Season 4, Ep. 40 – Founder to Founder: with Kate O’Neil, Co-founder & CEO, Teaming

(THE FRONTIER THEME PLAYS)

Bill, via previous recording (00:04):

Welcome to another Founder to Founder interview from Gun.io, your source for hiring world-class tech talent. Today, Gun.io’s CEO and co-founder, Teja Yenamandra, sits down with co-founder and CEO, Kate O’Neil, of Teaming.com, a site that helps users automate manager tasks and adapt their leadership styles to any situation. Okay. Here’s Teja. (THE FRONTIER THEME ENDS)

Teja (00:35):

So I think the first time you were on the pod, you were co-founder and not yet (Kate: Yes.) CEO of the company. That’s true? Cool!

Kate (00:46):

That’s true. Yeah.

Teja (00:48):

Okay. How did that sort of transition happen, and I think this is your first sort of role as CEO?

Kate (00:57):

Oh, yeah <laugh>.

Teja (00:58):

Like, what are your thoughts on the role, and how is it different from before versus co-founder? Like, just, yeah. How are you feeling?

Kate (01:08):

Well, I’m less than a year into the CEO role, so this is newbie <laugh> things that I’ve noticed. Well, how it transpired, you know, we are four co-founders. We all know each other from our previous company, and our CEO, Teamings former CEO, was our CEO at our last company, and that was a, you know, much bigger venture-backed, you know…it sold and did well and all that, and you know, he was a, I would say a big tech company CEO, or at least bigger than than we were now, than we are now, and when we, you know, when we started Teaming, it was like, wow, only three of us, the three of the four of us hadn’t done, you know, startup as the first co-founder, right?

Kate (02:07):

My other co-founder, Steven, he was co-founder of our last company, so he’s gone from zero to one, but none of us, none of the rest of us had, and so it has just been such a learning for us, and thankfully we’ve had Steven, you know, kind of guide us through that zero to one <laugh> process, but our former CEO was part-time. So two of us were full-time, two of us were part-time, and it got to the point where, you know, he was also CEO of another company. He is CEO of another company, and when we went to go out and raise, you know, our institutional round, which we just signed a term sheet this week (Teja: Congrats.) which is exciting. Thanks. (Teja: Yeah.) You know, the advice was like, they don’t wanna give a part-time CEO money <laugh>, or institutions don’t wanna give a part-time CEO money.

Kate (03:02):

So what’s the, you know, what makes sense for you all, and I think between, Steven and I are full-time, so between the two of us, it was like, you know, Steven’s running the tech side, I’m running the go-to-market side, and you know, we’re both incredibly close to customers, but I think from telling the Teaming story, you know, it just was like, natural that it would be me, and yeah. I think getting to this point <sigh>, you know, it’s such a learning experience. I mean, I’m really curious to get your thoughts on this. It’s the most humbling experience. You realize how little you actually know <laugh>. It’s a very, yeah, very, very humbling experience, and so I’ve enjoyed it, but at some point, like, you also realize, like, you get to deal with all the crappy stuff, like all the problems.

Kate (04:07):

You want that, because you wanna clear the path for everyone else to really focus on the things that need to get done, and that’s something I didn’t expect. I don’t know. I just didn’t expect that, I guess, and it wasn’t my, like, the CEOs I’ve had before have done such an amazing job of that, I think, that I didn’t realize that that’s what they were doing, right? Dealing with a lot of problems (Teja: <Laugh>.) <laugh>. So yeah. That’s probably the new…or the first, I think I’m 10 months in now, so first 10 months would be the learnings. How about you? I mean, you’re well into this path, but you’re relatively like, you guys were bootstrapped, and then you raised not that long ago, right? So this job must have changed a lot for you too.

Teja (04:59):

Yeah, totally. Yeah, I mean, it’s funny. My friends, like, family, and like, partner would say, it’s not been a humbling experience for me. (Kate: <Laugh>.) They often all make fun of me. They’re like, “Don’t ‘CEO’ my life,” and I’m like, “Okay, sorry,” <laugh>. (Kate: <Laugh>.) So <inaudible> in the opposite way for me, because I’m like, “Cool, you’re coming with a problem. Here’s what you should do. I encourage you to do this,” they’re like, “Don’t talk to me like that.” I’m like, “Okay, sorry. My bad.” (Kate: Yeah.) That’s like, you’re just in that mode like, 10 hours a day, so that’s how you tend to operate. (Kate: Yeah.) Yeah, I don’t know. I mean, I think like, when we were bootstrapped, you know, I think maybe the biggest difference from today is like, I really only had like, one reality to manage, and the reality was like, it was very aligned.

Teja (05:50):

Like, this is what we wanted to do with the company. There were no other stakeholders like, really on the cap table that like, you know, needed to achieve a return, and so you could just be honest with like, the team, and be like, “Hey, okay, I dunno what we’re gonna do, but like, we’re gonna try to grow as fast as we can and try to spend as little money as possible. Like, that’s what we’re gonna do,” and when you sort of have like, an institutional partner, at least this is what I’ve ran into, it’s like, you have to be really, like, “I don’t know,” is not an acceptable answer, really. You just have to, (Kate: Yeah.) like you have to make a bet, and you have to be like, “We are raising this money to do ‘Y,’” and then that’s it, and then simultaneously, you know in the back of your head that like, the first three attempts at doing “Y” with, you know, “X” resources are not gonna work out, and you have to give patience and kindness, but also maintain standards. So that’s been like, an interesting…that’s just been interesting to develop into, but for me, I like to like, optimize for like, fun and adventure personally, and so like, having like an institutional partner like, allows you just to take bigger bets and like, have more fun like, at work, at least for me. (Kate: Yeah.) So, yeah. So it’s been good. I mean, are you part of any like, peer groups, like CEO groups, or anything like that? Have you explored joining any of those things?

