“We Were Gonna Run Out of Money” — Arrows CEO Reveals Make-or-Break Go-To-Market Pivot

# Bridge the Gap Podcast - Episode Transcript

Welcome back to another episode of the Bridge the Gap podcast powered by Revenue Reimagined. I'm trying to change the voice a little and change up the intro.

We have with us today someone I guess we could say is a client, a customer, a referral partner—we're a little bit of all of it here, and you'll learn why in a little bit. But we have Daniel Zerik, who's the CEO and co-founder of Arrows, which according to what I'm supposed to read here is a digital sales room and customer onboarding platform built for teams that run on HubSpot. I think it does a whole lot more. We could talk about that. I think you're putting yourself in this little box of digital sales room and I think you're better than that. But Dan is a product-focused founder passionate about building software that sales teams actually use, based in LA. You're apparently a big F1 fan and a movie lover. What kind of movies?

**Daniel:** Embarrassing. I'm actually wearing an F1 shirt today because the season starts tomorrow.

I didn't know that. Did you go to the one in Vegas?

**Daniel:** No, I went to one in Mexico City last year. But I got sick for race day, so a challenge of going to Mexico for a race.

Yeah, yeah. Well, welcome to the show, Daniel. It's good. I got to meet you. We talked a little bit. We haven't talked before. I know you've been working with Adam a lot, and we talked about whether this is really genuine or not.

**Daniel:** It is totally genuine. So we internally have been talking a lot about what you guys are doing. We believed in deal rooms for a long time. It's not just the Arrows world. It's totally in this world of deal velocity and sales. It's super important to have things like deal rooms. But before we get into deal room pieces, we want to talk a little bit about some of the challenges you might have. So if we take a moment and think back to one of the challenges you had where you felt like your go-to-market strategy was out of control, where you're like, is this really going to work? And it could be Arrows or any other place you worked. Tell the audience a little bit about what that moment was and what you were doing to fix it.

**Daniel:** Yeah, you know, I think one thing that's interesting with the story of Arrows is we focus solely right now on HubSpot customers. That's been pretty strategic as a decision for coming up on three years now. And when we first launched on HubSpot in April 2022, it really didn't work for like three, four, six months. We made the strategic bet. The product felt amazingly better. The iteration of the product we had before was doing okay but not actually working to justify having funding and the team that we had. But when we launched on HubSpot, we're like, our product is immediately night and day, ten times more powerful. People get it, but we weren't closing deals. We weren't getting in front of deals.

And you know, I think the thing that we try to remind ourselves a lot is we just launched into the sales part of the stack about six months ago. It takes a lot of time to make a change, to figure out messaging, to figure out all the nuances of how to package it, what's the trigger point for somebody to buy. I think we're still learning it a little bit on the sales side. And it's a constant reminder like we've had Adam set up—we've had nothing come to us easy in a lot of ways, and we're actually happy for that because as a team we have to remind ourselves that nothing comes easy. The team really had to work for it.

So back when we launched HubSpot, it really came down to finding where there was existing demand, existing pain points. Nobody was looking for a customer onboarding tool on HubSpot, but they were trying to run customer success on HubSpot. So we posted a lot of content on YouTube and the HubSpot community forums—guides on our site on how to run customer success on HubSpot, how to set up a renewal pipeline in HubSpot, how to do health scores with HubSpot workflows before HubSpot had it natively. And all of that captured existing demand for people trying to do those things. And those were people who were then looking like, oh, we actually do have an onboarding process that's in a silo or something. Maybe we should bring it into HubSpot as well. And this tool looks like a pretty good fit. So that was what we figured out then, and a lot of what we still do now is demand-adjacent content that then can capture what people are trying to do with Arrows hopefully.

So you like HubSpot, huh?

**Daniel:** Yeah, we like HubSpot.

I think they've made a ton of improvements in the past year, maybe two years. And you're right, you guys haven't had it easy. There's a lot in your space—it's crowded, man. I won't name competitors out of respect for you on this show, but there's people who have been around for a long time, people who have massive LinkedIn presence. I think your team does a really good job. Kim does a great job with her content. I think you guys try to educate people. But when you are looking at the space that you're in and the journey that you've gone through, talk to me. There has to be a moment where you just looked in the mirror and you're like, this is out of control. Like what we're doing—I don't know if this is going to work. I don't know if we're going to be here. Walk me through that. That "oh [expletive]" moment where you're like, am I gonna have a company in six months?

