The Jennifer Kamara Podcast

Steph: And the example that I often give because I do think it was like the first true aha moment with this was going on exchange. My school, at least at the time, basically no engineers would go on exchange cuz it was really hard to find the requisite. Courses abroad that would make sure you graduate on time.

I ended up doing it. Long story short, I came back and I had this like new view of spending a year in Sweden and like seeing the world and I came back and everything else was the same for everyone else. . And I was like, what? And, and I remember looking back at just the fact that it was this one micro decision of just being like, oh, let me just go on exchange.

Jennifer: Hi everyone. We talk with the one and only Steph Smith today. She's an indie hacker and podcast host at a 16 Z. She's a walking example of creating her own path in life. Steph tells me all about being a creator, her dream, and what growing up as multicultural person is like.

I had so much fun. Thank you, Steph. Enjoy everyone.

Jennifer: Steph, it is amazing to have you with us today. I'd like to get started with taking a walk back down memory lane and getting a sense of what growing up was like for you. I know you grew up in Canada and so eager to understand what some of those formative moments that made you into the person you are.

Steph: Yeah, I mean, I think one aspect of my childhood is that I grew up in Toronto, and Toronto is, a lot of people don't know this, but the most multicultural city in the world,

Jennifer: Oh wow.

Steph: is. Or if it's not number one, it's definitely up there. And so, I grew up also in a multiracial household. My mom's from Taiwan.

My dad's originally from the uk, so I think that was pretty formative, just having a really diverse, whether it was in my core family or where I was living, a diverse set of experiences. And my dad was also the type of person to throw us into absolutely everything. So my friends, Often make fun of me. Now they're like, wait, so you played competitive chess, but you also curled and played competitive soccer and like

Jennifer: Oh, that's fine.

Steph: he literally was like, let me just throw you into everything and see what hits.

Um, yeah, seriously. Um, and so that was, I think formative where I just got a lot of exposure to things. Started many of those things not being very skilled at them. And then the few that stuck, as we said, I learned how to kind of ascend, you know, a skill curve or really stick to something, which again, often I wasn't great at to start.

I think those were a couple form formative experiences, but also we didn't grow up. We didn't grow up super wealthy. So I think that still to this day, I did a, a podcast the other week where I was just reflecting on how many habits I still have today, where I have now, um, I guess you could say ascended in ways or I now make much more than I honestly could have ever imagined.

But I still have so many of those habits from when I was younger where I'm just like, wow, I just, I can't get myself to spend money or to like live in a different way.

Jennifer: Oh my gosh. I resonate with so much of what you just said. I, we also grew up poor. We grew up in Sierra Leone. It was the seventh poorest country in the world. My dad was one of 50 doctors in the country of over 6 million people. And I joke with my brother because we have this habit of, we still, like, I think people will use paper towels to a point where, for me it feels like I.

Can I the paper towel? You say, people always

Steph: My mom does the same thing. She'll literally rip, rip a paper towel in half and I'm like, mom, we're past this. But I do similar, similar stuff and I mean, I, it's not like I grew up on the street or anything like that, but there was just, I mean, there's so many interesting aspects to wealth where it's like, We, we got a lot of the things actually we asked for, but then there was this like undertone where I kind of knew, my mom was like, certainly in six figures of debt along the way.

So it was like, what are we doing here? And so there's this weird relationship with money where, yeah, it's, it's taken me a long time and I wouldn't say that I'm even past like reconciling that perspective.

Jennifer: I imagine it's gonna be an ongoing journey for me it's also about safety. How do I make sure that we're safe and that we have a roof over our head and view money as that? In that weight as well. The other thing I wanted to talk about is being, growing up in a multicultural household.

So my mom is Ukrainian, my dad is Sierra Leonian. My mom was white, my dad was black in Sierra Leone. I was. White in Ukraine, I was called black. And it was just a fascinating, uh, way to grow up where neither of my parents really fully understood my experience. And I'm just so curious if you ever felt that way.

And I, I personally view my diversity as a huge strength, just being able to look at various people and be able to understand their points of view, but curious for you, if you, if any of that resonated.

Steph: Yes, definitely. I mean, I think interestingly enough, I, I don't know if you'd agree with this, but this is based on experience many times in my life where a lot of people just see me as white. So I have this interesting layer to that where, . I am fully half Asian. Um, I grew up with a mom with a very strong accent.

Her family's still all in Taiwan. She's still, um, you know, Mandarin is her first language. I would see how people would often, especially when I was younger, um, when race I think was in a different place. Would mistreat her and not realize, like, that was my mom. My mom used to say things like, yeah, I used to take you to the store, and people thought I was your nanny.

And so I had this interesting perspective where, quite frankly, for most of my life, I was treated as just fully white. And, um, you know, people, most people didn't realize that I was, uh, multiracial. But then I did get to see, again, that other perspective where I could see how someone. My mom. And so, yeah, I mean, I think to your point, I think it was an experience that most people don't get.

They don't get to see both of those lanes. And, um, yeah, I'm, I'm really glad I got to see that. But it's also interesting, again, like having the perspective where most people, in fact I've been told like, you know, my name is Smith. Like, I, I look, um, probably not as multiracial as as I am. And so, you know, it's also been, it's also interesting to like have the perspective.

People almost don't think I have the right to be multiracial. Um, if that makes sense.

Jennifer: me so crazy. This like, people imposing their own views on you. I, I, yeah. I could, I could just go on and on on this and I just, I can just cut it short and say I'm so grateful that. Folks are finally becoming more open-minded to asking a question, how do you identify what is your experience as opposed to trying to label you by whatever boxes that they're accustomed to.

