Russ Heddleston, Co-Founder and CEO at DocSend | Best Fundraising Strategies For Growing Your Business

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They, my guest is Russ Hedleston. He is the co-founder and CEO of Docsend. Now, previous to Docsend, Russ did a few different things. He was a product manager at Facebook. He ended up at Facebook because Facebook acquired his first company, pursuit.com. He also held roles at Grace Stripe and Trulia. He sold Docsend to Dropbox for $165 million in 2021. He holds an MBA from Harvard and an MS at computer science from Stanford. So what did we speak about? We spoke about his journey building Docsend, how he ideated the first concept of Docsend and how he found that product market fit. So we spoke about his startup strategy and a broader context. We spoke about fundraising tactics that lead to investment, inside the venture capital market, insider advice on investors and investment management, founder opportunities, obstacles and successes. We spoke about product-led sales strategy, acquisition insights and basically everything that he went through in both pursuit.com as he built that and sold to Facebook as well as Docsend that he built and then sold to Dropbox. So let's jump right into it. This is Russ Hedelsen. He is the co-founder CEO of Docsend. Sure. So I'm from South Dakota originally. There's not a lot of tech there. There's a lot of farming, a lot of great people, but I didn't grow up and tack it and grow up with computer science. And then I got out to Stanford. It was very fortunate to get in there and study like engineering undergrad, study computer science for a master's degree. But I got into tech there just because there's so many startups out of Stanford. And I graduated college 2006. And at the time, there was still the dot-com bust. Everyone's like, oh my god, all the engineering jobs are going to get outsourced. There's nothing there. I was like, I want to study computer science because it's fun and interesting. And so I did that. And I got to work at some awesome places. I interned at Microsoft and undergrad as a product manager interned at Trulia when they were like six people or four people. Pete and Tommy had just started it as a software engineering intern there. When I graduated from Stanford, I went and worked at a mobile ad network called Gray Stripe. It was like seven people. I was like, I want to go work in startups and had an awesome experience, learned a ton, ended up like running the engineering team, which I wasn't qualified to do at all. You get battlefield promotions and startup land as a thing that happens. And then I went back to business school out at Harvard mainly because I just wanted to go learn some of the business side of things. I wasn't really sure if it would have like an R or Y, but I just thought it'd be a fun life experience. And interned at Dropbox that summer when they were like 16 people. I've had to have it historically of just things I like. Yeah, I mean, you see products you like that makes sense. You track them down a lot of times and it being successful. The intern there decided I wanted to start my own thing. So started a company called pursuits. It was my first go around. I had two co-founders who also worked at Trulia and our awesome people. And we raised a seed round, did it for about a year and then realized it wasn't going to work. So we either had to pivot or pivot. That was that was our option. And so as you were shutting down our product, Facebook was an early user. They said, Hey, come here. Like we'd love for you to work on some some stuff for us. And so interviewed that Facebook and LinkedIn went to Facebook. And so that's what I would call like a talent acquisition, which is a great outcome for, you know, for us at the time and ran product for the pages team at Facebook for a couple of years. Got to see Facebook go public and then decided I wanted to go try again. And my two co-founders at Docsend, we all went to undergrad at Stanford together. We all worked at Grace Tribe together. And so Grace Tribe had been acquired. They left and you know, it's a lot of times you glass like, Oh, how do I find a co-founder? And it's hard. You know, there are people you've worked with before and you like working with them. You keep in touch. And if you get a chance to work together again, those those things happen pretty rarely. So yeah, I left a lot of money on the table at Facebook. And it was a wonderful place to work and I learned a ton there. But I wanted to go try again. So we started Docsend in 2013. And ran it for eight years almost exactly. And ended up selling it to Dropbox in March for 165 million. And we raised only 15 million for Docsend. The topic I'm happy to get into is, you know, how much to raise when to raise, you know, is that the metrics I always told our company at Docsend that, you know, we don't keep score based on head count or dollars raised. We keep score based on just building a great company. And so we saw a great fit with Dropbox. And so now I am working at Dropbox. And you need to work on on Docsend. But, you know, so that's kind of the story to date as it is. Not bad, man. Not bad. I can, you know, you say it's so casually like we just sold it for 100. And not what 168, what was it 165? 165. Yeah. 155. I feel proud of it because they bought a real company. Like we were profitable at the time of acquisition, growing really, really fast, figured out a lot of really interesting things. So anyway, yeah, it was a good acquisition for Dropbox and they integrate out come for the team. Did you you were like going to stand for you were like, I'm going to build my own thing. That was always it. There was no other other career path for you. Oh, absolutely not. No. And I still don't really think of myself as like an entrepreneur in the sense of like some people like, I just if age of four, I knew that was going to be my path there. I don't know. Some people have these origin stories where I'm like, good for you. I wish I had clarity on age. I feel like I often still don't have any clarity. No, I had no idea what I wanted to do in college. And yeah, I kind of ran around looking at like, oh, who wouldn't employ me? And so like, well, a lot of people out of Stanford go work in management consulting. And so I had a bunch of friends at McKinsey. I actually went through and I was very fortunate to get an offer from McKinsey at a Stanford. And I remember being at Seldener and kind of seeing all the managing directors kind of like bragging about business school and stuff like that and just trying to think about it. And I was like, I just think startups are fun. There's just so much uncertainty there. One knows it's going to work because like, you always get a good story out of it. It's an accelerated pace of learning. So, you know, I did the real risky thing