- Platform: meet
- Source: Read.ai 01J5RF1M6NH41VDR8485VJ7MYV (via Ben Ornstein’s account, imported 2026-08-06)
Transcript
Ben Ornstein: Bye bye. Ben Ornstein: Bye. Ben Ornstein: you you Bye-bye. Keith Corso: Keith, what is going on? How’s it going, man? You know, strangely enough, I tell you this every time I see you, my phone still thinks it’s that I’m gutch slash Keith. So as I always say, I think about you all the time, even better to see you. How are you doing? I love it, man. Ben Ornstein: That story makes me smile every single time. Ben Ornstein: Yeah, no, I’m doing well. Ben Ornstein: I’m doing well. It’s been. Quite a journey these last few years. So it’s been fun, I’m sure. Same on your end, for sure. Yeah, yeah. Keith Corso: What is the highest high and the lowest low? Ben Ornstein: You know, I’ve learned probably everything that can kill a startup. And to me, that’s like a crazy high. Like, I don’t expect anything anymore. Or I guess I can say, I do expect everything anymore. And lowest low? Ben Ornstein: yeah, getting my salary cut a few times and then eventually like leaving the day to day of the company, even though they’re still technically around trying to sell to like a larger competitor. Yeah, it wasn’t fun. Luckily, I don’t I’m not paying like crazy rent or anything. I kind of set my life up just in case because of working at the early stage startup. So yeah, no, I but I’m not I am not I want to stay in the startup world. So, um, I wasn’t, uh, I’m, I’m trying to think of a word. I can’t think of it, but, um, yeah, so yeah, that’s been, it’s, that’s been it. Keith Corso: Yeah, well, I read a quote recently, excellence is the ability to take pain. And there’s something about people who throw themselves in the ring or day after day, when things are not working out, that deserve a ton of credit. And there’s so few people that are in the arena, I’m sure you’ve heard of the quote, versus sort of outside moving money to and from and sort of viewing what’s going on. And I’m not saying that we are exactly in the arena, everyone kind of has their own perspective, but to take the risks that you have is super admirable. Yeah, I appreciate that. Ben Ornstein: I mean, it’s been, it is what it is. But I remember last time I talked to you about startups, I didn’t know the place I was supposed to be, but now I know operations is where I thrive. So, um, which is great. Keith Corso: So awesome. Keith Corso: Yeah, yeah, definitely. Keith Corso: Are you still keeping up your tennis game, golf game? How’s that coming along? A lot of tennis. Ben Ornstein: I’ve been playing a ton. I actually have a tournament tomorrow. It’s like a, it’s like an individual, like There’s four people in the draw, so I start in the semifinals, a small one. But yeah, I’ve been playing a lot of tennis. I’ve come home a couple of times to play golf. Your brother actually came back from North Carolina with Liam Gorman a couple of weekends ago. We played in Maryland around here, which was hilarious. So not too much golf, but a lot of tennis. Keith Corso: Yeah and wait, are you staying in Maryland for the foreseeable future? Is there a significant other of yours that’s keeping you there or what’s the tie? Ben Ornstein: So I was in Baltimore for Morgan Stanley when I first graduated school for two years. I met my girlfriend there. We’re actually living in Delaware now. So I moved home for a year. Now we’re living in her sister’s house in Delaware and we’ve been here for two years. So eventually, We’ll move out and get our own place. I have no idea if it’s going to be in Delaware, Maryland or wherever. No idea. But it’s not going to be in New York. Keith Corso: I don’t think it’s going to be in New York. Ben Ornstein: Why is that? Her family. She has a huge family. She has five sisters. Ben Ornstein: Four of them are very close. One is a little, the oldest is a lot farther away. Not a lot of fun significantly compared to the others farther away. And then then there’s the two that are Okay, one’s far away three are close and then the other two are you know, we live with the other one so And they’re there they’re very close. But yeah, so that’s that’s where I’ve been That is crazy crazy crazy. Keith Corso: And so and so this podcast new podcast I would love to hear a little bit of background on what you what you’re up to here. And of course how I can help Yeah. Okay. Ben Ornstein: So this necessarily isn’t exactly the podcast. So do you know who Michael Houck is? Keith Corso: Uh, I do not. Ben Ornstein: He’s a newsletter called Houck’s newsletter. Um, it’s a startup startup newsletter. He’s a former founder himself, a founder of launch house. UNKNOWN_SPEAKER: Yeah. Ben Ornstein: So I’m working for him and that’s what this is. So, um, I met him during my no ramp days. I interviewed him for the podcast there. So that’s how we create a relationship. After I kind of saw the writing on the wall, I said, Hey, I’d love to work together. Long story short, we’re working together. We’re doing a podcast. We are doing a podcast, but, uh, for, you know, startup founders and all that, but this specifically is a case study. And this case study is, um, He wants to release the best way for founders to raise money. And what better way to do that than by speaking with founders who have actually done it? And so asking a bunch of questions, they’re softball