With Scott Orn

A Startup Podcast by Kruze Consulting

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Scott Orn

Scott Orn, CFA

Russ Heddleston on DocSend's Content Management & Tracking System

Posted on: 09/23/2018

Russ Heddleston

Russ Heddleston

CEO - DocSend

Russ Heddleston of DocSend - Podcast Summary

Russ Heddleston of DocSend on the Company’s Content Management & Tracking System that helps sales and marketing teams be more efficient. DocSend is the preferred Content Management system for the startup world. Russ talks about his journey founding the company, figuring out what worked and now scaling the company.

Russ Heddleston of DocSend - Podcast Transcript

Scott Orn: Welcome to Founders and Friends podcast with Scott Orn and Kruze Consulting, and my very special guest today is Russ Heddleston from DocSend. Welcome, Russ.
Russ Heddleston: Hi, Scott. Thanks for having me on.
Scott: Yeah, so our mutual friend, Benjamin Wayne, introduced us. He is a good buddy of ours or mine, and he sits on your board. Right?
Russ: Yeah, he’s our independent board member. He’s fantastic.
Scott: Yeah, he’s awesome. We met a couple weeks ago or maybe a couple months ago. I’ve used the DocSend product for a very long time and so I immediately was loving what you’re doing. You mind tell the audience how you had the idea for the product and retrace your career a little bit?
Russ: Yeah, absolutely. Happy to, and it’s also funny that we’re two blocks away from you, so the people creating DocSend were just two blocks away this entire time. My background, I studied computer science at Stanford. Before that, I am from South Dakota originally. There’s not a lot of computer science in the state of South Dakota, so I got out to Stanford. I was like, “What’s the cool stuff going on?” “Software! The software’s pretty great!” I actually started by building robots in undergrad, and then I was like, “Robots are slow.” It’s a slow industry, so I was like, “Software’s better!” I got into software, worked at a whole bunch of different software companies. I was the first intern at En Trulia way back in the day.
Scott: No way!
Russ: I was an intern at Microsoft. Yeah, Pete and Sami are awesome. I’m still friends with a lot of people from Trulia. I was at Microsoft. I then joined a company called Greystripe. It was a mobile ad network. After I did my master’s in computer science at Stanford, hired two of my friends from Stanford who are actually my two co-founders for DocSend now into Greystripe. I went back for business school out at Harvard. I think the computer science was probably more useful. It actually changes over time. I appreciate the MBA the farther in the future I get, especially being the CEO at DocSend. All of that stuff is kicking in. It’s pretty helpful. While I was at HBS, I did an internship at Dropbox which is where some of the concepts behind DocSend came from or at least my familiarity with the space. I then started another company called Pursuit. We raised a seed round funding of 500K, ran it for about a year. I’m sure a lot of startups get to this moment where like, “Uh-oh, this isn’t working like we thought it was working.” We were gonna shut it down. We were lucky enough that Facebook was one of the first companies to use DocSend, so we were one our their talent acquisitions. Then we went and joined there and ran the product for the Pages team for a couple of years. It was zero engineers when I started and then we had four and then we relaunched it in the timeline design which they’re still using, and then I left Facebook ‘cause I wanted to start something again. I met up with Dave and Tony, and when we were starting DocSend, we didn’t know we were starting DocSend. We actually had a list of ideas because with Pursuit, I just saw something, and I said, “Great, you know what? We’re gonna build it.” Then getting a year into it, I was like, “I should’ve thought through this in more detail.”
Scott: More methodical, yeah.
Russ: We actually did a lot of customer interviews around asking questions of business like do we wanna sell software to car dealerships or maybe there’s another reviews website that needs to be made with a different take on things? The concept behind DocSend is basically the questions: Why do people still send attachments? We just interviewed a lot of people in different business contexts and trying to figure out, “Why do you send attachments? It doesn’t make sense. There’s just so many ways to not send an attachment.” The theory we had, and this whole time we weren’t writing any code because one of the problems as a software engineer is you just wanna write code. You don’t think a whole lot about what you’re writing code to do, and the problem is typically not that you can’t build it. The problem is that you build something that nobody wants.
Scott: That’s the Y Combinator thing. They always say build something that people want. It’s that simple. That’s the advice.
