Founded On Purpose

How do you sift through the noise of advice, embrace the messiness of life, and find success on your terms? Startup and venture capital veteran Anastasia Simon shares her framework for evaluating advice, how she’s redefining success in her life and, perhaps most importantly, her stance on Drake vs. Kendrick. 

Episode Summary:
In this episode, we dive deep with Anastasia Simon, a force in the venture capital space, about her refreshing perspective on mental health, play, and what success really means. Anastasia candidly shares how she navigates the complexities of taking advice, embracing challenges, and learning to play again in a world that often prioritizes productivity over well-being. She reveals her strategies for maintaining mental health in a demanding industry, the importance of intergenerational relationships, and why it's crucial to discern which advice to take and which to leave behind. Whether you’re a founder, creative, or just someone trying to make sense of the noise, this episode is packed with wisdom on how to rethink success and find joy in the process.

Key Themes:
  • Navigating Advice: How to determine what advice to take and what to leave.
  • Mental Health & Self-Care: Strategies for maintaining well-being in a high-pressure environment.
  • Rethinking Success: Challenging conventional ideas of success and finding your own path.
  • Relearning Play: The importance of play and imagination in adult life.
  • Intergenerational Wisdom: The value of learning from both younger and older generations.
  • Being Right & Wrong: The importance of introspection and humility in decision-making.

What is Founded On Purpose?

Welcome to Founded On Purpose, the podcast where business meets impact. Hosted by Kt McBratney of Renew VC, each episode features founders, investors, and ecosystem builders answering the same set of questions. While the questions stay the same, the insights and conversations are always unique and thought-provoking. Join us to explore how these innovators are aligning profit with purpose.

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Kt McBratney: [00:00:00] Hello everyone and welcome to Founded on Purpose, the show where we get to know the people working to align business and impact, profit, and purpose. I'm your host Kt McBratney. Each episode we ask a different person building an interesting company the same set of questions. Some are founders, some are funders, and some are players making the ecosystem thrive.

And while the questions are the same, The answers and the conversations they open up are wildly different and wildly interesting. Today, our guest brings depth and breadth. Anastasia Simon has worked across the startup ecosystem for more than a decade, from marketing, business development, programming, and venture capital.

She's held roles, including managing director, investment principal, advisors. And so much more, she's known for this expertise across industries and her unwavering commitment to practically helping founders, especially those who have been historically overlooked. You'll find in this conversation that she's proof you can [00:01:00] be both no nonsense and a lot of fun.

Anastasia, welcome to the show.

Anastasia Simon: Thank you for having me. I'm excited to have the conversation.

Kt McBratney: Awesome. So we'll just dig on in. There are eight questions we asked and the first one. Is one of my favorite in one word no cheating by like smooshing words together. What's your purpose?

Anastasia Simon: Oh, it's a good one. Um, I would

say existing Right, right, right like right now i'm very much in this the space of What does it mean for me to just exist?

I've spent a large portion of my career focused on achieving and overachieving And doing all the things And now it's, how do you learn to just be, you know, in that maintain kind of state? Um, without having to constantly climb the next mountain.

Kt McBratney: How do you navigate that, given the [00:02:00] roles that you've had?

The fact that people see and see all these things that you can do, and really the culture of our industry. Is perpetual climbing. How do you navigate that? Also knowing you're ambitious, you are extremely capable and can and have incredible things. How do you balance that? Given that the culture that surrounds us isn't always the best ground to do that.

Anastasia Simon: Um, so I think some of it is me reframing what success looks like and feels like for me, um, which I'm deep in the work with a therapist to do like, please go to therapy. We love therapy. Don't do it by yourself. But so what I would say is it really is just me rethinking success, rethinking what does, what does having it mean?

What does achieving mean? Um, because at some point you, you have to stop, you have to stop climbing. You know, and you have to also look back and say, like, I did good. You know, I don't [00:03:00] think we as a society do that enough. Like, give people the space to look back and say, oh, I did well. It's, oh, so you did this thing.

