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The wave of the future.

The career world is not how it used to be. The idea of picking one job after college and sticking with it for a lifetime is no longer sustainable. Nor should it be. Having a community where you can learn new skills, familiarize yourself with tech, and get advice from others is priceless in today’s world. The rapid reskilling movement is the wave of the future, and we should all jump in.

A business relationship, the co-founder relationship, is a marriage. And you have to have something that ties you deeper than money

Ruben HarrisCEO of Career Karma


Becoming the Category Kings of the Rapid Reskilling Movement with Ruben Harris

Katie Hankinson (00:02): Hi, I’m Katie Hankinson.

Mickey Cloud (00:04): And I’m Mickey Cloud, and welcome to Building While Flying, a new podcast from the Sasha Group where we interview business leaders about how they tackle challenges, stay resilient, and navigate ever changing skies.

Katie Hankinson (00:22): Welcome to this week’s episode of Building While Flying. Our guest today is Ruben Harris, who is CEO at Career Karma, but also has a pretty diverse background across, originally, investment banking, but you’ve also touched education and healthcare and community organizing and outreach, and you’re also the creator and host of Breaking Into Startups podcast. Welcome.

Ruben Harris (00:49): Thank you. Thanks for having me on the show.

Katie Hankinson (00:50): Well, it’s great to be chatting to you. Given how varied the background is we just talked about, what are you doing, Ruben, right now? Where are you right now and what’s going on in your world right now?

Ruben Harris (01:02): I’m in Atlanta right now, where I’m from, but I’m working on building a company called Career Karma that we started in 2018. It’s the easiest way to find a job training program online, so essentially it’s a marketplace where we match workers to job training programs so they can get high paying jobs in three to 24 months. What’s unique about our community is not only will we match you with a training program, we’ll give you support during the program, during the job search, and for the rest of your life. That’s my current focus.

Ruben Harris (01:32): We have over a million people a month that come to our platform. We have 450 boot camps in our directory, 7,000 trade schools, colleges, and universities, and we are positioning ourselves to not only be the number one destination for career advice on the internet, but also the category kings of the rapid reskilling movement.

Katie Hankinson (01:48): I love that, and I like this term, the rapid reskilling movement, because I guess, let’s talk a bit about that, that is really about the fact that there is a bit of a skills gap in America right now. Was this where you started out when Career Karma came to you? What was the instigation of thinking of Career Karma right from the get go?

Ruben Harris (02:11): Yeah, there’s multiple things. I’ll address the skills gap thing. That’s always been this thing that people talk about a lot. I would say COVID-19 accelerated a lot of these trends, given the fact that there’s over 55 million Americans that had filed for unemployment since the pandemic hit. A lot of these jobs that are being created are in the tech industry, because tech is what the world is running on now. We’re on Zoom right now, right?

Katie Hankinson (02:38): Mm-hmm (affirmative).

Ruben Harris (02:39): Most people aren’t aware of what skillsets to get for those jobs, and our college education system actually isn’t able to keep up with the trends. That’s why we have to go into rapid reskilling. Actually, on the interview that we did with Gary on the Breaking Into Startups podcast, he actually talks about what’s going to happen to the brand college.

Gary Vaynerchuck (03:01): The brand college is going to go through the same thing the brand banks went through. We don’t blame ourselves. Your friend, Omar, who has $413,000 in debt, who has an $89,000 a year job, who decided to borrow $500,000 to get that apartment so he can take the ladies home, he’s not going to blame himself. He’s going to blame fucking Bapsen. Then we’re all going to do that and guess what’s going to happen. People are going to stop sending their fucking kids to college.

Ruben Harris (03:30): Going back to how this came about, you mentioned I have a very diverse background, right?

Katie Hankinson (03:35): You do.

Ruben Harris (03:37): I didn’t go to an Ivy League school. I didn’t have the GPA. Where the world is going is, people aren’t going to stay at one job in one company forever anymore. They’re going to go from school to school to school and company to company to company. Back in the day, you’d just pick one job and you do it forever. But I’ve lived my life this way before it was the default way of everything going. Career Karma just came about, us building a product that we wished that we had when we were breaking at the time.

Ruben Harris (04:13): The podcast is what we use to talk to people who had these same type of experiences. Then through talking to them, we learned what we needed to do in order to go to platform that’s scaled up to where it is today.

Katie Hankinson (04:23): Let’s rewind to that, because to me the whole track that you have really followed, I feel like there’s little pieces along the way that have built to create. It’s almost like you couldn’t have got to this point if you had not had those previous steps before, but you’re still doing exactly what you’re describing, which is that lily pad career, where each step along the way organically feeds the next. So let’s rewind.

Katie Hankinson (04:52): I feel like a good point to rewind to is when you wrote that blog post, Breaking Into Startups, that was the unlock that became what is now a full on show. Do you want to talk a bit about that?