questions. They’re nothing crazy. And then payment gating these behind his newsletter to his paid audience to see a whole bunch of cases. We’ve done almost these 60 by now. Ben Ornstein: And, and they’re great. Ben Ornstein: They’re, they’re all different. Everyone’s got their own stories. So you can be relatively candid. Uh, like a lot of founders are saying like their valuations and stuff like, for example, like that, um, any stories you want, this is obvious. The only reason we have the AI guy in here so I can create the transcript afterwards or use the transcript. Yeah. Keith Corso: And if you want to get rid of mine, uh, feel free. I think there’s no worries. Ben Ornstein: It’s never heard of day. That’s a new one for me. Yeah, there’s a lot of them. But yeah, so feel free to be as candid as you’d like to be. Ben Ornstein: We’re just going to turn this into a document afterwards. I’ll send you the draft. You can be like, hey, I want to take this out. We’ll leave this in, et cetera. And then, yeah, it’s never going public. This video is going nowhere. Again, solely for the transcript use. Ben Ornstein: Yeah. Any other questions? Keith Corso: I don’t think so. Let’s do it. UNKNOWN_SPEAKER: OK. Ben Ornstein: All right. Ben Ornstein: Let’s do it. All right. Ben Ornstein: So yeah, if you could just start by introducing yourself and your startup. Keith Corso: My name is Keith Corso, co-founder and CEO of BusRite, and we are increasing the safety and efficiency of the nation’s largest mass transit system, being school buses. School buses transport 26 million students to and from their education daily, and that system is largely being run on pen and paper or super antiquated software, which is causing a crippling driver shortage, increasing route complexity, overwhelming parent demands, and threatening a lot of what K-12 was. So hopefully that summarizes it. That’s amazing. Ben Ornstein: Yeah, obviously, I know bus ride from its earliest days. So it’s so cool to be able to talk about it today. Yeah, if you could share, you know, about the fundraising journey so far, if you talk about How many rounds you could give as much detail as you’re comfortable with how much raised valuation? Etc. Keith Corso: Yeah, so we’ve raised about 15 million dollars to date um across four different rounds of financing um And oh man, there’s so many different paths to go down the one that really speaks to me the most is how people can become different as you raise more money. There’s a, in my mind, there’s a clear distinction between, hey, like you have a good idea and you’re workshopping with a buddy and someone gives you 500k or a million bucks. Once you actually start to build something that has legs, people People look at you very differently. They look at you strictly as a vessel to make more money and that’s okay, but when you think that those people are the same and they’re still your buddy and they’re still the investor that wants to workshop with you and so on, then it can be very jarring because that person is now very different. And furthermore, as you raise more money, ideally you also have more traction and product market fit and so on. And I don’t think people speak enough to just the way that people change around them as there is any bit of success, especially when you start to hit repeatability. And that is a really interesting problem to solve for, because you don’t know what angle it’s coming from Everything from customers, to early team members, to advisors, to investors, the list goes on. Keith Corso: I would say that we’ve had certain investors who have said things like, 350 grand is nothing to me. I’d much rather see this company die. They didn’t say die, but a word that’s related, because they’re frustrated because they don’t get this small term into a term sheet that they think they have the right to. Keith Corso: And then you have lawyers that go back and forth with each other and then it becomes a contest of, you know, who pays more for their lawyers. So there’s just a lot that’s wrapped up in the emotional journey that can split relationships or just add tension that takes a toll on you. Because then you look at the world as, well, then who can you trust? Who is really there with you to the end? And that’s what makes it a little bit lonely. And I would also, if I pivot away from sort of the emotional Side of it and the relationship component if there’s money on the table take it. Uh, we During two or three of our fundraisers, we ended up raising a bit more money. And in some cases, like our pre-seed round, we raised $500 versus our goal And during our seed, we raised $2.5 versus And people always talk about, oh, protect dilution, especially when the market was a lot better. And looking back on it, each time that we’ve raised more money, it is the only reason that we’re still alive. And that is so hard to wrap your head around when you’re like, wow, if we just did not take the additional 250K, we would not have gotten these two months, which gave us this ability to meet this person and stay alive for this much longer, get through COVID, you name it. And so, of course you want to be mindful of dilution, but at the same time, there’s something to be said about the sanity and the ability to keep winning if you can stay in the game, and often cash is your ability to stay in the game. And then if I