YouTube transcript
Video ID: CHcFVYhTDuk
Language: en
Captions: auto-generated

[0:00] He's really successful. They've raised
[0:01] multiple rounds. They're absolutely
[0:03] crushing it. And he's still learning
[0:05] every single day and growing as a
[0:07] leader. And so, you don't have to have
[0:09] it all on day one to start your
[0:12] business. The adventure of life is go do
[0:15] cool things and make friends along the
[0:16] way. Why would you want it any other
[0:18] way? We made some very expensive
[0:20] mistakes. We were kind of told that was
[0:23] the norm. And we realized after we take
[0:25] a few steps back like what is actually
[0:27] true to us as an organization, true to
[0:29] our users and maybe it's not
[0:33] applying this more standardized play.
[0:34] Welcome to Ambition Align. Today I
[0:36] talked to my good friend Claire, CEO and
[0:39] founder of Kipsy. So I've known her for
[0:41] almost 10 years now. She was a
[0:44] accounting professional with me over at
[0:46] Deote. Then she moved her way to
[0:48] Blackline and then ultimately another
[0:50] startup and then started her own startup
[0:52] after going through an incubator like
[0:53] event. And she talks about her whole
[0:55] journey, how she went to found her own
[0:57] company, speed dating through founders
[0:59] and ultimately the challenges of being a
[1:01] founder and leading with value and
[1:03] integrity throughout it all and
[1:05] self-leading as well. It's just an
[1:07] awesome awesome interview. I think you
[1:09] get a lot of value out of it and I
[1:10] really want to thank Claire for coming
[1:11] on. So stay tuned, subscribe, watch and
[1:15] let's dive into it. Hey Claire, it's so
[1:17] good to have you on Ambition Aligned.
[1:18] It's just really my pleasure. I can't
[1:20] believe it was what it must have been 10
[1:24] years ago when you and I or eight to 10
[1:26] years ago when you and I were working at
[1:27] Deote together on impulse. You finally
[1:29] reminded me the name right before this.
[1:31] So and now you're a founder and you own
[1:33] your own company and you're a founder
[1:35] and CEO. How did that happen? Like what
[1:38] what what was that what happened from
[1:40] being that audit assistant with me and
[1:42] then now you're a founder of Kipsy? Tell
[1:45] me the tell me the story. Yeah, it's uh
[1:48] it's been a while uh since then. Um
[1:51] let's see. Well, I I I love working with
[1:54] you. I didn't entirely love working in
[1:56] audit. So, I knew I wanted to make a
[1:58] career uh pivot out of uh accounting.
[2:02] And luckily, a recruiter reached out to
[2:05] me asking if I wanted to go join a uh
[2:08] software company. You're building
[2:10] accounting software uh out in LA,
[2:12] company called Blackline, also female
[2:13] founded. Super cool. Oh, I remember. I
[2:16] remember Blackline. Yeah, I remember the
[2:18] referral process for that. Yeah. Yeah.
[2:20] Yeah. They're they're super cool. Um I
[2:22] had some great mentors working there and
[2:23] I joined the product management
[2:25] department. Got really passionate
[2:26] building software and felt like, you
[2:29] know, if we knew how to even better
[2:31] tools at Deote, I probably would have
[2:33] had a better experience working in audit
[2:35] there. and it kept me really passionate
[2:37] wanting to build for the accounting
[2:38] space and kept growing my career in
[2:41] product. Flash forward a few years
[2:42] later, I get this opportunity to start
[2:44] my own company. Obviously, I'm going to
[2:45] pick accounting software. Um, and I
[2:49] really I think relied on my background
[2:51] as an accountant, but also as a PM to
[2:54] help scale up the early stages of our
[2:57] software product to where we could
[2:58] actually start selling it. Um, but I
[3:00] think like from early time on, I always
[3:02] knew I wanted to start something. It
[3:04] just back when we first started working
[3:06] together, I always thought I wanted to
[3:07] like make partner and go go that route,
[3:09] but like have a large impact on a
[3:11] culture in some way, an organization,
[3:13] whether it was a brand new organization
[3:14] or one that's been around for a while.
[3:16] Um, it just so happened that my path
[3:18] took me into actually starting my own
[3:20] company from the ground up. But yeah, it
[3:23] was all kind of centered around I'd say
[3:24] want to build a healthy culture for
[3:26] people to grow their careers like I was
[3:28] able to grow mine.
[3:30] Yeah, it's really interesting. You said
[3:31] something there that it'd be fun to
[3:32] unpack a bit because you said that maybe
[3:35] if I had a tool like this in audit, I
[3:37] would have stuck around. And it's
[3:40] something I've talked to other
[3:41] professionals on here before that it's
[3:42] unfortunate the culture we have in audit
[3:44] and the unsophistication of the tools
[3:47] because it makes a unnecessarily harsh
[3:49] environment, right? Like it's fun to
[3:51] learn. It's fun to have mentors. And did
[3:53] you mean I guess my question is do you
[3:55] mean that seriously? Do you think was
[3:56] there something that would have kept you
[3:57] there was there something you liked
[3:58] about audit or was that transition I
[4:01] want to say about like audit as a as
[4:03] like a like a workflow? Um, but I liked
[4:07] admittedly I actually liked traveling to
[4:09] go on site for clients like you got to
[4:10] touch all these different industries,
[4:11] work with a lot of different people. And
[4:13] so I really enjoyed those aspects of
[4:16] Deote and now that I'm at a startup, I
[4:19] still do miss some of like the benefits
[4:21] you got working at a really large
[4:22] company like you don't have to worry
[4:25] about running payroll, right? Or like HR
[4:28] compliance and stuff like that. It just
[4:29] like just taken care of for you. And I
[4:32] think um that was like a benefit that I
[4:34] definitely appreciate more now as a
[4:36] founder. But yeah, I think there would
[4:38] have been some things that definitely
[4:39] would have kept me there if you know it
[4:41] would just been a better experience
[4:42] earlier on. But ultimately I'm really
[4:46] happy where I'm at. I wouldn't even be
[4:47] where I'm at without Deote and so it all
[4:49] worked out.
[4:51] Yeah. I I I mean I'm I'm super proud. I
[4:53] mean super impressed. I know proud is
[4:55] the right word or impressed the right
[4:56] word. You too. You've been crushing it
[4:58] on your end too. like you run his
[5:00] podcast, you're writing a book
[5:02] apparently. So that that was awesome. So
[5:05] yeah. Yeah. But it's still it's still
[5:07] the risk of running payroll and starting
[5:09] your own company is just amazing. So how
[5:11] does that go? So what did you learn at
[5:12] Blackline and what was the kind of the
[5:15] inclination that oh I'm going to go
[5:17] start what was the catalyst to start
[5:19] your own business? Yeah. Um well I was
[5:22] working at Blackline and I felt like I
[5:25] was getting exposed to a lot of other
[5:27] parts of a company that we didn't really
[5:28] get to see working in audit like we
[5:30] mainly talk to just people in the
[5:31] accounting and finance function at Deote
[5:33] and at Blackline I met or I had to work
[5:36] with on the daily basis like engineers
[5:39] um you know a lot of people in
[5:40] operations even sales actually too
[5:42] they're very salesled um technology
[5:44] company and so there was a lot of go to
[5:46] market motions that I would be involved
[5:47] in more passively on the product side
[5:49] but I still get exposure room and I felt
[5:52] like I could kind of start piecing
[5:54] together like how they came to be and I
[5:58] had immense respect for um Theres Tucker
[6:00] who's the CEO and founder of Blackline.
[6:03] Uh just you know she built this really
[6:05] large now publicly traded company and
[6:07] different types of people were welcome
[6:08] to work there. It was very um friendly
[6:11] for working parents which I have a lot
[6:14] of respect for just in terms of like the
[6:15] health benefits and the flexibility
[6:17] which I think especially precoid wasn't
[6:20] super common yet. Um, so I always say
[6:23] it's like, hey, like that's super cool
[6:24] that you did this. You built something
[6:25] from the ground up and you've had this
[6:28] monumental impact on all your other
[6:29] employees. Like when the IPO, people
[6:31] were able to send their kids to college,
[6:33] buy a house, like these big milestones
[6:35] in their lives, and I was like, I want
[6:37] that. Like I want to do what you did.
[6:39] Uh, the only problem was, uh, when I
[6:42] joined, they were already this massive
[6:44] company. And so while I was still kind
[6:46] of piecing it together, I felt like
[6:48] there was still a really big gap between
[6:50] like starting out and like how did you
[6:52] get to where you're at now, right? Um
[6:55] and that's when I ended up leaving
[6:56] Blackline to go work at a Sequoia backed
[6:58] startup called LILT uh in the AI space
[7:00] and that were a little bit smaller at
[7:02] the time only about 100 employees to get
[7:04] more hands-on experience at an earlier
[7:06] stage company.