Ruben Harris (05:05): Yeah. I love that you bring that up. For the people that don’t know, I wrote an article before we had a podcast called Breaking Into Startups, and the subtitle is From Cello to Investment Banking to AltSchool. That’s important to understand, because I started my career as an artist. I’ve been playing the cello since I was 4 years old, so almost 30 years. As an artist, you have to really understand the power of media, which you all understand very well.

Ruben Harris (05:35): When I was in school and I graduated, I was performing in different places and I knew I needed to be a good business person, because essentially if you want to be a good, successful artist, you got to master business. As a classical musician, you meet business people. I met a private equity guy that told me if I want to learn business in a short amount of time, do investment banking. None of the alumni from my college actually was an investment banker, so I had to find an online course called Breaking Into Wall Street that I discovered from a blog called Mergers and Inquisitions, where I taught myself financial modeling.

Ruben Harris (06:14): Literally upstairs, I’m at my parents’ house right now, literally I sat at that table every single day where I was going to sit earlier, but there was noise outside, but I literally sat every morning at that table, day and night, just really learning financial modeling. I was going to be an investment banker, despite my background not meeting all the qualities, I shouldn’t be able to be into investment banking. Long story short, through that process of publicly declaring what I was going to do, I was able to not only get into investment banking, but I also got thousands of emails from other people and I helped over 50 people get jobs in the investment banking world that are still bankers today from small schools with diverse backgrounds like mine. Then I named the Breaking Into Startups blog post after Breaking Into Wall Street. Then that lead to becoming this centralized source that guides people into these rapid reskilling programs to help them get into jobs.

Katie Hankinson (07:11): It is such a perfect through line. I think the other really interesting thing about it, which is so true, and I’m sure you and Gary talked a bit about this, too, is part of it is the documenting of your journey to provide education for others who want to take the same journey. The “document, don’t create” type sense, or “document, then create” sense of it is what helped really drive the beginning of it.

Ruben Harris (07:38): That’s actually super interesting that you bring that up, because this is a very in vogue thing that a lot of entrepreneurs are talking about related to building in public, which I think Gary’s talked about and things that I’ve talked about. The things that I’ve talked about have been less on the entrepreneur perspective and more on a personal ground perspective. Document your daily journey for your career, because here’s the facts, right? Certificates and degrees don’t get you jobs, and neither does learning how to code. An employer’s going to Google your name and what pops up is what’s going to be what matters the most. There’s going to be other things, right? Obviously, like how you work with other people and whatever.

Katie Hankinson (08:19): Totally, totally.

Ruben Harris (08:20): But we all have the same experience. We all have the same skillset. Who you are is what matters the most. A good way to demonstrate who you are is not just by building up a portfolio probably that you built, but documenting your life. That’s why in Career Karma, we encourage people to literally ask a question or give an answer every day, create a post every day, engage with content every day, because that helps build up your personal brand, which makes you more relevant for employers in the future.

Katie Hankinson (08:46): I think the other brilliant thing is when you said publicly declare what I wanted to do. I think that’s the other piece. There’s almost building the skillset of documenting, learning, capturing what it is that you’re learning as you go, which has multiple benefits, but also telling the world what you want to do so that people can reach out and help you, and you can be held accountable.

Ruben Harris (09:14): Exactly, telling the world what you want to do before it happens, and make sure it’s a big, scary goal, something that’s completely out of your element. You can’t have courage or bravery without a little bit of fear, or a lot of fear, right? You have to make it this big goal.

Ruben Harris (09:29): What’s interesting about publicly declaring these things is that it’s kind of a forcing project. I know we’re going to talk about this later, but when COVID-19 hit, the most people that were affected were women and people of color. A lot of these people don’t have access to laptops or devices. I was like, “Well, what can I do for them?” I said, “I’m going to raise half a million dollars and give away 5,000 laptops.” And I just publicly declared that, but I had no infrastructure set up to do it. Very quickly, I was able to get over $200,000 and get over a thousand laptops donated. It’s still in process, it’s not done, but now that I’ve said I’m going to do it, I have to do it. There’s a lot of power in publicly declaring it. It puts your feet to the fire.

Katie Hankinson (10:14): Do you think the space is doing enough to try and close some of these gaps? What are you seeing that’s positive in terms of moves in the right direction? And where do you think we all ought to be looking to hold ourselves accountable to some of these big, hairy goals?

Ruben Harris (10:33): Let’s start with positives. I see a lot of amazing entrepreneurs that are doing what they can to address the needs related to future work, not just skills gap or devices, but also financial support through innovative things like income share agreements or deferred tuition. You see a lot of people innovating around housing. A lot of really cool things on the entrepreneur side of things.

