Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring About this episode Jason Boehmig is the Founder & CEO @ Ironclad, the startup that provides powerful legal contracting for modern legal teams. To date, Jason has raised over $84m with Ironclad from some of the best in the business including Sequoia, Accel, Greylock, Emergence, IA Ventures, Semil Shah's Haystack and Ali Rowghani who led their recent $50m Series C from Y Combinator Continuity Fund. As for Jason, prior to founding Ironclad, he was both a corporate attorney with Fenwick & West and then also an adjunct professor of Law at the University of Notre Dame. In Today’s Episode You Will Learn: 1.) How Jason left the world of law and made his way into the world of startups and came to be founder of one of Silicon Valley's hottest startups, Ironclad? How did Jason's experience at Lehmann Brothers impact his operating mentality today as a founder? What were his big lessons on personal conviction from seeing Lehmann unravel? 2.) Ironclad is famed for their customer discovery process, so how does Jason think about product development in the early days? What core questions does Jason ask to understand customer needs and desires? How does Jason determine what to implement and what to prioritise? How does Jason think about the balance between data vs gut in product decision-making? What have been his lessons here? 3.) When it comes to hiring, how does Jason approach keeping top of funnel constantly full? Why does Jason believe that when hiring, "when there is doubt, there is no doubt"? What are the common reasons that Jason does not hire a potentially strong candidate? How does Jason determine between a stretch VP and a stretch too far? 4.) How does Jason think about relationship building with VCs? Where do so many founders make mistakes in this process? What advice does Jason have on successfully negotiating with VCs? What works? What does not? What value-add has Jason realised VCs really can and do provide? Where is there a suggestion that they do but rarely do? Items Mentioned In Today’s Show: Jason’s Fave Book: Meditations by Marcus Aurelius As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? You are listening to the 20 minute VC and Founders Friday with me, Harry Stebbings at H Stebbings 1996 with two Bs on Instagram and it'd be great to see you there. But to the show today, and I'd heard so many good things about this founder from many of his investors, and this episode could not have come at a more perfect time with the announcement of their Series C led by Ali Ralgani at Y C Continuity just a fortnight ago. And so with that, I'm delighted to welcome Jason Beaumig, founder and CEO at Ironclad, the startup that provides powerful legal contracting for modern legal teams. To date, Jason has raised over $84 million with Ironclad from some of the best in the business, including Sequoia, Excel, Greylock, Emergence, IA Ventures, Semel Char's Haystack, and then obviously Ali Ralgani, who led their recent $50 million Series C from Y C. As for Jason, prior to
0:43 Harry Stebbings? founding Ironclad, he was both a corporate attorney with Fennec and West, and then also an adjunct professor of law at the University of Notre Dame. I do also want to say a huge thank you both to Jesse at IA and Semel at Haystack for providing some fantastic question suggestions today. Mojito's on me for that, chaps. But before we dive into the show today, I have to talk about the company that's taken this ecosystem by storm, Brex, the company which built the corporate card for startups and who is the fastest company to reach unicorn status in history. Brex founders Henrique and Pedro built a payments business in Brazil but kept getting rejected for a corporate card in the States. So they built Brex with no personal liability, up to 20 times higher card limits, and huge rewards like 7x points on Uber and Lyft, 4x on Brex Travel, and 2x
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2:51 Harry Stebbings? Learn more today at dialpad.com. But brace yourselves, it's now time for the very special episode with Jason Beaumig, founder and CEO at Ironclad.
3:05 Speaker 01 You have now arrived at your destination.
3:08 Harry Stebbings? Jason, my word, it is such a pleasure to have you on the show today. 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?
3:22 Speaker 02 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 2000, 3000 B.C., 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 can 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 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.
4:07 Speaker 02 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 they'll cherry on top of that for 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 in year, where you've got people that are just incredibly unhappy in the job. And it's because they're stuck doing so much low level work that people outside the profession don't understand, that we can take that off their plates,
4:50 Speaker 02 restore them to giving the advisory council level work that they were intended to give. And so it's kind of this interesting mix of really important technology moving into the next generation, the digital age, and the restoration of a profession that I care a lot about to member of it.
5:09 Harry Stebbings? Do you know, Jason, I've done 2,800 episodes. I'm not sure I've ever heard anyone quite as passionate about contracts as you in all 2,800 episodes. So that's a first, but I do want to 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 a lot of that, 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.
5:38 Speaker 02 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 happen 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.