had to add a third… I’ll actually pause there, unless you want me to keep rambling, but go ahead. Keep going, keep going. Yeah. So my, my next thought related to fundraising is that, uh, be my like top quote unquote, like tier one investors don’t always solve all your problems. And at the end of the day, I had one of our investors who said, I said like, Oh, like, how do you think about adding value to your portfolio? And they said, we’re going to write you a check and we’re going to get out of your way. And at the time I was like, huh, I don’t know how to feel about this. Like I want people who are value add, who are supportive. And I’ve come to appreciate that that is one of the most helpful perspectives an investor can have. They’re just not in the weeds. Right. And, and frankly, I think about this all the time is I try to help my own team members who are more boots on the ground, customer success and product. And I’m like, am I that investor that thinks they’re adding a ton of value and I’m just too far removed from the day to day? And I try to live in it as much and create safe spaces where team members can share when you’re helpful and not. But at the end of the day, you know, investors can be helpful. Helpful. Their networks can be really helpful. But, you know, don’t always get wrapped up in the shiny, you know, logos and bring money in the door as quick as possible because the opportunity cost of continuing to fundraise to try to get a slightly higher valuation does have a huge cost associated with it. UNKNOWN_SPEAKER: Amazing. Ben Ornstein: Yeah, no, that was all Super helpful. There’s a section later where I ask about advice and you already gave so many, so that’s awesome. When you look at your fundraising, what did you plan ahead of time to use that money for? Were there milestones you wanted to achieve before subsequent rounds? And again, how did you allocate that cash? Yeah. Keith Corso: So in the earliest stages, like your first few rounds of funding, There’s, the capital is meant to just experiment as much as possible. Experiment on go to market motion, experiment on does this type of team member or department even make sense? Like support operations versus strictly customer experience versus both. Does it make sense to have a small schools sales team versus a large schools versus, but like, it’s all about experimenting. And I say this all because there’s only so much visibility that one can have in those earliest financing rounds of they’re going to put cash in here and they’re going to get cash out here. That said, there are definitely clear metrics that a company wants to hit to be attractive to their next round investors, right? So like series A, people say like a million dollars in AR, they say like, you know, a few other things, right? And it’s good to be aware of what those broader guard rails are, but also knowing that, especially in those early days, like in my mind, you’re just trying to prove product market fit as quick as possible. Are people pulling out their wallets, paying you and staying with you? And like everything else is just noise. So you back to your question of where their milestones certainly, but, uh, and is there, um, a general idea of how we want to allocate these resources in broad strokes, definitely. But there’s a lot of flexibility in those early days around where that money actually gets allocated, even in these buckets. And they can get switched between from one bucket to another rather seamlessly as you figure out what works, what doesn’t work. An example We initially thought that we’d be able to use free tablets from T-Mobile. When you buy a data plan, you get a free tablet. Well, unbeknownst to us, those tablets don’t work in extreme temperatures. You drop them on a bus, they break. With dust, they don’t work. They don’t have the right port to connect to power ground. Of ignition, they don’t have a GPS sensor or a telematic sensor. So, so we ended up having to spend several hundred dollars on one tablet. We have thousands of these now across the country. So, uh, there’s again, there’s only so much visibility in debt, especially when you’re figuring, figuring out there’s still the foundation of the business. Ben Ornstein: Yeah, no, that’s tough. And the broad stroke of kind of phrasing it instead of phrasing exactly what you use the money for. Kind of saying what it’s broadly used for is really helpful too. When you were considering investors, how did you decide which ones would be a good fit? Keith Corso: Yeah, I mean, it depends on the, I mean, first off, like, do they invest in your round? Are they comfortable with a pre-seed company, a series A, et cetera? Because if a lot of investors say they invest across these stages, but go look on their LinkedIn. Are their last five board observer or board director seats companies where they invested at your stage? One of the reasons why that’s important is because they might say that they invest at seed, but really they only do A and B, but they say seed because they want insight into who are the up and coming companies that they can build relationships with. And furthermore, the metrics that they benchmark you against are relative to the other companies they’re looking at during their day. So if they’re mainly A and B, but you’re raising a seed, then you’re already starting off on the wrong foot. So yeah, an