This episode's guest and Huddle investor, Stephanie Engle, is best known for role as a product designer at Snapchat, and as an angel investor into product driven companies. Before Snapchat, where she works mostly on AR experiences, she worked at Airbnb, she was the first product designer at Cruise automotive, where she designed interfaces for self-driving cars, and she started her career in Silicon Valley at Facebook designing VR experiences.
Mike Saloio Instagram, LinkedIn, Twitter
Huddle Website, Instagram, LinkedIn, Twitter
This episode's guest and Huddle investor, Stephanie Engle, is best known for role as a product designer at Snapchat, and as an angel investor into product driven companies. Before Snapchat, where she works mostly on AR experiences, she worked at Airbnb, she was the first product designer at Cruise automotive, where she designed interfaces for self-driving cars, and she started her career in Silicon Valley at Facebook designing VR experiences.
Mike Saloio Instagram, LinkedIn, Twitter
Huddle Website, Instagram, LinkedIn, Twitter
Why don't we just start over from where we just were?
Stephanie Engle
·
04:39
Perfect.
Michael Saloio
·
04:42
Where are you in the world and how's your day going so far?
Stephanie Engle
·
04:46
I am currently in Santa Monica. I am actually at Snap's headquarters right now, which is fun and very glamorous and lots of secret things behind me. But yeah, today, overall, can't complain. It's a little rainier than I pay for in California, but mostly pretty nice.
Michael Saloio
·
05:08
Nice.
Stephanie Engle
·
05:09
How about you? How are you doing?
Michael Saloio
·
05:11
I'm doing great. I'm in Miami, Florida.
Stephanie Engle
·
05:13
You? Can't complain.
Michael Saloio
·
05:15
No, it's all good. So thanks for joining us today. Joining me today on our second episode of the podcast, which we now have a name for called Lone Geniuses. I'd like to just start off by your background and a little bit about how you got to where you are today and why don't we start? Where are you from?
Stephanie Engle
·
05:47
Well, first of all, if Lone Geniuses is the name of the podcast, I feel like I'm on the wrong podcast. Where am I from? So I was in San Diego for specifically Del Mar, if people know that, until I was 13 years old, right before I started high school, like literally the month before I started high school, and then I moved to the Bay Area. So when people ask me the question, I'm like, oh, kind of Bay Area, kind of San Diego. I spent the very formative years of my life making a brand new set of friends in the Bay Area in high school. So mostly there and then from the Bay Area, I kind of knew I was going to come back. Like, I kind of saw tech around me, and that was what everyone was doing.
Stephanie Engle
·
06:32
And so I was like, I think I'll probably come back here. But in the meantime, basically my college criteria was I want to go to Stanford as far away from home as possible. And so I ended up going to Duke, which fit that bill pretty well. And so I spent four years in Durham, North Carolina, which is still one of my favorite places probably in the country, and then I made it back to San Francisco through a winding set of ways, and now eventually I made it to Los Angeles. So I don't know. It's kind of a winding history of cities, but we can get more into it.
Michael Saloio
·
07:08
Yeah, well, I was Durham a favorite place of yours?
Stephanie Engle
·
07:11
Oh, my gosh. First of all, I had such zero expectations. Maybe I'm a typical designer in this way, but when I was picking colleges, I truly went for a vibe and a feeling. And so when I visited schools and I went to Duke, I just said, I love this place. It looks like a gothic, beautiful place. And I knew that if I was in a beautiful place, I would probably feel important. And if I felt important, I would probably maybe do a few more important things and maybe fun people would rub off on me. And that was honestly my very silly criteria. And Durham, I had very low expectations for all my family members sent me like, crime reports from the area and all this stuff before I went. And I was like, oh, God. But actually it was unbelievable.
Stephanie Engle
·
07:55
There's actually a really great little startup scene there. People are super friendly, the weather is super mild. We got like a very chill seven days of snow a year and it was like two inches and the whole school and everything would shut down, which is amazing. And just the food. The food is like unbelievable there. Yeah, I don't know. Big North Carolina person.
Michael Saloio
·
08:19
Nice. That's so cool. And you said that you were following beautiful places because you feel, I think you said important. And then you would do more important things. Like when were chatting before this, you told me this epic story about horses and photography, which I hope you'll share. And one of the threads that I pulled out of that was by your very nature, you're looking around and finding people to get inspiration from and it sounded like that's been a big part of your journey.
Stephanie Engle
·
09:04
Yeah, there's like kind of two influences to that and I will tell that embarrassing story in a bit, but two influences to that. So one is at one point in my life I wrote this article and I really wish I could recall the name of it. It was just very brief in one of my courses and it was about so I took public policy courses, which is all about designing cities and systems of government and people. And we had this kind of urban design class that I took. And one of themes in the class was about designing really beautiful spaces for people who maybe feel like they don't deserve dignity in situations. So one of those was beautifully designed hospitals and it was talking about why are cancer wings really stunning a lot of the time?
Stephanie Engle
·
09:53
And there's some of the prized points in a lot of hospitals and obviously that comes from donors and personal interests and things like that. But it also spoke about how a lot of these people are maybe in delicate stages of their lives. And so being in a hallway that doesn't feel like a hospital and feels more like a home or something like that is actually really inspiring and important and leads to good outcomes. And so that's a long way of just saying that I really prioritize the spaces I'm in because I know that if I feel like I'm in a space that makes me feel warm and loved and happy and comfortable, I'm going to be able to do a lot more things. And then, yeah, in terms of people, I was just really influenced by my dad at a younger age.