**Daniel:** Which one? Which moment? There's multiple. Pick your poison.

No, I think I mean, you hit on something interesting in the intro—that we're putting ourselves in a box with the sales room concept, and we agree. You know, we've tried to position Arrows to be more focused on killing your next steps email because it's really all of us. When interacting with customers in sales and onboarding, customer success, we send these follow-up emails, next steps emails. And they're generally not very effective. They're not connected to the context of what's going on. They take a lot of work. Nobody's interacting with them. They don't drive towards an action or actual follow-through.

So we spend a lot of time thinking about that. And when you know, we really looked back at Arrows—the first year and a half, two years—we were building an onboarding tool that was totally disconnected from the rest of the journey. It wasn't connected to CRM. We were trying to build everything on an island. Arrows was its own self-contained thing where we tried to close a deal that happened in Salesforce or HubSpot. It would trigger something in Arrows. You'd run the project entirely inside Arrows. And there really wasn't...

You weren't always native.

**Daniel:** We were not always native. That's one of the main reasons I love Arrows is you are in one spot. There's nothing worse when you have a rep who has 27 logins.

Exactly. And so we really had something where it was a totally separate system. None of the data from Arrows went back into the CRM. We were purely extracting data from the CRM. And that's when we were like, there's no pull from the market either in buying demand or actual usage of the product. We realized people would just forget to log in and use Arrows because they could keep going and doing what they were doing before.

And you know, that's when we saw the writing on the wall. We've got a team of I don't know, six, seven, eight at the time. And we're looking around and we're just going to run out of money at some point, and nobody's really pulling us forward. That's when we made a dramatic change—delete our dashboard, build on the CRM, chose HubSpot as the first place to do that. And then when we launched in HubSpot, the product was obviously better, but it was not necessarily where the market immediately demanded pull. You know, pulled it out of our hands. And HubSpot's not necessarily a platform that engenders apps to have the capability to grow very quickly. You have to create your own distribution in a lot of ways. We thought it was going to be, oh, we launch in the marketplace and it just goes. And so that's where we really saw the writing on the wall—nothing. If we do nothing right now, it's not going to work. We built this awesome product, but it's just not going to work. We'll run out of money. And so now we're luckily in a spot where that's not the case. We're going to be around for a long time.

Well, and you just mentioned something very interesting. And I think when we talk to a lot of companies on this go-to-market gap concept, one of the issues is really value and usage. So there's this place where when we—our third stage is really repeatability and scalability—but the bigger problem is they use it in the beginning or they use it for the first thirty days and they see a little bit of value, and then they forget about going...

Back to it, or you know, kind of not out of sight, out of mind. You know, you have to go into your CRM, but it's not like you're always going into your deal rooms or looking through things. And I think that embeddedness in HubSpot is super interesting because you are going into your deals, or you should be going into your deals fairly regularly. And with Arrows being embedded in there, it's like a constant reminder that it is getting used through HubSpot.

So my question is, how should founders or revenue leaders or CEOs be thinking about being usable? Is it like weekly? Is it bi-weekly? Is it daily? Like, where's that sweet spot in the B2B tech space?

I would say, changing the question or, you know, inverting the question a little bit. It's more about being there when the work is happening, whether that is daily or weekly or monthly. Like, when is that work actually happening? And what we did wrong the first two years of Arrows was we weren't thinking about the entire workflow. Like, if you think about workflows in any role as plumbing, there's a series of pipes, and those pipes are steps. Arrows is sliding into a piece of that plumbing. So we have to know the inputs. We have to know the outputs.

And so for us, with the deal room on the sales side or an onboarding product, those are people who are in roles that are reaching for that every day, multiple times a day. Whenever I get off a call, when I'm prepping for a call, when I'm on a call. And so we think about ergonomics a lot. You know, if I'm sitting here at my desk and I want to drink water, I've got a big jug of water here on my left. I know if I have that water here, ergonomically, I'm going to reach for it. So when I'm thinking about a deal room or an onboarding product, I want to know that when somebody goes to their pipeline in their CRM, where that data should be or where that thing should be, it's right there. It's easier to reach for it than to not reach for it. And that's when we think about ergonomics.