Ruben Harris (10:58): But the fact of the matter is venture capital is a very small drop in the bucket when it comes to workforce development. The bigger people that focus on workforce development for the most part is philanthropy and government. In my opinion, this is my personal opinion given that I’ve been working with a lot of philanthropists on the Reskill America campaign, there’s a lot of money in philanthropy, but it’s also very, very slow. A lot of the money doesn’t actually go to the communities that you think it would go to.

Ruben Harris (11:38): My buddy, Edgar Villanueva, I believe is his name, he talks about how I think less than 8% of philanthropic dollars go to communities of color, surprisingly. Something like that. Don’t quote me on that, but that’s an issue, right? If we have all this capital that should go to help people, I think that’s a big deal. There’s also a lot of things that governments can do. I think if you look at what government did with America Job Corps and the WIO Act and things like that.

Ruben Harris (12:11): If I was going to think about what we can do now versus what’s been historically, I would study what happened during World War II. I think this is the greatest reallocation of labor since World War II. One of the biggest things that happened during World War II was women entering the workforce, which I think is actually one of the biggest economic events of our life. I think it was six million women entered the workforce, something like that. There was also the GI Bill that was created for veterans.

Ruben Harris (12:45): Whatever happened with this election, either party, and both parties, by the way, are for things related to reskilling. I know with the Obama Administration there was the WIO Act, Workforce Investment Opportunity Act, and with this administration there’s the Find Something New. I know Ivanka said about find something new in trade schools and things like that. Either one of them, whatever they decide to do, I think that if we could create something related to a skills package or giving every American access to some kind of a stipend to be able to get an education, not just from college, but from a trade school or a boot camp, I think that would be massive.

Ruben Harris (13:30): I also think for a lot of these private boot camps, they aren’t able to access the student loan stuff that you can with colleges. If you can make that type of stuff available, I forget the exact level, I think Title IV Pell Grant type stuff available for boot camps. I think that would also be a very big deal as well. I’m not a politician, so I’m not going to pretend like I know a lot about government, but I will give credit that I do know that government does a lot, not just in the United States, but globally. I think that the solution to the rapid reskilling problems of our day is going to require a combination of public-private partnership to get that done.

Katie Hankinson (14:12): I think that’s such an important thing to call out. I think so often business and the capitalist machine tends to focus on, “What can we do from within the world of enterprise?” There’s a huge parallel with starting a business, the actual idea of being in tech. That exact thing is almost what the Zuckerbergs or the historic great leaders of tech companies have done time and time again.

Ruben Harris (14:41): Can you imagine if Jeff Bezos had a daily blog or a daily vlog? That would have been amazing. Or Elon Musk or Zuckerberg? All these people, nobody has ever documented the journey of the creation of a billion dollar company, and I want to do that.

Katie Hankinson (14:58): I love that. That’s awesome. Break Into Startups was a bridging experience. You took what you’d learned about breaking into Wall Street, you applied it yourself to Breaking Into Startups. You have a series where you help other people do the same, and Career Karma is now a platform. Can we talk quickly about how the platform works? I think the Karma bit is really interesting.

Katie Hankinson (15:20): It’s free to students, right? You’re not-

Ruben Harris (15:22): That’s right.

Katie Hankinson (15:23): …asking people to front cash at this point, which is important at this point in their career? So how does the platform work? What is your business model?

Ruben Harris (15:29): That’s right. Most people come to Career Karma for career advice. To your point, it’s free for them. The vast majority of people are just looking for guidance for where they are in their career, but for the people that want to take action on their career, they’re able to sign up for something that we call FastTrack that you can see at What that does is, it allows them to pick different career paths and different preferences about whether they want to do it online or offline or part time or full time, what their current financial situation is, et cetera, and they’ll get matched directly with job training programs that are best for them.

Ruben Harris (16:06): Once they see these different job training programs that are narrowed down, because it’s hard to choose from thousands of programs, then we narrow it down to two to four programs. They’re able to click interested on a school and they get called within five minutes, or if they’re too busy, then they’ll get reached out to within 24 to 48 hours. They’re able to speak with the school and get the navigation support from other people like them in a group called a Squad to get accepted in a matter of one to three weeks. That’s what happens there.

Ruben Harris (16:38): Then once people are inside of a program, they’re able to ask questions and give answers daily, to create their profile, they’re able to take advantage of different workshops that we have going on, different scholarships that are available, but most importantly when they’re done with their program, they can upload their projects into Career Karma to get up loaded or downloaded, very similar to [inaudible 00:16:58] and Behance having a baby, and then we can actually connect them with other people that are like them, other moms or other dads that are already employed as engineers or designers that were previously bartenders to get vouched and get into a job without having to go through the website.