investor has to spend time in the stage that we’re in, they have to be comfortable with the type of metrics that a business like us might have in that stage. And ideally, they’re also familiar with what are the challenges that you as a business and as a founder go through at that stage as well. More specifically than that, for our business, we’re both hardware and software. So I love finding investors who have experience backing companies with that profile. So examples are companies like Toast, the POS system, right? We often consider ourselves like the Toast of student transportation. Likewise, investors who invest in logistics, businesses that have gone from offline to online, where they’re largely replacing pen and paper or antiquated on-prem technology solutions. Investors who are comfortable with EdTech. We sort of straddle a number of different spheres and any one of those investors could have gotten excited by a bus ride. A couple of our largest investors, the one who led our last round, He started a company also in college. He scaled it to 250 million of ARR, took the company public when he was like 30, 31 years old. And so the whole journey, and it was in the ed tech space, granted selling to higher ed, but similar sales motion, the focus on conferences, in-person relationships, the emphasis on the customer experience, a lot of similarities between the business that we’re trying to build as well. And then our second largest investor, their whole thesis is investing in software beyond the screen, meaning how do we make software ubiquitous in the physical world? How do you do that? Well, it largely comes with hardware that can deploy fully software really fast. And so you try to find investors who are thematic, also spend time in your stage. But at the end of the day, you also don’t know where that next investor is going to come from, because some of them, some of our most helpful investors have no experience in any of the domains that I just UNKNOWN_SPEAKER: shared. Ben Ornstein: Well, and you led me right into the next question, because there are so many ways you get in touch with investors. How did you get in touch with yours? Keith Corso: Yeah, so there’s a number of different channels, if you want to call it that. One of them was I was fortunate enough to lead the Entrepreneurs Club at Northeastern. It’s the largest club on campus. We held five, sometimes six events every week all year long, even during finals, midterms. Name it. And we had several programs that we ran from our, you know, Husky startup challenge, which is a classic pitch competition, all the way to our Tuesday speaker series, where we brought in, you know, investors, operators, founders, and several hundred folks would show up and we do a fireside chat, interview them, they give a presentation. And so, as the leader of the club, I was either often interviewing them, slash leading a fireside chat, or was there to greet them beforehand, thank them afterwards, and I’d always send follow-ups and take down notes from what these people are saying, and I still have my air table open where, ever since I was a sophomore in college, I’ve tracked every professional conversation that I’ve had that’s been one-on-one. That list is now 2,414, but a lot of these come from those early folks that we brought into the Entrepreneurs Club. I was able to raise over a million dollars from these people that came in the door to a club on campus where everyone else is like, You know, all right. I got this thing to worry about with with my exam tomorrow like sure I’ll show up But like really I have like this date that I’m going on this party tomorrow night But we’re you know, I was so focused on how do I capture all this insight? How do I write it down and how am I gonna follow up with this person, you know next month three months after that? And stay in touch with them and ended up kicking off our first financing round and then subsequent rounds. Those folks are the ones I went to for pitch feedback, fundraising advice, and ultimately a number of them wrote checks and made really helpful introductions as well. So yeah, you don’t just open up a curtain and all of a sudden you’re flooded with money. It does take years. Ben Ornstein: Did you do any cold outreach in the beginning? Keith Corso: Yeah, it did some cold outreach, uh, but it’s incredibly rare for investors to ever consider anything that’s cold. So, um, I, I just took the, I went on all the LinkedIn networks of the folks that were sort of in my circle at that point, even if it was someone who came in for a Tuesday speaker series once. And I had one conversation with them and I would filter their LinkedIn network by investor title. And then I’d filter the 200 people in their network. And I’d go back to them saying, hey, I saw you’re connected to ABC. Any chance you can make an intro? Of course, I would make this ask after I then asked them for feedback on the deck, made revisions based on feedback and so on. But, you know, early on to raise $250K, $500,000, you don’t need a thousand people and their networks, right? You need hopefully five or ten. And that’s definitely doable, especially when, you know, you’re connecting with these amazing people at university events. UNKNOWN_SPEAKER: Absolutely. Ben Ornstein: Yeah, that was a cool way for you to meet so many people. If you think about