- Platform: meet
- Source: Read.ai 01J8T1DWN4A5KX3YSST7B0WM5H (via Ben Ornstein’s account, imported 2026-08-06)
Transcript
Charlie Greene: for making the time to chat. Ben Ornstein: Of course. Yeah, no, thank you. So how much context do you have for this call? Nearly zero. Okay, no worries. I can give you that. So I work with a guy named Michael Houck. Are you familiar with Michael? Charlie Greene: Yeah, I’m on the newsletter. Ben Ornstein: Okay, so you already know the newsletter, that’s big. That’s a lot of it. Charlie Greene: Which is great by the way, like such a great resource for founders. Ben Ornstein: Isn’t it great? Well, I enjoy it as well. I really like it. Charlie Greene: How you connected? Ben Ornstein: So I was connected because I interviewed him on a podcast when I was working for a former startup and We I really enjoyed the interview I figured it might make a it would be great to work with him because I also loved his stuff and I’m pretty good with podcasting and it turned out that he was about to launch a podcast So timing wise worked out really well, and so we’re launching that podcast next week actually, but so We a resource that we wanted to create alongside the newsletter was a a case study library of of interviewing founders about their fundraising journeys because what what else would be better than Interviewing the founders themselves that actually did it and how they did it So we have a library of like 60 of these it’s it’s live now there are Founders across all different stages, industries, et cetera. And it’s an amazing resource. We’ve had great feedback on it so far. And so that’s what this call is. It would be to be another one of those founders that gets to tell their story and is a part of this resources for other founders to check out and learn from Charlie Greene: So is the library part of Michael’s collection of content, or is it in your world, or is it something that you guys are building together separately? Ben Ornstein: This is Hauk’s world. So instead of Hauk’s newsletter, we rebranded all of this stuff to be, all of his brand to be Founding Journey. And this is like the Founding Journey case studies. Cool. So yeah, this is his world. I’m kind of working, I guess you could say with him, but for him. UNKNOWN_SPEAKER: Nice. Charlie Greene: Okay, cool. Yeah, he seems like a killer guy to work with. Ben Ornstein: So good for you. He’s been awesome. He’s been amazing to work with. Yeah, 100%. Charlie Greene: How did you get into the podcasting world? Ben Ornstein: So the quick background that is my senior year of college, I, I interviewed the, or I did calls with alumni from my university. I wanted to learn all about, you know, what they were doing mostly in the business world. Uh, cause I had a finance degree and I wanted to learn about, you know, industries I didn’t know about or, or within business, what, what areas I wanted to learn more about also what I didn’t want to go into like learning about like insurance. I did an internship that was never again. Charlie Greene: I did all that and I learned so much that could have potentially saved me years of pain, places to live, industries to work in. Ben Ornstein: It was amazing. And so I told a friend about that who gone to school with, and he loved it. He loved the idea. I think he did it himself too. We said, you know what? Why don’t we just do the same thing, but do calls with people across all industries, not just alumni, and broadcast it to the world. And so we launched it together, but he ended up working at M&T Bank doing the PPP loans. So it was essentially just me doing the podcast. And I did every aspect of it, 50 plus episodes. And I loved every second of it. Not having a full-time job at Morgan Stanley. So, it was an amazing experience and while the quality then wasn’t very good back in 2020, I learned a ton and it was so much fun. Charlie Greene: What’s your tech stack for doing podcasts these days, if you don’t mind me asking? Ben Ornstein: Yeah, Riverside. We love Riverside. And when I was doing the editing myself, it was just Adobe Premiere Pro, but Now we are working with an external team to make it even better. Charlie Greene: So hell yeah. Great. Yeah. We, um, I was using Riverside like three years ago. Yeah. I’m like very, I don’t know when you started using it, but at the beginning it was like, it was dog shit. It was so bad. Like at least half the calls were like unrecoverable. Yeah. And I remember they were looking to raise money and I was like, this is such a loser of a company and then losing money to like fix that. And It’s just absolutely just a killer product now like it’s It was really bad back in the day. Ben Ornstein: And when I was doing my soul podcast, I only did audio only so I was using a product called zencaster Not bad, not bad. But yeah, I remember riverside in the earlier days were just it was bad. Charlie Greene: Yeah no, we um, we do all of our customer testimonials through riverside.fm and um It’s like every month they like come up with just like an increase mental change that makes it easier for someone who’s spent the last four years just trying to figure out how to use Zoom over the age of 70. I’ve now gotten to a point where I can pretty confidently get someone on Riverside without having to worry about them being able to figure it out. And then now I just stop recording, and then I see how much time there is to upload, and then I just have to find a way to small talk them so I don’t have to explain to them later how to upload this shit. That’s great. No, I’m glad you And we use the script for all of the editing, which I aspire to have a third party that does all that for us at some point. That’s definitely the way to do it. Ben Ornstein: Yeah, I mean, happy to intro you to the guys we use. They’re Eastern Europe, but they’re very active. Yeah, if that’s interesting, I’d be happy to make an intro. Charlie Greene: Is it pretty cost effective? Ben Ornstein: Yeah, they’re not bad. They’re definitely cheaper than like, we’ve been in talks with some of the top podcasters cast editors for top shows, way more expensive. It’s not even close. I’m working with these guys to perfect the flow, but they’re pretty good and definitely cost-effective. Charlie Greene: Cool, nice. Yeah, nothing that we’re doing is particularly high fidelity, so we probably don’t need the cast. I’m looking for people who can just string stuff together, mostly for internal and some external. But yeah, I’ll keep that in mind as we start to build that out. Thank you. Ben Ornstein: Yeah, of course. Sounds good. Yeah. Do you have any other questions before? These are softball questions. There’s going to be nothing that you haven’t answered before. And this is obviously recorded. The only reason I have the read AI guy in is what happens is we turn this conversation into a text-based transcript, or we take the transcript from the document and translate it into a document. I’ll send the document. To you for review. You can