Thankful for the unexpected

26 Nov 2025 · 39 min · 12 chapters

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In short

Thanksgiving-themed career gratitude, emphasizing unexpected turns, people who supported them, and the role of luck/coincidence in professional paths. The hosts also riff on tech culture (AI “nano banana” deepfakes, Roblox child-safety PR misalignment, and ongoing Rippling legal/ethics chatter) and discuss how tech leaders’ behavior affects reputation.

Guests (hosts)

Ashley (host), Helen (guest), Mac (guest). Backgrounds mentioned: Ashley is an investor/venture-adjacent operator (Homebrew/Coalition/Kauffman Fellows referenced); Helen has worked in comms/tech and leadership roles (Glossier, social capital, Amazon PTSD joke); Mac worked at Palantir and later in comms/strategy.

Key claims

Tech morality/reputation is being ignored due to “move fast” incentives; deepfakes raise serious societal risk; career narratives can be reframed as intentional in hindsight; supportive mentors and scaffolding shape trajectories.

Notable examples

Hunter Walk and Satya advising Ashley (Homebrew); Kauffman Fellows mentoring; Marge at Palantir coaching Mac; Amy Sherman’s 360 feedback to Helen; leaving Glossier without a next job leading to venture; nano banana height/shoe clues; Roblox CEO interview mismatch; Rippling LinkedIn legal screenshots.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Childhood Bedrooms and Remote Work

0:37 to 2:18

Discussion about childhood bedrooms and working remotely during the holidays.

“My first meeting this morning was a tour of everyone's childhood bedrooms.”

HR Tech and Legal Updates

2:18 to 3:21

Conversation about HR tech, recent legal developments, and transparency in business.

“It was something about how like the money was transferred from like the business account into someone's wife's account.”

Tech CEO Accountability

3:21 to 5:20

Exploration of accountability among tech CEOs and their public interactions.

Nano Banana Image Analysis

5:20 to 9:06

Discussion on identifying fake images and the absurdity of viral content.

“And he thought he was just coming to hang out.”

Paid Substack Strategies and Drama

9:06 to 12:18

Reflections on the monetization of personal drama in media and its implications.

“And Sally's like, I can't tell if this is real.”

Tech Industry Reflections

12:18 to 14:00

A critical look at the tech industry's evolution and its disconnect from societal needs.

“Like I said, I wish I could bleach my eyeballs.”

The Seriousness of Current Tech Trends

14:00 to 19:21

Discussion on the serious implications of technology trends and societal disconnect.

“And people will use this in nefarious ways.”

Gratitude and Nonlinear Career Paths

19:21 to 28:06

Exploration of who influenced their career trajectories unexpectedly.

“the three of us, actually all five of us on the pod, have had pretty nonlinear careers.”

The Value of Vulnerability in Leadership

28:06 to 29:25

Learn how sharing vulnerability can enhance team dynamics and personal growth.

“And if, you know, somebody on my team is trying to get something done and it's met with, well, you guys seem to have it all figured out.”

Gratitude for Setbacks and Career Turns

29:25 to 32:05

Discover how setbacks can lead to unexpected opportunities and personal growth.

“OK, so then the second question is like a setback that you're now grateful for.”
Show all 12 chapters

The Role of Luck in Career Success

32:05 to 36:59

Explore the impact of luck and chance encounters on professional opportunities.

“send off and, you know, have everything sort of like all tied up with a bow because it forced me to spend some time exploring other things.”

Sharing Your Journey and Lessons Learned

36:59 to 38:46

Understand the importance of sharing personal stories and lessons to inspire others.

“know I think luck and being at the right place at the right time like you said Mac um has been such a such an important part of all of our stories.”
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Transcript

Automatic transcript. May contain errors.

0:05This week on Great Chat, we discuss what we're thankful for with a focus on our careers. But it's not the shiny accolades. It's the things we didn't expect and the people who helped along the way. I'm Ashley, and this week I'm joined by Helen and Mac. Great Chat is brought to you by Mercury, the fintech used by entrepreneurs through every stage of company building. We use Mercury to run this podcast and love recommending it to other founders and fund managers. Try it for yourself. Visit mercury.com to join over 200 ,000 entrepreneurs, whose mercury to make managing their money unbelievably simple.