[7:10] So So let me recap it. I want to make
[7:13] sure I'm hearing you right. It was
[7:14] intentional to go to LILT. It was how
[7:18] did you didn't see clearly how you can
[7:21] get to a blackline size? You're already
[7:23] at Deote which is the as big as it gets
[7:25] and then Black Line's still pretty huge
[7:27] and you're saying I want to see how to
[7:29] build it. So you're already having the
[7:30] building mindset going into Lil. Is that
[7:32] right? Yeah, definitely. I think that's
[7:34] I realized that that was where like my
[7:35] gap really was. Um I was lucky that
[7:37] Black Line and that like I got a really
[7:39] good um product mentor. Um so the
[7:42] director of of product was like this
[7:44] really really smart um product expert
[7:47] who I think guided me a lot early on my
[7:48] career also taught me to like make more
[7:50] space when I enter a room and just like
[7:52] I think being a woman in tech you need
[7:55] to learn how to navigate that and
[7:57] ironically he's not a woman in tech but
[8:00] he was a really great advocate for me in
[8:02] my career and I benefited a lot from
[8:04] that now as a CEO um but I learned the
[8:07] really great basics of how to be a good
[8:08] product manager um got a lot of
[8:10] certifications took a lot of classes all
[8:12] provided through Blackline and I also
[8:15] had the opportunity to work on a product
[8:16] that was um kind of selfisolated. So we
[8:19] actually got to operate a little bit
[8:20] like a startup inside of a publicly
[8:22] traded company and that was super fun
[8:24] but ultimately we still had the growing
[8:27] pains of big company bureaucracy and
[8:29] stuff like that that you had to deal
[8:30] with all the red tape multiple layers of
[8:32] management that ultimately realized I
[8:34] was going to slow my growth if I didn't
[8:37] stretch myself and go to a smaller
[8:38] company where there were less layers of
[8:40] management um and that that's exactly
[8:43] when I decided to leave and go work at
[8:44] Lil. Can you can you tell me a little
[8:47] bit more about the creating space?
[8:48] That's kind of interesting. He said so
[8:50] he taught you one thing is really big.
[8:52] Same for me as like being an advocate.
[8:54] If you're not a woman, you can still be
[8:55] an advocate for women, right? It's
[8:57] really important and support your female
[8:59] colleagues uh especially. What what did
[9:02] he do or what did you learn from him
[9:04] about creating space if you don't mind
[9:06] sharing? Yeah, definitely. So, I think
[9:08] for starters like just being present
[9:10] like having regular check-ins especially
[9:12] like I was coming from Deote. I had no
[9:14] idea it was normal, very young in my
[9:16] career. And he was like, "We're going to
[9:17] have dedicated time, one-on ones, and
[9:19] like we're going to check in, see how
[9:20] you're doing. We're going to give you
[9:22] certain goals to execute on." And I
[9:23] responded really well to that structure.
[9:25] And then just again working in office,
[9:28] he would notice certain things in our
[9:29] meetings. Like if I was running late
[9:32] from one meeting to another, um I was
[9:34] coming into the room, even though I was
[9:36] one of the presenters, I might come in
[9:37] through the back or like just try to be
[9:38] very quiet when I come in. He's like,
[9:40] "No, like he's like you're one of the
[9:41] main reasons that this is even
[9:42] happening. you help from this initiative
[9:44] like take more ownership, speak up more,
[9:47] command the room more, like just garner
[9:50] more attention. And so he really pushed
[9:51] me in certain ways. I don't think I got
[9:53] that experience while working in audit
[9:55] at Deote cuz it wasn't really something
[9:56] we would get much experience doing
[9:58] there. Um, but he was just very
[10:00] observant and noticing like my
[10:01] behaviors, I think, in physical spaces,
[10:03] but also how I present and carrying
[10:06] myself around other colleagues. and then
[10:08] he would give me really good, healthy,
[10:10] constructive feedback that was very
[10:12] objective on how I could make
[10:13] improvements to just kind of better
[10:15] present myself.
[10:17] Well, I think there's two sides there. I
[10:19] mean, thank you for sharing that. That's
[10:20] that's great feedback and I completely
[10:22] agree like confidence especially with uh
[10:25] is with women and certain I'd say
[10:27] certain ethnicities too like certain
[10:29] cultural right there's certain cultural
[10:30] boundaries where you just don't feel
[10:31] comfortable speaking up or asking
[10:33] questions but there's that perception if
[10:35] you are kind of louder and more in
[10:37] charge in a room it it's noticeable and
[10:40] people are looking for that they're
[10:41] looking for someone to add value that's
[10:42] why you're there in the first place um
[10:45] but I'm curious
[10:47] what
[10:49] trying trying to think of the right way
[10:50] to ask this.
[10:52] You
[10:54] It takes I guess it takes someone to be
[10:56] coachable. Like the fact that you were
[10:59] open to that advice that's quite
[11:01] confront there's a bit of confrontation
[11:02] with that advice, right? Like someone
[11:04] comes to me and like hey I noticed you
[11:05] came through the back room. Next time go
[11:07] through the front room. Part of me wants
[11:08] to be like screw you buddy. Who the who
[11:10] the hell do you think you are? But but
[11:12] what got you in that mindset? Was it
[11:14] like did he build some trust with you
[11:15] beforehand? Um yeah I think so. like the
[11:19] I I could feel it during the interview
[11:21] process. I remember being pretty nervous
[11:23] leaving Deote to go work at this
[11:25] technology company um that I admittedly
[11:27] didn't really know much about and a
[11:28] career that I didn't know anything about
[11:30] either for that matter. Uh but it was
[11:32] pretty obvious when I was going through
[11:34] like the um the series of interviews of
[11:37] different people on his team that people
[11:38] were really approachable um very
[11:40] empathetic just like generally cared
[11:42] about getting to know you. And that
[11:44] sense continued on if not only got
[11:46] stronger while I was working at
[11:48] Blackline over the years. And so I think
[11:50] like that definitely just helped like
[11:54] this is a really weird analogy but it's
[11:55] just something honestly that I still
[11:57] remember to this day. I was wearing
[11:58] really comfortable shoes one day at work
[12:00] and so I I didn't notice but apparently
[12:02] I was walking with like a slight limp
[12:04] because I had a blister at the back of
[12:05] my heel. My boss noticed and actually
[12:08] asked he's like oh like are you okay?
[12:09] Did you injure yourself? I notic like
[12:10] you're walking a little bit differently
[12:11] when we were coming out of one of the
[12:12] elevators, but he was just like very
[12:14] observant and in a very thoughtful way.
[12:16] So when he would give me that kind of
[12:17] criticism, I always knew it was coming
[12:19] from a place of care and he wanted what
[12:21] was best for me. And so I never had, I
[12:23] think, any defensiveness whenever he
[12:25] would bring anything like that up. If
[12:26] anything, I was hungry for more feedback
[12:28] like that because I knew he just wants
[12:30] me to be better and it was coming from a
[12:32] really positive place. And so the
[12:34] intention was definitely there. I just
[12:35] had to be ready to receive it.
[12:38] Yeah. And I think you you bring
[12:40] something really powerful there. And I
[12:42] can already see it and how you've you've
[12:43] structured your language around your
[12:45] your company of KFC is the importance of
[12:48] putting people first and that is really
[12:51] leadership, right? To to build trust by
[12:53] actually caring and giving a crap about
[12:56] your people. Yeah. That's that's how it
[12:58] it sounds silly. It sounds so basic, but
[13:00] that's what you need to do. And it it's
[13:02] pretty rare. You and I know it's very
[13:04] rare actually to have a leader who cares
[13:06] to see that you have a blistered foot
[13:08] and make wants to make sure you're okay.
[13:09] Most people just want to see outcomes
[13:11] and kind of don't want to deal with the
[13:12] hassle. But that's the best part of
[13:14] leadership in my view or the best ever
[13:16] since it is just working with people and
[13:17] seeing if you can make their lives a
[13:18] little better while you build something
[13:20] do something cool together, right?
[13:21] That's the whole point of life is that
[13:22] the adventure of life is go do cool
[13:24] things and make friends along the way.
[13:26] Why would you want it any other way? Um,
[13:28] so that that's interesting that you had
[13:31] that with someone and you mo that
[13:32] modeling you you're carrying that
[13:34] forward into your other companies. Seems
[13:35] very powerful. Um,
[13:38] so how does LIILT so you're there now so
[13:42] you went from Black Line, you wanted to
[13:43] get the exposure to a smaller company.
[13:46] What did you learn? What was that
[13:47] experience like? Uh, it was great. I
[13:50] mean I think has an amazing product.
[13:53] They're in the language translation
[13:54] space. um they use AI to help localize
[13:57] um all sorts of different content and it
[14:00] was a much smaller organization and so I
[14:02] had a lot more reach from day one and I
[14:05] just I loved that it was basically like
[14:08] if you don't get this done it just it's
[14:10] not going to get done kind of mentality
[14:12] there. So very humble people would just
[14:14] pick up whatever need to be picked up.