say, hey, I actually don’t want this. Actually, I wanted to add more context here, etc. And then we’ll give you before it kind of goes live, you get a chance to kind of edit it. Charlie Greene: That sounds great. Yeah, perfect. Ben Ornstein: Awesome. Okay. Yeah. Do you have any other questions? Charlie Greene: No, no, let’s let’s do it. Ben Ornstein: Amazing. Okay. Well, yeah. Charlie, please introduce yourself and your startup. Charlie Greene: So my name is Charlie Greene. I’m the co founder and CEO of Remento. Our mission at Remento is to help families capture and preserve the stories of their family. And the Remento product is the first no-write life story book that has ever been created. We help families take the memories of aging relatives and turn them into a book of stories that can be written without anyone in the family having to write a word. And a little twist that we add is the books get printed with QR codes that when you scan will bring you directly to the recording that was used to write each chapter. So a lot of families use Remento to be able to create a book for the future. And what they come to realize is the journey of learning stories in their family that they never knew comes to be just as valuable as the kind of like keepsake that gets to be preserved. We’ve been at it for three years. It’s been an amazing journey. We’ve raised institutional capital to fund the team and the research and the product. And yeah, everyone on this team has a different reason for being involved. But all of us recognize that there are just so many people who have incredible stories to tell. And ultimately, we have all of the technology that we need to be able to document those stories. And for many families, we just need a little bit of an inspiration to get started. And what we try to do with Remento is just make it as easy as possible for people to not wait until tomorrow to do something that really ought to be done today. Ben Ornstein: I can think of both of my grandparents. My grandpa died at 68 years old. I never even got to know him. And then my other grandpa, who’s still alive at 93, he wrote an entire book for himself. Both of those would have been valuable to use your product. That’s two stories within my family alone, so I can’t even imagine. Yeah, exactly. Which is so cool. But yeah, could you dive a little bit further into the fundraising journey? You could say how many rounds you’ve raised, if you’re comfortable, valuations that you raised at, a lot of founder. Because again, this is not going to be public, it’s going to be behind a paywall. But again, whatever you’re comfortable with. And yeah, anything around that. Charlie Greene: Yeah, so we raised our first round in July of 2021. We raised a total of two rounds. We did a pre-seed and a seed. And Upfront Ventures led our pre-seed round. And we had two other institutions that were involved, Flybridge and Alumni Venture Group, as well as, back then it was Seven Angels that joined in partnership with us, people who had deep expertise in technology leadership, CPOs, Chief Product Officers of a variety of large companies, and then people who really understood the world of marketing and communication and storytelling, which is ultimately our business. So I was in business school at the time. When I was raising the money, I can share more about what that experience was like, But I remember hearing, the best money that you can take is like quiet money, like, you want to get the money in the door, and then you just want to like have investors that are like, they have faith in you, and they just let you do your thing. And I remember thinking, like, this is my first time building a business, why on earth would I take money from people that don’t want to be involved? I have so much to learn. And I’ve made a whole lot of mistakes along this journey. But finding investors that were committed to what we were doing and experts in their field was not one of them. So I was really proud with the group that we assembled when we originally raised the round. And then we raised a seed round to fund our growth 18 later and brought in a couple of additional angel investors, one other institutional investor, and then a participation for the previous rounds. We raised a total of $4 million. Ben Ornstein: And what was the split between those two rounds of how much money you raised? Charlie Greene: The first was two and a half. And then the second round, we raised another one and a half. Awesome. Very cool. Ben Ornstein: Yeah, no, we have a bunch of questions later on about like, you know, interesting stories, challenges you had. So I'm sure you're about to dive into those. Charlie Greene: Yeah, happy to. Awesome. Ben Ornstein: So when you were raising the money, you know, what did you what did you plan to use the money ahead of time for? Were there milestones you wanted to hit before the for the next round of funding? And yeah, how do you allocate that cash? Charlie Greene: Yeah, so from the very beginning, we We raised our first round with what, from my perspective, was a really strong team, a very clear problem for us to go after, and a really strong hypothesis for the solution that we would need to build to be able to make that work. And we had done a lot of experimentation, and we had built a very early MVP, but it was clear that to be able to have the impact that we wanted to in the space, we were going to need to allocate a meaningful amount of money into actually building the product itself. So the first amount of money that we raised was to build a product team that could go out and build a product in the way that we had envisioned it. And we ultimately, within a year of having raised that money, transitioned from the kind of like earliest, earliest kind of like road, like pre-MVP, like kind of like rough learning oriented prototype towards actually building MVP slash V1 of our product. And it was actually very different than the way it exists today. It was a mobile app for facilitating in-person oral history interviews. We had tens of thousands of people download the app, and many of them loved it. But ultimately, what we realized fairly quickly was the engagement was really not doing what we needed it to do. And we faced kind of like a decision point where we could either double down on the concept, double down on the solution, which we felt well, you know, there may have been an opportunity to be able to actually turn into a real company or pivot. And that was one of the hardest decisions that we had to make because for every founder that doesn't pivot, there's another founder that pivots too soon. And I remember thinking like, I believe that this thing could work. And we have people that are telling us this is exactly the thing that I've always been looking for. Part of the thinking for us building in that product was that there were tens of thousands of people every year who were Google searching, how do I do this? And the only thing that was available was a