Episode 77
· 48:14
Love the people that you're building for because you're gonna do a better job and you're gonna do right by them. That type of sentiment also is inspiring to employees, investors, and everybody else around you.
Jack Bridger:Hi, everyone. You're listening to scaling Dev Tools. I'm joined today by Dana Oshiro from Heavybit. And I'm really excited to have Dana on because Heavybit was the first VC firm I discovered that specialized in Dev Tools, and I've read a ton of Dana's content. So thank you so much for joining, Dana.
Dana Oshiro:Thanks for having me.
Jack Bridger:Could you tell us a bit about Heavybit and and how you how you operate, why you invest in dev tools?
Dana Oshiro:Yeah. Yeah. So, HubiBet started in 2013. We started actually as an accelerator program. So the entire point of it was that there was, like, a large community of dev tool founders that were coming up, and they they would join, like, different programs and meet other founders.
Dana Oshiro:But I think the reality was that the way a dev tool company, operates and is measured is a lot different from some of the other types of consumer SaaS, say, companies that were around. So we found as, like, operators in DevTool companies or or, you know, executives in DevTool companies and, ex founders that we got a lot of questions, and a lot of those questions seemed to be pretty similar to each other. So we were like, we should probably make this a thing, and built an accelerator and a program to test out, some of our you know, try to answer some of those common questions that people had, and that ended up morphing into something that became a large community. And then we raised a fund, and now we're doing direct investments in dev tool companies. But I would argue that the time that we spend with companies is probably a lot more valuable than the actual cash.
Jack Bridger:Yeah. That's that that makes sense. And you've you've worked with, like, some amazing dev tools, so, like, dev tool household names. Right?
Dana Oshiro:Which Yeah. That's been great. I think, it's super rewarding to get to work with folks who are sort of building out their initial hypothesis around what they, wanna build as far as the company is concerned. And so we've worked with folks like, Netlify and LaunchDarkly and Snyk, Circle, folks who, in the days when we first met them, were 2 to 10 person teams, and then are now, like, much larger at this point.
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Jack Bridger:So if you're looking to cross the enterprise chasm and make yourself enterprise ready, check out WorkOS. We've also done an episode with Michael, the founder of WorkOS, where he shares a lot of tips around crossing the enterprise chasm, landing your first enterprise deals, and making sure that you're ready for them. Thanks, WorkOS, for sponsoring the podcast and back to the show. That's actually incredible to, like, imagine that these kind of companies were ever at that size. And it kind of brings on to this question around, like, how how you get started.
Jack Bridger:And I know you've spoken a lot about, like, finding the one sharp thing, I think you call it.
Dana Oshiro:Yeah. I mean, I think the reality is just, like, most founders have a very big vision of how how we should build. Right? And it usually starts from, some major industry shift and then, a bunch of tools or workflows becoming sort of obsolete or at least, like, really clunky clunky and hard to work with. And then from there, they get this much bigger vision of, like, this is the type of toolset we should be working with, or this is how what we deserve to this is what we deserve to function and do our jobs.
Dana Oshiro:And yeah. So it everybody has a good vision of, like, something much larger. But the reality is when you are a 2 to 5 person team, you kind of have to bite off, stuff you know, you you can't bite off more than you can chew. Right? Like, you can't take on the data dogs or the huge industry leaders with a 2 to 5 person team, usually.
Dana Oshiro:And so what you what usually a founder will do is they have this much larger vision and this much larger market they wanna go after, but the way that they enter that market is kind of through a side door with a small sharp tool. What I mean by that is, it might feel, like a much smaller version of what they're hoping to achieve down the line, but you can't really achieve, you know, total market dominance or whatever, if you don't even have a support team and and you don't have people who can work on accounts. And you you know, there's a lot, as you're scaling a company that you kind of have to sequence in once you've, got a few things working. And I I mean, I think I'd argue for Heavybit. We think the first thing working should be you should be beloved by practitioners, and your end user first before trying to optimize for the, you know, large scale commercial, optimization.