Stephanie Engle
·
10:36
My dad is I would call him like a turnaround CEO. So he joins struggling biotech companies and he tries to help them turn around or not. And so his mantra to me, like, when I was a kid, he would really advocate for, like, you should always be the dumbest person in the room and be around people who make you sweat and just go follow them around and whatever they do. And you'll pick up all of that by Osmosis. And so I think, yeah, definitely a theme for me has been put myself in spaces that make me feel good and also follow people who maybe make me sweat and maybe make me feel uncomfortable in some ways. And I will succeed almost simply based on that. Like absorbing those things.
Michael Saloio
·
11:24
Yeah, just being there.
Stephanie Engle
·
11:26
Just being there and just being in the right conversation and hearing the right terms. I mean, that's obviously why a lot of people flock to specific cities, like SF at one point. Being a hub, it's just like you learn the references that you can use in the conversation. Right. So it's just sort of like yeah, it's just that being in the right sort of place and the right dialogues and that eventually you kind of can become them. Hopefully you have more substance than that, but yeah, that's really cool.
Michael Saloio
·
11:56
I've never heard anyone say it like that before, be around people that make you sweat. I was just trying to think about when the last time that was for me. Probably our investors at Huddle, which you are actually one what's an example of that for you in your life or career where you put yourself in a room like that and took that advice?
Stephanie Engle
·
12:22
Yeah, I mean, many times, I think so when I was gosh, actually, sorry, I'm pausing trying to think of what's the best story to tell here, I guess. So when I was at Duke, I didn't really actually know what kind of job I was looking for. I just knew that roughly I wanted to be in tech and startups. And I had a set of creative skills that came from that photography business and all that. And I don't know if we should mention that first before I get into all this, but anyway, so I had a set of creative skills. I didn't quite know what I wanted. And I had this portfolio online and I was sort of active on Twitter and talking to folks.
Stephanie Engle
·
13:07
And I remember one day, the founder of a company at the time that was very kind of notorious and had raised a lot of money very quickly. It was called secret. And the founder of that company, David, actually reached out to me and he said, hey, are you doing anything this summer? And at the time, I actually was going to go work in a consulting internship that I was very unexcited about. And I said, no, I'm not doing anything. And he said, okay, great. Do you want to come and just hang out with us and see maybe what you could contribute. And so I said, sure. So I came out there and he asked, what skills do you know and what have you been doing? And at Duke, there was no design. People weren't designers at Duke.
Stephanie Engle
·
13:49
And so I had seen what creative folks were doing, and the kind of creative things I had done at Duke I thought was marketing. And so I told them, oh, yeah, I could do marketing. So I started doing writing content, and anything they asked me to do. Actually, at one point, they asked me to work on a content moderation tool, which was fascinating and a good experience. And then eventually, I saw what the designers were doing all the time, and I said, oh, like, I can learn that. I can I know how to use figma and photoshop. Well, I guess at the time, it was photoshop transitioning to sketch, right? And so I picked up those skills and I just said, oh, I can do that.
Stephanie Engle
·
14:31
So I started working around these folks, and all these folks had been like super early to huge Google projects and things like that. Everyone was like an all star cast of folks. And so the way I learned design was really through this group of people who the app was also known for its design, and it was anonymous social network, so that was one part of it. But then from there, I immediately took that experience and I said, okay, what's the next thing that I can be doing? And so I took the portfolio from there and some other things I'd been doing, and I just direct messaged it to the VP of design at Facebook.
Stephanie Engle
·
15:08
I knew that people at Facebook used messenger to communicate, and at the time, messenger didn't have any spam walls, and I knew I really wanted to work at Facebook and believe it. Back then, it was like the coolest design company to be working at, basically. And so I just DMed her my portfolio, and she just passed on to the recruiters. I don't even know that she looked at it. I think she literally just forwarded it on, and they just thought it was like a recommendation. And so they ended up taking me on to work at the company and become an intern on the profile team. So I worked on designing Facebook profiles, and I think at Facebook, at that particular moment in history, they had this all star cast of designers. And every week I was in design critique.
Stephanie Engle
·
15:58
And I think design is really interesting in that it's one of the only functions where you sit and you look at everybody's work and you kind of undo it and offer feedback every single week and work that's quite personal. And especially to me, at the time, it felt really personal because I didn't have the mature skills yet to be able to distance myself from the things that I was working on. But I would sit in a room with folks like Mike Mattis, who designed some of the first iPhone screens, or Alex Cornell, who's just this unbelievable designer who's worked at a few different places, and folks like that, and I was just, like, sweating all the time. I lived and breathed their feedback, and I couldn't distance myself from it.
Stephanie Engle
·
16:37
And I would see their work, and I was like, oh, that's what we're expected to present here. And so as an intern, because the bar was set for me every single week that you have to come in and it has to look like Mike's work or something, I just had to get really good at prototyping. I forced myself to just learn a ton of skills really quickly and make these super cinematic videos of prototypes and things like that. And that was just a great time where literally every week I had a session where some of the best people in the whole industry were just, like, making me feel panicked. At that point, at that point, I was like, oh, my gosh, I can't even keep up with these people. But now, looking back, I'm like, that was the growth period.
Stephanie Engle
·
17:21
That was where I really compressed a lot of years of looking at average design or not even really knowing what design was and being boot camped into being like, those people. Right. So that was definitely a time where, yeah, I had a weekly outlet to be around, a bunch of intimidating folks who are very nice and wonderful, who really pushed me into a new skill set.
Michael Saloio
·
17:50
I want to dig into something you said that's a little bit unrelated, but how do you review a body of work or designs in a room with a bunch of people like that without taking it personal? Like, I'm kind of curious of what the process actually was like.
