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Mar 21, 202440mEpisode 34

How do you save a round when your COO quits mid-raise?

The short answer

Ask AI founder Alon Talmor explains how he navigated a fundraising crisis after his prospective COO quit mid-process, ultimately securing a $9M seed and $11M Series A. His core lesson for founders: radical honesty with investors is non-negotiable when a deal is falling apart, as it's the only way to rebuild trust and save the round.

Highlights

  • Saved a seed round after his prospective COO quit post-term sheet by being radically honest with his lead investor.
  • Closed an initial $7M seed round, then added a strategic $2M extension from smaller GTM funds and angels.
  • Secured an $11M Series A term sheet just one week after a dinner meeting with a lead investor he almost skipped.
  • Avoided inflated 2021 valuations to prevent a future down round, prioritizing sustainable growth over hype.
  • Sold his first company to Salesforce in 2012 after bootstrapping it to a few hundred thousand dollars in revenue.

The full breakdown

Alon Talmor, founder of Ask AI, is a self-described “crisis-time founder” who built his first company, BlueTails, during the 2009 downturn and sold it to Salesforce in 2012. For his second venture, Ask AI, he raised a $9M seed and an $11M Series A by navigating another difficult market, but the biggest challenge came from an internal crisis. While raising his seed round in late 2021, his prospective COO—who he had already presented to investors—backed out after a term sheet was on the table. The sudden departure created a crisis of trust that threatened to kill the entire deal. Talmor’s recovery strategy was built on immediate, radical honesty. He advises founders in similar situations to “have an honest conversation with your investor and tell them the truth. Tell them exactly what happened and exactly why, even if it sounds horrible.” This approach helped him maintain the relationship with his lead investor, State of Mind Ventures, who agreed to continue but required him to find a co-lead. After an intense, last-minute push, Talmor secured Vertex Ventures to co-lead and successfully closed the initial $7M round. Following the initial close, Talmor raised a strategic $2M seed extension in mid-2022 from smaller US-based GTM funds and angels. This move broadened his investor base and fortified his balance sheet just as the market began to turn. His subsequent $11M Series A came together opportunistically, not through a formal process. He met the lead investor, Leaders Fund, at a dinner he almost skipped. The meeting resulted in a term sheet just one week later, reinforcing his advice that founders should “always meet investors” to build relationships, because you never know when chemistry and timing will align. Talmor’s fundraising approach is rooted in a conservative philosophy that prioritizes validation and sustainable growth over hype. Before raising his seed, he secured design partners like Yotpo to validate the product need, and he consciously avoided the inflated valuations common in 2021. “If you would raise an inflated valuation, then you would need to fight now in 2023, 2024 for a next round, not to down round yourself,” he explains. This focus on building a real business with strong investor relationships allowed him to successfully raise $20M across two rounds during a period of extreme market volatility.

Who's on this episode

Alon Talmor
Alon Talmor
Founder & CEO · Mosaic AI

Alon Talmor is the co-founder and CEO of Ask.ai, an AI platform designed to support customer-facing teams. He is a serial entrepreneur who began his journey by co-founding BlueTail, a software company acquired by Salesforce in 2012. Following the acquisition, Talmor served as Chief Data Scientist at Salesforce before taking an unconventional path to pursue a PhD in AI and Natural Language Processing (NLP) from Tel Aviv University. This deep technical expertise informed the creation of Ask.ai, where he focuses on building practical AI solutions for enterprises.

Questions answered in this episode

References & resources

Hosted by

Jason Kirby
Jason Kirby
Host · Founder, Thunder.vc

Podcast host, angel investor, and serial entrepreneur with 4× exits ranging from small businesses to VC-backed tech companies. Jason has been personally involved in over $100M in transactions and now helps founders close their next transaction at Thunder.vc, from pre-seed rounds to $100M exits. He coaches founders through their next major transaction and gets the deal done by introducing them to the right people in his network.

