Startups, AI, and Radical Honesty - Sasha Pasulka - Elka AI - Episode #46

If it can do good work 70% of the time, that's gonna be good enough for people to appreciate it.

Welcome to Not Another CEO Podcast. I'm your host, David Politis. Every week we talk to inspiring leaders and get the true stories, the ups and downs, the lessons learned, and come away with actionable advice for our own journey. Welcome back to another Failing Forward edition of the Not Another CEO Podcast. This is the show for the rest of us where we explore the other side of entrepreneurship, where we listen to the journeys of those who, like me, gloriously fought but lost, and where we hear the lessons of those with the guts to start something that maybe just didn't work out. Today I'm honored to introduce Sasha Pasulka, a serial founder, longtime marketing executive and software engineer. The arc of Sasha's career is fascinating. She started as a software engineer working on aerospace systems at Northrop Grubman, including the F35 Joint Strike Fighter, which I don't know if we're going to talk about today, but is pretty awesome. She's a digital media founder. She founded and served as CEO as of Evil Beat Gossip, one of the earliest and most successful independent blogs of its time. And she grew to over 10 million monthly readers before she exited the business. Since then, she's been a marketing executive and leader at fast scaling SaaS businesses including Tableau Integrate and Splash, helping these companies navigate critical inflection points. And most recently, she was the CEO and co founder of Elka AI, an innovative B2B martech technology company which had a really interesting AI product that she's going to talk to talk with us today about. And beyond her extensive operational and leadership experience, Sasha is also a thoughtful voice and mentor in the tech ecosystem. She's written for many outlets including GeekWire, she's spoken at south by Southwest and TedX, and she's an active mentor and advocate for rising leaders at places like General Assembly. I'm just really thrilled to have Sasha on the show today, so please join me in welcoming her and Sasha again. Just thank you so much for joining us.

I'm so thrilled to be here. Thank you for having me, Nick. And you did your research. That was such a generous introduction. Thank you.

Of course, of course. Well, I, I try my best, I won't lie. I have my, some of my own help with, with AI on, on the, on the, on the deep research, but I write the intros myself so. But let's, let's jump into it, I think. You know, first question for you today, just tell us, you know, with the most recent company. Tell us about your aha moment. Right, like that moment where you just knew you had to go out and start this, this new venture.

Yeah, yeah. There's a number of ways I could approach that. Approach answering that question. Right. But I think as you mentioned, I'd been a serial entrepreneur, but I hadn't, hadn't founded anything in quite some time. I just hadn't felt inspired to. I couldn't think of anything that I wanted to work on myself. People kept asking me, when are you going to found something again? And I just was like, what am I going to found? And if I had to put one aha moment on was when ChatGPT released publicly. I think about two and a half years ago. I think it was late 2022 was when ChatGPT released publicly. And that blew my mind. It just absolutely blew my mind in a way that technology or software at least hadn't resonated with me in a long time. And I thought to myself, okay, now we can start solving some problems that weren't solvable before, because I come from the world of marketing, and in most cases it's challenging to build technology that's fundamentally disruptive in marketing because so much of what marketing is, is consuming and outputting human language. And that wasn't a strength for computers until very, very recently as these LLMs evolved. So as I was playing with ChatGPT in the early days, I just, I got excited again and I started to say to myself, oh my gosh, now we can solve some of these marketing problems that were not solvable with technology previously.

Yeah, amazing, amazing. And I think those problems that you're, you're alluding to, I would, I would assume those were, those were problems that you had experienced quite a bit as a, as a leader and as a, as a marketing person throughout your career.

As a leader and as an individual contributor. I mean, I can give you kind of the little pitch for Elka and the problem we solved.

Yeah, sure, let's hear it.

