What's Stopping You? - Episode 1
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[00:00:00] Christian: Hello and welcome to episode one of What's Stopping You. Joining me is my co-host Shai Schechter, and Drew Bredvick. Drew works at Vercel. I don't know exactly what you do. I think it's something product sales or something.

[00:00:13] Drew: Yeah, it's sales engineering. It's an interesting role. Not a lot of people know about, but

[00:00:17] Christian: Sales engineering.

[00:00:19] Drew: Sales plus being a developer.

[00:00:21] Christian: Our goal for this episode is to help you.

We're gonna try to help you through a problem that you're currently stuck on. If we can help you through this problem, we have been successful. Can you tell us a little bit of a background of the project that you're working on, and then we'll get into the specific place where you're stuck and talk about how we might be able to help you.

[00:00:39] Drew: Yeah, so I'm working on a project called registered.dev, and I started this project after seeing quite a few problems in the sales engineering space. So what is sales engineering?

Right?

We should probably start there because most developers have no clue what sales engineering is. Sales engineering is pretty much just the going back and forth of figuring [00:01:00] out in a sales process, being the technical resource for both the company, so I work at Vercel, and companies that might be considering using Vercel. So I'm the like, go-to technical person when you are evaluating if Vercel's a good fit for you or not. And that is a field where it's great to know a lot of business. Like what business value is Vercel going to be adding to these people's day jobs.

But also what technical blockers, when you're migrating from Next hosted in a Kubernetes cluster to Next on Vercel, what are the common gotchas? How can I help you get up and running? And I transitioned to this role almost two years ago and it's uh, kind of a, a bit of a jump from just a traditional engineering role, right?

It's a lot more customer facing, involves sales. I work hand in hand with an account executive, pretty much just the person selling Vercel. And [00:02:00] so it's slightly less technical than a traditional, standard engineering job. But one of the pros is you get to see the inside of a business and like how it works.

Registered.dev is born out of seeing all of these problems that exist in the process of buying software, but skewed specifically towards technical products. So I don't wanna build a sales tool that helps, if you're just selling some random SaaS on the internet, this tool isn't going to be built for you.

It's more built for dev tool companies specifically. Because there's some things that are a little bit different in a sales process for a company like Vercel than, I don't know, just some standard SaaS.

Okay. It's a Salesforce for dev tool companies. Something where there's more of a technical aspect to the sales cycle. It's not just emails back and forth. There's some other technical thing that's happening that needs to be kept track of.[00:03:00]

Yeah. Salesforce has no concept of what a GitHub repository is, right? That's just something that is entirely missing in that space. And there's quite a bit of manual work, some things that could be automated, some things that could be shared across deals. Because if you're doing a bunch of bespoke work for one deal, it's kind of the same concept of, dry, do not repeat yourself.

You wanna reuse those assets across deals so that you're not doing a bunch of bespoke work every single time to, close a deal.

[00:03:32] Christian: Why is this important for you to work on? You're enjoying your job at it sounds like, making a lot of money. Is this something to help you make your job easier to be able to automate and scale? How are you thinking about this?

[00:03:45] Drew: Yeah. So the problems I've seen I guess to start, I've always been someone who like tinkers and builds projects on the side. Even before I worked at Vercel. I think I've, the other, I think two years ago I did a retro on how many projects I had started [00:04:00] and maybe shut down or failed or killed or something like that.

And it was at least 12 that had gone like full, the full through the full cycle of idea to domain to actually having code and actually having a working project. If you count the graveyard of domains that I have that have never seen the light of day, they just sit in my Google domains.

That, that's even higher. So I'm always thinking about what I want to build and things like that. And I'll always do that regardless of where I work. But joining sales engineering has been very eye-opening in terms of products or spaces that are underserved. Part of it is, yes, these are all things that could be made a lot better during Vercel's like sales process.

But I think the thing that happens at a lot of these companies is you solve it at your current company and no one pulls back and generalizes the solution. Like we're working on making all of these things better at Vercel right now ourselves by just making a new Word doc [00:05:00] and creating a new format and all of these different things.

But that does fix the problem at Vercel to an extent. But I just saw a really good opportunity to kind of take the generalizations learned, take the learnings from these fixes that we're applying at Vercel and generalizing them a little more.

[00:05:20] Christian: Okay. I see that, I see the benefit to society that you can take this these SOPs that you're developing at Vercel and bring this to the world. I think what I'm more curious about is individually, what is this doing for you? Is this a compulsion to start new projects, which Shai and I both share

Is this, that you would like to be moving into SaaS? What how would this change your life

if

this became a product?

[00:05:40] Drew: So part compulsion, right? I will always start projects but also have always dreamed of someday running my own SaaS full-time and things like that. All of that to be said I love my job at Vercel. I'm not leaving any time soon. But I think if you were to, you know, sitting back in [00:06:00] a new year, coming up good time to reflect and think, what do I wanna be doing in 10 years?

In 10 years I would like to be running my own profitable SaaS and kind of with a small team in in that vein I wanna be doing things that make progress in that direction.

[00:06:16] Christian: Okay. That tracks. Shai, anything here before we move to specific problems?

[00:06:20] Shai: The main thing I'm curious to know is, it sounds like you're building something that would benefit you in the day job right now or benefit your team. How much have you done to identify who else it would help? Are there other examples that you could pinpoint? Here are a dozen companies, people in companies even that I know immediately, like this would help them as well?

Or is it, are you coming from, I know this would help me. I haven't spoken to other people, where are you at with that?

[00:06:47] Drew: Yeah, so I've done a couple things here. One is I've found competitors that already exist and so have validated that. And they've, some of them have raised funding. Some of them are a little bigger and more [00:07:00] established. Some of them are newer and in the space, so I've done that validation in the sense of, I think there is a market here.

And with those tools, essentially, I'm just niching down a little bit. So if you're taking the top down approach of is there a market for this? I've, I think I've justified that for the specific functionality and differentiators. I do have quite a few relationships with folks at various dev tool companies.

And if you are one of those people actually and you're interested in sales tooling and you work at a dev tool company, my DMs are open on Twitter, please slide into them. But the approach I'm gonna be taking there is I want to get something demoable first that feels real, and then I'm gonna take it to a bunch of those folks. It's also I was previously using the excuse of Hey, it's the holidays, nobody wants to hop on a call over the holidays. But that ex, that excuse is running to its end here shortly.[00:08:00]

[00:08:00] Shai: Yeah, I wanna dig more into that. So you've got the holiday excuse. Fine. I would push back more on that if this were the beginning of the holidays, but that excuse is running out anyway, so I don't need to push back. But the other one of, I'm curious why you want to, why you want to move the product further and how much further you want to move the product before you bring this to those peers that you have in the industry.

