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Jeff Rinehart, now a partner at venture capital impact firm City Light Capital, is a self-proclaimed linear thinker with a nonlinear career. From his 11-year tenure at Capital One, where he started as a statistician and ultimately oversaw the company's marketing strategy for the U.S. consumer credit card function. He then went on to join early-stage ed technology startup 2U as their chief marketing officer, and, two years after taking the company public, became a full-time professor at American University's business school. From there, he started advising companies and angel investing, which led him to City Light Capital—the lead investor on Teal's recent $6.3 million round of funding.
In this episode, Jeff touches on overcoming impostor syndrome, the power of lateral moves, how his background as a drummer led him to study economics, and why he's always been drawn to opportunities that challenge him and force him to grow.
Everyone's career path is different, built by pivotal moments and choices. We're on a mission to amplify those stories and examine how our decisions shape our careers.
Nonlinear is hosted by Dave Fano, Founder & CEO of Teal—a genuinely consumer-first platform designed to help people grow and manage their careers. Our goal is to empower people to land jobs they love with free tools that guide and automate the process. Learn more at tealhq.com.
Jeff Rinehart: [00:00:00] That has more common than not that imposter syndrome, especially when you're pushing yourself in new directions, right? Like you're, you're pushing yourself out of that status into this realm where you don't know everything. It's still scary. You're stepping in and meeting a new team, your now accountable for things that you don't know how to do.
And you feel like you're faking it for a long time. And I think.
David Fano: Hey, everyone. Welcome to nonlinear a podcast about the decisions that shape our careers. I'm Dave, the founder and CEO of teal and the host of this show. If you're enjoying the conversation on this episode, please make sure to subscribe, share, and rate us wherever you're listening to the show.
It really helps shine a light on these amazing careers and increases the chances of us learning from each other. Again, thank you so much and let's jump into this amazing. Thanks for joining today. We're with Jeff Reinhardt, who I've had the pleasure of getting to know over the last six months and has quickly escalated to being one of my favorite [00:01:00] human beings on the planet.
Now it's for you guys to hear a little bit about Jeff directly. So Jeff, can you tell us a little bit about yourself? Yeah.
Jeff Rinehart: Happy to thanks for having me. My name is Jeff Reinhardt. As you mentioned, I'm a partner at, in venture capital firm called City Light Capital. City Light Capital is what we call an impact firm.
So we only invest in companies that can do top decile venture returns financially, but also do measurable social good. We invest in three sectors. Primarily we invest in company. Building tech driven solutions in climate education and care. And we've been doing that for almost 20 years at this point. So before the term impact investing even existed.
So I I've been at city life for about four years, spent 20 years before that, as an operator, I started in the early days of capital one. I started there as a statistician. So I'm a math guy by training and spent 11 years at capital one did a whole host of things. The last of which was running marketing strategy.
The U S consumer credit card function. So had their direct mail [00:02:00] engine, all their online channels at a time when. You spoke was becoming Facebook and Edwards was becoming ad-words and kind of get to see that ecosystem get born, which is pretty neat. And then left there and decided I wanted to try my hand in startup land.
So joined an early stage education technology company as their chief marketing officer, and we timed it well in the ed tech boom and raised a bunch of venture money and took it public on the NASDAQ. You got to ring the bell, got my daughters on the big screen. That was cool. That stayed for two years, post IPO and the decided.
I was going to retire and be a professor for the rest of my life. So I went to American university in Washington, DC, and was a full-time professor in their business, school teaching, mostly graduate level, ML, AI kind of stuff, and started advising companies and doing a little angel investing. And that's really what, what led me to city lights.
So, you know, I give you that background and narrative because. There are a lot of twists and turns in that journey and a lot of pivots and LSU pivots, even before that. So happy to dive into [00:03:00] whatever you think is more.
David Fano: I think your career highlights, how many careers are, you know, and, and people probably just see like the CMO transition to VC, but you know, you studied math or a statistician came at it through the tech angle.
Marketing's become much more data-driven. So I'm excited to talk through that. And for people to see that these things are generally nonlinear, you're probably more of the standard, you know, you're probably more the norm than the linear career, but people just, again, just don't talk about it. So let, let's take it back to the beginning.
When was the first time in your life? You started to take actions or think deliberately about your career and kind of like what you wanted to do in air quotes.
Jeff Rinehart: Yeah, that's a great question. I probably pegged that back to somewhere like second year undergrad. So I think up till then I was largely. Under some form of inertia and, and not proactively driving towards a particular career.
