How do you raise $48M from a tier 2 city?

Jason Kirby (00:01.263) Hey everyone, this is Jason Kirby with Fundraising Demystified, and I have Daniel Goldstein joining us, CEO and co-founder of Trust and Will. Welcome Daniel. Daniel Goldstein (00:10.646) Hey Jason, thanks for having me. Jason Kirby (00:12.419) No, we're excited to have you and you know, give you the audience some background and some color on, you know, your background and the history of Tristan Will. Can you kind of just share a little bit of the story? Daniel Goldstein (00:23.03) Yeah, for sure. Absolutely. So at Trust and Will, we're building what you'd imagine as the turbo tax for estate planning, right? We set out six years ago to make estate planning accessible and affordable for every person in this country. And my background personally was in custom software development and strategy and business development. And as I was going through life stages, along with my co-founders, we were going through life stages. We realized that there was no company in the space that we felt like we trusted. that appealed to our demographic. And then also we were looking at the marketplace and we were like, I wouldn't use really anything out there. And so we started Trust-A-Will. We wanted it to be affordable and accessible for everybody. And we've been doing it for six years, have about a half a million families that we've helped so far in our missions to help every family leave their legacy. Jason Kirby (01:13.487) Now it's a great story and something I wanted to unpack a little bit is just the fact that you guys were founded in San Diego, correct? And so in that journey, I'm originally from San Diego. I went and raised capital in San Diego and it's considered a tier two market when it comes to venture capital. What was it like starting the company in San Diego? Why did you choose San Diego? And share that story. Daniel Goldstein (01:40.802) For sure. So I'm originally from Chicago. I moved to San Diego to take a job in custom software development. And so when I got there, I would say the tech ecosystem was in its early days. This was, I moved in 2015. We ended up starting Trust and Will in 2017. And I had made, we had made community in San Diego. And let me tell you, San Diego has been amazing to us. Absolutely. Like we talk about a city that has surrounded us. are from the very beginning of the company. We started the company from a pitch competition put on by San Diego Venture Group, okay? That catapulted us into introductions to investors in town, into Techstars. The Techstars managing director for Techstars Anywhere was at the pitch event. His name's Ryan Cooter. He saw us at the pitch event. He's a San Diegan. And he said, hey, you should apply to Techstars. We're like, okay. So then we went through Techstars. And as we went through it, we raised money through San Diego Angels. Like they surrounded us, but I will say like this was the early days of San Diego tech. Like now you have a ton of unicorns in San Diego. You have some amazing entrepreneurs who are building huge companies that are changing the world. And we were really lucky to be right on that upswing of when people were starting to look. Investors from LA, San Francisco, New York, they're all starting to look at how do we get out of the Bay Area? How do we get out of the major markets? How do we get different valuation structures? And so there was a lot of attention down in markets like San Diego and other markets too. Denver was getting a ton of attention. Austin is getting a ton of attention. Even if you look across the U S you had places like Chicago and Columbus, other places that are getting a ton of attention. So, so anyway, San Diego has been amazing to us. We are so grateful to be a San Diego company. We still are. We're fully remote, but the majority of our team is still in San Diego and we consider it home. Jason Kirby (03:30.895) No, that's great. It's great to hear because when I was there back in 2010 to 2013 raising money, it just the ecosystem wasn't ripe enough to support a lot of founders coming in. That's why I'm here in New York. So you kind of mentioned that you guys got your start with Techstars. Well the Centering Adventure community got the idea rolling, got some introductions, started making things happen. Did you guys have a product before you got a... got momentum on that front. Daniel Goldstein (04:02.006) No, so when we entered the pitch competition, we entered in August of 2017, all we had was a pitch deck and an idea that Cody and I had been rumbling on. Cody, my co-founder, we had been basically whiteboarding what the future of the entire industry could look like based on what we've seen in software. And we were just blown away that this hadn't been done at a level that we thought, which is like an industry-leading brand at scale that people recognize immediately like they recognize TurboTax. Jason Kirby (04:16.964) you Daniel Goldstein (04:31.998) Okay. And so, uh, we only had a pitch deck and we had an idea and we had assembled a small team and we, we knew we were going to run fast after a big problem and we had started to raise cash and so we had started to move that direction, but we didn't have a product until we had, we were like exiting tech stars. And so we built, we were building our first version of our, our basically will-based and it was just an easy way to make a will online and we built that from basically like November through. April and we went through Techstars in January through April. Jason Kirby (05:03.367) That's great. And so basically what it sounds like is you really kind of tapped into a market that. was just massive opportunity, not a lot of attention or major brands addressing it. For me, with my trust in well-to-do, going to a lawyer, paying thousands of dollars, lots of paperwork back and forth, and being on your site, it's more of filling out forms and just going through a UI experience that's more tailored to all the different possible cases. So it's very intuitive and more accessible for