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

Daniel Zarrick, CEO of Arrows, faced a critical juncture when his startup was running out of money. Originally built as an isolated onboarding platform, the product lacked native CRM integration, causing users to abandon it after the initial novelty wore off. Realizing the product wasn't aligned with natural workflows, Daniel and his team made the bold decision to scrap their standalone dashboard and rebuild natively within HubSpot. This pivot taught him the power of "workflow ergonomics"—the idea that a tool must be positioned exactly where the user is already doing the work. Beyond the pivot, Daniel shares deep insights into the evolving landscape of digital sales rooms and the reality of AI in B2B sales. He emphasizes that while AI will excel at structuring CRM data and automating administrative tasks, it won't replace the human element of business relationship building. Instead, it will free up reps to make strategic decisions rather than drowning in data entry. Daniel also dives into the stark realities of startup leadership and hiring. He advocates for the "Sunday test" to ensure new hires are a definitive "hell yes," noting that the startup environment requires a unique resilience. From learning to fire faster to shifting his stance on VC funding, Daniel’s journey is a masterclass in adapting to market realities and building products that sales teams actually use.

Discussed in this episode

• Daniel's realization that building a standalone product on an island was causing user churn.
• The make-or-break pivot to delete the Arrows dashboard and rebuild natively within HubSpot.
• How capturing existing demand via adjacent HubSpot content fueled Arrows' early growth.
• The concept of workflow ergonomics and building software where users naturally spend their time.
• Why giving up proprietary data control to integrate seamlessly with a CRM drives product stickiness.
• How AI will augment sales reps by structuring CRM data rather than replacing human relationship building.
• The Sunday rule and why startup founders should only hire candidates they actively want to work with on weekends.
• The painful leadership lesson of realizing that failing to fire underperformers quickly hurts the entire business.

Episode highlights

1. 0:00 — Escaping the digital sales room box
2. 3:15 — The reality of the HubSpot launch
3. 7:30 — Running out of money and pivoting
4. 11:00 — Mastering workflow ergonomics in software
5. 15:45 — Trading platform control for CRM stickiness
6. 19:20 — The Palm Springs offsite strategy shift
7. 24:10 — The future of AI and go-to-market
8. 31:00 — The Sunday rule for hiring talent
9. 36:45 — Firing fast and shifting VC mindsets

Key takeaways

• Build tools where the work actually happens.
• Isolated products die from workflow friction.
• Use the Sunday rule for startup hiring.
• AI structures data; humans make decisions.
• Qualified pipeline solves almost every problem.

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. Uh, we have with us today a, I guess we could say we're a client, we're a customer, we're a referral partner, we're we're a little bit of all of it here and you'll learn why in a little bit. But we have Daniel Zarrick, 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. Um, but Daniel's a product-focused founder, passionate about building software that sales teams actually use.

Based in LA, you're apparently a big F1 fan, uh, and a movie lover as well. Which embarrassing. What kind of movies? Embarrassing.

I'm actually wearing one shirt today because the season starts tomorrow, so I didn't even know that was my. Did you go to the one in Vegas? No, I went to one in Mexico City last year, uh, but I got sick for race day. So challenge of going to Mexico for a race.

Yeah. Yeah. Oh, yeah. Yeah.

Welcome to the show. Dale, you're supposed to say you're supposed to welcome our guest. Daniel will give the show. It's good actually.

I got to meet you. We talked a little bit. We haven't talked before. Um, I know you've been working with Adam a lot and we we talked about, is it really genuine or not?

It's totally genuine. So, we, uh, internally we've been talking a lot about what you guys are doing. We've believed in deal room for a long time. It's not just the Arrows world, it's just in this world of deal velocity and sales, it's super important to to have things like deal deal rooms.

Um, but before we get into the deal room pieces, um, 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 the challenges you had where you felt like your go-to-market strat, like strategy was out of control, uh, you know, you were like, is this really going to work? And it could be Arrows or any other place you worked. Um, tell the audience a little bit about what that what that moment was and what you were doing to fix that moment.

Yeah, you know, I think one thing that's that's interesting with the story of Arrows, we focused 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, April 2022, it really didn't work for like three, four, six months. Like it, we we made the strategic bet.

The product felt like amazingly better. The the iteration of the product we had before was, you know, doing okay, but not actually working, uh, to justify having funding and and the team that we had. But we launched on HubSpot, we're like, our product is immediately like night and day 10 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, you know, 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 what's the trigger point for somebody to buy? What's the, you know, time like that they're going to buy on? All this stuff.