Apply to work with Jason

Full transcript

Jason Kirby (00:02.636) Welcome to episode 34 of Fundraising Demystified. Today we have Alon Tamor, co -founder and CEO of Ask AI, an AI sidekick for customer-facing support teams. They recently raised an $11 million Series A after previously raising a $9 million seed. Alon is a serial entrepreneur who previously built and sold a software company to Salesforce and then decided to pursue a PhD in AI. He shares his insights into the future of AI, where the market is today, and how every company is trying to keep up and adapt. How he built deep relationships with just a select few investors and the challenges he faced raising capital in a down market in a crowded sector. As a reminder to get notified of our weekly podcasts and newsletters, be sure to subscribe at join.thunder.vc. Again, join.thunder.vc. Now, on to the show. Welcome to the show. Alon Talmor (00:10.012) Hey everyone, happy to meet you. Jason Kirby (00:11.098) And I'm really, really excited to have you on the show today. You have an impressive, you know, serial founder background, technical background, and I'm excited to learn about your story and what you're doing at Ask AI. So if you can just tell the audience a little bit about what you're doing at Ask AI and a little bit about your background. Alon Talmor (00:29.716) Perfect. So maybe I'll start from the beginning. I'm a second timer for startup was sold to Salesforce .com. We were sold in 2012. We actually did back then, a company called BlueTails, something that today in our current company, Ask AI, is what we call a single app out of a variety of solutions we're doing. We would actually aggregate multiple information from the web about a prospect and show it. as if it's like a LinkedIn on steroids back then in 2012. That was pretty new. It seems to be also a bit new today or needed. And we were sold to Salesforce, opened the Tel Aviv office. I was chief data scientist at Salesforce. And 2015, when my vesting ended, I went to do something a little bit strange for an entrepreneur. I went to do a PhD in the field of AI and NLP. I was looking to... Jason Kirby (01:06.234) Yeah. Alon Talmor (01:26.836) see where the future is taking us. And I was pretty lucky to meet a professor coming back from Stanford to lead the NLP efforts in Tel Aviv University. And back then, NLP was nothing near, or AI, nothing near what we see today with ChatGPT. Deep learning was the word people would use back then. It wasn't applied too much to NLP, mostly to vision, computer vision. And... We actually were lucky enough to see the whole revolution unfolding in 2018. We got a best paper in 2019 with people that were the authors of what they call BERT, a foundational language model. And in 2020, when I finished my PhD, we actually realized that something big is going to happen with generative AI and OpenASK .AI. But our focus was actually not to be a foundational model company, even though I brought with me a professor, a few other professors and PhDs, like really great minds. But our focus was actually to become a solutions company around generative AI as kind of our core offering. And our philosophy around that is actually interesting. We see generative AI as something analogous to personal computers. You know, it's going to make us all more productive, more efficient. It's pretty obvious to everyone, but it's not very obvious how actually, especially in industry. And so if you look at the beginning of personal computers, it's actually a little bit similar to that. Like when Apple II came out, people would learn how to code, play a few computer games. That's pretty much it in the beginning. Only when another company, not Apple, but Microsoft came along with Windows, And with kind of Office and word processor, then companies really started buying it for employees. Until today, it's pretty obvious every employee needs a computer. That's the first thing you buy. So we in Ask .ai aspire to be like the second thing you buy for an employee. A real AI helper, or what we call an AI sidekick. And that's kind of our vision to empower every employee, not replacing people, but actually empowering them with AI. I can get deeper into the product too. Alon Talmor (03:43.22) But yeah, that's kind of the overview of who we are. Jason Kirby (03:47.834) I can see how you raised money. I think you do a great job of telling the narrative and one coming in with an incredible, you know, technical background, getting your PhD. Yeah, that's an unusual path. Um, but it seems like it was worth, uh, pursuing. What did your, you know, when you were leaving Salesforce and you're kind of pursuing that PhD, that's such an uncommon path for founders to pursue. Um, what were people around you kind of telling you when you were making that decision? Alon Talmor (04:18.676) that I'm bored. You must be bored. Why are you doing this? And the reality of it is that like all my co -founders open actually successful companies. One of them is the CEO of Placer AI. The other one is the CEO of Plank and the third is the CTO of Fungard. So I'm really admired by my previous partners. I was actually looking for a technological breakthrough to Jason Kirby (04:20.702) I'm out. Alon Talmor (04:48.148) to