6:23 Speaker 02 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 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 market, the actual problem and the actual product that we were selling. And so I vowed to really never do that again. And I think some of that independent mindset helped me a lot in the early days of Ironclad,
7:05 Speaker 02 where a lot of people thought that what we were doing was the wrong approach. And a lot of people told us to not sell to the legal vertical. You know, these people haven't bought software before. They're not going to be the base for building a game-changing technology company. It's kind of a backwater. Don't do that. And we were able to independently go through the analysis and say, we think things have changed. We're going to have a viewpoint here and we're going to stick to it. We're willing to work years in the kind of silence and the zone where people aren't paying attention in order to see that bet play through. So I think that that kind of grit really was something that I got out of that Wall Street experience and going through that boom and bust cycle.
7:44 Harry Stebbings? It's super interesting to hear that grit and that kind of importance of independent thought. And off-schedule, so I apologize for this, but I tweeted and I actually got quite a lot of shit for it last night. I think the most annoying bit of advice that I hear is like, oh, no one knows what they're really doing. And to me, it just creates this false sense of comfort. And actually, some people do know what they're doing in certain things and you can learn from it. 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?
8:18 Speaker 02 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.
9:01 Speaker 02 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.
9:25 Harry Stebbings? I totally agree with you in terms of not fitting into the cookie cutter. And I really appreciate you sharing that on a personal journey. I do want to dig into that later for sure when we focus on people. But I want to start actually on the product itself today because I spoke to a couple of your masters 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 and approach product development in the early days?
9:48 Speaker 02 So I'm this 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.
10:30 Speaker 02 And 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 their feedback on something we just drew on a napkin the evening before. So that rapid iteration and actually constraining ourselves to a really small geographic area. I think helped us move a lot faster than companies that are trying to go on a much larger scope right from the beginning.
11:08 Harry Stebbings? Can I dig in and ask just, you know, I 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?
11:30 Speaker 02 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 in that they need to collaborate with the rest of the company that they work in in order to be successful.
12:07 Speaker 02 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 the 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 a pretty rapid way, I think overcame a lot of lack of experience that we had.
12:47 Harry Stebbings? Totally. I mean, one other element that is super interesting in terms of the mistakes, but you also said about the rapid iteration there. And it's super interesting for me because it's one that I always think about, which is how do you balance between when you release a new product, really getting a 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?
13:13 Speaker 02 I do think you've 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.
13:57 Speaker 02 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.
14:13 Harry Stebbings? Before we move into the people themselves behind the product, do you want one final question on, you mentioned the users there multiple times. In terms of your use, a lot of the companies that are loving the product are tech companies. So I'm interested, Jason, I hope it's not too, how would I say, conflicting, 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?
14:45 Speaker 02 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 500 when we were still a 25-person company. And I actually think that's a unique thing about contracts is if you look Look at the legal team at Dropbox and you look at the legal team at L'Oréal 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.
15:29 Speaker 02 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'Oréal and the sales team at a Major League Baseball team. So you really have to actually do some significant product work to jump over those gaps. But for Ironclad, it's been relatively easy to get outside of tech. And I'll actually say that I'm excited for a recession or a downturn because legal is an extremely countercyclical industry. And I think now that we've established ourselves as a market leader within our vertical, that we're going to see a lot of folks actually adopt this in a downturn.
16:12 Speaker 02 So I'm excited to see how Ironclad fares during, you know, the next cycle.
16:16 Harry Stebbings? Totally, absolutely. And I must commend myself for one of the world's shittest questions in that regard then. Thank you so much for taking that one apart. But I do want to dig into the people behind the product, 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.
16:45 Speaker 02 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 has 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.
17:29 Speaker 02 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 were still four people because he did a whole bunch of research on the contracting space and who might be the next generation of companies there.
18:12 Speaker 02 And just obviously you're going to take an intro when you get someone of that caliber reaching out. And so we've kind of assembled this band of misfits in the early days that attracted some other like minded misfit and went from there. But I don't know if I have advice, we're always trying to keep that can pipe more full than it is.
18:28 Harry Stebbings? 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 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?
18:45 Speaker 02 Yeah, I think what we look for is someone described Ironclad culture to me once as laid back and tense. 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.
19:30 Speaker 02 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.
19:58 Harry Stebbings? Jason, you said to me before, when there's doubt, there's no doubt. What did you mean by this and how does that apply to team building?
20:04 Speaker 02 Yeah, somebody, I don't remember who it was, but gave us that advice really early on and it is so true. If you have an iota of doubt in the hiring process and you feel like you could not be that disappointed if this person didn't join. Anytime that we haven't gotten to complete certainty, I think is a mistake. And you should almost be heartbroken if the person doesn't want to join your company. That's the level of conviction that we like to have in order to make someone an offer. And I still try to stick to that today, even when we're, you know, 125 people.
20:37 Harry Stebbings? Totally. I mean, in terms of the scaling of the team, but also you mentioned the scaling of employee number six. I do want to talk a little bit about the scaling of you because, you know, when I chatted to 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?
21:01 Speaker 02 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've 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.
