#49, Joe Thomas, Co-Founder and CEO of Loom — Why it’s essential to track your time; how to get b...

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. Welcome back to From Startup to Grownup, and today I'm so excited to have Joe Thomas, the co-founder and CEO of Loom on the podcast. Loom is an async communication tool. You record a video, and while you're recording, you can also show what you're doing on your desktop. Then you can send it to someone or to a group, and they can all watch it whenever it's convenient for them, and they can speed it up or slow it down or watch it again. Joe and I had a fantastic conversation. We covered the early days of Loom, what Joe called the grind, when they pivoted 3 times in 9 months. We talked about the agreement the 3 co-founders made to get Joe to move to LA and sleep on a twin mattress on the floor in his co-founder's home, mind you, and how Joe learned to fundraise, which did not come naturally to him. We talked about the counterintuitive way Joe prioritizes his time to make sure he is working on the right things. And we also talked about why Joe thought it was so important to codify their values when they were only a team of 7 people and how those values have helped them run the company even during difficult times. And we covered the tools that Joe uses to make sure he is in a good place so he can make good decisions. This is such a great conversation with a really outstanding founder and leader. So please enjoy this great conversation with Joe Thomas, co-founder and CEO of Loom. Joe, welcome to the show. I'm so excited to have you here today.

Thank you so much for having me, Alisa Cohn. Feels like a long time coming.

I— yeah, that's for sure. I feel— I totally agree. So tell us about Loom. Let's start with Loom. What was the founding insight?

So the goal for Loom, we actually were 3 founders that showed up to a whiteboard one Sunday and we had a good balance of skills. I was a product manager by trade. We had an engineer or like CTO and then designer by trade, although Shahid had been working in VC for a little bit. Either way, we had all said, why are we not building together? We had been best friends for over a year at that point. And we showed up to the whiteboard, and what we actually decided to work on, we all had to come up with 3 ideas. And we felt like video at work, we were using Snapchat in our day-to-day communication, but we would show up to work and we were using Outlook for email, and we were like, one feels like the future, the other one feels like the past. Now, we ended up having very specific applications of video at work. So we started with a user feedback platform that we wanted to be a two-sided marketplace of experts giving feedback to companies, whether it's like PRD or design file or even like live production experiences. Can you have an expert network that gives feedback for microtransactions? Now, we kept pulling on threads as we were launching these and hearing from our users and customers that the ones that we wanted to build for, those that actually had money, were saying that this sort of video feedback that was a screen and a superimposed camera feed that they wanted that from their real-time users. So we ended up building a Chrome extension that enabled you to collect NPS feedback. And then you could offer a discount to users if they ended up responding in a certain way. So for those that remember Soylent back in the day, they were actually one of our early beta partners. And they would offer a 20% discount if a user would give video feedback as to— the product overall or maybe why they were potentially planning to drop off out of the checkout form. And then through going and working with 5 different companies and partners with this product, we actually started getting feedback that, oh, this recording with the Chrome extension and then the camera bubble, which is fun because we had changed it from a rectangle to a bubble just to make it feel friendlier and nicer. They're like, can I record a video without having to upload some sort of user feedback? On the website. And so we separated out the Chrome extension from the user feedback platform and launched that. And that is when we were like, we got something that works. We're off to the races. And that's what we turned into and rebranded to Loom after we launched that product.

That's fascinating. So I mean, it's like you really iterated pretty fast, it sounds like. If I'm not mistaken, it was like 7 months, and you went through a few iterations of products like you're just describing. You know, I guess I'm just curious, like your, your customers were speaking to you, but like, were they literally speaking to you one-on-one? Like what made you realize the thing that people really want is to communicate in quick videos and thus the, the Loom insight was, was founded?

Yeah. So it was an absolute grind in the early days. It took us, so we started building in September of 2015. We didn't launch what is now Loom until June of 2016. So it was about 9 months of rapid iteration and a couple major pivots. And in those days, it really was one-on-one conversations. Like, you can get a lot of earned secrets, is like a phrase that an early product manager at Loom used. And it was just through talking to people directly. I mean, part of the grind was, you know, we got blocked from our Gmail accounts a couple times because we were sending out hundreds of emails per day trying to get in front of people in order to say, would you use this platform? And then if you send out 200 and you only get a couple conversations, like those conversations are worth gold. And so it was a relatively small subset of feedback. But if you actually look at what's required for essentially like an insight, you don't need to talk to that many people. You really only need to talk to 6 or 8 to say, okay, this is a representative insight if you hear it from 6 or 8 different people. And so that, that was how we really decided when and how to pivot. Like, obviously there was the usage metrics and feedback, which is, hey, we launch on Product Hunt, we spike up in terms of usage within the first 12 hours, and then it goes back down to zero. So you're like, okay, something's clearly not working here. What's not working? And then what are the bright spots? What is working? What are people really interested in? And just being willing to make massive shifts in the early days because You have no idea what you're gonna be working on longer term if you just start building. And velocity is really important. And then being able to be a really good listener and understand what users are asking for of you and then acting on that.

Yeah, I love that. And we were just talking just before this podcast, before I hit record, and we said, you know, Loom has now become like a verb or a noun, like to mean I'm gonna send you an async video, right? To describe it with like, you know, graphics in the background to show what's going on. How did you, I mean, it's great that it's now like, I'm gonna send you a Loom or I'm gonna Loom you. That's wonderful. But like, you know, when you started the company, it was by no means a household name. Why did you pick the name Loom?

So when we had launched, it was under the brand Open Test was the multi-sided network that we were working on. And then, uh, you know, one of my really terrible branding mistakes was calling the Chrome extension OpenVid. So people were confused about how did the Open Test platform map to OpenVid? And we're like, well, they're two kind of like separate different systems right now. So, you know, use OpenVid as much as you want. Like, you don't need to use OpenTest in order to utilize OpenVid. But we knew when we launched on Product Hunt on what was basically like Thursday night, but like Friday evening at 12:01 AM, because that's how you gamified Product Hunt, that, you know, Friday we had that spike in usage. And then Saturday I woke up and I looked at the analytics dashboard and we were having more users and more recorders on Saturday than we were on Friday. So at that point, said, we did it. I don't know what we did exactly, but we did it. And so from there, it actually took us about 6 months to rebrand to Loom because we were really busy listening and talking to customers and building product features that they were asking for because all of a sudden we had thousands and thousands of users when we were used to having none. And so it took us a little bit of time to rebrand, but we had been throwing around names for months and there was this, we liked the um sound, honestly. I don't know how else to describe it 'cause we were talking about Plume or Flume. You just want a single syllable name as much as possible. And I was, we were all broke founders and I had a long distance girlfriend at the time who's now my wife. And I was riding a Megabus from San Francisco to LA. And I told Vinay and Shaheed that I was going to get off the bus ride and decide on a name. And that's what we were moving forward with. And I looked up and I was researching online things around Loom. And there's this concept of superluminal communication, which is theoretically faster than the speed of light communication. Then it's also you could tell a story around like weaving people together through async video because there's a very real human component And so you brought those together, and I had looked up some of the trademark things around Loom, and it was like, it's an open space for communication collaboration software. So that's how we landed on it. I mean, it really is a, it's a nice word to say. It is like there's a story to be told around it, and there was an opening for us to go after the name. And fortunately, just to round out the story a little bit, we were under the URL useloom.com for a long time., but we knew that Dropbox owned loom.com through an acquisition. And we were bugging them a lot for 2 years. And when they were going to go public, they were offloading some of their static IP that they didn't need anymore. And so we were able to purchase the loom.com domain from them.

