Tech Brew Ride Home - (BNS) How To Know When To Kill Your Startup

Episode Date: November 16, 2024

We talk to @cara_jacqueline about what its like when your startup dies. How do you know when it's over? What were the lessons she learned from her journey? One of my favorite episodes we've ever done. Learn more about your ad choices. Visit megaphone.fm/adchoices

On April 4th, 2023, around 2 in the morning, a man was found stabbed multiple times on a sidewalk in downtown San Francisco. Hey, who did this to you? What happened next turned the story into a political firestorm. Reports have identified the victim as Bob Lee, the founder of Cash App. From Bloomberg Podcasts, this is Foundering, the Killing of Bob Lee, beginning April 16. Welcome to another bonus episode of the TechMeme Ride Home podcast, another portfolio profile episode. This one's unique so far in these portfolio profile episodes. Let me introduce my guest first.

We're talking today to Kara Bornstein-Marin. Kara, thanks for coming on again to the show. Thanks for having me. Excited to share some learnings. Yes, this is going to be a show of learnings because when I conceived of doing portfolio profile episodes, you know, it's not just talking my book or doing promo for companies we invest in. The idea was that this would be a way for people to follow the whole lifecycle of a company, you know, from when we get invested to, you know, evolving the product, finding product market

fit, getting, raising rounds, et cetera, et cetera. But that also includes companies that do not make it. as people know VC investing is a power law sort of thing where the majority of your investments do not make it and unfortunately Kara's company which we invested in I don't know two years ago now maybe more than that has shut down so Kara is here to as she said tell us her learnings and and to do that Kara I think we should start from the very beginning like you have been on the show. We have talked about this before, but remind us, start from the moment that you're like, hey, this is a good idea. Maybe I should do this. Literally the inception of what would become Stashpad. But what was the first idea and when did you know I'm going to do

this? So before Stashpad, I was a software engineer at Twilio. And while I was there, there was one thing that I noticed just about myself and where I draw energy, which is talking to customers. And so whenever I was pulled into customer calls where there was an engineer on the other side and something wasn't quite working on our end and we could tweak something and then get a big deal going together, I was like, this is amazing. And so that made me really excited to pursue entrepreneurship if I saw like a problem that I was excited to go after. And so kind of not too long after I realized that that was giving me so much energy, I started to notice. a problem around knowledge management for software engineers. And pretty much every software engineer is going to agree, knowledge sharing knowledge management, it's a pain point.

And so the question is, well, how do you want to go about doing this? And so the first insight, which was kind of like when we really first started the company, it was called bite-based before it was called sashpad, was the idea that engineers largely weren't writing to a wiki because they didn't know if it was helpful, the things would always fall out of date, they didn't want to have the, all sorts of things. They didn't want the burden of keeping it up to date. And what they were doing was writing to personal notes instead in order to keep track of all that important company knowledge that they would need to do their jobs effectively. And something that we noticed when we did a bunch of research is like over 90%

of software developers were using like a really bare bones notepad. So like Apple notes, notepad.tXT files, whatever on their, on their local machines. And it was really disorganized and just kind of felt like they were doing it wrong. And so what we started with was the concept of making like a power developer notepad. Ultimately, this became called SaaSpad lists. And the idea was to give you the immediacy that you had when using like notepad on your desktop, but then designed in such a way that it would be organized by default. And so this gets into like company inception starting point.

So kind of like with this insight and we had a little bit of like news coverage that we were able to get, we got into techsars to pursue this idea and do a bunch of customer research. And so we did TechSars, narrowed down the ICP. It's going to be more senior software developers who value this. And using my network from Twilio, my co-founder's network from Nextdoor and the TechSars network, we went to like engineering leaders to start, told them what we wanted to build and used that to raise that ended up being a $1.8 million round. And that's kind of when we, when we got off to the. the races and grew the team a bunch. I could pause there because the story continues.