Stephanie Engle
·
18:09
Yeah, I mean, at the time, for me, it was very personal, right, because there's the classic IRA Glass quote on how your taste doesn't match your skill. And so my taste was rapidly developing because I was seeing such good work, but I literally did not have the skills. I didn't know how to prototype. I barely knew how to use any of the tools. Right. And so I would see what they did and rapidly had to figure it out. So at that time, it was quite personal to me. When they would ask a question, I took it as like, oh, God, I have to question everything. I can't just take that as an isolated thing. I think one of the most important things is understanding.
Stephanie Engle
·
18:48
And I think a lot of people could benefit from critique and having weekly critique in this way, I think it's just understanding that it is feedback from people who you might admire and you might feel good about, but ultimately, they don't have the full context and you don't have to accept it. It's okay to just hear it and put it away and think about it later and maybe use it or not. And so I think just over time I had to get better and better at understanding that feedback. Truly, the goal of those sessions is to get as much as possible from each person and then to do something with it. Whereas I think at the time I was like, oh, it's like a debate.
Stephanie Engle
·
19:27
I have to make sure I'm correct by the end and they have to know why my decision is so good by the end. And actually that was very much the wrong mentality. It was just sort of like they have input and they have their own curiosities and questions about their own work and just that it's not a question of right or wrong in that scenario.
Michael Saloio
·
19:48
I love how you said it's not a question of right or wrong. That's very much what I've had to train myself to think in these situations. I'm just going to use fundraising again as the example. Like, I have to be able to sit in a room and be really confident about the way that we're doing it while also listening to a lot of other people's opinions on how we should do it. That's actually what I was going to ask you next. How do you stick to what you believe? Let's say your skill clearly now matches your taste. I'm just going to say that as like a fact. And so how do you stick to your taste and view and still take into consideration everyone else's critique?
Stephanie Engle
·
20:39
Yeah, it's interesting. I think I've not so much had that problem. I think I've always been sort of someone who stuck to my guns. And I think where that comes from for me, especially honestly, being a woman and being the youngest person in a lot of these situations, I was really lucky that at an early age I had a few instrumental folks. Like my dad and like my early fourth and fifth grade teachers and things like that, who really built up a lot of my confidence and confidence to say when I feel conviction about something.
Stephanie Engle
·
21:17
I also did a lot of like, my parents didn't make me do any sports or anything like that when I was a kid, but for some reason my dad really wanted me to do toastmasters, which is basically where you get in a group and you present speeches really often, and often they're like arguing a point. And so I just got better and better at doing that, I guess, and understanding points that I had no feelings about. Right. I didn't really care about the particular subject, but I just had to argue it. And so I realized that a lot of my work is the same way, where it's like often a point I need to make, but it doesn't have to be a personal point. It can just be like, I'm a good soldier. And that happens a lot of times.
Stephanie Engle
·
21:57
There are times when I work on designs and I'm like, I am just being a good soldier. I'm doing what the group thinks is right. I don't fully know yet. When I join a new company, that's often the approach I take is like, I don't know, so I'm going to try and find out, but I'm not going to stop the motion and I'm going to trust people around me in order to do that. I think one thing that I've actually had to get better at and struggled a lot more with is I think the people I admire the most and I realize are actually the most talented people, are the people who are the conduits for everyone else's ideas. So a few coworkers in particular stand out. One was named Bradley Ryan, and I worked with him at Cruise and brought him in there.
Stephanie Engle
·
22:41
And then one is one of my manager now, CC. And those two folks are just brilliant examples of like they just always are asking everyone questions and they're always showing their work to others in a way that makes them feel like they're sharing a secret with them. Like, hey, check this out. And Steph, I really want your feedback on this because you did that really smart design last year about something related. And for a while I was like, wow, they have a lot of questions about their work they must not like or they need a lot of feedback. Maybe the people who need tons of the feedback actually don't know what they're doing. But obviously that as you mature, everybody starts to learn that's not actually the case.
Stephanie Engle
·
23:26
And what I realize is that these people are so fun to brainstorm with, so fun to tell ideas to, and they make everyone else feel so good about sharing their ideas. And I realize that's the most brilliant skill because you absorb everyone else's thinking. Like, you become the smartest person just because you make so many other people feel good about sharing their intelligence with you. And so by the end, you know everything right? And so I think those folks are the most interesting to me. And so a common theme for me in my recent years is like, how do I become the person everyone wants to tell their secrets and their ideas to? And I realize that's how I find the people who get more out of me, who get me to be more vulnerable, and who get me to share my ideas more.
Stephanie Engle
·
24:16
And it allows me to influence my ideas more. Because if they see me as a conduit and they trust me and I give them an idea and I share something, they might start repeating the phrase or sharing the idea around the organization just because they enjoy it, or they are made to feel good about it. So anyway, that's a skill I've always super admired and tried to figure out how I could bring out in others, but also to find other people who bring that out in me too.
Michael Saloio
·
24:49
That's super cool. All of my favorite people are that too. I love people that create space for creativity to happen. Like, I'm really obsessed with music producers for this reason. Ever since I was like ever since I can remember, I was looking up who produced which songs that I liked, and I ended up finding out that a lot of them were produced by the same people. And it's also a reason why I started to train in coaching a bit, because what I've learned about coaching is it's really just about asking really powerful, open ended questions. But I love the piece about just getting other people's ideas to shine through. It's like empowering creativity in a big way.