because I had had other offers from big tech companies as well. And I went and joined a, you know, seven person startup because my mentor had just done their series A. So I knew they had funding. I like the team. I thought it was a smart space to be in. And it was. They had a really good value prop and a really good idea. They ended up being the number two to add mob. And so, you know, as interesting case study and like, some spaces are a winner take most. So, you know, Graystripe is still good outcome. But it wasn't add mob, but it was for me an awesome learning experience. So, having observed a few different startups, I wanted to try myself. And so I don't necessarily think of myself as an entrepreneur, although the kind of joke is amongst my friends or entrepreneurs as well. Like, you know, you start a company. There's definitely low points. It's really frustrating. And then typically what you're most qualified to do is start another company at the end of it. If you have an exit or whatever happens. So it's probably what I'm most qualified for. But as an entrepreneur, you end up usually being a jack of many trades is kind of the skill set, especially early on that helps helps kind of get done. Whatever, whatever needs to get done. I just want to take a second and thank the sponsor of today's episode Shopify. And don't you love that sound as a sound of another sale on Shopify, the all in one commerce platform to start run and grow your business. 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Connect with your customers, drive sales, manage your day-to-day, accept all major payment methods and integrate with any third party app you could possibly think of. If you want to try out Shopify right now, go to Shopify.com slash success story that's all lowercase for a free 14 day trial and get full access to Shopify's entire suite of features. Grow your business with Shopify today. Go to Shopify.com slash success story right now. Remember, success story is all lowercase that's Shopify.com slash success story. So how did your process so you've worked in startups? You want to start something? So walk me through the mental process that you went through in determining what you wanted to build out. How did you leave an ideate on first startup, second startup? What was that? Yeah, sure. And one thing I also say about myself is like, I think historically I've been pretty impatient in many ways in my career, leaving too soon, or as a Facebook, I was like, oh, it's already too big. It clearly wasn't. Everything needs to be faster and go the sorts of things. There's a lot to be said for patients, like the more years of experience I have. The first startup, pursuit, we wanted to solve a problem we had as three engineers, which was that it was really hard to hire engineers. And a lot of the great engineers that we got at the different companies and worked at were through referrals. And so we're like, let's build software to help track and manage referral programs, which is still a valid idea. I think it's probably a better feature of a full ETS applicant tracking system. So like a lover or a greenhouse or the play others, some really big ones. But we didn't do a lot of research on the market. We just solved the problem that we ourselves had. And so that's how it came up with the idea. And then you know, you did post mortem on it and kind of like, we would have just done more research on it ahead of time. We as engineers wanted to get in there and start building. And so, you know, when we, when I left Facebook and started Doxon with Dave and Tony, I was like, guys, we should be more thoughtful about what we do. Let's not write code on day one because it's tempting to write code, but as soon as you write code, then you're kind of already committing yourself to a particular path. Ironically, this happens with pitch decks as well. When I talked to entrepreneurs, if they spent too much time making something look pretty, they don't want to go back and read you their pitch deck because it's just like they're too far in the irrational escalation of commitment, which is never not necessarily good. So for Doxon, we explored a number of ideas and before building out the concept behind Doxon, we did a lot of research. We went back and looked at like, hey, who started something like this before? And then, you know, my belief is that there aren't really any new ideas. There's just good timing and good execution. And I also ran around and talked to all the other companies I thought should build Doxon. And I was like, hey, why don't you build this concept? And, you know, this came from a learning I had at Facebook where, you know, it's a product manager, you know, kind of running product with the pages team. I got introduced to a lot of founders who were kind of curious about what his Facebook doing. I've got an idea in the space and they were often very cagey with me about their idea, which is from my perspective, it was kind of silly because I would have been terrible at my job if I was like, oh my god, this entrepreneur without any traction and an idea, it's just such a good idea. Everyone, drop what you're doing. We got to go copy this person, you know, that's just like really not how it works. The entrepreneur has way more to gain than to lose by trying to get for me like what Facebook is doing and how we're thinking about things. And so I for Doxon ran around and kind of tried to get that information and people were receptive and said, hey, we think it's a good concept and, you know, we might do it someday. We're not doing it now. We got a couple of talent acquisition offers, which was very flattering, but it had been through that and we wanted to go build a business. And I also asked, hey, what were we working on? And it was something totally unrelated to the Doxon, you know, other other things they had. So I was like, okay, I guess you're not going to build it. So that was the general process that we used for Doxon. I do think it's in general going to have some knowledge of the, you know, space in which you're starting your company, either through just a lot of diligence or through past experience. So Tony had worked at a startup that ended up selling to the box kind of at an undergrad. And yeah, it in turn to drop box and, you know, generally kind of knew the space. And we just, we did a lot of research on it. So, but it wasn't solving a problem you had at the time. It wasn't, it was a little bit different. It was so, so Doxon's got 23,000 plus customers at this point. And is, I don't think I can share stats, but we're growing really fast. And, you know, so the, we described Doxon as a horizontal product that we market vertically. So some of those applications of Doxon are problems I have. So I'll give an example of one of the earliest use cases for Doxon, which was startup fundraising, which we've