So when I was at Tableau, this is the first time I really deeply encountered this problem. When I was at Tableau, we would have these conferences around the world and they would be like three day conferences with five different session tracks and hundreds and hundreds of speakers. And we would pay to record a lot of those sessions, particularly the sessions with the customers. We do a bunch of on camera customer interviews. And we would have literally hundreds and hundreds of hours of footage from just one event, right. That we paid money, a lot of money to have the AV on this. And what ends up happening is marketing tries to go into that footage and edit something interesting. Maybe you'll put the whole sessions on YouTube, but nobody watches a 60 minute session anymore. So just a fraction, just a fraction of those hundreds of hours of video end up getting used by either marketing or sales. And meanwhile, particularly in Tableau had at its North American conference, often 100 customer sessions over three days. Right. And you know, I might get a call from one of our strategic sales guys, like a top sales guy saying, hey, Sasha, I'm trying to close an oil and gas deal, but I've got someone on the buying committee who does not think Tableau is going to be easy enough for his guys in the field to use. Do you have any customer evidence? Someone in oil and gas talking about ease of use? Right. And I'll think to myself, well, gosh, we had two customer speakers last year from the oil and gas. And so I'll grab a coordinator level higher and I'll tell her, go replay those sessions today. If they mention anything about usability, clip it and we'll send it over to John. You know, and for the senior guys and gals doing the multimillion dollar deals, I would pull someone out of her job for half a day and say, go listen to all the oil and gas sessions and grab anything about ease of use. Right. And that would help, help those guys and gals close those deals. But for the smaller deals or even the mid sized deals, I wouldn't do that. I would say, you know, search our website, see what we've got. But I'm not going to take someone out of their job for half a day to solve this, you know, to try to close a $10,000 deal. Right, but the content's probably there. The customer evidence the salesperson needs is probably there. They just can't find it. And no, you know, it hasn't been cut. Nobody knows where it is. So what we did at Elka, and this is a problem, by the way, that tons and tons of B2B companies have and tons and tons of revenue teams have, where they're just sitting on thousands and thousands of hours of this kind of owned footage that could be used, closed deals could be used in a customer evidence capacity. And it just isn't because there's no good way to do it, because it took so long for a human to go through and edit and tag all that content. So what Elka did is it allowed you to upload that footage. We would go through it, we would find the highlights, we Would clip them, we would tag them eight ways from Sunday and we put them in a library for your sales team to search so they could go in and, you know, search by industry or search by keyword, or search by person and see what we had on that topic.

Amazing. I mean, I totally can see why AI could be such an unlock for a product like that. And as someone who spent a lot of time doing B2B startup video, the problems you, you were solving, you know, you know, you're kind of talking a little bit about the product and there's so much that I want to ask you, but maybe just talk to us a little bit about how you then like approached building the product. Right. Like the, the alpha phase, the OR and, or the beta phase. Like what did those programs look like? And kind of share with us a little bit about that journey.

Yeah. So I'll give a shout out to my technical co founder, Jason Meltzer. He was fantastic and couldn't have done it without his help. So I don't want to take full credit for any of this, but I will say what we built in the time we had with the money we had. I'm so impressed with us. I'm really proud of it and I'm really proud of the team we brought on initially three people. I think it's really important when you are building software for a sales and marketing audience that it has to look and feel good. It has to be built like a consumer product because a sales and marketing audience is different from a dev audience. They want their software and they expect their software to look and feel effortless, to be super intuitive. And this was, you know, not a super complex product at its start. But I wanted a library that felt really, really intuitive. I wanted search features that felt really, really intuitive. So one of my first hires was ux. I thought it was really important to bring in UX and get it right the first time and not have to fix it later. So was referred from someone in my network to a guy named John Billet who did our UX and helped product. He was amazing. And then we also brought in a backend dev and a front end dev and we just, we just started creating this thing. It took probably five months, I think, to get to kind of an alpha right where we had something up and running that actually kind of sort of maybe worked. And then I think we probably moved to the beta phase a little too quickly. But we were also kind of up against the clock in the sense that we were running out of money. So we moved to beta. There were tons and tons of people who wanted to be in the beta. We had.

Sorry just to cut in. So sorry to cut in and sorry to interrupt you. So with alpha, like, was that internal testing? Did you have like, alpha partners at that phase as well, or like, and, and then you were expanding. Like, what was that dynamic? Like?

Alpha was internal testing and a handful of like, friends, right? It was just like a handful of friends. It wasn't probably, in retrospect, it wasn't as comprehensive as it needed to be before moving to beta. But again, also, you know, we were up against the clock and I had hoped that having a beta with actual named enterprises in the beta could help with fundraising. So there was that pressure that, you know, pushed me to open the beta sooner than the product was probably ready for it.

Those, those competing pressures are always, are always difficult to navigate. You know, obviously there's a lot of AI, like AI companies today. You're really, I think, part of one of the first big waves of these, these companies. What, what's different? Like, what do you think was different in your alpha and beta journey as an AI company? If anything, you know, like, were there, were there unique considerations or factors at play for you kind of building on this new technology?

