GTM Unfiltered

Judd Borakove: [00:00:00] And because of Craig, who's awesome, we actually all watched your content too. So we actually

know stuff.

Alexis Gay: Oh my God. you

prepared for the guests that you invited on your own show?

I'm sorry. This is just so emotional that you would do the bare minimum before

inviting me to participate.

I know. Seriousness, it's always flattering, um, to, to show up and have people know, uh, what you got going on. So thank you guys and thank you for having me.

Craig Rosenberg: Yeah, no, no problem. so, uh, I, I found Alexis on Twitter, but then follow her humor on Instagram and now, uh, everywhere. So I'm really excited as you guys know. So here's, what's interesting is, um, so Alexis actually came from the B2B [00:01:00] go to market world, right? So she was an SDR Twilio, which, so when I was looking her up, I'm like, Oh my God, because I did want to work with the Twilio before she got there, she ran creator partnerships Patreon, which is like, so, you know, basically create a world, which may or may not have been part of her inspiration to leave, I believe during the pandemic or after to go become a new kind of entrepreneur.

So you are a different entrepreneur than we've had on the show. And that's really exciting because Uh, you are now a comedian. You have a great podcast. We need to talk about your guests are really good. And I was really jealous, um, looking at those and listening to those. Um, but like I think about comedians and folks that are sort of becoming creators and how much you have to put yourself out there, part of building your business.

It's really incredible. And so, um, you came out of left field and we're really excited to have you, but for the audience, Alexis

Gay, she's here.

Alexis Gay: [00:02:00] hell yeah. Thank you so much for having me and thank you for that introduction. I really appreciate

Craig Rosenberg: Was it good?

Alexis Gay: I think it was good. I think you nailed all the key points.

Judd Borakove: He gets better

every week,

Alexis Gay: that's great.

Craig Rosenberg: mean,

Alexis Gay: How many episodes have you guys done?

Matt Amundson: right

Judd Borakove: like

seven or three. No,

Alexis Gay: I was going to say when I looked it up, it looks like maybe four or five.

Judd Borakove: I think

like eight, I think eight released. We got a bunch that

are still that we're, we release one a

week

Craig Rosenberg: yeah,

Alexis Gay: Oh, very cool. Okay. Exciting. And is this the first foray into podcasting for most all of you or is this, uh, a second go around?

Craig Rosenberg: I think we doubt, I mean, everyone

dabbled.

Alexis Gay: Everyone dabbled.

Matt Amundson: Uh, Craig had the podcast, uh, with Gartner. Uh, I've been on podcast and according to my Spotify wrapped, I've, uh, I'm in the top 4% of consumers of

podcasts. So,

Alexis Gay: Oh,

Craig Rosenberg: No way. Look at you,

Judd Borakove: and I've done two different

podcasts and I hate

[00:03:00] podcasts. So, you know,

Alexis Gay: Okay. Interesting. And

Judd Borakove: yeah, here I am.

I know

Alexis Gay: coming back for

Judd Borakove: someone's

got to wrangle these two. Cause you know, they're so

out of control.

Alexis Gay: what would they do without

you?

Judd Borakove: Probably a lot better.

Craig Rosenberg: clear, like without Judd, there would be no show. And so like, cause Matt and I talked about it for like eight months and just like, yeah, let's do it. And then like a month later, he's got like a production team and like, he's got the whole thing going. It was incredible.

Alexis Gay: Yeah, you need the just do it guy for sure.

Craig Rosenberg: is the Just Do It guy.

I mean, like, there's, there's no holding him back. All right. So quickly though, uh, tell us more about, I, I'm just, I'd like to dive in on the transition

here. Like, just give us the whole rundown. You're sitting there and B2B go to market and you decided to become a comedian, like, or you were a comedian, but you decided to make that your business.

What, tell us

about that.

Alexis Gay: definitely the latter. I started doing comedy When I was working at Twilio and I started doing improv comedy specifically because [00:04:00] my whole life started to feel like it was in tech, about tech, around tech, talking about tech. And I loved and still have a lot of love and appreciation for the tech industry, but it was just, I couldn't get like outside of it.

And I needed something, I needed to do something with my time that would like. Just wash it off for like a couple of hours at a time. And I, and especially because being very early in my career, I was about four years into my career when I was at Twilio. A lot of your friends are in tech, your social circle, et cetera.

So it felt all consuming. Doing improv, it was just like this way to do something different once a week. And growing up, I had done a lot of acting and really loved acting, but unfortunately you can't really. It's actually becoming increasingly easier, but at the time, especially, there wasn't really a way to act as a hobby, but improv comedy does afford you that opportunity to be up on stage, to be in front of [00:05:00] audiences, to be making something with other people.

It's incredibly collaborative as a team sport, but. No one expects you to then go and do it full time. You can just kind of do improv for fun. And there's a lot of benefit actually in the business world to being a strong improviser. I think it's just good for life. You have to listen really well and be very collaborative and very open minded.

And so I think there's a lot of benefit to it. So I started doing improv for all those reasons, mostly because I needed the brain bath at the end of the day. And I loved it. I loved it so much. I like physically remember what it was like the first time we got a laugh at our Improv 101 grad show. I just remember that feeling of like, Oh, I want, I want to do that again, you know?

And it was not the kind of thing that was 2017. It was not the kind of thing like, okay, as soon as I felt that lightning strike, I was like, I'm going to leave tech behind and bust out of here. It was just like, Oh, great. I love this thing. I'm going to do both. Improv led to making short form sketch videos.

