The Exchanges

Q kick off with a little bit almost before the world of law, because you spent four years at Lehman's and I recently tweeted about how impressed I was by kind of a lot of, uh, maybe more traditional wall street bankers turned startup founders. My question to you is how do you think that first experience affected your operating mentality today, especially kind of having that now as a founder?

A Yeah. So I'm always a little embarrassed To have a Wall Street background, I think, because it's becoming a bit cliche in the Valley to have gone from Wall Street to Silicon Valley. However, it was an incredible experience for me. And I think for me, at least the mindset and the ability to manage your own psychology and truly think for yourself was something that I took out of that experience. I happened to be on the securitized products, sales and trading desk at Lehman Brothers, which was really quite central to a lot of the Ups and downs that that firm had and the markets in general had. And what I learned from that was as a junior member of the desk, I came in and I was so impressed by everyone at Lehman. I mean, Lehman had some incredible people. It had an incredible culture. There's a lot that I actually admire about that firm, but I came in and I really was almost unable to think for myself because I was so impressed by the backgrounds and the experience of the people that I was working with. And in hindsight, after going through that boom and bust cycle, I realized to That I sort of took everyone's word for what was going to happen. And that was, Hey, it's all going to be fine. We'll get through this. It's only going to be bad if we see a great depression level default. And I didn't do the intellectually rigorous work that I should have done to understand the actual mar…

AI assessment note: “ability to manage your own psychology and truly think for yourself was something that I took”

Q for sure when we focus on people, but I want to Let's start actually on the product itself today, because I spoke to a couple of your investors before the show, including Jesse, and he said, you have to dig in on their approach to product development. So kicking off with this, Jason, how do you think, and did you think in the approach product development in the early days?

A So I'm a big believer in this concept that there are just timelessly good business principles. And one of those timelessly good business principles is be as obsessed with your customer as you possibly can. And the way that that impacted our product development early on is we said, Hey, we're in the middle of Silicon Valley. We're sitting here at third and King street in Soma. And there are hundreds of thousands of companies in the world that we could work with. Let's be super intentional. And let's deliberately try to work with companies that we can literally walk to their office because maybe someday they'll let us come by for lunch, or maybe they'll let us look over their shoulder as they're actually doing some of their work. And so we actually set up with this goal to become the number one contract platform in Soma. And that was all we cared about. We just wanted to be the number one contract platform in Soma. And it That developed this really virtuous cycle where we would go out in the afternoon and watch one of our customers doing their actual contract work over their shoulder, and we could come back and sketch up a prototype of something that might help them, and we could take some of my legal knowledge and maybe tweak that prototype a little bit, and then we could, the next morning, meet someone for breakfast, and they would tell us about that, and we could actually get …

AI assessment note: “constraining ourselves to a really small geographic area, I think, helped us move a lot faster”

Q Can I ask, when someone's credible and very nice, so if Toby's the absolutely stellar profile, as you mentioned there, but if someone's, say, maybe a rung below or two, and they're credible and very nice, how do you determine whether to pull the trigger or not, and what does that determination process look like to you?

A Yeah. I think what we look for is someone described Ironclad culture to me once as laid back intense. And I think those are the people who really excel at Ironclad where they're really laid back. They're really nice on the surface, but there is a hunger and intensity underlying that. And you can very quickly when you work with someone establish whether that exists regardless of pedigree. So, you know, we have folks like Toby with the Oxford Harvard pedigree, our First marketing person came from Harvard Law School, could also work anywhere, and she had spent some time at Palantir. But, you know, when we look at employee six, who joined right after Toby, doesn't have a college degree, started doing data entry for us for, I think, 10 bucks an hour, and was so thoughtful and humble and motivated and competent at doing that, that we just kept giving her more work. Now she is running our entire support function at the company, and Has just been this incredible cultural leader. So I think I'm a big believer in letting people show and prove the caliber of their work. And if you can do that in the early days through consulting agreements, or just kind of bringing some folks in and letting them prove themselves, I think that's a worthwhile thing to do too.

AI assessment note: “letting people show and prove the caliber of their work. And if you can do that in the early days through consulting agreements”

Q kick off with a little bit almost before the world of law, because you spent four years at Lehman's and I recently tweeted about how impressed I was by kind of a lot of, uh, maybe more traditional wall street bankers turned startup founders. My question to you is how do you think that first experience affected your operating mentality today, especially kind of having that now as a founder?