listicle. So we were providing a resource to be able to facilitate basically sitting down with a grandparent and interviewing them. But for so many people, what we heard was the problem resonated really clearly. I downloaded the app, and then I realized it was going to be a good amount of work for me. And so I'm saving the app for the future when I'm with my grandparents. And ultimately, we just weren't able to get enough people using the product in a way that would make make a freemium pathway to monetization actually viable. So we made the decision to pay that, and we embraced kind of like the AI wave, which was making a lot of the things when we originally raised our funding at the beginning possible that weren't possible when we raised at the beginning. And that was specifically around being able to facilitate asynchronous interviews, which the idea of in 2021 getting a grandparent to share their story without you being there. It was just like there was no way that was going to happen because of all the things. It was ludicrous. It really was. And then a combination of the pandemic happening, but then also AI allowing for the kind of elaboration in real time and the follow-up questions and things like that gave us an opportunity to do something that historically wouldn't have been possible. So that was when we raised the extra money from existing investors had gone after was incredibly valid, which is one of the hardest things to do when you're building your startup is to validate the problem, to build a very different solution. And we went ahead and did that. And it took us, I think, eight months to go from the decision to pivot to actually launching the MVP of the Remento book as it exists today, which was going from memories to a written book of stories. We launched in October of last year, right before the holiday season. And we've been refining every part to the product experience since, and then increasingly focusing a lot on distribution, go-to-market, and scaling our customer base. Ben Ornstein: Wow. Yeah, that's a crazy pivot story, especially when something was like, quote unquote, working. That's hard. That must have been a tough decision. Yeah, the early stage game is insane, right? It's like, you could go down that path, and especially because you believed in the product. That's so, that's even more tough. Usually when founders pivot, there are relatively clear signs that it's not going to work. Charlie Greene: Looking backwards, it actually may have worked. If we had really focused on how to market that product, there could have been opportunities to find a way to monetize it in a way that was different than the way that we were thinking about it. It was clear to us the freemium pathway wasn't going to work. But I think if we had decided to shift into a B2B2C approach, that technology that we had developed, which is quite powerful, could have been used in other ways. But ultimately, the reason why we all decided to work on this product was for the impact that we knew that this could have in the lives of everyday families. And so it was really important for us to be able to, over the next couple of years, have tens of thousands, if not hundreds of thousands and millions of people have access to our product, not because that was what we owed to our investors, but because what we had committed to ourselves was important, which was trying to get as many people as possible using Rementa. It's because when I talk to people, like I talk to people who hear about our product, and I almost always hear one of two things, which is one, like, oh my God, my grandfather would be perfect for this. Like, we've got to use it with him. Or it's the opposite, which is like, I wish I could have, right? And you literally did both of those when you started, right? But it's always one of two things, and it's rarely both. So if you've been. Ben Ornstein: Yeah, well, no, that's fair. I guess I'm your ICP then. There you go. Charlie Greene: You totally are. You totally are. Yeah. Ben Ornstein: No, that's so cool. I love this product. If I had the money to invest in the earlier days, I definitely would have. But yeah, so how would you decide which investors would be a good fit? Charlie Greene: A couple different things. Charlie Greene: we set out to build this business, we spent a lot of time thinking about what was going to be important for us from an investor perspective. And there's no question that a top-tier investor lends credibility to a business that will help with things like recruiting, future fundraising, and things like that. But the other thing that was really clear to me from folks who had raised money in the past was that there are certain investors who are just experts in very specific things. And what we found and Upfront, who's been a phenomenal partner for us, is a fund that is more deeply connected to the world of storytelling in Los Angeles than any other fund in the world. If you were building a storytelling-adjacent business, you'd want to go find probably the best investors in Southern California. And we had the opportunity to work with them. And for that reason, it was really a no-brainer. They have a phenomenal event every year that brings together basically and Hollywood at their summit. And they've just been great partners with us, connecting us to that world. Because so much of the marketing of this product is by way of promoting the stories that exist within our platform. So they've been great partners in that regard. And then the other thing that I, when I was starting to raise money, was once we had secured our lead, the question that I asked myself is like, what are all the things that I think we're going to run into as issues? And I can either give people equity to become advisors to help me solve those issues, or I can take people's money and ask them to help me solve those issues as investors. And that math still kind of boggles my mind that that's the way it works. But we went out and we said, product is going to have to be best in class to be able to work. So let's go find the chief product officer at LinkedIn, at Snap, at Figma, and let's invite them to be investors. And they were excited about the mission because it resonated with them. Let's go find people who know the the things about the world of storytelling. So we have Reese Witherspoon, CEO of Hello Sunshine, as one of our investors, who knows the world of storytelling better than anyone. Let's find people who know a thing or two about leading a technology company. So we have a former CEO of Fandango, CEO of Protege in LA on our cap table. And then also, let's make sure that we actually know a thing or two about marketing and communication. So we have a public relations guru, Brooke Hammerling, as one of our investors. So for me, it was quite simple. It was like, where are all the areas that I I think if this business doesn't work, we will ultimately be able to point our finger to and say, why? And let's find people who can, in an hour