I listened to a founder share his thoughts on initiatives he chose to pursue. He considered both the probability of success and the size of the potential payoff. The ones he green-lighted weren’t the ones most likely to succeed—they were the ones with the biggest potential payoff. He knew some were long shots with only a 50% chance of succeeding, but if they did succeed, the payoff would be enormous. He was comfortable with a 50% chance because the payoff would be game-changing for his company.

I love this founder’s thought process. Most people look for a sure thing, or close to it. This founder understands that most things in life aren’t certain. There’s always a chance that things won’t go as planned. He’s thinking about the probabilities in conjunction with the upside. Said another way, he wants initiatives with a potential reward that’s orders of magnitude larger than the risk.  

Thinking about more than the probability of success is hard to do when something is risky, but it can lead to outsize outcomes!

I’ve been paying close attention to Apple’s push into financial services. It’s a huge company. Financial services for consumers and small businesses is one of the few markets large enough to move the needle for a company of Apple’s size. I’ve thought that Apple becoming a financial services company makes a ton of sense. Everything is going digital, and consumers are shifting from in-person banking to digital banking. This has created an amazing opportunity for Apple that it can’t ignore. Apple’s products, such as the iPhone, are the perfect distribution network for digital banking products and services.

Apple officially announced its Apple Pay Later loan product this week. The interesting revelation is that Apple is handling key financial tasks internally and has created a separate legal entity to do so. This is a first. It’s usually partnered with other firms, such as Goldman Sachs, to handle these types of tasks. Read more here.

Banking for consumers and small businesses is overdue for disruption. Offerings from banks don’t meet the expectations of their smaller customers. The banking experience for consumers and small businesses will improve drastically over the next few years, and I can’t wait!

Sean McVay, head coach of the Los Angeles Rams, shared how he led the Rams to win the Super Bowl this year. Sean is the youngest head coach in the NFL. Some of his players are his age or older. I was curious about what he had to say. Part of his formula for success is listening to his players. He acknowledges that he and other coaches don’t have all the answers. He cares about what’s right, not who’s right. This stood out to me and reminded me of something similar Ray Dalio said:

I just want to be right—I don’t care if the right answer comes from me.

Dalio also tweeted a similar thought a few months back.

It’s telling that two credible people in different industries are saying the same thing. If you’re a founder, consider taking a second to ask yourself: Do I care more about being proven right or about getting to the right answer?

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Today I talked with a founder who recently relocated from Miami to Atlanta. Since I visited Miami last week, that city was top of mind. Given what I observed, I was curious about why he left. He shared his reasons for moving to Atlanta (diversity, various industries, talent pool, etc.) and told me that he purchased a home and plans to be here for the long-haul.

One of the things that sets Atlanta apart is that many founders who relocate see themselves putting down roots and calling Atlanta home for a long time. People can see themselves building a great company and a great life here—they don’t have to sacrifice one for the other. In some major metros, it feels like people are just passing through.

Atlanta is a great city. I’m excited to see what the future holds for it, but I already believe that being a place that people want to call home will be a big part of its legacy.

I was listening to a successful entertainment entrepreneur detail his journey to outsize success. One thing he overemphasized was that he’s in a relationship business. He built the right relationships with people and used the relationships to open doors at opportune times. Eventually, he developed relationships with executives who had immense power, which made an unprecedented run of successes possible.

The key to his success was partnering with someone different from himself. He came from a nontraditional background. He quickly realized he had a hard time connecting with people in the industry, who didn’t know him and weren’t sure what to make of him. So he sought out someone in the industry who had the traditional background that people tended to trust. The two of them were different and had different perspectives on life, but they shared a goal. They saw a massive opportunity that no one was paying attention to. They wanted to be at the forefront of introducing this new market to the masses. They formed a partnership, with the traditional partner being the conduit. He understood both worlds. He was able to lend credibility to two sides who had a distrust of each other. Because of him, the two sides embraced each other and had a crazy run that to this day is hard to believe.

I love this story. It exemplifies how two people from different backgrounds can work together to achieve massive success. And it shows how valuable conduits can be . . . especially in emerging markets!

I had a great chat with a founder friend recently. We talked about what helps people be successful. Many things on the list were what you’d expect. But my buddy elaborated on emotional intelligence, also known as emotional quotient, or EQ. I don’t hear that attribute mentioned too often, so I was curious.

He believes success is usually the by-product of working with others. To maximize your working relationships, you must be self-aware—aware of your emotions and how your reactions to them will affect others. And you must be aware of others’ emotions and how they could affect the task at hand. He went much deeper, but that’s the gist of his position.

I partly agree with my buddy. EQ is important, but you can have success without it. But if you have it, it will help you get the best out of yourself and others.

Today marks the end of my one-hundred-fourteenth week of working from home (mostly). Here are my takeaways from week one hundred fourteen:

• Probabilities – I learned a valuable lesson in probabilities this week. I ignored the >50% probability of something happening, and I paid for it.  
• Serendipity – I met some great folks unexpectedly. One of them is a successful investor with roots in my hometown. I think there’s something to be said for increasing your odds of serendipity by hustling.
• Short week – I enjoyed my holiday on Monday, but it made for a short week. It made me a feel as though I was a bit unproductive, even though I know better.

Week one hundred fourteen was busy. I’m looking forward to a normal pace next week.

Today I visited Miami for some meetings. I hadn’t been there in a few years, so I made a point of paying attention to the start-up ecosystem—the parts of it I saw, anyway. A few quick thoughts:

• Energy –There’s a different energy in Miami. It’s hard to explain, but there’s a buzz in the air. Proximity to the ocean’s probably part of it.
• Diversity – The start-up ecosystem has more international diversity than other cities I’ve visited. Miami is more of an international city, so that makes sense.
• Density – The WeWork space I visited was full of people and activity. I spoke with the community manager, and she said all their Miami locations have 95% or greater occupancy. A few are at 100%. As of today, WeWork’s website lists seven locations.
• Passing through – I visited a few places to meet with founders and investors. I got the feeling that, like me, most people were just passing through. I assume this was more a function of where I visited than a representation of the entire ecosystem. I’d like to validate this with more visits.
• Serendipity – Lots of chance encounters are happening in Miami. Lots of people with connections to various start-up ecosystems are moving around the city. It looks like a great place to build relationships with people who have ties to other cities and countries.

I was in town for only a few hours, so these are just flyby observations. I’m looking forward to going back and learning more about the ecosystem.

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I caught up with another investor this week. We recounted her journey from tech start-up founder to venture capital fund founder. As she raised capital from VCs, she recognized that she had the chops to be on the other side of the table as an investor. She also realized there was a lot she didn’t know about the business of venture capital. She knew she had a knowledge gap, in other words.

She was passionate about being an investor, so she set out to fill her knowledge gap. She started by becoming an angel investor to build her muscles around getting deals done. Next, she invested in a few venture capital funds as a limited partner (LP). These investments helped her build relationships with other fund managers and LPs, which helped her develop a better understanding of how to build, grow, and lead a fund.

Fast forward to now: her fund has raised eight figures in capital and is off to the races investing in great founders.

I love this story. It shows that regardless of your starting position, if you’re self-aware and willing to put in the work you can overcome any shortcomings (perceived or real).