From Lawyer to $3B+ Founder: The Ironclad Story with Jason Boehmig

So the very first version of Ironclad was email, alias adminironcladai. And if you were doing a contract, you would CC that email address. It was just me doing all of the stuff. And we were like, well, eventually we'll make this AI. For now, it's just me. There were some funny moments in there where I had to get off Caltrain to respond in a timely manner. As Ironclad, that was obviously not scalable. So I think we realized that one pretty quickly. And AI was like, nowhere near being able to make that idea work.

The Library of Alexandria was an attempt to capture all human knowledge. Fire and war destroyed it. Today we try again. Welcome to the Library of Minds, where you'll learn the frameworks and mental models of the world's greatest thinkers. And when our conversation ends, yours begins. Each guest has created a digital mind on Delphi that you can talk to anytime, anywhere. I'm Dara Ledgevardian. Let's dive in.

Thank you.

Thank you for giving the idea and for coming. I think the way that we met was we were sitting next to each other at Ascent and Jess texted me, holy shit. The guy next to you is so impressive. You need to talk to him. He was an AI in 2014. But I think before we jump into some of the specific questions, is there anything. Talk us through your path in Ironclad just to set the stage for our conversation.

Yeah. Well, great to be here. I'm excited that you're doing the speaker series, and it's really an honor to be here with you guys. It's exciting to be in just this environment. I mean, you're really lucky to be here right now. And when I think about my journey at Ironclad, like, I really look back on this almost exact time as, like, some of my favorite memories of the company. I know there's lots of really hard stuff that you're going through, and there's lots of challenges with this time, but they're fun challenges at the end of the day, and I think you all look back on them really fondly. So my journey with Ironclad, I was a law firm associate. I didn't plan on starting a company, and I started basically doing automation hacks for myself at the law firm I was working at. Followed that train down, eventually kind of became this little bit of an expert at my firm on building productivity tools. Internally, I ran the evaluation of IBM Watson, which, if you guys remember that, like, Watson won Jeopardy, I think, in 2013, maybe. And so, like, it was the. There was a lot of enthusiasm about AI, which is how we got to the ironclad AI founding back in 2014. Quit my job, met my co founder, and I'm sure we'll like have a chance to talk about other parts of that journey, but that's kind of a little bit of like how I got started.

Yeah, yeah, yeah.

I think help set the stage.

Definitely. And I think there's also two interesting things that have happened recently. One is that you just stepped back from being CEO after 10 years. Yeah. And maybe talk about like, also just the explanation of what Ironclad is and like where you guys are right now in the journey of the company.

Yeah. So Ironclad is a contract lifecycle management platform, clm. And what that means is we help businesses of scale with the whole life cycle of their business contract. So everything from like the idea that a salesperson wants to enter into a relationship with a customer, or that the company wants to hire an employee, or that the company wants to buy a piece of software, all of those are kind of like ideas that result in contracts. And. And we help those people turn that into the right template, the right approval chain, the right signature process and logistics. And then we track all of the data in those contracts at the end of the day, so that when someone needs to act on the information in a contract, they've got it in the system that they need to take that action in, or they can easily pull it up so that they can find it. And you know, like, that's important for a company like you guys. But imagine some of our customers like L' Oreal or MasterCard or Heineken, that are running global supply chains and have millions of contracts, like it's essential for them. So that's kind of like what Ironclad does. And we have AI sprinkled on top of that. From everything that helps with contract redlines and like the diffs between versions of contracts, to extracting data from PDFs that might be like 30 years old in some cases.

That's a problem for our content extraction system is getting well structured data out of the data that people give us. I think one of the things that you said to me that made me realize, holy shit, this is how the scale of this problem is. You think about Walt Disney, think about the hotels and the people they hire for the amusement parks and everything, the TV shows. Imagine how many contracts there are. Like, how do you even know what you've agreed to? So I think that leads well into the thing that we were just talking about right before we Started, which was an interesting strategic decision that you guys made early on. And I think you even in a Instagram reel called this category expansion play recently. Could we talk through maybe some of the like how you arrived at this?