Well, you're not on the Forbes 30 under 30. Oh, well, now you are, but you're not a billionaire. And then now, well, you are, but. It's like, sometimes being good enough is good enough.

Kt McBratney: It reminds me of this conversation I had with the founder earlier this week about how so much of the work has us fixated on the doing.

When we need space stop to do this being so very much parallels here on this, like existing can be a purpose. It's not about, it's not about it. And like, we've had lots of good conversation getting into the realness of navigating these systems that we were all born into and different at different intersections.

And. It's, it's so powerful, just even doing that work yourself to redefine success. I've been, it's something I've been playing around with is this idea of [00:04:00] wealth. What does wealth mean for me at this season? Is it financial? Is it emotional? Is it physical? What, what feels like wealth? And, and I love to hear that we're on parallel tracks in different unique journeys.

Anastasia Simon: And I think that's interesting because we're both like elder millennials who came of age in the girl boss era. And girl boss is called girl burned out. So We're we're trying to figure it out. We're not going back to that craziness No, thanks,

Kt McBratney: and also helping other people not fall into those traps themselves, which I think is Often a rarity, um to say like not only am I going to help myself Not either fall into the same trap or avoid it.

But like I don't want to see Founders, operators, anybody, anybody, you don't have to be in the startup ecosystem experience burnout the way that I have multiple times in my career. And I think that that is, is also very linked to that purpose of existence is what of me do I have to give? And what do I need to save?

I need something for me too. And that's [00:05:00] okay. Yeah, for sure. For sure. Well, this is an interesting followup to that question. Number two, what's your most recent win?

Anastasia Simon: Oh, that's a good one. So I think I have. So I think, you know, immediately I go to career wins and getting a recent promotion like that's great.

Um, but I'm going to go back. So I just came back from the Bahamas on Monday. I have an intense fear of flying. I hate flying. I probably will never love to fly and I'm making peace with that. Um, I've been flying since I was a child. My dad was in the military. Um, is that thorough? I got on the plane. I had my music that I, you know, listened to.

I was doing my box breathing. I was talking to myself to talk me into getting on the plane. And as I was telling my therapist all of this, she goes, you were coping. That is, you did a great job of [00:06:00] coping. That is a win. And I think we don't celebrate the little wins. We don't celebrate the wins that feel like it may be a law because to me, I'm still afraid to get on the plane.

It's still, it's not comfortable. I hate it. I will never like it. I'm making peace. It's just, it is what it is, but. Me reframing, Hey, you got on the plane, you move through this process. You were able to get to your vacation, enjoy your vacation and come back. That's a win. That's an achievement. You know,

Kt McBratney: it's a beautiful reminder that so many of our wins are internal as well, or at least they're not externally visible, right?

Like people saw you on the plane. That is true. And also that win. Was internal and yet you can still share it with others by sharing that story.

Anastasia Simon: Yeah. Yeah. And I think it's because we as a society have such an external focus, [00:07:00] you know, everything is, how does it look to other people? What can other people be proud of?

And it's like, sometimes you need to be proud of the little thing. Be proud that you Said no to second slice of cake. I don't know. I don't know why you were saying no to cake, but we're saying that you said yes to the second slice of cake, right? Right. You know, be proud that you said no to having a beer when you know that like you're trying to cut out alcohol.

Like that's, that's enough. You know, it doesn't have to be, I won the Nobel peace prize.

Kt McBratney: So we are going to switch gears to career now on purpose. What do you think or believe to be the single biggest missed opportunity in your field? And this is an interesting question as I thought about it for you, because I'm like, how do we even define your field?

Right? You work in startups, you work in entrepreneurship, you work in innovation, but you also work in helping people be them best, their best [00:08:00] selves. So what's the biggest, the single biggest missed opportunity?

Anastasia Simon: Okay, cause there are a couple of different things that I'm thinking about, like I'm thinking about like the biggest missed opportunity I had for myself personally, which is, that's going to get us into a tangent of I should have been like a basketball wife or something.