Um, and yeah, absolutely. I think it, it's just extremely sad to see the injustices and unfairness of how folks get treated because of how they look. Very interestingly, it's very obvious to me that you're multiracial, and I think it's because also being multiracial.

Steph: you

Jennifer: I'm always looking for other multiracial people and I'm always like, oh my God, that's a multiracial person that's like

Steph: No, it's so true. It's so true and I bet, I mean I think multiracial people spot generally people who are mixed race more easily, but also the specific multiracial combination that you're from. Like I can spot a half Asian just like that. Even if you know a lot, a lot of other people can't. But it's interesting cuz I, a lot of people I meet.

A substantial number who are like, oh, of course. Like I knew as soon as I met you. And then there's other people, like I had a boss for a year who I told one day, I don't know, it just came up. I was like, oh yeah, my mom's from Taiwan. And he was like, floored. And he even started asking , you know, another coworker of ours, like, did you know this?

And it was totally, you know, genuine and there's nothing wrong with it, but it was just so funny where he was like, he couldn't believe it. So,

Jennifer: And you know what, Steph, we're taking over by 2050, multiracial folks are gonna be the majority of the United States. It's gonna be awesome. I hope it'll make us all kinder and just more open the more mixed the world gets. I think it's such a beautiful thing. Again, just for me, having both cultures like African and Eastern European culture and then moving to the United States.

amazing. Being able to see all these different worldviews and be able to appreciate other worldviews and love of languages and culture and human beings and their experiences. So I'm so excited for where we're headed.

Steph: Me too.

Jennifer: Tell me about this. You played chess and you love soup.

I feel like Eastern Europeans love soup and eat soup with every meal, so I'm so

Steph: You know, I've never tied those two. I mean, I just, I love soup. I'll eat soup on, you know, I'm still Canadian, so I think in Celsius, but like a 30 degree

Jennifer: Me too.

Steph: Okay, great. Yeah, so. So, yeah, I don't, I still can't do the Fahrenheit conversion.

Jennifer: Me too.

Steph: gonna have to Google that. But yes, I'll eat soup anywhere, all types of soup.

But I think it's also because like I, I traveled for a long time and soup is just a distributed form of food, , right? Like anywhere you go, that culture will have a form of soup and often amazing. And it's often also because think about like every country has a set of spices or a set of herbs. Is kind of part of their culture and it'll be in soup because that's kind of just like, again, like what, uh, what anyone around the world, if they need to create food that is probably not, um, or other things won't stay good for very long soup.

Like in Vietnam, , people make jokes that like the same place will be brewing fu for like months, like that same bowl because it stays good. So anyway, I love soup. And then yes, I played chess growing up. Um, I

Jennifer: Wait, before we move to chess, what's your favorite soup?

Steph: I mean, people are probably gonna judge me for this cuz it's such a simple soup.

But I love miso soup. I, I feel like when I go to, you know, a Japanese buffet, I'll literally order five miso soups, , so,

Jennifer: Yeah, that's great. It's also great for your tummy, for your gut bacteria. So good on you. I agree. I think soup is just universally comfort food in Eastern Europe. It's like e every meal starts with a soup. If anyone doesn't know now, you know, like every single, it's like, it'll be like you said, like 35 degrees Celsius heat of summer and you start your meal with a soup and I, I love it.

Steph: Yeah. Yeah. So, no, you're good. Um, in terms of chess, I played growing up, like I said, my dad kind of threw us into things. He was kind of, he was the dad who

Jennifer: I

Steph: good at things himself. I mean, a lot of people probably resonate with this, but like wanted his kid to live the life or like live up to the potential that he maybe thought he could.

So both me and my sister were thrown. Into chess pretty early. We had a chess coach that would come over, um, and we'd played in tournaments. We represented Team Canada when we were younger. And, um, both of us quit pretty early. I think I quit when I was like maybe 12 or 13. Um, but we were pretty good . So, um, yeah, that was a,

Jennifer: gambit. Missed career here.

Steph: I mean, it's funny, a lot of people if, if they follow chess now because it's had this kind of second wave, uh, they might recognize the name Alexandra Botez and she was on Team Canada with me. And so it is kind of funny, you know, if, if people watch that movie like Everywhere All at once, um, I'm messing up the title, but that movie where you kind of see the, the different paths that you can take in life.

Because my dad threw us into so many of these things, I am like, oh, I can actually see someone from that chess team and like, what they ended up doing, and now she's a chess streamer, has, you know, signed contracts with like eSports teams. And so I'm like, oh, interesting to, like, dwell on. But um, yeah, I did that for years and I think that was a great experience because Jess is really, um, There's no gray area, if that makes sense.

Like you win or you lose, uh, you get better. You don't, your rating goes up or it doesn't. Um, and so it was a great practice to actually see if you spend a lot of time and dedicated effort, even at a young age, like you will get better at something. And it was also a test where it's like, you know, you can tell when you're not putting in the work.

Jennifer: Sounds like it's great for discipline, analytical thinking, problem solving.

Steph: Yeah. I mean, people joke that, uh, professional chess players, they'll sit at a board for hours on end and there's all these crazy stats where it's like they're burning more calories than someone actually running for that same time period, which doesn't surprise me. Cuz you're literally like frying your brain just like a, a true computer.

Imagine like a G P U trying to like go through all of the alternate paths on the board. That's what your brain is doing.

Jennifer: Fascinating. I don't know much about chess, and I sadly never got to play chess, but I feel like I would really enjoy

it

Steph: not too late.

Jennifer: It's not too, it's right, it's never too late. And I love the thought experiment with everything everywhere, all at once of all the different paths we could have taken.

