Shailvi Wakhlu is an accomplished data leader with 17+ years of experience in Fortune 500 companies and startups. In this episode, Shailvi discusses growing up in India, childhood interests, swimming, education, moving to America, the quantified self, data science, and a career that has included stints at Strava, Komodo Health, Salesforce, Fitbit, Prezi, Monster, and more. She also talks about enterpreneurship, investing, public speaking, and her process for writing a book.
[00:00:00] Welcome to Konabos, a conversation experience platform hosted and curated by Konabos Consulting.
[00:00:06] Konabos is a global technology leader and while this podcast will be connected by technology,
[00:00:12] the glue is human stories and narrative. Technology can bring us together. It can make our lives better
[00:00:18] and more efficient in myriad ways. But it cannot replace human discourse and the magic that can
[00:00:23] happen by the interchange of ideas. Hope you enjoy our podcast. Welcome to the Konabos,
[00:00:32] this is Akshay Sura and this is Matt McQueen. Today we have with us our friend Shelby. Hey Shelby,
[00:00:38] welcome to the show. Thanks so much for having me. Absolutely Shelby, so we just met you but we're
[00:00:45] going to go back to the beginning. Where were you born and where did you grow up? Yeah absolutely,
[00:00:51] so I was born in India. I was born in the middle of the country because my dad was in the army so we
[00:00:58] moved around a lot. So I lived in India growing up but I must have moved at least five, six cities during
[00:01:04] my time there. What did your mom and dad do while you were growing up Shelby? My father was in the
[00:01:12] military so he was in the Indian army and my mother was a teacher so she taught computer science in high
[00:01:19] school and later she moved into her nonprofit organization. Wow and do you have siblings Shelby?
[00:01:27] I do, I have a sister who's four years older to me. Wow so I'm assuming we've had some military friends
[00:01:39] and our cousins moved always from a different posting. How was that growing up like moving from place to place
[00:01:48] making new friends? Was it adventures? Was it hard? I definitely thought of it as an adventure. So I think my record
[00:01:58] goes something like that. I think the longest, until I turned 18, the longest I stayed in one house or one
[00:02:07] apartment for continuously was maybe two and a half years. So that was the longest I stayed in at one address.
[00:02:13] And then I kept moving. So I had a little bit more consistency with my schools because my dad moved a lot
[00:02:22] more and so at some point we ended up staying in the same place and he kept moving. So at least we stayed
[00:02:28] in the same city. But yes, restarting new friends at least, if not in school then at least at home,
[00:02:36] that was very very common for me. So I think even as an adult it's something that reflects in my personality
[00:02:42] that I'm very used to just starting over. When you have to move a lot, I assume that your
[00:02:48] personal interests become very important because they can be almost an anchoring thing. What were the
[00:02:56] things, whether it's personal, whether it's in school, your hobbies, what were those things that you
[00:03:00] like to really do throughout your childhood? Yeah, I think that's an interesting perspective because
[00:03:06] you're absolutely right that your personal interest becomes the way you bond with people,
[00:03:14] especially when you know you have to do it in a shorter time frame. You know, you don't have five
[00:03:18] years to sort of form a deep friendship. But I think the other side of it is also that I ended up
[00:03:25] having a lot of varied interests because you also try to adapt a little bit or fit into whatever is the,
[00:03:32] you know, whatever other people, whatever most people seem to be doing in whatever new place
[00:03:37] you're at. So I was, I was pretty active. I was in a lot of sports. Some of them were solo sports.
[00:03:45] So it was sort of fallback option that, okay, if there's nothing else for me to do, at least I can
[00:03:50] go swim. And so swimming, I swam a lot. I used to swim five hours a day when I was a child.
[00:03:56] And, but, you know, I played a lot of sports. I went biking with friends. I loved going to the
[00:04:03] library. So I had a couple of friends who would enjoy sort of going to the library, reading a lot
[00:04:09] of books. And within school, I was very involved in a lot of the extracurricular activities.
[00:04:15] Because you're absolutely right, like it's a great way to form quick friendships. And it's fun.
[00:04:22] And I enjoyed it a lot. Growing up, did you know what you wanted to be? Did you have like a career
[00:04:30] that you had in mind growing up? Great question. I don't think I had a career as such, but I knew
[00:04:38] what I wanted to do very early. So I've, I've shared this sometimes. It's, I think it's, it's
[00:04:44] pinned somewhere on my profiles, various profiles that I knew I wanted to code since I was eight years old.
[00:04:50] I think I was very, very lucky that I was exposed to computer science. You know, I'm, I'm a kid who
[00:04:57] grew up in the nineties and I was exposed to computer science very early because my mom taught computers.
[00:05:04] So she famously tells the story that I learned how to type before I learned how to write. And that is
[00:05:12] absolutely true. And my handwriting will prove that because, you know, I never really saw the purpose
[00:05:18] of having, having a sharp handwriting. So coding was something that I learned very early. My mom taught
[00:05:24] me and it was just the coolest thing for me. I felt, I thought of it as puzzles that, you know,
[00:05:30] there's these puzzles and you solve them. So for me, it was something super exciting and I knew I wanted
[00:05:35] to be a coder since I was eight. And eventually I figured out what's the career related, related to
[00:05:42] that. And that's what I started working towards when I, by the time I reached high school, but coding was just a
[00:05:49] sincere love of mine since of a young age.
[00:05:53] And so did you carry that into university? Was that your, was that your focus in education?
[00:06:00] Yes, it was. So I was doing computer engineering. That was what I did my bachelor's in.
[00:06:07] Interestingly enough, I think I, what I wanted was computer science, but in India, I think they
[00:06:12] called it computer engineering. So that's what I signed up for when I came to the U S because I
[00:06:16] moved, I moved to the U S to do my bachelor's. And then I came to the U S and in computer engineering
[00:06:23] in my college, they also made you work on robots, which was kind of fun, but not like that wasn't,
[00:06:29] that wasn't what my core interest was. It was the coding aspect. So I wanted computer science.
[00:06:35] I ended up with computer engineering and then I kind of just stuck with it. It worked out.
[00:06:40] Did you see, what do you call, did you see a difference in the teaching styles between India
[00:06:50] and the U S when you came over and you started studying here?
