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:

1. Persistence

2. Efficiency

3. 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.

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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.

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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 Subbu, thank you both for the great long chat which, among many other things, inspired me to get some Substack articles pumping again.

Nothing triggers the frugal accountant in me like seeing a payment notification for a streaming service we didn’t log into that month. Having a kid has naturally meant our time to stare at the glass rectangle on the wall has gone down significantly, and with it our need to subscribe to all these services.

We used to get home, throw dinner in the oven and watch something together, maybe two somethings. Now we get home and the bedtime routine kicks in. We walk in the door and immediately start getting dinner ready. We try to eat together, which usually turns into a series of performances to get those last few bites down. We might start with reading a book, then move onto interesting distracting objects, and by the end we are blowing bubbles while the dog tries to bite them.

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Sometimes it’s a delight, sometimes it’s a circus, but by the time it’s all said and done we might have an hour of downtime before our own bedtime routine needs to kick in. No binge watching happening here.

We don’t pay for a TV package or cable in our home, but we do subscribe to multiple streaming services. Netflix, Disney+, HBO, Apple TV, Paramount Plus, Amazon Prime, YouTube Premium. It’s a lot. A never ending stream of content being funneled our way. We are wasting money on subscriptions we don’t always use. So we decided to try an experiment. It was time to let one of them go.

We had just paid for a yearly subscription for Disney+, so it was too late to let that one go and I may need to watch The Devil Wears Prada 2. in a few months.
Apple TV comes bundled with our other Apple services and I need the cloud storage for the five business ideas I’m simultaneously working on.
We only have Paramount Plus to watch Survivor and cancel it as soon as the season ends - can’t miss Season 50!
Our Prime subscription is more about free fast shipping than Beast Games so it doesn’t matter much that we rarely watch it.
We signed up for HBO Go / HBO Now / HBO Max / Max / HBO Max again??? when they were desperate for subscribers and locked in a great rate where we barely pay anything for it.

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So that leaves Netflix and YouTube Premium on the chopping block. If you are not paying for YouTube Premium and suffering through all those ads today you are a patron saint of patience. Once you stop watching ads, it’s very hard to tolerate them ever again. My MKBHD, and our Mr Beast and Ryan Trahan viewing must remain sacred. YouTube stays.

So Netflix got chopped. We weren’t watching anything in particular on Netflix, the movies and series we had watched more recently felt formulaic and forgettable. It didn’t feel like a big sacrifice.

I wasn’t sure it would last that long. But after five months we’ve barely noticed it’s been gone. We missed Stranger Things and even that couldn’t get us to sign back up. There is still way too much content to watch on the services we currently subscribe to.

That doesn’t mean we will never subscribe to Netflix again, I still want to see what happened to the girl that keeps getting nose bleeds but doesn’t carry around any wet wipes. But it has made me think that using a subscription-rotation makes more sense than subscribing to them all at once. $15 to $20 a month may sound small but when you’re paying that for five subscriptions you don’t use over a year it can add up to a plane ticket!

Take it from your columnist accountant, use five minutes today and cancel a subscription to a service you never use. You could use that money for much better things, like supporting this column instead.

The end-of-year sales bonanza used to be a one-day Black Friday event. Now it’s a smorgasbord of sale emails from every company you’ve ever interacted with, running from November to Christmas. For this frugal dad, it’s basically the playoffs.

Throughout the year, my wife and I have gotten better at anticipating big things we need/want to buy and holding off for a big sales event. Why pay full price when you can delay that gratification and add the budget euphoria of getting it at a discounted price? Living on an island where everything is at least a week or two away anyway means impulse buying doesn’t hit quite as well as walking into a Lululemon and walking out a much poorer but better dressed man.

Sadly, many of the sales advertised during this period are just scams. A marketing ploy to get you to spend money on things you don’t need, simply because there’s a false sense of urgency that you won’t see a price this good again. Luckily we’re smarter than the average bear.

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If you can find that magical crossover where the thing you were going to buy anyway at full price, suddenly goes on sale - it’s straight fire. That’s what the kids are saying these days. I learnt it watching Survivor.

