Episode Transcript
[00:00:00] Speaker A: Countdown.
Is we good?
[00:00:02] Speaker B: We're live.
[00:00:03] Speaker A: All right, well, hey, welcome back to the Gregory and Paul Show. I'm Gregory, everyone.
[00:00:09] Speaker B: Paul.
[00:00:10] Speaker A: And we always break down the Latest in startup SaaS, AI, whatever the Internet is debating this week. You know, we always aim for smart takes. And of course, I personally have lots of dumb ones and you always let me know.
We stream live on x LinkedIn roll late today, but that's okay.
We upload it to YouTube tonight where you can watch this episode, past episodes, clips. We're doing awesome on YouTube. And Paul, how's Spotify going?
[00:00:42] Speaker B: Spotify is great.
We're getting consistent listeners, getting everyone involved.
[00:00:48] Speaker A: Court, we've been promising to upload it on Spotify for like months.
Months and months and months. And we finally put up there and I think there's like five people that listen to it.
[00:00:56] Speaker C: Yeah, well, you got to start somewhere.
[00:00:58] Speaker B: Gotta start somewhere. Exactly. Soon we'll be number one.
[00:01:02] Speaker A: Awesome.
[00:01:02] Speaker B: Okay.
[00:01:03] Speaker A: And then of course, we have our guest who I. I wrote a nice little intro for you. So let me give you the formal Gregory and Paul show interview.
So, Court Lorenzini is an accomplished entrepreneur and investor based in Seattle, Washington, where I now live.
And he's best known for co founding DocuSign in 2003, which revolutionized signatures. So I think everyone out there is familiar with, with that company.
You have a long history of founding and leading innovative technology companies including Point.com, metabright, Primus, Bio Vision, and has served in leadership roles at various startups and venture capital firms. In 2024, he launched founder Nexus and I've been to one of your events, an invitation only community for venturescale founders aimed at improving the odds of startup success through mentorship and shared experience.
Lauren Zini is an active investor in 19 VC funds. Wow, that's. That's a lot.
And dozens of private companies around the world. And you serve on the board of directors at the United States Olympic and Paralympic foundation as an advisor and board member to over a dozen companies.
Welcome to the show.
[00:02:28] Speaker C: Hey guys, great to see you and thanks for having me on.
[00:02:31] Speaker A: Of course, of course. Why don't we just get started with the very beginning? We would love to hear the origin story and about how you started DocuSign. Like, our audience is mostly founders, entrepreneurs, tech enthusiasts, and I think they would all love to like, hear, hear about that.
[00:02:51] Speaker C: Well, let me. Let me start with sort of my how I started being a founder in the first place. I think that's an interesting place to start because I think it leads to what has become of my career. Ultimately, I now live in Seattle, but I grew up in the Bay Area and I had the great fortune that my father was a very prominent inventor and business person and entrepreneur at the dawn of Silicon Valley. In fact, he's been considered one of the founding fathers of Silicon Valley because he invented the commercial process for growing silicon.
And it was his company that provided all of the silicon to, you know, every startup that was building chips in the 60s and 70s and 80s.
And he was also one of the first venture capitalists. He was one of the, he helped start Band of Angels in the Bay Area.
And later in his career, he was even on the team that brought solar power to the planet. So he's, he's, he had an extraordinary career. And one of the things that I had the opportunity to observe is not only the fact that all of these other great founders, Gordon Moore and Jim, Jim Morgan and all these guys that were legends of Silicon Valley and still are to this day, Don Valentine, were just family friends to me. They were just people that I knew and vacationed with as parent, parental friends.
And so it was very clear to me that being a founder a was a path to success potentially, and that the people who were founders, the people who were these legendary CEOs were just, @ the end of the day, people that you could talk to and had life challenges and families and things going on that you could approach them on. So I was able to learn firsthand what it took to be potentially successful as a founder, entrepreneur.
And that led me to want to start my own company. So literally from the time I was 14 years old, my very first job, which was at an upholstery shop, I started a habit that carried on for the next 20 years of my life, which was taking notes, observational notes. I carried around those old college ruled notebooks. I don't know if you remember those, but I would carry one around with me pretty much all the time.
And it wasn't a journal so much as it was a place for me to observe the world, think about products, thinks about if I was doing a job working for somebody like, oh, if I had that, if that was my decision to make, or I had to handle that employee situation, or I had to launch that new capability or feature, Do I think they did it right? Would I have done it differently? And I would just keep these little running notebooks. All right, so years and years go by and every year I would make a habit of going back and twice a year reviewing every one of those notebooks from first to current.
And what that did over time was give me my lifetime of observations to scan through routinely, and to be able to then piece together different thought processes as my own understanding of the world evolved.
By the time it was time for me to go start my first company, I had this huge compendium of observed knowledge. And that served me tremendously well. But I did that from the time I was 14 through my mid-30s.
And a number of those things were things that ultimately became businesses or became ways that I approached building businesses and building teams, raising capital, you name it.
So it was always my life's journey to be a founder. And here's the other funny part is that I determine the concept of founder as being a unique discipline, meaning I never was trying to be a founder in an industry.
Meaning I always have said, if somebody said go be a founder of a toilet paper company, cool, I could have done that.
Because my love is the concept of founding and bringing new ideas and new energy to something.
So that was really where my passion has lied. And so my whole career has been around becoming a fantastic founder. First of all.
[00:07:09] Speaker A: Awesome. I had no idea. So that was like the Fairchild days and all that stuff, like the real origin of Silicon Valley. Yeah. If you don't know anything about it, you should go to Wikipedia and read up on the Fairchild stuff because it's an incredible, incredible story for people that are listening and don't really know about that. That's even like technically before my time. I know I'm older than I. Than I look, but I wasn't around for the, for the fair trial days.