[00:06:55] Absolutely. In my case, I went back and forth of whether I would move to the U S for bachelor's
[00:07:02] or not. So I had already started college in India. I was doing a bachelor's in math,
[00:07:09] math honors in, in, in New Delhi. And so I did actually go to college in India for a few months
[00:07:14] before I, before I moved to the U S. So it was not just the teaching style. It was also the
[00:07:19] expectations. I think at least in my, at least in my experience, I think the U S education system
[00:07:27] or, you know, the college education system gives you a lot of independence, but also holds you
[00:07:32] accountable a lot more. In India, it's, you know, you're, you're, you're sort of advised to do,
[00:07:40] to do certain stuff and you don't have a lot of independence. Like you don't get to choose your
[00:07:44] classes. There's a, there's a fixed set of classes that you are assigned every year. And after that,
[00:07:50] you know, you're, you're kind of like reminded and pushed towards meeting those objectives.
[00:07:55] So I, I think I thrived in the, in the U S system. I, I think it fit better with my personality and
[00:08:02] with what I was seeking. But, you know, regardless of that, like even the time that I had in India was
[00:08:08] super fun. Shelby, was that your first time in the United States or had you come when you were
[00:08:15] younger? That was my first time I moved to the U S when I was 17 years old for, for my bachelor's.
[00:08:23] So that was my first time. I, I didn't have family in the U S I didn't have, I think my parents had
[00:08:29] some very distant family friends, but I didn't have any, like nobody in my family, none of my cousins
[00:08:34] had gone to the U S. What was that experience like for you? What do you remember about
[00:08:40] the first feelings of being in the U S? It was quite an interesting ride. Um, one thing for me,
[00:08:48] because I came, because I initially, like I still went to India for the first few months and then I
[00:08:54] switched. Um, so I ended up joining in the spring semester, uh, which is not usual. I think most people
[00:09:00] who come for bachelor's, they, they join in the fall. Uh, that's the standard time. And in my case,
[00:09:06] I was studying in Chicago. Um, it was super cold when I came, it was, it was January, it was snowing.
[00:09:13] I had never seen the snow before. Um, so it was quite a, quite a, quite a wild transition.
[00:09:19] I would say to go from New Delhi to Chicago without really knowing, um, anybody and in a completely new
[00:09:26] system at, at the age of 17. Um, I I'm, I'm still very grateful for it. I think, I think that experience
[00:09:33] 100% has defined me for the rest of my life. Um, just the fact that I, I went through it and I did
[00:09:40] it and I enjoyed it was, was super, super, um, I'm super grateful for that.
[00:09:47] Yeah, it definitely is. So you come here, you finished your, uh, degree. Did you, uh, pursue
[00:09:56] for the degrees or did you, uh, end up getting a job?
[00:10:02] Yes. So I got a job while I was still, um, still working. Um, it was interesting. Um,
[00:10:09] I was looking for, you know, something like an internship. I found, I found a full-time opportunity
[00:10:14] and, uh, I was still, I was still finishing my degree. And one year later I asked my boss,
[00:10:20] I said, I need Friday off cause I have my graduation. And she said, what do you mean?
[00:10:25] You haven't graduated yet. So that was, that was really funny. Um, cause I basically started
[00:10:31] working full-time, um, while I was still, while I was still in college. And so I just continued
[00:10:37] that job, um, that job that I got while I was still in college, um, it ended up lasting me six
[00:10:44] years, uh, across three different continents. So I, I had that job while I was in the U S.
[00:10:50] Um, and I, I stuck with that job for like two more continents after that.
[00:10:57] Wow. So did you even, you probably didn't even realize when you were telling this boss, this,
[00:11:03] uh, that that was something that it's funny. It didn't even come up right before that.
[00:11:11] It was, I, I, I, I, I really thought they already knew, but, um, yeah, it was, I, it was quite,
[00:11:19] I was quite surprised. I said, how do you not realize I'm still in college?
[00:11:24] And then do you remember that job interview, Shelby, when you got your first job? Because
[00:11:30] like for most of the people we speak with, it's very memorable. Their first interview
[00:11:34] was anything memorable about that interview you went to for your first job?
[00:11:40] Yeah, it was, uh, I, yeah, I absolutely do remember it. I think, I think you're absolutely
[00:11:44] right that you don't forget your first job interview. And also because I kept the job for
[00:11:49] such a long time. And after that I worked for myself for a bit. So in a sense, I did not
[00:11:54] have another interview for almost a decade after that. And, uh, yeah, I do remember it. It was, um,
[00:12:00] it was, it was very memorable because it was actually only my second time interviewing ever for,
[00:12:06] uh, for a, for a full-time position. And, uh, the only reason it was my second time and not the first
[00:12:12] was because when I got this interview, um, I actually, I, I, I felt that I had a higher chance
[00:12:18] of getting, getting this role. So I actually wanted some interview practice. So I scared,
[00:12:23] I found some other company that would just interview me, uh, right before this one. So,
[00:12:28] so that's why it ended up being my second and not my first. Uh, but then I got the job the same day.
[00:12:32] Like, um, I, I guess, I guess those were the days, but, uh, you know, they, I, I finished the
[00:12:37] interview. I had, I feel like it was at least half a day, if not the full day, but I remember it was,
[00:12:42] it was very long. Like it was a couple of hours. Um, and I started getting hungry at some point
[00:12:48] and wondering when I could eat something. But, uh, I remember I left, um, and, you know,
[00:12:54] started wandering around town before I made my way back to, back to my dorms. Uh, and, and they
[00:12:59] actually called me and, and, and made an offer, um, just a few hours after I'd finished the interview.
[00:13:05] So it was, it was quite wild. Like I thought that was the norm for the longest time, because
[00:13:09] that was really one of my only experiences interviewing at that point.
[00:13:15] And I, that was this monster.
[00:13:17] Yeah, this was monster.com. Yes.
[00:13:19] When you see the, it's always fun to see the trajectory of a career, but you said that you
[00:13:25] were there a while. It looks like about over five years or more.
[00:13:28] Six years almost. Yeah.
[00:13:31] You went from web engineer to software engineer to business, senior business analyst. How did that,
[00:13:37] how did that path come about? Um, you know, cause usually I feel like you, you know, you might be
[00:13:43] in programming, but you crossed over to really the business side. How did that happen for you?