[14:16] There was really like no ego about like
[14:18] this isn't my job description. Everyone
[14:19] was kind of there to help out each
[14:20] other. Uh it was very much a hustle
[14:22] mentality and I really honestly picked
[14:26] that job not necessarily because I was
[14:28] particularly passionate language
[14:29] translation space although I I did
[14:31] become more excited about it while I was
[14:33] working there. Um I picked the job
[14:36] because of the hiring manager. Um I
[14:39] thought was like a really experienced
[14:41] product leader. I really again
[14:43] appreciated the way that he communicated
[14:45] uh very clear direct but again coming
[14:47] from a place of care and also very
[14:49] objective. So, I think I had to like
[14:52] worry about politics or things like
[14:53] that, right? It was just like, "Here's
[14:55] what you do. Here's what I recommend and
[14:57] like I trust you." And it was also a
[14:58] leader where I could go and push back on
[15:00] and say, "Hey, I don't think we should
[15:01] do this." And he would just like look at
[15:02] me for a second and be like, "Okay,
[15:04] yeah, you explained why that makes
[15:05] sense. Sure, let's not do it." And like,
[15:07] no ego, nothing about it. He's just very
[15:09] rational. And that again helped boost my
[15:11] confidence even more about executing
[15:13] which you know when you're starting your
[15:15] own business you have to be very very
[15:17] good at execution to survive especially
[15:19] that that first year of starting like a
[15:21] technology startup. Um so he was great
[15:24] ended up having a baby and then um after
[15:28] the paternity leave um didn't come back
[15:31] to the company unfortunately um he
[15:33] started his own his own thing which
[15:34] actually makes a lot of sense given his
[15:36] background. Um so I was bummed about
[15:38] that but ended up actually becoming a
[15:41] really great opportunity because I then
[15:42] end up reporting into um the CEO for
[15:45] quite a while um from my ring of time at
[15:47] LUL actually I spent a lot of time
[15:49] working directly with the CEO and seeing
[15:50] how he operated um how you interface
[15:53] with some of the investors other um
[15:54] heads of different departments and it
[15:57] just felt a a bit more real I guess cuz
[16:00] again it was a smaller company they're
[16:02] still figuring things out um obviously
[16:06] everyone's super smart and amazing
[16:07] product. But like again, he was just
[16:09] very humble about like, oh, I didn't
[16:10] know this how you could approach product
[16:12] management. I didn't know this. And
[16:13] there were certain conversations I
[16:15] realized where like actually I knew
[16:16] something more than he did, which wasn't
[16:19] really something I got to experience
[16:20] working at larger companies. And I
[16:24] appreciated that cuz it made me realize,
[16:25] okay, like he's really successful.
[16:27] They've raised multiple rounds. They're
[16:29] absolutely crushing it. And he's still
[16:32] learning every single day and growing as
[16:34] a leader. And so you don't have to have
[16:36] it all on day one to start your business
[16:39] is basically where like that kind of
[16:41] light turned on in my head. I was like,
[16:42] "Okay, like I think I could probably I
[16:45] could probably do this." Um, and then a
[16:47] few months after that, that's when I I I
[16:49] left a little and started Kipsy.
[16:53] Wow. So it was something that's an
[16:56] interesting jump. You kind of got that
[16:58] promotion, battleground promotion,
[17:00] battlefield promotion, whatever you'd
[17:01] call it, from your hiring manager who
[17:04] luckily had a kid but unfortunately left
[17:05] even though you're very close and
[17:07] sounded to them or respected them and
[17:09] then worked with a CEO directly and
[17:11] gained confidence through that that
[17:13] exposure, right? But how do you
[17:16] translate that? How do you translate
[17:17] that to that? Okay, I'm it's not like
[17:19] money comes up from thin air or like
[17:21] some great idea. How did you how did
[17:23] that spawn into and I know a little bit
[17:25] about this but I'm just for the
[17:26] audience. How did that spawn into
[17:28] building Gypsy? So I guess one thing
[17:30] that was probably worth mentioning is in
[17:32] between Blackline and Lilt um I've been
[17:36] approached by a recruiter to interview
[17:38] to be a founder through like an
[17:40] incubator program and I was super
[17:43] excited about it. That was really really
[17:46] great experience because they're
[17:47] basically going to give you like funding
[17:48] on day one to launch an idea and they'll
[17:51] help you uh find your technical
[17:52] co-founder. It was like this really
[17:54] great again structured program that
[17:56] would kind of help you get past like the
[17:57] initial hurdles of starting a business
[17:59] which for me as someone who'd be a brand
[18:01] new founder I I found very appealing. Um
[18:04] and I interviewed for it and I didn't
[18:07] get it and I remember being super bummed
[18:09] about that. And the feedback from that
[18:12] was I didn't have real like startup
[18:14] experience because Blackline was too
[18:16] mature at the time and it showed when I
[18:18] was going through the interview process.
[18:20] And so that was really a major catalyst.
[18:22] I was like okay now's that was like this
[18:24] is now the time like I need to go to a
[18:25] smaller startup and like you know really
[18:29] like learn the ropes and everything. Uh
[18:32] can we pause there for a second because
[18:33] that's really I can't tell you how many
[18:35] times I get that note from recruiters or
[18:39] I have throughout my career is like hey
[18:41] you have too much big company experience
[18:43] like me I've done the Google thing I've
[18:45] done the uh deote thing and I've done
[18:48] but I was at a boutique consulting firm
[18:50] but they still that perception having
[18:51] that brand it's actually an interesting
[18:53] thing to get over of like hey that's a
[18:56] different brand you actually being at a
[18:58] startup's a little a different game and
[19:00] you really won't understand it unless
[19:01] you've done it right. And so it sounds
[19:03] like you that that's the feedback you
[19:05] got. Yes. Yeah, that was exactly it.
[19:07] Like they could just see that like I I
[19:10] didn't have like enough like on the
[19:12] ground experience probably to to start
[19:14] from going from like zero to one
[19:15] ultimately. And so I was like well
[19:18] like that case I got to go get that
[19:20] experience somewhere. I need to I have
[19:21] to go to a smaller company like this
[19:22] like this is what I need to do if I want
[19:24] if I want to take advantage of an
[19:26] opportunity like this again in the
[19:27] future. may not that exact same
[19:28] opportunity, but something like that. I
[19:30] need to be prepared for it. So, let's
[19:32] take control of my career and move on to
[19:34] the next thing that where I can help
[19:36] kind of level up my my role as a as a
[19:38] product manager. Um, took a senior PM
[19:41] role at LILT and was like a great great
[19:46] confidence boost like you know building
[19:47] things from the ground up very hands-on
[19:49] with engineering team. They were much
[19:52] faster in how they released software
[19:54] updates as well compared to Blackline.
[19:56] Again, just apples to oranges. Clearly
[19:59] different comparison of like how these
[20:00] organizations are structured.
[20:01] Blackland's publicly traded company.
[20:03] They do all these investor updates. You
[20:05] know, Wilt's still private, much
[20:06] smaller, probably like a tenth of the
[20:08] size at the time. Um and I was like just
[20:12] having to like run all these different
[20:13] initiatives and engineering. I was like,
[20:14] "Okay, cool." Really comfortable
[20:16] executing at a fast pace. And it just so
[20:19] happened that um the job at LIILT
[20:21] brought me back to the Bay Area which is
[20:23] where I grew up but you know we we were
[20:25] working down in LA stayed in LA for
[20:27] quite a while after that too. Um, but
[20:29] LIIL was hybrid, so I had to come back
[20:31] up to the Bay Area. And I was working in
[20:33] the Bay. And the recruiter from that
[20:36] program that rejected me had a post on
[20:39] LinkedIn uh, saying that they were going
[20:41] to do a like women in tech event in the
[20:44] city one night. And I was like, you
[20:46] know, I'm going to go to that and
[20:48] reconnect with her. And I did. And we
[20:50] reconnected. And she's like, I really
[20:52] liked you. I think you should try
[20:54] applying again for the program. And I
[20:57] was like, "All right,
[20:59] you know, I got rejected once. Like,
[21:01] let's try it again and see how it goes."
[21:05] It been like a year, I think, at that
[21:06] point. Um, and I interviewed, you know,
[21:10] prepped a lot and I think also the
[21:12] experience at built really helped. And I
[21:13] got in the second time around and that's
[21:16] what ultimately was the catalyst for me
[21:18] leaving LOL and starting the company.
[21:21] Well, pause there. That's so brave. I I
[21:23] can't even just imagine going and seeing
[21:27] someone who already rejected me and just
[21:29] connecting with them again. I I I mean
[21:32] that not imagine is not the right word.
[21:33] I've done it, but it's like it's not an
[21:35] easy thing and especially after
[21:37] something as but not in in that capacity
[21:39] where you're really applying for a big
[21:41] program and then go meeting after.