only recently started marketing towards. We originally came out with Doxon. It just said document analytics. That's like all it said. And then we like kind of changed it up to being like sales enablements. And we still have a bunch of like big sales teams, which is great. And then only in 2018, did we kind of change our marketing site to be, you know, Doxon brand promises around control. And it's a horizontal technology that we market vertically. But ever since the very beginning, we've had a lot of people use Doxon for fundraising. And that's a need I've personally had, you know, and I was raising money for pursuit. I put together my pitch deck. I sent it around to people. I just got crickets back. And it was so hard to raise money. And, and, you know, invariably leaked to competitors. And we get I get it sent to me by other people being like, hey, just so you know, your deck is getting sent all around. And I was just like, well, that who who sends it around? I don't know. I've said it like 30 people could have any of them. So I was like, there's got to be something better here. And so the one of the initial concepts behind Doxon was just like, hey, being able to create as many links as you want pointing to a document, each link is unique. Each link can have different settings. And when people look at that document, you can see how long they're reading each page. Not rocket science. I just think that's a service that should exist on the internet. So our first users were, you know, friends of mine who were founders who were off raising capital. And I'd say, hey, we don't even have a marketing site for this thing. It's just in beta. It might break just like, you know, it's free. Hey, just use this. It's better than an attachment. People be like, ah, it's okay. I'm sure. And then, you know, people like, oh, this is quite interesting. I really like getting this. And then I'm like, oh, cool. But like the idea was never to build like a vertically integrated solution for fundraising or something like that. The idea was always that Doxon is like pretty widely applicable in terms of like how often this particular set of workflow shows up in like a B2B context. But it was helpful to be guided early on in that I cared about it because I used Doxon for my fundraising. I used Doxon for my investor relations. I use Doxon for all of our sales or customer success. Like anything we're sending outside of our company is a Doxon link. That's it should be because then we can track it centrally. We understand what versions are performing and like where they're going. We can, you know, have a lot of lists to make sure they're not, you know, share it beyond the desired audience, all the data feeds back into Salesforce. So we do use our product a lot, which has been awesome in terms of understanding, you know, the nuance of it. But that isn't to say that, you know, a lot of people use Doxon in ways that, you know, I just don't have those use cases. And so we have built it in such a way that it is extensible beyond the things that we use it for. So it seems because the use cases have evolved and probably use cases that you like the application of something like that has like unlimited use cases. Anytime you just mentioned, anytime you send an email to anybody, there's a there's a potential use case for Doxon. But okay, so let me let me ask you this. So how do you at an early stage when there's so many different ways that you can brand it and market and position it? How did you find product market fit? And then of course to teach people that are listening, how should they look for product market fit when their early stage is to validate the idea? That's a great question it's got. And, you know, there's a real natural tension between when you're starting a company, it being venture scale and being able to raise money and solving something that is kind of more understandable, you know, like as a as a founder. And so you're on the one hand, you're like, oh, I got to pitch this thing. We're going to be a giant company and you take over the world and like, you know, like, oh, cool. It's like, you know, my pitch tech needs to be like, we're going to be Amazon, you know, but then what you think that is that when Amazon started, like, they had a real tough time raising money because they were like, we're just going to take used books and sell them online. And so, you know, the thing I tell entrepreneurs is like, don't confuse your pitch tech with investors with like what you need to do today to start getting traction. And it can't be the case that what you tell investors is a lie, but it is, it is a greater, it is greater than what you're currently doing. You can aim small to start. So, you know, for for, you know, doxen, you know, a lot of like the kind of gorilla marketing we did in that first couple of years was like, yeah, we just released it, a tech crunch, we kind of saw, hey, who's using that? Who's liking it? And then, you know, like, how do we document those use cases? And then like, try to figure it out. And we we found a really good fit in sales. It's kind of like how we got into the sales enable again, which is still a great vertical for us. But, you know, I think my vice, the founders would be try to find an application of your insight that has enough urgency for a user that they're actually going to care about what you do for them. Because I often see a founder say, hey, I've identified something. It could be huge. It could be massive. It's going to be everything. It's an API for blah, blah, blah. And then we're using, you know, AI on the back end and like, okay, I can see how like that, like general, differentiated approach to note taking could be to interesting and maybe useful, maybe a company. But it's like, to whom is this like so important that like tomorrow, they're still going to open up your site? And when people have a difficulty with that, then I'm like, oh, and then if they're like, oh, yeah, here's an example. I'm like, okay, well, then just give me the pitch for that person. Like, how does their life change based on like what you're building for them? Are you replacing something? Are you consolidating things? Like, are you saving them time? Are you saving them stress? Like, what are you doing for them? Because I think in software, one of the things I love about it is that if you solve a small problem, small problem, you're often solving a big problem. Like, you know, a lot of companies that, you know, end up not being big software companies, I think fail in execution or timing, not necessarily that what they're doing is an extensible if they're at the right place in the right time and executing well. So solve something small and then continue to think about like, well, how might this be extensible? Because just like in the example of Amazon, you do something well. It opens up new