#004: Anna Whiteman - Designing Your Physical Environment for Optimal Happiness

We met when I was like doing that hustle, and all of the fascinating people I know was because I was a yes person for so long. And it was like every coffee meeting I would just like— you had one crumb of something that might have been interesting, I would like show up, I would have coffee. And I met so many fascinating people, but I realized that I had to stop expanding the circle. Like there were too many people that make sure I was keeping in touch with, you know, that can start to become transactional. And you really gotta like have discipline around your schedule and your time to figure out who's stimulating you and who's like making you a better person, who's making you more thoughtful to keep in your life.

Anna Whiteman is a principal at Coefficient Capital, a venture fund based in New York City that leads early growth investments in digitally powered consumer brands, including household names like Magic Spoon, Oatly, Odinki, and Hawthorne, among countless others. In this episode, we cover how to design your physical environment for optimal happiness, why she decided to move out of Manhattan to New Jersey, and her own turning pro moment. Welcome back to the Turning Pro Podcast, Episode 4. We have Anna Whiteman from Coefficient Capital on. Thanks for joining us today, Anna.

Thank you so much for having me.

I've always been impressed with Anna because you were living in what, Nomad, Union Square, Brooklyn?

Yeah, uh, Brooklyn. I was in SoHo and then I was in Brooklyn.

Okay. You were one of the few people that are active in VC. Your job is to run around, source deals all day, talk to people all day, and you intentionally made a decision to leave that go to Jersey.

Yeah.

And essentially like be proactive about who you spent time with and how you spent time with them. So walk me through that decision.

So semi-COVID induced, went home, uh, for the pandemic, lived in South Jersey at the Jersey Shore with my parents and just had friends down there that had nothing to do with VC or like sourcing deals or running around New York. Um, and they were teachers and they were firefighters and they were just like these great people that I didn't want to like flip that segment of my life off when we came back to the office and we were back in New York. So cut to the decision of like where to move back in New York. And like, I had always kind of rolled my eyes at Hoboken where it was like, something must have gone really wrong in your life that you're not in SoHo, you're a Hoboken kid. So I just fell in love with Hoboken though. I started like touring it and my sister and I got an apartment together. So I live in Hoboken and then I found myself going back to the beach every single weekend to just kind of decompress because it was kind of hard shifting back from like living at home, living at the beach, and then being back in the office like 5 days a week immediately. And the like code switching I found to be like so exhausting. So driving back to the beach every weekend to just kind of decompress and like phase myself a little bit slowly back into the like work-life thing and just bought a house at the Jersey Shore so that I could go down every single weekend and not be in my parents' space. So now it's like, if I don't get to Jersey for a weekend to the beach to like look at the ocean and be away from the world of like VC New York, I can like very quickly burn out and get fatigued. So yeah, Jersey, the Hoboken side, like, as I come to work 5 days a week, and then, uh, down at the shore for 2 days a week.

Were you like— was that intentional decision essentially? Like, did you see your life and you were like, okay, I want to stop running around to every single coffee meeting that I get invited to? Or was it just a natural evolution of like, I really like being near the water and having my space?

Yeah, I think it was a natural evolution. I think I Didn't realize until I went home for 2 years that I actually love quiet and I love like deliberation and thoughtfulness and the like go, go, go of New York can very quickly turn into like a rabbit hole that you can't spiral out of. So, um, I studied philosophy in college. Like I just love being in a quiet place, like reading a book and thinking about one thing for a very long time. So it was just kind of like I didn't want to like keep running around, keep doing the coffee— like if I didn't deliberately pull myself out of it, it was just going to become like an automatic lifestyle. So yeah, I think just being able to like zoom out of that and be in a quiet place and hold a thought for a long time and just like look at the ocean. I don't know, the ocean always reminds me that like there is so much more to the world than like your little small coffee shop where you have coffee meetings all day. Um, so it just is grounding for me. It's like very— I was never like, coming from Philadelphia and being like a Jersey person was like not spiritual, not in touch with, you know, that side of me. But it's like very kind of just grounding and energizing for me to like be back around the beach and the ocean.

How do you find it affected like the way you manage relationships or your like points of communication when you were so used to being at coffee shops all the time, like having more touchpoints with people and founders probably than you would have liked in hindsight. Yeah, but obviously it's still your job at this point, so I'm sure there's been some shift. I'd be curious to hear about that.

Yeah, I actually— that's a great question. It started to make me think way more intentionally about the meetings that I was having and the people that I was talking to and not just making it so like transactional or like relationship building. Like a lot of those terms get thrown around in VC that like you have to relationship build for a long time before you can invest in something, which is very true. But it's like, don't do that just because that's the pattern. Like if I, and I'm only here, you know, 4 or 5 days a week. So being here is like a very limited amount of time and like a very specific amount of people that I can actually spend time with. So you have to make that count when you're around people. So it has made me like far more deliberate and thoughtful. And furthermore, having the time to like be away for 2 days a week and just think about like the meetings that you have in the week ahead, you pre-plan them. You think about like what you want to get out of those meetings. You become more thoughtful about the relationships that you do have and that you do commit to. So I don't know if it's like a time and space thing, but for whatever reason, like, recently the evolution for like the relationships that I have has been that they're very thoughtful, they're very intentional, and they are the ones that I believe, you know, will be around 10, 15, 20 years from now.

I want to dig a little deeper into your relationships in general. I think this is something that Adrian and I talk about all the time, especially as like a founder and entrepreneur. I found that my like work life and play life, the relationships have very much intertwined itself.

Okay.

Because like the people that I do business with so oftentimes are the same people that can intellectually stimulate me in conversations when we're like not necessarily on a Zoom call, but like, look, we're nerds, right? We're sitting out at a bar or whatever. We're still talking about like business things because it's fun for us.

Totally.