Jack Bridger:In terms of, like, that finding that kind of that one sharp thing and finding that kind of love, have you got any examples of some of the companies of, like, where they started versus, like, where they are now?
Dana Oshiro:Yeah. Yeah. I mean, I think there's a few. I mean, I think I I actually worked at Heroku before coming to Heavybit. And so I think the one sharp thing that Heroku had, and I don't even think it was, like, a complete product or anything, but the one thing that people were very excited about was that initial kind of moment around, like, one click deploy.
Dana Oshiro:It was this idea around what developer experience design should look like and how things should be basically as easy as, like, consumer application, experience. And so I think that that's an example. I think Stripe had, you know, as far as their documentation and their API design was concerned, it was just very easy to implement. And if you make it very easy for people to kinda come through the front door in that way, there is more opportunity for expansion down the line. In other cases, you see folks building a, you know, open source, version of the product as a way to try or as a rate way to demo, value, before actually having to do a whole scale database migration or something along those lines.
Dana Oshiro:So you really are thinking about, you know, these small, sharp tools as the initial onboarding into a much larger opportunity and perhaps a, you know, bigger opportunity to, like, expand value with your customer base. But you don't get that chance, and you can't sell them this massive thing. You don't have any social proof, or you don't have an initial and easy demo or front door to, you know, welcome them into your home.
Jack Bridger:Yeah. And I I actually still use Heroku now. I I've always really liked Heroku, by the way. So, yeah, that's awesome. So you kind of I guess, the the key part is that you're you're just finding something to get that kind of initial, like, foothold that's lower, friction, and then, like, pivots kind of expanding from there.
Dana Oshiro:Yeah. I mean, I think that experience is listen, if you're going to build something that is bottom up and and dev first and truly is a dev tool that developers will reach for and that and, you enter, like, a sale or an organization through individual through IC developers, you basically have to create an experience that's empathetic to the way that they work, and one that makes them love that experience so much that they are willing to, you know, contribute to your open source project, contribute as advocates to the organization or to well, to the 2 founders that are probably running it at that particular time. Yeah. There's a I mean, it it's it's going from a cold start to something, to trying to disrupt a large incumbent, and then that is so different from having a center too long handed down to you, from on-site, from some unforeseen, like, management level that's, like, 3 levels above you. You just don't as a developer, you don't feel that same level of, like, empowerment as you would if you just brought something into your org.
Dana Oshiro:Probably, you bring something into, like, a hobby project first and play around with it before bringing into your org.
Jack Bridger:Yeah. And I guess a lot of these, developers, like, at the individual level are are not necessarily paying. Do you think it's important to kind of get revenue early on?
Dana Oshiro:Not if you're gonna be a ventures and, like, if you don't wanna be a venture scale business, then no. Right? But I think, if you are if you want to raise venture, you do, you know, you do have to have an eye for what do I think I could potentially monetize down the line. That being said, a lot of folks build, even an an open source project and get massive traction as part of the discovery. Right?
Dana Oshiro:So they are this is a problem area that they wanna solve for. They specifically are getting, like, getting a lot of contributors or getting a lot of users to, kinda test it. And they're just trying to figure out, is this something that I wanna build into a a larger commercial, like, company or a start up? Right? Like, you don't not everyone has to be a founder.
Dana Oshiro:It's perfectly fine to run, a bunch of different open like, have a bunch of different open source, projects and repos and, you know, we see that all the time. But down the line, you probably wanna think about how you're going to commercialize it prior to that if you don't raise money. No. You don't really have to think about, am I gonna charge money immediately, or am I going to drive revenue immediately? And then even in that 1st year, if you haven't really figured out what the product is going to be, it then trying to think about, oh, should I charge money for it seems a bit silly.
Dana Oshiro:Like, the the real question is, what is this? And, is it of value to people? And is it of enough value to people that they would pay money to make this problem go away?
Jack Bridger:Yeah. And kind of you touched on that, like, about, like, whether some people would want to, you know, be founders. But I know for for some people, it's like you've spoken when we spoke last time, you were talking about the journey that some founders go on in terms of, like, putting themselves out there and, like, could you talk a bit about, like, about that and overcoming fear and you know? Because I know that you have put out such incredible content for for instance.