doors for you. Things you couldn't do on day one, you can do on day five. And once you, especially if you're a business model of SaaS, like you get a flywheel going where that cash flow starts to help fund your business and can help you expand into other things. So docs on started is just like a way to send and track links to documents. But then over time, we realized, okay, we can get into this like deal room space for sales or we can get into data rooms. Data rooms is like two and a half billion a year in revenue. It's crazy how big it is and it's like legacy software. No one especially likes it. It's pretty entrenched. And so, you know, hey, we're like, we can go into the data room market and like, hey, a lot of people use e-signatures as well. Like let's just get into the e-signature market. And so, you know, as you find success, it opens up new avenues to you. So as a founder, don't necessarily be too concerned around, you know, what you're doing is too tiny. And when you create the pitch for investors, yeah, the pitch division, like where could it go over time? And that's a demonstration of how you could think big. But in terms of the path to get there, like no one goes from like zero to huge overnight, like there's usually more nuance in the beginning. And so, it's okay to do unscalable things and aim for like relatively small markets early on. I just want to take a second and thank the sponsor of today's episode. Hello, fresh. Now, hello, fresh gives you fresh pre-measured ingredients. Mouth watering seasonal recipes delivered right to your door. I've used HelloFresh for a while. All the ingredients, all the recipes, they're incredible. It saves you tons of time. It lets you skip those trips to the grocery store that you dread. It makes home cooking easy, fun, and affordable. That is why it is rated America's number one meal kit. Now, it saves you tons of time and stress. 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What was the main, the main, the main focus or was it both simultaneously? Well, we, we definitely did a lot of things wrong. Uh, and in docs and has been like a really great learning experience. I think if you talked to most entrepreneurs who had as successful access or have a successful company that they're running it, they usually would say, yeah, if I did it over, I could probably do it in half the time because, you know, especially as a founder, you're usually on like the edge of your knowledge. You're kind of pushed to the edge of your comfort zone because you're necessarily working on the things that no one else in your company is an expert on as you try to figure them out. And so for docs and we didn't know who the end user was going to be when we launched it originally just document analytics. Yeah, attachments are bad. People want to see who's reading documents they send. We released it and we just kind of waited to see what happened. And then we at a certain point because we raised a series A, it's a we've raised like 10 million and we're like, okay, we got to create a business now. Like unfortunately, every entrepreneur at some point needs to go from fun technology project to real business. And so we spent a couple years selling up market and sales enablement. And one of my key learnings from from that and we still do a good job selling up market is that especially with limited resources or relatively small team, you kind of have to decide if you're building for the end user or the economic buyer in VDB software land. And there's a big distinction there. Like if you're selling a thousand seat, 10,000 seat deployment of your software at a company, you're building for the economic buyer. Who is buying your software on behalf of the others? If it's not a great experience for the end user, the economic buyer doesn't really care. Like does the usability of Salesforce hold them back from selling million dollar deals? Like no, no, it doesn't. Like they would make in their UI a little more intuitive. Be helpful to me as an end user. Absolutely. You know, but they're building for the economic buyer. They actually did start building for the end user with worth noting. So you can go from one to the other. It's usually easier to go from end user to economic buyer. DocuSign being a great example. But for for docs and we we started building for the end user. And that's been our strength the whole time. And so even though we spent some time selling at market, if we had to make that work, we could. But by building for the end user and also following the strategy of horizontal product that we market vertically, that works out really well for us. Because the product spreads awareness of the product. And then the marketing side educates the different ways to use our products. And then that converts really well for us. So I would definitely call that product led growth more so than like demand, like demand. And it doesn't really contribute a lot for us. It's not like channels contributes a huge amount for us. It's not like we do outbound sales or anything like that. Organic is the number one kind of channel for for docs and and and how we gained users. And that's really just us continuing to make the product better and to continue to educate people on like how flexible the technology we built is and just the number of ways that you can use it. So there's there's a lot that that goes into that. But it always leaves hopes in the option of us going up marketing enterprise, which I assume, but I'd like to do at some point. I was I'm just curious if if like has now we look at you just mentioned the great case study with with Salesforce. Do you think that that only potentially worked because that was more of a blue ocean when Benioff brought Salesforce really just created he created the category of cloud. But do you think in a in more of like a red ocean having the end user in mind leads to a quicker ramp? I think that it's something that's new in the last decade like the possibility for this just because and and I dispute that for Salesforce it was a blue ocean. I think that's a way of painting it historically. Like when they started Salesforce it wasn't clear that being in the cloud was a differentiator at all. Like if everyone agreed it was a differentiator that incumbents would have moved faster to it. So they as part of their marketing and I think part of what they were so good at is they they were able to like really point that out is like, Hey, this is a great differentiator. Then they made a market. But you know in the early days, yeah, they were selling to SMB. They were selling on the edges. Everyone else is pitching enterprise and by selling down market it gave them enough time to build a product to start going at market. Same with DocuSign. DocuSign for many many years was like 50 people and all SMB and then you know, they're 90 plus percent