North Star Leaders Podcast

Lindsay Pedersen

The world needs what only your business can bring, and as a leader, it's your job to deliver. But where do you focus? Where do you direct your time, your team, your budget, and your emotional energy? We're learning this together on the North Star Leaders Podcast. In this podcast, I talk to purpose-driven leaders about the choices that they make to create audacious economic value while also realizing their distinctive purpose. I'm Lindsay Pedersen, brand strategist, author of Forging an Ironclad Brand, and host of the North Star Leaders Podcast. Let's get to it.

Today, I am really happy to be joined by Court Lorenzini. Court has been co-founder and founding CEO of many companies, including DocuSign, and is now CEO of Founder Nexus, a community for venture-scale founders. Court, welcome to the show.

Court Lorenzini

Lindsay, thanks for having me. It's so fun. I love having these conversations.

Lindsay Pedersen

I'm so glad to have you. Court, to start us off, what is your favorite thing about what you do?

Court Lorenzini

Oh, man. I work with venture-scale founders, and I think my very favorite thing is when they have that moment of the lightbulb moment, as I call it. The moment when some new insight has struck home with them, and they can see themselves leaping forward on their journey very quickly based on some new insight that we've been able to uncover.

Lindsay Pedersen

So that moment. It's like that moment where you see the insight happen.

Court Lorenzini

Yeah. When you see the lightbulb go off in somebody's eyes and that you can just feel the energy rise in their spirit and in the room, absolutely, that's infectious.

Lindsay Pedersen

It's like magic. I love that. Talk about Founder Nexus. What is Founder Nexus? What led you to start this?

Court Lorenzini

So Founder Nexus evolved from my own experience in the sense that I started, this is now my fifth company, and it is a tough, hard, lonely, unforgiving experience, almost inevitably doomed to failure. Meaning as I talk to founders across board, I'm normalizing the fact that the statistics will tell you that anybody that is a founder is almost absolutely guaranteed to have one or more true abject failures on their record, and that that actually is okay, because those are the statistics. Recognizing how hard this job is, I also, on the other side, recognize founders to be perhaps one of the most valuable resources we have on this planet. They drive the world's economy. They drive ideation and everything that fundamentally we experience in our lives. And if there's a way for us to make not only their journey better, but raise their odds of success so that we don't waste their time and other people's resources in terms of money, it's a global game. We will do better as a world if we do that. And so the Founder Nexus concept revolves around bringing venture scale founders together to help each other share experiences so that they raise their overall odds of success. That's the founding premise.

Lindsay Pedersen

Love it. Because they are in a unique position to share hyper-specific, hyper-relevant stories and lessons learned that really no one else can.

Court Lorenzini

Indeed. And I would expand on that to say, I get called in a lot because of my history to consult with, advise, be on boards for companies. And yet, my own experience is my own experience, meaning it's a singular human. And when I'm expressing that to another founder, they have to filter that through their experience, their culture, their roadmap that they're following. And they're usually only able to take or implement a tiny fraction of my experience because that is all that is relevant to them. And yet, if I introduce those same people, 8, 10, 20 other founders who have had their own experiences in that situation, together, the assimilated knowledge from all of those people, they can bring together a much better outcome than they would with only one person's advice. So really, Founder Nexus is about creating a circumstance. And I call it structured serendipity. And structured serendipity means I'm creating a reason why people would come together and share experiences in order to help others gain a faster traction, foothold, and success rate.

Lindsay Pedersen

I love that. It strikes me in a funny way, it's also about scale, because you yourself can share a lot. And a lot of it will be relevant and useful, but there's still only one of you. And there was a peculiar set of circumstances that led to those being good lessons that you learned that may or may not be relevant for somebody else. So if you can just multiply it by something double-digit instead of just single-digit, they're going to be able to bring to bear more, not just success stories, but failure stories, and stories of hardship, and stories of celebration, and super specific things, and less specific things. But all together, because it's a community, instead of an individual mentorship or advising relationship, that person's going to have higher odds of success.