[00:13:50] And it's great to be able to do it in one company, right?
[00:13:53] Oh, I think, I think it's amazing to be able to do it in, in one company. I think it is, uh,
[00:13:58] really special to have a company that you trust and like working for, um, that allows you to sort of,
[00:14:05] uh, you know, that presents new opportunities of growth. Uh, and in my case it was, it was very,
[00:14:10] um, not planned. Uh, so I think when I started in Chicago, the title was web engineer, you know,
[00:14:17] it was, it was, it was standard software engineering. I don't know what, what the web part really
[00:14:21] meant. Uh, and, uh, so my job didn't really change when I moved to, I moved to Europe after that.
[00:14:28] And then I moved to India and my job did not change like for five years in that company,
[00:14:32] it was the same job. Um, it's just that they had different standards of titles. Uh, so the software
[00:14:37] engineer shift was just that, that it was just a different continent had a different standard for
[00:14:42] the title. So they said, okay, you're a software engineer. Uh, and then when I was in India, I,
[00:14:48] I continued that, that previous job that I had for a year. Uh, and then after a year, uh,
[00:14:54] they essentially had layoffs in the U S team. So I was still attached to the U S team this entire time.
[00:15:00] And I was, I think I was literally the last person left on the team. Um, so I think I was
[00:15:05] the last person, um, you know, who I was the final person who was on the team who received a
[00:15:11] notification that, you know, we're shutting down this team, which I had known for years. Like,
[00:15:15] I think, I think it had been slowly sort of, um, coming to that conclusion for a while. And,
[00:15:20] um, I was by that time, since I was based out of the India office, uh, they essentially gave me an
[00:15:26] option. They said, you know, um, here's, you know, you know, the team has been shut down.
[00:15:31] Here's the severance option. Uh, and they said, Hey, but you're in the India office, uh, that office
[00:15:37] is hiring. So if you are interested in continuing to work with monster, uh, there are other opportunities.
[00:15:44] So, um, I like, I was, I was very lucky that the, um, the AVP of that office, um, interviewed me the
[00:15:52] same day and he said, do you want to be an analyst? And I said, I have no idea what that means.
[00:15:58] And he said, you'll get to code at least half the time. So I said, okay, sold. And he asked me a
[00:16:04] couple of coding questions. He asked me a couple of math questions. And that was how I made that
[00:16:08] transition to being in analytics. And I was assuming that it, it grabbed you because the rest of the
[00:16:16] career, you moved more towards like the data intelligence and the, that part of the business,
[00:16:21] like what was, so the, obviously the, the gentleman mentioned you can code for half the time. So obviously
[00:16:28] you need to do stuff to move data around and try to figure out what's happening. But what is so
[00:16:34] intriguing about tons and tons of data and data intelligence to you?
[00:16:40] Yeah, I, I, I feel very grateful that I, uh, I, I almost feel like I lucked into data without,
[00:16:47] without really fully, fully understanding, uh, sort of the depth of it. Cause this was, again,
[00:16:52] I think, I think when I made that transition, it was, um, maybe 2011 or 12, I'm, I'm, I'm blanking
[00:16:58] on the exact year, but you know, that was the time I made that transition. I, I did not have,
[00:17:03] uh, sort of that awareness of what's, what's, what's the stuff regarding big data. What is exciting
[00:17:08] about it? Uh, but once I got into it, I realized that it was, um, I think the, the role that I had
[00:17:15] at that time, it was at that perfect intersection of engineering product and business, um, which I
[00:17:22] completely thrived at. Um, it, it had a creative aspect, um, you know, monster.com at that time. Um,
[00:17:28] I, I think I was one of their first, uh, first analysts, uh, based out of the India office. Uh,
[00:17:34] so the problems were pretty ambiguous, you know, it was very wide, like, okay, what are we trying to
[00:17:39] optimize? Um, you know, they had, we had many different directions that we could, that we could
[00:17:44] go in. And so I, I love that aspect of it that I can, I can shape direct outcomes for, uh, for the,
[00:17:52] for the business success. Uh, you know, how do we, how do we actually make more money? How do we get
[00:17:56] more users? How do we retain more of our paying customers? And, um, so I'm, I'm very grateful.
[00:18:02] Like, I think the data aspect of that, that, you know, you can have like millions and millions of
[00:18:06] rows of data that you use to make a decision that shapes the future of the company. It was, it was pretty
[00:18:13] cool. So coming out of that, it appears you went and founded or co-founded your own company. How did,
[00:18:23] how did that come to be? And what were you looked about three years? Like, what were you,
[00:18:27] what problem were you looking to solve there? Um, the initial thing was, I mean, one of the
[00:18:33] problems was, so that company, uh, my husband and I co-founded together. So he at that time was just
[00:18:39] exiting his own venture funded startup. Um, so he was kind of winding that up. And, uh, I, at that
[00:18:45] point was sort of done with monster.com. Like I'd been there for them, with them for six years. It was
[00:18:50] super, super great. Uh, but I'd also moved, uh, locations and I don't know if any of you are
[00:18:56] familiar with new Delhi traffic, but I used to spend three hours commuting every day. Like it was,
[00:19:01] it was not fun. So, um, you know, I, I often quote that as I lost it at that company for six years.
[00:19:08] And then for six months I had to do that three hours commute. And I was like, okay, I, I love this
[00:19:13] job, but I'm done. Um, so it's, it's an odd thing to say, like, you know, most people will have
[00:19:18] some really fancy, like, Oh, I really wanted to start my own company. But honestly, that is the honest
[00:19:23] truth that that was the trigger for me that I'm like, I, I don't want to do this anymore.
[00:19:27] Uh, and my husband and I started brainstorming, like, you know, I obviously like I was, I thought
[00:19:32] I'd apply to other jobs. Uh, but then both of us had this itch to, um, one try working together.