[00:08:24] Drew: Yeah. The way I'm thinking about it is it needs to be real enough for, because what I'm going to go for is if I build this, will you commit to buying it? And so I'm looking for, I'm looking for kind of a strong verbal commitment, and that's one thing to do. Like customer. I think there's two buckets.

There's kind of the customer research bucket, and then there's the like pre-selling bucket I, in the customer research bucket. I've been rather thorough about examining our sales process at Vercel, [00:09:00] asking some of my peers at Vercel for feedback. And then my, my boss Ben Seymour, he's also on Twitter has been doing sales engineering for a very long time, and I'm going to be getting some feedback from him as soon as I have something tangible as well.

So I think between getting quite a bit of feedback from people internally. And then I guess what I'm saying here is my goal is to have something a little more real before I do too many interviews because I know the problem really well. Like I've been doing, I've probably, how many deals do I think I've been on at Vercel?

I don't think I can probably share that number. But I have been very involved in quite a few deals. So I think from the sense of building the, like scratching my own itch thing, I think is at least going to solve the problems for a company like Vercel.

And I think a company like Vercel is my perfect target customer, if that makes sense.

[00:09:56] Shai: Okay. So it sounds like you're saying [00:10:00] that because you're essentially, you're building this product for you as well as for others. Like you think you've got a good sense of what needs to be built, that you could take that demo, you could take the building process a little bit further before you need to get too much research from

[00:10:15] Drew: Yeah. It, yeah, because if it was a niche that I didn't know a lot about or or a niche that that didn't have clearly defined competitors already I think I'm using those two things to justify not spending a week doing customer calls. And then my hope is to have something real when I do those customer calls so that the feedback means more, if that makes sense, because if I show you a demo and you've got feedback I think your feedback's gonna be much more actionable than if I just talk about something in the abstract.

[00:10:50] Shai: Okay. And how do you feel about the idea of those customer calls when they come? Is that something that, like, really excites you, is that something you're kind of [00:11:00] putting off?

[00:11:01] Drew: I'm, I would say I'm putting it off in the nature only of, like I've done plenty of calls. It's probably in the thousands. So I'm not putting off the fact of like, I'm, I'm happy to hop on a call and talk to people, but the act of going to your network and saying, Hey I'm working on this thing, please.

Please give me feedback on it. That's the thing I'm putting off, if that makes sense.

[00:11:25] Shai: Okay yeah. And so with that in mind, that's why I'm that's why I want to get a good sense of like the justifications you gave for why you are, why you're not bringing this to other people yet. They're convincing. But given what you've said about your feelings about that next step, I am curious to dig into whether they are true

[00:11:46] Drew: Yes. I think we've arrived at um, probably what is the like, um, what do you call the, is it your Achilles heel? Is it something like that? Pretty much my wife [00:12:00] says I can convince myself of anything, and I think she's probably right. , this you've probably picked a rough first guest in terms of, are these things true or not?

In my mind they are. So I guess I think I can probably, the reason I'm letting myself not do the customer calls is because I think I can probably get to a good enough outcome with with just skipping this step. Now, if I was giving this advice to somebody else, would I say, Hey, skip this step?

Probably not. Even if you do know the domain really well because it starts these relationships, then it can be easier to do the presale thing later. And then they're warm instead of, I don't know, like mildly warm, like lukewarm. They'll actually be like warm or hot. Yes, I agree with you.

There's, There's plenty of good reasons to go do this. And I probably should.

[00:12:53] Shai: Okay. Um, This is cool. So So there's no, but this is good, [00:13:00] right? This is

[00:13:01] Drew: we're getting to the bottom of my psychology,

[00:13:03] Shai: yeah. Are you feeling a little bit uncomfortable right now?

[00:13:05] Drew: Yeah, that's perfect. A little bit uncomfortable is perfect.

[00:13:08] Christian: We'll ride

[00:13:08] Shai: No. And look, the thing is, it's, it, there's a spectrum, right? On the one hand, you could sit and build this completely in the dark for years. With no landing page, no communication with the outside world. NDAs with anyone you tell, like I've been there before many years ago.

That, that's one end, that's one extreme. And then in the other extreme, you could decide to go out and do these calls before you've built anything, thought about anything. And the perfect spot, there isn't one perfect spot. And it's not a clear black and white. And so one of the questions is like, if you could do this building stage, you, if you could throw a demo together very quickly and then take that to, to your peers, to the market for feedback, then yeah, fine.

And even if you are doing it as an avoidance tactic if the downside isn't much like then whatever, with it. lean into weaknesses, it's fine. So I guess the question is how long will this actually take to get to that point?[00:14:00]

[00:14:00] Drew: Yeah,

If

[00:14:00] Shai: it would take a long time then it might be worth digging more into " let's question this".

[00:14:04] Drew: That's a really good question. So I've been making to talk about the estimation of what I've got to build. A little bit of a plug for my day job here Vercel, Next.js, the starter kit um, platform starter kit that Steven Tay made. I'm using all of the things that I've, that I regularly learn about at my day job.

So it speeds things up quite a bit. I'm actually moving rather fast on development of this, like what I have as an ideal state for kind of a rough MVP, the things that will take longer. So there's the platform. Then I probably need to integrate with some different CRMs. One being Salesforce, even though that's the tool I'm despising in my landing page copy I probably do need to integrate with them maybe HubSpot. For which CRMs to integrate, I definitely want that to be a customer led , what are customers saying they want me to integrate with? So that's something where I do a bunch of [00:15:00] user research and not really build it before getting that validated. Those pieces are gonna probably take a little longer though. I think because it put simply my app is a big CRUD app, right?

It's just a bunch of simple logic. Mostly it needs to send a couple emails, it needs to enforce state in a couple weird spots. But it's mostly a CRUD app. I can build that rather quickly. The like crazy syncing engine back and forth with Salesforce and complying with their crazy API requirements and then getting in their marketplace and all those other things, like that's gonna be a beast.

So my thought was build the MVP for the first thing and kind of get feedback on that before I build the crazy Salesforce syncing stuff.