how many investors you reached out to. So it’ll be harder for you to think about like of the ones that you reached out to cold, but how about like the total amount of people that you reached out to or got connected to, maybe then the subset of those people that you had initial meetings with, and then the subset of those that ended up actually investing. And these can obviously be rough numbers. Yeah. Keith Corso: I mean, for our seed round, I remember the day that we closed, Our CR investor CRM hit 100, 100 rejections. These are not email rejections. These are media. Like you had a first meeting and even if you have five meetings and you get to the partner pitch in the CRM, it’s still one rejection. So we’re talking about 400 something meetings and that’s how many. Rejections right and that’s the day that we closed as well So it’s you know, just like venture. It’s it’s the power law All you need is a few people to say yes but when you’re getting berated day after day and really smart people are telling you that there is no place in this world for this company and this product can’t scale and selling the edtech socks and the whole nine it I mean it It crushes you, crushes you. So all that to say, yeah, that was for our seed round. We probably had, you know, 10, 12 investors in our seed round, 15 and yeah, a hundred rejections there, but that doesn’t include the probably 50 others that we got in email intro that just said, Hey, it’s not a good fit for us. That were already in network. And I’m sure I did some cold outreach too, does not include the ones that, you know, it could have kind of blow you off from there. So yeah, it’s the funnel gets short real quick. Yeah, but that’s all you need. Ben Ornstein: All he needs a few, right? And that’s all that matters at the end of the day. Few believers. Yep. Ben Ornstein: When you were pitching, what did you emphasize? Ben Ornstein: What were you, you know, what, how’d you get people to invest in you? Keith Corso: How do you get people to invest in you? Ben Ornstein: Well, no, the real question is like, what did you emphasize in your pitch? Keith Corso: Yeah, there’s a lot of people with really good ideas. I believe there are very few people that are out there knocking on doors, building their company brick by brick. I’m a little bit biased, but in our journey, we’re going school to school, knocking on doors. Before we even had a product, I was selling the product. We didn’t even have a product, right? We had wireframes. And there is a part of investors that really leaned into and cared about, wow, like if this is what you can do when you don’t even have a product, when you hardly have a team, imagine if we could put some capital behind this kind of ambition. And so I think one thing that stood out again was like traction from the earliest days. Number two is There’s a, it is a class of investors who really like investing in like sleepy markets that people aren’t paying attention to. And I kind of, I played into that narrative a lot, which is not many people like look at who the competitors are, right? Pen and paper. This is what the leading software looks like right now. And here’s how big this market actually is. Can be. We also have a vision that I think is pretty compelling where, you know, we have our vision broken down into three acts. Act three, the end game, is how do you take school buses that sit idle for 80% of their life and use that extra capacity to, you know, for last mile delivery, public transit, charter transportation, non medical emergency transport. And you have these districts that are looking for more revenue, you have bus drivers that are looking for more income, you have buses with all this latent capacity. And the only way to get there is if you actually digitize what is the largest mass transit system and by digitizing it, I I mean, putting tablets on buses, I mean real-time routing, real-time tracking, real-time telematics. Once you bring it online, the possibilities are endless as far as how you can use this massive transportation market to unlock all new transportation markets, frankly. Leaning into that vision a bit. One investor that got really excited by that, Cyan Bannister at Long Journey Ventures. She was one of the first checks in Uber when it was a black car company. They had a vision to turn these black cars into everyone’s personal driver the same way that we’re trying to turn these school bus fleets into all these different types of transit networks. So yeah, I think that those are a few things that stood out. And then the last thing I’ll say is during COVID, School buses weren’t on the road. So, you know, we’re sitting there scratching our heads like, wow, all these investors are telling us that K-12 is going remote forever. And there’s no place for like in-person brick and mortar education. And your team is looking to you every day to figure out what are we actually doing with our life? Why are we here? Why am I not just at Google making twice as much?” And you have to stare them in the face every day and say, no, no, no. This world is going to open back up at some point and kids are going to have to get to school and the problems are only going to be exacerbated. Driver shortage is going to get worse. All these drivers are going to quit. Routes are going to become more complex. Parents are only going to be more frightened