Uh, [00:06:00] also in 2017 and then that led to making longer form YouTube videos where I was writing and telling stories, but then I would edit in cuts and sounds, which is very common at the time. Still around now, but there was definitely a boom in this style of telling stories. And then recognizing that I was both actively getting on stage, doing improv and writing these YouTube videos, it was honestly like it occurred to me I could do standup.

Which previously, I'd always been really afraid of because in my mind, I was like, what if they don't laugh? What do you do with your sense of self? Like how, what do you do? Literally, how do you keep living in the skin? Like, do you get a new body? I like didn't understand. Do you go into witness protection?

I did not understand what you did after that moment and it held me back and then I just had this realization that I was like, But I'm getting on stage, and I love that, and I'm writing, and I love that. And if I just combine those things, then maybe I [00:07:00] could do stand up. And so I went to an open mic, and uh, the way I tricked myself into doing that was by making it, by making the success metric not to get laughs, but to do the mic.

And that was the trick. And when the success was just do it or don't, that was easy. Just do

it. Laughs are, laughs are later. And then Lather, Rinse, Repeat, I was doing all of those things. Improv, Stand up, and creating videos. This is while I was working at Patreon. I loved my job at Patreon. Uh, I joined to do creator partnerships and operations, but I ended up running the creator partnerships team and building out a biz ops team on the go to market side.

And by the time I left, I was managing a team, those two teams of, um, in total seven people. And I loved my job, but I became increasingly passionate about all the stuff I was doing outside of it, all the stuff with comedy. And during the pandemic, my following online started to grow at a pretty unexpected clip.

Because I had been making things [00:08:00] online for several years and it's not like I felt angsty that no one was watching. I just was aware some people watched but it wasn't anything meaningful and that didn't bother me because I had my job and I love my job and this is for fun. And then sincerely during the pandemic, I started making one video every week because I was going crazy.

Let me be very clear. I was going insane. I was living alone. In a studio apartment in San Francisco, California in the year of our Lord 2020, I was losing my mind and making one minute videos was just like all my brain could really compute because I was used to making like seven minute YouTube videos and my brain was like, that's hilarious, you're never gonna be able to do that again.

So I started making one minute videos. And as a way to stay, um, as a way to do something outside of work, work being then sitting on your computer all day in Zoom meetings, I started making a video every week, and then one of [00:09:00] those videos got the most views, um, I think it still tops the views actually that I've gotten on a single video on Twitter.

At that point, the most views that a video of mine had gotten was 1, 100. It was 1, 100. I was stoked about that, by the way. I was like, hell yeah. 11, many people 1, 100 people is? So many. They all saw my video.

That's dope.

Judd Borakove: hundred.

more than a

thousand.

Alexis Gay: Yeah, exactly. Can you imagine? It's, uh, and it's 1, 000 more than 100. So I, uh, was stoked on that and then the next video I posted got 3.

1 million views and in one week my following went from 950 Twitter followers to 15, 000. Um, because, and my theory is that when I think when people landed on my account, driven by those 3 million views, they, there was so much content there. There were so many videos, so many jokes I had written over, you know, months and years of regular output that I think people thought, this is a comedian.

That's a very natural conclusion to draw, right? [00:10:00] And so they, a bunch of them thought, she's a comedian. Um, they weren't like, well, this looks like a, a head of creator partnerships and business operations to me. And so, um. It was kind of intimidating to have all those followers all of a sudden. It felt like I'd been performing stand up to an intimate group of 50, and then 5, 000 people walked in the door and I'm still holding the mic.

That's how that moment felt. But I decided that night, because it got like, you know, a million views in the first day, and I was like, what is happening? I decided literally that night, I was like, okay, some of these people are going to leave when I start, when they see more. I, that's just what's going to happen by the numbers.

Right. And so. So I'd rather rip the band aid off and let that happen so that people with whom my stuff will resonate can find me. And so that night I remember being like, you have to tweet a couple jokes. You just have to do it. Rip the band aid off. And that's been part of my ethos ever since is, is I'm going to, I have to keep putting [00:11:00] stuff out and putting stuff out that.

is from my perspective, whether I am positive that's what people will like or, uh, or not. And, um, after that initial following and after the excitement around how good it felt to make stuff and have it seen, oh my god, it feels really good, you guys.

Craig Rosenberg: We

Judd Borakove: No,

Craig Rosenberg: have a hundred. I mean, this is a,

Matt Amundson: Alexis, in our defense, this podcast has been called not terrible.

Alexis Gay: Wow, by,

Craig Rosenberg: our producer?

Judd Borakove: by my mom. who's my

Alexis Gay: yeah, I was gonna say, who's

mom?

Craig Rosenberg: Like, yeah, I went on and gave you guys a rating. It was like, this

isn't terrible. I'm like,

oh,

Alexis Gay: This isn't terrible. I, you know what? I will, I'll say it. I am not having a terrible

time. Whoa. I

know.

Craig Rosenberg: And

Judd Borakove: We just won.

And now that was about as

Matt Amundson: yeah. We're good

We're

good. Yeah.

Craig Rosenberg: picture of Alexis just in everyone because it was the quietest that we've ever been as you were [00:12:00] talking.

Cause it was so engaging. It's an incredible story. Um,

I I just, but like, was it, I mean. You sort of got to this point, but then you're out on your own. Like, do you, like, was there, is there a business plan or do you just go, you know, enough to make it work? And then what does that look like? It's

Judd Borakove: And how, how did your experience in business

affect it? Because I'm so

Alexis Gay: god,

Craig Rosenberg: Jesus.