Russ: Seems like really good advice, yeah. We did all these interviews. What we came up with is it’s got to be easier to send a DocSend link than to send an attachment, and it has to provide enough value to the sender that it really changes their behavior. I always say you can’t prove something is a great idea. You give a period of time when you prove to yourself it’s a bad idea. We got through a lot of different bad ideas. With DocSend, we just like this thing should exist.
Scott: Like what? Whoever said this is a bad idea is on the DocSend [inaudible].
Russ: Oh my gosh, well, before it was DocSend, it was DocSha like document sharing, and we had a whole bunch of other really horrible names. DocSend was the only one that made any sense. We were joking with our employees the other day like, “If we were called, would anyone work here?” Everyone’s like, “Nope.” Nope. I don’t even know why the name makes sense, looking through the list of [inaudible]. It’s really hard to find a domain.
Scott: Do you look at co-founders and be like, “See I told you, we did the right.” Whoever of the three of you had the wrong idea there.
Russ: They made fun of me for coming up with such a long list of brainstormed names for our company, but DocSend was one of them. If you’re gonna brainstorm, you gotta a lot of ideas out there before you get a good one. Tony really wanted the company to be called Docraki.
Scott: Oh, like Dothraki in Game of Thrones?
Russ: Yeah, exactly. Yeah, exactly.
Scott: Think you made a wise choice.
Russ: Yeah, exactly. That’s a little whole niche. Anyway, we convinced ourselves that okay, this DocSend thing, this should be a thing that exists in the world. We’re gonna go build this. We raised a seed round maybe six months after incorporating. We probably spent three months ideating and interviewing people about the domain, raised a seed round, and then we raised a series A maybe a year and a half after that. In total, we raised 9.7 million. August Capital was the firm that led our series A.
Scott: You guys are doing really well. I see the product out in the wild everywhere, but do you have some stats on adoption? People who are listening to this podcast probably know it’s really well, but what’s the world look like to DocSend? You guys have such a granular view of all the views and the data.
Russ: Yeah, the data we have in our system is really cool. It’s also funny that we can see when people are working or not. There’s actually annual seasonality to our business. No one does any work in Q4, but it varies by different country. Then you can see over Thanksgiving, everything shuts down ‘cause DocSend is only used in B to D context, so it’s really neat to see that data. Yeah, but when we raised our series A in 2015, it was three years ago which is crazy, we weren’t making any money. We actually didn’t know what our business was. We’re like this is a great technology. You couldn’t even give us money if you wanted to [crosstalk]
Scott: You mean revenue like subscribing.
Russ: It was a poor choice. Yeah, this is what happened to me. I watch engineers build something. Build it and they will come and maybe we’ll monetize later. I don’t know. At that point, we raised our series A, we weren’t making any money. Since then, we’ve had to turn a great technology into a great business. We’ve got at this point, a little over 6300 companies that pay for DocSend, and they really vary in size. Everything from Pinterest down to startups by whole different use cases by vertical, so commercial real estate, consulting, a lot of financial services. I remember when we were starting off DocSend, we did this research piece on fundraising ‘cause we thought it would be cool to have some aggregate stats around that and so we got people to opt into it. We sent out a survey to people, being like, “Hey, would you let us use our stats. Privacy is a huge concern for us, so you’re definitely an opt-in sort of thing.” I sent out this automated email for people who filled it out, and it came back with billions of dollars that were already at that time being raised in DocSend. I was like, “Oh, man. I didn’t realize that there were these many people raising this much money.” It’s like a hedge fund. It’s like, “Yes, I raised 500 million dollars using DocSend.” I’m like, “Wow, that’s great.” Fundraising is certainly one use case, but of the 6300 customers, I think fundraising only accounts for 15% percent of our revenue. It’s actually a very small component. A lot of that is fundraising in the sense that most people don’t think of it, it’s not the startup fundraising. It’s a much bigger institution of some sort using DocSend for fundraising.
Scott: I totally would’ve thought ‘cause immediately my brain went to startups, but it makes sense that hedge funds or mutual funds or all these other folks would be using it.