Katie Hankinson (17:15): Amazing. It’s almost like an educational accelerator that mimics so much of how accelerators work in terms of you have your cohort, but also with that whole air of giving back to the people who are climbing up. None of this pull up the ladder behind you.

Ruben Harris (17:35): Exactly.

Katie Hankinson (17:35): It’s the exact opposite.

Ruben Harris (17:35): That’s exactly right. I like that you bring that up, because you mentioned it’s free, right? What we say is the only cost is if you get any value out of the app, that you help somebody behind you in the future. What I talk to investors, like, “Okay, so what’s the incentives? Why are people helping each other?” Well, if I’m trying to get into a program, the best person to talk is somebody that’s currently in the program versus somebody that did it three years ago, because the curriculum changed.

Ruben Harris (18:01): If I help people at my level and I get access to a person above me and to the program, what’s their incentive? Well, the people that are currently in the program want to get to talk to people who are in the job search, because they’re about to be in the job search. In exchange for helping somebody get into the program, you get access to someone in the job search. What’s the incentive for someone in the job search to help somebody in the program? Well, they want to talk to people that are employed, right?

Ruben Harris (18:23): It’s this never ending ladder that really doesn’t end, even all the way into entrepreneurship and venture capital, because the fact of the matter is, the tech industry is just like everything else in life. It’s all about relationships and people helping people. It would be frowned upon to charge money for a mock Y combinator interview, for example, or an introduction to a venture capitalist. It doesn’t make sense.

Ruben Harris (18:45): It’s about love. It’s about friendship. It’s about looking out for each other and, yes, it is about money, but there’s different places where those things get introduced.

Katie Hankinson (18:54): I think that’s also so important, because back to that point about it’s the soft skills that you’re building around building trust, building rapport, being able to make a pitch to people. The name of this podcast is Building While Flying and we talk a lot about how fast everything is moving. Yes, there’s a karma thing to helping the person behind you because you’re giving them the knowledge you’ve learned today, but I think probably there’s also quite an advantage to having a little connection back to what’s happening right now with the people going through it, because shit’s already changed.

Ruben Harris (19:31): Exactly.

Katie Hankinson (19:32): You’re learning from the people who are behind you as well.

Ruben Harris (19:36): Exactly. The only way to stay on top is to be aware of what’s happening. That’s why Gary’s talking about the work from home movement and how that’s going to change real estate over the next few years. That’s why he talked about LinkedIn stories and all the stuff that you all are talking about as well, and that’s why you all have a business, right? To help people stay on top, because the world’s moving so fast. So, yeah.

Katie Hankinson (20:00): Let’s talk. I had a question at the end of my little list actually about the cello. I was curious about how the musical part of your background and beginnings has impacted the way you’ve thought about the other parts of your world. How has that part of your life influenced others?

Ruben Harris (20:21): It’s everything. When I was in college, I was teaching cello lessons. I had 20 students. One of them was a 6-year-old kid. He was like, “Mommy, I don’t want to practice. What’s the point of practicing?” Like I told him, I was like, “The ability to play an instrument well is a by product of the life skills that you’re learning.” It’s not about playing the cello, it’s what do you develop from playing the cello?

Ruben Harris (20:47): Jujitsu’s not just about kicking people’s behinds. It’s a philosophy of life. It’s a way of being successful and a bunch of other stuff that we could talk about, but going back to the cello. Very simply, doing something consistently every day. That’s basic. You started learning that. You learned how to not just do something consistently every day, you learned that it’s a waste of time to do the same thing every day. The better thing to do is identify where your weakest areas are and focus on that for the most part. You might breeze through the things that you know, but then pinpoint the weakest areas and just drill on that area for the rest of the time so that when you summarize at the end of your practice, when you run through it, now that’s the new baseline.

Katie Hankinson (21:40): You’ve evened everything out, yeah.

Ruben Harris (21:42): Exactly, that’s the new baseline. A lot of times, when you start a new practice, it’s very easy to just run through and do everything that you know all the time. Over time, you realize that that’s not an effective use of your time. It’s not about you need to practice an hour or two hours every day. It’s what’s the quality of your practice? Did you get into a flow state? It’s not just enough to just play and note feel it. Learning the notes is the easy part. Now you got to learn how to express yourself. You got to memorize it and now you’re not playing no more. You’re just talking. You’re communicating. You’re feeling it. That’s why you-

Katie Hankinson (22:20): It’s the language.

Ruben Harris (22:21): [crosstalk 00:22:21] over somebody else. Now, that’s more solo type stuff, where you’re stretching. You’re doing all these stretch goals, and we can go into that later. I would say the bigger thing for me, giving that I’m very alpha, I learned how to work with other people. Even if you’re the best musician, you got to learn how to work with others. You can’t always play loud, sometimes you got to rest and let the other person shine when you’re doing chamber music or if you’re playing in a symphony. You got to learn a lot of leadership skills.