Oh, I love that. Oh, that's such a great story. And I love how you sort of— it came together and it makes it— it has resonance as it has meaning. But also to your point, it's easy to say, It's easy to spell, which is not always the case. So it's like a happy good fortune, happy coincidence.

100%. I mean, it really is. There was a window of time where software products had cutesy names and they all ended in -ly. And to us, we wanted something that felt like it could be a household name. That was obviously like a really high bar to set. But that was something that we felt like we had captured lightning in a bottle and we needed a name that represented how big the opportunity was. Like you hear—

Yeah.

You hear Apple and you're like, what does that have to do with computers? It doesn't need to be such a direct through line to be a great iconic brand. It doesn't need to be a literal translation. Pick something that you feel like is going to feel good to somebody when they talk about it to somebody else. I think it's a really, really important kind of thing to keep in mind.

I love it. I love it. So during that grind, as you call it, you know, if I'm not mistaken, and we're like, kind of fill in the blanks for me, because I think you were using your personal credit cards to fund the company. And also, I know that you said in one of your talks that you were like, you had 2 weeks of runway left. If you're using your personal credit cards, you actually had zero, like negative, right? Runway left. So like, talk about that early days of like, feeling like we have a limited time that we can really fund this business. Like, what was going on then?

So I had set a bar with Vinay and Shahid, who were both living in San Francisco, that if we raised at least $25,000, that I would uproot my life from LA and move to San Francisco to build this. And we landed at $25,000 exactly like that. We had two angel checks, $10K and $15K.

You should have asked for more. You should have set a higher bar.

Exactly.

Right.

In retrospect, it worked out, but I did have some regret when I had a twin mattress on the floor of my co-founder's room for 6 months. But the thing was for us is that when we were deciding within these major pivots that we were making, we kept pulling up and asking ourselves, and each other, are we still having fun? Do we wanna continue to do this together? Because they were big changes and there was no guarantee and we were sinking some of our personal fund, like our savings and checking, we all had good paying software jobs as relatively young individuals and so we did have some savings in the bank and we were clearing through all of those because San Francisco rent is not cheap and that we all had to progressively start to get rid of things like our cars that we had payments for. I had student loans that I didn't pay off until finally in 2020. And so there was very real, like, major expenses that we had that we, that we didn't offload right away or literally could not. And so that was dwindling very quickly in terms of the $25K in our personal savings. But we kept talking to each other and being like, is this worth the dollars that we're putting in, including our own? And every time we said yes, you know, we're having fun building together. It's hard, but we feel like we have insights that we should absolutely continue to go after. And so then you fast forward all the way to when you talked about of having literally 14 days of runway left. Like, yes, our credit cards were maxed out. We had run through that $25K in our personal savings, and we knew that this was our last shot on goal. We had been maintaining relationships with VCs like 15, 17 had actually asked us to start sending them weekly emails in terms of what we were working on, what the updates were. And we were doing that because we were like, we need more funding. And so we'll take on this additional workload. And but we knew this was our last shot. And then finally, when we sent them that email around post-launch and like, here's the first 72 hours of data, more usage on Saturday and Sunday than that Friday. They came to our apartment on that Monday and we told them that we're running out of money and they're like, okay, well, we'll just send you the $250K that we plan to invest. We'll like figure out deal terms, but just so you all feel okay. And they sent us the wire by Thursday. Wow. And so like, it really was this— we had no regrets. Like by the time we had gotten to that 14 days left of runway, you know, we obviously, it would've sucked to potentially have to like go back and then potentially move into our parents' places for a little bit. But Jeff Bezos talks about regret minimization framework and like if you look back on it, would you regret having given up because you were starting to run outta money but you hadn't actually run out yet? And all of us were like, no, we need to absolutely run out before we give up.

Hmm. You know, spoken like a true founder, like, I guess I want to probe a little bit more on like what you're experiencing. So like, you could say, hey, as long as we're having fun and we have— we're getting insights, we're making progress, we're having fun. But you can have a lot of fun in life without founding a company. So like, what is the drive inside of you and your co-founders that was saying like, and this is significant, or, and we can't give up, or something like that? Because it wasn't just about having fun, although of course, that's part of the game.

So, I think that I appreciate this more in retrospect that I can articulate a little bit more, but I don't know that I fully appreciated at the time, which is that it just felt special. I don't know how else to like describe it. Like, I think that we really were best friends that were living together in an apartment that we're building together that we had all experienced full-time roles. Where we felt like we were running our heads against a brick wall at the companies that we were working at, that we felt like we had more to offer, but we were being told no in a lot of ways. And so, you know, it was just as much about, hey, what can we do together? It's like, we don't want to go back to that, you know. We, we all felt like we could do something together, and it was the best working experience that we had in our careers thus far. Because like I was saying, we were all relatively young. The average age between us when we were building at that time was 24. And so I felt like we all had this experience of working together that we hoped that our future careers could look like. And so I think that that to me was what really kept us going, was that we didn't want to go back to the old worlds, which is part of why we started the company together is like, we're not necessarily bad employees because we're ambitious and we wanted to drive impact. But a lot of times, we felt like there were bigger opportunities that the company that we were working at should go after, and we were misaligned, you know? And that misalignment is painful when you experience it. And so sometimes you just need to be your own boss.

Yeah, that's so true, to have that kind of control. So that's amazing. And so you landed that first, like, really small-ish check, although it kind of kept you where you needed be. And then of course, you— how much money have you raised total now?

A little over $200 million.

$200 million. My God. So I think that you probably learned a lot about fundraising in this process. So first of all, how did you set about like improving your fundraising skills? Or was it like a natural strength of yours?