So the full unpacking of how we got to that. So CLM is a big category and I mentioned started with AI and just this kind of idea that hey, if Watson can win Jeopardy, Watson can probably help or technology like it, lawyers with all of the complexity of their work, long form text, dealing with complex information and like finding a fact in a large body of documents. So the very first version of Ironclad, which was like the truly hacked together version was email alias adminironcladai. And if you were doing a contract, you would CC that email address. So you'd be like, hey Sam, I want to do an NDA with you. I've cc'd Ironclad on this email transaction and the system will help us get the NDA in place. And Ironclad, which was actually me, Ironclad AI would be like, hello Sam, we need the following information from you to do the NDA. And then you would get like this DocuSign request and I would fill in the template and it was just me doing all of the stuff. And we were like, well, eventually we'll make this AI. For now it's just me. And there were some funny moments in there where I had to get off the train caltrain to respond in a timely manner as Ironclad to do contracts get back on the train. That was obviously not scalable. So I think we realized that one pretty quickly. And AI was nowhere near being able to make that idea work. But we realized like, well, the thing doesn't need to be on an email thread. Actually people would probably prefer to use an interface here, especially at scale where they can click in and they can fill out some information and then Ironclad will fill in the template, right? And then when Ironclad is ready to get signature sent out, like we know that right order to send them in. And since we filled out the template and we collected all the signatures, we actually know a bunch of metadata about the contract anyways without even doing any data extraction. So like we can start tagging some things. So basically the, the initial version of Ironclad was really good contract workflows and contract workflows wasn't really a category. I mean we could sell it. Like I would, I would go to Dropbox and I would say, hey, what contracts do you guys not like doing over and over again that are really repetitive. And they would say, well, our NDA, yeah, we'll pay you 500 bucks a month to get an NDA workflow. We'll pay you 1000 bucks a month to do a sales contract workflow that our sales contract people could do. So we were kind of just like slinging contract workflows to anyone that would buy them. It wasn't really a category. We would often have to explain what we do. There was enough of a problem there that people would buy it though, and pay us at least some amount of money. And then I remember getting an email. We had HelloIronCloud AI on our website. And I remember getting a literal one line email one day that was, hello, are you a clm? And I had not heard of CLM before. And I almost deleted this email. It's actually crazy to think about what would have happened if I deleted this email because it was so influential in our company trajectory. And I Google, what is CLM Contract lifecycle management? And it basically describes a database for keeping track of your business's contracts. And I'm like, well, we don't have a database. I mean, we have all these contract workflows that we've sold. We do have some information that we could pretty easily use to populate a database. And then after I googled it, figured out what it was, I was like, let me see who sent this email. And it was apigee.com, which was like a pretty small cap public company. Google has since bought them. And I was like, okay, well this is from a public company that wants something called clm. And it like wants it bad enough where they're emailing us who has like a really crappy website one page up that's very vague and asking us if we're a clm. So of course I responded, yes, we are definitely a clm. Would you like a demo? And we booked a demo for like that Friday or something. And then I told my co founder, I was like, hey, you're going to need to code up a database. He's like, dude, what are you doing? Why are we doing this? I have to take the train down to San Jose. And I was like, it's okay, you can just code the database on the train. We'll do the demo, we'll see if they like it and I'm sure we'll be fine here. So we take the train down, he codes up the demo on the train, we do the demo, and the person is like, wow, I've evaluated 25 different CLMs. I've tried to find everything I possibly can. I love this because you guys have contract workflows and everyone else has really bad workflows or they don't have them. So we eventually go through this process as a really small company, get this account as a publicly traded company, and all of a sudden we're a clm. So that's like the in the weeds answer. But maybe some relevancies in there of to how we got from AI to workflows to now our category.

Yeah.

And that took about two years.

I mean, the thing that happened. So when you were like, when we sat down, we started talking about this, one of the first things you said to me was, you guys should think about positioning yourself as a CRM.

Yeah.

And I just had this instinctive reaction like, CRM, we're not a CRM. And then he told me this story about how it was kind of the same where you're like, we're not a clm. We're so much more than a clm. But for some of these people and a lot of customers, you have to bring them along the journey. And so you have to put it in terms that they understand.