A Yeah. So I'm always a little embarrassed To have a Wall Street background, I think, because it's becoming a bit cliche in the Valley to have gone from Wall Street to Silicon Valley. However, it was an incredible experience for me. And I think for me, at least the mindset and the ability to manage your own psychology and truly think for yourself was something that I took out of that experience. I happened to be on the securitized products, sales and trading desk at Lehman Brothers, which was really quite central to a lot of the Ups and downs that that firm had and the markets in general had. And what I learned from that was as a junior member of the desk, I came in and I was so impressed by everyone at Lehman. I mean, Lehman had some incredible people. It had an incredible culture. There's a lot that I actually admire about that firm, but I came in and I really was almost unable to think for myself because I was so impressed by the backgrounds and the experience of the people that I was working with. And in hindsight, after going through that boom and bust cycle, I realized to That I sort of took everyone's word for what was going to happen. And that was, Hey, it's all going to be fine. We'll get through this. It's only going to be bad if we see a great depression level default. And I didn't do the intellectually rigorous work that I should have done to understand the actual mar…

AI assessment note: “mindset and the ability to manage your own psychology and truly think for yourself”

Q Can I ask, when someone's credible and very nice, so if Toby's the absolutely stellar profile, as you mentioned there, but if someone's, say, maybe a rung below or two, and they're credible and very nice, how do you determine whether to pull the trigger or not, and what does that determination process look like to you?

A Yeah. I think what we look for is someone described Ironclad culture to me once as laid back intense. And I think those are the people who really excel at Ironclad where they're really laid back. They're really nice on the surface, but there is a hunger and intensity underlying that. And you can very quickly when you work with someone establish whether that exists regardless of pedigree. So, you know, we have folks like Toby with the Oxford Harvard pedigree, our First marketing person came from Harvard Law School, could also work anywhere, and she had spent some time at Palantir. But, you know, when we look at employee six, who joined right after Toby, doesn't have a college degree, started doing data entry for us for, I think, 10 bucks an hour, and was so thoughtful and humble and motivated and competent at doing that, that we just kept giving her more work. Now she is running our entire support function at the company, and Has just been this incredible cultural leader. So I think I'm a big believer in letting people show and prove the caliber of their work. And if you can do that in the early days through consulting agreements, or just kind of bringing some folks in and letting them prove themselves, I think that's a worthwhile thing to do too.

AI assessment note: “I'm a big believer in letting people show and prove the caliber of their work.”

Q and from your personal experience, and it's twofold. And it's, there's a lot of discussion around VC value add. And so on both sides of the table, one, what value have you found that VCs can bring? And then on the second is kind of conversely, what value do many founders think VCs bring that they actually don't? Let's start with the positive and then move to the less positive.

A Yeah. And I do think tying into our earlier question too, I do think that the value that VCs can bring pre-investment is a great way to test that Relationship and see how helpful people actually are. We recently did our series C round with Y Combinator continuity fund, and we've obviously known Y Combinator for years now at this point, but Ollie was so incredibly helpful with thoughtfully picking out some right customer intros and helping guide us through that process. There's one really large company that we've been trying to get into, and it's kind of our dream account. And he had a relationship with one of their subsidiaries. Made a very thoughtful intro. And I think it was really helpful for both parties because he was able to, as he was getting up to speed with the space, have the back conversation with his contact and say, Hey, how was that really? Like, you know, why are you interested in Ironclad? And was able to, I think, really gain some understanding about our space from having a conversation with this potential customer. We closed a deal in a pretty quick deal cycle off of that intro. So it really was this very win-win scenario where we got an intro we wouldn't have gotten. We closed a deal off of it. And he was able to sort of get some information from that process by talking with his contact. So I think that's a really great place to start is just a few customer i…

AI assessment note: “Ollie was so incredibly helpful with thoughtfully picking out some right customer intros”

Q for sure when we focus on people, but I want to Let's start actually on the product itself today, because I spoke to a couple of your investors before the show, including Jesse, and he said, you have to dig in on their approach to product development. So kicking off with this, Jason, how do you think, and did you think in the approach product development in the early days?

A So I'm a big believer in this concept that there are just timelessly good business principles. And one of those timelessly good business principles is be as obsessed with your customer as you possibly can. And the way that that impacted our product development early on is we said, Hey, we're in the middle of Silicon Valley. We're sitting here at third and King street in Soma. And there are hundreds of thousands of companies in the world that we could work with. Let's be super intentional. And let's deliberately try to work with companies that we can literally walk to their office because maybe someday they'll let us come by for lunch, or maybe they'll let us look over their shoulder as they're actually doing some of their work. And so we actually set up with this goal to become the number one contract platform in Soma. And that was all we cared about. We just wanted to be the number one contract platform in Soma. And it That developed this really virtuous cycle where we would go out in the afternoon and watch one of our customers doing their actual contract work over their shoulder, and we could come back and sketch up a prototype of something that might help them, and we could take some of my legal knowledge and maybe tweak that prototype a little bit, and then we could, the next morning, meet someone for breakfast, and they would tell us about that, and we could actually get …

AI assessment note: “the way that that impacted our product development early on is we said”

Q hope it's, uh, not too, how would I say, uh, conflicting, uh, conflictive, whatever the word is, a question. But how do you think about customer diversification? We see a lot of companies now selling to, I mean, purely almost tech Cohorts of clients. How do you think about that in regard to potential macro downturns, and how do you think about that customer diversification with macro concerns as well?