No, I mean, we got 100 nos before we got that one primary yes. And it is a little bit cliché to to say, but you just have to go out there and put yourself out there and have at-bats. But the one really important thing that I think if you're in the earliest stages of learning how to fundraise for the very first time is right when you're done with the meeting, take detailed notes about what went well and what didn't go well. And a lot of times we would ask explicitly of investors who decided to pass, it's like, can you just give a sentence or two as to why? You have to assess on your end is like, is this valid feedback? Is this like, did they take the time to actually write real feedback? Or is there things that I think in retrospect, a lot of professional investors passed on us because of the fact that we were all first-time founders and that we just didn't have extreme kind of credentials. We didn't go to prestigious schools. Just universities. We worked at some solid companies, but were they like the premier companies?

No.

And so all of those things is like, they're not super clear about what they're working on. They don't have traction yet and they don't have the pedigree. So then from there, I think you kind of like the pre-seed is more about selling yourself because pre-seed investors know that the idea changes over the course of time. So they're really investing in the founders. And I think that to me, that's where we just had to prove it with usage. That was like the real unlock for us was that we had real users and real traction. And that's when we got real money. From there, you really have to articulate clearly what dollars that you're raising for, for what are relatively simple goals of what you plan to do with that money. And I think that that was a really critical insight for us as we went to go raise our seed rounds was, what do we plan to do with like, okay, we raised a couple hundred thousand dollars. What are we going to do with a couple million dollars? That's like an order of magnitude increase in terms of dollars. And so for us, it was simple. We wanted to get to 25,000 paid customers and we wanted to grow the team from what was 5 people at the time to we wanted to build it to 15. And here's the the roles and functions that we're hiring for. And that's it. Like, if we could go from users to paid revenue and we could prove that we could increase the talent level of the team, then that would bridge us to the Series A. Now, did that work out in practice? Absolutely not. We did not monetize before our Series A. And that in and of itself was an incredibly painful round of funding to raise because I got a lot of questions around, are you all a consumer product in disguise because no B2B SaaS product raises a Series A pre-revenue, at least not back in 2018. And so it was a good filtering mechanism because we got a lot of nos, like 85% nos right on the front. But that means that there was 15% who are real believers in what we were building for. And then from there, like I said, you have to understand what the investors that you potentially want to work with understand in terms of de-risking the value of the business between What story are you telling today? What progress have you made? But what are you going to do next? And there is— when you do get to Series A, it will likely be your first board member. Right. And so this is where you have to make sure that you are aligned on a 10-year vision in terms of what you're doing today, but also how do you ladder up and de-risk the business over the course of time?

Yeah. So lots of questions like how actually do you make sure that you have that values alignment with that first, as you said, the first board member? Like, how do you do it? Because you solve, oh, we want to build a good thing. Oh, we do too. We are in for the long term. Oh, we are too. You know, how do you actually test that?

We, and this is more of a, I heard it once from another founder and CEO. And again, this, like, you, you do start to appreciate these sorts of things that you logically understand, but don't feel in your bones until, you know, now I'm 5 years into my relationship relationship with Ilya Fushman, who is our Series A investor and our first board member, is that it is a 10-year relationship. And so I think that the most important thing you can do as CEO and founder is investor relations is a real part of your job and work stream. And I think it's a big mistake to not be meeting investors and building relationships with them over the course of time. Because those that will spend real time with you as a founder and CEO, before you're fundraising, kind of like wrestle, be open with investors that are not around the cap table yet. Bring real problems with them and see how you solve problems together. And so I knew Ilya for a little over a year before he invested in our Series A. It was the same thing with Andrew Reed. I knew him for about a year before he did our Series B. DG I'd met when we were raising our B+, and he's at Andreessen Horowitz. But I had known him for about a year at that point. And so the average length of time that I knew an investor before they officially became part of Loom is at least a year across the major board members or board observers that we have at Loom. And so while it is your early stage, I was there with any founder that's listening to this in the pre-seed, seed, Series A, I was exhausted all the time. And you're like, one more work stream, I'm like, I'm recruiting the entire team. I'm running the entire product roadmap. I'm like dealing with all of the HR stuff that we have to. And you're like, you're telling me I have to also build relationships with investors? And I'm like, yes, it is absolutely critical if you want 5 years on to have a high-functioning board.

Yes. So wise. I actually, I want to keep asking about fundraising, but I really have to key off what you just said too. Like actually all the founders I work with, especially in earlier stage, are exhausted. They're working all the time. And everything you just described is mission critical. You know, the idea of spending all your time recruiting the team, all your time making sure the roadmap's on the right, dealing with big customers or small customers in the case, right? And then you've got to go out and you've got to, you know, build relationships with many people, but certainly investors. How, what advice do you have or how did you think about managing all the things when literally there was not enough time in the day?

I spent a lot more time on this than I do now in terms of trying to be as rigorous with time tracking as possible. I forget the name of the software, but it actually was a desktop app that kind of like tracked all the different softwares that you were using. And at the beginning of each week, actually, Vinay Shahid and I would meet for what was originally founder dinner, and we would do it every Sunday, and we'd just have 2 hours together and like talk openly about the business. But we would also share what are we doing with our weeks next week? What did we do with our weeks last week? How would we rate ourselves in terms of productivity? And I wanted, I'm a like product person by trade and like I want data if I can get data. And so again, I forgot the name of the software, but there's more now that have come out at this point. But I really track my time in terms of how often or how much time per week was I spending with for people that I was recruiting? How many customer conversations was I having? Like, even if it was working sessions of like product roadmap, I would track that on my calendar. And so all of this would be, I would reflect how am I splitting my time and then rearrange as appropriate because for me, the biggest thing was there was always a million things to do. And unless I created that process prioritization and clarity for myself, then everything felt bad. You know, I wasn't doing anything well. And I think that it's really important for you to understand what's the most important thing for me to work on, and then try and hold yourself to that as much as possible. So that way you feel okay about all of the other fires that are burning, because there will always be fires burning, especially at those stages. And you just gotta make sure that you're prioritizing your time most appropriately, and that comes through tracking.

That comes through tracking in terms of knowing. But then how do you really know? How would you say, on the one hand, the product roadmap, because the product is our thing, it's our lifeblood, as compared to talent? Literally, how can you decide which is more important, how you can prioritize?

I think people default when they're really uncomfortable or tired to their strengths. True. I found myself, I still love to work on product, right? Like if I could spend 110% of my time on that, I would. But I still love other parts of my job too, of talking to customers and working with Lumates broadly in order to build the best company and product possible. But I know what my default is, is I spend time on product. And so to me, I knew, and you you kind of have to map your own strengths and you have to understand where you default spend your time. And then what are the things that you're avoiding because you feel uncomfortable, like the most uncomfortable during it? And to me, it actually manifested a lot in hiring for roles that I had what I felt like no business hiring for, right? Like hiring our first business operations person, hiring our first product marketer, right? Hiring our first HR person. Person, right? Like, these were all really painful for me. And when you're hiring for a role and it's been open for about 4.5 or 5 months and you're still doing the job yourself and you know that you're indirectly avoiding it, you just need to hold yourself to the fire. And I think that that's one of the more painful things about being a founder or specifically like a founder CEO is that you have to wear so many different hats, especially in in the early days. And so know yourself is really, really important. And then hold yourself accountable to doing the things that you really don't wanna do.

