Raising $40 Million and Building a Company Through a Podcast

Adam Vazquez 00:06
Our guest today is an entrepreneur fresh off a $40 million series B raise. That is Ruben Harris, CEO of Career Karma. Ruben and Career Karma help job training programs find qualified applicants, and they have the huge mission to help 1 billion people find careers. Ruben’s been at the helm of a rocket ship since going through Y Combinator and raising a Series A and B, but today’s episode he shares how he and his co-founders started Career Karma, which was originally born out of a podcast. Oh, you guys know I’m not going to shut up about that. They started a podcast, got the momentum rolling, built content and audience and then built a company out of it. We talked about how the Breaking Into Startups pod launched their business, what it looks like to empower people who don’t look like the status quo to be able to command the careers they deserve, and where he has found the most fulfillment in his journey so far. Ruben has been nothing but kind, generous, and inspiring in the little time I’ve gotten to know him so I’m so excited for you to hear him yourselves. Let’s get into it with Ruben Harris.

Adam Vazquez 01:35
Alright, welcome back. Happy New Year. A little delayed, but we’re back here at Content Is for Closers. Carlton, the people, I’ve been getting tweets left and right: Where’s Carlton? What’s going on? Do you have him in a hole? People are concerned for you, so tell us how you’re doing. Happy New Year.

Carlton Riffel 01:51
Man, if people were tweeting about me, I feel my self esteem has just risen three points. We’re doing good over here. You know, just hunkering down for the winter, for the Omicron season and trying to stay healthy. How about you guys?

Adam Vazquez 02:07
Yeah, it’s been good. We are obviously back with our new cadence. We’ll be back with our weekly episodes now. One note I should say is that we won’t be doing the typical content snacks episodes that we were doing for the back half of last year. I did get a lot of good feedback on those. I’m thankful for that, but we are going to fold in a new episode type. Carlton, why don’t you talk a little bit about that.

Carlton Riffel 02:34
Yeah, so we just had so much content that we wanted to bring to you guys for “Have You HEARD?” that we couldn’t keep it to just one thing a episode. What we’re gonna do is we’re gonna keep this short and sweet for these interview episodes so that you guys can hear what you came for and then we’ll just do a separate breakout episode once a month or something like that, that will dive more into things that we’re hearing, maybe trends in the industry, as well as some things that Adam would have previously done in those snack episodes. So he’ll still be bringing the food, just in larger meals.

Adam Vazquez 03:07
Speaking of relevant news and people eating, today’s guest, Ruben Harris, fresh off a $40 million Series B raise. You’ve heard the episode, Carlton. What stuck out to you or what do you think people should specifically listen for?

Carlton Riffel 03:22
Yeah, so it’s awesome because he started in content before he started his business. He was building in public before people were doing that. He had a lot of really great advisors and people he was talking to, but it started from this place of discovering their industry through content. Even now, they’re still pumping out a lot of content and he talked a lot about bringing it with who they are and bringing it with simplicity, not trying to overcomplicate it and be someone they’re not. It’s a great episode. He really shares his heart behind why he does what he does, and so it’s a great episode for several reasons, but specifically, when it comes to content, it’s just neat that they started creating and they’re still creating.

Adam Vazquez 04:06
Yeah, and I would just add too, I really appreciate Ruben and his commitment. We scheduled this back in November, I think, and it just ended up coinciding with the announcement of his series B the same week. He easily could have pushed it and never even showed a hint of that, so really appreciate it, think you all will enjoy it. Let’s get into this conversation with Ruben Harris. All right, we got Ruben Harris here, CEO of Career Karma on the show with us. Ruben fresh off the slopes and, more importantly, fresh off a Series B. $40 million raise, is that right?

Ruben Harris 04:52
That’s correct, man. People putting that dry powder to work.

Adam Vazquez 04:56
Congrats. Before we go too deep, I gotta say congrats, obviously, and what did it feel like when you saw that wire come through or the email or whatever that notified you? What was the first feeling?

Ruben Harris 05:08
It felt good. It felt good to be in a position where capital is not our biggest concern, that we can focus on solving problems to help people at scale. It also felt good to know that the capital came from impact-oriented people that can fund us all the way through our IPO, so that’s not our main stressor.