[00:19:38] Uh, and then we had a couple of ideas that we, that we thought would be fun. The Indian startup
[00:19:44] scene at that time was booming. Um, there was a lot of, uh, companies coming out. We both had a lot
[00:19:50] of experience in, in, in different pieces. Um, so I, um, managed kind of the technology aspect of
[00:19:57] the company. So we basically were, uh, as they call them the, the gold, the gold rush, um, vendors,
[00:20:06] you know, while the gold rush was going on, we were sort of providing the service. So, uh, the,
[00:20:11] the, the, our, like our, our company was essentially making the first alpha or beta product for another
[00:20:17] startup. So we were not invested like for them for the whole time, like, but we helped them sort
[00:20:22] of launch their MVP, uh, MVP product. So it was super fun, got to work with tons of different
[00:20:29] industries, tons of different companies. Um, obviously we initially started with some companies
[00:20:34] that were in India. Uh, at some point we realized the arbitrage of working, uh, with someone who's paying
[00:20:40] you in dollars while we were spending in rupees was great. So we started looking for more customers
[00:20:46] in the U S um, cause both of us had lived there. Both of us had been there. So we had a couple of
[00:20:51] clients in, uh, San Francisco, in Chicago, ended up having a few clients in the Middle East. Um, so
[00:20:57] did that for a few, few, few years. And it was, it was honestly like, I, I really love, uh, love,
[00:21:03] love those years. Um, cause it was a lot of learning and I think it was a lot of, um, shift in perspective.
[00:21:09] Cause for me, I'd been with the same company for six years. And then in like those, you know, two and a half,
[00:21:15] three years, I ended up working with so many different small, uh, small companies.
[00:21:20] That makes sense. So I'm going to switch it up just a tiny bit. What are your current hobbies?
[00:21:26] Shelby, what do you like to do to when you're not working, working?
[00:21:30] I'm a solopreneur. So one thing is I'm also always working. Um, I, uh, yeah, but I think,
[00:21:38] I think outside of that, like I, I, I love, I love plants. Uh, so my, uh, my apartment,
[00:21:43] I live in San Francisco apartments. It's not, it's not that big, but I've somehow crammed 70,
[00:21:49] uh, plants in my apartment. Um, and I keep propagating them cause a lot of them are succulents. So,
[00:21:55] uh, next time you talk to me, there'll be, there'll be more. Um, uh, but yeah, that is,
[00:22:00] that is something that I really enjoy, but I'm also very interested in sort of just artwork. Um,
[00:22:05] I, I have my own version of artwork. I, I paint, uh, short glasses with Indian, uh, Indian designs.
[00:22:15] So really interesting. Like when you look at all the places you've worked, it's like,
[00:22:19] you could talk about those places and the industries they go to. And the next one I see is Prezi,
[00:22:25] which I think is amazing because what are we almost 10 years from that? And people today,
[00:22:32] they're like Canva this, you know, that Prezi was like everything at that point. I remember we
[00:22:38] tried to use Prezi for everything. Now we're kind of back to, uh, PowerPoint templates, I guess. But
[00:22:45] was that like kind of the, the moment when you were there, when it was really hitting or was that a
[00:22:50] little after what led to Prezi and what do you remember about that time?
[00:22:55] Yeah, I, I was absolutely at Prezi at, I don't know, like when exactly the peak was, but I would
[00:23:03] say pretty, pretty close to it. Um, I think back when I worked at Prezi, uh, it was really cool company.
[00:23:09] I think, you know, I, I wish, um, uh, you know, they're still around, but, uh, I think they, um,
[00:23:15] I think Google slides came out like shortly after or around that time. And, and, you know,
[00:23:21] that, that was a big shift in sort of, you know, just the value add, I would say, uh,
[00:23:25] but just as a tool, as a presentation storytelling tool, I thought it was so cool. Uh, and the fun
[00:23:30] fact was that I was working out of the San Francisco office, um, which was really nice, but, uh, they
[00:23:36] are originally like they, they started as a company in Budapest and, uh, I got to go to Budapest for a
[00:23:43] month. And when we went to Budapest and, you know, even if I'm at a, uh, at a restaurant or a bar
[00:23:49] and someone just casually says, you know, where do you work? And I said, I worked at Prezi. It was
[00:23:54] as if you were a rockstar because, um, for Hungary at that time, I think, uh, Prezi was their first,
[00:24:01] um, uh, sort of Silicon Valley funded company. So it was, it was a huge deal when I was in Budapest
[00:24:08] that, uh, you know, that I was working at Prezi. Yeah, that's awesome. And then we're just stepping
[00:24:16] through, right. We're going through your life and we're at Fitbit now, but, um, just the, so looking
[00:24:23] at analytics. So now we're talking about data intelligence, then analytics, what is the one
[00:24:30] thing people don't do with data that they should do? And I'm kind of giving you the answer, but you
[00:24:34] already know the answer anyways. Um, I think, I think, I think, uh, they don't, they don't trust us as
[00:24:43] much as I think they should. Um, I think, I think data is meant to be a tool it's meant to sort of aid
[00:24:48] decisions, but if you've already ate up, made up your mind and then you just kind of want data to
[00:24:53] agree with you, that's, that's not the right way to use it. And I think, I think that to me is the
[00:24:57] most common thing that people don't do correctly with data. Well, it's funny. You look at Fitbit,
[00:25:03] you look at Strava, you really, you know, we're in this whole quantified self thing. And I think
[00:25:09] a lot of people still are very into it. You know, we've seen Apple really come in and like,
[00:25:16] they normally do take a market a bit, but what are some of the things? Cause data is everything
[00:25:22] and that you're, that's the currency, right. Of, of these kinds of companies, were there things
[00:25:28] that surprised you, whether it was like how ridiculous super users get, uh, like, what do
[00:25:34] you take away from those kind of quantified self health tracking experiences?
[00:25:41] So I'm, I'm huge on the quantified self, uh, sort of, you know, track everything, uh, figure,
[00:25:47] figure out how to make it actually shape your life in a, in a, in a positive way. So working at Fitbit
[00:25:53] and Strava, like, honestly, like it was, it was amazing. Like, uh, I think Strava is one of the largest
[00:25:59] sports data set in the world. Um, so it was just, it was just fantastic. Like, I think they didn't even
[00:26:04] have the sort of health leaning applications, uh, you know, maybe they will in the future, but, uh,
[00:26:10] just being in that space was fantastic. And I, uh, you know, for the super users, um, my, my sort of fun,
[00:26:16] uh, fun story is that while I was at Strava, um, even more so than normal, I think because part of it,
[00:26:23] like I started there when it was still the pandemic, uh, I did a ton of speaking engagements.