Yeah, well, I think the operative word here is non deterministic. Right? It's, it's very, very challenging to put an LLM wrapper kind of product into production because, and particularly, you know, trying to do it, you know, a year ago, right. These products have gotten dramatically better even since we were running, since we started, like building this thing and opening it up. It. I had gone in with the premise that if this thing can work 60% of the time, 70% of the time, that will be helpful enough that people will find value in it and, you know, we'll continue to improve, we'll continue to close that gap. But I had had this kind of hypothesis that, that if it can do good work, 70% of the time, that's going to be good enough for people to appreciate it. But for a number of reasons, users would run into issues. Some of those issues had nothing to do with the AI and were just issues we didn't catch in our own testing and could have been fixed with more time. But a lot of times they ran into issues with the AI, that the AI just didn't do what they needed. And because I think the beta, they hadn't, I didn't do. They didn't, they hadn't paid to be in the beta. They had, you know, they were participating, but they hadn't paid for it. And so I think because they didn't have any skin in the game, when they would run into a couple of problems with the AI, they'd kind of just abandon ship. Right. Just be like this, this doesn't work. I'm not going to play with this anymore. And you know, that was, that was maybe a misstep on my part. I did try, I did personally onboard every beta customer. So I didn't just turn on like hand over the keys. I made them get on a 45 minute onboarding call with me where I walked through everything and I trained them and everything because, you know, I wanted them to be equipped to succeed. But you just don't know what the AI is going to do, you know, And I think a lot of our beta customers got quickly frustrated when the first kind of thing went wrong and weren't, didn't have any reason to stick it out.

Yeah, I mean that's a, that's so hard because that's like, to an extent, like the point of your beta program is to figure out what is going to work and what is not going to work. And so, I mean, you probably could have spent two years trying to get the AI to act in a really, really consistent way, but no founder has time for that.

And I actually think what would have been more effective again if we'd had the Runway was just waiting for the AI to get better. You know, it just keeps, I mean it's, it's so much better today, so much better today than it was when we launched our beta. And you know, we needed it to do certain things with math. Right. Like we needed it to work with time codes and understand how to do a 30 second clip instead of a five minute clip. Right. And we, we kept running into issues where it's just that thing just couldn't do math. Math was hard for, for the LLM and I think even in the past year it's kind of data literacy has, has increased. Yeah.

So I mean there's so much that I, I, I want to ask you about and talk about, but you know, we've kind of already started to get into your journey, but I think maybe just to rewind back a little bit, like what were your like core motivators and drivers for this? Right. Like, I think as having done it myself. Right. Like founding entrepreneurship, it's kind of this crazy irrational act, at least in my opinion. Like why, why go on this journey in the first place?

Well, probably for starters, because I'm A little bit crazy and irrational, right? Like you got, you got to love the game. You've got to just love the right. And I, you know, I would say I have, have all sorts of, not all sorts of, but like I'm scared of heights. I won't go on roller coasters. Like I have all sorts of fears in the physical world, but in the world of abstraction and kind of ideas and companies and that kind of thing and, you know, just life pathways, I, I don't think I have the same fear that I think and I think you would agree, I think you'd see that across a lot of founders where I don't spend a lot of time worrying about, well, what if I fail, right. I just, I just do the thing because it feels like that's what I'm supposed to do right now. And it does involve a lot of fearlessness. But I think a lot of us are wired in a way that it's scary maybe, but it's not terrifying. It's almost like you have to do it. And I'd spent. So I'd built a successful company in my 20s and sold it, and then I'd spent Most of my 30s working for other people for some really cool companies. I mean, I was lucky, but I was tired of working for the people who could raise the money but maybe weren't the most qualified to be running the company. Right. And, and it wasn't everyone. And I'm not going to name names, but you know, sometimes, not always, but sometimes this skill set of who can raise the money and who can run the company, they don't always overlap in a person. And some people are very, very good fundraisers who have no business actually leading a SaaS organization. And I started thinking, you know, like, I just want to do it. I just want to do it. Like, why can't it be me? Why can't I just do it myself? And I found out why, because I can't raise the money because I, I hundred percent have the skill set to build the business. I feel like we did a phenomenal job where we got to. I'm super impressed with our team and with what I was able to achieve, what my co founder was able to achieve. But ultimately we couldn't get to revenue and we needed more funding. We needed. Not a ton, but we needed more funding and I couldn't get it. I didn't have that skill set. Overlap.

Yeah, yeah. I mean that's just that set of points is, is, is fascinating to me. You know, the, the difference between the, let's say the, the, the builder and then the person that can, that can go ahead and sell and, and what skill set is like more important and better. And you know, especially in today, you know so much, we speak so much about real leadership, authentic leadership, you know, leading with your heart, all of those things. And at least from, from my personal experience, I felt very comfortable like in that mode. And then where I didn't have necessarily. Well, I mean eventually I had problems like raising more capital, but like we also didn't have the metrics to back it. But where I struggled in the fundraising, like part of the game was just almost like the pure selling, like, just like the crazy Adam Newman style selling that like, let's say throws caution to the wind. And I don't think every founder CEO is always there, but there's like some elements of that that's valuable and it can be hard to navigate probably one way or the other. Like if you're really good at one, you probably struggle more with the other and, and, and vice versa.