Um, have you found the ability to like delineate between the two, especially now that you don't live in the same place where you work? And then I guess the other piece of it is how you think about like preferring to have friends that you can maybe hang out with who have no interest in talking to you about your whole venture capital world.

Yeah, absolutely. Um, I work and life do obviously mix in this. Like, one of the great privileges of what I get to do is that I meet incredibly smart people. I like talk to somebody who saw the world in a different way and created a solution that they saw as necessary. And like, that just like that storyline for me is so engaging and so intriguing. So like I find the people that I get to talk to Monday through Friday to be like eminently fascinating. And just again, from like an anthropological standpoint, it's just, it's like a very cool kind of group of people to be in. Um, with that said, I do think that the world of VC, and it gets criticized a lot for this, can be such an echo chamber. And if you're only talking to the people that are building within the very specific, like, consumer demographic that you're targeting and the stage and sector that you're looking at, then, like, you really can start to just run around the same track a million times. And so, you know, talking to people who— you just said you're from Buffalo— like, going to Buffalo for a week and talking to a bunch of people that have nothing to do with, you know, have no idea what Verbatim is, have no idea what GoBuff is, and, like, figuring out where they grocery shop and, you know, what their lives are like. And I just think that, like, I do love that I get to be friends and And that, like, I find the people that I do get to talk to all the time so fascinating, but I also love just introducing people that have nothing to do with my work at all into my life.

Yeah. Wait, question for you actually, because you've made the decision now to be in Jersey to like, in a sense, go on offense when you want to instead of just responding to coffee meetings every day. Yeah. You're the opposite. We are literally filming this in SoHo and I feel like right now, obviously it depends what stage of life you're at. But I feel like right now it's really beneficial for you to be in the middle of it and like feed off the energy of it. So like, I don't know, how are you thinking through that right now?

I think the difference for me was more so the role that I— like the job that I had, right? So previously I was working at GoPuff doing business development. I think it was great. You know, I was learning a ton, but I had no control over my calendar. Yeah, like I was on meetings all day, all the time at the expense of other people. And I had zero autonomy over like how to manage that. When you start your own company, like, it's a blessing and a curse having that autonomy. But like, if I don't want to talk to anyone for 5 hours, I'm just gonna block my calendar and not talk to anyone.

Yeah.

And so for me, I like being where I'm at right now because you're in the center of it and I have the ability to flip that switch. It's a little bit more, I would say, convenient for me than it is for you to wake up on a whim and be like, all right, like, yeah, today's the day, I'm gonna go do 3 podcast episodes in my living room and like go do 4 coffee meetings, whatever it is. You're like, I have to get in the car, I have to drive to New York and think about it. Yeah, uh, the switch for me was, uh, having more discipline around being able to just protect my space and protect my mind. Yeah, which admittedly, when I first moved here, impossible. Yeah, like, I— we're in like one of the busiest corners in the city, and it's so fun and it's great, but there'd be moments where I'm like, oh my God, dude, you need to like disconnect and not talk to anyone for a minute.

I think it is like a little phase of life thing too, because I did I did that so hard in my 20s and I don't regret it for a second. Like all of the fascinating, we met when I was like doing that hustle and all of the fascinating people I know was because I was a yes person for so long. And it was like every coffee meeting I would just like, you had one crumb of something that might've been interesting. I would like show up, I would have coffee and I met so many fascinating people. But like I realized that I had to stop expanding the circle. Like there were too many people that as a people pleaser, I wanted to like make sure I was keeping in touch with. You know, that can start to become transactional, and you really got to like have discipline around your schedule and your time to figure out who's stimulating you and who's like making you a better person, who's making you more thoughtful to keep in your life.

The, the rela— the shift in my mind was one piece, relationships.

Yeah.

But the other piece, to actually like make every minute count and be productive. Yeah. Right? Like, I think there was a moment in time where I would take a meeting just to like check a box, and at the end of the day I'd be like, wow, I had such a great day, I met so many people. It's like, what did you really accomplish? Like, yeah, of these meetings, how many of these people did you actually stay in touch with? What materialized from these meetings? And did you actually push anything else forward? Probably not, because you were stuck in meetings all day, right? So for me, it's intention. It's actually having depth to these relationships, and it's also being very hyperaware around like when I need to pull myself out of situations. I think the beautiful part about this space, right, like we have a great outdoor space. We— you wouldn't do that unless you like to host and have a communal vibe. But if I want to go lock myself in my room and not talk to anyone, like, I will.

Yeah.

And I'm not scared to do that.

Yeah.

Yeah. I think it's important. I think what you mentioned is interesting because when we met, I think we were both in like a rushing around trying to meet people. Yeah. You're a few years more advanced in your venture career than I was.

Mature.

But true. Um, but we were very like, I remember that distinctly because we met at the Ace Hotel and then we like got drinks a couple of times. And I remember I was like, okay, I vibe with Anna. We can co-invest. Like you were definitely like in the, not inner circle, but it was like we get along, right? And then the time that I actually—

clearly not in the inner circle, just a real—

so these are like the cool people and then you're here.

Oh my God, I'm like right on the outside fringe.

We, we were becoming friends, I'll frame it like that. But when we actually—

it's on camera—

when we actually became friends though, I feel, at least in my mind, was when it was mid-pandemic and I was very selective. I was like, okay, Anna, I want you to come upstate to my house for a weekend.

Yeah.

And hang out all together 24/7 for a few days with a handful of other people. And again, that, that reminds me of like what you're doing with your beach house, right?

Totally.

You can, it's helpful to meet a lot of people when you're in that phase, but then when you actually wanna go deep in a relationship, you can say, I wanna invite you out.

Yeah.

For a couple days and really spend time with you.

Yeah.

And I feel like that's when we actually be like became really good friends.