a lot more people that just want to have a safe way to make sure that they're taken care of the other, you know, an unfortunate event, you know, might happen. And you're going through the fundraiser experience, so you guys graduate Techstars, you get the product to market, kind of what was the growth from there? Like kind of from both product, customers to, you know, raising next round. Daniel Goldstein (05:59.126) Yeah, yeah. So one of the benefits that we have as a company is that the problem that we're solving is very easy to understand. Like when we tell people that we're making estate planning easy, they're like, oh yeah, that should be easy, right? They think of an attorney, they think of an office, they think of expensive, they think of inaccessible. And so from the start, that's one of the reasons that I think that we could get going in Techstars and that we could get going with investors really easily because we could say, hey, we're making estate planning, wills, trusts online easy. And they're like, oh yeah, that makes sense. Then the next questions that were on their mind was always like, well, what's your go-to market and what's your pricing strategy and how do you know you're gonna be able to acquire customers? And what about willing.com and tomorrow and freewill and like these other people who were trying and had raised cash in a similar area. So then it wasn't like we had to explain the problem. I find oftentimes in the early stages of, I work alongside a ton of entrepreneurs and especially through our Techstars community. Jason Kirby (06:56.315) Thank you. Daniel Goldstein (06:56.382) and the local community in San Diego and Dallas. And like the problem, if I gotta struggle to understand the problem, it's gonna be hard for me to be an investor in your company. And so our problem was really easy. The solution was pretty direct. And so then we got to the mechanics of like how we built the business. And so, you know, you're asking about, what did it look like? So we raised a half million dollars as we were going through Techstars, including the Techstars money that they kick in for the accelerator. We raised like half of that going into Techstars, then Techstars kicks in. I think it's 150,000 if you want, it's like optional. There's, you know, you give them equity as part of the Techstars program, and then there's an optional note that you can take cash on a note. And we took it and then we raised a half a million dollars. And that was through pitching. I think we pitched like 160 angels throughout the course of a six month period of time. Okay, and so then we had a half a million dollars and a half a million dollars doesn't get a company very far as everybody knows, right? Jason Kirby (07:46.875) Thank you. Daniel Goldstein (07:52.986) And so especially a company that just launched products, we launched a product in April and it was our first Will-based estate plan. I remember when our first Will customer came in. It was right in May. It was the first person we didn't know. And we still have a photo of that person's Will. I won't share the name, but we still have a photo of that person's Will. We were like, this is the first one. We didn't know. We had a lot of friends and family that went through it. And so our goal in the first round is to prove our concept. That's it. Jason Kirby (08:04.752) Yeah. Yeah. Daniel Goldstein (08:20.37) it got a half million dollars to prove that you can go out and get somebody to buy your product that hasn't bought your, that you don't know. And in our business, it's a direct to consumer. So you have to prove that you're one of your direct to consumer channels works. And so as we were, as we started to scale some of our direct to consumer channels, we were on all the like kind of easy ones to start off with. We were Facebook, we were advertising on Facebook, we were running a couple like small partnerships and we were trying to prove who is our target demographic. And what we realized is that moms from the age of basically like 35 to 55 who have kids in the home are the primary drivers of estate planning activity. They just are. Dads get involved because they have to get involved. And there are definitely dads out there that get involved, like, you know, even if they aren't forced to. But what we found is that almost every mom has an experience where they wake up in the middle of the night after they have their first kid, they look over at their husband and maybe you had this experience with your 18 month old. And, and, and, you know, your spouse says to you, what happens if we die? Never thought about that as a guy, never thought about it. I'm in, I'm in estate planning. I still never woke up and did that. And so, so that's, so that first half a million dollars was figure out your, who is, who are you selling to? Who's your ideal customer profile? Figure out if you have product market fit. Okay. And then figure out a little bit of scaling channels. So then we raised a million and a half dollars. Jason Kirby (09:24.428) Yeah. Daniel Goldstein (09:43.194) And so that would be, so we raised like the half a million. We closed that in like April. And then we just extended the note. It wasn't like we did like, the first one was like on a $4 million note, right? Like on a cap. We just extended that to six. It's like, we didn't even do that much more. And we raised a million and a half then, okay? And so to get the million and a half, we had to pitch, I think we pitched around 70 investors to get the million and a half. And all we needed was one lead. And we did that over the course of the summer and we were showing them our metrics, our products and market, like all of these like early, early things. But really they're still betting on us. They're betting on our, our ability to do it. And so like revenue wise, like, I don't, I don't even remember what revenue we were doing that I think in our first year we did like, um, in 2018, we did a little less than a million dollars in revenue and And so we hadn't like, we didn't hit like