This Week in Startups - DocSend CEO Russ Heddleston on pitch deck insights, leaning into criticism & more | E1161

Episode Date: January 13, 2021

Check out DocSend: https://www.docsend.com Check out DocSend's Fundraising Network: https://www.docsend.com/fundraising-network FOLLOW Russ: https://twitter.com/rheddleston FOLLOW Jason: https://linktr.ee/calacanis

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topsy-turvy. Download and subscribe on Spotify, Apple, or wherever you get your podcasts. Hey everybody, hey everybody. Welcome to another episode of this week in startups. I am really excited to have our next founder on the program because you've all gotten his links in your email. But it's a little bit uncomfortable. It's a little bit uncomfortable because, you know, you do a podcast, you do 1,100 episodes, and you try to keep it real.

I always try to keep it very real for people on the podcast. And so I give you my candid opinion. And sometimes I say something and I'm like, well, I think Robin Hood's going to have a better IPO than Airbnb when I did my IPO episode. And lo and behold, ding, ding, ding. What are the founders of Airbnb? It's like, hey, I'm just watching the show. I think we might do better than Robin Hood. And I said, well, great, can you come on the show?

And so in 2021, we will have one of the founders of Airbnb on the pod. He said he loves, he's a big fan of the show. And I just had done a throwaway comment. Hey, throwaway comment. I don't know. I invited the guy from Airbnb on a couple times. He said no, so I don't know, maybe he doesn't like me. And he wrote me, he's like, I love you.

I think your podcast is great. So one of those throwing comments I had was we were having a comment about one of my investments, Superhuman. And I had previously had David Hammeyer Hansen on, or maybe it was Jason Free, and they were talking about their new email product, Hey.com, which took up all the room in the, all the air in the room for a couple of months there. And he was really going hard at Superhuman, which is one of my investments. And I invested in Rahul twice. And one of the things, he was like, oh, my God, read receipts. You're letting people, you're spying on people. tracking their emails. And I'm like, yeah, I guess they do have that very subtle feature.

We're in Superhuman, you know if somebody's open it called read receipts. And I said, well, it's not as as Doxend. I hate that company. I can't stand in Doxend. I get those Doxend links. I can't take it. Because all these founders send me a Doxen link to protect their IP. Rightfully so, it is their right to do. And they want to know what pages do investors look at when they get their decks. And we've all gotten them as investors. And the cognitive disdiscuit. then hit me in the head. I was like, oh my God, I can't stand this being tracked, but I kind of love my founders being able to track investors and have some information if they open the deck or not. And I always told people, I don't open doc sends. I don't open spyware. I don't want spyware on my computer.

I just send me, and I was being hyperbolic, but just send me your deck. Or I would go to a website. I don't know. Some website, we can convert a doxend into a PDF. And so anyway, Russ Edelston is the CEO and co-founder of DocSend. And it turns out he's a delightful guy. And I listened to a podcast with him on one of these SaaS podcasts. There's a bunch of SaaS podcasts out there. And he's a real genuine, hardworking founder. And he just emailed me and he's like, I don't know, Russ, what you said.

Welcome to the program. But you said like, hey, I'd love to be on the pod sometime. And, you know, the product's not all that bad. And I was like, oh, no, it's another one of these situations where I was a little brutally honest about my opinion. And now I've got to own it. So let's, number one, thanks for reaching out and coming on the pod. Let's just tackle the issue that I had from the beginning, which is, hey, doc send.

Let's just, you know, clear the air here. What did you think of my criticism when you heard it? It can't be easy being a founder. And then, you know, I'm not if you're a fan of the pod, if you've heard of it before, if one of your friends told you of it. No, I'm a long-time listener. I'm a big fan, Jason. So I appreciate you having me on.

It's actually the thing I had to do yesterday in prep for this was I had to listen to you at normal speed because I always listened to it at one and a half X. And I was like, I wonder what it sounds like at normal speed. I'm already talking too fast. It's hilarious. You just made the whole producer channel light up and laughter. So I think it's very big of you to come on the pod. I don't even remember what discussion. Do you remember what discussion?

And this is the nature of my life running this podcast. I can't remember what episode out. Who was I talking to? What was the context? What did I say? It's pitch.com, kind of the PowerPoint competitor. Oh, right. Which I think has a little bit of doxendish stuff in it.

I've always said I never want to compete with PowerPoint. But no, I don't take it personally at all, Jason, and I always appreciate your candor. So I just thought it might be, you know, fun to have a discussion and just share a little bit more about what's behind it. Because a lot of people don't really think about us as a company. We have been running under the radar for a while, but we have over 16,000 customers. We're profitable. We're growing really quickly.

I heard eight figures in revenue. You guys get tens of million in revenue. You've been incredibly capital efficient. And as we get into it, let's start off just talking about the issue of tracking people looking at decks, just as an issue. How do you think about that? And how do you frame it with people who use the product and then customers who maybe are privacy sensitive? Privacy sensitive. Yeah, it's a great question. And it's a, it's a thorn. one too, right? Because it's really at the sender's discretion, what they want. And I certainly that agree that for some materials, it's, you know, you do want to have a local copy. And the sender can always turn on downloading. And once you download, we stop tracking. It's just in the browser. So

we're not doing tracking at any level that is kind of above and beyond what any other website would do. We're just taking a document making into a website and, you know, showing engagement information. And for some people, that's really critical and valuable. Oftentimes in fundraising, where we get used the most is, or the beginning part, is just that pitch deck that gets you the meeting or not. And there are a few things that are unintuitive there about why analytics are helpful. That document gets updated a lot. Like you, Jason, are looking at these things really fast. On average, investors only spend, but it used to be three and a half minutes per pitch deck.

Now it's down to three minutes per pitch deck during the pandemic. It's a whole other story. But then, you know, there's a lot writing on that. The founder's updating it a lot. So if I send you, you know, an attachment, which is my deck, and then I don't hear from me for three days, but now I've suddenly updated a bunch of stuff in there. Do I send you the new one?

I don't even know if you've looked at the old one. And it's just kind of an awkward way to start off. So I can see if you've looked at it. I can update it. I never have to tell you that I updated the thing. So you basically have this way of controlling who has seen what and having this audit trail. And the per page analytics are useful sometimes,

but more just like, you know, do you look at it? Did you care? So the flip side of this is that when you spend time reading someone's deck, you're giving that founder a really big compliment because you're giving them your time. So, you know, in some instances, you're like, yeah, I don't really want to know. But it does dissuade a practice where investors will just forward decks to other investors. Yeah, that is completely unfair. And you're protecting them there.