But

Kt McBratney: I'm here for that alternate reality.

Anastasia Simon: I thought, wow, yeah, that's a wall. That's a wild, like alternate reality. We're going down a rabbit hole. We're not going to go this. Um, but I think like in the field that I am in, so working in venture capital, um, I think the biggest missed opportunity is, and this is gonna, this is a controversial take, is that people need to stop pattern matching.

Like pattern matching is creating a ton of missed opportunities because it's just reinforcing biases. And so for people who are not familiar with a term like pattern matching, [00:09:00] essentially It is when investors are saying These are the types of people that fit this profile for a winning company And it's these are the types of businesses and these are the individuals And some of the heuristics that they're looking at in these individuals are incredibly biased towards gender and race, um because When we talk about things that would be labeled assertive in a man, they're usually labeled bitchy and aggressive in a woman.

You know, and so they may see that as a positive in a man and not as a positive in a woman. And so you don't invest in women who may fit that pattern, but because you view it differently. And so I think that is creating a huge miss opportunity because founders who don't fit the pattern because historically they couldn't fit the pattern.

Those founders are consistently being blocked out of an opportunity to one, get access to capital and to [00:10:00] create. Meaningful businesses. That's not to say don't use data to make decisions like yet We love a good data driven decision, but sometimes you need to check that data against your own biases.

Kt McBratney: Well, and then you layer on the intersectionalities on top of that, right?

And, and it gets much more complicated and those patterns feel like facts. And, and that, that is such a brilliant synthesis because typically I tell people no cheating. Don't pack like six problems into one because they're connected. But that the identification as a pattern matching. Actually threads a lot of systemic issues within, within the field.

Together very beautifully. And also, not a controversial take on this pod. At all, it needs to be said and said and said and said until not just people believe it and it stops being controversial, but also things have changed.

Anastasia Simon: And I'm going to say it's [00:11:00] controversial for some people because, um, I think it's the way business as usual has been done, but most people recognize that.

If you are saying, Hey, these are the things that you have to have gone to Stanford, like, that's not, that's not a thing. There are founders who did not go to Stanford, who did not go to MIT, who are amazing and brilliant and building game changing technology. That, that should not be your benchmark that you went to a certain school.

It should be how you see it. Are you intensely curious like that to me, a founder who's intensely curious, they will always win because they're trying to solve problems from a different angle. How do you receive feedback? Like, that's the stuff I should be looking at. Not like, who does your dad know? And where did you go to school?

And where did you grow up? And that's, that's not really telling me anything other than you are, have a certain level of resources. [00:12:00]

Kt McBratney: You know? Yeah. So. Oh my gosh, we could do an entire episode just on that note to future self to maybe dig into that. I'm gonna, I'm gonna, question four, the halfway point, we might actually elaborate on some of that, or it might be a different, we might take a little detour.

When was the last time you were wrong?

Anastasia Simon: I'm wrong all the time. I'm wrong all the time. I tell that to founders, like, every time I sit down and advise a founder, I'm like, look, I'm telling you my opinion based off of my unique experience, my background, all of the baggage that makes me me. I am wrong. I can be wrong.

I'm not invaluable. Like you should assume that I'm wrong. You should assume that what I say is well informed, but could possibly be wrong. You know, like I'm wrong all the time. I'm wrong all the time. I'm not, when I say wrong all the time, it's not just like, Oh, I'm wrong about this investment. [00:13:00] Like sometimes I am wrong about the investment.

You know, it is what it is, but yeah, I'm wrong. I don't, I don't have a time when I was most wrong. I'm like, I am the reason why my closet fell apart in my office. Because I did not listen to my fiance and the people who were building the closet. And I was like, this is what I want. And they put something in there and I overloaded the rack and now it is on the floor.

I'm always, I'm wrong. I'm wrong as often as I'm right.