I completely agree and I think there's even, yeah, I think some amount of not, not tethering yourself too closely to the whole truth can be valuable in that process. And what I have found about myself is I tether myself to the whole truth and I really struggle to tell, you know, tell a story that's maybe bigger than the reality today or. Yeah. To kind of answer anything in a way that isn't authentic. And I, I think if you want it fundraised, it's almost just part of that game. You've got to, you've gotta, the VCs expect you to, they expect you to lie. I mean, they expect you to lie a little bit. They really do. And if you don't know how to play that game or you're not willing to play that game where it's like they lied too, right? Everyone's just lying to each other and at some point $50 million gets exchanged. I don't know how it happened, but it's not through like sheer authenticity.

Yeah, well, I mean like it's, it's a, it's a tough game and it's as much, I think as art as it is a science. Right. Because it's like a pure bold faced lie will come back to bite you for sure. But there's like some level, I think to, to, to quote you, like, of fibbing. Right. That's probably, I mean it is just incorporated into the cost of doing business. And so, and how do you find that? How do you find that right balance. You said something earlier about kind of timing, and it's the timing of this technology, and obviously it's. It's rapidly changing. And, And. And how. To an extent, there was a driver there in what happened. Like, to an extent, you're kind of talking about, like, the element of luck, like, timing and luck. Right. Like, how do you think about. How do you think about the role of timing and luck and all of this versus agency and like your own. Our own role as founders and CEOs in our own journey?

Yeah, I mean, they say you make your own luck, but I. There's also just luck. You know, I've had a lot of luck in my life. I've had so much luck in my life. I think Jason and I, my co founder and I, we wanted to be early in this space. We intentionally wanted to be early in this space. We wanted to have something in place so that as the underlying technology evolved, we could evolve with it and we could kind of just be on that wave and ride the wave of the underlying technology improving and becoming cheaper and all of that. I mean, that was an intentional decision that we made. It's possible we were a little too early. Again, I think if there had been a way to extend Runway for another year, we would have been in a very different situation. I mean, part of our plan was contingent on, you know, being able to raise a little more money. But I don't think. And you know what? I don't want to say, like, we were unlucky because we were able to raise the initial angel round. That got us to obey that. Right. And I'm, you know, I'm so grateful, so grateful and so lucky that people bet on us in the angel round. That was. That was luck to some extent, that we got that money, but then we just didn't quite get the luck to get the rest of it, and we didn't. The underlying technology wasn't quite where we needed it to be yet.

Yeah, I mean, it's definitely both. There's a role of both agency and luck. I don't. I don't know what part is what, but there's, you know, it plays a part in all of our journeys and all of our stories. You know, when you think about your journey, you know, from beginning to. To. To. And, you know, are there any key forks in the road or paths, pathways you took that you, you know, you think a lot about that. They think took the business in one direction versus the other.

I think we made some really good hires. If Anyone is looking for contract help on any of your projects, ping me, I'll give you some names. I think we did a really, really good job of hiring and that was a game changer in a positive way. You know, having, having a players on your team changes everything. I think I had a really good co founder in Jason and that is a huge plus. We the, the people who bet on us early on, who were willing to give us money based on an idea and who we were, that was me that the hugest fork was when we were able to raise our angel round and it was like, oh my gosh, we have, we have money now. We can actually. We'd been dreaming about it and we'd been kind of thinking about how we'd architect it and we had a little bit of the software built out, but this allowed us to really kind of finish that job and get that data out. So that was a huge fork in the road. Jason and I decided we weren't going to relocate to San Francisco or anything like that, even though a number of people recommended it. I think, you know, I don't wish I lived in San Francisco now. I think staying, we, we both live in Phoenix and I think that was the right choice for us. But it did really. I think being in a city like San Francisco or LA or New York or Seattle is really helpful for fundraising compared to being in Phoenix. Phoenix is a tough city to fundraise from. So that was definitely a decision we made that I think had an impact. And then there were just lots of people who gave me lots of little pieces of advice. Right. That was, that were. That really helped me move the needle or move forward. But I would say generally from start to finish, I was still executing on the vision I'd started with. Like we, we built the V1 that I had initially conceived. Like we pretty, we didn't pivot and it was, we didn't pivot much.

