June 14, 2026

Oracle FY27 Sales Kickoff: Fired Up in Las Vegas

 

Oracle FY27 Sales Kickoff: Fired Up in Las Vegas

Todd Swank's Diary Entry for June 14, 2026


I flew into Las Vegas Monday morning and flew home Friday, and this picture is about as much of the Strip as I saw all week. Normally Vegas offers temptation, bad decisions, and stories you probably shouldn’t publish on the internet. This time I was there with 4,500 Oracle coworkers getting fired up for FY27, talking AI data centers, and behaving like a responsible adult. Which is really disappointing for my brand.


The Venetian was our home base for the week, which sounds glamorous until you realize we basically turned it into a very fancy corporate ant farm. Oracle somehow moved 4,500 of us through meetings, meals, security, and caffeine refueling stations without the whole thing collapsing into chaos. Honestly, watching them feed that many salespeople in a two-hour window may have been the most impressive infrastructure demo of the week. And yes, the bomb-sniffing dogs were everywhere, which is reassuring right up until you start wondering what they know that you don’t.


You may remember from last week’s post, A Beautiful Day to Quit Golf, that I lost my temporary tooth, flipper, and retainer in Clear Lake two days before this trip. I couldn’t get a replacement in time, and my emergency Shark Tank-style TempTooth science project went about as well as you’d expect. I even thought about skipping Vegas, but then I reminded myself I’ve looked different my entire life. This wasn’t the hand I wanted, but I’ve been dealt this hand before. So I decided to own it, smile anyway, and not let one missing tooth stop me from doing what I love most: talking to strangers who didn’t ask for it.


The first night I had dinner with several of my recent teammates. At Oracle, every June feels a little like corporate musical chairs, except the music stops and suddenly you have a new manager, a new team, a new product focus, and three fresh acronyms you’re expected to care deeply about. Honestly, it’s not a bad thing. You get exposed to new styles, new ideas, and new ways of doing the job. Plus, changing managers every year keeps you sharp. Mainly because by the time you figure out what one of them wants, congratulations, here comes another one.


We had dinner at WAKUDA inside The Venetian, and the sushi was incredible. But honestly, I spent half the meal staring at the art on the walls. It had this erotic modern punk thing going on, like the first time I saw The Matrix and realized movies could be cool, confusing, and slightly dangerous all at once. I didn’t totally understand what any of it meant, but I knew it was working on me. The whole place felt like Tokyo, Las Vegas, and a tattoo parlor got together and made excellent sushi. That’s how they get you hooked before the bill arrives and commits a second-degree felony against your wallet.


People always ask why I love Las Vegas so much, and the answer is simple: it’s Disney World for adults. There is no other place on earth where you can walk through a fake Italian shopping mall inside a fake Venetian hotel, stumble past a full Wizard of Oz display promoting a show at a giant Sphere, and have every single part of that feel completely normal. Nobody here is pretending to be something they’re not, which is ironic because everything here is pretending to be something it’s not. That’s the magic of Vegas, and I fall for it every single time.


Tuesday morning the FY27 Sales Kickoff officially kicked off, and that’s Mark Hura, Oracle’s President of Global Field Operations, on stage. Mark has a way of making 4,500 salespeople feel like they’re part of something bigger than a quota, which is harder than it sounds. The FY26 numbers were record-breaking across the board, but honestly, what got me wasn’t the revenue figures. It was the AI story. Oracle is building data center infrastructure at a scale most people can’t picture, powering technology that’s going to change how doctors treat patients, how drugs get developed, and how the world actually works. I know AI makes a lot of people nervous. I get it. But sitting in that room, I walked away genuinely excited about the future. Not the scary sci-fi version. The one where people actually get helped.


Tuesday morning the FY27 Sales Kickoff moved from Vegas spectacle to full-on business mode, and this was my first time seeing Oracle CEO Mike Sicilia speak in person. He laid out a vision for an AI-enabled future that felt less like corporate hype and more like the ground shifting under every industry at once. On the earnings call, he talked about customers moving past AI experiments and into real enterprise solutions that improve productivity, service, and competitive advantage. That’s the part that gets me fired up. Not the doom-scrolling version of AI where everyone argues with strangers for sport, but the version where we solve harder problems, move faster, and build things that actually help people. He said the world will look very different three years from now. I believed him.


Tuesday night was the awards ceremony for the North America OCI organization, called The Larrys in honor of Oracle founder Larry Ellison. They do a really nice job turning it into our version of the Oscars, with presenters, nominees, big production value, and plenty of people dressed like they’re one acceptance speech away from thanking their agent. I’ve never been cool enough to be nominated for one of these awards, which I’m totally fine with because I also haven’t been cool enough to own a tuxedo. So really, the system is working.


We had around 120 partners in attendance too, which meant the happy hour invitations started piling up fast. I actually had to turn down several of them, which is wildly out of character for me and frankly not the kind of personal growth I signed up for. I did make it to a few, though, and they were a blast. There’s something energizing about being in a room full of smart people, good conversations, and appetizers you only eat because they’re on tiny plates and therefore legally don’t count.


I also got to spend more time with my new teammates, including Chris in the middle and my new boss, Michael. We were both more than happy to accept the free cowboy hat swag, because I am nothing if not easily bribed by accessories. I honestly can’t remember ever wearing a cowboy hat before, but now that I’ve seen the evidence, I think I pull it off. If this whole thing ever falls apart, I may ride into a dusty border town, clean up corruption, win the respect of the locals, and still be home by dinner because my horse has sleep apnea.