And, you know, 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, you said, we've had nothing come to us easy in a lot of ways and and we're actually happy for that because we as a team have to remind ourselves that nothing comes easy and, you know, the team's really had to work for it. Um, so back when we launched on HubSpot, it really came down to finding like 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, you know, on YouTube and the HubSpot community forums, guides on our site that was, you know, how to run customer success on HubSpot, how to set up a renewal pipeline on 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 are then looking for, oh, we actually do have an onboarding process that's in Asana or something. Maybe we should bring it into HubSpot as well. And this tool looks like a pretty good fit.

So that was, um, kind of what we figured out then and a lot of what we still do now is, you know, demand adjacent content that then can capture what people are trying to do with arrows, hopefully. So you like HubSpot, huh? Yeah, we like HubSpot. Uh, so I we're we're super bullish on HubSpot as well.

Um, I think they've made a ton of improvement improvements, um, in the past year, maybe two years. And and you're right. You guys haven't had it easy, right? There's a lot your your space is crowded, man.

Um, you know, there's a lot of people out there. I I won't name competitors out of respect for you on this show. Um, but there's people who have been around for a long time, um, people who have massive LinkedIn presence. Um, I think your team does a really good job.

Kim does a great job with her content. Um, and I think you guys try to educate people. But when you are looking at like the space that you're in. And the journey that you've gone through.

Talk to me like 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, like I don't know if this is going to work. I don't know if we're going to be here. Um, Yeah.

Walk me through that like, oh shit moment where you're like, am I going to have a company in six months? Uh, which one? Which moment? There's multiple.

Pick your poison. Um, Yeah. No, I think I mean, you hit on something interesting in the intro that, you know, 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 ups email because it's really is all of us who interact with customers in in sales, in onboarding, customer success, we send these follow-up emails, next steps emails and, you know, they're generally not very effective. They're not, 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 or actual follow through. So we spent 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. Like it wasn't connected to CRMs. It wasn't, um, we were trying to build everything on an island. You know, Arrows was its own self-contained thing where we tried to, you know, close one deal happened in Salesforce or see, you know, in HubSpot, it triggered something in Arrows, you'd run the project entirely inside Arrows.

And there really wasn't. So you weren't always native. We were not always native. And that was That's one of the main reasons I love Arrows is you 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 data extracted 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. And we realized people would just forget to like log in and use Arrows because I could keep going and doing what I was doing before. And, you know, that's when we saw the writing on the wall of like, look, we 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.

And that's when we made a dramatic change to delete our dashboard, build on the CRM, chose HubSpot as the first place to do that. And then when we launched in HubSpot, there was uh, like I mentioned, 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 like apps, uh, 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 launched it on a marketplace and it just goes. And so that's where we really saw the writing on the wall of nothing, if we do nothing right now, it's not going to just, we built this awesome product, but it's not just going to work. We'll run out of money. And so, um, now we're luckily in a spot where that's not the case, we're going to be around for a long time.

Um, and uh, yeah. Well, that's always good. Yeah. Yeah.

Well, and you just mentioned something very interesting. And I think when we talk to a lot of companies on this this go-to-market gap concept, one of it is really value and usage. So there's this place where, um, when you we our third stage is really repeatability and scalability. But the bigger problem is like they use it at the beginning or they use it for the first 30 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 room and looking through things. And I think that embeddedness in the 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, like you're it's like a constant reminder that it is getting used through through HubSpot. So, um, my question is like, how do you how should founders or how should revenue leaders or CEOs be thinking about being usable?

Is it like weekly? Is it bi-weekly? Is it daily? Like, where is that sweet spot in the B2B tech space?

I would say changing the question, 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, you know, workflows in any role as plumbing, there's a series of pipes and those pipes are steps.

Arrows is slotting into a a piece of that plumbing. So we have to know the inputs, we have to know the outputs. And so for us, um, with a deal room on the sales side or an onboarding product, those are 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 I'm sitting here at my desk, I want to drink water. I've got a big jug of water here on my left. I 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 and their CRM, where that data should be or where that thing should be, it's there. It's right there. It's more 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 and this this next action, uh, more easily than it would be to ignore it. Interesting.

Again, that's a good way to describe it actually. I I love I love the analogy. I don't think people think like that. Um, when they are trying to properly position their product, right?

It's like, oh, we we we help you do this. But the ergonomics one I think is important. I think it's scary for a lot of people too, right? You 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. 100%.

And with us, you know, Adam, as you know, like Arrows puts a lot of our own data back into HubSpot. We have 60 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 will 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 is, 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 uses 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.

But that's what makes the 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 by by.

And that's letting helping me run my business. So, And all those reports, like if you turn those off, 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, and it's it's very hard to create a new workflow path once the sales world is actually happening. Like like once you have a path, it's very hard to break that path. Um, so I have a uh shift of a question question a little bit. Like looking back at some of those real gaps that you had as you were going through the process.

Um, was it like was it a mindset shift? Like was it 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 like something else before you're like, ah, we got to change it up.

