little bit more like kind of longer term planning? 

Ben: (01:03:30)
No, I sat, let me, I’m just looking at my calendar. Yeah. Sat in a meeting, uh, in a meeting where I was kind of finalizing kind of like a, a role discussion for actually myself. I’m my co founder and one of our senior leaders just to kind of like a hash out, a sort of timeline, some communication planning for it for us. A team. Aye. I ran to the bank and, and I got this call and that’s, that’s basically a day. And it’s like a bunch of other like little stuff in there. But like, you know, that’s kind of a big, the big chunks of the day actually. I, Oh well last night, last thing, I did spend a good amount of time looking over like our, our direct, here’s our higher level managers, quarter debriefs and brought in feedback on that too. And that was something I was kind of rolling in before I ran to the bank just cause like we do more or less okay. 

Ben: (01:04:27)
Ours. But yeah, and for your listeners, OKR, uh, it’s objectives and key results, but it’s a, it’s a high level. So I all objective accomplishment chains up to me. So like if you’re like head of marketing, not a product set of CS like I am, I’m the person that’s holding accountable and the person who’s running like your mid-quarter check-in and a quarter check-in. And so it was the end of quarter check-in because we’re remote team is mostly done asynchronous. So there’s like a bunch of questions that you fill out and answer in advance and then we’ll have a meeting next week for like a short meeting next week to talk about like last quarter and this quarter. But in between getting your reflection in, not in that meeting, there was normally a bunch of asynchronous communication back and forth. Like I’ll ask some follow up questions, they’ll answer them. Mostly what I’m interested in is like did he hit your objectives? Why or why not, what, what could be improved? What have you learned that you can apply next quarter? And just kind of helps me keep a pulse on where we’re at towards our bigger milestones, how I can make sure to unblock. But at this stage like I’ve found it, my biggest libraries is definitely not like it’s individual contributor in this vanilla, like a huge, huge growth opportunity for me cause it took me, no, took me nine years to figure that out. 

Ben: (01:05:44)
You were asking me a question, sorry. And I think that, well I appreciate you sharing that because that’s a really important point and I think you recognizing that you don’t know that your role isn’t necessarily to be in the weeds but more to manage the business. So you’re working on the business, not in the business and you’re, yeah. Oh my God, I love working in the business. So this is an ongoing challenge for me. But I think sometimes you have like these customer calls and stuff like that, like it’s been okay, amazing to see the rippling effect of some of this stuff. Or is it just like it’s, it’s really neat when you can do work that you see like multiplicative ripples across stuff, but like if you’re so down in the weed you never see that. So it’s, yeah, I think this last year has been a year. 

Ben: (01:06:32)
I’ve been focused a lot more on that and really being mindful. I have like this little like I have like this little thing I made. Like I have an exact coast and I made this little note for myself that says like don’t jump in, get dopamine from the big picture. And like literally the help remember or remind myself, they’re like, well I do get a lot of enjoyment from solving shit really quickly. That’s not where I needed to get my dope. And it’s like, it’s a way of like training myself to kind of step back and be a much better leader. But I think that’s awesome. Maybe it’s just a ism that you made up, but then I made it up. But, but it separates you as a human in saying, Hey look, it’s the dopamine here that’s doing that to me and I need to recognize that I still need that. 

Ben: (01:07:20)
I still like that hit but I’m going to get it somewhere else. Yeah. Yeah. And actually it’s really interesting. I think I basically trained myself to get more dope me from the big picture if you’re out this year, but like at the beginning of the year it’s just like, ah, I want to get in there and solve that problem. Well I think that’s a, you know, that’s a a huge lesson in you. That’s a congratulations to you cause that’s a big transition. It takes a lot of self awareness to be able to do that. As a leader. I feel like that’s like honestly that’s the most fun thing about doing this for 10 years is that you are constantly learning and you’re learning by yourself like and you’re just growing. I think that like do things like learning, growing and working with a great team. 