Yeah. Yeah. It, uh, it's funny, I have always been very like, cognizant of the boundary between like making a work person feel like an actual friend and that, that like is, that was so fun. And it was like, you actually just get to know people outside of like the, you know, thing that they are working on, which you can talk about in friendly terms. And that can make it seem like they're your like dear friend, but like get to know people like where you grew up. I didn't know about like you going to spend summers in upstate New York and like the cat, like we were on, your house was on this camp and it was like, this is where I went to camp and this is where I played tennis. And you're like, these are like salient details about this guy's life that like I will now know 10 years into the future. And yeah, it's very nice when like you're able to like cross past being like work acquaintances into like being an actual friend. But yeah, you have to like commit to getting to know people on like an actual personal level and like the commitment of like 2 days, 3 days, like that's a lot. That's a lot to ask of somebody. So it was, I was like so appreciative to come up there and the group that you gathered was so just interesting. And again, it's just like such a privilege to be able to be around smart people and like get to know them as people and why they're doing the things that they're doing, which we got to do at your house.

I also think it's undeniable and you both can probably speak to this, but like the best deals I've ever done in business are with people who felt like friends by the time you actually sign the deal.

Yeah.

Yup.

Like, it wasn't just this transactional thing of like, here's what you get, here's what I get, sign here, right? You actually got to know the person and be like, wait, I kind of like this person. It incentivizes me to want to do something more with them.

Mhm.

Um, and that isn't always the case, and it makes things a lot harder. But I also think you have to be very intentional about that because you can't devote that level of relationship building to everyone, right? Right. So like, when you decided to invite her to your house in New York You know, you could have probably invited 10 different people instead of her, but there's a reason that you chose her over them. And for that, you have a deeper relationship probably with her. So I'm actually saving you by telling you she's now in the inner circle.

Thank you. Yeah, we worked our way in. It took 5 minutes.

It's so true though. The, at least speaking from experience at Verbatim, like we get so much better as a company when we work with friends of mine or people that I become friends with. Yeah. Because they can give me such honest feedback about as a friend where if you're just a client, like a client-client relationship or a founder to VC relationship. Yeah, it's really difficult sometimes because there's, there's walls between you.

Yeah.

You can't be like, hey, as a friend, I think you can do this better. Like I was talking, I won't name their name, but like I was talking to a client who I've become really tight with. He's been on this podcast and we were catching up yesterday and he was like, you guys are doing these things really well. I think you You can improve this thing and by doing this and like by delivering this in a faster way or a better way, or this could be more seamless. He would've never given me that information if we were just client to client. 'Cause he is like, yeah, all good. And then all of a sudden contract ends in 2 months.

Yeah.

And you're like, wait, what happened?

Right? Yeah.

And I'm sure with founders in your portfolio.

Yeah.

Like having that transparency and honest communication as a friend.

Yeah. I think that's like the way that you get better at what you do is just like I've had to evolve where I can take feedback in a very kind of objective manner and not emotionally, but you do need people to tell you the truth, and you need to be able and willing to hear that truth to move you to a place that is not so robotic and not so just running around being transactional into like, am I giving this person what they need? Am I helpful for them? Or is their time better spent you know, with somebody else and my time better spent with somebody else. So, um, yeah, I think it, it, it is nice that you get to like develop these like great relationships with people because the most progress and maturity that I've had in my life has been from the people who have been able to like tell me very hard truths because we got close enough that that was like, okay.

Um, so I think part of your ability to define how you manage relationships probably is a huge testament to the fact that you're a badass female in VC. The Forbes list— I know you're— there's definitely a lot of other women out there that look up to you in, in the space. What drives you?

Ah, oh my God, that's a great question. Um, a lot of things, I guess. Uh, I look up to my dad a lot. Uh, he is like the happiest guy that I know and he loves his work. And I just like the way that he's constructed his life has been so much about his family and happiness. Like, I guess the central feature that drives me is just happiness. Like, are you happy doing what you're doing? Are you happy in the relationships that you have? Are you stimulated? And like, I am obsessed obsessed with consumer culture. Like, that— it's so, like, all-encompassing to me that, like, I really just don't feel like— when I— I know it's, like, cliché, but, like, I don't feel like I'm doing work when I'm at work. I feel like I'm, like, very privileged and lucky to be in that world all day. And just, like, it's literally like jumping into a pool of glitter where, like, you just love everything that you do. Like, you love every, you know, every new consumer business that is moving culture forward or that like has developed an innovative solution to a problem. Like that to me is just like, it's happiness. Like it, it, and if I stop finding happiness and fulfillment in like what I'm doing, I will not be doing the right thing. You know, like have to move to something different. So I think what drives me is just feeling happy, like, like going to work to feel happy every day. And my dad is like the example of that. He just like, his family makes him happy. His work makes him happy. His relationships make him happy. And like, The second something stops making him happy, he just stops doing it. So like, that's kind of what I drive to. What drives me is happiness, and like, I model it after him.

How would you, how would you advise to someone who's maybe struggling with that to course correct, to ultimately find that? Because I think, I think you find a lot of people who, I don't want to say go through the motions, but in some sense of the word it kind of is. Like, and look, there's, there's financial implications, there's personal reasons and whatnot, but I think there's a large subset of people out there who could afford to course correct to find something that does make them happy. Yeah, but I think people like struggle to, to take that leap.