really disrupt industry. And that's the main reason that I went to do a PhD. Say, you know, something romantic about it as well. Like my father did a PhD before me and I felt like I always wanted to do one. I was before that, before my first company, I was doing kind of brain science and I started a PhD and didn't continue. So I always felt that something was missing there. So that was the kind of second reason. And yeah, the third is, it's true, I was born. Like I was looking for interesting things to do. I was traveling the world one year between 2015 and 16. And then I thought, what would be interesting to do? And it was a click when I met that professor, Jonathan Barron, that was coming back from Stanford. He actually didn't want to work with me in the beginning. He was asking, why should I work with you? You don't have any kind of certificates or, you know, why do a PhD with you? But eventually I was able to persuade him and I was happy to do so. Yeah. Jason Kirby (05:45.69) No, that's a great story. And so something I want to kind of highlight a little bit more, going back to Blue Tail, your company that you sold to Salesforce, what was the market like back then? Because this, at least from what I looked on your LinkedIn, this was a 2009 to 2012, like terrible market for most. And to build a company and sell it to a behemoth like Salesforce in three years. Alon Talmor (05:45.908) Good chemistry. Yeah. Jason Kirby (06:10.714) What was that experience like? Did you raise outside capital to do what you had to do there? And kind of how is that different back then versus now? Alon Talmor (06:21.364) It was very hard back then. I'm what you may call a crisis time founder. I always found a company when there's some kind of a challenge in the market. Now it's the 2023, 2022 challenge. And back then it was 2008, 2009. Back then, I can say that it was much harder from two reasons. First, the more local market. The whole market was not that involved around SaaS. Jason Kirby (06:27.258) Mm -hmm. Jason Kirby (06:34.33) Yeah. Alon Talmor (06:50.932) So it was harder to sell. You didn't have Zoom. You would need to sell face -to -face. The selling was much more old school. And so back then, we actually started bootstrapping. Like we had consultant jobs in data science. And then three days a week, we would build the company, the four co -founders. And we had one co -founder that would go, I would go and that co -founder would go to San Francisco to try to sell. to, you know, Valley companies, like companies that were young back then, like Marketo were our first customers actually. And we were doing that while bootstrapping. We actually got to a few hundred thousand dollars before we were actually looking to fundraise. And around that time, we were looking for partnership with Salesforce and eventually they just acquired us. So that's, that's the story, but. I can say that back then, even if you were to raise the amounts, we're nothing near the dollars you would raise today. Jason Kirby (07:57.882) Yeah, a very, very different game back then to now. And so, right. You sell the company, you're, you know, living that big corporate life, uh, vesting at Salesforce, you know, for, for founders out there that haven't had that experience, what's that transition like post exit and transitioning your team, your product, and, you know, going to that big corporate position. Alon Talmor (08:21.492) It's actually not very easy. It's very different when you're a very small startup. And even back then, Salesforce was a bit younger, was already a pretty big corporation with a hundred thousand customers. We were actually the first external location Salesforce had. Back then they were mostly San Francisco and Bay Area. But I can tell you that corporate life for me personally, some founders find it easier. For me, it was a little bit harder. Like I was... looking for quick impact and in bigger companies you need to have patience. And so that was a little bit challenging. Yeah. Jason Kirby (08:58.554) I think that's well said. That was my experience when we sold our company to Walmart was it was, you know, you want to go 90 ,000 miles an hour and you can't. There's speed bumps all the way. Yeah. Let's, let's energize everyone. So, all right. So now, now you're, you're building Ask AI. You've got the idea, you know, at what point did you decide that you're going to need money and how did you go about raising the capital that you needed for, for Ask AI? Alon Talmor (09:07.764) Yeah, and the meetings, right? There's a lot of meetings. Alon Talmor (09:29.396) Well, the challenge in the beginning in 2020 was there was no hype in market like now. If you look at chat GPT, it was out November 2022. So we actually didn't sell generative AI because no one knew what it is. We started with kind of foundational solutions. One of them was enterprise search with generative AI on top. But the reason we coined it that way, we didn't even call it generative AI. We call it Google like answers, Google answers. Like, say, something that would just answer your question. Because back then, people would not know that you can even ask a machine a question. But the market of enterprise search was there. There were companies that were doing