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.

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.

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.

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.

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.

A few thoughts on knowledge. Knowing or understanding how something works increases the chances of achieving a goal. A knowledge gap decreases the likelihood of achieving it. I recently listened to close friends share how they were caught off guard when their child was rejected for admission to a private school. They learned after the fact that an acceptance decision by some private schools is multifactorial—a child’s intelligence tests scores is just one factor. For better or worse, parents who understand the admissions process and act based on their knowledge increase their probability of success. This is just one recent example. Knowledge can have an outsize impact on outcomes in various aspects of life (e.g., entrepreneurship).

I like to think of it like this. Imagine you’re in a room trying to get out. Not knowing is the room being pitch black. You’re simultaneously trying to figure out (1) where you are in the room, (2) where the exit is, (3) where any obstacles are, and (4) how to move toward the exit. Knowing is the room having all its lights turned on and someone in it pointing to the exit door. All you have to do is move toward the exit. You can succeed either way, but in darkness it will take you longer.

The bad thing about knowledge is that it’s not universal. Some people have more knowledge than others about specific topics. They understand the edge it provides and the compounding impact it can have over time. They can accomplish more at a faster rate. Their knowledge is the result of the large amounts of time and energy they’ve put toward acquiring it—firsthand or by studying the knowledge of others before them. It’s their competitive advantage, and it’s unlikely they’ll readily share their competitive advantage until they’ve achieved their goals. Doing so prematurely could boost their competition and decrease the likelihood that they’ll achieve their goals. Regardless of how we feel about this, it’s a reality we should accept. It’s just how life works.

The good thing about knowledge is that it’s not static. Because augmenting our knowledge is within our control, we can increase our chances of achieving a particular goal. Adding to our store of knowledge isn’t easy; it requires time and energy. But the payoff from combining knowledge with execution can be enormous. Many who have achieved outsize success consider themselves lifelong learners. They’ve committed to learning throughout their life. The knowledge they gain is a significant contributor to their success, and they’re happy to put the time and energy into continuously acquiring more knowledge.

If you’re looking to achieve a goal, consider thinking about how big your knowledge gap is and what you can do to fill that gap and increase your chances of success.

With the new year approaching, many people are thinking about what they want to accomplish. A friend told me his weight loss goal for 2023 and asked for feedback. I think he was hoping I’d share my experiences with food or exercises. Instead, I had one piece of advice: start simple by weighing yourself daily. It takes five seconds and doesn’t require changing your life as you’ve known it.

Losing weight is hard for many people—especially when they make abrupt changes. Starting with a feedback loop, instead of big changes, can be a great first step. By measuring something every day that you want to improve, you’re more likely to change your behavior. And if you change your daily behavior, you’re more likely to form habits that contribute to achieving a goal. For example, if you weigh yourself every day, you’re more likely to rethink eating a piece of cake after dinner if you don’t like what you saw on the scale that morning. If you establish a habit of not eating desserts, that reduces your calorie count, which can get you closer to your weight loss goal. Of course, you need to do other things, including upping your physical activity—but you get the idea.

Feedback loops can be a simple but powerful way of taking the first step toward forming powerful habits that align with a goal. Next time you think about something you want to accomplish, ask yourself what feedback loop will send you down the right path.

I had a chat with my family over the holiday about truthful feedback. I asked them to share with me any observations they have about me (positive, negative, or neutral). I let them know I wanted the truth and wanted to understand different perspectives to improve my decision-making. I value the feedback of those who’ve known me longest. I may not agree with it, but I still want to hear it. Ideally, I want to hear their raw thoughts, not a watered-down version that I have to interpret later.

The request was embraced, and I got some valuable info. One family member thanked me for giving them permission to provide feedback. They said they’ve had feedback for me in the past but didn’t feel it was their place to share without my asking for it. I always assumed those close to me know how I value candid feedback. I also assumed that knowing this meant they would readily share any feedback. Today that assumption was proven wrong.

As I’ve matured, I’ve become more intentional about seeking out people who will readily share candid feedback. What I missed is that people in my circle might have something to tell me but not be comfortable doing so absent an explicit request.

In 2023, I want to have the truthful-feedback conversation with more credible people in my circle. I suspect this will be a positive exercise that takes some relationships to the next level in the long term and unlocks some valuable observations in the short term and long term.