What Generative AI Means for Startups, and Are Executive Coaches Worth It?

Sophia Amoruso: This bra is fine, right? Whatever. It's not, like, lewd?

Alex Lieberman: What does the word lewd mean?

Sophia Amoruso: Come on.

Jesse Pujji: Best interaction ever. Did we record that? Lewd is such an old man word.

Sophia Amoruso: The definition of vanilla. No. It's not.

Alex Lieberman: I'm looking it up right now.

Sophia Amoruso: No.

Jesse Pujji: And that Alex didn't know it was just icing on the cake.

Alex Lieberman: A drug taken to relieve anxiety. I think that's Quaaludes.

Sophia Amoruso: No Quaaludes. L-E-W-D.

Jesse Pujji: L-E-W-D.

Sophia Amoruso: It's L-E-W...god.

Alex Lieberman: "Crude and offensive in a sexual way. She began to gyrate to the music and sing a lewd song." Yep. I did not know what that meant.

Sophia Amoruso: Takes effort for me not to be. I'm kidding.

Alex Lieberman: What's up, everyone? I'm Alex Lieberman.

Sophia Amoruso: And I'm Sophia Amoruso.

Jesse Pujji: Yo, this is Jesse Pujji.

Alex Lieberman: And this is The Crazy Ones. Okay, we are back to The Crazy Ones, a show that is for entrepreneurs by entrepreneurs. I'm Alex Lieberman, as always, joined by my co-hosts, Sophia Amoruso and Jesse Pujji.

Now, before we hop into the run of show for today, few reminders. First of all, it is amazing all of the feedback and response that we've gotten to the show so far and how quickly the show has grown in just four or five episodes. With that, we would love to hear from you. We want to get to know the audience, so shoot us an email at thecrazyones@morningbrew.com. Let us know any ideas or feedback you have for the show, or just introduce yourself and you will definitely hear back from Jesse, Sophia, or myself.

The second thing: There is so much going on Twitter right now and with Twitter and everything involving Elon Musk, if you haven't already heard about it. So make sure to check out our emergency episode, which came out earlier this week, where we talk about what's happening with Twitter and Elon, what we would do if we were Elon, what are the decisions we'd make, and it'll just bring you up to speed. So make sure to check out that episode on The Crazy Ones' YouTube channel or where you listen to your podcasts.

Now, let's talk game plan for today. We are going to be talking about generative AI. Why it's blowing up right now, what it is, and what are some of the business possibilities that we see within this space. Then we're going to talk about the long-awaited, very heated conversation around executive coaching: our experiences as co-hosts with executive coaches, if we see value in it, and lessons you can learn from our stories of having executive coaches. And finally, we're going to play a new game. You're gonna want to make sure that you stick around for this. We call it Product Hunt Roulette. Product Hunt is this website that I have loved perusing for basically my entire career as an entrepreneur. And we're going to play roulette—we're going to look at interesting startups and we're going to analyze them as both investors and entrepreneurs.

So let's hop into this thing. Generative AI. It's something that you hear it and I feel like I just get a bad taste in my mouth. They really need to figure out a way to rebrand this. What do you guys think about just this space in general?

Sophia Amoruso: I think it's super fun. I took, not the deepest dive, but a deep dive yesterday and came up with some really fun stuff on DALL-E and have been thinking about all of the incredible applications of it. And it's something that I understand that can be applied in a way that the metaverse doesn't. There are other technologies being built out there and gold rushes happening. And what I love about generative AI is that there aren't any clear kind of financial reasons for pursuing it. Like, there is, but also it feels like people are pursuing it because it's an important and interesting technology, and not an opportunity to sell real estate to Gucci in the metaverse.

Alex Lieberman: Sophia, what I think is really cool is that you came into this topic being relatively fresh to it and you did a bunch of research to get up to speed. You just talked about these different gold rushes. So you have the metaverse, you have crypto and Web3, and now let's call another one being generative AI. After doing this research, where would you put generative AI in kind of the leaderboard of where you actually see the most real-world applicable opportunity?

Sophia Amoruso: I think generative AI, I think it's really fun. I don't want to run around looking like a Lego in a land talking to people in what feels like a chat room.

Jesse Pujji: I want to back up just for a second to explain, based on even some of the stuff I've learned, of what is generative AI. And I thought there was that article you shared, Alex, that Sequoia wrote, which I thought was very good. And the way they framed it, which I thought was very easy to understand, was like, look, computers are great. We know computers are better than some things at humans. If you want to do a really hard math computation problem, it's been like for 30 years, computers have been better at lots of fast calculations. And then there was a little bit of this, like, can they analyze problems? Can you use AI? Can you run regressions? And we all sort of know that one intuitively, but the idea that they could write better or make better pictures, that seemed like total sci-fi shit until now.

And when people say generative AI, they mean AI that can actually make something. And typically so far it's been in writing and it's been in pictures, but there's a bunch of other use cases, but anything you could imagine, and it's been pretty surprising I think, at least to me, that you wouldn't have expect...the first thing was like fine, mathematicians didn't have jobs anymore, theoretically, because computers could do their jobs. Now it's like, wait, artists are next? That's strange. But that's kind of what it's been.

But I think, just so anyone listening, that's what generative AI is. It's something that generates using AI and there's even more categories of AI, which I was not aware of, that you could think of all the different things a human can do really well that then, can a computer start to do it better?

Alex Lieberman: Oh yeah. It is such a deep rabbit hole and I think that definition is super helpful. I think the other question beyond what is generative AI is why are we talking about it now? Because this isn't actually new. There's been so much work around generative AI that's happened basically since OpenAI, which was once a nonprofit; now it's a for-profit. It was co-founded by Sam Altman from Y Combinator and Elon Musk, who everyone knows, and four other founders. They've been working on this idea of ultimately getting to AGI: Artificial General Intelligence. Basically the notion of a machine that has the ability to learn and reason as well as the median human being, that's how Sam Altman defines it.

