From Learning Disabilities to AI Leadership: Jeremy Jakubowicz’s Unconventional Career Journey | Ep034

Episode Information Show Notes Episode SummaryJeremy Jakubowicz’s path to becoming president of multiple AI companies is far from conventional. After struggling with learning disabilities throughout his education, Jeremy carved out a unique career trajectory through film, education, casino promotions, and tech software before landing in his current role. His story demonstrates how challenges can become stepping stones and how following the “natural path” can lead to unexpected success. In This EpisodeJeremy shares how his reading and writing disabilities shaped his approach to career development, emphasizing experiential learning and relationship building. From working as a pizza delivery driver to teaching film production, from MC’ing casino events to transitioning into software sales, Jeremy’s journey showcases the power of turning every experience into an opportunity. His decision to move to Las Vegas for $20,000 less than a competing offer exemplifies his philosophy of betting on long-term vision over immediate gain. Jeremy breaks down how he recognized cultural mismatches in his career transitions and eventually found his home at VizExplorer for seven years before moving into AI. Key Takeaways– Alternative Learning Paths: How Jeremy compensated for reading/writing challenges by becoming hands-on and experiential– Network as Currency: Building genuine relationships opened doors across industries– The Expiration Date Philosophy: Knowing when to pivot based on growth opportunity, cultural fit, or new challenges– Value-Add Mindset: Continuously bringing past experiences to enhance current roles– Cultural Fit > Money: Learning to evaluate opportunities beyond compensation– Natural Path Theory: Why forcing opportunities often leads to resistance Notable Quotes“Don’t overthink things. No matter if it doesn’t work out, you’ll gain valuable takeaways from that experience regardless of its failure or success.”“Everything in life has an expiration date. The thing you need to figure out for yourself is when is that expiration date?”“I always found my path through relationships and building friendships that help open those doors.” Jeremy’s Career TimelineEducational Foundation: Struggled with learning disabilities; found alternative learning methodsFirst Steps: Pizza delivery, film school graduateTeaching Years: Film production teacher with side videography businessCasino Industry: MC, promotions coordinator, progression to managementThe Vegas Gamble: Took pay cut for better opportunity in Las VegasTech Transition: Software sales for casino player tracking systemsVizExplorer Era: Customer success role that lasted 7.5 yearsAI Leadership: Current role as president of multiple AI companies Connect With Jeremyhttps://www.linkedin.com/in/jeremy-jj-jakubowicz-9848a431/ Listen & SubscribeAvailable on all major podcast platforms. Subscribe to Career Downloads for weekly conversations with professionals who’ve navigated unique career paths. Episode Length: 1 hour 4 minutesRelease Date: May 6, 2025 Transcription Manuel: Welcome everyone, my name is Manuel Martinez and this is another episode of Career Downloads, where each episode I basically hit the refresh button, bring on a different guest, to really learn how they navigated their career over time, with the intention to really help uncover any actionable advice that you can use as you’re managing your own career. So for today’s episode, I have with me Jeremy Jakubowicz. We connected, we had a couple conversations and he shared a little bit with me about his journey, you know, the different triumphs and struggles that he’s dealt with. And I thought that was really interesting. So decided to ask him to come on and share his story with everybody. So with that, I’ll go ahead and let Jeremy introduce himself. So welcome Jeremy. Jeremy: Yes, good morning, thank you for having me. Manuel: I appreciate you coming on and being willing to kind of share your experiences. And, you know, we talked about them, so I don’t want to reveal too much, but if you just go ahead and kind of give us a synopsis of, you know, kind of what you’re currently doing, you know, and just a little quick summary of, you know, your career over time. Jeremy: Yeah, no, absolutely. Like I said, thanks so much again for having me on the show. So currently right now I’m the president of a handful of small AI driven companies. Started this about six months ago. And yeah, it’s, I’ll never look back, frankly. So yeah, it’s been fantastic. You know, it’s been a, it’s been an interesting journey to get to the point where I have gotten myself today, starting off as just through grade school, if you will, you know, and getting to a point where I find success and, you know, being able to in my career and obviously raising my family. Manuel: So kind of want to get started. If you give me an idea of, you know, just want to explain to us where you grew up and kind of what eventually, you know, I know we’ve mentioned it before, but you got into technology a little bit later on in life, but just kind of what, you know, what your early aspirations were. Jeremy: Yeah. You know, I think if you get to know me a little bit more, again, raised in, you know, pretty standard middle-class family down in South Florida, in an up and coming area down there back in the early 80s, excuse me, late 80s and early 90s. And you know, at that point, it was just a, again, a nice clean, safe, you know, family-friendly area to grow up. As I was growing up through grade school, I found some challenges along the way. I was, it was an understanding that I had some reading and writing disabilities as a child diagnosed with these understanding of that, you know, it’s going to be a little tough along the way. And it was, it definitely was, you know, I found myself trying to overcompensate in different ways. And that’s, and I set the stage, you know, with saying those different things, because I think it’s important to anybody’s journey and anybody’s, you know, life as they continue to go through their trials and tribulations of, you know, of career and life that you need to understand yourself. You need to understand, you know, what you, who you are first. And then of course, you know, for everybody, that’s watching this, of course, understanding for me, my journey and the struggles that I had. So point is, is that growing up, again, I struggled with some reading and writing disabilities and, you know, and I would have some help along the way, you know, if it wasn’t tutors or if it was guidance counselors or different mentors along the way that I found to be able to help me in my life, I found myself overcompensating in different ways. So if I struggled in reading and writing, I, you can tell probably that, you know, maybe it’s my personality and different things like that, that I was able to latch onto. I was voted class clown in high school. And so I found myself trying to be more outgoing and funny and things like that to overcompensate for my, the inefficiencies on the reading and writing side of my life. So although struggling through actual grade school, I try to use my personality to overcome those different types of challenges. So with that, you know, I always found myself doing other things besides learning through reading or books or, you know, or traditional styles of education and being more hands-on with different things. So if it’s building skate ramps as a kid or taking apart my toys, you know, and then putting them back together, I found myself doing those types of things was the type of, you know, person and personality that I had that I was gonna learn in other ways, learning by doing, learning by experiencing, learning by failure. And to set the stage, that’s really the different things that I find myself doing in order to get myself and propel myself where I am today. Manuel: And that’s pretty interesting, the fact that, you know, you decided to find other ways to learn, right? Because a lot of times, and I’m sure, even with it being a struggle, did you feel that you put in an extra effort on your own to try and kind of surpass that? Or was it really other people kind of helping push you, right, because again, both ways are good. I know sometimes we need just that kind of that motivation, you know, you mentioned you had tutors and people that are like, “No, hey, you can do this.” But then was there also some of that self-determination to say, “Oh, I’m gonna do this.” It may not be the way that you expect me to, but I’m gonna overcome this. Jeremy: Yeah, I think that’s a, I think you nailed it right there. Definitely the latter on this one. I was determined to find a different path than the traditional one that maybe, you know, I grew up believing that you needed to take, right? I know these days with kids, you know, it’s not so traditional in the way that you need to learn and understand things to be successful in this world. But I do believe in the early, you know, in the 90s and things like that, that was still kind of the, you know, the understanding of how you, you know, you get a job and, you know, how you become, you know, a functioning person in society, right? So with that being said, yes, I definitely had some help along the way that was pushing me in certain ways and motivating in others. I, as I mentioned to you, it’s, there’s not a lot of people that actually know that I even have, I struggled, you know, with, you know, those different areas of, you know, in my education and still to that, you know, today, you know, that’s something that kind of sticks with me. But I’ve always, I was able to find those other paths of relationship building and path of, you know, learn...