- Platform: meet
- Source: Read.ai 01JBW9CAY0XMAE28Q8AK3CDFAE (via Ben Ornstein’s account, imported 2026-08-06)
Transcript
UNKNOWN_SPEAKER: Hey Ben, how’s it? Will Goto: Hey, well, how’s it going? UNKNOWN_SPEAKER: Good. Ben Ornstein: Nice to meet you. Will Goto: Nice to meet you as well. Ben Ornstein: You hear me? All right, I can I can can you hear you? Can you hear me? Will Goto: Well, yeah Where are you based? Oakland, California. How about yourself? Ben Ornstein: Nice. I’m in Newark, Delaware right now Newark, Delaware, interesting. Will Goto: Yeah, very random spot, that’s for sure. Ben Ornstein: Yeah, what brings you there? Will Goto: Is that home for you or just? Ben Ornstein: No, I grew up in New York about an hour north of the city, but I am living here right now. Right now I’m just living with my, well, with my girlfriend, recent fiance. Oh, nice, congrats. Thank you, thank you. So, you know, we’re living with her sister for now, but we move out soon. Will Goto: Sounds great. UNKNOWN_SPEAKER: Oh, yeah. Ben Ornstein: So how much context do you have for this call? Will Goto: Very little. I have, the only context I know is it’s about fundraising and Mike, Michael does like, you know, his, his founding journey and stuff. And I found that he does a lot of like fundraising content. So I figured it’s something that we’ve done several times already. Ben Ornstein: So. Amazing. Yeah. So, so, you know, you’re familiar with how can, Michael Houck and all his stuff? Will Goto: Yeah, I did like a brief overview of like what he was doing and stuff. I’m not part of the email list or anything yet, but it would be nice. Ben Ornstein: Oh, good. Yeah. So he is a founder himself. He has the email newsletter, all that stuff that you looked at. And so another resource that he wanted to create for founders was specifically for fundraising. And we figured what better way to do that than by actually speaking with founders themselves that have done it and hearing about their journeys. So we’ve done about 75, maybe 75 plus of these at this point. All different stages, all different regions, all unique in their own way, which has been a lot of fun to do. And so I’ve got this preset list of questions here, softball questions, nothing you’re gonna have trouble answering or if you haven’t answered before, it won’t be a problem. And it is, yeah, mostly just softball, easy questions. The recording here goes nowhere. It is just for, as in the video recording, I have my read AI guy in here because we turn this call into it. We use the transcript to turn it into a text-based document. I’ll send you the draft when I finish it. And then you’re going to have a chance to obviously review it before it goes live. Will Goto: Cool. Ben Ornstein: And when it goes live it’s going to be behind a paywall for the premium subscribers. So, um You can talk pretty candidly because this is truly for founders who are you know, right, right? This sounds good Yeah, any other questions? Will Goto: Are you good to go? Ben Ornstein: No, I’m good to go. Let’s do this. Let’s do it. All right So will can you please uh briefly introduce yourself and your startup? Will Goto: Yeah, so my name is Will Goto and my startup is rise.io Um, and then before rise I started another company called humble dot, which I’ll probably talk about a lot because we did two rounds of funding for that. Ben Ornstein: And then we only did one round of funding for rise so far. Cool. Sounds awesome. Yeah, can you share a little bit about the fundraising journey? So this could be, you know, the, how many rounds you raised? How much the rounds were, if you’re comfortable sharing the valuations, that’d be awesome. If not, of course, no worries. And, and how they took to close roughly? Will Goto: Yeah, so we went through three total. And the first two were my previous company. So I guess I just start from there. Chronologically, because I think that would make the most sense. So the first first one was about 550k was a precede all done in safes. And I think our valuation cap was 4.5 million or something like that. I think we got connected with A4 Capital, who, quote unquote, led our pre-seed round. They’re the ones who committed a majority of the 500K. I think they actually did like 400K of it. And at the time, so my co-founder, his name is McGill Davis. He’s my current co-founder and was my co-founder for the last company as well. We were actually working at Twitter at the time and we had gotten acquihired into Twitter from a company called Peer. And this was a startup that was founded by the former COO of Salesforce and their general counsel. So we were like, I was like employee number 10. He was like, I think 11 or 12. So really, really early at this company. And then what we were building there is kind of relevant to what we were doing a lot because we got acquihired into Twitter. And then we took like those ideas for from that company and kind of turned it into like a new company. And then, yeah, we got connected to a for capital through a mutual friend at Twitter. And they, they were like, really like the idea of what we’re doing, like their experience of working at a startup previously to working at Twitter. And then obviously, you know, our ability to get into that startup and working directly with the former CEO of Salesforce and the general counsel there. And I just became really valid social validation, essentially, for our work. And so they decided to back us just