enterprise. So it's morphed pretty quickly into that. Other companies like SurveyMonkey probably should have gone enterprise sooner and and did not. And so now they're trying to play catch up. Other companies like SurveyMonkey never went enterprise. So you know, there's like no right answer to these these sorts of things. What is new though and probably the past like eight five to ten years has been how big a company can get only building for the end user without having to go up market to enterprise because it was previously thought, sure, you can get a foothold there and then you go enterprise and that's the interesting thing. And if you look at Calendly or Lucid Chart or Grammarly, you know. Mailchimp. Mailchimp. They actually have been around for a very long time. So they were one of the original ones to kind of run that playbook and one of the amazing exits for them. And so yeah, you can build a surprisingly large company by staying down market for a long time. But it varies on the company. I think for early stage founders though, it's like, is it a win or not? You know, like no one, you know, especially for the average person, you're like, did you sell your company for 100 million or 10 billion and like, or it's like, oh my god, you had a successful company, you know, so most startups fail and say it's like when I talk to founders, I'm like, let's let's be reasonable about, you know, like what you're aiming for here. And usually you're just aiming to, you know, you have an insight, you want to make a successful business and it's all first fun because it has the unintended consequence of often being much larger than people expected it to be. But I think for the purposes of like as a founder or advising other founders on like how to get started, you know, it's like kind of those early things. And I think it's okay to just focus on the end user early on there, enough case studies now where like you can build a great business out of that. And then by the time you have that option of when to go up market or if to go up market, you've usually already created a business of some success at that point, which is an amazing milestone. And it's like a privilege to be able to have that conundrum to even think about at that point, you know, hey, I'm going to raise a series B or C or you know, I'm going to raise 40 million bucks here, like how much is that? Am I going to be able to like building a separate team to go up market? Like, yeah, it's a stressful decision, but like you're already in a position of like, you're doing okay. Yeah, no, it's very good. Okay, I want to, I want to, this is, I love this and I didn't know where this was going to go, but I appreciate some of the insights that you bring to the table on this because I haven't had this conversation with many other people on the show, but I want to also pull out some fundraising and investment insights from you, because I know that you speak a lot about this. This is obviously something that you've done multiple times. So, um, let's, let's jump into that a little bit. So fundraising tactics. Um, I even heard, uh, on, uh, this week and start up, you're speaking about 18 month fundraising sprints. Um, maybe you want to like dive into first time founder. They want to go raise money should they? And how do they do it? Yeah, that's, that's a great question. Um, and there, there are a lot of pieces that go into that, uh, maybe we'll start with real early stage. Maybe haven't even created a company yet. Should I create a company like, you know, how do I raise money? And, uh, I'll use an example like my first startup pursuit. Like for pursuit, I, I had, you know, I was in business schools. I had like, you know, personal debt for, for that. And, you know, I was like stressed about money. And it's like really not a fun spot to be in. So I think if you're thinking of starting a company, make sure you have a year of personal runway, like not savings, but just like, you know, you and your providers can put in 100k each or something like that. There is like a precede now, which is actually great. It's like three or four hundred K that you can raise. And you don't have to have necessarily anything to show for it. You can just be a couple people in an idea. And that can be great. But that's also kind of expensive. So some founders will skip the precede round. It kind of depends. If, if you're, you know, let's just say you, you are going to go, uh, do a precede and you've got enough personal runway to last a while. I'll get a co-founder that sort of stuff like when, when to raise money. It's all about, you know, how much research you've done and what you have to show for it. So, you know, to get a precede round raised, you've got to go research the market. You've got to have the means of building a product. So that means you've got to have, you know, if you're a non-technical, go convince someone technical to be your co-founder. Like, that's a pretty important thing. You can kind of do that on nights and weekends or go network. Um, let's just say you're, you're our stress about money. Like, go save. Go, go get it all but a big company. Maybe you'll get a job at a big company in a vertical that you might want to start something in a few years. Like most founders are, you know, in their 30s or 40s, you don't necessarily have to be in your 20s to start a company. And, you know, you can, you get a lot of time to go start a company. So anyway, you can, you can be patient. And then let's, you know, say you've got an idea, you've got a co-founder, you know, you're even able to like self-fund a little bit, make some traction. You know, the question I'd ask is like, are you stressed about kind of minutia having to do with like, like either your own personal finances or like buying a white board for your office or, you know, like server costs. And if you can raise money and that helps you focus on your business, you should probably go do that. So for docs and we didn't need money for ourselves. But, you know, we didn't feel comfortable footing the bill going and hiring a team. So we built the first version on our own. And we didn't make it look pretty. We just made it functional. And then we did enough like beta testing with people to be like, people like it. Like we can't find a reason why this is in the great idea. And we think we should go make a company out of it. And so the thinking there was like, let's, because I also learned from pursuit that, you know, you can drag this out a long time. And a lot of first-time fathers especially tend to dip their toe in the water with fundraising. And I'm like, no, no, no, don't do that. Just like, just go all in. See how fast you can get to know. See how many meetings you can line up in a two-week window a month in the future. And get a good read unlike, do you have something that's fundable now or not? And if