Dana Oshiro:Yeah. I mean, I think everybody is comfortable with their own mediums, if that makes sense. And, admittedly, like, broadcast or, like, public speaking is not my most comfortable medium. And so I started as a journalist. You know, that putting out written content for me has always been pretty easy.
Dana Oshiro:And, I I mean, I think the reality is is if you are a founder and you want people to actually adopt your product, use it, or even just offer you feedback, you have to get comfortable with, to some extent, some level of humiliation, quite frankly. Like, you have to get up and stand in front of, you know, large rooms of people, of the meetups that might only have 3 people, and, treat everybody with the same level of respect as you would hope to be treated. The I think the pandemic has changed the social dynamics. Before lockdown, you know, there would be, like, 20 different events a night, at least in San Francisco, and that is part of the reason I was drawn here because I could be in the same room as people who maybe would have been who were, like, my computing heroes. Right?
Dana Oshiro:Like, I've been to meetups where it's 30 people, and it's like, you know, the guy that wrote Cathedral in a Bazaar or, Richard Stallman or like, these are, like, heroes of open source. Right? And when you're in the room with them, you just realize that they're normal humans and the banality of having to go and stand next to somebody and pour themselves a coffee is, like, kind of great. Like, I went to a, kinda demo event on Friday last week, And, one of the guys that got up and did a demo did a great job, but basically, started packing up his bag while the other people who were on stage were demoing. And I was kind of like, what are you doing?
Dana Oshiro:And he's like, what do you mean? And I I said, you just demoed to 200 people, and you're just gonna leave? Like, the whole point is to talk to people at this thing. Right? It wasn't one of my founders, but
Jack Bridger:Yeah.
Dana Oshiro:It was just somebody who'd never, like, been in that, I don't know, in in that groove of, like, we now is the networking time.
Jack Bridger:Mhmm.
Dana Oshiro:And I think it's because, you know, we have a lot of things to fall back on. We have, Discord groups that we feel, like, comfortable with. We have, different types of social media that we can use as a, kind of filter over, yeah, liminality of being just a dumb human in meat space. Right? But I think being a dumb human in meat space makes you a human.
Dana Oshiro:And so, therefore, users will have a more, I don't know. They'll have more empathy and understanding for you. If, like, if you're like, tell me what your problems are. Here are some of the ways that I'm hoping to solve those things. Here are some ways that I have no idea how to help solve those things, or maybe we're not gonna be able to touch on that with this product.
Dana Oshiro:But people, when they are heard, feel, there's just more loyalty that they have towards you, and and they are willing to especially when you're early on and the onboarding process or, the initial user experience is kind of bad, they're willing to, like, crawl over broken glass to try your thing out because you're a human being, not because there's any, like, huge, I don't know, immediate loyalty that they have. It's a loyalty to, like, somebody actually came and and talked to folks to try to find out how to build a solution.
Jack Bridger:Yeah. And, maybe this is obvious for a lot of people listening, but some people, it might not be. Why is it so important to, like, not just shoot off, like, at the end of that, talk?
Dana Oshiro:Because it's not a marketing activity, I think. So there's kind of the speaking at people versus, like, having a discussion with folks. And so understanding that there's a dialogue that is had via both the product as well as, actually, IRL that allows you to understand, okay. Is this is this needed, or and what am I building here?
Jack Bridger:Yeah.
Dana Oshiro:I mean, I guess you could take off and then send a bunch of, like, emails, but, like, could you I I even right now with the pictures I get, I understand the difference between something that is automated or is something that has been sent out to, like, 30 other people in the exact same way versus what a conversation looks like, and I'm far more drawn to a conversation. So, I don't know. What do you what do you think? I mean, you had No.
Jack Bridger:I I agree with you. I I agree with you. I think, there's, like, so much stuff that comes from, like, serendipity as well. And I think it it ties with, I hadn't really thought about it the way that you put it about, you know, with with listening and the importance of like being of listening to people to learn, but also because they value that. And they if you leave at the end, you've kind of opened the conversation, but you haven't actually listened to them.