0:41Hey guys. Hey. Hi. Hello. Happy almost Thanksgiving. My first meeting this morning was a tour of everyone's childhood bedrooms. Oh yes. Yeah. I was like, wait, what? Oh yeah. On Zoom. Exactly. Because everybody's back home. Oh, sorry. Yeah. Maybe you should have added a little bit of context. No, no. Exactly. Cool. Cool. different kind of co-worker bonding. Got it. Exactly. This is what we're just like really, really close. No, uh, everyone, everyone is like working remote and they're all working remote from their childhood bedrooms. It's really funny. Cause like the walls are thin and people are like, I can hear my brother, you know, it's great.

1:22I just cannot relate. I moved like 12 times before going to college. And so the idea of still having like an intact childhood bedroom does not compute. I can't even imagine. Moving 12 times is crazy. My dad was very millennial and he listens to this podcast. So hi dad. I'm not, I'm not too damaged. Wait, he was millennial. He was like, he was remote working. No, he was living a portfolio life. I guess there have been many eras of millennial, but like, do you remember when we were younger? It was like, oh, millennials change jobs like every two years. And that was. And addresses. Yeah. Yeah. My dad was just very like ambitious and willing to like move us around the country and uh sweet and yeah and as a result no childhood bedroom for me my parents also live in the house that i did not grow up in so it's like bizarro town as well my parents live in the same house but my bedroom is now a yoga studio so oh amazing do you do yoga in there uh no but mom does um okay so i feel like the rippling deal saga has been a consistent theme throughout seasons and throughout mac episodes so the update this week or last week was love for hr tech i know she loves it um last week i guess there was some advancement or some some something that happened in the courts but the um chief legal officer at Rippling, like took to LinkedIn and wrote a post about what that victory was and also shared like screenshots with like arrows and, you know, pieces from the court filing.

3:07Oh, yeah. It was something about how like the money was transferred from like the business account into someone's wife's account. And so it was basically linking up that this was all like company sponsored and there was a trail. Yeah. and like LinkedIn was interesting um you know it got a lot of engagement but like it also felt like people were so desensitized by it even on LinkedIn like I feel like LinkedIn is so earnest I would expect them to be scandalized on LinkedIn most of the comments were like other attorneys that probably follow her and like live not in Silicon Valley who are like wow thanks for the transparency because let's be honest it is wild that like a general counsel gets on linkedin and starts sharing pieces right like great i love yes yes and then i don't really feel like there was a peep on twitter so i don't know do people not care because i feel like we've we've brought that up on the pot as well like does nobody care about bad behavior anymore like is it they're over it or somebody made this point where it was like well deal keeps posting w's in terms of like growth and revenue and it's like maybe that's all people care about like I you know so yeah I mean I think it's worth remembering people really cared initially like when when Parker dropped the honeypot reveal everyone like lost their minds and so I wonder if part of this is just we're on like chapter 10 of this saga and the new details aren't like as fun as someone like hiding in a bathroom with a cell phone and like some of the early drama so I do think I get why Parker is still on this quest but I think for the rest of us if you're not you know if you're not in that particular universe it's a little bit less exciting but Helen it reminds me I was um I was listening to Hard Fork and Casey Newton and Kevin Roos interviewed the CEO of Roblox and it's an interesting interview only because it seemed that there was some misalignment about the topic Like they thought, based on conversations with his BR team, that they were talking about like child safety on Roblox and like what the company was doing to address some recent issues.

5:26And he thought he was just coming to hang out. And so it was like a little awkward at times. But Casey wrote an essay yesterday after that was basically like, do tech CEOs have no shame anymore? And what does it mean when there is like no shame left in the tech ecosystem? because this CEO just kind of refused, David, I forget his last name, just refused to like even say the things you would expect someone to say, which is like, we need to do everything possible to protect children. And, you know, he just, he just wanted to hang. He like, he was like, nah, fuck them kids. Let's get back. As a former comms person, I was like, I could have given you some talking points.