[00:26:27] Like I was speaking at 25 events a year. Um, and I, I still do that, um, maybe a little bit more now,
[00:26:33] but, uh, even at that time, um, I think a lot of people, the minute they'd hear that one of the
[00:26:39] speakers is the head of data at Strava, uh, there'd be some section of the audience who were just,
[00:26:44] they were just ready. They're like, okay. Um, one, I'm going to tell you, I love your product.
[00:26:50] And then two, I'm going to tell you the 10 things that really annoy me that I want you to fix tomorrow.
[00:26:54] So, so like that was, it was, it was actually kind of really fun. Like just, um, I think that is one of
[00:27:02] the joys of working for a consumer tech company that you really get to hear from real users, real
[00:27:08] customers, you know, in your daily life. Um, when I was working at Salesforce, that did not happen.
[00:27:13] Like people did not, um, stop me at a conference to, to tell me what they love or hate about my,
[00:27:19] my product or the product that I was helping build. But at, uh, Strava at Fitbit, that happened
[00:27:24] all the time. And even when they were complaining, it was a complaint still out of, I love this
[00:27:30] product. Why doesn't it work exactly how I imagined it to be? I had this gentleman say that he was on a
[00:27:38] 13 hour bike ride and his device died. And he says, somehow Strava should be able to stitch together
[00:27:44] the rest of my data because it's so important. And I was like, I hear you.
[00:27:52] Yeah. I know there's joy in listening to consumers, but there's also pain in listening to consumers,
[00:27:59] I think. Um, but just dealing with that amount of data, right. And you just touched upon it,
[00:28:04] like what makes you want to go out there and keep presenting? Like what, because it isn't easy,
[00:28:10] right? You have to prep for it. It takes time. You have to, you can't talk about the same thing
[00:28:16] again and again and again, but it takes so much time and effort, but what pushes you to present more?
[00:28:23] Yeah, that's a, that's a great question. Um, so I think in my case, it was something that I started
[00:28:28] doing when I was at Salesforce. Um, I would say I had a boss who, you know, um, I think he encouraged
[00:28:34] it, uh, quite a bit. So I think, I think I really, I really think that that helped. Um,
[00:28:39] one of the reasons was because part of my job, like in data, uh, storytelling is a part of the job.
[00:28:46] Um, so no matter which part of data you're in, you are going to have to explain technical things
[00:28:51] to a non-technical audience that is, that is part of the job. So I, I think I initially,
[00:28:57] when I started doing it, it was also for sort of a direct skill that relates to my, uh, to my daily,
[00:29:03] to my daily work. Um, and then eventually I started branching out in topics that were not
[00:29:08] just about data. Like I started talking about a lot of other topics as well, but I would say that
[00:29:13] that has been sort of the huge motivation. Uh, now I also just enjoy it. Um, I think you're right
[00:29:18] that you can't keep talking about the same thing, but, um, I have, you know, I would say four or five
[00:29:24] core topics that I talk about. Uh, but then even when I talk about that, like there's always a new spin
[00:29:29] to it depending on what's the difference in audience or what's the difference in
[00:29:33] or what's the difference that I want to talk about. Uh, you know, I used to talk about data quality.
[00:29:37] Like I've been talking about that for almost four, five years at this point. Um, initially I used
[00:29:42] to anchor it all to, um, to healthcare because I was working with a health tech company at that time.
[00:29:48] So I was not quoting direct examples, but, uh, it was just, we were also in the middle of a pandemic.
[00:29:53] Uh, so it was just easier to, uh, it was a good way to get people's attention, uh, talking about
[00:29:58] something that was relatable on a daily basis. Uh, and now sometimes I try to switch that.
[00:30:03] I'm like, okay, what is a new spin on the same topic, but relating to maybe a different industry
[00:30:09] that can also help influence decisions there. Yeah. I mean, presenting and thought leadership
[00:30:16] are such important pillars of really all of our, uh, industries. I'm interested just from the point
[00:30:24] of view. If you, if you, if you do 25 talks in a given year, that's one every two weeks and they're
[00:30:30] probably jammed together in some cases, how do you, it's almost like doing a standup comedy routine.
[00:30:35] Like, how do you always make sure that you're feeding in something you just thought on the drive
[00:30:40] to work into one of them? Or do you do that? How do you, how do you approach the presentations
[00:30:46] each time and have the little spin that you need to have on each one? Yeah. Um, so I like one,
[00:30:54] just to manage it. Like I, I have a, I have a very large spreadsheet that I maintain about each thing.
[00:31:00] And I have all these pre, pre, uh, event things that I do and post event things that I do. And then
[00:31:06] for each one, I do have a prep doc that I always keep, uh, keep kind of handy, uh, depending on the
[00:31:12] format. Like sometimes I don't have access to the, to the doc. So if I'm on stage, um, you know,
[00:31:17] I don't have access to the doc. Uh, so then it's really like just narrowing it down to the three
[00:31:21] things that I want to land, uh, in this particular engagement, uh, that are either different or it's
[00:31:27] something that I feel like I didn't do as well last time that I want to make sure to, um, sort of
[00:31:32] land it in this moment. Um, and yeah, the, the spin, like some, some of it is organic. Um, like,
[00:31:37] I think, I think just, I really feed off an audience, uh, like in, in the situations where
[00:31:43] there is an audience, um, it's really, I think for any speaker, uh, the tiny head nods that people
[00:31:49] give are really valuable. Like you kind of, you, you get a sense of, um, you know, are people jiving
[00:31:55] with your sense of humor, uh, or are they a little bit more serious? Like what is, what is the tone?
[00:32:00] And you, and you sort of adapt. Um, and I would say now having done so many of these over the years,
[00:32:06] um, it's a little bit second nature. Like I don't think anybody's ever perfect at it and I'm nowhere
[00:32:11] near that. Uh, but every single talk I do, I get better at that audience management, at that thinking
[00:32:16] on the feet, um, or adapting to what the mood in the room is. Um, and I would say some of it, yeah, if I,
[00:32:23] if I've woken up with a bad mood, like there is going to be a difference in how I kind of show up. I, I,
[00:32:29] I've reached a point where I can, uh, power through it a lot more easily, but, uh, you know, I, I,
[00:32:35] um, if I haven't slept properly, like that's, that's going to make a difference to, um, my ease
[00:32:40] of adapting on the fly. So, uh, a funny thing, maybe five or six years ago, I joined a Facebook
[00:32:49] group called the basketball barbershop. And it was basically, I'm from Northern New Jersey and it was
[00:32:55] all these people from high school and all this at this point. And we just talk about basketball.