enterprise search. And so we were trying to sell enterprise search with kind of a whole new flavor. That was kind of our first offerings and the first design partners. We started with design partners before we fundraised it. We fundraised one. maybe privilege that I had is that I can actually fund my own kind of beginning. So instead of taking kind of a pre -seed of sorts, I actually funded the first kind of month in which we will build the prototype. We started with design partners. And then when we got kind of early validation, then in the end of 2021, we actually fundraised and officially opened. Jason Kirby (10:50.394) Gotcha. So you worked on it for a little bit and I think this is an interesting thing to kind of highlight because this is something that I thought was the case is you kind of got going and because of your background, you had some success before you were in a fortunate position to kind of sell fun, to make sure there was something actually there before going through the hassle of, you know, formalizing everything. So I appreciate you kind of sharing like that process. And when you kind of said, when you said you had some validation, How did you define validation and did you decide on what validation meant before you got it? Or did you just kind of look at yourself like, all now this looks good. Alon Talmor (11:28.692) Well, it's a combination of two things. First, find a substantial stakeholder you want to kind of target. Then see that they actually have the need and listen to them first. Like what needs do they have and are you, before you tell what you're doing, are they already saying that this is a need they have? And afterwards, if you actually build a prototype and let them use it, see that they love the product, you know? CSAT is high, they're using it with a high kind of usage. That for me is good validation. It obviously depends on which market you are. But for instance, when we started with one of our first kind of design partners, Yotpo, they were about 800 people strong. And when I talked to the VP of delivery, he said, you know, our product is a bit complex in terms of documentation. We get a lot of questions for success and support. And it's not like these kind of chat bot questions, like how do I, I don't know, disable my account or upgrade my account. It was more kind of a long tail kind of how do I do something complex with a product, like remove a user, add a user, do some troubleshooting and stuff like that. So we felt there's a gap with these kind of complex knowledge companies. And many of the PLG companies have that problem because they're self -serve, their product is out there. There's a lot of documentation and customers find themselves asking questions of how do I do something with a product? And that, if that's not treated, creates a lot of friction internally for support, success, a lot of questions going to product. It actually infiltrates all the way to Slack and then to the product people. And everyone is working around this customer trying to answer questions, right? So we felt that pain before we actually built the solution. Like he was really expressing it. It's everywhere. It's covering my Slack. Everyone is asking questions all the time. It's as if they work just to answer questions all day long. Jason Kirby (13:33.722) So you get that validation from the customers and that's the point in which you guys kind of decide this is real and decide to move forward. Alon Talmor (13:34.164) Yes, sir. Alon Talmor (13:45.812) Yep. Yep. Only then we actually decided to, to fundraise an actual round. I'm a bit of a conservative founder from even my first company. I always look for actual either validation or revenue to match the state that I'm in. I know that in 2021, it wasn't necessarily the case. Like companies back then would just raise money for having nothing. Just, you know. surfing that hype wave of a lot of companies having, you know, raising money. But the challenge there is look what happened next. Like if you would raise an inflated valuation, then you would need to fight now in 2023, 2024 for a next round, not to down round yourself. So I'm a little bit more conservative. I was lucky enough for that to actually pay off in this situation. I wish that, you know, wasn't so challenging in 2023, 2024, but you know, that's the way it was. Yeah. Jason Kirby (14:47.834) Well, let's break that down. So, you know, you kind of formalize the company into 2021, peak of market. You go out and raise a series of capital rounds going into kind of culminate into the seed round. So could you kind of explain to the audience, you know, what that was like? How much did you initially raise? And then what was that? The timing, like, what was your process, that kind of stuff. Alon Talmor (15:11.796) So some interesting times there as well. I was looking to bring a COO to have kind of leadership to help me build the company. That COO was actually working from another much larger company and we were playing around one day a week. And he said, you know, if we raise around then I'll join full time. And I wasn't lucky in a sense that we actually started raising money together. And I actually presented him to investors. And in the middle, he got some promotion or if