[00:15:50] Shai: Okay. And how far through that are you? How much if you think about what that MVP needs to have in your mind, how much of that have you done? How much is still to do? How long does that take?[00:16:00]

[00:16:00] Drew: Let me look at my whiteboard for one second.

[00:16:02] Christian: He's got a whiteboard. That's a good sign.

[00:16:05] Drew: whiteboards are a good sign. It's a green flag.

[00:16:10] Shai: It's, in fact, it's all you need for a successful

[00:16:12] Drew: yes. Oh, we're good. We're good here. Okay, so there's probably a bunch of styling things I need to fix, but two main pieces of functionality out of 10 remain. So I've, I've kind of done decent there. That doesn't include anything with the Salesforce syncing, though I haven't even touched that bucket of stuff.

[00:16:36] Shai: The reason I'm pushing so far down this line is because in my own experience and the experience of everyone I've ever seen deal with things like this, the there will like, once you bring it to those people, you will learn that, that there are things that they want that are very different than you envisaged, even if you're building something for yourself.

And so the further you go down the building line [00:17:00] the more uh, challenging that becomes.

[00:17:02] Drew: That's very fair. I think I think that means

like what are those core assumptions that break

[00:17:09] Shai: and I'm not sure you can even guess. And that's the thing, like I, I have tried very hard in, in these things in the past to try and guess them beforehand. And even, even to the point of like, ,, I've done that thing of, okay, I know that this is not ready. I know that this I know that everyone is gonna get to this point and get stuck, but I'm just gonna do it anyway on a call with them.

And I'll watch them get stuck and then we'll figure it out from there. And they all blast straight through that point without any difficulty. And I'm like, oh, they did not get stuck on the point where I knew they would. And then they get stuck on some other point that I was totally convinced would be super intuitive for them.

Look maybe that's just me. Maybe you are better at estimating these things than I am. I've just I've never seen it. It's just, it

doesn't

[00:17:47] Drew: just work. I agree with that. I think the takeaway there then is I probably shouldn't spend too much time on any, like UI polish or anything like that. I should just get their core functionality working and get it [00:18:00] in front of people as, as quickly as possible in that sense. So that they can.

so that I can do these. Hey, let's get you an account and try this out and see how it's working for you and things like that, and get like actual product feedback earlier rather than spending time on, on the polish.

[00:18:19] Shai: that sounds like it could be a reasonable approach. How do you feel about that?

[00:18:22] Drew: It feels pretty good. I think the demo thing that I was hoping to do though was pretty much even before I would be at that state.

So I think, um, I think I'm still gonna stick with the demo thing of if I can, because to get to a demo state, right? Like I don't need to have payments working.

I don't need to have a million things working. You can just, you can do a demo of , like here is an account that already is populated with data, so you can just skip all these other CRUD places to build because you've just manually inserted things in the database. And so I think that approach is what [00:19:00] probably gets me feedback the quickest.

I'm not sure though is there a difference between feedback from me demoing something versus feedback from, me giving you an account and you signing into it. Like those, it's easy to watch me drive through something when I know where I'm going. Like the, a very weird comparison here, but like I've, I had a friend growing up who lived in the country as a kid and I'm pretty sure he could drive that with no headlights.

Just going home cuz he knows the road. Is that a good idea? No, he probably could I would turn my brights on, like I am I drove to his house many times, but, I need the brights and somebody else driving through my site. Probably it's different to sit in passenger and watch that person drive versus driving yourself.

[00:19:51] Shai: Okay. So which of those are gonna be most useful? Is it, does it make sense to get to the quickest possible point where you can demo it to them and then do that? Or

[00:19:59] Drew: [00:20:00] yeah.

[00:20:00] Shai: Yeah, you're right. It's not the same kind of feedback as when they're using it, but I guess the fundamental question is, what do you want to get from these

[00:20:07] Drew: Yeah. That's what I was I guess it's like my gut instinct says am I solving a problem your business would pay for? Is what I want an answer to.

[00:20:18] Shai: Okay.

[00:20:20] Drew: Not is my UX well designed? Cause I don't really like to all the UX people out there. I do care about ux, I'm not, but at the MVP state it's not as important to me.

[00:20:33] Christian: learning, if you're solving a problem that a business would pay for, is something that you could do with no product if you're just describing what the product is. And something I think that the thing that I'm most interested in pushing on is like the, there are lots of reasons for doing interviews at one stage or another, what the advantages are.

But the thing that I find myself most curious about is that there seems to be emotional resistance for the way that you phrased it is pleading for feedback. It feels like there's [00:21:00] something there that you may be intellectualizing a reason for not talking to more people upfront. That maybe it's like a fear of rejection, that you're gonna show someone this after you've thought it's a, is a really cool idea.

And when you ask someone if they would actually pay for it, the answer might be no. And that, that would suck. That would that'd be painful. And so the longer you can push that down the line, the. Safer it's gonna be, that's a

[00:21:22] Drew: that's fair. That's

[00:21:23] Christian: for a lot of projects. For yeah.

[00:21:26] Drew: okay. So maybe my um, so I've, I've identified 12 target customers. I think I was mostly putting off talking to them via the reasoning that you know, early on, Google's founders said, it's better if people find out about Google later because we don't want you to use it today, because tomorrow it will be a better product.

And so your first interaction with the product will be better. , I think I'm probably using that justification to say look, I want these [00:22:00] 12 target customers here. These are like my only good leads that I know have a high chance of closing, so I don't wanna waste them. Now if you can correct my thinking here in the sense of like maybe bringing them into building the product and letting them see it at an earlier phase is better.

[00:22:17] Christian: Are there only 12 customers for this thing

[00:22:19] Drew: No there, there are quite a few more. The dev tool market, according to Crunchbase, is 3,768 companies. And it's compounding annually at 14.6%.

[00:22:32] Christian: So let's say you hop in a call with each of these 12 people and you just completely embarrass yourself. You insult them. They end the call and they hate you. They're like this Drew guy. He's terrible. How might you find out of those thousand people, how might you get 12 more of them on the phone?

[00:22:48] Drew: I would probably just look through Vercel's Slack Connect and see who else I could find that I have a good connection with. And go add them on LinkedIn and go message them of Hey you're in a similar [00:23:00] space. We're in right companies. Vercel has a very extensive slack Connect setup.