Actually, I mentioned I had even a pivot or a few [00:04:00] before my story, but I started college as a music major. Oh, wow. So I thought I was, I, I'm not sure what I thought I was going to be. Like, I played music in bands all through high school and I was like, well, I'm going to keep playing music. So I went to college, I was a music major and that lasted probably a semester or two.
And I was like this, I'm not sure this is the career I want, I love music, but I'm not sure this is the career. And then I think I, I wandered aimlessly as an undergrad, as many of us do for awhile. And I ended up finding a professor, which is often the case. Uh, that happens for a lot of people that really clicked with me and that professor was in economics and I really took to econ for a number of reasons.
I think it's the same reasons that I like marketing. You know, it's a, it's a social science that's rooted in mathematics. And I love both sides of that continuum. And as I started getting into economics, the more mathy sides of it around econometrics, I decided to [00:05:00] stay and do my graduate degree and really felt like that was the path for me.
I'd always been, even though I was a musician, I was a drummer. Percussion tends to be fairly rhythmic and mathematical. I, that always sort of clicked with math. And I think it was in that period that I really started thinking about career and jumped from that master's degree straight to capital one.
David Fano: So you got a master's
Jeff Rinehart: degree in economics?
I did. Yeah. Applied micro with a concentration in econometrics.
David Fano: How did you make that shift from a degree in economics to then landing.
Jeff Rinehart: No. It's interesting that that role of capital one in my mind at the time was going to be shortlisted. So I loved economics and I got my master's degree. My plan was to ultimately go get my PhD and teach, which 20 years later I actually accomplished.
But it took a long time. As you say, these things are winding. So I went to capital one. Took a job as [00:06:00] a statistician. I only had a few stats classes in college and I didn't particularly like them. You know, I like them for implied parts of a kind of metrics. But as I got to better understand the role of what statisticians in places like financial services do, it was really about, it was more kind of metrics than it was pure stats.
Right. It was building predictive models. I like to tell people at the time. Using math to predict the future because that's what we were doing and felt like something I could do. And capital one at the time seemed like a really interesting and unique company. You know, this was the early days where we were going to take on the big banks with math and sort of disrupt the norms.
And it was very entrepreneurial and fun place to work, still think incredibly highly of the place, you know, as it as a math guy, Growing up at capital one, you never had to convince people there that data mattered, that analytics mattered, that math mattered. And that's not always the case. [00:07:00] Right. But it was just in the DNA there.
So I think I got there planning to only be there for a while to save up enough money and go get my PhD and just fell in love with the work and the culture and the development that I was afforded and had a, even there oddly circuitous career, you know, I started there as a statistician. And grew through the ranks of the stat family there and became what's called a scoring officer, which is a capital one that drive business strategy actually wanted to try my hand at driving business strategy.
So even though I was having a fairly successful run in that stack family, decided to pivot and became an analyst and started to learn that. And that's where ultimately moved into marketing and did a bunch of stuff along the way. But
David Fano: did you need to go down. A few levels when you made that shift, because I would imagine a, the person who signed off on the models was hierarchically fairly high up in the company.
So what, what was that? And also even just like, in terms of compensation, did you need to take a comp hit to do that? [00:08:00]
Jeff Rinehart: I, luckily I didn't, uh, you know, I was afforded the ability to take what was a sort of parallel move, I guess. Right? Like, so it wasn't a step down in terms of title or level scope. Right.
Like in the stat family at the time as a scoring officer, to your point, I was people were bringing models for my approval and you know, that level of authority didn't exist in that horizontal analyst mood that I went over to it now, I ultimately grew in that role to like the now. Officer at the time.
And the analyst role is called a credit officer. So, you know, I mentioned the business analyst would develop a strategy where that model would be a piece of that strategy had to be approved by credit officer before it could be rolled out and become part of capital and strategy. I ultimately became a credit officer as well.
I think I was the first person at capital one to be both a scoring officer and a credit. Uh, at the same time, you know, it took a while to get back to that same [00:09:00] level of authority and approval,
David Fano: but what was kind of. Going through your mind at the time that prompted the change. Cause I think a lot of people have these feelings, you know, I call it the career growth loop where you kind of search, transition, develop, and, you know, we searched for something.
Then we, we transitioned into it, which takes a minute, could be turbulent. And then we start to develop and then. And then we search again. Right? So you, I would imagine you started to hit that like plateau and the develop and what, you know, to make a shift like that. Right. It's just kind of easy and, you know, and you tell people, they're going to say like, Hey, just keep doing what you're doing.
You have a great job. Why would you like rock the boat? You know, what, what was going on inside that said, you know what? I gotta, I gotta shake things up.