Kt McBratney: Most people are. Yes. And that's the thing. I think, I think for me, certainly as an operator, and when I was a founder, there's this weird insolubility that gets associated with. People on the VC side, right? That they know more than you, they are right more often.

And I don't exactly know why we can, we can unpack that if, if we want, why founders often believe that, but that's a bias that I think we need to pick apart because like, yes, [00:14:00] investors, um, accelerators, mentors, advisors, they know a lot, but they don't know your business the way you do. They don't know your experiences and the lessons you've learned from being right and being wrong.

And I, I think that like. By, it's funny, everybody who comes on answers that question, they're like, a lot, all the time, like, I was, I was wrong this morning, and discussing this idea of right and wrong and how we've decided somehow, it's another false binary, that you're either right or you're wrong, there's a hell of a lot of stuff that falls in between, we were like, well, I actually got that piece really, really right, and I'm glad about that, but these pieces weren't meeting through.

What I thought it would be initially, and that's okay. So it's back to like what you said about celebrating the small wins and looking at things in terms of like, it's not an absolute and investors don't know everything.

Anastasia Simon: Well, I also think, you know, in our society, we have this deification of successful people where if you [00:15:00] are someone who is like Elon Musk.

Who has objectively been very successful as a founder and as an investor, that that means somehow he is more intelligent than you or I. Yes, he has some subject matter expertise that you and I don't have, but overall that does not make him more generally intelligent. Intelligence is not like a thing that's a blanket.

People can be very intelligent in one area and not so intelligent in another. That is very common. You just, but I don't think people think of this that way. You think we, we think of it particularly in this space. If you're a successful investor, meaning you've made a lot of money, you're a CTO, you're deeply technical.

That means that you are knowledgeable about a lot of things, and that does not necessarily mean that it's so. You may have some really great subject matter expertise, but then [00:16:00] I can talk to you about something and you're like, I've never heard that before. And that's fine, that's normal. But we have to really start to lean into that.

And I always tell people, I live by Michelle Obama's vote, where she talked about being in like the G20s and all of these different rooms, um, as a first lady meeting with so many people who are Nobel Prize laureates and all of this other stuff. And she's like, but not that smart. And she's not saying it to say that that's stupid, she's saying it to say that you are equally as intelligent as these people are who have seats at the table.

You deserve your seat at the table. So yes, when you're talking to an investor, there's probably a ton of stuff that they know that you don't know as a founder, and that's fair. But there are also some unique things that you know that you can teach them. And so you have to really rethink what you perceive as a power imbalance,

you know?

Kt McBratney: And that gets me thinking about what you said about being curious, [00:17:00] and that being a trait and characteristic of a great founder, where does that curiosity come into play when, when looking at Your own or other people's intelligence and this idea of being right or wrong in the degrees of that. Do you think that there's a relationship?

Anastasia Simon: I do. I think that people who are intensely curious tend to understand that they don't know everything because that's why you're curious. That's why you fall down rabbit holes and listen to podcasts and pick up books and talk to people who are smarter than you. Um, I think that that kind of goes into that, but I also think again, a lot of this is.

The perceived power imbalance that I'm asking this person for money. They have something that I need. So some of it is I want to stroke their ego and make them feel good. Some of it is because they are at a place that maybe I want to be later in life that maybe they know something that I don't know they're in on something.

And in some cases they are, in [00:18:00] some cases they aren't. But I think it goes back into having a sense of self, you know, like you have to be, have a strong sense of self as a founder. Like super strong unshakable sense of self.

Kt McBratney: Oh, yeah. All right. This is your chance to take a stand Which I know you're not afraid of or shy away from at any point in time But question five you get to choose a hill that you would die on What is something that you are like, I will go to my last breath On this principle or this belief and it can be as serious as career related or As related to the best pop song of all time as you choose

Anastasia Simon: I mean, I don't have a lot of very tightly held soap boxes that I Won't stand on right now.