about their child’s safety. And our original thesis of building this company is only going to be more important. And as the months went by and it did not look like schools were going to open up, that was really hard to look at yourself in the mirror while you’re fundraising, telling the same exact story. But what I would say is, you know, we ended up using our technology and we pivoted our efforts and also Ultimately we routed, tracked, and navigated over $300,000 worth of goods from coffee, donuts, oysters, you name it, to several thousand homes, hospitals, community centers across the Northeast. And that showed investors like, wow, this team can be super scrappy and the technology might be applicable to other markets. So I think that partly answered your question. No, that was amazing. Ben Ornstein: Yeah. I mean, I do want to sit down at some point and just hear about the COVID journey. Like I heard it from Matt, but dear God, I don't know how you figured that out and how you got through that because that must've been one of the darkest times in your life. I can only imagine. Keith Corso: We raised our seed during that and it took us, I don't know, six, nine, we had one month of runway left. We had an investor who's like a perfect profile. Here are the terms, we're excited to invest. Friday afternoon call, we're wrapping up everything. And they say, actually, we're not doing this anymore. And that was the last time that I cried. I was in Long Island and I went downstairs and I was just crying. And it was, I was like, wow, everything that we've worked for, we have one month of cash left. And I already told our investors that we're moving forward with this investor. And somehow we got through. Ben Ornstein: God, well, there's another question a little bit later about interesting or unique fundraising stories. Maybe you'll be able to talk a little bit more about that and how you got through it after. Um, I love the use that the act three is very interesting. The whole like underutilization of assets. I think about this company I heard on this podcast called the pitch, you know, pitch, um, where they're using churches. I mean, everyone talks about this where churches are being used, you know, once, maybe twice a week. What the hell else are you going to do when it's just sitting there idle? So using those assets that are just sitting there, otherwise doing nothing is genius. So being able to use those other use cases and what you guys figured out during COVID and after, I'm sure, is really interesting. Thank you. Keith Corso: Yeah, we're excited to see that pan out. I mean, that's where the industry is going. So, you know, it takes a certain kind of company that has the routing data, that has the student data, that has the driver data to understand when are these vehicles actually available and what drivers are best suited for different trips and so on. 100%. Ben Ornstein: And when you were trying to close rounds, you know, what did you do to drive the urgency among investors? Sometimes that's really tough when there is not exactly urgency. So, yeah, how did you do it? Keith Corso: Try to close as much business as fast as you possibly can. Keith Corso: You set a round size that you hopefully will oversubscribe on, and creating urgency is like, hey, we have a million left in the round, or we have 500k left in the round. And as they start to see that the number dwindles, then they kind of jump on board. Hopefully this doesn't go out to the rest of the world, but something I would do is, I knew an investor had a certain check size range. And I would tell them, like, hey, this amount is available, and I'd give them something in that range. So everyone thought that, like, that allocation was available, and boom, they come on board. And so, yeah, it's worked, I think, every time, to a large extent. So that was helpful in creating some urgency there. And then, let's see what else. What else is helpful in creating urgency? I would say there's small things like, hey, you talk to an investor and then you're in San Francisco and then you're in New York and then you're in Boston and they start to see like, wow, they're going to be going back to San Francisco, but it's probably a partner meeting and where you are literally in the world. Actually does sort of create these narratives in other folks' heads. And then also, you know, playing hard to get a little bit, right? You don't wanna respond to everything like two seconds later while also being very diligent in your follow-up and not too delayed. There's that fine balance and yeah. Well, you started with there. Ben Ornstein: We spoke with Zaid Ali from Valley. Maybe you know him. He answered this question saying, sell something, that's all that fucking matters. How do you create urgency? Get revenue. And that's what you started with, which reminded me of that, which was hilarious. Ben Ornstein: And so you obviously had some challenges that have come up during fundraising. What was the biggest one? UNKNOWN_SPEAKER: Yeah. Keith Corso: The biggest challenge is when your co-founder leaves you one week before you have to fundraise. UNKNOWN_SPEAKER: God damn. Keith Corso: And that's during COVID. And that's when school buses aren't on the road. And that's when your market is zero. And that's when you can't drive revenue. And that's when the rest of your team is