PSA: Don’t bother trying to plan your tech career

0:05This week on Great Chat, we talk about five-year plans. What are they? Do you need one? And how to think about planning in such an uncertain environment. I'm Mac and I'm joined by Ashley and Angela. 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 2 ,000 entrepreneurs who use Mercury to make managing their money unbelievably simple. Hey, guys. Oh, my gosh. Mac, you are Steve Jobs brought back to life today.

0:42I was going for spooky season because I always think that this sweater gives a little bit of like skeleton. And I did like the whole like, you know, 2000s makeup. So I feel very grungy. But I like it. You know, if you really want, I could talk to you like this all episode. Yeah, that's I don't know if that's a Steve Jobs impersonation or Elizabeth Holmes impersonating Steve Jobs impersonation. I think it was Holmes. Because if we're being honest, I think I'm giving more Liz Holmes than I am Steve Jobs. Yeah. Where do we fall on the whole Liz Holmes? Has she been vindicated in the whole media was too harsh on girl bosses of the 2000s?

1:21She was just in founder mode, guys. Like, what? Is she still in prison? What's the latest on her? She is, but she's tweeting up a storm. I don't know if you guys have seen this. I think the rumors are it's not actually her. She has a team. Maybe she's like on the prison phone to them, but she has a team that she's just become like a Twitter thought boy. So love this era for her. I don't know if I'm ever really going to get be able to be able to get behind medical fraud, but I do. Like she is a compelling and funny character. Like I don't, I don't know if I can founder mode my way to, to harming people's health, but like I do think I do think she's funny so you guys I have to tell you about a thing that I discovered it is this girl Mara she's like I don't know she's got to be like late teens early 20s and she comes on the internet she's like hey guys if you had to pick a like scary Halloween character, horror movie character, like main villain to take on, who do you think you could beat?

2:31I think I could take on Jeepers Creepers. For those of you who like aren't super deep in spooky season lore, Jeepers Creepers is like a seven foot half bat, half man, rabid fucking scary thing that has like a disc of human teeth elongated as like one of his primary like killing weapons so like kind of an odd choice for a five foot three girl and the entire internet has just been sort of dogging her they've been like girl like what are you doing what are you thinking you are like a chihuahua in a purse uh at the dog park like surrounded by saint bernards and she's like no like i can take him like i'm not scared even a little bit come at me jeepers creepers it turns out jeepers creepers has social media oh of course freddy krueger like all of the classic like Halloween characters are now like on the internet, just like making all of these social videos about, about Mara.

3:29Like Jeepers, Jeepers like literally like planned her funeral and did a video on it, which was like low key, very scary, but she's just into it. And she's like, Mara's army, like pull up, like, let's go. Like, I'm ready. I'm ready. I can take on any of you idiots. Like she's such a fucking icon. This is a great Sora use case. Like she should make her cameo available and then we can all create like fan content around her showdown with jeepers creepers as long as there's not any like ip there that um that we can't touch uh i wonder i wonder which which era or which uh which conglomerate owns the jeepers creepers ip and how litigious they are because that would be kind of fun to watch team mera by the way i will always be team Mara, I 100 % behind her.

4:15I think she knows something we don't. Like she knows either like she has a superpower or he has like an Achilles heel and she is ready to exploit it. So I think her superpower is just confidence, which is a thing that all of us should adopt. Like just the audacity, you know, like the entire internet's like, girl, you're going to die. She's like, no bitch, I'm going to win. I mean, the part that I love about all of this is like the intense debate that has arisen about something that could actually never ever happen it's like a totally hypothetical but I love how I love how on board people are with this whole I also just love like corners of fun I think it's like easy to feel really like you know there's so much going on no matter really what you believe there's a there's like a lot of things that feel like deeply heavy and scary and so having just like these constant reminders like I think one upside of social media.

5:05We talk about the downsides all the time. But one like really fun thing is just to see like humanity connecting with each other, like just being like, let's go, let's go laugh and joke. And just like, I think that's really beautiful. This reminds me of, um, there was a wave of debates around like, could one grizzly bear take on a hundred eagles or whatever? And And people were so passionate about these animal showdowns. And there might even like be videos, explainer videos around like who would win. It was the 10 men versus one gorilla, right? Like that one was like the one that really set people.