Kate (07:20):

There’s a group in town, actually. You should be part of it. (Teja: <Laugh>. Okay.) It’s a <laugh>, it’s just a group of, it’s like, tech CEOs that run product companies, which you know, is kind of unique, (Teja: Interesting.) I think. Yeah, and they’re mostly non-healthcare. So we get together once a month, I think. Yeah, once a month. Sometimes I can’t go, so it ends up being like, once every other month or whatever, just timing wise, but it’s just a casual, like, we meet at a restaurant or at someone’s office and talk through stuff. You know, everyone’s [in] a little bit different stages, so I think that is something like, I wish I had more at our stage…peer people <laugh>, but it’s really nice to meet in person. 

Kate (08:17):

Like, the digital groups that I’ve tried to like, get involved with, I just haven’t like, fully committed. I don’t know. It’s hard to find the time, ’cause it’s not as structured. It’s more async, (Teja: Yeah.) and that just lends itself to like, I don’t know if I feel like I can call this person to ask for advice, right? I need to Slack them and figure that out. Although, you know, one group…there’s basically two Slack groups I am part of. One’s a marketing one that I love, and, you know, I’m just part of, and then the other one is StartupNash. If you’re in that one, I’m not as, that’s probably the one that I’m just not as committed to or into, but I love it when I do engage. Are you in that?

Teja (09:01):

I think I’m in StartupNash. Yeah, I think so, and I’ll follow up with you separately to get a sense of the product CEO group. (Kate: Yeah.) That’s definitely like…like, I’m in a couple, and one of my challenges is like, one of the ones I’m in, they’re like, great people, but they have like, their businesses operate differently than ours, you know? (Kate: Yeah, yeah.) Like, they’re just…the profile of the business is a little bit different. (Kate: Yeah.) So you guys are all like, basically, I mean, how extensive is the diligence process with this fund? Like, do you get a sense of that yet, or it’s pretty easy?

Kate (09:44):

No, it was not easy <laugh>, I would say. Yeah, I mean, look, it’s been interesting. Like, we, you know, we started fundraising at the beginning of this year, and you know, in January and February, (Teja: Oh, wow.) If you look at the venture checks that were written, it was basically nothing. (Teja: Yep.) It was right before SVV failed, you know, and it was just like, the market was just tanking. So we kind of reevaluated, then we focused on growth. We, you know, put our own money in for, to survive this year, and thankfully, we did, and that was the right move, because we then had the like, proof points to show, right, that this is a good business to invest in. It’s, you know, there’s a huge opportunity here, and we’re also able to survive. Like <laugh>, there’s so many startups that failed this year, primarily because, not ’cause they’re bad businesses necessarily, but because they just couldn’t keep going. The market, you know, (Teja: Yeah.) money was expensive. So, yeah. What was your experience going through that process?

Teja (10:53):

So we raised last year, yeah, last year. We started raising around February, and we had like, been in touch, because we had been operating for a while. Like, we had been in touch with a couple of funds, And so the process to get the term sheets was like, quite straightforward (Kate: Nice.) and like, pretty easy actually, and I would say the difficulty for us was like, we had a set of offers that were like, really good economic terms, but, you know, this is just my worldview. It’s like, when you bring out like, an institutional partner, like, you are married, basically, you know like, (Kate: Yeah.) through the life of the company, and so the harder part for us was like, figuring out who like, just was like, aligned with like, our philosophical like, view on the world, and how we wanna build the company, and how we think about things, and who could like, compliment us and make us better. (Kate: Yeah.)

Teja (11:59):

So we found a fund that, I mean, they had done a really good job of staying in touch with us, and we just really liked their like, vibe and like, who the partner on our deal was gonna be, and who the partner on the board was gonna be. I was just like, I was very careful about signing somebody, you know, (Kate: Yeah.) like, partnering with somebody, and that’s probably on me for sure, but I would say a year into it, like, makes me wish I’d done it sooner, for sure. (Kate: Mmm, interesting.) You know, yeah. I don’t know if I would’ve been capable of like, being like, responsible enough and mature enough to like, handle like, the amount of resources that you get injected into the company, truly, but I think that, like, for me personally, just like, the added diligence, the thoughtfulness that happens like, when you have a proper board, (Kate: Mm <affirmative>.) you know, that stuff is just not stuff that we had before, and like, they’re actually helpful like, when it comes to like, budgeting and like, “Hey, here’s how we think about this role. Here’s what we’ve seen people pay at our portfolio companies.” “Cool, we need to hire this role.” Like, “Here’s how you gotta think about this role.” Like, “Here’s maybe what you can get them to manage,” and you’re like, “Cool. I don’t have to go and like, ask a bunch of people, get their opinion. I guy who’s actually economically invested in the outcome of the company. Like, here’s our worldview.” Like, so (Kate: Yeah. That’s huge.) That’s been really…

Kate (13:32):

It’s interesting. It was the exact opposite problem. So the (Teja: <Laugh>.) term sheet process was <laugh> was really hard for us. I think mostly, ’cause <inaudible>.

Teja (13:42):

 It’s a different time.

Kate (13:42):

It’s a different time.

Teja (13:43):

It’s a different time. 

Kate (13:45):

Also the company that we ended up working with is my old boss from a decade ago, (Teja: Got it) and so that was someone like, I know, right, and I think my co-founders now know well enough that our worldviews align really well, but that was like, that was an easy decision for me. He sold a company to a company that I worked for, and then he ended up being the head of product, and I reported to him a decade ago, and so I knew, you know, known entity. He’s been through this before. He’s raised money before. He sold companies before. He’s been in, you know, my seat. Like, this is, you know, we’re, yeah. Just…same page, you know, that was easy, but I do think that that’s such a big problem. That’s where it becomes expensive, right? If you don’t make that, is your worldview the same? Are your values the same? How do you make decisions if that isn’t aligned? Like, that’s the most expensive choice, (Teja: Yep.) or opportunistic choice, like, right? Like it’s the biggest lever, I think.