of their time a month, help us avoid all of the pitfalls that every founder is very much positioned to kind of fall into. Ben Ornstein: Yeah, I'm always amazed that founders don't always approach it the way you do, because that makes so much sense in my mind. Like, wouldn't you get, wouldn't you want, I guess it's not always easy to raise funding for certain businesses, obviously, but I love how you approach that. Just filling all the gaps and getting amazing people as angels if you were able to. That's a great group of angels you amassed there. Charlie Greene: One thing I would say, just maybe in addition to, and I agree, I don't know why more people don't do it than me. Again, I have the benefit of not having done this a bunch of different times, so I'm not jaded by the way other people do it. Oppression this with I think common sense generally but one of the things that I think is fair to say is there are professional angels who invest in 50 or 100 companies a year and you'd be fooling yourself to think that you'd have a couple hours of that person's time a month right and so what we found actually was going after people that weren't making 10 20 or 30 angel investments a year but who could afford to put some amount of money into our business was meaningful for them. And also because the story of what we're doing connected with them personally, you know, it gave them an opportunity to feel good about supporting us. And we can talk more about like kind of like the strategy with with raising, but raising money in every other part of building a business is all about storytelling. That's my background. And that's the only reason why I've been able to do any degree of have any degree of success with raising money is because I've just fallen back on what I know, which is how to tell stories. And there's a lot that goes into fundraising, but ultimately, if you have a compelling team and a compelling story, that has been what has, I think, allowed us to be able to differentiate ourselves from other companies, you know, in what has been a really crowded marketplace. Ben Ornstein: Yeah, I think there may be aspects of that that you might be able to touch on in this answer to this question, which is, How'd you get in touch with investors? Charlie Greene: So at the time I was in business school, when we started raising money, and I remember spending a lot of time within the business school accelerator, just speaking with anyone that would talk to me. I had a calendar, and I was like, if I can do 20 meetings a week, where I'm not asking for money, I'm asking for advice. That would be great. And at the end of every call, I would always ask the same question, which is, is there one person that you think I'd be smart to talk to? And every time I asked that question, almost without exception, I ended up talking to someone who was probably more qualified than the previous person to give me relevant advice. So by the time I was five degrees down the rope of having been connected to people, I was talking to the people who knew the space, who had built companies that did not in this space, who made acquisitions in this space, who were connected to people who knew a ton about product and marketing and storytelling. So for me, it was just, it was asking questions, going in with a humble mindset and being interested in learning with a mission that I think for many people resonated, that I was able to really quickly network my way from, you know, exploratory calls towards kind of like creating a deck in between calls to at some point being connected to people who I didn't realize we're venture capitalists. Then realizing that we were in the middle of a fundraise before I ever decided to start a process. And that's one of the things that I think a lot of founders do better than I did which was be really rigid at the beginning with how they run their process. And we were not that way at all we were just in the market having conversations learning about what was out there. And we ended up getting connected with people who had faith that if we had money, we could do something really exciting. Ben Ornstein: Ask for advice, not money, and then you'll actually get it, is that quote that everyone always talks about, right? That's right. UNKNOWN_SPEAKER: Yeah. Ben Ornstein: And you, I love, there's a distinct thing that you did that I think is interesting. Some people ask when they speak to someone, can I have three people that I should talk. You said one. And I think that's a distinct thing that you did that I think that's interesting because then there's one person in the person's mind that you're speaking with, instead of three decent people that you could have chatted with that might've added value, they probably connected you to the one that could have had the most value, which I think that is interesting to think about. A lot of people approach it with, oh, we're five people that you might be able to connect with. Charlie Greene: You understand what I'm saying? Yeah, 100%. One of the things, I spent a lot of time before I started raising money trying to get jobs in Washington, DC, which is where I spent my career before going to business school. And the thing that I learned with networking is fundamentally everyone, when they take on a networking call, would love to be helpful to the person they're speaking with. Going to bed at night feeling like you helped someone is a wonderful feeling. And for many of us, we're just really busy, which means that we don't have the time to think about how we can help that person. So actually, if you're asking someone for help, the greatest gift you can give them is specificity as to exactly how they can help you. If someone comes to me and says, like, hey, Charlie, do you mind if we talk for 30 minutes? And at the end of that, they say, hey, by the way, I saw that you're connected with Ben Ornstein. I'm thinking about starting a podcast. Would you mind connecting us? I'll shoot you this note if you could just forward it to him. That'd be great. I'm like, hell yeah. But a gift, yes, I would love to do that for you. Ben's going to be excited to connect to you. You're going to be excited to connect to him. And I'm going to feel great knowing that I helped you out. So it's just the more clear you can be with how someone can be helpful to you, the better. And one of the things that I learned early on is asking for help is an act of humility. Really, it's an act of vulnerability. It's not an act of hubris. And I think that mental shift takes time to learn. It's only when you start asking for help can you actually position yourself to get it. And anyone who thinks they don't need help to do anything like start a business is going to lose. Ben Ornstein: I couldn't agree more. I couldn't agree more. And so in the early days, you talked about it was a more unstructured process than how you might have approached later rounds now. Did you do any cold outreach in the early days? How many people did you reach out