A Yeah, I mean, I think that is a concerning thing for a lot of tech companies. We certainly, our early customer base was heavily tech. One of the things we have always been excited about with Iron Cloud is that every company in the world is a contracts company, and we did see some very early adoption in the Fortune 25 person company. And I actually think that's a unique thing about contracts is if you look at the legal team at Dropbox, and you look at the legal team at L'Oreal, and you look at the legal team at some of these professional sports teams that we work with, they're all very similar. Like the folks went to the same schools, they are fundamentally dealing with the same problem that contracts are slow to make and difficult to keep track of. And I do think that's an area where we've gotten Lucky focusing on the legal vertical. There's so many commonalities outside of tech that it's actually pretty easy to jump over that gap. Whereas some other companies have a hard time because the sales team at Dropbox looks completely different than the sales team at L'Oreal and the sales team at a major league baseball team. So you really have to actually do some significant product works to jump over those gaps. But for iron cloud, it's been relatively easy to get outside of tech. And I'll actually say that I'm excited for For a recession or a downturn, because legal is a extremely c…

AI assessment note: “it's been relatively easy to get outside of tech... legal is a extremely counter cyclical”

Q and from your personal experience, and it's twofold. And it's, there's a lot of discussion around VC value add. And so on both sides of the table, one, what value have you found that VCs can bring? And then on the second is kind of conversely, what value do many founders think VCs bring that they actually don't? Let's start with the positive and then move to the less positive.

A Yeah. And I do think tying into our earlier question too, I do think that the value that VCs can bring pre-investment is a great way to test that Relationship and see how helpful people actually are. We recently did our series C round with Y Combinator continuity fund, and we've obviously known Y Combinator for years now at this point, but Ollie was so incredibly helpful with thoughtfully picking out some right customer intros and helping guide us through that process. There's one really large company that we've been trying to get into, and it's kind of our dream account. And he had a relationship with one of their subsidiaries. Made a very thoughtful intro. And I think it was really helpful for both parties because he was able to, as he was getting up to speed with the space, have the back conversation with his contact and say, Hey, how was that really? Like, you know, why are you interested in Ironclad? And was able to, I think, really gain some understanding about our space from having a conversation with this potential customer. We closed a deal in a pretty quick deal cycle off of that intro. So it really was this very win-win scenario where we got an intro we wouldn't have gotten. We closed a deal off of it. And he was able to sort of get some information from that process by talking with his contact. So I think that's a really great place to start is just a few customer i…

AI assessment note: “the value that VCs can bring pre-investment is a great way to test”

Q hope it's, uh, not too, how would I say, uh, conflicting, uh, conflictive, whatever the word is, a question. But how do you think about customer diversification? We see a lot of companies now selling to, I mean, purely almost tech Cohorts of clients. How do you think about that in regard to potential macro downturns, and how do you think about that customer diversification with macro concerns as well?

A Yeah, I mean, I think that is a concerning thing for a lot of tech companies. We certainly, our early customer base was heavily tech. One of the things we have always been excited about with Iron Cloud is that every company in the world is a contracts company, and we did see some very early adoption in the Fortune 25 person company. And I actually think that's a unique thing about contracts is if you look at the legal team at Dropbox, and you look at the legal team at L'Oreal, and you look at the legal team at some of these professional sports teams that we work with, they're all very similar. Like the folks went to the same schools, they are fundamentally dealing with the same problem that contracts are slow to make and difficult to keep track of. And I do think that's an area where we've gotten Lucky focusing on the legal vertical. There's so many commonalities outside of tech that it's actually pretty easy to jump over that gap. Whereas some other companies have a hard time because the sales team at Dropbox looks completely different than the sales team at L'Oreal and the sales team at a major league baseball team. So you really have to actually do some significant product works to jump over those gaps. But for iron cloud, it's been relatively easy to get outside of tech. And I'll actually say that I'm excited for For a recession or a downturn, because legal is a extremely c…

AI assessment note: “for iron cloud, it's been relatively easy to get outside of tech.”

