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Life Lessons

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Capitalizing on Rare Opportunities

A friend called me today to say he’d been offered a complimentary, all-access pass to this weekend’s Formula 1 race in Las Vegas. He was on the fence at first but decided to accept the offer because it’s a once-in-a-lifetime opportunity. He pulled the trigger and made travel arrangements.

Once-in-a-lifetime opportunities don’t come my way often (of course), but when one does, I try to quantify the magnitude of the opportunity and then act quickly to capitalize on it if it’s truly great and rare. I’ve found that truly rare opportunities don’t last long. If you don’t take advantage of one, someone else will—with lightning speed.

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Make Better Decisions Using Suzy Welch’s 10-10-10 Method

I recently came across the 10-10-10 process of Suzy Welch. It’s a framework to help consistently improve decision-making by identifying regret before a decision is made. It works like this:

  • Crystalize the decision you’re making.
  • Understand the options available to you.
  • Identify the consequences of each option in the immediate future (10 minutes).
  • Identify the consequences of each option in the medium future (10 months).
  • Identify the consequences of each option in the long-term future (10 years).

Thinking about the consequences forces mental time travel. You’ll understand how “future you” will feel about the consequences of each option you’re considering. If you’re likely to regret a decision (i.e., an outcome doesn’t align with your vision of your future), you can factor that into your decision-making process and pick the decision (and likely outcome) that best aligns with the future you want to create.

An easy example of applying this is working out:

  • Decision: Should I work out now?
  • Options: Work out or don’t work out.
  • 10-minute impact of not working out: relaxed, comfortable, do something enjoyable, etc.
  • 10-month impact of not working out: feel bad, look bad, lack self-confidence, etc.
  • 10-year impact of not working out: increased risk of long-term health issues, etc.

Using this framework, it makes sense to push through the immediate discomfort and exercise to reduce your risk of health issues in the future and enjoy the other medium- and long-term benefits of working out. I know that’s easier said than done, but you get the idea.

I like Suzy’s approach. It’s a simple tool that most people can use to make consistent, rational decisions.

For more on her 10-10-10 method, watch this video.

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How Aggressive Is Too Aggressive When You’re Negotiating?

I was at a social event where aggressiveness in deal negotiations was discussed. The main questions being asked were how aggressive should a party be in negotiations and when have they taken it too far.

This gathering was attended by founders (early-stage and mature), VC investors, people in the start-up ecosystem, people not involved in start-ups, and a few non-start-up lawyers. The perspectives were diverse, which made for an interesting conversation.

After a while, people mostly ended up in one of two camps:

  • There’s a point in deal negotiations where you can be too aggressive and jeopardize the long-term viability of a deal. Negotiate to that point but don’t take it further (even if you have the leverage to do so), because it will have negative consequences down the road.
  • Deal negotiating is an example of what has applied to humans for a long time: survival of the fittest. You must fiercely negotiate for your best interest in any deal. Not doing so leaves an opening for others to take advantage of you. Negotiate like your survival depends on it.

The conversation was much more involved than that, but I’ve tried to simplify it. I really enjoyed hearing the different perspectives. At the end of the conversation, most agreed that how people thought about aggressiveness was influenced by their upbringing and professional experiences.

I don’t think there’s a right or wrong way to think about aggressiveness. I’ve come to believe that the answer to how aggressive one should be in negotiations is it depends. It depends on the dynamics at the time, on what you’re negotiating, on what leverage you have, and on the parties you’re negotiating with.

One thing holds true in all negotiations. Be mindful of this when deciding how aggressive to be: no one will look out for your interest more than you will. If you don’t look out for yourself, don’t expect the other party to do so.

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The Power of Compounding: A Simple Example

Albert Einstein famously called compound interest the eighth wonder of the world. Compounding is indeed a powerful force. Yet I’ve noticed that many people don’t understand just how powerful it is. More importantly, they don’t understand that compounding is applicable to other aspects of life, not just money. Relationships, effort, knowledge—all of these and more can benefit from compounding.

I tried recently to communicate the power of compounding to someone but failed miserably. The concept didn’t resonate with them. It wasn’t their fault. I realized I wasn’t doing a great job of explaining it in a simple way that everyone can grasp. I searched for a simple way to communicate this powerful concept and found a helpful monetary example.