6:10Like, you know, there's some basic, basic things just to say. And he seemed very like frustrated that he was being asked these questions. And so, um, you know, this is, this is a part of the same thread of like, if business is going well, um, and, uh, and your customers don't seem to be concerned or even aware, like, do we care anymore? And I thought Casey's essay was like a really good zoomed out view of, of, you know, where we might be from like a tech and morality perspective? I saw it covered like maybe briefly. I did not listen to the episode, but I saw a little bit of the fallout. And the comment that I saw was somebody saying this comms person thought that this would be a good softball interview format, like a la 20 minute VC or TVPN.

7:03And it wasn't, you know, like they, they came prepared with hard questions. so just a reminder everyone the new york times is not a softball interview it's like and actually that connected the dots from hard fork is a new york times podcast like and and yes and casey and kevin are real journalists right like it's so as someone who like listened to the whole thing they also were not like going for the kill in any way like they thought that there was an agreed upon topic and it was going to be child safety and what roblox was doing and they were like asking questions. And of course, Casey, the platformer is all about like the intersection of tech and like regulatory and safety and all of that.

7:45So he's like, just like deeply embedded in this world. So, so hard fork is, is that they ask like, interesting questions and real questions, but it's not, you know, it's not the hot seat. I don't know, I would love to, I would love the behind the scenes of like, what went wrong with like the PR pitch and the CEO brief. And there was clearly some misalignment there um another one that we had in the group chat this week was sally sharing a bunch of um nano banana images and being like i can't tell if this is real or fake and then one of us pointing out like okay this is obviously fake do you guys have like a a trick or something that you consistently look to look for in these sort of images where it can tell you it's because it used to be the like six fingers right it used to be like the weird the weird hands look at the hands yeah but now I feel like they fixed the hands and so you have to look for other things and so I think maybe we pointed out like height differences um but that was me they were also all wearing the same shoes this was in case people have seen it it was like a photo in quotes of like, you know, Sundar and Tim Cook and Sam Altman and Mark Zuckerberg and Jensen, like all like hanging out.

9:07There were like seven or eight of them. And Sally's like, I can't tell if this is real. And I was like, well, I know most of these dudes are like five foot seven. And then some of them are tall because it's like a meme that like powerful men are like five foot seven. Oh yeah, five seven. It's a thing. It's a thing. And I'm like, well, Tim Cook's not five foot seven and Sundar is not five foot seven. and Elon's not five foot seven, but they all kind of look like the same height. So I knew it was bullshit. And then like four of them were wearing the exact same shoes, which just seems unlikely. Is it just me or is it like so low imagination to put all those tech luminaries together in a nano banana photo?

9:44I would want to put way crazier combinations and have like much wilder. Oh, Helen, I want to see your nano bananas. No, I literally haven't tried yet, but I don't know. like Mac who would you put together I think it was perfectly designed for the audience like they know the audience yeah okay well I mean I mean I guess I guess like I it's it's not for me I'm not target audience but like you're not target audience but I think like yeah you know the crazy amount of engagement the fact that we're even talking about it means that people people knew what would get people started I don't know guys I fantasize about all these titans of industry hanging out in a parking lot wearing the same shoes totally when i go to bed i hope i have a dream i hope we i have a dream with all of these characters in it i mean it's very predictable totally has anyone caught up all the way and paid for the ryan lisa sub sub stack subscription um for parts two and three part one was enough for me does anyone else feel kind of icky like I feel like I'm getting you know like when you have two friends break up and you're like oh wow I really like both of you and then they both start telling you things and you're like oh god I wish I could unhear this shit like there's some there's some stuff where I've like seen I've seen like screenshots and whatever and I'm just like oh god I I could have gone my whole life without ever reading this well Well, I was more curious on like, how do you sustain this as like a paid sub stack strategy?