Yeah, I mean you had, I mean it sounds like you had issues with, with kind of design partners, beta partners, like ghosting. You know, I struggled with the same thing and managing that dynamic is really difficult, but it sounds like that was more around like kind of bugs in the underlying like quality of the AI technology. Not necessarily like the promise of what you were, what you were trying to build or the core problem.

I think we went to beta with too many bugs and we didn't do a thorough enough alpha and I think, you know, there were the issues, there were the issues with the non determinism of the AI, there were the Issues with the kind of data literacy of the AI, the, its ability to just like do math. But no, there were also just bugs. There were bugs that had nothing to do with AI that we just hadn't caught in our testing. And those were frustrating too. Those, I mean I, I think, you know, I'm not saying like everything would have been perfect if it hadn't been for the AI. We definitely had more bugs than I would have liked in a beta that could have been resolved had we caught them.

Yeah, yeah. I mean I was the same way. I was always so annoyed every time we, a customer would find a bug and then my co founder Chris would be like, nick, this is part of the process.

So I, in retrospect, but I'm a perfectionist. I'm sure you are too.

Of course, of course. I mean I, I just, I, I, I, that's, that's a, that's a really, really tough one. I think your experiences with a, like with the non determinism of an AI product is, is unique and is different and it's something that I think more and more founders are going to have to try to navigate.

Yeah, and we tried so hard by the way. We, we built in all sorts. We tried so hard to solve for it. Like we had all these sanity checks, right? Like we take the output out of the LLM and we had all these ways to like sanity check it and send it back if it didn't pass the sanity checks. And I mean we tried so many different ways of making this thing just a little more deterministic. We didn't, we didn't, we didn't land on the perfect answer. And I don't know that anyone has yet.

Yeah, I would agree with you on that one. You know, you've spoken about it a little. You know, you know, your co founder, your team, other folks, like who are, you know, there's a lot that goes into this journey. So many ups and downs, you know, who are the folks maybe that just that you haven't mentioned yet that were part of your support system or talk about your support system as a founder, CEO and the role they played in your journey.

Yeah, well, so, yeah, definitely. Shout out to my co founder, shout out to my team. They were fantastic. I think the, again, like the first people that were really game changing were the angel investors who bet on us early not just because they gave us money, but because they gave us confidence, they gave us that morale boost that they would bet on us. So those were huge people. But you know, it was surprising, kind of who really showed up. You know, I talked to some old bosses, you know, some who had founded companies who really made the time to advise me and to guide me through fundraising and to guide me through building the product. There was a guy I'd worked with at my job before I started this company. He was head of legal, and he started his own company, a software company, at the same time I was starting Elka. And so we were facing a lot of the same problems at the same time, but he understood so much more about the legal and financial side of it than I did. And he would get on a call with me like every two weeks and, you know, just walk me through the basics of how do I even do this. Like, you know, I didn't understand that you could just do a safe in Carta. Right. That I could basically just configure Carta, press a few buttons and issue a safe and have money in my bank account. Right. I just had no idea how to do any of that, like the logistics of raising an angel round. And he helped me a lot with that. Another former coworker was a fractional CFO for us then. He didn't charge us anything, he took a portion of equity, but he worked really hard helping us do projections and modeling and that sort of thing. And it was just interesting. And then, and then, you know, of course, again, without naming names, there are people that you think are going to show up for you who don't. Right. That kind of surprises you and hurts you. And then there are these people that you wouldn't expect to show up for you, who show up for you in really huge ways. And it's an interesting learning experience.

Totally. I mean, I think, you know, I'm not going to get this right, but there's like this adage that you, you really know who your friends are when things get bad or, or things get tough. And sometimes, sometimes there's just like the crazy startup story where everything just goes right. But those are definitely the exceptions. And so you, you just see that as a, as a founder in your journey and no matter what your outcome is, like, there's gonna be a lot of really tough moments and the people that show up for, for you in those moments, it speaks a lot about who they are and your relationship to them. You know, you were, you were talking about some of the, the, the learnings, like the column, like the non sexy founder work, the back office stuff like issuing safes in Carta. You know, when I, when I like read through, I like look at your background like, you are so accomplished. You are a previous founder. You, you're, you're not 18 year old who's never had a job. You are far from that. What were, what were like some of the, the big like growth moments or growth areas, learning areas for you on your, on your journey.