to? Charlie Greene: I didn't do a single cold outreach. No cold outreach, it was all connections. No, yeah, I've never had luck with cold, never have. And when I say not cold, I don't mean like smoke and warm. I'm saying like, hey, this was someone that you're connected to on LinkedIn. And they say, haven't talked to that person in 15 years. I'm like, awesome, here's my email for you to send to them, that's great. So it doesn't have to be hot, but I've never, I've sent a lot of cold emails and none of them have ever materialized. But just anything that's not super, super cold generally has just such a higher degree of working. And I think spending time building your network in the areas that you want to be able to build your community allows you to never be more than a connection or two away from being in touch with someone. So yeah, I mean, you have to just put in the time to meet a bunch of different people. We were raising money in the peak of COVID, which meant that people were very comfortable with Zoom, which meant that I could do 15 calls in a day. And there were some days where I did. And it was just back to back to back. And I created a CRM for myself, which is always advice that I give to a new founder. We didn't have Fathom or Read AI back then, so it made it a little bit more difficult. Just as soon as you get off a call, take notes about what was said, send a follow-up email, and add that person to Elissa where you're staying in touch with them going forward, right? And just like get into the habit of doing that, stay organized as you're having those conversations, and then make sure that you stay in touch. Ben Ornstein: Yeah, no, 100%. It's great advice. And so I guess I'll ask a different follow-up to that. Of the people that you had first calls with, how many materialized into, I don't know, second and third calls, if they went that far? And then at the end, how many of that funnel turn into actual investors? Roughly, rough numbers. Charlie Greene: Yeah, I'm thinking about the best way to break it down. I mean, we really, I started out this journey by talking to hundreds of people. And some of them were investors, some of them were entrepreneurs, some of them were marketers, some of them were product people, and I was just looking for advice about how to start a company. There was never really a process for us in that first round where we were actually looking for money. It literally just kind of materialized on its own. As soon as we started getting term sheets, it was like, okay, let me circle back to all these people and let them know that we hadn't been looking for money. We now have a term sheet. We're really excited about building this business because we've spoken to so many people. Are you interested in being involved. And that worked, that ended up working, I think, really well for us. So I don't really have numbers. I'm like, we had 427 people that turned into 70. One, it was just I, my favorite part of this job has always been talking to people. And one of the things that's unique about this business, I think that's special is, you know, our ICP is not, you know, a fourth year engineering student who wears the color black in their t shirt, right? It's like, anyone can buy our product, which means that every kind conversation that I was having was literally customer discovery work. So I was taking furious notes trying to understand, you know, this VC actually interviewed their dad seven years ago and didn't do anything with the tapes afterwards. This other person had a parent who passed away and did something really interesting in the memorial service. So I don't remember the conversation that we were having. Ben Ornstein: Yeah, no, that totally makes sense. And I actually like the way you approached it, because I've had such a wide range answer. Sorry if you hear that dog, she goes nuts upstairs. Oh, good. Okay, good. I guess the mic does a good job of blocking the outside sound. And so I like the way you approach that because it's like, and it maybe is the form of your business just being different from like having not a specific ICP and that might've been it. But so when you were talking to investors, when you were having those conversations like prior to receiving term sheets that were in the form of like a pitch. What did you emphasize? Charlie Greene: I emphasized a couple things. I think for us, I was going into those meetings knowing that investors would really, really care about the team, the problem, and the opportunity. And so the first thing when we were thinking about team, I was thinking to myself, why would someone invest in me to solve this problem and my co-founder versus anyone else? And for that reason, I always started with my own story. And I made sure that when someone walked away from our conversation, if they didn't know anything else, they would walk away knowing that Charlie is the guy who's going to be waking up every day for the next five years thinking about this problem, not because he's interested in solving it hard problem to solve, but because he's the person to solve this problem specifically in a way that no other deck that's going to come across my desk is going to. So that was always priority number one. They can say whatever they want about me, but they should know when I leave that meeting that I am the guy to solve this problem. The second thing I wanted to do is make it really clear that we were not coming up with a solution for a problem that didn't exist. So we focused really hard on saying, there is a real problem here. And let me help you understand why we're thinking about it in a way that is unique and special. Because companies can pivot if they have a problem and they're coming up with different solutions. But if you've got a great solution for a problem that doesn't exist, your pivot is going to be inconsequential. So the second was always thinking about the problem and making it really clear how we had created some insight into the problem space that allowed us to differentiate ourselves from anyone else. And then the third was the approach to the opportunity that we saw in front of us. But frankly, if you were to talk to our investors, I think many of them would have said, yeah, the opportunity that they put forth, I didn't really care as much about that because I knew it was going to change. It's early stage. They had to build, they had to talk to customers, and they were going to refine the vision as they went. So I would say the thing that we really focused on is team and then problem. Ben Ornstein: Yeah, makes a ton of sense. In the early days, you're betting on the team, right? Investors know people are going to pivot. That just happens. Most of the time, probably, I'd argue. You kind of touched on this already, but what did you do to drive urgency among investors? You kind of said like you kind of circled back when you did receive a term sheet, but yeah, did you apply any tactics or anything to apply any urgency? Charlie Greene: I think the advice that I've gotten early on was you don't want to be raising until it's really go time. Right? So build your network within the context of wanting to learn. And that worked really well for us, looking at someone in the face and saying, we are not actively raising, but I've heard amazing things about you. And I'd love to build a relationship so that if we find ourselves raising, I can be in touch. And that allowed us to meet a bunch of different people, which was awesome. And then there was a sheet that we did receive. And actually, remember, we received a couple term sheets. The first term sheet we received, the terms were absolutely shit. Garbage. And I remember thinking, like, we're not ready. Like, I don't feel like I understand enough about who the best partners for us to work with could be for me to begin this process. So we just said, we're not interested right now. Thank you. But, you know, we're not going to move forward. And we went on for a little bit longer. And then we got a second term sheet. And I remember thinking like, okay, I understand who I would love to bring together to make our pre-seed round. And that was when I went back to all the people that I had spoken with and I said, look, this is moving faster than I anticipated. We're gonna be raising in the next three weeks. No pressure, but if you're interested, like I'd like to talk in the next three days. And there were plenty of people who said, you know, no, like, that's, that sounds great. Like, I'd love to be involved down the road. And I'll pay a premium for some of the risk taken off the table. And then there were other people who said, like, it was just a matter of time until you got your term sheet. I wasn't in a position to lead, but I sure should have been in a position to follow. And I'd love to. Ben Ornstein: That's awesome. Now, you like applied FOMO without even really trying, it just kind of happened. Charlie Greene: It's like, that's kind of the whole game of this. And And it is one big game of creating FOMO. And I think the people who are best at fundraising are able to do that in a way that feels really honest and authentic. Because creating FOMO doesn't have to be at the expense of trusted relationships. It can just be because you've built a great product that people are excited about, and you as a founder share that excitement. So you're just trying to find the people that are as excited about the business as you are. Again, that's always worked really well for us. 100%. Ben Ornstein: And in hindsight, I mean, you are a great storyteller, and you do make it sound like sunshine and rainbows, but there were of course challenges, I'm sure that came up. What was the biggest challenge that came up during fundraising? Charlie Greene: I mean, we pivoted our business, right? Like that was pretty hard. That's a hard thing to do. I think the other hard thing to do is figure out how much money you need to raise. At your early stage, the idea In the perfect world, you're raising exactly the number of dollars that you need to reach the inflection point in your business where it becomes worth meaningfully more money, at which point you can raise a higher valuation. And as a first-time founder, the reality is that so many of us are thinking about what that number is, and we're generally off by about 150 to 250%. Generally, it costs twice as much time and money as you think it's going to take. So trying to figure out the amount of money to raise it was difficult. And generally speaking, if things are going really well, it's easy to raise. But more often than not, if you're halfway through the time that you thought it was going to take, and things are not going well, or it's taking longer than you think, it's generally not the time where you want to be going and raising more money, particularly if you're still pre-product. So thinking about the amount of money we were going to raise and how we were going to spend that as a team, we knew exactly what we wanted to do. But thinking about exactly how we were going to pace that out, that was a challenge. Pivoting was definitely a challenge. And then the second time that we raised, you know, we raised our first round in second 2001, round in 2000, sorry, sorry, 2021. The second round was in 2023. And a lot had changed macroeconomically between those two periods of time. So finding investors that were still bullish in the space after we had gone through, you know, one solution that hadn't worked, but were more confident than from the beginning that the problem could actually be solved. You know, that was a whole nother challenge in and of itself. So I was really proud of our team that we were able to pull together another, you know, another sum of money to be able to go bring this new iteration of our product to life when, you know, a lot of my friends' companies were not able to raise and ultimately shutting down because the economy had changed. UNKNOWN_SPEAKER: Yeah. Ben Ornstein: No, 100%. Are there any other unique or interesting stories related to fundraising that you haven't touched on yet? Yeah. I mean, it might not be, but we like to give that option in case there were multiple stories that are worth telling. Charlie Greene: Yeah, no, it's great. Let me think for a sec. Ben Ornstein: Yeah, yeah, take your time. Charlie Greene: Yeah, maybe. I don't have a specific story. It's just fundraising is really hard. It's really hard. And for founders who are going into it, I think the thing that I've just been reflecting on is that I remember when I started this journey, the TechCrunch article that gets written after you raise your first round was like, it felt like the victory line, the finish line. And I think the thing that I've come to realize is that fundraising Fundraising is really not much of an accomplishment. It's really an obligation. And it needs to be viewed that way. Because it's a commitment to your investors to do the thing that you promised you were going to do. And on our team, we take that really seriously. So yeah, I don't have any other great stories to share. Ben Ornstein: No, that's all good. And no problem at all. You kind of already gave some great advice there. Is there any other fundraising? Advice you'd like to give to founders? Charlie Greene: Yeah, I think if you are a founder and you don't love talking about your business, you got to rethink what you're doing. Because that's your job. You are the chief storytelling officer of your company. And for some people, that's a real strength. And for others, it's a real area for development. And whether you fall into the first category or the second, the way that you get better is by practicing. And my advice would be, don't start telling the story of your company in fundraising conversations. Start in the context of just sharing your idea with people who will listen. And those people can be venture capitalists, but those people can also be smart people who are willing and interested in helping. And I would