Mm, I think that is so wise. I think it's so wise. Where did fundraising fall into that for you? I, I wanna go back 'cause I know that you wrote a document for your employees about what do we learn from our Series A? But would you say for yourself fundraising was like in my strike zone once I figured it out? Or would you say, no, I put it off?

I would say that there are parts to the fundraising process that were my strike zone and the parts that they were energy-draining in the sense that you have a lot of anxiety associated with it. And so to me, I love storytelling. I really do. I think it's such a powerful human thing that if you end up telling a story that people resonate with, I mean, my goodness, is that such an amazing experience to be part of. And so I loved building the deck. I actually loved the part specifically around you're forced to dig into your data and try to find key insights. And so finding those nuggets that you're like, wow, how did I not know this? I'll just tell a quick side story, which is we were raising our Series A, and Ilya Fushman was like, you need to— to kind of tell the intra and intercompany network effects or virality that's happening. So show how Loom spreads across organizations and then show how it spreads within organizations. And we were analyzing HubSpot specifically, who had the most users on our platform at that time. And I knew that the CEO had signed up and started using it, but what Loom specifically did he sign up from, and to be clear, I didn't watch the Loom, but I could see the user was an IC engineer. I went to their LinkedIn profile, had seen that they were an intern during the time that he had recorded and sent the Loom, and that was the Loom that got the CEO, Brian Halligan, to sign up to Loom at the time. Wow. Yeah, it's like a really incredible story that like the fundraising process really forces you to dig into your data and find. Incredible nuggets about the value that your product and platform offers. Now, the parts that I didn't like so much was partner meetings. You know, like you had built a relationship with one individual, but you learn over the course of time that their jobs are to champion for you in the background. The partner meetings are for the rest of the partnership to grill you on, first of all, like how legitimate is the story? Second of all, how legitimate is the founder, right? So they're going to intentionally pressure test you you and see how you show up under pressure. And so those, when I didn't really understand the full dynamics, I'm like, Ilya, why are you not stepping in here? Help me out. But just know that you're going in there and you're proving the worth of the company and the products and yourself because they're investing in you as CEO and your co-founders. And so you just got to show up to the best of your ability, but it's still hard.

It's hard. Getting so many rejections is hard. I think it's easy to say, well, we got 85% rejections. Easy to say that now. I think when you get like 20 rejections in a row followed by 5 additional rejections in a row, et cetera, et cetera, et cetera, it's not easy. Can you take us back to like that moment where you were getting a bunch of rejections for any of your phases and what that was like?

Yeah, I think that the, um, when we were earliest stage, when it was 3 co-founders doing it, you know, we all live in the same apartment. So like It would be real time that we would share with one another, like, hey, we got this email, we got passed. And honestly, you build a little bit when you're— the default is no, you build a little bit of a thick skin to it. I think that the first few are hard. You start to get a little bit desperate in the end, you know, and so the nos hit harder. But in the middle, you're kind of like, are we doing everything that we can to improve the product and the story? And if we are doing doing that, then you're okay with the no because you're learning and you're improving. Like, I think that that's a really important resilience mindset to adopt in the earliest days of building a company is because you will get more nos than yeses by like a wide, wide margin. So you just got to get mentally comfortable with that. And then as time goes on, you think that like, oh, we're making progress, we're crushing it, we got this many users. How could they say no? And so you build an ego, right? And that's— an ego serves you only as much as it's like, well, I have to puff up my chest a little bit going into these partner meetings, but it doesn't serve you in practice in the background when you're like receiving the no. And it's like, how quickly can you move on and move forward? And I do think that one really important but subtle thing is how confident are you truly in your product and company, right? Because it's way, way, way more important to find the right partner who deeply believes in you. Then I felt like it was harder because when we finally cracked the story for our Series A based off of feedback from Ilya and other investors about what are we looking for, and we could have shown the inter and intracompany virality and how Loom is spreading, and it's like, whoa, this story is incredibly compelling. So all of a sudden we have you get 4 term sheets and you're like, well, I have to decide between the 4 of who's the best and right partner. To me, take the nos as being like, well, it's actually a door that's opening to the right partner, the real right partner. And so, if you can adopt and flip that mindset a little bit, I think over the course of time that you'll be okay.

It's resilience. I love that.

Yeah.

It's resilience. And by the way, everybody, founders need that, but guess what? Everybody in their career, if you want to do something interesting, if you want to go for something, if you want to try something which is hard, then you need to build that resilience because it's not always going to work. In fact, what I always tell everybody is like, go out and get 10 nos because if you keep getting yeses, you are not pushing yourself high enough.

Somebody just tweeted this the other day and I was like, absolutely, this is right. It's like, you got to send like a cold email a day, right? Somebody you don't know. I love it. Like, and to me, that's what I'm gonna be doing with new feature sets coming out with like CEOs on our platform that I haven't talked with before. It's like, send a cold email because one, keeps you humble. And two is like, it's a, it's a, um, practice in like resilience. And so you never get out of the stage of receiving nos or rejections ever, ever, ever. So you may as well get good at it.

I love it. I, that's so powerful. I'm gonna do that myself as a practice. I'm gonna do that just because you told me to. I love it. It's so good. You know, you're talking about mindset really. And as you built, you know, the 3 of you co-founders hired a bunch of people. Do you have like, I, the last I saw you had like 185 employees. How many employees do you have now?

Yeah, we're at about 175.

175. So you've talked about team mindset. And so the 3 co-founders certainly had a founder's mindset, but what do you mean by mindset mindset and how important that is in terms of the success in building your company.

