Navigating the Nuances of Unreasonableness in Leadership

This chapter examines the challenges of interacting with unreasonable individuals in start-up leadership. The speakers highlight the balance between being disagreeable and being a jerk, offering insights on how these traits can influence a founder's effectiveness and support.

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Is there a secret recipe for start-up success? Probably not. But if you take a close enough look at some of the massive success stories like Twitter and Lyft, patterns start to emerge.

Venture capitalists Mike Maples, Jr. and Peter Ziebelman pull back the curtain and examine how start-ups go from seedling ideas to billion-dollar companies in their book, Pattern Breakers: Why Some Start-Ups Change the Future.

Mike, Peter, and Greg discuss the roles that insight and implementation play in determining a start-up’s chance at success, how investors distinguish between genius and crazy, and why the best founders are like artists.

*unSILOed Podcast is produced by University FM.*

Episode Quotes:

Distinguishing idea vs. insight

25:33: [Mike Maples Jr.] A lot of people confuse risk and uncertainty. And so, like, I might have an idea in an existing market that there's a clear need for, but it's a bounded upside idea. But I can connect the dots between the idea, customers wanting it, and a successful business. I might, on the other hand, have an idea that's like Justin TV, right? Which is a reality 24/7 streaming TV show, which is crazy online. But it embodied a lot of inflections and insight. It was a terrible idea, but a great opportunity. And so what we're interested in is not certainty about the future, because if we're going after a non-consensus idea, if we have real insight, we can't know we're certain yet. All we can know is that we're non-consensus. Just because we don't know how the dots will forward connect doesn't mean they won't forward connect. And it doesn't mean that the expected value of the upside isn't higher. So that's what we kind of encourage people to say: just because you don't know how success will happen doesn't mean that it's not way better to pursue that path.

The crucial elements that contribute to startup’s breakthrough

06:10: [Peter Ziebelman] There's still a lot of luck and perhaps intuition and guesswork to determine whether you're going to find a breakthrough or build a breakthrough. But having said that, we do believe there are elements that can tip the balance—inflections. Another element is seeing that the entrepreneur has insight, something they know to be true that others do not yet believe, and we believe insights are one of the things that explain a lot about startups.

Being a founder is like being an artist

52:34: [Mike Maples Jr.] A lot of people think about what type of business person is an entrepreneur. And what I've come to believe is that the right way to think about it is they're more like an artist than they are like an engineer, a salesperson, or anything else. [53:06] And by that, I mean two things. First of all, artists notice something that other people don't notice, right? And then the other thing that artists do is convince people to abandon their logic. And so, like, no rational employee would join a startup. No rational customer would buy from a startup. No rational investor would invest in a startup. [53:45] So the founder has to convince all of us to abandon logic and go on a journey where we're 85 percent likely to not succeed. And so the best founders I've ever met have those. Attributes of the artist, and they have the artistry to notice from their sensitivity, and they have the artistry to persuade and convince people. They have the artistry to notice from their sensitivity, and they have the artistry to persuade and convince people.

How does a founder balance persistence with openness to new data and insights?

21:06: [Mike Maples Jr.] If you have the right insight, when we talk about pivoting, your insight, like in basketball, is like your pivot foot. You hold it planted firm, and you move your body by either modifying your implementation, modifying the audience that you talk to, or some combination. But if you have to leave your pivot foot, you're no longer attached to anything as a startup, right? You might as well start over. You might as well try a new idea or just give up. And so that's where I think you reconcile it. You want to be flexible in your experimentation of navigating your insight to the desperate, but you want to be fixed about what you believe is different about the future.