Q Okay, so next step, we identify those incredible people, be it the Steves, be it the Jesses, be it the Jesses of the world. Once we get into kind of past that engagement and getting to know you phase and one has to negotiate, you're a former banker and lawyer. Tell me, what advice would you give on successfully negotiating with investors? Yeah.

A So if I'm talking to other founders, I would say don't discount the importance of the legal terms. So sometimes I'll see when I was a lawyer, I would see founders get in a little bit of trouble because they'd be in such a rush to sign a term sheet that they didn't really have a lawyer look it over. And even in the best intentioned negotiation, you can really accidentally get into something that's kind of a pain to unwind when you actually go to deal docs. So I would say like pause, take a deep breath, have a lawyer very quickly look it over. Spend some time getting a lawyer that you actually value their advice and you think approaches it the legal side of things the same way you approach the business side of things. So I'll make that my one piece of advice is lawyers are actually valuable and you should bring them in when appropriate and listen to their advice.

AI assessment note: “don't discount the importance of the legal terms”

Q I hear you're learning to be a DJ. Why? What do you get out of it?

A So one is just fun. I think it's important to have fun in life, and I love music, and playing music for friends is really fun. Hot take, though, DJ software is such a good analogy for what many of us are building in the valley, because my friend is a DJ in New York. He spent A decade or more learning how to DJ on vinyl and learning how to understand BPMs and beat match and DJ software. Now I can come in, I can load my music library. It will figure out all the BPMs for me. It will auto mix some of my stuff for me, although I try not to use that function. And so it's the power of software has enabled me to be a part-time competent DJ in a way that I also find fun to relate to the work that we're doing in building software for lawyers.

AI assessment note: “So one is just fun. I think it's important to have fun in life”

Q comfort. And actually some people do know what they're doing in certain things and you can learn from I'm intrigued with the independent thought and the importance of it. Would you agree with that statement of, you know, nobody knows what they're doing, carve out your own way? How do you think about that tweet from me? And would you join the haters in saying, no, Harry, you're talking BS?

A Well, I might do the classic lawyer thing and go a little bit middle ground on that. I agree with you in that there's definitely people that know what they're doing in their space. And I'm so impressed by founders that I see that really know what they're doing in their space. I worked with people on Wall Street that really know what they're doing in their space. But I also do firmly believe you have to find your own way. And you can't just, if you really want to truly do something new and innovative and push the envelope forward, you do have to find your own way and you have to find that thing that works for you. This is part of my own personal journey as a CEO is I don't think I'm a typical CEO. I'm kind of an introvert. I'm almost a little shy in many ways. And I don't think that I fit the classic mold of a CEO, but I've looked at other CEOs and I've been able to take I think inspiration from parts of what they do and find my own way. And I think it's only as I've committed to finding my own way, my own molding of these different traits together that I felt more confident in my own personal journey there. So I think it's a little bit of both. You have to respect what people have done and realize that they are doing a great job of it, but also not just try to fit into the cookie cutter.

AI assessment note: “I might do the classic lawyer thing and go a little bit middle ground”

Q I wish you could see my face. I'm totally smiling now. Both The really personal element that you mentioned there, but also the using fundraising for customer acquisition. Couldn't agree more than also, obviously for VCs, it's crucial as part of the diligence on the flip side, then conversely, where do you think founders think that VCs really help where maybe actually they don't?

A Yeah. I think it goes back to that intellectual rigor before is a VC can't make a critical business decision for you. And it seems like a failure to me just on first principles of a VC is driving a critical business decision for you. That means you, by definition, have not done the real, real work. They might agree with the decision you've made, but it really should be your decision. And sometimes I see particularly newer founders or younger founders almost be awed by the experience of the VC, particularly if they're coming from a relevant space to the product or something like that. And I just don't think that that ever works out well. You have to do it for yourself. Even if it's the wrong decision, it's got to come from within. And I think great VCs really understand that and are very careful to avoid that situation. But I also do see it happen in the market more than I would like.

AI assessment note: “a VC can't make a critical business decision for you”

Q I'm totally with you there. I do have one final question in terms of the developments I'm super passionate about increasing vulnerability and bringing one's whole self to work. How do you think about vulnerability as a leader and a CEO?