Jeff Rinehart: Yeah. I've never been good. Stasis and not, not rocking the boat or taking the easy seat, even at times when intellectually, I know, like, what are you doing?
Like, things are just fine. Like, why are you going to go do that? But I think [00:10:00] it's you, you articulated it well, right? Like you, you hit this plateau and it's not that I necessarily plateau it from my career arc standpoint, but from a like, always feeling. Like I'm learning and you know, that part of me doesn't understand what's going on.
And I, and the feel of that, I kind of like, right, like being in a space where I don't know it all and I have to learn and I have to go figure things out. I think at some point in that statistician role that became less, that, you know, that feeling of, oh, I got to continue to push myself and you know what I mentioned, like the statistician rule.
Definitionally was building tools that somebody else would use to build the strategy. And I really wanted to try my hand at the strategy piece of it. I think the combination of that plateauing or, or Stacey has combined with just a desire to try something [00:11:00] new, pushed me into the analyst family, which I was there for.
My last six years there, six or seven years. And it ultimately similar similar things cause me to, to want to leave a company that I've had a ton of success in and love very dearly. Join some crazy at tech startup.
David Fano: Well, the in-between there, the analysts, talk to me a little bit about the transition from analyst into like the marketing function.
Um, or if there even was one, cause I know your next job was in leading marketing at the startup, but was there, what was the transition like from analyst to marketing within capital one?
Jeff Rinehart: Yeah, it's a great question. You know, and it was a six or seven year journey. Where I got to see an experience, lots of different things across the capital, one organization.
One of the, one of the great things about capital one is they really do allow people to move around and see lots of things and try [00:12:00] lots of things. I think, you know, their thesis and if anybody's ever gone through the interview process at capital one, it's, it's, it's pretty intense. And you know, they're looking for certain competency traits and those kinds of things with the.
If you hire a certain type of person, you just kind of figured it out, like you move around and they kind of figured it out. So when I first moved into the analyst role, I was working in us card customer management group on a very particular program. So customer management is once we book a credit card, customer, customer management is responsible for maintaining that customer.
And one program that exists in car, customer management is the credit line increase function. So whose credit line should we periodically increased? Because of X, Y, or Z. I was an analyst just on that one thing. Right. And then I, that role sort of expanded. And then I moved into our small business lending group and had some senior roles in small business lending.
You know, it was there for [00:13:00] a couple of years. And a manager I had worked with previously had gone to acquisition and you know, said, Hey, what do you think about coming in and running marketing at the time? It was just digital. Uh, and the digital team at the time, like all the digital marketing. For us card, we all fit in a room and it was sort of us jumping up and down saying like, no, this is going to matter, right?
Like capital one was instilled a very large direct mailer, right? Like, no, like these display ads are gonna matter. And so it was an interesting time, but to get there, there's a, a journey in and around capital one, uh, even to land in that room where we were running
David Fano: digital. And so then what was happening is, was kind of like a confluence of.
Your abilities and the market because advertising and user acquisition was, you know, obviously there was a lot of dollars spent, but in terms of return on investment was tricky. Right? I was at a home, it was mailers, it was TV and marketing was transitioning [00:14:00] into this like very measurable what you're calling digital marketing, but on websites in social platforms, very trackable, very measurable.
Marketing activities. So kind of, and then with your interest in economics, I would imagine it was like a perfect storm of, of all these things for you to jump into.
Jeff Rinehart: Oh yeah. That's so well said. I loved it. I still love it. Right? Like it was that social science that had a bunch of similarities to that econ degree.
Right. My studies there. Customer facing and creative and tech driven and new and ultimately rooted in mathematics, right? Like I, I, your point sort of timed it when direct to consumer marketing at least had become a big math problem. And it just had all these things that I loved. And, you know, as I, as I did that for a couple of years at capital one, decided because of [00:15:00] that.
Would cause me to try and take a leap where I would go run marketing somewhere, uh, and build a team. All right.
David Fano: So talk us through that. How did that switch happen? You're working at one of the best credit card companies with great commercials on TV. At the time. I remember watching all those. Now you're going to go work at a startup and how are you defining startup?
Right? Cause that that term can be, you know, teal, six people with great support with investors like you to. You know, pre IPO, 1000 people with hundreds of millions in revenue. So w what was that kind of jump for you?
Jeff Rinehart: Yeah, that was, um, that was probably the biggest jump, right? Like, you're going from, I had three kids at the time.