So they've been working on this since 2015. Why is it all of a sudden a huge thing? I think there's one piece that is, it's officially in the zeitgeist because of the applications you can do with it. And then there's one piece of, technology's actually in a place where it can be usable and practical. So even if you look at Exploding Topics, which is one of these great sites that you can view trends and come up with business ideas, look up OpenAI on Exploding Topics and it's up 1,900% in search volume in the last two years. And at a time in, especially the venture landscape, where it is really fricking hard to raise venture funding, unless you're Jesse Pujji and have a business like Kahani, it's really hard to raise money.

But I would say, going back to Sophia's point about gold rushes, investors are plowing capital into generative AI right now. Jasper AI just raised $125 million at a $1.5 billion valuation. Jasper...Sophia, we'll talk about it in a few...

Jesse Pujji: It's only two years old, by the way; the company's only two years old.

Alex Lieberman: Two years old. And I believe it was their seed or their series A.

Jesse Pujji: Yeah, it was their first round of funding. Amazing.

Alex Lieberman: Yeah. And what they help businesses do is basically create content marketing and web articles, et cetera. Then there's Copy.ai that's similar. We're going to actually play around with this as a group in a few minutes, so make sure to stay tuned for that. They raised $10 million in October and there's just, the list goes on of these generative AI companies that have raised.

I just want to point out, there's basically two big things that have made this the moment for generative AI. The first is processing power. So the big thing, without getting too in the weeds, is that there's kind of two big models that OpenAI has developed, these language learning models. There's GPT...I don't know what the acronym stands for, I didn't memorize it. And then there's DALL-E. And the way I think of the two is DALL-E allows you to put in text to output images and GPT is text to output more text.

And what happens is the way these models work is they've ingested, basically, especially GPT, has ingested basically the entire internet. I believe it's 175 billion data points. And so when you input something and it generates text based off of that, it's referencing billions of data points. And so my understanding is, processing power for computers and in the cloud finally got to a place where this can be done relatively efficiently.

The second is that a lot of this technology wasn't open source before; it was kept in private beta. For a while, OpenAI was only allowing Microsoft to use their technology and it was recently opened to the public. So now that people can access the API of these really complex models, an amazing amount of entrepreneurship and creativity is happening.

Jesse Pujji: I think one of the funny things, there's a couple pieces of this that is kind of funny when I think about them. One is, most people think AI, they think fancy technology and whatever. The reality of all AI, just so everybody knows, is all it's doing is looking at data. It just looks at lots of data and uses a bunch of historical things that have happened. Like which word follows which word in a sentence, and then predicts that that's likely to be the word.

And everyone, by the way, deals with AI every day, which is when you're texting, the auto-suggest is essentially an AI. It's basically saying, based on the sentence you're writing, here's what I think is going to be the next word that you should put, and then of course they give you a few options and then, by the way, on average which option you pick, they then learn and the learning gets better and smarter.

One other crazy one that you mentioned those two, just another one I want to throw out that's come up in Kahani actually specifically, is Copilot that GitHub built. And I think they're actually using GPT-3, I'm not sure. But what they've done is GitHub has every code repository from almost every company, huge code repositories, and Copilot sits there with a programmer while they're writing code and it auto-suggests the code that they should write.

Alex Lieberman: It's insane.

Sophia Amoruso: That's crazy.

Jesse Pujji: And my lead engineer was like, "Jesse, this code is the same or better than what I would write."

Alex Lieberman: Your lead engineer's like, "Jesse, please do not fire me."

Sophia Amoruso: He's like, "Yeah." He's like, "Lay me off. What's my severance package? Can we just negotiate that in advance?"

Jesse Pujji: His output is like double or tripled.

Sophia Amoruso: I think there's efficiency, but I think there's also, what it's taking care of for us is, for the most part, the baseline. How creative this software can be, I think, is still debatable, and just in our lives where when financially we feel stable, we're able to think about higher things like taking care of other people in our lives or having a purpose or being creative. These are all privileges. And to have software that lays the foundation for code that anybody could write, right? Predictive stuff that would just take him longer is driving efficiencies. I think there are just timeless things that exist in our lives that this kind of replicates where he can think about the really interesting features that he's able to build, rather than just the base level code that operates the thing and turns the whatever. I'm not an engineer.

Alex Lieberman: I want to play a quick game with you guys, because as I was playing around with this stuff yesterday, the question that was always in the back of my mind was, the technology is amazing but it's only as good as the quality of the output. If you don't feel like the quality of the output is good, not that it's useless, but it means the technology isn't there.

So I played two games yesterday. One game I played is, Sophia, I asked you to send me a bunch of pictures and there's this new thing called Avatar.ai where you put in 20 pictures of yourself and it spits out a hundred avatars of you. So I'm going to show that, and I want you to opine on if you think Avatar.ai did a good job. And then the second thing is I went to Copy.ai; I put a lot of information in about Jesse, one of your three companies, Unbloat, the bloating pills, and Copy.ai will turn it into either sales email or...

Jesse Pujji: They're already live on Facebook, in fact. They're literally already live. The stuff you produced is already live.

Alex Lieberman: I mean, that is crazy. So I'm going to show this to you guys and you give me your thoughts. Okay, let's go to Sophia's avatars. Can you guys see the screen now?

Sophia Amoruso: Oh wow. Oh my lord.

Jesse Pujji: Whoa. Cool.