Court Lorenzini

You hit the nail on the head when you said scale, because while I am starting the adventure here in Seattle and building it around the Seattle Founder Network, my immediate goal is to globalize it. So, I want Founder Nexus chapters in every community where there are sufficient venture and founder density to support them, and then network all those chapters together so that founders in any region of the world can access the experience of founders in any other region of the world. And the exponential impact of that is staggering.

Lindsay Pedersen

Yes. Yes. It also feels just like I'm putting myself in the shoes of a founder right now, and there's so much functional, practical utility to what you just described. There's also sort of like the human spirit of human to human connection and learning in a more almost emotional and connection-oriented way. And also, being a founder, as you just described, it is so unbelievably difficult and vulnerable and lonely. So addressing that with community, not mere advice, although that's wildly important, but it's both. It's the combination of those two things that's so important. Because you have all of the functional advice in the world, but if you lose heart because it's lonely, it doesn't matter how useful the advice was.

Court Lorenzini

In fact, I actually counsel the people in the organization not to lead with advice. In fact, as they express themselves to each other, I say, if you leave the sentence with, you should or I would, then you're off base.

Lindsay Pedersen

Wow.

Court Lorenzini

What I want you to lead with, in my experience, when I saw this situation, this is what I did, because that is far more useful input for a founder than somebody giving them advice. Because the advice may or may not be well-grounded in experience, and that can lead people easily astray. And I find that to be the case often when you get advice from folks that have not been founders before and have not sat in that hot seat and felt what it feels like to make those decisions in that situation. You get well-intended advice that is entirely off base and really sets the company in the wrong direction. So, to me, it's all based on grounded, lived experience.

Lindsay Pedersen

They themselves can glean from that story that's been shared and apply it as they see fit. It's not coming from a place of judgment or well-intentioned condescension. It's actually coming from a place of, well, I actually don't know, but here's what I did experience. Take from this what you will. Because there's something almost judgy about, you should do this, or I would do this. And then what if they don't do it, but it turns out that they should have? Then both people have lost face with one another.

Court Lorenzini

Exactly. So that's why I say lead with your experience. If you always start with that, then the person listening can extract from that useful bits that they can apply in their situation rather than trying to tie it into a directional piece of advice. Yeah.

Lindsay Pedersen

You have co-founded and led DocuSign to mammoth success. And I've heard you say that what you're most proud of is that DocuSign is considered one of the greatest places to work. It's still to this day, many years after you left DocuSign, it has that culture. How did you build that culture? What was the source of direction or inspiration that led to building the culture that you built at DocuSign?

Court Lorenzini

So to me, people are the most valuable and uniquely defensible asset that any company has. And I start with the idea that you need to both hire good people, but really develop them and give them a trajectory within the organization. So we built, even at DocuSign, an entire employment life cycle that began with how we reach out to and recruit people and concluded with them leaving the company and us supporting their departure into their next phase of career development. And it was an entire, constructed, visualized, talked about, and embraced culture of, hey, we recognize that you're going to come here, you're going to work for a while, and you're going to leave and go do something else. That's great. We want you to be highly productive while you're here. So we want to invest in you as a person and in your individual growth. And at some point, you're going to take that experience and go someplace else. And we want to applaud that and make you part of our family.

So regardless of where you came from or what you're doing here, you're always part of the DocuSign family. And when you start with valuing the individual and their ability to contribute to the whole, I think that leads to sustainable cultural strength. I often talk about the fact that I think of culture as product. Culture is as important as the main product that you sell. And you need to think about culture and add features, add capabilities, add structure, add support in a way just like you would your mainline product, because that's how you present a company to the world. Product is one instantiation of that. Your people and the way they interface with the customers, the support people, the community, that's the other way that you interface with the community and the world. And they both have to be world-class. So I put a huge premium on culture development in all of my organizations.

Lindsay Pedersen

The way that you describe that as culture is as important of a presentation of a company as is the product, it kind of answers the question, well, why is it smart to do that? When I'm hearing from you is there's, and I love how you said, the people are uniquely defensible. There's a competitive moat, if you will, to culture, just like there ought to be for product and so on. And so you could do it just because you're a good person and you want to create good culture, but you also could do it because it's just the smart competitive advantage to build.