5:43And people were like very confident. Obviously they were going to fucking kill the gorilla. And then some of the like gorilla experts were like, no bitch, no you're not. And I love that. I love like a low stakes righteous like battle. obviously not low stakes if this were happening in real life but you know on the internet it's pretty it's pretty low on Sora like like again like in in AI videos in in modeled modeled videos yeah guys this is 90 % of my life like my son my five-year-old son these are the questions he asked me like all the time like hey mom if Darth Vader were to fight you know like a B-52 bomber like who would win and like I should just send him on the internet you know like there there are like-minded people who spend their time asking random matchup questions.

6:33Send them to Auntie Mac. I also have strong opinions as a nerd and an aerospace person about who would win in a B-52 versus Darth Vader fight. So I'm also happy to answer that for him. Give us the TLDR. Who's winning? Okay. So obviously the B-52 on just like pure, like if it's a good pilot, I think that they'll win. But the thing is, is that the lightsaber is like pretty powerful. Yes. This is the debate, which is what can it cut through? Like what can a lightsaber cut through anything? It's like the real question. Yeah. The lightsaber can cut through most things and certainly like metal people.

7:14Has anything happened like in tech or the world? Note. I feel like a few things have happened in tech recently. Like we've had, we've had a lot of things have happened in the world. big things have happened in the world we should we should shout out ceasefire in gaza hostages back like those are those are huge wins um and uh we don't it's not not even a political statement to celebrate that so yay i'll take it um and the hostage reunion videos are like pretty incredible i like i don't know if you guys have gone down that rabbit hole but um but yeah that's that's been the content of the week for me.

7:58Yeah, no, I agree 100%. Like less suffering. Please. It's really beautiful and makes me really hopeful. Meanwhile, tariffs are back from what was it 100 % tariffs on China, and then crypto tanked. China also added insane, like very intense export restrictions and review on all rare earth metals so that means that doing basically any electronics or batteries or like infrastructure projects becomes really really hard because china has gone and taken over anywhere between like 60 to like 98 percent of various like depending again like on which rare earth metal we're talking about but like if we're talking about cobalt like they essentially own the entire Earth's cobalt supply.

8:49So yeah, it's escalating. Not loving it. But a lot of people have very strong opinions on how this plays out. I don't feel like a super expert here. But yeah, it's an interesting moment. I think there's also been some really unique developments in tech that we're starting to see that I can't tell if this is tied to geopolitical stuff or if this is just like the moment that we're in, particularly in and around AI with the industry ventures acquisition, I think is an interesting thing worth us discussing, just because this is not unprecedented, but certainly a very large venture acquisition, one that we haven't seen in a while.

9:29And I'm super curious, especially with you two both being in venture at very opposite ends of it, what your thoughts are. In case anyone's confused, Angela is at the big end and I'm at the tiny end. Okay. I was going to say that you're at the nimble end and she's at the established end. What about that? Everybody's a winner. They're not at that size. Because you get to move faster. She has to go do like 25 weeks of diligence and like a ton of negotiation. She has to fly to Europe. Yeah. That's true. She just gets to fly to Europe and debate the poshous accent, which is low-key a vibe. I love that for you, Angela.

10:03It's interesting because I think all of the major platforms, Goldman, UBS, JPM, the private wealth channel has become so important to them. And all of those clients care about access to all these tech deals, right? They're all trying to get access to open AI. And so to me, it feels like a very natural extension for Goldman and their alternatives platform to get into secondaries and get into venture and get access to deal flow for their private wealth clients. It's also interesting because multiple venture firms have launched private wealth arms, right? General Catalyst, I think Sequoia. And so that's like a place where folks are moving and optimizing.

10:48thing. I do think this is like a greater and interesting conversation too around like what is the future of finance like as we see a good amount of like I'm not saying that like private equity has reached its ceiling it certainly hasn't but I think like you're starting to see it consolidate around fewer and fewer categories as it's like sort of maxed out levels of efficiency on a lot of like a lot of verticals that it's gone after the last couple of years. You're starting to see like iBanks, like investment banks change their entire direction. This I think is a really good example of that. And so like, I'm super curious, like by the time our kids are grown up, what does finance look like?

11:25And what does finance look like in America and the West generally? Like it's still going to be a huge part of whatever we're doing, but I'm curious to see like what form it takes and if it's more like just big platforms sort of looking like banks used to, or if it's like highly specialized, almost more so than what we're looking at right now. I think it'll just be fun to watch. I think that's the natural evolution of all these different asset classes like private equity. You either become an asset aggregator like a Blackstone where you go into all these different types of strategies and you become a large multi-asset manager or you become very specialized in your playbook.