And it really is helpful, as you're saying, to know that the deck was opened. And it's helpful to know what page is. people dropped off on or they zipped forward or they zipped back. And in fact, I was literally getting prepared for the podcast this morning and I realized, oh my Lord, I'm a double hypocrite. Number one, I love that. I love what you do for my founders so they can tell me, yeah, you know, five people in the, at this venture firm opened our deck. We sent it to them and they've been in it like 10 times. Right. Like the partner says, I'm going to send it to my other partners and then they don't do that or they do that. And that tells you everything about how

really engaged they are, you know, and how likely they are to lead around. And the interesting about that was when I was starting the company Mahalo back in the day, I was, had created accounts for people to test it. And it had like a sort of like a little bit of a deck kind of thing, but it was more like an account to go check out like the prototype. And my tech guy goes, oh, do you want to track everybody? And I was like, yeah, well, what would that look like? And he's like, well, whatever you want. And I said, okay, just can you send me an email anytime or, you know, and he goes, well,

I made you a webpage. And so any, it will send you an email, you can notice web page and you can see everything they did. Long story short, I sent it to one of the most famous people in the world at the time, who's no longer with us, who was running one of the big tech companies. People could fill in who that might be. Like literally the one of the most iconic people in the world. world. And I sent it to him that day, and I had met him before. And I said, here's a new project

I'm working on. And sure enough, at 1.30 in the morning, I get an email. And then I see, this very famous person is going through the website for 45 minutes. And it was a search engine. And this company didn't have a search engine. And I was tracking them to make sure I knew if they were going to go see the prototype. So this idea of tracking people, if both people understand it, so do people understand when they go to DoxN that they're actually being tracked or not. I guess that's where the, you know, the criticism of superhuman was coming in is that people weren't tracking it. People don't know they're being tracked. And I guess for outreach and sales force and any number of products, people don't know they're being tracked necessarily unless they're sophisticated

users. So we can get back on this quick break. I want to know in the industry, if there is a standard yet for a global or a how the industry thinks about letting people know who are clicking on the link, hey, you're being tracked. We know if you've seen slide seven or in another product. We know if you've watched the video or not. Wistia, as an example. You can see in Wistia how far people have watched in the video when we get back on this week in startups. It's a new year. It's a fresh start. And you've got your small business over here, your medium-sized business, and you are now shifting business hours. Maybe you're hiring more remote employees. But the one thing that remains unchanged in the sea of change that we just experienced in 2020. And let's face it,

2021 is still going to have a lot of change, especially the first half. Well, you need to have the right people on your team. This is going to be a constant. No matter what happens in the world, talent is the most important thing for you as the founder. And the best way to hire people, we all know this. You know this, I know it. It's LinkedIn jobs. They can get you qualified candidates and they're going to find you the right person quickly.

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LinkedIn.com slash twist. Terms and conditions do apply because they're giving you 50. Welcome back, everybody. Russ Hettleston is with us. Thanks for coming on the pot. He's from Doc's End. They've got, I don't know, 50, 100 people working there now. Yeah, about that 55 or so.

Yeah, hiring is currently our bottleneck. I guess as we wrap up this sort of first segment on just privacy in general and privacy in the enterprise, what is there like a ground rule for the industry? And obviously you have to deal with now GDPR in Europe. And what's the California Privacy Protection Act? Is it CPP something? Anyway, we have those two really super duper hardcore privacy acts. Do those impact you? And then what is the industry standard?

And what are your thoughts on informed consent from the recipient? The person who opens the deck and is being tracked and maybe doesn't know they're being tracked. Yeah, it's a great question. And we've kind of gone back and forth on this. What we found is often that our users or new users will be worried about their recipients and if their recipients care. but by and large, we haven't really gotten complaints from recipients. Everything is cookie-based. So Doxend is fully GDPR compliant.

We comply with the California Privacy Act as well. And, you know, if you just delete your cookies, then, you know, we stop that. There's also an option as the sender of a link to request your email address. There's even an advanced feature that says you have to authenticate that you own that email address. We never make a recipient create a Doxend account. That's one of our differentiations. But as a sender, I have a lot of nuance control around what I'm requesting from you. So if I send you a link and I don't request email, it's just anonymous.

However, because of the way our system works and every time you send a link, it's a unique link, I would know that this link has just been sent to Jason. Another thing we do to protect the recipients is that if we've seen you before Jason and someone new sends you a docksend link and they ask for your email, we'll auto-populate that email, but you have to hit OK to give it to them. so they know who you are. And so that's in our mind kind of like the right compromise to have. We could, for instance, make it much more in your face around like, hey, we're tracking you.

And we actually did try that out for a while. Like we would show you the recipient, your own stats just to like let you know about that. But by and large it didn't really make an impact. And then the feedback we got from our users is that detracts from the content itself, which is what I want you to spend your time on. So it was viewed actually as salesy for Doxand in a way that detracted from our product. So, you know, I don't think there are any industry standards. We try to do the right thing.

We comply with all the regulation. But it is kind of the nature of the internet that based on cookies and like where you're spending time, all that stuff is being tracked anyway. It's just a question of in what ways is that surfaced and whom is that shared. It does seem to be a one-sided concern. Mark Suster absolutely demolished you back in 20. 2018 saying you should not use stock send. And, you know, on both sides of the table, he wrote, I know everybody told you to send your fundraising decks as a league. Here's why you should send a deck.

And, you know, the founders are like, the deck could have a spelling error in it and then it lives there forever or it could not have the October update and I sent it to you, you know, whatever date. And then you opened it two weeks later and I have the new data. So why wouldn't you want the new data? And what was your thought when you saw the, the both sides of the table post. Because I guess the issue is, do you build which side of the table, using Mark Suster's own words,

both sides of the table, and in his blog that refers to the founder on one side and the investor on the other. What was the climate like in the office when he wrote that blog post? It just gave you more customers, ultimately, I'm sure. It seemed like a nice form of advertising, although I think in his post specifically, he took great care not to mention Doxon by name,

so he didn't give us free advertising. He didn't give us free advertising. You know, that's fine. Oh, that's a bummer. Yeah, you should have told him like, hey, listen, if you're going to call me out, put a goddamn link in the first sentence. Did you reach out to him? I don't think I did, no. See, you've learned your first rule today, Russ. I know. Yeah. Of criticism, which is engage. Engage your critics. engage any criticism because every piece of criticism is like a roadmap to making a better product and just talking to you and working through my own cognitive dissonance, I just really thought of an interesting way to do it, which is, you know, if people had the ability to do the handshake agreement, when you send a doc send to somebody, when they click on it, if I had,

I want to do the handshake agreement, it just shows a picture of two handshaking and it says, you get the most updated deck. We know when you've read it and, you know, what pages you've looked at, and you just click okay. And so you kind of put it in the user's hands that they can do that. Is that how you do it now? Does you just have the ability to put like a little warning there when you put in your email address? Hey, by the way, wanted to let you know that we know when you open this and what pages you look at. Kind of like the little warning you get when you use Facebook to authenticate.