Adam Vazquez 05:40
So a little bit of relief, maybe, and some freeing feelings to just be able to go after it now?

Ruben Harris 05:48
Yeah, I mean, we’ve been pretty intentional about raising capital from investors that can fund us all the way to IPO. I think this was validation that they can because most of the people that gave us capital were internal investors or related to our internal investors, like the people that led our Series B were our LPs and initialized capital was all in the family so it’s really cool to be able to continue growing from within the people that we are. It’s kind of like promoting someone from within or growing the internal team. The reason why I like it, it’s relevant when you think about the demographic that we serve at Career Karma that are trying to break into tech. A big challenge that they have is living day-to-day and living check-to-check and not even having that time to think creatively and so this makes me more fired up to be able to put more people in a position where they don’t have to worry about living check-to-check and they can just focus on solving the problems or getting close to their purpose that they want to solve in life and being example to their kids and build a legacy.

Adam Vazquez 07:01
That’s awesome. It’s awesome what you guys are doing, awesome the goals that you have. I see you talking about having the ambition to help a billion people and obviously, when you have that sort of ambition, there’s something in there deeper than money or trying to raise a certain round or anything like that. Have you ever heard of the book Wanting by Luke Sturgis?

Ruben Harris 07:22
Nope, but I’m writing it down.

Adam Vazquez 07:26
Yeah, check it out. It’s about the idea of mimetic desire and why we want things and, listening to your Twitter spaces last week, it just triggered in my head, like, “Oh, he has something deeper that he wants. It’s not about the headline,” because most of the time, you’re going about it not necessarily the fastest way by being so careful with who you take money from and all those sorts of things. There’s an intentionality there. I was curious, around in the last, how long have you been doing Career Karma? Five years, six years?

Ruben Harris 08:00
No, about three years. We started in 2018.

Adam Vazquez 08:04
Wow. So in the last three years, is there an experience or an achievement outside of this raise where you felt truly fulfilled in what you’re doing and in the mission that you’re pursuing? That’s a weird question, but…

Ruben Harris 08:18
No, no, that’s a good question. I’m glad that what’s shining through when people view us externally, that they know that what we’re doing is bigger than money. You touched on why are our ambition is a billion people. Part of the reason for that is because that’s the size of the problem. There’s no bigger problem outside of healthcare than helping millions and billions of people get on their feet, and we truly want to solve this problem. We truly want to create a platform that helps people navigate their careers no matter what point of time that we’re in. When it comes to what makes me feel fulfilled on a day-to-day basis is seeing people get jobs or seeing people be able to provide for their families. Before we started Career Karma, we started up a podcast called Breaking Into Startups where we share stories of people that got jobs in tech. You were in that Twitter space last week where I’m not telling people what Career Karma does anymore. The people themselves are talking about it. You saw that people that are in the Career Karma community joined that space to talk about how Career Karma is changing their life and how they are dedicating themselves to giving back, spreading good career karma, and helping other people achieve what they’ve been able to accomplish and honestly to become better than they are. People talk about compounding a lot from a capital perspective, but relationships compound as well. I want people to be greater than who I am. I truly believe I’ve been put in this position to short circuit the time that it takes for someone to get to the point that I’ve been able to get to, kind of like what a book does to you. Like you were mentioning this book. That book saves years of time that some people got to develop through experience but I can give people my connections today and give people the insights today, I can give people the access to the companies today so they can be better and do it for others.

Adam Vazquez 10:22
I love that. The Twitter spaces, I don’t know if that’s even— I’ll try to find that and if we can link that in the show notes below. I jumped on it because I knew we were gonna have this conversation and it was crazy. Obviously, you talked a little bit about the things you’d expect people to ask about, but then person after person, like you said, kind of just came on stage in the space and talked about the impact that you’ve had and the different things that they’ve received from it. Anybody who’s listening who’d be interested in that, I’ll try to link that below. You mentioned Breaking Into Startups, that was your podcast. Or is your podcast. Are you still doing episodes for that?