like, what the hell are we doing here? Why are we building this thing? And the list goes on. That's definitely tough. Ben Ornstein: I mean, yeah, I don't have much to add there. That's insane. Ben Ornstein: Now it's that question about the unique or interesting stories. Ben Ornstein: You can talk about what happened when you got through that. You had a month left. That investor said no. I think it would be pretty interesting to hear, what the hell did you do? Yeah. Keith Corso: The best part about that week is that we had a month left of runway. One of our largest customer at the time in New Jersey, she called me and she said, your tablets are smoking and melting on our buses. Keith Corso: I was like, wait, there is no way. We didn't have the money to replace tablets, right? This is our largest customer. And the best part is 24 hours later, a new investor was going to call them that was going to lead the round to be a customer reference. And tablets are smoking and melting on those buses. So what do you do? You book a Airbnb at a house in New Jersey in the crawl space. Where there's spiders and roaches and you go with a couple of team members and you ask the Airbnb owners, hey, we need this indefinitely. We're going to book two weeks off the bath. We're going to live here. And we needed to live there because we have no life otherwise, if we don't fix this customer's issues. And in that house, you have the top of the house in the attic, there's an international arms dealer that has his business running out of there. In the middle of the house, you've got these parents with these homeschooled children who are talking about shooting people in the leg. And we find nine knives in the grass of the house and then us in the crawlspace and we're like we're just here like we have it we have no other option and and these tablets are melting on these buses and the there's short circuits and they're smoking and Wow, and you're trying to close around that seemingly doesn't exist anymore because you also just had terms taken from you And your market doesn't exist because kovat is there right? Yeah That sucked really bad. So your question, how do you get out of it? How do you get out of it? You go through people's networks every day. You ask for introductions and eventually you hopefully hit a super connector like we did with one of our investors, Sahil Lavangia. Keith Corso: Can you get a better one than him? Yeah. Keith Corso: So I was actually working from his office yesterday in Brooklyn, but he, I knew a ton of folks out in the Bay Area and ended up making a number of introductions to us on the first call. We said, yep, I'm going to invest $250,000 right now. And I was like, wow, there’s actually life. This is surreal. So yeah, we lived to see another day. And then the 250 turned into 500, turned into a million. And we just kept going and trying to keep a straight face on while you know that like literally you see the days are going by while your co-founder had open heart surgery. And so we had three co-founders. Other co-founder, open heart surgery is out for some time. And like, of course you need to make sure like they’re taking care of themselves and their family and whatnot. But yeah, you go back to these moments and you’re like, oh God. Ben Ornstein: I don’t know how you did it. That’s insane. Ben Ornstein: Holy shit. Ben Ornstein: I did not know it was that bad. I remember Matt giving me highlights. Didn’t sound like that. Keith Corso: The best part is that Every time a founder or anyone tells you these things, they’re happening in real time too. They always talk about them historically. Don’t think they just happen at a point in time and it’s gone and you’re like in the clear. One of my favorite quotes is, the rewards for solving problems is more problems. The only thing that you’re ever guaranteed is as you scale is you inherit so many more problems. Nothing else is guaranteed. Your product has become more stable. You’re not guaranteed more growth. You’re only guaranteed like, wow, the severity of these issues are going to increase. So if the stories are like that, then they only just, they only balloon as time goes on. And then it’s probably exponential too. Ben Ornstein: It just keeps, yeah, that’s crazy. Moving on to looking backwards, what fundraising advice, you’ve already given some great ones, is there any other pieces of fundraising advice you’d give founders? Keith Corso: Traction Traction is the most important thing like I said a lot of people with really good ideas So few that are like brute force brick by brick building a product and getting it out in the world a lot of people want to sit behind their computer and send out email marketing campaigns and to find the next get rich quick scheme, getting out in the world, find your customer, show up at their door uninvited. Those things go a long way in actually driving business, actually figuring out what the market needs, actually figuring out what product you need to build, us showing up at these prospect offices sitting in the transportation office when they did not want us there. That’s how we knew what we needed to build. That’s where we saw the ultimate chaos and how deep and crippling these problems were. If we just talked to them over Zoom or sent them an email and sent them a survey, we wouldn’t learn anything. UNKNOWN_SPEAKER: That’s