purely based off of our ideas and our experience. We didn’t have any traction at all. The only traction that we had was a spreadsheet of like, so the tool is essentially like a manager tool for managing your employees’ software stuff, how they feel, what’s their morale, and things like that. Automated survey that would go out to your employees and kind of get a pulse check on how they’re feeling. And we just did this through surveys on Google Sheets. And we kind of tried to quantify it somehow into ratings and whatnot. And it was trying to take a very analytical approach to people and how they feel like people, early people analytics stuff. So we got A4 on board, and it was of unintentional because we wanted to just work on the product. We didn’t really think about fundraising at all. But then as soon as they were like, we want to invest, we had the opportunity to work on Humboldt while being paid, which was the ultimate experience. You minimize the risk entirely. So we were like, hell yeah, let’s do this. And then soon after that, they immediately they started connecting us with their bunch of people from their network as angel investors. And then we ended up closing, quote unquote, closing the pre-seed round for like, at around like 550K total, I think. So we brought on just a bunch of other angel investors. Yeah, I think that was primarily the first one. I also think, I guess a crucial detail about the first one as well is that one of, so one of the co-founders of Peer, who was the former general counsel of Salesforce, he also invested in us as an angel investor as well. And I think we’re having conversations with him at the same time we were having conversations with A4. And so A4 was like, okay, these guys are capable of funding around and they have actual backing from the people they worked with in the past. So that was also contributed a lot to our experience. The availability of the cache. So after the pre-seed round, I think we were working for another maybe a year and a half. And then we actually started to see some pretty good early traction after one or two pivots. They were kind of soft pivots, so still like a manager tool, but kind of turned into more of a communication tool rather than one to be like people analytics. And then we had like good early metrics around adoption. And then also like validation, whether or not people would pay for it. But we still didn’t have like actual revenue, we had maybe less than, I think, 10k MRR. Okay, wow. Okay. UNKNOWN_SPEAKER: Yeah. Will Goto: And we were running out of money. And we’re like, we need to raise again. And we have some pretty strong metrics. We had pretty good retention and pretty good engagement. And then we had some few key customers and some pretty big companies. So we had a couple of contacts at Twitter trying the tool out that were really successful with it. And then a bunch of other teams that we acquired randomly just through contacts. And then they ended up sticking with us because they really liked the tool. And that early validation, I think, was really good because when we had random people using in our tool and vouching for us, that it really helped them out at companies like Twitter. And I think the other one was we had Quizlet on board. We had the whole tech department there. We had, I can’t remember the name of it. It was like an intercom type of product, customer service. The name just came to me. It’ll come back to me later. Yeah, so we had a bunch of things going for us, except for revenue. And we thought we were like, okay, these because we are also like discounting the price to to incentivize you to get a foot in the door. And we figured that as long as our other metrics like engagement, retention, and the the soft stuff to around the testimonials around the customers would be enough, that would be a leading indicator of revenue. So at that point, we kind of put everything together into a deck. And then Afora actually really helped us raise our seed round as well. They would give us warm intros into partners, into other firms like Sousa. So Sousa was actually the team that led our seed round for Humble. And I think for that one, we ended up raising around $2.3 million. And I think the post-money evaluation for that was like 19, I think. So it was pretty decent. I think it was 19. I'll have to double check those numbers. I think it might've been, it was anywhere between 15 and 19 or something like that. So it was pretty decent. And it was actually a syndicated round. So they technically led the round, but they didn't actually invest the most amount of money. We were actually aiming for 3 million for our round. And what we found is that we thought that once we had an initial person leading it, everything would fall in place. Everyone would just follow really quickly. A lot of people say that when you get a lead, it's really easy to close. But it wasn't necessarily that easy. We were going for 3 million. Sousa was willing to do, I think it was 750k. And then when they committed 750k, We were like, okay, we need to fill out this round, like a two and a quarter million left to finish out this round after our lead has already committed, which is a tough way to close this. But we kept going around and with Sousa already backing us, it was definitely easier to get a yes from most other investors, but it wasn't easy to get enough yeses to go to 3 million basically. So we got two other firms to jump in and then they were