Which leads me, let's chat about your path that you've taken. So you've been an independent creator, you led the Trends newsletter, grew it to 15 k plus subscribers. You were director of marketing at HubSpot. You had your own podcast, you had your. Blog, you created content like getting content right? And these days I understand that you are hosting, asic Sim Z's podcast.

I wanna chat about all of these things, but first wanna give you the opportunity to share. How would you describe what you do these days just to level set.

Steph: Well, it's funny because , this, this new job that I have as of maybe like six to eight months ago with a 16 Z is the job that I get the most questions about. As in when I tell people I'm a podcast host, they're like,

Jennifer: What is

Steph: what is that? But also even if they know what podcasting is or like, is that a full-time job and like,

Just th there's endless questions versus before if I just told people like, oh yeah, like, I work in marketing.

There's not many

questions that follow onto that. So yeah, I mean, I'm a podcast host. Um, and prior to that I worked in marketing for a while and, um, I don't know, I never know how to explain what I do because there is so much of, uh, You know, strange path that's led me here. There's not necessarily a very clear through line.

I would say that basically every job I've gotten since, um, basically including when I joined the hustle was someone reaching out and seeing what I had done before, or some work online and saying like, oh, I think what you do is really cool, or I think you're smart, or I think you're creative. I think we'd love to have you in this role.

And so they're almost like inviting me into a new kind of role and seeing potential in me there. And so, yeah, I think that's what one of the reasons why there's not a

very clear path.

Jennifer: Yeah. Also, so I feel like with podcasting it's a really new, relatively new medium. Like this medium is only going to grow. We're just scratching the tip of the surface right now. I think you see how people's behaviors have been evolving. More people are listening to it on Iran while doing dishes, errands, et cetera.

Um, and so because of that, I feel like it's just new and it requires some more explaining as it becomes more and more of an underst. job title, job description, per se, versus marketing, and then I so love that you've been just doing your own thing. One of my strong values that I hold is, uh, you're living your life for you.

I feel like there are really no rules in life. Most things, everything has been invented or dictated by another human who probably isn't smarter than you are. And, and so I love that you've been kind of playing your own game, making your own rules. I think we've got things in common on this path, right?

We both studied chemical engineering and didn't wanna work in an oil grid. I know that we both work for ourselves. I just learned we both work with our husbands

Steph: Yeah, well, to some extent, right, like when I work with him on side projects, but that's always fun because most people when they hear that, they're like, I could never . And I'm just like, yeah, well, it's not always easy.

Jennifer: Yeah, it's not always easy for sure. He can be a big pain in the butt and very stubborn , but it creates lots of opportunities for communication and feedback, uh, and I really think communication is the crux of a relationship. But it's such a, it's such a blast. I think just spending time with the people you love and adore and admire and getting to spend time with.

every day. Um, but I want, I wanted to set that context to bring up that not everyone goes their own way. And, and you've been really following a path, sounds like, of opportunities and projects and people that you admire. And how did you become that person? Or were you always that person?

Steph: I don't know. I mean, it's one of those things where you ask your parents and you're like,

You, you asked them about when you were a baby and the way you acted, and it does feel like, from my mom's perspective, that I always was.

Confident and got what I wanted ever since I was a baby versus my sister who was a lot more timid.

So I think there's a little bit of it just being inherent, but I will say it was learned. I think there was this, I, I actually sometimes look back to, this might sound strange, but to pictures of when I was younger and I can see this like confident child that again kind of like got what she. And saw life in this way where it's like, I can do whatever I want and, or at least I can, like I can aspire to be whatever I want.

And I think I, I always like wonder what it is about middle school, but like, I think that rough period of life kind of shook me in a way. Or like all of a sudden I was, I was this person who then was curating my life according to, you know, what other people thought was cool. All of a sudden I'm preparing myself for college and trying to find a job that I think will impress other people.

And I, I did that path, right? Like I, I went through college. I got my chemical engineering degree. And so I think there was, yeah, maybe, I don't know how long, maybe five to 10 years of my life where I was like off that path. Um, and what it took was, again, relearning. By trying, and that sounds really simple, but there were little instances in my life where other people were all doing one thing and I had just heard of something like an alternative path.

And the example that I often give because I do think it was like the first true aha moment with this was going on exchange. My school, at least at the time, basically no engineers would go on exchange cuz it was really hard to find the requisite. Courses abroad that would make sure you graduate on time.

I ended up doing it. Long story short, I came back and I had this like new view of spending a year in Sweden and like seeing the world and I came back and everything else was the same for everyone else. . And I was like, what? And, and I remember looking back at just the fact that it was this one micro decision of just being like, oh, let me just go on exchange.

Let me try this out. And so that was one of many examples where I realized that actually as we just discussed, a lot of people just kind of live their life according to inertia, and they don't even realize. How much of their life is curated by other people? And I'd done a few of those. Again, it's not like I all of a sudden woke up one day and was like, I have all this confidence to absolutely do everything on my own.

But within a couple years of going on exchange, quitting my job in consulting, becoming nomadic, um, that new job, like getting promoted and taking on new work that I've never done before, things like that. Um, . I'd say, you know, again, three to five years after that, I was at a place where I was like, I have enough data

You know, like I now see that actually it's not that. It's that much harder to take your own path. A lot of people just never think to do it.

Jennifer: Mm-hmm. . Mm-hmm. . Absolutely. And never think to do it because unfortunately these are the majority of examples we see in society. Go work this nine to five job until you retire and then live your life. And I know you also did a podcast on this, so I won't belabor everyone, but Yeah, unfortunately that is the example that we have been fed.

Um, . It's so interesting because similar, similar for me. So I also, it was not strange what you were saying at all. I also as a kid, was like the most confident kid ever. Uh, my mom called me Rubella cuz I would just refuse to follow the rules. Um, and what you said about middle school is like, so I don't know if you've heard of, of Rebel Girls.