Knowing the cost of the things you’re going to buy beforehand is therefore the key to not getting conned. Amazon very excitedly sent me a notification to say an item I had looked at before was 50% off. But the ‘50% off’ special price was the same price I had seen months ago when I first looked at it!

Despite the scammy sales floating about, this year we got some great deals I’m really proud of. I’m even more proud that I did not buy one thing on sale for myself on a whim. The baby was a different story.

This year’s sales haul savings report:

• Car seat for when the baby graduates from her current seat (and one which will last until she doesn’t need one anymore) - 20% off!

• Educational toys we were going to buy at full price throughout the next year - 25% off!

• Flight to see the grandparents - 33% off, making some smart use of a points sale and family card benefits! (Thanks Sharon!)

• Baby creams and soaps - 40% off!

• Broken outdoor camera replacement - 50% off!

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Saving money like this makes me unreasonably giddy! A 20% return on a no risk investment is unheard of. To save money on something you would have needed to buy at full price regardless starts to feel like you’re the Wolf of Wall Street - minus the drugs and unhappiness.

This doesn’t just have to be a Black Friday thing. Stores often have sales during other holidays in the year, allowing you to get great deals all year round. So the next time you need to make a big purchase, or maybe even basic supplies, put it on the wish list and start planning for the next big deal. Even the richest people love a good deal on diapers. Though maybe they’re paying someone else to change them.

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What’s Wrong With Legacy Banks?

Traditional retail banking - the kind that requires walking into a physical building, filling in tons of paperwork and begging for a loan with multiple weeks of review has begun its slow, painful death. For one simple reason: the customer experience2.

In a world where everything is digital, even some of your friends, legacy banks have been slow to move. You can argue this is for good reason. Your money is not something you want in the hands of people moving fast and breaking things3. But today people are starting to demand more from their bank, and technology-first banks are proving they can be trusted.

If our money is all digital anyway, why go into a physical bank branch? Why pay exorbitant fees to exchange that money into a different currency or send it to another country? Why on God’s human-infested earth should you be charged just to apply for a loan. One that will make the bank a fortune over your lifetime?

What we want out of banking today is convenience, speed and great customer service. Living on a small island for the last ten years, I haven’t gotten to experience any of that firsthand.

Banking in the Dark Ages

Opening a bank account took over a week, required an in-person visit, and so much documentation I felt violated. A car loan took multiple weeks with another bank. Our home loan - MONTHS! At one point, I was literally standing in the bank, in tears, begging them to release the money for an already approved loan so we could move in.

One day our primary bank decided they didn’t like people using eToro (an international, respected trading and investing platform), so they just blocked processing payments to them. When I submitted a formal complaint it was ignored. We’ve even had fraud on a debit card we had never used.

To be fair to legacy banks, the Cayman Islands is further behind than most places. The banks are protected by the small, albeit wealthy, population and unique legislative requirements. It seems most FinTech banks have not yet found the market worth tackling for the limited upside. That means less competition and more mediocre service.

Meanwhile, in the future

In South Africa—a supposed sh**-hole country according to he who shall not be named—legacy banks are actually world leaders4 in providing digital service and security. Winning awards, pricing their services to allow the less privileged access, and driving innovation.

The best bank I’ve ever used is Europe’s fast-growing digital disruptor, Revolut. A colleague from Ireland, where Revolut5 has dominated the market with 73% of adults now holding accounts6, shared them with me. Their founding niche was offering the same exchange rate as the bank gets (interbank foreign exchange market). The bank is accessed through an incredibly sleek app and now offers multiple services outside of just banking or investing, including international data, local cellular service and travel booking.

How does a legacy bank compete with a bank that you can open an account with using your face and passport in minutes? That will send your bank card across the world at lightning speed, that will let me send money to a friend in another country immediately - for FREE!?

While these are two extreme sides of the digital coin—island banks stuck in the dark ages and a fast-expanding digital powerhouse—they are still competing with each other in a world of global citizens and increasing customer expectations. If legacy banks don’t compete, capitalism will take its toll. And this time, governments are far less likely to bail them out.7

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My budget beginnings

I’ve always enjoyed playing Monopoly personal budgeting. As a kid I’d do chores for my parents and painstakingly record them in a notebook, charging them for each completed chore. Born to be an entrepreneur, but cursed with the risk-averse personality of an accountant. If I picked up ten dog poops in a week at ten cents each, that’s R1 for the week and one step closer to a new Lego set.