So like, CLM really was just database software then. Which is why we had the same reaction that you had to me saying CRM is we're like, oh my gosh, this is like super clunky database software. No, we're not. That. That is really lame. And we are so much better. And we will eventually disrupt that. But what we realized from that publicly traded company suggesting the term to us was it did open the door like one. The customer wants to buy a clm. You don't need to explain to them that they don't want to buy a clm, they want to buy a clm. And just saying yes to that allowed us to opt into so many. Before we had to create the demand almost for contract workflows. And people didn't know that they really had a contract workflows problem. When you showed them solution, they were like, oh, I can use that. But now it was like there was hundreds and thousands of people out there looking for the CLM to buy. And we could go in and say, hey, we're clm. Check out this, like everybody. And we actually use this position where like, everyone has a database, not everyone has contract workflows. And our database for many years was like truly bare bones. And I would say worse than other CLMs, which is the main feature of the category before we started competing in it and we have now shifted what a CLM is to be contract workflows. Like in 2025, you could not win a CLM deal unless you have contract workflows, which we remain the best at. But it really did shift the market and kind of expand the market to a whole new set of features that weren't considered part of the category before.

That's such an interesting progression of 10 years where at first it's just a side feature and then you just become so good at it that in 10 years people expect that.

Yeah. And I really think there's something to like. In some ways it's like bundling. So when you bundle workflows with a repository, like where those things live after the workflow, the sum total is greater than the individual parts. And I do think with AI there's a lot of power to that general bundling strategy.

Yeah. I think this leads well into the next topic, which is another parallel between Ironclad and Delphi is the fact that trust is such a foundational component of do I trust you to do all of my contract management? And same for Delphi, put all of my content into Delphi. I want to feel as if it's a trustworthy platform. And so how have you. What has been your thought process or prioritization framework heuristic for trying to balance time to market speed? Do things quickly, but we cannot violate customer trust.

Yeah, I think it's really finding a balance on a lot of different factors. I mean obviously there's like the startup truism that you move fast and break things, which is up on posters and walls and you can't move fast and break things. In the legal industry in particular, you have to kind of move fast and not break things. So we invested really early on in quality engineering is like one technical decision that we made. So actually I think our second hire, maybe our first hire outside the co founders was a quality engineer and she was a really early. Actually she was the first quality engineer hired at Palantir and she basically her superpower is breaking things. So she like once famously got on an airplane and started putting in stuff on the in flight entertainment system and broke the entire flights in flight entertainment system. She just has the mind of she's like, I'm going to break whatever I'm looking at. And having someone like that internal to.

Where does she work right now?

She's still at Ark. Okay. Yeah. So. And that's what she does. She's like, how can I break this before our customer breaks it? And she'll kind of report that back. So she's actually kind of like the old school version of, of quality engineering. And we have other teams that will be. Are more like test writers. She is break the software.

Interesting.

That's kind of her full time job. So we did some stuff like that. I actually think this is maybe counter to some advice in Silicon Valley too. But like branding and naming was really powerful for us. Like Spring CM was a much larger company than Ironclad at the time. And would you, would you rather have your contracts in Spring CM or Ironclad?

Ironclad's cooler, right?

Yeah, like it feels safer, it feels more trustworthy. And so and then we, we oriented our brand like colors and everything around trust. And we looked at kind of the way trusted entities like banks and law firms brand and then we flipped that into a more modern context. But we used a lot of those colors, but like different tones of those colors. We built in some cultural stuff too early on. I'd say there's like a theme at Ironclad of we want to appear to our customers as if we're like a bigger company than we actually are. A funny anecdote around that was this Apogee company that was our first kind of enterprise customer. I think we signed them up when we were maybe a three person company. And then the company had grown a little bit as we continued to work with them. And the first, they closed their quarter as a publicly traded company doing all of their contracts on Ironclad. So like all of their sales contracts. And I remember they were so happy. They were like, hey, we want to do a happy hour with you guys. Like our clients. Global head of sales is flying in from New York and the whole sales team is going to be there. Like we're going to do an Ironclad and Apogee happy hour. We get there and I think the company's maybe five people at that point. And so our entire company is there and like talking to their salespeople. And you could just see it dawn on people at Apogee that like, oh my God, this is a five person company that we're working with. Like, they clearly thought that we had like hundreds of employees and stuff. And then they like, wait a second, you do all of the software engineering, you do all the quality engineering, you're the CEO. But we obviously they trusted our solution. There was enough in the way the product showed up, the way they had interacted with our team, the way we had handled ourselves and interacted with them that we were conveying Trust. And I do think that's important.