We had their C E O Jess Wolf on and their whole mission is to instill confidence in girls who lose their confidence between the age. Six to 12. Um, and that is because between those ages is when we start to get all this information. . I never thought, I never really felt this thing. I feel like I really owe my parents who told me girls are smarter than boys.

Uh, but like girls start to feel like boys are smarter than them. Like girls shouldn't do stem, boys do stem, or girls should dance and boys do other things like science or robotics or whatnot. Um, and I think we, we unfortunately have some of these biases and message. Still out there, and I wouldn't even, I don't even think that it's for mal intended people, just folks that are unaware, and I think it'll take some more education to get that out of societies, et cetera.

But it's a very normal thing that happens for girls, unfortunately, in, in that age group. And then interestingly for me, I graduated and. With Kemi as well, and I just had a really strong why of, so I came from Sierra Leone and it was the worst place in the world to be a mom. I was in Boston around all these doctors, amazing facilities, and I wanted to go address maternal healthcare.

Basically walked up to the head of global health at. Harvard and told him, if you come to Sierra Leone, I'll set up a program and we will address this. And he, I think, was just taken aback by the chutzpah and said yes. And that's how I started my first organization, which was transformative for healthcare.

And now, like today, these days, I look back, I'm like, holy cow. She was so confident. I'm like inspired by her and I wanna remind myself to be her. So I say this to say, I think it, there are waves of it too, like the self-belief and they are governed by. our surroundings. Like life does beat you up and it's all about you get, you fall seven times, get up eight, but it does take a a lot to get up when you've been beat up by life.

And it's about forming these neural pathways for sure. And reminding yourself and learning and knowing, even now when it's uncertain that, you know what, I can get up. I can do it. And, and just, it comes from the practice and the

Steph: Yeah, y you know, that really resonates with me because I think a lot of people look to external mentors and so do I. But I think there's something so beautiful about looking at your past self and being like, wow, like good for you. And like you said, there's many points where I look back and I'm like, How did I do that?

It could be like taking on as much work as I did or Yeah, taking a chance that today I am like how did you make that decision at such a young age? And I think that's really beautiful cuz to your point, even though I'm much older now, I go through waves where I'm like, oh man, this is a really hard new job and I don't know if I can do it.

And then sometimes it's really helpful just to like look at that, whether it's like six year old me who had the utmost confidence, or 21 year old me who decided to, you know, quit my job before everyone. , you know, thought that was reasonable and so yeah, that really resonates.

Jennifer: I think with age and experience comes wisdom. , which rightfully so, makes us more cautious, helps us understand all the things we don't know, which, when we're younger we have no idea.

We're just, it's not even bravery, it's just plain, it's just naivete. And I think that is the beauty of growing older, is that we have the inside of wisdom. And for me, what I work, what I'm working on with myself is not letting that wisdom limit me too much and kind of balancing. Experience with the naive , you know, and kind of figuring out the right balance there.

Steph: I've been working on an article for a while because it's all I can think about. Lately I'm 29, so I'm almost 30. And um, I look again back to when I was like 21, 23 and I was just doing all these things, as you said. Not because I was so brave, but just cuz I

I didn't really have anything to lose also, and the, the article is called The Joy of Inconsequence.

It's just being in this space where there's zero expectations. If I write an article, there's zero association with previous things I've written because I'm new to this space. I have fresh eyes. No one expects anything from me, and I have just over time built up this repertoire of like, you know, a successful book, successful podcast.

I've grown my Twitter following and now everything I do, even something so micro, like a tweet, it has this embedded pressure. Um, and honestly the pressure mostly comes from me, but there is this association with, people view this differently than when I was just starting. And I love this idea of just, you know, young people, they really have this like joy of inconsequence.

No matter what they do, things are gonna be okay. And no one looks at what they do with this frame of like, you should have known better. or this should be better because you have this experience, or this wasn't as good as your last article. And so I'm trying to actually get myself back into that head space of like, how do I bring myself back there?

Doesn't matter if other people expect something from me, I just now want to do the things. Just like when I was, you know, 21, 22, 23. I just wanna do the things that actually excite me.

Jennifer: Steph, it's a work in progress. I feel like it's a work in progress for everyone. Anyone that tells you they got it figured out is lying to your

Steph: It's so true. It's so

Jennifer: And yeah, it's gonna be a journey and it's gonna be the constant reminder.

Steph: Yeah.

Jennifer: wanna chat about entrepreneurship and solo entrepreneurship in particular.

So, it sounds like right now you're working with the A 16 Z team, sounds like you have your partner, but just curious what was solo entrepreneurship like for you when you were writing blogging? How were you handling it these days? Even though you may have more of a team and any loneliness hacks and just productivity hacks in general that you like to go.

Steph: Yeah. So I mean, I think a lot of people, um, probably think that I have, especially for a while, not so much lately, but when I was putting a lot of my own stuff out there that yeah, I had like people supporting me or this team and I didn't ever really

have

Jennifer: is so impressive.

Steph: Well, I mean, it's impressive, but it's also something where I'm like, I'm, you know, as we talked about these lessons, like I need to learn to bring more people on, um, and help me with that stuff.

But yeah, I think another aspect is, Throughout my whole career from when I was like in that business consulting role until today, I've actually had a full-time job while I'm creating on the side. And that's actually been an interesting thing where a lot of people also will look to that and be like, why haven't you quit at this point?