say, make sure that you're spending a lot of time in those circles before you transition into the kind of like fundraising mindset. Because by the time you get there, you got to really be on your game. And those first couple hundred conversations will really help you get there. Ben Ornstein: That's amazing advice. No, 100%. Who's an investor that you'd recommend to other founders and why? Charlie Greene: I'd recommend Upfront Ventures, 10 out of 10, over and over again. Phenomenal, deeply involved, very strategic, incredibly thoughtful. So I think they've been great partners to us. And then, yeah, why don't I leave it there? I think we've worked with some great angels who don't make that many investments, so that's probably the most helpful thing for other founders. Ben Ornstein: 100% definitely. Are there any resources you would recommend to founders? This could be books, newsletters, podcasts, really anything. Charlie Greene: Yeah, I'm a huge fan of Matt Mockery's book, The Great CEO Within. If you haven't read that book, you should if you're starting a business. You can read the entire thing for free in a Google Doc. So I love that guy and his work. I listen to a ton of podcasts. I spend a lot time thinking about product. So Lenny's product podcast has been one that I spent a lot of time listening to. He's got a great breadth of different kinds of folks who all think about early stage in different ways. And making sure that you're spending time engaging and reading about things that have nothing to do with your business. Because I draw a lot of inspiration from podcasts that have literally nothing to do with anything related to my day-to-day today? Ben Ornstein: I mean, I just love the balance of that answer, because that's so true. And we're trying to model our podcast off of Lenny's, because it's so good. Charlie Greene: He's a phenomenal interviewer. If you just think about his development as an interviewer, he's gotten so much better since he started that podcast. And I think he's just a real master class in how to create engaging audio content. Ben Ornstein: 100%. I could not agree more. Yeah. Question is do you have any uptakes regarding the fundraising process? Charlie Greene: I think cold outreach works Like if you're doing cold outreach, it just means that you haven't you haven't done your job yet You know, find a way to be warmly introduced to someone. And if you need a LinkedIn premium subscription to figure out the three degrees to get to someone, just spend the money to do that. Charlie Greene: I think that being a founder can be incredibly lonely, or even a co-founder. So founders are really well-served to find community in some way. Whether that's through something like YC, tech stars, or just local meetups. Some of the best fundraising advice that I got was not from people who raised $100 million for a company 10 years ago, but from people who are actively in the process of raising money. That’s the other thing I would say, like, when you’re looking to raise money, don’t be afraid to take money from people who don’t have fancy names and titles. Like, focus on people who can actually help you with your business. Charlie Greene: And then I would consider myself in a privileged position where I didn’t have to take money from friends and family. And maybe my hottest My hottest take of all is I am so obsessed about our business, so obsessed about our business, that when I’m with my friends and my family, I really like not having to think about work. And I feel really thankful that I’m able to keep those worlds separate. So I know some founders don’t have a choice but to start off, you know, looking for money from friends and family, and they’re looking to be able to provide a return to their friends and family. But generally speaking, unless you have a friend or a family member who understands what it means to invest in a startup, which is a highly, highly risky investment with a very small likelihood of a return as an asset class. I’ve just been in a privileged position to be able to not have to tap into that audience. And I know a lot of people who have had relationships change in their lives because of things related to money. And again, I just I love that at Thanksgiving, people ask about my job because they’re curious, not because they’re expecting a return. Ben Ornstein: Yeah, no, that’s an amazing position to be in. And I think you’re thinking about that the right way. And yeah, lucky to not have to do that. Yeah, no, Charlie, this has been an amazing conversation. I really appreciate you taking the time. As I mentioned, we are doing a podcast. I love the way you tell stories. I can’t guarantee when or if but because I’m not the how the the host of the podcast Michael Michael Hawk is I Just kind of help them. I come up with the questions. I help with post post After the conversation and turning it into like a production But if you would be open to it down the road, would you want to feature potentially on the podcast? Charlie Greene: Yeah be happy to yeah, that’d be great. Ben Ornstein: I appreciate that. I I’ll definitely talk about it. I’ll reach out to you in the future about that. I just think you would be an amazing, amazing guest. Charlie Greene: I appreciate that. That’s really kind of you to say. Thank you. Yeah, I’d love to. Again, I think I’m excited to see more of the work that you’ve done in the past, but I’m a huge fan of his writing. Ben Ornstein: Oh, yes. No, he- Yeah. I think I can give you support, 100%. I really appreciate that. Yeah. No, thank you. Charlie Greene: What is your favorite episode of the Lenny podcast? Charlie Greene: If you want to think about it. Ben Ornstein: No recency bias, but the Nikita episode is amazing. I love the fact that he has been able to just build the same product twice and successfully do it. He is such an interesting builder. I’m non-technical, so I’m just innately just kind of jealous of technical founders. And just the way he describes being able to build businesses and what to avoid is, it’s so good. UNKNOWN_SPEAKER: Yeah. Ben Ornstein: What about yourself? I’m curious. Charlie Greene: That episode was amazing. We spent, I spent many hours. Did you ever download gas and like play with it? Ben Ornstein: No, I never actually did. Funny. Charlie Greene: Download it, download. Just like out of curiosity, like that app feels so good. So simple and like silly even, like playfully silly. But there is just so much brilliance within the most simple, like kind of construction of the way it’s put together. But for me, like the thing that stuck out the most in that podcast, I just listened to that like last week, was the fact that gas was, or TBH was their 15th try, right? And like Nikki DeVire is like the savant guru of the app world. And it’s just really important to remember that like, it literally his brilliance is not the fact that he pulled this thing out of his ass, is that they experimented their way into creating it, and it took them 15 times. And