It’s largely automated. I have a collection of Python scripts in a Jupyter Notebook that scrapes Meetup and Eventbrite for events in categories that I consider to be “tech,” “entrepreneur,” and “nerd.” The result is a checklist that I review. I make judgment calls and uncheck any items that I don’t think fit on this list.
In addition to events that my scripts find, I also manually add events when their organizers contact me with their details.
What goes into this list?
I prefer to cast a wide net, so the list includes events that would be of interest to techies, nerds, and entrepreneurs. It includes (but isn’t limited to) events that fall under any of these categories:
Programming, DevOps, systems administration, and testing
Tech project management / agile processes
Video, board, and role-playing games
Book, philosophy, and discussion clubs
Tech, business, and entrepreneur networking events
Toastmasters and other events related to improving your presentation and public speaking skills, because nerds really need to up their presentation game
Sci-fi, fantasy, and other genre fandoms
Self-improvement, especially of the sort that appeals to techies
Monday at 7 p.m. at Embarc Collective (Tampa): Tampa Devs presents Deploying at the Tactical Edge: Overcoming Air-Gap Constraints in Kubernetes, where certified cloud native associate Nathan Thrasher will break down the tools and workflows that make secure, repeatable Kubernetes deployments possible in isolated environments.
Tuesday at 10 a.m., online: Computer Coach presents The Job Seeker Journey Framework, a proprietary approach developed by Computer Coach and refined through 26 years of real-world job placement experience.
Instead of treating the job search like a collection of disconnected tasks, this framework maps out each phase job seekers move through, from preparation and positioning to interviewing and offer decisions. The session explains how employers think at each stage, where job seekers often get stuck, and how to move forward with intention using a clear, structured process.
Wednesday at 5:30 p.m. at Entrepreneur Collaborative Center (Tampa): Tampa Bay QA and Testing Meetup (along with Tampa Bay AI Meetup) presents Power Testmation (PT8N): AI-Enhanced Test Management.
Power Testmation (PT8N) is an Azure DevOps (ADO) Test Manager plugin built to cover core test management needs—now enhanced with an AI assistant named Alicia. Alicia helps teams create, execute, and improve test cases faster by generating tests from requirements and documents, analyzing existing coverage, updating tests when features change, and even running test cases through an MCP server.
This will feature walkthrough of a realistic, day-to-day workflow: how a QA engineer uses PT8N in a normal workday—from turning requirements into tests, to keeping suites clean and up to date, to executing and refining coverage.
Wednesday at 5:30 p.m. at spARK Labs (St. Pete): AI Salon St. Pete / Tampa presents a fireside chat with Nithesh Gudipuri (Associate Director of Technology, Raymond James) and John Adams (SVP of AI Architecture, VideoAmp) on the topic “How do you build — and lead — teams in the age of AI?”
They’ll talk about how AI is reshaping engineering, product, and data teams, what skills actually matter as AI moves from hype to infrastructure, how leaders are balancing humans + automation at scale, what builders should be preparing for next as AI changes how teams work.
Wednesday at 6 p.m. at Hays (Tampa): Tampa Bay Product Group presents The Sharkitect Pitch Lab: Master Your Message. Multiply Your Results.
This experience brings real-world, battle-tested pitchology into a hands-on lab where you’ll build and refine your actual message in real time. It will be led by Tony Greene, Co-Founder of The Sharkitect Group, the CMO and strategy team trusted by Shark Tank stars, like Mark Cuban and Kevin Harrington.
Designed to help entrepreneurs, founders, and business leaders engineer a clear, compelling, and confidence-driven pitch using the same strategic frameworks that power high-growth brands behind the scenes.
Thursday at 6:30 p.m. at Cigar City Brewing (Tampa): Tampa Bay New-In-Tech is holding Thursday Connect & Cheers — Whether you’re new to the tech industry, transitioning into tech, or just looking to expand your network, this event is designed to help you make genuine connections in a relaxed, low-pressure setting.
Thursday at 7 p.m. at Neon Temple (Tampa): Come join Neon Temple’s own Binary_badg3r as he walks us through an OSINT journey with a ton of Flair!