Russ: Yeah, it’s so crazy as we look through our customers and trying to understand, wonder what they’re doing with it ‘cause there’s just so many different use cases. What’s neat is that everyone thinks it’s built just for them even though they’re all in very different lines of work.
Scott: Well, I used to work at a fund, and we had this super old school portal. You had to have a log-in and all this, and it was terrible. You guys basically replaced all that. It’s just so easy.
Russ: We became a cashflow positive flow recently, and it was basically by accident. We raised prices is, I think, the old joke for startups. You need more money, you just raise your prices.
Scott: That’s the moment of truth, though, when you do that. Did you guys have a big meeting and be like, “Okay, are we really gonna do this?” It’s a little scary. It could have a lot of turns.
Russ: It’s super scary ‘cause we used to have three plans. There was personal, team, and enterprise. Then as I was interviewing customers and digging through, ‘cause we hadn’t redone our pricing in a while, as I was interviewing people, I was like, “This doesn’t make any sense. Just the way we’ve set this up doesn’t make any sense.” A lot of customers were getting into the enterprise plan for some of the features we had there, but they weren’t enterprise. They didn’t need the other stuff that was there. When we relaunched it, we gave the personal away at the same price point. That’s definitely what startups were used to. We also will give DocSend away for free through incubators like Y Combinator and 500 Startups and a bunch of the other ones. We left that alone, but then we added the standard plan. It’s $45 bucks a month, and that’s basically what was enterprise but in a self-serve. You can get these deal spaces to feature in there which makes a lot of sense. It’s like you’re a professional. You’re a salesperson. You’re a commercial real estate person. Then there’s another plan for finance that is more security oriented, so it’s things like whitelisting and watermarking and stuff like that. The only difference between a deal room for a salesperson and a deal room for a financing person, it’s just the security controls on it. Anyways, so we broke those things out, and we just started making way more money. We increased our rate of revenue growth by 5X. That was pretty cool to see.
Scott: Take a second to talk about what a deal room is ‘cause I’ve used the products, I know, but maybe just describe it. A lot of people get the presentation in their email, but I don’t know how new the deal room is but it’s this world where you can see all your different documents. You can explain it better than I can.
Russ: Yeah, the request came in a lot of different ways. It was like, “I wanna send a folder of stuff. I can send a link to one document, but I wanna send a folder.” That’s one way people ask it. Actually, the way we built spaces was is it came as a request from agencies. We actually saw agencies paying people to build websites where they would embed docs and links inside of them. They’d make a website, and then it’d have doc and links in them. We’re like …
Scott: Oh my god, like a Google site or just an actual real site?
Russ: No, they actually used WordPress. Someone was coding things. It was like it doesn’t make any sense, but the presentation was so important to them. They were building these websites. Then we looked at our database. We’re like, “Maybe one way to check for this is to look for documents in DocSend that have docs and links inside of them. We ran a query on that. What people would do is in Google Slides or whatever, they would make a folder by embedding docs and links inside of another document and putting that document into DocSend. At that point, for this particular feature, we’re like, “Oh, people really want this feature.” When we built the send-a-folder feature, we made it look a lot prettier. They’re very easy to use. You can chuck a bunch of stuff into what is effectively a microsite, design it for whoever you’re sending it to, break it up into sections, but notes on top of things. We built it for the sales use case as a deal room as your deal progresses. Then people started using it in the financing use case as well. It’s really interesting. Whenever we build a feature, more people always end up using it than I ever think are gonna be the case.
Scott: That’s incredible, though.
Russ: Another example in the finance planning ‘cause we’re like okay, we gotta add more value to that. People are paying for it. That’s great. It’s very exciting. We listen to their requests. The one-click NDA came up, so ahead of getting into deal space, you gotta agree to someone’s NDA. It’s like okay, that makes sense. What I didn’t realize since then is a lot of salespeople need to sign in NDAs as well, especially if you’re in cybersecurity or something. You need to have an NDA signed ahead of doing a proof of concept ‘cause your messaging is critical to you. You don’t want it to get to a competitor. All of these things blend together in what is effectively a very similar use case. Our challenge is just to brand them separately and verticalize them differently and explain to people why it’s a perfect fit for them.
Scott: It sounds like you’re really good at teasing out user behavior and user requests, though, to figure out your product roadmap. That’s really awesome.