And so as we've added, you know, AI into the product too, we're thinking a lot about, well, where's the data already? What's already happening? How do we layer on top of that and make it easier for you to reach for this next step, this next action, more easily than it would be to ignore it?

That's a good way to describe it actually. I love the analogy. I don't think people think like that when they're trying to properly position their product, right? It's like, oh, we help you do this, but that the ergonomics one, I think, is important. I think it's scary for a lot of people too, right? You think about, you know, this is my data, this is my platform. I don't want to let go of it. I want to control it. I want people to live in my tool every day.

And with us, you know, Adam, as you know, like Arrows puts a lot of our own data back into HubSpot. We have sixty something data points that you can sync into HubSpot for the onboarding product and a couple dozen, maybe, on the sales product. And I think a lot of people would say, "Well, we're giving our data away," but I know that we are generating the data. We have some of our first party data, and we own the relationship with the customer who, you know, we're the intermediary between your HubSpot, your CRM, and the customer. So we actually have a lot of value in that process. But it has to be, you know, if we are not fitting into where the existing workflows are. If Adam you go to look for a report in one of your clients who use Arrows, if you go to look for a report that's about onboarding and the data from Arrows isn't there, then that would be bad. So we'd much rather fit where the team is actually going every day at the expense of control, knowing that that's how we, you know, that's what makes the product sticky, right? Like, you can get all this data, which is great, but if you could pipe that into my system of record and give me more data than I've ever had, albeit being created by your widget, great. Your widget becomes that much more important to me. Now, because the second I disconnect it, all that goes bye-bye, and that's letting me run my business.

So all those reports, like if you turn those off, or all the automations that are driven off that data, like, it's you can't turn it off because all those things break too, right?

Right. Yeah. Well, it's very hard to create a new workflow path once the sales work is actually happening. Like, once you have a path, it's very hard to break that path.

So I have a shift of a question, a little bit. Looking back at some of those real gaps that you had as you were going through the process. Um, was it like a mindset shift? Like, originally when you were building this thing, was it like an ego or a blind spot or fear before you actually made that decision? Or was it like something else before you were like, "Ah, we got to change it up?"

I think it was a blind spot. I mean, think of every product, every CRM integration that existed three, four years ago, right? It was, "Oh, I go plug into the CRM. There's a gold mine of data there. Let me suck that data into my system, and we'll do some cool stuff." And, you know, it took us as a team having a lot of very honest conversations. Every winter now, for four years, we've gone to Palm Springs for our winter offsite. So I remember we were there and we said, "Okay, we're getting together. The goal this week is to rethink, you know, if we were building everything from scratch today with what we know today, both about the systems that we plug into, the workflows, our customers, what would be the product we would build today?" And we tried to rethink everything and we said, "What is, you know, what is Arrows? What is the unique value that we provide?"

We were getting customers asking us like, "Oh, I want reports, I want Kanban view, I want automations, I want all these things, everything that you don't do." Yeah. And they're logical requests. Like we had no problem with the request, but we had no capacity to build them. And when we looked around, we go, if I could snap my fingers and spend all of our energy on one part of the product, it was the customer-facing space. It was the thing that we put externally that layered on top of the CRM. And so we realized it was like kind of a light bulb moment. That's the unique value. That's where we have a unique point of view. That's where we'd like to spend all of our time.

Why are we spending any time on a Kanban board or automations or reports when, even if I could build the best version of them, if I could rebuild all of HubSpot's capabilities, you don't actually want to go log into Arrows. Adam does not want to go, what's that tool we use for onboarding? I want to go look there for a report. You know, Dale, you don't want to go log in there to move your task along. So we said, actually, we're giving by giving the option for there to be a feature request here. We actually are letting customers expect that we should be building more here. We need to actually pull back dramatically.

And so that's what we thought. You know, when I'm looking at a deal or a ticket inside HubSpot in my CRM, I want to be able to go on the right side, click a button, and create my onboarding plan or create my sales room. And as long as I can do that, then everything else kind of fell out of that point of view.

Yeah. So totally makes sense. Let's step away from Arrows as a whole for a moment and shift to go-to-market as a whole, right?