So for sure. So good idea you raise a round off of the idea. Did you have a prototype or was it still sort of like pre-product that you were able to raise that round? We had a very minimal prototype, but it was honestly not very intuitive. So when we, I don't remember if we did a demo with you, but I remember some of our investors we did. Yeah, but some of our investors who did end up investing. We did a demo where we gave the whole concept, but then they tried it out and like it was, there was a lot of work to do to make it really intuitive. So we'd see them clicking in the wrong places. So really kind of prototype level product. Like that meme of the designer and the person putting the shapes in the wrong holes. Yeah. So you raised the round and so

what are we talking about? Like six months a year? to build out what the product that you think it's going to be is going to be. Does that sound like the right timeline to you? Around that. I don't remember exactly. But something like that, we got a team together and went to work to really deliver on the vision for that product. So again, I've founded companies before, but one of the things that I say a lot is that when I was writing my book, I would outline a chapter and then I would sit down to write it and the chapter would immediately go in a

different direction and I was always wondering who's writing here if it's not being like but a product a a company is completely more complex than that so was there as you're doing as you're building out the product in that year does it change even before you get feedback from users even before, like, does the product evolve because as you're building it, you're saying, you know what, our original idea for this kind of, we should really go over here. Just give me a sense of, were you able to go A to B like you planned, or did it evolve as you're building? So I think probably we should have, and this is a learning, we should have evolved it more strongly. And we tried to do that later on in the company, but it didn't end up working out.

So our process was, we were lucky to be working with a very talented designer. And so as like we went through the full process of like doing wireframes and seeing what people expected off of those and then developing and getting tons of feedback. So it followed the idea of a power tool. I think one of the places where we went wrong is we were fortunate to have some really wonderful people who were really amazing. early adopters and we over indexed a bit on like the feedback of like one person or two people in order to then kind of go in the weeds on something that wasn't then ultimately validating the product. So an example is like, oh, you need Linux support, right? Or you need support for images when in reality we understand that certain use cases need support for images, but we probably

could have been winning over other ones instead. And so I think that's for me a key learning is like I love that customer feedback. I love the energy of working with early adopters who are like willing to take the risk of putting time and important information into a startup that could shut down like we did. But we needed to be a little more rigorous with like kind of okay, even in this pre-launch phase, it's not taking off.

There's something promising. Why is it not taking off? And are we making sure we're building against that hypothesis versus building against what we know people are saying they would like, but we're not actually sure that we don't have conviction that that's going to change the trajectory. So because what I was kind of almost leading us to was I've seen a lot of times where when people are just purely building, they stick to the vision. And then when they get, you know, the first adopters and they get the feedback and the product is completely something else.

and they're like, you know what, we kind of had an inkling it was going there, but we stuck to our guns, we stuck to our vision. You're saying almost the opposite that maybe if you had stuck more to the original vision or was more disciplined in terms of, yeah, tell me. I think if we, yeah, it's a great question. I think we did stick to the vision of making a power notepad. What the power notepad looked like was a little different than we envisioned, but somewhat similar in that it wasn't, like another option could have been make a notepad that's just built on Slack instead of like a native app, right? So we overall did stick with the vision. But what I think we went wrong with is like what are the main hypotheses we have as to why this should exist.

So like capture now, organize later. That was the whole like ethos of stash pad list. And if it's not, if we're not getting like a really high hit rate with who we think our target ICP is, then adding long-tail features to get to feature completion of like a Microsoft product is probably not going to do it. And so we kind of like sat with the long-tail feature completion too long, which we didn't do in our second product. Right. But yeah, I don't know if that's.

Well, okay. So because we have to get to it's originally bite-based, but it becomes stash-ped. But okay, so let's get to after that year, the product has been developed and you start to send it out into the world. and as you're mentioning, even when you're developing, you're not feeling like you're getting traction, but then, because I've experienced this, what happens when you put a product out and people are like, yeah, that's cool, and then you look at the logs,

and they're like, yeah, but they never came back. To the degree that you want to go into detail about that, like, if that's what happened, or, again, I don't want to put words in your mouth, when you're actually hello world and then the world kind of doesn't jump up and say hello back what does that feel like and what do you think at that point yeah so the and one thing i'll say also disclaimer for things that are a little older in the company history i may be misremembering it because it's been a few years but the more reason what i'll know but this this i can remember

i feel pretty vividly so so um so we launched on product hunt this first version the feedback was pretty positive and we got a bunch of buds he came on the podcast found some people who were really excited about it um and then something that we saw was we just weren't growing all that much and this was in this like summer of uh 2021 and so what we did was we wanted to understand like we had a hypothesis of our ICP being like a senior software engineer but that's actually really vague because there's like all sorts of different kinds of engineers and all sorts of different kinds of people who may have an engineering role whatever and so we wanted to try because we saw that we weren't growing that well we wanted to try to bring out who values it the most and so we did a very painful