he felt that leaving corporate right for a startup back then, it was a much, a little bit of a trend because, you know, people would think, wow, startups are raising so much money. Maybe I leave my corporate manager, you know, executive job and I'll just, you know, be able to live the great startup life. And yeah. Jason Kirby (16:07.172) So great, so easy. Alon Talmor (16:10.388) It seemed back then, you know, it seemed a little bit like that because they were reading the newspaper and saying, wow, people are raising insane amount of monies for nothing, you know, and why can I do that? I can probably do that. And not realizing that it's obviously much harder. And then when, you know, Pushka came to shove, we actually were offered a term sheet. He backed off and didn't continue. And obviously that created a lot of, a lot of problems in the round. Cause you know, the investors are seeing you, they're seeing that you presented someone in the company that was supposed to be an executive and they're not continuing. And so that makes the round much harder. I needed to work very hard to complete the round. It was, it was really day and night. Like I, I didn't sleep those days just to complete the round. Cause I was already in the middle. And it was kind of a more of a formal round. Like I put a lot of investors and they were all, you know, in the same timeline, trying to get to kind of a closing and kind of a more orchestrated way. And that happened in the middle, almost towards the end. So very hard. Yeah. I don't wish anyone that experience. Jason Kirby (17:33.946) So kind of in the middle of this, your main, you know, kind of the part of this executive that was supposed to come aboard just drops and you're stuck with having to change your complete narrative mid -fundraise after already starting conversations. So definitely can erode trust or, you know, commitment to an existing round. So how did you overcome that? Did you have to go out and convince the investors that were already interested that it's not going to make a difference or did you have to go bring in new investors with a new narrative? Alon Talmor (17:49.844) Exactly. Alon Talmor (17:53.684) I was. Alon Talmor (18:03.892) So I'll be, so the investor that already was, that was state of mind ventures call and Mirav, our director there, she, I actually, and that's what I recommend every founder, have a honest conversation with your investor and tell them the truth. Tell them exactly what happened and exactly why, even if it sounds horrible. They would appreciate that and you managing that situation much better than to try to make it look more pretty or nicer or change how it looks, you know? Because they've seen hundreds of companies. They actually want to see probably a founder that's able to face challenges and know, heads on, than to see a founder trying to make it look prettier because they know that if that happens now, when revenue is not great, it would happen again to a point that they don't know if they can trust. So trust is the most important thing. And I think I built that trust relationship, but telling her the truth, she was, she actually wanted to continue the term sheet. It wasn't the same terms like in the beginning, she was looking for me to, obviously she was looking for me to find maybe a co -lead. I told her, yeah, that makes sense. Maybe I'll find a co -lead. And then it was not obvious to find that kind of co -lead in the middle of the round. So those few days were really hard and I needed to kind of really, really, really be in intense conversations with many investors in that final few days until we got the co -lead from Vertex Ventures. And yeah, it all kind of finalized in the last moment. Yeah. Jason Kirby (19:55.994) And how many investors did you talk to to kind of get this round together and finally get Veritex in the door? Alon Talmor (20:04.148) Actually not too many, surprisingly. Like, she was probably one of the first we talked to and we didn't talk to many more. We were actually lucky enough to find the right ones. And yeah, it wasn't too many investors. I don't know if it's more distracting to talk to too many investors at the same time. What you really aspire to have is like to have two, three, good ones that are kind of competing for kind of the final term sheet and kind of focus on who they are and the good chemistry there than to be very widespread and talk to everyone at the same time and say, I'm in a round. And, you know, that's, that's very distracting. And you would find that you can't pay attention too much to each one of them, like you could, if you really focus. Jason Kirby (21:00.186) I think that's incredible feedback for a lot of founders because everyone's journey is a little bit different where some are like, we talked to 100 and then some are like, we talked to five. And with that, how did you narrow down who you should be building those relationships with and how did you facilitate those introductions? Alon Talmor (21:20.948) think it's all about, in the end of the day, it's chemistry with the GP. You want a good VC that are well -backed and have a good name. But in the end of the day, it's your chemistry and trust in the general partner that you feel they would be a good add