Okay. Sales rooms, for lack of better terms, have come to be for a plethora of reasons, not the least of which is what you said, right? Like it's the checking in email, it's the thirty-five emails. Like Dale and I are in the process of closing a deal now. It's actually the first one where I think we've used Arrows from soup to nuts. Every time I follow up with the customer, it's, "Hey, thanks so much for the meeting today. I've updated the, here's your link for your Arrows room," and I could probably snippet it, but I do it manually anyway. And I've driven them to the Arrows room. They wanted the MSA, I drove them to the Arrows room. They...

Want to book a meeting, I drive them to the Arrows room. But this started somewhere, and I think this ties into where go-to-market is heading, right? Whether it's sales rooms, whether it's AI, whether it's AI SDRs, whether it's outbound at scale—like you're Nostradamus for a second, right? Put on your go-to-market hat. Where's go-to-market going? What's going to change fundamentally? Whether it be sales process with things like sales rooms, or every salesperson is dead because we're all just going to go online and do our own research and everything's going to go PLG. I don't think that last point is at all true. I think you all agree.

Yeah. I think what we're doing right now is actually this is the thing, right? We're talking, we're building relationships, we're understanding each other. Humans do business, and I think there's a lot of room and going to be a lot of room for a long time for humans to keep doing business and solving problems together. Now AI is going to continue to, and the systems that we plug into around that are going to continue to assist us in that work. But why does a CRM exist? It exists because we used to have spreadsheets or even pieces of paper where we just kept track of our notes. And we had our little flip book of all of our contacts. Now we need to put those contacts into a system, into a spreadsheet. Oh, it'd be nice if that worked across computers. That would be nice if that was online, etc., etc. Oh, we're doing email. It'd be nice if the email showed up in there too, right? But we're doing a lot of manual work to keep up to date all those systems, keep the associations up to date, keep all the communications logged, keep the next steps in a structured format, keep the close date in a structured format, what's going to close this month, how big is that deal, who's all involved. That stuff is a lot of junk that is really hard to stay on top of for humans, but is incredibly easy for a computer to do—remember dates, make sense of data, unstructured data, make structure out of that data, make suggestions to you. And what we're really good at, the three of us and all the reps we work with, is making decisions on options that are presented to us. You know, if I had three follow-up emails put in front of me by a system, I go, "That one's good and relevant, that one's not. Maybe I'll tweak that line a bit, click send." And so for us, I think—and why Arrows has been particularly interesting for us for a while—is that layer between me internally and the collaboration between my client externally. That's actually where a lot of the value is. Historically that's been done in email, on Zooms, maybe in person, etc. But now, like, we're big fans of call recorders, all of us, and the data that comes out of that, the relationship there. But, you know, there's a lot of data, a lot of context that comes out of this call if you're paying attention to it and the system's paying attention to it. Arrows is, and sales rooms are another version of that. There's a lot of context in there. You sent the MSA, did they interact with the MSA? How long did they look at it? Did they not? You know, how many times have I linked them to this? Are they engaging with it? How many people are engaging with it? All of that mashed up with the call data with our interactions, that's the relationship of our deal with our buyer and our customer.

Yeah. All the stuff in the CRM is just a database representing that. It's not super, and nine times out of ten, it's not even an accurate database representing.

Exactly. So what we hopefully get I think in the future, Nostradamus style, is an accurate representation in that database because the system can keep it up to date. But that means instead of me ending my day doing two hours of follow-ups, hopefully it's just kind of happening for me, or at least I've done it in a couple clicks. And I think then I can spend more time on—I have more capacity to be on calls or to help customers or spend more time strategically with customers. And that is the hope. It's not like some AI avatar is likely going to replace me on all my calls. It might expand my capacity a little bit, but I still need to be there to make those decisions in real time. I hope these systems help us make those, or at least present us some options.

Yeah, you were just talking about the massive amounts of data, and I think this is where revenue teams, revenue leaders get super overwhelmed because yes, we have lots of data, but there's not good ways to distill the data. And then do you trust a distillation of that data?

Yeah. So how do you guys deal with that from a sales room perspective? How do you make sure that you're only surfacing the right data at the right time? And how do you gain that trust from the salespeople?

Trust is something we think about a lot on an ongoing basis as you're using the product, but also like when you're signing up. How do we show that we understand you and understand your data in a way that you will start to offload some trust onto us and we can fill that trust battery? Right now our onboarding into the product—the product-driven onboarding—is pretty lightweight. But we're thinking a lot about how, you know, you have to install Arrows into HubSpot to use it. So in that action we can go do a lot to understand your sales pipeline, the types of communications you send, the links you send, all that stuff.