Ben: (01:07:59)
Like what more would you want? And that’s why like I have a very hard time understanding people that are like all they want to talk about. Is there fundraising strategy or something like that. Just like man I understand this stuff is important. I understand like how much money you raise, your evaluation is important. Well like I literally just don’t care. Like it’s like I will like we can have this conversation, I can ask you a couple of like useful questions or something like that. But like, yeah, for me like I just not really that interested in this kind of stuff. Like I’m much more interested in figuring out like how do you build a really great team and how do we solve a problem? Not like the finance side of it, but there, you know, there’s plenty of people that care a lot about that stuff. 

Ben: (01:08:35)
It’s just not me. Yeah. I love that about you actually Ben. I think that’s why we hit it off a little bit because I like that, you know, and you know I was a DC, but no sir. I’m like, Hey, let’s just build a real business that we enjoy cause we’re going to be dead and like, you know, I don’t know. We’re all going to die basically. Guaranteed. We’re all dying. So let’s, let’s enjoy the time we have. Yeah, I don’t think, uh, I don’t, you know, I don’t think you were, I are going to talk about what valuation we had on her deathbed. That’s really not what we’re going to talk about or remember. Well, anyone who’s doing that, probably a waste of their life. I would agree with that. So what I was going to ask you just quickly is in your whole day, the interesting part for me is it, I hear any time that you were answering emails, so do you batch process that or you just not even care? 

Ben: (01:09:22)
I just don’t care who is emailing me that I care about today. Who needs a response on Friday? Well how about Thursday? Like only emails that I am more so our companies are on Slack. So one no, none of my employees are emailing me. Okay. Or teammates. But the main use of email for me is external parties. External parties be like okay I’m working on some sales thing. I mean I did. Do you want to, when I kind of like said for a second like Oh yeah there were some other things I probably did send a couple emails. I do not, I’m not inboxes Euro. I’m like inbox a million inbox. It’s going to crash GMO. I make aggressive use of kind of the GML importance like starring like auto filtering and anything that doesn’t get selected in there. Probably not going to read cause I got so much junk, like so much junk. 

Ben: (01:10:11)
But it’s just, it’s tough. And so my sent email folder is a way of tracking stuff I’m trying to keep track of cause that’s that I know like I care about everything. Well that that totally that totally makes sense. And I don’t want to spend too much time. I just wanted it for the listeners cause sometimes they get like how do you handle it? And it sounds like you’ve got a good grip now. Right? I know Nora is going to get up soon cause uh, so far so good. But I want to end with three HPTs high percentage tips. Sure. From Ben to the entrepreneur community. Anything from starting a company, growing a company, what would those [inaudible] yeah. Okay. So thank you for asking about these in advance. So that could be a little bit smarter about, just felt like five minutes for a half on the call thinking maybe, maybe 30 seconds. 

Ben: (01:10:56)
So yes, your HPTs one, I think you should probably read the book radical candor. I think radical candor is an amazing way of framing feedback. It’s written by a lady named Kim Scott, uh, that worked at Google work, the Apple university in order to try to spin kind of like a thought leadership, a company called radical candor. But the book radical candor provides a really good framework of thinking about feedback. And in particular what you want to do is you want to get care Bhutan and you want to challenge directly. Like that’s the ideal quadrant for her. A little uh, yeah, feedback quadrant. But within that book it talks a lot about how it’s important. It’s in her opinion, she values correct, obnoxious feedback more than kind of like a passive. Like I think a lot of times people hold back, I’m kind of speaking their mind and like for fear they’re going to find the other person and her argument is based with this better to find the other person, let them know what’s on your mind than it is to a be insincere and just like shape that message. 

