What happens when a strong vision, real traction, and early funding still aren’t enough? In this Failing Forward episode of Not Another CEO Podcast, Sasha Pasulka shares the journey behind her AI startup, Elka.
Sasha opens up about the thrill of building, the challenge of fundraising, the reality of launching with imperfect tech, and the emotional toll of shutting down a business you deeply believe in. From her days as a software engineer to founding one of the most-read blogs of its era, Sasha reflects on learning to trust herself, ask for help, and move on with grace.
Takeaways:
The AI Aha Moment: Sasha was re-energized to found again after ChatGPT launched publicly in late 2022. She saw an opportunity to solve marketing problems that hadn’t been addressable before due to the language limitations of software.
Solving a Real Problem from Experience: The product idea came from Sasha’s time at Tableau, where hours of valuable customer video content went unused because it was too hard to search. Elka aimed to automate finding and surfacing those insights for sales teams.
Alpha and Beta Lessons: The team built fast and launched a beta early to help with fundraising, but users got frustrated with AI inconsistencies. Sasha onboarded every beta customer herself, but admits they may have opened access too soon.
The Limits of Non-Deterministic Tech: Building on an LLM proved unpredictable. Despite numerous safeguards, the AI struggled with tasks like basic math and clip durations—issues Sasha says may have improved if they had more time to wait out tech advances.
The Fundraising Wall: While Sasha successfully raised an angel round, later fundraising stalled. She reflects on her discomfort with the performative aspects of pitching and how authenticity may have hurt her in a system designed for bold salesmanship.
Support and Disappointment: From angel investors to past coworkers, Sasha describes the surprising people who showed up to help—and the ones who didn’t. She credits her team, co-founder, and a few critical mentors with getting them as far as they did.
Learning, Letting Go, and Looking Ahead: Sasha closes with advice to bring on a co-founder who can fundraise and a reminder to stop being intimidated by others’ confidence. She shares how the journey helped her understand her strengths and what she’ll do differently next time.
Quote of the Show:
"They may be in positions of power right now, but they're not necessarily smarter than you. They're not better than you… Don’t waste so much energy being intimidated by these people." - Sasha Pasulka
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#NotAnotherCEO #BusinessSuccess #ElkaAI
Chapters:
00:00 Intro
03:07 The Aha Moment: Founding Elka AI
04:30 Challenges in Marketing and AI Solutions
09:42 Building the Product: Alpha and Beta Phases
18:07 The Struggles of Fundraising and Leadership
25:22 Navigating Luck and Timing in Entrepreneurship
27:38 Key Decisions and Reflections
31:56 Navigating AI Non-Determinism
33:01 Support System and Key Influences
36:38 Fundraising Challenges and Lessons
42:40 Gender Dynamics in Fundraising
48:47 Personal Journey and Reflections
56:01 Advice for Future Founders
01:00:05 Outro
Transcript:
Sasha: [00:00:00] If it can do good work 70% of the time, that's gonna be good enough for people to appreciate it.
Nick: 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 s Sasha [00:01:00] Paska, 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 Northrop Gruman, including the F 35 Joint Strike Fighter, which I don't know if we're gonna talk about today, but is pretty awesome.
She's a digital media founder. She founded and served as CEO as of 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 and Innovative B2B MarTech Technology company which [00:02:00] had a really interesting AI product that she's gonna 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 writing Lead a 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.
Sasha: I am so thrilled to be here. Thank you for having me, Nick, and you did your research. That was such a introduction. Thank you.
Nick: Of course, of course. Well I I, I try my best I won't lie. I, IGI have my, some of my own help with with AI on on the, on the, on the deep research. But I, I write the intros myself. [00:03:00] So but let's ju let's jump into it. I think first question for you today. Just tell us 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, and start this, this new venture.
Sasha: 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 f founded anything in quite some time. 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 gonna found something again? And I just was like, what am I gonna found? And if I had to put one aha moment on it, was. When chat GPT released publicly, I think about two and a half years ago, I think [00:04:00] it was late 2022, was when chat GPT 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 chat GPT in the early [00:05:00] days, I just, I got excited again and I started to say to myself, my gosh, now we can solve some of these marketing problems that were not solvable with technology previously.
Nick: 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 uh as a, as a marketing person throughout your career.
Sasha: as a leader and as an individual contributor. I mean, I can give you kind of the little pitch for EL and the problem we
Nick: Yeah, sure. Let's, let's hear it.