Alex Lieberman: So what are your initial reactions?

Jesse Pujji: Can you zoom in a little bit?

Alex Lieberman: Yeah. Here.

Sophia Amoruso: Yeah. Let me make my screen wider and my eyeline drops. Holy shit. I really like the top middle one.

Alex Lieberman: This one?

Sophia Amoruso: It's a little like '90s.

Alex Lieberman: I feel like this is your speed. Like this is your vibe.

Sophia Amoruso: I mean, my face being eaten by zombies on the top right...I'm not so sure about that. I don't know if you put some text in with opinions about me, or Google headlines.

Jesse Pujji: What'd you write to get that?

Alex Lieberman: By the way, for people listening on podcasts and not watching on YouTube, first of all check out our YouTube. Second, what we're looking at right now is avatarai.me. Put in 20 photos of Sophia, and it spit out, in an hour, a hundred avatars of her. So these are fake photos, but I can just say, from personal experience, these look very close to what Sophia looks like and they're different genres. One is Sophia under a Christmas tree and the other is her as the Queen of England. And another is her as a zombie from The Walking Dead.

Sophia Amoruso: I like the bottom center one because I look smart and rich.

Alex Lieberman: You're saying the one of you looking like the queen?

Jesse Pujji: The zombie.

Sophia Amoruso: Or I'm sorry, the bottom center. Yeah.

Jesse Pujji: Queen of some Dutch country.

Sophia Amoruso: I look smart enough, but not like a bitch.

Alex Lieberman: We're going to go to game two quickly. So this is, I'm on Copy.ai, I'm gonna share my tab. Basically on Copy, I put in that I'm creating a sales email. I put in the main points I want to cover. So I literally just copied a bunch of information about Unbloat that's already on your website. You can pick a tone. So there's witty, adventurous, bold, professional, relaxed. I picked witty, and I'm just going to click "create content" and see what happens.

Sophia Amoruso: That's such a neat input.

Jesse Pujji: You shared this with me in Slack yesterday and I sent it to the team and we made ad copy. We just took the questions because we thought the questions were pretty different, like they were funny examples of eating a watermelon. I forgot what they were exactly.

Alex Lieberman: Okay, wait, it spit out a bunch. So what I put in is, this is a sales email. So the first one that came out is, "We know you can't stand bloating. We get it. It's like a kick in the gut to feel like your insides are bigger than your outsides. But we also know that it doesn't have to be this way. That's why we created Unbloat, a supplement that helps you create the gut you need and deserve." And then it goes on. Honestly, that is as good as I can write.

Sophia Amoruso: That's really good. That's really good. I had a worse experience with Jasper. Can I share my experience with Jasper?

Alex Lieberman: Yeah, you can share it.

Sophia Amoruso: So I was like okay, business names, that's the thing that I do. I write ad copy, but the topline here is very formulaic in terms of the way people write Facebook ad copy. Like, "Hey we relate to you. Here, we have a solution. Ha ha, catch your attention." It is really perfect.

So I typed in some...so it was like the function that says, "Let's name your business." And I asked it, I said, I put "an online business course for people who have or want to start businesses. It encompasses an online community and live videos, prerecorded video lessons, and worksheets." I didn't put an essay, like you put a lot of copy in there, so maybe my input wasn't good enough to get a great business name out of it.

Jesse Pujji: And what did it output?

Sophia Amoruso: The business names I got were Bootstrapping your Business, The Bootstrapping Entrepreneur, Founder's Academy, and Founder's Boot Camp.

Jesse Pujji: Yeah, that's pretty shitty.

Alex Lieberman: Let's wrap this up. Let's talk about takeaways that you have from just generative AI, what's going to happen with it and any lessons or ideas that entrepreneurs who are listening to this should be taking from this conversation. Jesse, you want to go first?

Jesse Pujji: Yeah. I have two kind of conflicting thoughts. I'd say one is, I wrote it down when we started Gateway X because Sam Altman's from St. Louis. Go St. Louis.

Alex Lieberman: Do you know him?

Jesse Pujji: I know his brother Jack pretty well. So I got GPT-3 access two years ago. And when I was writing the business plan for Gateway X I was like, I thought of AI as a "how," kind of what you did with Unbloat. We're going to use it in each of the businesses but not necessarily build a business around it. So I think at minimum, if you're a services business, whatever you are, use AI at the core.

Last night after I read your article, one thing I sent to Adriane, the CEO of GrowthAssistant, I go, what if we trained all of our Philippines people in the various AI tools? And it was just like a feature we sold in. Hey, not only are they great at all this other stuff, but they know how to use AI tools. And so I think it's going to become a critical part of any kind of business-building. Not dissimilar to what coding was. 30 years ago, businesses didn't rely on engineering at all and now it's just core to every business. I think the same thing will happen with AI generally. And so getting smart on it's super important.

In terms of building a business backed by AI, you know, I have my hesitations. It's awesome what Jasper did. I think that's great. I think, I don't know for sure, but I think Jasper uses GPT-3, and I think a lot of these companies, they risk getting commoditized because the real tech, the real deep tech is GPT-3s, it's OpenAIs. And if you're building on top of that, everyone's going to have the same functionality at some point. And so I don't know. You have to think about how to differentiate very carefully on top of somebody else's API, and actually building the tech of something like what OpenAI's built is billions of dollars of investment. So it's not an easy thing to do.

And so that's why I was just thinking to take a step back and think, eventually AWS will offer it. Microsoft will offer it, OpenAI offers it, whatever. They're all going to offer APIs that do the heavy lifting for this stuff. Then you have to really think how you build on top of them to be differentiated. I don't know the answer to that.