A I honestly think it's honesty and that there is no way that any founder who has not done this three or four times before can be a competent CEO scaling from seed to C and D and eventually IPO. And I think step one is just admitting that You need to hire and work with people who are so much better than you at every function. And part of the reason I think we've been able to attract incredible talent is just admitting that and letting go of the pretense that I'm a great sales leader, I'm a great customer success leader, I'm a great marketing leader. I'm not. I'm happy to be curious about it and hack together a solution and work harder than just about anyone else is willing to do. But what I really want for the company is As a whole is to get those great leaders in and to make them successful. And if you ask around, I think one thing we've really got a reputation for at Ironclad is an incredible leadership team, particularly as mapped to our scale. And I'd say that's one of the things I'm most proud of is getting those folks working together and on board on this interesting problem.

AI assessment note: “letting go of the pretense that I'm a great sales leader”

Q I'm totally with you there. I do have one final question in terms of the developments I'm super passionate about increasing vulnerability and bringing one's whole self to work. How do you think about vulnerability as a leader and a CEO?

A I honestly think it's honesty and that there is no way that any founder who has not done this three or four times before can be a competent CEO scaling from seed to C and D and eventually IPO. And I think step one is just admitting that You need to hire and work with people who are so much better than you at every function. And part of the reason I think we've been able to attract incredible talent is just admitting that and letting go of the pretense that I'm a great sales leader, I'm a great customer success leader, I'm a great marketing leader. I'm not. I'm happy to be curious about it and hack together a solution and work harder than just about anyone else is willing to do. But what I really want for the company is As a whole is to get those great leaders in and to make them successful. And if you ask around, I think one thing we've really got a reputation for at Ironclad is an incredible leadership team, particularly as mapped to our scale. And I'd say that's one of the things I'm most proud of is getting those folks working together and on board on this interesting problem.

AI assessment note: “admitting that and letting go of the pretense that I'm a great sales leader”

Q Okay, so next step, we identify those incredible people, be it the Steves, be it the Jesses, be it the Jesses of the world. Once we get into kind of past that engagement and getting to know you phase and one has to negotiate, you're a former banker and lawyer. Tell me, what advice would you give on successfully negotiating with investors? Yeah.

A So if I'm talking to other founders, I would say don't discount the importance of the legal terms. So sometimes I'll see when I was a lawyer, I would see founders get in a little bit of trouble because they'd be in such a rush to sign a term sheet that they didn't really have a lawyer look it over. And even in the best intentioned negotiation, you can really accidentally get into something that's kind of a pain to unwind when you actually go to deal docs. So I would say like pause, take a deep breath, have a lawyer very quickly look it over. Spend some time getting a lawyer that you actually value their advice and you think approaches it the legal side of things the same way you approach the business side of things. So I'll make that my one piece of advice is lawyers are actually valuable and you should bring them in when appropriate and listen to their advice.

AI assessment note: “I would say don't discount the importance of the legal terms.”

Q got Sequoia, you've got Excel, you've now got YC Continuity Fund. In the earlier days, when it really was the early days, did you ever have that And nerve around the investor base that you had around the table being as prestigious as it was also for getting IA there. Sorry. Did you ever feel that intense pressure just given the real status of the investors being so world class?

A I mean, it is on one hand. Yes, it's pretty amazing. And, you know, every time I kind of walk into the Excel Sequoia office and even saw Ironclad's logo kind of go up on the logo board at Excel the other week, And it's just like, oh my goodness, I can't even believe that that's happening. And it is extremely intimidating and awe-inspiring to work with people that have built billion dollar companies before. I also think going back to my Wall Street experience, I know that very smart people can be very wrong about big, important things. And I have appreciated the humility with which all of our investors have approached our business. And they've been very upfront of, we don't Understand this as well as you do, and we're going to figure it out together, and we're going to offer thoughts, but we're not an oracle. We really do need to do the work to figure it out together. So from that perspective, I've actually never felt any pressure from our investors to do something that we didn't think was right, or I've never felt psychologically swayed to change how we operate. I do think also kind of going through, you know, Jesse is incredibly Visionary, and I mean that in the true sense of the word, venture investor to have invested so early in Ironclad before many people saw the promise of what we were doing, but we did spend a couple years in such a backwater with so few people caring abo…

AI assessment note: “I've actually never felt any pressure from our investors to do something”

Q Really. And you know, you've built an incredible team and scaled an incredible team over the last few years with Ironclad. I do want to take it from the beginning. So with candidate pipe itself, like fundraising, it's all about top of funnel. And so in such a competitive, fierce war for talent, how do you engage in really keeping candidate pipe super full? Let's start from the beginning there.

