Sean Sheppard | Stoicism, Smooth Waters, and Censorship at Scale

[00:00:23] Hi everybody, this is Andrew Gadomski and welcome to the Reciprocity podcast. Today I'll be interviewing and sharing with Sean Shepard. Sean and I have known each other for a long time and certainly admire his leadership and innovation. So Sean, welcome to the show.

[00:00:43] Sean Shepard Thanks for having me brother. Always fun to be with you.

[00:00:45] Sean Shepard Thank you, appreciate that. So why don't you give us your elevator story here.

[00:00:50] Sean Shepard For 30 years as a serial tech entrepreneur from Silicon Valley, three exits, three venture funds, started the world's first product market fit startup accelerator and a school focused on helping educate talent to work in startups in Silicon Valley, about GrowthX and GrowthX Academy.

[00:01:07] Sean Shepard Four years ago, I bought a significant stake in a corporate venture builder called Uplus. In the last two years since then, we've transformed the business from a services business to a software business using AI to automate most of the work we're doing around venture building and innovation.

[00:01:23] Sean Shepard And that's been challenging, but also a lot of fun and looks like we'll be coming out the other side stronger than we were before. So that's exciting. We left California about four years ago, moved to Montana, very close to where our kids are going to college. And as you know, you know, I've got free time on playing golf.

[00:01:41] Sean Shepard That's right. So how's your handicap?

[00:01:44] Sean Shepard It's all right. Still floating around scrap.

[00:01:47] Sean Shepard I don't know how you do it, man. I can't get at a one six for a while, but I don't play enough.

[00:01:53] Sean Shepard Well, you live on a golf course.

[00:01:54] Sean Shepard I think the key is to play a golf course with a very high course rating because they're much more giving to your scores, especially when you travel and then you play easy courses and then you shoot really low numbers. Having a low handicap is not a good thing. You know that we get pencil whipped by our friend.

[00:02:09] Sean Shepard I love that my handicap went up to like a seven or whatever.

[00:02:12] Sean Shepard I would be a really good. Yeah, I'd be a really strong five, you know.

[00:02:18] Sean Shepard All right. Let's get into it.

[00:02:22] Sean Shepard So the first question is around leadership. Talk about a trait or technique you've learned about from someone else and how you've executed it for success.

[00:02:37] Sean Shepard I think probably from my father who was an officer at Intel for 30 years. I was lucky enough to watch how he operated. More than anything else, it's leading from the middle.

[00:02:49] Sean Shepard Okay.

[00:02:51] Sean Shepard Demonstrating that you are willing and able to do the same job that anyone else is willing to do. Nothing's beneath you and that you have the emotional intelligence and empathy to support and understand these people.

[00:03:03] Sean Shepard Listen to them and manage personalities and difficult conversations in a non-threatening way, especially in today's day and age.

[00:03:12] Sean Shepard I think we're, I'll just be honest and say it. I think we just have thinner skin now than we've ever had.

[00:03:17] Sean Shepard So communicating and managing emotions and people is more fragile and delicate now than maybe it ever has been.

[00:03:26] Sean Shepard And then around all of that, I really, in the last decade, dove in and heavily into stoicism and stoic philosophies and try to use those every day in my own life and in my work and impart them not through necessarily proselytizing stoicism as this great virtue or set of virtues, but just sort of in my behavior, right?

[00:03:50] Sean Shepard When things are difficult for everyone, as the leader, you need to be the one that's the most stoic and calm, right?

[00:04:00] Sean Shepard It's easy to be a captain in smooth waters, but what's it like when the storm hits and how do you react to that?

[00:04:07] Sean Shepard So I try to pay very close attention and be mindfully aware of how I react more than how I act.

[00:04:14] Sean Shepard Hopefully that spills over to the people around me.

[00:04:18] Sean Shepard And then I think the other thing is you genuinely have to love and care about the people you work with and they have to believe in that.

[00:04:25] Sean Shepard I love that.

[00:04:26] Sean Shepard I see that, you know, they'll go, they'll go a little, you know, they'll go the extra mile.

[00:04:32] Sean Shepard That's right.

[00:04:33] Sean Shepard When you lead through those troubled waters and you care at the same time, the reaction and the proactivity is excellent.

[00:04:39] Sean Shepard Okay.

[00:04:45] Sean Shepard Tell me about a food that you make or buy from others that you believe makes them feel love from you.

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[00:04:55] Sean Shepard That did the same for you.

[00:04:58] Sean Shepard Wow.

[00:04:59] Sean Shepard To me, comfort food is leftovers.

[00:05:04] Sean Shepard Growing up, we didn't have a whole lot.

[00:05:05] Sean Shepard My mom would make a crock pot on a Sunday and we would eat that until it was gone.

[00:05:10] Sean Shepard Sometimes three, four meals a day.

[00:05:12] Sean Shepard So when my wife makes a pot of chili on a Sunday, she'll have one bowl and I'll eat it all week.

[00:05:18] Sean Shepard And she thinks I'm crazy, right?

[00:05:20] Sean Shepard That kind of stuff causes misunderstandings.

[00:05:25] Sean Shepard But I think anything that is made by someone with you in mind the way you want it is special.

[00:05:32] Sean Shepard Love that.

[00:05:33] Sean Shepard I have dietary restrictions, for example, for physical reasons.

[00:05:37] Sean Shepard There's certain things I can't eat and somebody recognizes that in advance.

[00:05:40] Sean Shepard I won't bring it up.

[00:05:41] Sean Shepard I'll just power through it or try to eat around it and not say anything.

[00:05:45] Sean Shepard But if they do it proactively, that means a lot.

[00:05:48] Sean Shepard That's awesome.

[00:05:49] Sean Shepard I love that.

[00:05:50] Sean Shepard It's being deliberate and planning around it.

[00:05:53] Sean Shepard One of the things that Shara does is she's very conscious of what not what's going to make people feel good,

[00:06:00] but what allergens or methods do they like to eat?

[00:06:04] Sean Shepard And then this way it creates that, especially given the healthcare situation our country tends to be in.

[00:06:11] Sean Shepard You want to help.

[00:06:12] Sean Shepard And that's one of the ways to do it.

[00:06:14] Sean Shepard Sugar is the enemy.

[00:06:15] Sean Shepard Sugar is the enemy.

[00:06:17] Sean Shepard I'll talk to you about corn syrup story after we're off recording.

[00:06:23] Sean Shepard Okay, mental focus.

[00:06:32] Sean Shepard How do you keep that focus at work and where did that model come from?

[00:06:37] Sean Shepard So you've known me forever, but for the benefit of the audience, I've got radical ADHD, always have.

[00:06:44] Sean Shepard And the easiest way for me to calm it down is either through substance abuse or physical exercise.

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[00:06:51] Sean Shepard Just kidding.

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