[00:07:32] Speaker C: So. Yeah, awesome.
[00:07:33] Speaker A: Awesome. So, so, so okay, so you had this notebook full of all this crazy notes and all this cool stuff. So is that what inspired DocuSign or help us understand how you go from there to.
So what was.
[00:07:45] Speaker C: It? What was.
[00:07:46] Speaker A: The. The in. In. In a. In a. You know, in a nutshell, like how did you go from like that to.
To starting like a really significant tech.
[00:07:54] Speaker C: Company?
So DocuSign was my second startup, not my first.
And all I was first startup was a very early e Commerce play from 96 to 1, which I ended up selling.
One of the guys that worked for me at my first company, Tom Gonser, had gone off in the midst of all that and started his own company and approached me in 2003 and said, hey, my company has acquired, had acquired some intellectual property of a failed company here in Seattle and my board wants to sell it. I think there's some value I enjoyed working with you would you be willing to take a look with me and see if there's some value here.
So Tom and I said, so the original concept was Tom. So he approached me and then we sat down and looked at what his company had.
And from that we, I just determined that there was a trade name DocuSign was in, was in the pool of assets that he owned or his company owned, and a patent that had been issued on electronic signing via the Internet.
And so together we put our heads together and came up with the original business plan of DocuSign. And so I then acquired the asset from his company so that we could spin it out into something separate. And then he quit and came to join. And so that was our co founding team. And so they realized the value there was that we had an issued patent to start with and ultimately that became one of the key levers we used to fend off, you know, wannabe competitors in the early.
[00:09:35] Speaker A: Years.
Interesting.
[00:09:38] Speaker B: Interesting.
Was there, that's really cool. Is there, was there a point where you thought for, in order for us to grow bigger, you have to chase larger clients like enterprise? What did that like transition from early stage startups to enterprise look.
[00:09:55] Speaker C: Like?
So if you imagine DocuSign as a very horizontal tool, right. It can be used in pretty much any use case you can imagine. We had to be very thoughtful about not spreading ourselves too thin in terms of where we sold it. But in fact we went to market, selling to mid market companies mostly. And once we understood the business model we were pursuing, which was this concept of a virtual digital envelope that could then be repurposed and sent around the world, then the scale was obviously in the bigger companies, right? So you could, you could go and sell to SMBs and midsized, but you really couldn't get a tremendous amount of scale there quickly.
What happened though was that we were running up against, in the bigger companies, we were running up against the chief legal officer in every turn because even though there was federal law on the books that said that these were legal, there was no courtroom precedent. And if you imagine that a company adopting this at scale is basically saying, we trust that our most valuable documents, which are primary sales contracts are defensible, that if somebody were actually challenged them in court, that they would hold up. So it became a huge hurdle for us to get over the objection of the chief legal officer because the business people all loved it, right? The business people like, oh my God, this makes complete sense. We want to do this. How quickly can we adopt it? And the Clos were always the stopping Point. So what. What I believe was one of my better entrepreneurial moves at the time was in kind of in desperation, frankly, because we really. Having struggled to get over this, I went out and I hired a judge, a jury, and a prosecuting and defense attorney, and I found a case of prospective fraud, document fraud, that was tied to an insurance policy.
And I had that entire group of people retry the case as if the document had been signed, being docusign, and in the hopes that the outcome of that would be a favorable legal decision that, in fact, it was defensible in a courtroom.
What I got greatly exceeded what I asked for in that. In the end, not only did the case find the judge find in favor of the DocuSign document being defensible, he actually went farther and he wrote an opinion paper. And the opinion paper said, as a, you know, member of the judiciary, I have tried many of these cases. I've overseen many cases like this.
This was far and away the most proof positive, easy case to try because there was so much more evidence to support this signature than an ink signature or a fax signature.
And armed with that, I now had something to take to the clos and get them to relax, basically, and get out of the way, because really, CLOs are never going to help you. They're always, ever going to stand in your way. And it was just like, right now, guys, wait.
[00:13:04] Speaker A: Wait. I want to make.
[00:13:04] Speaker B: Sure.
[00:13:05] Speaker A: Wow. So how did. How did you. Like, how did you. I'm curious to understand the execution on this. Like, you found a judge. Like, how did you go about, like, recruiting these people? Just put an ad, like, on Craigslist. Like, it's fascinating. So I didn't realize you could do.
[00:13:19] Speaker C: That. Yeah, so, exactly. So I didn't either. And it was a matter of basically going out. And I hired a firm to help me corral the right people, is the short answer. So I don't know where they source them from. All I know is that I had, I believe the judge, I believe everybody was in the state of California, if I'm not.
[00:13:40] Speaker B: Mistaken.
[00:13:40] Speaker C: Okay.
So it was, you know, but it was tried in a courtroom setting based on the laws and of federal and state laws. Yeah, yeah, yeah. And that was just sort of the framework we provided. And so this was just done in their off hours when they could provide this. This service to us. And so we paid for everybody's time.
[00:13:59] Speaker A: And.
[00:14:00] Speaker C: Fascinating. That.
[00:14:01] Speaker A: Worked. Yeah. I mean, obviously, I could see why it's compelling. I didn't realize that this was a service, and I didn't realize that judges could do that either. I mean, I'm not. I'm not. Obviously I'm not a member of the bar, so I don't.
[00:14:12] Speaker B: Know. But.
[00:14:12] Speaker A: Yeah.
[00:14:13] Speaker B: Fascinating. Yeah. So that probably also means that no matter how good the product is, you couldn't really move ahead. You had to do this side.