[21:42] That's that's not easy. That was a
[21:44] really brave thing to do. Thank you. I
[21:45] appreciate that. Um and luckily the
[21:49] Bridget is her name was awesome. Um,
[21:51] she's super approachable. I loved her. I
[21:53] thought she was super cool and I think
[21:55] that also helped a lot. And then the
[21:56] people who interviewed me through the
[21:58] process were really great. Um, and just
[21:59] kind of honestly coaching me through the
[22:01] interviews too, which is really, really
[22:03] sweet. Um, and I end up getting in,
[22:06] joined the program, and that's how we
[22:08] got started. But I've been very grateful
[22:10] to the program itself and everyone I met
[22:13] through it, including my co-founder,
[22:14] because part of their structure is the
[22:16] five people who are really good at
[22:18] executing. So again, I learned how to
[22:19] execute through Lil. Um, and you either
[22:21] get in as like a future CEO, like a
[22:24] business founder, or a CTO, like a
[22:26] technical co-founder. So I got in
[22:28] through the CEO track. The next step was
[22:30] to get you matched with your CTO, which
[22:33] is a very strange emotional experience,
[22:37] kind of like speed dating
[22:40] in a way, almost worse or harder, I
[22:41] guess. Um, it was very, very tough for
[22:45] me to make a decision. And luckily I met
[22:47] my co-founder Shaolong um in that
[22:50] program and he's like the best engineer
[22:53] ever worked with and I didn't even know
[22:55] he existed until we both got like the
[22:57] bachelor or what was what was the like
[22:59] like a little bit like
[23:02] like it's it's very structured which for
[23:04] someone who like myself who has like
[23:05] really bad ADHD I I loved getting these
[23:08] instructions right um but you would have
[23:12] like these different rounds of like
[23:14] almost like dates with these different
[23:17] potential like co-founders. Um, and they
[23:20] even gave you like it was like a talk
[23:22] track, but like a list of like these are
[23:24] good topics or things to ask on the
[23:26] first call and like you should do like a
[23:28] 30 minute to an hour long and if they
[23:30] make it to the second call and you're
[23:31] both kind of vibing like you get a
[23:33] little heavier and you talk about this
[23:35] and then there's the third one and the
[23:37] last one you need to meet in person and
[23:39] see who really like can click, you know,
[23:41] have that chemistry in person with your
[23:43] co-ound.
[23:46] Yeah, it's like dating. It's very
[23:47] similar. Yeah, it's very funny. At least
[23:49] you got instructions for it. So I
[23:51] there's dating it's like you don't know
[23:52] where it's going to go kind of a thing.
[23:54] Um but it's that's what I did. And one
[23:57] thing I really loved on my co-founder
[23:59] was I I had talked to a lot of these
[24:00] other engineers basically. And most of
[24:04] them just cared about product
[24:06] development and that was it. and they're
[24:09] like, "Yeah, this seems like, you know,
[24:10] a good thing to build for. Requirements,
[24:13] check, check, check." Kind of they all
[24:15] just kind of center around building the
[24:16] software. My co-founder comes in like
[24:18] guns ablazing and he's like, "Do you
[24:20] think this will make money? And are you
[24:22] the one who can actually sell it? Like,
[24:24] are you able to sell?" And I was like,
[24:26] "Okay, I like you." Um, because like
[24:29] this is all something you need to care
[24:30] about. You could have the best, most
[24:31] amazing product ever, but if you can't
[24:32] actually take it to market or the
[24:33] market's not there, you're going to die
[24:36] because you just won't make enough
[24:37] money. and he had that business mindset
[24:40] while still having again big company
[24:43] experience coming from like Apple and
[24:45] Netflix from engineering. So he had um
[24:48] this really great background of like how
[24:50] to build best-in-class software at scale
[24:53] um but then also he went to work at a
[24:55] startup before joining Kipsy with me. So
[24:58] he had that startup kind of scrappy
[25:00] experience as well. So it was a really
[25:01] great combination. Um, and he at the end
[25:05] of the day was very business-minded like
[25:08] it wasn't just about building a cool
[25:09] feature or building in the certain
[25:10] architecture. It was about how is this
[25:12] actually going to drive real business
[25:13] value for the company for our customers
[25:16] to where we can take it to the next
[25:18] level. And that was something I feel
[25:20] like I didn't see in all of the CTO
[25:23] candidates that I was interviewing.
[25:26] And I I've I've also seen I've advised
[25:28] quite a few different startups
[25:30] throughout my career and uh it's a shame
[25:33] that too many people aren't thinking
[25:35] about the customer. They're thinking
[25:37] about their idea and I always say like
[25:39] do you think you could sell this
[25:41] tomorrow is can you sell this idea and
[25:43] that means you have to have a good
[25:44] product and someone who's reputable that
[25:46] can sell it for you. You need those two.
[25:48] So I like that CEO CTO founder model. it
[25:50] sounds like a great I want to pick I
[25:52] want to ask more questions around there
[25:54] but so many people just like oh I have
[25:56] this great idea there's this great
[25:57] product it's like well if no one's going
[25:59] to pay you for it then it's not that
[26:01] great I'm sorry like someone people
[26:03] still need to use it even if it has cool
[26:04] functionality if you can't figure out
[26:06] how to monetize it then you don't you're
[26:08] going to falter and it's not going to be
[26:10] sustainable for the long run um so it
[26:12] sound that sounds really cool that you
[26:13] met someone who was like that and had
[26:15] that mindset that's so helpful and so
[26:18] first what so what did that program look
[26:19] like what did you But so you win the
[26:21] application, you meet this founder,
[26:23] co-founder, and then what happens on day
[26:25] two? You go to Lil and say, "Hey, I'm
[26:28] going to start my own company. Screw you
[26:30] guys." What what what goes on next?
[26:32] Yeah. Um like a little bit.
[26:35] I mean, luckily, um so this the CEO,
[26:39] Spence, um who I actually still talk to
[26:42] the last few years, he's let me borrow
[26:43] their office space when I want to get
[26:44] out of my house, which has been really
[26:45] sweet, too. Um Oh, cool. He was really
[26:48] understanding about it. And you know, he
[26:50] was telling me he's like, "I hate when
[26:51] people leave, but the reason that you're
[26:53] leaving, like I can't even be upset
[26:55] about like this is a great opportunity
[26:57] and as a as a CEO and as a founder, I am
[27:00] so proud of the fact that like the
[27:01] experience that you got at Lil led you
[27:03] to be able to do this because that means
[27:05] I'm doing the right thing as an
[27:07] employer, which I was just like, that's
[27:11] you're you're so perfect." Like, who
[27:12] says that? Um, but that was like that
[27:14] was a culture at Lil and like I still
[27:16] talked to a lot of like my old
[27:17] engineering team and people that I
[27:19] worked with and I missed them a lot
[27:21] actually. They're they're all phenomenal
[27:22] people. Um, but starting my own company
[27:24] was just too good of an opportunity to
[27:26] pass up. So luckily Lil was super
[27:28] understanding about it. Um, and there
[27:30] were people even afterwards who were
[27:32] like, "Oh, hey, like you want like the
[27:35] sales leaders, um, Sylvia, she was like,
[27:37] I'm happy to, um, give you advice on how
[27:39] to hire your first, uh, you know,
[27:40] salespeople when you get to that point
[27:42] and what to look for." And she even
[27:43] shared like this kind of like rubric of
[27:45] how she evaluates candidates and stuff
[27:46] like that. And that was super sweet. Um,
[27:49] lots of people in the engineering design
[27:50] side offer to be um, kind of resources.
[27:53] We're first getting started. And it was
[27:55] just really nice to see that kind of
[27:56] culture. again very lucky to work at
[27:58] great organizations like Lil and
[28:00] Blackline to then start my own company
[28:01] and see like okay this is what I want to
[28:03] grow it into is have a culture that's
[28:05] like this where people are supporting
[28:06] one another. Um, yeah. So, Lil was like,
[28:08] "All right, cool. Like, we understand
[28:10] that you're, you know, tendering your
[28:11] resignation. We get it. Please stay in
[28:13] touch." And I did because they're great
[28:16] people. And yeah, it was super weird.
[28:18] Like, one day you have all these teams
[28:21] of people that you work with and like
[28:23] the next day you're kind of on your own
[28:25] because I think I I quit before I
[28:28] matched with my co-founder. I think was
[28:30] how the timing of it kind of worked out.
[28:32] Um, so I left Lil in June of 2022
[28:38] and my co-founder joined in mid August.
[28:42] So there was kind of this weird in
[28:43] between phase. It was really just me and
[28:45] the people um who were part of like the
[28:47] program they launched out of um kind of
[28:49] coaching me like here's what you do to
[28:51] get started like you got to you know get
[28:53] like a website domain, you got to like
[28:55] incorporate your company and here's all
[28:56] other things you got to do like the
[28:57] paperwork side of things. um you should
[29:00] also start doing market research which
[29:02] luckily given my product background I
[29:04] was like okay like I can actually wrap
[29:05] my head around that part more than all
[29:07] the legal junk. Um, so I started doing
[29:10] that and getting a good understanding of
[29:11] like what would we build for our MVP?