Alexis Gay: I can do both. No, I love these

Craig Rosenberg: I know I was going to follow up with that, but anyway, go ahead. Go

Judd Borakove: I got to come over the top.

Craig Rosenberg: jumps in with these. Yeah. He's just,

it's no, go, go.

Alexis Gay: It's okay. I mean, it's very exciting. Business strategy is very exciting. We're all very excited to discuss. Um, so okay, there's, uh, I'm actually, this is a, this is a three part answer. So the first part is I, we are missing one step of the story, which is between that initial following build and then the actual resignation from Patreon, because that was between April and December of 2020.

What a [00:13:00] time to be alive, by the way. So I say that for a couple of reasons. One, this was something that in my mind, as much as I ultimately did make a decision to resign, it really felt more like I continued to follow what was most engaging to me. And then being pretty honest with myself when my job, which had been so exciting and which I had been so passionate about, I started being honest when that started fading in interest to me.

Which was really hard because I've always loved, or it's always been very important to me to love my jobs, and then all of a sudden I was like, I would rather write tweets than participate in this very important headcount strategy meeting. And if I had been in IC, Maybe I would have stuck around a little longer, but it was very important to me as a manager.

I think that's a service position and I was fearful that if I started delivering it less than a hundred percent. I would be, it would be detrimental to the careers [00:14:00] of people I cared a lot about who were looking to me to help them grow. And I took that incredibly seriously. And so the first time I was like, I'd really rather edit my video than work on this thing.

I was like, listen to that red flag and check in on it. And then I kept checking in on it and it just kept getting louder. And so in some ways, as much as it was definitely a choice to leave, it felt like once the scroll was on the table, once this idea of leaving was on the table, all I kind of had to do was like, Watch it unfold.

And the decision to leave became very clear because I wanted to know what it would feel like to be in control of my own time. I wanted to see what I was capable of, which remains true to this day. I'm still intensely motivated by, I did this. Ooh, what does this plus one look like? How, what's a little bigger than what I've accomplished?

Um, and the, how did I leave from a business perspective is actually, I have a very clear answer to this, which is I treated this. idea of leaving and quote, doing comedy [00:15:00] full time, which in December of 2020, everyone was like, I literally don't know what you mean by that. And I was like, don't worry. I also don't know what I mean by that.

So what I did was I said, we're going to do this as like a sixth month, six month experiment. And I essentially took money out of my savings account and made what I considered an investment. In this idea and I budgeted for six months I had also moved into my mom's house because it was pandemic time and I was tired of that studio So my burn was so low no rent.

Come on crazy Um, and so I knew I had enough money to not Cause future financial detriment detriment for if I did this for six months. I was like nothing really bad is gonna happen um And I also looked at it as money. I was spending for my future self so that at 40 or 50 in looking back, I wouldn't have that feeling of.

What if I had just done it? Like, what [00:16:00] if I had done that? And then when I contextualized that investment as, um, preventing that future pain, I was like, this is gonna be money well spent no matter what happens. And I said after six months to myself, here's what you're gonna do. In six months, if you have not figured out a way to monetize this at all, you need to pivot all your energy into monetization.

Um, and if you don't like it, You have to be honest about that and you have to either go back to tech or figure out what you want to do next. But that was really important to me because I didn't want to set it up in the way that some people actually framed it to me. Which was, oh, you're going to leave tech and you're going to go try to make it as a comedian?

Implying that there is some destination to arrive at. What? That's not a thing. That's not really a thing in most careers. And so instead it was, in six months, if you have spent all of this money, Um, and you haven't figured out a way to monetize, you need to either figure that out or leave and go back to tech.

And I was [00:17:00] just very fortunate that in having started my podcast Non Technical Uh, two weeks before I left Patreon, I started selling sponsorship into that show from day one. And so that became my salary. Small salary, but enough to, to not, to not go broke. And then, uh, over time I was able to cultivate some sponsorship deals for, uh, videos.

Few and far between. I do not want to treat my audience like a cash piñata. And also, the few and far between, I think, as go to market leaders, you'll appreciate this. Um, the scarcity of that makes them intrinsically more valuable as, as little moments online. Uh, and I specifically get to work with tech companies because of my audience and my general vibe.

Uh, which means it opens the door to do a couple sponsorships for cash, but also a cash equity split. And so I've built over the years, just like a small equity portfolio by doing a few sponsorship videos. Um, and then non technical is a huge part of that, but I was just [00:18:00] very lucky that after six months, when the come to Jesus moment arrived, I had done the thing that I set out to do, which is monetize to the point that I could continue and, um, we are coming up in one month, uh, on the three year anniversary.

So I will have been doing this full time for

three years.

Oh man, thank you so much.

Judd Borakove: Wait, but, but the serious question, what'd your mom

think?

Alexis Gay: Oh man, she was like, she was like, what do you mean? She truly didn't understand and it was hard to explain because as much as I kind of understood what I wanted to do, part of it was acknowledging that I wasn't going to be able to get concrete about it until it arrived. And that knowledge, you mentioned earlier, my relationship to like the, oh god I can't believe I'm gonna use the term creator economy, but my relationship to the creator economy as a result of my job at Patreon.

And one of the biggest takeaways for me from Patreon and watching all these incredible, incredible [00:19:00] creatives build sustainable financial, um, income and businesses around their work, it didn't give me a blueprint for how to do it, but it did show me it's possible. And I think that was the, that was the mental unlock for me there because I was like, And saying to my mom, I'm like, I totally hear you.

I know this sounds insane. I know we are legally not allowed to go out of doors and I'm saying I'm gonna go be a comedian. But I know that this can work, I just have to figure it out.