[00:14:24] Speaker C: Piece. Yes. So. So I would point out. Super.
[00:14:27] Speaker A: Cool.
[00:14:28] Speaker C: Yeah. One, this was one of three critical things that.
[00:14:32] Speaker B: Happened.
[00:14:33] Speaker C: Okay. To launch the business. So I had to get over that one. That was a huge hurdle like that.
Without that having been done. No.
[00:14:39] Speaker B: Chance.
[00:14:40] Speaker C: Wow.
Second thing that happened is that by. No, by the good graces.
I don't know whether it's monthly or quarterly. Microsoft has a meeting in their executive briefing center where they bring representatives of various technology divisions within Microsoft to present to the executives latest and greatest progress, etc. We happen to be one of the very earliest adopters of. NET technology. That was the era in which. NET had been released.
Unbeknownst to us, the Net team came to the EBC that particular day and gave a presentation saying best in class worldwide use Case we can present to you is this company locally here in Seattle called DocuSign. They are really pushing the envelope. They are doing everything we would hope to be ever done in.
They're amazing, we love them, blah, blah, blah. They didn't tell us they were doing this. This was just some. The next thing I know, I'm getting a call, an inbound call from Kevin Harang, who is the deputy chief legal officer at Microsoft, working for Brad Smith who was the CLO at the time, saying, I just got out of the ebc. Turns out you're using our tech, we should be using you.
How do we become a customer? How does Microsoft become your customer now?
In 2003, Microsoft was the biggest, baddest gorilla in the jungle. There was no company even close to Microsoft in terms of corporate weight or influence in the world.
And the simple fact that they took us on as a customer and they started using sales contracts and other things with DocuSign combined with that legal opinion, by the way, those two things meant that the legal officers were now free to completely release and be like, great, if Microsoft can do it and it's. And there's a court case that we. Or even even a manufactured court case that demonstrates this is defensible were good.
The third leg of the stool which came in close succession was the national association of Realtors. And nar they go by, had a piece of software that they used to create documentation for buying and selling homes across the country. They had 3 million realtors associated with that platform. And we negotiated an embedded licensing arrangement where DocuSign became a button inside of their software.
And I let it be completely white labeled.
But the only thing I demanded was that the signature itself be branded. The signet, the stamp that was applied to the digital document said docusigned by person. Right.
And so what happened, that was the critical third leg, is that got millions of home buyers access to it. And anybody buying and selling a home is also employed somewhere.
They have a day job. And if their day job is also buying and selling things, they're like, my God, I just use this digital tool to buy the most valuable asset I will probably ever own. Personally, I probably could use this for my.
[00:17:53] Speaker B: Company.
You got the.
[00:17:55] Speaker C: Distribution.
That was our distribution moment. That was the moment when the country certainly woke up and said, damn, I can actually use this and what other use cases can I put this into? And that's what really those three things were.
[00:18:09] Speaker A: Catalytic. Oh my God. So, because it's funny, like I bought a. I bought actually more homes than I care to like think about. But we always wondered like, we'd always wonder like, why do they all use DocuSign? Like I remember like people asking me that question.
I hadn't realized that. Because like real estate, it's basically ubiquitous. Like that platform. Yep. In the industry. No matter who they are. Right. If they're not involved with like nar. Just independence, like even like signing. I was signing like documents like look at homes during COVID and just like the release forms and stuff.
[00:18:43] Speaker C: Everything. Yep, yep. So that was our. Those, those three things were really what catapulted the business forward. And once we had that. Getting back to your first question, that's what gave us the opportunity to sell to enterprises.
Because the. Once we could get out of the SMB's restricted market and get. And then start selling at scale where they could start buying in bulk.
And that's, that's what really made the hockey stick.
[00:19:08] Speaker A: Happen. Yeah. Yeah. So the credibility of those, those three things essentially. Or if there was just enough kind of momentum from all of.
[00:19:18] Speaker C: That. Yeah. And look, because we were working with mortgage companies and banks on the financing of these homes and other things, those documents were all getting sent around between financial institutions. The next thing we know, we're doing student loans, auto loans, all sorts of other bank related transactions that needed documents for backing them up for lending. And then that just. It kept expanding. The use cases kept expanding from.
[00:19:45] Speaker B: There.
Do you think looking back what was the first moment that you found product market fit?
Was it the.
[00:19:53] Speaker C: Realtor?
Yeah, the realtor. The realtor use case was by far. We leaned into. That was the biggest revenue producer for the company for years.
It was just such a breakthrough. And it took probably another four or five years for another business to come even close to producing the revenue that one was.
[00:20:10] Speaker B: Producing. Gotcha. So, okay, so next question is kind of, do you have any advice for the founder that's looking to go from the 0 to 1 snap into product market fit? Because I. I personally see that part of the business as being very creative. Like all of your stories, right. It's not formula. You can't just say, let's do this and follow this path. What's your. What's your best.
[00:20:34] Speaker C: Advice?
And I give this. These stories as examples, Paul, because the reality is you kind of have to be super creative and you're. You got it exactly.
[00:20:45] Speaker B: Right.
[00:20:46] Speaker C: That. Don't get stuck thinking that you have to follow a playbook. In fact, quite the opposite. You kind of need to break the rules. Or as I was saying to Greg, that, like, hey, who knew you could hire a judge and a jury and a set of attorneys for this kind of thing? Yeah, that was. It's still not common knowledge that that's even possible, so I had to kind of make it up and. But it was necessary. So I look at founders who can really think on their feet and try different approaches, and those are the ones I tend to like investing in.