11:22Right. Like, oh, I think he has to know that it's a moment. Right. Like I like ideally he has readers who do love his content, but I think like and hopefully some of the people who came for the drama stick around beyond. I think that's right. How do you how do you even match? Also, everything that I'm saying, it feels less about like monetizing the moment, although that seems like a nice side effect and more about like you know getting revenge on the ex who cheated that's inserting himself what it's about yeah into the news cycle which would not be my preference but he's going for it i am no i read the first one and then i saw someone referring to some term that's used in the second one he's like you don't want to know what this is and i was like you know what i don't want to know what that is like i like in 2025 either it is a choice to not know something and I choose it sometimes.

12:16I'm just going to say you guys made the right decision. Like I said, I wish I could bleach my eyeballs. I wish I could go backwards to a time that existed before I knew all this. I'm just like, Oh God, like I don't need to be in someone else's bedroom. Like, I just don't want to know. I like, I like God to your earlier point about like, do tech bros feel or do tech, do tech videos feel no shame. Can we all feel a little shame? can we all just kind of like keep it to ourselves like there's a shame that will be this kind of one thing one thing I was reflecting on this week after like after like with all of the articles that we've been sharing and with some of the stuff that we've been talking about is I think like there was a moment where it was really novel and really refreshing to see Silicon Valley enter into the scene with this like youth forward energy and it probably was because I was young I think part Part of it too was because it was so deeply refreshing to like have people out there succeeding despite being, you know, not a buttoned up suit.

13:12It felt inclusive. It felt like actually genuinely new. Now, given the stakes of what we're up against, given the stakes of this moment, given the realities between what was promised in the tech world and the tech revolution and what has actually been delivered, what was promised disruptive industries, better jobs, better like more prosperity, easier workflows. It turns out that work is still just as hard, but a few people are very, very, very, very wealthy. And those people are out here acting like 10 year olds. Like, I think it's still kind of crazy. Don't get me wrong. I'm super impressed by Nana Banana.

13:48I think it's incredible technology. It's such an insane feat, but you see this piece of technology come out that is going, that has massive implications. Like we can no longer tell what is real and what isn't. And people will use this in nefarious ways. And it is serious. It's really meaningful. Like it is a massive step forward. And we're calling it Nana Banana. This is something that will drive our parents crazy. This is something that will make us believe things that are not true. And we're treating it with like the seriousness of like, I don't know, a three year old's birthday party. And I think there's something that's like really gross about the arrested development and the stakes of this current moment that like to all of the other points that we're talking about just show how deeply out of touch tech is and like how how far removed from the like the rest of society we've become and I think that that's like something worth like reflecting on uh because I think it's just kind of like I don't know I think a lot of us entered into this space because we were really excited about the like prosperity that we could go create for everybody and I think like this feels different than that anyway like really chill yeah I love the rant.

14:58I love the rant. I think that like tech leaders are thoughtful and long-term oriented when it serves them to be. And right now, no one believes that it is in their interest to think about reputation, to think about impact. Like the only way I can explain some of the behavior that's happening now is that like everyone believes the future is going to be decided in the next couple of years. And so all that matters is moving really fast and winning whatever the current maybe like AI arms race is. And so morality or like unintended consequence is just like out the window a little bit right now. And everyone's like fully on offense.

15:40And we'll see, we'll see if that ends up being the timeline or if we're all paying the price for this in five, 10 years or the next election cycle. Like, I really do worry about the long term reputational harm that a lot of these actions will have for the tech. And as an early stage investor, I'm like, by the time my companies are mature, what is going to be the climate that we're in? And so I think it will be a reset. Yeah, I think about that, too, Ashley. And like, I think that I bet that there were conversations like this before the dot com bust. right like pets.com as a concept you know like kind of wild like I'm not saying it's the silliness you know level as we saw but I think personally for me my moment um of sort of like disillusionment was a little bit earlier which is why right now I'm like whatever I think for me it was really like the NFT craze it was truly like people I thought were very intelligent right like people I looked up to my entire career going all in on monkey JPEGs.

16:50And I was like, okay, but when I worked at Facebook, you know, the mission was to make the world more open and connected. And we were told to build something beyond ourselves, right? Like I was a very junior person who slept at my desk multiple nights because I thought that the contributions I made as like a lowly marketing manager were like essential to the future that Facebook was trying to build. Like that was like how tightly wound like the mission and like everybody's role was. And then those same people, you know, who were like helping with the rally cries then were like going all in on, on NFTs.