It gives you the blowpoints to kind of educate users. Have you considered that? Well, we've thought about it. It just has never really risen to the level of concern. Like, for instance, in 2018 and 2019, 50% of venture capitalists that raised a fund successfully used Doxend for their fundraise. So, you know, people will complain about it on the one hand, but then they'll often tell their founders to use it on the other. And so there's been kind of an organic awareness of what is Doxend and how it works. So to take up more UI and to interrupt the flow there,

It's just not been something that's risen to the top of the list. We also just try to be really helpful to the startup community, even though it's a minority of our revenue. It's not that much. But we do some really interesting marketing. Like we have a free intro service called the Dox and Fundraising Network, where for pre-seed and seed companies, they send us their deck.

If it meets our bar based on some tech we've built and kind of a human review, then we'll actually match them with lead investors for pre-seed and seed. Oh, wow, that's cool. Yeah. Because it's just a nice thing we can do. What's the URL for that for people who want to try it? It's just... I'll give you the plug.

I'll give you the plug. It's just Doxend Fundraising Network. If you just go to Doxon.com under the resources tab. DocSend Fundraising Network. There it goes. It filled in. For those of you who want to check it out, that's a great idea. It's very helpful.

Doxend.com slash fundraising dash network. Wow, that's great. So you're putting your time and money into helping people find an investor. Very cool. Yeah. So, I mean, it's good for the investors, right? One of our investors, Uncourke led around recently in a company that we sent it that he wouldn't have seen otherwise.

Very excited about it. Oh, wow. Yeah, Jeff Clevey, a good friend of the pod. He's been on a bunch of times. What do you think when somebody makes something like deck, the number two, pdf.com, which is what I use sometimes if I, if somebody on my team gets a PDF, a doc send, I say, just give me the PDF, send me the PDF. And, you know, I have different security concerns than other people because, you know, I'm a little bit higher profile and people are trying to hack me to get to Bitcoin wallets or whatever.

So, you know, having my IP address out there or anything that could potentially, you know, loot me in. I use all kinds of tricks to keep myself secure. And you guys don't make the website deck to pdf.com, I'm assuming. No, we do not, although that would be fascinating if we were our own enemy just to create controversy. No, so we know when people use deck to PDF or any of the other scrapers and we alert the sender. So, you know, that's just the signal you're sending to them, that that's what you want to do. But that's also just in the basic Doxend version, the personal plan, it's like $10 a month. If you use the advance plan, which is what financial institutions use, or if you're going to

use it for investor relations or board updates or you're an investment banker, you're going to M&A, use our advance plan. And in that one, we're able to block all of those services because we have some other features in there that preclude them from being able to get in and scrape it. So it's not a problem by and large for our larger customers. And it's just really in the startup fundraising world if they're using the personal plan. Let me ask you a question about pitch.com, really slick product. And you make the, and basically their value proposition is, hey, you make a deck in keynote or PowerPoint.

And then you make docks. You convert it and you upload it to docksend. What if those two things were put together? That's their basic value proposition. So when you watch that podcast, I'm curious, as a founder, a new competitor, comes out and they decide they're going to put two things together. When we get back from this commercial break, I want to understand when you have an at-scale company that's got a huge loyal fan base and you've got, you know, tens of millions of dollars

in revenue, you guys are incredibly capital efficient and you have a product that requires zero marketing. Every time somebody sends a docusend link, you get all that built in marketing and they have to put their email address in and the workflow starts. And we all know this Dropbox style phenomenon, and you, in fact, were an intern at Dropbox. We'll get to that. But I'm curious when you watch as a founder of the pitch.com podcast where this comes up, how do you, as a leader of a team, this is inside baseball, but how do you reconcile investors emailing you, your team, and even yourself and your own psychology of dealing with the new competitor that is going to stand on your shoulders? And they're specifically doing

that saying, hey, you use Product A, we're putting peanut butter and chocolate together, and you're going to love this new variant that we're creating on top of their shoulders and we get back on the sweet startups. Do you ever wish that you invested early in some of the best performing IPOs of 2019 and 2020? I bet you did. Well, our crowd investors were able to invest in many of those IPOs because our crowd allows accredited investors to invest directly in these startups. And they can do it easily and they can do it early. And that's what it's all about. And you know, these companies go on and sometimes they IPO and other times they get bought. Our crowd investors benefited from investing early in companies like BeyondMeet that IPOed.

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and then you can start investing. Our Crowd is free to sign up for, and you just go to O-U-R-C-R-O-W-D.com slash twist. Okay, let's get back to this amazing episode. Welcome back to this week in Startup. The founder of Doc Sand is here. His name is Russ Hettleston. You can follow him on the Twitter, R-H-E-D-D-D-L-E-S-T-O-N,

and he is active on the Twitter. So tell me, Russ, when you see competitors taking and you're a horizontal service, horizontal meeting, anybody can use you for anything. A student could use you in our project, a VC raising money for their fund or a founder trying to get that money from a VC or anybody in between. What do you think? And then how do you deal with it internally? How do you deal with it with the investors and how do you deal with it with your own psychology? Yeah, that's a great question. And it, I mean, as you well know, like as a founder, you have to have deep conviction in something

and building a company is much more of a marathon or a super marathon than it is a sprint. So, you know, there are a lot of things that have happened historically to Doxon where big public company says, hey, we're going to clone your entire product. And, you know, it's like, okay, that could be scary. Or apparently there are a lot of like Doxen killers that investors get pitched on in various forms. Yeah. Yeah. And so I'm flattered by that. I mean, I don't think we're at the scale that, you know, someone should try to copy us. You should be going after a really, really big market. And I do think Doxon is going after a big market. I don't think we're, we're not a public company yet. So I don't, And we're also pretty nimble still.

So I don't think we necessarily the best to compete with. The conviction I have is, and why we started Doxend is that years ago, we saw that creation of documents and collaboration were going to go hand in hand. I interned at Microsoft and undergrad. And I really don't want to recreate PowerPoint or keynote. Those products work fine. And that's hard behavior to change. So we saw creation and collaboration going hand in hand. And then file sync and share, it has less value proposition.

But then we saw this external sending thing. And there are all these niche companies. There's like diligent or introlinks or all these, you know, like sales enablement players or, you know, even LinkedIn has a smart links thing. And so what we want to do is just, and our mission statement is to combine common workflows for sending documents externally into one intuitive solution, which also means that we're building out the full virtual data room feature set. And we're also building out the full e-signature feature set. So we want to combine all those into one. So if you take that lens on things, if pitch, uh, it adds some basic tracking function out on top of it.

That's awesome. They should totally do that. That's really, really smart. I still think as a market share of the world of how people create decks, I'm not too worried about them taking over. Like most of our users are already trained on keynote and PowerPoint. They'll continue to use those things.