Russ: My background is, as a product person primarily, that’s been the most common job I’ve had. I don’t involve myself too much in the product at DocSend anymore. We’ve got Justine who’s our Director of Product Management who’s awesome, and she does a lot of really good work talking to customers and figuring it out. You never wanna build something that’s so specific for one person. You wanna make it general it in a certain way. I get a kick out of that where you can build software that’s just used by a variety of different people. That’s success.
Scott: You know when you’ve made it when people are doing that. That’s really cool
Russ: Yeah, whenever people use the software you’ve created in ways you didn’t anticipate … We had this thing recently where, for some reason, the ICO community just decided that DocSend was the best way to send out ICO Whitepapers.
Scott: No, that’s awesome.
Russ: I was like huh, I didn’t even think about it. I heard about this ‘cause our CTO, Tony, was complaining that the server costs were going up. I was like, Oh, I wonder where that’s coming from.
Scott: That’s good, though. It means it’s a lot of usages.
Russ: People sending their ICO Whitepapers all over the world is I guess that’s like free advertising for us. That’s nice.
Scott: That’s amazing.
Russ: That wasn’t the use case we targeted.
Scott: Going back to one of the first things you said was you have to create a reason for the sender to change their behavior which I think is so smart. I don’t know if this is the killer app for you guys, but getting those stats on who’s using it, who’s reading. As a sender, if I build a presentation in DocSend, send it out, I can see who’s reading it, who’s using it, what pages they’re on. Was that the killer app for you guys? Was that was swayed everyone to change their behavior and start using it?
Russ: I think people probably associate DocSend most closely with that per-page analytics. Another smart thing we did very early on is whenever you send a DocSend link to somebody, we’ll take a look at what company you’re sending it to, and then we’ll bucket all the data underneath that company. If I send a DocSend and link it to you, Scott, it’ll show up under Kruze Consulting in DocSend, and then I can see who you forward that to. It tracks the forward path of it ‘cause there’s always a unique link. I basically, if I’m using DocSend over fundraising, for instance, in DocSend, I have a little dashboard that shows me every VC I’ve sent my pitch tech to, who’s read it, who they forwarded it to. If someone forwards it to someone they’re not supposed to, I get that data …
Scott: That’s huge.
Russ: … Which is really helpful. If you’re a salesperson, you also think of the world this way, you need to figure out who’s involved in the buying cycle. You wanna take a look through the different prospects that you’re selling to. You wanna understand which of them are at risk, which of them care a lot, and who might be spending a lot of time in content and I didn’t know they’re a part of the buying cycle, I need to figure out what their agenda is.
Scott: That makes so much sense of the buying cycle, and you probably are picking up extra leads that way ‘cause they send it outside their company. You can see that, too. You’re like, “I sent it someone at Dell, and now this person at HP’s reading it. That means HP is a target customer, too.”
Russ: Yeah, yeah, yeah. It’s very exciting, although it’s surprising to people how rarely the content they send is actually read.
Scott: Like social media, not that many people are actually listening to?
Russ: Exactly like a Facebook post, got one like. Whomp, whomp. Yeah, so it can be a double-edged sort of thing, but then when people are looking at it, the nice thing is that there’s pretty much a one-to-one correlation between someone’s interest and if they’re reading the content you send them. That content usually is the highest value information for you. It’s your company’s branding, your messaging, that sort of stuff. We came out with some research recently called The Secret Lives of Prospects where we were just looking at the average number of people for mid-market deals that were involved in the buying cycle, and I think we came up with 5.4 or something, and just the number of pieces of content that were involved and that sort of thing. It’s just really interesting to see some of the stuff in aggregate, and I love having this much data for us as a company that we sit on top of because we’re getting got the point where we can actually do some really interesting research.
Scott: Yeah, also, every time someone new gets it, they get the chance to opt into the product and try it out for free and all that kind of stuff. It’s really powerful … What is it? I forgot what is. The coefficients? The new user coefficients?
Russ: The viral coefficients?
Scott: This isn’t a Facebook E-Term. Yeah, viral coefficient. Right?