not, that's okay. Try again in three to six months, you know. And if you can afford to wait that long, but try to get to know quickly as opposed to having one-off meetings here and there over a six-month period. So for docs and we set up all of our meetings in a two-week window. And I was like, hey, we can erase awesome. If we can't, we'll just go back to building for another, you know, three to six months. And then we'll go try again. And we were fortunate. And that Jeff Pavey at Uncork was like, yeah, in his mind, this kind of reminded him of Sengrid. He was like, you know, I feel like there are a lot of ways to like not send an attachment. You know, you can use Dropbox for instance or something else. Like, but you know, Sengrid at the time, that was a really crowded space. And, you know, I think especially from a VC perspective, like everything is a red ocean because I haven't seen everything before. He's like, but he's like, yeah, I'd use docs and and so sure we'll fund it. So, you know, and for us, that allowed us to go hire a team, you know, hire, you know, a good designer to like invest in like taking the learnings from our beta, putting together a marketing site, and then launching it at TechCrunch Disrupt. And so, you know, that was really useful. And then that gave us no signal that we raised, you know, Series A. And the idea behind that was like, well, like, we were not to like revenue generation yet. Like, we need to do some iterating, figure out what is the business, but people clearly like the product. And so, you know, we were fortunate to raise that. So, there's kind of like a hurdle at each kind of stage, depending on like what you have to show for it. But yeah, I think that the main things as a founder are like, take stock of like what you've learned and the evidence you have that says what you're working on could be a big company. And then try to get to know as quickly as possible in terms of like getting all the meetings and like, you know, getting all that feedback. And by the way, fundraising is of necessity a depressing process because everyone gets almost all knows, you know, it's like, and a founder who's successfully raised, you say, congratulations to them. And what they don't respond with is, oh, by the way, 95% of my meetings were all like really like harsh nose. And they were, you know, really mean to me, but I got one yes. So, we were able to raise it. It's like, no, they don't tell you that. They just say, yay, we raised, you know, so a lot of times in the middle of fundraising is kind of a lowest point. And then you just, you just need one yes to make it to success. So a lot of times, like, founders who haven't been through the process before, I try to like, kind of coach them on like, hey, make sure your spouse knows or your, you're signaling other, your friends know, you're going to go through kind of a rough period here, your co-founders know, you know, kind of like mentally brace for it because it's just like a thing that happens. So let's take a second and thank the sponsor of today's episode true bill. So let me ask you a question. How often have you signed up for a free trial and then it converted into a paid subscription and you forgot to cancel it? 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I saved about 578 bucks but that's just because I spent so much time in the past having to go back and cancel. I'm sure if I knew about them two, three years ago, it could have saved me like thousands of dollars by now. So stop letting CEOs and bad businesses get rich off you being unable or just forgetting to cancel. Don't fall for subscription scams. Start cancelling today with true bill at true bill dot com slash success story. Go right now. True bill dot com slash success story. That's true bill dot com slash succ ss st or why it could save you thousands a year. That's true bill dot com slash success story. Take control of your subscription. And do you think that founders should go and get those get those nose ASAP before that like pre revenue or do you think that you should wait till you have revenue to actually go out to raise that even series a. Well, yeah, series a and seed and docks and has research on all these different stages. We've tried to quantify it because and the research that docs and doesn't this stuff is just of interest to me personally because when I was starting pursuit and I was asking for advice, I got just so much anecdotal advice. I'm like, this is what I didn't work to do that or this is what I didn't it didn't work. So don't do that. And it's like, has anyone like done any like kind of research on this and why I went to conferences. It's usually like like older venture capitalists who pontificate about like what they like to see in the company. And if you're going to get me to invest, here's my investment philosophy. And it's kind of more geared towards like them pontificating on why they're so brilliant and successful, which you know, as an entrepreneur and the audience being like, I just need your money is like not necessarily super helpful to me. And I'm like, I don't even care if it's your money. I just need someone's money. I'm trying to fund right here. You know, so for the docs and research, we try to come at it from the entrepreneurs perspective. And so we break out how series A is different than series C then precede and so on. Even venture capital fundraising is something we have enough data on to have some interesting takeaways. And it's not so much like what should you do? It's just like common takeaways from all the companies that we can get to participate in this research around like what are common factors of success and failure. And so the narrative that a company tells really depends on what they're doing. And so it's kind of hard to give specifics, which is kind of annoying. And to your question around like, is it better to raise like pre revenue or like pre launch or the answer is usually like it depends because that's what I mean by take stock of like what you have to show for yourself kind of as evidence like if you're a second time founder, you know, awesome. If you've got a like a really great track record and career is like a Google machine learning engineer or you've gone to like name brand schools, you know, these are all things that can count in your favor. If you're you know, if you're like, oh my god, I'm a nobody. I'm non technical. I have nothing of note on my resume that a venture capital should be like, oh, at least that's a, you know, impressive something or other, you know, then yeah, maybe you need to have a little bit more traction or revenue or something to show for it. Maybe you have to be a little bit scrapier. And so the answer is it depends. And so that's why, you know, it's just good to like get advice from folks and, you know, the nuance of your business. And typically