So, I mean, we always say that we're running our own race. And, you know, I'm pretty open. A lot of founders are very secretive about what they're working on. I was like,

well, no, here's our traction. Here's our roadmap. app, like, here's the theory we have. And, you know, no one else has the exact same view that we do on the market. Well, and you worked at Facebook. So you got to see this firsthand, correct? Yeah, that's actually a funny story. Like, so the first startup I had was talent acquired by Facebook. And as you know, when someone says acquired, that can mean a range of things. In our case, like we- What does it mean aquired? Yeah, exactly. They can mean a lot of stuff. But we had to start up before, me and two other

co-founders, and we raised the seed round. I didn't think it was going to work. So we're going to pivot, Facebook used it early on. And so we interviewed with them and LinkedIn and decided to go to Facebook. And so it was a great outcome. I got to have some great experiences there. I also realized while I was there that, you know, I talked to founders and they're always very cagey being like, oh my God, you're going to copy my idea. And my response was like, no, I'd be terrible at my job. If, you know, some founder says, here's this thing. It's like, there are no new ideas. They're all in a spreadsheet. The founder has more to gain by sharing with the big company at that time me. because then I could give them feedback on why we think that is or isn't a good thesis

and why now might be a good time to do that or not. So fast forward to when I left Facebook and we started Dox End, one of the first things I did was went to every other big company that I thought should build out the concept behind Dox End. And we got some talent acquisition offers, but like no one was going to build it. So we were like, okay, I guess we have at least a few years to like make a go at this. And it turns out we had even more than that. And still there's nobody who's thinking about it exactly the same as we are.

Yeah, it does get into people's head, you know, like, oh, my God, talking to this company and trying to be protective of your ideas. And what really matters is execution. And if you just look at how long it takes, you know, for a company to copy another person's idea and their likelihood of doing it, in all likelihood, they already know the idea. It's a 98% certainty that at some offsite, a bunch of Facebook executives, you know, who are trying to one up each other are going to come up with great ideas around some roundtable while, you know, at some corporate, you know, retreat. It all goes into some spreadsheet somewhere with all the ideas or maybe today on a

notion or a Coda page. And then they have to build a roadmap. And when you're building at scale, it takes, you know, 12, 24, months to roll these products fully out, you know, to the base of users. So they get to like fire a bullet every whatever, six months or every three months as an organization. They may have five or six products getting updated. The likelihood of them stealing your idea is incredibly low. They probably have it in that Google sheet already. And they've only can do four of those 400 ideas. Is that kind of what happens? That's kind of what happens. Yeah, you can only make a few bets.

Like it's interesting being at Facebook. I mean, the kind of pattern that I saw a couple of times is that Facebook would want to build a new product. Internal resourcing was hard. And then someone really senior would say, okay, we got to move faster than they'd buy a company to plug that hole. So if a big company is really coming after you and you are their big bet, they'll usually approach you first

to buy you. But even then is the company you have to consider, like how well are they going to execute against it? Are they thinking about it exactly the same? And I think by and large for startups, just keep building your vision out. And don't stress. too much about what other companies are doing or what they're saying.

At least that's been our thinking so far. And having vented some big companies, I think that's by and large true. There are obviously counter examples to that. But everything is already on the spreadsheet, as you said. It was interesting about your previous idea of pursuit. I remember this time period in the 2010-2011 time period, right when this boom started, right? You started that company.

right after the financial crisis or there about? Yeah, I was in business school actually at the time. So we kind of had the idea in 2009, 10, and in 2010, we started building it out. And what we probably should have done was build out an ATS, like a greenhouse or lever. But we instead tried to build out a recruiting product to help with referrals at companies. And so that was a great experience for me. I learned a ton in kind of launching something for the very first time. But yeah, that was an interesting period of time to start a company because everyone is still recovering from the financial crisis.

But there are a lot of great companies built out of that vintage. Amazing. Yeah, I mean, that's when I started angel investing was right around that time. So, you know, if the market crashes in the next two or three years, just so, you know, that is the time I'm going to push all the chips in, which is essentially what I did during this financial crisis that happened in March and April. I just put my equities in wealth front on 10 and poured a bunch of equities and then started investing in more startups. I knew there would be a lull. Pursuit was a pretty good idea, actually, your previous company, which was using social networks and your sort of your network to then win to get bounties or, you know, what do they

call them? A referral bonus. A referral bonus, right. The referral bonus was a big thing when there was a talent more. But that business didn't work or it was just too small of a business? It didn't work. She said you learned a bunch. What did you learn about why it didn't work?

and then take me through your process of saying, I'm giving up, I'm just going to sell it and go work at and lick my wounds and work at Facebook for a couple of years. Yeah, so I had two co-founders who are also engineers, like I'm a software engineer by background. And we were solving a problem that we had, like scaling engineering teams

and found that most of our best hires were referrals, but there wasn't a great way to, you know, kind of programmatically do that. And so, you know, we actually had a bunch of ideas on a list, and this is just the first one. And I said, okay, we'll just try to see how it works. So one of my big lessons is like, you do not have that much time as a company. As soon as you start writing code, you're really entrenching yourself.

So we ran it for about a year. We launched it. I think we got like 50, 60 companies signed up using it. And the real big like oops moment was that we realized the people who do make the most referrals and are best at making referrals. Like I'm sure, Jason, that you make referrals to your companies all the time. You're probably a great source of like, you know, someone, a talented person. and looking for like their next thing, you're connecting them to the right people.

But once you get money involved, people feel weird about it. So we were actually... Incentives matter. Incentives matter. So we actually did get a lot more sharing of job opportunities, but people went out of the network in order to refer those people. They didn't go back through. So our kind of thesis around money itself could help motivate people to spread the word about

high value jobs ended up just not being quite right. So... It's interesting. Everybody's kind of learned that over time. I remember at my couple startups ago, Mahalo, we had Mahalo answers and Quora had done a Q&A site, and Google was actually doing a question and answer site like Quora. And they were paying researchers at Google for this Google research project. I forgot the name of it exactly.

I might have called the Google Answers, actually. And they had full-time librarians who you could pay 30 bucks to go research something for you if you needed it, right? So if you're like, I need to know more about this. And that was just a particularly hard search to do, they would do it for you. and Quora added some kind of gold or some kind of way to incent people and you could earn gold and I could earn gold and that would help you promote stuff. And it turned out that's not why people use Quora. The reason people use Quora is like you did when you started DocSend is like somebody's

like, how do I put a password on a PDF? How do I track a PDF? And it's like use Docsend. There's like other motivations like people want to get status. And status is just such a much bigger motivator for folks. So one thing I thought was very interesting about how you run the company is you think about what you want to accomplish in the next 18 months and then you work backwards to how you have to staff and fund based on that and then you raise money on it. So these sort of like

18 month sprints as a corporate sort of concept, I want you to go into that process. Maybe tell us how many times you did it, how you came up with that cadence. And if you're still pursuing it now since you kind of have escaped velocity. In other words, I think you're either profitable or very profitable when we get back on this week at startups. Everybody knows that Zendesk is the go-to tool for customer support. It's the gold standard. But what you may not know is Zendesk also offers a suite of sales tools designed to remove the difficulties of sales software. So sales teams like yours can go spend more time on what really matters to their business, which of course is having better customer conversations. Even better, Zendesk is

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Steezy, one of our great investments here at launch, they teach people how to dance. it's a subscription service. Think comm meditation. It's easy for dance. They rely on Zendesk, and they love it. They use the combination of Zendesx Explorer and their ticket tagging system so that they can track which features their users want

and that they're most excited about. And then they take all of that information from the customer support channel and they give it to the product team, right? Get six months of Zendesk for free at Zendesk.com slash twist. And to qualify for this program, because they're giving you to it for free,

they just ask that you have under 15% employees and you've raised a series A or below, right? So if you're a series B and you got 100 employees, why don't you go ahead and pay for the product? Okay, but this is Zendesk for startups. It's free. Zendesd.com slash twist. All right, welcome back. Russ Hedleston is here from Doc Send. As I mentioned, they have a cool product called the Doc Send fundraising network if you're trying to raise money, which if you're in this audience, they pre-screen your deck and then send it to folks, which, by the way, is how Naval and myself started in the industry. We would just send emails to folks and say, hey, we're raising, here are people we've met with who are raising money.