I think every dev tool company I've ever heard of has a channel with us. And so just figuring which companies fit into that bucket of ones that are obviously in the dev tool space and are probably a little younger. I think it's probably easier to sell to a dev tool company who is.

a year or two old versus Microsoft. So definitely biasing earlier in the life cycle. But all of that to say yes, I think I could find 12 more companies that are on this list.

[00:23:37] Christian: How does that feel? Is that hopping on the slack connect and finding new ones? Is that

[00:23:43] Drew: It feels it feels like it's okay. I probably just need to go have these conversations anyway. Finding the correct people shouldn't be too hard cuz I picked these companies because I have good connections there. So finding the right people to actually go talk to shouldn't be a big deal.

And then, 30 minutes on my [00:24:00] calendar's not a big deal either. All of that to say. There's not that great of a reason that I haven't had those calls, Christian.

[00:24:08] Christian: Okay.

[00:24:08] Drew: I do wonder though if I'm, there's this concept of I guess in my mind I'm viewing these sales opportunities the same way I view Vercel's sales opportunities

Where say something goes wrong in a conversation, deal goes bad or whatever the people just disappear and then they'd never talk to me again.

That is not going to be necessarily true for these early feedback customers that I'm talking about here, right? These are friends that I have that work at other companies. They're not just going to disappear if if the tool isn't a good fit for them. So I guess. I guess I'm falsely conflating these two things.

[00:24:53] Christian: And this is the core thing that we'd like to help you on. You don't you have no obligation to justify to us while you're taking an action or

[00:24:58] Drew: Oh, yeah. This is the [00:25:00] best way my brain works anyway, is like just talking through things out loud. It's quite annoying to all the people around me. But at a podcast setting, it works pretty well,

[00:25:07] Christian: sure. That's a, that's insightful also that the making a bad impression, having a customer call go bad in the context of your day job at Vercel has a very real consequence. And those people just disappear and you don't see them again. So it makes sense to me that you might be framing the conversations that you would have with people about registered.dev in the same sort of context that you really need to make a good first impression.

You gotta nail it on the first try, and if not, they're just gonna disappear and you're never gonna see them again. So I, I think the thing I'm most curious. Of at this point is digging for other resistance in that spot particularly the way you phrased it, pleading for feedback.

Tell me more about that. What, because that does sound bad. I don't wanna

[00:25:49] Drew: Yeah, that does sound bad. That does sound bad.

[00:25:51] Christian: You framing that, that sort of

[00:25:52] Drew: I'm not sure why the phrase pleading for feedback came out but you're probably onto something there. People have busy [00:26:00] calendars. They owe me nothing. asking for 30 minutes for feedback on a product that's not real yet. Also feels maybe they're taking this call because, drew works at Vercel and would sure would be nice if Vercel promoted our tweet or whatever, I, I'm cautious, I don't wanna be dipping into any buckets of goodwill that aren't necessarily mine to dip into, if that makes sense.

Like I'm cautious about the the Vercel affiliation piece of it, if that makes sense, because obviously this is not a Vercel product. This is my product. It's hosted on Vercel and uses a lot of Vercel open source. But which is there's a lot of overlap here between my day job and.

this side project space. So I guess I'm just cautious to those relationships I'm being extra cautious and guarded with, if that makes sense. So maybe it'd be better if I just picked random companies. I think I [00:27:00] would feel better if these companies didn't have a Slack connect with Vercel and I had never even heard of Vercel or don't even use it in any way, that would almost make me feel better.

[00:27:09] Christian: that's interesting that that would feel better. I could say that also in increasing your feelings of abundance of this audience, if you know that there's a channel in a way that you can just get. Tap into this unlimited bucket of these thousands of companies and get 'em on the phone

[00:27:26] Drew: Yeah. Okay.

[00:27:27] Christian: that method is of getting them on a call can then become part of your sales pipeline.

[00:27:31] Drew: Okay. So we've decided it, feels like that is the easiest switch. It's just switching from companies that have very tight close relationships with Vercel to ones that have no relationship to Vercel, at least for customer feedback. I think it's also a good way for me to, something Stripe did that was pretty impressive early on was they intentionally set their fees higher than their Com competition.

And it's because it made them build a more [00:28:00] useful product. You're not gonna pay higher fees if your product isn't great. I think if I go after customers that have a lower propensity to say yes to me I might build a better product. If I go directly to someone who might just buy it out of having a good relationship with me that feels like a less solid data point.

[00:28:23] Christian: It does seem like there's a lot of emotion tied up in the relationships that you have with these companies that were built through Vercel, that you may not fully trust that the motivation is there, there are myriad other reasons why that company would be interested in something you were building that aren't necessarily because the product is good and it solves a problem that they wanna pay money for.

[00:28:46] Drew: Yeah. And also just the being cautious of double dip is the wrong phrase here. I'm kind of looking for, even though I'm serving a segment that is very close to Vercel, I kind of want a strong segmentation between Vercel and this project, right? I don't want [00:29:00] the walls to be blurred between them, cuz this is definitely my project.

There are things that I've learned at the day job that I'm taking into it, but, , yeah, I gue I guess just the segmentation there matters because I wanna feel good about when, if, say someday I have to go into court and answer, did I use any of my Vercel resources to to um, complete this project? And is this project my IP? I would like to say, yes, it is my IP.

And so the caution here comes out of two places. One's maybe emotional but the other might be like actually legal now is this me rationalizing something, using something that I know to decide, I don't want to do the thing that I just put up on a emotional wall around maybe. But but also it sounds reasonable, right?

[00:29:40] Shai: That may well be the reason. That may well be what got you to saying it, but I think it is also it's a.

legitimate concern and even, there are cases where there are stories where things like that have happened and then even though you, even though the person hasn't used any of the resources from their company, the fact that they were doing it, on work time or even while they were employed there, like it, [00:30:00] it can cause some messy situations in the future.

So it is a valid thing to be thinking about is this entirely separate? Am I confident that it's gonna whether it's a, whether it's taking people from Slack connect or not, like you do wanna make sure that it's, that it is seen practically legally as your own separate thing.

That's valid.

It shouldn't stop you from making any progress, but it's something to make sure of.