Alex Lieberman: Yeah, I was watching a video of Reid Hoffman interviewing Sam Altman, and Sam's answer to that is basically, the protocol layer is going to be set. Like GPT-3, DALL-E, Google's version of this, and it's going to be the middle layer where companies build. And his view is that there's going to be training of AI in a vertical fashion. So there's going to be a business that does this for healthcare or biotech or financial markets, because you can't just rely on the data set that GPT-3 has in order to do really interesting things in specific categories. That's his view. Sophia, what do you think?

Sophia Amoruso: I mean, I think specifically for entrepreneurs looking at this, I'm realizing, wow, if this gets really sophisticated, there could be a computer that can mimic my voice better than any human.

I write every word of copy on every website that I've ever made. For Business Class, it's so much copy. Every word of copy for the 300 pages of worksheets, I'm real. It's like my voice. You can't replicate it. It's what I'm trading on. It's why people are emotional about the brands I create. It's why they read my newsletter. It's not about news. And even that...you know, Morning Brew has a voice, and that's something that...you can input requests, so okay, it's witty, but at the same time there is that kind of human element. And references to things that we've experienced that software's just never going to be able to predict.

I think it can really drive costs down for entrepreneurs and I would be pretty ruthless about that. I think it can increase speed for your business. It's something I would absolutely adopt, but primarily for creative work. As an introvert who has built my best things from behind a computer and then got pushed in front of a bunch of people to be like, "Yay, I did a thing." And now I lead teams. I do my best work behind a computer with as few people as possible. At dinner, I'm better one-on-one than I am in a big group. And to be able to sit behind my computer and create work with a machine is kind of an introvert's dream. So if you're that kind of an entrepreneur, it could be really a better fit for you when it comes to what usually comes with the territory, which, we may or may not be better at leading or managing teams, holding people accountable. Collaborating with some software that is much easier to hold accountable feels like an opportunity for us as founders. If that's not your strength...

Alex Lieberman: Sophia just wants to boss around some AI.

Jesse Pujji: Sophia hates people, she just wants robots.

Alex Lieberman: She just wants to boss around AI.

Sophia Amoruso: I just want to move fast and I want to be in the weeds and I want to collaborate with things or people who understand me and my voice so that I don't do all of it. I do a lot of it.

Alex Lieberman: Okay, we need to push forward. The one idea that I wanted to share is I ultimately think within entrepreneurship, generative AI is going to make entrepreneurship significantly faster. Meaning that the speed to be able to start and test a business is going to go down by multiples. So I think the cost of entrepreneurship came down with the internet. Speed is going to come down a ton with AI. I am waiting for the day— it is going to happen, mark my words—where I fill out a 20-minute quiz and my business is created and already being tested in terms of a landing page has been built, T-shirt design is created, ads are already running on different platforms and being optimized, and the business will officially launch if I hit a threshold. I think it's a matter of when, not if.

Jesse Pujji: There'll be robots around Sophia analyzing her face.

Sophia Amoruso: I'm game. They'll be brushing my teeth.

Jesse Pujji: "Sophia seems angry, we must...immediately."

Sophia Amoruso: It'll be like Wallace and Gromit over here. Alex is too young for...

Alex Lieberman: Sophia's iRobot.

Jesse Pujji: Just imagine these robots that could analyze a human's emotions and she doesn't even have to say anything. And they know what to do.

Sophia Amoruso: Yeah, all of my disdain, and they just make me feel better.

Alex Lieberman: Okay, well, I believe you guys are going to have as strong of opinions on this next topic as robots surrounding Sophia, and that is executive coaching. We've talked about this a little bit in bits and pieces in past episodes, but I want to get to the heart of it. So I'm going to just start with a very simple question, and we'll start with Sophia. Have you used an executive coach, and do you believe in executive coaching?

Sophia Amoruso: I absolutely believe in executive coaching. I have only worked with one, and I've worked with him actually for the last seven, eight, nine years. From the very beginning when my company could afford it, when Nasty Gal could afford it. He was a big expense. Nowhere near the expense I'm about to take on with Dave Cashin, who Jesse so generously introduced me to, who's the coach I'm going to have my first call with in the next couple weeks.

Alex Lieberman: Why are you switching?

Sophia Amoruso: The executive coach I've had leads with heart, but for the most part has led with advice on how to manage people, how to think about when I was putting together my thesis for what was really going to serve me after I left Girlboss, my second company. Thinking about, I've talked about this before, Business Class feels like a project because we launch it twice a year. It's not something that's on every day where there's just this onslaught of stuff.

And with Girlboss, we were doing brand deals, we were hosting conferences, there was such a human capital lift. And so he helped me clarify that I wanted to do things that felt more like projects and less an undertow business.

When I had issues with executives or with management, for example, my nature is to run to the fire and fix things. I'm not avoidant; it's a problem. I'm actually very reactive and it shows up in all areas of my life. It can work in business; it can also be really bad in relationships. And he taught me—this is one of the most interesting things he ever taught me, is that there's a really healthy amount of avoidance that a leader needs to have to redirect people to solve their own problems instead of allow your team to come to you, ask you what you think about it or how you should solve the problem, and deputize them to come back with an answer, which I had never thought before that avoidance could be a healthy thing.

He was a lot more practical of a coach. Dave is like a heart-led guy. He loves, he's used the word "love" on our call, and we'll see how much I can love and I think it's going to help me love myself and whatever. Hopefully more therapist-y. It's not that different from a therapist except therapists don't have the understanding of what leadership really looks like, often in a way that consumes our lives as much as our time with our families or our friends and the other things we might go to a therapist about, but they can't speak to you at all.

Alex Lieberman: Yeah. Jesse, what's your experience been?