Teja (14:53):

Yep. No, totally, and like, you know, one of the, you know, it’s funny, like, one of the things that I think a lot of funds like, I mean, I don’t know, I’m sort of like, my experience with like, working with an institutional fund is like one, so I might be like, extrapolating a trend that doesn’t exist, but I feel like what makes our relationship work is that like, I have like, a deep amount of respect for who the person on our board is, and that’s because of just like, the way that like, they carry themselves, and like, the way that they help us, like, work through problems, and I think a lot of, and this is just my impression, but I think a lot of folks like, expect to be given that respect if you’re like, a venture investor, just because of the nature of their work, and because they’ve seen a lot of companies, but like, so much of like, your respect for somebody in a working co professional working capacity, is like, based on your relationship with them. It’s not based on their track record. (Kate: Exactly.) It’s like, maybe that gets you the first two meetings, but like, for them to have influence on your decision making, you need to like, actually be like, “This person’s awesome,” and like, “I wanna listen to them,” you know?

Kate (16:13):

Yeah. You’re so…I so, so jive with that, and I would say too, like, we talked to, you know, over a hundred funds, and I would say 85% of ’em on the first meeting. I was like, “No, I don’t really wanna work with you,” (Teja: <Laugh>.) for that reason. You know, I mean, I hate to say it, like, at some point it becomes like, well, do you want the company to exist or not, right? At some point, right? If you’re struggling to raise, thankfully we didn’t get to that point, but you’re right. Like, you expect, there’s this like, weird dynamic where it comes across as we’re the experts. We’re the ones with the cash, we’re the ones with the control. Like, we control your destiny, and that’s how it feels, and that that doesn’t feel good. That’s not (Teja: Yeah.) what I wanna sign up for. So, (Teja: Yeah.) yeah.

Teja (17:02):

That’s the opposite of why you start a company. Like <laugh>, (Kate: Yeah, yeah.) yeah.

Kate (17:08):

Yeah. Totally, totally. So you said you have like, people come to you with problems, and you “CEO” them a little. How do you get to that point? Like, I have fallen in love with the problems that I’ve solved in the past. Marketing problems. I love the problem that we’re solving for customers, I love, but like, you know, the accounting and legal problems and, you know like, stuff like that. I just, I don’t know. I haven’t discovered the enjoyment of solving those problems. So I’m curious how you do that.

Teja (17:46):

You know, this is like, easier said than done, and this only works for my psychology, so I can’t…it’s hard for me to like, provide advice on this, because every company’s different. Every CEO operates differently. It’s not about the problem to me. It’s more so like, who I get to work with to solve that thing, and so there are aspects of the business where like, I really love engaging with certain people on whatever like, is under their purview, and it’s like, a joy to be on a call with them or in a meeting and be like, “Alright, like, let’s work through this,” like, and it’s fun, right? So like, yeah, I mean, I don’t know. There are probably some CEOs who love like, doing accounting, but like, it’s kind of boring, but like, I love the dude who is like, running that aspect of the business for us, and so it’s like, I can tolerate like, going through like, “Here’s our BBAs. Here’s this, this, this,” and I’m like, “Okay, sounds good.” So I actually, yeah, I find…absent of any person, there are obviously things that I like, like focused areas of the business that I enjoy solving more than others, but for me, it’s more about like, you know, I’m just extroverted. Like, I like dealing with people, and I enjoy solving problems with people. So does that answer your question?

Kate (19:11):

I think that…it does, and it actually does speak to me. I think we’re, you know, we’re earlier stage than you, and so we don’t have someone to do that thing, so it’s sort of like, a divide and conquer, right? (Teja: Yeah.) There’s just so much stuff to get done, and we gotta close this round to be able to go hire the people that go do the, you know, that can be that, you know, that can have that engaging problem solving mindset with, and we’d have that as co-founders for sure. Yeah, talk about people who have totally different functional areas of expertise, but come together to solve problems. That gives me motivation, and energy, and all that, but at the times when it’s just like, we just gotta divide and conquer to get this done, that’s when I struggle, I think, you know, (Teja: No, same.) to love those problems <laugh>.

Teja (20:00):

No, no, same. I mean, like, practically, I know this about myself. It’s like, you know, sometimes I love working on like, a Saturday, because like, I know that it’s like, important to people like, that I unblock a certain thing that’s maybe the only time in my week that like, I have to be able to do it, but if it’s like, a rote thing that I just, like, I need to read a report. Like, this report’s really important to like, inform my worldview about like, something, I will procrastinate that to like, the next weekend, right, because it’s like, there’s no like, actual people dimension to it. I’m not talking about it to anybody necessarily. So I try to create hooks in my life, especially with work that like, have a dimension of social accountability and some social output to motivate myself to do it, and like, actually enjoy doing it. (Kate: Interesting.) I just know that about myself, yeah. Yeah. It’s hard for me to do anything that’s like, a fundamentally like, siloed, alone thing.

Kate (21:00):

Yeah. Same. Yeah, I find I do this habit, and my co-founders have called me out on it before <laugh>, where I’ll say, you know, it’ll be something that isn’t urgent, but is important, and I’ll say, “Great, I’ll have that to you back tomorrow. I’ll have that to you by tomorrow,” and we’ll get off the call, and my co-founder will say, “Why’d you put the ticker on it for tomorrow?” Like, you know <laugh>?

Teja (21:24):

<Laugh>. I do that.

Kate (21:27):

I care about doing it in the time that I say I’ll do it. So like, I have to put that ticker on, because I care for me to be that accountable person, and I care that someone else sees me as that accountable person. (Teja: Yeah.) Which, you know, maybe that’s bad, but I care <laugh>

Teja (21:46):

No, that’s powerful. So like, have you developed…like, it sounds like, you’ve just carried forward your habits previous to the role, basically into the role, and like, that’s why it’s working. Like, this is, like, even if the title’s new, fundamentally the way you operate is not really that new. Does the responsibility feel different or feel the same as before?