Just like that, it was the final day. Four and a half days, 4,500 people, more sessions, hallway conversations, and tiny appetizers than I can fully account for, and somehow I walked out the other side genuinely fired up. Navigating an event this size is its own endurance sport, but the energy in that room never really dropped. One Team. One Goal. No Limits. Easy to put on a slide, harder to actually feel, but by the end of the week I felt it. We still had one more session to go though, and let’s just say the closing speaker made staying in my seat an easy decision.


The week ended with Oracle founder Larry Ellison speaking to us, which was pretty incredible. I’ve always viewed him as one of the top technology visionaries of all time, so hearing him talk about Oracle’s future and the AI-enabled world ahead was a great way to close things out. At one point he was asked if he owned a Tesla Optimus robot yet. He said no, but he did have one from Unitree, then casually predicted that within five years we may see more humanoid robots walking around than actual humans. The part that hit me was when he said finger dexterity is still one of the hardest problems to solve. The base robot might cost around $16,000, but the one with really good hands is more than $50,000. As a guy who has spent his entire life navigating a world built for hands that work better than mine, I found that oddly validating. Apparently functional fingers are the premium upgrade. Tell me something I don’t know.

June 7, 2026

A Beautiful Day to Quit Golf

 

A Beautiful Day to Quit Golf
Todd Swank's Diary Entry for June 7, 2026


Thursday night we met Luke and the Walters at Crooked Pint in Savage for bingo, which sounds relaxing until you realize every number called that isn’t on your card feels like a personal attack. None of us came close to winning, but the urge to yell “BINGO!” kept building inside me like a medical condition. I’m pretty sure later that night I woke up in a cold sweat and screamed it into the darkness just to get it out of my system, because it sure as heck wasn’t happening during the actual games.


Saturday I drove down to Clear Lake, Iowa to golf at Oak Hills with my high school buddies “Krazy” Kory Madson and a pair of Jasons, Davis and Alexander. It was one of those perfect summer days where the weather was beautiful, the company was great, and for a brief shining moment I was able to pretend I belonged on a golf course. History would prove otherwise, but at this point we were still enjoying the fantasy.


I really noticed something on this trip. I’ve been playing golf with these guys for about 40 years now, and somehow they all got pretty good while I’m still out there duffing shots, launching worm burners, and swinging with all the confidence of a man trying to kill a mosquito with a shovel. So after a long and terrible career, I have decided to retire from golf. I know this may shock the sports world, but God did not make me to be a golfer. He made me to ride in the cart, get a little rowdy, and provide the kind of moral support nobody actually requested.


Normally I get together with these guys in the fall for Jason Alexander’s golf tournament, so it was great to see them in early summer when my golf game still had plenty of time to embarrass itself before Labor Day. I rode in the cart with Jason and really enjoyed catching up. He spent a lot of years in enterprise software before retiring a few years ago, and now he’s focused on entrepreneurial activities, which has pretty much been my dream for years. Retire early, build something fun, and hopefully avoid meetings where someone says “circle back” with a straight face.


One of Jason’s new entrepreneurial projects is Dryp Golf, where he’s starting to sell golf club covers. This putter cover is his first release, made intentionally for the center shaft medium putter, and I have to admit I was fascinated by the whole thing. He just received his first batch of inventory, and demand is already strong, so if you want one, you better grab it quick. Limited quantities of Early Birdie pricing are available, which is a much better use of golf terminology than anything I was doing on the course.


Jason’s other venture is Surf & Serenity House, a walkable vacation rental right in the heart of Clear Lake, which is honestly one of my favorite towns on the planet. It’s a two-bedroom, two-bath home built for couples, small families, two-couple weekends, or girls’ trips, and the location looks pretty ideal for bouncing between the lakefront, downtown, and the Surf District. The reviews are already glowing, which doesn’t surprise me because Jason has always been the kind of guy who pays attention to details. Meanwhile, my entrepreneurial gift is mostly buying domain names and then ignoring them for eight years.


After golf we stopped at Lakeside Landing for food and a drink before I headed back to Minnesota. It’s right on the lake, which made it the perfect place to sit, relax, and pretend I had just completed a serious athletic event instead of mostly riding in a cart. The food was good, the view was beautiful, and for a few peaceful minutes, everything felt exactly like summer is supposed to feel.


Traditionally when we’re in Clear Lake, we eat at the Other Place, or the OP as the locals call it because apparently saying two full words is exhausting. But Kory really wanted to eat somewhere on the water, so we ended up at Lakeside Landing instead. It seemed like a great decision at the time. Beautiful view, good food, cold drinks, and absolutely no warning sign that this innocent little change in plans was about to make my next week significantly more annoying.


Some of you may remember I’m missing a front tooth, although you haven’t seen much evidence of that here because I had a temporary tooth in a retainer that looked real enough for photos. While we were eating, I wrapped it in a napkin like I’ve done plenty of times before, only this time a gust of wind picked up the napkin, launched my temporary tooth into Clear Lake, and sent it straight to whatever underwater kingdom keeps sunglasses, boat keys, and bad decisions.

Jason was incredibly kind and actually waded around trying to find it for me, but the bottom was rocky and the lake had clearly already claimed its prize. I really appreciated him trying. I’ll get another one, but the timing is spectacularly terrible because tomorrow morning I fly to Vegas to spend a week with 4,000 Oracle coworkers for meetings, dinners, and professional schmoozing. On the bright side, I’ve looked different my entire life, so I guess this is just another chapter in that book. Either that, or I’ll be joining Jason Alexander in retirement a little sooner than expected.