amazing. Ben Ornstein: Yeah. There’s a section here we have, you know, who’s an investor you’d recommend other founders work with? This could be as many or as little as you’d like to add. You don’t even have to give specific ones if you don’t want to, but up to you. Keith Corso: Yeah, I would say, underscore VC out of Boston. They’ve been a huge supporter of ours from the get-go. We were a part of their summer accelerator. They were our first ever institutional check. They’ve, you know, followed on each financing round. But more importantly, they’re just like an incredible group of people. And I was working out of their offices all last week and reminded of how people first they really are and how they care so much about the journey and they don’t just look at a company as many spreadsheets and tabs. And then I would also add that Long Journey Ventures, they’ve been a pretty strong supporter as well. And it’s a strong supporter. I mean, they’re the ones who said, we’re going to write you a check, get out of your way. And when I go back to them and ask them for introductions to their network, they are more than willing. But they are not there slowing you down and asking 30 questions after every investor update. Ben Ornstein: You’re right, those are the best investors to have. In terms of resources that you recommend founders, books, podcasts, blogs, whatever, again, feel free to list as many or as little as you’d like, Keith Corso: I’m reading a book right now called Losing My Virginity. Richard Branson’s book. And it just shows you how limitless the human potential is and how much we can actually endure. So every time I’m dealing with one of these challenges, we have no idea how much further we can go. The only way I can wrap my head around it is, one of the best analogies, I go to the gym and I’m like, the only way that I actually grow, get bigger, is when I’m going through extreme pain. When my muscle is shredded, that is the only way that I’m going to grow and get better. If you apply that to your life, personal and professional, the more pain that you go through, just the better you become as a person, the more pain you’re able to navigate, a.k.a. The more risks you’re able to take, a.k.a. The more impact you’re able to have. And there’s this thought that, oh, mentally I need to limit the pain. But physically, when I’m at the gym, I need to get to the pain, because that’s when I actually grow. No, no, no. It goes both ways. And when you read a book, like, super pumped about the founding story of Uber, and you put yourself in Travis Kalanick’s shoes, or likewise with Richard Branson, or even Obama. I don’t care what people think about politics, but you put yourself in someone’s shoes like that and you realize we are capable of enduring so much more. And if you apply the same, you probably know David Goggins, but you callous the mind, your mind just gets so much more sort of stable as you get knocked over many times over. And it sounds so cliche, but it really is true. Those are great. Ben Ornstein: Yeah, I mean, those are big highlights of some, Super Pump is one of my favorite books ever. That’s a great one. And last question, do you have any hot takes regarding the fundraising process? Keith Corso: Hot takes, hot takes. Keith Corso: Hot takes is that I don’t have any, you know, I don’t have any crazy hot takes. Nothing that probably has not already been discussed on here. Sounds good. Ben Ornstein: No worries. Okay, thanks so much for the time. This has been amazing. I really appreciate it. Cool. Keith Corso: I’m excited to see what this what this turns into. Is it like a blog? Is it kind of like a paragraph in a newsletter? Or what’s the what’s the final form look like, Ben Ornstein: It’s going to be payment gated behind his his newsletter. And it’s going to be just a document. So document with like questions and answers. And yeah, we’ll, we’ll kind of send you like the final version when it’s done. But um, yeah, that’s, that’s pretty much it. Awesome. Keith Corso: And so you take the transcription, throw in a chat, GPT, have it summarized certain points, dump it in the newsletter, maybe, maybe not. Well, you know, it’s hilarious. Ben Ornstein: So we had we gave the we gave the document to the doula founder and he was like, yo, it’s like, what chat should be T prompt did you guys use? And Michael Houk goes, Ben, because I do it. Which was a great compliment to me. But yeah, so no, it’s basically just me kind of like reading the reading the transcript and kind of putting it in into the document for now. Yeah, Once if this scales, you know, we’ll apply some AI, but for now, just doing it pretty manually. But, um, yeah, no, it’s, it’s that, that’s pretty much it. That’s the process. Great. UNKNOWN_SPEAKER: Great. Keith Corso: Um, cool. All right. Well, I am a, I’m a call a text away. Hopefully I’ll see you out on the Island at some point soon. And, uh, thanks for having me on. Of course, man. Ben Ornstein: Is, is Matt still actively working at bus ride? Super. Keith Corso: He’s been doing great. Keith Corso: Yeah. Ben Ornstein: Yeah. Ben Ornstein: That’s all I wanted to know. Yeah. I’m glad he’s adding value. Keith Corso: Yeah, definitely, definitely. He’s had a good run. So I know it’s going to continue, but thank you again for doing this. Of course. Ben Ornstein: Thanks, man. Appreciate the time.