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Another thing that you emphasize heavily in some of our conversations is just the talent density of the early ironclad team as being so critical to success. And I'm wondering, you've had to interview so many people in 10 years. What has been or what is an interview question or questions that unintuitively give you a lot of signal.

My favorite one is I try to like subtly goad someone into complaining about a previous job that they've had. And if I basically, if I can get them to complain, then it's like instant failed the interview. Because I just feel like if you're gonna. And the people that are like gleefully, like some people will just gleefully go into complaining about their former job. I don't mind like a little bit like, yeah, that wasn't great, that's fine. But if I catch that they like complaining about their previous job, that's the instafil because like, it's a startup. Like, there are just going to be so many things you could complain about. And I kind of feel like this stage is you have to find the one thing that's working in the 99 things that aren't working. And so if you like complaining about stuff, you're going to focus on the 99. And what you actually want is people that are like, get really locked in when they start to see that one thing and they're going to make that one thing great and they're going to get excited about that and they're going to kind of be able to put on blinders on the 99 Things that Suck. So that's probably my one thread that I've carried through the years, the one that I picked up later, which I think is maybe it's more important later. But I've realized that I personally don't work that well with the negative way of saying this would be like people that are insecure about their ability and I and like need positive reinforcement about how they're doing. I. I think that's more of a personal chemistry thing of like, look, if you're doing a great job, I'm going to tell you you're doing a great job. But like, if you're just doing your job, I'm. Let's focus on winning. I'm not gonna like be negative, but it's just not who I. How I really show up that much. So I. I've kind of Learned that that is a. Isn't as good a fit for me personally.

How did you go about evaluating Dan, the new CEO?

Well, Dan, yeah. So our new CEO I. Someone I've known for a while because DocuSign's kind of an adjacent company to IronCloud. Like, we have a great integration and we're partners. And I just gotten him to a few touch points with him over the years and I'd always thought he was a really thoughtful person. Iron I. I love that you guys have this library here. Like, people at Ironclad love to read and talk about weird stuff. So, Dan, I remember the first interview that I in this role. He like threw off this Tolstoy quote from Anna Karena in his first interview, like offhand. And I was like, that's a really good fit with Ironclad. That's just kind of our culture. And so keeping an eye out for little things like that.

Yeah. And so sort of one of the unique things that as I was doing research for this, I found in a bunch of different things is the fact that you read poetry to the team. And so at the start of every year you read a poem.

Yeah.

And I'm wondering, is there any particular year or poem? Cause I imagine they're motivated by whatever's going on or a lesson that you want to convey. Is there a particularly memorable one?

Yeah. So my favorite poem is that I read to the company and is one of my favorite poems is Ozymandias by Shelley. And this has particularly special meaning to me. So I got really lucky. I did my. I know there's some Notre Dame people here. I did my undergrad at Wake Forest, which is in Winston Salem, N.C. and Winston Salem also happens to be where the late poet Maya Angelou retired. And she, in part of her retirement, she taught one course at Wake Forest every year or something. And I think there was 15 people in the class. And so you had to like lottery into this. And you know, I just remember being like, I was not interested in poetry at all. I thought it was dumb, but I was like, ah, I could potentially take a course from Maya Angelou. That's cool. I like throw my name in the lottery and for some reason I get a slot in this class. And it was like the definition of a life changing class. And I always remember the first day that she. She walks in and just before she says anything, she just recites in Latin this quote that translates. I am a human being, therefore nothing human can be foreign to me. And it was written by this Roman Poet Terence, who I think, like, went from being a slave to kind of like a literary fig figure in Rome. And the whole course was about unpacking this. This concept of no human experience can be foreign to you. And her way of having you experience things was through reading poems. So she would take someone who had grown up in North Carolina, had never left the state, and she would give them Robert Burns poem about like a red rose in Scotland. And she would have them, like, really try to inhabit the character of Robert Burns, like walking around a lake in Scotland, finding a red rose. Read it in a Scottish accent, like all of that stuff. And she would select a poem for everybody. The poem she selected for me was this poem, Ozymandias. The visual description of the poem is there's a traveler in an antique land, like, walking through the desert. And he comes across basically two legs of stone in the desert and a shattered face next to it. And he brushes away sand from the pedestal and the pedestal reads, my name is Ozymandias, king of kings. Look upon my works, ye mighty, and despair. And then the last line of the poem is, and the lone and level sands stretch far away. So basically there's like this shattered statue in the middle of the desert with this look upon my works, ye mighty in despair. And I read that poem to the company and I talked about, what does it mean to be a great company in the face of that truth, that our company will die, we will die. So what does a great company mean, knowing that it ends in, you know, just like that statue did. And I. I think the definition of a great company, which I talked to Ironclad about, is a company that changes the trajectory of an idea even after the company is gone.

