Transcript: ‘Prompt Your Way to Personal Growth’

The transcript of AI & I with Steve Schlafman is below. Watch on X or YouTube, or listen on Spotify or Apple Podcasts.

Timestamps

1. Introduction: 00:01:07
2. The power of treating your startup as an evolving entity: 00:03:00
3. Building a business as a means of self-expression: 00:05:27
4. Prompting ChatGPT to do Jungian dream work: 00:17:45
5. Why you should listen to this episode, especially if it feels too “woo’” for you: 00:21:44
6. Visualizing Steve’s dream with ChatGPT: 00:36:31
7. Creating living records of meaning experiences with AI: 00:47:38
8. If you tend to think faster than you can type, lean into voice interfaces: 00:49:37
9. How Steve writes with AI: 00:52:13
10. How AI will disrupt traditional coaching and therapy: 00:54:03

Transcript

Dan Shipper (00:01:07)

Steve, welcome to the show.

Steve Schlafman (00:01:09)

Hey, Dan. So good to see you, brother.

Dan Shipper (00:01:10)

So good to see you too. So, for people who don't know, you are the founder of Downshift. You are a former VC and now an executive coach who specializes in transitions for high-performing people like founders. Your main claim to fame, of course, if you're an original Every investor. And one thing that we were talking about, which I kind of wanted to start with is, I think you were reflecting a little bit on, I guess, the journey that you've seen us take and what that says about what it's like to start something new vs. what people typically expect to start up to look like. Can you just tee us up for a second?

Steve Schlafman (00:02:15)

Yeah. Well, Dan and I were reflecting for a few minutes before the show began to roll. And one of the things that I really appreciated about Dan when he was starting his fundraising process was he was like, I don't think I want this to be a venture-backed company. I don't even know what it's going to become. But hey, we're going to build something special. And I think there was something really magical about that because he wasn't here kind of giving this grand pitch and this vision of the way the world was going to be and how everyone's going to fit into it. And as I've been sitting with it and watching you and the way you've built it, I'd imagine that that version of you five years ago couldn't have predicted whatever it was going to become. 

Dan Shipper (00:02:52)

No way. No way.

Steve Schlafman (00:02:54)

And as I think about us building Downshift. I see Downshift as a container for emergence. So I think a lot of the time in startup culture, we have this idea and we see it as a company from day one, and then it becomes a thing that's rigid. And instead of seeing it as a company in the earliest days, just seeing it as a container for emergence.

Dan Shipper (00:03:20)

I love it. How do you define emergence in this context?

Steve Schlafman (00:03:27)

I love the idea of the adjacent possible. Stuart Kauffman at the Santa Fe Institute coined it. Steven Johnson popularized it. They use it in a technological sense, where there's a set of capabilities and that current set of capabilities eventually unlocks the adjacent possible, which is an entirely new set of capabilities. And so the way I like to think about emergence is that we have that— In a company, there's a set of ideas, a set of capabilities, values, and as we move through time and space, we learn. And the container emerges and the opportunities emerge and things are proven, disproven, and it becomes almost like this organic process vs. this process that's forced.

Dan Shipper (00:04:28)

Yeah. Here's how I think about this. And I think this fits in really well, to your point. And I've only recently been able to sort of articulate this, but I'm curious what you think. I think it'll be interesting. I think the thing that you're pointing to, when I showed up and was fundraising and wasn't like, here's a big thing, it's definitely going to change the world or whatever. But I was like, here's some things I know. And here's some things I think. And I want to create a space to play around basically. I think the reason why the other way of doing things is sometimes helpful, but a big reason why it's not helpful and why it becomes rigid is because that is basically people doing what they think they should do or telling the story they think they need to tell in order to raise money. And sometimes that is actually true. You actually do need to tell that story. But as I've run Every for for a longer and longer period of time, and just generally have been starting companies for basically my whole life, I've started to realize how much of a company building is an expression of who you are as a founder. And how much better companies go when a company is an expression of who you authentically are vs. who you think you should be or think you need to be or whatever.

And the reason why people end up doing those pitches is because they're not particularly comfortable with who they are and they want to start a company in order to be seen differently or whatever, which is totally real. I do that too. I did that a lot. I raised money in this way that was like, hey, I don't know what this is, blah, blah, whatever. But even still, right after I raised money, I just pretended basically to be a venture-backed CEO for the next two years, which was horrible for me and horrible for everyone, because I was like, not at all. Then I was grinding against my nature and once I really just admitted, hey, I want to be a writer and I really want Every to be a great business. I want to be an institution, but I want to do it by spending most of my time writing or at least half my time writing, which I know I'm not supposed to do as a venture-backed founder. You're not supposed to do that. But as soon as I did that, everything sort of unlocked in this kind of crazy way. And I was actually extremely important for that because I realized that I wanted to be a writer and that I wanted to start a business, but I also wanted to have it be part of building a great business. And then I asked you, has anyone else done this, which is an un-Google-able question. You cannot Google for that, right?

Steve Schlafman (00:07:16)

You cannot. Absolutely not.

Dan Shipper (00:07:16)

ChatGPT was like, yeah, Sam Harris for example, a writer and podcaster has a Waking Up app. It's a gigantic, amazing business. Or Bill Simmons, a podcaster who started the Ringer and Grantland and sold to Spotify for a couple hundred million bucks. And I was like, oh, wow, I can do this. And there are patterns for how to do it, but it's not talked about at all because it's not the typical Silicon Valley story. And I bring all this up because I think that sort of the way that things end up emerging organically is you're in a position where you can allow yourself to be sort of your full self and that is going to be that business that you build is going to be a sort of unique shape. That is actually sort of illegible because it's hard to describe in terms of past patterns. I think those are the best businesses. And obviously, you can go back once you have it and start to put words to it and start to describe it. But the ones that are the businesses that are most legible are often the businesses where you're fitting into a pre-established box that works. That's actually not particularly compatible with you or compatible with the world. Anyway, now I'm rambling, but I thought you'd like that.