I'm very curious what terms I agree to and what I give you access to as well.

Nothing we will generalize, or you know, we're not going to, but we want to use that to improve the experience we give you, right? You know, Adam, I should know, and Dale, I should know, our system should know what sort of emails you send, what sort of links you send. So when you first signed up with Arrows, we can get you to a pretty good sales room pretty quickly that should be trust-building. If we can show that we understand you and your revenue reimagined within a few minutes, then on an ongoing basis, we right now do not trust the models, the LLMs or AI stuff, to take actions on your behalf. Like we want to go 90 percent of the way or 80 percent of the way, and then present something to you. So when you get an LLM or AI-powered suggestion from Arrows that says, "Hey, it looks like you just got off a call you recorded with attention, those notes are in the CRM, we think you should update this sales room with Arrows to add these next steps or update the milestones," we don't go update them, but we prompt you and say, "Does this look like a good update?" And that prompt is where you hopefully, you know, we're constantly vying for your trust. And the trust is also saying, "We're not going to do it on your behalf, but we give you the option in a click or two to update it."

Yeah. Maybe in two years or a year, it'll be on read it, still, and they just click and put it in anyway. But some people maybe...

Yeah. But then they're the people that are going to be doing, you know, mediocre follow-ups anyway. So we're probably at least over time reinforcing a slightly better standard.

Yeah. Yeah. I'm deep in thought for... It's interesting because, yeah, right? We got this. This could be a first. We got Adam. This could be a first, Daniel.

Yeah. We don't. Adam went quiet.

I know. Oh, it's very never heard, never heard it. It's very rare. I mean, normally I'm not quiet, but normally Dale overtakes the entire conversation, so it's okay.

You should see us in a meeting.

Um, as you continue to build and add—and you guys are a small but mighty team, but like you're a startup and that's great—what do you look for when you're hiring people? What are your non-negotiables? I'm going to bring someone on this team. I need them to do and be what?

It's a really—we, not Dale.

Yeah. Number one, not Dale.

From what I can tell, we get in our own heads about it a lot. We're constantly debating. One thing we definitely think about is writing ability. You know, we want people who can communicate clearly, simply, without fluff. You know, I think we try to—it's maybe nuanced, but we try to communicate a certain way in copy, in our guides, in our posts, in our email comps with people. That usually the team has kind of said has come down for me. We're generally pretty open and direct with folks in a way that's fair. We care a lot about people who kind of are more likely to reach out or kind of provide help first. You know, there's kind of a natural willingness to help. We look for taste, and you know, that's a loaded word, but like do they like the same sort of things we like in marketing, in product, in the types of visuals we put in our guides? You know, Kim just put up her AI note-taker guide and just the image that she had to Photoshop of all the cards of all the different tools she reviewed. There's like a certain amount of...

Taste in there that a lot of marketers might not have done, but you know, that's the sort of thing we reach for. And that's a hard thing to unpack on a call.

I think what we've been thinking about a lot in hiring is just spending a lot more time with people. Like, how much time can we spend with them and do we still get excited to spend more time with them?

What does your interview process look like?

Usually they talk to me first. I like to. So a lot of companies, that's a big flip from most companies. I think we've done different processes where people have talked to others first, and I think we've generally liked it with me. One, I get people. I can sell them on what we're doing. That's a pro and a con. Maybe we, you know, by the time we've sent somebody an offer, I've tried to scare them away a little bit. Like, hey, it's going to be hard and these things are bad, but I want them to be excited about the opportunity at the start. You know, see that, hey, I'm talking to the CEO, and then I go talk to everybody else, and like, wow, everybody was pretty sharp. They're generally pretty excited.

But you know, a lot of people post, "Oh, we got 1,200 applicants for this role. We got 2,000 applicants for their role." I look at that as a negative. I don't want 2,000 applicants. I want like 20 or 30 people reaching out that are a really good fit, and we talk to 15, you know, or 10. We don't want this massive influx of people. We want a job posting that's really well done. Like, very dialed in, very targeted, very honest about what we're looking for and what the state of the business.