So.

The two examples I gave at the time, which were Tesla for electric vehicles, like my garage of my apartment building over Covid went from like one electric car to basically being probably 95% electric cars. And Tesla changed the sort of definition and trajectory of electric vehicles. So I think Tesla is a successful company. I think that's an interesting way of thinking about, like, what a successful company is, that even if that company ceased to exist, the idea itself is different.

Yeah.

So a little bit of a long winded answer, but you asked me about a topic I'm passionate about.

No, that was fantastic. And I, I again see parallels where something that we're hopeful for is that Delphi is going to change your trajectory of what it means to capture and preserve and transfer knowledge.

Yeah. And I believe that. And I think the fact that, you know, that and can answer that is very unique. I appreciate it.

And so I think we just touched on a bunch of interesting formative experiences you had, you know, prior to the company. During the company. Has there been a value or a lesson from uppering your early career that you have realized has been critical and maybe one that you had to unlearn?

You know, I think, like, upon reflection, I think taste is really important and that's something we inadvertently got right in our early hiring and early team. Like taste. If you have taste, you're gonna make the lots of little decisions that you are gonna have to make on a daily and like hourly and even down to the minute basis. Like, so many little decisions that people at the company have to make and y' all are so consequential to the future trajectory of the company that like, little things you do now, you know that are not part of your job, but you just like take upon yourself to set up like the support ticketing system. Someone probably made a decision on that already and like, someone may regret. Yeah, but like, you know, like, you have to. And like the, the messaging that you put into the support ticketing system and like, what's the first message? What's the email like? There's just so many little things and you're gonna. Hiring people that have like some shared sense of taste is like, goes a really long way. And I can actually see that you guys do have taste. Like, the office is cool, but it's not too cool. Like it's. It's the appropriate. Like there's lots of tasteful things that have happened in getting this together. Like the idea library. That's so cool. I love that. And I think holding onto that and being intentional around the taste that you have and looking for that in future teammates is important. And that should be everyone at the company, in my opinion.

I love that answer. I feel you were early to that as well, because now everyone's talking about how taste is the only thing that's going to be around.

Oh, really? Cool. I actually didn't know that.

Yeah, this is a thing that people, the idea people on Twitter have been talking about recently, that in a world where execution is abundant with AI, the only thing that matters is taste.

Cool.

So there you go. AI in 2014 and taste in 2015.

Cool.

So I think maybe like one or two more questions and then we'll open it up to everyone here. I think one of the things that I'd also be curious here about is, and I think this goes in relation to taste and also Speed and trust at different threads we've been pulling on is sometimes you have to make difficult decisions about saying no to things. Yeah. And I'm wondering what has been maybe a memorable time where you had to say a very difficult no and what was the thought process?

We had to churn a lot of our early customers, which was really hard and it felt really risky at the time. Um, so basically the first contract workflows we ever made were for YC companies. So we kind of like coded together this system that it's still in use today. Hilariously, that is the system for YC companies to do safes. And we coded that up like a couple hours before demo day. And so like, that was kind of our first success as a business. Like, we just powered demo day after coding that and then we're like, okay, well like, we should do this for all YC companies. So we went out and signed up, like, I don't know, 300 yc companies doing like initial contract workflows. And that was exciting because like, we were month over month, growth was great. Like, usage was up. Our friends, like had organically used our product. But eventually we realized like one, actually a lot of YC companies go out of business. So like, your churn is relatively high. If you're signing up like the two person version of a company that might pivot their idea like six times. Like a lot of those go, go away. They're also super price sensitive. Like, we would have people like upset that we raised our price from like 100 bucks a month to like 125. And they're like, I'm churning, this is ridiculous. Because they're running on like ramen, you know, budgets and stuff. So we just realized like, this isn't a great business to be in, like selling 100 bucks a month to YC companies. Even though we, we are getting some growth on it, it feels kind of good. And so this was like we had this big tension between the couple businesses that we'd signed up that were enterprises like the Apogee, but we didn't have enough of them to like be confident that that would work yet. And then we had these hundreds of YC companies that were kind of like taking up most of our daily time. And so we had to kind of like shut that down. And it was painful and scary and it resulted in like, I think the only time in company history, which is a few months time where our like, revenue went down. So all of a sudden we went from this to like, this, and it was scary and I think it was scary for the team, it was scary for me. But we sort of like bridged that gap eventually and the new momentum came in. When we cleared, we said no and we cleared the space to work on the thing that ended up working.