[00:32:59] And then one of the moderators was this guy named web son, and he was really intense into moderating
[00:33:07] and like doing all this stuff. So then I become Facebook friends with him off of this. And then
[00:33:13] all of a sudden I'm like, wow, this guy co-founded a major healthcare tech company, Komodo. He's one of
[00:33:19] the co-founders. So I'm always fascinated by the fact that he is in there. He loves basketball so much.
[00:33:26] He's in there moderating a Facebook group for Northern New Jersey basketball thing. And there
[00:33:31] he is. So I would have to say, what was it like at that point? It looks like you were in leadership
[00:33:36] there. Um, what was it like interacting with folks like this? And it shows you the, the,
[00:33:42] the point of having interests outside, I guess. Right.
[00:33:45] So that's so funny because, you know, literally the last time I met web son was at a, at a Warriors
[00:33:52] game and it was a playoff game. It was fantastic. We ended up winning. It was, it was, it was fantastic.
[00:33:59] And, uh, yeah, it was, um, so Komodo, I was, uh, yeah, I was, I was part of the engineering
[00:34:05] leadership team. So I had a lot of exposure to sort of, uh, the C-suite web son was based out of our
[00:34:10] office. Like I was in the San Francisco office and he was fantastic. Uh, both him and Arif, uh, are the
[00:34:17] co-founders of Komodo and like, hands down, I have worked in a lot of startups. Uh, they are the best
[00:34:24] co-founders I have ever worked with. Uh, they are both really sharp. They have fantastic chemistry.
[00:34:29] Like I, I, I enjoy just, uh, observing their sort of personality and how it kind of shaped the company
[00:34:37] so much. Um, that's, that's so funny. Good story, Matt. I didn't, I didn't expect that. I had something.
[00:34:45] I'm like, okay, go on. Um, coming back to this though. So you do all this work done with pandemic.
[00:34:53] And then after that, you go decide to write a book. Like what made you think of writing a book?
[00:35:01] Because it's not the most easiest thing to do because it's a pain in the behind.
[00:35:05] Uh, yeah, absolutely. A hundred on the, on the, on the pain. Um, in my case, it started from a doc.
[00:35:13] So, you know, like I mentioned, I had, I'd been very intentional about speaking, um, and, and thought
[00:35:18] leadership and, and, and, and that for a while. Uh, so I think almost five years ago, I was at a
[00:35:24] conference, uh, which was actually a tech conference, uh, but they had some non-tech content as well.
[00:35:30] And they, uh, said that they gave me the choice. They said, you know what, you can talk about whatever
[00:35:35] you want. Um, so I had done enough data related talks, uh, in the recent past. This was the first
[00:35:42] time I talked about a non-technical topic. Uh, it was a talk titled how to hashtag humble brag effectively.
[00:35:49] Um, and, uh, it ended up like, I think I would say, I think it did end up changing my life because,
[00:35:56] um, I just gave that talk on a lark. It was based on my own, um, experience with self-advocacy
[00:36:04] and the structure that I had formed on that. And I, I shared it to a room full of like, there was,
[00:36:10] it was a packed room of a hundred odd people. Uh, and I was surprised at how many people resonated
[00:36:15] with that topic. Um, so then I started becoming more intentional about speaking about that topic.
[00:36:20] Um, and eventually I got to a stage where half the speaking engagements were data, half were self-advocacy.
[00:36:26] Um, but I just had a lot of people ask, they're like, okay, your talk was amazing. You know,
[00:36:32] can we follow you? And then they asked, do you have a book? And enough people asked that I said,
[00:36:38] maybe I should write a book. So that was, that was kind of how that came to be.
[00:36:44] And how did you write it?
[00:36:46] Um, very slowly at first, uh, I, when I was working full-time at Strava, I, I, I, I set a goal
[00:36:54] and then I was came nowhere near to meeting that goal. Like, I think the whole year, uh, I, I wrote,
[00:37:00] I wrote 3000 words in, uh, one year, uh, I'm just for context. My book is 45 ish thousand words.
[00:37:07] So, so really in, in, in one year I made, made very little progress, but, uh, after that, like,
[00:37:13] that was the time that I decided, uh, you know, to, uh, to, to leave Strava. I, I really just wanted
[00:37:19] to finish my book. Um, I also wanted to switch to working part-time. Um, so I started my, uh, my sort of, uh,
[00:37:27] role as a fractional, uh, fractional head of data in, uh, in various companies. Uh, but the book then,
[00:37:33] like, then it went really fast. Like in the next four months I'd finished the draft. Um, I found,
[00:37:38] I, I talked to a lot of people about self-publishing versus traditional publishing. And like, I think,
[00:37:44] I think from the time that I, um, was like, okay, I'm committed to this goal. Like it took,
[00:37:49] it took less than eight months to get it out of the door, which, uh, which was almost, yeah,
[00:37:53] it was, it was almost exactly 11 months ago that that happened. And what is, um, committing to it
[00:37:59] mean to you? I I'm really fascinated by book writing and on my own podcast, I've had a lot of authors
[00:38:04] and some will go to a diner and just drink coffee until they've hit 10,000 words or something, or
[00:38:11] what was your, especially as someone who's in data and really efficiencies and all this,
[00:38:16] it's like, what was your, was it Coke zero and, uh, four hours or how did you,
[00:38:22] what does commitment to writing mean to you?
[00:38:25] So it's interesting because, you know, we were talking about that whole quantify, uh,
[00:38:30] quantify yourself. Like this, this is almost a small data version of it. Uh, but for me, um,
[00:38:36] I am a, I'm a person who's very self-motivated. Uh, you know, I, I spent so much time in my
[00:38:41] childhood, like swimming by myself for hours on end. Uh, if, if I have my own goal, um, I am more
[00:38:48] likely to meet it that someone else setting a goal for me. Um, and for me, the goal is rarely,
[00:38:55] uh, you know, so I'll, I'll, I'll give the example in sports. Like if I'm swimming, I'm not going for
[00:39:00] speed. That is not a thing I track. That is not a thing I care about. I'm going for consistency.