Ruben Harris (22:57): Again, going back to what it is as an artist, there’s a very famous thing about if you want to make a living as an artist, you need 1,000 true fans. A true fan is defined as someone that spends $100 on your product. All right? Almost anybody can do this. You can count to 1,000 and you just got to get somebody to pay $100, make it $50, right? Now you’re making $50,000 a year and all you got to do is just get them to the page for your digital content, to come out to your shows, your merch. You can pass out mix tapes, whatever you got to do.

Ruben Harris (23:32): One of my friends, Brock Luker, who’s the CEO of 808 Mafia here in Atlanta, his whole thing is music sells everything but music.

Katie Hankinson (23:41): Oh, that’s so true.

Ruben Harris (23:43): In tech, we talk about distribution. Who knows distribution more than artists? All right? Most artists that are famous aren’t good musicians and they didn’t go to Julliard. They’re just really good at distribution and practicing.

Katie Hankinson (23:59): Is that something you see on the platform? That there are people coming in from really incredibly different backgrounds and in some ways they’re the ones that do the best or have the most interesting journeys? Are there any examples that you’d speak to?

Ruben Harris (24:13): Yeah, absolutely. I would say when you think about what happens on Career Karma after you enroll into a program, you’re able to take advantage of the social networking aspects of it with other people. You think about it like an alternative to LinkedIn for blue collar workers. The reason why I bring this up is because LinkedIn did a lot of brilliant things by putting the resume online, which I think is awesome, but it’s focused on white collar people. If you didn’t go to college and you don’t have prestige, you don’t look good on LinkedIn. It doesn’t look good.

Ruben Harris (24:46): In Career Karma, it doesn’t matter what your background is, you’re always going to look good. What we teach people to understand is that whatever work experience that you have, or life experience that you’ve had, all of that is valuable. Whatever struggle you’ve been given, you’ve been given it for a reason. For example, my father’s an oncologist so if you live with cancer and you’re a cancer survivor, you probably know more about cancer than most people. If you are trying to get into the healthcare technology field and you’re applying to tech companies that focus on curing cancer and you built projects during your boot camp related to cancer survivors or people dealing with cancer and you apply to those tech companies, and you’re competing against an engineer with 10 years experience that never lived with cancer, you’re not a junior developer, you are a cancer survivor that knows how to cope and probably knows more about cancer than even the CEO. So you have an advantage.

Ruben Harris (25:44): All these different people that feel like a minority or underrepresented or underserved, I tell them eff all of that. Change all of that mindset. It’s about we’re underestimated. If people are underestimating you, it’s easy to exceed their expectations. You got to change your mindset and just be like, “Everything that I have is an advantage. Now I got to figure out how to present in a way where people can see how dope my life is or why I’ve been given these trials.” Right?

Ruben Harris (26:16): Some people’s been through some hard things, whether it’s adoption, whether it’s abuse, whether it’s a struggle, whether it’s being formerly incarcerated. You name a situation that somebody’s dealt with, we got it.

Katie Hankinson (26:29): Yeah.

Ruben Harris (26:30): Domestic violence, all of that. Currently. People trying to damage their journey while they’re going through their journey because of [inaudible 00:26:39] mindset, all of that exists. That’s real life. If you want to address the needs of blue collar workers, you got to understand what their needs are where they are, and not be afraid of that. That’s how we get it done. I think that’s why we created this magical community.

Katie Hankinson (26:53): I think that sounds awesome. Have there ever been moments along this journey, because the description of it feels so organic and, I don’t know, one thing just so seamlessly moved into the others. Have there been times where you were just like, “Oh, shit. Maybe I’ve gone down the wrong path. There’s a pitfall. There’s been a disaster.” What have been some of the tougher moments of this trajectory so far?

Ruben Harris (27:17): A whole lot. I know it sounds like it’s a very clean art, but I’ve been laid off three times in my lifetime. Fundraising journey is a great example of people that I’ve known my whole life that I thought were going to be down for the movement that weren’t down for the movement at that time, that joined the movement later. The thing that’s important, going back to the point about relationships, you never want to burn your bridges. No’s turn to yes’s, yes’s turn to no’s for good reason.

Ruben Harris (27:50): Sometimes, even if you did your best, for example to get into investment banking I absolutely crushed my interviews for investment banking to get into SunTrust and they rejected me. I ended up at BMO Capital Markets in Chicago. Then I ended up getting recruited by SunTrust later inbound and I came into SunTrust with rank, which is how I came and met my first co-founder, Artur Meyster, and then that’s how I met his twin brother. None of us knew how to code, and through that experience one of our buddies quitting the bank, he copped up and became an engineer. That’s how we discovered boot camps, and he was in the same cohort as Jack Altman, who was also an investment banker. That’s how we discovered Y combinators. That’s how it happened.