Ben: (01:12:01)
And I love my wife. Yes. So like in, in that book, I think that framing is like super valuable and it really resonated with me. And there’s also a bunch of applicator like apply lessons for management and stuff in that book too. Packs a lot in, well I want to wait before you go to two. I want to cover myself because I said that’s why I love my wife, not because she’s a noxious because she’s honest with me. Always gives me the straight feedback. Number two, Ben. Yeah, my wife, the same one also isn’t in the same way. Probably helping me learn a ton. Just gave me a framework to realize why cam was so awesome. But the brands don’t work. So that’s fantastic. And I think that’s what you look for in a partner. A coworker. Okay. I, I don’t want anybody thinking that I was saying my wife’s a notch and my wife has made me a better person. 

Ben: (01:12:52)
No question about it. So number two, band number two. Alright, so this is a useful lesson. I think some people are very impatient and I think that they try to see things happen very quickly. So like if you, if you look in the, in the, the metaphor I’m gonna use for this is the story analogy. So like basically we went through Y Combinator, I back in those days, I think maybe there’s 28 other companies in our batch, something like that. I would say all of those companies, maybe five are still alive right now and operating mentally. So, and that, that might be a slight exaggeration, but there’s just like very few of those companies in that batch are still alive right now and very few of them have. And those that I’m counting are dead of them. Very few had good exits. You have to imagine that like if you’re like running a race, right? 

Ben: (01:13:38)
And you like see these people that are like way ahead of you and that’s how they raised all this money, there’s killing it. They may be running really fast at the beginning, but that does not mean longterm success. And I think that by focusing on customers, creating value for customers, if you do that consistently and grow that that scales and that works and that’ll get you to where you want to be. Trying to like accelerate that process with a ton of money does not work for many people. It may seem like it when you go out and you’re like, I read about a couple successes but if you imagine the amount of money dumped into VC versus the amount of money that actually have huge successes, a few of these like giant year earlier, like we work and your therapy doses and your like, there’s plenty of examples of companies that raised tons of money and like I think maybe it didn’t provide the customer value that they, their investors thought they were going to get out of it. 

Ben: (01:14:32)
That’s a great advice. So, so yeah, so I think that just think about that long term, be patient and don’t get caught up in that like, Oh like you have to move like super freaking fast and be successful. I think like so many companies fail because they try to move too fast and they don’t, they try to go somewhere before they’re ready to be there and they just put themselves in a situation where they can’t win. I think for example like increasing your burn to the extent where now you got to lay off a ton of people to survive. Yeah. Killing off people is like incredibly depressing and the people that are still around, it’s going to be super depressing for them. Like it’s, it’s hard times and you don’t have to, you can avoid putting yourself in a situation like that. It’s just one small example. 

Ben: (01:15:12)
Um, and then my last, my last piece of advice is to think about, I like to call them kind of feedback loops, like around sort of listening, learning and improving and I think you can apply these like framings of basically any situation you can apply it to customers, right? Like come up with some process where you can listen or you actually hear what people are saying. We’re going to learn like internalize what it is they’re saying. Like maybe consolidate a bunch of interviews. Think of patterns and stuff like that and then improve, like actually act on the information to do something new so you can do it from a customer standpoint. You can do it from a management standpoint like listening to your, your employees or your reports and taking the time to like learn and taking time to craft like how this is going to lead to improvement. 

Ben: (01:15:56)
And I think that just if you can like put that like framing in your head, it can be super valuable to approach problems in that way. I think a lot of times people will sort of jump and really quickly to say like problem solution or they try to like move like pretty fast from just like Oh here’s a problem, here’s immediate solution. Not like here’s like 500 solutions or something like that. There’s another kind of like slow down think before you act. And then my bonus tip I’m gonna go for feedback is super important and there was a very, it’s straightforward way to look at it. I think a lot of times people, like especially engineers and the way that you interact, provide feedback over say like positive feedback in particular. A lot of times people will be like, Oh like I don’t know Brandon plus plus like in a channel or bought and they’re like, Oh karma goes up. 