around like the half million ish each. And then a few other like angel investors and just basically like as many other, like it's basically just like a group party. It was just like a bunch of like investors investing anywhere between a hundred to like 600 K and then you have your handful and we had Sousa. And we actually had one investor, I think, that put in more than Sousa did, even though they technically didn't lead the round. Yeah, it was a really interesting round. It's definitely really, really interesting. So I guess maybe Sousa was okay with the 750, because whatever percentage they were getting from the valuation, it was enough for them in terms of ownership. But everyone else wanted to get in. We got a lot like Village Global, we got Core Ventures Group, and then 10.1.10 Ventures as well. And then Brynn Kimmel, I think, wanted to join in as an angel investor. I think she invested us through, at the time, she was a scout for Village. And so she invested us through Village. Yeah. But the whole process was just like any other fundraising process. So you have to build your entire list of prospects and then work together with whoever you have as your current investors to give you warm intros, and then just treat it like a sales process. So you have to get the prospect, you have to find out which ones are probably going to be the best fit for not only your round, but also the type of company you are, and the type of founder. Ben Ornstein: I'm actually going to cut you off because you're answering like four or five of the questions. Will Goto: No, this is great, by the way. Ben Ornstein: I'm going to cut you off because I want to hear more detail. Yeah. Right. Okay. So this sounds amazing so far. And I think if you're okay with it, it seems like the humble dot. Is that correct? Yeah. I think the humble dot experience, it seems like you got way deeper in this. Would you want to make the case study catered to humble that? Will Goto: Um, maybe, maybe that's up to you. Like, rises, rises, fundraising was clearly not interesting compared to the other two. Sure. But I mean, rise is what we're working on now. And I think like, maybe it might be more interesting in terms of like how we're thinking about our next round, if we're if we're doing it. So I'll include both. Ben Ornstein: And we'll I'll turn it in, because obviously I want to promote what you're working on now, right? For you, I want, and I know you, I'm sure you want that too. So I'll find a way to weave it all in, but just wanted to know. So we got the fundraising journey, crazy round, but what did you, when you were raising that money, what did you plan ahead of time to use the money for? Will Goto: To be honest, we didn't really have much of a plan. We need to pay ourselves. And then that's basically it. I would say that was like the surface level of how we were thinking. But in reality, we actually needed the money for growth, right? Whenever you're building something you're selling to mid-market level companies, and even enterprise companies, which we were doing at the time, you need a full sales team. So we hired. But it's funny, because our approach to the whole thing, and this was part pitch was that we were attempting to get managers on board directly. Kind of like how Slack did whenever like, you know, Slack entered into companies and they would kind of land and expand to the companies and they would acquire like a whole enterprise sale because everyone used the tool at the company already. So yeah, we were trying to do a very similar strategy with our tool to get a manager on board land expand because the manager would add their team and then they would communicate with other tools like with the tool itself. And then absorb more teams into the tool. And we had early indications of this in the tool. But we still needed people to get that first touch point to actually install the tool. So we had a bunch of SDRs that we hired to do a lot of cold outreach, a lot of straight up sales, early sales pipeline stuff. And then we tried to hope that the rest of the tool would land and expand itself, and that would take care of the sales process. On its own. So that was primarily where the money went was just people and sales and then obviously you know paying for the product side of things as well. Ben Ornstein: We hired a designer and then also an engineer as well. So basically growth of team and you know basic infrastructure costs and just growth in terms of what like actual marketing spend? Sales. UNKNOWN_SPEAKER: Mostly sales. Yeah. Will Goto: Cool. Okay. Ben Ornstein: That's great. This is a two part question of, and you started to get into this, which is why I wanted to get involved. How did you get in touch with investors? And when you did, how did you know who, or actually, you know what, I'm going to break it up into two. Will Goto: How did you decide which investors would be a good fit? Yeah, that's a good question. So one is, You just have to look at their website and what companies they funded in the past. And usually they'll have some... Every fund has a thesis, right? They're always like... Because they need to raise money from other investors, right? They need to make the case of why their fund is going to be more successful than anyone else. So they all have a theme. They'll have their own choose your adventure kind of thing. So one's going to be like, oh, we're security. Or the other is going to be like, we're interested