So this, again, like a macro theme of this podcast, is like you really respect it and appreciate it looking back. But, you know, I— we got early advice from an investor, which is— and they, they had built their own successful company and, uh, was a full-time investor at that point. They're like, don't undervalue being intentional a lot about the culture from the early days. And we were only 7 people when we did our first offsite in Mexico. And we actually spent an entire day codifying our first cultural values as an organization. And we had one individual who was like, "We're 7 people, why do we need this? We know how we each other work." And to be clear, I was also a little bit in that camp too. But I was like, 'Hey, somebody that I really respect told me that we should do this, right? So like, we're gonna do it.' And we ended up coming up with 6 values. We have 5 today. And while like the wording changed for the 5, are actually like the essence of them are still the same. So to me, when I think about team and company mindset, codifying your values early, like forcing yourself to look in the mirror because the other thing that the investor told us is as much as you probably want to think about like a meritocracy, especially in the earliest days, you will realize over the course of time that as founders, you are the ones that are at the business for the long haul, right? Like most everybody else, even if they're there for 6, 7, 8 years, you all will be there for 10, 15, 20 years. So you have to understand that values are more reflection of yourselves. As founders than anybody else. And so you actually have to look in the mirror and say, what are the things that I care about? What are the things that we want to imbue with the rest of the organization? And when you go through this a couple different turns, because like I said, we iterate on them, that you actually realize that there's just kind of core tenets to successful companies that if you go out and you study Amazon's leadership principles or Stripe's cultural values or insert any company that you really respect their culture and company from the outside, there's a lot of overlap between them. And so I do think that there's a corollary between successful founders, what they believe in, what their personal values are, how you translate those into team culture values, and how you own them over the course of time. And so for Loom, it's an optimistic owner who acts with velocity, keeping it real and human. And so there's like 5 words within their ownership. Optimism, velocity, real, and human.

Mm-hmm. And do you— first of all, I love how you said, like, there were 7 people and we did a whole day on values and, you know, sort of building culture. And even you were like, I can't believe we're doing this, right? It feels like we're playing Startup or something. But I appreciate that you took that advice from somebody who'd done this before and took it seriously because I guess I'm going to ask you, what kind of business impact has it had that you have those values codified, and what kinds of tough decisions have you made as a result of having those values codified?

So I think that that's exactly right, which is like values are good when times are good, but they're imperative when things are hard. So for us, really, the values are most important when you do have to make hard decisions, as you were alluding to. And I think that, like most companies over the last 15 months, they've had to make a lot of hard decisions in terms of, uh, how are you thinking about corporate efficiency? How do you think about the long term of the business? Um, do you believe, based off your run rate, that you'll be able to raise additional capital, um, within the time frame time that's needed because you should never go under 12 months of burn. And if not, then you have to make hard decisions and hard changes. And for us, that was when I actually, within the executive team, we really leaned on the values of real and human in terms of what is the reality of the situation. Look at the financial model. It does not make sense. But with the changes that we're making, We want to be human about them as best as we possibly can be. So what does that mean in terms of how we run the operations behind a reduction in force?

Right?

Like, how do you make it as compassionate as you possibly can? And that was just like a rallying cry for us is like, we, we have to keep it real with ourselves and the rest of Lumates, but we can do it with human at the core. And then on the other side, it's like, okay, yes, this is an absolute absolute shock to the entire company. A lot of us are going through a macroeconomic downturn for the first time in our careers. So how do you process this, even at the executive level? And there is— we have to own the decisions that we made as executives, which is the ownership side of it. But we also have to be optimistic that this is not— this is so far from the end. We have a job and a duty and a mission to show up for our customers in a certain way. And we need to obviously give Lumates time to process generally, but we also need to be the optimists who are saying, okay, let's move forward. We have a job to do. And so that's where, to me, it really was our values were showing up more often in our executive communication, especially to each other as we were navigating and helping navigate the company through the reduction in force that we did in May of last year.

Yeah. Yeah. And that's such a hard thing for everyone to do. How did you— I guess I would love to know when you had to then galvanize the team, because that's what happens. You have to unfortunately part ways with people through no fault of— it's not performance. It's not their fault, right? And yet you have to do it for the good of the company. So coming to terms with that is very challenging. But then how do you narrate and what advice do you have do you have for founders going through this literally right now? What advice do you have for founders and how to articulate the difficulty but also specifically articulate the optimism?

I think that you have to kind of like break them apart from a time perspective, right? Like you can't immediately shift into optimism within the same talk track. That you're giving in terms of the changes that you're making, the reduction in force that you're making. And so the way we thought about it was we need to take ownership at the very top. Like, these were decisions I made as CEO to hire the people that we hired, and I fucked up straight up. This is my fault. And from there, it's like, here's the reality of the situation. Here's the burn rate that we have. I think transparency is is like so, so, so important, especially in these scenarios. So here's essentially the most important metrics within the model. Here's our burn rate. Here's the runway that we have if we didn't make changes. Here's what it is when we did. And so this was a necessary adjustment that we needed to make. From there, when you do that, like you just let it land and you give time for individuals to talk to their managers afterwards. And what we had done was, we had let leadership know a week in advance. We let managers know 2 to 3 days in advance. So that way you can actually have conversations within those reporting structures to make sure that they're ready to own it at the individual employee level. So when that actually rolled out to the company, the managers could have conversations with their reports. And I think that in terms of giving people time to process played out at the, like, when delivered it to the entire company, we did it on a Wednesday, which was basically like people had Thursday to talk to their managers. And then Friday was, okay, are you starting to do a little bit of work? But if you wanted to take Friday off, all good. We totally get it. But Monday, after everybody's had a weekend to process, is when it's our job to start moving towards optimism. And you go back to— hopefully you've hired as many missionaries as possible. And the thing about the financial model, it doesn't change the mission at all. You have to continue to focus on the customer as much as possible. And if you do that, then I think that you can move towards optimism in terms of, here's the adjusted strategy going forward. We obviously have less resources. We can't do as much as we've been doing. So here's a strategy in terms of pulling back into the core. And that was one of the other core lessons that we learned through all of this is that we just went too wide, too fast in terms of all the things that we were trying to do. And by having a reduction in force and having less resources, then you have to ask yourself, what are the most important things? So then the optimism is not just focused on the mission and customer, but the specificity around how you're focused on the core value proposition and what, what adjustments you're making from an execution perspective. And that takes time to be clear. People don't hear that. Part of our jobs as executives is to be chief reminding officers. And so you just have to be ready to be like, not everybody's going to hear it on the front end. And so you have to have a steady drumbeat of that optimism and changes that you've made to move folks forward.

Yeah, I think chief reminding officers is so powerful and so very true. I'm curious. Like, was that hard for you to learn that you realized, like, I need to be the chief reminding officer?

Absolutely. I mean, I think that that's why I say it all the time, is like a self-reminder as much as anything else. Yeah, I think that that is one of the things that when you start to like build and grow the company, it becomes more and more of your job over the course of time, right? Because there's more disparate teams, there's more layers in terms of a messaging getting through, there's less touchpoints with everybody in terms of like individuals. When you're all in the same office, it's easy to like talk about the same things, everybody being on the same page. But as the company grows, you're going to have to say the same thing a lot of times over and over again in many different conversations, and you'll start to bore yourself. I mean, a funny example of this was that we're raising our B+. During the beginning of the pandemic, my wife got to see what the fundraising process was like for the first time when I was pitching a bunch of different investors. And when we finally signed a term sheet and she knew the pressure was off, she was like, okay, let me see if I can do the Loom pitch at this point. And so she just parroted it back because I was just saying the same thing over and over and over again. And it was pretty good. It was just close enough to be hilarious. And so that to me is like the best representation that I have about what becoming a CEO over the course of time is, which is like, get comfortable with saying the same thing over and over again because people need to hear that from you, right? Like consistent narrative in terms of what's valuable, why.