12:01Like I think the Vistas of the world and the Toma Bravos of the world have their playbook around software and they've really stuck to it. But I think a question for all those firms, to your point, Mac, is with AI and the disruption in software, how do they adapt their models and how do they take their strategy and change it? So I think the same thing is happening in venture. And you see General Catalyst and Sequoia and others expanding into multi-asset and then others like Ashley doubling down on venture as a strategy. Should we head over to our main topic for the day? This was just something that was top of mind for me while we were debating posh accents in London and evaluating companies' five-year plans is, you know, I spend a lot of my time judging is a very strong word, but testing the five-year plans of companies that we're looking to invest in.

12:53And it really made me think about how I run my own life and my own career and whether I should be more structured around having a five-year plan. And so I took the opportunity where I have both of you wise women here with me to get your thoughts on how you plan for the future and how you build some structure around your career. So I'd love to hear if you guys similarly do five-year plans and if not, what some of your approaches have been. Here's the deal. I know what I'm good at. I know what I'm bad at. I know who I work well with. I know who I don't work well with. I know what circumstances I like can do exceptional work in.

13:32I know what circumstances I can do fine work in. And I know what circumstances I can work in. And I can probably do it for like six months before like wanting to off myself or those around me. I don't think that I could have. I feel really happy about my career. I feel really happy about the like choices I've made in life and where it's ended up. This is probably like one of the few areas that I'm like really type B in because ultimately Like, I just don't think that I like to plan. I like to think ahead. However, in no universe could I ever have anticipated all of the like incredible opportunities that have come across my plate.

14:08And so while I think that there's a huge amount of value in like really getting clear on your priorities, strengths, weaknesses, and like values, goals, whatever, planning against life just feels kind of insane given like all of the shit that will happen to you as a human being in the world and also like on the nice side like all of the things that you never could have predicted like I think if you talk to us a decade ago and you said like what is the like biggest technology going to be in 2025 what is going to be like what will the economy look like I think there's no universe in which I would have said yeah I'll be working in a factory you know like no universe there's a universe where like I could have guessed that I would do VC at some point but like I didn't think uh I yeah no universe could I have picked that and I probably also wouldn't have picked AI like I'm just not a I'm not like that so um but I get I get the uh anxiety around it I just sort of feel like life hands you it's shit and you take you make the best of what comes your way.

15:17Yeah, it's interesting. I used to really envy people who had a clear picture of what they were working towards. I think it's also how you're wired. Like, Mac, I'm more like you, but I know people who are, you know, they wanted to be a Fortune 500 CMO and they had an idea of like, okay, here are all the things I'll need to do to like get to that place. And I've never had that like end destination in mind. And so the first 15 years of my career were very opportunistic. I mean, my first startup job, I was there for six years. And so I got to see the benefit of like being in one place for a while and through multiple chapters.

15:55And so I've always had that desire and orientation whenever I go into something new. But when it's time to make a change, I like to maximize for like, how do I broaden this aperture and make it as wide as possible and see what the universe might have in store for me. The big shift for me was in choosing venture, but raising my own fund, because then you really are signing up for a decade plus, or if you're building a firm and you're raising from institutional investors, multiple decades. And that was a huge shift for me and was actually a very uncomfortable thing to think about as someone who had always liked the optionality that comes with, you know, working at other people's companies, but also one that I think was beautifully timed with, I mean, I'm like 40 now.

16:47You start to think, like scarcity stops being like a bad thing in some ways, like really choosing a lane. And then also knowing that even if I'm doing this thing for a couple decades, it's going to change so many times. And how do I want to think about my goals within that context? So I've switched into like I know exactly what I'm doing in five years. Now how I'm doing it is going to change and evolve in ways that I can both anticipate and ways that I cannot. But there's some like fun in having that lens that I wouldn't have appreciated in my like operating days. Angela, how about you? How do you think about this?