His became, his venture deals became Angelist and my Open Angel Forum became launch and all the other projects I do. So I had heard you talk about this 18-month sprints that you do and that planning that you do around it. Maybe you could explain that a little bit for founders and why it's important. Yeah, I mean, everyone runs their company differently. So, you know, examples of all sorts. And ours has worked well for us.

We talk about it as kind of the strategy in Neapolitan where there are a few different layers. Like mission vision, like, you know, we think of that on like a, you know, five-year horizon, like three to five-year horizon. And then, and so those don't change very often. That's our North Star. But then, you know, we have departmental OKRs that are quarterly. And that's way too big a difference between those two things. So we have two other layers in the middle. there is a strategy that is an 18-month strategy, so we kind of revisit that on that time frame.

And then there are company OKRs that are every six months. Every year is too long. Six months seems like the right kind of like cadence to optimize for. So there's kind of the first half of the year company sprint, the back half, but then every quarter each department is updating their OKRs. And so that feels, what's nice about that, especially as the CEO, is I'd like to not be critical. path for everything. You know, we really want to push down in the organization decision making, which has a lot of benefits, right? People feel empowered. They feel appreciated. They have a bigger impact. And I don't really like to micromanage. So if you can kind of get everyone on the same page about

where we're going in 18 months, people can start to be smart about how they slot things in now versus later and kind of have those open cross-departmental conversations about what are the tradeoffs and what's the right ordering of stuff. So, you know, and then based on that 18-month roadmap, Yeah, we look at, well, what's the team we need to get that done? And then from that, we kind of back out, okay, well, you know, like on what time for we're going to hire them, how much is that going to cost? And then do we need to raise more money. And, you know, the last time we raised money was in 2018.

We raised $5 million from DCM. And we actually had a term sheet for 20. But we just saw I to I'm with DCM and Kyle Lewis on our board there from there. And, you know, he's really on board with how we run the business. And so, as you mentioned, we're now profitable, very cash flow positive. And I always tell our team that that's not the goal. But we also don't keep score based on headcount or dollars raised. We keep score based on growth.

Like, are we building a big company or not. And my co-founders are also engineers. And so the three of us have worked at hypergrowth companies before. And especially when you're trying to scale up engineering, if you scale it too quickly, it ends up being confusing. People don't know exactly what they're working on. You spend most of your time interviewing. and it can actually be detrimental to your ability to make progress, you know, on, you know, a 12, 18-month horizon.

So we'll grow our engineering team 50% in the next year. We grow other departments based on need. As you mentioned earlier, 100% of our deal flow is inbound. It's 90, 95% self-serve. And engineering and product and design is our biggest spend as a company. And that's where we think we have the longest term differentiation. And you try to do. SaaS sales and have a big sales team. But the problem with your sales team was if your average

sale was 20 grand, or it cost you whatever, 20 grand to make a sale when you take the entire SaaS sales team together and you divide their whole book of business, you know, it might cost $20,000 for an at-scale enterprise SaaS company in your case to make a sale. But that was your average yearly spend. So you're basically in the hole and you only make money if they're new for the second year. So you disbanded the whole thing, correct, as a failed experiment? It wasn't a failed experiment. I think it would have been much more capital intensive to do that. And when I see Aerootta founders who are kind of starting out, sometimes they'll be like, oh, we're going to have self-serve and enterprise sales. And I'm always like, no, no, no,

you've got to pick one go-to-market motion and stick with it. Like superhuman being a great example, I'm sure that superhuman could spin up an outbound sales team. The question is, is that the use of their time right now. And the answer is probably not. And so you do see a lot of examples of product-led growth companies that then later on put on top an enterprise sales motion, which is probably what we would do as well. It just happens to the case that we can get more growth out of the strategies that we're currently pursuing. So we did spend two years selling up market specifically in sales enablement. And that was working fine. It was more capital intensive. And the math, as you point out, means you just need a more upfront cost. There's a lot of risk in

terms of, you know, your SDRs, maybe not working or, you know, scaling your AE team. And you really need to have big, big ACVs for that to be worthwhile. And average customer. Average contract value. Contract value. Right. So if you're, you know, paying, your cost of acquiring your deal is $20,000 and you're only making $20,000 in the first year, that math is not going to work out. It needs to be like 100K or above. And opinions on this vary. But you want to be really targeting those companies. And Doxon has a lot of public companies. We have a lot of big contracts. But for a 55-person team, I think it's better to just focus us on building for the end user,

which is not necessarily SMV versus enterprise. It's just that we build for the person using our software versus the economic buyer at a big company. And those are just two different feature sets. And both strategies can work. I just think for small companies, you probably should pick one because then you are setting yourself up to be, better at it. So what type of marketing has been the most successful for you? If you were to like, as look back on the history of the company now and say, here are the three top channels for us. I'm going to guess and it's pretty obvious to everybody that the number one channel is people sending

the link to people. And then after you look at a document, you then go create your own document or you have an account, et cetera. We've all been through that kind of workflow. I'm assuming that's number one, but I don't know if it is. Tell us what were the channels that you click into and that drive your growth. Yeah, so actually the number one channel is not product virality. It's actually word of mouth. Yes, 60% of our signups are direct, meaning that we've never seen them before. They just type in doxen.com.

The number two channel is product virality. Like you get enough doxen links where then you come to doxen. But because we've cookieed you, unless you clear your cookies, right? In which case we wouldn't know, but most people don't bother to do that. We would know that like, oh, this person has just seen doxin links before. So we're going to put them in that direct product virality bucket. So making the product better and easier to use has always been our biggest growth channel. It's just kind of unintuitive for some people that, you know, word of mouth is like the bigger driver than the kind of.

I think of that is the hot mail kind of viral loop where it's like, you know, I'm using hot mail. There's a little signature. Superhuman has that viral loop as well. But in our case, it's not always the situation that a recipient of a doxon link is a sender. Like, you don't send as many decks as like a founder fundraising or a salesperson or someone in investor relations at a big financial services firm. Like, those people are senders. So I think that kind of cuts down on the viral opportunity for us.