Kate (22:10):

On the habits piece, I would say I’m trying, how I managed habits before, but I feel like I had mastery of that in marketing. Like, this is the cadence, this is the, you know, scale. You know, this is the next decision we need to make like, and be able to do it fast. Like, I got to the point where I mastered it, and I could do it fast on a day-to-day basis on a weekly, monthly, quarterly, yearly. Like, I knew the flow, if you will. With this, I do not know the flow. I feel like I’m getting <laugh>…like, I’m not controlling it. It’s controlling me, right, and that’s really hard. So I’m trying to get outta that for sure on the habit side. How it feels from a responsibility perspective, it does feel different.

Kate (22:57):

I think, you know, there’s just things that we, you know, as a founding team, you know, if there’s a struggle to decide something, now, sometimes it falls to me, right? Like, okay, you know, we are deadlocked on this. Kate decides <laugh>. You’re like, “Okay.” You know, it is just a little bit different. It’s rare. It’s incredibly rare. We’re such a fluid team in that way, where I don’t feel alone in that, but I feel a deeper sense of responsibility, I don’t know, that I did before, maybe. Not by much, but it’s like, it’s different. I also think the thing that’s most different is the way that people look at you from outside, right? 

Kate (23:51):

Like, they’re like, “Oh my gosh,” you know, “You’re CEO now,” and I’m like, “Okay, yeah,” but I mean, I own the same amount of the company mostly, right? <Laugh>. You know, like, the title changed, yes, but ultimately the responsibility of all this hasn’t necessarily, so I would say it feels a little bit different to me internally, but what I notice most is that it feels different to other people a lot, and I don’t fully understand that, I guess. I don’t know, maybe it’s just different. I don’t know <laugh>. (Teja: Yeah.) Do you feel that, (Teja: Totally.) or you’ve always been CEO, so you haven’t had to go through that transition.

Teja (24:30):

I mean, it gets more real, with every like, added level of commitment, you know, (Kate: Yeah.) measured in increments of employee or, in increments of revenue, or increments of capital. Like the, (Kate: Yeah.) well, the one thing I told like, one of my colleagues is like, the most interesting thing about today versus like, 18 months ago, is like, now you have people making commitments on your behalf to other people, and you have not met those like, I don’t know every customer, you know? (Kate: Yeah.) I don’t know every developer, and like, there was a time in which like, I did, and so that’s always like super interesting to think about. Like, you know, as the CEO, like, if something is poorly delivered in terms of experience, like, that’s ultimately on on us. (Kate: You, yeah.) Yeah, yeah, and so that’s been interesting to grapple with, and I just try not to think too hard about it, because I think you can drive yourself insane if you…

Kate (25:32):

Have you…yeah. It’s interesting. Maybe I have a different perception of CEOs as well. We have a vendor who we are their customer, and we had a really crappy experience multiple times, and it was not our fault <laugh>. It was, basically the essence of the situation is we got shut off out of nowhere to their software platform, and I was like, you know, “What the heck is going on?” You know, I emailed our sales rep and finally heard back like, “We’re so sorry. You know, we just made the mistake. We just shut you off for basically no reason.” We’re like, “Okay, great,” and then for the next two quarters, we were on quarterly billing, and the first quarter, they just didn’t send us a bill and then shut us off again, right?

Kate (26:36):

So I’m not thinking about paying it. I expect I’ll see a bill, and then I’ll pay it. They shut us off. Like, “Hey,” they’re like, “Well, we shut you off for nonpayment.” I’m like, “I never got a bill from you,” and they’re like, “Oh, yeah, okay. You’re right. We didn’t send you one.” I’m like, “Okay.” Like, what? Then the next time, they actually sent us the bill, but the link didn’t work to pay it. So I, you know, I lost it in my mind, right? I was late on it, because I couldn’t pay it, and then I didn’t like, stay on top of it, essentially. So they shut us off again! (Teja: Yeah.) I finally was like…they shut us off again, and they sent us a note saying that they were escalating this to their legal department, because we didn’t pay.

Kate (27:22):

I was like, “Are you kidding me?” Like, so I laid it all out, and I CC’d the CEO of this company. Like, this has been our experience, and we get this like, veiled threat of legal action, because we didn’t pay a bill that we couldn’t pay, you know, through this portal that you sent us. No response. I got no response from the CEO. I was like, “Wow.” They’re not, I mean, they’re much bigger than us, but they’re not a huge company, and I was like, that’s shitty. I am not gonna be that CEO. I am gonna respond to this. I’m gonna try and be proactive too, even if you don’t CC me, I wanna know about it, and I wanna reach out and say, “Hey, I’m so sorry you have this experience,” (Teja: Yeah.) ’cause that stuff’s gonna happen, you know? I dunno. (Teja: Yeah, yeah.) Have you had to deal with that yet, and what is your like, principle behind it?

Teja (28:16):

Yeah, I personally, like, I love dealing with the bad. (Kate: Yeah.) That’s, I think, where we get to earn our stripes. So, yeah. I like it. Like, many customer problems are escalated to me, and like, we’re in the people business, you know? Like, we’re hooking up developers and companies, and like, people are like, they’re not bits. They’re not like, consistently delivered, you know, all the time, and so, yeah, we deal with a lot of that stuff, and my psychology is like, well-suited to handle that stuff, and I share the same opinion as you. Like, ultimately, it’s meaningful if you care about customers and like, resolving an issue, and like, your team sees that. Like, so I think it’s really important. (Kate:Totally agree.) So you guys are raising your first round, the first institutional round. You guys have raised a round before or…?

Kate (29:08):

Friends and family, angels, us, was the before. So now, yeah, this is our first institutional round.

Teja (29:15):

Got it. Are you guys thinking about this like a seed round or like a Series A?

Kate (29:19):

Seed. Yeah, I would say it’s a seed still, but I don’t know. It’s like, what do you call it <laugh>? (Teja: Yeah.)  Even the institutional people are like, “I don’t know. Call it whatever you wanna call it,” <laugh>. I guess we’d call it “seed,” ’cause It’s from a seed fund, honestly. That’s why I think about it. The institution is a seed fund, so, you know, but they do make some big investments, so I don’t know. Are they a seed round <laugh>, or seed fund?