Totally. Consistency being everything. And I love that story. You should have hired your wife to then give the pitch. You know, one thing that we connected over when we first talked, I mean, it just, when you're talking about sort of like being the reminder and repeating yourself and having to like actually have a process around that. But one thing you and I connected over was meditation. I know you've had a very long-term meditation practice and I know it's been a big part of your life. How did you get into meditation and what is it like now Now, and specifically, how has it impacted, would you say, your leadership style?

This is one just incredibly fortunate skill set that I ended up picking up as a result of— I had a design agency when I was in college, and it was with my childhood friends. And Adam was always a little bit different, you could say, even growing up. He, when we moved out to California to run this design agency, he started going to ashrams in order to like go to these meditation classes. And he said, you should really start doing this. Like, I think, I think that you'd like it. And so I started going along with him. And to me, I think that meditation is one of those things that it's hard up front. Like it's, it's not like a super intuitive thing to do. And at that time, Headspace and Calm had just come out. You know, they were like brand, brand new products in 2012, 2013. But going to an actual physical location with my co-founder at the time in order to get through that initial phase, to me, got me to the breakthrough point of I actually started feeling it in myself where I would notice it in actually like day-to-day behaviors. So the way I think about the core value of meditation, other than just kind of like calming yourself down, I think is what a lot of people go into it with. To me, it was actually, am I making better decisions for myself overall? And do I spend less mental energy on the anxiety that I have so that way I don't have decision fatigue by the end of the day? Because that's like, you know, your brain, actually runs out of decision-making power. That's part of what happens and why you need sleep. And so to me, I actually felt like I had more longevity to make good decisions throughout the day. And then that compounds over the course of time. So when I started seeing and feeling that, I was candidly addicted to it. There was no really going back because I hadn't experienced anything that was like, first of all, when you do get to a breakthrough point, you're at a low point with meditation and you sit down for 15 minutes and then you stand up and you like immediately feel better. I mean, that's incredible. But the mid to long-term effects of like compounding better decisions versus like bad decisions is where it's like, I could never go back to not having a meditation practice.

Yeah. Gosh, I love the way you described that. Has it also made you less reactive, would you say?

Yes. One thing that, I don't know what else to attribute it to, but I got 3 siblings, I'm a middle child, and so there's an element of being a middle child that maybe you're a mediator, and that was certainly the case 'cause I had 3 sisters and I was the only boy, and so they were more kind of like fighting amongst themselves and I would have to negotiate with them to get everybody calmed down a little bit. But so like, I think I've kind of like grown to be less reactionary as a result of my meditation practice. But I think that I always kind of had a lower reactivity than the average population as a result of that. And then from there, you do have to have that as CEO as well. Like, I think that what I was talking about with resilience and not reacting emotionally, things only kind of get harder over the course of time as the company grows and scales. Things feel, they always feel big, but consequentialness of certain decisions that you make or the level of severity of issues that come across your plate, they only get bigger and bigger and you just can't be reactionary. You always have to be the calm force in the room. Now to be clear, you have to know when it's appropriate when it's appropriate to use stern language and when to say like, hey, we need to get our butts in gear. But the default mode is to be non-reactive, and meditation absolutely helps with that.

Yeah. You know, I love that you just said that. I think it's so important, like, to be able to choose a response rather than have a reaction. And sometimes this response you need to choose is, hey, I need this from you, or hey, that's unacceptable. Like, do you think about that consciously? Like, when should I push and when should I— kind of comfort or how do you kind of build that balance?

Yeah, I think that when you talked about building that balance, I've worked with the same executive coach for 4 years. His name is Khaled Halim. He's amazing. In our second session, he called out the fact that your greatest strength is usually your greatest weakness. Your greatest strength is how deeply empathetic you are, how that shows up in listening to customers, what they potentially need, and wanting to serve them. But also being empathetic as CEO, it will end up being your greatest weakness unless you hedge against that from you can't make everybody feel comfortable all the time. And you have to deliver tough feedback. You have to make tough decisions. And this is going to be one of your hero journeys over the course of your CEO arc is learning how to give tough feedback feedback when required, he's dead on, like 100%. And so when you ask about intentionality of when to use this, it's like, yes, because it actually takes a lot from me in order to overcome that hump to like give people tough feedback. So I have to push myself to do it more often. And the intentionality is not necessarily like leveraging at certain times, it's just like doing it.

Mm-hmm. Right. Well, like you said earlier that, you know, you sort of shy away from the things that you aren't good at or that make you uncomfortable. So like, how did you learn to get more comfortable or how did you expand your repertoire, your toolkit around saying the hard things?

You know, I think that this is similar to like the at-bats things that I was saying with fundraising, which is like you just, you, need to see that giving tough feedback actually is okay. People are fine. They actually, a lot of times, appreciate it. And so you just need to do it more often, and you'll see that everything will be okay. I think that the other side of it is there is a good framework from Netflix, which is the 4A framework. And I don't know all the A's by heart, but I do know that the framework is really powerful in terms of one, how do you think about setting up the feedback that you wanna give to the individual? And so that's the first two A's. And then the other two A's is for the person giving feedback, it's supposed to make them feel okay about it because when you give feedback, it's actually on the other individual to decide if they wanna take it or not. Is it valid feedback? And so if you've kind of like reduced the anxiety around, you know, somebody is going to hear this feedback and they're either going to take it or leave it. Like, that's really empowering to them and it should be empowering to you that you're just going to express how you feel in terms of what needs to change and why. And so I think that to me, the combination of those two things of repetitions and that framework are the two that I think has helped get me over the hump.

That is so powerful. I love that you said that. And the point about it's like there's two people here, right? There's me giving the feedback and I'm expressing my point of view and it's important. And then there's the person who's got to deal with it, as in like decide what to do with it. And I think sometimes the notion of people pleasing has to do also with like somehow taking care of that person, like that person doesn't have any agency themselves. So when you expect them to take care of themselves and them to deal with what was just said, it's like you're respecting them enough to give them that agency.

Exactly. And one of the fun framings— Anique is our COO. She's been at Loom for almost 3 years. And she's like, feedback is a way of being somebody's biggest cheerleader and fan. So if you can actually tell yourself that that is actually true, is you care, so you give feedback, and you are being their biggest fan as a result of it. That's when you would force yourself. You're like, I have an imperative as a manager to be their biggest fan and to help them grow. And you do that through feedback.