[00:30:24] Drew: I do think though Vercel has proven to be a very okay spot for side projects. If you go look at the dev-rel people at Vercel, they're all launching a million things of their own projects that and things like that. So I think my concern there is slightly unfounded because there's plenty of examples of people at Vercel doing similar things and being a hundred percent fine and getting

[00:30:46] Shai: The easiest thing to do is if you're confident that your boss will be fine with it, you get them to write something to confirm that they're fine with the side project, and then you never have to, but so yeah I don't think the concern is invalid. I think if you let it stop you from ever making any progress on this thing, that might be unfounded.

But yeah. No, [00:31:00] it's,

[00:31:00] Drew: Do the paperwork is what I'm hearing, which makes sense. I can, I'll see my boss Tuesday. I'll ask him about it.

[00:31:09] Shai: The, in terms of the, like what you said about not sure, not being sure how you feel about tapping into those relationships that you've got while you're at your day job. That I think that's very fair. And I think it sounds like you've worked your way towards a possible alternative that you might feel more comfortable with.

You might find that there are some exceptions as well. There could be some people who, yes, you interact with them through work, but actually you have such a, close personal relationship with them that, that if you sat down with them and said, look, I'm working on this side project.

You might feel very comfortable in that dynamic that they won't feel pressured to do it cuz of. Things getting in the way. You might, that might be something that you just feel out on a case by case basis. There might be some people who you think are cool to do this with and some people who you'd rather not.

And you'd rather go for anonymous people.

[00:31:55] Drew: Yeah. I like the approach, you're probably mixing the two because there are some [00:32:00] people where, on the list of 12. There are a couple companies where, I actually know these people from MicroConf and they just happen to work at this other company. And it's more a happenstance thing rather than this is how I met you thing.

So like I, I feel better about that connection than I do a different company where it's we hopped on a bunch of sales calls together and you were representing company A and I was representing company B, and and now I know you via that. So those are, bucketing them into those distinctions might be useful.

[00:32:33] Shai: Cool. So what's stopping you?

[00:32:34] Drew: Is the goal here for me to just say nothing? Because I feel like that could be the punchline of the podcast is just getting a bunch of people to say nothing. That kind of feels like my actual answer is nothing. I think I'm probably gonna need to write all these things down, but thankfully this is recorded.

So I can summarize it using, first I'll throw it into whisper, then I'll throw it into chat, G p t and and get my action items [00:33:00] from the transcript.

[00:33:01] Christian: I'm reminded of Mark Andresen of Andresen Horowitz has a quote that in the future there will be two types of people, people who tell computers what to do, and people who are told by computers what to do. You're effectively getting a computer to tell you what to do

[00:33:15] Drew: Yeah. I'm telling a computer to tell me what to do. It's both.

[00:33:18] Christian: There's one other angle of this that I'm curious to explore. You mentioned that there's a dozen projects in this project graveyard that you've taken from idea to domain name to MVP and then it died.

Why did they die?

[00:33:30] Drew: Ah, these are good questions. Different ones for different reasons. I've been evolving the, this segment I want to serve. I've been thinking about this as at first I would just come up with what do I think good ideas for products are? And it's, those kind of tend to start out in consumerish space.

They slowly moved into like prosumer space. This is the first like fully B2B thing I've built, and I really like, [00:34:00] I don't think scratching your own itch in the B2C space is a good idea. And I've done that plenty of times and it's failed quite a few. So I guess project selection is probably the number one reason a lot of my projects had failed. The other reason is motivation, right? I think I very much agree that like a startup dies when the founder runs out of energy, not out of money. And although a bunch of companies not able to raise rounds over the next couple months will disagree with that sentence. But the, that definitely holds true for my side projects.

When I've picked things where I wasn't passionate about the audience, passionate about the customer, things like that, I've had a hard time like sticking with those projects.

I've been building up my skill set over the course of all of these different tools, right? I've built plenty of things. My first one, I didn't even know how to collect payment, had no clue how to do. I was mostly a front end dev to start and so I didn't even know how to , get an API key for Stripe and do some of these [00:35:00] things.

I also always had like DevOps done for me at my jobs. So I didn't ever have the experience of creating a new C I C D pipeline and getting things deployed and getting like a cert and all these other things. And a slight plug for Vercel here, actually one of the reasons I joined the company is like Vercel is the tool that let me become capable of shipping full products because it's a lot easier to ship it backend and ship things that scale and you don't have to worry about.

Like serverless is just, it's so nice and its easy serverless. So that's yeah, I've just been building up my toolkit or tool belt. Rob Walling says, yeah you're building up. He's got the stairstep methodology, right? And each stairstep you're supposed to be , you're supposed to be building more tools in the tool belt and getting better at things.

Strangely, all of my projects have, failed and not made revenue , but I have learned quite a few things. And I guess failure. [00:36:00] Failure is a relative term, right? I've, I sold one of my projects recently that I was thinking about shutting down for a small sum of money. So I guess that's not a failure.

I just stopped supporting it though. But yeah, I learned things. I learned the customers I wanna serve via those iterations. And I've landed on selling to companies like Vercel, which is a dev tool company. That's the space I want to continue to serve because I think it's gonna continue to grow.

I also think that . There's not a ton of companies out there that are nicheing into that specific segment, and I've got a lot of knowledge there.

[00:36:39] Christian: Okay. Let me try to summarize it and see if I understand. Sounds like there are three main reasons why you characterize that your graveyard of a dozen projects have failed. The first is building something for b2c, scratching your own itch as a consumer is not [00:37:00] a way to get high paying customers.

That's a way to, to attract tinkerers, and that's not a great foundation for a business. The second is loss of motivation that I don't think I fully understand that. What helps you feel motivated when working on a project and what, what's happening when that motivation?

[00:37:18] Drew: Yeah. So one project I made that I just stopped was a tool for doing remote all hands software. And that was a tool that yes, served a business. But um, b like I just didn't really care about HR type software or company engagement software, like whatever you wanna call that space.

It's just something I didn't care about. It was a great idea. I was working on it before covid. It probably would've made a bunch of money if I had it live before everyone was forced into remote. But I just stopped building it because I, I just didn't, I wasn't passionate in that space, if that makes sense.[00:38:00]

[00:38:00] Christian: Okay.

[00:38:01] Drew: And like I could have pushed through on that. But life's short. Why build software you don't want to?

[00:38:06] Christian: Started the idea because you were passionate about

[00:38:10] Drew: I started the idea because my company adopted remote for the first time, and I was like, this remote, all hands sucks. Just watching a, just watching an all hands presentation over teams and then throwing questions into chat and praying that the live production crew sees them and answers them as it's horrible.