pricing change in January um i think i have the years right uh where we took what was a very generous premium plan, and we made it basically you have to pay if you're really using it. And so this loss of some customer trusts. So in retrospect, we definitely should have grandfathered an existing people because you can always find more people. But it did help us narrow down an ICP. And so something that we saw with the pricing change, so it took us a little bit of time to actually identify this longer than I would have liked, is yes, it's senior software

developers, it's specifically senior software developers with ADHD. Usually they are like 40 to 45 years old. They're looking for things like bullet journal or get things done. And then they came across us. And then they're like, yes. And so it's solving a real problem for them. It's not just like, oh, I could use some other notes. It's like, I need a system because I am a really smart, usually dude.

And I want to, I need a way to handle a high volume of information at work as I'm like in a more senior role and pulled into more meetings that I can stay on top of. So I pulled out that ICP. Two questions on that. Number one, when you're talking about growth, you're talking about literally user adoption. But are you also measuring like people's time, you know, creating notes, things like that. Like there's a difference between getting new users and then users that are actually. Right, highly engaged and coming back again and again.

Yeah. So I would say that both. So before the pricing change, we were seeing kind of like you're saying, like there were some people who loved it, but it really wasn't taking off. And then after the pricing change, we also weren't taking off, which we can get into. But what we found was that like if you were paying for the product, you often were using it a lot. And of course, there were exceptions where people pay and then kind of forget about it. But for the most of the most of the part, that was a good way to like indicate you're committed to this and getting value from it. And then it would be reflected in the engagement usage. Well, and then the second thing about that is it's interesting that the changing the pricing was like a forcing mechanism almost to help you find your ideal customer. But you keep talking about like identifying down to age, ADHD or whatever. Even if it's in a general way, how did you get that customer, like that demographic data of your, how did you do that research? So, that's a great question. So, so the ADHD insight

came from just, maybe there were like in, in like a three week period, there were like around 10 people who emailed me something on the lines of like, this is so helpful to me, this changed my life because I have ADHD and like, it's probably super random. Probably no one else has ADHD. He uses it. But I was like, okay, this is interesting. And so he started like looking for that more as we were talking to customers and seeing if that was something that resonated. As far as their years of experience, some of it was honestly just like because we were at a pretty small scale, like looking them up on LinkedIn, be like, oh, you have like 15 years of experience.

Okay, interesting. That's telling us something. And when we talked to them, asking them, oh, how do you find out about new tools? How did you find out about us? Oh, I was searching for bullet journal and then this came up in the Reddit thread or something like that. Okay. So at this point, is this the point where, okay, you're out in the market, you've identified your ideal customer, but you don't know that this is the ideal product for them. Maybe, take me to the next step for the evolution from bytebase to stashpad. And if this fits in the narrative, if you're seeing the initial uptake is not what you want, what sort of levers did you pull to try? You're mentioning people finding you on Reddit threads and things like that. Did you try? Did you try?

you know, ads, you know, no, yeah. Not really those, but tell me the story. So first, so BightBase to Stashpad, it was really just a rename where we liked that stash had a verb and it was about like capturing fast. And so that was a rename that was in our initial launch. So ByteBase never had like a full launch in that way. So you were always going to change the branding. Okay.

So we changed the branding to Stashpad. And then as far as, far as kind of trying to get it to grow, we tried a whole bunch of different channels. So let's see if I can remember. I should have pulled up my notes from this. Let's see. What did we try? Search ads, influencers, going on podcasts.

We did podcasts. We did like some experiments with influencers exactly on TikTok and Twitter. And you're paying, right? When you're doing influencers and stuff like that, that's a marketing spend at this point? Kind of. We never spent that much on it. We did a paid version. And then we realized that if we really wanted to do influencer marketing, well, we needed to actually get the influencers using the product.

Because otherwise, it comes across inauthentic. So in that case, then it ends up not really being paid. And you can do an affiliate program, which we considered. Um, we did product hunt launch was a big thing for us. We were able to get a bunch of organic press, uh, which was, was helpful also. Um, but we, we kind of, and there, there is a lesson and I'm, I'm working on growth, uh, now in my new role. Uh, there's a lesson of like, okay, you want to find your right channel and focus and stuff like that. Um, but at the same time, this was like, we had tried a bunch of things and it wasn't, it wasn't picking up. And so that also is like an early sign. Like, like any growth channel that's like reasonably right for your ICP should start to pick up some. And we were really seeing it slow. So any lever that you pool is not getting uptake.