it's easiest if you can get advice from like if you're raising a seed round series A investors because they'll be more honest with you hoping that they'll come back to them later and they'll have an advantage in funding your series A. As opposed to getting advice from seed investors when you're looking for seed round like they're just looking at you as like do I invest or not. So get that advice. But specifically to, you know, do I raise before revenue or after revenue or before launch or after launch. Like the common tradeoff is that it's always easier to sell the vision before launch because you can say it's going to be huge. And so you can be persuasive as a founder and just say like here's all the evidence I had docs and raised or seed round before we publicly launched. So we raised our series A before we had any notable revenue. So we decided to, you know, do those things earlier rather than later. But on the other hand, launching early gives you more information on like what is working or not working. So you can kind of get started like actually scaling your business earlier. So there's just tough tradeoffs to make for all of these decision points. And so, you know, fundraising unfortunately is time as a founder you don't get back. Like you don't get credit for the time you spend fundraising. You just get credit for building your company. So fundraising is a necessity. But you kind of want to get it done as early as possible or as fast as possible. I'm kind of get back to building your company. I know that you I know that you've mentioned that fundraising and like sort of best practices are very case by case. Are there are there any anything that that is more universal that you can sort of help someone walk away with it? Because listen, if you're fundraising like this is the best practice based on what I've seen or there's a probability that if you do this, you're going to end up being more successful. Or is it just really on a case by case you don't want to commit to any absolutes, which is also. No, no, no, I could go through a whole bunch of stuff for you. We could spend a couple hours on. I'm sure you. So let's do a few. Let's do a few. Okay, we'll we'll do a few. The first is like people ask like, do I need a pitch deck or not? And my answer is usually yes. If you're asking that question, yes, people who don't need a pitch deck have enough previous success to and the relationships to just walk in and say, here's generally what I'm doing, give me money and like, okay. And people also, most people yes, be like, oh, can I create a video pitch and like, well, maybe, but like just the way it works, at least in Silicon Valley or kind of like professional, you know, software investing like venture capital is like pitch decks, allow investors to be very efficient running through things. And so it's like three to four minutes per visit like view on average. And so they can just intake a lot of information about what you're doing. So yes, you're probably going to have to create a pitch deck. And then also by the way, that pitch deck is so helpful when you have to go higher a bunch of people, it's also very helpful informing like what your sales deck looks like if you're doing V2B, you're doing any sales. And it's just a really helpful document for what are you doing? Like document, like, and then you know, you're going to iterate on that in the future. So so create a deck and and be thoughtful. It doesn't need to be the world's best designed thing. Also in the creation of that deck, keep it simple. The most common mistake I see is that people make what they're doing sound more complicated and the hopes that it makes it sound smarter or more defensible. And it does not have that effect typically. You know, one of the nice tests of this is like, can you take it to a friend who's not in tech, your parents, an aunt, uncle, and tell them what you're working on and see if they can like repeat it back to you. And even when you're asking like friends for feedback, give them your pitch, show them your deck, give them your all that you're pitching, then ask them like, how would you repeat this back to me? And if they have difficulty with that, that means you got to dumb it down more because the best pitches seem like intuitive makes sense. And they might leave you with questions like, why hasn't that been done before? Or isn't that kind of like blah blah blah? And then you can answer and address those things. But if you start the pitch with why is it differentiated that gets in the way of like, what is it to begin with? And so a lot of founders, especially first on founders aren't comfortable dumbing down what they're doing to like that level of simplicity, which I think you kind of have to do in order to get across the point. There are other like best practices around like why now or why you, you know, type of things like those aren't obvious questions. Like I see a lot of founders where they're like, well, I don't need to add a why now section or why now page is obvious that this is a thing that it should be done today. And another thing to stress for founders is that nothing is obvious to investors, like assume no knowledge on the part of an investor when they're reading your deck. So, you know, like as you go through, I keep an eye out for like start with the obvious stuff, you know, like why are you uniquely suited for this? Why is this a thing that has to be done today? Why hasn't it done before? And there are also invariably going to be like holes in your pitch that you know about. So for docs and one of the holes in our pitch was like, why doesn't Google just go do this? Or why doesn't Dropbox go do this? And there wasn't a great answer. And for a lot of software, there's not a great answer as to why Google doesn't do it or some big other company. There's been a lot of research around innovators dilemma. And if you've worked in a big company, it becomes a little bit more apparent like why things just move real slowly. But in terms of like, you know, pitching it and, you know, how to represent that, you know, for us, I was like, well, I went and talked to people and they're just not going to build it. So, you know, for you as a founder, it's okay to leave some things unanswered. Like, don't overstress about them. If, you know, the question is like, well, why doesn't Uber do this? It can't be so close to Uber that's like, oh, they probably will do this. But if it's like, listen, they're focused on these things. There's a risk, but, you know, I've talked to some friends there. And I think we've got years in the future to do this. And some investors might say no, like that's too risky. Other investors might be like, I believe you. And I think you've got a great head start on it. And we'll back you. So again, you only need one yes. So instead of focusing too much time on like that