17:27You to me seem like the person most likely to have a framework. whereas Mac and I are like, woo, like flying around with the wind. I felt like I definitely had a framework when I was younger. There was like a very set path for people in finance where you do two years of thinking and then two years of private equity and then business school. And I feel like having that really strict lens in the world actually prevented me from seeing a lot of broader opportunity. And so I would say in the past 10 years, in the second half, I've been trying to operate more opportunistically, but it does feel very difficult because you're constantly bouncing around from different things and exposing yourself to a lot of different ideas and opportunities and not having a very clear framework for how to evaluate all of that makes it difficult to sort of prioritize everything.

18:17But I do think that I've shifted from a five-year plan to thinking about skills or experiences that I want to build versus like a linear trajectory. So I I guess I'm curious for you guys, as you navigate through the next five years, what are you focused on building? Like, is it for Ashley? Are there specific types of deals that you want to work on? Are there types of entrepreneurs or how do you keep yourself interested, learning, given that you know exactly what you're going to be doing in five years? I mean, at the highest level, I think the things that I am optimizing for in this next chapter of my career are three things, like people impact and then autonomy slash freedom.

19:04And then the way I get to put those together is going to look very different. I mean, the thing that I love about venture is you are building multi-decade relationships with people, right? Whether it's your partners that you're building with, the founders that you're backing, the LPs that are backing you. And so just being really intentional about those relationships and continuing to raise the bar both for how I make those decisions, but also how I show up in those contexts. It's a hard thing to quantify, but that's deeply inspiring to me. And then, yeah, in terms of impact, like I think for me, like how do we continue to build a product that makes some sort of dent in the trajectory of the people we back or changes the changes, you know, builds generational wealth for people who've backed us?

19:55I don't know they're all like very like big picture things and it's it's it's more sort of incremental and compounding than like you know in three years we take a total right turn and do this in a very different way I think venture the feedback loops are longer and so I think it's just like a constant like building that muscle of learning and improving and trying new things but but very different I think than an operating career where you're like okay I did this function Maybe I want to go over here and do this function and then try this thing over here, hop over to this other industry. So it's a different way of orienting for sure.

20:33I know, Mac. I'm so curious. I mean, you are in high demand in your role and your industry. Like, how do you decide if you're still learning and having fun versus, you know, when you have reached your maximum potential in a company and need to start looking for something else? I think if I just stay really connected to how I'm doing in the moment, like I like to focus on like today, this week, this quarter, like how are all of those going? Like how am I performing in those contexts? What am I learning from like – like I usually will do like a retrospective after like most big projects that I do.

21:10And I actually find that by doing like the retro versus like the plan, I learn a lot more. and if I keep finding out that like the things that I learned or the things that I or the direction in which I grew is like more of the same or like doesn't really resonate with me as much or like feels misaligned that's usually how I make that decision again like I've said it just doesn't really work to plan because most of the best things that have happened to me have been like completely out of the blue I also think that like just in this genre of work having a plan is really hard. Like I don't know too many people who like are super type A about their career who do well in startup land.

21:46Just because like you can't really plan your way into any like meaningful roles or meaningful projects, it tends to be a little bit more serendipitous. And Mac, you kind of alluded to this at the beginning, but I think this topic is especially interesting and maybe ironic in 2025 when you just think about what's happened this year and how impossible it feels to see around corners right now with like not just the pace of technology, but culture is shifting. Policy is all over the place. We are living in like very chaotic and uncertain times. And it feels like the skill to build is not like being super intentional about your planning, but is being comfortable with that uncertainty.

22:30And then the ability to see opportunities that arise out of that. And so I guess I just want to say for anyone who's trying to plan your career, it's important to know what the things are that matter most to you. But I think it's also equally important to be really flexible and open-minded about the details. And especially if you are graduating into this market right now and kicking off your career, I think it must be very daunting to try to plan exactly what that's going to look like because there are so many things that are sort of unknowable right now. And so I think as humans, we all just have to become increasingly adaptable and resilient to a constantly changing environment.

23:13And that is the move. That is a survival skill to build. And I do think when it comes to a plan, one of the most useful types of planning you could possibly do would actually be that resilience. So at any given point in time, I'm like, do you have enough cash where you would be fine for like 180 days? Like, do you have a compound in New Zealand that you can take? How's your bunker doing? Really? Like, I just want to know personally. And can I get an invite to the bunker? Do you have a friend with a bunker? You have a friend with a bunker? Oh, my God. Look, it's just so fancy. Do you have a friend with a bunker?