We just moved into a new house. I had a, you know, VP job running marketing at capital one and sort of taking a leap and joining a startup. And I'll tell you what I mean by startup was not an obvious. One should be doing. I had a bunch of people asking me, like, [00:16:00] what in the world are you thinking? So the startup at the time, at the time, it was a company called to tour the number two tr and it ultimately came to you.
Number two, you two U partners with hiring universities. So when I say hire and think like Georgetown, Harvard, Yale to primarily bring, or at least initially. Graduate programs online. So we would host the technology for a full graduate degree. You know, the data science degree at Berkeley or a master's in nursing from Georgetown, whatever the case may be.
It was the technology and it was at the time, you know, this is pre COVID, obviously. Envisioning how these classes could come alive virtually just like they would on campus. But, you know, instead of walking into a brick and mortar classroom, you log it the virtual one. So we built that technology to enable brands like that to come on and scale.
But we also wrap that with a suite of services, everything from getting a degree [00:17:00] credentialed in a certain state, right? Like university of Southern California was credentialed to deliver masters in midwifery degrees in California. We needed to get them credentialed in office. To, you know, the training faculty are about how to bring their courses online to the marketing and recruiting of the students, which is what I did as the chief marketing officer to you.
So I wasn't marketing to, you actually got to market Berkeley, Harvard, Yale, and so on. So a pin that for a second and we can talk more about what that job looked like. The going back to your question, how did I define startup and what did it look like when I joined. At the time too, you had two programs live with university of Southern California and had, and, and we're generating students in revenue through those two programs and had two contracts signed, but not get botched.
They were at the hundreds of employees. So it wasn't six. They had raised two rounds of financing. And when the process of raising their third, so they were post revenue, call it in the [00:18:00] 10 million ish revenue range, probably. Single millions revenue range. And so, you know, it wasn't the earliest days of a startup, but it wasn't the IPO, certainly wasn't a fait accompli, right?
Like it was, there was a lot of white knuckle days and events and trials betwixt me joining and the ultimate.
David Fano: So I think a lot of people face this, these situations where like, if you, if you were to describe to you on paper and revenues, like, oh, that's, that's pretty, you know, that's a big company, 200 people, but still, I would imagine most people, you talk to you and said, Hey, I'm going to make this transition.
Seemingly super stable thing, good career growth. I could eventually probably be an executive at this publicly traded company, or I'm going to go join the startup. Everyone's like, why would you do that? And, and you really got to have a lot of like confidence, determination, [00:19:00] intentionality. To push through and something I've seen through or heard through having these conversations now is that the books are able to make these leaps is actually not driven by like comp or title.
They're driven by curiosity. And they're just so excited about the potential to learn. And that's quite hard to communicate to other people. Everyone else is just kind of looking at like comp and title on the surface. So what, what pushed you to make that jump and like, how would you talk about it to people when, when they obviously ask you, you framed
Jeff Rinehart: it well, and it, you know, it was the same, ultimately the same thing that caused me to move from statistician to analyst, I had reached some level of state.
That was calm and easy. And I'm, as I said, I'm not good at that. Like, I want to be, I want to be in untested waters in a, in a certain sense, right? Like, I, I w [00:20:00] I always want to be learning that I want there to be a lot of things that I need to stretch myself. And I tend to gravitate in places where, where that's true and the ability to join an organization where.
I could really build out the team myself, right? Like the marketing team and function to you at the time was fairly nascent. And I had the ability to jump in and build the team almost from scratch and. Put the structures in place and build the culture and be accountable for all of them, which was scary.
Not the least of which to you is headquartered outside of DC at the time I lived in Richmond. So there was a lot of commuting involved cause we did. We, we, we debated it at the time, but decided I was just going to commute. I three very young children at the time, God bless my wife. She, she carried a lot of water during those those times.
So, you know, it was non-obvious for a bunch of reasons, but it was, it was [00:21:00] the best thing I ever did. Like it, it, it changed my life. My family's life. It opened up amazing opportunities that it's the reason I met you. And I'm sitting here today. Right. Like it, some of those non-obvious choices that are scary, you know, if, if it's not super scary, it may not be a big
David Fano: enough one.
Like what do you honestly, you know, I kind of want to shine a little bit of a light on how maybe some of these decisions aren't as intense as they feel in the moment, but you might disagree with me about, Hey, it could have been a complete catastrophe, like say it didn't go so great. What, like, what do you think would have.
Jeff Rinehart: Yeah. I thought through that, like
David Fano: as a future predictor, I would imagine,
Jeff Rinehart: you know, I, I'm a, I'm a coder, I'm a math guy, I think, through all scenarios on a very kind of linear thinker. And so I, I thought through that and my take was I built enough support and [00:22:00] externally and competencies internally that I felt like if I went and tried my hand at this.