Yeah, it's so true. What I always tell my clients is the framing is, I'm wasting my breath telling you this thing because I believe in you, right? Otherwise, I wouldn't waste my breath. I would just fire you.

Yeah, exactly.

Yeah, I think that's great.

How else—

You know, Joe, I can tell by what we're talking about, you've grown so much, you know, as the CEO, as a leader in the past, like, 5 years. Can you articulate other specific ways that you have grown as a leader, as a human being that have helped you as the company has grown?

Yeah, so I, I touched on a few of them, which I was just talking to Khalid about this earlier today, which is going through the number of years that we've been building Loom for, you do end up learning your hardest lessons through the hardest windows of time. And so I think that to me, I've come to appreciate the hard times. I think when I was an early-stage founder, when everything felt hard perpetually, it's like, when is this going to let up? But that is when you have the most growth, is when times are hard. Hard. And so I've actually started to be friends with hard times, is what you could say. And I think that that's really important. I think another part of— time doesn't stop, like your personal life doesn't stop as you're building a company and a business. And I think that one of the things that I've learned is how important taking care of yourself is. I've actually really, really started to prioritize emphasize that. A lot of folks talk about how important sleep is. If I was wearing a Whoop band back in 2017 or 2018, the average number of hours of sleep per night would probably be like 4.5 or 5 hours. But how many suboptimal decisions did I make as a result of that? And so I think taking care of yourself is unbelievably important. And it really is like it starts with sleep because It's free. It's free to get better quality sleep. It really is. And so, the other part of that, and I think why I've actually focused on it more in terms of taking care of myself is you can white-knuckle it for a while when you're younger and you have more energy, when you have less responsibilities outside of work. But I had a daughter 18 months ago, and so that really forced me to say, How am I prioritizing my time? How am I not just showing up for the company day to day, but how am I showing up for my family? And you can't show up for both of them in the same quality level because you start working right when you wake up and then it's maybe like 6:00 PM that I try and sit down and have dinner with my wife and daughter every single night. And if you're there and you're showing up exhausted, which to be clear, like, nobody's perfect. I absolutely do that someday. Days, but I don't want that to be the norm. And so I need to start taking care of myself. I need to work out. I need to have my meditation practice and quality sleep are like the 3 things that I really focus on. And if I do that, I'm actually a far better CEO than if I don't. Yeah.

Is there more you wanted to say? Because I think that that's really powerful. The notion of like taking care of yourself is a very powerful It's like a moment that you grew, like you used to get 4 hours of sleep a night and now you're recognizing the self-care tendencies are so important as a foundation of your role as CEO. Are there other ways that you think about that you've kind of grown as a CEO, as a human, as a leader?

I think that there's, as you have more time with a company, you also understand where your strengths are and weaknesses are in more nuanced ways. You understand the things that you're actually, like, you may be good at, but you're okay with passing the Legos. And there's things that you're good at that you're not okay passing the Legos. And sometimes I think that that's really important to understand about yourself because as CEO, as a founder, you actually have a lot more autonomy autonomy than you think. I think for me, I felt like I was riding on a lot of waves of feedback and advice to kind of create a mosaic of a company that was it representative of me, was it representative of the company that I wanted to build. And as you actually build a company over a longer course of time, you actually start replacing some of those pieces of feedback that maybe weren't more directly aligned with who you are. And who you are as CEO and what you feel like if you want to do this for another 10 years, what are the sorts of things that you need to swap out from a roles and responsibilities perspective? And how do you do that in a way that feels not just optimal for you as an individual, but how do you do that for the company as well? And so I think that that's where, to me, that is how I've really started optimizing company over the last couple of years is what you could say is like, how do you mix and match roles and responsibilities?

Like, what's an example? A few examples.

So one is that I do really love product, as I mentioned. And when Aneeq, who's our COO, she was our VP of product. And she hired a design leader underneath her. And I was like, I want you to feel fully autonomous with your relationship with Christina. But by having a design agency before I started Loom and I'm not adept with Figma, but back in the day, I was pretty good with the Adobe Creative Suite. And so I built an intuition and an understanding of user experience that I felt like was a real value add for Loom overall. But I felt like I had grown a real distance to the design of our product where I wasn't part of the design crits. I wasn't part of a biweekly sort of meeting that would help me get into the early stages of design because a lot of times I would only see it once it was in product and I'd record a Loom and I'd send it back to the team and they'd be like, we just got done with this. And so to me, an example of that was I asked, Anik and Christina, I was like, hey, can we set up bi-weeklies? Like, I don't need to give feedback directly to the team. You can translate it, but I want to like Notion document of all the Figma file links and I want to be able to go through it and we spend an hour and I give you feedback, you know? And so we brought that back and it's one of my favorite meetings that I have. And to me, those are the sorts of things that you learn over the course of time that you're like, oh, I feel distant to that and it doesn't feel feel good.

Right, because everyone tells you you've got to let your Legos go and you've got to delegate and you've got to trust the team and all that stuff, but you're like, this is not working for me.

Yeah, there's this really interesting concept from Matt Mochary who has like The Great CEO Within, and he has a framework called the energy audit. And it means like basically as you go through a week, what are the things that give you energy? What are the things that take energy? What things are neutral? And then what are the things that you feel like you're missing? And if you just go through that framework, you'll start to find the gaps in terms of how do you energy optimize? Because energy is the atomic level of what I was talking about, showing up for work, showing up for family. And so you do really need to be intentional with optimizing your energy over the course of time.

Yeah, totally. You know, Joe, we have got to talk about async leadership. We've got to, right? So Loom is an async tool. It's so, so useful. But I just want to say I have seen async bloopers in my time. Like I saw a Loom that a CEO sent his, his, one of his people. And it was like, he was like free associating on his computer real time. And I was like, oh dear, no, this is not the way to do it. So I'm just curious, first of all, what async bloopers have you seen? And what are some best practices when it comes to async Looms?

Leadership. So I actually think that to me, one of the bloopers is thinking that async is the end-all be-all. I think it's a tool in the toolbox. I think for optimal communication and collaboration, you kind of have to understand what is the core value of synchronous time versus asynchronous time. And I think when you lean too heavily on asynchronous, there's downsides to it. And so I actually, one of the frameworks that we talk about at Loom, and like part of the core value proposition of our offering is that it helps meeting reduction. And so we're not saying meeting replacement, although it does replace some meetings, but it's meeting reduction. So a 45-minute meeting can be 30 minutes if you sent out a 10-minute Loom in advance, walking through the deck. And what you should be optimizing your synchronous time for is bursty communication. And what that translates to, the visual is like, if you have a ball, right, and like that represents who's talking, you should optimize for the number of passes that happen in a meeting. And that is bursty communication because that means you're rapid collaborating on something. If somebody is standing up and talking for 10 or 15 minutes at a time, that should have been asynchronous context that was given in advance. And so then on the flip side of the most important kind of async framework that I think about is, how would I move this work forward if everybody on my team was asleep right now? Am I able to effectively communicate something when everybody's asleep? If so, send asynchronous communication, give them the context And a lot of times, it's actually, yes, I can move the work forward without synchronous. What you should really use synchronous time for is bursty communication as much as possible. And so the default becomes asynchronous. But I would be remiss to say that asynchronous is the end-all be-all, because we're humans. We biologically evolved to talk to one another. It's the most efficient way that we've learned to collaborate on something. Those are the two frameworks I think about with synchronous versus asynchronous.