Teja (29:45):

Okay, cool. That makes sense, and so as you think about like, capital deployment, you know, wher are some areas that you guys are like, really excited about investing in over the next, you know, two years?

Kate (29:57):

I don’t know how much you know about us, but there was a point in time where we thought we were dead in the water. We basically built a performance management system, which is like…do you do annual reviews and that sort of thing? Or do you have like, systems to review performance for employees yet? I don’t know. You might not be big enough yet. I don’t know. Do you do that, or do you do it in like, Google Docs?

Teja (30:23):

Yeah. Yeah, we do it like, in a janky way. We need to be better about that for sure. You know.

Kate (30:28):

Yeah, so we had basically built that, and there’s companies that are like…Sam Altman’s brother runs a company that does that, to give you an idea of like, the scale <laugh>, you know <laugh>, who we’re up against, and so we thought, man, we’re just not gonna win here, but what we were able to do, and AI has helped us tremendously do this, and this is the forward vision of the company, is individual feedback and coaching for employees at every time they interact. So like, the first example of that, is you use Teaming in your one-on-one meetings with your direct reports, and we do all the things that a performance management system would do. We keep track of your goals, you can create agendas, you can take your take down notes, you can manage all your tasks, right? It’s a task manager. It’s like, you know, every operational tool you need to lead your team, but there’s nothing differentiated about that really, right? It exists. The future and what we’re…we launched this in August, and it’s just been a <rocket vocalizations>, you know, growth chart for us with this, which has been awesome, (Teja: That’s excellent.) yeah, is we join your one-on-one with…have you ever used like, Otter or Fireflies? The note takers? So we built one.

Teja (31:57):

Yeah. Fathom, anything like that.

Kate (31:58):

Fathom, yeah. We built one. So we do that for you. We take your notes for you, but we use the information we get from the meeting, right? How you’re communicating with your direct report, how the direct report is communicating with you, and we merge that with that employee’s performance, their DISC profile, like, their, you know, communication style, their, you know, engagement, right? We’re measuring their engagement about how they feel about working on this team for you as a manager, et cetera, et cetera, and we’re able to provide immediate feedback of like, “Hey, when you talked about, you know, hiring Gun.io for your devs, like, that was a really good conversation with that direct report, because you communicated in this way, which is how this employee prefers to hear, you know, feedback,” or something like that.

Kate (32:55):

“When you talked about Project Cup,” I don’t know, I’m looking at a cup, Project Cup, right, “there was some tension, because you know, you dove into the details with them, and they, you know, that can feel like micromanagement,” and then the converse side of that, right, is that the employee gets the same thing, “Hey, when you talk about, you know, hiring Gun, you know, you dove too far into the details, and your manager just wanted a high level status update on it,” and so it’s just helping people flex to each other’s style, but it’s immediate, it’s contextual, it’s timely so that you can use that, over time, to build those really great relationships with the people on your team. So people…(Teja: That’s sick.)

Kate (33:45):

Yeah. The result of it has been just truly awesome. People, you know, I think people like you who are extroverted, and they get that motivation from working with people, and Teaming has been really helpful for people like that, because they feel like it’s a tool to do that better, or to know those people even more, and then on the reverse side, right, the more introverted or maybe more just like, work-focused rather than people focused managers (Teja: <Laugh>.) <laugh>, you know, find that this is like, Teaming is like, a playbook for them, you know what I mean? It’s like, “I know how to connect…I know connecting with Teja is important, but I don’t really know how to do that, and so Teaming helps me to do what I know is important, but I don’t know how to do.” So it’s been, yeah, it’s been great.

Teja (34:44):

That’s awesome.

Kate (34:45):

You asked about deploying capital, that’s what we’re investing heavily in, right, is the data we need to do that, the AI training, the AI to be able to do that, it’s all that, and we’re hiring a salesperson. We gotta get on that <laugh>. Right now, it’s still me <laugh>.

Teja (35:04):

Yeah. That’s cool. I mean, well, I’m sure you’re killing it in sales. You’re probably the best performing salesperson, so that’s interesting, and I mean, honestly, like, the way that our company works, like, the feedback system like, mirrors this process. So I feel like, I mean, I will have somebody, we will take a look at Teaming (Kate: Yeah <laugh>!) and hopefully be a customer.

Kate (35:29):

Yeah, no pressure, (Teja: Yeah.) but like, you know, in terms of what we’re investing in, there’s so much opportunity to do even more of what we’re doing, right? We’re in like, the infancy stage of it.

Teja (35:40):

No, totally, and like, maybe like, when we like, scale to like, a hundred people or something like that, like, it becomes like, we need more systematic performance reviews, but like, now, you know, you’re meeting everybody every week, you know? (Kate: Yeah.) Like, everybody’s thinking every week on something, and so you just wanna be like, “Hey, like, just do better here, because like, X, Y, and Z reason.” Like, that’s it. That’s the extent of the performance review, you know? (Kate: Yeah.) Like, in a year, the business fundamentally changed too much, at least in our context. In your context probably too. Definitely In your context, it sounds like, to where like, I feel like if I’m giving like, a quarterly or an annual performance eval, it’s like, not relevant anymore.

Kate (36:26):

That’s the thing, yeah. We barely do them anymore, honestly. Like, you can, (Teja: Yeah.) still, but like, it’s the maintenance of…the regular nature of having those good conversations, that’s the most important in, you know, businesses like ours, and honestly, even like, large enterprises <laugh> are like, you need to talk to the employees, and they’re like, “Yeah, I don’t know why we do it.” They’re like, “I don’t know why you didn’t tell me 11 months ago [that] I needed to improve on this thing,” right? Like, makes no sense.

Teja (36:56):

No, that’s exactly how I feel. Like, you know, if like, your friend is like, constantly showing up late to like, hang out, you’re not gonna be like, “Alright, October 1, I’m gonna tell my friend, dude.” (Kate: <Laugh>.) You’re like, “Yo, dude. Like, just like, can you work on this? Like, what’s going on?” You know? So (Kate: Yeah.) <laugh> yeah.