a million dollar run rate or anything like that, like until 2019. And when we re-raised our series A the next year and we had hit a million dollar run rate and we're like, we're a million dollar run rate. Look at the traction we've done over the last year. We've shipped a will-based plan. We shipped a trust-based plan. Here's our ideal customer profile. Here's what our cap looks like. Here's what, here's what our LTV, you know, kind of looks like. And so that's by the time we got to series A, we had a little bit of. Data behind it, but that's what the seed capital was for. I think of Angel. to figure out your proof of concept and your go to market. Then you wanna bet on that, so you raise a little more money, and now you're betting on that, seeing if those hypotheses work. And then if those hypotheses work, your series A is to accelerate everything you. Jason Kirby (11:24.291) No, and that's 100% accurate in terms of that. Having you follow the steps exactly as, you know, what most venture backable companies that have momentum, that have kind of figured out the product market fit aspect and executed across that. And especially as you mentioned, like, okay, you raise the seed to kind of get to that million dollar runway, which is that kind of arbitrary magical number that kind of triggers for series A raise. But you're smart in the sense of like, you've got all your stats together. And I think that's a lot of things that founders don't realize. When you're Series A ready, you've got to have your numbers. You're now looking at growth. You've got to be able to say, you give me $1, I make $5. And be able to have that calculation very easy for VCs to be able to calculate on their own. And then so you raised the Series A, which correct me again, how much you guys raised on the Series A? Daniel Goldstein (12:17.598) Six million. So small in New York or San Francisco at the time, that would be considered like a really, it would be considered almost like a seed round. Because this is 2019 when we did our Series A. And so we were calling it a Series A and people in like non- major markets were like, that's cute. Jason Kirby (12:37.679) And what's funny is I remember that because I still involved the alumni community in San Diego State and I saw the news coming through, like everyone's celebrating that you guys raised a Series A. I'm seeing all these articles and people I follow sharing it. It's funny because there's a million deals happening in New York, a million deals happening in San Francisco, and they just kind of become noise. But for you guys, it stood out because there weren't a lot of San Diego-based companies coming out. getting to a series A point. Nonetheless, to where you guys are now, where you guys, I think, have raised a total of 38. So kind of walk me through the rest of the journey and share what you can on that front when it comes to getting to that 48 million number. Daniel Goldstein (13:13.741) 48. Daniel Goldstein (13:26.25) Yeah. So series a, uh, we had a firm called link ventures out of Boston who led our series a they're an amazing data-driven VC fund that's connected to, um, uh, it's connected to MIT in a lot of ways, but they're connected to specifically, they have like a, a data science lab called Kogo labs, which, um, is an accelerator for all consumer brands. They have, that's just a massive data warehouse. So we loved them. We love their data-driven approach. We accelerated a lot of our consumer marketing by I would say it saved us about 14 to 15 months just by working with their data science team, which in the early days was saving like 12 to 15 months is unbelievable. Also a lot of money, right? Like that's 12 to 15 months of like spending on ads to learn the same thing. So then COVID hit, we raised our series A and then like five months later COVID hit and our business tripled in 30 days. And so we went from Jason Kirby (14:06.575) you. Daniel Goldstein (14:26.026) You know, I think we were doing about a hundred grand a month, a hundred to a hundred and twenty grand a month in January of 2020. And then we hit March of 2020 and we almost, we tripled. So we did about 350 in March. Okay. And this is like, so all of a sudden the entire world is focused on debt and they can't go to attorneys and we have a product that's easy, accessible online. We did a lot of things during COVID. Yeah. So like we were kind of. Jason Kirby (14:36.935) Thanks for watching! Jason Kirby (14:52.322) Yeah, correct. Daniel Goldstein (14:55.234) perfectly positioned in that market to help a lot of families. And specifically, we also provided free estate plans for all frontline workers. We did it for teachers. We gave away over 12,000 estate plans to any of the first responders and frontline workers just to give a little bit of peace of mind for the job that they were showing up as every day. And so during that time, I also had my first kid. So it was a whirlwind for me. And... So that kind of accelerated us into conversations that summer to raise another round. And people saw like, hey, look, actually, we do believe that there's going to be a brand here that wins. And we think that brand could be you. And we think that like the convergence of digital with online and look, now you have everybody's default with online during COVID, right? Every single tech stock was exploding. And so then we started talking to people in the summertime about a Series B, which we were like, I don't know if we, we don't really, do we have the metrics for it? I don't know if we have the metrics for it. And so, uh, we pitched, I think we pitched like 20 or 25 firms in the course of like a week and a half. We're like, you know what? We're going to do it. We're going to do it right. We're going to, we're going to condense all of the pitches into like one week and we're going to, um, and we're going to do it. So, uh, we had been talking with, um, Jackson square ventures for, I think we had known Victor. Jason Kirby (15:54.407) Thanks for watching! Daniel Goldstein (16:20.246) who led the round for two