[00:21:18] Speaker A: Myself.
Awesome. I mean, I. I hear that story too, and I think about, like, my experience at work, and I would say, like, you've got to be really optimistic because I can imagine, like, presenting that to people and everyone telling me, like, why it's not a smart idea to, like, do a mock.
Right.
I feel like the resistance just starts to emerge when you immediately, admittedly, immediately think of, like, trying to put that. That together.
[00:21:44] Speaker B: Right. Maybe it's like problem solving, right? Like, you're. You're always. You're always presented with problems, and you have to find creative ways to solve these problems. Would you say.
[00:21:52] Speaker C: That? I usually refer to it as adaptability, meaning the market will give you signals, and the best founders that I know adapt to the signals they're receiving as opposed to just bullheadedly moving forward on their own. Ideas usually ends badly if they're just pulling ahead without getting any kind of market signal. So for us, it was, you know, you search and you search and you try and find the signal, and then all of a sudden it's like, okay, now I got to lean in on the signal and I got to adapt to that signal and I don't want to stay tied to a particular way. I thought it was going to go, yeah, I'm going to adapt and move forward. And so that's something that's always certainly been a hallmark of my approach is most of the folks that have ever invested with me have, will tell you that that's something that, that they value about my.
[00:22:41] Speaker B: Approach.
Do you have any advice on the difference between conviction and.
[00:22:46] Speaker C: Adaptability?
You have to have a bit of both. And I think it's again, reading the signals.
I think there is a, there's stubbornness when you're avoiding this. You're either not getting signal and you're just pulling ahead, pushing ahead anyway, or there is just pure like, I'm not going to, I'm not going to listen to the signal. I know better than whatever signal I'm getting.
So, you know, you have to, there's, there's a fine line there. You kind of have to be convinced of your own approach.
You know, Steve Jobs always gets quoted about saying, hey, the customer doesn't actually know what they want.
And I often would agree with him. So I'm suggesting that it's not that the customer is always right, it's simply that you need to make sure that you're getting enough signal from whatever it is you're trying to validate your approach or invalidate it.
A number of different books, works, I studied this topic incessantly is how to be a good Founder. Talk about how to refine ideas over time and methodologies associated with that. And I'm, I think that's a great way to.
[00:23:57] Speaker A: Approach.
Awesome.
All right, if you were to like, you know, try to start DocuSign today, like what would you do? What would you do differently? And I'm sure, yeah, I'm sure you've got a bunch of ideas, but oh my.
[00:24:13] Speaker C: God. So the great news about today versus 2003 is that the tech stack is so much more accessible and inexpensive.
So if you were to do it now, you could do it with a tiny fraction of the capitalization because you wouldn't need the number of people, you wouldn't need the amount of compute.
Look, I mean in 2003, the DocuSign system is basically blockchain, before the blockchain was invented.
It's exactly the same fundamental technology. It's a server based point of truth that had that where the document itself is the token and you have to define the unassailable fact that there is a singular version of this document that everybody has accessed and talked, you know, interfaced with.
And we had to invent that. And by the way, back then there was no aws, there were no rental servers. You had to literally go build a data center from scratch. You had to go find a space, you had buy racks and put people and build all the backend infrastructure and all the support, all the network gear, everything that cost an enormous amount of capital and time and energy over the years. You could do that now at the push of a couple of buttons. And so look, I mean, it's so much simpler now. And I love the fact that today companies are getting started with just a small handful of people and yet reaching enormous both reach and revenue.
And that's the beauty of the modern tech tech stack is that you can get those economies of scale quickly without having to have a huge staff or a huge backend infrastructure that you're paying.
[00:25:49] Speaker A: For.
Yeah, that is an awesome point. Like I see that now. So I'm here in San Francisco and I was at a bunch of events this week and I remember even like 10 years ago you still needed like 10 person team, maybe a few million dollars to spin something up. So it was much further along than it was in the early 2000s. But now I meet people all the time. One person, two person, three person team with like a product that's in market and has revenue and is scaling and has significant amounts of revenue. Like a three person, a three person team. It's bonkers compared to like what it was even, even ten years.
[00:26:25] Speaker C: Ago? Oh yeah, I, I'd say even five years ago. It's, it's, it's really radically changed. Ten for sure. Yeah, ten for.
[00:26:32] Speaker A: Sure. Yeah.
It's exciting.
All right, let's move on here. So what are the most important lessons that you learned from that experience and what advice would you give to people today who are starting.
[00:26:49] Speaker C: Companies? Okay, so we talked about adaptability and I think adaptability comes from the hard won lesson that other people have experience in areas that you're going to go into. It's very rare, as I like to say, that an idea is typically been tried before by one or more people and if not in the exact same way you're trying it as an entrepreneur, but similar.
And one of the things I often encourage is go find the people who are your predecessors in a space and ask them to tell you what happened when they tried that similar idea was that if it succeeded or failed, normally you're talking to them after a failure. What failed? What are the, I call them the fatal flaws. What are the fatal flaws that drove you down?
And then as an entrepreneur, you absorb that information and your job in that moment is to not only bring your own product to market, but to have addressed all of the fatal flaws that cratered your competitor, your predecessors. Okay, so that is a piece of wisdom that I impart on.
[00:27:59] Speaker A: People.
[00:28:00] Speaker C: Now. I do that routinely. It is part of my methodology to try and do this fatal flaw analysis early.
The big takeaway for me though is ultimately what resulted in Founder Nexus, which is.
Or one of the big takeaways, which is the best guidance I got along my founder's journey.
I'm now at my fifth enterprise that I'm building.