Craig Rosenberg: man, I might, I don't know what, I'm, I'm, I'm not sure how to feel. You were like, those were the, that was the most mature story. I was like, my God, that like your decision making was so mature. And you know, when we started this, it's like, Judd's like, let's go now. Now I will

throw some stuff

out there.

Alexis Gay: That's the vibe that I've gotten so far, yeah.

Craig Rosenberg: Right. And so, uh, that is unbelievable. All right. So is the, do you sell your own ads?

Alexis Gay: [00:20:00] I, when I, so Non Technical, my podcast, it ran for two and a half years, but I wound it down earlier this year, which is, uh, we can talk about what went into that decision. While it was running, I did sell my own ads. Um, I experimented twice with someone else selling advertisement for me, and it just didn't really work. And I think that's because the product I was selling was an expensive, premium product. I only did one sponsor per episode. So, each episode was exclusive to one company. I felt that was the way that I could stand behind the value of what I was selling. Because I don't really believe in the value proposition of, you're gonna be one 30 second ad in the middle of six others.

No one is listening to that. I didn't feel right selling a thing that I'm like, I'm pretty sure no one is gonna hear this. And on top of that, if you are selling six ad blocks per episode, you've to sell [00:21:00] six advertisers. If you are selling to one company, I only have to do it once. And so I was selling a premium product at a CPM that is, was so It's unbelievably expensive that I would get on the phone with marketers and I would be like, I'll tell you the CPM, but if you're using CPM to evaluate this decision, you this, you're probably not going to want to sponsor the show.

And I think that it required a, it was a really bespoke sale every time. And I think me as the host was a really integral part to closing those deals. And I think that's why, even though I had competent people partnering with me on the ads, I just, it always seemed to need to be me to like hold their hand through why. I dunno what you guys think about that from a go-to-market perspective, but that was my theory.

Judd Borakove: like founder

led. It's that really.

Yeah, it's it's the passion from your product because it's

you comes through from you and nobody else

can capture that like you, but but I,

so what, one thing we like to do on unfiltered is like, everybody's a part of this and you're part of our [00:22:00] conversation.

So hopefully we're not just going to keep peppering you with

question after question after

question. And I want to pose this to

everybody because you made me think about it. Like, you know, there's a lot of serious topics out

there right now. And I love the fact that you make fun of. 98 percent of them. What's the one topic you like to make fun of or think is the funniest?

Not just you, everybody. Cause I know Craig has a couple,

uh, that they're out there because I, I think like at this point business has gotten

so serious and we need, and that's why I loved when he invited you. I was like, yeah, we need a little comedy in this world these days. So I'd love to hear like you, everybody like. What is that one thing right now that, that it's so serious that it's funny and you make fun of it?

Craig Rosenberg: Are there rules around this, Jed? Because like, like, for example, my first instinct was you and Matt.

I can't say that.

Judd Borakove: You can, but I don't consider me and

Matt business. I

Matt Amundson: well, I I mean, this is coming from somebody who called me three times before 8am this morning.

Craig Rosenberg: I was, I really wanted to talk to you. I mean,

Judd Borakove: didn't call me at 8am.

Craig Rosenberg: not normal?

Matt Amundson: [00:23:00] Cause you're on the East coast, dude. It's

Craig Rosenberg: I would have to wake up at before five to reach you before eight. So that didn't work. All right. Um, I, do you want Alexis to go first? Do you want everyone to throw it out there?

Judd Borakove: No, let's let you go first. I think she

should go last. Cause she'll

Alexis Gay: Oh, cool.

Judd Borakove: suck. So, you know,

Craig Rosenberg: Oh yeah, no. Well, yeah. Well, hold on. I don't know my answer. You're gonna have to give me a sec. Does anybody know what they would say? Huh?

Matt Amundson: Man. Uh, I mean, I, so it's funny because, uh, it, it vacillates. It's really fun to make fun of AI, I think. Uh, so like there's, there's like a little bit of a treasure trove there. Uh, but then also like going on record and making fun of it when like, uh, what yesterday, somebody just raised 102 million series a like.

Um, yeah, they're laughing, uh, like they're, they're laughing at me making fun of them. But I think, uh,

Craig Rosenberg: Well, a hundred and two,

Matt Amundson: a hundred,

Judd Borakove: [00:24:00] 102.

Alexis Gay: It's very

Craig Rosenberg: which yet similar to before that's a hundred more than just two. But yeah,

Matt Amundson: and it's two more than a hundred, but, um, I've always loved, like, to me, the comedy has always existed between like marketing sales and sales development. And I think it's because that's where the lion's share of, uh, existed. Um, and, and, you know, like, whether it's yourself or, or other comedians that sort of play in that space, um, I think why that comedy is always popular or why it's funny to make fun of those situations is because it's so universally

true. So universally true. And the best comedy always is very universally true. And that's one of the things that I pulled out of, uh, of your story is. Your, your motivation to always be authentic,

uh, which whether you're being authentic as a business or whether you're being authentic and comedy or whether you're being authentic as a thought leader, like it is such a critical component of all of that being [00:25:00] successful and the people who try to be what they're not.

Uh, you know, it, it, it rarely works out for them in business, in comedy or in content, uh, in, in, in any form. So, um, so I like making fun of that stuff and I, uh, um, as a marketer, I, you know, I, I get made fun of a lot by sales organizations and I a hundred percent see their point.

I definitely

Alexis Gay: Hmph! Ahaha!

Matt Amundson: thank you. I don't know. I think

Craig likes to think of himself as the funniest person.