Starting with just a single image, this presentation demonstrates the power, and danger of open-source intelligence (OSINT), by tracking down wrestling legend Ric Flair’s location from just a single image using freely available and commercial tools. Through this practical example, attendees will see firsthand how OSINT analysts piece together clues from a variety of sources to pinpoint exactly where someone is. This isn’t just about finding a celebrity; it’s about understanding how these same techniques can be used against anyone, from executives to everyday individuals who unknowingly broadcast their locations through digital breadcrumbs. Whether you’re stylin’ and profilin’ or just posting vacation photos, this session reveals the gap between perceived online privacy and actual exposure, while providing defensive strategies to protect yourself and your organization from location-based tracking.
It’s largely automated. I have a collection of Python scripts in a Jupyter Notebook that scrapes Meetup and Eventbrite for events in categories that I consider to be “tech,” “entrepreneur,” and “nerd.” The result is a checklist that I review. I make judgment calls and uncheck any items that I don’t think fit on this list.
In addition to events that my scripts find, I also manually add events when their organizers contact me with their details.
What goes into this list?
I prefer to cast a wide net, so the list includes events that would be of interest to techies, nerds, and entrepreneurs. It includes (but isn’t limited to) events that fall under any of these categories:
Programming, DevOps, systems administration, and testing
Tech project management / agile processes
Video, board, and role-playing games
Book, philosophy, and discussion clubs
Tech, business, and entrepreneur networking events
Toastmasters and other events related to improving your presentation and public speaking skills, because nerds really need to up their presentation game
Sci-fi, fantasy, and other genre fandoms
Self-improvement, especially of the sort that appeals to techies
Tuesday at 10:00 a.m. (online): Standing out on LinkedIn takes more than just having a profile. It takes intention, clarity, and the right approach. This live webinar is designed to help professionals cut through the noise and get noticed by recruiters, hiring managers, and industry peers. Led by the Computer Coach Career Services team, this session breaks down how LinkedIn actually works and how to use it as a tool for visibility, connection, and career growth.
Tuesday at 5:30 at Hidden Springs Ale Works (Tampa): It’s the last Tuesday of the month, which means it’s time for another TampaTech Taps & Taco Tuesday! Come connect with industry peers, have some of Hidden Springs’ fine beers at 15% off, and of course, free tacos!
No speakers, no presentations — just great conversations and a raffle (because that’s way more fun!)
Thursday at 4:00 p.m. at American Legion Post 138 (Tampa): It’s the January 2026 Tampa/MacDill AFB Orange Call!
In a military context, an “orange call” refers to an alert signaling a heightened cybersecurity state of readiness.
This orange call’s purpose is to gather and network amongst fellow communicators, guardians, and enablers of all ranks, titles, and experience levels, share resources and seek professional development. They will conduct an informal meet & greet and discuss MacDill communicators and missions, including the increasing role of cyber and the importance of defending our nation’s networks.
It’s also an opportunity for anyone looking for a job or internship — you get to make a 2-minute elevator pitch! Same for anyone looking to hire.
Friday, starting at 8:00 a.m. at the Hilton Downtown (Tampa): Tampa Bay Generative AI Meetup is partnering with the Seventh Annual Tampa Official Cybersecurity Summit!
This is the must-attend event for CISOs and senior leaders looking to strengthen resilience, reduce risk, and align security with business goals. Join top executives, innovators, and experts for a full day of actionable insights, cutting-edge solutions, and high-impact networking. Experience interactive panels, exclusive solution showcases, and strategic discussions that go beyond theory to deliver real-world results, all complemented by a catered breakfast, networking lunch, and closing cocktail reception.
Also, Tampa Bay Generative AI Meetup organizer James Gress will be on the AI and Emerging Tech at the 2026 Security Frontline panel at 11:10!
It’s largely automated. I have a collection of Python scripts in a Jupyter Notebook that scrapes Meetup and Eventbrite for events in categories that I consider to be “tech,” “entrepreneur,” and “nerd.” The result is a checklist that I review. I make judgment calls and uncheck any items that I don’t think fit on this list.