And so what do you think at this point? And tell me how you're thinking evolved and how the product evolves and how you get to sort of the end state of of what we recently had. So, so we realized that like ADHD might be something that we could lean into for marketing stuff, like it's a way of targeting people and finding them. My co-founder and I, to our knowledge, do not have ADHD. So we didn't feel super authentic jumping into that community. So we were hesitant there.

And then at the same time as we were thinking through, on our own, the market size, because we had taken venture capital funding. And with some of our investors, we were thinking that we weren't confident that the market would be big enough. And in retrospect, perhaps it actually is. Like, I think it's a real ADHD is like a lot more prevalent than we realize. But we were concerned about the market size and concerned about our ability to authentically go after that market. At this point, something that we considered and maybe should have considered more rigorously. I think we really should have considered more rigorously is we had this ICP of like people who,

by the way, we loved working with so much. It's so special to get to work with our early adopters. And for some people, their note system was a top priority, but for others it wasn't. And so what I wish we had done at that point was be open-minded to, other problems that have nothing to do with notes that we could have solved for these customers, like understanding just what their P1 was. But as we were doing the customer conversations, we still tended to skew more towards things that are written down in note style. And so we did find what I think was a bigger opportunity, which is what we pivoted to. I could talk about that.

But still ultimately ran into like not not being a, top priority for who we were targeting. So if this is reductive, please correct me immediately. But what you eventually pivoted to is what I would call sort of like a skinny version of a Google Doc where it's not tied to an account. You can literally send a link and collaborate without having to have accounts or sign up or whatever. And listen, I was not in the target market for what originally you were building.

but when you pivoted to that, Chris and I used it a lot. And so I actually, so as from an investor perspective, you know, I invested in the idea that I liked, that you originally pitched. And you pivoted to something that I was like, hey, I even like this more. So, but to bring it back to the founder perspective, you're pivoting to something. something that you did you just say that you made that choice because you thought it was a larger addressable market or did you also have some data from customer like what was the what was the call that said we're going to pivot to this was it seeing what users were doing or was it more a bet on an addressable market so this is actually I really fun I think I even in in retrospect

so so basically to get sash pad lists to grow we were like classic, let's just try team, right? And so it was all about personal notes, but we were like, let's try to get some team adoption because this was a fully monetized product, basically no free tier. And so we wanted to get teams using it. And so as I was doing discovery, in quotes, calls,

aka trying to figure out what to build so that I could sell it to people, something that kept coming up is, when it comes to team notes, notes. We officially use notion or confluence, but everything is happening in Google Docs. And at the same time, Google Docs doesn't have my dark mode, which I love, and it doesn't have very good markdown, which we ultimately learned was the thing people love the most about our first product, Sashped lists. And even more than that, especially for an ADHD mind,

the comments is really overwhelming. The links are getting lost. all the time and when it comes to like quickly collaborating these permissions are getting in the way where I can't jump in with someone fast enough so I end up using like weird things like Slack DMs for meeting notes and brainstorming yeah and so basically we we I did a whole bunch of customer calls like let's say like the last like seven or eight weeks of the year and I was sharing the notes from that with my teammates and we had an interesting thing happened, which was my co-founder, looking at those notes and the recorded

calls, was like, okay, I feel like there's something here of like a Google Docs alternative. And I think it would actually be pretty lightweight for us to build it, given what we already know how to build from our time building slash publicists. And so over the holidays, he built a prototype. He came back into the office early January, presented it to our two teammates. And one of our teammates is being very critical of it and like not too into him. We're like, okay. But it turns out that over the holidays, he had built exactly the same thing, basically just taking not my suggestion of building it, but just the customer notes and seeing like Google Docs, Google Docs, Google Docs, and it's really aggravating. And so the team kind of just naturally got really excited behind this idea.

And so we decided to go full force with that. And one of the data points that led us that decision is We started with the prototype that my co-founder had built over the holidays. And I started giving it to a bunch of friends, some of our investors. And some of the immediate response was positive. Some was very lukewarm. But in any case, we then started to watch the usage data come in. And so unlike with the first product where the usage was not close to what we wanted, this really had growing usage.