Stephanie Engle
·
25:36
Yeah. I mean, also on a more selfish level, it is like you are becoming the conduit of information. So when someone has an idea or a piece of information, they tell you first, and not in a competitive way or anything else. It just means that when people get defensive, others don't want to tell them their ideas. Right. If you're super critical or if you're super defensive, you actually are blocking out good ideas. You are blocking information from getting to you. And I think those are the folks who really struggle.
Michael Saloio
·
26:13
The ones who block the ideas.
Stephanie Engle
·
26:15
Yeah. The ones who are defensive and critical and need to be right about things. Like, no one wants to share ideas with those people or collaborate with those people, frankly. And so I think those people really are stunted in their ability to acquire that type of information.
Michael Saloio
·
26:32
Right, and probably stunted in their ability to attract people with great ideas.
Stephanie Engle
·
26:37
Exactly. Yeah. To hire or to get people on a team within a company or anything else. Yeah.
Michael Saloio
·
26:44
I also love what you said about being a soldier. And I really mean that because I think the more that I remove myself from the thing I'm creating, the better the thing goes. Because then I just do the tasks necessary for whatever that thing is to succeed without worrying about how I look, is what I really wanted to say. I think that's I think that's my own version of this, but like, without worrying about, like, what I might look like if it doesn't go well or if they don't pick my idea or whatever.
Stephanie Engle
·
27:20
Yeah. It's something I've learned only more recently in my life, is that I used to think that I was just someone who was just overly ambitious and was trying to do way too many things at once. And then I realized over time that actually, when I have a few more focuses and passions and areas where my creativity goes that aren't my work, I become better at my actual job. Because I don't have so much invested in it emotionally, and so I'm able to kind of distance myself. And so I think for me, something in recent years is just like exploring other outlets of creativity and business. And actually I just feel like at work I'm able to kind of present work, let it be, get all the feedback on it, make it better. Like you said, like a good soldier.
Stephanie Engle
·
28:04
Often I have my opinions and I'll stand up for certain issues, but a lot of the time it is just like, oh, Data says this, people I trust are saying this, and maybe there's nuances to how I think I should do it, but it is going along with it. And I think that having a diversification of things that I'm creative and passionate about definitely makes me able to be the good soldier, I guess, at work, which is often what's needed.
Michael Saloio
·
28:33
Absolutely. That's certainly true for me as well, in terms of just removing myself from just taking it personally. I don't know how else to say it. It's like the ability to go treat the work like the work and make good, objective, creative decisions. What are some of those things?
Stephanie Engle
·
28:58
Yeah, probably too many things.
Michael Saloio
·
29:03
No, it's not. You just told us it's not.
Stephanie Engle
·
29:05
Yeah, exactly. No, I'm perfectly balanced and have no issues with my time management. It's things like this where I love working with folks like you all at Huddle and other startups, kind of asking for my support and investing and things like that. I think that's one dimension. Another is I actually run an Airbnb, which is super specific, but I basically bought this dilapidated house and I remodeled it from scratch from the studs to a house and wow, that was my first house I ever bought. And I put so much care and love and detail into everything. I think the designing the place and the space was a huge labor of love and something I really enjoy doing. And then the other part of it is the Airbnb business and hosting in it has been just really fun as well.
Stephanie Engle
·
30:03
And I meet all kinds of super cool people. So I think that's one. Another is I have a horse business, which is really odd for me to say, and I can get into my horse origins, but it's called Stable Assets LLC and I basically buy and sell horses through it. I basically do like horse flipping house. Not flipping, but airbnb stuff. I help out with startups. I work at Snap. I think that's good for now, pretty much.
Michael Saloio
·
30:38
That that's amazing. You got to tell us about photography and horses.
Stephanie Engle
·
30:47
Okay. Yeah. So a lot of people, when they ask, how did you get into design? Sometimes I give them this, like a very abbreviated version, but I'll give you a little bit more information. So when I was a kid, I was about like eleven years old, I had a. Pony. And I was just really fortunate that my parents supported that passion growing up. And I had this pony and he actually passed away, and I had never had anyone or anything in my life pass away. And I was a very strange, enterprising kid. And I thought, how should I help everyone who goes through this? This is a horrible feeling.
Stephanie Engle
·
31:25
And so I actually decided that I was going to start a photography business where I would shoot photographs of my friend's horses, because I didn't really have so many photos of my horse at the time. That was back when we didn't have smartphones and every photo at a competition or something was super expensive. And so I was like, well, I'm going to just take photos of everyone and give them to my friends for free. And so I would just do that. I would go to different competitions and I would shoot all my friends horses. And I eventually started to kind of turn that into doing things like messaging Olympic level photographers and things like that to say, hey, what lenses should I get? And how should I invest in this and how can I get a lot better?
Stephanie Engle
·
32:07
And so I ended up speaking with a few folks who were really famous photographers, actually, who were really nice and gave me tips. And so I turned that into a business. I would get chased off the competition grounds by all the horseshoe people. So I kind of thought, like, maybe I should try something that's not like this. And I had a friend at the time who was still one of my best friends and went to Duke with me and all that at the time. We were in high school still, I should clarify. And I always just thought she would be a great model, like high fashion model. And so I said one day, like, hey, can we just take photos of you? And can we just, I don't know, we should just send them in.
Stephanie Engle
·
32:45
So we took photos of her in her backyard and we sent them to Elite Model Management, which was like one of the very top agencies at the time. I think they probably still are. And they actually called her and they said, hey, we'd love to bring you in, but also, where did you get these photos? Like, who took the photos? And she said, oh, my friend Steph. And so we actually both went out there and I started working for Elite, and I was kind of a de facto photographer for all the younger models coming in because it was just easier to shoot with me and get good content than an older man or something. And so that started happening. And then I started traveling around, going to fashion weeks and doing editorial threads and things like that.