Job postings are hard. Getting a good job posting. I don't think people recognize like nine out of 10 job postings I see—and I'm curious your thoughts—are some copy paste of someone's with the company name changed, period, the end. Like, you know, go to ChatGPT, please create a job posting for a startup's customer service representative. We get people saying, "Wow, this resonated with me so much. Whoever wrote this did a good job." And then I get to go reply and say, "That was me, the CEO. Here, let's go schedule time to talk." You know, and like, there that is a signal to them of how we want to show up in the process.

One thing we've tried to do, I think historically, is move very quickly in the process because, you know, people hate being in a long interview process.

What's very quickly?

Two weeks, that is relatively quick.

Yeah, maybe three at most. We'd like to do that. I think we're changing on that. We've liked, back to what I said at the start of this, like we'd like to spend more time with people, make sure our initial excitement is still warranted a month later, a month and a half later. Like, we'd like to do a lot of calls in that time and actually, like, do we still get excited to talk to this person? Like, if you're not looking forward to the call every single time, it's not someone you want working with you.

Exactly. Stripe—I was friends with all the early Stripe people and their founders—and I remember early on they had this thing, like the Sunday rule or the airport rule. Maybe there's different variants of this. But if you were at the airport and your flight got delayed for like six hours and you were on a trip, you know, Dale and Adam together, are you more excited to spend that time together or less?

Less.

Exactly. You shouldn't be working with Dale. But you know, if you had to go in on Sunday to work, are you more excited that that person's there or less?

There's like an initial reaction that you get when you see somebody that you didn't like working with. You're like, "Uh, they're here," versus like, "Oh, that's great. They're here. Let's go get to work." You know, and we want that feeling. And I think you need some time to build up to that.

Yeah. I joke. I can say honestly, like, there—and he's never going to take this recording and never let me live it down. But there is no one else I would rather build this with. Like, it's hard, man. Like, I've said this to absolutely almost every founder I've ever spoken to. Like, having a co-founder, whether it's a services business like this, whether it's a tech business like yours, it's like a marriage. Like, I text Dale as much, if not more so, than my wife. Like, if I have something I need to bounce an idea off of, like, it's Dale and Jake that I go to. Like, it's hard. And I agree with you. If you during the interview process don't get excited to get back on, like literally, "Wow, I can't wait to talk to you again," probably the wrong person.

It it's you said it in a much more eloquent way of what we say a lot, which is: if it's not a hell yes, it's a hell no, every single time. You have to really. There's so much trust that you have to give to somebody to go solve problems on your behalf or your business's behalf and to trust that they're going to go do it and run with it. And if you don't have that obvious trust, it starts to feel like a hell no for sure.

Yeah, 100%. And I also feel like in the startup world, it's just a whole different world. Like, if you're in a more established company, it's a little bit different. But in the startup world, not everyone's built for the startup world, and it's hard. Like, everyone thinks it's so glamorous until they get in it and they're like, "Oh, I didn't know you had to work 75 hours."

Well, I think the thing is it feels exciting. You're frustrated at your big company job with all the red tape you have to jump through, and then you go to a startup and you're like, "Oh, it's actually great. You can do stuff," but you're also like, "I'm terrified. There's no rope. There's no net. I have to do everything. I didn't realize I had to do everything. Like, where's the enablement person? Who's going to create this stock for me? Who's going to go do that? Who's going to do this?" And it's like, "Oh, it's you."

No, it's you. And people don't realize what that actually entails. They don't realize how much structure, when you tell them.

Yeah. Even when you tell them in an interview, like, "Guess what? You're not going to have a deck. You're going to have to build your own deck," you're like, "Oh yeah, no problem." Then like the first—not only you're going to have to build your own deck—and then you're like, "Why is the CEO giving me feedback on my deck? Doesn't the CEO have something better to do?" And then it's like, "No, the CEO exactly wants to give you feedback on your deck." And people get a little put off by that. They're like, "I didn't have executives at my last company on my case about this." And it's like, "Yeah, I'm the standard bearer. I'm the editor here to make sure we're putting stuff out that is consistent and has the context of the whole company." And that's a weird pressure that people don't. Like, there's a line between I'm not micromanaging your work, but I am going to micromanage the quality of the stuff we're putting out.

Yeah, I love it. All right, time to get into some rapid fire as we wrap up here.