Kate (37:18):

<Laugh>. You’re exactly right.

Teja (37:19):

Okay. So as far as the seed round, you guys are like, heavily investing in product and in engineering. So when you say like, “train in AI,” like are you guys thinking about like, basically having a custom sort of language model that is gonna be trained and help, you know, orient people and inform people around the right way to communicate?

Kate (37:44):

Yeah. So right now, we’re working with OpenAI, ’cause (Teja: Cool.) we just don’t have the ability to do it ourselves, right? We’re not enough people <laugh>. (Teja: Yeah.) But yeah, I think that’s something that we need to figure out. I think there’s like, a crawl, walk, run on it, where we’re in crawl right now. Walk would probably be using multiple LLMs, because they have different ways of analyzing the communication that’s happening, right, because it’s not just the AI piece of it, but it’s actually being able to intake the information, and understand what we’re feeding it <laugh>, and then the output, right? Then I think, you know, and this is probably years, many years down the road, like, I think there is a world in which every company is gonna end up building their own LLM, because it’s defensible, you know, but who knows? I don’t know. I’m curious what your thoughts are on the future of that, and if you’re using it to help match or pair people and companies and that sort of thing.

Teja (38:55):

Yeah, I’m like, kind of like, a layman when it comes to like, understanding the direction of AI. You know, but I’ll give you my thoughts since you asked.

Kate (39:12):

Yes, please. We’re all laymans. We’re all laymans <laugh>.

Teja (39:15):

<Laugh>. Yeah, yeah. Well, you know, what’s interesting is I actually, I just did an interview with this dude who is CEO of a company called FireTail, and it’s a cool company. They do basically like, API security, and he was actually talking about, like, it’s interesting, and maybe I’ll have to connect you guys. He was talking about how, especially as like, companies build like, their LLMs, or as they’re leveraging like, other LLMs like, security becomes a huge issue, because you’re sending basically personally identifying data to a third party, and like, how do you make sure that like, it’s secure, it’s not vulnerable, you know, that sort of thing. So, I dunno. I’ll reach out to him, and (Kate: Yeah.) if you guys would like, I dunno, if that’s on the roadmap, but sounds like it is.

Kate (40:02):

It is. It totally is. It’s interesting, like, we’re still small enough where there’s basically three schools of thought when we get into the executive level of a deal. One is basically like, we’re not gonna be able to control this, so we’re just gonna go with it <laugh>. The middle, and then the other side is like, we have a hard stance. No AI. We will not allow employees to sign up for anything. You know, we’re not gonna get into this thing until we really know what the impact is, and in the middle, it’s like, basically, large enterprises are trying to architect deals with, you know, ChatGPT, OpenAI, where they’re getting their own version, essentially, of OpenAI, and they’re signing their own privacy agreements that like, OpenAI won’t use the data that they’re getting from Square, right, or Stripe or whatever, to train, to continue to train.

Kate (41:05):

I think that’s probably the future, right? The lawyers are gonna lawyer <laugh>, and they’re gonna figure out, basically, you know, until these companies can build their own LLMs, how can they safely, and in the right privacy settings, be able to empower their employees to move faster, ’cause I think it’s a foregone conclusion with all of the tech companies, anyway, that they’re gonna get left in the dust if they don’t use it and build it. So, I don’t know.

Teja (41:37):

No, I agree. I agree. We have a policy now that’s like, you cannot feed proprietary information into OpenAI. (Kate: Yeah.) That’s like, that’s a company stance, and there’s like, there’s a couple of reasons. I think the primary reason is like, we have a government contract, and so like, there’s certain regs that you have to follow around information security and things like that. I’m in the camp, though, that like, we’re comfortable sending it to like, Bard or Azure, like, building our own relevant (Kate: Yeah.) model that’s trained to our business, (Kate: Yes.) right, because I think building your own LLM is like, prohibitively expensive. (Kate: Yeah.) You know? It’s <laugh> takes like, a ton of money and a ton of engineers who are really smart to do it, (Kate: Yeah.) right? That’s like, I mean, that’s OpenAI’s business, so you need to have like, a separate business to do that. So I think that’s <inaudible>.

Kate (42:36):

Exactly. I totally agree. Totally.

Teja (42:38):

Yeah. I think over the long term, just like, what happened like, with you know, being able to host on the cloud versus like, having your own racks, I think that’s like, the direction that AI will go, you know, (Kate: Yeah.) and you could probably lease, you know, the service from these big software companies who’s made businesses like, hosting saves me a ton of time. Like, (Kate: Yeah.) for sure.

Kate (43:05):

So much, so much time. Yeah, yeah, and what’s possible is…it still blows my mind sometimes, like, on big things, right? Like, for us it’s, you know, how do we break down communication to make it more effective, right? That’s super complex between every individual person on the planet, down to like…I bought new sheets last week <laugh>. I fed it my requirements, and I got back the best, like, most inexpensive sheets, and I slept on them this week, and I freaking love ’em. I’m like, this is great. Like, you know <laugh>?

Teja (43:47):

Whoa. Yeah. Do you like Egyptian cotton, (Kate: <Laugh>.) or PET, TENCEL, or linen…like, give me your like, I’m sure you’ve thought about this, and you’ve researched this. I actually have strong opinion on bedsheets, so I’m just curious what you…

Kate (44:02):

Yeah, so I fed, my requirements <laugh> are, I like crispy, cool sheets, (Teja: Okay.) right, that are smooth, and I got back percale weave of Egyptian cotton is the best for that. (Teja: Okay, nice.) So percale weave, I’ve learned, has a single thread over/under. Like, it’s how they’re made, and that’s how they get the really smooth, crisp, clean feel. What are your thoughts <laugh>? What’s your preference?

Teja (44:36):

Those are <laugh>…my favorite are eucalyptus-based TENCEL sheets.

Kate (44:48):

I’ve never even heard of that.