Ruben Harris 10:57
We still have the podcast. We still are in a position where we can drop episodes. The last episode that we did was with the CEO of Softbank when we raised our Series A. We haven’t dropped an episode since then, however, since we launched live audio rooms inside of Career Karma, we’ve done more rooms than we’ve done podcasts so whenever we launch a recording, then we’ll be able to do interesting things with the podcast again that’s aligned and consistent with the work that we do on a day-to-day basis.

Adam Vazquez 11:26
Got it. So you started that a couple years right before Career Karma or a while before?

Ruben Harris 11:34
A couple years, yeah. We launched in 2016, yeah.

Adam Vazquez 11:38
Was that intentional? Did you know that was gonna be a forerunner to a company you were eventually gonna launch? Or was it just something like… Talk about how that onboarded you and kind of paved the way for what you eventually did in launching the business.

Ruben Harris 11:49
It was not intentional to become a business. It was intentional from a documenting the journey perspective. I remember when my co-founders were going through their boot camps and how challenging it was for them. Not technically, really, but more psychologically, and how we really had to pump each other up. They would listen to music or workout or talk to somebody that could encourage them. They would always get pumped up when they would read a story that somebody blogged about related to getting a job in tech and they were like, “Man, how awesome would it be if you just get daily motivation of somebody else that got a job in tech to validate that you are on the right path?” It just started off as a love project and then once it started taking off, schools started reaching out saying, “Hey, man, you guys got a big audience for the people we’re trying to reach. We’d love to pay you to get access to your audience.” And we’re like, “Oh, is this a thing? Do schools do this?” That’s when we realized that schools are kind of like startups as well and corporations as well. There’s 1,000s of schools that teach the same thing, but they have their own way of teaching it, so in order to differentiate themselves, they spend money on marketing kind of like how startup does to reach the right users and they leverage not just Google or Facebook, they leverage different platforms from a lead generation perspective. But what they realize is that lead generation is not enough in order to get people to make a life changing decision, so you need community and human beings to speak with these individuals. Even after you serve them, the best recommendation they can trust and even after you connect them to the right schools and the right people, they have to make the decision by talking to people that have gone through it before.

Adam Vazquez 13:56
So you did that, you started having these conversations with folks giving that free advice out, then connecting people with schools, etc. How did that eventually transition to “we’re working with schools, but we’re gonna build our own platform to make those connections?”

Ruben Harris 14:15
That came through encouragement from Michael Seibel, who’s the CEO of Y Combinator. We’d been talking to him for a while when we first moved to the Bay Area in 2014. He kept talking to us about Y Combinator, and we discovered Y Combinator when we were in Atlanta. We knew that in order to start a multibillion dollar company, we needed to know how to code and talk to users, and so my co-founders decided to be the coders. I was going to be the CEO, but we didn’t know what kind of company we wanted to start. Every time we would meet with Michael and he asked us, “Are you ready to start a company or a business?” we would tell him that we had the podcast, and then he would ask us, “Have you quit your job yet?” We would say no, and then he said, “You are not ready, so let me know when you quit your job.” After that happened several times, we decided to quit our job and to build something that’s not a media company but a career navigation platform that leverages the media to reach the right audience and that really has a distribution, leveraging the things that we learn before this. That was the seed of what we have today.

Adam Vazquez 15:45
Cool, yeah, ’cause it’s not a media company but it was kind of burst out of that and continues those themes. I asked people like, “Hey, what should I ask Ruben when I get to talk to him?” One of the questions was, “Your content works without doing a bunch of different gimmicks. It doesn’t seem like it has a ton of brand spin on it, or whatever. How do you all go through that process to create these—whether it be the show episodes or now the conversations in your platform—to just make them relevant and organic?” Is there a process you go through? Is that just who you guys are? What does that look like?