Ruben Harris (28:33): It’s not about having everything figured out. It’s about pointing yourself in the right direction and to continue moving. I like this term, but it might come off the wrong way, but I’m going to say it. The great quote that I learned when I was in DC is called, “Sharks are born swimming.” You got to keep swimming and keep one eye open all the time.

Katie Hankinson (28:53): That’s a classic alpha statement, that one right there. My next question was literally going to be, what would be the advice you would give to an entrepreneur seeking to start out who may not come with the everything on a platter or the easy path ahead of them? I think point in the right direction and keep moving is pretty damn spot on, in terms of you’ve got to stay focused and drive that momentum. Any other real specific life lessons or real direction, the things that really keep you going when you’re in some of those pitfall moments?

Ruben Harris (29:41): I’ve got this one a lot. A lot of people asking about entrepreneurship lately, so I always recommend if someone has not worked in the tech industry at all, that they should work in the tech industry for at least one to three years. I think that’s number one. Startups are hard. Running a business, period, is hard. Most of them never get to a million dollars. Most of them fail. The reason why I say you need to work at a tech company is because, if you don’t have tech at your core, you’re a dinosaur and your company will die. It’s fact.

Ruben Harris (30:16): You have to have some kind of tech elements to it. If you want to run a tech company, and I’m biased because I’m in tech, if you want to run a tech company, how you going to know how to run a tech company if you’ve never worked for them or seen how it works on the inside? It’s possible, but why would you handicap yourself? It’s not necessary to handicap yourself.

Ruben Harris (30:34): Now, let’s say that you do have that type of experience, but you don’t have the right skills or that you agree that you want to get into tech. The next thing I tell people is the two skills I would focus on is you either want to learn how to sell or learn how to code. Ideally, you could do both, because if you do both, you’re unstoppable. This is why I say that. The fastest way to break into tech is sales or coding, but something that Y combinators ask about is doing things that build scale. If you want to build billion dollar companies, you want to start off by writing code and talking to users. The reason why you want to talk to users, and you’re going to learn that through selling, is because you want to make something that people want. Ideally, you’re making something that people need, especially during a pandemic, so people are dependent on whatever it is you’re doing to relieve their problems.

Ruben Harris (31:33): Once you do that, the other reason why that’s important is because both of these jobs pay well. You’re going to be making a good living and you’re going to learn a lot of the things that you’re going to be needing in order to have a job.

Katie Hankinson (31:44): Right.

Ruben Harris (31:45): Once you’re inside a company, your top priority, in my opinion, is to find co-founders. The reason why I say that is because I don’t want people to get it twisted. Don’t go out there trying to find the co-founders. Go out there just trying to be you. It’s kind of like being like, “I’m going to move to X place to get married,” or, “I’m going to just go find love.” You don’t do that. It happens sometimes, like, “I’m going to find my wife right now.”

Katie Hankinson (32:14): Right out the front door, that’s going to happen.

Ruben Harris (32:19): Exactly. You got to be you. Have conversations that have nothing to do with business. Can you talk for hours about nothing? Can you get into healthy disagreements about things? Or can you guys have healthy conversations about things you disagree on and still be friends? Those things matter, because a business relationship, a co-founder relationship, is a marriage. It is a marriage. You have to have something that ties you deeper than money.

Ruben Harris (32:45): That’s why a lot of these accelerators historically focused on colleges, because usually college isn’t about jobs. It never has been, even though that’s how it’s been sold. College is about the social experience and exposing you to different ideas and meeting people and proving that you can start and finish something. That’s what college is about in my opinion, because you could also talk about numbers. 41% of college grads are underemployed. It’s not about jobs. Now that it’s acceptable to get a job whether you went to college or not, all these big companies like Google and Amazon, Facebook, they’re all dropping the requirement to have a college degree. Now you can find co-founders, not just from college or boot camps or trade schools, but also from [crosstalk 00:33:36].

Katie Hankinson (33:35): But on the career ladder, yeah, yeah.

Ruben Harris (33:37): The career ladder. I recommend that, because it’s already difficult to start a company if you’ve never worked at a tech company, but it’s also even more difficult if you try and do it by yourself.

Katie Hankinson (33:50): Right.

Ruben Harris (33:51): If you do do it by yourself, you need to learn how to code. You have to be a coder. That’s my opinion. If you decide to get a co-founder and you’re not the coder, you need to make sure that your co-founders are technical. That’s where I would start.

Katie Hankinson (34:08): I think that being a practitioner to me is just such a huge theme. Very much in the world of tech, understanding how to code, but you could apply it to almost anything. Gary’s mantra, too. He was a practitioner in the world of social media before he started telling everybody else how to leverage it to grow their business. You need to be dangerous at the thing that you’re about to try and sell to the word, basically. Bit more than dangerous, ideally.