21:45 Speaker 02 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 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 interacting, the right information is flowing and that all of the arrows are pointing in the same direction at the company. Because if you, as a CEO, can just move your company to be 5% more aligned,
22:29 Speaker 02 the more people you have behind that alignment, the more powerful it actually is. It's like helping to aim an arrow that's being fired. And that's a really exciting part of the job for me. So I kind of nerd out on that alignment and communication and empowerment across teams as opposed to being some sort of Jobsian character who's out there yelling at people and coming up with some visionary release on stage.
22:52 Harry Stebbings? I'm totally with you there. I do have one final question in terms of the developments. And it's, 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?
23:03 Speaker 02 I honestly think it's honesty in 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 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 or I'm a great customer success leader or 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.
23:45 Speaker 02 But what I really want for the company 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.
24:07 Harry Stebbings? We mentioned the investors quite 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 quick fire 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?
24:27 Speaker 02 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 Relate IQ. 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 run into that say Relate IQ, hands down.
25:09 Speaker 02 Incredible culture. I remember talking to someone who said, just getting in in the mornings and working at Relate IQ 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 it's, it's like tracking down people that are like-minded in their curiosity for developing great companies. Jess is kind of similar in that not an obvious fit for Ironclad, pretty consumer focused investor.
25:53 Speaker 02 But the more you get to know Jess, the more you get to know that the things she's passionate about are community and viral products. And delighting users through the product and those are all really ironclad things. So I really look at our board members as being parts of the team and putting just as much effort into hiring them as we do with a normal team member. So we've got this great board that hits a number of different strengths and diverse strengths across the members.
26:19 Harry Stebbings? 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?
26:36 Speaker 02 Yeah, 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
27:19 Speaker 02 should bring them in when appropriate and listen to their advice.
27:23 Harry Stebbings? I love that. Lawyers are actually valuable. The title of this episode. Knew I should have stayed at law school, Jason. I do want to ask one final question. It's all actually post deal 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.
27:50 Speaker 02 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 Ali 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
28:33 Speaker 02 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. It's just a few customer intros. It really doesn't hurt anyone to make those and it's a bad sign if your potential investor isn't willing to make them. That's one way to stress test. I also think just spending time, you know, you were talking about authenticity. I think
29:15 Speaker 02 like actually just drop the bullshit and spend some time actually getting to know the other person. I remember both with Jess and Steve, we kind of had more, a few sessions where it was just like, hey, we love the business, but we're not going to really talk about that. Like, who are you? And what's going on with you? And tell me more about you as a person, since we're going to work so deeply together over a very long time horizon. So I think it's totally worth pausing on that and spending some time there. And it's one of the values of getting to know people in advance of the round, because you can't really force that type of interaction or dialogue. You have to let it breathe a bit.
29:48 Harry Stebbings? 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?
30:05 Speaker 02 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. If 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
30:48 Speaker 02 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.
30:56 Harry Stebbings? Can I ask, and this is a little bit personal, so do say if it's too personal, but you know, as a first time founder, you've 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 awe 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?
31:22 Speaker 02 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 Iron Cloud'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
32:07 Speaker 02 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're doing. But we did spend a couple of years in such a backwater with so few people caring about what we were doing, that I also think it developed some conviction that once people actually come around.
32:46 Harry Stebbings? Listen, I love hearing about that early conviction from Jess. And that's awesome to hear in terms of kind of that unwavering nature from you and the team. I do want to move into my favorite element, Jason. So I want to move into the quick fire round. So I say a quick statement and then you hit me with your immediate thoughts. And you give me your thoughts in 60 seconds or less. Are you ready to be intense pressure?
33:04 Speaker 02 Hit me.
33:04 Harry Stebbings? Okay, favorite book and why? What must I read?
33:07 Speaker 02 Such a hard question because I'm reading all the time. I'm going to go with a book on my desk right now, Meditations, Marcus Aurelius. And the reason I like it is because it's a practitioner of philosophy. And it's just his raw notes as he's practicing philosophy. So there's no narrative. He's a stoic philosopher who also became an emperor of Rome. And it's literally his notebook. We're not even sure it was meant to be read by anyone. Sometimes it's indecipherable, but it shows you kind of the real behind the scenes work, almost like the 20 minute VC version of being a stoic philosopher and someone running an empire.
33:41 Harry Stebbings? Jason, please can I frame that statement? Marcus Aurelius and the 20 minute VC in the same statement is one hell of an interview. So I'll take that all day long. What advice do you know now that you wish you'd known in the beginning of your time with Ironclad?
33:53 Speaker 02 Spend a ridiculous amount of time hiring people. You really can't, I think I knew this at the beginning, but you can't know it enough is it's the most important thing that you do. The team will help you climb every single hill you encounter. And it is impossible to spend too much time building that team. We knew like our VP of Sales a year before he worked here. And I wish that I would have invested even more time getting to know people way in advance, years in advance of when we would actually want them to join Ironclad.