Yeah, I, I agree with that. And I think there are a lot of things that like you need to have a certain level of ability to do these things, as in like it's not always just, you know, easy to hop like into a new job because you're like unfulfilled doing in what you're doing. Um, but I think, I guess just like one character that, like, trait that I have that has a little bit to do with the fact that I'm like the third of four kids and just grew up like idolizing— I just like, I have this fearlessness because I have had two models of people go before me that like I kind of saw how that worked out, I saw that worked out. And like, I've just never been afraid to like just try something totally new. So I It's not— I don't know what the right— I don't give good advice to people because everybody's on their own path and everybody's on their own journey. But when something wasn't working in my life, I kind of had the model for not just following that and being complacent in it. It's like, jump, do something a little different, try something new. And it's like, whether that's moving across the country or you have to kind of— and I'm working on this now— be aware of when you're unfulfilled with something or when something— when you're just like going through the motions and being automatic at something. And I didn't have that awareness for a long time. So like, to a certain extent, like I didn't course correct when I should have a lot of times in my life, but now I can kind of hear it in like the things that I'm doing and the like feelings that I have when I wake up that something's unfulfilling. And like, when I hear that, I'm like, okay, move, like shift. And that was like, I was working, you know, for a long time towards having this house at the beach. But like, I finally listened to myself and was like, you get happy at the beach. Like, you get happy when you remove yourself from the chaos of the city and the like, you know, coffee and then cocktail and then like out to a bar. And it's like, you like being elsewhere and just like, listen to that and like mobilize around that. So it was like, once I heard that, started saving, stopped going out, stopped spending money on clothes, like started saving money, like started working towards this house. And I think it's just like identifying and knowing when something switches and knowing when you're like ready to make a move and like being fearless to do that.

I love that. Um, I think the hardest part about that— I think the, the easy part is being honest with yourself of like, hey, or at least trying to notice when you're happy or unhappy or could be happier. The hard part, at least for me, is when I know that, say, going upstate more is going to make me happy. Yeah, but there's a lot of people that I care about and they care about me. Yeah, that, that version of you or you doing that isn't going to benefit them or they don't want that for me. They're not being malicious. Yeah, but you being in SoHo is actually better for them.

Yeah.

Could be partners you work with, could be friends of yours. And so disappointing those people and actively saying like, um, we're not breaking up, but like, um, I need to go do this for myself. Like, I'm going to be able to spend less time with you. How do you navigate that?

I'm working so hard on doing that. I'm not good at that today. I think what I have come to is that when you communicate your needs to other people, very often they hear you and they understand. Um, But I was a huge, and still am, like a people pleaser. And it's like, I want everybody to like me. I want everybody to think that I'm cool and that if they invite me to coffee, I'll be there. And it's like, it doesn't work that way. And I have to protect my space, to your point about making boundaries. And I don't know, I kind of like, I zoom out existentially a lot and look at my life as I see it, like in a, in a very kind of detached manner. And you're living your life for yourself, like you're living it for other people and you have obligations and stakeholders and family and people to care for. But like, it's your life. And I guess to some extent you'll never course correct if you're not living your own life and you're not like listening to your own feelings. So be great to people, show up for people when you've committed to them. But manage your boundaries and like just live your life for yourself because that's how you're going to be the best resource for other people.

I also think the people that are meant to be in your life long term are those that will actually understand what it is that you're doing, right? Like, I definitely fell into the trap for a long time being in the people pleaser bucket as well, is like trying to change who I am to try to get validation from like very specific people for very specific reasons.

Yeah.

And it's like when you pull out of a relationship for just a minute and realize that person never reaches out to you, that person doesn't— they're not proactive. Look, it's tough, tough love, but there's just certain people where you have to let go and pull the plug and accept that, like, you don't have to be enemies, but they weren't meant to be as close to you as you thought they were.

Yeah.

And I think when that light bulb moment went off for myself, yeah, it changed the way that I viewed relationships, because then I wouldn't lose sleep over the fact that, like, I thought I was supposed to be friends with this person. It just never materialized the way that I thought. Yeah, it's like you just move on.

Yeah, it's like, if you don't live your life for yourself, you will not like create distinctiveness in your life. You know what I mean? Like, to be yourself is to be the guy that all those people want to be friends with. So like, you gotta, I don't know, you gotta carve out that time for yourself. And you're right, the people that should be around you are the people that admire you for doing what you do.

Yeah, I think the The hardest part for me with that has been the people that you've known for 5, 10 years or something like that. Yeah. And I mean, even to like, today's Friday. The people that I used to spend a lot of time with, say friends from college who I love dearly.

Yeah.

But the best thing for them in this relationship is they're going to go drinking tonight and go to a party and stay out till 4 a.m. And a few years ago, I definitely wasn't as honest with myself about what actually made me happy.

Yeah.

Because what I actually want to do today is hang out with Ben and talk to cool people on camera for all day. And then because we're not getting any work done, I actually want to go do work tonight.

Yeah.

And I want to go work out. And like, that's my perfect day. And a few years ago, like, that's not what's best for a lot of people. Yeah. And but that like transition was tough.

Yeah.

That will weed out so many people in your life though. Like there's so many people who can't wrap their head around what you just said. And even if they find their way to this podcast and hear that, it's like, dude, what are you talking about? Like, I don't understand.

It's not every Friday night.

No, no, no, but yeah, it's not— that's not the point though. It's the fact that like you can say that and I, I don't react. In my head I'm like, well, I'm probably gonna do the same thing. So like, I get it. There's levels to it, right? Like everyone, you need to let off steam at some point. Of course there's different ways to do that. Like it's okay to put your computer away once in a while. Like we find ourselves drowning in like the thoughts of work all the time because it's an addiction, for better or for worse. It's a whole nother conversation. But I think that finding what like drives you also allows it to not always feel like work because you have fun with what it is that you're doing.

Yeah.

To your point earlier about like you love everything consumer, you don't feel like you're working when you're actually working.

Yeah. I, I have found it funny that when, if like you to your friends are like, hey guys, have a fun night tonight. I'm going to go stay in and work and work out. Guaranteed, like 3 out of the 4 of them are like, Man, I wish I was doing that too. Like they don't want to go— like it's funny, it kind of like if you strike out and you do your thing, you find that people are like, hey, so how did you find that you love going to the shore and that like the beach gives you peace? Because like I'm looking for a place of peace too. It's like everybody wants it. We're all just kind of like social animals, like doing like lemmings, like doing what the other one's doing. And so you do your own thing and people are like, hey, can I tell you where I've gotten that?