17:31And like, I think maybe I was a little closer to it because of my like fintech background. Right. And there was like, it was like a closer bridged from fintech to crypto to, to, to the NFT craze. But like, yeah, that was like a bubble bursting moment for me. So now I'm just sort of like, yeah, it's more of the same of that. I love it. This took an unexpected twist, but. Totally. I saw on Twitter that there was a big announcement of a maybe Series C round that was led by an endowment. And I was sort of curious, like, oh, then what are we doing? What are VC firms even for? um like lulu's go direct advice is now going to lps they're making you know big they're leading rounds um i think this is common bubble behavior like i and and not something that i have personally paid attention to in prior cycles but helen inspired by that like uh endowment going direct saw a commentary on yep this happens whenever the market gets really hot like other people come in and think they can do this and, you know, no offense to that endowment.

18:38Maybe they can, but a lot of endowments are not resourced to do direct investing in that way. And so, yeah, so we'll see. Although there was some, I wish I could remember this, there was some like pension fund. I think it was like Toronto Teachers Pension Fund or something like that. Oh, yes, they've been active. It's like in Anthrop, like in some great companies that it did directly. And I'm like, you know what? Props to them and may their teachers live long, prosperous lives. I'm all for it. So it's Thanksgiving week and we're doing the obligatory gratitude episode. And these can feel a little cheesy, but the reason why we're actually doing this is that the three of us, actually all five of us on the pod, have had pretty nonlinear careers.

19:26And so we've all left companies, started things, failed at things, ended up in venture from very different paths, left venture. And I think if you talked to any of us, you know, five years ago, we wouldn't have predicted that we'd be where we are now. So the question to dig in today isn't so much like, what are you grateful for in the generic sense? It's more like what or who actually shaped your trajectory in ways you didn't see coming. and specifically the stuff you didn't appreciate at the time that you can now sort of look back and see and actually feel thankful for even at the time it kind of sucked and the first question is what is one person who sort of changed everything for you and you can name them or not name them and they could be like a champion you know like an obvious mentor or somebody who like gave you really harsh feedback that you know at the time was not well received but now you're grateful for or or exactly maybe it was exactly what you needed at the time well maybe we'll start out with ashley oh my gosh does anyone come to mind changed everything like everything like if i don't say like like my husband i'm gonna be in trouble uh but i well i'm glad because that's my mom like or my parents or my dog let's constrain it to careers because I feel like we do a good job of not getting too off track although we'll have a special episode just on that I'm gonna maybe use this opportunity to embarrass uh hunter walk of homebrew and screen door of fame and like there are a couple moments that are pretty poignant for me one was that when I left social capital um I like I wanted out of venture I wanted out of San Francisco I moved across the country to New York I worked in beauty which was like the opposite of anything I'd ever done and shortly after that uh Hunter and then also Satya reached out and asked me to be like an advisor to homebrew um and I really liked them respected what they were building and and so I I said yes.

21:39And that kind of kept me connected to venture in a way that I don't think I would have otherwise been. And then from there, eventually I started angel investing. I started scout investing. I raised Fund One. Hunter and then through Hunter Satya were some of the fastest yeses to invest. And I'll always be grateful for that. But then the thing, the other thing that was really helpful for me is I did this program early in the early days of coalition when I was like building the plane while flying it and losing a lot of sleep over what I might not know. Did this program called Kauffman Fellows. It's a two year program.

22:18And one thing they make you do is you have to like pick a mentor and meet with them. I forget what it was monthly or like every two months for the duration of the program. And like, I would never ask anyone to be my mentor. That feels like so cringe to me, but because I had to do it, I asked Hunter and he said yes. And it was actually like, I'm so grateful for that scaffolding because there were so many things I either didn't know I didn't know or needed to like talk through with someone. And it was just easy because we already had these Zooms set up and like already had that relationship. And also he gave me some really great feedback on, I was getting a little too creative with some elements of the coalition model.