Sasha: so. When I was at Tableau, this, this, this is the first time I really deeply encountered this problem. 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 [00:06:00] 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'd paid money, a lot of money to have the AV on this. 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 a hundred customer sessions over three days. Right? [00:07:00] 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. Year from the oil and gas space. 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 [00:08:00] 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-size deals, I wouldn't do that.
I would say search our website, see what we've got, but I'm not gonna take someone out of their job for half a day to solve this to try to close a $10,000 deal. Right. The, the content's probably there, the customer evidence, the sales person needs is probably there. they just can't find it.
And no it hasn't been cut. Nobody knows where it is. what we did at, 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 to close deals, could be used in a customer evidence capacity, and it just isn't.[00:09:00]
'cause there's no good way to do it because it, it took so long for a human to go through and edit and tag all that content. 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 'em eight ways. From Sunday and we'd put 'em in a library for your sales team to search. So they could go in and search by industry or search by keyword or search by person and see what we had on that topic.
Nick: Amazing. I mean, I totally can see why AI could be such an unlock for a product like that. And, and as, as someone who spent a lot of time doing B2B startup video the, the, the problems you, you solving you know you're kind of talking a little bit about the product and there's so much that I wanna ask you, but [00:10:00] 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.
Sasha: 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 wanna take full credit for any of this, but I, 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. But we brought on initially three people. I, 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. [00:11:00] it has to be built like a consumer product. 'cause 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. this was 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. was referred from someone in my network to a guy named John Billett who did our UX and helped with product. He was amazing. And then we also brought in a backend dev and a front end dev. and we just, just started creating this [00:12:00] thing. It took probably 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
Nick: Sorry. And 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?
Sasha: Alpha was internal testing and a handful of like, friends,
Nick: Okay.
Sasha: It was just like yeah, a handful of [00:13:00] friends.
Nick: Okay.
Sasha: probably in re in retrospect, it wasn't as comprehensive as it needed to be before moving to beta. But again, also, we were up against the clock I, I had hoped that having a beta with actual 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.
Nick: those, those competing pressures are always, are always difficult to navigate. You know, obviously there's a lot of ai com like AI companies today. You're really, I think, part of one of the first big waves of these, these companies. What, what's diff like, what do you think was different in your alpha and beta journey as an AI company?
Um if, if anything like were there, were there [00:14:00] unique considerations or, or factors at play for you? Kind of building on this new technology?
Sasha: 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 production because, and particularly trying to do it 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 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 [00:15:00] helpful enough that people will find value in it. you know, we'll, we'll continue to improve, we'll continue to close that gap. But I had had this kind of hypothesis that if it can do good work, 70% of the time, that's gonna 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 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
Nick: Yeah.
Sasha: uh 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 [00:16:00] into a couple of problems with the ai, kind of just abandon ship, right?
Nick: Yeah.
Sasha: be like, this, this doesn't work. I'm not gonna 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 in everything.
'cause you know, I wanted them to be equipped to succeed, but you just don't know what the AI's gonna do.
Nick: Yeah.
Sasha: And I think a lot of our beta customers got quickly frustrated when the first kind of thing went wrong weren't, didn't have any reason to stick it out.
Nick: Yeah. I mean, that's a. That's so hard because that's like, to an extent, like the point of [00:17:00] your beta program is to figure out what is going to work and what is not going to work. Yeah. 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.
Sasha: and I actually think what would've 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 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 32nd clip instead of a five minute clip. Right. And we, we kept running into issues where it just, that thing just couldn't do math. Right.
Nick: Mm-hmm.
Sasha: for, for the LLM. And I think even in the past year [00:18:00] kind of data literacy has, has
Nick: Has increased a things.
Sasha: Yeah. lot. Yeah. So I mean, there's so much that I I, I wanna ask you about and, and talk about, but we've kind of already started to get into your journey, but I think maybe just to rewind back a little, 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, why, go on this journey in the first place?