23:51I don't. I don't. But we should get a great chat bunker for sure. I love this for us. Yeah, yeah, yeah. I don't own a house, but I could get a bunker. That feels like the correct prioritization. I think it's right that we've taken the five-year planning question into dystopian prepper territory. That is the right trajectory. That's the logical end. I mean, like, why else would we be asking ourselves these questions if not to prepare for the end of the world? It all ends in spam. I just want us more canned food. Like, Angela, how do you help your kids plan for the future right now? Like, I really, I just think it's, I mean, they're young, so they probably don't have five-year plans, although maybe they do.

24:31Yes, become a TikTok influencer asking the hard-hitting questions of, you know, who would win in a Darth Vader battle. That's the five-year plan. Yeah, I think that could do very well. No, I'm actually just, I actually have a cousin who genuinely does do that for a living. He doesn't ask Darth Vader questions, but it's the craziest thing. He makes something crazy like 17 grand a month, and he is just, he does like these, you know how people have ASMR? He just does like, he pretends to be your boyfriend asking questions. That's it. That's it. And it's crazy. It's like soothing for people. Like on YouTube.

25:06Exactly. How was your day? I was super curious. So I like opened up a video and then I was like, this is too weird. I can't listen to this. But it was just like, Hey, like, how's your day going? He's like an AI boyfriend. What I'm saying is that this Darth Vader plan could be real becoming an influencer could be real I could see it Angela like he's he's a lover not a fighter like we have enrolled him in soccer and you know the the teams are like on the field and the coaches are like wait like we're missing a player like where's Asher and he's like on the sideline eating snacks chatting with his friends like totally unconcerned about the game that's happening so we're gonna we're gonna have to figure out what the right career track for him is.

25:44No, I think this is the nervous system that we need to survive this period. He's just, he's like, yeah, you guys can play your game. I'm going to be over here living my best life. I think, I think he's our guru for this, for this eating spam, you know, favorite spam, like undefeated, undefeated favorite snacks. It really does all end in spam. Yeah, you can really stock a basement with those. So he's ready. So he's purpose built. All right. Well, since Max started us off with spooky season, let's continue rapid fire autumnal fall themed questions. So what is your favorite seasonal drink or snack?

26:29Is anyone going to not answer pumpkin spice latte? And if you do, why? oh I don't I don't drink those for all the listeners only please tune in just for max space to that response I'm not I'm like I'm not into the Starbucks industrial complex or like flavored flavored coffee beverages of any kind I'm sorry I mean I support your right I will fight for your right to drink a pumpkin spice latte but I will not partake I too support women's rights and wrongs. And let's be really clear. This is a wrong. Like this is, this is just like an objectively bad opinion and bad take. And I love you, Ashley, because you are so brilliant, so accomplished, so smart and just wrong on this count.

27:12Like you don't have to go to Starbucks. You don't, you really don't. There's all sorts of places where you can get a pumpkin spice latte and they can come in different flavors. You can get a caramel apple latte. I'm like a savory girl. Like my cravings are never, I want something sweet. Like I want like my seasonal craving is I I want like oxtail stew or something like really like rich and fatty and flavorful. So I'm low iron. So I just like assume that all of this is my body begging for what it needs. So yeah, so I'm just like in an entirely different, you know, different vector of cravings. No offense to your pumpkin spice latte.

27:53It's okay. You're never going to hear me say anything bad about oxtail stew. Okay, great. Come on over then. They don't have any good Caribbean food down here, or at least I haven't discovered it. Listeners, if you live in Los Angeles and there's good Caribbean food, tell me about it. But yeah, OK, this you you are making you are making more sense now. And I hold my opinion, but I still I understand you more. I didn't anticipate this question unearthing so much about each of our personalities and desires. But this was a hard hitting nutritional deficiencies. Yeah. Well, we're getting real on the pod.

28:26Yeah. Yeah. I love that. Angela, what's yours? I'm in the basic camp of apple cider donuts. That's just like the fall treat. With a pumpkin spice latte. No, I was going to say we're going to Boston next week and that's like on the list of things to get. They have those at the farmer's market like on my block and I haven't had them, but they look delicious. So Angela, come visit. I'm so jealous, Ashley. Ashley, what other fall savories are you into? Like I'm thinking like a persimmon salad with goat cheese sounds really yummy. Oh, I would love that. That's even a little sweet. I actually love the pumpkin flavor or any squash flavor.