23:03And he like reined me in at one point in a way where now I look back and I was like, what the, what was I thinking? So anyway, so, so there are the people who like make a big show of wanting to support you and there are people who just like show up again and again. And so he's done that for me and, and some like pretty key moments in my, in my career. So thank you, Hunter. Yay. Friend of the pod for sure. A friend of the pod. Mac, who comes to mind? I joined Palantir in one role and then ended up switching to a different one. And it was all because of, all because of, I genuinely don't, titles were such a question mark thing there.

23:42They didn't really mean anything, but Marge was leading so much of like our strategy around how do we develop people? How do we hire people well? And I don't know, I genuinely don't even know how I ended up like getting connected with her or getting, becoming close with her. But, you know, just those people who see something in you that you hadn't yet seen in yourself and who are like, hey, this is great. Like she was one of the first people in my career who did that for me and ended up being like, hey, like this seems to be going okay, but I think you could be doing like 10 times more over here.

24:19I really think you should consider doing that not only like pushed me to do it but also like facilitated every single step like you know how sometimes when you're young like you feel like you're banging your head against a wall trying to make something happen and then also sometimes when you're young you're like oh like if I want this thing or if I'm vaguely thinking about this thing it will just happen and obviously that's not how it works um this was one of those things where I got like basically every single thing like spoon fed to me because this woman how old were you because I you're hitting on something really, really specific that I think is very unique to tech where you're given like an extraordinary amount of responsibility, very young, but you're still sort of transitioning out of a very structured life of like, you know, high school, college.

25:03And then it's like, you think that there's a rubric and you're following and you're like, if I just, if I just follow the rubric, I'm going to get an A plus like, you know, and, and I think that you're describing kind of like that exact. So were you young? I think I must've been like, I don't think I was young enough to be honestly, to be thinking that way. I think I must've been like 24 or 25, that's young yeah yeah yeah I was I was a baby at 24 so yeah clearly I was too but I also meet so many 24 and 25 year olds who are like oh yeah so much further ahead than I ever was and I'm so deeply impressed by them all the time so I just like it's one of those things where I'll be constantly just being like these guys really have their shit together in a way that I did not don't get me wrong I mean oh my god like at least I wasn't that bad but like you know I uh I yeah So that was really meaningful.

25:51And in a way where it's like, again, like it's deeply flattering and so nice to be seen and to have someone push you in a direction where you then end up like, where they see something that like a pattern that you hadn't caught yet. That was awesome because the work that I did after that was like so big and so exciting and so fun and did feel much more aligned with my strengths. But then on top of that, not only have that, but to have someone more or less teach you like, here's all the steps you need to take. Like, because even though I wasn't the one actively leading those at the time, the lessons that I learned from the way that she handled it were so instrumental later on.

26:26Like, if you want to make a change, how do you make it? Like, how do you like get buy-in from multiple different people? How do you do it in a way that's like not necessarily super politically? Like, so it was, it was really cool. I think it's super cool how like people early in your career, like really disproportionately like make an impact on you. I tried to remember that when I was a manager of young people where it was just like the experience I give them they're gonna like hold with them forever in this way that I remember really imprint totally because you're just like a sponge then right like and later I still have PTSD for one of my bosses at Amazon my god good and bad good and bad it imprints but good and bad um so my answer to this question is a little different um mine is somebody who maybe gave me a hard truth or just sort of like changed me very meaningfully.

27:12And at the time, so my person is Amy Sherman and she was my EA. And she did this like 360, you know, sort of like review of me before, like as part of her own onboarding. When she and I met for the first time, she said, hey, so, you know, I collected feedback on you, like what it's like to work with you, like how you're perceived in the organization. It just helps me sort of like navigate. and I was like what and she shared with me she's like oh yeah everybody thinks you're so smart and impressive and like um you know very talented uh but there's also this thing that came up pretty consistently which is that like you don't really need any help and I was like what do you mean I need so much fucking help what are you talking about right she's like well there's this idea that like you have it all figured out and so does your team and that actually was like this really really helpful feedback for me to hear because I'm one of those people that I can be very buttoned up and not show you how hard things are that has like been my superpower and it was at that moment for the very first time that I considered that wow maybe doing that actually like is a disservice to my own team because imagine being on my team and you're trying to like get shit done which as we all know in a large organization is like cross-functional relationships, like horse training, like, you know, supporting one another.