Russ: Yeah, I was actually just looking at this the other day. I think it’s 28% of our users have come from having looked at a DocSend link, which is great, but 42% of our users have come from just typing in Our buyer reality’s actually more word of mouth than it is as a recipient, you become a sender. That happens, sometimes, but it’s less common than someone just saying, “Oh, I got this really cool new thing. You should try it out, too.”
Scott: Maybe it’s one of those things where they need to see it a couple times, then they finally type it in or something like that, yeah.
Russ: Yeah, we actually looked at this histogram for the people who sign up after seeing DocSend links, the number of DocSend links they had before they signed up. I remember one of them … We scrolled down to the bottom. Someone saw 427 DocSend links before …
Scott: They finally were like, “Okay, I’ll do it.”
Russ: What is this? Go ahead and get signed up for it.
Scott: Okay, doggie. Also, this is amazing. Your business is cashflow positive. That’s fantastic. How’d you get it there? Did you architect the sales cycle in self serve to be able to get you there? What was the thought process on that?
Russ: There is a lot of thought process on that. I’ve been a mentor for StartX for a number of years, although I haven’t done it in the last year, but it’s been funded by companies on that, and fundraising is a big part of that. I’ve done some angel investing on the side as well which is really fun. Somehow I always end up being the angel investor that has to help a lot.
Scott: I was gonna say everyone wants ‘cause you’re good at thinking through all these problems, yeah.
Russ: Or you just want help from someone who’s done it before, but for other startups, I always say when we raised our A round, there’s one mentality that says whatever you raise, plan to burn it in 18 months. That makes sense for some businesses. It depends on the type of business that you’re creating, especially if you’re going upmarket. You’ve got an outbound sales or you’re an enterprise motion, that makes a ton of sense. If you’re doing what DocSend’s done which is really tweaking things to get product market fit and really trying to have an inbound and very low cost and transactional sales model, that can take a little bit longer. When we raised our series A, we weren’t planning to burn in 18 months. We were planning to use that money as we iterate on the product and found our found market to fit. It just happens that by the time we did that, the revenue was high enough that we got to be cashflow positive which is actually a great spot to be in. As soon as you don’t need money, everyone would like to give you money. If you really need money, you can be in a really tough spot.
Scott: Yeah, sounds like you may have gone through that in your previous startup. All these lessons you learned at the company that was acquired by Facebook have now landed at DocSend where you have a cash flow of positive business, and it’s a lot of self-serve customers. It’s a little easier probably to run.
Russ: That is a very …
Scott: Maybe not easier.
Russ: That is a very nice property of our business is that … I would say how many people have called Gmail for support? No one has problem with docs, and it just does what it’s supposed to do. You can actually run a really lean organization that way. There’s no services component to it or anything like that. I definitely worked a lot working at Pursuit, although we didn’t actually spend any of the money that we raised. We did 500K. We were just doing it for years, just the three of us. Then we were like not working. DocSend, you get to the frontier of your own knowledge as you … It’s like the concept of everyone rises to the level of incompetence within an organization. I’m definitely in a new zone for DocSend.
Scott: That’s exciting, though. It’s probably fun for you waking up every day.
Russ: It’s super fun for me. Yeah, it’s great. We got a VP of Sales. I’ve got an inside sales team and so just watching them and helping them. I never worked in sales before, so it’s really fun to have all these functions of the company. Now we’re just hiring up on our marketing team, so it’s really fun to basically go through and figure out what type of people do we need? What are the skill sets? How do we define the role? All that stuff is super fun. Working at Facebook, for instance, as a Product Manager, the scale of things is much larger, but you’re in a corner of the organization. I’ve always liked being a Product Manager because you get to work with so many different other types of functions. Being a CEO is actually like that, just more so.
Scott: Pages is a big product. Everyone uses that on Facebook, so you were seeing this huge amount of behavior, and it was probably incredible training for running DocSend.
Russ: Yeah, it was, especially just getting buy-in across other groups inside, and there’s some politics and stuff with anything that large. Yeah, it was great. At one point, I flew myself around the world and just interviewed customers to get out of the ivory tower which was really fun. I went to Singapore and then I went to Japan. I went to India. I remember just being in Japan and having this Japanese company give me a presentation on how they use Facebook Pages. I remembered a stat from many years before, actually, while I was at Dropbox where Japanese businesses have the highest numbers of words per slide. Then when I got this pitch from this company in Japan, I was like that is absolutely accurate. I have no idea what’s going on [inaudible] page.