Um I think Like right now when I think about that I think about the hill that I will die on is take your [00:19:00] pto Please take your pto Like It's there for a reason. I know in our culture, in America, it's like, Oh, I don't want to be seen as a slacker, but you also don't want to be seen as burnt out. You will either take it now or be forced to take it later.

Um, so that's one of the things that I'm, I'm very big on like mental health and balance and stuff like that. I think the other stuff is like that Kendrick Lamar unequivocally won the beef with break. Like his, his. I was never a Drake fan to begin with. I will stand on that hill. Never a Drake fan.

Kt McBratney: I will join you on both of those.

Let the record show that the vote in this podcast is two to zero. It's unanimous. Kendrick one. Yeah. All right. We were talking about mental health, uh, wellness, self care. I know that's so important to you, as you mentioned, which segues perfectly into. The [00:20:00] next question, which is how do you play? Like, what does play look like for you either in work or life when you're not trying to chase or follow some predefined idea of success, how do you play?

Anastasia Simon: That's a good one. Cause I'm relearning this. But like, I think as an adult, a lot of it is just like, I'm zoning out. I want to dissociate. And so I put on like anime and I'm like, let's just like zone into something wild for like the next few hours. Reading is another one that I use. Which I find that now the two are connected.

It's like reading, scrolling, like doom scrolling, and then being a binge watcher. Those all are the same thing. It's just, you're trying to dissociate, you know? So yes, that is a big thing. Um, another thing is like, I see you have your kitten. So I have my dog, he's asleep. He's an old man. So I do a lot of spending time with the dogs in the house.

Um, we do a lot of outdoor activities. So [00:21:00] like hiking, um, In a paddleboard, kayaking, that kind of stuff. Um, and then another one is like, talking to kids. So a couple of my friends have small kids. And I love, like, we were at a friend's house last night, for Juneteenth, and her kids were talking to us. And one is nine, one is like, five or six.

And the youngest one is like, wild. Like, I don't know what he's talking about. He's all over the place. Everything you say, he has like a rebuttal to it. It has a yes. And I'm gonna tell you this story. I don't know where we're going with the stories, but I'm here for it. And it just stretches your brain in a different way to hear how they like, see the world.

Kt McBratney: I, yes, I have a, I have a kid about that same age and it's just such a good reminder because like how you said relearning to play, like we get it. Kind of conditioned out of us by busyness, by pursu by pursuit of success, quote unquote. Um, that it is. I feel like it's a practice and so it's always a good [00:22:00] reminder to me like, I'm like, what is my kid doing right now?

What thing is she believing and fully invested in and not thinking about what's next, what's next, what's next, what's next? Oh, I've got to do this. Um, she's not worrying about going to help like clean up her room. She is thinking about this entire vampire drama she has set up with her Barbies and her Hot Wheels.

Um, but that like, imagination, I, I hear also echoes of that in the reading, in the getting outside, in the anime, right? You're, you're visiting other worlds in a way and exploring. But also in a way that is recharging, in a way that isn't having to generate things yourself. Because that's the other side of it, is this belief that to be creative or to be playing, you have to be generating something.

And sometimes you can just be generating joy and relaxation and curiosity. And following what a five year old has to say is the wild ride of all of that. Yeah.

Anastasia Simon: Yeah. And I mean, what five year olds have to say is very important, [00:23:00] like hearing where their, where their brain is going is very, like, that's how you stay up on things.

Like, I'm a big fan of, like, engaging with people younger than me, because I don't ever want to be one of those people who's, like, an old, because you can be older and not be an old, you know? Right. Yeah, I'm not trying to be old before my time. I don't want to be 45 feeling 65, you know.

Kt McBratney: And that wisdom comes from everywhere.

It's also like the beauty of intergenerational relationships. I feel like that's where I've learned some of my best lessons. Personally and professionally. And not because I'm trying to be that person when I'm that age, but because there are different people at different points in time than I am at. So like, even though I maybe have been that age and hopefully will be that age, not, I won't be that at the moment, at that moment in time and as that person.