[29:14] And that was helpful in the
[29:15] conversations I ended up having while
[29:17] vetting out these CTO candidates because
[29:19] they're also vetting me, right? Like I'm
[29:20] not the only CEO that they're
[29:22] interviewing. They're interviewing other
[29:23] CEOs in the same program who are
[29:25] building other types of companies to
[29:27] decide if they like this person as a
[29:29] co-founder and if they also like the
[29:31] idea that this co-founder is going to
[29:33] build for if there's enough, you know,
[29:35] kind of market to support growing a
[29:37] company for that space. And um luckily
[29:40] my co-founder Jalong thought that there
[29:41] was and we end up matching. But before
[29:44] that, it was kind of weird. I was like
[29:45] just alone in my house basically taking
[29:48] a bunch of video calls and trying to to
[29:51] get organized and taking lots of notes
[29:53] and things like that. And then he
[29:55] joined. Um and then we brought on a UX
[29:58] designer and some engineers a little bit
[30:01] after that. Okay. So they gave you some
[30:03] seed capital and then you you kicked
[30:06] off. How long how long between getting
[30:10] seed capital, ramping up teams? There's
[30:12] a lot there, but ramping up teams and
[30:15] then having a product in the market and
[30:16] selling selling it. Um, Xiaolong is like
[30:20] an absolute beast. So, we were very
[30:22] lucky in that regard. Um, we started I
[30:24] think building in October is when we
[30:28] actually really started building the
[30:29] product. Um, before that it was like
[30:31] market research, getting the designs
[30:32] mocked up and then we actually executed
[30:35] on it. and we signed our first customer
[30:39] late December and they onboarded to the
[30:41] software the very beginning of January
[30:43] 2023. So we had enough of MVP to go to
[30:46] market within a few months. Um and that
[30:48] was I think because we had very strong
[30:50] design requirements set up. I think I
[30:52] had very good user empathy and then my
[30:54] co-founder is just an absolute machine
[30:57] of an engineer. Like it's it's insane
[31:01] like how much code even today the team
[31:03] will push out on a daily basis. And
[31:05] that's because we have a very very
[31:06] strong engineering leader and
[31:08] engineering culture within the company.
[31:10] That's it's a testament to you that you
[31:12] speak so so well of the team. You know,
[31:15] it's that's great to hear. There's not
[31:17] enough not enough of that in leadership.
[31:19] So, good on you. Um what does
[31:23] I guess what does getting your first
[31:24] customer look like in that like it
[31:27] sounds interesting to get your first
[31:28] customer be while you're building the
[31:30] product, right? Yeah, they were pretty
[31:32] openminded. We're very very lucky. Um,
[31:35] it's an accounting firm out in the Bay
[31:36] Area. Although, ironically, the people
[31:38] that we work with are based in Indiana
[31:40] of all places. Um, but they're an
[31:43] accounting firm called Sensiba. So,
[31:45] they're headquartered out in the Bay
[31:46] Area. Um, top 100 firm. They're growing
[31:49] great organization if you know anyone
[31:51] who's looking for an accounting firm to
[31:52] work with. And I met um one of their
[31:57] like R&D tax like leaders within the
[32:00] firm. Uh we were introduced I think
[32:04] through the I think it was the CFO of
[32:06] the like incubator that we launched out
[32:09] of. Um I think that's how we got
[32:11] connected. And I remember talking to him
[32:15] cuz I I was taking a lot of like
[32:16] informational interview types of calls
[32:18] at the time. I remember leaving that
[32:20] call being like I'm never going to talk
[32:22] to that guy again. He did not seem to
[32:25] want to talk to me. I felt like he was
[32:26] just doing it as a favor
[32:29] for the CFO. Um, and then in no it was
[32:32] November um of 2022, so like probably
[32:36] got to be like two months maybe after I
[32:37] I I talked to this guy. Um, his name's
[32:39] Cole over at Sensa. Um, I got an email
[32:42] from him and I remember cuz I was about
[32:44] to board a flight and um it basically
[32:47] just said like, "Are you guys still
[32:48] alive?" And I was like, "Yeah, yeah, we
[32:52] are actually." And like, "And this is
[32:54] we're working on this. We're building
[32:55] this." And he was like, "I think we have
[32:56] a need for this. Do you want to
[32:57] reconnect?" Um and we reconnected and
[33:01] that was also part of the reason why we
[33:02] were able to execute so quickly on
[33:04] building the MVP is we met with um him
[33:06] and some other people on his team um who
[33:09] gave us a lot of feedback on the
[33:11] software that we were designing like
[33:12] okay hey what if we do this have this
[33:14] feature here like no you should do it
[33:16] this way or think about this edge case
[33:17] and here's what we see like in the
[33:19] day-to-day work that we do and it was
[33:22] really generous of them to give us so
[33:24] much of their time and we really just
[33:26] had mockups in Figma And that was a but
[33:29] I think they were willing to do that
[33:31] because they saw like how excited we
[33:32] were to be working with them and also
[33:34] how quick we were to incorporate their
[33:36] feedback and respond. And I think you
[33:38] know we're still doing that today.
[33:39] Whenever we we get feedback from any of
[33:41] our customers we're very quick to
[33:42] execute on it and that helps build a lot
[33:44] of trust at the end of the day. Um I
[33:46] think you were telling me right that
[33:47] you're like your northstar before is if
[33:49] someone gives you feedback you're going
[33:51] to try to get that out ASAP, right?
[33:53] You're like you're and your team does it
[33:55] in remarkable amounts of time. Yeah.
[33:57] Yeah. Absolutely. We're very very big on
[33:59] user feedback at our company. Um the way
[34:01] I see it, especially for accountants,
[34:03] like they're not usually type of people
[34:05] who like to speak up a whole lot. You
[34:07] think about like the traditional
[34:09] archetype anyway for an accountant.
[34:11] They're a little bit more timid. Um not
[34:14] the people we work with, they're pretty
[34:15] passionate about what we build. That's
[34:17] just great. I feel very lucky for that.
[34:19] Um, but it's like I want to encourage
[34:21] that type of culture. People are
[34:22] comfortable speaking up and people
[34:25] aren't comfortable speaking up and
[34:26] giving you feedback or sharing their
[34:27] thoughts if they feel like it's actually
[34:29] being received well and you're you're
[34:31] considering the type of feedback that
[34:33] they're giving. And I think we show them
[34:35] that really by doing, which is okay,
[34:38] hey, you you mentioned this thing that
[34:39] you thought was really important or you
[34:41] felt like was a gap in the platform.
[34:43] Well, now we've built it. Here you go.
[34:46] and now please give us your feedback on
[34:47] the new thing that we built based off of
[34:49] your original feedback and let us know
[34:51] if we can make it better and they
[34:52] responded really well to that. Um so
[34:54] Senso was a huge um you know huge
[34:57] contributor to our initial MVP
[34:59] development and they were just really
[35:01] generous with their time and meeting us
[35:02] multiple times a week to help kind of
[35:04] flush out those design requirements. And
[35:06] so I think that also helped build a lot
[35:07] of trust with that process to where they
[35:09] were comfortable signing that contract
[35:10] with us early on and being our very
[35:13] first customer.
[35:15] And how many calls before they were your
[35:17] first customer? Like how many pro almost
[35:19] first customers were there?
[35:21] Uh, you know, that's a good question. I
[35:24] mean, there were other firms that we
[35:27] were talking with. So, Kipsy is a
[35:30] software platform built for accounting
[35:32] firms, I guess, for background. Um,
[35:36] that's a good question. I'm trying to
[35:37] think of how many people I I probably
[35:40] talked to like
[35:43] over like a hundred people probably.
[35:45] That's right. By that time, some of it
[35:48] were like they weren't the right fit,
[35:50] but they would be really good for
[35:51] informationational interviews. Maybe
[35:52] like the firm themselves wouldn't be a
[35:54] good use case for like the platform that
[35:56] we were trying to build. Um, but Senso
[35:59] definitely for like the size, the volume
[36:02] of clients that they deal with, how
[36:04] they're growing as a firm, perfect,
[36:06] perfect use case. And also just like
[36:08] their mentality
[36:10] about software, like they're not your
[36:12] average accounting firm. They're they're
[36:14] much more open-minded to adopting new
[36:15] technology. Um, they have a really great
[36:18] product mindset. Like they know when to
[36:21] ask for something or they're asking for
[36:23] multiple things at the same time.
[36:25] They'll actually say, "Okay, out of
[36:27] these five things I'm I'm giving you
[36:28] feedback on, this one's the highest
[36:30] priority, and here's why." Which is a
[36:33] really smart way to kind of present that
[36:35] information, whereas other people would
[36:37] just be like, I need all these different
[36:39] things with no rhyme or reason as to
[36:41] like why they're asking for it. Sensible
[36:43] was smart enough to always give the why.
[36:45] And again, that helped us from an
[36:47] engineering perspective build with
[36:49] better empathy for the end user. Um so
[36:51] again just they were a perfect fit for
[36:53] us whereas a lot of other firms that we
[36:55] work with or even don't work with might
[36:57] have more old school approaches and as
[36:59] we come more mature we definitely
[37:01] widened our reach in the market. Um but
[37:03] in the early days we definitely wanted
[37:04] more like those like early adopter
[37:06] personas and we found that in firms like
[37:09] Sensa.