Daniel, what's a piece of advice that you once gave that you now look back and completely disagree with?

Oh god, that's a good question. Because maybe I've flipped around. You know, I don't know that I completely disagree with, but for a long time, I was staunchly anti-fundraising, anti-VC. I worked at Twilio like you mentioned, um, 14 years ago. And when I left, even in college before Twilio, I was a big Basecamp proponent, 37 Signals, and really wanted to just have my like solid, steady SaaS bootstrapped business. In many ways, I still just want my solid, steady SaaS business. But I started to look at capital as a tool that, you know, taking a little bit of money is not a negative. It actually is a massive boost if, like, I don't need to put all my financial resources and my time into my business. And I did that for a long time, and that was painful, at least with a software business where it does take some time to develop.

What's interesting is now with AI and Cursor and all these tools, like, maybe I would go back. And you don't need to take money to develop something. You can get to something very quickly. So I've kind of come around on that in another way. But I think you shouldn't raise indefinitely unless you have obvious revenue. Like, the market is pulling you so fast that you can't help but need cash to deliver more of it. And I think that's where a lot of people just get into a fundraising cycle. And I think we are still hesitant about that. But I was so staunchly against it. I had it as part of my identity. It took some time to shed that.

Yeah. What's the hardest leadership lesson you've learned the hard way?

Fire fast. I think that is probably one of those things that, you know, you hear a thousand times.

Probably told people, you told friends. You know, even just the whole process of letting people go and we try to do it very fairly. We try to do all that. But, you know, almost every time we've had to do it, it was probably a few months, if not longer, too late. We tried to be fair with people and give them a lot of shots and we probably look back and go, you know, that hurt the business broadly and other team members maybe more by trying to be fair to one individual. So, you know, I look back and go like, okay, we've had to get comfortable with this idea. And the fact that it is just painful and there's almost no good way to do it perfectly. Nobody's going to love it. But it's probably necessary.

What's a mistake that you still regret related to the business?

Yeah. Well, I'd say not joining Stripe at like employee 40 or leaving Twilio after two years. If I'd stuck around for five or six, I probably would have been like GM of a business unit. But those aren't regrets like I'm happy with where we are and I look back and you know life would be very different. Ben, you know you talked about Dale Benedict, my co-founder, is one of my closest friends. If I didn't leave Twilio and moved back to Chicago, I wouldn't have met him. We wouldn't be working together. There's a lot of things that are hard to look back and regret.

I think when Benedict and I look back at the business, the stuff we talk about is we wish we had a much better understanding of markets and how to size markets and categories and the maturity of those at the start. We went into an onboarding product and category far before I think the market was really there developed. It still is developing. You know, I think we have a much better—not an amazing A+ sense, but a much better sense of—like if we were starting from scratch today, we at least think we could evaluate markets and opportunities more effectively so that way we could get more, you know, tap a wave that's already going instead of having to generate, you know, a lot of demand. Um, so I think if I were starting over, the thing I regret is not understanding existing demand and not understanding how to tap into that.

Totally. Totally makes sense. Last one as we wrap this thing up. If you were a revenue leader right now and like you were having struggles like you didn't know exactly what to do, what's one thing that they need to hear right now for a business in the B2B SaaS space?

It's always hard to give generic advice because you know every business and every problem's different. But I think the thing we always think about is like pipeline solves everything in many ways. And so you know actually make sure you have the right pipeline or big enough pipeline, whatever it is—qualified pipeline.

Yeah. Yeah. Needs to be qualified, needs to be big enough, and needs to be growing.

Yeah. And you know most likely we're avoiding solving that almost most painful problem. Um because if you have a decent product, you have a decent team, you should probably be able to be growing well enough if your pipeline's big enough and qualified in.

There you go. Love that. Daniel, thank you so much for joining the show. If you have not checked out Arrows and you're looking for a deal room or a way to accelerate your sales process, a way to smooth out your onboarding, a way to make sure that you have a holistic view of your customers, check out arrows.to. Yes, I actually got that right. But go check out Arrows. And if you go over there, make sure to tell them that RR sent you. I'm sure we could work a little something out for that. But even at the cost of full price, like I told you this—I think one of my first calls that you guys are undercharging.

Daniel, thanks for joining the show, man. Appreciate it.

Thank you so much.