Scott: Why are they like that?
Russ: I don’t know.
Scott: Is it just thoroughness or something?
Russ: A couple different schools of thought for a presentation, certainly if it’s a leave behind, you wanna have text in there, but it doesn’t make a whole lot of sense to put something on the wall that has a ton of text on it and then also do a voice over because I don’t know if I should read to it or listen to you. Anyway, their pitch in Japan …
Scott: That’s how they roll.
Russ: There was a lot of information in there, and they had a lot of opinions on Pages, so it was very educational for me.
Scott: I love it. Another thing we were gonna talk about was, ‘cause you have different segments. You have, I think, the standard, and then you have enterprise. How do you decide what your target market is, or do you have a different team at DocSend going at each target market? How do you structure that?
Russ: Yeah, that’s always a tough question for startups ‘cause if you’re gonna go enterprise, you basically have to pick as narrow of a vertical as possible. You gotta sell big companies. I’ve heard that referred to as the bowling pin strategy. You can get an anchor account and then maybe give them a really good deal on it, make a case study out of them, and then go to their four other competitors and call them up and say, “Hey, you’re getting not good in the market because your competitor bought our product. You can buy our product, too.” You go from company to company that’s there.
Scott: It’s expensive sales people that have to do that, too.
Russ: Yeah, yeah, that’s an expensive sales cycle. If you’re doing what we’re doing where it’s more of a horizontal bottoms up sort of thing, and our product is freemium, and we intentionally made the price pretty low, so it’s a transactional sale, as you were saying earlier, you get to observe people using the product in ways you didn’t initially intend. That’s why we added the DocSend for Finance product. I would send this auto email to a bunch of people who were in some sort of financial use case. They all got back to me and said they’d love to talk. I remember talking to this managing director of an investment bank in Toronto, and he’s like, “I use DocSend every day. I love it.” He’s like, “It’s ridiculous. We don’t pay you anything.” I was like, “I think your secretary pays us $10 dollars a month.” He’s like, Yes, as I said, we don’t pay you anything.
Scott: You’re like, “Note to self. I need to change that.”
Russ: Yeah, note to self, this guy won’t care at all if I increase pricing on him.
Scott: Exactly, yeah, yeah, yeah, yeah, yeah.
Russ: If anything, he probably doesn’t trust it ‘cause it’s like, “It’s too cheap. I can’t pay this little for this.” A pair of shoes is too inexpensive, “Yeah, they’re not gonna last more than a week.”
Scott: I love it.
Russ: Yeah, so the pricing is a really tough challenge. Everyone says they’ve figured it out if they have, but it’s such a dark art.
Scott: We have the same thing. We never know if we’re not charging enough or charging too much. We find that it depends who you’re talking to that day. Startup founders are so opinionated on our services that we get conflicting advice constantly.
Russ: Yeah, we surveyed a bunch of our users when we were talking and thinking about launching this DocSend for Finance product. We’re asking them, “What else do you need in it? Would you pay this much? Would you pay this much?” There actually is a formal process you can use to try to find that maximum where enough people pay that price, but then if you go too high, then it drops with a number of people.
Scott: Then there’s a math equation. It is a [crosstalk] . Yeah, except maybe it’s just our customers. They’re too smart. Everyone said I wanted it to be free. We’re like, “How much would you pay for it?” They’re like, “$1 dollar.” It’s like, “Yeah, no. You’re an investment bank in Toronto. That doesn’t make sense.” They knew what we were doing. Then we had to be like, “Okay, we’re just gonna pick a random number.”
Scott: Then see if people churn it or not.
Russ: Well, the funny thing is that the upgrade rate went up. Normally, the upgrade rate will go down, but you make more money off each person and so you make more money in total. It’s like if it’s too cheap, you don’t trust it sort of thing when you hit a price point where you think people are just more comfortable using the software ‘cause they pay us a little bit more for it.
Scott: That’s awesome, and then do you think it’s ‘cause you’re gonna be around for a long time? Do you message the cashflow positive nature in your press and things like that because you wanna instill that in the customer base? You can trust us. We’ll be around or a long time kind of thing. Is that just … Am I overthinking it?