In addition to events that my scripts find, I also manually add events when their organizers contact me with their details.
What goes into this list?
I prefer to cast a wide net, so the list includes events that would be of interest to techies, nerds, and entrepreneurs. It includes (but isn’t limited to) events that fall under any of these categories:
Programming, DevOps, systems administration, and testing
Tech project management / agile processes
Video, board, and role-playing games
Book, philosophy, and discussion clubs
Tech, business, and entrepreneur networking events
Toastmasters and other events related to improving your presentation and public speaking skills, because nerds really need to up their presentation game
Sci-fi, fantasy, and other genre fandoms
Self-improvement, especially of the sort that appeals to techies
Yesterday evening, I headed to spARK Labs to attend the CTO School Tampa Bay meetup to catch their session, Lessons in Scaling Engineering Teams with Leon Kuperman of CAST AI, where organizer Marvin Scaff conducted a “fireside chat” with CAST AI’s CTO.
Leon Kuperman has over 20 years of experience, having been Vice President of Security Products for Oracle Cloud Infrastructure (OCI). This role followed Oracle’s 2018 acquisition of Zenedge, a cybersecurity and Web Application Firewall (WAF) company where Kuperman was Co-Founder and CTO. Prior to that, he had leadership roles at IBM and Truition. He’s widely recognized for his expertise in cloud computing, web application security, and engineering leadership.
CAST AI is a Miami-based cloud automation platform that optimizes Kubernetes clusters using AI, founded back in the pre-GPT (and pre-COVID) era, in 2019. They recently launched OMNI Compute, a unified control plane that allows organizations to access compute resources (specifically GPUs for AI workloads) across different cloud providers and regions seamlessly. Just this month, they joined the “three comma club” and hit a valuation of over $1 billion.
My original plan was to arrive early, but a combination of last-minute calls and making the cross-bay journey led to my missing the first half hour of the talk.
Still, I took some notes, and I’m sharing them here. I hope you find them useful!
The fireside chat with Leon Kuperman
Marvin and Leon’s chat was a compressed master class in managing a software engineering organization. They walked through what it takes to scale engineering without losing velocity, drawing on lessons from building CAST AI (now at around 160 engineers) and Leon’s earlier BigCo experience, including at IBM and Oracle.
I caught three-quarters of the talk, which included:
Scaling needs structure, especially especially distributed teams. Leon framed “scale” as a move from informal coordination to explicit systems. Rather than adding bureaucracy for its own sake, his approach is to add just enough structure to prevent chaos when the team is remote and distributed.
The “two-pizza team” model: Amazon popularized the “two-pizza rule,” a general guideline that teams work best when they’re small enough that two pizzas will feed them. This typically means a team size of 10 people or fewer. CAST AI teams are “two-pizza” teams, and most teams are dedicated to a specific scope.
A deliberately flat hierarchy: Leon described a simple reporting chain leading up to him: directors → VP Engineering → Leon. Despite scale, he aims to stay close to reality by interacting with every team at least every two weeks, and often weekly.
Peter Principle was (the younger ones in the room didn’t, probably because it’s an idea that was popular in the 1970s-80s). He talked about how people get promoted into roles they’re not suited for, and then get stuck because nobody ever goes back to IC.
CAST AI’s answer is a “manager candidate” program, where a prospective manager is assigned a small pod, where they get the chance to “do the job before you get the job” for about six months. If the candidate is a fit, they retain the manager role, otherwise, they return to an IC role with “zero repercussions” and no stigma.
Common leadership failure modes: Leon highlighted the usual suspects, including micromanaging, weak delegation, and not building motivation through mentoring. He also stressed that trust is built through honesty and vulnerability, as people won’t fully commit to a leader who presents as a “robotic individual.”
Unifying product and engineering
“If I fail, I fail.”
CTOs must be both “product people” and “customer people.” Even for introverts, he argued this is non-negotiable: a CTO needs the customer context to make good product/engineering tradeoffs.