And it flamed out, right? Like the company didn't make it or I wasn't a fit. Right. Like, cause that's another thing that's not obvious. Like somebody who's grown up in a big company, like you could have making the leap into startup world. Sometimes there's just organ rejection there. Right? Like sometimes it just doesn't work.
But my thought was given the, given the support and. Skills that I've built over time. You know, I, my bet was if in two years I came back to capital one, they probably hire me again or some other bank, or like, I felt like it really wasn't existential. Right? Like to your point, it feels like a. Stephan. It is scary because even with that backdrop, it's still scary, right?
Like you're li you're going in and saying, I'm leaving, you're stepping in and meeting a new team, your now accountable for [00:23:00] things that you don't know how to do. And you feel like you're faking it for a long time. And I think that's natural, but you're right. It wasn't completely. Yeah.
David Fano: Actually let's talk about that for a second.
You said something that I think a lot of people wrestle with, you know, we talked about imposter syndrome, you went from being super successful at a really big company to now having a bigger title in a smaller place, a different kind of. But yeah, well, I mean, you know, I look at that happened to me at, we work.
I was, you know, for a long time, the youngest executive there, and it was definitely deja. I'm like, what am I doing here? You know, like empirically putting up the numbers, doing what my job was, but I was, you know, I was sitting next to someone who was a CFO of a publicly traded company, someone who had taken like multiple companies public.
And I'm like, what am I doing here? Like, this is crazy
Jeff Rinehart: all the time I had that feeling. Right. Like, and I do think it's natural having. Been through a fairly windy career. That's had a bunch of pivots and having worked with, you know, hundreds, [00:24:00] thousands of people in different parts and stages of their career that has more common than not that imposter syndrome, especially when you're pushing yourself in new directions, right?
Like you're, you're pushing yourself out of that status and into this realm where you don't know everything and feeling like I didn't belong or like, What am I doing here to your point? You know, I stepping into board meetings and you know, the first couple of rounds at two, you were led by Highland and red point and Bessemer.
These are kind of very top tier firms and I'm sitting around a board table with. Uh, board member from Netflix and a board member from, you know, and I'm like, what, what happened? Like, you know, I was kind of senior guy at capital one. Now I'm in a board room representing like, you know how we're gonna make CAC better.
And like, it's all going to be good. And you know, that's stressful and it's hard not to feel like, you know, you know,
David Fano: So that's the [00:25:00] funny thing about careers, right? We kind of like want that. We don't, we were sort of bored with the status quo. We want to learn, we want to grow. We throw ourselves into and they're like, whoa, wait a second.
Should I be here? But it's, you know, I often reference the, the sort of gym, no pain, no gain. The truth is like, if it's not uncomfortable, then you're kind of not growing. You're not stretching the muscles. You're not, uh, which then is where we kind of then get uncomfortable with the lack of growth. So it's a tricky thing, but you went on.
Objectively crush it at at to you. So talk us through, you know, getting there as a startup to, I think essentially was a quite successful IPO, which is really what a lot of people who join startups. That's really, the goal is to have that big exit. So to say, so what were some big moments
Jeff Rinehart: there? So I joined probably three and a half years before the IPO, as I said, there were two programs live.
We launched two more. I came in for me that the biggest thing was about building a team and building the right team and hiring the right people and surrounding myself with [00:26:00] people who are smarter than me. And. You know, clearing the way for them to do great things. And, you know, ultimately after a couple of years, and my non-solicit was over, I brought in some friends from capital one and, you know, building the team, getting the right instrumentation in place.
Because if you think about the challenge, one of the things that was interesting about to you from marketing standpoint is a we're marketing behind these centuries old brands. They've never really had true performance digital put behind them. Right. Literally, these brands are older than. And so to be able to come in and put digital marketing behind them was really unique.
And we were selling our marketing a hundred thousand dollar things from a distance, right? These were very considered purchases, which meant there's all kinds of unique aspects of the marketing piece of it. It was a very warm fall. So, Hey, you got to get people. Interested. And then you've got to manage them through the point where they've [00:27:00] actually submitted an application and are contemplating enrolling.
So we would manage that process all the way through, to a completed application and then hand the application to the school like Berkeley decides who gets into Berkeley and they hand the application back to us and we would help get them enrolled, but getting somebody through to a completed application, that's a long process.