Well, probably for starters, 'cause I'm a little bit crazy and irrational, right? Like, you gotta, you gotta love the game. You've gotta just love the game. Right? And I I would say I have all sorts of, [00:19:00] not all sorts of, but like. I'm scared of heights. I won't go on rollercoasters. I have all sorts of fears in the physical world, but in the world of abstraction and ideas and companies and that kind of thing, and just life pathways, 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 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. [00:20:00] And I'd spent, so I built a successful company in my twenties and sold it. And then I'd spent most of my thirties 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, it wasn't everyone, and I'm not gonna name names, but sometimes, not always, but sometimes the skillset of who can raise the money and who can run the company, don't always overlapoverlap
in a person And some people are very, very good fundraisers who have no business actually leading a SaaS organization. [00:21:00] And I started thinking gosh, like I just wanna do it. I just wanna do it. like, why can't it be me? Why can't I just do it myself? And I found out why, 'cause I can't raise the money because I a hundred percent the skillset 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. 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 skillset overlap.
Nick: Yeah. Yeah. I mean, that's just that set of points is, fascinating to me. You know, the, difference between the, let's say the, [00:22:00] builder and then the, person that can go ahead and sell and, what skillset is more important and, better. especially in today we speak so much about real leadership, authentic leadership leading with your heart, all of those things.
And at least from, my personal experience, I felt very comfortable, in that mode. And then where I, didn't have necessarily, well, I mean, eventually I had problems raising more capital, but we also didn't have the metrics to, back it. But where I struggled in the fundraising, part of the game was just like, almost like the pure selling, the crazy Adam Newman style [00:23:00] selling that let's say throws caution to the wind.
And I don't think every founder, CEO is always there, but there's 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, vice versa.
Sasha: I completely agree. And I think there's even,
yeah, I think some amount of not, tethering yourself too closely the whole truth can be valuable in that process. And what I have found about myself is I tether myself to the whole truth. I really struggle to tell a story that's maybe bigger than the reality today or [00:24:00] yeah. to kind of answer anything in a way that isn't authentic. and I, think if you wanna fundraise, it's almost just part of that game. 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 lie too, right?
Everyone's just lying to each other and at some point, $50 million gets exchanged. I don't know how it happens, but it's not through sheer authenticity.
Nick: Yeah, well, I mean, 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 boldfaced lie will come back to bite you for sure. But there's like some level, I think to, quote you 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 [00:25:00] that, how do you find that right balance? You know, 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, how to an extent there was a, a driver there in, in what happened?
Like, to an extent you're kind of talking about like the element of luck, like timing and luck, right? Like I. How do you think about, how do you think about the role of timing in lockin and all of this versus agency and like your own, our own role as, as founders and and CEOs in our own journey?
Sasha: yeah. I mean, they say you make your own luck, but. 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 [00:26:00] 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, would've been in a very different situation. I mean, part of our plan was contingent on being able to raise a little more money. But I don't think, and. You what? I don't wanna say like, we were unlucky because we were able to raise the initial angel round that got us to a beta. Right. And I'm, know, I'm so grateful, so grateful and so lucky that [00:27:00] 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, and the, the underlying technology wasn't quite where we needed it to be yet.
Nick: I mean, it's definitely both. There's a role of both agency and Locke. yeah. I don't, I don't know what part is what but there, there's it, it plays a part in, in all of our journeys and all of our stories.
Sasha: Yeah.
Nick: You know, when you think about your journey from beginning to, to to end are there any key forks in the road or paths, pathways you took that you you think a lot about that that you think took the business in one direction versus the other?
Sasha: [00:28:00] I think we made some really good hires. If anyone is looking for contract help on, on any of your projects. Ping me. I'll give you some names. I think we, 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 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, I mean, 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 built out, [00:29:00] but this allowed us to really kind of finish that job and get that beta 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 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 advice, right. That was, that were that really helped me [00:30:00] 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 V one I had initially conceived. Like we, we pretty, we didn't pivot in those,
Nick: There's no major pivoting. I mean, you had, I mean, it sounds like you had issues with, with kind of design partners, beta partners, like ghosting, you I struggled with the same thing and, and, and managing that dynamic is, is really difficult. But it sounds like that was more around like kind of bugs and 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, the core problem.
Sasha: I, I, think we, we went to beta with too [00:31:00] many bugs and we didn't do a thorough enough alpha. And I think 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, 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 not saying like everything would've been perfect if it hadn't been for the ai. We definitely had more bugs than I would've liked in a beta that
Nick: Yeah.
Sasha: resolved had we caught them.
Yeah.
Nick: 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 like part of the process. So I, I, in retrospect,
Sasha: perfectionist. I'm
Nick: of course. Of course, of course. I [00:32:00] mean, I, I just, I, I, I, I think that's, that's a, that's a really, really tough one.