A Yeah. I mean, this is a tough one. I think we're still always learning on this. I'm not sure there's a good way to do early stage startup recruiting. If I look at what worked for Ironclad, it's just, I have an incredible co-founder. So I'm sure you've heard of, since you've talked to some of our investors, Kai. Kai is two computer science degrees from MIT, like key engineer from Palantir. He's just an incredible person. And in addition to a highly competent engineer and product person. But when I look at our first employee, it was somebody that Kai worked with. And basically the calculus on her end was, I love working with Kai, and I don't even care what he's working on, even if it is this random legal idea. I want to be a part of it because I'm motivated by team. And if we look at our second employee, it was someone that I had worked with at a previous job, and we just got along great. And that teamwork vibe was the selling point there, as opposed to even the vision of the company at that point. So super hustly and network-based in the early days. And then I think we saw a snowball effect once we had a few of those Folks join. We also got lucky with, we were just talking about Toby at the beginning of our chat. Toby, Oxford, first class Oxford law degree, went to Harvard Law School, got his LLM, and could work at any law firm in the world, but sends me a cold email when we wer…

AI assessment note: “super hustly and network-based in the early days”

Q comfort. And actually some people do know what they're doing in certain things and you can learn from I'm intrigued with the independent thought and the importance of it. Would you agree with that statement of, you know, nobody knows what they're doing, carve out your own way? How do you think about that tweet from me? And would you join the haters in saying, no, Harry, you're talking BS?

A Well, I might do the classic lawyer thing and go a little bit middle ground on that. I agree with you in that there's definitely people that know what they're doing in their space. And I'm so impressed by founders that I see that really know what they're doing in their space. I worked with people on Wall Street that really know what they're doing in their space. But I also do firmly believe you have to find your own way. And you can't just, if you really want to truly do something new and innovative and push the envelope forward, you do have to find your own way and you have to find that thing that works for you. This is part of my own personal journey as a CEO is I don't think I'm a typical CEO. I'm kind of an introvert. I'm almost a little shy in many ways. And I don't think that I fit the classic mold of a CEO, but I've looked at other CEOs and I've been able to take I think inspiration from parts of what they do and find my own way. And I think it's only as I've committed to finding my own way, my own molding of these different traits together that I felt more confident in my own personal journey there. So I think it's a little bit of both. You have to respect what people have done and realize that they are doing a great job of it, but also not just try to fit into the cookie cutter.

AI assessment note: “I might do the classic lawyer thing and go a little bit middle ground on that.”

Q have now arrived at your destination. Jason, my word, it is such a pleasure to have you on the show. I've heard so many great things from Jesse at IA, and so I do want to kick off, though, with a little bit about you. So tell me, how did you make your way into the world of startups, and what was that founding story for you with Ironclad, Jason?

A Yeah, so for me, I've always been fascinated by the contract. So the contract is, I would say, the most important piece of business technology ever invented. It's been around since Two, 3000 BC. First record of human writing. First record of a human name. And it's kind of been this transformative technology for business. It's the first permanent verifiable record of a transaction that could be easily understood and shared with others in a way that they can understand. And I've always thought it's amazing that we're living in this world where we're still doing contracts like the middle ages. And it's so obvious to me that we're going to move that into a The digital age. And to get to play even a small part of how the contract looks in the digital age is really exciting to me. It's something I got turned on to a little bit when I worked at the law firm. And the more and more I investigated and deeper I got with it, the more exciting it is to just even play a small part in that transformation. And I think the cherry on top of that for me is if you solve this problem correctly, you also help one of the most Interesting professions in the world, the legal profession kind of return to what it's supposed to be doing and restore it to a good place. The legal profession has been in this crisis for the past couple of decades, really. And it's just getting worse year and year where you've…

AI assessment note: “something I got turned on to a little bit when I worked at the law firm”

Q scaling of you because, you know, when I challenged Toby, he was saying about just how humble and as you said, less of the chest thumping CEO that maybe we see in traditional media. I'm really intrigued. How have you seen the development of yourself as a CEO? And a question from actually a lot of your investors was how do you continue to evolve and grow as a leader?

A Yeah. I actually think it's kind of related to that curiosity I was talking about with How do we understand our customer problem better than anyone else? And I genuinely enjoy getting to know the intricacies of a legal ops person or a general counsel and even anything from what Instagram accounts are they following to what's the most annoying part of their morning to who do they interact with the most. That curiosity stuff is just really exciting to me. I found the same thing about, and my favorite part about being a CEO is you get to learn about every single function in your company. So I actually get to go As part of my job, have a conversation with our engineers about what technology stack we're using and why we might choose one of these pieces over the other. I get to go talk to our sales team, and I get to understand our go-to-market. I get to think about how our marketing team is going to reach out to our next batch of customers and how we're going to use our community events to really just provide value to our customer and then let them experience our brand very organically. So I love these just Connecting these dots between other areas that don't normally talk to each other. And I, as I've learned more and more about the CEO role, I do think that one flavor of a great CEO is one that takes all of these disparate parts of the company and makes sure that they're interacti…

AI assessment note: “my favorite part about being a CEO is you get to learn about every single function”

Q a few times there, and you know, they're part of that extended incredible leadership team also being the board itself. So I do want to touch on the fundraising and investor element slightly before we move into the final element being the quickfire round. So starting at the beginning of the process again, how do you think about relationship building with VCs, Jason, and what really works in your mind?