So if you think of. For the marketers out there. And you're thinking about CAC, which is the thing that unifies all marketers these days and thinking about it, stressing about CAC, the actual event, right? Like, am I converting? Someone can be six months after I show somebody. I can't wait six months to know whether that ad was effective.
Right. So we had to build all kinds of predictive instrumentation along the way to be able to predict what conversion would be and thus what our CAC would be or else I didn't have an instrumentation on any of the marketing does. Right. So it was a very, very mathy. Approach that we had to take. And the other thing that was interesting about it [00:28:00] is each time we would watch a program, right?
Like how you go market and find somebody who might be interested in a master's degree in data science at Berkeley is very different than how you market and find somebody that's interested in a nursing degree, Georgetown. Right. So you're having to relearn at every program watch and like, that was tricky.
So it just took time to get that. Instrumentation built in those teams built and those skills built, and it was not a linear path. And there were some very Rocky moments along the way, but we got it figured out and, you know, IPO and I think to you at its peak had something like a five and a half billion dollar market cap.
It's lost several billion since then. They all
David Fano: For anyone listening. Well, one for anyone listening who doesn't know what CAC is, it's customer acquisition costs, which is a super important number for all businesses at this point. But I'd love to hear from [00:29:00] like a head count perspective, roughly what was like your function distribution. And yeah, I would imagine kind of what I'm teasing out here that I think you had a pretty big data science group, but if you were to say your, like your direct reports, how big were each of their functions proportion.
Jeff Rinehart: Yep. And that what's interesting as a company grows like that, that can even evidence flow. So for everybody in marketing, there are points in that journey where I managed marketing. So all of the marketing functions, which are come back to in admissions, so think inside sales basically, right? So we generally, and then that lead comes in and then there's somebody who picks up the phone and says, Hey, this is Joe Smith from university of Southern California.
Get you through, right? So we had an inside sales team as the org scaled that organization of all of marketing, all of data science, all of admissions, that's thousands of people. Right. So that ended up breaking off and I just ran marketing and admissions plugged in separately because it became such a beast of its [00:30:00] own.
Right. So even that role changed as the org, as they often do, but you know, inside of marketing, Even that's grew to be hundreds. So I had the data science team that was probably 10 or 15. And then inside of marketing really broadly, I had a, kind of an analytics optimization function, more of a brand marketing function because we were stewards of these brands, right?
Like everything we did had to be approved by the school. So, you know, we had a function or. Uh, sooner on that and then think like growths, marketers out there actually tracking ads.
David Fano: So like performance marketing is what I want for anyone listening. Who's like exploring marketing. I think there's, you can still be analytical and math oriented.
It doesn't mean you have to go to finance. It doesn't mean you've got to be in the operations department, right? There's a lot of different ways that you can instantiate these skills on different domains and different subject matters. And that's kind of [00:31:00] what I want to highlight for folks in the. About marketing as a function bias.
I'm a growth guy, but is you can see the impact of your work. You know, a lot of things aren't yet are kind of hard to see, but in marketing these days, it's becoming much easier to see the impact of your work. All right. So to you w I mean, I feel like we still have, we're short, not we're running out of time.
We've got so much cool career stuff to talk about. So, all right. Two, let's call them two grand slams career, crushing it, and then you're like, you know what, I'm gonna go do. I'm going to go back. I'm just going to say that again. I'm sure. Everyone's like, what, what did you and you just a company you're going to go teach.
So, so talk us, talk us through that because I think a lot of people wrestle with this. I'm going to go back to school. You know, it feels like a pure passion play, you know? Yeah. Well, how, kind of, what, what was the thought
Jeff Rinehart: process? Boy, are you right where people, like, what are you doing? Right. Like I was the COO of a publicly traded company that was doing incredibly well.
Again, like I'm bad at Stacy. I just am, [00:32:00] you know, I hit a point where the team had been built and, you know, we were launching new programs and there was some marginal optimization that can, you would continue to happen. But I felt like that was leveling off the, the big learning opportunities, the ability to kind of.
Be in that uncomfortable space and push myself had started to wane not to say that there weren't plenty of opportunities there, but I just, I felt like that was the case. And you know, I'd always wanted to teach. I mentioned my plan when I joined capital one was I was only going to be there a couple of years.
And because of two U I'd built some really solid relationships with deans and provosts and things like that. Those things started to come together and realize I had an opportunity to go do that. And I, I took it, you know, thankfully because of the two U experience, uh, I was able to put a little bit of money in the bank, not a ton, but enough where I could make [00:33:00] a career decision, not so optimized around one dimension like salary, right?
