My Journey into AI

Original Post on Medium: My Journey into AI. A short post detailing my entry into AI… | by Sam Bobo | Feb, 2025 | Medium

Last week, I was fortunate enough to speak with members of my high school (well… elementary, middle, and high school) alma mater in an interview style format to build content for an upcoming alumni magazine that will be published centered around alumni working in Artificial Intelligence. Many of the questions centered around my journey into AI and I realized that I had yet to write about such a topic as a blog piece, so here we are today!

My Journey

Since I was a child, I’ve been fascinated by technology. My mom recalls me sitting down at the computer at the age of 5 and booting up Encyclopedia Encarta to learn different languages. I grew up playing video games, had my first laptop in the 4th grade, and, like my peers, became increasingly technologically savvy. Now, I was never a hacker or into IT related work. My friends were duel booting their laptops in Linux and trying to workaround firewalls with proxies but that was never me. Fast forward to college where I pursued a duel degree in Business Administration (specializing in Information Systems and Operations Management) alongside Mathematics, a combination our business school could not anticipate as most went big accounting, finance, consulting, and the like, definitely not big tech (10 years later, big tech and AI are a top focus). A college buddy of mine and I started the Data Analytics Club and I was a Teachers Assistant for an Excel Basics to Blackbelts course. I even spent an entire semester focusing on algorithms and computer science (in retrospect I should have also pursued a minor in Computer Science). The most notable influence was my wife, who saw the passion in my eyes for technology and continued to push me to pursue this dream (thank you!).

I attribute the start of my AI career to IBM, who, unexpectedly shifted my job interview intended for the Global Business unit to IBM Watson in a program called Blue Spark, which was a college graduate incubation program that was sales based, but provided rotations across multiple fields of work from marketing, product management, consulting, and more. I spent countless hours researching IBM Watson and Artificial Intelligence to learn all that I could. For context, this was in 2014 and IBM Watson played on Jeopardy! in 2011 and the IBM Watson HQ opened in New York shortly after I joined the company. My passion and enthusiasm radiated among the cohort interviewing my and I landed the job at IBM Watson. With a wealth of knowledge at my fingertips, I took every course at IBM I could get my hands on, from learning about bi-grams, tri-grams and n-grams largely for natural language processing but about corpora, supervised and unsupervised machine learning, and the like. This was also the era of Conversational AI capabilities so that included natural language classification, sentiment analysis, text-to-speech and speech-to-text, and dialog systems.

While in the Ecosystem Team, I managed a portfolio of 40 leading technology start-ups in the Education Technology, Internet of Things, and Data Analytics sectors. I advised CEOs and CTOs from detailed product design and implementation through revenue maximization, utilizing leading AI technologies on the IBM Cloud. These entrepreneurs and early adopters of AI spanned some highly unique and diversified use cases. Many of these companies tried to adapt AI to fit non-AI use cases, others were too early to the market and could have benefited from Generative AI, others thrived on current Conversational AI capabilities, and a few are thriving in the world of Generative AI!

As with most of the general populus, I was absolutely fascinated by Generative AI capabilities debuted by OpenAI’s ChatGPT. Similar to my early Watson days, I took to the internet to learn about attention mechanisms, prompt engineering, text-to-image processing, and more to ground myself in the capabilities. This time, my modality of learning took a new approach, blogging, which is why I started my blog here! Through writing about my experiences with Artificial Intelligence, I was able to formulate frameworks around the world around me, share my perspective on the world, and catalog my thoughts to resurface in the future.

Drawn to AI

What fascinates me about Artificial Intelligence is twofold:

1. Natural Language Processing — its truly fascinating that we can “translate” human language into machine understanding. Simply from “studying” the placement of words (n-grams), building corpora of knowledge, and engineering algorithms of mass prediction (a la Generative AI), its truly remarkable that humans can design such a system.
2. Impact and Potential — simply by building supervised and unsupervised models, again, that are probability and statistics based, of highly complex domains (healthcare, financial services, law, etc), we are actually encapsulating highly specialized human intelligence into a reusable asset and one that can operate at scale by discovering the minutia of details. That is why I am so in favor of the Leader-Agent Model I devised!

My background, again, was mathematics and business technology, what better way than AI to combine the two! I continue to be in awe about the transformative nature of AI, the debates over foundational principals and the sheer ideas of entrepreneurs (I, myself, included in that mix with a few ideas of my own!). My hope for the world is that we focus on the Leader-Agent model to combine our collective intelligence into a set of systems that can solve complex problems in the world! I am fascinated on how we can use AI to open accessibility, bridge communication gaps, and uncover truths the human eye can not see.

Concluding thoughts

If readers can gather anything from this blog post is that AI is a probability and statistics machine that can solve highly complex, specialized tasks, at scale. The world is surrounded by hype, debate, fear, and imagination about where the world will travel towards utilizing AI but we should embrace the technology, debate intellectually and fair, and help bring society as a whole closer to greater intelligence! As the technological landscape evolves rapidly (I nod to quantum and new distillation techniques), I continue to be hungry for knowledge, to learn all I can about AI, and share that knowledge with anyone interested in listening. I am truly grateful to be at the point in my career where I am invited to speak on panels (Sarasota.tech), visit my alma maters to talk to students, and practice a career I am passionate about and learn daily. Thank you all for this opportunity!