I think your experiences with a, like with a 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,
Sasha: And we tried so hard by the way, we, built in all sorts and we tried so hard to solve for it. Like we had all these sanity checks, right? Like we'd 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 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.
Nick: Yeah, I, I, I would agree with you on that [00:33:00] one. You know, you, you've spoken about it a little you know, your co-founder, your team, other folks like, who are 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, the role they played in your journey.
Sasha: Yeah, well, so yeah, definitely shout out to my co-founder. Shout out to my team. They were fantastic. I think the, like the, the first people that were really game changing were the angel investors who bet on us early, not just 'cause they gave us money, but because they gave us confidence. They gave us that morale boost that they would bet
Nick: I.
Sasha: us. so those were huge people. But you know, it was surprising who. Really showed up, [00:34:00] I've talked to some old bosses, 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, 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. so we were facing a lot of the pro 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, he would get on a call with me like every two weeks and, just walk me through the basics of how do I even do this?
Like I didn't understand that you could just do a safe in Carta, right? That I could basically just [00:35:00] configure Carta, press a few buttons and issue a safe and have money in my bank account, right? I just had no idea how 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, and he didn't charge us anything. He took abortion 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 of course, again, without naming names, there are people that you think are gonna 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.
Nick: Totally. I mean, I think I'm not gonna get this [00:36:00] 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
Sasha: Yeah.
Nick: 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, in your journey. And, 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, 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 and carta. You know. When I, when I like read through, I like look at [00:37:00] your background, like, you are so accomplished. You are a previous founder.
You you're, you're not a 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.
Sasha: 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 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. so this was my first time on that journey. Yeah, there was [00:38:00] just so much to learn there. And I learned a lot, not just, not just the operational and logistics stuff, but 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. just, I just really struggled with that part of it. That was a huge learning experience for me. not just, not just ramping up on all the logistics stuff, but 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 gonna be a salesperson.
They're gonna, they're gonna be in charge of fundraising. Like, we don't, we're done with this. We don't wanna do
fundraising the fundraising piece.
done with this. It is not, [00:39:00] is not my zone of genius.
Nick: Yeah. So I mean, maybe just we talk us, like, can you talk us through a little bit what the, the dynamics of, of, 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, 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.
Sasha: 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 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 [00:40:00] 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. I could not do that. I could not do that. And people, 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 talk 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 talk to are, I like, whoa, you are so smart and you get this and you're asking really tough, but fair [00:41:00] 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 gonna name names, but like do, they would ask the dumbest questions where you're like. How, why are you 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, and again, not all of them, so some of them, some VC firms, they'd hear my pitch and they'd write back within a couple of days and be like, we're not gonna move forward with you. Here's why. that's great.
Those people are great. Right? And then there are other. VC firms that, like, they just wanna drag you along. I think they, they want the right to say no, right? Like, they, they don't, they don't wanna quite let you get away, but they're not willing to make a decision. So they make it seem like they're gonna invest [00:42:00] in you and they just need more information and more paperwork, and another interview and another demo and whatever. And I've realized that that's a bad sign. Like the people who are actually gonna give you money are gonna do it fairly quickly. They're gonna get it, they're gonna wanna bet on you, and they're gonna do it fairly quickly. And when you're that early, when you're, looking for a pre-seed or a seed fund, if someone's dragging you on for months, they're not gonna fund you, like
walk away.
Nick: so this, this might put you on the spot a little, so I apologize. But you know, there's, there's 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.
Sasha: Yeah.
Nick: Do you feel like that's true? Do you, if so, or in general, do you have advice for other women [00:43:00] founders just based off of your experience?
Sasha: Yeah, I, I do feel that there is 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 have to wonder if I were a 28-year-old white guy coming and pitching the same idea might they. Respond differently. Might they ask different questions? And in fact, there's a lot of research that investors tend to ask women lot of like failure based questions. Like, well, what about this problem? And what about this problem? 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, [00:44:00] 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,
Nick: Yeah.
Sasha: Because it's just like, yeah, yeah. I'm like, I'm obviously qualified to do this.
Like I. You know, I, I know the guys you people give money to, like I am as qualified as 'em, but I never wanna blame that. I don't think any woman founder wants to point the finger at, I just couldn't raise money 'cause I'm a woman. and then I think the other thing that's really important to note being a woman versus being a man, and I think this is also very true of people of color too, is much of this game is your network.