Court Lorenzini

It's good for the business. It actually is a competitive moat just like your product is. If you do it right and think it through and create it like a product that has to be continually cared and fed and nurtured, that creates a competitive advantage over time.

Lindsay Pedersen

Did you know that going into DocuSign that this was going to be a hugely, because DocuSign was not the first company that you founded. So was this born from not having done that and wanting to do it differently with DocuSign or was this always something that was important to you to build into companies you've helped found?

Court Lorenzini

DocuSign was the second company I founded. I had started and founded one that ultimately got sold. I was leader of another in a transition period before I co-founded DocuSign. And it became increasingly clear to me as I was moving through that early phase of my career as a CEO, how important and how critical it was. It was always important to me, but I think in the first iteration, I didn't quite get it right. It still was very good, but it wasn't what I ultimately built with DocuSign and have built into the subsequent companies. So I think each of us as a founder has certain learnings that we pick up along the way and things that we want to change and evolve into. And I think that again, is one of those strategic advantages of being in a community of other founders and that you as a founder should always be looking to advance yourself as a leader in terms of how you address your company, your customers, your community, your investors, your board, et cetera. And if you just stick to what you know and what you have individually learned, you will not iterate fast enough or grow efficiently to make a real dent in the world.

Lindsay Pedersen

Yeah. I imagine, and tell me if this is true, that there are times and seasons when it's easier to do this than others, that there are moments when if you have to choose whether to invest in, I don't know, product or culture, something that's more short-term urgent versus long-term important, that sometimes there's a tug that you have to resolve. Is that true? Are there times when it's actually really hard to prioritize culture since it's not going to shut down the company tomorrow if you don't build it to the best of your ability?

Court Lorenzini

The short answer is no. I don't find that those two things are intention because the things that you do to invest in culture are typically done throughout the cycle of building the business. And the things that are critical to building product are often brief moments in time where you're needing to invest a certain type of resource in that outcome you're desiring. And rarely are they the same resource. So you're not usually conflicted in terms of how and when you do it in my experience. So no, I haven't found that to be in conflict.

Lindsay Pedersen

I love that. Okay. I've also heard you talk about how you yourself have developed a process to help people figure out their superpower. Could you talk about what you consider to be a superpower and how that bolsters leadership?

Court Lorenzini

Absolutely. So let's back up to the fact that I consider people the most valuable asset in an organization. Start there. And then understand that over time as I was looking to build teams and create effective outcomes, I found that all the tools that were out in the world that currently exist to help understand humaneness or how we act as people were insufficient in terms of their ability to guide decision-making around hiring and team building, team construction. So I ended up constructing my own tool set. And the premise there is that every human in the world has what I describe as a superpower. And a superpower is something that they do better than anybody else that they know or come in contact with. It's something that is so innate to them. It's like breathing. They can't not do it. The hard part is discovering what that is.

Most people cannot put a finger on their superpower. They often might describe a skill, not something that they've learned or are inherently good at, but that's not getting at the heart of the superpower in my experience. So to me, superpower is not only something you do inherently well, but it actually has a couple of layers. What I've learned in my research is superpowers in the broad community, if you take the world and you run them through a series of questions to help them discover their superpower, which is what my process does, is it's an interviewing process to help people discover their own. It's not prescriptive. It's discoverable. Then you realize that there's a relatively small percentage of what I call four superpowers in the global population.

It's not millions or even hundreds, it's dozens. And yet the next layer is, and then how have you applied that superpower and what domain do you imagine your superpower is most effective, given where you are in your life cycle or your career development, because a core superpower can be applied to many different domains and have different outcomes. So when I look at myself and I'm self-diagnosing, my core superpower is optimization. I can look at any situation and figure out how to optimize it. And I can't not do that. It's just the way I see the world. My domain is startups. So I am one of the optimizing early stage company development. That's where my domain has been expressed. I could have taken optimization and been an astronaut or a politician or a banker and equally been successful in those realms if I knew how to apply that superpower, but by being able to tie it down to a singularity, like the one thing that I'm really good at, and I'm very focused on making sure people can get to a single word description of their superpower, that helps immeasurably as you start to say, well, then what roles and responsibilities should you have? What kind of decisions will you naturally be good at making? How? And then when I see that superpower, I recognize that every superpower has a, what I call the dark side, which is the thing that you're vulnerable to when you're expressing your superpower.