Jack Bridger:And they may come and give you, like, a brain dump of their thoughts. Yeah.
Dana Oshiro:Even if they're a critic. Like, actually, honestly, the critics are the best people. Right? Because, well, the in person critics are the best people. Because it's not like somebody trolling you and and getting points for kind of, kind of outsmarting you or something like that.
Dana Oshiro:It's like somebody is having a conversation with you and is telling you exactly all the reasons why what you are your why your approach is, like, problematic or whatever, and that is the person that cares enough. Like, that's the person that gives shit enough to come up to you and give you all this information because they have high intent to try to use your product.
Jack Bridger:Mhmm.
Dana Oshiro:I think that that's some of the best feedback there is. It's just it's far worse when it is in a flame flame war style anonymously. Like, you can't do anything with that. Right? Like, you can't go back and ask that person questions.
Dana Oshiro:You can't go back and say, have I solved for what your concerns are? Or and you can't interrogate whether that's a way out there edge case that you were never interested in solving for.
Jack Bridger:Yeah. That's a good point. I guess, also, like, even just whether it was coming from, like, a helpful place or whether they just wanted to, you know, dunk on you.
Dana Oshiro:Yeah.
Jack Bridger:Yeah. That's yeah. I think it's it's a really good point.
Dana Oshiro:I think so so few people will try to downtime you, though, like, in person. Like, who does that? It's ridiculous. Like, why, you know, why waste your time doing that? Why waste your time making someone else feel bad when you could be having a good conversation about something that you like, you know, 2 people over in in the same group.
Dana Oshiro:You know?
Jack Bridger:Yeah. Probably, you don't get someone telling you they could build your product in a weekend very often without networking.
Dana Oshiro:No. Or that it runs fine. They can run it fine locally on their machine. Why would why would they see a product or I don't know.
Jack Bridger:Yeah. That's that's really good. One one thing like this is I don't know if if you have any, just because something I've been thinking a lot about, but, like, when it comes to, like, this kind of fear of putting yourself out there, some of this involves doing things that you may not be super comfortable with. Is there anything that you see people do that helps to kind of improve, those kind of things?
Dana Oshiro:Yeah. I mean, just doing more of it. I think, I mean, I think Edith Harbaugh, who probably did I mean, she was face basically at keynoting every conference at one point, and she's the cofounder of LaunchDarkly. She started, and she was like, you know, I smart people doubt themselves. Right?
Dana Oshiro:And so she was getting up there, and she's practicing her pitch and practicing the way that she it wasn't even really a pitch. It was practicing the way that she talked about, feature flagging and and belief management. And I think she was very doubtful of herself and probably a lot harder on herself than other people are. And just the more that she did it, the more comfortable she became. But she would sit us down.
Dana Oshiro:She you know, we would mike her up, and it wasn't that many people. It'd be, like, 15, 20 people out of our founder group, and it specifically was a public speaking, kind of public speaking feedback session. And one person would have, a page in which they would write down the crutch words that she uses, and one person would have a page in which they were trying to catch if she's doing anything weird with her body, like putting her hand somewhere weird. And others would talk about, you know, I don't I don't know if you've connected the dots between this first idea and this second idea. Like, I think I'm missing something in between.
Dana Oshiro:And so through that, and through it being less about the human being on the stage like, it's not about judging the founder on stage. It's about if you need to communicate something, you will work your hardest to, make that happen. When you treat the entire thing like a project versus it being like a, you know, harsh reflection of yourself, it becomes a little easier.
Jack Bridger:Yeah. Like, if you're if you're, like, solving an engineering problem and or, you know, just you're in an area that you're not that great at, you probably, like, go read up on it and try and improve it. You wouldn't think, oh, I guess I'm just bad at this thing.
Dana Oshiro:Yeah. Yeah. Yeah. I I mean, I I think a lot of founders feel like they're letting themselves down, because on the one hand, they can't get others to, kinda join in that larger, approach or that larger, area of, like, best practices for practitioners. And on the other, like, how are you going to hire anybody or sell this thing down the line?