Okay, so I think maybe we'll do rapid fire questions. I have four of them and then we'll open it up. So I think first, have you made a decision that seemed irrational to others, but in hindsight was actually right?

So working on legal was considered a small market. Like you know, ironclad 600 employees. I think there's five people on our legal team. So people investors were like, why are you going to do this? Like that's just not a large team. You know, we have hundreds of people in our go to market organization, our engineering organization and investors are like, why would you sell to the small team instead of the big team? And then furthermore, we decided we were going to focus on legal operations which like is one person. So at Ironclad 600 person company, one person. But being like really focused ended up helping us. That was longer and then a rapid fire thing.

You will miss the most about being CEO.

You have a lot of agency. I mean you, you like, you can change anything.

Even with a board.

Yeah, I mean it's like more so than. And I will. That's the thing I'm adjusting to the most where I'm like, oh, I can't say yes to that anymore. I need to like try to follow the process internally and be a good citizen. So I'm adjusting to that.

Favorite memory from Ironclad Series A. I.

Mean even if you remove the series A like the, that that's the thing I would say at the beginning, like I would go back to this time.

Yeah.

We had an office that this really reminds me of and we would just do fun stuff like this and like we would have law professors in and like they would talk about some legal concept to people at the company. And I think if you went around ironclad of people that were there at the time and asked, they would just pick a random day around this time of company.

Cool. And then the last one is. Why are you excited about Delphi?

Yeah, I mean I think you are going after a really big idea and I like that. Like you're going after something really big and. And if you're successful, which I really believe you will be, the world is different. And the in the concept of not like how we think about knowledge as human beings is different and changed. And I love the historical Reference in your name to that.

Awesome questions. Yeah.

First of all, thank you for coming. I agree with you. Today is a very exciting period to be in AI but you were able to build a business in a time before people turned irrational, before AI had so much hype.

Yeah.

Are there any lessons or principles they would like to share with deli? So we were able to like really find signal in all the noise that is going on today.

Yeah, I mean, this one sound, this one is going to be uncontroversial, but I just think it's worth hammering home because there are decisions that all of you can make that will increase the surface area of the company here, which is spending time with your customer. And like going back to the Maya Angelou thing of like deeply understanding your customer. I like, I, I would want to know for our early customers, like, what do they read? What does their day look like? You know, what's. Do they have a long commute to the office or a short commute to their office? Do they like working on their phone? Do they not like working on their phone? Like, when they're not at work? Like, what are their hobbies? I mean, we would just want to know everything about them and we would turn like nuggets from that into our pitches. Even, like, I remember our customer saying, like, you know, the most important thing for me is to like finish my work so I can go home and spend an hour with my kid before they go to bed. That became a big part of the ironclad pitch. Like, you can actually take some. And I love working on my phone. When I can ever, I can approve something on my phone, I love to do it. But the way that like PDFs display on my email client, I can't get them. All of a sudden we're going from, hey, save five minutes on a contract workflow to you can spend more time with your kid. Like, actually true. We got that from deeply understanding the customer and less of like, do you like this interface or this interface? And more like, what's your day look like? And I think everyone at the company can and should do that and pass that along. And the coolest thing about the stage, you can all talk to each other like you have a customer conversation. Great. You're going over the person that built that feature found this about you're going up to someone who's selling found this. And we are not going to do anything that's not scalable. But we are going to make sure that we deeply understand what they're doing and we're going to not have any rational reason for our competitor to go with that company. And there's been two or three moments where we kind of put to bed some competition there later stage form where.

You are, though, really grateful for you coming and talking to all of us today. Thank you.

It's been really fun. Thank you.

Thanks for tuning in for personalized advice from Jason. Head to Delphi AI and ask his digital mind.