Planning: vision is long-term; execution is short-loop. He rejected long-range roadmaps as fantasy (“estimates are always wrong”) and described a system of:
Quarterly OKRs
Frequent priority reviews (about every two weeks) to stay aligned with customer needs
An overall bias toward time-to-market as the top validation lever
Hiring, culture, and performance management
Dunbar’s Number), you need explicit performance management to avoid letting mediocrity hide in the system.
don’t want, while also being willing to move on from sustained underperformance.
A technical exercise (preferably collaborative/live)
A culture check where each interviewer probes one value deeply
He gave a concrete example using “customer obsession” as a trait: asking for times someone pushed back internally to fight for the customer, and treating “not really” as a signal of poor fit.
Foundational CS > language trivia. In the Q&A session, Leon emphasized hiring for fundamentals, such as distributed systems and concurrency, because those are hard to fake (and languages can be learned fairly quickly).
DevX and DevOps
DevEx is a scaling strategy, not a perk. Leon explicitly dismissed vanity metrics and refocused on developer experience quantities that matter: friction in onboarding, docs, local dev, and pipelines is what slows teams down. CAST AI has a dedicated DevEx team of four focused on removing that friction.
Measure friction with DevEx + DORA-style signals. (by the way, DORA is short for “DevOps Research and Assessment”). He described using GetDX to produce quarterly “heat maps” of where developers are least happy, then prioritizing platform work to make those pain points “not suck.”
“The antidote to change risk is more change.” A highlight of the evening: Leon pushed back hard on enterprise “change approval board” thinking. Enterprises lock down change because change causes incidents; his view is that the remedy is smaller changes released faster, backed by automation so that rollback is quick and boring.
Automated quality, modern delivery, and canaries. At their release cadence, manual QA doesn’t scale. Leon said they do zero manual testing (no QA team), rely on automated checks (including AI “first-pass” checks), and called out Argo CD for Kubernetes delivery plus canary testing as the next level of release management.
Blameless root cause analysis and “5 Whys”: When things break, Leon described a blameless postmortem discipline, where they enforce psychological safety, run an honest “5 Whys,” produce near-term action items, and ensure everyone is heard. No finger-pointing!
He reinforced the mindset later: “It’s the process that broke, not the guy.”
AI tools and the future of coding
Tool adoption is becoming a performance separator. Leon’s framing: engineers who don’t adopt strong tools and absorb best practices will get outpaced, even by “average” engineers who do.
Claude Code, expense, and velocity: In the founder funding discussion, Marvin referenced that tools like “Claude code” are “expensive… a couple hundred bucks per person per month,” but enable teams to ship quickly.
GSD (short for “Get Shit Done”) as a workflow aid and “context manager” style approach—breaking work into phases to reduce context-window pain and keep momentum.
Writing skill as a proxy for critical thinking. One of the spiciest takes: Leon said he “over-indexes” on writing. Bullet points aren’t enough; if you’re writing something for him, he wants narrative because it reveals whether someone can truly reason and communicate. He also suggested using LLMs to critique your own documents (first-principles critique, “strawman” the argument) to find logic holes before presenting.
Advice for founders and startups: moats, funding, and being lean
Competing isn’t about coding faster; it’s about differentiation. Leon argued that competitors are a symptom; the real challenge is building differentiation that holds even if someone else has more resources.
He then explained CAST AI’s “data moat” concretely: a read-only agent collects cluster state/events continuously, creating a unique multi-cloud vantage point used to train algorithms. It’s something that individual hyperscalers can’t replicate as easily.
Raise funds to scale a working flywheel, not to “find it.” Leon advocated staying lean and bootstrapping where possible, warning against raising money “to compete.” Instead, raise when you’ve hit an inflection point and want to scale what’s already working.
first customer signal and getting validation before building for scale.
Summary: The “scaling engineering teams” playbook Leon kept returning to
As I said at the beginning, this talk was a compressed master class in managing a software engineering organization. Here’s the evening’s “tl;dr” that condenses Leon’s approach:
Small, service-owned teams, with a deliberately flat hierarchy
Safe leadership experimentation, with manager trials and no stigma for returning to IC
Product/engineering alignment by design, whereone escalation path, one accountability point)
Performance management as culture, not an HR afterthought
This meetup group is a little more exclusive, with membership is by approval and organizer referral, and it’s limited to technical people only. If you’re a senior tech leader or on the path to becoming one (say, a tech lead or senior developer), you’re eligible.