The best guidance I ever received at every stage was from other venture backed founders who had experience, who had lived this, who had actually lived the thing I was doing in one form or another.
Conversely, the worst guidance, worst absolutely that I ever got came from my investors, advisors and board members who had not been founders themselves. Now I like that.
I love those people. They're my dearest friends and I would never throw any of them under the bus because they were giving me their best possible guidance.
The fact is that as executives at big companies, however they achieved their personal success to have been an investor in me or a board member or what have you, did not include being a startup founder. And therefore their journey to get to that space in life didn't include the having to make a decision in that instance. They'd witnessed it as other people making those decisions and therefore their guidance was based on those observations, but it wasn't their own personal discussion.
So, so the, the net of that was to say, how can I solve that problem?
How do I solve this problem? So Founder Nexus was the result of this, which is to say Founder Nexus is a global community of experienced venture backed founders who share experience with one another in order to increase their odds of.
[00:29:46] Speaker B: Success.
That's perfect.
[00:29:49] Speaker C: Yeah. So really that was a big takeaway from not just the docusign experience, but from all of my companies was that. And so where I sit today professionally is letting founders interface with one another and share those lived experiences to incrementally improve every single decision they make to multiply dramatically change their odds of.
[00:30:11] Speaker B: Success.
Okay, you've spoken about ideas of finding and identifying one's superpower. I really like that term. Could you tell us more about.
[00:30:22] Speaker C: That?
Yeah, Greg Paul, that actually came out of years of trying and failing as a hiring manager where I was trying to find the right people to build teams and build great teams, obviously. So what I had observed was that all the tools that are available to me as a hiring manager, strength finder and Myers Briggs, and behavioral interviewing, and you name it, there's every number of tool for trying to find the right fit failed to give me a significant enough insight to determine two things. Number one, was the person I'm interviewing going to be any good at the job they were going to be hired for?
And number two, how are they going to perform as a team member within the context of the broader organization?
So neither. None of the tools gave me that. So this thing I call superpower analysis was my own creation. It's been evolving for the past 30 years that I've been working to build it.
It's now been boiled down to a very succinct assessment process that I can put somebody through very quickly.
And its specific objective is it is not prescriptive.
I don't tell you what your superpower is.
We as a pair discussing it. We discover it together.
So I lead you on a path of discovery such that you ultimately fall on and understand and come to the understanding of what your native, innate superpower is. Once I understand an individual superpower, I can do the two things I need to do. I can understand what role and responsibility to assign them to, because if I give them a role that's directly aligned with their superpower, fundamentally, doesn't matter how much experience they've got, they're going to knock it out of the park. So this gave me an opportunity to identify diamonds in the rough people early in their career who didn't necessarily look on paper like they were going to shine yet in their career. But knowing their superpower, I could assign them a particular role and responsibility, and. And they always outperformed. So that was a huge unlock. Simultaneously, it gave me enough insight that if I did that for everybody that joined an enterprise, then I could see how pieces would fit together, because I could see not only where superpowers aligned, but also where they might clash and where there was duplication that could often be a problem, depending on how it's assigned. Also, every superpower has what I call a dark side, which is the negative aspects of your superpower and how those come to play out. And understanding the superpower also exposes the dark side, which then gives you language and means to address the disconnects and the natural things that happen in a team when somebody's annoying somebody else.
And so it really was a critical piece of building outstanding individual performance and outstanding.
[00:33:09] Speaker A: Teams.
What is the process like? I'm curious to understand a little bit more like yes questions like, yeah, process.
[00:33:17] Speaker C: Greg. Basically I walk people through a series of questions that I've developed which ultimately yields a thought process to get them to try to frame and think about what their superpower actually is or might be. And then there's a follow on process where they go through a discovery model that I build for them which then yields the.
[00:33:38] Speaker B: Outcome.
Do you find people understand what their superpowers are or do you look for.
[00:33:45] Speaker C: People?
No, no. In fact, it's been my experience over the, over the many years I've been doing this that if I say superpower analysis, somebody might say, oh, I know what my superpower is and they'll tell me. And it's. It's never, it's never correct. It's never.
I think one person in hundreds that I've done this interview with has active accurately understood it. And these are very thoughtful, creative career type.
[00:34:11] Speaker B: People.
[00:34:12] Speaker C: People. This is not just a bunch of young folks. This is very senior in their career folks.
So the beauty of this is that the discovery moment is almost always illuminating to the person and very freeing. Actually, the response I often get is, oh my God, I feel super now. I actually have this jolt of confidence and this idea that in that arena I'm going to naturally outperform everybody I know.
And, and then if you give me a problem that allows me to lead with my superpower, I am going to knock it out of the park. So there's this. It's also self reinforcing.
And then when you expose that to teammates, oh, super power, you know, teammate 1, 2, 3 has superpower ABC, then they can each lean on each other in different ways. And the way I often have used this from a leadership perspective is if a key business decision needs to be made, I will try. We as a team can talk about what is the superpower that would make the best choice in this for this type of decision. And then we let that person be the decider rather than by, by title. So it's not always the CEO that gets to decide just by, you know, their role.
It's whose superpower is more likely than others going to have the best instinct in terms of making this decision. They get to lead this decision and make.
[00:35:34] Speaker A: It.
Yeah.
How is this different from like strength finders and the Enneagram? I've done all of these Enneagram, Myers Briggs.
I'm just curious. I'm familiar with those. That's why? I'm just curious more than.
[00:35:47] Speaker C: Anything. So those are all prescriptive. You take those exams and they tell you what they think you.
[00:35:52] Speaker A: Are.
[00:35:53] Speaker C: Okay. Yeah.
I dare you to put that to use.