So much of this game is your network. And I had [00:45:00] a number of people I went to for advice who would say things like, oh, you need a half a million dollars, all that. You just gotta find, find five friends who will write you a hundred thousand dollars check. Right. And I don't. I have tons of female friends could write me a hundred thousand dollars 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 men, men are more inclined make those transactions when their buddy calls them up and says, Hey, I'm starting this big tech company. It's gonna be huge. You wanna put in a hundred grand. I think men feel much more and comfortable saying, yeah, buddy, I'll give you that money. Uh assuming it's comfortable for them financially. Right. know, I, I, my, my girlfriends [00:46:00] were 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, I just think. I, 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?
Nick: Easier said than done. Just calling your.
Sasha: they would say it like, it's a no duh. 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. 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 [00:47:00] 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.
Nick: Yeah. Yeah. I mean, there's so much that that goes into it and, and, and so much that has to, let's say, just to break your way into order for it to, for it to all come together and, and all work. And to your point, you probably had a, a, a pretty amazing network that came out in lots of ways, for example, like around your beta, right?
Sasha: Right. it, it kind of only takes one chink in the armor. Um but at least around the fundraising process 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 founder to be prepared [00:48:00] for that, right?
Nick: To, to know that you're gonna have to overcome that objection or those sets of objections and being ready.
Sasha: 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 stuff that came outta 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'd throw out object objections that I was like, oh, why would you even ask that? Like, that's the dumbest question I've ever, like, how did you get this job? But I was really prepared for it.
Nick: so we, before we wrapping, like I would love to just hear more just hear more about you on a, on a personal level tell us a little bit more about [00:49:00] yourself. Who you are up to becoming a founder, who you are outside of being a founder how your work identity might in inform your perspective on life.
Just, yeah, tell us more. Tell us more about yourself.
Sasha: 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, 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,
Nick: Interesting.
Sasha: 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 mean, [00:50:00] 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 started to fill 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.
Nick: I.
Sasha: but no, I think I'm, I'm someone who I. 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 [00:51:00] skillset 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 build a successful company. I think you do need a little bit of it to fundraise.
Nick: Yeah. Did you, 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?
Sasha: I didn't, I didn't know that until I kind of ended up doing it the
Nick: I.
Sasha: 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. [00:52:00] And I, I was not interested in it at all, but I was always a leader growing up.
Right. I was always even if I was like the, the, 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 and. I think once I did it, I realized that I was really comfortable in leadership and that, I, 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 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, [00:53:00] 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 put under me in a job, who was a girl. She was great. She was great. I. And 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 skillset of leading a team, not through working harder like yourself.
Nick: A hundred percent. Yeah, I mean that, that also, that dynamic is [00:54:00] also really hard. Is a, 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, to make as a founder. Um and a lot of that is also just like personal, like what do you enjoy more?
Sasha: yeah, yeah. 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 the, the behind the scenes kind of managing bank accounts and taxes, all that kind [00:55:00] of stuff. I didn't like that stuff, but, I've 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. think 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 trust I'm, either I'm gonna trust you or I'm gonna fire you. There's no two ways about it. Like either I, 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, and they did.
They did, given the time and the resources, they got the job done extremely [00:56:00] fast and extremely well.
Nick: So last question before I let you go. And you've been very generous with your time today, so again, thank you. Yeah. What's one piece of advice you would give to your future self if and when you'd decide to start something again? Uh.
Sasha: I mean, like I mentioned, biggest thing is I would want to involve a co-founder that could help with fundraising and with the sales side of it. I realize that that's really a strength that I need, some help with and. Yeah. 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 [00:57:00] also helped with that. Yeah, I think that's about
Nick: Yeah, no, I mean, I think 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 if nothing else that lesson is, is such a valuable one.
Sasha: Yeah.
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, there were, it was so intimidating. There were so [00:58:00] many guys in these CS 100 classes who used 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 catch up. 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 outta computer science.
They couldn't, they, they, they, they had all the buzz words, 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 [00:59:00] realized, reflecting back on it by the way, I graduated with honors. I graduated cum laude, computer science degree.
I had almost a 4.0 in my major. You know, I, I did fine. I did fine. And I think looking back, what I would tell myself 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, waste so much energy being intimidated by these people and, and having all this fear around this process because you know, back on it, I'm like, it is. [01:00:00] Yeah. It's the same thing. I'm as good as any of them. I just didn't know the language.
Nick: 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.
Sasha: you so much for having me. It's an honor to be here.
Nick: 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.
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