Friends and family joke that I have no shame about asking for what I want, especially when traveling and in other service-related situations. They’re right, and I own it.

I view knowing what you want and asking for it as a positive trait. So many people accept what’s offered to them in life. Life happens to them. They may want more, but they never take action to try to get more. I’m not wired like that. By taking the step of saying what I want and asking for it, I’m increasing the chances of getting the outcome I’m aiming for. I’m also making others aware of my goal or expectation.

I want to be clear that I’m not saying it’s okay to bully people into doing what you want or ask in a negative or nasty way. I don’t believe in that. I try to ask for what I want in a manner and tone that mirror how I would want someone to treat me.

I’ve explained to family and friend that I think about this in terms of risk and reward. In many of these situations, the upside dwarfs the downside. The upside is often a more enjoyable experience or a positive impact on you and those with you. The downside is just hearing no.

Family and friends still joke with me about this. When they do, I remind them of the famous Wayne Gretzky quote: “You miss 100% of the shots you don't take.”

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I was listening to a podcast today that mentioned a quote from Bruce Lee that I hadn’t heard before:

If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them.

I like this quote. It speaks to the power of mindset in what you can achieve. If you believe there are limits to what you can accomplish, then you will unknowingly limit yourself in everything you do in life. When you’re trying to accomplish anything hard, periods when you feel your progress has stalled are inevitable. But you have a choice in how you handle them. You can view them as your having reached your limit, or you can persevere and push through them and go further.

Over the years, I’ve learned that mindset matters a lot. For example, when exercising, I’ve always been able to lift more or run farther or faster than I thought possible. I learned that limits hinder my growth. I learned to keep pushing as hard and as far as I can (without hurting myself). It’s hard and painful in the moment, but when it’s done, I’ve always been glad I kept pushing. This approach led to achieving new personal fitness goals and realizing I’m physically capable of much more than I thought.

I’ve been thinking about the kind of discussions that I and other entrepreneurs enjoy since I read this quote from former first lady Eleanor Roosevelt:

Great minds discuss ideas; average minds discuss events; small minds discuss people.

Roosevelt was blunt in her characterization of discussions that don’t revolve around ideas. To be fair, people are free to discuss whatever interests them. For some that’s events and others it’s people, and that’s okay. But I get what she’s alluding to about the discussion of ideas. I’ve experienced the power of conversations about ideas many times, and I’m always blown away. Conversations that energize me and other ambitious people I’m close to always revolve around ideas and the sharing of knowledge. They can last for many hours and regularly go off in unexpected directions. I’m always fired up after I’ve had a great conversation that exposed me to unfamiliar ideas and concepts.

The process of being educated via discussions with people I respect is energy to me. It adds fuel to the fire in my belly and sparks creativity. I think these conversations align with my desire to learn and better myself. Hearing about interesting new ideas causes me to focus intensely. I immediately want to learn more and figure out how to incorporate the ideas into what I’m working on.

Roosevelt, who was born in 1884 and died in 1962, figured out something that has stood the test of time. Discussions about ideas are powerful and energizing for ambitious people who have a thirst to learn and better themselves.

This week I listened to a friend describe a proposal they’d been presented with. I recognized it as a classic “heads I win, tails you lose” scenario: the party on the other side from my friend would win regardless of the outcome. To be fair, these situations don’t always end badly: if the other party wins, you could win also. But if you lose, they still win.

I’m not a fan of this type of situation because of the misalignment of incentives. The other party is fine regardless of the outcome, so they usually have minimal incentive to push for an outcome that benefits you. This is different than a situation where your incentives are aligned and you win or lose together—in that case, the other party is much more likely to push for the outcome where you both win.

These situations are much more prevalent that people realize, but I do my best to identify and avoid being part of them.

You may have heard this proverb:

If you give a man a fish, you feed him for a day. If you teach a man to fish, you feed him for a lifetime.

This makes sense to me. Sometimes people ask for your help with a problem, but they really want you to solve it for them. If you do, you’ve satisfied their immediate need but not set them up for future success. You’ve just taught them to call you whenever they encounter that problem.

I don’t believe in leaving people hanging when they ask for your help. Instead, I believe in supporting them. I won’t solve the problem for them, but I’ll be there to help them think and navigate through the problem. I make it a point to not lead; instead, to follow their direction. I try to support, nudge, and encourage along the way. When the problem is solved, they’ve solved it—I haven’t. The process of figuring out the solution sticks with them, and they can comfortably solve problems like it in the future on their own. And you’ve helped them become more confident. When someone succeeds in doing something they thought was impossible, they become surer of themselves and their abilities. They start to look at other problems not as insurmountable but as puzzles they can solve if they focus and put forth the effort.

I’m not sure who wrote this proverb, but it’s spot on. I prefer to teach someone how to fish.

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.

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.

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.

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.

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.