Knowing what you are doesn't help. There is no way for. Really, it's very little insight in my experience to be able to tell you to say if you're. Whatever you are, that you're going to be successful at the job I'm about to hand you.
Yeah. It just doesn't. I have not seen that to be effective, whereas my analysis does yield.
[00:36:22] Speaker B: That.
I think one thing that you said that's super interesting is the negative.
The. The dark part of the superpower. I think that's super interesting because most likely the superpower always comes with a dark side, which is.
[00:36:39] Speaker C: 100. 100 true. In fact, the way I say it is, once we are sort of honing in on the superpower, I will walk you through a process of understanding the dark.
[00:36:49] Speaker B: Side.
[00:36:50] Speaker C: Right. That will be a strong indicator that we've actually landed on the right.
[00:36:54] Speaker B: Superpower.
[00:36:54] Speaker C: Because. Because if the dark side is uncorrelated, we probably aren't there yet. So there is always a.
[00:37:01] Speaker B: Correlation. Yeah.
So, like, I'm thinking a lot about this, so I'm really good at early stage of the founding process, super creative work, but I'm terrible at operational things. Okay, so I.
[00:37:15] Speaker C: See. But those are.
So somewhere underneath that, those are what I would call the attributes of your.
[00:37:20] Speaker B: Superpower.
[00:37:21] Speaker C: Right. They would be. They would help us sort of hone in on the thinking rather than illustrative of your superpower in and of itself. So normally when I. When people think they know their superpower, they describe it as traits that they have learned or something that has evolved through resume or experience.
And I will tell you that what I have found is that it's not that at all. It's something that you were innately born with. It's something you've been exhibiting in your life from the time you were born.
And it might come out in professional ways, but it's not ever something that you were.
[00:37:55] Speaker B: Taught.
I see.
Okay, very interesting.
[00:38:02] Speaker A: Wow. Can you share with us what your superpower.
[00:38:05] Speaker C: Is? I can. Yes. So, yes. My is optimization means that I go through the. I cannot go through a minute of any day ever, and not think about what I'm doing and how I can further optimize it. And that is from, you know, how many steps it takes me to make a brew, a cup of coffee in the morning, what lane I pick in slow traffic, to you know, what restaurant, what type of restaurant we pick to go out to when we were picking a restaurant.
So that's my superpower.
I also say that every superpower also for most people to make that unique, it also is paired with a domain or an industry or an area of focus.
So my personal area of focus is venture backed startups.
So if you combine that. I am a world class expert at the optimization of venture backed startups.
Thus why I run this company, founder Nexus now, because that's what I'm doing. I'm working with global venture founders to optimize their businesses and make them more successful. I've literally built my, my superpower is what I get to bring to work every day now. Like it. And it's also what made me great at being a founding CEO. Like, why was I, why was I reason more successful than many? Because it drives right into, it falls right into the sweet spot of my superpower.
And so the dark side of my superpower, by the way, so that's to flip to that point is because I'm always trying to optimize. It can be incredibly annoying to some people because I, I can disempower teammates early in my career. Yeah, the team would come together, we, we'd, you know, ideate on a topic and I could always immediately see a better way forward. And I'm like, wait, okay, the best way is bump, bump, bump. And I just say, okay, well, that disempowers everybody from wanting to contribute to a conversation like that.
And it really takes the news out from a team and it's terrible. So it was, it was stood in my way.
So the good news is I learned how to manage it in a team. Likewise in my home environment, if I'm, my wife is cooking dinner and I'm like, oh, honey, if you just do this, it'll cook the chicken a little better. She's like, shut the F up. Like, get out of my.
[00:40:19] Speaker A: Face.
[00:40:19] Speaker C: Stop.
I do not need to be optimized right now, God damn it. And, or, you know, oh, I, oh, I'd like to go to Chinese. I'm like, oh, but we could also do. She's like, stop Chinese. So it definitely, it definitely shows up all the time and it's hard for me. It's hard for me to manage it and it would be hard for anybody to manage.
[00:40:38] Speaker B: It.
[00:40:38] Speaker A: So. Oh, that's great, Paul.
My dark side is obviously my sarcastic jokes because my wife is like, please just not. That's not the time. Can you just.
[00:40:47] Speaker B: Stop?
[00:40:47] Speaker A: Right. I know oh my God.
Funny.
So let's switch gears here a little bit. We've talked a lot about like the origin of DocuSign and like your experience, founder Nexus, and I'd like to talk now about like what's happening in the market and like there's a lot of hype around AI through like a number of hype cycles. So based on like your experience, you know, going all the way back, it sounds like you know, your experience like in the.com on forward and you could divide it up into as many different ways as you like. A lot of people like to talk about like, you know, you had the mobile and web 2.0 and we had crypto. So there's given all these tech cycles, like give us just kind of a perspective on where you think we're at right now with the, let's call it the AI.
[00:41:35] Speaker B: Boom.
[00:41:36] Speaker C: Okay.
So having watched many, you know, like I started my professional career in the late 80s and so it's, you know, I've been at this a while and having watched a number of different cycles occur over the last 30, 35 years, is that they are, that they are cycles and they all have highs and then they have releases, I won't call them crashes because not all of them crashed, but definitely releases from the hype. We are definitely in an AI hype cycle right now and that's.
[00:42:10] Speaker B: Great.
[00:42:10] Speaker C: Right? And like a lot of our the preceding cycles it starts with a few enterprises, companies, adopters. For us now it's the LLM model producers and the hardware providers usually and every other cycle it matures past those at some point to being systems and application layer development where it can actually be deployed. I think my own observation is LLMs are not a lasting differentiated characteristic. I think the cost and value of those will go effectively to zero over time.