Stephanie Engle
·
33:28
So going to Milan with my friend for Fashion Week was like a normalish high school occurrence that happened for a few years. And yeah, so I went all over and did that. And then I kind of got a little weary about it and just the industry itself was really tough. And so I thought like, oh, maybe I would rather do something. Is there something philanthropic I can kind of do with this? Or something that's a little more altruistic and makes me feel better than shooting fashion, necessarily? And so I actually basically pushed my way into this National Geographic internship. And so I ended up working with them and traveling to places like Central America, like Guatemala and places like that to do, like, documentary style photography.
Stephanie Engle
·
34:17
And so I went down there and it was just this amazing experience, although terrifying because I had never really traveled by myself and I had no phone or anything like that anyway, so I did that for a bit. Then I was fully burned out on photography. Completely, fully burned out on photography. And so I actually explored doing video editing. And so when you do photography, you just get kind of good at photoshop or lightroom. Like all these technical skills that I didn't realize until later would really help me in my career now. But then I got into video editing. I actually started editing videos for YouTube of my horses. Because I was like, we had some horses. We were selling them. My parents were like, hey, let's get them all sold before you go to college, all this stuff.
Stephanie Engle
·
35:01
So we sold the horses, or were selling the horses and other people started remixing the clips I was posting to music. So it was like, my horse is jumping to a Florida Low song or something.
Michael Saloio
·
35:13
And I was like, that's very specific, it sounds like really happened.
Stephanie Engle
·
35:18
Oh, completely. Yeah. And I saw that and I was like, that is so weird. I kind of want to do it. And so I did that and I got really good at editing clips of horses to music and in Final Cut and all this other software after Effects, all that good stuff that's super relevant now. And so I became this kind of famous horse, YouTuber, which sounds just comical to say now. I had, I think, 100,000 subscribers or something like that. Like something just absurd. Anyway, so the point is, I just acquired all these creative skills. I went to college, I left all of us behind. I completely was just like, no, I don't do any of that. That was what who did that?
Stephanie Engle
·
35:57
And when I got to college, there was this company that was like it was run at Duke by students, but it was actually very antagonistic with the administration. And so it was called Campus Enterprises. It's still there. It's been at Duke for like 30 years at this point. And what it does is it basically any service you can think of that students might want. The company just tries to build a business around it and offer it as just a service you can pay for. So, like, for example, there was no Uber at the time, Uber Eats. And so it was like, there was no service back and forth between the campuses. There was no service for delivery.
Stephanie Engle
·
36:35
People wanted bigger mattresses one of the campuses, so they would sell bigger mattresses just like any kind of we would do party planning because we knew when all the parties for all the frats and sororities were every year and how many cups they needed and, like, DJs and whatever. So we did all these things. And so I applied to join this company. I ended up joining it. And again, they were like, what do you do? And I was like, oh, I think maybe marketing seems like something creative I can do. And so I did marketing. And then I ended up becoming the CEO of the company by way of like, at first, I was just designing flyers. Then I was like, hey, we should have a website, because we didn't even have a website.
Stephanie Engle
·
37:13
And I was like, hey, we should have an app that connects all these services together. And so we started doing all these things. And our big linchpin into the university was that were a food points vendor. And so everyone at Duke has to have a certain amount of food points every semester that they have to pay for, and so they could pay us for any service like this on food points. And so we just had this captive audience of people, and I was like, well, why don't they subscribe to us and then we can give them a few different things? Anyway, the point is, went all through all this, and so I got adjusted to what was like running a company. Or I had moments where we had delivery drivers who wouldn't show up. And guess what?
Stephanie Engle
·
37:56
At some point, even though we had like 30 or 40 students involved, the buck stops with you. And so I've delivered food on campus to my friends. I've helped carry mattresses to campuses. We had these cleaners, so we had a cleaning service, and I had to bail one out of jail. All kinds of insane things were happening. And then from there, basically, I had all these skills and kind of this. I had already been designing apps and websites for the company, which I thought was marketing. And so it was, like, kind of a natural transition when, again, this company reached out to me, secret to come intern with them. I had all the skills to end up designing apps and websites. So when I saw what their designers were doing, I was like, oh, I'm not in marketing.
Stephanie Engle
·
38:40
I'm actually a designer, and I can be a product designer. And so that's kind of how my career actually started. Or the super long winded answer to that.
Michael Saloio
·
38:50
That's amazing. I have so many questions. The company at duke was not affiliated with the school.
Stephanie Engle
·
39:03
No.
Michael Saloio
·
39:03
And they just created businesses for students.
Stephanie Engle
·
39:07
Yes. And actually very antagonistic with the school. I have had screaming fights with the principal of Duke University because it was.
Michael Saloio
·
39:15
At odds with education.
Stephanie Engle
·
39:17
No, it was just like so. First of all, the whole organization was perceived as a bit elitist, I think, because the people who tended to join it were like the people who went into consulting and finance like that. Stereotype, even though over time, that was actually a huge effort for me, was like diversity, inclusion in the company and recruiting people from very different backgrounds. But anyway, so there were some elements like that, I think. Also, they didn't love that were a food points vendor and that were doing other services on it, but weren't technically breaking any rules. So it was just a lot of antagonism. There are so many other reasons.
Michael Saloio
·
39:54
I love this organization so much already. And you became the CEO while you were in college.