Why haven't you gotten all in on your, your side projects? And I still, I mean, I think I will, um, at some point, but I actually find it really freeing. Um, may sound counterintuitive to have. Side projects, which are separate from my full-time job because I've just seen so many people who go all in on quote unquote their passion, and it destroys it.

things

no longer become fun. You become, you start to optimize them for, you know, being able to live off of those projects instead of just doing what you want and more importantly, how you want to execute on them based on truly just what you're excited about. And so I guess coming back to, uh, productivity, that also plays a role where I only work on these things when I'm excited, and so I'm not pressured every day to sit down and say, okay, actually this side project, I need to make progress on it.

And so what that ends up looking like, at least for me, is these. There's a saying where it's like, you know, work like a lion, not like a cow. It's like these sprints where like the book I wrote, I wrote that in I think around seven weeks because I just had this idea. I capitalized on the, the idea. I got it all down on paper and then I never thought about it again.

And I think it's also part of knowing my own psychology, where if I let things drag on for long enough, I'll never do them. I'll never complete them. So that, it sounds really simplistic, but I think. if more creators actually worked, when they were excited, when they were drawn to something, they not only would get things done much more quickly, but then they would have this free space to not constantly be grinding.

And I've also, by the way, designed my projects in that way where I never wanna be that YouTuber host to wake up every morning vlog for four hours and do the same thing the next day. Like I've designed the projects I take on or the, the, you know, solar printer. Businesses that I, that I start so that I never have to do that.

And so that was kind of a windy way to answer that question, but I think that's actually, you know, if there's any takeaways is like, again, designing your work so that you actually don't have to be constantly grinding. Yeah. On those projects at least.

Jennifer: it's a really important point. Important to manage your energy I am so curious then, how are you spending your time these days?

How are you structured?

Steph: Yeah, so I mean, I have a full-time job, so I spend a lot of time there and then, . I also probably work too much. I spend a lot of time on the weekends. Um, I would say that one of the reasons I actually went remote years ago is I don't really abide by a schedule . Like I can't, I really can't stick to one. Um, and so again, like it's kind of, it sounds like I'm just like this, this person who.

Just needs to do things her own way or like won't listen to anyone. But it's actually more so just like if you give me the space to figure out how I can work most effectively, I'll get way more done than you expect. But it might be at like two in the morning, it might be on a Sunday afternoon. And so, yeah, I don't, I, I know it's not a great answer, but I really don't have much structure.

In fact, I tried to reduce like the number of meetings or the number of fixed things on my calendar cuz I just, I don't do well with them.

Jennifer: Again, you're managing your energy. You're working when you're excited, which is when you're doing your best work and you're in flow state then, and you can just knock things out and you don't need to be working in eight to five.

You can have enough super productive sprint at. , whatever time you have it, and then you can do whatever else makes sense at another time. So then to be clear, is your full-time job the podcast with a six and Z or something else? And then what are, I'm just curious what, okay. And then what is, what is important to you these days in terms of how you're spending your time?

Steph: Yeah. So I think there's, again, talking about this like pressure that builds up over time. I've had so many people who are like, when are you gonna start your next business? When are you gonna start like a big business? Um, I've talked on a few podcasts. How about how I want to like , I mean, this sounds silly, but like, be a billionaire or like create generational wealth.

And so, Yeah, I think right now though, as I'm working, still working at a 16 Z and have a full-time job, there are a few projects that I'm just really excited to get out there and they're, they're small projects that are not the road to like being a billionaire or anything like that. Um, but again, they're things that like, truly I, I like go to bed and I'm like, oh, I wanna work on that the next day.

And so I don't, I can't share some of them yet because um, they are the kind of projects where I. I haven't seen someone do this before. And again, they're small. But um, yeah, those are the kind of things that I'm optimizing for right now of just like, what am I excited to work on, um, the next day. And then I think over time, like there will be an idea where I'm like, this is, maybe this sounds extreme, but like the change I wanna make in the world.

Um, this is like the mark I wanna leave and at some point I do want to. Something that I'm, you know, five, 10 years down the road, maybe 20 years, maybe 30 years, I look back and I'm like, I'm really proud that I created this.

Jennifer: I love it. And Steph, I'm an executive coach, and I coach women and multicultural folks and folks that are minorities. And so I'm really attuned to this. And I've been hearing you say, this may sound silly. I've talked on a podcast about I wanna be a billionaire, or this may sound weird.

I've talked about how I wanna change the world, and I just wanna say that it's not silly whatsoever, and I want you to feel. Full permission to dream as hugely as you want and you can do it. Uh, you've been, there's no reason why you won't be able to do it. And you've got tons of supporters along the way.

You will likely fail along the way. Nobody gets there on one straight shot. Some people do. Um, but like you'll get up again and you'll keep going and you'll learn and you've got tons of supporters and it'll be an interesting. The journey will be fascinating and you'll get to wherever you wanna go. And I feel like in those, in those journeys, it's so important to understand what your why is and that'll drive you through all the ups and downs and bumps along the way that come with building projects.

And I'm so glad that you're not succumbing to the pressure too and just doing the things that feel fun and exciting these days, cuz

Steph: Yeah. And to clarify on, on the billionaire thing, I think what you said is really important, but I think there's just, I think, you know, you talked about your why a lot of people are like, why, like, why, why do you care about becoming a billionaire? And I think that's just, that is maybe just a, like an arbitrary mark.

I don't necessarily need to have, you know, that number of zeros. Right.

But I think, I think there is something really beautiful to having an amount of wealth. Whatever you wanna work on. And that, by the way, can be impacting change, not just for yourself, but for many others. You are able to do, you have the resources to do.

And as, as we talked about earlier, coming from a place of extreme scarcity in the past, having that and being like, oh, actually I don't need to limit myself to these indie projects. Oh, I can't actually hire 10 software developers and not have to do things myself and hack, you know, hack this thing together.