Jesse Pujji: Yeah, I mean I think I've told you guys about this story, but I'll share just for everyone's benefit. I started Ampush when I was 25 and we grew the business super hard, super aggressive, bootstrapped it to $30 million in revenue in four or five years, and killed ourselves. I mean it was rough. And killed other people too. All the while having good intentions, let's say. There's a time where, it's still on Glassdoor, people just rip me to shreds, I'm sure same as you guys have had similar experiences, and then we had...

Alex Lieberman: Do you think there are people that still dislike you from Ampush?

Jesse Pujji: I'm sure. And I don't blame...when I look back on it, I go, "Oh yeah, okay, I see. I see how I created that." And we had this kind of exit and we sold a big chunk of the company, had the success check mark, quote unquote. And then I had this period after my daughter was born where I just felt totally like, didn't want to go to work for probably six months. Would wake up, cancel my schedule, go in at 11, hang out, leave...just didn't want to be there anymore. Started kind of like, "Oh, why am I doing marketing? Advertising?" Just questioning everything. Just felt rudderless.

Alex Lieberman: And it makes sense, by the way. It makes sense, because your whole life up until that point, from the youngest age, you said literally you were known as the guy who was going to be an entrepreneur.

Jesse Pujji: Totally.

Alex Lieberman: In high school, this was your identity.

Jesse Pujji: Yeah, absolutely. And I had gotten it. And so Ric Elias, the founder of Red Venture, he literally was like, Jesse, you're the luckiest MF-er in the world. You have beautiful kids, you've done really well, you do what you want and yet there's some inner work to be done. And that was like, okay, this guy. I was like, I'll do some inner work. 

And I started talking to a coach, Dave. And we ran a process, by the way. I think this is an important part of selecting a coach, because Sophia mentioned it. We met with probably five or six, and it quickly emerged to us. We sort of called it, again, another two by two. There's on one end of the spectrum is like, are they a business consultant or are they like a, let's say, spiritual coach for you as a person or a business consultant? Are they going to tell you to reorg or how to give feedback or advice? And then the other part of it was, how experienced...how much were they a professional coach versus an entrepreneur? Somebody who had been in our world being a coach.

And we wanted someone in that top right who was more spiritual. We didn't want someone to teach us how to reorg or run our DCF or whatever. And we met with him and he sort of presented this framework of motivation to us, which comes from the conscious leadership group. And he said, "You've used fear to motivate yourselves." And I was like, "No I haven't. I'm happy, I'm good." And that's how I felt. And then he laid it out and I was like, "Oh, you're right." It's shown up everywhere. It's shown up everywhere as a thing for us to motivate.

Alex Lieberman: What does that actually look like in practice? Leading by fear?

Jesse Pujji: Yeah, I mean the framework was is there's five types of motivators. There's fear, there's extrinsic, there's intrinsic, there's play/genius, and then there's like empathic love. And fear could be anything from, I don't think much highly of myself, so I have to prove that I'm a certain way. Or it could just be, in my case, was I don't think I'll be successful. I wanted to be successful so badly and I didn't think I would be. And so I would just use that gap to constantly motivate myself.

And there's examples of, one of my favorite ones they always share is Bill Gates, and I don't know if this is true or not, but this is a theory, is very fear-motivated, sent a coffin of Lotus software to Lotus after he crushed them with Excel. Was just notoriously that intense guy, became the richest man in the world.

And this is the challenge with fear. Fear is very effective. You put a gun to my head, I'll run faster than I've ever run. But then as soon as the gun's gone, I stop running. And in his case he became the richest man in the world and Microsoft didn't sustain his motivation. Then he went all the way to the love of helping people, which is like, I'm going to go cure polio. And that's the other flip of it.

And so a lot of the work that I've done with Dave is how do I shift from using fear and extrinsic motivators to these more pure, more sustainable motivators? Because fear leaves a negative residue on people around you, like the people who wrote Glassdoor things about me, that this guy is a jerk and whatever. And then it also runs out. And mine had run out after having that successful check mark and I didn't have anything else to latch onto. And so a lot of the work was, what actually gets me motivated beyond money? Beyond success? And for me it was just transformative. And there's a bunch of other ways. EQ made me a better husband. There's so many places that it's shown up for me.

Sophia Amoruso: I also believe that what shows up in your business life as a leader is a direct parallel to what shows up in your personal life.

Jesse Pujji: A hundred percent.

Sophia Amoruso: And it's more amplified kind of example with sometimes what feels like higher stakes to weed through, and the consequence is it's so many more people and money and things that are a lot more tangible as consequences of the things that you haven't solved or worked through.

For me, reactivity can work when I'm operating independently. It doesn't work in a relationship. Reactivity doesn't work if I'm in a conversation with my team and I want to correct something or someone. Taking a pause and being thoughtful. Simple thing. Most people understand this and all of us have small things that it seems like other people just innately understand. But it's that kind of stuff that even talking to a leadership coach about business allows you to be a better person with your friends and your family.

Jesse Pujji: And you're the same person. I mean, that's the weird thing. It sounds so obvious when I say it, as why would they not be related? And why would you not be the same thing? Because you're just one person. And by the way, my version of that reactivity for you, Sophia, was also one for me. But empathy. I had no empathy...I was raised in a household where if you were doing something right, nobody said anything. And if you were messing up, you heard about it. That was it. And so the idea of appreciation and gratitude didn't really exist. And in a nice way, if I ever said thank you to my parents, they'd say, "You don't have to say thank you." Right? That's how their worldview was.