Stephanie Engle
·
40:02
Yeah, and it was just a crazy I mean, so we had 30 students who worked directly in the operations of It, like the head of the business, XYZ business. We were kind of like a holding company for a few different little businesses. And so we had leads for each of them. And then we had 75 other employees throughout all of the businesses. So, yeah, somehow I was a CEO. Although it's really interesting because I look back and I had this amazing COO who I would still he actually founded this amazing startup called Growth Therapy. His name is Jake Cooper. And this other guy as well, Raheem Gokle, who was my CFO. And they were just so amazing at what they did. And they've worked in those positions that they had then at high level places now.
Stephanie Engle
·
40:48
But back then, I truly saw myself as the very product minded CEO, where I just tinkered on, like, what's the new service? Or how do we package the product of services into a bundle, into an app or something? Whereas they were very fixated on costs and operations and everything else. Right. And so I just look back and I remember one time, evan Spiegel is CEO of Snap, and someone I'm fortunate to get to speak to quite often. And he said to me one time that every CEO should just pick the thing they're good at and hire away all the other things that they're just okay at or bad at. And at the time, I didn't realize it, but I was really empowered by those two other folks in the C Suite roles to just be the creative.
Stephanie Engle
·
41:39
And so accidentally, we just kind of ended up in this spot. Whereas if I had to be the true operator or I had to truly run the financials of the organization, I actually think I would have been super ineffective. But just because I had those two people there. It was just like it all worked extremely well.
Michael Saloio
·
41:56
Yeah, it's cool that you had two people that empowered you to do what you were great at. I talk about this with a lot of founders because I've found it hard. Well, I have found it hard to let go of parts of the business because I want them to go well, even though I know intuitively and intellectually that it's not the best thing to do. It's just hard. And I don't think it's hard maybe it's hard because I or we as founders or managers are trying to control things. I also think it's hard to just own up to what you really like to do. I think it's hard to just be like, I like to create stuff. I don't like operations. I actually think that part is harder.
Michael Saloio
·
42:50
That part is harder for me, just owning like, you can have a successful career doing what the things that really give you energy.
Stephanie Engle
·
42:58
Right. I think it's also like if you feel an absence of true peers in some of these other dimensions, you might also feel unable to let those things go because you've never seen what fantastic operations looks like. And so you also might think you're okay at Operations or finance or whatever because you don't know what excellence looks like in that dimension. And so I think that's something I feel is like I was always the person on the group project. Two people are like, stuff will get it done, but I would realize that it was just getting things done. Yes, that's important, but it's the skill we have to obviously really value in people. But what I didn't know was what excellence looked like across all these different dimensions.
Stephanie Engle
·
43:42
And something I always tell people, too is it's reminiscent of what were talking about earlier about putting yourself around great people. But I think the goal is that when you see what excellence looks like and success across all these different dimensions, you really start to realize like, oh, my gosh, I'm actually bad at this. Or it's like a blocker for me to be working on this. And I know there's a lot of different schools of thought on startups and big companies and what to work at early on in your career and all that. I do think because I kind of went the big company route and had this other experience at this campus enterprises, although I did have a startup in between, I just saw what excellence looked like. I knew what amazing design was or amazing whatever.
Stephanie Engle
·
44:25
And so that when I ended up going to Cruise after Facebook. I had seen what top tier design looked like. I had no idea how to hire a team or do any of that, but I knew the picture of what it looked like so I could work towards it. Versus if you've never seen that or had peers you felt comfortable with on those dimensions. I think it's hard to let those functions go and delegate them.
Michael Saloio
·
44:48
Yeah. I want to ask you how you personally choose the things you're great at, which might sound funny because you're doing design, but you're also doing investing. You also do run a business, several businesses, actually. Do you find yourself wearing a lot of hats inside of the different enterprises that you're involved in? Or do you see there's a common thread?
Stephanie Engle
·
45:16
Oh, totally. The thread. Yeah. I don't get to choose what I'm good at. You are or you aren't? I think at some level, I would very much go out and say I'm not the best designer in any of the scenarios. I think what I'm actually decent at is creating a lot of energy around a clear picture of where things should be. And so whether it's design, it's like, hey, getting people excited about a vision. Like, when I worked at Cruise, I joined, I was the first product designer hire, and I didn't really have peers in the same way I had in the past, but I knew what it looked like, and so I knew I could go out and find those people.
Stephanie Engle
·
45:56
I knew what amazing designers looked like, and I could bring them in and tell a story about what were going to make that was going to be great, even though we didn't have a consumer product team or really a product team at all. And so I think I've always been good at riling people up and aligning people around a cool vision or idea or something that helps it materialize. And also I can get into the details of how to get to that particular vision. And so even with horses, I know what good looks like. I do not need to be an expert on vetting or anything like that, but I know what amazing looks like, and I have some great inspiration in those areas. And I trust professionals.
Stephanie Engle
·
46:38
But I know what great looks like, and I know how to sell and kind of market the business and name the horses. All this stuff that makes it appealing for others. And so even my little business, Stable Assets, gets a ton of attention because it's announced on loudspeakers, and people always come up to me and talk to me about it. So I think it's just sort of knowing, being able to see a vision and align people around it is actually what I'm okay at. And then just all the design skills help support that skill and speaking and all these things. But it's not that I'm not the best designer, I'm not the best speaker, I'm not the best any of that. It's just the combination of those things towards that goal is something I can put together amazing.
Michael Saloio
·
47:22
And it's also clearly about people for you. Like, our last conversation was a lot about different stories you had about supporting friends, and you named two personal mottos both of which I wrote down. And one of them was, we're always closer to where we want to be than where we think we are. Tell us a little bit about how and why that became one of your personal mottos.