Ruben Harris 16:26
Yeah, it’s a few things. Simplicity is complexly resolved. If you hear the message we’ve communicated pretty much every year, and even before Career Karma was a thing, it’s the same story. There’s little changes, but for the most part, it’s a very clear, focussed message without distractions so that people understand what’s going on. They may not understand it in the beginning, but eventually they think, “Oh, wow, he’s been talking about that for years,” so that’s important. The other thing is to recognize that people outside of tech don’t understand tech jargon, so you have to really understand the language and how to bridge both worlds. When I’m talking about things that my executive coach is teaching me, I’ll talk about things using the letter P that our people will understand but people in tech may not understand, just like how I’ll say breaking into tech without code switching. That’s P. What does that mean? That’s player, that’s cool, that’s amazing. You can be yourself in this world without switching it up. Well, a lot of people feel they got to switch up in order to fit in, but what I tell people is I don’t want to fit in, but I’m still here. Not fitting in is actually what you want to be. That’s how you become contrarian and create those outsized returns and that’s what gives value to the organizations that you’re going to be joining. That’s part of the magic to our message: we’re not catering or trying to sound right. We’re just speaking truth to power and showing people that you can speak truth to power too. For example, I’m from Atlanta, Georgia. There’s a rapper named who just became number one, beating the weekend’s album. For some people that are from Atlanta, they know who he is. Most people, I would argue, don’t know who he is but he has this new term that he’s using called P that you’ve probably seen me post a lot. He’s pushing P, which is short for player, but can be used in different ways when you push it a little bit: when you refer to things like purpose or power or priorities or plans.

Adam Vazquez 19:02
It seems like historically the model has been “this is what it looks like.” You go to school to learn that thing, but you also go to school to learn how to act to be able to do that thing. What you all are doing is saying, “You can look like whatever you look like or sound like however you sound like and then here’s how to do the thing,” the work or the task, rather than trying to play the character. That’s cool. What about you just personally? How do you balance CEO of a successful company now— I’m sure that brings a lot of attachments or obstacles or whatever job, responsibilities, but you’re still out there creating a lot of content, probably kind of leading content for the Career Karma firm. How do you balance those two roles?

Ruben Harris 19:49
It doesn’t come without sacrifice. I recognize that what I do in my personal life will affect the company. No matter what you do, you just have to always think twice and be like, “If I do this in my personal life, will it affect the organization? And if it does affect the organization, is it a good thing or a bad thing?” As chief storyteller, which part of the responsibility of CEO is to tell the story of the company, and as someone that recognizes that every tech company is a media company, part of the reason why these VCs like Andreessen and others are getting are getting their first round and others are getting serious about their content games because that’s how they’re going to be set apart, how they’re going to be visible to others. Every company is starting to evolve, to figure out how they can be more relatable to their people. I do need to figure out how to balance personal and professional because I am kind of a workaholic. The only thing I really do outside of work is exercise or some type of extreme activity, or I watch anime a lot and do things that can feed my mind that I can create analogies to. Then also, I do music. I’ve been doing cello and then I like things that you juice. As I’m speaking about this, everything is more like active rest, where my mind is still thinking about Career Karma all the time. As someone that grew up in the church, there’s admonition and some on Friday and some on Saturday is religious time for me and time to reflect on God in front of the family. That’s a good time where I’m supposed to shut my brain off, but to be perfectly honest, I don’t always shut my brain off on Sabbath and I’m thinking about how to do the Lord’s work.

Adam Vazquez 21:49
I mean, it’s tough. I feel like, yeah, I’ve gone through similar things. I’m not nearly as busy, I don’t think, as what you are. The idea of Sabbath is, I think everyone is at a core level attracted to it. There’s something about just rest and peace and all those things. Then the text comes in or the tweet does well or the opportunity comes through and you have to react to it, so I totally get that. You talked about how everything affects you personally. There’s a negative side of that, but I would hope there’s a positive side to that. When the company gets $40 million wired to it, is there any special celebration purchase that you made or anything thing that you could do like that? I guess maybe some of your trips?

Ruben Harris 22:35
Look, I still got the same hoodie on. I got the same shorts from a Marshalls store that I had on from the beginning. I’m actually moving out of this apartment at the end of this month in San Francisco and I’m moving to Florida, but like, I’m actually in the process of getting rid of most of my material things and going more like on a digital nomad type of thing. Just like using a— Oh, I’ll just use another religious analogy. We think about spreading the gospel. You don’t do it by sitting in a really fancy place. You go from town to town. I’m taking more of that type of approach where like, “Hey, have you heard the good news? You actually don’t have to do these things. You can actually pursue this route and you can change your life.” That type of thing. I don’t want this to get confused where like I’m talking about Career Karma as a religion. I’m not doing that. I’m just saying that I learned a lot of things around like— Just ignore religion, think about the best organizers. We just came out of Martin Luther King weekend. What did Dr. Martin Luther King do? He didn’t stay at Ebenezer Baptist Church. He literally went. If you look at his work schedule, it was insane. Same thing with Malcolm X. He would go from place to place. All the biggest organizers and leaders would have to— even the president. They literally go from city to city, time to time shaking hands, kissing babies, so I have to take that approach. Have I got things that I like? Yeah, I got some new running shoes. I got some cool workout equipment because I have to build up some new muscles to carry this new weight.