[00:38:31] Christian: But then the motivation evaporated because you realized you didn't actually care about the

[00:38:35] Drew: yeah, like it was a good problem, but I wasn't passionate about fixing it. I just saw a good problem that businesses would pay for which, is good. That's a good skill to have of identifying those things. But I think I've just over time become more aware of things I will and will not follow through on, I know myself better in that sense.

And so I. Slowly but surely whittled down that [00:39:00] that range of products that I want to work on.

[00:39:03] Christian: Okay. It's, it sounds almost like a joke to me to say that working on a sales tool for like dev dev tool sales pipelines, fixes that like passion thing that , that sounds like a very like, boring, corporatey project.

[00:39:20] Drew: That is the beauty of it, is it's so boring. No one else is gonna be interested in it but me. And it's also it's also something like, so when I was interviewing at companies, Vercel was top of my list. It was the company I wanted to work out most. So I don't see myself, leaving Vercel anytime soon.

And this is something that will definitely make my job better at Vercel if I can use it in the day job. . So I've also got that forced like I'm not going anywhere, plus this tool makes my day job better, so there's a little more fit there, if that makes sense.

[00:39:51] Christian: Yes. Yeah. And the fact that you're living and breathing this problem day to day that, that does track for me that this is a [00:40:00] problem space that you're thinking a lot about. This is I would also feel passionate about building a thing that would save me personally a bunch of time

[00:40:06] Drew: Yeah. If you've seen all the emails I had to send back and forth, you would understand why I'm passionate about this space.

[00:40:12] Christian: , for sure. Shai what are your thoughts here and the reasons that the previous projects have failed?

[00:40:17] Shai: Yeah, I think I can relate to a lot of it. is the first thing, and I think there is something to be said for like those spaces where you are passionate, and I understand what you are saying about you can be passionate about the. Day-to-day work of the initial stages of building something whilst not being passionate about the wider problem space that you're solving.

Like I, I hear that you can be very motivated and passionate about doing that initial work, even if you don't care about the the end goal that it's serving. And if you can get those in alignment and be passionate about both, then that's awesome. I'm also the thing that's front of mind in my head as you say this stuff, is this idea that motivation that we have it the wrong way around when we talk [00:41:00] about motivation being the cause of action that more often it's the other way round that it's cyclical, but it can be more useful to look at it the other way round like that action causes motivation. You might not be motivated, but then you sit down and you grind and you do the thing

anyway, and that causes things to become exciting again. So it's also, that's a trap that I think a

[00:41:21] Drew: I agree with that. Actually, we've probably, what we've probably through this conversation just witnessed actually, is just that I've grown up a lot over the last five years. I, I used to much more fall into the camp of if I'm not mo motivated to work on this than I won't and things like that.

But the change, I think some folks at YC talk about this, like they actually see founders become more passionate about their business as it's successful. They start out and they're like passionate about it, but because it works, then they become passionate about the space. There's a good video they just put out on their YouTube channel [00:42:00] about like picking a problem to work on and.

I think for me it's much more that I I think I've learned that yes, you're a hundred percent right. Taking action does generate the motivation. I have a much better productivity routine now than I did when all of those projects failed. Even though I'm busier, I somehow get more done.

So a hundred percent agree on what I've been doing recently is, wake up at 6:00 AM go to the gym for 30 minutes, come back and code for two hours every morning on this project. And that itself has kept me motivated in making progress on this even when I don't have a ton of time to work on it.

I don't have any customers yet. Things like that.

Very much agree. That action gives you energy.

[00:42:50] Shai: Yeah. And that, like what you're saying there about if you are, you've it sounds like you've shifted perspective a little bit to like your marker of success and feeling , [00:43:00] fulfilled in what you're doing is I've gone and done this action, like I've gone up, I've gone to the gym and I've sat down and coded.

Rather than it being tied to the the external out of your control, like this must be, this needs to make X amount of money for me to feel, like it's focusing on those intrinsic motivations and actions

is I think is the way forward. Uh, The, and then I think like within that, it's important to draw that line and make sure that you don't have any of your, like that sense of those previous ones that didn't work out, that those don't play into any kind of Identity, self-image of, oh, I build things that aren't successful.

It's like drawing that line in the sand and saying, you know what? I've learned from those things. And those ones didn't make tons of money, but this is the new one. And this is, this is the first one that I'm ever doing with all the knowledge and skills and everything that I've learned from the past.

[00:43:52] Drew: yeah, this is the first one I've built. The la the last one I worked on Tri Slater that was the first one I built where I felt I actually [00:44:00] had enough knowledge to build a full SaaS, like a full, multi-tenant. Scalable payments work, everything works. That was the first time I took a stab and felt.

I built a really good product here that works. And so in terms of all the, like other 12, yeah I, I don't really put them in the same bucket of failures cuz I was just learning how to deploy a website. What my first one I built was share-a-podcast.com. First of all, don't put dashes in your domain names, pay for better domain names.

And I didn't even know how to like, build a backend and connect to a database for my front end website. Then, so is that a failure or is that like me playing with new tech and learning it? I'm, I'm not gonna put it in the bucket of a failure because I actually figured out how to deploy something.

And I think it might have been the first time I used Vercel back when it was called Zeit.

[00:44:49] Christian: Oh, I remember that.

[00:44:51] Drew: yeah, like I, I think a lot of these things. At least for me, the fact it led me to even getting a job I really enjoy is we talked about the [00:45:00] money piece of it too. It's like, actually don't at, at previous jobs, my goal was how quickly can I make this thing make money so I can quit my job?

At Vercel I very much enjoy my job and I'm not going anywhere. And so that motivation has gone away. So now I'm, I have removed the,

I don't wanna call the money thing it's not an impure source of motivation, but it can be one that distorts your view a little bit. Like money can if you need money and you want to leave your job I think you'll tend to, at least I'll start project, stop projecting here and talk about myself.

I tended to work on things I thought could make me money more quickly. Because I was like, Hey, if I can get to 10k MRR, then I can quit, or whatever that number is, right? But now since that's not on the table, I'm actually working on a bigger project that I think can have more impact that will be more useful.

Anyway, just food for thought for people who feel like, if you do want to quit your job too badly, [00:46:00] you might accidentally look for shortcuts. So maybe don't look for shortcuts is my advice to the audience here.