I can think bigger and. Wealth is a part of that. And so that's one of the reasons where people are like, you know, why, why do you care about that name or that number? Um, and so it's not so much that, but it's like as we, as you talked about, like thinking bigger and getting excited about what change you wanna make in the world, and I think that inevitably becomes part of the equation.

Jennifer: And there's so much bravery too, to thinking bigger past where you come from, past what you've seen growing up and. Feeling like, you know what? I want that for myself. That in of itself is brave. And I also wanna say that cuz I get really annoyed with this. It's, it's not about everyone else and what they think about your dream, it's about you and your dream.

And hopefully again, we, we start to get to that point where people aren't trying to label you based off that their experiences, but they can listen to you and accept you for who you want to be. We are, we are the work in progress. We're getting there.

Steph: absolutely.

Jennifer: But I'm really excited for you.

Steph: Thank you.

Jennifer: what are you learning these days?

Is there anything you can share with us? No pressure if you can't.

Steph: Absolutely. So I think, you know, in the past I've learned what people might consider more concrete skills like learning to code. Um, but these days it sounds silly, but it's actually, it's been a. It's been as much of a learning curve as something like learning to code, which is becoming a good podcast host, and that includes the like technicalities of how my voice sounds, how I speak, how quickly it is, but also it's, you probably have experienced this.

You get so much feedback and you also don't realize little minuscule things like, do I interrupt someone? If so, how do I do it? Do I talk about my own experiences or do I feed into more so what people wanna hear from this guest? And when you are a listener to a podcast, you don't notice any of that because the best podcast hosts have mastered that skill.

And so that is something. Since I took on this job. You know, it's not so much that I expected to be amazing immediately, but what I will say is it's been much harder than I expected. There are many more nuances than I expected, and again, like that's, I'm focusing on both the technical aspect, but also like just how to interact with people more effectively.

And maybe that sounds really clinical, but again, the best podcast hosts make it sound easy to the, to the listener, and I think a lot of people. it's not easily apparent to them how difficult it is to create a really great podcast, especially when there's so many out there today.

Jennifer: Hence a bit of the frustration with what do you do? You're a podcaster. What is that? Is that a full-time job?

Steph: Yeah, well, I mean, I tweeted about this the other day. There are just some jobs, podcast hosts is definitely one of them, where a lot of people, um, just think anyone can do it. And in a way it's true, right? Like it is democratized. Anyone can start a podcast today, but it's also like the same phenomena where everyone's like, oh, I can manage my own money just as effectively as like, you know, someone who, who has done it for 50 years and it.

Yeah, maybe. And partially because again, like you can technically do that. Um, but I think there's just certain industries, certain professions that just sound way easier on the surface. Um, and once you get under the surface, you see this big iceberg where you're like, whoa,

this is not what I

Jennifer: Absolutely. and fyi, same thing here. I'm constantly evaluat. It's like a constant conversation in my head. Do you interrupt now? Do you share this? Maybe don't, like, how do you like get into the next topic of the conversation.

Steph: Right. And I think maybe the reason this job, and I mentioned like managing finances is another example. There are certain jobs where there's no right answer and that's why it's even harder because as a podcast host, you'll sometimes get literally conflicting feedback, or at least I have. Some people are like, I'm so glad you don't interrupt.

And then literally the next piece of feedback is like, I wish you interrupted more. And I'm like, and that's just like, Micro example, but there's so many cases, and I think ultimately what I've come to learn is simultaneously I can work to be better, but I can also realize that my podcast style, even my voice, for example, is just not going to resonate with some

people. and

that's why there's different podcasts out there. And some people love Joe Rogan. Some people hate Joe Rogan. Some people love call her Daddy. Some people think she's obnoxious, right? And that's okay. Right? And so, Having to retrain myself because other things I've done, it's like I can back in business consulting, I create a model in Excel and it's like there, there kind of is a right way to do that and this is a role where I'm like, there actually is no correct answer.

Jennifer: right? It's almost like there is no right way to be you. You're just gonna be you. It's your way to be you and that's what makes people love you and come back to listen to you. And it's almost like the more you try to hack and become something for everyone, the the less successful you'll be. And it's almost, it's a great thing to have some people that just can't stand listening to you and other people who love listening to you and rave about you and wanna.

as you can hear, I'm also in this process and we'll definitely love to hear more for another time though. Um. speaking of podcasts and, and all your jobs, et cetera, and working on being you, I'm so curious. Who are some of the folks that you've talked to that you've been really impressed by?

And not necessarily because they make a certain amount of money, or they're super smart or whatnot, you can be impressed by folks for different reasons. I'm curious what folks come to mind for you and what you've learned from.

Steph: Yeah, so I mean on the A 16 Z podcast, I started like six to eight months ago, but I think the through line from a few of the folks that. I really resonated with is that they've been thinking about, you know, a problem in the world for like forever. Right. Since they were a kid or, or like long before they actually founded a company

Jennifer: Oh no. I've been just moving from thing to thing. I feel

Steph: I know. Well, that's what I'm saying. So there are some folks that I've interviewed where I'm like, this is so impressive that you have had the dedication, the focus. towards this one thing, and you are just like hell bent on fixing this issue in the world. And so I think that is something that, you know, as I talk to these folks who are like much, in many cases, much older, much further along in their career, I mentioned this before where I'm like, I don't know exactly what it is.

There are things I'm passionate about today, but there hasn't been one thing where. , I wanna spend the next 10 years on this. I wanna spend the next 20 years on this. And so I think that's what I find really, you know, inspiring about some of the entrepreneurs that, um, again, they're just like laser focused.

Jennifer: Mm-hmm.