to your board of directors. And they understand you. And you speak the same language. And like, you complete each other's sentences almost like you just see the world the same way. And also I really recommend, you know, GPs that are founder friendly in a sense that they, they're not too old school, you know, like not to, if the going gets rough, I just found fire, the CEO and that's it. That's my job. No, like more modern kind of approach. There are a lot of GPs that, you know, today are more like that. So I think it's both, it's kind of that kind of chemistry that you feel is, I don't think you can really express it in words. You have a conversation, you feel it. You feel that they understand what you're doing. They understand why you're doing it. What's the pain? What are you trying to solve? They see it, you know? And I think those are the ones you need to continue your conversation with. Not just the ones that say, yeah, this field looks interesting, but you feel they don't really understand what you're doing at all. It's just some... you know, general this field looks interesting or something. Yeah. Jason Kirby (22:52.634) Yeah, no, I think that's a good sentiment. I've definitely seen the, I would call them more traditional finance type VCs than I would like the VCs that are, as you say, modern that have a more founder friendly approach where it's about the relationship and acknowledging the fact that VC means there will be losses like that's just the name of the game and focusing more on trying to nurture your best. you know, poor co's and not stressing over firing a CEO or those kind of things which can create a lot of drama for VCs. Alon Talmor (23:21.972) Yeah, it doesn't always get there, obviously, but you know, even in the day to day, you want to feel that they're backing you up and not fighting against you. There's enough trouble for a founder. He doesn't need more trouble from the board. Like just running a company is hard enough. You don't need to feel that the board is not aligned with. Jason Kirby (23:44.666) Yeah, it could be exhausting to, you know, as you have to convince the board to, you know, justify whatever you're doing as opposed to then having that relationship and trust there. Cause yeah, then board meetings become a distraction as opposed to a tool to enable the founder. Alon Talmor (23:45.62) you can integrate. Exactly. Alon Talmor (24:02.644) And then the worst comes about that you're not honest with your investors. If you don't feel that you, you know, you build a good relationship, you could talk about anything. It's not a problem. Even if there's a problem, you can say it. They're not going to be too harsh about it. Then there comes a point in which you won't tell your investors the truth. And then it all goes sideways. Jason Kirby (24:27.482) Yeah, the, the stress level of a founder to have no outlet to be able to communicate and share the real deal of what's going on. Can one drive the founder to complete burnout and, or make them non -functional unable to perform. If you are carrying that burden of, you know, not disclosing what's really going on and carrying that entire burden on your shoulders, as opposed to being able to release it and share and collaborate. Alon Talmor (24:40.212) you Jason Kirby (24:54.818) with your closest confidants, which should be your board. Alon Talmor (24:57.716) Exactly. Exactly. And even small, quote unquote lies could become very quickly much larger ones if you're not honest from day one. And then it can become even too big to disclose. You say, wow, this is huge and I didn't say it. What would they say now if I say it? We didn't see any revenue. We didn't see revenue for two quarters now, three quarters. We didn't, you know. So. Jason Kirby (25:08.45) Ah. Jason Kirby (25:16.922) Yeah, and just, yeah, keep stacking, stacking, stacking. Jason Kirby (25:26.554) Yeah, I've invested in some founders that didn't disclose what was going on and that led to the, because like it was such easy fix. Like the things that were going through, they just first time founders, they didn't know any different. But they held it in, didn't get the help. And then it became unfixable because they drained the bank account to the point where it wasn't solvable anymore. So advice to founders. Alon Talmor (25:46.58) Yeah. Yeah. But then who do you go to, right? You go to your investors. You want them to, but they need to feel if they're going to give you a bridge or they're going to, you know, put their faith in you, they first want to feel they trust you. So if you didn't build that trust, then they won't come back to help you again when you really need it. Yeah. Jason Kirby (26:11.066) Yeah. And then, so, all right, let's go back to the seed. You've had that falling out, then you were able to secure it. How much did you end up raising and how long did it take you to raise that initial round? Alon Talmor (26:27.604) So the first kind of funding was around 7 million. Then when 2022 struck, we raised a little bit of an extension. There was two reasons for that. 2022, I mean the challenging market there. Kind of in the middle of the year, June, July, August, something like that. Not too far from our seed round. Jason Kirby (26:45.274) Yes, very. Alon