years at that point. Like he had been coming down to San Diego and he was one of the SF venture VCs that had been like looking at San Diego and specifically because Mike Crenn from San Diego Venture Group had really nurtured relationships with all of these like off-market VCs that, you know, this is like why we benefited massively from San Diego because we got a lot of attention as one of these startups. So Victor had been following us for a while. loved what we were doing, believed in our thesis, believed in our go-to-market and led our series B. And again, small series B, 15 million, right? And so 15 million series B, that was in 2020. From 2020 to 21 to 22, we just continued to double or more than double our business every single year. And so doing our series B extension in 2021, we raised 10 million from UBS and a few other Jason Kirby (17:11.098) Thank you. Daniel Goldstein (17:17.614) that was kind of like contributed in, but UBS, we didn't go out and find that. They came to us and said, we really love what you're doing. We believe in your thesis. We'd like to invest. So we extended our series B. And then in 2022, technically we closed it this year, but we also had the same inbound from a few organizations. Like Northwestern Mutual was already on our cap table. We had USAA, Amex, and SCI who, I got a call out like, Jason Kirby (17:26.663) Thanks for watching! Daniel Goldstein (17:46.83) Cody, my co-founder, is I think the greatest fundraiser of all time, right? He drives all of these conversations. I come in after they're warm and teed up and talk about and brag about the work that our team is doing. And so Cody nurtures these relationships. So when I say inbound, it's inbound because the relationship has been nurtured over a long period of time. And so we raised another 15 million from Jason Kirby (17:52.071) Thanks for watching! Daniel Goldstein (18:14.77) Northwestern Mutual SEI USA Amex that closed in January of this year. And so, but those conversations started last May. So that's, that's how it all adds up. 500 million and a half, 6 million, 15 million, 10 million, 15 million. And like the last 25 that we raised was easier than the first 500. Jason Kirby (18:38.071) Yeah, no, and there's a couple things I want to point out for our listeners here, like things that you kind of mentioned, like number one, I want to go back to Lean Ventures from Boston, like choosing the right partner. And that's something that I think a lot of founders just like, all right, who's ever gonna give me money, I'll take it, you know, kind of mindset. But when it comes to this firm that you mentioned, like they brought immense value to the table. This was not just a check. Uh, and a babysitter, this was like massive value add in terms of accelerating your growth. And that's something that I think, you know, founders need to look for when you're building your business is, you know, don't just go for money, go for who you're going to, who you're going to be in bed with for the next 10 years, potentially, and, uh, and establish that, that kind of relationship, make sure it's a, there's value on both sides. And that, and that's a rare case. Not most VCs have that kind of value to bring to the table. So that's amazing to kind of hear that you got that. Um, The other thing, as you mentioned with Cody, establishing those relationships, because again, it sounds like that one week when you raise a series B in a week, that's pretty impressive. It was on a whim, and granted, it was the peak of the market, so people can argue that it was easier in that timeframe, because money was flying like crazy, and you had the perfect fit, the digital online platform, and everything was going online, and there's cash flowing everywhere. It sounds like you're still very strategic. Like you tested the markets just to kind of see what was out there. You didn't want to like do the whole campaign. You know, maybe, let me ask you, did you, if it wasn't, if you didn't get term sheets, were you guys just gonna like get back to building or were you guys gonna try to hit the road again on the fundraise? Daniel Goldstein (20:18.562) for which round. Jason Kirby (20:20.005) the series B. Daniel Goldstein (20:22.966) Yeah, we would have had to keep fundraising. Like it was like, we had gotten to the point where we believed we were going to raise and we had been building our company up to the point where that assumption was true. And so if we hadn't raised our series B, we would have had to go back to our strategic drawing board or go figure out a fundraise because ramping up into it, our business was accelerating so fast that we were, that we, along with the rest of the market, right? like favored growth over anything else. And so we, like we had a cash, we had a cash out date. And, and so when we raised our B, I think our cash out date was still 12 months away, 12 ish months away. And so it wasn't like, it wasn't like urgent at that moment in time, but we knew we're like, well, what's, when are we going to raise next? If we don't raise in that fall, we can't really raise in Q4, nobody raises in Q4. And then you got to raise in Q1. Right. And so that cash out date gets a lot closer. And as cash out date gets a lot closer, your negotiation with investors gets a, uh, different, it changes. That's just how it is. Like when you need money, it's hard to raise it. When you don't need it, it's easy to find. And so, you know, going back to what you said about the series A investor. So we, you know, during the series A pitch again, like as soon as a pitch was harder than the series B pitch, like our, our metrics, nothing is ever where. Uh, people want it to be. And. Jason Kirby (21:30.084) Yeah, exactly. Daniel Goldstein (21:49.358) And no matter what your business does, like, look, there's there, you take a, you take a curve and there's going to be businesses that everybody's going to invest in. No brainer, the metrics, the growth, the team, the everything is exploding. Okay. Most businesses fall within this two thirds majority