I love that so much. I especially love the notion of bursty communication. That's so good. That's so good. And also, right, like the idea of moving it forward so that you can give the context and that you then you leave the meeting. I mean, I love meetings. No one else loves meetings. I love meetings because they have that social interaction and the possibility of bursty communication as opposed to someone lecturing us in the middle of the room. So I love the way you frame that. It's so great.

Totally. And I think that the other thing that's interesting about, for Loom, asynchronous work has actually been a default as a result of the products that we're building and delivering. And so one of the things that I think some folks feel a challenge with in terms of that framework around moving work forward if everybody's asleep is like, man, how long would it take me to document this thing? And then for Loom, that was one of the core value propositions is it's super high-fidelity communication with minimal amount of work. And so you're minimizing back and forth on the other side of it, which is like when somebody views it, it's really hard to misunderstand a video. It can be easier to misunderstand a plain text message. And so for us, I think that we've always had this in our core where it's been like organic and natural as a result of the product that we built.

Yeah, I love it. Joe, just a few more questions. 2 questions. Tell us about any experiences you've had with imposter syndrome. So many founders and frankly, many highly successful people experience imposter syndrome or severe self-doubt. Have you ever experienced that?

I think to me over the course of time, like, imposter syndrome is kind of a default, right? It's atypical if you don't have imposter syndrome no matter what your role or function is. You know, when I I was working at MyLife, which was a company before Loom, and I was a product manager and I would get up in a meeting of like 25 or 30 people and be presenting a roadmap. I'm like, who am I to be saying this? You know, like what do I know? And I think that to me there's a couple things. One is the more successful the company is like over the course of time, like imposter imposter syndrome will never go away. I really, I think that that's okay, you know? And because what it does is it allows you to kind of like self-reflect and be like, okay, well, what value is it that I'm offering? You know, what is the unique perspective that I do have? And regularly asking yourself is actually really healthy. It's almost like standing in the mirror and doing like the self-esteem talks, but more specifically about like, who you are, what product you have, like what value that you're offering. And so that's one thing. I think that the second thing is when you have more repetitions over the course of time, like if we were doing this podcast when we were like 9 or 12 months in, I would've been so nervous for like weeks and weeks and weeks leading up to this. But what you do is like you get comfortable with certain things that you feel like maybe you'd have imposter syndrome for. Like, I actually— it probably resonates with quite a few folks listening to this, but, you know, getting up on stage and presenting is not a default for me. I actually have whatever, like, physiological responses that, like, my palms sweat, my hands shake, my voice shakes a little bit. But over the course of time, I've kind of, like, built up my comfort with it, you know. And, and, like, you You just have to familiarize yourself. And so to me, the imposter syndrome part about like, who am I to be like saying these sorts of things and sharing my opinion? It'll never go away, get comfortable with it. But over the course of time, you will get more and more comfortable with parts of your role that you feel like, oh my gosh, I could never do this. And then you'll wake up one day and you'll be like, oh, I'm presenting at a conference. That's pretty cool.

Totally. You're like, oh, I'm on stage in 5 minutes? Oh, okay.

Right?

Expanded your comfort zone. You've got to kind of get out of your comfort zone in order to expand what's possible for you in a comfortable way. That's so well said. Joe, what do you wish you had known earlier on your journey?

I wish that I had known that Loom was going to be successful. No, I'm just kidding. Yeah, we're not. First of all, we're not successful yet, and also we probably wouldn't have worked as hard.

Right, you are successful, but it's easy to say that now. Yeah.

Yeah. I do think that one of the core things that I've been reflecting on over the last year and a half is Airbnb had this philosophy about having a culture of culture interview that was run by one of the founders until they were like 2,000 people or something. Like they were like meaningfully slowing down their hiring pipeline. And to me, I think we went through this window of time in 2020 and 2021. It was really hard to hire and you end up kind of like lowering your bar a little bit and bringing folks in. And what I'd say is like, you gotta just be patient. So the, tropes feedback is like hire slow and fire fast. And I don't like the phrasing of that exactly because I actually think it's more about what I've learned over the course of time is it's more about like a company-individual fit. And the thing is when you let somebody go, it's like they'll find another better fit. You know, like this, this isn't the end of their career, but you should never lower the bar on the front end because firing is always hard. You never get over that. I still get very nervous going into conversations where I have to let someone go. And that's just the reality of the situation. But to me, I wish that looking back, that was the one thing I wish that we had not done when hiring was really hard was trying to put butts in seats because that's never the right answer ever.

Yeah, yeah. Hard one wisdom. I totally hear you. And last question, Joe, what advice do you have for other founders as they embark on their journey to grow into leaders?

I think it's a lot of the things that we touched on, but I'll try and do it in like brief bullets. One is I hope you have a co-founder that like you deeply respect and you love in a way that like you can like love your co-founder because it's going to be hard along the way. You're going to go through a lot of things together and the co-founder relationship is unbelievably important. The second thing is listen to customers. That like never, ever, ever goes away, right? Like deeply respect customers, try and translate them to the best of your ability, but never stop listening to them about what value that they want from your product and platform. Because I think we lost that a little bit along the way in 2021 when we were like expanding into these surface areas that even just call it basic research would have told us that this was not going to be the best use of everybody's time and resources. So listen to your customers deeply. And in the early days, it's probably going to mean pivots. Later days, it means better iteration and better servicing of your customers. And then the other thing is just get comfortable with discomfort because it never gets comfortable. As a founder and CEO. It never ever does. And so the more that you can reframe that in your head to the best of your ability, which is that pain is growth and it's usually the fastest form of growth, that you'll start to befriend pain and discomfort in a way that is necessary if you're gonna do this for the long haul.

So well said. So wise, Joe. So wise. I love it. Gosh, this is such a valuable discussion. Discussion. I just wanna know, it's been so great to talk to you and I really appreciate you bringing the real talk to the table and I just know people are gonna really benefit from this. So thank you so much for joining me today, Joe. It was really great to spend time.

Thank you so much for having me on, Alisa Cohn.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, Drop me a line through my website, alisacohn.com.