Judd Borakove: but that's just

Craig Rosenberg: think of himself, you

know what?

Judd Borakove: Hey, look, his mom told him he was, so it's

Craig Rosenberg: No, my mom did not. That's part of my psychosis. So the, um, by the way, I do on the marketing sales thing, that has always been my ticket, which is I personalize to the audience.

Alexis Gay: Mmm. Mmmhmm.

Craig Rosenberg: fun of sales when I'm with marketing, and I make fun of marketing when I'm with sales.

I make, and I got [00:26:00] all, you know, I can, I can do it all. It's always been my technique. By the way, this is not a business one, but Matt can attest this. The number one thing I make fun of right now are, are, are baseball dads, travel baseball dads. Yeah, they, they are. We live in the Bay Area. Okay, you guys are rich.

They're in their Teslas driving and they're still wearing Oakley blades and the baseball jacket. It's like you don't have to wear the uniform. Like, I, it's just crazy and their arms are always folded. I, just the folding of the arm, the, there's so many really interesting, I just watch. I'm just like, you guys, you're like supposed to know better, but they, something

Alexis Gay: Hmph!

Craig Rosenberg: attacks them.

Like, it's like this virus that, you know, they're like travel baseball dad, you know, I gotta wear literally like, cause like, you know, my kids on the team be like, well, do you want to buy gear? It's like for him? Yeah. No, no. For you. What, like, I, okay, I'll get the hat. Well, you gotta get the hoodie too. And now I [00:27:00] realize like the, they come out, geared up.

They've got, you know, the baseball style glasses, whether they're Oakley's or, uh, you know, whatever. They, um, you know, they, there's like in the, in the bathroom there's zen packets everywhere, so they feel like they're probably still playing baseball. So they've got their, uh, chewing tobacco and whatever, and it's like, it's amazing arms folded in packs.

You know, making comments, talking about how the reason they had to quit was because some coach didn't like them. Whether they quit in

junior high, high school,

Judd Borakove: Hey, Craig, show her your glasses though.

Cause this is this, this will

lead into mine. Cause. Oh, he has the

best sung, he has the best

glasses in the world.

Craig Rosenberg: doesn't, yeah.

Alexis Gay: Oh, yeah, okay. This is like if Elton John went to Coachella. These

Craig Rosenberg: little bit. Yeah. So anyway, there you go, but not a business one yet. Um,

so yeah,

Alexis Gay: yeah, I like, there's, yeah, that makes a lot of sense.

Craig Rosenberg: does. Right. I mean, I saw you nodding and I was like, well, you know, she might not go to [00:28:00] suburban baseball games, but she can

feel me on that one. Right.

Alexis Gay: well, here's, here's why, and do you mind if I, can I comment on these two so far before

we,

okay.

Craig Rosenberg: analysis.

Alexis Gay: So, well, here's what I, here's what I'm, and if you see me jotting down notes, it's cause I want to, I'm trying to make sure I'm keeping everything straight. Um, so a lot of what you said about baseball dads, um, would be the kinds of things that I might identify about people in my life and what you're actually identifying in my opinion is like, uh, repetition, you know, so like if you saw one baseball dad wearing Oakley's, that's not really interesting or notable, but six out of seven baseball dads wearing Oakley's, that's a trend.

That's repetition. That's okay. That's interesting. And so in my life, what I'll notice is if, um, right, if one person is wearing Uh, a Canada Goose jacket. That's not that interesting. But if every single person at this goddamn restaurant has a Canada [00:29:00] Goose jacket, I'm like, what's going on? You know, like, what's, hmm.

Judd Borakove: Wait, do you, do you say that or do

you go, this is good content? I'm curious.

Alexis Gay: Hmm. Typically I don't evaluate something as good or bad, I just evaluate it as unusual or noteworthy, and then jot it down, and then later we'll figure it out. I don't like to live, I think I'd be very unhappy if I lived my whole life like, Oh, this is good content.

Like, that sounds I also think I would be miserable to be around. And also I would be totally out of the present moment at all times, because I'd be watching the present moment. So I try to be there, experience things, and then if something is like, that's unusual, I'll just jot it down, or I'll try to retain it for later.

And so, even though I don't, um, I've never participated or been around, uh, travel baseball, I still take the same approach to noticing like, well, what's the behavior? And so then I might also say, what else do they all have in common? Or, where am I where I see this? And what's another thing they all have in common?

Okay, a [00:30:00] lot of the women are wearing Cartier love bracelets or a lot of the men are doing this. And then I'm like, why does it stick out to me? And I'm like, well, cause that logo is so huge. Why is this logo so big? And then I'm like, oh, it's so that everyone knows how much you paid for your coat.

Craig Rosenberg: Right.

Alexis Gay: Oh, okay.

That's interesting. And so then I'm like, so then what is, what's that? Cause you can get And by the way, the coats are great. I've worn a friend's. They're so warm. So I'm like, okay, it's a good coat. It's a good coat, but the price tag is on it. You could get a good coat that the price tag isn't on, but you want the one with the price tag that is.

And so then I'm like, what is going on there? And so then I might find something interesting about this group, this blob amorphous group I'm referring to of like Canada Goose jacket wearers. Obviously making huge generalizations, but it was born from the repetition of seeing it again and again and again And so like the travel baseball Um, dad point you made that was particularly interesting to me is them telling [00:31:00] stories where oh, well they could have gone pro if only such and such coach hadn't liked them.

Cause now you're starting to understand why they're buying, why they have packets of zint. What the, come on, you're an adult. And it's like, okay, so then I might think more about like if this is a common comedy thing, like, well, if this is true, what else is true? So if their attitude is this sort of like, could have been me.