I think the enterprises that are starting to understand how to use the transformer model and ultimately what, what comes after that will, you know, on captive data sets or whatever powers their business to create specific application layer outcomes for their business. I think those are the ones that are going to really leap forward or be the next driver and then you know, as this, as this hardware, you know, as Nvidia and OpenAI start to become a little less exciting, you're going to start to see application layer companies because that's been true in every other preceding cycle that's gone before this one. I don't know why this one would be any.
[00:43:32] Speaker A: Different.
Yeah. Do you think like cursor an example of, of the application layer or I'M curious, like how you.
[00:43:41] Speaker C: Would. Yeah, I mean, because that is applied to coding. Right? I mean, we're talking about something where you can take the concept of a transformer idea and apply it to.
[00:43:51] Speaker A: Coding.
[00:43:52] Speaker C: Yes. I think that's the beginning of that sort of thing where you start to see well, well honed applications of this base technology.
Likewise, you. You've heard all this talk about blockchain for all these years, and then the coin cycle, which only recently is sort of hit a fervor, but I'm still unconvinced that there's any value in the.
[00:44:13] Speaker B: Coins.
[00:44:15] Speaker C: Right. Blockchain as a technology is very interesting and has very broad and potentially interesting use cases. The idea of creating a currency using that is an interesting one and it's certainly creating some paper wealth for some people, but I don't think it's sustainable.
In other words, there's no underlying value creation in a coin.
It just doesn't until there's other things that happen around it.
So I bet on things that are blockchain based, technically based on the blockchain, not necessarily bet on.
[00:44:49] Speaker B: Coins.
Gregory, I think we were talking about this.
The fundamental value comes from transformation. Right. Transforming some kind of raw resource into something.
[00:45:02] Speaker C: Usable.
[00:45:02] Speaker B: Yes. The token creates no value. Right. So you could use that as a store of value, but fundamentally it does not contribute to the economy at.
[00:45:12] Speaker A: All. Yeah.
We haven't talked much about crypto on our show, but I agree 100%. So I guess I would define landscape pretty simply in this way. Like, I think bitcoin is open source, it has some value, maybe it's digital gold. And I would define it differently than all the private tokens.
I'm not a huge believer in it, but I think that's what's emerged in the market and I think it'll continue.
All the private tokens, I 100% they don't have the value they even bitcoin has. It's open source. And maybe everyone will adopt this as some kind of store value or something.
But I did like that because the way the tokens work that people are now applying to what I think is the basic use case of incentivizing computers to work collectively. And I'm seeing people selling infra and stuff like that with some type of crypto network, which I had a friend of mine who started a company doing that, and I was like, awesome. Because that's the only use case I actually see for a private token is you can just incentivize different machines to work together. So I Think there's some core fundamentals to it, but like pushing the value of a coin up as some kind of scheme. Yeah, I'm just.
[00:46:28] Speaker C: Not. Yeah, that is, there have been.
I can't see that that is sustainable value.
[00:46:33] Speaker A: Creation. Yeah, I agree.
[00:46:34] Speaker B: 100%.
Do you have any predictions where in the next three or five.
[00:46:40] Speaker C: Years?
Okay, so it depends on the time horizon. And I think we all have our own opinions on predictions.
I think that the more powerful AI gets, the more two things are likely to happen. Jobs will get displaced or repurposed and education as we currently understand it related to the creation of jobs will also have to fundamentally.
[00:47:07] Speaker B: Change.
[00:47:08] Speaker C: Right. Underneath all that, I think I don't see if, I don't see any future that does not at some level include universal basic income provisioning in, in society. Because I think there's going to be enough job destruction over time that we're going to need to have a.
Something to fill the.
[00:47:28] Speaker B: Gap.
[00:47:29] Speaker C: Right. Because there'll be a lot of people out of work and nobody earning money and then that'll crater every economy everywhere if that doesn't get addressed quickly.
And if you run the camera forward a fair ways, if we have machines, and I won't call them AIs, I'll just call them machines that are very highly specialized, not only producing thought processes like they're doing now with the current transform models, but physical product, we will have a society where everything can be produced at its lowest possible.
[00:48:02] Speaker B: Price. Price, our.
[00:48:02] Speaker C: Cost.
Okay.
So rather than right now we have market inefficiencies that will create market, should over time create market efficiencies, which again means fewer jobs, fewer. So we have to rethink how society, how humans play in that world, which then ties back to education.
And my big prediction, if this is what could be decided, is that our fundamental educational system is going to radically have to be remade from the ground up. Meaning the current educational system that we have is built upon the foundation of the post industrialized age, which is to say that we are building workers for factories.
Right. So our educational system was memorize things, be able to regurgitate certain facts so that you can be a cog in a much bigger.
[00:48:53] Speaker B: Machine.
[00:48:54] Speaker C: Right. When the machine is the machine and it doesn't need humans to be cogs. What's the purpose of a human? Okay, the purpose of a human is to elevate the thinking so that new things can come about.
So what preceded the industrial age and the modern education system was apprenticeship.
So my thesis, you can clock me here, interesting. Is that we will go away from what we understand as Western educational structure back and we will revert back to mostly an apprenticeship model where you, when you come of age, in your early teens, you start to apprentice in various roles in society and that's how you learn and are taught and are trained to be a productive member of society rather than going to a high school or college and to become a cog in the machine. So that's one of my predictions. How about.
[00:49:46] Speaker A: That?
Do you, do you think that would be like the private market or do you think the government facilitate, like, is it outside of the, like education system, this.