Their goal? To provide a forum where tech leaders can exchange ideas and have discussions about tech, process, management, or whatever issues affect them during this highly accelerated period in the industry.
Tuesday at 10:00 a.m., online: Get ready to crush your next interview with real-life scenarios and practice. No more awkward pauses or sweaty palms! Interview success doesn’t happen by chance. It happens through preparation. Join us for Interview Action Prep, an interactive session designed to help job seekers build confidence, refine interview techniques, and learn how to present skills clearly and professionally.
Are you learning Python or want to catch up on extra work? Interested in meeting new friends for the upcoming new year? Bring your laptop and join Tampa Bay Python for a Study Group Meet & Greet, where you’ll be surrounded by like-minded Python beginners and professionals. The study group is for everyone on their Python journey, whether you’re just starting out, already an experienced Pythonista, or anywhere in between.
Thursday at 5 p.m. at Kress Contemporary (Tampa): “Tech, Tunes, and Tails” will be an unusual gathering for Tampa Bay’s tech/tech-adjacent scene, with not just networking, but an open mic jam session, and puppies! Join us and a LOT of Tampa Bay’s tech meetups at Kress Contemporary in Ybor this Thursday from 5 – 8 p.m.
Tampa Bay Tech Week Is officially coming April 8-10th! Join us for the launch party! This is a multi-day tech takeover across the Bay, celebrating the builders, founders, and community members helping turn Tampa into a true economic force. From startups to seasoned leaders, creatives to investors, we’re bringing together the people shaping what’s next.
It’s largely automated. I have a collection of Python scripts in a Jupyter Notebook that scrapes Meetup and Eventbrite for events in categories that I consider to be “tech,” “entrepreneur,” and “nerd.” The result is a checklist that I review. I make judgment calls and uncheck any items that I don’t think fit on this list.
In addition to events that my scripts find, I also manually add events when their organizers contact me with their details.
What goes into this list?
I prefer to cast a wide net, so the list includes events that would be of interest to techies, nerds, and entrepreneurs. It includes (but isn’t limited to) events that fall under any of these categories:
Programming, DevOps, systems administration, and testing
Tech project management / agile processes
Video, board, and role-playing games
Book, philosophy, and discussion clubs
Tech, business, and entrepreneur networking events
Toastmasters and other events related to improving your presentation and public speaking skills, because nerds really need to up their presentation game
Sci-fi, fantasy, and other genre fandoms
Self-improvement, especially of the sort that appeals to techies
Wednesday at 6 p.m. at the Entrepreneur Collaborative Center (Tampa): It’s the Data Analytics & AI – Tampa Bay – January meetup! For most businesses and organizations, data analytics and business intelligence is used to support mandatory business functions. For data scientists, the tools and technologies are ever-changing.
Join local experts in discussing current trends and topics in the analytics field, including AI and ML, data science, business analytics, systems design, database management, data mining, and more.
Thursday at 6:30 p.m. at Wild Rover Brewery (Tampa): It’s a Lean Beer on the Tampa side of the Bay!
Lean Beer is an alternative to the early morning Lean Coffees, for folks who can’t always join us at 7:30AM. Lean Beer is a great place to ask questions and share your stories of using Agile and Lean software approaches, over an adult beverage, if you choose. They discuss any topics on Agile and Lean that are of interest to whomever is gathered. You suggest the topics, then the group prioritizes that list democratically, through a good ole’ fashion vote. We manage our discussions via time boxes, and a Roman vote (drinks up/drinks down). Vegas rules apply!
Lean Beer is a non-formal group who like to loosen their ties and roll up their sleeves at the end of a long day, and gather with other like-minded Agile Practitioners to exchange ideas and information. Come see what Lean Beer is all about and get your Agile on.