28:38And if, you know, somebody on my team is trying to get something done and it's met with, well, you guys seem to have it all figured out. Like that's really bad. And so it was like the very first time I reflected on this thing that I felt like led to, like helped me get to where I, you know, was at that moment, but it was also going to hold me back from like where I was going. And that was when I was like, I never considered like actually sharing my vulnerability or sharing that. Yeah, things are really fucking hard for me, actually. Right. And I still think of that as like truly like career course altering feedback that I am so grateful for and continue to be like, you know, as I keep moving through my career.

29:24So at the moment, I remember feeling crushed and like not really understanding why she was sharing it. And now I am actually just so grateful. So happy to share that story. OK, so then the second question is like a setback that you're now grateful for. Maybe it was like a job that you really wanted that you didn't get. Maybe it was getting fired. Maybe it was like, you know, something that a track that you were on that didn't end up working out through no fault of your own. but now you're like so happy that it didn't actually work out the way that you wanted. Does anything like that come to mind?

30:00I think because I was lucky that my first startup job like ended up being like a six-year ride and like ended in an IPO. And I felt like I had like a lot of impact and influence and built an amazing team. And like, you know, just really was kind of a magical experience. I've always looked for that with every subsequent role. And I didn't get that fully with social capital. And at Glossier, when I was three years in, half of those three years in the pandemic, I was just like deeply, deeply, deeply burnt out. I also knew that it like wasn't the right fit. Like I missed technology. And, but I felt really stuck.

30:43And I felt really like I wanted that. I wanted that narrative arc. I wanted that journey again and also felt like deep, deep loyalty to the team. And so leaving was really hard. And I was lucky that I could leave that job without having my next one lined up. So I, like, focused on hiring my replacement, like, getting things as good as I could before I left. But really left with, like, no plan for what I would do next aside from some consulting. And, and which is not, you know, it's not like the beautiful send off that you want for yourself, or the perfect like narrative for Twitter or LinkedIn, as we've talked about previously.

31:21But in hindsight, I'm so grateful that I was in that state and, and had the like, economic flexibility to like, you know, not have my next thing lined up. Because without that, I'm sure I would have gone into like another comms job or something that was a little bit more linear. And instead, I ended up taking enough time that I accidentally raised a venture fund and completely shifted my career. So I think like really amazing things can come out of like uncertain times and limbo times and giving yourself space. And so I'm grateful that I did not have the sort of trajectory and send off and, you know, have everything sort of like all tied up with a bow because it forced me to spend some time exploring other things.

32:14Amazing. Okay. I have a different question for Mac. So is there like an unfair advantage that you're grateful for that you don't really talk about? Like something that you're thankful for and have honest gratitude for, like that's, that could be in the category of like privilege or luck we can't just talk about what a hottie mac is yeah you're like well i was blessed hair you know the blonde hair isn't natural right like that's not an unfair advantage that's one i pay for

32:50um i this is so funny helen is asking this because we talked about this earlier but um I was saying how it seemed kind of insane that so many amazing things in my career have happened just because like truly like I spend so much time trying to like architect every single moment of my life to like add up to like long-term goals and yet like most of the like incredible opportunities that I've had have happened because like I was at the right party or the right dinner at the right time and not like a networking dinner like um hello great chat dinner exactly great chat dinner that's one of my examples like I like I and these and these friendships have been so helpful for me beyond the pod even like professionally like I we were just talking about how I call you guys both on a regular basis now that I'm doing um more comms work because I have no idea what the shit I'm doing.

33:44Like, it's been very awesome and very exciting. But yeah, it's, I think this is one of those things where too, I think it comes back to some of the questions that we've asked in prior episodes around like, you know, startup cities, like, do they matter? Like, yes and no. But one of the ways in which, yes, like I met my now boss at a dinner or at a, yeah, actually I think at like a dinner party. I remember there was this one time where we had this like really big blocker for a launch that we were trying to do at Brex. And it got resolved because I happened to meet the person who I had been cold emailing for six weeks in a row out in Presidio Heights at the park.