In terms of marketing, content marketing has been our biggest driver. And so we always talk about docs and being a horizontal technology. We have to market vertically. And we've always built it, the product in mind, where it is very horizontal across our 16,000 plus customers. There's like there are all sorts of crazy use cases for it. But from a marketing perspective, last year what we really focused on was the fundraising use case. So we have that fundraising network. We come out with a lot of research reports and like what does a pre-seed or a seed round look like,

which is just really useful because we've all been to these conferences where it's always the investors talking. And our research tries to really represent the founder perspective. So when you sign up for docs and you say what you're using us for, if you say fundraising, then we'll ask you six months later if you want to participate. participate in research. Like, we're very security oriented. This is all opt-in. But we have thousands of founders who are like, yeah, sure, I'd love to take the survey. You can in aggregate and anonymize all my data. And so then we code their decks and then we can say, you know, here's what a successful pre-seed deck looks like and what a successful pre-seed fundraise look like.

It takes me this long and average. What did you learn from that? And that specifically, what does a successful pre-seed seed deck have in it? And where do VCs and investors spend their time in decks? What do they step over and what pages do they screenshot? Because you know if people screenshot? We don't track that, no, because we don't have code on your device to do that. And we could do that, but then it would make it even more annoying as a recipient. And so we try to strike that balance between making it easy as recipient and giving the center control. But even if we did detect screenshots by putting code on your computer, which you probably wouldn't install, that would be kind of scary.

You can still take a picture with your phone. So if the pixels are on someone's screen and someone's sufficiently motivated, then they can get them. Yeah, it's like the same thing that Clubhouse is going through. right now. Everybody knows how to do screen recording on your phone. You know, you hit that little screen where it's built into iPhones now. They actually, I think, can understand because people were clubhouse shaming people by recording their clubhouse chats that they thought were anonymous or secret, which is so dumb. Like, it's, it's, it's, you can put it on speakerphone folks and just take another phone out and record. Exactly. That's exactly the same thing for Docsend. It's like,

this is a kind of mouse game. So even if we did that and Clubhouse can do that, detection because they're on your device. It's how Snapchat does, you know, their screenshot detection. But Doxon does not put code on recipient computers. You're limited by what the browser can do. But the interesting part is the time spent. And it really is interesting that the time spent is what per how many seconds does an average VC spend looking at slides? And are there slides that VCs just really care about, i.e. team or something else, revenue. Well, yeah, team is the most commonly included slide and preseed and seed decks and series A decks. Although surprisingly, no category of slide is in 100% of successful decks.

So there are, I don't know, like 5% or 10% of preseed decks that just don't have a team page, which is shocking to me, but okay. No, where people spend a lot of time in preseed is on the product pages. And one of the interesting takeaways here is that pre-seed is all about the product. And so you can see investors spending more time and more time spent there correlates to being more likely to be successful. Because remember, we also have all the failed decks. Or I should say many of the founders who don't raise successfully still opt into this research. And so then we can compare and contrast the two. So more time. So a failed deck versus successful deck, if they spend a lot of time in the pre-seed area looking at the product sections, it correlates with

Success. Correct. And then seed onwards, spending more time in the product sections, actually correlates with not with failure. That's interesting. Inverse correlation. Yeah, yeah. And then you want to see more time spent in the business model or the traction or kind of other areas later on. Like if you have financials in your pre-seater seed deck, that'll get a ton of scrutiny from investors. But I mean, personally, I don't think you should put your financials in there. If the financials are the best part about your company at that stage, you shouldn't raise money. You're probably doing just fine.

And so typically it's just like, yeah, you're losing money or you've had got some crazy projection that I'm just going to discount. You know, so yeah, it is really interesting that the takeaways in terms of ordering, which pages get the most kind of time spent on them. But one of the other takeaways is that having a good deck is all about storytelling. And that kind of varies company to company. To your question about time spent, it used to be three and a half minutes on average, starting with the beginning of the pandemic,

we also track in real time. For the entire deck. For the entire deck. You as a founder pour your life into it. And what's the average number of slides in a deck? I think it's 18, I want to say. There's a lot of stats in there. So people are basically rifling through five seconds a slide or something.

Mm-hmm. They're flip, flip. Because again, this is the thing that just gets you the meeting or not. And so different people look for different things. One of the interesting things since the pandemic started is that that decrease in average time spent is due to a lot of just, 20 and 30 second views. So you might go through a deck, but after page 5 out of 20, you're like, I don't think this is a fit. You know, like, people are just dropping out. It's a much higher bar to

like read the whole deck. So we just didn't see that many kind of abandoned decks before. But we're also seeing record numbers of founders sending out their deck. So record numbers are not just existing founders, but new founders. Like as you mentioned, like now is a good time to start a company if you can afford to. And we're also seeing record number of VCs like going through. decks. And, you know, I attribute that to people. Everybody is at home. There's no in-person meetings. Exactly. It makes total sense. And, you know, the interesting thing was I always had a rule when I was, you know, running companies and had a lot of VC interests. I just would say, we're not raising. That was my number one. We're never raising. And the number two thing I would say is if you're ever,

we'd say, we're not, they would try to set up calls. And I'd say, yeah, if you find yourself in Santa Santa Monica and you want to come by and, you know, have a hamburger come by anytime. I'll take you out for a Berg or love to meet you. And they'd say, hey, I wouldn't jump on a call. I was like, yeah, no. But if you're in Santa Monica, don't have time for a call, but if you're ever in Santa Monica, do come by. And I would be like a jerk about it. And man, did people come to Santa Monica? Like, I literally had BCs who we just fly down there. It's fascinating. Yeah. I just took like a very, you know, strong-handed approach to it, which was, if you want to meet me, if you want to be involved with the company, I want to see you get on a flight and meet me in San Francisco.

I will get on a flight for San Francisco and come have a burg with me and let's spend an hour. And the people who did, it was like really awesome because you, the whole relationship, the whole dynamic changed, I think. I don't think you can pull that off now, but what you can do is you can get an investor on a 20-minute Zoom because nobody wants to be on a Zoom for an hour. No. It's too long, especially for a person. It's too long. And because everybody's been forced to, I think that this becomes the thing that carries with us post-pandemic right now in America. This is being taped and distributed in January of 20. 2021. Yep, that 2021, the time period between January 6th and January 20th when everybody was

white knuckling it, trying to land the plane in American politics. I keep joking that this is the 13th month of 2020 still, but I guess technically it is 2021. Yeah, I think I'm going to continue this month in 2020. It's a great one. But really, you know, the pandemic is going to end. I mean, we have a lot of vaccines going in arms. Some states in America are already at four or five percent. shots in arms and have 6, 7, 8% of shots on shelves. So we're kind of entering the end game of the pandemic.