So I haven't had a sip of alcohol in 4 months.

Nice.

The amount of people who are like, dude, how? Like, you got to explain it to me. Like, I hate drinking. Yeah, I realized, like, by stopping drinking, I realized how many people drink who hate drinking.

Oh, totally.

So like, I just— I hate it. I'm like, okay, then like, why do you do it? Yeah, I don't know, it's just like everyone's drinking. And like, do you have fun when you go out if you're not drinking? And they go down this rabbit hole of self-reflection. I go, look, I don't push my agenda on anyone, right? I'm not going to sit here and tell you all you should stop drinking because that's not what this is. It was a personal choice for me, right? Because I just feel better without it. And people are so interested in it, yet they can't get themselves to do it because I think they're like scared of judgment, number one. Number two, social interaction sober out at a bar or in a social setting is very hard for some people. And three, I think you realize that there are a lot of other shifts in your life when you stop because you inherently will prioritize other things or do other things. Like I was saying, this is the first time in my whole life where I can wake up on a Saturday morning at like 9 AM and have a productive day.

Oh, totally crazy. It's also like the addiction of getting stuff done is like, is enough to override alcohol. Like, I give credit to a couple people. And this, this is, by the way, this is like obviously a huge trend in consumers, non-alc, and people like Sober Curious, Sober Curious, and just switching off and being like, wow, actually my life. And I think you just age into this too. Like when you're my age, you will like probably never drink again. But it's like, it is really a fascinating life hack to cut that down. I didn't think I could ever stop drinking habitually. And I come from a very Irish Catholic Philly family and it's so ingrained in our culture. And then I saw one person who I never thought would stop drinking, stop. And I was like, oh my God, it's happened, like the glitch in the Matrix. And then I was like, I can do it. Like, I saw that behavior, like, modeled and followed it. And it's just been like— I still— I mean, I'll still go out like 2 nights a week, but I won't go out 5. And just the ability to like function more in society is so nice.

I remember, I think it was upstate that time, where Anna woke up at like 7:00 AM before everyone else, and you went for a swim across the lake and back. And it's so wild. Like, I'm sure if we spent every day together, I would just start modeling that behavior instantly.

Yeah.

Because that would make me feel good.

Yeah.

I mean, even this week, we got to talk about this, but this week I was telling my girlfriend about that Ben was doing 75 Hard and then another person was doing 75 Hard and I was like, okay, I don't know if I'm like ready to commit to that right now, but maybe I do it for like a week. And we'll see what happens. And over the past week, I haven't done everything. Like, the reading part is still tough, but I think I've done like 6 of the 7 things. And every time I see people that are doing it, it reinforces. Every time I see you, I swear you have like more energy than last time.

That's awesome.

I'm like, what is this guy doing? And it reinforces that I'm like, okay, this thing is interesting. I want to go try it. And increasingly I was like, oh, I'll do 75 Hard next year. I'm like, it could be next week.

It could be next week. So I'm just going to cut you off and tell you that like The number one thing about 75 Hard that I've learned, there will never be a convenient time in your life.

Yeah, to do it right.

That's the reason people can't do it. It's like, right, but I have a wedding coming up, so how am I going to stop drinking? But I have to travel, so like, how am I going to exercise? It's travel. That's why I was in Austin, Texas for a bachelor party 2 weeks ago.

Yeah.

And I skipped the golf Saturday morning and went and did 2 workouts instead, like a crazy person.

So I was like, I'm just not gonna forfeit this, but not like a crazy person. It's just the life.

Yeah, it's a mindset shift, and it's just like you learn to realize that like you can make inconvenient things convenient. It just takes a little bit of extra discipline, right? There's no doubt there's been days through this where I'm like, this is brutal. Like, today's a great example. I was out last night until like 11 because I was at an event that a friend was having. I woke up this morning at 5 o'clock. I've done 2 workouts already, and then I had a call at 8:30. Because I knew I had 3 podcast shoots and a dinner later. Yeah, like there was, there was no other time in my day that I was gonna be able to get the workouts in. So like if I didn't do it in the morning, I was, I was out of options. Yeah, I mean, look, it's not like ideal though, but I have, I have a ton of energy right now and I feel fine and I'm happy that I did it. And like, here we are. So you just, like, my advice to you is if you ever contemplate like wanting to do it, like wake up tomorrow and just do it. Yeah, because you're always gonna, always gonna find a reason to like not do it. I'll do it in a week, but I'm traveling, but this There's always reasons.

I mean, this is very analogous to what we were just talking about, like course correcting. It's like, just, just start. Like, start in any way, shape, fat— like, listen to yourself. Like, dismiss the excuses. Go. And like, after a year, you will be in, like, habitualized in all of that.

Um, just one day.

Yeah, yeah.

That's like taking it one day at a time. Yeah, it's, uh I mean, oddly enough, I have a lot of friends who are sober but for different reasons.

Yeah.

And like the one thing I learned from them, just from like the AA track, is how they teach you just to think about tomorrow.

Yeah.

Like just think about the next day, cuz when you start to think days ahead is when you start to justify and rationalize things in your head.

Yeah.

And then the inconvenience piece comes up and then you get anxiety about it, and that's when you don't start doing it, cuz you're like, okay, no, no, no.

Yeah.

Think about how to solve tomorrow and it makes life a lot easier.

I'm traveling in a couple weeks. That's why I'm—

that's why I'm— it's inexcusable. But no, I'm just kidding.

On a, like, an important related point to that is having grace when you fail, like, for yourself. It's like, if you missed a day of workout, you can keep going tomorrow. Like, it doesn't make 75 hard, like, you only did 30, so like, throw it out.

What is— James Clear has a good quote for it. I don't remember the exact language of it, but it's like, if you miss something for one day it's like, fine, just make sure to, you know, go hard the next day and course correct. But it's like, if you miss 2 days in a row, yeah, that's when it's now becoming a habit to stop executing on the thing that you set out to do.