But all of a sudden in both my marriage and my work, people were like, "Dude, you're thankless. All you do is ask people to do stuff and you're never empathetic. You're not aware of their feelings or emotions." And I really wasn't. And by the way, I'm still probably at a second grade level of life of empathy, of truly understanding another person and trying to walk in their shoes and what they're feeling and what it feels like.

And so there's so many things to develop, and a coach holds up a mirror to you and shows you things. One, just a small example. I do it with a lot of entrepreneurs because it immediately clicks is, one of the first things Dave noticed about me and my co-founder Nick, was, "You guys use the word 'should' a lot." And I'm like, "Huh? What do you mean? Why does that matter?" He's like, "Well, is 'should' an inspiring word? When you say 'We should do a reorg, we should grow revenue 50%.'"

And then I realized in my marriage I was like, we should go to this party this weekend. And by the way, "should" is such an arguable state. Like, no we shouldn't. And then you start debating it. And both in work and at home, I started using the phrase "I'd like" or "I'd prefer." I'd like to do a reorg. Or how amazing would it be if X. And that little language shift...by the way, there's words like "need," "must," "have to," "should," all of them seem to drain energy from me, at least, and also feel like it's another way of, in a mini way, putting myself as like, I'm not where I'm supposed to be. I need to be better. Fear. I have fear to get to where I need to be. And that little thing was just so transformative for me. And I don't know how I would have, who would've shown me that, if not Dave telling me like, "Hey dude, I just noticed you used this word a lot." Right? So that's a cool tactical example.

Alex Lieberman: Yeah.

Jesse Pujji: Alex, what's your experience? 

Sophia Amoruso: Alex, Alex, Alex. We're recruiting you now. We are enrolling you in executive coaching. I'm pretty sure.

Alex Lieberman: First of all, Dave sounds amazing and I may need to try out Dave, get on the Dave payroll. I started executive coaching late. I started working with my executive coach right after we sold Morning Brew in October of 2020.

And first of all, what I'll say...I heard it from both of you guys, and I think it's such an important point for any entrepreneur who wants to work with a coach, is that coaches have specialties. I didn't think about it in as clean of a way as Jesse did with his two by two on "spiritual guru versus business consultant." But it is such an important point. And what I would just say is when you think about who is the coach that you should work with, I think first of all you should pick your coach in the same way that you pick a partner in life, or an employee. There's a recruiting process, and you shouldn't just say yes to the first person you're introduced to, because you have no reference point and odds are that the first person you talk to is not going to be the right person.

The second thing is understanding what are like the acute challenges you're trying to overcome, I think is so important. So for me, what I was trying to work on after we sold the Brew and then in April of 2021 I moved out of the CEO role, is there were a few very clear things. One is I was planning to sell kind of a second chunk of my equity back to the owner of our business, and I needed help in the navigating that experience. How to negotiate the right way to have that conversation, because it's something I had never done before. So I would say that was on the business side.

On the personal side, I was incredibly lost after moving out of the CEO role. Very similar to what Jesse said about this loss of motivation and this loss of identity and questioning what he should do. That was literally me to a T. I think what happened was I went from spending, let's call it 80 hours a week to 30 hours a week on Morning Brew when I moved into the chairman role, and all of my thoughts, and your thoughts end up becoming what you say, and what you say becomes who you are, all of my thoughts ended up becoming self-hating or confused. So as one, how am I going to find fulfillment for the rest of my life? And just asking that question became so lofty it felt like an insurmountable question to answer. And the second, honestly, I lost self-love. I was the most self-conscious that I've been I think in my entire life. I was saying, clearly I messed up as the CEO because I'm no longer the CEO of the company. Clearly I didn't do a good job. And so then the question started bleeding in of, should I start another company so I can prove that I can run a business at this stage? Clearly this proved that I'm not a good operator. Clearly this proved that I'm not analytical, clearly this proved that I'm not strategic and forward-looking and that I'm a procrastinator. That was the flurry of thoughts.

And I would say what Ryan, who probably...he has this amazing balance of the business and analytical side, but also deep knowledge and spirituality, mostly steeped in Eastern but has spent more time focusing on Western. And so for me, the things we spoke about was negotiating the sale of my equity, process moving into the chairman role, and with that, having love, like learning to be excited about the things that I'm really good at. Which, it was such a hard thing for me because the world was celebrating me as this young media entrepreneur. But it is not at all, going back to what Jesse was saying about the mirror and seeing a reflection, I couldn't have seen a more skewed reflection in the mirror.

And then we talked about also my relationship with my co-founder. Because Austin and I were so young when we started the business, I think I shared this with you guys a few conversations ago, we never had level-setting conversations. And I think Austin, similar to you, Jesse, he operates at a speed where you talk about the things that need to be fixed, but you never talk about the things that are going well. And so I'd never received a compliment from Austin in seven years of running business together. And what I realized about myself, probably because of experiences earlier in life, is that I need a little bit more of that validation to give me something directionally that I know that I'm competent. And so I found it largely helpful.

But what I'll also say is, it's okay to then at a point feel like you're no longer getting all of the benefit out of your coach anymore and to stop working with them. It also doesn't have to be, in my opinion, a lifelong commitment. It's okay to challenge the status quo when you feel like you've plateaued in the benefit you're getting.

Sophia Amoruso: I told my therapist yesterday "What got me here won't get me there," specifically in relationship to my work with her, and that I need to work with someone who's more active, not necessarily tells me what to do, but she's a traditional psychotherapist and she kind of sits back and I have to come to my own conclusions, and that is such a slow process and it's been great for me for several years and have told her, "I have specific things that I want to work through. And I don't know if that's something that I can do with you." And I think realizing that even, you can be really loyal to a coach who feels like an emotional relationship, but it's still a professional relationship. One more thing I'll say is it's a write off. You can't write off therapy.