But the thing I think that stays is, and I'm interested in if your data says this, you tell me if you see this in the data. First meetings, second meetings, are all going to occur online with data rooms front-loaded, and then

the socialization and in-person will happen if you get past one or two Zoom meetings and all the data and all the information up front, then the socialization and in-person will happen at the end. As opposed to how we used to do it, which is you come to Silicon Valley, you meet 50 investors over, you know, two months or you meet 15 and you get lucky and you do it in two weeks. And then you do the diligence after the in-person meeting. So basically, you're as an investor being pretty open-minded about letting people into your office

to pitch you. Now it's going to be the opposite. To get into the office, to get a pitch, it's going to be a higher benchmark. What do you think? I mean, I agree with you. It's hard for our data to be predictive in that way going forward. But I mean, I do think the market is remarkably more efficient in the last year. It's just as you pointed out, investors looking at more things, having more data points.

The flip side and the downside for founders is that they have to get in touch with more investors. But if it's less time per investor, then that can be okay. But it is a little bit harder as a founder just to orchestrate that, you know, getting in touch with 100. The pipeline is harder, but the pipeline process and the managing of all the relationships is harder. But you get a better chance at finding a match. I think people can do three times. My math, we did it internally, was we are capable of doing three times as many meetings,

not in person. And we got a very, very, very, very fast in-person process for our accelerator where people came in for interviews, like they fly in for Y Combinator interviews. They would fly in for launching accelerator interviews. and we would do them back to back. We'd have somebody in the lobby organizing people. They would come up. They would go to one table.

Then they'd go to a second table. Then we'd call them back the next afternoon or whatever if they got to the next round. And as efficient as it's still a third as efficient as doing it remote. Yeah. Well, the other thing to keep in mind is I keep hearing about this exodus from Silicon Valley, people moving elsewhere. And I think it's been the case for years now that you can start a software company anywhere in Silicon Valley has more knowledge. It's not like that people are necessarily not as good elsewhere.

It's just they don't have that institutional knowledge, right? Being a multi-time founder, getting to talk to people like you. But as that information gets more widely disseminated, you know, hopefully the cost of running a company can go down and we can like move some of these jobs to other areas because, you know, pre-pandemic San Francisco, I just joke, it's like a competition of business models to run a company in San Francisco is just so insanely expensive. So if in the future you have more things being started elsewhere, then, you know, yeah, it's fewer jumping on planes. It's like one thing if it's just like, you know, 10 minute part right in San Francisco, but plane flight, as you put it, is a big ask.

So I would imagine that the first couple meetings being on Zoom will continue. But I don't think it'll be kind of, you know, the in-person thing will go away. Obviously, based on the check size and based on people's personal preferences, you know, some might not need the in-person. Some are going to require the in-person. but I hope the efficiency is here to stay for sure. When you look at what you've accomplished in the first 10 years with the company and you started looking at the, or are you getting, how long has it been around? Seven years, eight years?

Seven years. We started in 2013. We started monetizing in 2015, 2016 and 17. I learned all the lessons of a technical founder getting into outbound sales. And then in 2018, we changed our pricing, positioning, and packaging. So we did not a rebrand, but kind of like a really doubled down on the self-serve horizontal technology. We market vertically.

And so I'd really say our current growth curve was set in 2018. But yeah, your question still stands. Like, okay, we started in 2013. Like, how do we think about having been added this long and like what the future holds? Is that kind of fair? Yeah, that's kind of where I'm going. It's like you've been at it for six or seven years. Now you've got to make a decision.

You have investors. They're looking at SPAC. They're looking at SaaS being the greatest, you know, most amazing run of all time. How do you think about, you know, I'm assuming you're at, or I understand you're at tens of millions of dollars in revenue, but maybe not enough for an IPO or a SPAC or maybe getting close? And then are people contacting you when you're in this sort of, let's call it a tweener stage? You know, you're maybe don't have over a hundred million in revenue, but you're way above

10 million, right? So how do you think about that? Well, yeah, I don't think we have line of sight to going public. And I don't, it's just not something we spend a lot of time thinking about. You know, we have these 18 months strategies, right? And so like we kind of know what the market looks like. We did our last one in July. And we see the opportunity.

And it's interesting as a founder because every like, you know, year or two, you're in a different spot if your business is growing and things are available to you now that weren't available to you a year or two ago. So for us, we're just in a really interesting position. It's a really fun company to be involved with. We've got a great team, morale's high. And, you know, like, as I mentioned before, like no one else is really thinking about things the same as we are.

So, you know, we're just kind of full steam ahead. And I think it depends. If you're, if you as a founder have like flatlined or run out of ideas or you're just tired or she's just too stressful over time. Like that can really build up and make it no longer fun to work on. But I mean, for Doxon, my two co-founders, we all went to undergrad together. We've worked together before. So we've been friends since 2003, right?

So you guys like doing the company. You guys love doing the company. You're slow and steady wins the race. But you must be getting a ton of, I mean, if you were going to sell, this would be the time to do it. You must be having people knock your doors down to add that revenue, whether it's Salesforce or you know, Slack or, you know, well, like I bought my cell phone soon. But all these enterprise companies must desperately want to own you, Carter, et cetera.

And then some of them have gone public already. Like has DocuSign or Hello Sign? Did they go public? Dropbox bought Hello Sign. DocuSign is public and crushing it. They're very, very enterprise focused. I think as a founder, there are a couple things to consider for that. Enterprise companies like buying other enterprise companies, by and large.

They don't or they do? They do. They do. They like, yeah, go to market where they can like throw it through their sales team. And since Doxon doesn't have an outbound sales team, you know, it's unclear if we could, you know, sell it through a channel. I think we could, obviously. But there's that to consider. No, I think for us, you know, if we were going to sell, it's something we evaluate when people are interested. But there is one quality to Doxend is that it feels easy to use. And therefore, it feels easy to copy. And so in the build, versus by people try to build.

Yeah. However, it's unintuitively large, especially when you get into the data room workflows inside of Doxend or the e-signature. There's just a lot of smart stuff we've built in there. So as a recipient, it looks pretty simple. As a sender, it's easy to get up and running, but there's a lot of room for mastery in there. And there's probably some kind of comparable analogy to superhuman because I have to imagine like they're in a similar situation.

They're building something differentiated, interesting. It's growing quickly. but by and large we're just running our company and having fun in the meantime. And I also have a belief that software just tends to grow. Like, it's just the best place to be in. So if you have interesting ideas and you're under your own power. And it compounds, right? I mean, it just compounds and compounds.

So every day that you don't sell, you're accruing more value to your equity if it is, in fact, growing the way it is. So it's, you know, I had these YouTube channels that people kept trying to buy off of me. And one of them was called exit. It was like a cross-fitness one that we had done because when YouTube was looking for partners, they were partners with my previous company, Mahalo, which is now Insight.com. We had this YouTube channel, exit. It has three million followers.

And it makes, I don't know, $200,000 a year in ads, just every year, year in and year out. And it just keeps growing. And I don't know what to do with it because every time I go to sell it, nobody wants to pay a dollar per subscriber. But I was like, you know, it's worth a couple million bucks to the right person, but I don't have time to sell it, but it keeps throwing off money. So why would I even sell it? It just keeps baking. That's like SaaS.