Russ: Yeah, I don’t think that’s been a concern, really. Sometimes if we’re signing a much larger customer, hundreds of thousands of dollars a year … We’re an interesting business in that there’s a really wide range of sizes of companies that use DocSend. We’ve got some opportunities in our pipeline that are a million dollars plus which is a big deal for us. Those companies are the ones that are like, “We gotta see your financials.” You’ll have the conversation, “I wanna make sure you’re around. If I’m even signing a two-year deal with you, I wanna make sure you’re around.” For the self-serve side of our business, I have no idea if it even occurs to anybody.
Scott: Probably not, yeah.
Russ: Yeah, it’s just software they were told that’s useful, and they’re gonna sign up for it if it works really well, and it’s free.
Scott: It’s a monthly thing, and they can cancel if they need to or something like that. Heaven forbid they actually cancel. One of the other things you talked about was a positive NPS. Do you know your absolute number? If you don’t wanna share that, that’s totally cool. As a company, do you stress that? How do you guys talk about it internally?
Russ: We never have measured NPS scores in the official way of actually asking people for the NPS score. There are a lot of anecdotal ways of testing for us. When a company churns, we’ll reach out and ask for feedback. It happens very, very rarely. It’s really hard if you’ve got, especially, a company like 10 or more people using DocSend, to remove it ‘cause all your content is out there with DocSend links. You can get off of it, but it takes a while, so very, very low churn there. Typically, companies churn if they go out of business is the primary reason. Then wherever they go next, they’ll use DocSend there as well, so it’s interesting to see that people, as they move companies, they’ll bring DocSend with them which is a very, very good sign.
Scott: You’ve really built a really cool business, and it’s just so viral. It’s amazing.
Russ: Oh, thanks.
Scott: Going back when you made this huge list of functions or features your company would build in different industries, did you purposefully build something so viral, or was that just a happy accident in the way the product was structured.
Russ: It was more of a happy accident. I think for a lot of entrepreneurs, they’re solving a problem they themselves have or at least they’re solving some problem that really irks them, especially if you’re doing more of a bottoms-up type of thing. You’re doing an enterprise sale, you might actually have a very specific knowledge about the problem that you’re solving. For me, it was really just annoyance that people still send attachments. Then we thought people would be using it for internal use cases as well, and some companies do. People use DocSend for their newsletters and stuff like that. By launching it, and then seeing what happened and who used it, it really highlighted the B to B use case as being just such a critical one, and so that continues to be where a lot of our usage comes from. It makes sense. Everyone’s insecure. You send things. What happened to them? Do you care? That is, also, just naturally viral which works out well for us.
Scott: We talked about this before I turned the mics on, I love when VCs complain about the accountability of DocSend on Twitter. “Don’t you dare send me a DocSend presentation. How dare you!” Does your mentions light up or anything like that? Do people come up to you at a cocktail party?
Russ: It’s probably my primary use of Twitter these days.
Scott: Is it?
Russ: It’s just listening to these conversations. It’s especially funny when a VC says, “I’m gonna build a scraper for DocSend use.” My first thought is you shouldn’t say that on Twitter. It doesn’t make you sound very entrepreneur friendly. DocSend, people can turn on downloading. It’s very easy to do in the system, so when people are turning off downloading, it’s because they don’t want you doing things with their tech that they don’t allow you to do. We’re just the arms dealer, the middleman, in this, and it’s really a data rights question. Who owns the data here? Is it the sender? Is it the receiver? In an attachment based world, you get the attachment, it’s yours. It’s yours forever. In the model that DocSend has, it blurs the lines a little bit. People will still screenshot DocSend links, but we can’t prevent that, so we’ve never said that we’re completely making it secure. There’s no way to do that. The pixels are on someone else’s screen, they have your data. It’s just more annoying for them to …
Scott: It’s inconvenient for me to send to their friend.
Russ: Right, and so as I was saying earlier with the amount of revenue for us that comes from fundraising, it’s such a small amount. It’s not a market that matters for us. Unfortunately for VCs, they’re just collateral damage. That’s a huge case where a technology like DocSend has a clear fit. If we didn’t do it, somebody was gonna do it.