Alex Lieberman: I love that.

Jesse Pujji: There's two things that came up when you were saying that about your journey, Alex, and one that I think will just help people. And it's another example of how coaches can be so valuable.

An exercise I did with Dave around that 2018 period, which sounds like you did a version of it, is just called facts and stories. And I would be shocked, by the way, Sophia, if he doesn't have you do this in the next few weeks.

But it's like, okay, you have this journey, you have this story—what happened? I would tell the story of me and I'd be like, "Oh, I wish I would've sold the whole company in 2015, not just sold a part of it. Because then I'd be done." And he's like, "Well, what's the fact and what's the story?" And well, the fact is company offered X. Did not accept that offer, took this offer. That's the fact. And the story is, "Oh we shouldn't have done...it was a mistake."

And then you write them down in two columns, facts and stories. And it's actually harder than you think. Sometimes you call things facts that are not in fact facts. So it actually takes some time to realize. A good example is, "We had a bad quarter. Like our quarter wasn't great." That's the thing we say all the time.

Alex Lieberman: That's a story.

Jesse Pujji: That's a story. That's not a fact. A fact would be revenue was up 20%. Our plan was to be up 40%. So anyway, you have to separate this. And the more you practice it, the more you do it naturally. And then you actually just try to find how the opposite of the story could be just as true as the thing that you believe. It doesn't mean you have to believe that, but you're willing to accept that you've just made up a point of view. That's not actually truth.

So when I had taken on this truth of big regret, should have sold the company, it would weigh me down and I have a charge attached to it. When I said, "Well no, I wouldn't be coaching with you, Dave, or I learned all this stuff from this mentor guy, Ric." All these reasons why it was great that I didn't sell became...all of a sudden I just didn't feel so strongly about it and it didn't hold me back in the same way. And so same thing for you. It sounds like there's that facts versus stories, which, for me, has been such a powerful thing.

The only other thing I'll add, by the way, just from what both of you said is, I told this to Sophia before she started coaching. Coaching is your responsibility. If I show up to Dave and he's like, "So what do you want to work on today, Jesse?" I'm like, "No, I'm good." He's like, "Okay cool. See you later, bud." He won't even talk to me. Because his view on it is I should be pushing the envelope of my own personal growth and trying to get better.

So whether you switch your coach, whether you keep your coach, the thing to remember is they're here to help you with your development. Like a star tennis player. Star tennis player, they're trying to be the ones who are the winners of Wimbledon. Their coaches are there to make them better, but if they don't have the drive and they don't go, "Well, I want to get my backhand to be better this month," then there's not going to be...so I think it is important to come in and you yourself have to have things you want to work on and get better at to make the most out of a coach.

Alex Lieberman: Oh yeah. Taking ownership over the relationship you have with a coach, just like a therapist, is so important. For the longest time with therapy, also, when I was given homework to do in between weeks, sometimes I wouldn't do it. Or if there were things that really helped me in our discussions and things that didn't help me so much, I wouldn't communicate what those were. Yeah, to your point, you have to take ownership over your experience that you have.

Sophia Amoruso: I think ultimately what you guys are talking about is what does success look like? What does success look like for me personally? What does success look like? Okay, Alex, I peaked, I'm not a successful CEO. Oh, shit. I pocketed millions of dollars. I'm 28 years old. What's next? Is that success? Something that we are just kind of running, just continue to run and run and run as entrepreneurs. And even when we hit that level of success, Jesse, if it's 20% growth or even what success looks like in therapy or in executive coaching without kind of laying that thesis out for ourselves, it doesn't matter how much time we spend on it, therapy, our business, whatever, making money, we're never going to get to a place where we're building real meaning long-term unless we think about that. That's my summary of everything that we just said on the most kind of meta level, from what success looks like in executive coaching all the way to what success looks like when you're talking about your business or your personal life or your feelings about your life.

Alex Lieberman: Yeah, I mean at the end of the day, all of this is just based on mostly stories that we've had for such long times and it's the constant tension between our old stories and new stories that we're trying to create. Okay, let's end this episode on a high note. We're trying a new game. I appreciate you guys being guinea pigs because I literally came up with it five minutes looking at my ceiling being like, what would be fun? It's called Product Hunt roulette. Are you guys Product Hunt fans?

Sophia Amoruso: Yes.

Jesse Pujji: Medium.

Alex Lieberman: Medium? To me, it is my favorite place to nerd out on new startups and just discover new ideas. So here's what we're going to do. I'm going to share my screen and there's this thing on Product Hunt called Time Travel. So you can go back to any day ever on the site and you can see what startups were hunted that day and which ones finished at the top of the list. We're going to pick a day and then we're going to talk about one or two of the top-rated startups that day. So here's how we're going to do it. Sophia, give me a number between 1 and 12.

Sophia Amoruso: 9.

Alex Lieberman: Okay Jesse, give me a number between 1 and 30.

Jesse Pujji: 23.

Alex Lieberman: Okay. 9/23. September 23rd, 2022. So just over a month ago, we have the top Hunted products are Versify: Engage and reward your customers with digital collectibles; BG Eraser: Clean up and remove unwanted objects and background from images; and then The Hustlers: Stories of people making money while having a full-time job.

So we're going to start with the first, Versify. So I'm checking out Versify. It got 581 upvotes on the day. And by the way, at some point in the future we'll talk about how to have a successful launch on Product Hunt, because Product Hunt has been such an amazing accelerator for a lot of businesses that are now unicorns. But just to talk about Versify for a sec. It says Versify's product suite makes engaging your customers with digital collectibles effortless for any business. Instead of building an entire Web3 taskforce with Versify, companies can now have their engagement strategy up and running in 10 minutes or less. I'm going to stop there. First of all, do you guys understand what their product is? And what are your initial thoughts?