Dana Oshiro:More probably immediately, how are you going to hire anybody on the engineering and product side, if you can't clearly articulate what you're trying to build towards.
Jack Bridger:Yeah.
Dana Oshiro:And you even have to kind of convince other partners that you're a worthy partner and that you will be kind of a good citizen in this ecosystem.
Jack Bridger:Yeah. Actually, and that's probably a good segue, talking about ecosystems. And I think you you touched on, like, best practices earlier. I know you you've kind of we spoke about movements before, and I know that a lot of your portfolio companies have kind of led movements. Could you share a little bit about that?
Dana Oshiro:Yeah. I mean, maybe the way that maybe the reason why I frame it as a movement is because I come from a grassroots organizing and, with nonprofits and political background. It so I saw a lot of similarities in the early days, even with Heroku of back to some of the work that we were doing, like, around antipoverty and and homelessness services. And what I mean by that is, Adam Wiggins in particular, who was the CTO of Heroku, wrote the 12 Factor app, and that was a set of best practices specifically on how to design, applications for modern cloud. And that kind of became a guiding document for a lot of developers on how they were going to build moving forward, which lowered the barrier to entry to them then trying Heroku.
Dana Oshiro:I think more recently, you see that, like, a more recent example is, Netlify putting out the best practices around it best practices around Jamstack and, some of the major changes that had happened, to the industry, building a practitioner group, building, like, a large ecosystem of other Jamstack players, and then finally launching the Jamstack or the Netlify commercial product. And between those two things, there's, like, far more Jamstack developers than there are specifically, Netlify users. But, you know, it's it's those kind of movements and those kind of kind of cultural shifts that make or break, companies. I think if you're, basically just trying to build against, a a legacy, set of of, best practices, for instance, you're likely to be left behind, particularly at a time like this when there is, like, a wild west of AI everything happening. So I I think, you know, there's going to be a next iteration of what the Jamstack looks like as well, because, basically, every time something becomes very popular, it gets co opted and then kind of some of that meaning washes away.
Dana Oshiro:But the early adopters feel a great deal of loyalty and ownership, and, they literally call themselves Jamstack developers, or, you know, the folks from DevOps. The DevOps wasn't a thing before, and and that's another one where, it was a set of best practices put together via, my colleague, Jesse Robbins and Adam Jacobs from Chef who were building out a set of best practices for DevOps at the Velocity conference years years ago. And now you see a ton of DevOps, engineers. Right? And that's specifically their job title.
Dana Oshiro:You see a ton of Jamstack's developers, and that's their job title. I guess observability is another one too. Like, Honeycomb definitely pop popularized, observability, and there's a lot of people who work in observability monitoring and are observability like, directors of observability at major, corporations now.
Jack Bridger:Yeah. Yeah. I I have 2 questions on this. How do you know if you're the kind of company that should think about a movement? And then the second kind of related question is, like, why why is it a good thing to kind of try that at all?
Dana Oshiro:I mean, if you're doing something that is fundamentally different than the way that most people are doing it, that's, like, a good indication that you probably have to do a ton of education upfront from a best practices standpoint even to get folks to try your product, for instance. But even ahead of that, like, there is this feeling for most founders who build these types of, practitioner movements that practitioners deserve better.
Jack Bridger:Yeah.
Dana Oshiro:Yeah. It's usually, they're just so mad at the way that things are working right now, or they're so frustrated with the way that things are working right now that they're willing to spend 8 to 10 years on building a start up and, advocating for a specific set of best practices, to then change how, you know, software is is delivered or deployed or maintained.
Jack Bridger:What if you're coming at it and you're maybe not this person that's, like, just coming at it from, like, I'm so frustrated, but maybe came at it from, like, this this should be better. How important is that, like, frustration, I guess?
Dana Oshiro:It this frustration is less important than the understanding of the problem, if that makes sense.
Jack Bridger:Yeah.