[00:39:05] I'm going for the fact that I want to swim, uh, you know, three times a week and I want to swim
[00:39:11] at least 20 minutes each time or something like that. Like I do not care, uh, about being the slowest
[00:39:16] swimmer out there as long as I'm doing it. Um, and I think that's a different mindset. I think,
[00:39:21] I think some people are completely not motivated by something like that. Um, and so even the book
[00:39:26] writing for me, it was, it was, um, not about like how quickly can I get this book out or what is
[00:39:31] the biggest book that I can get out? Like I'm going to write a hundred thousand words, nothing
[00:39:35] like that. I was like, I think I have something of value to say. I think there is an audience that
[00:39:41] would like to hear it from me. So getting a book out of the door, which is valuable, which I am proud
[00:39:47] to put out there. Like that was, that was the goal. So, you know, I'm not, I'm not trying to hit
[00:39:52] like a lot of different metrics in it. Uh, and then the, then the sort of daily, uh, accountability
[00:39:58] was a consistency thing that, um, I timed myself a couple of times, uh, you know, just free, that
[00:40:04] free, free form writing. I would note down the start time, note down the end time. And I got to
[00:40:09] that stage where I said, okay, I, I roughly write about a thousand words, uh, in an hour. And, uh,
[00:40:15] so then it was like, okay, how many hours of, uh, writing a week do I want to, do I want to commit
[00:40:21] to? And I had a, I had a document that I tracked like, you know, like what was the total word count
[00:40:26] at the end of this day, end of this day. Uh, and I'm very good at shaming myself into doing more.
[00:40:31] Like if I, if I saw that I, you know, a few days had gone by and my word count had not really
[00:40:36] increased, like I, I, I myself, I'm shamed into, into, into sort of doing it. Um, so, so that was,
[00:40:43] that was sort of my process. I don't drink coffee, so I have no idea what caffeine would have done for me.
[00:40:51] And then, um, can you tell us a little bit about your work at the, uh, invest in data,
[00:40:58] shall we, uh, of how you help out early stage startups, uh, who are into data?
[00:41:05] Yeah. Um, this was also super, uh, super fun. Cause right around the time that I was leaving Strava,
[00:41:10] um, investing data reached out. Uh, so this is an, uh, for, for, uh, sort of the sake of the audience
[00:41:16] as well. This is an angel investment. It's a, it's a, uh, it's a date, it's an angel investment
[00:41:21] collective. Um, so we, uh, sort of invest as a group. Um, what that actually means is that we do
[00:41:28] due diligence as a group. Um, you know, we're not required to invest in, in everything. Like
[00:41:33] people still have personal, uh, sort of decision on whether they invest their money or not, but having
[00:41:38] due diligence done as a group. And we had about 50 data leaders from across the country, um, is really,
[00:41:45] really interesting. Cause, um, I mean, I, I'm so grateful that I, uh, that I, that I was invited
[00:41:50] to join, uh, this, uh, this collective cause, um, I've learned a lot from, uh, everybody else who's
[00:41:57] on the thing. And, um, also when you are investing, it really helps to, um, have trustworthy people
[00:42:03] who are vetting it, you know, who are vetting the same thing and who are vetting it similar to how
[00:42:09] you'd vet it. Uh, how we think about data companies is, is, is, is, is very similar. Um, and I
[00:42:14] would say for the companies that, uh, I do end up investing in, um, I think it's, uh, you know,
[00:42:21] they are series A or seed seed companies. Typically we don't invest in series B or, uh, like beyond
[00:42:27] series B. Um, but, um, it's really cool to, cause I also am very close to them. Like they give regular
[00:42:33] updates. Um, just today, one of the companies that I'd invested in, they raised their series
[00:42:37] a B round. Um, so it's kind of really cool to sort of have that, um, semi front seat, uh, sort of view
[00:42:45] of what's going on. Um, you know, we help out the companies by connecting them to other, um, other
[00:42:50] companies that might use them as a vendor or something like that. And, and also provide advice
[00:42:55] on the product itself.
[00:42:59] Shelby, you have, as we went through, you've worked at just, you know, if it were a logo list for a
[00:43:05] company, it would be like an enterprise company. If you look at who you've worked for and each one
[00:43:10] seems to have added really cool experience industries, new ways of utilizing data. How,
[00:43:18] how did you decide? Um, because none of the decisions were like, they were all moving to even
[00:43:27] cooler places or adjacently cool. How do you decide, okay, it's time to look at the next thing. You know,
[00:43:34] when you're looking at one and two year stays and like, how do you, especially in this time of
[00:43:39] post pandemic and, you know, a lot of job loss in this, we'll knock on wood here, right. A lot of
[00:43:44] job loss across these industries. How do you kind of decide internally when it's time to go somewhere
[00:43:51] else? Um, yeah, you know, that's a, that's a great question. Um, I think it's a, it's a difficult
[00:43:57] one because my perspective has definitely changed a lot over, I would say the last few years.
[00:44:04] Uh, so one context is I am based out of San Francisco. Uh, the average length of job for
[00:44:09] most people here is a year and a half. Uh, you know, if, if, if, if your experience is really
[00:44:15] bad, it's six months, if it's really great, it's usually two years, but that's, that's the range.
[00:44:20] Like, you know, so I, I think there's almost this, uh, itch that people start having, uh, that if
[00:44:25] they're not, um, I think if they're not growing or the company is not growing, um, that is a very
[00:44:32] good prompt to think about what is next for me. Um, and I would say that when you work with startups,
[00:44:40] uh, I think except for maybe two companies, I have mostly worked for startups my entire career.
[00:44:46] Uh, you know, most startups don't, don't last beyond two years. Um, so it's a little hard to
[00:44:51] sort of hitch your wagon to, uh, to something that you're not, not super sure, but that's not always
[00:44:56] the only reason, you know, like I care about, uh, personal growth a lot. So what opportunities
[00:45:01] is a company providing for me? Um, I've also been in the situation where I have been poached a lot.