Yeah. So definitely. And I, I have an mba and I learned a lot in my MBA program. You know, I think that was, it was very helpful to have gone through that program. But, you know, an MBA doesn't really prepare you for the day to day of kind of the operational stuff of running a business. And I had never done fundraising before. My, my last company, I had bootstrapped. This is my first time on that journey. And yeah, there was just so much to learn there. And I learned a lot. Not just, not just the operational and logistics stuff, but also about myself personally, like where I have strengths and where I have weaknesses and where I have fears and where I have insecurities and where, you know, I just, I just really struggled with that part of it. That was a huge learning experience for me. Again, not just, not just ramping up on all the logistics stuff. Everything I learned, learned about myself if I had to. Jason and I both agreed, like, if we do this again, we're bringing on a third co founder and they're going to be a salesperson, they're going to, they're going to be in charge of fundraising. Like, we don't. We're done with this.

We're done with the fundraising piece.

We're done with this. It is not, it is not my zone of genius.

Yeah. So, I mean, maybe just, you know, we talk us, like, can you talk us through a little bit? What the dynamics of fundraising there at the end for you? Like, what kind of, what happened? And you know, what, what was that experience like? You know, you said you're out in the future, so I'm, I'm just, I would love to hear more about kind of those exact dynamics and, and, and, and what you heard and maybe what you learned.

So I think part of it is that you have to be really persistent and you have to be really good at asking and you have to be really good at, you know, maybe creating fake scarcity. Right. Like, a lot of the advice I got was tell people you're closing the round in three weeks and you're oversubscribed and this is their last chance to get in. And it wasn't true. Right. And people would be like, no, tell them that anyway. Just pick a date and tell people that you're oversubscribed and you're closing the round on that date and this is their last chance to get in. But I could not do that. I could not do that. And people, you know, a number of people gave me advice like that and acted like, well, obviously, obviously that's what you do. And I was just like, how, how? And, and then also, yeah, I mean, I talked to so many VCs, and there's a lot of different types of VCs out there. They are, I think probably all really smart people. I don't think all of them. So there are some, some VCs I talked to where I was like, whoa, you are so smart and you get this and you're asking really tough but fair questions and you're bringing up a lot of valid points and blah, blah, blah. And then there were other VCs that would grill me and I'd be like, you're an idiot. I'm not. Again, I'm not going to name names, but like, they would ask the dumbest questions where you're like, oh, even asking that, how did you not, how can you not figure out the answer to that question? Like, they just, I don't know, they just wanted to hear themselves talk and then the other game that they'll play. And again, not all of them. So some of them, some VC firms, they'd hear my pitch and they write back within a couple of days and be like, we're not going to move forward with you. Here's why. And that's great. Those people are great. Right? And then there are other VC firms that like, they just want to drag you along. I think they, they want the right to say no. Right. Like, they don't, they don't want to quite let you get away, but they're not willing to make a decision. So they make it seem like they're going to invest in you and they just need more information and more paperwork and another interview and another dem. And, you know, whatever. And I've realized that that's a bad sign. Like, people who are actually going to give you money are going to do it fairly quickly. They're going to get it, they're going to want to bet on you and they're going to do it fairly quickly. And when you're that early, when you're looking for a precede or a seed fund, if someone's dragging you on for months, they're not going to fund you, like, walk away.

So this, this might put you on the spot a little. So I apologize. But you know, there's just so much data conversations out there just about like how it is a more difficult fundraising environment and process for women than it is for, for men. Do you feel like that's true? Do you, if so, or in general, do you have advice for other women founders just based off of your experience?

Yeah, I, I do feel that there's some truth to it. I, I never felt like actively discriminated against no one, no one did anything creepy or rude, nothing like that. I don't feel like I was treated poorly in any way. But you just have to wonder if I were a 28 year old white guy coming in, pitching the same idea, you know, might they respond differently, might they ask different questions? And in fact there's a lot of research that investors tend to ask women a lot of like failure based questions like, well, what about this problem and what about this problem and what about this problem? Whereas they tend to ask men more like open ended visionary questions like how big do you think this market could be and what is the potential here? And there's a whole research paper on that. And I do think there's some truth to that where there's just a, almost like a ingrained presumption of competence that men get that women don't.

Yeah.