And so we thought that we were onto something pretty interesting. I was going to ask about the almost the morale question. How big is the team? It was four at that point when you pivoted? At that point it was four. We had been eight at our peak. But you said that everybody got excited about it.

Is that true? I'm not asking you to air dirty laundry, but to the extent that even you as one of the founders, you're like, okay, I'm giving up my original idea, my original baby, kind of. And I'm just, give me the sense of a team like that when you pivot and then are people coming on board because not to use this word, take this in the spirit it's intended. People are desperate because it's like, well, we didn't get traction with this. We got to find something that we throw against the wall and sticks.

What is what is the dynamic of a team that's pivoting even from your perspective where it's like, well, we're not doing what I set out to do? How do you all like get the juice to then go in a different direction? I think, yeah, it's a great question. I think we felt we felt disappointed by the traction that we were seeing for the first product. And at the same time, we were still getting like a handful of new paying customers each week and like a trickling of like really, really enthusiastic. Like this changed my life. And I still, it makes me like sad that I still am getting emailed.

like that like oh this is like i really it's really really bad for me that this is gone now and so we were getting some validating things there but it really was just flat and so we were all feeling a little bit or i can speak for myself and my perception of my teammates like we're chugging away at this how long is it going to take for this to start to take off and and just feeling kind of down there um and then when it came to this different concept it started as an experiment so we were the we decided to sprint towards a product at launch and just see how much growth we could get. And the idea was we would try multiple experiments

if we wanted to. And so this we chose as our main experiment, but we were like, when we made the choice, we were open to like, like I said, should we build it on Slack? Should we build some, like open to a whole bunch of different things? And then I think with the initial customer feedback here, feeling so different from the first product

and the usage data coming in so differently, and even the team internally just having a love for the product in a way that they liked the previous one, but it wasn't as simple and just singing. One of my teammates said it's the most energized he had been since the day he started at the company. Well, let me pause you there because, okay,

you said that you're seeing more uptake. The team is excited about it, but I want to underline in a pivot for founders especially, but I don't know, for a whole team, there's a, there's a death of what the original idea was that, you know, if you recruit people to the company, I buy into this company and then six months later, yeah, we're doing this. And that's something that is, you know, people sometimes get deep into the psychology and the psychiatry of being in a startup. but there's something that a team and a founder has to,

you have to internalize the death of the original idea. And some people can do that well. And then other times I see founders and founding teams where it's like they're almost too, because the original idea didn't work, they're almost too willing to abandon it. And they throw too much out with the baby out with the bathwater because, yeah, but you're, you're animating spirit of that idea, you shouldn't, you know, it's complicated. But if you could speak

a little bit to like that sort of, you're, you're on a mission, you're evangelist for this great idea and then guess what, we're going to do this and how do you internalize that and make that sort of like that morning period that you might have to have or the transition in your head. Yeah, yeah, I think. So for us, and perhaps in retrospect, like, I, We, I think, I think in retrospect, when we saw sashpad lists slowing down post launch, we should have just taken that ICP and ditch the note space altogether and then saw just like what general problem we could have gone after. But we didn't do that.

And so for us, even though sashpad doc was an entirely new product and had like a very different, even different positioning and things like that, it still was going after the original problem of solving knowledge management. And so like, what started with like, okay, people don't write to the wiki. They're capturing and personal notes. Then became, okay, we kind of lost at that. And I'll say we, Obsidian was doing really well. I'll give a shout out to bear, which is also who we're using.

So we're losing at that. And we're like, okay, where else is knowledge happening where we could have an impact? And that was in Google Docs. And so even though it was a new thing, it's not personal notes, it's collaborative, a very different vibe and way that it's used. it still was continuing the vision we have of going after knowledge management. It was your core animating principle of knowledge management. By the way, I just want to say real quick, because we keep using ICP,

so if people don't know what that means, it's ideal customer profile. Okay, so can you take me to going to StashPad as the thin Google Docs client to almost where we are now. You're optimistic, things are getting traction, and then what happens? How long is this period? From then to, let's say, two months ago, what is that, a year maybe, a year and a half?