And so. I'm here for it. It keeps you grounded. Maybe we should do a [00:24:00] special kid episode where it's just like I just bring a bunch of kids and have to talk to your kids. Let's see what happened. Yeah. Round up the founder parents, right? Cause from there,

Anastasia Simon: that actually is a great idea. That's a great idea.

Kt McBratney: All right. All right. I see. This is what happens when you actually like put away the inbox and we can like dig into the human pieces of this business, right? Like you and me can nerd out on spreadsheets. We can number it out. We can. Do all of that and do it really really well and also this piece of it I'd argue is equally if not more important for connecting dots and building relationships because what else matters?

Exactly. Okay. We're rounding, we're rounding towards the end. We got two questions left. Number seven I'm excited, I'm really excited for your take on this because I know a lot of people come to you for this But you've also been receiving end. How do you know what advice to take?

Anastasia Simon: Okay, so there are a couple different ways The first thing I [00:25:00] always tell people is index for, is this person, are they qualified?

Is this person qualified to give me this advice? There are a lot of things I'm qualified to give advice on. Mental health is not one. I am not a mental health professional. I can tell you my thoughts on that, but because I'm not a therapist, I did not go to school for that. It probably shouldn't ask me that.

Um, I'm also not an attorney. I can tell you what I would do. I can point you to an attorney. I'm not an attorney. I'm not an accountant. I'm just giving you general ideas. You need to go to people who are qualified to answer those types of questions. So it's the first thing, is this person qualified to give me answers?

Does this person have the background? Have they done what I want to do? Don't ask your friends who are divorced. For relationship advice, not because they're going to give you bad advice, but because I tend to find my friends who are either going through a divorce or just got out of a [00:26:00] divorce. They're salty.

So their relationship advice is going to be full of saltiness. Don't ask them that. Don't do that. You know, think about it from that perspective. Um, the other thing I would say is go with your gut. A lot of times when someone gives you advice, it doesn't feel good. If their advice doesn't, Let's get in, let's unpack that.

So the advice doesn't feel that the first thing you need to ask yourself is, does this not feel good because it's not true for me, or does it not feel good because it's challenging me? So things that challenge you usually don't feel good and you need to sit with this. Like, is it because this specific person told me this?

What about this person delivering the message makes me uncomfortable? Is it the way that they told me the message? Like really take some time and sit with it and unpack it. But at the end of the day, if it comes across that you're just like, nah, this wasn't for me. My gut is telling me this really doesn't work.

This does not feel good. Let it go. Like it doesn't apply. Let it fly. It's [00:27:00] fine. Um, Also have space for knowing that you might be wrong because you get a lot of advice from people. Um, and you might be wrong in your assumption. And that's probably why they're giving you that advice. They're giving you, you might be wrong.

Sometimes just to lead with that. But I think it takes a lot of like introspection to say, you know, Hey, what are the things that I'm bringing to the table that make it difficult for me to receive feedback? What are the things in the way in which I'm like laying out this question? So whatever it is I'm asking for, am I not clear?

Like check yourself first. And then kind of say, Okay, does this work? If it's not work, it's fine. I don't need to hear it. Um, the one thing I would say is always look for the trend, though, in the data. So if you ask five people the same thing, and they all tell you the same thing, that's probably what they [00:28:00] answer it.

Kt McBratney: And I love that introspection, too. Like, it's, it's, it's still that slowing down a bit and saying, Wait, instead of rushing and implementing something or letting somebody's quote unquote pedigree where they went to school or how much money they have Lead the answer when that's not related To what you asked them about right navigating and just like taking a beat I feel is a step that I've failed at sometimes when knowing what advice to take or quite Honestly, like lots of things just rushing because the pace of our world is what it is and that small pause To check yourself and ask is this person qualified?

What if I am wrong? How am I showing up? How what am I bringing to this? To this conversation about advice that is independent of this person or maybe is related or triggering or connected somehow. That pause can be well worth. And be, be so much shorter than the time and the cost [00:29:00] and energy of just wildly going after it without thinking.