Stephanie Engle
·
47:53
So I am a person who takes on obviously just crazy big things, and often more than I can handle. And I think that when you take on super large challenges, like again, mentioning a few of being the CEO of that company and around my peers who thought it was kind of a strange thing or just going doing the photography and being the youngest person carrying a huge camera around or being early at Cruise, I saw in all of those scenarios I had to figure out how to get from my skill level to my taste level. That's always kind of I have the vision, I have the taste, but I have no idea how to get there.
Stephanie Engle
·
48:35
And I think if you see it as one big, overwhelming blob of things to do, you're always going to feel overwhelmed, you're going to feel stressed about it. And what I've just always found is you truly are like one person or one opportunity or something away from where you would like to be. So one example was at Cruise when I just knew I really wanted to hire Bradley Ryan. He was someone I knew from Uber. And I was just like, God, this guy is so talented. He had invited me to speak at some course he was teaching, and I was just, like, so blown away by his talent and just really enjoyed him.
Stephanie Engle
·
49:10
And I was like, I know if I can hire him and convince the company that we even need another designer, I was like, I know we can make things happen somehow. We did hire him and convince him to come. And it was so true. It was just like, the combination of us, were able to woo the next people, right? Because having such talented people in the company allowed us to say, hey, we have talented designers. Come join us, or his abilities were able to sell the company on, hey, we should make a rideshare app, which actually wasn't like a given or something we planned to do. And so I think that's what I mean is you're often one person, to be honest, away from what you actually want. I had to learn that skill because otherwise it was just so hard.
Stephanie Engle
·
49:58
It was like, I had to do a million things in that scenario. Like, I had to figure out how to convince the CEO and learn all these new skills about how a car drives and all this stuff. And so if I had worried about all of that, instead of just focusing on, like, okay, what's one thing that would exponentially take me towards that vision I'm trying to get to or at least turn into a snowball, right? Like, if he's here. Well, I should be at Cruise, right? That's the reaction I wanted to create. So that's kind of why I've had to learn that skill, I guess, or embrace that.
Michael Saloio
·
50:29
And it goes both ways, which I'm realizing now, because the other motto was, all you need is one person to give you a shot, because I think the other thing you're doing when you're saying, wow, if we could only get that one person into this project or this organization, they would help us so much. On the other side, you're giving that person an opportunity to contribute to something awesome, right?
Stephanie Engle
·
50:59
Well, yeah, I think in that case, it was more like, I hope it'll be awesome. But, yes, you're absolutely right. And I think it's really important. And I think I always look for those folks, too, who I know will grow at least within six months, like 20% into the role that I think I'm hiring them for, sort of thing. They don't need to perfectly be there, but they need to be super close. He was, like, far excelling away from where were at that point, but helped us create an organization around him that actually was super compelling for people. And now people ask me all the time, like, hey, I'm talking to Cruise. And I'm like, God, wow. That was not the case a while ago. It was really a struggle.
Michael Saloio
·
51:44
Very cool. So I want to ask you about your investing activities, because that's how we met. We met through my co founder Stephanie Golek, who you worked with at Cruise, and you were one of our first investors, which we're forever grateful for, and you've been super helpful both in terms of advice and making really cool introductions. Tell us a little bit about your investing activities, and I really want to get into how you select the people, which sounds I'm realizing as I say that out loud right now, it sounds like you could be talking about me and Steph. You know, Steph better than me, but I think it's really cool how you source your opportunities based on just sort of who you like to work with, it sounds like.
Stephanie Engle
·
52:35
Yeah, when I got into investing, it was not that I had a nice spreadsheet laid out and said, oh, well, this makes financial sense. Actually, it makes very little financial sense. I think I've just been it's truly the cliche of, like, when you follow good people, like, more value will follow you, sort of thing. Like, if they're creating value, it's sort of all by osmosis. And so there was a certain point where I realized that I had this class of founder friends who weren't actually founders, but maybe had the inkling towards it. They were all at big companies thinking about starting things and going off on their own. And I had known them for all these years, and then they eventually started doing it.
Stephanie Engle
·
53:20
So they had been the people at the facebook or however I had known them when I was younger, and they went off and started their own companies. And so when that started happening, I was just like, wow, these people are doing cool stuff. And I realized some of them like they really needed money or they needed help and that was the way money was the way we could help right? And so it started off with just giving some friends who I thought were brilliant just checks of money and they would say, hey, I'm doing friends and family and I didn't realize at the time the sort of value exchange of like, oh, they're giving me equity.
Stephanie Engle
·
53:50
And around I just kind of saw it as like, man, yeah, I would bet on that person to make a giant thing happen and I would only love to be, I don't know, kind of intertwined on that journey and helping that person. So that was kind of how it started and it was just truly like meeting great people, being energized, being so convinced that they were people who could will concepts into the world. Like I'm thinking of a lot of people but some folks like the Rich brothers, Ryan and Ross Rich, they founded a company called Accord. They were both in sales, they never built product but I knew they were literally the best salespeople at Stripe and at Google Cloud I knew they were just everyone said amazing things about them and they made a project management for sales tool.
Stephanie Engle
·
54:42
They got into YC, they got funding from Stripe, like all this crazy stuff but it was just started with like I know these two people know what they do better than anyone else and they're such go getters and they're going to will it into existence. And Steph, who I had worked with at Cruise, was the same way. I've told you before, but from the start of when she interviewed, she showed us the company she had worked at. Map Fit. And I was, like, looking at it, and I was like, man, this must be a big team. Or, like, lots going on here. And then I was like, oh it's just her. The whole brand, every single Map style, every detail was her at a startup like also helping with product or leading product.