Dana Oshiro:So, like, when VCs look at it, they have this they have all these, like, special terms and they're they're like, do I feel like there's founder market fit here? Which is basically, like, has this person ever worked, as the person they're going to end up selling to or, you know, having as a champion? If the answer is no, then, you know, it's a bit weird. It'd be like, I don't know, if I just decided that I was going to build a, like, electric aviation company. Like, what?
Dana Oshiro:I don't know how to build that. I don't I've never had the problem of spending too much money on my airplane. Like, you know, like, what what makes me there's nothing credible about my background that ties into the narrative of building that type of a company. And and so I think that is you know, there's a a greater authenticity to having some lived experience, having felt some pains, and then trying to build and and solve against those solve those problems. And, yeah, whether or not somebody is super frustrated with it I mean, if they weren't super frustrated, but they're like, this could be better, I question whether that is, painful enough for anybody to pay for.
Dana Oshiro:And so maybe it is a project or something that is more a goodwill than it is a large commercial business.
Jack Bridger:Mhmm. Yeah. That that makes sense. So one question I wanted to ask was just, like, if someone's, building a dev tool and, you know, they're thinking at some point they would raise money, have you got any kind of, like, rough, guidance on what that journey might look like?
Dana Oshiro:Usually, when somebody has a dental that they're building that they have probably already some, they've built something around that it's not just like a deck and an idea, they usually will raise their first funding from, angels or, from smaller investors. So these are folks who maybe don't have, like, hardcore, ownership targets or things like that. And, usually, they're raising on, what we would consider, like, a convertible debt, which is, like, a safe or a note. These are kind of the terms that people understand. And what that basically is is, somebody is lending you money with the promise that they're that, that that that everything will get priced into the next round.
Dana Oshiro:And so, therefore, their ownership, etcetera, will convert to some kind of preferred stock down the line. So the first is usually angels and and, like, friends and family.
Jack Bridger:Is that, like, a 100, 200 k or something? Or is that
Dana Oshiro:Yeah. But it's usually and it's usually small checks. So anywhere from, like, I would say, like, 10 k to 20 fives. They're probably 50 k checks. Right?
Dana Oshiro:And that is usually enough to sustain you to build at least a working MVP and do a bit of discovery. At the point in which you want to look at raising, venture capital is when you wanna start, usually hiring folks and when you have seen some early momentum. And I would say those checks tend to be or those round sizes tend to be somewhere between, you know, 1,500,000 through to 4 or $5,000,000, on the proceed.
Jack Bridger:And I guess, like so to make a good impression of you, if you've got if you've got, like, an email landing well, I guess, also that's kind of a question, but, like, how if someone wants investment from HeavyBet, they would just, like, drop you an email and say, we've done this, this, and this, and here's our product or, like, how what's kind of a good approach for that?
Dana Oshiro:Yeah. I mean, usually, if they it I I get, I mean, I get introductions all over the place where I'll get an e a cold email. I mean, the best way in is to actually talk to one of our founders or somebody who's in our broader community because we have, at this point, 8 800 advisors who've, contributed to our content and our events and all of that. So the likelihood that you will meet somebody that, can get you a warm intro is pretty high, but, also, I'd like for folks to have an understanding of the type of investor that we are and what we do. And I would say, I mean, we are pretty hands on.
Dana Oshiro:Right? Like, we take, we take board seats when we lead. We try to meet with our founders, a minimum of, like, every 2 weeks, if not more.
Jack Bridger:That's a lot.
Dana Oshiro:Yeah. Yeah. And we're I mean, the DNA of the original accelerator still exists with our portfolio companies and that we try to build a, you know, plan of action and a a series of benchmarks and milestones that founders can hold themselves accountable to, in the same way that, you know, it doesn't make sense to build an entire product without having sort of incremental checks and balances. We think the same thing is true for in a way you build a business. So interactions through our founders, showing up to events and stuff like that that we're doing, like, taking a read of of some of our content is probably pretty useful.