particular hole in your deck, maybe put more effort into what is your go-to-market? How are you scrappy in the beginning? Or, hey, what's your hiring plan? Or like, list all the engineers you know that you're going to recruit once you get the funding in the front door. So there are those things. I think another common one is like, uh, financials. If you're like a seed sage company, don't put financials in there. I think this is like a thing in like the 80s or maybe 90s or something where it's like the business plan thing. And then you had to like have pro forma numbers. And like, especially early on, like don't, don't do that. It's like very rare that that needs to be a thing. Like, to the extent your business has like, uh, clogs or it's like a physical product, you need to demonstrate that you understand kind of like how those things work. But like, you know, if you put financials in there, people will spend a lot of time reading them. And that's not necessarily what you want. Because usually your financials aren't the bright spot for your startup and anyone can make up math and make it look like a hockey stick. So I'd say, you know, that that's like a made-up exercise like not to put in there. I'll pause there. There are other things I can go through that are just kind of like, that's the best thing. We'll do it. We'll do it part two one time, man. I'm sure you could go on. Okay. Um, I want to, uh, I want to, I always finish these up with a like really quick rapid fire. But, uh, for people that want to connect with you, uh, where should they go? Uh, social website, where do you want to point them? Uh, Twitter is great. Um, so you can follow me there. I mean, there are LinkedIn or just, uh, Russ at Dropbox. Uh, okay. It's the other one. So, I just want to take a second and thank the sponsor of today's episode HubSpot. 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Learn more about the HubSpot CRM platform and how it can help your business grow better at HubSpot.com. All right, I'll put that in the show notes too. Okay, so Raptifier, um, biggest challenge you've had in your life. What was it? Had you overcome it? Oh, biggest challenge. Oh, um, oh, man, that, that's a, that's a great question. Um, I've been very fortunate in my life. There have been a bunch of challenges. I mean, one with, with Docsend was like we in 2018 needed to like, we were selling a market and, um, you know, it wasn't working super well. And so, you know, we had to kind of pivot our whole marketing site and kind of our go-to-market, which was, that was, that was a scary, that was a scary year. Um, and so, you know, like adapting to change is like one of those things as a founder like no one else might know about it, but for you, you're stressing out. Um, you know, even in like undergrad, like just figuring out like what, what jobs go get or like work stuff has always been a challenge. I, I'm sorry, I'm not able to come up like anything like specifically. I don't know. It's good. It's, it's good, man. It's, it, it, it is what it is. It's, it's what you've lived and it's, that's, that's, that's the bad. I thought the pivoting and the iterating and leaning into change as a founder. That's pretty damn good. I don't know. Just me. That's a good, a good advice. Um, if you could tell, if you could tell your 20 year old self one thing, what would it be? Um, probably just be patients and also keep in touch with people. It's interesting, especially being in tech, how long our careers are and how, you know, it's a lot of the same people over and over again. Like it's the same story is being repeated over and over again. It's a really fun industry to be in, but, you know, it's a, it's a long-term game. So I would tell my 20 year old self, like be patient, you'll have time and the people you're going to school with now are going to do lots of interesting things, make friends, stay in touch and, you know, career, career will happen and good things will happen. Good. Um, a book or a podcast or audible or something you'd recommend people go check out. Um, let's see, uh, a book, a man called Ove, I just find that to be like such a tear jerker. That was, that was such a good one. Um, like a, or a brief history of nearly everything I've been told is one of the most difficult books to finish. So I actually found it to be relatively interesting. Uh, so those, those are two or, um, another, another book would be, uh, you know, uh, thinking fast and slow by Daniel Kahneman is a great one. I find behavioral psychology to be so relevant to anything like software related, especially anything product blood growth related. Very good. Um, a person that had a major impact on you. Who was that? What did they teach you? Oh, there have been a lot of people, um, uh, over the years, um, Benjamin Wayne was an independent board number for Doxon and he's the CEO at Clisto Media and he's just such an impressive and smart guy and I think this is the fifth company he started and he's the CEO and he's done B2B and B2C and he's had such an interesting career but having him on our board for a couple of years was just really fantastic because whenever I was stressing about something in the weeds, he always just had a good way of kind of elevating the conversation and bringing clarity to it in a way that I was just like, man, I want to be that good of an entrepreneur someday or that good of a leader. So I learned a ton from him and he's just a great guy. So for any entrepreneurs out there, especially if you get past Series A, you'll usually have an open independent board spot and take that seriously. Like it's a opportunity to get a really good mentor to get someone really good to come in and really guide you, go to help your company, a tremendous amount. Perfect. And then last question, what does success mean to you? When I interviewed at Harvard Business School, they asked me why I wanted to go because I was an engineer and it's kind of unusual and I was like, you know, I don't think I'm going to regret like the money part or the kind of like opportunity cost. I just think it's going to be an interesting story and I think I'm going to have a good time. So, you know, in terms of my aspirations, I think software is a lot of fun and it's just really interesting. I take a lot of pride in all the people we've hired over the years for docs and that we kind of like started their careers, helped them advance in their careers and, you know, been a really powerful avenue for me to just create a culture and environment that, you know, I like to be a part of and it's just so cool that we live in a time when, you know, like people can just pick up and start a company and it scales and, you know, and there's just so much left for software to help with and there's just so much software left to build. So, I think that I just find to spend my career there.