Start with a penny. Double it on day 2. Then keep doubling the amount you have every day for thirty days. How much do you think you’ll end up with? The answer is over $5 million, an astronomical amount, all because of compounding. To be exact, $5,368,709.12. Not sure how you go from a penny to over $5 million in a month? Here’s a breakdown of what happens when you double the amount you have every day:

A few things to note:

  • It takes 15 days for the value to surpass $100.
  • On day 18, the value surpasses $1,000.
  • On day 21, the value surpasses $10,000.
  • On day 25, the value surpasses $100,000.
  • On day 28, the value surpasses $1,000,000.

This is a great example that most people can understand. It demonstrates that most of the benefit from compounding is backloaded.

  • Days 1–15: $100 added
  • Days 16–30: $5.3+ million added
  • Days 28–30: ~$4.7 million added (or 88% of the final amount) in 3 days!

This example also does a great job of showing how powerful it can be to stick with the process even though the payoff is small in the beginning. The small amount you have in the early days provides the base required for future compounding. Without the $100 gained in the first 15 days and the continued compounding, you never reach the $5.3+ million on day 30.  

While this example is monetary, the concept of compounding is applicable to various aspects of life. If you start something and stay consistent over a long period of time, you’ll likely see outsize benefits toward the back end due to the compounding of your consistent efforts.

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Errors of Missed Opportunities

When I decide to take an action and it doesn’t turn out as I’d wanted, I reflect on it. I try to identify what caused the outcome (a bad decision on my part, or bad luck?) and take those lessons forward. As I began investing and studying successful investors, I started to reflect more on my decisions that resulted in missed opportunities. It’s not something most people think about, but the actions you don’t take can have a bigger impact on your trajectory than the actions you do take.

For example, if I make an investment and it goes bad, the most I can lose is the amount of capital I invested (assuming I didn’t use leverage). If I decide not to invest in an opportunity and it ends up returning 10x, not acting was a bigger error. Let’s quantify this:

Decision A: Invest

Investment: $10

Return: –100% (lose everything)

Capital returned: $0

Loss: $10


Decision B: Don’t Invest

Investment: $10

Return: 1000%

Capital returned: $110

Loss: $100 ($110 capital returned – $10 investment)


The decision to not invest was 10x more costly than the decision to invest. Of course, these are made-up round numbers—the extremes of both decisions—that I’m using as examples. Naturally, you won’t miss a 10x return every time you don’t invest, and every investment won’t go to zero.

The big takeaway is that missing an opportunity can be as important, and sometimes a bigger mistake, than the opportunities you take advantage of but get wrong. I used the example of investing to quantity this concept, but it applies in many other aspects of life too.

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Work–Life Harmony vs. Balance

I listened to an interview of Scooter Braun recently. Scooter has had a wildly successful career in the entertainment industry. He’s credited with discovering Justin Bieber, and he managed several other top entertainers. He recently sold his firm, Ithaca Holdings, for $1 billion and acquired Quality Control, one of the most successful rap labels—which happens to be in Atlanta—for around $250 million.  

Braun shared advice he’d received from Jeff Bezos, founder of Amazon.com, on work–life balance. Bezos thinks you shouldn’t have to balance two things you love and that harmonizing them makes more sense. To do this, he communicates to people in his personal life how much he loves what he’s doing at work and what the latest developments there are. At work, his team knows how much he loves his children and what’s going on with them. The idea is to integrate and harmonize your work life and home life by making everyone feel in the loop, part of what’s going on in the parts of your life they can’t see. If you must miss a work event because of something child-related, everyone understands because they’re in the loop and know your children take priority.

Braun went on to share that for many years he kept his work and personal lives very separate but cared deeply about both. This ultimately created issues in his life because, as he put it, “it was like being married to two different people,” which wasn’t fair to the important people in his life.

I’ve been more of a balance person historically—I tend to try to keep work and my personal life separate. Sometimes it’s worked and sometimes it hasn’t. The advice Braun received from Bezos definitely resonated with me. It has me thinking about sharing more about the important parts of my life with people who are important to me. I’m naturally a private person, so I want to harmonize in a way that feels comfortable, given that trait.

Here’s the clip of Braun sharing what he learned from Bezos and how it affected him.