[37:12] Yeah. Wow. Well, it's it's interesting
[37:14] because you brush over the hundred
[37:16] people pretty quick, but you had a
[37:19] hundred calls and that takes a lot of
[37:22] confidence, a lot of perseverance. And
[37:23] through all those calls, you still
[37:24] maintained a customer first
[37:27] curiositydriven mindset of, hey, I'm
[37:29] here. I want to build something special
[37:31] for you and we're we're trying to
[37:33] customize it to your needs. And they
[37:36] even came in, it felt like a no and they
[37:38] came back later with the yes, right? And
[37:40] that just goes to show and I think
[37:42] everyone can copy that model. I think
[37:44] that's something to replicate in
[37:46] business to like care about your
[37:48] customer, not to build assuming you know
[37:49] what they want, figure out what they
[37:51] want, listen and to have perseverance
[37:53] through the process because you never
[37:55] know who's going to be the right fit.
[37:56] But if you put your best foot forward
[37:58] and with a listening ear and and really
[38:00] try to customize to it and take customer
[38:02] feedback into consideration, who knows
[38:04] what can happen, right? Yeah. It's
[38:06] pretty ironic actually. a lot of the um
[38:08] the firms that I had initially reached
[38:09] out to even some of the ones that didn't
[38:11] respond to like my cold emails um are
[38:13] customers now funny enough. So it it
[38:16] really kind of came back full circle. Uh
[38:18] but Sensible was the one that like very
[38:21] early on was willing to take that risk
[38:22] on us and we're very grateful for that.
[38:26] Yeah, that's great. And accountants
[38:28] should take more risks like that.
[38:29] There's great software out there.
[38:31] No one should be using, you know, what
[38:33] was the old uh like the QuickBooks
[38:35] predecessor. Like no one wants to use
[38:37] old software. Like there's a competitive
[38:40] advantages to using new stuff. So why
[38:42] why are we stuck in the past as a
[38:44] profession? There's great products like
[38:46] what you're making. Um Okay. So that's
[38:48] amazing. So you got your first customer.
[38:50] I'm grilling you a ton. I hope you're
[38:51] doing okay. I'm not wearing you out yet.
[38:53] Yeah.
[38:54] It's just fun getting to hear about what
[38:57] is that? You've you've been there for
[38:58] three years now. So, what's been that
[39:00] journey like? I'm not going to ask you
[39:01] every day of every week, you know, but
[39:03] um even though I want to. Uh what is
[39:06] that what has that journey been like?
[39:07] Where are you guys at now from getting
[39:09] that first customer? That what's that
[39:11] change been like? Uh it's been a lot. I
[39:14] mean, the first really I want to say
[39:17] like year, year and a half
[39:19] in some aspects. I almost feel like it
[39:21] was a little bit easier because it was
[39:22] just me and a bunch of engineers at the
[39:25] company. So I really got a play in what
[39:28] I felt more comfortable doing, which is
[39:30] predominantly product management with
[39:31] like a light sprinkling of productled
[39:34] sales. And so I was like, "Oh, like this
[39:36] is this is great." Like I go into a
[39:38] sales call and I would forget to talk
[39:39] about pricing and I would just go into
[39:41] the demo and want to get feedback for
[39:43] the entire hour that call lasted.
[39:46] Luckily for the type of user we were
[39:47] selling to, they reacted really well to
[39:49] that because they felt like that made us
[39:51] look more trustworthy and they could
[39:53] tell we really cared a lot about what we
[39:54] were building. Um it's not great when
[39:56] you actually want to scale like you need
[39:58] to get a little more organized when you
[39:59] go to market. And after we so we
[40:02] basically then the money that we got
[40:03] through that incubator program was
[40:04] essentially like our preede and then we
[40:06] went and raised a seed round a little
[40:08] bit over a year after getting that that
[40:10] initial preed funding. Um, uh, the
[40:13] firm's Harlem Capital, so they're a DEI
[40:16] focused VC, which is really cool, very
[40:18] values based. And, um, the main focus of
[40:21] using that funding, uh, was to to grow
[40:23] the team and primarily the go to market
[40:25] area. So, we brought in a customer
[40:26] success manager who's an absolute
[40:28] rockstar and a really great, um,
[40:30] founding sales team. And then I had to
[40:32] learn how to manage people. This is like
[40:36] early kind of middle of 2024 at this
[40:38] point. Uh, and that was like super hard
[40:41] adjusting to that. And I can't just hang
[40:45] out with engineers and focus on product
[40:46] as much as I wanted to or was used to.
[40:49] Um, and build out new processes
[40:52] internally and stuff like that. And
[40:53] luckily we've, you know, ironed out some
[40:56] of the kinks on the go to market side of
[40:57] like how to stay organized and also like
[41:00] learning a to let go a little bit for
[41:02] certain things and not always be in that
[41:05] kind of icy mentality, but also try to
[41:07] think of being a good manager. um we're
[41:10] in a really good good place where
[41:11] everyone's able to run autonomously on
[41:12] the go to market side of things and that
[41:14] allowed us to book more meetings, you
[41:17] know, book more demos, close more deals
[41:19] at a much faster rate because we had
[41:21] more people now in the team to do that.
[41:23] Uh and that's been really great for us
[41:24] now. We've grown a lot um kind of in the
[41:27] accounting firm space across different
[41:29] sizes of firms. We're primarily I'd say
[41:31] focused on larger firms for the most
[41:33] part, but we do have some really small
[41:34] even like solar practitioners who use
[41:37] our platform. Um, but ultimately I'd say
[41:39] we we tend to play more like in the top
[41:40] 100 to 200 kind of ranking and we
[41:43] haven't had a lot of traction in that
[41:45] area in particular. So much so that some
[41:47] of the firms we work with are
[41:48] international and we're now expanding
[41:49] international and building out um our
[41:51] product for the United Kingdom for their
[41:53] R&D tax credits. We're not just going to
[41:54] do the United States anymore, but we're
[41:56] also going to go Wow. across the pond.
[41:59] Yeah. Wow. That's that's amazing. So
[42:01] what's how many people do you have now?
[42:02] What and what does that what does the
[42:03] future for Kipsy look like? What's your
[42:05] plans for over the next year? We are
[42:08] What is Claire up to too? Like what is
[42:10] or is Cla kipsy as a or have they merged
[42:12] to make Clarypy or something? You know,
[42:14] that's a good one actually. I'm going to
[42:16] use Claripy. Uh I definitely merged
[42:19] where most of my personal life was
[42:21] focused on work. I'm now learning to
[42:23] unmerge that. Um it turns out that's not
[42:26] sustainable like physically, mentally,
[42:29] and emotionally to do that for multiple
[42:30] years. like you actually have to get
[42:32] regular sleep and exercise and have
[42:34] relationships outside of work ones. Um
[42:38] so I've been really trying to strike a
[42:41] healthier balance just in general with
[42:43] that cuz I do think it has an impact on
[42:44] my ability to perform at work. Um so
[42:47] that's I think something for us like my
[42:49] co-founder and myself
[42:52] to work on. We, fun fact, never really
[42:55] hung out socially
[42:57] um until this year. Even though we meet
[43:01] all the time virtually and we've been
[43:02] working together for insane hours for
[43:04] years now, we never really like
[43:08] hung out as friends, I guess.
[43:12] Um even though I like to think I think
[43:14] we both really like each other, we get
[43:15] along well with each other. Um it was
[43:18] just like laser focus on like again
[43:20] executing just work work and we're
[43:22] realizing it's work can also be more
[43:24] wellrounded. Um and you know just it's
[43:27] going to be a lot more meaningful that
[43:28] way too and so I think that's been a
[43:30] kind of a big area of focus just for us
[43:33] as individuals. Um as a company you know
[43:35] we've grown our headcount about 10
[43:37] people right now and I'm very happy with
[43:41] that. I think when we were first
[43:43] modeling out our growth, it was very
[43:45] much a you add a headcount, you get this
[43:48] much in growth
[43:50] kind of model. Um, turns out you can
[43:53] also optimize more for certain
[43:55] individuals on your team. And if you can
[43:57] do things to better prioritize their
[43:58] time or train them, you can actually get
[43:59] even, I think my opinion, more ROI per
[44:02] head that way. So, I'm very happy with
[44:05] our our group of 10 right now. We'll
[44:06] probably keep it around that size for
[44:07] the time being before we make our next
[44:09] big push. Um, but we've been able to
[44:11] optimize our resourcing to be very
[44:14] capital efficient. Um, which is as an
[44:17] exac accountant I find very appealing
[44:19] because it allows us to control more of
[44:21] our timeline as a company when it comes
[44:23] to fundraising and um, things like that.