in companies that are doing network effects, right? And so every single one of these has a theme. So if you go out and you just take every single investment company, every venture capital firm out there, and try to pitch them, you're just going to be wasting your time. And so you've got to go look at them, look at their website, look at what their companies, like what they say in their about us page is enough. Usually in the first sentence, they're like, we're interested in companies that are x, y, and z. And so if you look at their website, and if it's not clear if they're agnostic whatever, then you can just look at the companies they have invested in the past and see if they're kind of similar in the same kind of space as you are, maybe not competing, because if they're competing, then they're not going to fund you either. So you've got to watch out for that. So in terms of concept-wise, yeah, you've got to filter out which ones that don't make sense for you. And it's an easy no for them, because then it saves you a lot of time. The other thing would be the stage at which your company is in. So a lot of funds will not fund anything below seed. A lot of them are just straight up like A, B and C and beyond. Some are just even C and D beyond. Like one of the biggest indicators of this is just simply looking at how big their fund is. If their fund is like a $500 million fund, they’re not going to care about spending their time investing a hundred K into your business. Like they’re not going to return your email. So, One is like, yeah, so the first is like concept-wise if it fits, and then the other is just stage of if it fits. Even if they say they invest any stage and they’re like a $500 million fund, they’re not going to care about you at the early stage. If you’re a pre-seed company, look specifically for pre-seed venture funds because they’re the ones who actually care about you. Ben Ornstein: That’s really good advice and not many people have brought that up because that’s It’s such a good point. It’s like, yeah, I want Sequoia on board. All right, what have you done? Yeah, no, that’s a really great point. And so the second part of that question was, how did you get in touch with these investors? Will Goto: Yeah, it’s all network, unfortunately. I wish I had a better, you know, more egalitarian response for this, but it’s just straight up who you know. Like, yeah, like our connection to a four was through a friend at Twitter. And then David Shellhase, he was the first angel on this that we got on board. We worked with him at Peer. And then he was able to connect us with people as well. So it’s just, honestly, it’s just network. And the best way to get and build your network is to work for early stage startups as an engineer, as an employee, and then build those relationships, because that’s really the best way to get in. Honestly, that’s the way I did it. And then I think if you’re trying to build these these relationships, just like directly, it’s it’s too forced. And it’s very rare that you get some really good relationships out of it. Like maybe occasionally you might meet someone that you might click with, but like it because the the underlying guess, underlying message or whatever you want to call it behind the connection in the first place is to get investment from them. It’s not really building a genuine relationship with the person. So maybe finding ways to build your network and connections genuinely authentically is really the only way, in my opinion, to get really, really good connections into the VC industry. But I think that’s changing quite a bit, actually. I think since the pandemic, it’s been changing. And I think a lot of people, a lot of VCs, see venture firms are open to just getting more cold emails. And I think like they’re filtering methods and algorithms or whatever they use are getting a little bit better. But I think nothing beats a warm intro from someone that is already established and is introducing you to someone who they have a relationship in a venture capital fund. UNKNOWN_SPEAKER: 100%. Will Goto: In the early days, did you We did a few, but I think the only time it would work would be when we had our lead already. So we would say, we’re fundraising, we have a lead already, and then here’s what we do, and then here’s how much they’re investing. Here are the details of the round, and then are you interested or not? And that would give them a straight up like, okay, they already have a round going, they’re going to close in a week, and then we need to get a decision right away. And so So like that not only created the validation of us being proven, but it also kind of created urgency for them to make a decision as well. Urgency is like one of the biggest things to pressure investors to give you a response. It’s like one of the best things to do. Yeah. Ben Ornstein: I’ll ask a little bit more about that urgency. It’s like, you already know the questions before I have them. We had that one in a couple of questions because you’re a hundred percent correct in that. Um, if you had to think about it like a funnel if you turn in terms of how many Investors you did outreach to slash work intro to um if you could How many of those roughly turned into first and second meetings? Will Goto: Third meetings, however many there were and then finally into the into an investment just rough numbers um our our funnel actually had really good conversions because Because