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I think it was a blind spot. I mean, think of every how every product, every CRM integration existed three, four years ago, right? There 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. Uh every winter now for four years, we've gone to Palm Springs for our 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. We said, what is, you know, what is Arrows? What is the unique value that we provide?

You know, we were getting customers asking us like, oh, I want reports. I want Kanban view. I want automations. I want all these things.

Everything. I want everything that you don't do. Yeah. And they're they're logical requests.

Like we had no problem with the requests, 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 the 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 requests 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 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, you know, point of view.

Yeah. 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, um, have come to be for a plethora of reasons, not the least of which is what you said, right? Like it's the checking an email. It's the 35 emails. Like Dale and I are in the process of closing a deal now.

It it's actually the first one where I think we've used Arrows from soup to nuts. Um, every time I follow up with the customer, it's, hey, thanks so much, you know, for the meeting today. I've updated the, here's your link for your Arrows room, and I can probably snip it, but I do it manually anyway. Um, and here you go.

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. Um, but this started somewhere.

And I think this ties into like where go-to-market is heading, right? Whether it's sales rooms, whether it's AIs, whether it's, uh, or A I S, whether it's A I S D R S, whether it's outbound at scale, like, you're you're Nostradamus for a second, right? Put on your go-to-market hat. Where's go where's go-to-market getting going?

What's going to change fundamentally, whether it be sales process with things like sales rooms or every fucking sales person is dead because we're all just going to go online and do our own research and everything's going to go PLG. I I don't think that last point is at all true. And I think you'll all agree. Yeah.

Uh, I think this what we're doing right now is actually just this is the thing, right? We're talking, we're building relationships, we're understanding each other. Like 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, you know, why does a CRM exist? It exists because we used to have, you know, spreadsheets or even pieces of paper where we just keep track of our notes. And, you know, 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 would be nice if that was networked across computers. That would be nice if that was online. Et cetera, et cetera. Yeah.

Oh, we're doing email. It would 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 their associations up to date, keep all the communications logged, keep the next steps in a structured format, keep the closed date in a structured format. What's going to close this month?

How big's that deal? Who's all involved? Yeah, yeah, yeah. That stuff is a lot of like junk that is really hard to stay on top of for humans, but it's 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 and all the reps we work with is making decisions on on options that are presented to us. You know, if I if I had three follow-up emails put in front of me by a system and go, that one's good and relevant, that one's not. Maybe I'll tweak that line a bit and click send.

And so for us, we think, you know, and why Arrows has been particularly interesting for us for a while is, you know, 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 Zoom, maybe, in person, et cetera. But now like the, you know, we're big fans of call recorders, all of us and and the data that comes out of that, the relationship there. Um, but you know, there's you know, Adam, what we were messaging about is there's a lot of data, a lot of uh context that comes out of this call if you're paying attention to it and the system's paying attention to it.

Yeah. Arrows is in 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 slinked 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 our deal with our buyer and our customer. Yeah.

All the all the stuff in the CRM is just a a database representing that. It's not super. And nine times out of ten, it's not even an accurate database representation. 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 clips. And I think then I can spend more time on I have more capacity to be on calls or to help customers and spend more time strategically with customers. And that is the hope.

It's not like, you know, some uh AI avatar is likely going to uh 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 the options.

Yeah. You were just talking about, um, the massive amount of data. And I think this is where, um, 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 the distillation of that data? Yeah.

Um, so how do you guys deal with that from a, uh, sales room perspective? Um, 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 from the sales people? A trust is something we think about a lot, both 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 that we can fill that trust battery?

Um, right now our onboarding into the product, like the product-driven onboarding is pretty lightweight. Um, but we're thinking a lot about how we, 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. Yeah, 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? Um, 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 and 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% of the way or 80% of the way and then present something to you. You know, so when you get an LLM or AI powered suggestion from Arrows, it says, hey, it looks like you just got off a call, you recorded it with attention.

Those notes are in the CRM. We think you should update this this sales room and 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 to update it. Yeah. Maybe in two years or a year, it'll be automatic. And they don't really read it still and they just click and put it in anyway.

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

I'm deep in thought for it's interesting because right? We we don't always This could be a first. This could be a first, Daniel. Yeah.

We we don't. Think he's quite. Yeah. I know.

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

You should see us in a meeting. Um, as you continue to build and add, you know, 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 of I'm going to bring someone on this team. I need them to do and be what? Not Dale.

It's a really We not Dale. Yeah. Number one, not Dale from what I can tell. Thank you.

We we so you a lot of companies. We so you a lot of companies. I think we 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 excited.

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 are things are bad and blah, blah, blah.