The R is a symbol for Rand - the currency of South Africa. So like the dollar but worth less. South Africa is a country, on the African continent, in the south of it… you get it.

I’ve found other people don’t have quite the same passion for tracking and planning their finances as I do. A friend once described their money management plan as, ‘if there is enough money in my bank account to pay for it, I can have it.’ Naturally I spat out my drink.

Why budgeting is important

Tracking where your money goes is an essential part of keeping it under control - and keeping your obsessive-compulsive tendencies at bay. Businesses report where their money comes from and what it gets used for in order to assess their success over a period of time. The stock market then ignores that information and throws money at them because the CEO is a crazy, charismatic individual who will defy the odds and make them rich. It’s not gambling, it’s math and science. Maybe this isn’t a good example.

Having a good knowledge of how your personal finances are being used can set you up for success in the future. See where you have breathing room to spend. Maybe it’s time for a date night? Or see where you can trim things down. Do you really need that expensive adult Lego set? You do? OK, why don’t you cut back on soap this month, who needs that?

Today you don’t have to be an Excel wizard - a title I used to have on my LinkedIn profile before my wife laughed at me - to be able to budget. There are all kinds of fantastic apps that can take care of all the hard work for you and make the whole process super simple. If you bank with a great bank they may have a built-in one, or you can use your own. I personally got rid of those tedious Excel spreadsheets and now use an app called YNAB (You Need A Budget)1.

Before we get into it, it’s important to note that budgeting looks different at different income levels and stages of life. If you are in debt, maybe your budget will focus on getting out of debt. Maybe you just want to stop living paycheck to paycheck. Or if you have a lot of excess, maybe it will focus more on investments. Focus on where you are at, and where you want to be. Don’t worry about the guy in the fancy car at the traffic light, it’s probably the bank’s car anyway.

How I like to budget

OK, I’m about to talk about how I do this budgeting thing, try to stay with me. You’re welcome to pour yourself a gin and tonic if it’ll make this go down easier, I’ll wait…

You only get paid so much money each month,

That money needs to cover some essential things like food, water, shelter, debt, and Lego. The envelope budgeting method is where you take the money you earned and put it in different envelopes that should only be used for that purpose. So you put some money in the food envelope for example. When you go grocery shopping you take the money from that envelope to pay for things. When the money starts to run low it’s two-minute noodles until payday. YNAB uses the digital version of the envelope method.

Once you’ve allocated your income into each of these essential digital envelopes, if there’s any left, you can split that among saving for the future: emergency funds, mortgage down payment, car services. Then the good things in life: eating out, vacations, a new phone. If there’s no money in that ‘envelope’ you don’t have money for that thing.

I made the grave error of telling my wife that our budget can be flexible, she reminds me of that at least once a week. What I meant was if you really do run out of grocery money, you can reallocate some of the money you had set aside for a less essential thing like eating out so you can have the avocado you deserve.

Planning for the future

Organising your finances in this way helps you build a discipline around covering important things first, and not spending money you don’t really have. Avoiding bad debt and building a buffer for when life throws you lemons. Yes you may be blessed to have money in your bank account, but that money may be better saved towards new tires on your aging car than another outfit for your already overflowing closet. You still look good in that fit you bought last year, work it until it’s vintage and then work it some more

Budget with an end in mind

The little high you get when you have a shiny new thing is hard to resist, so having a budget with your true long-term goals guiding your spending can keep you on track to build the life of your dreams. That doesn’t mean you can’t have nice things, just make sure the Lego budget line is filled after you’ve paid your electricity bill so you don’t have to build in the dark. You don’t need to compete with the Instagram Influencers buying gold toilets with their Bitcoin. A happy life is one free of debt and financial stress, start there. Happy budgeting.

This column was not sponsored by Lego. But if someone from Lego ever reads it, let’s talk.