Steph: I mean, I think I tweeted this a long time ago, but, and it got a lot of flack. Cause it, you know, anytime you mentioned Jeff Bezos, people are like, oh, he's a billionaire, he's bad. Um, but I think it was when he stepped down from. And I was like, I think he had by that point been working on it for 31 years or something like that.

And I was like, man, like regardless of what you think of him 31 years, like most people don't spend more than two years on something. Probably the thing I've spent the most time on is somewhere around five years, right? Like, so six x that and, and so I think that that's been across the, the folks I've spoken to in the short period of time that I've been doing this is that is like if you really wanna make a difference in the world, like you mentioned before, anyone can do it, but also to make a large difference, a sustainable difference.

I do think like you need to have that focus. We talked about this, like we mostly haven't done. That doesn't mean we haven't made change in the world, but like that does inspire me seeing those people who have focused for so long.

Jennifer: Absolutely. It's huge. It's interesting that you bring that up it feels like seeing something in others that you want to work on in yourself is something that you admire and are inspired by. Um, what, what that brings up for me though, is I don't necessarily think it's a bad thing to have been exploring.

Like you have two, two types of people, right? You have like the one person who's extremely good at. that's something and goes really deep and is super talented at that thing. Then you have other people who are generalists and can do other things well and their strength is bringing a ton of perspective and I actually, I think there is a ton of value in merging these two types of folks together in the world and a ton of like opportunities there for both to exist.

And it doesn't, it doesn't mean that one or the other is the right way. Again, there is no right way. , but I, I have had this thought and I am gracious with myself about that too. And I want, I do wanna say that because I think a lot of folks our age, a lot of millennials who have been uh, transitioning, may feel guilty about things like that.

And, um, I feel like as long as you're learning and per going after things you're passionate about, , um, you're eventually pursuing growth in learning and improving, and

you will eventually figure out, find a way to be more impactful. Um, and yeah, I feel confident that you will continue to make change. And same for me and same for others.

But I'll let you in. I know you, you've wanted to.

Steph: No, I mean, I was just gonna add on like, you're, you're absolutely right, and I do think it's important for people to take the time that they want to explore. And actually there's this really incredible, um, there's this book called Algorithms to Live by, have you heard of it?

Jennifer: Yeah, yeah,

Steph: the, the example from that book that I think is really, um, applicable to, to anyone's life because it's, it can be applied to relationships and dating.

It can be

applied.

Jennifer: rule.

Steph: yeah. The 37% rule. And, and it's, it's this idea that you should, you should in fact go explore. Um, and so if you like, the example they give is with dating, but if you were to look at your life from the perspective of a computer science problem, and you have this idea where you're not sure of when to settle on something or to explore further, The conundrum that again, applies to most things in life.

Like when, when have you found something good enough, um, to go deep with? And so with the example of the relationship, it's this idea where like, let's say you have this time period where from like 18 to 30, this is just an example you want to date, but also at some point by the end of that period, Be with someone.

Um, you're supposed to take 37% of that. Again, if you take the pure computer science problem route and apply that as your exploration phase, which is just, I'm going to go and meet a bunch of people, or again, if this is a job, I'm gonna try a bunch of jobs. Or if this is an industry I wanna go to a bunch of different, um, I wanna try a bunch of industries.

And at the end of that, You have seen a lot, but during that phase, that exploration phase, you're not supposed to settle down at all. You're supposed to explore, and then at the end of that, you have this remaining remaining period where you continue exploring, but as soon as you find something that's as good or better than what you explored during that 37% period, then.

Go deep. And so I think to your point, I, I don't feel bad and I don't think people should feel bad if they're still in that exploration phase. And it doesn't need to be 37%, but you should explore in life.

Jennifer: Yeah, absolutely. And to the specific example of Jeff Bezos, he also didn't, this wasn't the first thing he did,

Steph: Yes, exactly.

Jennifer: he brought in his experiences from investing, for instance, to figure out that, oh wow, there's this big trend here. Um, speaking of, uh, like algorithms and data, let's talk about money, if that's

okay. So similarly, I think a lot of millennials, a lot of creators now who are Gen Zers, um, in this economy. Are faced with a decision of, you know what? I have this passion. I have this project that I'm excited about, hopefully managing their energy really well in how they do it and want to be able to monetize their value.

A lot of them are also faced with a fear or an insecurity of charging for their services, et cetera. So given that you've been doing this and been going through it, wanted to invite you to share what, what have you learned about monetizing your value? I know you used to share your goals, et cetera.

So curious where you're at these days.

Steph: Yeah. And the only reason I stopped doing that is because I haven't had the time to update it . But it's not because I decided, you know, I hit a certain

Jennifer: you're gonna be

Steph: therefore,

yeah, no. Um, although there's a whole dynamic to that, right? Where like, again, this idea of joy of inconsequence, when you're making your first thousand dollars, people are jumping up and down for you when you're making your first million dollars.

That changes. And certainly when you're making a lot more than that, you actually. Probably an inverse reaction, but coming back to, to learnings, I mean, people used to tell me this, um, when I was first creating my own projects and for the first like four or so, I didn't monetize at all. And I had this friend in Bali who just kept telling me like, throw up a PayPal link.

Just like, add a button. Just add a button. And I was like, no, no, no, no. Like this. Like this stuff isn't worth. anything. Um, and in that case maybe it wasn't, but when you do have something where you're having this debate with yourself, like, should I charge? And also how much, I think that's actually the perfect opportunity to get data and to just accept the fact that you might not like the data.

You might actually love the data that comes back, but you need that information. And so what I did with my book is I think I tweeted something like, Hey, would people pay 10 bucks for this? Um, I'm thinking of creating it, so I hadn't even created. And a bunch of people said, yeah, yeah, yeah, I would. But some people also said, oh, you should totally charge more than $10 for this.