Sophia Amoruso: Seems like a loyalty program that's run on Web3. It sounds like what Tyler Haney is doing, who built Outdoor Voices. I'm not exactly sure.

Jesse Pujji: I think I get it. I like it. I like it.

Sophia Amoruso: I like it.

Alex Lieberman: Just so I understand, it's like you buy something...I'll just use an example of Bonobos because I'm on a big Bonobos kick these days. Buy something from Bonobos, I get a pair of pants and they send me an NFT as someone who has bought product, and as I buy more and I have more loyalty to the brand, I get new NFTs. Is that your understanding of this?

Jesse Pujji: Yeah.

Sophia Amoruso: I think it could also be a potential referral program. I mean that's what has helped build Morning Brew, which is, at the bottom of the email it says "Refer this many people, you'll get this" and there's multiple tiers of it. People buy into the brand, they're excited, they get their name featured, maybe at the bottom of the email. Everybody does it a little bit differently. But seems like something where you're gaining digital assets. That may be an application as well.

Alex Lieberman: Yeah, I mean guess my initial reaction is I feel like part of this or the way that a lot of companies are going to apply this is going to be kind of stupid, and customers aren't gonna get excited about it. Like, getting a badge after buying a pair of pants? I would be really unexcited about that.

I think there's an aspect where it allows for creativity. So I think there's an aspect where it can be a really...I'm thinking of the craziest applications that I don't know if they're possible. Well, one is utility-based NFTs. So how, if I hit a thousand dollars in spending in three months with Bonobos, does the NFT I get give me access to happy hours on a monthly basis at Bonobos's store in New York City. Or at a crazy level that I don't think is possible yet, but it's like what if NFTs actually gave me Bonobos equity. Like as a customer I could actually start building up equity in the business.

Jesse Pujji: A rev share. I had an idea like this.

Sophia Amoruso: I would do it for money. I would only do it for money.

Jesse Pujji: I had an idea this that we actually wrote up, and I think my big use case was, imagine the sneakerheads, and I'm one of the thousand people who gets to buy a little piece of the revenue of this awesome Air Jordan or whatever because I'm good at that and I know it, then I'm on a leaderboard and I show that I was one of the first people to figure this out. Then it actually has some value so I could sell it because I'm done with it now and somebody else wants to buy it. And the digital collectibles...do you guys remember when Facebook was selling stickers you used to put on your Facebook profile? You may be too young, Alex.

Alex Lieberman: Yeah.

Jesse Pujji: That was like a nine-figure business they shut down. Because Zuckerberg was like "Eh, it's too small." But at the time, I remember, I bought one for my now wife. I was like, "Here's a heart for you." It's like I spent $2. You have to, like you said, figure out the right angle, but there's something there.

Alex Lieberman: Well, I think to your point, we're always going to care about status. It's just a question of, in what context is status going to matter? Because I'm not going to care about being like gold pants of the month for Bonobos.

Sophia Amoruso: I mean it's like Twitter blue.

Alex Lieberman: Yeah, exactly. Okay, we're going to do one more of these. Okay. Stop sharing. Okay, the second one we are doing is BG Eraser. I don't know if it's just big and big wasn't available. So let me click on this.

Sophia Amoruso: We need Jasper to come up with a better business name.

Alex Lieberman: BG Eraser. Okay, I'm bringing it up now.

Sophia Amoruso: Background. Background. Background.

Jesse Pujji: I can't see it but I remember what it was.

Sophia Amoruso: It's background.

Alex Lieberman: Okay. Yes. Oh, that's what it stands for. It's not big, it's background. Jesus, Alex. Okay, so this had 297 upvotes. BG or Background Eraser, thank you, Sophia, could remove unwanted objects, people, text, detects, and watermarks from any images for a hundred percent free. First of all, companies that have watermarks on their images are going to be really freaking pissed about this. What do you guys think about this thing that basically you put an image in and it can remove background. I've seen background removal before. I've never seen object removal, which is kind of cool.

Sophia Amoruso: I love it. I love it. I've been trying to mock up chairs in my dining room because mine are just shot. But I've literally been going into Photoshop and magic wand, whatever, selecting the chairs, pulling them out. There is no background, then dropping in, again, dropping out the background and the chair that I want.

Alex Lieberman: Oh, you're like doing this as a way to test how things would look in your house.

Sophia Amoruso: See what the chair would look like at my dining table. I would love for this to help me with that.

Alex Lieberman: What do you think, Jesse?

Jesse Pujji: I like it as a product. I mean I think there's a need for someone's photo bombing and you want to get them out of the photo because it's a good photo. And I think whatever million versions of that, I struggle with it as a business. 

Alex Lieberman: Yeah. It feels to me like it could be a feature at five different massive design companies.

Sophia Amoruso: Canva is going to do this in like a month.

Jesse Pujji: I just don't know how you grow businesses like this, because they don't make enough money to pay for customers. It just, it's a tough one from that standpoint. For me. Maybe if this person has a secret, great.

Alex Lieberman: Okay, so it sounds like thumbs down on BG Eraser as a business. Thumbs up on whatever the last one is, the digital collectible loyalty business. Any parting words before we call it a show?

Sophia Amoruso: This was fun. We're getting better at this.

Jesse Pujji: No. This was a good one.

Sophia Amoruso: If you haven't subscribed, you really should.

Alex Lieberman: Make sure to subscribe to the show and shoot us an email at thecrazyones@morningbrew.com. Introduce yourself. We want to meet our audience. Send us ideas, send us feedback, and we'll see you guys next week. Later, everyone.