Adam Vazquez 24:10
On that itinerant speaker schedule. All right, last question for you. 2022 is obviously starting off with a bang from your perspective, but what has you most excited? What are you looking forward to? And why is that answer running 1,000 miles as part of the Strava club?

Ruben Harris 24:27
Oh, yeah. I like that we started off this year in a way where we’ve got people’s attention now. I think the press run that we did announcing the series B was a home run because the message wasn’t “you raised $40 million” it was like “look at who you raised from.” You’re not just using boot camps. You’re working with higher education now. You’re figuring out how to work with corporations so not only can they pay for education but they work with any education institution to legitimize them. If you have corporations on board that can not only fund tuition but also bless any school with a job outcome, that’s really powerful and, most importantly, for them to know that we’re growing the team, that we’re not going anywhere, that we have to watch has to really become a player that just doesn’t want to get acquired unless you really want to solve this problem and become the biggest player in the game. That was a homerun from a messaging perspective, just by the questions that you’re asking me, which I like a lot. Related to the 1,000 mile club, for the people that don’t know, last year I was able to run over 500 miles. During the beginning of the pandemic, I could barely run half a mile. I tweeted out this year that I want to double it and I want to do 1,000 miles, which turned into a bunch of people creating a whole club that I’m now the de facto leader of so I have to run 1,000 miles. What’s cool about it is that, in tech, a lot of people talk about a marathon mindset (and the marathon continues, RIP Nipsey Hussle), but how many people have really run a marathon? The whole reason I started running was because I wanted to see what it feels like to run a marathon. Now that I’ve done that multiple times, I want to continue that, and there’s a lot of, like, running to me is kind of like moving meditation where I get a lot of time to think and the active rest I was telling you about. With the series B, there’s a lot of analogies where there’s a cool side where we have raised all of these resources to help people, but the stakes are higher, so it’s not time to play games and just splurge and go crazy. It’s time to put that capital to work to help more people. If I’m doing that from a business perspective, I need to do it. From a personal perspective, a lot of people think that their health goes to waste whenever they are running a business, but I want to prove the opposite. By taking care of your body, your mind, your spirit, and your emotions, that makes you a better leader, better CEO, better executive, better operator, better job searcher, better worker, a better husband, wife, family man, whatever.

Adam Vazquez 27:39
Love that. I just got the notification right before we jumped on that the Running In Public episode you do a Chacho that we produce is getting ready. That’s live by now. Go check it out if you’re listening. Ruben, appreciate everything you’re doing. I appreciate all the people that you’re serving and the way you’re doing it. I’m sure everyone knows, but where can people find you if they want to check out what you got going on?

Ruben Harris 28:03
Thank you, man. If you have really enjoyed this episode with my brother Adam and you want to take the step to break into tech, I would go to careerkarma.com/apply. That’s our best recommendations for schools for you and career paths even if you’re not sure. If you want to talk to me directly in our live audio rooms, you can go to careerkarma.com/events. If you want to follow me on Twitter, Instagram, my Twitter name is @RubenHarris. If you want to email me directly, it’s just ruben@careerkarma.com.

Adam Vazquez 28:41
Cool. Appreciate it, brother.

Ruben Harris 28:43
All right, man. Thank you.

Carlton Riffel 28:44
And that’s a wrap. Thank you for listening to this episode of Content Is for Closers. We hope you find this show really helpful as you grow your business with content. Maybe you know of other people who would find this show helpful as well. How about you send them our way? If you didn’t like this show and you want to tell us that, then you can head over to contentisforclosers.com where you can send us a message, give us some feedback, ask questions, or find detailed notes for every episode. Until next time, keep creating and keep closing.