again, our initial connections were based off of warm intros, mainly from before or some other angels that we knew. So in terms of straight up numbers, I think our conversions would be significantly higher than what a normal person would go through in their seed round. But it was still pretty brutal. I don’t know, maybe I’d say a tenth of the people that we reached out to probably got back to us. And then maybe half of those, or maybe anywhere between half to maybe 75%, were a first meeting. And then from there, it’s like half each time, basically. So it’s a brutal process. But again, it’s a numbers game. And you’ve got to figure out how to optimize the funnel, just like a sales process. Ben Ornstein: And so when you were doing these pitches, what did you emphasize in the pitch? Will Goto: Because we didn’t have revenue in our seed. So I’ll specifically talk about our seed round, because I think this is probably the most relevant. But I think we talked about the TAM, right? Is probably one of the most important things. I think no company is going to be interested in you if you don’t have a large, like theoretical market that you can acquire, right? Like if that’s not there, then there’s no reason for your company to be a venture backed capital company, period. So convincing people that one, the market for what you’re attracting is absolutely insanely large, but also growing. And then the other would be how your product solves a specific problem, but also has a vision to being something that this huge market will use essentially every day, or be a huge part of their, their lives. And so if you connect those two, and you do it in a way that you’re showing them that it’s possible for you to do this. So like for us, it was it was taking them through our product and how it worked. And then also talking through our engagement metrics of like how often they’re using it, how like deep this the whole like their engagement metrics were with our tool and how long they retained as well. And then also the testimonials that we get from customers as well. So it would be that. And then we would also talk about our land and expand strategies. So that would be tying into how our product would essentially acquire the entire market fairly easily at a super low cost. And ultimately, our vision was like, this really large people analytics thing that essentially the company lives and breathes with so that it becomes core to the company’s communication system. So it’s kind of like telling this narrative that connects your TAM with your product, but also not just telling them, kind of showing them through your products and your metrics and your strategies. Ben Ornstein: Nice. Yeah. That’s a great pitch. And so you really, you start talking about this. And in fact, you actually give it a lot of detail, but what did you do to drive urgency among investors to close the round? Because it is a huge piece of the puzzle. Will Goto: Yeah, it’s, I think the hardest part about creating urgency in the beginning when you don’t have someone who is already committed is you kind of have to create like a false sense of urgency, right? It’s for them. It’s like, okay, there’s you’re not gonna close the round anytime soon. You’re still looking for a lead So like what urgency is there for you other than like my company is gonna die and like, you know Two months, but then that’s like a negative signal. They don’t want to be hearing that right? That means you’re just burning way too much money For us it was more along the lines of we’re doing we’re doing well like we got all these customers and stuff and we just want to get fundraising out of the way as soon as possible, just so we can get back to work. And we kind of framed it as like, we’re not looking to optimize on our valuation or anything like that. We just want to raise money. And it kind of got them the sense of like, okay, they just care more about the product than actually raising money themselves, right? They don’t really care about, you know, like optimizing their shares or anything like that. They just want to keep building this product, keep making it great. And I think coming off that way, it made it seem more genuine, at least in terms of urgency. And I think that that kind of worked pretty well for us, because Miguel and I are product people, and we’re like really obsessed with making really, really great products. So I think that was probably the more genuine way I’d say like, there’s probably plenty of other ways to do it as well. As long as it comes off genuine and not like, Oh, we’re gonna close, you know, we want to finish fundraising in one week, and then you don’t a lead yet, they’re gonna obviously see that and call you out on it or just ignore you. Ben Ornstein: Yeah, now it makes sense. I love that approach. It’s like, look, the more time you waste with me, the company that you’re gonna invest in, the longer it’s gonna take for you to see money. So invest in me now and I’ll go back to building. I like that framing a lot. And so, What was the biggest challenge that came up during fundraising? Will Goto: The biggest challenge? I would say the fundraising process is just brutal. They got a formula for how they decide, and a lot of the bigger venture funds have the same formula. It’s just like the email intro, the first meeting, and then you got to meet with the second partner, and it’s literally the exact same meeting. You’re just picking pitching it again, and then a