It starts a new habit if you do it.

It starts a new habit. Sorry, that's what it was.

Yeah.

Um, which is a great— it's a great way to live with anything that you're doing. So with 75 Hard, it's like, oh, you're traveling and you couldn't get your second workout in? Don't beat yourself up over it. Like, it's you versus yourself. There's no one— there's no one out here like watching you. I think what I've found The reason that I actually enjoy it and the way that I've found success in a lot of aspects of my life is gamifying things. Like, I'm a very competitive person as a former athlete, and so like, I need to challenge myself and play games with myself to like get myself excited, right? Because like the thought of not waking up and working out twice tomorrow, I'm like, I only got to day 39 and not day 40. Like, I lost.

Yeah.

And that's not— that's not healthy for everyone.

Yeah.

That's what drives me. And I've found like peace in doing it.

Yeah. Anna, what are you— we're talking about doing hard things. What are you not good at right now that's really hard for you that you're actively— that you actively know you need to work on or you need to get better at?

Um, a ton. Uh, I, um, I've fallen off like the reading wagon. I first of all love that I'm on this podcast. I haven't listened to like more than 5 minutes of a podcast in my whole life, so like people who are able to like walk around and get smarter as they're like walking down the street. I am like blasting Donna Summer in my ears, like, and just like annihilating my brain. Um, so I want to work on, you know, being able to like be a bit more, I don't know, functional, balanced, uh, over the course of the day. Um, I'm not like— I don't want to say I'm not good, but I, I feel like you knew this— I like used to work out Every single day. And I actually still do, but like less hardcore. And it's just like, that is a little bit the like having grace with yourself. And it's like, you don't need to run 8 miles every day. You can run 4 and like, you're still a success and you didn't like fall off the wagon. Um, so I'm giving myself a little grace with that. Um, and I think just like being almost to the point again of like showing up for people, being just a very thoughtful, like. Transitioning from being around people, like where I'm expected to be, to being like how I'm expected to be. And just being a thoughtful teammate, being thoughtful to my family. Like I'm trying to be— all my family's at the Jersey Shore. So like, on the Saturdays that I'm there, like inviting everybody over to my house and making sure that I host them and like, just being thoughtful for other people. And I kind of look back and I do tend to have like a very self-punishing voice, but I'm like, I just lived life so selfishly for like— and so like lucky that people who I consider friends like allowed me to live selfishly around them for 10 years. But like now I'm trying to transition to a period that I live life for other people, like that is fulfilling to me, but like just being more thoughtful and being kinder to other people around me. Because that's the right thing to do, not because it serves me in any manner, you know what I mean?

Yeah.

So I don't know, that's kind of an ambiguous answer, but that's like what I'm not great at today that I'm working on.

It's a good answer. I think, um, I think parent relationships with parents is really interesting because anytime— I grew up in Miami, so anytime I go home to Miami, I realize that when I'm hanging out with my parents, the first thing on their minds is, how's Adrienne doing? How's Amelia doing? My sister.

Yeah.

And all checking up on us, know where we are, know how we're doing. When are we next seeing our kids?

Yeah.

How are we planning our summer? How are they doing?

Yep.

And I realize when I'm around them, that is always the first topic of conversation.

Yeah.

Then it's their work, right? And then it's their life.

Yeah.

But it's always what is going on with kids.

Yes.

And when are we next seeing them? And I realize, I mean, definitely like when I was younger in like college they were not at the top of my list. It was like, I want to go enjoy college, right? And over time, I think—

which they wanted for you. They wanted you to be like, yeah, yeah, focused on you.

But I think over time, I don't know if it's getting older, but like increasingly I realize that, and they're also rising to the very top of my list too.

Yeah.

Of like, it's just such a punch in the face when you realize that, of like, yeah, well, yeah, even if they're— if they're not at the top of my list, I'm being selfish, right? Because I'm at the top of theirs every day.

It's, it's such a blessing to have two parents that love you and support you. And, and it's funny, they're like, now that I've transitioned into this phase of life, they're like, now you kind of see how you were.

And you're like, I can't— like, I'm laughing, like, assuming my mom and dad are going to listen to this and my mom's going to call me and be like, I told you so. Yeah, I like get so frustrated with them, so annoyed all the time, and you just like It like, it's just that you don't appreciate how important it is to actually have people checking in on you like that. Look, I'm 27 years old. My mom still calls me to ask me like, do you have your passport? Like, you're going on an air— I'm like, oh my God, those are important calls.

Do you know my mom?

Can you send me— I'm like, I book a flight home to Buffalo for like 6 weeks from now. My mom's like, Ben, send me your flight itinerary. I was like, Mom, yeah, that's just not the thing I'm thinking about right now.

My dad will check the weather wherever I am and be like It's going to rain, get a raincoat. And you're like, I'm 32 years old, my dad is still calling me to tell me that it's about to rain, and I need it. Like, I'm dependent on it for my life.

My mom says, you'll miss me when I'm gone. Like, appreciate it while it's here. And I'm like, all right, you know what, you're fine.

They're the greatest. And it, it is a nice switch when you want to live your life, you recognize that, and you want to live your life to be of service to these people because that is fulfilling to you. And like That was not the case for me for a long time. And I kind of look back on that and I'm like, "Anna, you were kind of a monster." But it's lovely. And you can feel that way towards friends. You can feel that towards anybody. But it's like, man, the relationships in your life that like are around you in the good times and the bad times, when you, you know, were going out every night and when you stopped, like those are really just special people. And there's like, That's inner circle. That's like, you're allowed to have rings of people and they're allowed to fall in or out. But like, man, it's a privilege to have family and people that love you.

I want to shift gears here a little bit. Um, so the name of the podcast is Turning Pro. I think what, what that means to Adrian and I is like digging deeper into those moments in your life, like those light bulb moments, those aha moments where you you know, as an analogy, got up from the poker table you're at and was like, I need to go to this table that's higher stakes with like different people.