Stephanie Engle
·
55:24
Anytime I see someone in my life who I just know can will anything into existence and they can just create a whole thing from scratch I'm just happy to back those folks and so that was kind of how it all started and folks like you. So I think a huge criteria is this propensity to they make things happen, whatever it is, they will things into existence no matter what they are. So people with the propensity for that obviously other things have to start to make sense but as you know, investing at that early stage really isn't a financial numbers game. It's got to be a little bit more feel and intuition and the ideas obviously have to be somewhat sensible.
Stephanie Engle
·
56:05
But all of that changes so much on the journey towards what they end up creating that you just have to believe in that person. These days I'm actually a scout for Spark Capital, which is awesome. I just adore that team and they're wonderful and they're very similar. We call ourselves kind of like people who seem like type A, but we're actually kind of type B. Like we're way more chill than we actually front as or seem like we actually are. Anyway, that's a lot of my activity more recently and something I appreciate is like they do often do go after very strange and odd ball founders who maybe aren't the typical resume or anything, but they just see people who again just will things into existence.
Stephanie Engle
·
56:55
One of my favorite founders right now is his name is Jarrah Orphan and he started a company called Wayro that has basically what they do is they help map the ocean surface with AI. And the first time that was just like on a boat. And I couldn't have known if he was like a deck hand or a physics PhD, which was the latter, but he just knows everything about the ocean, just loves the ocean and also happens to be like ultra technical as well. And so for him it's just like, yeah, obviously I'm going to create this technology and I'm going to sell it to my friends who run cargo operations and things like that. And I was like, you just will not find that person walking around San Francisco that was in Wales or something. I met him.
Stephanie Engle
·
57:45
Just super random journeys, but anyway, just stuff like that where it's like people who he's like helped build a ship, so obviously he probably do this, right? So anyway, it's that quality of people who are able to will things into existence because it's not a financial it's a financial transaction at some point. But truly in the beginning, you cannot put it on a spreadsheet like Huddle. I could not have put your idea onto a spreadsheet. I had no idea how it was going to work out that way. And the idea is morphed a lot, but not the values. Like the values and the insights have not morphed, but the concepts and how you all are doing it is definitely a little bit different. So you can't invest in that, I guess.
Michael Saloio
·
58:26
Yeah. My experience is that you can't either in terms of like before Huddle when I was just helping founders with their pitch decks and kind of working to be a coach, and I had a similar insight, which is the idea has to make some sense. The person has to think that the impossible is at least probable or highly possible. Almost like a weird conviction about the future is going to look, even though there might be no evidence for. It and then integrity in terms of like, they're really going to do it right. That's been one of the biggest things that I've seen, even just in companies coming through Huddle. It's funny to talk about Huddle because we're also still a startup. We're very new, but this is what I'm learning so far. All right, cool. This has been like a really amazing conversation.
Michael Saloio
·
59:30
I'd like to end with to whom or to what? Or and to what are you most grateful in terms of your own journey and what you get to do every day?
Stephanie Engle
·
59:47
Gosh, I could pick a lot of answers here. I feel like if I do to whom, I'm going to upset someone or leave someone out. But something to what I think something a lot of people don't know about me is actually truly how many times I've had to start from zero. I think that if you hear my background and you hear horses and you hear Southern California, it's really in Duke and all that, it's easy to make clear projections about where I've come from and what's gone on.
And it's super true that I've had a lot of privilege when I was growing up, but when I was actually going to college, my parents split up and separated and my dad stopped working and just kind of went a little bit off the radar in some ways and money was stressful and all kinds of things. I think just like living this, keeping up with the Jones's lifestyle when were kids. And as a kid I didn't really know. And so when I went to Duke, basically I had to pay for everything. So I didn't get any aid. I had to take out full loans on the entire experience and I didn't know I was going to have to do that.
And so part of the reason I started working at that company was also because they paid money and I didn't want to do like a normal campus job or something. And so I wanted to do something that was maybe going to help me find my career. When I graduated college, I had like, over debt and just had to figure out how to deal with that and pay it all off within two years and just really pull myself up from that. And there's just been a few other scenarios where I've really had to go to zero and it's super hard and at the time I wouldn't have looked at it as like, wow, this is going to be a great lesson in the future. It was just stressful and hard.
But I think what it's really taught me compared to some of my other peers, is that I can do that and that I can be at zero and as long as I have my hands in my brain and I can actually really figure something out. So I do feel like if I were dumped in a field somewhere and just had to do it again. I probably could. And it's why I've diversified. It's why I've landed in some of the things I have, is just because I've had to just claw back from scratch and do it quickly, right, and really figure it out. So I think that's something that at the time, very ungrateful for, I guess, or really did not appreciate. But now I look back and I'm like, yeah, I can start from zero. I don't need every advantage to get somewhere.
But of course I want to acknowledge that I've had significant advantages as well. But, yeah, I think that's been a huge thing for me.
Thank you very much for sharing that story, for having the courage and the generosity to share that with us.
That's really cool. We all have our struggles. No, I think you're a founder. Like, there's plenty of, you know, companies always it's a guaranteed part of it. Right. Or other people have student loans and all kinds of stuff. So I think it's, you know, I get accused a little bit too much of, oh, everything seems great, and you seem quite competent and stuff successful. Right. And so I think it's good for people to just be open and actually just talk about this stuff sometimes because most people have this experience. Most people have a related experience.
Yeah. I really appreciate you sharing that with us. And thank you so much, Stephanie, for coming and having this chat with us today.
Oh, my gosh, thank you so much.
And for everything you've done. For everything you've done for Stephanie and me and for Huddle.
Oh, well, I love you guys. So easy.