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Convinced, but Flexible Too

I tend to be someone who has strong opinions about a decision once I’ve made up my mind. When I was younger, I’d stand with my position no matter what. I wasn’t open to considering other perspectives or new information. My mind was made up, and it wasn’t changing. That trait led to some painful situations when I’d clearly made the wrong decision but refused to admit it.

Today I try to have flexibility in my thought processes and decisions. I still have conviction about my decisions, but I’m much more open to listening and trying to understand perspectives I haven’t considered. Equally important is new information. When facts or data that I didn’t previously have come to my attention, I consider them with more of an open mind.

Being open to listening and reviewing new data doesn’t necessarily mean that I change my decision, of course. Often, I stick with it because I still feel it’s the right decision, all things considered. But there are times when being open-minded has allowed me to accept that I’ve made the wrong decision, reverse course, and avoid unnecessary pain.

Now, when I’ve made a decision, I make sure that along with having conviction about it, I have mental flexibility too.

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Nothing Works Unless You Do

Maya Angelou once said, “Nothing will work unless you do.”

If you want to achieve goals in life, work, relationships, etc., work is required. Nothing will go the way you want unless you put in the work. There’s no substitute for hard work—no sustainable way around it. If you don’t put in the work, things likely won’t go your way.

Instead of viewing hard work as an obstacle to my getting what I want, I look at it as a requirement for me to get what I want. It’s part of the journey. I don’t always like it, but I accept that it’s a package deal. No hard work, no good outcome. It’s a small mental shift that’s been helpful to me over the years.

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Biggest Takeaway from My Parents

Our parents have an outsize influence on us, whether we realize it or not. It can be positive or negative. The environment they create and the actions they take shape us. We’re usually in the environment they create and under their care for approximately eighteen years. That’s a long time. And that period is when the brain is still developing.

Today I thought about what I learned from my parents. I came up with a long list of things, but one trait especially stood out because both my parents displayed it. They consistently pursued the professions they’d chosen. Said differently:

They got up in the morning and went to work every day, whether they wanted to or not.

I remember having conversations with my dad about this. He worked for the same company for over thirty years. He openly shared that he often didn’t want to go to work. He didn’t enjoy the work or the culture (racism, etc.), but he was great at what he did, and it provided for the lifestyle he wanted his family to have. So he consistently went to work for over thirty years.

My mom was the same. She worked for the same organization for over forty years. She enjoyed her work and being able to have an impact, which helped, but it was still demanding. There were days she didn’t want to go, but she always did . . . for over forty years.

I think . . . I hope . . . I learned from them to persevere and be consistent, no matter what.

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Acquiring Knowledge

Last week, I shared a few thoughts about knowledge. Knowledge is the understanding of a topic or of how something works. Today I want to talk about a few ways people acquire knowledge:

  • Others’ experience – As I said last week, people still actively working to achieve their goals are unlikely to share their knowledge and give up their advantage absent a preexisting relationship or some commonality. Those who have achieved their goals are more likely to share their knowledge. For example, a young entrepreneur building his empire will be more guarded, when asked by a stranger to share what he’s learned, than someone who’s thinking about legacy at the tail end of their career. The good news is that the learnings of highly successful entrepreneurs are readily available in biographies and autobiographies. These books often result from reflection by these individuals and contain the key learnings that allowed them to succeed (or that caused early failures).
  • Your experience – It’s often said that experience is the best teacher. You gain experience by acting. As you make mistakes or have success, you learn from experience and your knowledge grows.
  • Your insights – This one is tougher to describe, but I’ll try. Sometimes no one understands a subject, or the few who do are inaccessible. In these situations, to understand something, you may have to look for insights. This involves taking in information from various (credible) sources, digesting it and thinking about it in different ways, and finding nonobvious connections between seemingly unrelated bits of information that others have overlooked. These connections are your insights, which can lead to a superior understanding of a situation or topic. This approach isn’t easy, and it’s the least-often-chosen path. But it’s the approach that allows people to spurn consensus and act with the conviction that leads to outsize outcomes.

This isn’t an exhaustive list, but I believe these are three effective ways that people can acquire knowledge today. Combining the knowledge gained from these three approaches with execution can be a winning formula for success.

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