curve, right? Where it's like there's, there's great things about it and there's, and there's ugly things about it. And you have to figure out, I think a lot of investors are figuring out theoretically, does this align with where they think the market is headed? Do they believe in the thesis of the organization? And that's what they're betting at the series A because you have some metrics, you have an LTV to CAC, but again, your LTV to CAC at that early stages is early. Like who knows if that can scale? Like who knows if like a million to $5 million business can scale an LTV to CAC to a $500 million business? Like, so you have to believe that there's something that's happening that's more magical than just the numbers that are there. And so in the series A, picking the right partner was huge. Like Rob from Link Ventures is still on our board, right? So this is three years later and he's been an incredible ally for us. Kogo Labs has been an incredible ally for us. And so, you gotta be careful with that. So we had three term sheets for our series A. We ended up picking Link. I think we picked an amazing partner and we're incredibly grateful for them. Jason Kirby (23:13.627) No, I'm glad you kind of got honest there and kind of said like, you know, you guys had a good growth trajectory, you were like a solid opportunity, but you weren't like, you know, growing 500% of the amount, you know, anything like that, you know, would be a slam dunk type deal. And you guys still pitched a lot of investors. But I think still the outcome shows that, you know, getting a couple term sheets kind of shows that you've done something right, you've built a good model and a good market and you're showing up, you know, that you have the right data that it's worth a bet. And then you brought up some really key things that I think a lot of founders don't understand of like, you know, they look at benchmarks online like, oh, like a five, you know, three to one CAC ratio is really good. Yeah, LTV to CAC ratio. But then what they don't realize is VCs have also seen that a million times, but they also see it how it plays out over time and how those sometimes aren't sustainable, you know, especially as things get more competitive, markets kind of shrink a little bit, your target audience, you got to find ways to expand and you have to get more aggressive with spend. And they think that, oh, the more you scale, the cheaper things get. And that's not always the case. And so VCs always have that, that lens when looking at numbers. And I always try to remind founders like, okay, this might look good, but you've spent 50 grand proving this, not tens of millions. Daniel Goldstein (24:26.374) Right. Yeah, our acquisition numbers in the early days, we were like, VCs, you gotta check this out. You gotta check out our acquisition numbers. Look what we spent on Facebook. We spent two grand and we're getting registration for like $9. We gotta do this. $2,000, that's not it. Yes, we were targeting the most relevant customer and getting in front of them. And that's not how markets are built. Not everybody is like. literally about to buy an estate plan. That's just not how it is. Jason Kirby (24:54.423) Yeah, it's not always top of mind and then there's nurturing and it's like it's an entire life cycle of managing that customer's experience. And I'm glad you mentioned that because again, like founders are like, oh yeah, the $2,000 number. It's just like to you as a founder, it means so much. Like it's such an accomplishment. But when VCC, you know, a hundred of those a week, you know, it's just like it's a different scale that... Daniel Goldstein (25:01.471) Exactly. Jason Kirby (25:19.107) founders have to kind of reflect on and put themselves in their shoes to kind of acknowledge that don't be offended when they say no just because they've seen it not work out many times. Daniel Goldstein (25:29.334) But those stats are important in the early, you know, like you don't get to spending 200 grand a month or $2 million a month before you spend $2,000 a month. That's just how it is. So, and if you're not spending the 2,000 well, you're probably not gonna spend 20,000 well, you're probably not gonna spend 200,000 well. Like you have to work through the hoops of building a business. And so, and that's what these stages are all for, these stages of capital. They're stages of your business that you're building and everyone has its own. complexities and functions that you're going to wrestle with. Jason Kirby (26:04.311) No, brilliant said. I love that. So, you know, something that I recognize is like, the opportunity of Trust and Wills was very clear because, you know, again, wealthier people who have prioritized it, they have assets to distribute, who you're raising capital from, that you have that experience. And albeit you're potentially solving that problem for them, but you're also bringing it to the masses. Like, how did you guys kind of like scale up the market? Because like, current spend on Trust and Wills versus what... you know, at least my assumption, but you can correct me if I'm wrong, is that you're essentially expanding the market. You're making it more accessible for more people across the country. How did you kind of like come up with the market opportunity? Daniel Goldstein (26:47.798) Yeah. The market opportunity, I think is one of the most overlooked functions of the industry that we're playing in. And it is the reason that we have, uh, in our opinion, such a head start because, uh, we believed in it prior to a lot of VCs prior to a lot of market participants and I, so here's the thing. People make assumptions about when people do estate planning and they're oftentimes wrong. And if you go out and you survey people and you ask, when did you do your first estate plan? What you'll find is when they had kids. And what people think about is people doing estate planning when they're old. And so there's a gap. There's a gap in consumer understanding that in our research in the very early days of Trust and