Teja (44:51):

Yeah. Super soft, like, amazingly soft, and then in the summer, I like linen, obviously, and I think the linen might be like, like, if you wanna optimize for comfort and health, typically I’ve found that like, linen sheets have like, the least like, I’m such a weirdo. Like, I don’t like to have anything like, processed or like, (Kate: Yeah.) you know, anything that’s like, bad for me. Although obviously, I still like to party and like, you know, have the occasional alcoholic drink. (Kate: Yeah.) So I dunno, I’m like, grappling with that, but like, I like those, and it’s cool that you’ve leveraged basically AI to help you make that decision, because I would spend like, 30 minutes trying to figure out like, which ones to buy, and you could dispute it into <inaudible> (Kate: Yeah.) to figure out that for you. Yeah.

Kate (45:41):

That’s so interesting. I’ve not thought, you know, you spend so much time with sheets on your skin, it’s almost like, worse than clothing, or as important as clothing, right? Like, (Teja: As important.) I’ve never thought about that. Yeah, yeah. (Teja: Yeah.) Yeah, I read some article…

Teja (45:58):

Super important.

Kate (45:58):

There’s like, some chemical they use to process leggings, right? I don’t know if, I think Lululemon uses it, but it’s like, been linked to ovarian cancer, and like, you’re like, wow, you know, that’s really bad.

Teja (46:17):

Hundred percent. No, you’re putting like, basically like, a petroleum-based thing near your, like, on your skin.

Kate (46:25):

Reproductive organs.

Teja (46:26):

Yeah, yeah. It’s, yeah, it’s crazy. So I definitely am super bent on like, not doing that (Kate: Yeah.) to the extent possible, you know?

Kate (46:38):

Yeah. I’ve never tried linen sheets though, but I can see, I guess I’ve always thought, are they, do they feel scratchy? You know?

Teja (46:46):

Okay, you gotta wash ’em like, 10 times, (Kate: Okay.) and then they don’t feel scratchy anymore, but real good ones, like, high quality ones, will like, feel scratchy for the first, you know, let’s say you keep your sheets on for two weeks, it’ll take you about half a year to get it like, (Kate: Damn <laugh>!) soft. Yeah, yeah, yeah. If you change every two weeks, but like, you know, but it’s worth it, (Kate: Yeah?) because in a half a year you have like, these fully natural, awesome sheets, and like, I’m big on sleep. Like, I wanna sleep well, ‘cause, you know, you gotta use your brain like, a lot (Kate: Yeah.) during the day.

Kate (47:28):

Yeah. Heck yeah. Yeah, I’ve had, that’s something, I don’t know if it’s age or stress from being an entrepreneur, (Teja: It’s both. It’s both <laugh>.) <laugh>. I’ve had a really hard time sleeping, and it’s this like, vicious cycle, which I don’t know if you feel this, but like, I used to be pretty good about working out. Physical fitness helps my brain focus like, a lot. If I don’t get physical fitness, I’m just not as smart. Like, that’s the <laugh>, it’s just not gonna be a good day, but I haven’t necessarily felt that with sleep in the way I have my whole life with physical fitness, but I broke my foot this summer. (Teja: Oh, geez.) Like, you can’t do anything with a broken foot. It’s like, I was doing yoga, no yoga. You know, walking? Like, no. You’re running? No, you can’t do that, right? So it’s been very hard to get that, and so it now affects my sleep too, right? If I don’t get exercise, then I don’t, my sleep is crappy, right? So it’s like, this vicious cycle of I have to work out so that I can be a productive human, and then I have to sleep to be a productive human, but I can’t sleep if I don’t work out. It’s, you know, that sucks <laugh>.

Teja (48:51):

Yeah. Yeah. It’s a thing. Do you feel like working out like, helps you deal, like, and with and process like, work-related items or…

Kate (49:03):

So much. I used to be a runner, and that was really good for me to create focus, just straight up focusing on tasks with my brain, but now, and especially since becoming an entrepreneur, yoga has been like <laugh>, it’s almost like yoga, running doesn’t work anymore, because my mind doesn’t focus on running. It focuses on the other things, and that’s not good. (Teja: Yeah <laugh>.) So yoga <laugh> helps me like, ’cause like, a teacher is there saying like, “Bring it back to this moment,” you know, “Don’t let the other things seep into your mind.” You know, like, they’re actually, it’s mindful as well as physical fitness, and that’s huge, and you really, it’s still painful to do. I broke it in August, and it was, you know, I was cleared for working out again, doing yoga again eight weeks later, and I still am struggling. It’s still painful. I’m like, God, ugh, you know? I really miss it. (Teja: Yeah, yeah.) What do you do?

Teja (50:10):

Okay, do you have the Peloton app? (Kate: Yes.) Have you tried like, the Pilates or the yoga?

Kate (50:20):

No, only the bikes.

Teja (50:27):

Okay. They have like, some really cool like, ten, five minute like, stretching, yoga, Pilates, also weights, (Kate: Okay.) and like, dance cardio as well. So like, what I normally do is like, I have like, a gym in my house, so if I’m working from home, like, it’s pretty convenient to be able to lift in the morning, you know, during the work week, and then Saturdays and Sundays, I’ll like, go to a proper gym to train. I also like training jiu jitsu, but I recently tore my ACL, so I can’t do that for a while. So similar to you, (Kate: Sorry.) that’s a thing where, yeah. (Kate: Yeah.) No, it’s okay. It happens. It’s part of the game. So I feel like, yeah, with jiu jitsu, I can take my mind off of work, and like, you’re forced to, ’cause like, you’re like, you’re physically grappling with another human being, and like, you can’t really think about anything else except that, (Kate: Yeah.) because like, they’re literally trying to like, choke you, (Kate: Yeah <laugh>.) so you’re just like, okay, I’m focused.