34:22 Harry Stebbings? I hear you're learning to be a DJ. Why? You get out of it.
34:26 Speaker 02 So what 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.
35:10 Harry Stebbings? I'm sure your friends in New York are absolutely thrilled that their 10 years of hard work has gone to such good use. But I do have to ask, the checklist manifesto, what did you take away from that?
35:19 Speaker 02 Arguably the inspiration for Ironclad. So the checklist manifesto, incredible book. I believe Ted introduced it to me when I was working at Fenwick. And if you can reduce routine work to a simple checklist and do the same thing each and every time, it's one of the best ways to have an impact in anything from surgical outcomes to legal transactions. And so what Ironclad does is actually puts a checklist for each and every transaction and make sure the same thing is happening the same way every time. And so Ironclad has always had a little checklist somewhere in the UI. And I think that that actually traces back to the checklist manifesto and reading that at Fenwick West.
35:57 Harry Stebbings? I love that pivotal nature. I do want to finish, though, Jason, on the next five years for you and for Ironclad. Paint that exciting picture for me.
36:04 Speaker 02 Yeah, so keep building, always keep our nose to the grindstone, keep being obsessed with the customer, keep the focus on hiring. And, you know, we want to become the most important vendor that our customers use. We want to be the central hub for business contracts across every company in the world. And we're going to keep making as much progress as we can towards that goal every week, every day, every minute. So keep it on the grind.
36:28 Harry Stebbings? Jason, as I said at the beginning, I had so many great things from so many of your investors. This really has been such a pleasure and a huge congrats once again on the very exciting YC news. That's fantastic to hear.
36:38 Speaker 02 Thanks so much, Harry. It's been a real pleasure to be on this podcast. I really appreciate what you're doing and the authenticity and genuineness which you're bringing to it. Appreciate you having me on.
36:49 Harry Stebbings? I have to say, I'm super excited for all Jason and the team are building with Ironclad. And if you'd like to see more from Jason, which is a must, then you can find him on Twitter at JBoemig. Likewise, it'd be great to welcome you behind the scenes here. You can do that on Instagram at HStubbings1996 with two Bs. Love to see you there. However, before we leave you today, I have to talk about the company that's taken this ecosystem by storm: Brex. The company which built the corporate card for startups and who is the fastest company to reach unicorn status in history. Brex founders Henrique and Pedro built a payments business in Brazil, but kept getting rejected for a corporate card in the States. So they built Brex with no personal liability, up to 20x higher card limits, and huge rewards like 7x points on Uber and Lyft, 4x on Brex Travel, and 2x on SaaS software. If you're
37:33 Harry Stebbings? a VC-backed startup based in the US, see if you qualify for a Brex card at brex.com and get card fees waived for life by entering the code HARRY during signup. And before Brex, the consumer experience for corporate cards was broken, and it's the same for bookkeeping. I doubt you started a business to track financial statements or make cash flow spreadsheets. However, now we have Pilot, and Pilot for bookkeeping gives you back the freedom to focus on your business. Every month, your dedicated account manager will send you an accurate, detailed financial report. Pilot does accrual basis bookkeeping in QuickBooks Online, so you're never locked into a proprietary platform. Plus, you'll work with the same person each month, so you can rely on them to become an expert in your business. With Pilot, you can say goodbye to exporting CSV files and emailing attachments to a bookkeeper
38:16 Harry Stebbings? you can never get a hold of. Get your company's books in order and get your time back. Check them out today at pilot.com/20vc. That's pilot.com/20vc. And we mentioned the crucial nature of keeping track of your financial position there, but the other crucial element is communication amongst your team, and that's where DialPad comes in. DialPad allows you to connect your team with a communications platform that powers voice, video, messages, and meetings across your existing devices. Plus, with DialPad Voice Intelligence, you can do more than just listen, and you can really unpack powerful, real-time insights into customer conversations. And that's why some of the world's most innovative companies use DialPad today, including the likes of Stripe, Uber, HubSpot, WeWork, and many more incredible companies. Learn more today at dialpad.com.
39:00 Harry Stebbings? As always, I cannot thank you enough for your support, and I can't wait to bring you another set of fantastic episodes next week.
Previous 20VC: Brad Feld on Why Market Size At Early Stage Is Not Helpful, His Biggest Learnings From The Boom & Bust of The Dot Com and How The Best VCs Work For Their CEOs Next 20VC: The Ultimate Episode For Emerging Managers: How To Determine How Big A Fund To Raise, What Is The Right Closing Strategy With LPs & Why We Will Not See The Eradication of Pre-Seed with John Fein, Founder & Managing Partner @ Firebrand Ventures Page updated September 29, 2026 · transcript and summary are machine-generated