What else might they do? You know, so there might be like really hard on their kid or they might give them like really specific baseball feedback, right? About like the position of their ankle when they were sliding. And so I would try to like find what are the other angles based on what I know about them.

Um, so I really, I think what you're picking up on is like exactly the kind of thing that I would. And then the previous example about. Um, sales and marketing, uh, I think is interesting because it reminds me of like wanting to be seen and also wanting to see yourself in the comedy. And I think that that is one thing that I am always, I always feel like I did a good [00:32:00] job when people comment, this is so me.

Or, oh my god, this is so true. Sometimes people are like, this is so accurate, it's painful. I've gotten that comment many times.

Craig Rosenberg: amazing.

Alexis Gay: And it's a compliment. It's a compliment. Because I'm like, oh yes, we've, we've had the same experience. You know, and it's this moment for me as the person creating it where I get to go, okay, I'm not alone.

And

Matt Amundson: yeah,

yeah, I think, I think that that is why like the comedy around tech plays so well because

Alexis Gay: Mm.

Matt Amundson: it's funny because it's true and it's engaging because We've all lived that

experience.

Alexis Gay: Yeah.

Yeah.

Mm. Yeah. Recognizable. Familiar but safe. Because you can watch a video. Um, about layoffs and not have the fear that you are about to get laid off while watching it. And so you can be separate from it a little bit and still feel the catharsis of having been there before.

Judd Borakove: So, so what's [00:33:00] yours?

Alexis Gay: Um, actually this is a great segue because I really love, um, and I should clarify that if you were to look back at all of the, we'll talk about specifically the sketch videos, if you were to look back at all the sketch videos that I've made, less than half are about tech and business.

Interestingly, um, and part of that initially was an intentional choice because I feared if I only made jokes and videos about a specific topic, I would only be expressing one part of myself and then if I ever wanted to move away from that, the audience that I would have built would not be interested.

So I intentionally, I think I grew more slowly, but it was a conscious choice by not only leaning into tech and business. The Internet Rewards. knowing what to expect from your content. And I was like, I know that. And I don't want to look back in three years and be like, I can only make jokes about APIs. Like, can you imagine? That would be so boring. So I say that only because it's true, a lot of the [00:34:00] work of mine that has gone the farthest or gotten the most views has that tech business bend to it, but that I like to create things about all aspects of my life, but the common thread between the tech and business stuff and other stuff is often like a lack of self awareness, um, and hypocrisy, uh, and I use, like I said, repetition a lot.

And so one of the ways I think about like what to make, make fun of or poke fun at next is if I, if I just hear the same thing a lot, I'm like, what's going on with that? Why am I hearing that so often? And, um, I also really enjoy making jokes that are fun, funny, ideally, but don't make anyone feel bad. I don't, to me, it's like not putting net good out there into the world.

I'm not like creating net joy.

If in order for like group A to feel good, group B has to feel bad. And so, I try to, if I am making fun of somebody, it's usually some version of [00:35:00] me. Uh, and then if I am making fun of someone that's not me, and the reason I said it was a segue is that I made a video called Venture backed CEOs.

Judd Borakove: It's like, wait, I don't even

Alexis Gay: sorry.

I know I was like,

Craig Rosenberg: Yeah. Cause

Alexis Gay: no, I, I, no, sorry. I forgot. Uh, my groceries are early. Can I just buzz them in real quick? Sorry, sorry, sorry.

Judd Borakove: buzz.

Good thing we have editing.

sam_3_11-30-2023_150434: be Auto Blooper

Reel.

Matt Amundson: it's the same thing.

Craig Rosenberg: We gotta leave the grocery delivery thing on for

sure.

Judd Borakove: for sure.

Craig Rosenberg: I mean, you guys left the one where I went to go tell my kids to be quiet and close the door and you were talking about me on the video and I got to see it when the video was released.

Judd Borakove: wait, she's back. Shh. Just kidding. So, so, just so you know, most likely you getting groceries will be in the,

in the video.

Alexis Gay: No! Can you see my Birkenstocks? No!

Craig Rosenberg: What [00:36:00] that is. Yeah. I mean, come on now. We, we like to

Alexis Gay: Actually, I kind of love these shoes so much, um, because the Birkenstocks are so comfortable, but these are, these are my house shoes. Do you guys wear Birkenstocks? You're Bay Area

Matt Amundson: yeah.

Alexis Gay: you Birks? Birks

people?

Matt Amundson: of Arizonas and

Bostons.

Alexis Gay: Dude, they're so comfortable. And so they're my, I never wear them outside of the house. And so I bought them in my favorite color, which is this like light lilac y purple.

And they bring me joy every single time. Every single time I put these shoes on, I'm like, this is a great purchase.

Judd Borakove: also like that you call them your

Craig Rosenberg: sponsoring

the show Judd.

Judd Borakove: Yeah, yeah, yeah.

We, we know who to

reach out

to.

Alexis Gay: Yes!

Judd Borakove: freeze frame on the

Birkenstock

Alexis Gay: Oh my god, please do not. I'm sure I look insane. I'm wearing full, I'm wearing full length wool socks tucked into Birkenstocks. I'm wearing socks with

Judd Borakove: I, yeah, but you're not, you're not allowed to wear birken socks without full length

socks. I mean, come on,

Alexis Gay: But not in the winter, anyway. I get cold. Anyway,

Matt Amundson: heading for a big portion of the sort of viral Brooklyn dad outfit, right?[00:37:00]

Like

skirts,

Alexis Gay: oh my god, good

point.