Dana Oshiro:The relationship that we have with our founders really is a 8 to 10 year journey, generally. And so, I would hope that, folks, you know, value us more than, the cash that we're able to offer today or to, that we're able to, like, put into a company today.
Jack Bridger:Like, yes. It's seriously so useful. I recommend it to everyone, especially on the kind of, like, enterprise side of things. I think it's especially, like, unique. I don't think there's really anywhere else that has such good content on enterprise level go go to market and all that sort of thing.
Dana Oshiro:Oh, thanks.
Jack Bridger:So what does it look like in terms of, like, you get an email, say, you get an a warm introduction from someone that, you know, you respect. How do you start thinking about whether this is, you know, a good investment, whether this company is is at the stage where you would want to work with them?
Dana Oshiro:Going back to the idea that the founders should have some understanding of the problem that they're trying to solve, I think that's, like, one of the main things. I I think there's a lot of investors who say, like, we invest in teams, which is like yeah. That is like legally the entity that you have to invest in. Smell the lie. But, yeah.
Dana Oshiro:I mean, we invest in Sanders who know their shit. Right? Like, they're not trying to build something that is completely, foreign to them and sell into an audience that is completely foreign to them. We are looking for people with, strong opinions on the technical side of the house who often have, a very good handle of, what they are building and, in some cases, have built those same things in internal to a large organization. And, usually, where we find that we can add most value is on the go to market side in helping a technical founder go from, like, a great, you know, technical manager or engineering manager or or architecture or product person to turning them into a CEO.
Dana Oshiro:And I think those are are they're very different, I think. You know, I think there's there's nothing more scary to a technical founder than the idea of having to hire up a marketing and sales team. And maybe those marketers and salespeople are actually also technical, you know, have have worked inside of a dev tool startup in the past. But there is something about the title of marketing and sales, something about the title of or something about building content or a thought leadership that just is so foreign and uncomfortable to folks. And so helping them understand, okay.
Dana Oshiro:Well, this this is actually what this means. This like, let's translate what this actually means. It's like, content marketing, in effect, is is is you writing down, you're doing it wrong. Here are the ways that we should be doing things because this is what we deserve. It's not that hard.
Dana Oshiro:It's just longer format than the hacker news comments, greeks that you're going to put in some other, you know, post or whatever.
Jack Bridger:I mean, I think you're maybe slightly underplaying something that you're very, very good at, but yeah. Because I I feel like it can be hard. Right? Like, it's like you're you're great at writing content to, like, still felt it can't be hard, but yeah.
Dana Oshiro:How If
Jack Bridger:I know what you mean.
Dana Oshiro:Well, I mean, the other thing is is doing nothing in obscurity achieves the exact same thing as doing, something wrong publicly. But at least if you did something wrong publicly, you've learned something. Yeah. And you can always roll that back. You know?
Jack Bridger:Yeah. Yeah.
Dana Oshiro:Unless it's like you've done something like a Greek you know, like, you're just like a bad human being doing something egregious in public. That's a totally different thing. But, like, the idea that that wouldn't, that no one would take notice of that is Mhmm. It it's bizarre. Right?
Jack Bridger:Yeah.
Dana Oshiro:Like, doing something is almost always better than doing nothing. That's true. Yes. And, like, that's the thing a lot of people don't understand with raising money is that once you are once other people, are dependent on you returning that investment, you've kind of you've put yourself on a path. Right?
Dana Oshiro:You have a timeline, and you have a certain number of months in which you should be hitting specific milestones in order to figure out if if this is gonna be the business that that you, like, dream of building. So having $7,000,000 in the bank or whatever might feel amazing on day 1. But on day you know, I but on 20 20 months in, you might be like, okay. The expectation is that, you know, I'm gonna I'm gonna 3 x whatever our user base is, our revenue looks like, and all of that. And, that's scary.
Dana Oshiro:So just understanding that, like, if you take venture money, like, you're going to do a capitalism. You are agreeing to do a capitalism. Like and that is, like, something that I you know, coming from nonprofits and coming from and not coming from venture originally is something that I try to underline you folks. Yeah. And and maybe, you know, I don't think they had anything wrong with with not taking venture money or I mean, the best thing for most businesses is to, not take any money from anybody and just, be profitable.