Do you find that to be true?

Anastasia Simon: Yeah, and I think that pause though, people think it's like, oh, I need to get off the call and sit down and meditate. No, literally sometimes the pause is I say something to you and before you respond, you stop and you think about what I said. Yeah. And then you respond. It's that simple.

Sometimes I'm just like taking a beat to think through like, and feel through whatever is going on. And like, that's a very underrated skill because again, in this industry, it's, you know, move fast and break things, you know? And it's like, sometimes you need to know what things to break, what things not to break.

And that may take you. Slowing down for a beat. Not slowing down forever, just for like a quick like a pause. Yeah,

Kt McBratney: that was it. Just like hold for a beat. [00:30:00] See where that takes you. All right, we're, we're closing out. We're at question eight. I'm fascinated to know where you're going to take this because this has been so fun and I'm like, I'm going to say it.

I'm proud of my self restraint because I've wanted to go down about 18 different rabbit holes of things that you've brought up and we've stayed, we've stayed on track. So I'm going to applaud my self discipline there. It's something I'm, I love being a leader and I am not my own best self manager. All right, we're closing out on the last one.

What is your least favorite thing about your job and what is your most favorite about what you do?

Anastasia Simon: I think like Honestly, the least favorite and the most favorite are the same thing. Um, I love Working with founders, talking to founders. Um, I tell people on an average day, I probably have like five to 10 founder calls, what portfolio companies, [00:31:00] companies that were diligent, saying things like that, um, but at the same time, it can be very draining because your context, um, just so that people kind of can get an understanding of what it's like to work in venture.

You have a lot of calls 70 to 80 percent of your day is on the phone and it's going from how can I help this founder and really dig deep into maybe there's a problem with their sales process and we're going to spend like An hour digging deep into that and then my next call is you have to pitch me And then I have to kind of switch my brain to that and then the next thing is I may have a gap where i'm not doing anything and I have to go in and like Read memos and write memos and check emails that are overflowing and so you're constantly you don't really get into a flow state Because it's the constant like context switching and that happens because i'm on the phone all the time And so while I love talking to investors and founders and everybody [00:32:00] It is very draining, and it puts me in a position where at the end of the day, I'm just like, I need 30 minutes to go for a walk, to do something that will shut my brain down, or I end up sitting down at dinner, and like, just spewing things to my fiancé about like, let me tell you this, and we were talking about that, and blah blah blah, he doesn't care.

Like he doesn't he's not the context Yeah, and I mean like he'll do that to me sometimes with stuff that he has going on at work and it's a little bit different because he's um Technical and so he works at a startup that was recently acquired and so we'll talk about some stuff but like I start going in the weeds on businesses and things like that.

And he's like, what is, we're talking about cap tables and we're talking about like a fund structure. And he's like, I don't know, where are we going with this? And how did we get here? You know, so yeah, I need time to like come [00:33:00] down off of the million calls a day and it's not just the call is the text messages.

Like since we've been on this, I've gotten so many text messages from founders and other folks at my company and from like all kinds of stuff. And I'm just like, I know when I get into it, it's going to be, Oh, I had to jump from this to this, to this, to this, to this. And it's,

Kt McBratney: I'm with you. I feel the same way.

It's like at the end of the day, it's not that I need to vent or to, because a lot of times I'm feeling great from these calls, from these conversations. I, I am a very curious person. So I love going deep and I'm like, okay, well now I really know a ton about how the vintage resale market works. And wow, these are some really interesting unit economics, but also let's talk about hair and also let's talk about agriculture.

And in the moment I'm, Loving this context switching because I'm not aware of the cumulative draining that happens and at the end of the day, it's almost just like a release valve. I have to let it out because I'm holding it all in. [00:34:00] Um, so thank you. I feel seen by that. No, I feel like it's, it's probably a much more common experience that a lot of people don't talk about it.