[00:46:06] Christian: I like this framing that the place where you're at now, having walked on these stairsteps, this is the third thing I was gonna bring up. You are more capable as a founder, you're more capable in building things. This last project you work on, try Slater was the first thing that you built that was deployed, that had the DevOps thing figured out, that had the billing thing figured out.

And you're now shifting towards more of a B2B mindset. You figured out things from a business perspective. So building registered.dev has the highest probability of being I don't like using the word successful. I think Shai had a good point there of changing that framing to profitable Yeah.

A, a profitable project. Yeah. This sounds like you have a high profitability of getting to this place, certainly in the next decade, I think you said. Was your goal of shifting towards having a product be the main source of your income? I'd like to bring us home a little [00:47:00] bit. How are you feeling about this project and what do you currently see as your next steps?

[00:47:04] Shai: Oh, okay. Can I do a bring it home cuz it's gonna lead well into that.

[00:47:08] Christian: Yes, of course.

[00:47:08] Shai: I wanted to just, I know you said that you wanted to build out your action items moving forward by taking this transcript and putting it in chat g p T. But I would like to encourage, I, I would, I'd love to see just a brief summary yourself of what are your takeaways of immediate next actions

[00:47:24] Drew: Yeah. . So immediate next actions, I think I'm gonna try to find 12 more customers that I am interested in this early feedback stage. So if I frame the 12 that I already had lined up as the 12 that, I want to have a good first impression of the product and yada, because I think they're the most likely to close then I'll just go find 12 more that look like them, but are different that I don't have those feelings about protecting the, those relationships.

So I'll just go find 12 more of those and then send them some cold email or, a LinkedIn connection or [00:48:00] actually. The nice part about selling to dev tool companies is all of these people are on Twitter, so I will probably just find them on Twitter and DM them on Twitter, cuz that's going to work way better than a LinkedIn dm.

And that's the phase for getting feedback on. not going to wait until I have something fully finished, I think I'm just gonna go have those conversations. And I'll reach out to 12, probably expect a 20% yes rate. So I'll only have a couple conversations, but it's better than none.

And then I'll get just, I'll probably go steal the deploy empathy scripts and just do those conversations. With that bucket of 12 if it confirms what I'm building. Then I'm probably just gonna go full speed ahead on building and getting to that demo state where then I can reach out to those other 12 customers.

There's probably another bucket of like, how do I wanna start thinking about the CRM stuff and into integrating with it? But that's a problem for [00:49:00] tomorrow. Or not tomorrow, but future drew. He'll figure that out.

[00:49:04] Shai: Okay. So that next step of finding those 12 and reaching out to them, how long is that gonna take you, like waiting to hear back from 'em is different, but like the action that you can take, how quickly can you do that?

[00:49:13] Drew: I could probably find 12 today, then send those messages. I was planning on coding more today, but maybe I'm maybe I'm doing cold outreach instead.

[00:49:22] Shai: maybe, or? Definitely cuz it's already today.

[00:49:25] Drew: It's already today. Okay. So I'm doing cold outreach

today. Yes. I'm doing cold outreach today. That's the take.

[00:49:31] Shai: To 12 people by the end of today.

[00:49:33] Drew: Yeah, it's very doable.

[00:49:36] Shai: Wonderful.

And now

[00:49:37] Christian: by the timeline, we're currently recording this today.

[00:49:39] Drew: Yeah. This is today.

[00:49:41] Christian: Today's the day

[00:49:42] Drew: Today is the day

[00:49:43] Shai: Okay. And so now with that in mind can we, do you wanna circle back to Christian's question, which I believe was, how are you feeling about this action list moving forward?

[00:49:53] Drew: fairly good. I think it's rather straightforward. I think. Um, [00:50:00] I think,

yeah, because I think the only thing that I'm like, ah, getting all these, spending all this time on conversation is a waste of time when I could be coding and making progress on the code. , but I think that's the developer's intuition, right? That's like a good time is coding time and all other time is wasted.

But I, I know that's not correct. Like I work in sales now. So I, I understand how much of how much work can happen that is not coding. But

yeah, I guess there's no, but that's the point of this podcast is to remove the qualifying but statement from whatever your blocker is, right? If you are indeed blocked for remove the qualification and just let the sentence stand on its own. So I guess there is no, but,

[00:50:48] Shai: Yeah, and I guess, I mean, look there, there can be a but of but that feels scary.

[00:50:51] Drew: Oh, that's fair. But the, I think the. The problem space I'm working on is one that I'm very interested [00:51:00] in, and I don't plan on changing the problem space for quite a while. If this product doesn't work, I will build another product in the same space. So until I solve problems from this set of customers and they're willing to trade me money for solving those problems, I'm not done with.

So any work I do in that direction is useful. So I think I guess even if it is scary, what I'm saying is there's no escaping it. Like I, I've decided this is what I'm doing.

[00:51:26] Shai: Yeah. And I mean that, that's the thing with this is the typical, I love how you framed it just now as that developer's intuition that the best thing to be doing is coding. That's such a like nice diplomatic way of saying we're really scared of marketing,

but

[00:51:39] Drew: Marketing, sales. The sales engineering. I actually, I took this job for a couple reasons. One was one was to the who wouldn't pick a job at Vercel? Vercel's amazing. I love working here. It's such a great company. It's amazing to see the future of what's being built on the internet before it's built.

I can randomly [00:52:00] DM the person who made the decision on why React server components works the way it does rather than just like reading some blog post on a forum or something. But the other reason was I really wanted to like, learn the rest of the business, learn sales, get comfortable on sales calls.

I remember two jobs ago, . We used to do demos where like we'd make a feature and then you'd have to demo it to, to the rest of the engineering team. And after your sprint was over and I remember getting like really nervous for those and now I can go

yeah, I can do lunch and learns for big companies that, that I can't name. And do a lunch and learn for 150 of their engineers and be fine. So that's the other reason of like why I took this job is it, I knew that if I wanted to jump into the founder space just cranking code out every day is not the best way to.

[00:52:51] Christian: That feels reassuring to me that even with this base of this professional experience at your day job [00:53:00] demoing and doing sales calls you're in a sales role. If there can still be some emotional resistance to doing marketing for your own

[00:53:06] Drew: Oh yes.

[00:53:07] Christian: the phone to

Show them something that you've made can still have that emotional resistance.

Yeah.