Around a year, I think. So basically January 2020, three, 2024, I guess, yeah, January 2020-4. It's recent. We start sharing the first version of Sashpad docs with friends, our network, our investors, and stuff like that, and are seeing usage grow. So we're feeling optimistic about it. The team sprints together to do as strong of a launch as we can for March. And meanwhile, we're like runway is low, so we're knowing we're going to need to fundraise.

And so we need to have really strong metrics. And the launch itself goes pretty well. So we didn't get featured as number one on Product Hunt, but we were the feature the next day, which at the time, probably now it's even more, was going out to 800,000 people. And so that was a massive reach. We see usage ticking up.

Now, one thing I should say is one of the bets for Sashpad docs was growth over everything else. and we'll worry about monetization kind of after with the idea of fundraising off of really good growth metrics. And some of the reasoning there is sash pad lists we feel to a certain extent that the reason that it failed isn't because of our pricing model, but it definitely wasn't helping us grow. And it wasn't a great pricing model. So we went the other direction. Let's focus on growth. And so then what ended up happening is like two months post-launch.

Again, growth is not like it's growing more than. than our previous product for sure, but it's not super, super strong. And it's definitely not strong enough to fundraise off of. And when we dug into it, what we were learning is that we kind of had these initial adopters, largely like tech leads and stuff like that, who really loved what we were building.

And they were sharing docs with people on their team, with external collaborators and all of that. But when they shared a doc with someone, that person they shared with usually didn't care that much. If it was a Google doc, a Sashpad doc, whatever, they just didn't care. And so it kind of ended there. It's not, it wasn't that classic Hotmail model where everybody that got an email from Hotmail

signed up for Hotmail, you didn't get that sort of flywheel effect. Got it. No. Is there, do you have a theory on why that didn't happen? So in talking to people who were that kind of like second layer out, docs just were not a top priority to them. they had bigger fish to fry. And so I think, I think ultimately, and this is for both product iterations by the company, like notes and docs for the people who we are targeting is just not a top priority, not in a way that we could produce a big enough differential in our

implementation. When you say that not a top priority in the sense that that's not something that is top of mind, oh, that's a problem I need to solve, I'll pay for that. Or is this already solved for them so they're not necessarily in the market for a solution? For most people, who I've talked to at least, they are in the market for a solution, but they're kind of getting by okay enough with what they have and they're their problems that are hair on fire problems before this. And so I think that's where like some of the ADHD segment comes into play where a neurodiverse population might become more interested in productivity tooling because it can be a burning problem and it can really make an enormous

difference in their ability to be effective at work. We didn't lean fully into that. And from what we were seeing, especially looking to get, like, we had that first person sharing, right? We even had some people who were sharing with 50 to 100 people all the time, right? And still we're not seeing that next level. It's because that second layer just at a, high rate was not caring that much. Of those 100 people, you're not getting 30 people also saying, hey, this is a tool that I'll use to. Before we get to, obviously, the ultimate question,

which you know I'm going to ask, this is sort of jumping ahead, but what do you think ultimately killed the company? Was it the runway because you have a limited runway and because you're not showing the growth to be able to raise on? Is that why? No. Oh, you're shaking your head.

So please. What's your theory? I think, so in the end, we raised two and a half million dollars for stash pad. We, I think we overhired early on because we didn't have product market fit. And we kind of did the move of fundraising and thinking that that was signs of product market fit, of early market fit, which it is not. Wait, wait, underline that. Raising is not a sign of product market fit. So you're saying because people are giving you money, you're saying that you made the assumption that that's?

I think that especially because, and I didn't share this, the way how our first fundraise went, our main fundraise, which was 1.8 million, was it started by me showing my former colleagues from Trilio who also had been in engineering the concept and pitching them on the problem and all of that. And so a lot of our, like the beginning of our fundraise, the first several hundred thousand came from people who used to be in our ICP, but we're no longer in our ICP. And so I think especially with that combined with then the excitement and validation of fundraising, we kind of saw, you used to be in my ICP and there's all this validation of fundraising. We're on to something if we just build it right. Interesting. When in fact that that was not, that definitely was not product market fit. Okay, so I interrupted you. What is your theory for what ultimately led to, killed, killed the company before I asked the ultimate question? So, so, so I don't think it was fundraising. I think that the difficulty that we would have trying to fundraise towards the end. And we did have trying to fundraise at the end of the company was really just a reflection of the limited growth that we were seeing. But it wasn't, that wasn't the cause.