And again, this was a point where like many people, I was like, okay, well you're saying more, but is that like $15? Is that a hundred dollars? And also, are you like the only person who would be willing to pay that or is everyone willing to pay that? And so I did this thing, um, where I like tiered my pricing and people don't have to do exactly this, but find a mechanic where you can get.

Answers. You need to feel confident in whatever you're doing. Um, and also by the way, whatever price you set isn't permanent, you can change it whenever. Um, but what I did was, I said the first, I think it was 30 copies were $10, and then for every subsequent 30 copies or so, it increased by $5 and someone.

Who comes from marketing, like I used to do this kind of stuff for companies, but for some reason a lot of people forget that you can use the same testing, the same tactics with your own products. And what I found was like you could look at the data, I had some answers where I was like, oh, at least during presale things kind of leveled out.

Once it got above $30. So I actually then said, okay, experiment over. I'm keeping it at $30 for now. And then since it's gone higher as people, you know, there was social proof and people liked the product. Um, but I think that if anything is the main takeaway, like a charge probably before you're comfortable, but also.

It doesn't need to be this fixed dollar amount that sticks with you forever. Get the data you need and then you can adjust it over time, especially if you're building something that evolves over time. You probably should revisit your pricing.

Jennifer: And then the thing I will add to that, cuz that was so well said. and with respect to a charge, folks that are worried about charging, uh, often tell me, oh, but it's not nice. I feel like it's not like it's not worth it, like what you were saying, but I'll offer this perspective of it. When you charge someone, they value the product more.

They become more invested in the product if you're helping folks learn something or if you're giving them a service. So it's almost not nice for you not to charge. So just sit with that, see where it gets you. We're running outta time, Steph, and I wanna be respectful of your time, but before we let you go, I'm so curious.

You've, you had been no matting. I know that you just moved. I'm curious where too, I know you are now married, and so I'm just curious how the stability is hitting you and if you're getting

Steph: old.

Jennifer: feet about novad again.

Steph: No, I mean, we talked about. I guess what's inherent in you and like what's learned over time. And I do think there's this like need to roam where I've, I've settled down. I actually moved to a place called Encinitas at the beginning of the pandemic. So I've actually been, I mean we've traveled in the last couple years, but I've been non nomadic now for around three years, which is kind of like,

Jennifer: Oh wow.

Steph: it kind of pains me to say that

a little bit. Um, I know. Um, but um, we just moved to San Francisco and so I think there's a part of me that. is like, I needed this, like I needed to slow down. I think most nomads you probably were the same, where when you're moving around like crazy it's not sustainable and

you're

not creating

Jennifer: to just get me to be anchored. I gotta be home every three-ish weeks.

Steph: Yeah, exactly. And you know, creating a true community and I kind of, I, I was able to achieve aspects of that in places like Tanu, cuz I, I would go back there very consistently and. Large amount of time there, um, or like several weeks to months. But yeah, I mean, I think one of the reasons I want to be wealthy is to have that freedom, that untethered freedom, where my goal is to have probably like three permanent homes around the world in my favorite spots, and not be no nomad like I did before.

Um,

Jennifer: Oh my

Steph: Have.

Jennifer: would you have your homes,

Steph: So, as you know, when you're married, it's not so simple, but

if it was just

me,

Jennifer: them in this decision. Oh

Steph: yeah, there's, there's some balancing there. But if it was just me, it would probably be in, um, maybe in Bali, maybe in Japan. Definitely somewhere in Asia, Scotland, probably in Edinburgh, and then maybe somewhere close to home in Toronto.

Jennifer: Mm-hmm.

Love it.

Steph: worth

Jennifer: I wanna come visit. I want a home in Shamini, in the Alps in France. I really like Paris and New York City. I also need a lot of money for this,

Steph: Well, that's the

Yeah. Well, that's the goal. Um, so that, yeah, I, I think that. Candidly, I would be unhappy. And that sounds so, uh, silly probably to many people, but I would be unhappy if I was fixed in one location for,

Jennifer: I think it's something that comes from this lifestyle, right? Cuz similarly, I grew up in Sierra Leone. I would spend summers in Ukraine. I moved to the us. I was in Boston, San Francisco and New York. Now I live in Austin. We travel a lot visiting family in Poland and Sierra Leone. And it's just not used to being in one place as well.

Like if we're, if we haven't traveled for four weeks, we start to get like, okay, we need to do something, we need a trip. And I think it's just a. experience from folks who have used to being, staying somewhere and both can exist and be true, and it's just who we are.

Steph: Yeah, I mean, I think so. Cuz I look at people who have been living in the same place for 10 years and I'm like, I don't know how you do that. But they

probably look at the life. Yeah, exactly. And they're like, well right back at you. So I do think there's a part of me that just needs to

roam

Jennifer: Yeah.

And,

and make all these friends in these different places and learn from them and have them infuse into your world.

Steph: Yeah, exactly. I mean, I don't know if you found the same thing when, um, I was nomadic for a few years, but they're, because most people weren't for a period of time, there was also this degree of self selection where I just felt like I connected with those folks so much more than, you know, if I was living in one place at one time.

Um, so it felt like a special time. It feels like things have changed a little bit. That part of building a community like I, I don't know if I've found a community since then that I've resonated with to the same degree.

Jennifer: Mm. I feel like we will continue to find each other, and it's such a beautiful journey to be on together and finding your own paths, and creating your projects, and hopefully making the world better while we're at it.

Steph: I agree.

Jennifer: Steph, this was amazing. I will let you go. we gotta do this again

Steph: Definitely.

Jennifer: coming on.

Steph: Thank you.