A few weeks ago, I flew to Chicago to spend two intensive days with some of the smartest, and surprisingly nicest, minds in the world. The first-ever MasterClass Executive cohort. We skipped the small talk, got into the hard questions on AI and the economy and shouted TOGETHER while punching the air… I’ll probably need to explain that last bit.
If you haven’t read my column from last week, you may want to start there.
When I signed up to do MasterClass Executive, I didn’t even know there was going to be an in-person element. I thought I was going to sit in my pyjamas, watch some beautifully filmed educational videos, and hopefully learn a thing or two about business and AI.
But as the course kicked off, my understanding of what I was doing here started to change. There were a lot of calls. Like A LOT! Calls with amazing people from across the business world. At first, I had no idea what to ask them. They’ve all achieved incredible things in their lives. What does little old Dad the Accountant want to know from the man involved in negotiations between Disney and Pixar’s Steve Jobs? I’m still just trying to negotiate with my toddler to stop screaming when some dirt gets on her hands.
But my fellow classmates? They had no problem asking them anything and everything. Hard questions. Good questions. As great as the content was, perhaps bringing together this eclectic group of people was what would make this course special.
So when the MasterClass team shared they were planning a meet-up, before they could think of an agenda, I wanted to go. I am not a fan of small talk, and definitely not a fan of talking to strangers, but as Yes Theory likes to say, “life's greatest moments and deepest connections exist outside of your comfort zone.” So I got on a plane and flew to Chicago for the weekend.
I won’t bore you with the nitty-gritty of every interaction and lecture. You’re a busy person and we’re all still gushing about how wonderful everyone was to each other in a group chat anyway. Instead, here are three core takeaways, as the LinkedIn crowd would call them 🤮, from my time in Chicago.
It’s all about solving problems
The world is full of problems. Big ones, small ones, some as big as your head… ahem. A great business solves a problem. Betsy Ziegler (CEO of 1871) encouraged us to focus on the problem. If you can find a problem you are obsessed with, that could be a great business. Even if you’re in the corporate world, finding the right problems to become obsessed with could lead to an exciting career.
But the problem is, we all tend to overcomplicate everything. Bobbi Brown (Legendary make-up entrepreneur and founder of Jones Road Beauty), sat cross-legged on the stage giving one-liner answers to some loooong-winded questions. “Most things are overcomplicated,” she said. “Simplify things.”
In my own role, I am learning when to run off and automate something or when to take a step back and ask if the process is the thing that needs fixing. Are we handling this problem correctly before we run to automate it? Instead of speeding up bad processes, these are opportunities to get these processes right.
During a Q&A with Andrew Hotz (CMO Crate & Barrel), Matteo Caloia, who has the most incredible title (Chief of Cheese at (P)RiND), took the opportunity to shoot his shot. Matteo is working on perfecting his product’s packaging, so he asked Andrew to critique it. It felt like we were on Shark Tank! Matteo pushed Andrew for real feedback and Andrew hit him with good questions. It was so cool to watch. It also spoke to the entrepreneur inside of me. Look at that, did you see that? Let’s do that one day!
You can be ambitious, demanding AND kind
I attended a lecture from Steven Kaplan (Professor of Entrepreneurship and Finance at Chicago Booth) in which he started by asking what essential qualities we thought a good CEO had. The hands flew up and the suggestions went on for ages until he eventually pulled the plug. He was playing with us. We all have so many ideas of what makes a great leader. From Kaplan’s research, one of the things that matter most is execution. Just get stuff friggin’ done! This was a moment for me because as I grow in my professional career, it feels like there are a lot of pie-in-the-sky things I need to be good at. His three key focus points if your goal is to lead:
Persistence
Efficiency
Proactiveness
Some may see this one as an excuse to be an a**hole in the workplace because you’re getting things done. I see it as the opposite. There’s no excuse not to be a kind leader creating a positive work environment. You just need to ensure that doesn’t hinder you or your team from getting things done. Not every team will be perfect or full of A-players. All the more reason to step up and be a kind leader without accepting mediocrity.