And therefore, how do I pair you with somebody with a complimentary superpower that will fill in your dark side and you'll fill in theirs? And now I can actually start to put groups of people together where the outcome is superior to a standard team. They will actually all perform at much higher levels with higher personal satisfaction, higher output, better accomplishment and wealth metrics. And they'll be self-satisfied. You create a culture of I'm doing something I'm so naturally good at and excel at in the world when I'm being asked that I can't not be successful. And so that creates a culture of picky crust and delivering on high-level goals and objectives.

Lindsay Pedersen

And it sounds like there's an ease to it because if it's like breathing, you're not using brute force to bring to bear a given skill, you just have it. And so there isn't like a striving that creates tension or is tiring or exhausting because it's what you do.

Court Lorenzini

It's the opposite of that. The way I describe it to people is when they can finally uncover the one word descriptor of their superpower, it's like a tuning fork going off in your brain. You can't help but like smile and get a tingle in your body because you're like, oh my God, that is me. Wow. That's like so core to me that I'm so excited to think about it in those terms. And now I can apply that thoughtfully in my life, not just in my work. I can express that with my friendships, with my relationships. I mean, everything I do inside and outside of my work can be influenced by a core understanding of your superpower. And it's amazing the unlock moment that has for people. Very exciting.

Lindsay Pedersen

You said that there are like dozens, not hundreds or thousands, but like dozens of families of superpowers. And it made me think, you could tell me if this is silly, but it made me think of how humans in most of our history have only known about 150 people. So like the size of the tribe is small. So a tribe that's high performing where people succeed, live, survive and thrive, probably have a bunch of superpowers or a bunch of natural skills that are brought to bear. And it makes sense that there would be probably only a handful, like some dozens of these, not hundreds or thousands. Otherwise we wouldn't have evolved the way that we did. And so there's like the success of the tribe, or you might say the success of a company or a family or a community comes back to like what's the optimal grouping of these superpowers, of these natural tendencies that make for a more successful, cohesive group.

Court Lorenzini

I think that's a very wise way of looking at it. I hadn't gotten to the point of describing the why there are so few. I just experienced the fact that when I guide people to figure out their own superpower, the results are a fairly narrow set as it turns out. So it's good for you to think about the why.

Lindsay Pedersen

I mean, I don't know. Yeah. Like that's just me putting an anthropologist hat on. It's always fun to be an armchair anthropologist. But I love it. And there's such a kind of joyfulness about that as well. And almost like a mutual respect, human to human respect, because I've got a superpower, you've got a superpower. They're not the same. But we are humbly coming together to combine what we bring to bear to create more fruit in the world.

Court Lorenzini

That's exactly it. And I think that was born from the fact that as I looked at companies and the failure rate of startups, again, my application is in the startup world. The thing I started to recognize is how often, in fact, the vast majority of failures or failure modes can be traced back to the cohesive nature of the startup, the founding team. What were their superpowers? Were they actually complimentary? Were they duplicative? The one you see most often is people assigning themselves the wrong role. So the person who was the domain expert and maybe the technical lead or the market expert, because that was their idea, assigns themselves the role of CEO, when in fact, that role was probably ill-assigned in that moment. And they should have been a different role to combine or to access their superpower in a more native way. And that there's other people that are better at being the CEO, for example, or the CTO or the CMO or the CRO than they might be, even though that's the role they assigned themselves initially.

So having that self-awareness allows certainly me as an outsider coming in to help guide best role alignment with superpower and therefore team dynamics. You can actually create better team dynamics and therefore better outcomes if you get that right. And you can fix it. Even if you get it wrong, you can go in after the fact if you're willing to listen and pay attention. Again, once you've understood your superpower and those of your teammates, you can now say, Oh, I actually probably should switch roles and give this role to somebody else who has the superpower that's more aligned with the net positive outcome for that role assignment.