The cause was the limited growth. And to me, to me reflecting on it, it really comes down to not solving a top priority problem for our ICP and for a large enough ICP. And some of that is the problem choice to begin with, which is like being in the notes and docs space. Some of it is also just like, are you able to actually offer something that's 100x better? And so for a sash pad docs, I love the product. but it was definitely leaning into simplicity.

And so for some people, it was better. For a decent number of people, it was better, but it wasn't 100x better that it was really going to get a long-term flywheel going. So to me, that's where we went wrong, is not going to the ICP and figuring out what is the top priority problem and letting go of anything in notes and docs and trying to solve that. So here's the ultimate question that I've been hinting at, which I prepped you for before we talked. But to the degree that you're willing to get personal about this, like how and when do you decide to shut down your startup?

Even if it's a mechanism that you saw something and you're like, well, that's it. It's over. Or the vibe shift. or how do you come to the conclusion that we got to pull the plug? So for us, docs was really a bet on growth. And we had decent growth. We had 50,000 docs created in just a couple of months. But as we were getting towards the end and we're seeing, okay, after two months,

the growth isn't continuing to go up. We knew that that was a serious problem. And so once we saw that growth, we were we, once we saw a growth slowing down, um, despite the product being so optimized for growth, we, we knew that that we weren't going somewhere good. And so at that point, we did one more, uh, attempt at trying to find an ICP that may value it even higher. And we found something interesting. Uh, it happened to be like copyrighters who we hadn't marketed to at all, uh, some of whom would, would pay us, um, a hundred, even $300.

a month for what we had built if we tweaked it a little bit. So there was something there. But at that point, to pursue that market, that's not my background. We knew very little about it. We would be starting with a lot of unknowns already far in on Sashpad. And yeah, we knew it was time. Is there a personal time when you like wake up in the morning and be like, that's it.

I'm saying this as a person that's done that, you know, you look in the mirror in the morning and you're like, you know what? Time to wrap it up. Like, what is that like, or is that a gradual thing that just is sort of like the frog boiling thing? I think it's a good question. So for me and my co-founder, it was, we both had moments where we had pause. and those pauses like the pause at the end of last year led to major pivots and major changes.

And so whenever we're pausing and saying we're not on a good track and our time is valuable, right? So if we're not on a good track, we're not on a good track. We either make some changes or if there are no changes left to make like in the end, it felt like we really had turned over, not every stone, but a lot of stones. we just knew it was time to call it. But it's really just kind of that feeling you get that we're pushing a boulder up a hill. It's not going. And I do think like if we had spent X amount of time more on it, we could have gotten it going.

But X could be a really long time. And we don't have the funding to do that. And we have tried so many other ideas like with X being before, if that makes sense. that we just, we lost conviction in the underlying, like, knowledge management hypothesis and our way of going after it. Yeah. You might have already said this so you can repeat it if you want, but the final question before we find out what you're up to now, is there one learning lesson, takeaway,

bumper sticker that you learned from these last few years doing this, that you would pass on to someone that is about to start a company right now? Yeah, so I would say two things. So one is, I think, ultimately where we went wrong is in the problem validation, where yes, knowledge management is a problem, but it's a difficult problem. problem to solve. And the way that we were going about it didn't wasn't effective. And one thing actually that someone had told me is like, look at the comps in the space, like especially for personal notes. There's Evernote. So that's like your best scenario is you become Evernote.

Right. And that's not great. That's not an amazing scenario. Yeah. I mean, better than our scenario by a lot. But yeah, but looking at comps in the space is probably a good idea. But just starting with being really open to problems for the ICP, where I think ultimately we were limited by sticking too strongly to notes and docs and not taking those customers who were talking to and saying, okay, forget this. What's going on? Tell me about today. And what are the real problems that, like, right now you're losing sleepover and then let's see if there are patterns in there and if we could solve it. So to me, that's the big, just like the fundamental choice of the problem, had had flaws in it for us.

So that's the big learning there. The second big learning, I would say to anyone starting out, and this is from someone who just shut down. So it's raw and that was sad and it really sucked is it was an incredible experience. And the people that I got to know and learn from along the way, like Brian on this podcast, it was just the experience of my lifetime. So I had so much fun doing it.