Dana Oshiro:Yeah. Right? Like
Jack Bridger:That's, so I guess it's hard, isn't it? Sometimes in dev tools just because of it's often requires a lot of a lot of developers, I guess, basically, before you
Dana Oshiro:Yeah. It just I mean, it depends on how sophisticated you're gonna build out the system in the beginning. Right? Like, if you're doing something in distributed cloud or database or whatever, it's, like, very, you know, engineering intensive. Yeah.
Dana Oshiro:But maybe start with something that's more lightweight on the application layer that you can get away with just your friends working on. And that that's cool too. I mean, some people lock into big businesses that way by building something that people really love and then, just having enough initial revenue, also that small, sharp product to then fund the next stage of growth.
Jack Bridger:Yeah.
Dana Oshiro:But it's it's rare to go, like, IPO and not have taken on any money.
Jack Bridger:Yeah. That's interesting. I think that's yeah. That's why I understood it. So it's interesting that that is the case.
Jack Bridger:Yeah. Guess the best possible way is if you own the whole thing and it just makes loads of money and you can just
Dana Oshiro:That's a dream. Right? Like Yeah. That's that's the dream of what a dream. Like, it has been the dream of how people have sort of, people have avoided taking venture money for a long time, and they might come to us.
Dana Oshiro:And they're like, I just thought if you build an amazing developer experience, Like, it's kind of I mean, it's literally, like, the premise of Field of Dreams. Like, if you build it, the developers will come, and then they will pay us. We will be rich. Dot dot dot. And, like, there's no
Jack Bridger:They were not.
Dana Oshiro:Connecting the thread.
Jack Bridger:Yeah.
Dana Oshiro:Yeah.
Jack Bridger:Yeah.
Dana Oshiro:But it's it it it it takes, like, a certain stomach, and it takes a a certain amount of grit. And it also takes, like, I think, patience and pragmatism and, and, like, a good understanding of how to project all this stuff because as much as, you know, having a good relationship with your investors is important. Understanding how to communicate, your progress, in a way that, doesn't immediately, like, set up alarms or, isn't an underplaying of of or sorry. Isn't overplaying where you're at is also pretty important. Right?
Dana Oshiro:Like, just being able to manage people's expectations all around is one of the hardest skills that I think a founder has. Managing the expectations of your employees to understand, like, this is something that we have to do by this date, you know, what your timelines look like around your fundraising. And if they're like, why is it taking so long? They'll get very, very worried about that. There's a lot of people whose emotions are kind of riding on the way that you communicate.
Dana Oshiro:So, yeah, it's a it's for sure a high pressure job, much much higher pressure job, I think, than, so maybe something that people have done for 15, 20 years. It's like, if you're a great engineering manager, you're a great engineering manager. Half the time, your team will follow you anywhere. I I don't know that that's always the case with, being a founder.
Jack Bridger:Yeah. It's a hard job. Yeah. Dana, I think that's all we've got, time for. If you had one kind of takeaway for founders listening, what what would it be?
Dana Oshiro:I love the people that you're building for.
Jack Bridger:That's a great one.
Dana Oshiro:Because you're you're you're gonna do a better job. You know? Like, you're gonna do a better job and you're gonna do right by them. And that type of sentiment also is inspiring to employees, investors, and everybody else around you. If you really do wanna improve the lives of of people, you should know who those people are.
Jack Bridger:That's that's amazing. Where can people learn more about you and about Heavybit?
Dana Oshiro:Yeah. So, heavybit.com is, like, our website, and we have tons of content there. I I mean, I'm just Dana at Heavybit, so feel free to email me. I'm danaoshiro on basically every social media, whatever thing that you wanna contact me on. I'd maybe avoid, like, TikTok or Instagram because I never check that kind of stuff.
Jack Bridger:Yeah. Amazing. Well, thank you so much, Dana, and thank you everyone for listening. We'll be back soon.
Dana Oshiro:Thanks.
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