Scott: Totally, totally. Do you have any good stories of a VC who drank too much at a party or something, coming up and getting after you? Is it just Twitter mentions? They seem very passionate about it. It really bothers them.
Russ: Very, very passionate about it.
Scott: It’s weird.
Russ: Yeah, people are always very reasonable in person, although well, I’m trying to think. Yeah, some …
Scott: There goes that guy Russ.
Russ: Some people have really tried to make me feel bad. They’re like, “You realize it just doesn’t matter. Security is an illusion on the internet.” I was like, “I know. That’s not my problem.” It’s like, “That’s not what we’re building this for.”
Scott: I’m just trying to get some stats to the person who sent it to you.
Russ: Don’t blame DocSend for this sort of thing. You can always ask them to turn on downloading. You could try that. Actually, the very first DocSend link ever sent was to a VC, and I won’t say which one. Our C pitch deck, the first page was our team page. Me, Dave, and Tony, all Stanford CS engineers with good backgrounds. It’s a good founding team. This person opened the DocSend link, went to the team page, didn’t look at anything after that but replied saying, “I love what you’re working on. I can’t wait to hear more.” I was like, “We don’t have a website. There’s literally nowhere you can learn what DocSend is, and you were the first person to get caught in the act of lying about what you …”
Scott: Peer pattern matching. Then at the moment, you’re like I’m onto something. This is gonna work.
Russ: Yeah, exactly. Actually, he did forward it to a colleague, and then I met with that person, and we were laughing about that.
Scott: You’ve built an awesome company, awesome product. People love it. Can I ask one South Dakota question? Oh, of course. My roommate from college was from SoDak, as he calls it. He claimed it was the 49th worst state because North Dakota was worse than South Dakota. Do you think of it in that way? He didn’t have a lot of SoDak pride. He was glad to go to California.
Russ: I like South Dakota. I was back there for a wedding …
Scott: I like it, too. I went to the …
Russ: … Three weekends ago.
Scott: What’s the monument? It’s amazing.
Russ: Mount Rushmore.
Scott: Mount Rushmore and then also …
Russ: The Badlands.
Scott: … The Native American monument and the Badlands. The Badlands is amazing.
Russ: Crazy Horse, yeah.
Scott: Crazy Horse, yeah.
Russ: Well, it’s true that there is a rivalry between South Dakota and North Dakota. It’s a rivalry that no one else even knows about or cares about. I think probably in reality, the U.S. Should be shaped like the cold fronts that come down from the North with a U in the middle, and they should just give both Dakotas to Canada ‘cause they feel more like Canada than it does like the rest of the U.S. There aren’t that many people there anyway.
Scott: I [inaudible] through there many times and spent time there. It’s an awesome place..
Russ: Yeah, it’s a really fun place to be from. Not that many software companies, though. There’s one in Sioux Falls called Click Reign. It’s doing really well.
Scott: A friend of mine’s a CFO, and one was just trying to recruit him. It’s a software company. I was shocked. Anyway, total digression. Russ, thank you for coming by. Can you tell everyone where to find DocSend and give the quick pitch again?
Russ: Yeah sure, so DocSend is just D-O-C-S-E-N-D. One other little funny story, when we go to career fairs, we’ll often have people come up that are pre-med or in medical school. At first, we didn’t realize what was going on, and then we realized that they thought we were sending doctors. DocSend as in doctor sending.
Scott: Doctors on demand.
Russ: I will with a straight face tell people that we used to do that, but we had to pivot because doctors are large.
Scott: Too expensive.
Russ: They’re loud. They’re annoying. They’re very expensive to send places. We had to pivot into documents where we had the perfect name for it. People hear this and they’re just like, “Is he being serious? I don’t know.” I was like, “Unfortunately, we can’t send you anywhere. I’m sorry.” Then they walk away.
Scott: Oh, that’s amazing. That’s amazing.
Russ: Yeah, just Send links instead of attachments. See who’s reading them. See where they forward them. Really easy to use software. It’s self-serve. There’s a free trial, too. You can use it. I’m just if anyone ever wants to get in touch, or @rheddleston on Twitter.
Scott: It’s a great product. Congratulations. I’m really happy for you.
Russ: Great. Thanks, Scott.
Scott: All right, Russ. Bye

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