Because it's just like, yeah, yeah, I'm like, I'm obviously qualified to do this. Like, you know, I, I know the guys you people give money to. Like I am as qualified as them. But I never want to blame that. I don't think any woman founder wants to, you know, point the finger at, I just couldn't raise money because I'm a woman. And then I think the other thing that's really important to note about being a woman versus being a man, and I think this is also very true of people of color too, is so much of this game is your network, so much of this game is your network. And I had a number of people who I went to for advice who would say things like, oh, you need a half a million dollars, all that. You just gotta find five friends who will write you $100,000 check. Right. And I don't, I have tons of female friends who could write me a hundred thousand dollar check who have that kind of money in their household. Right. But that's not what women do. It's just not what they do. Right. Whereas like, you know, men, men are more inclined to make those transactions when their buddy calls them up and says, hey, I'm starting this big tech company, it's going to Be huge. You want to put in 100 grand? I think men feel much more empowered and comfortable saying, yeah, buddy, I'll give you that money, you know, assuming it's comfortable for them financially. Right. You know, I, My girlfriends were kind of like, what are you talking about? And some of them would say things like, I don't think my husband would go for that. You know, like. And I just think I couldn't believe how many people gave me this advice, like, well, you just need to find five people to give you a hundred thousand dollars. Just call your friends. And I'm like, what are you talking about?

Easier said than done.

They would, they would say it like it's a no duh. And, you know, I'm like, what world do you live in? But I do think certain people live in networks that, where you can, you can realistically do something like that. It was, it was always white men giving me that advice. Never did a woman or person of color give me that advice. But, yeah, so much of it is. Is your network. And I had an amazing network in so many ways that was so supportive of me, which was a huge advantage. But I think other people have better networks, and I think men tend to exist in networks that are more likely to hand each other money.

Yeah. Yeah. I mean, there's so much that, that goes into it and so much that has to, let's say, just break your way in order for it to. For it to all come together and all work. And to your point, you probably had a pretty amazing network that came out in lots of ways. For example, like around your beta. Right. But it, it kind of only takes one chink in the armor, but at least around the fundraising process, you know, what you, you said was fascinating just around the types of questions being more like around failure versus around vision. So at least as a woman found her to be prepared for that. Right. To. To know that you're going to have to overcome that objection or those sets of objections and being ready.

Yeah, yeah, I did a lot of objection handling work, but. But I think I did it well. You know, I, I felt like I was prepared for most of the questions they threw at me, even the ones that I hadn't prepared for, you know, stuff that came out of left field. That, again, sometimes it was really thoughtful where I was like, oh, that's a really good point. I hadn't thought of that. And then sometimes they throw out objects, objections that I was like, oh, how would you even ask that? Like, that's the dumbest question I've Ever heard, like, how did you get this job? But yeah, I was really prepared for it.

So we, before we wrapping, I would love to just hear more, you know, just hear more about you on a, on a personal level. You know, tell us a little bit more about yourself, who you are up to, becoming a founder, who you are outside of being a founder, how your work identity might inform your perspective on life.

Just.

Yeah, tell us more. Tell us more about yourself.

I'm an Arizona gal, born and raised. I've lived all over the world, but I came back to Phoenix. This is home and I love it here. I, let's see. This feels like, like when someone's like, what are your hobbies? I'm like, I don't really have hobbies, but I will put in a plug here for I, I, I have a bad cooking show on TikTok and interesting. So I am a. Yeah, so I am a terrible cook. I am like the world's worst cook and I, nothing I do can make me a better cook. So I decided I would start, like, filming me trying to cook things with some commentary, and I started putting those videos on TikTok and they have started to build a following. So it's just Sasha is cooking one word on TikTok. I highly recommend people go check those out because that's, that's my side hustle now. Bad cooking videos.

I love it.

But no, I think I'm, I'm someone who tries to be really, like you said, authentic in everything I do, show up in my relationships a hundred percent, be truthful, be compassionate, be of service, and be kind. And, you know, I think, I think there are people who balance that skill set really well with just the right amount of, kind of like ruthlessness and like killer instinct. And I don't think I have the ruthlessness and killer instinct. Right. I don't. And I can make hard decisions, but I think that's, that's a little bit different from Killer Instinct. And I, I, I don't know that you need that to, you know, build a successful company. I think you do need a little bit of it to fundraise.

Yeah. Did you know you've run and founded two companies now? I mean, did you always know that you wanted to be a founder, that you wanted to run your own business when you were younger or how did, how did that come about?