That is a beautiful piece of these roles, but also comes with challenges. Because we are, we are more human and we're living all these different pieces deeply. Mm hmm.

Anastasia Simon: Yes. You also have like 50 different windows opening your brain when you're doing it. And that's what, I don't know who told me this. I can't remember who told me this and gave me this analogy, but they were like, your brain is like a computer.

And you have all these different tabs open, you know, and you have to kind of shut them down at some point so that you can move into a state of rest. So you have to close the tabs, which I don't close any tabs on my computer. I have several windows. I'll probably have like 100 tabs open at any given time.

But when you're having that conversation around like. Talking about unit economics and oh, let's talk about the vintage resale market. And then, oh, we're talking about hair care and what's going on [00:35:00] with this. And then you're jumping from that into like deep tech and oh, let's talk about what's going on in sustainability.

And you have these like rabbit holes that you're jumping down and it also. Plays to like an ADHD brain. And I'm not saying this, I'm saying this more colloquially, obviously, where your brain is just like hopping all day around, around, around. And it makes it difficult. I've found the longer I've been in this space, it makes it more difficult for me to have conversations with people who don't, their brain doesn't work like that.

You know, like most of the people I talked to in this space, their brain works like that where we can have five conversations in 10 minutes and have them all to completion on totally disparate topics. But yeah, it lasted down, like, with my family or my friends who are not in the space, and I started doing that.

They're like, like, I don't, I know how we got, how did we get from there to there? And you know,

Kt McBratney: like, it all makes sense if you can see the [00:36:00] tabs.

Anastasia Simon: No, I oh my god It's like the guy the meme where the guy has like all this stuff on the wall and he's like And here and here it's like you're showing a conspiracy theory kind of map and it's like I don't I don't know how to explain it, but it worked.

Kt McBratney: No. No, i'm here for it. And I feel like that's yeah, that's why uh, I had my time in corporate life, and that's why I am in this world is because my brain works like that. I'm happy with my brain working like that, and I'm also learning how to care for myself and my, and my brain. Yeah. And other people who work the same way, so that we're not all tabs on all the time because Yeah, we, we can't.

Anastasia Simon: This is beautiful. That's another deep dive and so we're gonna, another deep dive for you to get into for another conversation is all the spicy brain people that work in this space. It lends itself to Spicy Brain.

Kt McBratney: You have just introduced a new fun rabbit hole that I'm excited to open an additional window with additional tabs.

[00:37:00] Uh, I am in research mode, so this is perfect. Yeah. To conclude this amazing conversation, because I could stay on here all day, and also I need to let you go and respond to these founders and help people build these beautiful businesses. We have shame free self promotion here. We don't have shameless self promotion.

Is there anything that you want to plug anywhere you'd like people to get in touch with you? Um, last chance. Bring it up. Whatever you'd like.

Anastasia Simon: Um, so I would say Find me on LinkedIn. It is my name. That's it. It's just my name. You will find me on LinkedIn. Connect with me I'm going to be dropping office hours probably.

Um sometime end of july So I'll do a little late summer kind of office hours, flash office hours for founders and funders who are in the space and want to connect. Uh, so keep an eye out for that. Other than that, I mean, I'm again, I'm in like maintain mode. You have [00:38:00] create, maintain, destroy. I'm in the exist, maintain mode even right now.

So nothing to promote. And I'm not, I have no shame around promoting myself if I have anything to promote, but yeah, I got nothing right now. You love it. Keep it

Kt McBratney: simple, right? Find Anastasia on LinkedIn, take advantage of those office hours. Uh, when you see them, I can say that I have had multiple founders mention, like, I've talked to people right after they've come off of those calls with you and they are absolutely worth it.

your generous time and brain power. So take advantage of those. And thank you for sharing your time and your brain and your heart with me here and with everyone listening or watching multimedia. It's the future.

Anastasia Simon: It's the future video and sound all that was wild.

Kt McBratney: It's a talkie. We made it. All right. Take care all.

Anastasia Simon: Thank you.

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