Like you don't go teach because you want to get rich at it to go teach because it's something you're passionate. And I wanted to try my hand at a different type of impact, right? Like actual working with students, like to you as a mission driven company. But I really wanted to try my hand, like actually working with.
And I didn't know whether I'd be a good professor, whether I would like it. And
David Fano: I loved it, really committed, really committed to it. You actually, one funny little story is that, you know, as we raised our last round C light and Jeff led it every time Jeff would make an introduction to me, uh, I would talk to the person.
And so, yeah, we, we really tried to hire Jeff when he was teaching and he just said no. And then I think I had that conversation. Five times where people said, yeah, we tried to get Jeff to join our company and, and he just wouldn't like to have that kind of like career diligence or like, you know, life diligence I think is, is pretty impressive.
But I feel like you were committed to [00:34:00] a thing. Can, you know, w where those hard was, like, every time you had to like, sit down and like weigh out the options, or because you had given yourself this framework for like, I'm doing this, did help make that.
Jeff Rinehart: It was hard every time it's hard. Right? Like, and in particular, when you're stepping into something, that's a little scary.
Right? So when somebody comes in, offers you something, that's a little more certain, like the minute I left to you, capital one came, Hey, you want to come back? And here's this big role. And you know, that's hard to say no to, right? Cause you're stepping into something that's uncertain. In particular when, you know, it's not just about me, I got a wife and three daughters and responsibilities and weighs on you.
Right? Like even, you know, you're doing things for the right words. It's hard, but I was committed to doing it. And it was a tremendous experience. And I, I taught all the way through last summer. Like I joined city life four years ago, but you know, I was still teaching, but I built a bunch of courses. I, I loved being in the classroom.
COVID was hard. [00:35:00] Professors, teachers, students, that was a tricky period. But you know, it was in that period. I started angel investing and advising and. There's other things I really enjoyed. Like I surprised myself at how much I enjoyed working with these early stage founders in a different way. Like, I I'd always assumed I'm an operator.
I got to have my hands on the wheel, but I was totally loving, like the advisory work I was doing. And that's what ultimately slowly led me to city light, which happy to talk about, although I know we're getting
David Fano: short of time. So another theme that continues to come up in these conversations is careers or.
Either shaped or not shaped by awareness. And like, I can only really pursue the things I'm aware of. You know, sometimes I have an interest in a domain or an activity, and then it'll kind of drive me. But in particular, VC, I think is a tricky one. Cause just a lot of people don't have awareness to this field.
They don't understand. You know what I'm talking to, like the general population doesn't understand the new Airbnb was made possible by [00:36:00] a venture capitalist, you know, Google was made possible by venture capitalists. And so I'm curious what your exposure to like the field and the domain was, and then kind of how that transition happened as you started to do a little bit of advising and investing in and you got super excited about it.
Yeah, it's a great
Jeff Rinehart: question. So my exposure happened through to you, but prior to that, when I was at capital one, I knew next to nothing. Venture capital and private equity or any of that. Right. But it, to you, I was on the team that was raising the capital. So it was myself and the COO and the CEO that were out when we would raise rounds of financing, we'd have to go out and essentially pitch the company to venture capital firms to try.
And to your point, raise capital, just like Google did, just like Airbnb did is bring that capital in to try and grow the business. So. I got introduced in a very quick, very real way to trying to go raise hundreds of millions of dollars from venture capital firms. And so built a network that way and an [00:37:00] understanding of how that works and how.
Yeah, all the way through IPO. And what does that mean? And board meetings. And so just built network that way. And then that network, again, going back to the point of, you know, people you work with, you want them to hire you again and so on and so on. And the networks are long and windy. When it, when I left to you and was teaching a bunch of those venture firms knew my skillset.
They knew I was a good, direct marketer. They knew I understood. And when they had a company that they thought could use some advising there, they give me a call and say, Hey, I've got this company that needs help here, help there. And like, because of those networks, these VC firms would just drop me in as an advisor.
And that's how I've realized, wow. I really kind of like this and city light, I'll just sort of tease that. So city light I'd known for a long time. City light was one of the first outside investors in you. They came in with. There's a bridge round to the series. They finance as we're city like Cayman. So I got to know my partner.
Now, my partner, [00:38:00] Josh, he was the lead partner on the deal and was on the board early days of two U. So that's how I got to know city light. And as all the, you know, Josh and I had stayed friends over the years and our wives are friends and kids were friends and we'd always kind of talked about doing something together.
And as I started having these realizations of, wow, I'm really digging this kind of advisory work and, you know, Josh and I started talking. Things we could build together at city light, you know, the next transition just happened.