Talmor (26:56.116) It was kind of a not a very large amount, another two million and mostly from US investors. The strategy there was to actually take multiple smaller investors that are strategic like GTM funds, Interplay and many other kind of angels or other kind of smaller that had good industry names. I really recommend that to do that, especially in the seed or pre -seed. You don't know when these guys. And they always do eventually, either finding new prospects and new deals, helping you with other investments later on, connecting you to people. And there's always something they can help you with. So I really recommend not just taking, you know, two big VCs or something like that or one, but actually having kind of a, if you can, cause it's. It's really demanding you find yourself doing conversations with each. So in a sense, you're raising money. If you took like 10 or 20 other kind of small VCs or stuff like that, you find yourself doing the conversation with each one of them. But if you do have kind of the, the, the time and power to do it, I really recommend it. It really helps you later on. You have like a much broader investment base. Jason Kirby (28:12.954) And with that seed extension, did you guys change the terms or just kind of tack onto the existing terms? Alon Talmor (28:19.668) Yeah, it was more like a safe round. So our company was growing. We were seeing revenue. So it wasn't the same terms, obviously. We were growing. Yeah. Jason Kirby (28:26.458) Gotcha. So good opportunity to kind of bring in some extra cash, build up the war chest as we go into what ended up being a terrible market to have to go out and get more money if you needed it. So, you know, wise decision on your part there, but, you know, jump forward, you're growing, you're building. When did you decide that raising an A round was the right decision and how did you time that? Alon Talmor (28:31.464) Yeah. Alon Talmor (28:54.868) We didn't. So I'll tell you exactly what happened. We were not looking to raise actually there. You know, all the investors say that all the founders say that to investors and it's a game everyone plays that you think if you're saying you're not looking for money, then you obviously are. But the reality was that leaders fund that funded our A round. I actually one evening, you know, you never know, you should always meet investors always like if you can. Jason Kirby (29:13.4) Yeah. Alon Talmor (29:24.724) Meet investors if they want to meet with you or you get an introduction or they're interested. You should always meet them. There's two reasons for that. One, even if you don't get investors, you're building a relationship. That relationship, they want to see you grow, especially in later rounds like A, B, and C. They want to see how the evolution of your company unfolds, how your revenue grows, how your market fit becomes better. So even if you don't get that investment, it's just a friendly call. It's very good to have these checkpoints. Okay. But specifically with leaders, it's that they are like a boutique venture. They do only three investments a year. And we got a very warm recommendation on them from other companies that I know the CEO there. And it was actually pure luck. Like they invited me to a dinner. It was very late at night and I was tired and a little bit sick. I remember telling my partner that I won't go. It's just too much. And eventually I did go. And the chemistry with David Stein had also sold his company in 2012, repulsed to Salesforce and with Gideon and both of the partners there that were really close to us was really amazing. Even from day one, it was really good chemistry. They were in a visit. And we then met every day after and a week after we were with the term sheet. So it was, you could, you can call it luck, but I think that a founder that takes enough meanings, suddenly this chemistry strikes at some point. So it's not exactly luck. It's you working to get that luck to happen. Jason Kirby (31:10.506) Manufactured luck is what I like to call it. You gotta do some work. It doesn't just fall in your lap. You gotta go out and put yourself out there. You gotta. Alon Talmor (31:12.668) Exactly. Something like that. Yeah. Yeah. And you never know. That's the thing with investments. You never know who would want what, who would be in the right timing with the right kind of perception of your market and the right thesis. You know, investors build their own thesis. They don't just come to invest. They research, they think about what they're going to do and what they want to strategically. invest in and you never know what state they are. Jason Kirby (31:43.898) I hope they do. I felt like 2021, there was a lot of none of that going on. Employ as best as possible. No, that's amazing. But you know, also like, you have to build a good company too. You can't just have great chemistry, you got to build something that's investable. Yeah. Alon Talmor (31:48.678) Yeah, they were just, now it's much harder. Yeah, yeah. Alon Talmor (32:02.324) Yeah, I'm over. Yeah, I'm overstating the chemistry. If you're going to get to, I think in seed round and the pre -seed, it is about the founder more about trusting the founder. I think in a round it's about, you