A Yeah, my whole philosophy on this has just been life is too short to work with people that you just don't really enjoy being around. And I kind of have used the venture process to discover wonderful, interesting people. And I would say Jess at Sequoia, Steve at Excel, Jesse at IA are just some of the people that I've been fortunate enough to run into. And they're incredible. I mean, these people, Steve built RelateIQ. I asked for an intro to Steve at the Series A round, specifically because I love asking people that I meet in Silicon Valley, what's the best company you've ever worked for and why? And I was amazed. I didn't have any connections to Steve in my network. I was amazed at the number of people I would run into that say RelateIQ. Hands down. Incredible culture. I remember talking to someone who said, just getting in, in the mornings and working at Related Q and having coffee with people is one of the fondest moments of my career because of the bonding and culture that that company had. And so I'm, as a curious person, I wanted to track down Steve and I just wanted to learn from him and to go into the room, meet him for the first time, happened to be around the time of raising our series A and not only get to learn from him on building culture, but have him want to partner with us on the next stage of the company. That's A incredibly fortunate result for us. So I think …

AI assessment note: “my whole philosophy on this has just been life is too short to work with people”

Q often speak to very young and often first-time founders, and when they're in that customer development, customer exploration phase, they actually don't often know the right way to dig into how to uncover customer needs and desires. What did your process look like? What were the core questions? Is it simply watching them? And how do you advise founders on the most effective way to understand what your customer needs?

A Yeah, I think it really does come down to just pure raw curiosity and wanting to understand that problem better than anyone else. Good example of this is for Ironclad. We were from the very early days focused on building a system for all contracts at companies. We didn't think that this was a technology that had existed in the market. And I'd say still don't see Anyone else really doing comprehensively every single contract type that exists for legal teams and limiting ourselves to a particular buyer, the legal team at a company, obviously it's a very collaborative buyer and that they need to collaborate with the rest of the company that they work in, in order to be successful, help that constraint. In addition to the geography constraint really helped us be specific and focus that curiosity into something that had that Compounding effect because we would talk to a lawyer at Dropbox, and that lawyer would tell us something, and then we could go validate that with a lawyer at Reddit, and then we could go validate that with a lawyer at Stripe. So I think putting ourselves within those constraints and being genuinely curious, it just takes care of so many wrong turns. I'm sure there are a million things we did wrong, and I may not even know all of them because I'm a lawyer and Wall Street person coming to technology, but just that ability to continually ask questions and do it in …

AI assessment note: “we would talk to a lawyer at Dropbox, and that lawyer would tell us something”

Q scaling of you because, you know, when I challenged Toby, he was saying about just how humble and as you said, less of the chest thumping CEO that maybe we see in traditional media. I'm really intrigued. How have you seen the development of yourself as a CEO? And a question from actually a lot of your investors was how do you continue to evolve and grow as a leader?

A Yeah. I actually think it's kind of related to that curiosity I was talking about with How do we understand our customer problem better than anyone else? And I genuinely enjoy getting to know the intricacies of a legal ops person or a general counsel and even anything from what Instagram accounts are they following to what's the most annoying part of their morning to who do they interact with the most. That curiosity stuff is just really exciting to me. I found the same thing about, and my favorite part about being a CEO is you get to learn about every single function in your company. So I actually get to go As part of my job, have a conversation with our engineers about what technology stack we're using and why we might choose one of these pieces over the other. I get to go talk to our sales team, and I get to understand our go-to-market. I get to think about how our marketing team is going to reach out to our next batch of customers and how we're going to use our community events to really just provide value to our customer and then let them experience our brand very organically. So I love these just Connecting these dots between other areas that don't normally talk to each other. And I, as I've learned more and more about the CEO role, I do think that one flavor of a great CEO is one that takes all of these disparate parts of the company and makes sure that they're interacti…

AI assessment note: “As I've learned more and more about the CEO role, I do think”

Q have now arrived at your destination. Jason, my word, it is such a pleasure to have you on the show. I've heard so many great things from Jesse at IA, and so I do want to kick off, though, with a little bit about you. So tell me, how did you make your way into the world of startups, and what was that founding story for you with Ironclad, Jason?