Ruben Harris (34:35): I was just going to say, I’m not a coder. My background’s in sales and startups, but I know how to speak the language of engineers. You just have to be able to not just communicate in their language, but also get their respect and trust as their leader, pretty much, and also empower them to be leaders as well and not micromanage them, either. We need to be able to trust that things are getting done so that you don’t become a micromanager and that you delegate properly.

Katie Hankinson (35:01): Hell, yeah. That’s a trap, that one. Trust leads to the ability to delegate, for sure. As we draw to the end of this conversation, which I could have for ages, because I just love all this stuff. I think it’s so interesting how people learn as well and the platform that you’ve built I think is just so perfectly timed for where we are today, but what is next? It sounds like you’ve got some irons in the fire. What are you excited about for what’s to come?

Ruben Harris (35:33): Yeah, we’ve got a big announcement coming out that’s going to be super cool. It’s going to take the company to the next level, so it’ll probably drop November. Stay tuned for that. Two big announcements, so that’s going to be really exciting, to take java skill to the next level. We also currently offer six different career paths, but we’re going to be expanding to offer many more career paths for people, so people can choose from all those things.

Ruben Harris (36:02): Like I said, we got about a million people a month coming to our platform. We’re shooting at about 20 million a month over the next couple of years and we’re going to be building a lot of really cool features, for not just our workers, but also for all stakeholders in the community. For schools, companies, governments, nonprofits, so that they can create relevant content that these workers can engage with for their various missions and these goals. Stay tuned for the software that we go for that.

Katie Hankinson (36:31): Really expanding the platform into a platform on steroids. That’s so exciting.

Ruben Harris (36:39): That’s right, that’s right. I will say, if you think about where the internet was before, the internet had all these directories, right? That will aggregate a bunch of information and give you reviews. Kind of like Consumer Reports or Better Business Bureau. That’s great, but we think directory 2.0 is going to look less like the Yellow Pages and more like [inaudible 00:37:03], so you need that community side of things. That’s what we’re building is this directory 2.0 that people are able to take advantage of.

Ruben Harris (37:12): If you think about what we’re positioning ourselves for, there’s currently over a billion education and career related searches per month on Google, and only I think less than 5% of education searches are branded. We want to be that brand that everybody thinks of whenever they want to get a new skill or get a new job so that we, like I said before, are the category kings of the rapid reskilling movement.

Katie Hankinson (37:37): By the way, I just do like the way that trips off the tongue. The category kings of the rapid reskilling movement. Watch this space. I’m feeling it, I’m feeling it. Well, I’m excited. I’ll be keeping an eye open. We’ll share the details in the show notes as well as just as a reminder of the Reskill America initiative, so if anyone wants to get involved or spread the word they will be able to do that. But in the meantime, I’m so grateful for your time.

Ruben Harris (38:10): Likewise. This is super fun, I really enjoyed it.

Katie Hankinson (38:10): This was so fun. Really looking forward to seeing what’s next for you guys on Career Karma-

Ruben Harris (38:17): Thank you, thank you.

Katie Hankinson (38:17): …as well as Breaking Into Startups. Thank you so much, Ruben.

Ruben Harris (38:22): Thank you, thank you.

Katie Hankinson (38:26): Well, now that we’ve finished that thoroughly interesting interview, we’re getting ready to land. But before we do, Mickey and I spent some time unpacking some of the key takeaways that really stuck out to us.

Mickey Cloud (38:37): We liken this to the post-game show where we break down the really extraordinary nuggets that we can all benefit from, including us here at the Sasha Group. So get ready for it, the Sasha Sidebar.

Mickey Cloud (38:54): Katie, that was an awesome, awesome conversation with Ruben. I am legitimately just inspired by what he’s building with Career Karma.

Katie Hankinson (39:04): Yeah, what a journey. What a path. Such a great concept and such great momentum.

Mickey Cloud (39:10): Yeah, and obviously it’s this great reskilling of America is a critical need. It’s something he talked about where he was like, “I went back and I’m studying what happened in World War II and how that was transformational for our economy, and it was about women entering the workforce and the GI Bill. How do we take what we’re doing and are we doing enough to support the folks that have been most disenfranchised by COVID and just generally?”

Mickey Cloud (39:39): He talked about the need to scale something like this through public-private partnerships, and that just immediately sparked in my mind public-private partnerships is not something I knew a lot about when I lived in New York, but having lived in Chattanooga for the last five and a half years, it’s something that this community really embraces. I think this community genuinely does a great job of it.