know, product fit. Like, are you, are you closer to the millionaire or are you, are you customers loving you? If the investors called the customer without even telling you what would they say to the investor? they love you or not. Like that's critical and the good investors would just do that. They would if they see you're interesting, they would just call your customers without asking you at all. Jason Kirby (32:43.93) They put the logos on your site and they go and try to hunt down, access those people and figure out how to make it happen. Now did Leaders Fun take the entire round of the Series A? Alon Talmor (32:53.876) The seed round investors that put their pro route as well. But yeah, that didn't leave any room in the round. We didn't, we weren't looking to raise too much money, even though even now there's a lot of startups in the field of AI that raise hundreds of millions and that's awesome. But look, you know, reality strikes eventually with every founder. If you raise a lot of money with a big inflated valuation, if you don't match that, with your revenue, push would come to shove eventually. So you're just delaying what would inevitably happen. We're not in 1999, we're not in 2021. Even if there's hype in AI, that would inevitably happen that they would want to see that your numbers match something around your evaluation. Jason Kirby (33:27.322) again. Jason Kirby (33:45.338) No, I think that's good advice. And I think a lot of founders get too hung up on, I'd say it's really a first time founder versus a second time founder mentality in a lot of cases. First time founders get so hung up on maximizing valuation as early as possible and retaining as much ownership. And yeah, they just. Alon Talmor (33:59.028) Yeah. I'll have a hundred percent out of a company with a lot of valuation. That's kind of the state of mind. They're not, I'll build a company that can really make money and one day be profitable. Jason Kirby (34:14.426) Yeah, like a real business as I like to call it. There's startups. Alon Talmor (34:16.86) Yeah, a real business. Like not making money as a goal, but something that would really work. Yeah. Yeah. Jason Kirby (34:21.882) Yeah, customers love it and they pay enough to sustain it and you have good unit economics, you have a real business. So, you know, in this process, you know, I appreciate kind of your candor and kind of sharing how you've built these relationships and the chemistry. Were there any mistakes that you felt you made in the fundraising process? Alon Talmor (34:25.556) Yeah. Yeah. Yeah. Alon Talmor (34:47.7) I think the only one is that I didn't build enough relationships maybe early on with bigger investors. You could never start that too early. That's the only thing I can say. Like, start talking to investors, whatever you can. It's better if you can get introduced to GPs. There will always be principles or... not principles, but early investors that would scout for you. But I think if you, so you don't have to take all the calls because there's always scouting out there. But if you can get introduced to a GP, it's really, really important to build those relationships early on and let them see you early on. That's the only thing I think we should have done even more. Jason Kirby (35:39.514) I appreciate that. Would there be any other parting advice as we wrap up this podcast for founders out there looking to raise capital? Alon Talmor (35:50.804) I think it's more about being very candid with a lot of investors nowadays because the market is hard and investors want that kind of trust to invest in the company. So again, if you're able to build relationships and show how you're building a great business, you have to build a great business. That's a given. If you're showing them that you're building a great business and you do... having kind of multiple touch points with them. Eventually they see how it's growing and how you're building it and how it's evolving. That's probably a very good place to be to eventually fundraise. Sometimes founders say, and now I'm going to do an investment round and I'll say hello to all the investors first time. That would probably work less well than to build a relationship. Yeah. Jason Kirby (36:46.978) That's good parting advice. And for our audience here that wants to learn more about you or Ask .ai, what's the best way for them to learn more about you or follow your journey? Alon Talmor (36:57.14) So website has a pretty maybe catchy name ask slash ai .com. So you can learn about us there. And yeah, even, you know, shoot a message to us on LinkedIn. I'll try to repost this as well. And yeah, we'd be happy to talk. Jason Kirby (37:16.186) Perfect. I appreciate that. And I really appreciate you sharing your insights. There's some really, really good nuggets of information that I was able to capture from here. I have this clip feature where I take these little clips every time there's something really good coming out. And I think you hit a record in terms of the number of clips we got so far. So I really appreciate you sharing your insights and joining us on the podcast today. Alon Talmor (37:38.868) Thanks, thanks for having me. It was a real pleasure. Jason Kirby (37:41.85) awesome. Alon Talmor (37:43.284) Okay.