Matt Amundson: socks. You've got

Alexis Gay: Yeah. I have kind of a dad sweater, and I'm wearing sweatpants. Just black, plain, plain black sweatpants.

Matt Amundson: You're just missing a workwear jacket and a hat.

Alexis Gay: I, I have several. Yes. Wow. I guess I do kind of dress like a Brooklyn dad

Matt Amundson: Break, break out the Detroit jacket. We want to see

it. We want to see it.

Alexis Gay: and I'll be ready to go.

Judd Borakove: get your

Alexis Gay: Um, get my oakleys out. So the video that I was about to reference, uh, was venture backed CEOs after laying off half the company. And the reason why this video sticks out to me is one that I was happy to have been able to make was that the dominant conversation at the time was layoffs.

Everyone was doing layoffs. Everyone was talking about layoffs. Everyone was getting laid off. It was the dominant conversation in my social circles. However, [00:38:00] sensitive topic. Because people are losing their jobs. So I was like, wow, this is coming up again and again and again and again. Interesting. Okay, so right, I file that away.

And I'm like, jeez, I'd love to do something about this. Um, but, the, the recipient of the joke, the butt of the joke, cannot be the people getting laid off. It can't be a joke that comes at the expense of these people. These are real human people who are losing their jobs. So I was like, okay, that's a good guardrail. And then I was like, what is sticking out to me about all of these layoffs? And I started realizing that it was the way that CEOs were delivering the news and then writing these unbelievably self aggrandizing posts. about the fact that they had to struggle through doing the layoffs. And then I'm like, the, and the thing that really bothered me about this was like, these are the same people who one year ago, when [00:39:00] everything was sunshine and roses and everything was getting overfunded and overvalued, were showing their investors these hockey stick growth curves and being like, we need to expedite our hiring and hire So many more people and get an even bigger, whatever.

And it was just like, how did you not have the foresight to understand that this, this global pandemic was actually not going to go on forever, God willing. And so it just struck me as so hypocritical. And I, I thought there's gotta be like a way in. And so I thought, okay, it's, it's not, and it's also not making fun of this individual, the CEO, but it is the specific hypocrisy of being like, Oh gee, I don't know what happened.

When it's like, no, you did

this.

Judd Borakove: what happened. Yeah,

Alexis Gay: Yes, exactly. And so that is the kind of thing that when I can find that in, um, I, it's more, it's more interesting because it's also unexpected. Um, and in talking about making fun of AI, fun fact, I actually, I don't find personally, I don't find [00:40:00] making fun of AI interesting at all.

Um, because there's so much of it, uh, that I'm sort of like, I don't know what the joke is, cause it's a real technology that's going to be around for a long time. And, uh, so instead I would try to find a way in of usually, like, how people talk about it. And so I made a video last week, or a couple, or I made a video amidst the OpenAI drama called, When There's Big Tech News.

And the way that we all, like, crabs just gobble it up and we're like, More news! You know, more tweets! And I thought, yeah, and I thought, like, that's to me what was, quote, funny. Because again, that's real people doing real things. And I am very aware that as someone with, like, an online following, people directly involved in these situations could end up seeing the work.

And so it's important, I try to be respectful of everybody. And that video doesn't Hurt or demonize anyone involved in that situation. It just pokes fun at the [00:41:00] way several of my friends and also me were just like, did you see that tweet? And so I tried that's the that's the type of angle I like to find into those topics.

Craig Rosenberg: So that video, I just want to stop because we don't have much time.

So that video had lots of cut, like when you do those videos, there's lots of cuts. So like, how do

you produce that? Like, do you do a lot of, and then you splice it all back together?

Or what does that look like?

Alexis Gay: I, um, everything is scripted, so I script everything first. That helps reduce the amount of time I spend filming, which is important, because ultimately the goal for me is always to get these to about 60 seconds. And if you have 23 minutes of footage, Which I've done before, absolutely. Cutting that down to 60 seconds.

Um, what was the tech Oh, it sucks. It sucks. It's just like a It's

unpleasant, yeah. Um, in November of 2022, so a year ago almost, I made a big business pivot, [00:42:00] um, or structurally, which is that for the very first time, I started working with a video editor. I edited my own videos. 1000 percent all the way until about a year ago and I think you guys will like why I made this decision. This was about the time last year when the rumors around Elon taking over Twitter were getting really real and my biggest following is on Twitter and so what you might, uh, as a, as a business leader what you might say is that I had an extreme weakness in the fact that my largest following was about to be in the hands of somebody who at the time I was like, I don't, I don't know that he's going to pull this off.

And that really freaked me out because if Twitter went away, you know, that's where I have 130, 000 followers as opposed to at the time, about 23, 000 on Instagram. And so in November, 2022, I was like, Geez, I really need to double down on video in an effort specifically to build a more [00:43:00] robust following on other platforms to hedge in case Elon runs Twitter just right into the ground.

And so I, a video, a super, uh, a super young, uh, video editor reached out to me randomly around that time and was like, Hey, I don't know if you need a video editor. And I was like, no, I do it myself, but I'll get on the phone with you, I guess. And I got on the phone with him and he was very. I really liked his energy and I felt we could maybe work well together.

And so I sent him some raw footage of mine and I said, this is the most narcissistic thing I've ever asked anybody. Could you go back and watch my videos and see if you can turn this footage into something that looks like that? And he did a great job. He got, got it to about probably 75, 80 percent on the first try.