[44:25] So that's been pretty good and stable
[44:28] for us. So it's mainly just I'd say
[44:29] around overall revenue growth. um m
[44:32] maturation of the product is a big one
[44:34] going up market and maturing the product
[44:35] for more enterprise level features and
[44:37] part of that is that that international
[44:38] expansion that I mentioned earlier is
[44:40] providing more coverage for again those
[44:42] really large clients that some of these
[44:44] accounting firms are serving where they
[44:46] have R&D all over the world um and a lot
[44:49] of other um just maybe reporting
[44:52] requirements that they need to be aware
[44:53] of or keep track of that our software
[44:55] could help with
[44:58] you know what I love about everything
[44:59] that you said is that once that I hear
[45:01] like a dollar which is just awesome and
[45:03] something you've mentioned throughout
[45:05] the entire conversation is values like
[45:09] you're values driven you've talked about
[45:11] you know recognizing having the
[45:13] self-awareness to recognize that you are
[45:14] looking for some kind of balance not
[45:16] because you're missing out on the work
[45:18] but because you can perform better if
[45:19] you have that balance and um and you
[45:23] keep talking about like optimizing for
[45:24] the team and it doesn't sound and I know
[45:27] so many founders I've met who optimize
[45:29] for headcount optimize for dollar growth
[45:31] trying to get their go IPO, but it
[45:33] sounds like you're doing everything
[45:34] right. Like you're trying to optimize
[45:36] for outcomes for your customers. You're
[45:38] trying to out optimize for your team's
[45:40] dynamic and still like be have financial
[45:42] rigor like not just to make decisions
[45:44] based on optics but actually on outcomes
[45:46] and hats off to you. That's awesome.
[45:48] That's a very rare combination in
[45:50] leadership and I'm sure it took a lot of
[45:53] sacrifice to get there. So we made some
[45:55] very expensive mistakes to get to that
[45:57] that realization. um probably overhired
[46:00] a little too quickly. we spent a lot of
[46:02] money that we didn't need to spend in
[46:03] certain areas of the business um because
[46:04] we were kind of told that was the norm
[46:07] or you know you you're on LinkedIn you
[46:09] kind of see all this dialogue and it's
[46:11] it's like a playbook right um and we
[46:14] realized after taking a few steps back
[46:16] like what is actually true to us as an
[46:19] organization true to our users and maybe
[46:22] it's not applying this more standardized
[46:24] play that could work really really well
[46:26] for like maybe other B2B SAS companies
[46:29] but doesn't necessarily work well in
[46:31] space because admittedly selling into an
[46:33] accounting firm is going to look really
[46:35] different than selling into some other
[46:37] type of organization and we need to know
[46:40] our space well enough to have the
[46:42] confidence and how to execute off of
[46:44] that type of a playbook and recognize
[46:45] that it might be different. Um, but we
[46:47] definitely
[46:49] went through some growing pains I'd say
[46:50] in 2024 to figure that out and make
[46:53] adjustments and then get comfortable
[46:55] with like what actually is going to be
[46:56] like our approach to selling and also
[46:59] building the company.
[47:02] So, it was intentional to stay lean to
[47:04] stay to not get more capital, stay in
[47:08] that seed space, right? Yes. Yeah,
[47:10] definitely. Um that that was one thing
[47:12] like I fundraising is a very unique
[47:14] experience and um some some aspects I
[47:18] really enjoyed other aspects I did not
[47:20] enjoy. Um,
[47:22] it was a just a very different
[47:25] experience in like building software and
[47:27] the day-to-day and the shift from having
[47:28] to like step away from building the
[47:30] product and talking to your end users to
[47:31] going and pitching all the time to
[47:33] investors
[47:34] um was just like you spent your day
[47:38] doing very different things
[47:39] fundamentally. And I'm very happy that
[47:42] we got the funding that we did. I love
[47:43] our current investors. Um, but it was
[47:46] also very distracting to fund raise. Be
[47:48] perfectly honest. It's really hard to
[47:50] just try to run both things in parallel.
[47:52] Something something has to give
[47:54] somewhere to make room for the bandwidth
[47:56] for me to fund raise. And I feel like
[47:58] where we're at right now from a
[48:00] development perspective is so much more
[48:02] crucial for us to stay focused and
[48:03] executing on than for us just to go and
[48:05] raise capital right now. And the good
[48:07] news is we we don't need to raise the
[48:09] capital. So if I were to prioritize my
[48:11] day, I'm going to prioritize what can I
[48:14] do to make the product better so I can
[48:16] make the lives of my employees and our
[48:18] end users better as a result.
[48:22] Yeah. And not enough people focus on
[48:23] that. Not so many people I know are
[48:24] chasing funding. And my only my
[48:27] challenge to everyone is why chase
[48:29] funding if you can finance it yourself?
[48:31] If you can figure it out how to make
[48:32] money in your own business in order to
[48:35] not need financing, generally financing
[48:38] is going to be the most expensive way to
[48:40] get raise money to get money in your in
[48:42] your pocket. So look at look at just
[48:44] building it organically after you have
[48:46] your initial preed funds or seed funds,
[48:48] right? You're doing that, right? And
[48:49] it's not easy. It's not easy because the
[48:51] world's everyone else is telling you
[48:53] something different, right? Everyone's
[48:54] like grow fast. Throw money on the throw
[48:57] like throw money into the engine and
[48:58] just watch it burn and it'll go faster.
[49:00] But that's not honestly that's not right
[49:02] for most people. It honestly burns a lot
[49:04] of people out. Um yeah. So what are you
[49:06] doing from that from that from that
[49:08] lens? What are you doing uh to take care
[49:09] of yourself? Like it sounds like that's
[49:10] a priority upcoming. And taking care of
[49:13] yourself, I want to be clear actually
[49:14] helps businesses because then you can
[49:16] operate better, right? Like having a CEO
[49:18] who has some time to exercise and like
[49:21] take care of their health and mental
[49:22] health is like it that's how you can
[49:25] think better and execute stronger. So
[49:27] what are you doing for yourself? Um,
[49:29] ironically actually one of our investors
[49:32] um the for Harlem who led our round for
[49:34] the seed round has been very good about
[49:36] like pushing me or also co coaching me
[49:38] to like think more holistically about my
[49:40] life. Um, and that's something I've been
[49:44] been working on is like making more time
[49:45] to like I block time in my calendar to
[49:47] work out. Um, I disconnect pretty much
[49:50] entirely on Saturdays from work. So
[49:52] that's also been good too. So just again
[49:54] building in space for yourself um to
[49:57] have to just have the disconnect or time
[49:59] to focus on areas of your life um have
[50:01] been I think really really helpful for
[50:04] me. So I wouldn't say like I've picked
[50:06] up like a great hobby that I do
[50:08] consistently. Um although I do like to
[50:10] do random projects like we got a
[50:13] custommade claw machine um for the
[50:16] company just cuz I thought it'd be fun
[50:18] to have at a conference that we were
[50:19] sponsoring. Um, so I feel like I do fun
[50:23] side projects. They happen to be
[50:24] interrelated to work, but I get to flex
[50:26] in different ways. And that's part of
[50:27] the reason why I love my job so much.
[50:29] Um, is I get to wear different hats
[50:31] every day and do different things I
[50:33] wouldn't otherwise get to do at like a
[50:35] company like Deote. Like I I wouldn't
[50:37] need to touch anything related to to
[50:38] sales or marketing or even product
[50:40] development for that matter. Or build a
[50:41] claw machine. Yeah. Exactly. Yeah. Or
[50:44] like find a random dude on Etsy to make
[50:46] you a claw machine. Right. Like so
[50:49] that's awesome. Can you send me that?
[50:50] Because I am strangely addicted to claw
[50:52] machines. Like do not give me money in
[50:54] my pocket around a claw machine in
[50:56] Taiwan allow like a hundred bucks when I
[50:58] was in the night markets. I was like go
[51:01] through money. I don't know why I love
[51:02] those things so much. Especially
[51:03] collecting like little stuffed animals
[51:04] for my kid is like the best. It's it's
[51:06] so fun. Well, I got a bag of like 200 of
[51:08] them that we have left over from the
[51:10] event. So, if you're in need of any
[51:12] little plushies, we have a plethora. Um
[51:15] Okay. But yeah, it's pretty fun
[51:17] actually. I've learned all these
[51:18] different things that you can do like
[51:20] you can code the machine to give like a
[51:23] certain like payout rate make it easier
[51:25] or harder for the user. I knew it. I
[51:28] that's what I was wondering why. Yeah,
[51:30] there has to be a payout rate because
[51:31] these things are impossible half the
[51:32] time. No, it's uh you're you're like
[51:35] probably guaranteed to lose money if you
[51:37] if you go into like an arcade and try to
[51:38] use claw machine. But um if you already
[51:41] come up, you can practice to really hone
[51:42] your We got to go on a hike on the
[51:44] mental health like on the values-based
[51:47] uh health note. Let's go on a hike. I
[51:48] would love to play some claw machine,
[51:51] too. Funny enough. Yeah, that'd be a
[51:52] blast. It's so funny you made one,
[51:54] right?
[51:56] But yeah, I mean like that that part's
[51:57] been nice, actually. Um and so I will
[51:59] say like even like we're kind of like
[52:01] anti like we're not fundraising right
[52:03] now because we don't need to. um like we
[52:07] wouldn't exist without the capital that
[52:10] we raised from multiple investors and
[52:13] like the relationships with those
[52:15] investors that open up new doors for us.