Thursday at 7:00 p.m. at Hillsborough Community College Cyberlab (Tampa): Tampa Devs presents AI in the Engineering Workflow: Practical Use Cases and Implementation!
Connor Tumbleson, one of the core members of Tampa Devs, speaks to common real world use cases for AI, from accelerating software development and automating repetitive tasks to improving decision making and enhancing product quality.
Connor will break down how developers are integrating AI into their toolchains today and highlight the practical benefits as someone directly in the weeds of daily AI implementations.
He’ll also take a brief look back at the origins and evolution of ChatGPT to understand how we arrived at the current generation of AI assistants.
Thursday at 7 p.m. at Neon Temple (Tampa): The Neon Temple, Tampa Bay’s cybersecurity guild, presents An Intro to Always Obeying the Law: DMCA Edition with ShortRound.
It’s largely automated. I have a collection of Python scripts in a Jupyter Notebook that scrapes Meetup and Eventbrite for events in categories that I consider to be “tech,” “entrepreneur,” and “nerd.” The result is a checklist that I review. I make judgment calls and uncheck any items that I don’t think fit on this list.
In addition to events that my scripts find, I also manually add events when their organizers contact me with their details.
What goes into this list?
I prefer to cast a wide net, so the list includes events that would be of interest to techies, nerds, and entrepreneurs. It includes (but isn’t limited to) events that fall under any of these categories:
Programming, DevOps, systems administration, and testing
Tech project management / agile processes
Video, board, and role-playing games
Book, philosophy, and discussion clubs
Tech, business, and entrepreneur networking events
Toastmasters and other events related to improving your presentation and public speaking skills, because nerds really need to up their presentation game
Sci-fi, fantasy, and other genre fandoms
Self-improvement, especially of the sort that appeals to techies
Happy New Year! Here’s what’s happening in the thriving tech scene in Tampa Bay and surrounding areas for the week of Monday, January 5 through Sunday, January 11!
This list includes both in-person and online events. Note that each item in the list includes:
Wednesday at 7 p.m. at Armature Works (Tampa): Tampa Devs is hosting the first big tech social event of the year: the “TDevs Meet & Greet,” a social gathering for Tampa Bay’s tech scene. Whether you’re a long-timer or new to the area, experienced or new to the field, you’re invited!
Thursday at 6 p.m. at Capital One Cafe (Tampa): Tampa Bay Python is hosting another Python Study Group event!
This study group is for everyone on their Python journey, whether you’re just starting out, already an experienced Pythonista, or anywhere in between.
It’s a space to socialize, show off your current projects, ask questions with others studying for similar topics, and enjoy a nice cup of coffee! ☕✨
Not using Python in your day job yet? Whether you are doing school work, a passion project, or extra side work, we love to create a workspace for aspiring Python developers to socialize and be productive in a chill environment.
Thursday at 7 p.m. at the Neon Temple (Tampa): Tampa Bay’s security guild is kicking off the year with Kraken News Hour. Their very own guild-mates will be walking you through current events, cool topics, and much more. Come join Unh1ng3d, Chuck Brew, and the crew as they discuss news, interactive spam, and who knows what else.
It’s largely automated. I have a collection of Python scripts in a Jupyter Notebook that scrapes Meetup and Eventbrite for events in categories that I consider to be “tech,” “entrepreneur,” and “nerd.” The result is a checklist that I review. I make judgment calls and uncheck any items that I don’t think fit on this list.
In addition to events that my scripts find, I also manually add events when their organizers contact me with their details.
What goes into this list?
I prefer to cast a wide net, so the list includes events that would be of interest to techies, nerds, and entrepreneurs. It includes (but isn’t limited to) events that fall under any of these categories:
Programming, DevOps, systems administration, and testing
Tech project management / agile processes
Video, board, and role-playing games
Book, philosophy, and discussion clubs
Tech, business, and entrepreneur networking events
Toastmasters and other events related to improving your presentation and public speaking skills, because nerds really need to up their presentation game
Sci-fi, fantasy, and other genre fandoms
Self-improvement, especially of the sort that appeals to techies