Lindsay Pedersen

Is it also true that with a superpower, there's sort of no ceiling to how much value you can bring? Whereas if you're, I think like if you're offsetting an outage, like for example, I am terrible at accounting. I can get respectable at accounting, but I'm never going to be awesome at accounting. And so the time that I spend building my accounting skill is all it's going to do is like eliminate a little bit of negative. It's not going to bring a huge amount of positive. So if it's superpower oriented, there's really no limit to how much benefit comes. Whereas if you're focused on like mitigating weaknesses, you're really keeping your maximum kind of low.

Court Lorenzini

I would say plus one to that and say that my experience as a leader is don't invest in people's weaknesses, invest in their strengths. If you can, taking somebody and investing development of their strong areas yields far exponentially higher results than trying to teach somebody they're naturally weak at to get slightly better. There's no upside to that, usually just downside because it's distracting, frustrating and it consumes cycles that they should be spending doing something they're naturally good at. So if you really think that through, that determines how we all perform in the world.

Lindsay Pedersen

Yeah. And just like, why are we even alive? Right? Like, are we really alive so that we can mitigate a weakness? I mean, not to say that there's no role for that, but there's also just this like human, like we only live one time. And if you have a chance to be living in something that's close to why you were born and why you exist, like what a more kind of potent life that that is.

Court Lorenzini

I hear you talk a lot about purpose and is purpose aligned with business. And I would say 100% because if you can describe your individual purpose and how you will show up to work authentically every day and contribute, that aligns also with the company's purpose, which is how does the company align in the world and what are its missions and values and directives? And if those two things are done authentically, you get an outsized result often.

Lindsay Pedersen

I love this. Oh my gosh, Court, this has been such a great conversation. As we start to wrap up, I've got a handful of rapid fire questions for you. Just one or two word answers. Are you ready?

Court Lorenzini

Sure

Lindsay Pedersen

Okay. What is a guilty pleasure TV show you're enjoying?

Court Lorenzini

Slow Horses.

Lindsay Pedersen

Slow Horses? Okay. Morning Person or Night Owl?

Court Lorenzini

Morning.

Lindsay Pedersen

What is your go-to karaoke song?

Court Lorenzini

I don't like to sing, so I don't know that I have one.

Lindsay Pedersen

What is a karaoke song that you really appreciate hearing from other people?

Court Lorenzini

Again, I don't really participate in karaoke. Sorry.

Lindsay Pedersen

Okay. Cool. Neither do I, so it's unfair. I'm going to skip that one. Okay. What is the best way to spend a Friday night?

Court Lorenzini

Typically, dinner with friends and my wife and just sitting up talking about life and the world and getting closer to people, building community, building relationships.

Lindsay Pedersen

I love that. And lastly, what is your favorite kind of candy?

Court Lorenzini

Probably a Baby Ruth bar. Oh, that's an oldie but goodie. Plus there's a peanut and caramel. Rock solid.

Lindsay Pedersen

Love it. Baby Ruth bar. Awesome. Court, thank you so much for coming on the show. If we want people to be able to learn more about you, about Founder Nexus, where should we send them?

Court Lorenzini

So FounderNexus.com is definitely the place to learn about the organization. You can submit questions. Any inquiries that go there, I will see. So if people want to do that, there also is my LinkedIn page, which is, you know, both Founder Nexus has its own, and then I have my own and I post on various things I'm interested in there. So those are probably the easiest ways.

Lindsay Pedersen

Awesome. And we'll put that in the show notes as well. Thank you so much, Court.

Court Lorenzini

Lovely to meet you, Lindsay, and can't wait to hear all this come out. And thanks for doing this. I love that you're doing this and I think it's a lot of fun for the community. So appreciate it. Thank you.

Lindsay Pedersen

Thanks for listening to this episode of North Star Leaders. Make sure you don't miss an episode by subscribing on your favorite podcast app. If you know of a North Star Leader whose insights would be valuable for this community, please message me on ironcladbrandstrategy.com. Also on that website are show notes, transcripts, and a way to sign up for our monthly newsletter. I hope you join us again for another episode of North Star Leaders.