I was very stressed, but it was so much fun and so rewarding to get to know so many super smart people, both investors and customers who I otherwise never would have met and got into learn from. And I couldn't be more grateful for the opportunity. So enjoy it because it's, I think it's a really special thing also just in our industry. People are so generous with their time and lending an ear. and wanting to problem solve together. And it's just been such a fun experience despite not having the outcome that we want.

Indeed. But that is, it's all in the game, as they say in The Wire. So, Kara, Bornstein, Marin, what are you doing now? What is your next thing? Yeah. Yeah. So this is a fun one and not something I was exactly expected. because coming out of being a founder, like, as any founder will know, and non-founders too,

your identity is pretty tied up in what you work. And what you work on is really important because you spend a lot of time on it and really want it to be successful. And so I was worried as I started looking for what I was going to do next, that there wouldn't be anything that I was really excited about. And so I started talking to a bunch of people. And one thing that got me really excited was I want to. to think about because Dashpad ultimately wasn't solving a burning problem for enough people,

I really wanted to work on something that's solving a burning problem with smart people. And for myself, I was a customer of my now employer where what I had wanted to do was as a founder, I was doing customer outreach. And I was manually sending emails to do this. And someone on my team found that instead of manually sending emails, you could get the same deliverability with this startup. And it would cost $500 a month, but you'd get even better email deliverability and sequences and all of that.

So it's kind of like a founder power tool for email. And then I came across this other tool, relay.app, which is where I work now. And instead of $500, I could set up the same thing for $10. And so if I was willing to pay $500, it's clearly something that was really solving a need for me. And what relay.com is is a modern automation tool that just makes it very easy. It's very intuitive to automate different parts of your workflow. So I was using it on top of Gmail.

You can also use it on top of Slack and 100 plus other apps. So if you want to check it out, I guess is the CTA, you can check it out at relay. Or you can reach out to me either on Twitter, Kara Jacqueline, Kara underscore Jacqueline, or at my new email address, Kara at relay.app. I lied. I got one more for you. Oh, yeah. Job searching after your startup has gone under.

What was your experience there? And do you have any best practices for that? We work in an industry where, again, in quotes, failure is not necessarily failure its experience. But what did you find about going on to a new thing and advice for people that are in those shoes? Yeah. So the first thing was just thinking about what do I want? And so for me, I felt lucky. Like, even though I'm really sad to have shut down sash pad, I didn't feel burnt out.

I enjoyed my day to day. Like, I enjoyed getting up and going to work on this thing. So I was like, how can I have a job that looks kind of like this? And so for me, that meant either like product management at a larger company, relay is pretty small or going into something that's more cross-disciplinary, like growth at an earlier stage company. And so given that, just like we had made investor pipelines in the past, my co-founder made a list of like companies with roles open that he thought could be interesting

and that was kind of helpful for brainstorming. And then what really ended up being most impactful for both of us is like once we got excited by certain companies and even before learning about companies, we would just talk to people in our network who we had just built authentic relationships with by grinding it out for a number of years and we were like, hey, this is, this is what I'm doing. I really want to work on a top priority problem with smart people. Who do you think I should talk to? And those conversations, I think, again, this ties into just, at least in my experience, people in the tech industry being so open to talking if you're vulnerable and also very specific with your asks and like prepare well for the

the conversation. And that kind of series of networking is what led for both of us to our next roles. Okay. So to close that, again, how can people get in touch with you? Relay.com, but to get in touch with you personally, repeat that for us. So either Kara underscore Jacqueline, J-A-C-U-E-L-I-N-E at on Twitter or Kara at Relay. app. email me and remind me to put that in there. Kara with a C, I'll put that in the show notes. Kara, this is actually, this is ironic. I invested through the fund.

The fund is invested. We wanted it all to work out. But also, this was my vision for doing this from the very beginning was to be warts and all and learnings. And these were the mistakes we made. this, this, I'm so thankful to you for coming on and doing this episode, just how we did it. Like this, this was, this was kind of an episode that I envisioned happening one day. And, and it, this was been beautiful from my perspective.

That's, that's what I love to hear from, from investors who I lost money. That's what I'm going for. Yeah. Okay. Well, listen, we'll, we'll all get them next time. Yeah. Kara, thanks for coming on. And sincerely, thanks for being that honest and open about all this. Thanks, Brian. This is fun.