David Fano: And so now you are a professional venture capitalist. Do you ever think that'd be the case?
Jeff Rinehart: Never, never. It is the favorite job I've ever had. Like hands down. I probably still spend a day, a week coding and building stuff inside of city light. You know, we're very, data-driven tech driven. Like we approach our from. Startup founders do we, we build stuff in ways that super cool, but I love it. And you know, I started it at city light.
I was still teaching, so I taught a class here or there and [00:39:00] we just raised it. Fairly large pool of capital, other people's money having a side hustle bad for shepherding other people's money. So, uh, I, I stopped teaching, which that was a tough email to write to say, I wasn't going to seek reappointment at your so back and, uh, have been doing VC standalone, you know, uh, since then, and boy do I love it.
It's great.
David Fano: So question for you. Do you ever consider starting your own. Does it feel like you've got the credentials, you've got the network, you know, but that seems like it was a seems deliberate, but I'm curious as that w you know what teaching is kind of your own thing and this really interesting sort of way, but I'm curious about, you know, going out on your own was something you considered.
Jeff Rinehart: Yeah. I like it is something I never ruled out. Right. Like, I think.
The confluence of [00:40:00] events to make something like that happen, like having the right idea with a co-founder and you're kicking it around and sort of deciding to go do something like those pieces just never kind of came. And, and you know, it wasn't something that I was so passionate about that it needed to be mine.
I w I want to build something like that. Just those paths never happened, and I never forced it to happen. Having said that. We really have approached city light over the past couple of years, a lot like a startup, like, you know, this is I'm building stuff every day and building product and sort of, you know, things that I think are relatively unique, certainly in the impact investing lane of venture capital and really venture capital real large.
So I have gotten a taste of that, um, that.
David Fano: When I, when I think about careers in the folks that go out on their own, it's I think starting a company is just another like, mean. It's not really an end. And it feels to me [00:41:00] from like now having listened to your career, you didn't need that means you've you've wanted agency.
You want growth, you want it to be stretched and you've been able to craft your career in a way that you were always able to get that. And then as soon as you started to. Sure one path could have been to start a company, but you were able to through networks and opportunities continue to grow. And so I'm sure one day, if that happens, it's not off the table as a tactic, but what I think is cool about your careers, you never, at least from what you just told me, it doesn't seem like you ever obsessed on the tactics.
You were more concerned with the experiences and the opportunities, and it's worked out pretty.
Jeff Rinehart: I've never thought about it that way, but that's right. That's right. You know, for me at every step, major or minor, it was about feeling like I could continue to grow and learn at a pace that was steep. And the beauty of venture capital is sorry to interrupt, but you know, the beauty of [00:42:00] venture capitalist.
You're always learning something new, right? Like you're diving in and learning about carbon sequestration and bio char or, you know, cutting edge approaches to dealing with stimulant use disorder or, you know, so when it's on, like you just go deep, deep, deep, and learning new things all the time. Uh, so just definitionally this as a job, family works for me because you're constantly learning, you know, how.
David Fano: Well, from my interactions with you, I feel like that's always the case. And also the beauty is I feel like you reciprocate, you're always teaching. So I feel like I'm always learning. And so I think that makes for, for, for good exchanges. Well, Jeff, that was awesome. I don't feel like you've put a lot of your career out there.
I feel like, you know, you're usually heads down working, so I'm really excited to share your story and for people to see what a cool path.
Jeff Rinehart: Well, thanks. This was really great. Thanks for having,
David Fano: if [00:43:00] folks wanted to connect with you or anything you want to share cool ways for them to stay on top of what you guys are up to at city light.
Jeff Rinehart: Yeah, no. Feel free to find me on LinkedIn or go to city light.vc. You can find me there. If any founders are building something great in climate or education or care, please, please read.
David Fano: Awesome. Well, we'll link to their website in the show notes. Thanks so much, Jeff. I really appreciate it. And yeah, I hope we can do this again.
Jeff Rinehart: We'd love that.
David Fano: And that's it for this episode of nonlinear. If you enjoyed today's conversation, make sure to subscribe, share, and rate us wherever you're listening to the show, you can learn more about teal on our website deal. hq.com. That's teal like the color T E a L H q.com. Or follow us on social. At teal underscore HQ.
Thank you so much for joining us. And please tune back in to keep hearing about how we make the decisions that shape our career. The teal [00:44:00] career paths podcast is produced by rainbow creative with senior producer, Matthew Jones and editor and associate producer, drew Powell. You can find more information on them at rainbow creative dot C O.
Thanks again. We'll see you next time.