final pitch to all the partners or whoever the general partner is. And then it’s literally, again, the same meeting. And then just waiting, waiting for responses, following up. I’d say that was probably the biggest challenge, because it’s just stressful to be in that stage of limbo. The more difficult challenges were where you would get conflicting feedback or no feedback at all. All, because every step of the way, every rejection that you get, you can tweak your pitch to make it better or hear all the objections that you would get from an investor and then improve upon them on your next one. But a lot of times, sometimes one objection would be a plus for one investor, but a benefit that you would think was a benefit would be an objection for another. And so sometimes you get conflicting signals. But for the most part, I think just the grueling nature of the process of, okay, you meet with one partner and then it’s not until like maybe another week you get a meeting with a second partner. So it’s typically like a month long process just for getting an answer from one firm. Ben Ornstein: Yeah. Yeah, that is, it’s a waiting game a lot of the time. Yeah. Are there any other unique or interesting stories related to fundraising that you haven’t brought up that might be worth mentioning? Will Goto: That’s a good question. Let’s see here. Yeah, so this might happen to a decent amount of founders. So at a certain point, if you do get a lot of interest, and this happened in our seed round where we didn’t want to raise more than Let me backtrack. So when we got our pre-money evaluation terms from SUSE, we were like, okay, we can actually only raise this amount of money in order to obtain the same amount of ownership, essentially. And then we actually got the round oversubscribed because we cut down on the amount of money that we actually wanted to take. So we were like, okay, we actually… 1.3 million with our target money valuation. Susa came back, was like, we’ll give you this valuation and this much money. And then we’re like, okay, we can take that valuation, but we’re probably going to just raise less money because we don’t want to delude ourselves too much. So at a certain point though, when we got all of these yeses in the door, eventually became oversubscribed and we had to deal with this interesting problem where you have to ask investors to put in less money, but they want to because they want a minimum amount of ownership in the company. So either you have to raise more money, dilute yourself and include them, right? Or essentially, you can also bump up the valuation just a little bit to get that more money in and keep your ownership the same. But in those cases, it’ll also drop the amount of ownership that everyone else has, and then they have to put in more money. So it’s like this really balancing this really like intricate balancing act that you have to go through as a founder to make sure everyone is happy in the round. Everyone has the same amount or their their minimum amount of ownership in the company, but also making sure that you’re not diluting yourself too much and your founder too much. UNKNOWN_SPEAKER: Yeah, wow. Ben Ornstein: And so how did how did you solve that? What did you end up doing? Will Goto: We get so we ended up giving up a little bit more ownership. And in terms of giving more to the to the investors to allow them to put more money in. So it was less of an impact for us than it was for them. So we were giving up maybe a couple of percentage points of ownership. For them, it meant a lot more to them to be able to get that extra from 6% to 7%, for example, as opposed to being, for us, 30% to 35%. So it wasn’t as big of a deal for us giving up ownership for them. Ben Ornstein: Yeah. Makes sense. Will Goto: Yeah. And because that’s a blocker for a lot of venture capital funds. You just want to get them around close. You’re like, okay, whatever. 1% is not going to make much of a difference. Ben Ornstein: I’d rather have the 2 million right now for the company. Exactly. I’m going to build a big business regardless. I’ll get my money back someday. Another percent, who cares? No, that’s awesome. That was probably the painless, just do it and get it done over with. You’ve already given some really great advice. Is there any other fundraising advice you’d like to give to other founders? Will Goto: Let’s see here. So we went over prospecting. Yeah, I guess one of the more interesting pieces of advice, actually, is to strategize around how and what order you reach out to your investors, their prospective investors. So the first couple of investors that you reach out to are more than likely going to be no, just because you’re starting to pitch, you’re green still, like your pitch is not fully nailed down. And so they’re going to come with a lot of objections that you haven’t thought about yet. And if you, if you try to go for like your best fitting, best prospected investors right away, you’re hurting your chances. So it might actually be more beneficial to try to get meetings with people who aren’t as good of a fit for you in the beginning. And then as you start getting the pitch nailed down and you walk into the meeting, you can do the pitch without even hesitating. I have a single objection they can come up with. You have a really, really great answer for. And as soon as you get to that point, that’s when you want the most likely investors that you want to be pitching to. So