[00:45:07] Like I would say like at least three times when I made a switch, uh, I wasn't necessarily thinking
[00:45:12] about it, but someone came with an opportunity, which sounded just too good to pass up. And I
[00:45:17] always give, uh, you know, existing companies that opportunity to be like, Hey, this is like,
[00:45:22] it's, it's never, uh, I haven't, I have touched wood. Like I've never had a very, uh, a contentious
[00:45:27] exit from a company. Like it has always been something that was, uh, understood like on both sides,
[00:45:32] uh, how it was going to play out. Um, you know, I give very long, uh, exit times. Uh, for example,
[00:45:39] when I decided to leave Strava, like I gave them two months, uh, of a transition time. And I said,
[00:45:43] if you want it to be shorter, that's fine from my side, but I am willing to give you two months.
[00:45:47] And that's exactly what we ended up doing. And then, so what's next for Shelby? Um, good question.
[00:45:56] I would say that, you know, right now, I think, uh, I think the last year and a half working
[00:46:01] for myself has been, uh, has been fun. Um, it's also very tiring. Uh, as I was saying, the life of
[00:46:06] a solopreneur, I, I feel like I'm always on one of the reasons I switched to part-time work was
[00:46:12] because I was burnt out and I don't think working for myself really had that a whole lot, especially
[00:46:18] because I also got a, got a book out in that time. So, um, you know, I'm, I, I'm a very go with
[00:46:24] the flow person. So as, as things move on, um, I don't think the job market is great right now.
[00:46:30] Like I've dabbled occasionally, you know, trying to, I did get a few offers in the, in the last
[00:46:36] year, uh, and none of them excited me enough where I was like, okay, I'm not, so I am, I
[00:46:42] am earning less money than I used to before, but I am okay with that. Like I, I, I don't
[00:46:47] want to, uh, be earning less money and working a job that I'm not excited about. So at least
[00:46:51] this, this working for myself, it is, it is very fulfilling. Uh, and as the job market evolves,
[00:46:57] as my ability to continue making more money with my own business, it was, I might shift
[00:47:03] my perspective in what I would prefer to do. Uh, but for now I'm, I'm, I'm happy doing what
[00:47:09] I'm doing and it's, it's been fun. What made me think of something. Cause when we say the last
[00:47:15] year and a half, what's really been the huge thing, generative AI, how has generative AI affected
[00:47:21] you as a data person, is that the kind of, can I, can I ask if you'd be interested in
[00:47:27] working at open AI? I don't have the, I don't have the interest to do it, but just in general,
[00:47:33] what does generative AI kind of make to you? Yeah. I think, uh, it's, it's very interesting
[00:47:38] cause, um, you know, so again, like the, the work that I do right now, like I, I work with,
[00:47:43] um, seed and series a startups as a fractional, uh, sort of head of head of data. And it's very
[00:47:50] interesting. A lot of my conversations with these companies, when we're sort of, you know,
[00:47:54] doing the scoping call and figuring out like, uh, where I would fit in. Um, most of it is very
[00:47:59] regular stuff. Like it's, it's stuff that I've done before. It's stuff that I think, you know,
[00:48:04] in a very small amount of time, I can add a lot of value. Uh, and then there's usually this question
[00:48:09] that comes up, like our company would like to do gen AI. How can you help us with that? Um, and I have
[00:48:15] to balance, uh, politeness with reality. And, you know, some of these companies are really
[00:48:20] small. Uh, they have, they don't have the data maturity to even be able to predict things,
[00:48:26] leave alone, have the capabilities to sort of use gen AI, um, you know, with their in-house data,
[00:48:31] they can have capabilities that are plug and play for them, uh, where they're leveraging gen AI
[00:48:36] capabilities from through some other tool, but it is not necessarily with their own data. Um,
[00:48:42] and I think that is what companies would ideally like to do. Like they would like to turn,
[00:48:45] you know, as they say, like turn the gold, like with your own, with your own stuff. Um, so I do
[00:48:51] think it has changed the conversations quite a bit. Uh, I do understand that companies are almost
[00:48:57] required to be actively thinking about gen AI capabilities. If, especially if it's a consumer
[00:49:02] facing platform, uh, I think it almost is a requirement. Like you have to have something which
[00:49:09] may be normal machine learning, but you have to slap a label on it to, to kind of show your, your,
[00:49:16] your, your thinking about it. Uh, and I think there are so many applications that are actually
[00:49:21] very low hanging fruit. Uh, they may not, they may not be cheap to implement. They may not be easy
[00:49:25] to implement, but, um, from just a conceptual perspective of like, how would you incorporate
[00:49:32] this new technology that has a lot of limelight on it? I think there's, I think there's lots of options.
[00:49:39] So Shelby, what does the word community mean to you? Um, I think community when it's, uh, when it's
[00:49:47] intentional is, is, is, is great. Uh, you know, it's, it's, it's sort of, uh, people who have something
[00:49:55] in common that they choose to, uh, choose to amplify or, or, or align on the, on the basis of.
[00:50:04] So Shelby, our last question, we ask all of our esteemed guests, if you were to go back in time
[00:50:10] and give your 15 year old self, uh, some advice data-driven or otherwise, what would that,
[00:50:19] what would that advice be to the young Shelby? Uh, yeah, great question. Um, I feel like when I was
[00:50:28] 15, I had a lot of people giving me advice and, uh, you know, I think, I think all the elders I know
[00:50:36] said, Hey, it's great that you're getting so much advice, like lap it up. Um, but I would, I would
[00:50:41] add a shift to that, like, um, find actively find people who will support you, who will sponsor you
[00:50:48] and not just give you advice. You know, they, that they say like, find the sponsor, not just the
[00:50:53] mentor. Um, and, and that is sort of the distinction that I would draw to, uh, you know, 15 year old
[00:50:59] Shelby. Like, uh, I, I, I think I would have, uh, been well served with knowing that distinction.
[00:51:05] Like, you know, who's here to just give me free advice versus who's here to really have my back
[00:51:09] when I need it. Thank you so much for your time. Shelby, it was really wonderful speaking to you
[00:51:17] and learning all the things. Thank you so much for having me. It was a pleasure to speak to both of you.
[00:51:23] Thank you for entering the converse. We hope these discussions gave you something to think about,
[00:51:29] helped you learn something new, and provided a window into someone else's story. Everyone's story
[00:51:36] is worthy and important. Until next time, remember to be fair, be kind, and keep exploring.