That was a nice wake up call for me because I thought I was, uh, I thought that was my special sauce. I thought, I'm a cheeky, special little editor. And then this man who had watched, you know, 10 minutes of my content nailed it. But anyway, huge unlock for me business wise because Uh, that has enabled me to create stuff so much faster because [00:44:00] now I script and I film and then I send it to Alex, my editor, and he does the first pass based on my script and then he sends it to me for review and then we go back and forth a couple times and then ultimately he finishes the cut.

Adds the captions, makes it the right size and dimensions that I want for the various platforms. And I share that because that is the type of process that's now enabled me to flip something like that OpenAI video. That was our fastest flip ever. I filmed that at 6pm. Sunday night and published it at like 2 p.

m. Monday,

Craig Rosenberg: That's amazing.

Alexis Gay: fastest flip ever. And so I share that because at first I was very hesitant to hand over any, like a founder, hand anything over to anybody. I was like, no, it has to be me, but editing takes a long time. I love editing. So it's, it's tempting. It's, it feels productive, but I've been able to. Grow so much faster and actually since working with a video editor, which has enabled me to create so much more My like year over year growth on Instagram I've actually I [00:45:00] doubled my Instagram following in 2023 from like 23, 000 to 50, 000 And I really credit the the at bats that I'm giving myself By reducing the amount of time it takes me to make something.

Judd Borakove: All right. I got, okay. So I'm going to jump in here cause we're almost at time. So one, I love it. Everything you just said is easily correlated to

any business, anytime. It's this, it's like find the process, scale the process, grow, right? The other thing that I, that really hit me and while you say, you know, you diversify your content, honestly. I kind of think it's still the same focus. And I'll just give you why and why I love it so much, honestly. Cause I got in when Craig said, Oh, make sure, you know, check her out, know her stuff coming on the video. You know, I'm like, whatever, sure. And I got on and I started watching the stuff and I'm like, kind of funny, cool. I got deeper. And I said, this is the life of somebody in

tech. It's not that it's like you have to make fun of tech. It's anybody who is in tech. This is what you live on a

day to day basis is how you. Think how

you dress, [00:46:00] you know, who your friends are. And it's hilarious to be able to encapsulate that and then make fun of it.

Cause I do think, like I said earlier, we're all getting a little serious. And if we can't get that break point at some point, so I, so thank you. First off and everybody who's watched this, go check her stuff out,

Please.

I think you guys, you guys will get a laugh and you'll also probably cry a little bit, but it'll all be good.

Craig Rosenberg: Wait, when's your next live show? This is like, I

mean,

Alexis Gay: Next live Oh, I'm working on a new project. I'm working on a new project. My next live show is in, um, three and a half hours, but I, uh, I, uh, yeah, I know, right? Um, we should figure out what jokes I'm telling is really what we should be doing during this hour, but figure that out later. I am working on my first ever solo show, which means a full hour of, um, of, here we go. And, uh, it's on the topic of work, actually. Uh, that's a big part of it. It's also a little bit about, probably about failure [00:47:00] in a lot of ways. Um, but it's funny. It's a, it's a stand up show. And so this, so Tuesday, um, and we actually are about, we, did we just sell out? I think we just sold out. But it is, um, it's my first ever 30 minute preview of the show.

So I'm in this is kind of an interesting moment to talk to me because I don't really know how it's gonna go But I feel very confident at this point that I've prepared enough that I will like I'm gonna learn so much from Tuesday But I've only put up a 15 minute version of it meaning like only put up in front of an audience this is the first time I'll have ever put up a 30 minute version and We don't we don't know and it might it I mean this sincerely When I say it might not go well, what I mean is there may be uncomfortable moments for me on stage where it's quiet or where something doesn't land.

And I know that it sounds bad. I get it. I totally, even hearing it, I'm like, no one wants that. But I also am like. It is the only path to getting to an hour long show that you will all really love. Like it [00:48:00] is just the only, how else am I going to do it, you know? And so you're catching me in this really interesting moment for me where I'm like, well, we sold the tickets and it's going to happen Tuesday and I'm kind of ready and I'm, I'm excited and we'll see how it

goes.

Anyway, so that's what I've got coming

up.

Craig Rosenberg: Hey, I'll be, I'll be,

wait a minute. I'll be there Tuesday. Are there like,

Alexis Gay: God.

Craig Rosenberg: scalpers out front? Like,

can I, if it's sold out?

Alexis Gay: I I can, I mean, I can get you like a background comp ticket for sure. Yeah.

Craig Rosenberg: Boom.

Judd Borakove: wish I lived there now. I'm not

lucky.

Alexis Gay: I can't wait. I'm so excited. That'll be so fun. And, uh, yeah, and we will, we will, I'm going to be working on it for at least the next year. And so this is, uh, this will just be the first swing and like a product, this is the, you know, the MVP and then we'll make

it better.

Craig Rosenberg: That's

great.

Thank you.

Alexis Gay: If you're not mortally embarrassed by your first solo show preview, then you waited too long to ship it.

Matt Amundson: Nice.

Judd Borakove: And that's the way we end, like, uh,

Craig Rosenberg: That's a perfect

Judd Borakove: yeah,

Craig Rosenberg: All right. Well, thank

Judd Borakove: guys, yeah, [00:49:00] thank you so much. for being here, we really

appreciate it, and guys, definitely check her out, we can't say enough great things about what she's doing and how she's calling attention to

lives, her life, like, it's real, so,

guys,

Craig Rosenberg: Links are in the show notes. Judd,

Judd Borakove: it's in the show notes,

and we

Craig Rosenberg: All

Judd Borakove: have an outro, so I don't need to

say anything,

bye!

Alexis Gay: Perfect. Bye!

​[00:50:00]