the first month, it’s like a warm-up round. And then you have all the people that are kind of like loosely fits for your company. The second month would be like your best fit investors that you want to have an absolute best chance with. And then after that, you kind of want to just trail off in terms of like order of best fit. So as you start getting too good at your pitching, it becomes kind of mechanical and like you’re going through the motions, right? So like you want to hit that sweet spot with your best product. I love that advice. Ben Ornstein: And it’s so interesting because some people have said that, and I’ve had other founders say, any meetings meeting, take as much as you can get because all practice is good. So I tend to agree with you. I think that’s the way, if you can optimize it that way, you should. You want a red line when you’re going to your best fit investor. Yeah, I agree. Will Goto: Yeah, I think yeah, I think the every single thing counts like the the tiniest margins matter so much in fundraising because you get so much rejection, right and it only takes one Yes to flip the tables to get other Ben Ornstein: people to join so like any small thing you can do like makes makes a difference 100% um kind of a chance to, you know, recommend an investor and give them a shout out, you know, who’s an investor you’d recommend Will Goto: other founders work with? I would say village global. So, um, they’ve, they’ve basically been, I guess maybe this kind of gets into the rise round. So village global, we got an investment from through brand Kimmel, who was an angel investor at the time for the first round of humble dot. And then the second, they, they committed I think it was like 400k or something like that into our seed round and then we as like we worked with them and kind of we didn’t actually have that much of like a working relationship with them through first company but there were a couple times where I went to the village global events and I think I met Adam once or sorry Eric Thornburg once and then after we closed down that company and returned I think we returned just over half of the amount of money left. And we started a new one. Eric was actually really interested in investing in us again, because he liked us as founders. And I thought that was really cool. He was like, you know, he’s like, I think I believe in you guys as founders, and I’m willing to invest in you guys again. And we thought that was really cool. Because if because we returned the money in the first company, a lot of a lot of investors would see that as kind of like not a great like action of, I guess, maybe loyalty, if you want to call it that, they would expect you to just keep working on different ideas and keep pivoting until you run out of all your money. And that’s what they prefer to do. But we were like, no, let’s like, you know, this, this, this idea is dead. We’re like, we don’t want to work on this. And we, the next idea we actually had was more of a consumer SaaS idea. So it didn’t make sense for us to keep the same investors. Um, it didn’t seem like the network would be that helpful to us. And then I think, um, It was getting to a point where any idea that we’d come up with for a new company, they were all kind of like lukewarm about because they invested us initially for an enterprise, like messaging company in like enterprise sales. So we, yeah, we returned the money. And then, you know, when we came up with this new idea and we initially worked probably about like a year or so without investment, but then we’re like, okay, you know, We’ll raise a precede and see what happens and then eric was like interested and he was like, okay um, I like you guys I think I believe you guys as founders and I think that’s just like something that A lot of vc people don’t do after You return Ben Ornstein: money to them to be honest Yeah, so I thought that was really cool So village global and eric. Yeah. Yeah, eric’s awesome. I love his content. Um He’s he’s he’s the man. So that’s that’s pretty cool. Yeah, um Yeah, that’s a great one. Are there any resources you would recommend to founders? Books, podcasts, newsletters, anything? Will Goto: There was this one, I think it was an air table or it was a Google Sheet by Shea Goldman. And he had this massive list of investors and the size of their latest round and what they’re investing in and stuff. And that was probably one of the best resources to prospect your investors for fundraising. I think it had a bunch of stuff that you don’t even think about in terms of fundraising as well, like how old their fund is, for example, how much money they have unallocated left. You could have companies that just raised a huge round and are willing to deploy that very quickly. And those are more likely to invest at that stage than ones that have little funds left. They have been open for five to 10 years and they’re just kind of like cherry picking or waiting for like really good opportunities to come across. So I think any sort of like comprehensive list like that is really, really helpful for deciding who do you think would be good prospects for your fundraising. In terms of like books and stuff like that, honestly, each person’s experience is kind of different And I just, I’m always like, take what you know, and then you got to learn from your experiences. And oftentimes, like when people come to advice, and you give them advice, they like don’t listen to it until