A Yeah, so for me, I've always been fascinated by the contract. So the contract is, I would say, the most important piece of business technology ever invented. It's been around since Two, 3000 BC. First record of human writing. First record of a human name. And it's kind of been this transformative technology for business. It's the first permanent verifiable record of a transaction that could be easily understood and shared with others in a way that they can understand. And I've always thought it's amazing that we're living in this world where we're still doing contracts like the middle ages. And it's so obvious to me that we're going to move that into a The digital age. And to get to play even a small part of how the contract looks in the digital age is really exciting to me. It's something I got turned on to a little bit when I worked at the law firm. And the more and more I investigated and deeper I got with it, the more exciting it is to just even play a small part in that transformation. And I think the cherry on top of that for me is if you solve this problem correctly, you also help one of the most Interesting professions in the world, the legal profession kind of return to what it's supposed to be doing and restore it to a good place. The legal profession has been in this crisis for the past couple of decades, really. And it's just getting worse year and year where you've…

AI assessment note: “It's something I got turned on to a little bit when I worked at the law firm.”

Q often speak to very young and often first-time founders, and when they're in that customer development, customer exploration phase, they actually don't often know the right way to dig into how to uncover customer needs and desires. What did your process look like? What were the core questions? Is it simply watching them? And how do you advise founders on the most effective way to understand what your customer needs?

A Yeah, I think it really does come down to just pure raw curiosity and wanting to understand that problem better than anyone else. Good example of this is for Ironclad. We were from the very early days focused on building a system for all contracts at companies. We didn't think that this was a technology that had existed in the market. And I'd say still don't see Anyone else really doing comprehensively every single contract type that exists for legal teams and limiting ourselves to a particular buyer, the legal team at a company, obviously it's a very collaborative buyer and that they need to collaborate with the rest of the company that they work in, in order to be successful, help that constraint. In addition to the geography constraint really helped us be specific and focus that curiosity into something that had that Compounding effect because we would talk to a lawyer at Dropbox, and that lawyer would tell us something, and then we could go validate that with a lawyer at Reddit, and then we could go validate that with a lawyer at Stripe. So I think putting ourselves within those constraints and being genuinely curious, it just takes care of so many wrong turns. I'm sure there are a million things we did wrong, and I may not even know all of them because I'm a lawyer and Wall Street person coming to technology, but just that ability to continually ask questions and do it in …

AI assessment note: “we would talk to a lawyer at Dropbox, and that lawyer would tell us something”

Q I always think about, which is how do you balance between when you release a new product, really getting enough time for the users to really get a feel for it, really kind of experience it, but then also the balance to know when it's not hitting and it's not getting the engagement and traction that it needs. How do you balance between that data versus gut in these decisions?

A I do think you got to get a little bit lucky on this one. We from very early on had like users effectively yelling at us to build new features. And I think anytime you get somebody who's frustrated with your product in the early days, that's an incredible thing to lean in on because it means there's so many things against you as an early stage company. You're small. No one wants to bet on a small company. You're unproven. No one wants to work with someone who might not be around in six months. And you just don't have the referenceable customers that all of your competition may have at that point. And so if you can find someone who's frustrated enough with your product to almost be mad at you and be frustrated that you don't have these things in it that they want, that's a great sign. And we had that from pretty early on. So I don't know how to, I don't know if I have good advice on how to get to the point of frustration with your user, but I know that you need to really lean in to early frustrated users because that's Where you can really turn them into champions, and where you really get the best possible source of information.

AI assessment note: “anytime you get somebody who's frustrated with your product in the early days”

Q I always think about, which is how do you balance between when you release a new product, really getting enough time for the users to really get a feel for it, really kind of experience it, but then also the balance to know when it's not hitting and it's not getting the engagement and traction that it needs. How do you balance between that data versus gut in these decisions?

A I do think you got to get a little bit lucky on this one. We from very early on had like users effectively yelling at us to build new features. And I think anytime you get somebody who's frustrated with your product in the early days, that's an incredible thing to lean in on because it means there's so many things against you as an early stage company. You're small. No one wants to bet on a small company. You're unproven. No one wants to work with someone who might not be around in six months. And you just don't have the referenceable customers that all of your competition may have at that point. And so if you can find someone who's frustrated enough with your product to almost be mad at you and be frustrated that you don't have these things in it that they want, that's a great sign. And we had that from pretty early on. So I don't know how to, I don't know if I have good advice on how to get to the point of frustration with your user, but I know that you need to really lean in to early frustrated users because that's Where you can really turn them into champions, and where you really get the best possible source of information.

AI assessment note: “I do think you got to get a little bit lucky on this one.”