Teja (51:30):

I’m focused here, but to replace that, I have found like, if I can get like, an hour for lunch or something like that, I can eat in like, 30 minutes and like, maybe spend the first 30 like, doing like, a Pilates class or like, a yoga class. (Kate: Yeah.) That’s like, pretty convenient, and like, also, you know, if I go to like, a yoga class, it’s like, a big commitment. It’s like, 30 minutes there, it’s an hour there, it’s 30 minutes back, it’s shower, it’s two, three hours out of your day, you know, (Kate: Yeah.) but if you do it at home, like, after work or in the morning, like, it’s pretty solid.

Kate (52:10):

I gotta try that. I live on top of a CorePower, so I just have to walk downstairs <laugh>.

Teja (52:16):

Oh, that’s sick.

Kate (52:17):

Yeah, yeah, yeah. It’s still a big commitment even like, you know, ’cause you have to like, change your clothes, and get your water, and get your mat, and like, you know. I mean, I can do it in like, 10 minutes, but then you’re there for an hour, and then shower, and you’re right. It’s a lot. Yeah, I gotta use a Peloton app for more than just bike. So you’ve inspired me.

Teja (52:43):

No, it’s really cool, because like, I love weightlifting, but sometimes like, that’s not, I don’t know, this is like, you can really only do that like, once per day, but if you like, if you like, need to like, process an issue, and it’s not helpful to sit in front of a computer to process it. Like, I like to do something like that for like, 10 minutes and usually that really helps. So yeah, I’m big into like, trying to be physically like, I feel like, the better your physical health is, the better that you show up at work, generally.

Kate (53:18):

Yeah, definitely. So it’s mental for me. My mental health is so much better when my physical health is, you know, on point.

Teja (53:24):

Yeah. It’s dialed in. Eating right, sleeping well, yeah. Totally. (Kate: <Laugh>.) Yeah, on the concept of sleep, you know, it’s interesting. This would happen when we would go into an office every day. I would get so stimulated from being around my colleagues that I would not do any work around them. I would just like, spend time talking to them and like, solving problems with them, and I like, have this stacked to-do list of like, things that only I can look at (Kate: Yeah.) and do, you know, because like, they’re like, emails to me that have downstream to-dos, and like, I can’t offload them to somebody else, because like, I need to do them, and so I would just get home, slam another coffee, get it done, and then by the time we finish, it’s like, midnight or 11, and you’re just laying in bed, and you’re just like, okay, I need to not do that the next day, and then you do it again the next day. (Kate: Do it again <laugh>.) So yeah, yeah. It’s been a little bit easier to like, be more disciplined, because now I can like, segment like, in office time or meeting time with people differently since like, we’re a remote-first company.

Kate (54:27):

How do you get that, or how have you transitioned to get that like, stimulation that you do need, right, or connecting with humans remotely. How have you figured out what the right mix is for you?

Teja (54:40):

To the extent possible, I like seeing people in person, but, you know, and so I try to meet regularly with people like, in real life that are like, local to Nashville, like, grab a beer with them or maybe grab some lunch, and then we try to get the leadership team together every quarter, ’cause everybody’s remote. We do our quarterly board meetings, we’re like, you know, our investors fly in, so it’s pretty healthy, because those meetings, like, we do a lot together. You know, we’re planning, we’re talking, we’re hanging out, we’re going to dinner, we’re hanging out afterwards, and so that feels right to me, and then I’m also part of like, a number of different like, peer groups that meet monthly, (Kate: Yeah.) and so that’s actually been super helpful, and then like, also, you know, I go to the gym every week, or I go train jiu jitsu, you know, quite often. So I can get that stimulation in different contexts in different ways. For me personally, I’m more productive from an output standpoint, not going into the office every day, because if I go into the office every day, I’m not getting done the things that I need to get done, generally. (Kate: Yeah. Same, same.) So that, yeah, and it’s not the same for everybody, maybe, but it sounds like it’s the same for you.

Kate (56:00):

Yes, totally.

Teja (56:01):

Where can people like, oh, we’ve done an hour already, and I dunno if we got a chance to dive in too much into the company, but I think you did a great job at like, just like, feature casting and telling the world like, why people should sign up to Teaming. So where can people find Teaming on the interwebs, and where can people find you?

Kate (56:27):

Good question. Teaming is Teaming.com, though we are rebranding, so it will…(Teja: Okay.) we’ll forward it for sure, but we will have a new name at some point, but go to Teaming.com anyway, whenever you’re listening to this, ’cause it’ll be there <laugh>. For me on LinkedIn, it’s Kate O’Neil. I think my like, slug is O’NeilKate on LinkedIn, and that’s been a really incredible tool for me. I don’t know how active you are on LinkedIn, but you know, we get most of our sales leads that way, but for me personally, it’s been, you know, quite a great way to build a community and make connection, and like, anything with a community, you kind of have to contribute, right? So I try to post once a day about something that’s, you know, relevant to me, or what I know is relevant to the folks that I’m connected to, that’s relevant to Teaming and the problems that we help people solve. It’s not sales-y. I mean, I guess occasionally it’s like, “Yeah, we got this new feature,” you know but like, really problem solving with your customers and your prospects on LinkedIn has been (THE FRONTIER THEME FADES IN) such a great avenue and channel for us to be able to, yeah, get to know the folks that we’re serving.

Teja (57:50):

That’s awesome.

Kate (57:51):

So, that’s where you can find us <laugh>. Sorry.

Teja (57:54):

That’s cool. No. Yeah. O’NeilKate with one “L” in O’Neil.

Kate (57:58):

Yes. Yes. O-N-E-I-L. I’ll tell you the story of why O’Neil is spelled so many different ways at some point <laugh>.

Teja (58:06):

Yeah <laugh>.

Abbey, via previous recording (58:07):

You’re listening to the Founder to Founder podcast, powered by Gun.io’s Frontier Network. We release a new episode every Thursday morning, so be sure to subscribe on Spotify, Apple Podcasts, Stitcher, or wherever you stream your music. Please leave us a review and share with your friends. You can follow us online at the Frontier Pod or drop us a line at [email protected] to get in touch about hiring world class tech talent.

(THE FRONTIER THEME ENDS)