34:28This sort of thing, it's just the life will throw you these random things. And by going out and having us, it's just a good reminder, go out and have a social life because you never know what professional things it will unlock to have that. Totally. I mean, I think that there's so much power in sharing that part of your path. I mean, like, especially for you, Mac, like, even acknowledging that luck played a role. Oh, huge. Is really important. Because when we think about, like, why we started the podcast, why we share these stories, right? It was to help people who are also just sort of, like, maybe feeling stuck or, like, wondering, you know, if they're approaching a pivot and, like, sort of how to navigate those moments.

35:04And so something I've been thinking about for planning this episode is sort of like, we're sharing all these stories and what we're grateful for, but like, how do you pay like that luck factor forward? Or how do you like pay some of these like lessons that we've learned forward? And that's, that's hard because you can't like lecture somebody into reminding them how lucky they are and how much privilege they have and how like people have so much less and they do, you know, more with that. And so you should be, it's like, it's a very hard conversation. Um, but I was thinking about something that people turn to me very often for, which is like shaping their personal narrative when they're leaving a job, you know, whether they're taking time off or they're changing jobs.

35:41jobs. And something that I remind them is that like, even though you're feeling really exposed and sort of nervous in this moment, that you can create any story looking at the rear view, in the rear view mirror, and you can make it sound extremely intentional. Like, well, then of course I would take this job because it would lead me to this other thing, right? Like you can, you can tell that story with so much confidence and conviction in a future time. So even though you feel like, like I feel the need to explain these moves right like our episode on like you know when knowing when to quit right you're the only person who's feeling that way or thinking that way about yourself and so yeah so that first thing is like you can create any story um in the rear view mirror and make it sound really intentional and the second is that no one really knows all the luck and coincidence uh and frankly like mistakes it took to get exactly where you are and those are your stories to share and I share them very liberally one-on-one and also this podcast has been kind of cool because I get to like share all these mistakes I've made and like and for the very first time in many cases too and so I don't know I think like the luck thing is can can be uncomfortable right because you're just you're most of us like we're spending most of our time out there like trying to present ourselves as very confident and capable in our roles and you know I think luck and being at the right place at the right time like you said Mac um has been such a such an important part of all of our stories.

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37:09I mean, one thing you learn is that talking about things that were hard or where you got a lucky break, like when it's in the past is actually the biggest show of strength, right? Like, if you are in this amazing position, and you say, Oh, yeah, like I got here because I checked all the boxes. And I'm amazing. That is like way less compelling than like I got this lucky break and then this happened and it actually just makes you so much more interesting and someone people want to root for and is like again like a show of strength to acknowledge that that there's so much randomness um behind any great career story and so I love I love when people do that I think it's like you know the more successful you are, I think the bigger the obligation to be honest about how you got there and the bigger impact that can have for people.

38:10And so, yeah, so I think that's, I guess we don't get a ton of that these days. I don't know. There's a lot of chest thumping right now. But I think when people do share those like crazy stories, they tend to really break through. And so if you're someone who's lucky to have ascended to a place of, you know, envy or desire. Like it's, it's, it's truly one of the coolest things you can do. Don't be vulnerable while you're in it. I like not public, only with your friends, but when it's in the rear view mirror, that's the time. Totally. Yes. Perfect. Happy Thanksgiving, everyone. I'm thankful for you guys.

38:56audience yes yes thanks for tuning in all right see you next week bye bye guys thank you for listening to great chat have questions for us be sure to submit them at another great chat.com see you next week

From the publisher

Our obligatory Thanksgiving episode, with a twist. We're sharing what we're grateful for now - even if it felt devastating at the time. The setbacks, the lucky breaks, the uncomfortable truths. Plus Nano Banana, Ryan Lizza Substack part 3, Rippling v Deel part 17, and more. Happy Thanksgiving - we're grateful for our listeners!

Mercury is back as the headline sponsor for season three! Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

This podcast is edited by Eric Johnson from ⁠LightningPod.fm⁠.

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