Will, we identified from our own experience, we were going through life events, getting married, having kids and saying, wait, it seems like we would need an estate plan. Then we started talking to our friends and our family members who are going through life stages that are similar. Jason Kirby (27:21.487) Mm-hmm. Daniel Goldstein (27:44.51) And it's on their mind, all of them. It's like life insurance. It's like, oh, it's an adulting function. Do I need to do it? And so you're looking at, there's 40 million families in this country that have minor kids in their home right now, okay? And so you're looking at the 40 million and you're like, that's part of the target market. Then you look at it, there's 90 million Americans who say that they know they need an estate plan but they haven't gotten around to doing it. Then there's another 100 million Americans who have an estate plan. sitting like mine is right here in their drawer somewhere. It's not digital. Mine comes from Justin Will, so it's digital, but then we have to finish it offline. Right, and so like, so the market is massive. There is, there is like somewhere between six to eight million people who are doing a net new estate plan every single year, regardless of whether there's advertisements or anything online. They're gonna find an attorney, they're gonna go online, they're gonna do it, okay? And 85% of those people still go to attorneys. That's just how it is. So the market that you're talking about expanding is we're expanding the online market. We don't even need to expand the estate planning market. We just need, like, as we continue to capture more of the market, we're continuing to capture more of the market that would go to usually an expensive provider and the experience is subpar, right? Like the experience of doing estate plan online with your spouse over a glass of wine while you watch succession is a lot better. than trying to arrange childcare so that you can go to a law office in the middle of your work day. Like it just, the logistics don't make sense. So the market is huge. And I think it's understated oftentimes because the go-to market is hard because customer acquisition costs in our market is hard. It's, it is very hard. You're dealing with procrastinating parents like yourself who may or may not have set up their estate plan yet because they may or may not be tired because they have an 18 month at home. Jason Kirby (29:31.591) Thanks for watching. Bye. Daniel Goldstein (29:37.51) and they're trying to run a business and they're living in New York. There are complexities to life that prevent people from doing this that we have removed all the barriers for. So then the next step is how do you tap into that? And our primary hypothesis has been to build an industry leading brand that people trust, recognize, and identify with in the same way that TurboTax did it for tax. TurboTax has 40% of the tax market, 45% of the tax market. What does 45% of this industry look like? Because we believe there's going to be one winner and who takes the majority. So what does 45% of our market looks like? It looks like probably 30 to 40 million families who have used one platform to create their state plan. They manage it through there. And then when they or one of their loved ones passes away, they distribute it directly through our platform. So like that's what we're building. And we believe that like 30 to 40 million is Jason Kirby (30:11.042) Yeah. Daniel Goldstein (30:34.914) is the 30% of market mark, you know, because we know that there's 100 million people in this country with estate plans. Jason Kirby (30:37.699) Yeah. Jason Kirby (30:41.699) No, that's well said. And I think that's something that I want founders to kind of understand is like how to articulate your market. Cause that was not my impression. You know, I was in the impression that a lot of people don't, don't do this. And the fact that there's a hundred million that already do is, uh, it was pretty mind opening to me. Um, so that's, uh, that's something that I think it's a founder's job to be able to articulate the real opportunity and really understand who they're going after to be able to convince VCs. Cause that makes, venture-backable or not venture-backable. If you can't articulate that billion-dollar unicorn potential and make it believable, it's one thing for you to believe it, but you've got to make other people believe it. And if you can't do that, then in that case, it's going to be very difficult to raise capital just because the way power law works and how venture capitalists work, they just need to see that 10, 100X type potential returns. Daniel Goldstein (31:28.258) For sure. Jason Kirby (31:38.635) So you gave us the whole story of the fundraise and really appreciate that. You kind of got into the inside, some things were more difficult than others. What was kind of like a standout moment in your fundraise, both a kind of like a low and a high during the raise? Daniel Goldstein (32:00.782) Uh, I have one story specifically comes to mind. The million and a half really early company. I mean, we had seven employees. We're working out of a coworking space. We basically were all in the same room. The room smelled. It just had, it's like, it smelled like takeout and food trucks and, you know, and then seven people in a room. And we were raising this million and a half and nobody wanted to invest without a lead. And this is a common problem in early stage where they say, yeah, sure. I'll, I'll invest it just by the lead. I don't want to have to set the terms. And this is a Cody and I were wrestling with this. We're like, what do we do here? Like we have, we have more than two and a half million dollars of people who say they want to invest, but nobody wants to invest without a lead. So what are we supposed to do? Well, we had, um, we finally ended up setting the terms with one of our, one of the VCs that was not going to be the largest check, but they're willing to set the term. Okay. And we, we had flown out to San Francisco