there are very few founders who do 15 of anything. So like, yeah, that’s, it’s not like it was just randomly one in a 15 chance. It was the 15th thing they tried. Right. So it’s just a good reminder that like, sometimes it’s easy to get down on yourself as a founder that like, you haven’t figured it out, like even the best it Really takes time and they were like out of money and people were quitting on them and it was like really dark. Ben Ornstein: So yeah That was a cool episode Such a cool episode such a great show my my love for podcasting especially in this niche came from how I built this Um with guy rods i’ve listened to I think literally every episode that that podcast has released I’m like and I and I started late so I went back to the beginning and listened to all of them. Um, God, it’s that production is so good And the stories I still tell to this day about like, oh that reminds me of this company five guys when they did this Yeah, it’s my favorite podcast is recommendation wise like Charlie Greene: outside of the world of exactly what I’m doing is the acquired podcast I’m loosely connected with Ben Great great. Ben Ornstein: I’ve never actually talked to him. We just had like over LinkedIn conversations, but great podcast as well. Charlie Greene: Yeah. It’s like a little much sometimes in terms of the length, but the Costco episode, if you haven’t listened to that one. Yeah. I mean, it’ll take you, depending on how fast you listen to it, somewhere between two and three hours to get through it. But yeah, just like the depth of their research is just so incredible at Costco as a business. Is so much more fascinating than any of us know anything about. So that’s another really impressive one. Ben Ornstein: Absolutely. I’m going to have to check that one out. And just one question out of curiosity, what are you guys planning to build out further? Because I generally understand your business, but what are you building towards? Charlie Greene: So right now, the things that we provide our customers are these physical books. Okay, Google does weird blurry. Yeah, you can see Yeah, this was if this was a video podcast, we would figure this out. But basically, there’s a photo here. And this is my mom’s story that’s written right here. Well, it’s been fully automatically created. In this case, it’s actually written in the third person. So our speech to story technology took her transcript and actually turned it into a written story. And then if you want to actually hear the word, you just scan the QR code. So building towards is basically an experience that for people over the age of 70 feels a lot more like having a conversation with a professional interviewer who then is ghostwriting your autobiography than submitting a speech-to-text questionnaire about your life. And the great news for us is that there are a lot of companies that exist out there that are helping us do that because our core competency is not transcription or translation or writing stories. Our core competency is creating an incredibly seamless user experience that allows someone to go from feeling like they have all these stories in their brain to having something they can actually pass down to their family. So what we think about as a business is how do we create a platform that accumulates your family’s most precious memory content in your life? And how are all of the tools that are coming out, whether it’s the new speech-to-text capabilities of GPT, DeepGram’s ability to translate in real time or anything else, how do we lean on third party tools to enable you and your family to create, again, this platform of the most important data that you’ve ever experienced? So we’re thinking about that in a variety of different ways. And then, of course, the corollary is once we have all of that content, we can create a book that scans and links you back to it. But the possibilities to bring that content to life and make it feel like Steven Spielberg has just been designated to your family to create a documentary with all of the advancements in AI, allow us to use the data that your parents and grandparents have shared to basically build a world digitally around their past, which, again, is just such an exciting time to be building because the pace of innovation is just so fast. Ben Ornstein: Yeah, no, 100%. Oh, that sounds so cool. I’m excited. I’m going to stay in touch and keep learning about the business because I just love what you’re doing. Charlie Greene: Yeah, well, if you need a Christmas present for either of your parents or your grandparent, hit us up. And if you’re interested, I can send you a promo code, friends and family discount. Ben Ornstein: I appreciate that. No, I will certainly check that out. So I’d be happy to receive that. Charlie Greene: I’ll shoot that over to you. Thanks, Charlie. Ben Ornstein: Well, again, thank you so much for the time. This has been awesome. I don’t know how long it’s going to take, maybe a week or so, to turn this conversation into a document that you can see and touch and edit. And then we’ll go from there. Charlie Greene: Do you write it yourself, or do you just have Claude do it for you? Ben Ornstein: I do it myself. We will eventually have to do something like that, as we but it’s all me for now. Charlie Greene: Yeah, give it a shot. I mean, it’s what we do with our customer testimonials. UNKNOWN_SPEAKER: Yeah. Charlie Greene: I mean, please write it yourself. Like, I’d much prefer that. That would be great. But just in the last two months, I find Cloud to be better than GPT. Interesting. We put an entire transcript in the Cloud. We feed it an example of what we’ve created, actually writing as a proxy for what it should create. And I spent five minutes working on it, and it’s really good. And it’s pretty good. OK. Cloud is better than GPT, and you have to give it an example of what the output should look like, Because otherwise, it’ll do weird things with bullets and summaries and shit. But yeah, you can structure it in that way. And then for you guys, you guys are behind a paywall, so it doesn’t make as much of a difference. But for us, SEO is really important. So we can also feed the keywords that we want to rank for, and it’ll stack rank the headlines to be optimized for keywords also. And it does that better than I can. UNKNOWN_SPEAKER: Right. Ben Ornstein: That’s really interesting. Thinking about how to do that. That makes a ton of sense. Maybe I’ll use that as a test for one of the future ones. But yeah, no, I appreciate that. Thank you. Charlie Greene: Yeah, no problem. Give it a shot. It takes you literally two minutes to try it out. And you’ll be like, oh, this is shit. And then try it again in a month when the model improves and see if it’s better Awesome. Ben Ornstein: Charlie, thank you again. This has been a ton of fun. It was great meeting you. And I’m sure we’ll be in touch. Charlie Greene: Yeah, sounds great. Thanks, Ben. Ben Ornstein: Have a good one. Charlie Greene: Take care.