I had some inspiration from Coach K (three-time Olympic gold medal-winning coach of the USA Basketball team and all-round legendary basketball coach). Speak the truth plainly, and quickly. Sometimes in business we don’t want to offend people, or we work with hard people that don’t want to hear any voice but their own. How do I speak the truth plainly and quickly while remaining respectful and kind?
I absolutely haven't got all of this right. How do you help lead someone who is struggling without letting their underperformance hurt your team? How do you motivate somebody who is doing well to stay motivated and maybe even take things to the next level? Everyone is so different! Coach K wasn’t going to let me off easy while I sat in my thoughts. “Don’t make excuses, make solutions.”
Fellow cohort member Larry Reed exemplified these lessons when he came forward to ask a question during an AI fireside chat. After a quip on the stage about your grandparents not learning how to use AI, Larry confirmed he was in fact a grandparent learning about AI, and challenged the leaders on stage to build teams that are representative of the world and not just a boys’ club. No-nonsense, but respectful. This girl dad had goosebumps.
Like the dot-com boom, AI is an opportunity for those that take it
This AI boom everybody is harping on about. It may go bust or it may change the world. It’ll most likely do both. The dot-com boom did exactly that. So many companies disappeared in the investment hype, but those that survived used the technology to change the world. The time we are in is another opportunity.
Andrew Hotz did have some advice for this exact moment - Specialism can be developed by AI. Being a generalist allows you to be the connective tissue between specialist work.
Parth Patil (AI Strategist and MasterClass Instructor) was also dropping the inspiration. The man, who has a swarm of AI agents working for him, advised us to spend more of our day building tools that will compound our work instead of focusing on just getting the day-to-day work done.
I am still not sure what these opportunities will be for me, but I’m diving headfirst anyway hoping to find them. Pulling random problems I need to solve for myself (CPDTracks - a continuing-professional-development app I built for South African Chartered Accountants), learning as I build the plane while flying it. So when I find my big problem to focus on, I’ll be ready for it.
Now Go Out and Do Something
While these and many more insights sit with me from the weekend, the thing that has challenged me the most is the drive of the people around me. There’s something so powerful about the compounding effect of being surrounded by highly motivated people.
Fellow cohort member Lisa Nevans (Owner of The NOW Massage South Bay in El Segundo, CA) did not waste time. As soon as she left Chicago, she launched a GoFundMe to help fellow amazing cohort member Igor Riabchuk (thatukrainianguy.rocks) build an application for us all to stay connected. Within hours, it had raised more than twice its target. Just a few weeks later, it’s already up and running. A display of the power and effectiveness of highly motivated people working together, and with AI.
I’ve learned so much in the last few months of MasterClass Executive and still have more than 80% of the actual written material to get through. Am I going to be superhuman by the time I finish this course?
On Sunday afternoon, Coach K walked onto the stage for a rousing speech on leadership and team. Towards the end, he made us all stand, punch the air and shout TOGETHER in unison. It was such a sports coach thing to do. But you know what? I really did walk away from this weekend feeling this incredible camaraderie with these people. I flew to Chicago to learn about AI, but on the trip home I was thinking about the inspiring people I had met.
Shout Outs
To two of the Three Amigos - Frank and Carolina. Thanks for making a hotel lobby meet-up turn into a hangout for the weekend.
To Lisa, your energy and drive are infectious and awesome. I’m excited to catch up when you visit Cayman.
Moshe, thanks for digging into your emotions with me five minutes after meeting (it was a group exercise). See you in New York. I’m excited to try your broth!
Nicole, thanks for paying for my dinner and refusing to take my dirty Cayman money. I still owe you a consultation. Not sure who got the better value here!
Brett, my fellow South African living overseas! Looking forward to our Ottawa catch-up.
Carlos, thanks for telling me my app was cool and was going to be a hit.
Neha, my cheesecake buddy, and Sebu, thank you both for the great long chat which, among many other things, inspired me to get some Substack articles pumping again.