[00:53:11] Drew: yeah. Emphatically, yes. Vercel is, while it is an amazing company and everything, it's not my product. It's not me. Like I, I work for the company. The company isn't me. And I think with our startups we tend to wrap some self identity in them.

right? This is my thing. If they say no, are they saying no to me? Or are they saying no to the product? And so there's these two things naturally get conflated when it's the thing you've built, but when there's a bug with Vercel I just go create a ticket in a backlog somewhere, and it's not personal.

So yeah, I think the resistance will always kind of be there even if you are in a sales call and feel or in a sales based role. And I feel no shame talking about Vercel's features at large and getting pushback from [00:54:00] architects and principal engineers at, I'm having a hard time not saying companies here because I probably shouldn't be, but very large companies fortune 10 and getting.

Pushback about Hey, we can't deploy with you because X, Y, Z.

Yeah. So I'm fine in that whole domain, and yet I still don't want to go ask for feedback about my little side project from from somebody.

[00:54:23] Christian: If someone criticizes the product it's your idea. It's the thing that you've built that something I've only recently unpacked is how incredibly sensitive to rejection I am in criticism and Something as simple as doing customer support emails for file inbox was this minefield of people saying that I'm bad.

And I think therefore was the logic I was following. Because I'm bad, I'm unworthy of love and unlovable and like all this stuff that got tied into it. And being able to be aware of that and realize what was happening has helped me to be able to find effective ways to [00:55:00] manage it, which has been very helpful.

[00:55:03] Drew: Yeah. I think there's two ways people can go about learning things. I've started working on a blog post for like, why people might want to consider sales engineering. And way one of learning is go find a job that teaches you the things you want to learn so that you can build up this skillset and then take it and go on your founder journey.

And look, you've got the tools you're hopefully more equipped to handle this. But option two is people just, jump into the fire of running a startup. They don't go build all of the skillsets they think they need. They just, it's trial by fire. Jump into the deep end, add all the metaphors in here you want.

And I think both work. But the thing about the skillset I've been building at Vercel is it's very much companies post product market fit, like Vercel has product market fit. And so while I am learning a bunch of sales skills and things like that, I think they translate nicely to if you have product market fit.

My [00:56:00] skillset in the, like companies that don't have product market fit space is still very it's still very new territory for me. Yes all of my products haven't probably had product market fit, but the iterative process to get to product market fit, like I'm just inching along that continuum.

[00:56:18] Christian: Shai, do you have any closing thoughts for our first episode of What's Stopping You?

[00:56:24] Shai: The one thing I wanted to add is I think a lot of the things that we've talked about here, the, like losing motivation for things, the, just all sorts of things that have come up today. I think a lot of them get solved by taking this next step that you're talking about, which is to involve other people

Bring in those potential customers.

Do a bit of research. If this is what they would want or what, what problems they have. I think that next step just solves so much of this, and it's an incredibly scary or intimidating step to take in a lot of ways because the space that you're in right now the position you're in right now of, [00:57:00] I have these dozen people who in the future I could speak with.

That's a very comfortable place to be, that you have that in the future and to then go and actually speak to those, you are destroying that safety net that you have of lake, that you'll always have that to look forward to or to do when you're ready. Yeah, I think this is a very good step for you to be taking and. I, I look forward to seeing whether it gets done today or whether any new resistance comes up, which would also be totally legit and I'd be interested to hear that. But I think this is a good path forward just in so many ways.

[00:57:31] Drew: I think the takeaway is burn the boats just gotta burn the boats. If I think there's a lot of, if you were to look back at all my previous projects and I know we were doing takeaways and wrap up, so apologize for ruining it, but I probably didn't burn the boats on any of my previous side projects.

I probably didn't go all in on any of them. . Maybe you could say try Slater. I did, but that's debatable. I didn't even, I didn't even ask anybody in my network for feedback before pushing a V1 live. Yeah, burn the [00:58:00] boats. That's my takeaway.

[00:58:03] Christian: I'm gonna push a little bit on that. you're still burn, burn the boats for me would be like, yeah, quit your day

[00:58:08] Drew: Oh, burn. Burn The boats on the emotional, like

because of y

[00:58:14] Christian: away if they're not interested in the product as it currently exists.

[00:58:17] Drew: Yeah.

[00:58:18] Christian: Okay. Don't be afraid of the boats catching on fire if they happen to catch on fire.

[00:58:21] Drew: Yeah. If the boats happen to catch on fire, don't in intentionally set them on fire, but if they catch on fire, it's fine.

[00:58:28] Christian: I like that.

[00:58:29] Drew: Okay. it's not a big deal.

[00:58:31] Christian: The building a little bit off of what Shai said, the, that general problem of the fear of converting potential into realized output is consistently terrifying for me in my life. That's something I unpacked recently. , it's a very comfortable POS position to be sitting in. This thing might happen in the future, and I have, oh, all I have to do is send out an email to this email list, and then something cool

[00:58:52] Drew: then the good things happen.

[00:58:54] Christian: right?

And that's a very scary first step to take of, ooh, this is the test if that's actually gonna happen. So [00:59:00] that's a good fear to be conscious of. Drew, thank you so much for being the very first guest on what's stopping you. This has been a ton of fun. I'm glad that sounds like you, you know what your next step is.

Sounds the answer to what's stopping you right now is nothing. And I'm excited to find out what the next thing that's stopping you might be. Should we do like where to follow you or, I don't know what, I don't know what to do at the end of the episode.

[00:59:23] Shai: I thought you were gonna propose singing like a little jingle. I was so excited.

[00:59:26] Drew: you ready for the jingle?

[00:59:28] Shai: Yeah. Where can people find out more about you, Drew?

[00:59:29] Drew: I guess just drew.tech is probably the best place to find me on the internet. Or on Twitter, you can always find me on Twitter. But that's, those are probably the big ones. And then I guess if you're a dev tool person, please send me an email at hey@drew.tech especially if you're in the sales side of a dev tool company.

[00:59:50] Christian: Sounds good. Drew, if you know anyone who you think would benefit from having a conversation with Shai and I talking about what's stopping them or if there's any listener who would like to [01:00:00] go through the same sort of thing that Drew did, either on or off the record, we have an option if you would like a conversation not turned into a podcast, you can either go to whatsstoppingyou.fm or you can private message Shai or me on Twitter and we'll have links for those in the bio. Thank you very much and see you in the next episode.