to pitch WTI, Western Technology, which typically does debt financing. And I always, I always remember this. And, well, first off, because I had, I had curry the night before, and so my stomach was like, not in a good spot. Okay. We fly to San Francisco, that's probably TMI for your listeners, but it's just real life, right? We fly, fly to San Francisco in the first flight out and Jason Kirby (33:21.785) That's right. Daniel Goldstein (33:26.726) It's, it's a, it's our first like major, major pitch in front of a big firm with all of the partners and we get there and we're nervous, Cody's hyped, uh, and we do our pitch and I, I hope maybe one of the guys is going to listen to it, but I, one of the guys next to me in that pitch, no joke, fell asleep, not kidding. Like fell asleep and like, and look like the firm is amazing. They've been so supportive of us and, and maybe he was just very focused. but I swear he was asleep. And I'm like, we bombed this. There's no way that this is going well. I feel mortified. There's a lot of doubt that comes in as a founder, especially like I shouldn't be here, I'm not a real entrepreneur, all of these things. We get walked out, John Beiser is our contact there. He's been fantastic and supportive since we started. And so he's like, like you guys crushed it, you did amazing. And I'm like, there's no way, there's no way. Like I was here in the room, like I saw it, there's no way that it went well. He's like, I promise you, it went so well. So he walks us out and we didn't have a car, we're not from there. So we sit and we're like waiting for an Uber. Uber says it's like eight minutes away. Like, oh my gosh, this is so embarrassing. We're sitting with our backpacks outside this. Like, I mean, WTI like back, they gave venture debt to Facebook. They were like a behemoth in the industry. Like, and so. Jason Kirby (34:27.015) Thanks for watching! Daniel Goldstein (34:51.126) And we're just a bunch of kids like trying to raise for like a state planning startup. And John, and so we're nervous. We're feeling bad. We're just sitting there and John comes back out and he's like, Hey, uh, how much is left in this round? And we had, we had a half million dollars left and we're like a half million dollars. And he's like, okay, great. We'll take the rest of it and we'll send you the paperwork by end of day today. And we're like, we're having a moment where we feel so fake, right? But also we're like, act like you've been here before. Yeah, sweet. Like, yes. You know, like, thank you, John. Like. that you were, you know, we'd welcome you on this journey with us. But in the inside we're, we're exploding, right? But then, so we sit there, John goes back inside, but we're like, there's all windows on their, on their office. And we're sitting with our backpacks. We're like, what do we do? What do we do with our hands? You know, I don't even know. And, and we have to wait another six minutes for our Uber to get there. So we're just waiting and waiting and waiting. And finally we get the Uber and we're like, wait for it. Jason Kirby (35:37.179) Bye. Daniel Goldstein (35:45.706) wait for it and we like pull out of the driveway and like back onto one of the roads in Silicon Valley and we're like, yes, yes. And it was so exciting. So that was like kind of like a low to high. Like I was feeling terrible in the morning. I was feeling terrible during the pitch. And, and you know, I, I, one of the things with, with being an entrepreneur that I've said, and this is just a life thing is like, the more you show up, the luckier you get. It's just, it's how it is. And I think fundraising is like that. Like you have to show up. Jason Kirby (35:51.436) Yeah. Daniel Goldstein (36:13.238) You have to give it your best. You have to continue to grind and grind and grind. And you know what, the more you do that, it's a numbers game, the luckier you're gonna get. We have a list of investors that we've pitched that's almost 550 people long. We're not talking, we haven't been around that long. We're a six-year-old business. We send out monthly investor updates on the first or second of every single month since we started the business to almost 600 people now. Okay, so basically any investor that we've ever talked to, we say, hey, do you wanna be on our investor updates? We'd love to keep you informed with what we're doing in the business. And this is a secret weapon for us. Everybody should do this. This is a tech star thing. They told us to do this. We didn't invent this ourselves. And so anyways, the journey's been amazing, but that was one of the early moments where I was like, this is a crazy ride because it was high to low or low to high. Jason Kirby (37:07.583) No, and that's really I bet you wanted to kind of do the 80s high five, you know, jump in the air. But you're like just holding. Yeah, that glass, they're all probably looking at you like what are they? What are they? You're just like that that pressure of just like, oh, I want to get out of here. But I totally know. Daniel Goldstein (37:11.634) Sure. Yeah. You could have had a comic book moment. Daniel Goldstein (37:25.29) Yeah, in real life, nobody cared. They're all back in their office. They're probably not even thinking about the pitch anymore because it's one of many pitches. Just in our world, we're like so self-conscious because we think everybody obviously is thinking about us when the reality is like, nobody's thinking about you. Let's be honest. Jason Kirby (37:31.088) Yeah. Jason Kirby (37:41.428) 500k to them is like pocket change, you know, like it's not a huge investment. It's like, hey, we like these guys, let's take a bet, you know, it's like, all right, back to work. But it changed your life, you know, it gives you this massive window of opportunity and it's like this massive success moment. And it's just you and Cody as the founders, correct? Daniel Goldstein (37:44.307) Exactly! Daniel Goldstein (37:51.542) Yeah, exactly. Daniel Goldstein (38:01.906) And Brian Lamb, he's our third co-founder as