Yeah.

In any aspect of your life, like, what was that light bulb moment where you're like, it's time to become a pro and like elevate myself and take it to the next level?

Oh wow. Um, it's a great question. I think, I think there was a moment where I, I don't know if it was like a moment or I was building to it, but just I believed all of the nice things that people told me one day. And I was like, they're not just trying to like pander, like, I'm actually like kind of good at my job. And like, I can structure great deals and I can like do interesting things. And so I think when I just kind of like kicked into a gear of, I think a little bit of it is like, you're like roleplaying a lot as you're developing in your career, right? You're like, When you're a banker, you're like, how do I dress to be a banker? And like, how do I look to like make these people have me match their pattern? And so you're really just kind of like navigating these channels where you're trying to be what other people expect you to be. And then like, if you— I guess I decided that like, this is the career that I love. And this is what I want to do forever. And in order for that to be sustainable for me, it needs to be on my terms. And like, being on my terms means like, I need to own myself. I need to own like, how I want to do this. I want to own like, what segment I concentrate on, what like, type of company we look at. So I guess when I like, got into the mode of like, this is my path, this is like my forever thing, put it on my terms, then it's like, you start to control the conversation more than than you did when you were just trying to like fit what people like wanted you to be. So yeah, I guess I just got like, this is new, this is evolving, right? Like I'm not even remotely close to like how far I wanna be in this career. But like, I think just recognizing that you have autonomy and recognizing that like you can, you know, create a deal. You can like, you don't just have to like wait for like everything else to coalesce around you. Like you can be the agent that does that and you have the power and the control to do that. And like, you can do it in your style, like do it in your own way. I guess that was when I like moved tables, was when I was like, I am, I am having to do this for myself to make this career sustainable for me. Um, and then other people, when you come into that power, I think like see it and then can respond to it. Like that the kind of you surround yourself with, you know, people of the same persuasion, of the same ilk, and that kind of levels up your whole life.

Yeah. I think when you move to that, like, metaphorical table, the coolest part about that— I'd say I'm like at the beginning of that stage of making that decision, but okay, when you start to move to that next table, I feel like you did that.

You kind of—

I think one of the reasons we started this was that we're both feeling that now, that move. Yeah, we're still very much like in the throes of it.

Yeah, but we're inviting you to our table.

Yeah.

Thank you.

Welcome, man.

Inner circle table.

Welcome to the table.

Where else can I show up for our relationship? Yeah.

What was I saying? But the coolest part about it is that people at your new metaphorical table are almost like, we've been waiting for you.

Exactly. You see it and you're like, oh, thank you for dragging me along this whole time.

Like, where have you been?

I have come into my power.

I feel like a big part of it is just trusting yourself. Yourself.

Yeah.

And like, this is what I'm good at, this is my competitive advantage. And like leaning into that and owning that.

Yeah.

As like, I am good, but I have a lot of work to do.

Yeah.

And I'm gonna push down that path.

I think vulnerability is a big component of it for myself.

Yeah.

Yeah.

Like accepting what I'm good at, being honest with myself about what I'm not good at, uh, being able to overcome judgment from other people.

Yep.

And like really committing to my own values and morals and like just going for it, like diving into it. I think for me, like, the last couple months has definitely been a moment where I'm like, okay, this— like, I'm, I'm, I'm, I'm going to a different, a different place right now, and I'm like committed to it and excited by it, and I don't really give a shit like what other people think if there's people who have a problem with it, because it's just like that moment for me where I just feel like I'm, I'm, I'm moving to the next table.

Yeah, you're not going to grow if you don't make yourself vulnerable. I was just having this conversation right before this where it's like the— you're kind of like a trapeze artist and you're jumping, like you're on one cable and you're jumping to the other one. And in between that is this like liminal, unsteady space where your whole script that worked before no longer applies. And so you've ceded that control. And it's terrifying to be like up in the air between trapeze cables. And— but you're not going to reach the other one if you don't like accept comfort and like being able to hang out in that like vulnerable, unsteady space. And but in that liminal space, there's huge growth. There's huge— like, every— the bottom has fallen out under you and you have nothing to do but like look around and learn and pick up new pieces and like recreate, which I think is like a really cool opportunity.

I think I love the fact that we've barely talked about business on this podcast.

Oh my God. Yeah, we're like— we're in existential philosophy.

No, but I, I like We— one of the main reasons we wanted to do this is that like there's enough podcasts out there that will like bring you on and be like, oh, like what's the last deal you did? Like what's the company you're excited about? Which fine and great, but I don't think there's enough where it's like you double-click into these individuals' personal lives because like the Anna that people see on LinkedIn is like your accolades and like your accomplishments from a business perspective. But like they didn't know that you like to go hang out at the beach with your family and like do things of that nature. And so that's really interesting for for us.

Yeah.

Um, but I would feel remiss not to at least address it for like a couple minutes. We'd love to just kind of get your take on what, what you think are the next big trends in consumer and where you're focusing your time.