Steve Schlafman (00:08:32)

I love it. And it's interesting. So much was coming up as I was listening to that first, I'm thinking about one of my clients right now that started a unicorn, his previous business, he went and raised venture capital for his second business and what he's realizing is that it's boxing him in. It's almost as if his creativity and his genius isn't able to fully flourish because he feels the pressure of having to build a certain kind of business that's no longer aligned with who he is. 

And I just think that there's something really magical. And I think about Downshift and the way that we're building it. You use the word playground. I like to think of it as a sandbox. And for us, it's like a playpen where we know we're really passionate about this problem of helping professionals through transition. The way in which it's ultimately going to manifest, right now we do one on one coaching and we have our decelerator program, but we're already starting to see how it's going to change and it's going to change not just because what we're learning from the market, but because who we're realizing we are as human beings and who I am as a founder. And the last thing I would say, so it's like you're reading my journal. I wrote that the next chapter of Downshift is going to be like me really leaning into my genius and the things that I love to do, which is write and create and coach. And if I'm not doing those things, then I'm not going to be happy and it's not going to be the most aligned fullest expression of me.

Dan Shipper (00:10:28)

I love that. I love that. And it's so funny how hard those choices are. And it’s like, oh, I gotta make that choice again, but once you do it, even if it's scary, at least in my experience, it tends to work, which is great. Maybe I'm lucky. Because my passion isn't playing classical flute or something, but I love business. Another another way I've been playing around with thinking about it and describing it is that I think a previous version of business, the way that we thought about it is it's sort of science and building a business is sort of like a machine and you are a machine and therefore you need to think about it in those very reduced terms. And so if you're a unicorn founder and obviously the next thing you want to do is build the biggest thing possible. And the way to do that is to raise money from the most impressive VCs. And then you're like—

Steve Schlafman (00:11:29)

Yeah, go to Sequoia or any number of great funds.

Dan Shipper (00:11:34)

And you're like, cool, I'm going to be a machine and it's going to be a machine and whatever. And then you're like, actually, I feel very boxed in. I don't really, and I think that what that boxed in feeling indicates to me is there's a different way of building businesses that looks at building businesses as art as a creative expression. And that's not for everybody. Not all people need to think that way, but that's definitely how I feel. And that's sort of the happiest that I am. If you're building businesses as art, the choices that you make are going to be different because they're going to be about how you feel and whether you're in that sort of creative mode enough. And I think you can actually also build a really great, really big business doing that, but it's just going to look a lot different than other sorts of businesses. And you have to deal with the kind of side-eye you get from people for a while. It was really hard for a couple of years, building Every and be like, I'm building a newsletter—people didn't like that.

Steve Schlafman (00:12:32)

Newsletters can be very good businesses.

Dan Shipper (00:12:34)

I mean, but not to the people that we hang out with—or not all of them, but some of them. Even if your business is making $1 million a year, that's nothing—it's not even worth your time.

Steve Schlafman (00:12:47)

Yeah. And I think though, you're one of those founders that are unwilling to just stay on a track and you're open to what wants to emerge.

Dan Shipper (00:13:01)

I really try to be.

Steve Schlafman (00:13:03)

And look at Every now. It’s very much a playground for you.

Dan Shipper (00:13:11)

Yeah. And I think you made a lot of the same decisions. It's really hard. You had a really great VC job and you could have done that forever. And it's really hard to go off and do what you did. And I want to start to transition this conversation because I know you have a lot of AI stuff to share with us. One of the things that I think is interesting, I've only been watching from afar, so you tell me, but I feel about a year ago. I was writing a lot of takes about AI and therapy and coaching and blah, blah, blah, blah.

Steve Schlafman (00:13:40)

I saw those.

Dan Shipper (00:13:41)

Yeah, I definitely felt like you were sort of wary of it taking away the human element. And maybe be wary of using it. And I don't know what's changed, but I think that something has changed. Maybe you're still wary of that, which I think is a legit thing to be worried about, but to be clear, you at least seem to have found things that you are enthusiastic about. So give us a high-level overview of where you are in your kind of AI thinking and journey and where you started and where you are now.

Steve Schlafman (00:14:11)

Yeah. A few caveats before I share. First, I am not on the bleeding edge of AI. Second is I have been a lover of technology my entire life and so I've been very fortunate to see a number of pretty massive trends—internet, mobile, social, crypto. What I'm gonna say is that AI is the most profound thing I've ever seen. By each passing day, I just cannot believe the power, the cost, the depth, the breadth, and I really believe that we're on the cusp where—using my language, transition—we're on the cusp of what I've been calling the great transition and I don't necessarily think that we're prepared yet to based on what's coming.

Dan Shipper (00:15:16)

Interesting. Transition from what to what?

Steve Schlafman (00:15:18)

I don't know. I'm not a futurist, but I can feel it. I can feel that there's something about this technology that is so powerful that it's gonna fundamentally reshape the way that everything is done in a way that we haven't seen before. And I see it in my own life. I see it in my own life.

Dan Shipper (00:15:41)

Well, take us through. Pick something concrete that you're using it for that you want to talk about.

Steve Schlafman (00:15:46)

Well, I don't know if your audience would consider this concrete, but I have a lot of fun with it. So in my work, one of the things I'm focused on right now is, I love Bill Plotkin, who wrote a book called Soulcraft. He runs an organization called the Animas Valley Institute. He's an eco-depth psychologist.

Dan Shipper (00:16:09)

That's cool. What's eco-depth?

Steve Schlafman (00:16:11)