well. Jason Kirby (38:03.371) Oh, right. I'll try. And so, I really appreciate you kind of sharing this story and kind of sharing the background on both Trust and Will and kind of your fundraising history with our audience. If you could leave any nugget of information for a founder looking to raise their seed round or their pre-seed round, what would be your advice to them? Daniel Goldstein (38:26.454) Yeah, it's a numbers game. And so whatever number of investors you think you've pitched that you think is enough, double it, triple it, and then go back to the drawing board. So that's it. Like every entrepreneur I talk to in the early stages, it's just like, you need at bats to be able to see pitches. That's how it is. And so you gotta get to the plate as many times as you can. Pitch your friends, pitch your family, pitch your... your neighbors, pitch literally everybody, because that helps you get your pitch down. It helps you understand what your audience cares for. And then you get introductions. So you pitch and then ask for intros, pitch and ask for intros. And you just do that until your web is big enough. So, and just for context, like we didn't come from, we didn't have a, we didn't sold a company, we didn't have a venture network. Like we had to build everything from scratch. And so it was, it was a lot of grinding and a lot of pitching. Jason Kirby (39:24.107) Oh yeah, sounds like it. And then, when it comes to the numbers game, how much did you guys iterate from the deck? Did you have deck version 45? Kind of. Ha ha ha. Daniel Goldstein (39:33.43) Of course. Yeah. Yeah, yeah. Of course you have to. I mean, like, and we would pitch it. We've from pitch to pitch. Sometimes we would change it, you know? And then sometimes we wouldn't change it for two weeks. It just, there's some things that you find a groove on. And then sometimes you're like, this group just isn't working and you gotta stay, you gotta stay nimble, but like, you also don't want to, I know this is, there's probably the advice is that it always comes with contradictions. Like you have to know what your, the core of the businesses and you can't change the core. So yeah, you can change how your go to market strategy is communicated, or you can change how your product is communicated. You can tell better stories, so much as storytelling. And that's why getting at bats is really important because it hones your story more than anything. You don't wanna be changing your business in every pitch. That's not gonna work very well. Jason Kirby (40:26.595) No, I would agree with that. How did you guys go about finding investors? And what was your first initial outreach to kind of get those, that 600 people list, investor list? How did you go about kind of getting those first initial meetings? Daniel Goldstein (40:43.262) uh, shameless reach out. Uh, I mean, Cody is like shameless when it comes to reaching out. I mean, like, look, we, we started with people we knew, anybody who had money. We just thought, Hey, who do we know that has money? And who do we know that's in San Diego that has money? And what about other founders in San Diego that have had recent exits? Like, how do you think, like who, who in the world has money? That's what it all comes down to in the early stage. And we just reached out to every single one of those people. And then. asked them for other people that have money, and then did cold reach out on LinkedIn and cold emails, and connected with venture groups and angel groups, and looked at websites, lists of investors, and lists of firms, and it's, I don't know, what's the answer for everything? We didn't start with a list of 600, right? It started with one, and then we talked to somebody, and it became two, and then we talked to 10 people, it became 11. All of those are- you know, conversations that happen over time. And then, and what happens is you start to build a network. And that network takes a lot of time to build. It takes time to build relationships. As you start to pitch in your seed round, we were pitching series A investors, and they're like, you're too early, but then we kept in contact with them. And as we were in our A, we were pitching series B investors. And every single stage that we've gotten to, it's been easier to get ahold of people because our network's grown and then our also businesses have more traction. So. Jason Kirby (41:45.698) Mm-hmm. Jason Kirby (42:08.023) Yeah. And at the end of the day, I guess that's always the key. Have a great business and focus on building a great business. And things will... I think a lot of founders might be working on something that they haven't really found their click yet and they go out to raise. And that can often be detrimental to their growth of chasing money when they're not necessarily ready. Daniel Goldstein (42:30.058) Maybe, who knows? Who knows when you're ever ready? I don't know, when we're ready to have kids. It's like, you don't really, like I don't know if anybody ever arrives because your business is gonna be ugly. Like our business is still, is ugly now. Like, I mean, it's beautiful in a lot of ways, but like it's, there's some ugly parts of it. And that's the reality, especially the earlier you get. Jason Kirby (42:35.335) I'm out. Bye. Jason Kirby (42:52.999) Yeah, that's fair. Well, Daniel, really appreciate this time with you today. Where can our followers sign up for Trust and Will if they need to do their own estate planning, and how can they follow you? Daniel Goldstein (43:04.906) Yeah, trustandwill.com, really direct. Go there, get your estate plan. It takes 20 minutes. If you're a founder, you definitely need one. And then me, I don't know, I'm on Twitter a little bit, Goldstein222, Trust and Will's on Twitter. My co-founder's a little more active on Twitter if you wanna look at tech stuff, Cody Barbo. Jason Kirby (43:08.941) Alright. Jason Kirby (43:30.563) Awesome. Well, appreciate the time today. Appreciate the insights and really glad to have you on the show. Daniel Goldstein (43:36.47) Thanks, Jason.