Yeah. Um, I mean, consumer is amazing because it's always evolving, and probably the answer that I give no matter what is not going to age well because, you know, 2 years from now, like non-ALC will be, you know, connected fitness or whatever it is. And like the trends change so frequently, which keeps it super dynamic. I would say where I think there's huge growth and huge momentum, like undeniably so, is a couple of areas. I think kind of like contextual commerce is very interesting to me right now, which is like you have a Guia bottle over there and I want that Guia bottle. Like I, you have a method for me to pay you for that right now. And like, I think that kind of introduction of brand into like everyday life and like almost commerce into everyday life is going to have like hugely uprooting like qualities for distribution channels and for like how and where and like what the consumer experience looks like. And there's a lot of infrastructure. I'm sure you see this being built around contextual commerce today. I think that's going to be like massively kind of informed by like payment technologies and like peer-to-peer, all of that, like so that enables— and some people think that's a great thing and some people think that's a horrible thing. Like the fact that I can buy this microphone right now and just walk out the door with it, like makes me on all of the time in terms of like it's kind of a predatory feature of consumer culture, right? That like everything is for sale all the time. And I'm with them. And that's kind of terrible. But It's also kind of great because like, if this is the best microphone I've ever seen, then I can walk out of here without it, with it and like, have it in my life. And I don't know, I think it'll, it'll be very interesting to see how brand marketing evolves around that, how, you know, distribution channel kind of evolves around that. And I think it will upend like a lot of preexisting, like high inertia systems. The other thing that I am like trying to put— I've put this great panel together around that. Like, I'm very much a novice and learning, but is just like AI, ChatGPT, how that's going to change kind of brand marketing and content and copyright. Um, you know, I'm of the mindset that like it's an amazing tool that we can all use. And like, this is kind of the like philosophy, critical reasoning, but it's like, it's how you use it. And it's like what questions you ask it, not necessarily like this is evil. It's going to like override humanity and like everybody's going to become a robot. Like, I just think it's, it's going to be an amazing, powerful tool that we can start to use to like inform better systems, better judgment, better, like more, uh, effective, like targeting and like communication from brand to consumer. Um, these are all just kind of like big things that I think are going to move consumer culture forward very much in the next 10 years or so. Um, so I'm excited about those.

Is there any specific consumer brand right now that doesn't have to be in your portfolio?

Okay.

Um, that you're just jazzed about for some reason, like that we should have their products sitting on these tables right here?

A brand that I love?

That should sponsor this podcast.

That should sponsor this podcast.

Just something that you're blown away by.

So this is always the first question that people ask me, so I'm gonna try to come up with something that's like very, you know, outrageous right now. Uh, Okay, you know what brand I love? My little sister works there. So this is a plug. IKEA. I think IKEA is— okay. Side note, my favorite brand in the world, just for the record, is Margaritaville. Jimmy Buffett, Margaritaville, like could go on for days about that. We'll table that. I think IKEA is an incredible company. I just think that like, they're so, they're so huge and so sustainably minded at the same time that like those two things don't often go together and The way that they like have created this DIY like kind of infrastructure and like in doing so have done incredible things for the planet, have done— and like they're just an incredible business that like is growing a forest, you know what I mean? They're like doing so many things that are outside of the parameters of like we exist to serve you a product that we make this margin on and like that is our only responsibility in the world. I just think it's an incredibly iconic, enduring brand that, like, you know, has been around since I was a kid and I believe will be around for the next 100 years. And I think, like, the brands that I tend to be attracted to, and Margaritaville's kind of like this, is just, like, heritage brands. Just, like, things that you know will be a part of your kids' lives, like, and they're enduring. And I think with kind of VC consumer culture being like, quick fund rounds, quick exits, and everybody's navigating towards 5, 7-year timelines. I think that the brands that I find so incredible are the ones that just think in 10, 20, 100-year timelines.

Yeah. I think what keeps them relevant too is that they stand for something. This could be a software company too.

Yeah.

It's not just that they have a good voice on socials or have good email copy or good branding or really SKUs often.

Yeah.

That stuff is like on Twitter, LinkedIn all the time. Yeah, it's like, oh, that's a cool strategy. But the enduring ones like, yeah, have a mission and stand for something that is enduring too, and that people can buy into, right? It could be like having a big charitable component or like sustainability mission. Yeah, like those I get behind.

Yeah. There was a big clamor earlier this year about how Airbnb shifted all of its marketing from like performance marketing to brand marketing, and it was like non-attribution oriented and it was just creating like familiarity in a very esoteric kind of nebulous manner and like non-measurable manner. And everybody was like, ah, we can't, like, we don't know if we put $500 into that, will it get us $1,000 back? And like, everybody was up, like all the investors, everybody was all kind of like wondering where, and it's proven to be like the best. Now all these brands are trying to copy this.

Really?

Like, yeah, this like higher kind of brand architecture strategy that's not attribution oriented because not everything is performance, not everything is, you know, an effective ROAS like that you can take to the books. And it's, it's creating a brand, it's creating familiarity and awareness. And I think those, the brands that do that really well are like the kind of iconic enduring ones.

I think that's a good place to wrap. Um, any final thoughts?

Thank you guys for having me. I want to talk about Buffalo next time that we come on this pod.

Okay, well, round 2 Buffalo.

The only place I love more than Jersey is Buffalo. Buffalo. So wow.

Yeah, I think we might have to extend for like 20 more sessions.

Strong take.

All right, favorite buffalo wing restaurant?

Uh, I mean, I've been a Duff's loyalist, but Wingnuts— Wingnuts is the new Wingnuts, the new one.

All right.

Um, yeah, that's definitely, definitely the answer.

Okay, I'm going to Wingnuts next time.

I think like a Wingnut— Wingnuts and a Bills game, and like you can leave Buffalo and be like, I checked all the boxes.

And an Anderson's Milkshake and curly fries.

Okay. Oh yeah, it's like an iconic ice cream joint in Buffalo.

That's where Jim Kelly used to go 4 games to have a milkshake.

Wow, I love, I love the Buffalo plug. She's, she's welcome back whenever she wants.

Uh, next one is on the road, Buffalo.

Done.

Perfect.

Uh, Anna, do you want to just let everyone know where they could find you on socials, if you're active on Twitter, LinkedIn?

I have no socials. This is part of the disconnecting. I have a LinkedIn. Uh, you have to have my email to connect, so it's Anna@cofcap.com. I don't do much on it. I have no other socials. Sorry.

You got to look for her if you want to find her.

Yeah, I'll be in Jersey. Come to the shore. You can find me there. I'll be at the beach on the weekends. Everybody's welcome.

Amazing.