It just keeps growing. Like YouTube channels just keep growing. SEO links just keep accruing to the person who got them if it's good content, right? So it is a really difficult, yeah, to understand when to get off the treadmill. But if the market were to collapse, how would you look at it then that you missed the window, I guess? Is what you have to think about as a founder of it? Well, yeah, it depends on like what time frame you need money and how much money you need. We pay our employees really well.

They're great markets for doing secondaries. If that's something we wanted to do in the future, so we can get people liquidity. You haven't done the secondary thing yet? That would be it. It is undisclosed. Undisclosed, okay. Yeah, so this is the thing that's changed the game.

See, for people who are listening, it used to be in somebody in your shoes that wouldn't be able to do secondary. In fact, a lot of people in the industry, I think Ron Conway and Fred Wilson, friends of mine, or at least for friends of mine, they were very anti-secondary because they thought this might take people of the games and then they realized over time, oh, secondary keeps people in the game longer, right?

If you get a chance to take some chips off the table, buy an apartment, pay down your college debt, I don't know, maybe, you know, buy a ski condo somewhere. It just takes the edge off, right, as a founder? Yeah, and I mean, a couple dynamics to that. I think there are going to be more companies that are like Doxend. Like you, I mean, you've got some in your portfolio. There are things like Calendly. There are things like Lucid chart.

Companies that just or even survey monkey early on, right? Yeah. Things just keep compounding over time. And then things become more interesting and you have more options available to you. I think as a founder, one of the most important things is to just remember, it's a long road. So you've got to be engaged and you can't let your stress level get too high. Like you have to run your company well. How do you keep yourself from getting too stressed out about all this?

You seem like a pretty mellow dude naturally, but do you have moments of like incredible stress and dread in this seven-year journey where you've got existential dread or just been charmed that it's been up into the right? Well, a couple things. No, no, no, no. There have definitely been moments of stress for me, like, especially, you know, when we decided to go all on on the self-serve and not do the outbound sales stuff. And while we're doing the outbound sales stuff, we had our competitors in that market

have raised almost a billion dollars. and we've raised 10. So, you know, that's every time there's an announcement there, and then our sales teams are in these meetings, and then, you know, is this going to work? And so, why are we raising $100 million? Why aren't we bought? Why don't we do this?

Why don't we're falling behind? Salespeople are aggressive. And they don't, salespeople have no problem going into the founder of the CEO and being super agro and aggressive about like, hey, you know, this is what we need to do, Russ. Yeah. Well, our sales team was pretty, and I keep in touch with them. And we found good homes for them.

But, you know, so that was a moment of stress. But since then, no, we've got a good leadership team. Like, so that's really important, like good hiring. And one of the things we tell our employees is that, you know, like, we have a lot of the benefits of a startup or high growth. But we also have a really small preference stack, only, you know, less than 15 million that we've raised. So their equity is likely to be worth, you know, fair amount.

And, you know, basically the equity we would have given up to raise more money. or just generous with employees. And so if you hire good people and you run your business well, and one of the key things is just getting rid of underperformers, or even Google, I think, says they get 30% of their hiring wrong. And I think a lot of startups don't take the time to correct for that. Yeah, like every time, you know, HR, I think at the end of the day, ends up being the most stress for a founder, managing your team, managing egos.

And so if you can get those things right and continue to invest in them, I think it does take a lot of pressure off of kind of day-to-day firefighting. What is your ideal employee team member profile? Like, do you have one where now that you're seasoned and you've been at this for a decade and you worked at Dropbox for a little bit or did an internship and you worked at Facebook and you're on your second startup at least? Like, do you have like a certain type that fits with Russ and somebody who gels with you? And you know, founder employee fit, founder team member fit.

I try to let our hiring managers and the VPs and directors like have the final say. And I'm involved in every interview loop that anyone wants me to be on. And so my personal criteria is that you can correct for a lot of things, but you can't correct for motivation and inspiration. So I try to look to see is this position at Doxend a really, real win for this person, their career. Like are the things we as a company, the things we have to offer them, things that are going to be really valuable to them. So for instance, I've seen some other startups that will like try to hire like really big name execs. But in my experience,

it's like those people are probably going to want to build out a really big team underneath them. So you need to hire the right people at the right time. So we don't overweight on name brand like schools or name brand logos. You know, we really try to dig into like how. excited is someone about this. And for some jobs. So the level of stoke matters. Yeah. Yeah, it really does.

Increasing levels of stoke, folks. You just need to have that stuff. And it is true, like what you're thinking of. As the founder and the person hiring the person, you have to think about their careers, especially young people and their career arc more than them. Mm-hmm. Right?

It's almost like you have to take the burden on of saying, we need to make sure this person succeeds in their, career so that they stay with us for five years or six years because really the magic, I find the magic in relationships in business happens in year three or four or starts to happen in year three or four. The first two years you're like kind of getting up and running, but then like somewhere around year three, four, five when you're working with somebody, I have this with Ashley, with Jackie, I had it with starting to have it with pressure on my team and Matt, had it previously with Brian Av and my partner on a couple projects.

Like, you just kind of finish each other sentences. you can trust them to get the whole project done. You got the cadence, everything, right? Yeah, exactly. Yeah. It's a great point, too. Like, you, as the higher, like the company, do you need to think about people's careers more than they might necessarily because to your point, if they leave after two years,

if your whole company is like that, that means every year you have to replace half your company. Oh, sucks. That's crazy. And then you're also trying to grow the company by some amount. And then all that institutional knowledge is lost, and it's just a real pain. And as the founder, like, I can give a really good pitch to someone on joining Doxend,

even if it's not the best thing for them. But I don't do that. We try to figure out, like, is this really the best thing for them? You want to talk them out of it more than anything. My friend Tony, Shay, rest in peace. Used to pay people at the end of their training at Zappos. They would say, we'll give you a month's salary if you leave now. Here's the check.

It's sitting here. And they would literally put the check in front of them and say, if you want to take this check, you can leave with one month's salary. after like a three-week training program, they could just take a month salary and bolt. Yeah, I love that example. It's very clever.

Yeah. So. Rust and peace. All right, listen, Russ, we could talk all day, and we have to give back to your day.

You've been very gentlemanly in taking my insanity on the pod and just saying reckless shit as opposed to Mark Suster, who wouldn't even put the link in there. And I appreciate your honesty and candidness. And obviously, insightfulness. You are a, as one of the producers are saying, sleeper, sleeper guest. Sometimes we have guests, people haven't heard of them or maybe they haven't met them before, but they have a lot of great knowledge and you fall into that category. Russ. Thanks for having me on. This has been

great and I appreciate you. Don't ever change, please. I love the candor and the off-the-cuff remarks. It's really fun to listen to. All right, listen, continued success. Let me know when the next secondary goes in so I can wet my beak and we will see you all next time on this week. All right, I'm just bye-bye.