[52:17] So I guess it all kind of comes back
[52:19] full circle in a weird way. Um and like
[52:22] I I just feel like with fundraising you
[52:24] should be intentional like you should
[52:25] know like there's a reason a strong
[52:27] reason like why you're doing the raise
[52:28] at that time and it's really to kind of
[52:29] level up or go to the next step with
[52:31] your company. Uh but for us like it
[52:33] allowed us to to you know one exists MVP
[52:37] development was the first round second
[52:38] round was really to scale go to market
[52:40] um which was huge for us but I I've
[52:42] really enjoyed kind of like developing I
[52:46] guess my relationship with some of our
[52:47] investors. Um like I said like Harlem
[52:52] we have a monthly check-in. the first
[52:54] thing they always open with is like like
[52:55] what's going on in your life and they've
[52:58] been pushing me to not open by talking
[53:00] about work but like something else that
[53:02] I'm looking forward to in my personal
[53:04] life and like almost like kind of
[53:05] coaching me on that. Um they've also
[53:07] encouraged me to like find a coach uh to
[53:10] help with things like learning to get to
[53:12] delegate or public speaking or certain
[53:14] areas that you know I could level up in
[53:16] as a founder of a growing company. And
[53:19] so that all again has a trickle down
[53:21] effect I think in my again holistic
[53:23] personal professional intermingled life
[53:25] at this point and that's been I think
[53:27] really really positive to see.
[53:31] Yeah that's amazing and I'm glad you're
[53:32] getting that coaching and everyone can
[53:34] everyone use that and you're leading any
[53:36] organization. I always wish because I I
[53:38] joined an executive coaching program and
[53:40] I learned the old executive coaching arm
[53:42] but I met so many people who were like
[53:44] ex CEOs who who do something similar and
[53:47] it's so valuable. I wish I learned these
[53:48] things years ago. I had people in my
[53:50] corner who were challenging me to mentor
[53:53] better, lead better, take care of
[53:54] myself, look at like having people to
[53:56] give you the right questions to work
[53:58] through things yourself and challenge
[54:00] you to think differently is so valuable
[54:02] and can like span and improve your
[54:05] ability in all areas of your life. Yeah.
[54:07] Yeah, definitely. And like that could be
[54:09] through like you know finding a good
[54:11] coach recommendation like from your
[54:13] investor for example, right? like
[54:14] they're talking to so many different
[54:15] portfolio companies on any given day and
[54:19] a lot of the founders in similar stages
[54:20] as you probably deal with similar
[54:22] problems. Um they've seen that right or
[54:25] you have a network of like maybe like
[54:28] repeat founders that you know um in a
[54:30] similar space you could go to for
[54:32] mentorship um or a coach right that's
[54:34] been a founder before who could help you
[54:36] know share their experiences and lessons
[54:39] learned and kind of help guide you
[54:40] through that process you're going
[54:41] through now. I think there's a lot of
[54:43] great opportunities for different people
[54:44] in your life or people you can bring
[54:45] into your life to help guide you through
[54:48] this process.
[54:50] Yeah. Well, we almost had an hour
[54:52] already and I've been talking your ear
[54:53] off, so I don't want to waste your whole
[54:54] day. You're very busy and you need time
[54:56] for yourself, too. I'm curious what what
[54:59] do you wish I asked that I didn't is
[55:04] Oh,
[55:07] I don't know. I think this is pretty
[55:08] great. I mean, I just hope it's useful
[55:09] for people.
[55:12] I think it's inspiring and people are
[55:13] going to learn. I think people are going
[55:14] to learn a lot. There's a ton there a
[55:16] lot of takeaways. I I just wish I your
[55:19] brain I feel in mine could just meld
[55:21] with some of the take like great
[55:22] takeaways. Maybe it's the accounting
[55:23] background, but like seed money
[55:25] investors are great, but make sure it's
[55:27] more than just money. Make sure you're
[55:28] building relationships. Make sure you're
[55:30] getting the right coaches in your
[55:32] sphere. And don't just chase the
[55:33] dollars. customer first mentality,
[55:35] product market fit, like make sure that
[55:37] your customers actually want to purchase
[55:39] uh want to purchase something that
[55:40] you're offering and make sure you're
[55:42] constantly thinking about them. Making
[55:44] sure you're taking care of yourself as a
[55:46] leader um and making sure you're looking
[55:47] out for your people. Something that
[55:48] stuck with me is like that your
[55:49] valuesdriven leadership and I really
[55:52] admire that that throughout the
[55:54] conversation you kept talking about like
[55:55] values and how you care about your team
[55:57] and the de DEI focused investors that
[55:59] you found like all that stuff. I think
[56:01] this has been a hugely valuable
[56:02] conversation, Claire. So, Oh, thanks.
[56:05] No, I appreciate that. Yeah. I can't
[56:06] think of anything else like really maybe
[56:08] that would stand out just like Yeah. If
[56:11] you're the founder listening to this,
[56:12] you have a really good employee or you
[56:14] found like that really special hire,
[56:16] like take good care of them. It's hard.
[56:18] It's really hard to find good people.
[56:19] It's hard hard to find good investors,
[56:21] good employees, good customers to work
[56:23] with. And if someone's willing to be
[56:24] honest with you and vulnerable and share
[56:26] their feedback, like that's a really
[56:28] special relationship. Um, and like that
[56:30] type of truth is immensely valuable when
[56:33] you're building a product. So I feel
[56:36] like that translates directly to dollars
[56:38] on my end. And as long as you can
[56:40] maximize getting more input from a
[56:42] larger group, that's one of the best
[56:44] ways you can kind of aggregate all the
[56:45] feedback to build a really great
[56:47] solution that people will find and love.
[56:50] Oh, that's great. It's a great place to
[56:51] end, but I got to fire drill three
[56:53] questions for you and then we'll be
[56:55] done. Okay. Sweet or savory? Oh god. H.
[57:02] Oh.
[57:04] Oh no. It's dinner time, too. Yeah, it's
[57:07] it's Yeah. Uh, it's hard. I love boba
[57:11] and I love fruit, but I think savory has
[57:13] to win because cheese like any like just
[57:17] cheese crisps, like any anything like
[57:19] just cheese related wins. So, I'm I'm
[57:23] going have to go with savory just for
[57:24] that. Okay. Okay. Good. What's your
[57:27] favorite dessert?
[57:29] You seem like a sweet person based off
[57:31] that second question. Yeah, I know. I
[57:32] know. I'm just trying to keep you on
[57:34] your toes. I'm You're in the savory
[57:36] mind. I'm going to flip it.
[57:39] Man, that's really hard. I
[57:45] really like the berry chantelli cake at
[57:48] Whole Foods. Oh my gosh, that cake is
[57:51] Okay, maybe I'm having a sweet tooth
[57:53] today, but maybe you called me on it.
[57:54] That cake, that cake is delicious. Yeah,
[57:58] I like 700 calories a slice and it is so
[58:01] worth it. 700 grams of sugar a slice,
[58:04] too. It's just cond Oh, but the p Yeah,
[58:06] that flavor I nail. So many people love
[58:08] that cake. I don't know what they did
[58:09] there. They put crack in it or
[58:10] something. Um, what is one piece of
[58:13] advice that everyone gives that annoys
[58:16] you or you wish they didn't?
[58:23] Ice baths. I don't know if that counts.
[58:25] That's like too weird. But no, it count.
[58:28] You know what's so funny is I got I was
[58:29] in that ice bath kick for a while doing
[58:31] cold showers in winter here. No, don't
[58:33] be sorry. I did it one morning to where
[58:36] I was feeling a little off. Turns out I
[58:38] had COVID really bad and I did an ice
[58:40] bath that morning and it totally almost
[58:42] KOed me. I had to go to the hospital and
[58:44] the doctor was like, "What? What did you
[58:45] do?" And I was like, "I went in an ice
[58:46] bath." Like, "What are you, an idiot?
[58:47] Don't don't go in an ice bath when
[58:50] you're sick." I'm like, but they it's I
[58:51] suppose the YouTubers, you know, they
[58:52] told me that it increases immunity and
[58:54] they're not doctor. What are you crazy?
[58:56] Don't be in cold water.
[58:59] Yeah. Yeah. So, I'm with you. Lesson
[59:00] learned.
[59:02] Don't take ice baths unless you really
[59:04] like want it just to kick up. Yeah.
[59:06] Yeah. Yeah. It it will not solve all of
[59:08] your problems. Some of them it probably
[59:10] can actually, um, but it will not solve
[59:12] all of your problems. So, that would be
[59:14] the one piece of advice that I find a
[59:16] little a little annoying.
[59:18] Yeah. Fair. I I think that's a good
[59:20] place. It's a good place to close.
[59:21] Claire, I really appreciate you. This
[59:23] was a ton of fun. I'm serious. I want to
[59:25] find time. I put a reminder to keep
[59:26] bugging you about going on a hike
[59:27] sometime the next time in the area. And
[59:29] I'm just rooting for you. So, if there's
[59:31] anything I can do, would love to have
[59:32] you back on and see where you're at in a
[59:34] few years, even just keeping your
[59:35] 10erson team, but just global. Who knows
[59:38] where you'll be, but I'm so excited for
[59:39] you and so impressed to see where you've
[59:41] landed. So, thanks for coming on. Thanks
[59:42] for having me, Devon. I appreciate it.
[59:44] Yeah, of course.