they’ve experienced the same thing you have. It’s just just, you got to do based off what you what you’ve experienced. And I think a lot of people learn that way. So just do more as much as you can, as much as possible and learn from it as quickly as possible. Ben Ornstein: I love that answer. That’s great. And And the last question here is, do you have any hot takes regarding the fundraising process? Will Goto: Any hot takes during the fundraising process? Ooh, that’s a good one. I think a lot of founders, when they come up and they say they have trouble with fundraising, and they think like, something is wrong with their company or something is wrong with like their pitch or something like that. I think oftentimes the actual problem is the founder fit for the problem, to be honest. So a lot of people will say, I’m starting a company and I’m going to make like the next Uber, but they have no experience in taxi services or anything like that. And I think a lot of people get into entrepreneurship and startup because they like the idea of it and they like the idea of doing their own company. But I think the founders that have the most success come from an experience that they’ve had or a job that they’ve had and they were like, this can be done better and this is how I’m going to do it. And I think those are the founders that get backed more often than not. And I guess that’s not really a hot take, but I think majority of the people who are out there fall into that former bucket. And I think they need to really be more introspective about themselves so that they can fall into the second. No, I think that is a hot take. Ben Ornstein: And first of all, I think founder market fit is one of the most important things that not enough founders think about. I totally agree with you. And I think it is a hot take because a lot of people are just like, oh, if it’s a good idea, then it’ll be successful regardless, or that’s what they’re But yeah, if you don’t experience it yourself if it’s not a problem you face if it’s not something you’ve seen You know things around that I totally agree. Yeah, there’s a big so that is a good hot take. I like that a lot. Yeah Well, that’s all the questions I have for you. Um This has been awesome. Um, I really appreciate the detail um, do you want to give me a one-liner because at the beginning about um humble dot and rise just like About you know, just a quick one line summary of each so I can Will Goto: include that at the beginning Yeah, so humble dot was a communication tool for distributed teams Or maybe asynchronous teams if you want to call it that cool The rise is um an ai-based tracking tool to help you be more Ben Ornstein: productive So interesting so you’re going with the same a similar business Yeah, so one is like communication. Will Goto: The other is more time tracking and productivity, but I guess both kind of fall under productivity. One’s more messaging and communications. The other is kind of time tracking and analytical productivity. So Rise focuses a lot more around the concept of focus and focus time. So it’s kind of like individual productivity almost versus team. Yeah, that’s really cool. UNKNOWN_SPEAKER: Nice. Ben Ornstein: Yeah, and I think we came up with Rise. Will Goto: So we actually came up with the idea to work on Rise because of our of being productive at Humble. We were like, what are we spending our time on? Are we doing it efficiently? There’s nothing that gave us that granular of information whether or not we were doing what we needed to do, aside from the other conventional time trackers, but it also didn’t tell us if we’re actually productive or not, or if we’re focused or not. And I think Rise solves that problem pretty elegantly. Ben Ornstein: 100%. Are you guys still a two-person team? Will Goto: We’re four people now, yeah. For people where so we raised, we raised 600k for rise in safes. And then now we’re for people and profitable. So congratulations. That’s awesome. Yeah, it’s nice. Ben Ornstein: Yeah, that’s probably a much better game to play. Yeah. And I guess this maybe I’ll add one more thing. Will Goto: One more quick thing about our fundraising for rise is that we did a pre seed round. And we haven’t done a seed round yet. Even though we could have, because we’re not exactly sure if this is a company that’s actually venture scalable. And so this is something we’re still trying to figure out ourselves. It’s something that we can scale to billions of dollars, or if it’s going to be more like a quote unquote lifestyle business. So raising the pre-seed and not actually committing to a seed round yet has given that optionality still for us. Ben Ornstein: That’s so good that you’ve thought about that, because we interviewed We have a podcast as well. We interviewed Adam Ranklin of Pitch and Steven Galanis of Cameo. And they are two of many companies back in 2021 that raised behemoth rounds, not being able to run into their next round. So yeah, it’s very smart of you to think about that. Yeah, no, that’s awesome. Will Goto: All right, sounds good. Ben Ornstein: Yeah, so I will take up to a week to get this done, to get the draft over to you. You can make edits or say, hey, I want this. You can edit directly, add comments in the Google Doc, whatever. And then I’ll post it and we’ll give you the link and all that. Cool. Will Goto: Sounds great. Thanks so much. Thanks so much for the time, Will. All right. Likewise. See you, Ben.