[00:49:55] Speaker C: Apprenticeship? I believe it has to be. I don't think, I don't think the, the.
I certainly, I think there are a lot of people who would agree that the education system as it currently stands, certainly in the United States is not successful in, in the. Not broadly successful.
So it does need some rethinking anyway. I would just argue that the. Trying to just remake the exact same system we have and make it more efficient again. Because its purpose was to produce factory work.
[00:50:26] Speaker B: Basically. Yeah.
[00:50:27] Speaker C: Yeah. And we won't need many factory workers in the future. We're going to need people that, yes, we, we're going to need things like electricians and plumbers and people that interface with physical things.
Right. But we're also going to need people to think and advance science and other things because AI is not going to yet be good at that. AI is good at understanding what has come in the past, but it won't be always great at implementing future. And that's where humans are very well skilled and I think have a real purpose. And back to Founder Nexus and tying this all together.
So a big part of my goal and objective with Founder Nexus is to create an exemplar of humans working with other humans to solve common problems because that's what Founder Nexus is writ large. It's just done it at a global scale, focused on founders. Right now I've got a very narrow focus on my community, but the idea is put them in small groups, give them an incentive to help express their own personal lived experiences in order to. That you advance the thinking of all of the people in that discussion and that they can then collectively get better and better and better. So imagine that as the worldwide exemplar of how humans can advance humanity.
Where today I struggle to look around the world and say, where are the examples of people working with an AI where it's actually helpful as opposed to.
[00:51:48] Speaker A: Destructive.
[00:51:49] Speaker C: Yeah.
So I want Founder Nexus to be an example of people collaborating at a global scale irrespective of their politics, religion, skin color, race, nationality, socioeconomic background, educational background, any of that.
Right. So that's, that's a big. That's part of what I want to be part of. I want to create that future for my kids and the kids that come behind.
[00:52:15] Speaker A: Them.
[00:52:17] Speaker B: Awesome. Wow.
[00:52:19] Speaker A: Is. So just help me understand, like Founder Nexus. Like I went to one of the events in Seattle. Like, are you expanding? Like, what are you already like, maybe just tell us like your future plans. How's.
[00:52:31] Speaker C: That? Yeah, yeah, we expand upon regional chapters. So we have now chapters in Seattle where we started, San Francisco, I launch our London chapter week after next we'll be launching around, you know, Probably Tokyo in Q1 and all around North America following. So, you know, I don't know that we'll necessarily be at one a month, but we're probably going to get close to that in 20, 26 and.
[00:53:00] Speaker A: Beyond.
[00:53:01] Speaker C: Yeah. So we organize locally in order for local founders to get to know one another and to help.
But by stitching all of those chapters together globally and holding regular events that include members from all chapters, we're giving access to founders to not only learn from their local participants, but also to learn from founders in other geographies such that it's part of a bigger plan to figure out how to get venture success to happen anywhere in the world and not just in the power 20 or 30 cities where they all happen right.
[00:53:30] Speaker A: Now. Yeah, yeah.
Is it, is it invite only? Like how do the chapters get rolled out? Yeah. How do people get.
[00:53:37] Speaker B: Involved? Involved?
[00:53:38] Speaker C: Yeah. Well, so to get involved they apply and they have to have a minimum set of credentials. Their credentials we are currently asking for is you have to have been a venture scale founder for at least three years. You have to have raised some capital professionally, meaning not friends and family capital. Some angel or VC money has to invest it in you before and you have to be actively building or trying to build a venture scale business which I define as targeting 100 million or more in revenue.
[00:54:06] Speaker B: Annualized. Got.
[00:54:08] Speaker C: It. If you meet those three criteria, you apply to Founder Nexus and you're granted a pre qualification credential to come and experience a few events. Greg, just like the one you came.
[00:54:18] Speaker A: To.
[00:54:19] Speaker C: Yeah.
While you are evaluating whether this is a community for you, we are also evaluating you and whether you fit into our community. At which point after you come to one or two events, you will be invited to join. If we think you are going to be a qualified and contributory member to the community, then you can become a.
[00:54:38] Speaker B: Member. So you.
[00:54:39] Speaker C: Have. You do have to be invited. It is an invitation basis.
And we do have to meet you and get to know you. And likewise, you get to know us before that invitation can be.
[00:54:48] Speaker A: Issued.
I love.
[00:54:51] Speaker B: It.
[00:54:52] Speaker A: Yeah.
Awesome. You have fun.
[00:54:55] Speaker C: Today?
Oh, yeah, no, this is. I didn't. I didn't know if you wanted to wrap up here or not. All.
[00:55:00] Speaker A: Good? Yeah, no, I think we're gonna. We start a little late, but yeah, we kind of. For about almost an hour now and.
[00:55:06] Speaker B: So.
[00:55:06] Speaker A: Yeah. Yeah.
Any final words or stuff you'd like to close with or leave with our. Our.
[00:55:12] Speaker C: Audience?
No, I think I've covered it. I don't want to. I. I would just probably wax on, but I don't need. I don't need to do.
[00:55:22] Speaker B: That.
Okay.
[00:55:24] Speaker C: Perfect. Appreciate.
[00:55:25] Speaker B: Your. Yeah, really appreciate you sharing your stories and coming on the show.
Thank.
[00:55:30] Speaker C: You. Thank you again for your flex. Really good starting late. I really, really appreciate it. I got some. What ultimately became really good news. I was worried that I needed to go in for a very.
[00:55:40] Speaker B: Challenging. Can we just cut off the stream?
Yeah, yeah.
Thank you for coming. We're going to just end the stream and then we'll go off on it. Got it. Yeah. Okay. Thank you.