I didn't, I didn't know that until I kind of ended up doing it the first time. I, and people would tell me growing up, like, you're gonna, you're Gonna be a business builder one day. Like, you're gonna be a founder, you're gonna be a CEO. And I, I was not interested in it at all. But I was always a leader growing up, right? I was always, you know, even if I was like the, the, you know, on the playground and we were creating a dance or a play or something, right? Like, I was always the person directing everything. I was always the one in charge. I'm the oldest sister, you know, And I think once I did it, I realized that I was really comfortable in leadership and that I didn't think, I'll tell you this, I didn't think I ever wanted to manage people. I really didn't. I thought I wanted to be an individual contributor my whole career. I thought it's, it's so much faster to do it myself. If I do it myself, I'll do it right. You know, I had no interest in building a team and managing a team, which those people make the best managers, honestly, the people who never wanted to be managers. But when, when, against my will, an employee got put on, you know, put under me in a job who was a girl. She was great. She was great. I, I started to realize that, oh, like, if you train the team well and you manage them well, you can actually produce so much more by managing a team well than you can yourself, regardless of how productive you are. And that was such an aha moment in my life where I was like, I need to get better at management because this is, this is how you create something. It is through the skill set of leading a team, not through working harder like yourself.

100%.

Yeah.

I mean, that, that also, that dynamic is also really hard. That's a hard founder dynamic too, because as a founder, you generally can do things faster yourself than like, coaching somebody. But then being in the machine is not the best way to build the machine. And sometimes you have to do both. But when you decide to be in the machine and when you decide to build the machine, that's always a, I think, a difficult decision to make as a founder. And a lot of that is also just like, personal. Like, what do you enjoy more?

Yeah, yeah, I, I found, I mean, there were certain things I liked doing myself. I was really looking forward to the day where I could hire someone to handle all the operational stuff that, you know, the behind the scenes kind of, you know, managing bank accounts and, you know, taxes and all that kind of stuff. I didn't like that stuff. But I really enjoyed working on the product, collaborating with the team on the Product. But I was also really lucky. Again, so much of it comes down to hiring. And I think over the course of my career, I've been good at hiring. And that's been one of my strengths as a leader is I'm. I'm good at hiring, I'm good at coaching, I'm good at using people to their highest and best use, and I'm good at trusting people. Right. I'm good at. I mean, either I'm gonna trust you or I'm gonna fire you. There's no two ways about it. Like, either either I trust you to get the job done well, or I'm going to fire you. But luckily, I really trusted this team to get the job done well. And they did. They did. Given the time and the resources, they got the job done extremely fast and extremely well.

So, last question before I let you go. And you've been very generous with your time today, so again, thank you. What's one piece of advice you would give to your future self if and when you decide to start something again?

I mean, like I mentioned, the biggest thing is I would want to involve a co founder that could help with fundraising. And with the sales side of it, I realized that that's really a strength that I need some help with. And yeah, I think that's the biggest thing is just recognizing that that was not a strength for me and that I should have involved someone earlier on that could have been a part of the business and also helped with. Yeah, I think that's about it.

Yeah. No, I mean, I think, you know, obviously that lesson is, Is specific to you, but the general lesson of knowing thyself, knowing yourself, and through the journey, learning about yourself is something that every founder can, can take away. And I think just, you know, if nothing else, you know, that lesson is, Is such a valuable one.

Um, so I did have one more note on what I wanted to talk about in terms of advice to myself. So I studied. I majored in computer science in college, and as a freshman, first of all, I was one of very few women, and there were. It was so intimidating. There were so many guys in these, you know, CS100 classes who use these fancy words, and I didn't know what the words meant. And I, I was so intimidated. And I thought to myself, wow, like, they're already so far ahead of me, I'm never gonna catch up and I can't do this. I. I should just quit, right? And then a funny thing happened, which was by junior year, they'd all switched their majors. Those Guys, they dropped out of computer science. They couldn't, they, they, they, they had all the buzzwords, but they couldn't hack the actual coursework. Right. They were all out of engineering by junior year. Those, those kind of pompous guys with the fancy words. And I realized, reflecting back on it, by the way, I graduated with honors. I graduated cum laude, a computer science degree. I had almost a 4.0 in my major. You know, I did fine. I did fine. And I think looking back, what I would tell myself is this, this was the same thing. This was the same thing. Fundraising was the same thing. Where there's a lot of guys, they have a lot of fancy words. They may be in positions of power right now, but they're not necessarily smarter than you. They're not better than you. And don't, don't waste so much energy being intimidated by these people and having all this fear around this process. Because, you know, looking back on it, I'm like, yeah, it's the same thing. I'm as good as any of them. I just didn't know the language truly.

Well, thank you so much for just being brutally honest with us today about everything, not just that last point. And again, for, for taking the time to, to share your story.

You so much for having me. It's an honor to be here, of course.

Of course. Well, I think that's it. If you're listening. Thanks so much for, for tuning in. And this has been another episode of the Not Another CEO Podcast. Thank you. That's a wrap for this week's episode of Not Another CEO Podcast. Thanks for joining. For show notes and more, please Visit not another CEOPodcast.com we'll see you next week.