Ben: (01:16:48)
That is shit feedback. The good way to provide feedback is to say that like, like Brandon, the way that like when we hang out you’re like quite present [inaudible] although your whole mind is on the conversation. It has. Yeah, very good impact on me because I enjoy it. Like when we were at, when we know that we’re like focused and we’re like in it together, it makes me like, you know, respect you as a human being. Cause it kinda like helps. It helps me feel seen and heard. Well that’s very nice of you. And if you’re actually telling him about this grade and I, I’m totally am. And I think that your candor also like the like your willingness to just kind of speak and be vulnerable and have conversations. It makes our relationship stronger. And I think, and what that does is it makes me believe that like you do this some more relationships and it kind of shows me that like you’re a real dude. 

Ben: (01:17:34)
Yeah. It makes me feel like I can like, like trust you in many ways. Right. So likewise guys, just so you know, likewise, that’s why you and I get along well, but the point that I’m making is like when you have, when you’re giving to you that cause for negative feedback, I think it’s important to label like the behavior, what impact, uh, you perceive and then impact that that has on you and in the world. And I think that if you can frame feedback like that, it can be, yes, it’s more work, but it’s incredibly powerful for the people that receive the feedback. And you’ll get a lot of positive feedback yourself once you’ve kind of, I want you to think of that that way. And is that applies both for negative feedback and for positive. I think that’s awesome. That’s, that’s my final. No, that was awesome. The bonus. Well, I know that your daughter is going to get up and you have been really great. This has been awesome. I’m so grateful for you coming out. 

Brandon: (01:18:24)

Ben: (01:18:24)
truthfully, Dan, I love talking to you. I, I don’t know why you and I haven’t gotten better more, but we got that group. Totally. Yeah. So don’t give us an excuse and then we’re going to do dinner with our wives and everything. Absolutely, man. Absolutely. My wife gets back tomorrow. We’ll find a time. It’ll be, it’ll be fantastic. And so, yeah, you know, and I appreciate that about you. I feel appreciate that our conversations are always very real and very candid and not like when we come back after not talking to each other for a while, it doesn’t feel like time’s passed. And I think that’s another, another sign of someone who really like isn’t vested in the conversation was actually listening, you know, and actually like being engaged. So, yeah. Fantastic. I really appreciate the call. I’m looking forward to it. Enjoy your weekend when cat gets back. You would probably be relieved, but you’ll be here and a little less duty. Everybody, Ben from Olaroz, if you need a chat program, that’s what you want to do. That’s what you want and you will learn why they care about their customers so much. This is been 90 minutes of pretty much understanding that, so thank you so much Ben. Enjoy your weekend. For sure. Thanks Brandon. Take care. 

Brandon: (01:19:35)
Well, I hope you enjoyed that episode as much as I did. Ben, as you can tell, is a great co-founder, great CEO and just a great guy. So, uh, Ben, if you’re tuned in here, thank you so much for doing it. Really enjoyed it. If you enjoy this episode and you are thinking about funding your business, I put together a checklist for you and that checklist goes through all the things that you want to think about. If you are thinking about funding your company, and as you heard from Ben, it’s not always the right move to raise money for your company or you might just not want to go through the process and you can absolutely build a successful company. So I put together Gigi, a funding checklist for [email protected] forward slash nine that’s Brandon C forward slash nine go there, hit the download. 

Brandon: (01:20:32)
You get the sheet, fill it in. If you have questions you can always email [email protected] that is my personal email address or you can text me or call me at (415) 429-1229 feel free to, if I don’t pick up, leave a message or text me. I’ll text you back again. (415) 429-1229. All right, well if you enjoyed this episode, please hit subscribe and whatever podcast player you are listening on so you do not miss any of the upcoming episodes that we have. We have some great guests coming up. Also, if you enjoyed this episode, please leave us a review so we can hear from you on what we’re doing well and what you would like to say. So if you do that in your podcast player, leave us a review. We read all of them and we take them seriously. Love to hear from you. Until then, I’m rooting for your success. We’ll see you in the next episode.

Subscribe to the Build a Business with Brandon Podcast on your podcast player below

Build a Business with Brandon Podcast Homepage