But I want them to be excited about the opportunity at the start to 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. Like they're generally pretty excited. But what you know, a lot of people post, oh, we got 1200 applicants for this role. We got 2,000 applicants for this 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 the state of the business. Job postings are hard.

Getting a good job posting, I don't think people recognize, like nine out of ten job postings I see, and I'm curious your thoughts are some copy-paste of someone's bullshit with the company name changed. Period. The end. Exactly.

Like where can we 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 was a good job.

And then I get to go reply and say, that was me, the CEO and here, let's go schedule time to talk. You know, and like they're that that is a signal to them of like how we want to show up in the process. Um, one thing we've tried to do I think historically is move very quickly in the process because we, you know, people hate being in a long interview process. What's very quickly?

Dale Dale doesn't care about hiring, so I I have to obviously. I care about hiring a lot. I have to ask all the follow-ups here. Two weeks.

That that that is relatively quick. Yeah. Maybe three at most. We'd like to do that.

I think we're changing on that. We 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? You're not looking forward to the call every single time, it's not someone you want working with you. Yeah. Exactly.

Like at Stripe, I was friends with all the early Stripe people and their founders. And um, I remember early on they had this thing like the Sunday. It's either the Sunday rule or the airport rule. Maybe there's different variants of this.

But if you were at the airport, um, 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 person's there or less? There's like a an initial reaction that you get when you see somebody that you didn't like working with, really. Ah, 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 to build up to that. Yeah.

I I joke. I I I can say honestly, like there and he's never he's going to take this recording and never let me live it down. Um, but there is no one else I would rather build this with. Like it's hard, man.

Like I I I've said this to actually 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, like 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 the like, literally like, wow, I can't wait to talk to you again. Probably the wrong person.

It it it's you said it 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. Exactly. 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 like obvious trust, it it starts to feel like a hell no for sure. Yeah.

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, like not everyone's built for the startup world, and it's hard like everyone thinks it's so glamorous until like they get in it.

And they're like, oh, I didn't know you had to work 75 hours. Well, I think the thing, yeah, 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 terri- Well, you can do stuff, but you're also like, I'm terrified that there's no rope. There's no net.

I have to do everything. 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 doc 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 they have. Even 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 know, you're going to have to build your own deck. Oh, yeah, no problem. Then like the first 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 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 somebody 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 a weird pressure that people don't that 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.

I love it. All right, time to get into some rapid fire. Um, as we wrap up here. Um, 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. Cause 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 you mentioned um, like 14 years ago. And when I left I even in college before Twilio, I was, you know, a big basecamper proponent, 37 signals. And really wanted to just have my like solid, steady, SAS, bootstrapped business. And in many ways I still just want my solid, steady, SAS uh business, but I I started to look at capital as a a tool that um is, you know, taking a little bit of money is not a negative, it actually is a massive boost if you 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. Um, at least for the software business where it does take some time to develop. What's interesting is now with uh AI and cursor and all these tools, like maybe I'd go back and you don't need to take money to develop something. You can get to something very quickly.

Um, so I've kind of come around in in on another way in that way. But I think you shouldn't raise indefinitely unless you have obvious like the market is pulling you so fast that you can't help but um deliver uh 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 to not do that. Um, but I was so so staunchly against it and 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? Um, fire fire fast.

I think that is probably one of those things that, you know, you hear a thousand times. You probably told people, you told friends. Um, you know, even just the the whole process of letting people go and we try to do it very fairly. We try to do all of that, but you know, almost every time we've had to do it, it was probably a few months if not longer too late.

You know, we we tried to be uh fair with people and um 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. Um, so, you know, I look back and go like, oh, okay, we've had to get comfortable with this idea. Um, 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. Um, but it's probably necessary. What's a mistake that you still regret? Regret.

Related. Related to the business. Yeah. Oh, I was going to say not joining Stripe as like employee 40.

True. Too too true. 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.

Um, but you know, but those aren't regrets. Like I I'm happy with where we are and I look back and, you know, life would be very different. Um, Benedict, you know, you talked about Dale, Benedict, my co-founder is one of my closest friends. If I didn't leave Twilio, move back to Chicago, I wouldn't have met him.

Um, we wouldn't be working together. There's a lot of things that uh are hard to look back and regret. I think when 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's still is developing. You know, I think we have a much better not an amazing A plus sense, but we have a much better sense of like if we were starting from scratch today, we at least think we could evaluate um 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. Uh, last one as we wrap this thing up, um, if you're a revenue leader right now and like you were like having struggles, like you didn't know exactly what to do. What's one thing that um, they they need to hear right now for a business in the B2B SAS space. Uh, it's always hard to give generic advice, um, 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. Qualified pipeline. Pipeline.

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

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

Love that. Daniel, thank you so much for joining the show, man. Appreciate it. Thank you so much.