Mickey Cloud (39:58): An example of that is when COVID hit, our school system obviously had, we were doing remote learning and there might be homes where there’s only one laptop in the family or they might not have high speed internet. That obviously makes school such a challenge. Our local utility company was also our internet and cable provider here locally, and is the reason why Chattanooga has the fastest internet in the western hemisphere. EBP, they actually partnered with our local Hamilton County schools so that anyone on a free or reduced lunch in the school system is now eligible for no-cost home internet, trying to bridge that digital divide. Those families will now have high speed internet for free because they’re eligible for free or reduced lunch.

Mickey Cloud (40:53): I think those opportunities to pool resources is at the heart of the public-private partnerships. It’s like, “Yeah, how do we get Career Karma involved with chambers of commerces, of any talent workforce development initiative?” Because there’s so many of those going on around the country, and that’s what I just get so excited about. How does Career Karma expand and have as big of impact as I know that they can have.

Katie Hankinson (41:24): Yeah, 100%. I just think as an initiative, the Reskill America concept is so important. They’re obviously doing a lot of partnering with DNI leaders, different organizations.

Mickey Cloud (41:37): Another really cool thought that he shared that I just never thought about before, which is he described Career Karma as an alternative LinkedIn for blue collar workers. I had never really thought about the fact that LinkedIn, yeah, it is built for corporate ladder climbers who are showing off their resume and their skills and all that kind of stuff. Career Karma being a place where whatever work or life experience you have, it’s valuable, I just thought that was so interesting.

Mickey Cloud (42:10): His advice on you either ask a question or give an answer every day on our platform, and that’s the way you build yourself up, that could be applied to your social strategy, quite honestly. That’s a really great way to think about how you contribute and how you can do little things to help build your company or your brand. It obviously is a best practice with Career Karma.

Katie Hankinson (42:36): Absolutely. Ask a question, don’t be afraid to reach out, leverage the network, and help the people who are climbing up the ladder behind you. I think they’re all such powerful things, and I think he’s well on his way to building something that will be the category kings of the rapid reskilling movement, which I think is an awesome sound bite.

Mickey Cloud (42:56): Yeah, no, that’s great. I was so impressed with his whole story, but also how important that the work he’s doing right now is for America and for our economy and for so many people.

Katie Hankinson (43:12): Maybe that’s our question or our point. It’s less of a question, it’s more for those of you who want to get involved in Reskill America or have ideas about how to potentially contribute to that part of the program, let us know on our channels.

Mickey Cloud (43:28): Yeah, if you can get involved, because there’s ways your business or your organizations can get involved, we’d love to hear that.

Mickey Cloud (43:37): Thanks for joining us, gang, and for Building While Flying with the Sasha Group today. I hope you learned as much as we did. We’ll meet you right back here next time for another flight. If you’d like to hear more about how business owners and brands are navigating these times, tune into the next episode. And if you’re so kind, please rate and review us. Plus, we’d love feedback, so let us know what you think, what you’d like us to dig into next on Building While Flying, across brands, businesses, marketing, and more.

Katie Hankinson (44:03): This podcast is produced by the team at Original music by Fulton Street Music Group.

Welcome to Building While Flying!

This weekly podcast is brought to you by the Sasha Group. We’re the consultancy meets agency arm of the VaynerX family of companies. We help ambitious companies build strong brands that flex with the times through strategy, branding media and marketing.

In ever-changing times, businesses and brands have to shift and adapt. And across all sectors, there is an air of experimentation. Business owners are trying new things out in the wild;  building the plane while flying.

Ruben Harris wants everyone to have a space to learn new skills and build new careers.

As CEO of Career Karma, Ruben Harris sees the incredible need for reskilling. He describes Career Karma as “an alternative LinkedIn for blue-collar workers.” And with over 55 million Americans filing for unemployment since the pandemic hit, it’s a much-needed platform for those looking to reshape their careers moving forward.

It’s not hard to see how Ruben was able to see the gaps in online job platforms. With a career background as diverse as his, he was able to see the needs of those who may not be in the corporate ladder-climbing category. As an accomplished musician, former investment banker and startup enthusiast, Ruben noticed a trend. There was a gaping lack of platforms for those looking to reskill and shift directions in their career.

In this episode, Ruben enlightens Katie on the rapid reskilling movement and why it’s so incredibly essential at this moment in time. He shares his brilliant ideas for Reskill America: The Great Rehiring Initiative, a program dedicated to providing resources like laptops to communities that need them. And he gives us a bit of his background that gives context to his incredible passion for this type of work. Tune in, and then you can say you knew of Ruben back before his company were the category kings of the rapid reskilling movement.

Other in-flight topics:

  • The diverse career background that gave birth to Career Karma
  • What to expect when you join Career Karma
  • The skill gaps in America
  • The power of tech skills
  • Ruben’s brilliant WW2 tie-in
  • Reskill America
  • Mickey’s thoughts in the Sasha Sidebar

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Chattanooga, TN
Los Angeles, CA