Life Advice

A few weeks ago, I had lunch with my Godson, a sophomore in college. Towards the end, he asked, “Do you have any career advice for me?”

I immediately thought of this blog post on Capital Gains that talks about the dangers of giving life advice based on your own experiences. From the piece:

"…agreeable extroverts will probably tell you that the best thing you can do for your career is to meet as many people as possible, so you have lots of second-degree connections through which you can hear about opportunities. This is probably true for them, but someone who naturally loves nerding out about esoteric programming languages would dismiss this advice out of hand—meeting people is hard, getting them to like you is harder, so you should focus on simple, achievable goals like getting a thousand stars on your Github repository.”

Success comes from a combination of hard work, luck, and skill at the work one is doing. However, a less often discussed component is our inherent temperamental traits. In other words, depending on who you are, some stuff is easy for you, and other stuff is really, really hard. And this matters a lot.

Personally, it’s very easy for me to wake up in the morning and go to the gym. I almost don’t even think about it. I just go. On the other hand, it’s very difficult for me to keep in touch with friends and acquaintances. It takes lots of work.

I have a friend who is the exact opposite. He has struggled his whole life to find a way to build a consistent workout routine. I’ve seen him try enough to know that I don’t have more motivation or willpower than he does. I’m certain of it. It’s just inherently easier for me to do the thing we’re both trying to do. Conversely, he effortlessly keeps in touch with a huge network. Regular phone calls to friends when he’s driving. He stops in on people when he’s in town. Remembers birthdays. Sends gifts. I have to really work at it. It’s hard for me. Of course, it’s important to him, and he does it with purpose, but I can see that it’s also easier for him than it is for me.

Obviously, this applies to our work as well. So if you advise someone to get into the legal profession and, despite your personal success in that field, they have a really hard time consuming large amounts of complex text for long periods of time, all else equal, that person is really going to struggle, and you’ve given them really bad advice. Similarly, if you tell a math genius who is shy to get into a sales job early because that’s where the money is, you’re really setting that person back. Both because they’ll really struggle at the job and because they’ll suffer from a very high opportunity cost of not building multimillion-dollar machine learning models for an AI company or something like that.

People giving career advice are often biased and tend to lean towards their unique, long, and winding path to success. That’s a bad idea. The most extreme example is “follow your passion.” This is great advice if your passion is financial analysis, but not so good if it’s skateboarding.

All of this is to say that giving career advice is really hard, and we have to be cautious about not sending younger people down our paths because what worked for us in so many ways may never work for them.

A while back, I wrote a summary of my best career advice at the time titled 15 Things I Wish I Knew Before I Started. I went back to take a look at it to see if I was guilty of giving biased career advice. It's not perfect, but I was happy to see that it holds up fairly well.

Anyway, if you’re wondering what I told my Godson, I came up with two pieces of (hopefully) unbiased advice:

1/ Pursue opportunities with leverage (adapted from Naval Ravikant). You may not be able to do this in your first job out of college — honestly, your first few years are probably going to suck, so you’ll have to keep your head down and grind for a while — but always try to ultimately pursue work where your outputs are disproportionate to your inputs.

2/ Leave something on the table. Leave jobs, partnerships, and business relationships where the other person feels like they got more from you than what they paid. That results in a reputation with a surplus where people will feel good about working with you and will say good things. That surplus compounds. If someone thinks you’re good and they hear from someone else that you’re good, now they think you’re really good, and they’ll tell people that you’re really good, now those people think you’re really good. And on and on. If you do this well, your career will feel less like you’re climbing a ladder and more like you’re sailing on a boat with a steady wind at your back.

2024 Annual Review

It's that time of year when everyone sets their New Year resolutions and goals for 2025. I don't really do resolutions and besides setting a couple big goals for the year, I prefer to focus on standards and habits. It's also a time to reflect back on 2024. I came across a great approach to this in this post from Sahil Bloom that pushes you to reflect by asking yourself 7 key questions to reflect on the year. I went through it and typed out my own answers and found it really valuable. You might too.

Greatest Strength = Greatest Weakness

Early in my career, managers were traditionally expected to tell their employees their weaknesses and how to improve them. Then, they would check in every few months to discuss their progress. It took me a long time to realize that this was a mistake. Over and over, in my career, I've found that a high-performing person's weaknesses are what actually make them great at what they're great at. Identifying how an individual’s weaknesses actually support their strength can you give a lot of insight into how to best interact with and manage that person.

• People who are perfectionists and demand extremely high work quality spend too much time on unimportant things and have trouble prioritizing.

• People who are great strategic thinkers struggle with on-the-ground execution plans. 

• People who are extremely adaptable and can respond quickly to challenges struggle with focus and stability. 

• People who are really optimistic ignore potential obstacles and can be unprepared for setbacks. 

• People who are highly competitive can create friction in their team and struggle with collaboration.

Hire people who are the best in the world at what they do and let them run after that thing. Spending time having them focus on improving something that they don't do well and probably don't enjoy doing is a low ROI effort. Of course, they should know their weaknesses and how they might impact others and should develop the flexibility and self-awareness to know when to dial them back or complement them with other traits. But doubling down on a high performer’s strengths will lead to much better outcomes and a much happier team.

Asking Great Questions

Pushing oneself to ask great questions is extremely important. It forces you to think critically, accelerates your learning, improves decision-making, and helps build trusting relationships. Here are some things that have helped me ask better questions:

Tell yourself a story and use questions to fill in the gaps.

When I'm interviewing someone, being interviewed, or just having a conversation with a colleague or founder about a business problem, I typically take what the other person is saying and try to tell a story that makes sense in my mind. If someone is explaining a new company they'd like to start, I'm listening, but as I hear them talk, questions pop into my head about things I want to know more about or inconsistencies with my preconceptions. This is the trigger for most of the questions I ask, and it’s a useful way to generate dozens of questions in a single conversation.

Of course, you have to temper your questions and prioritize the most important ones so you don't sound like a nut. But forcing yourself to tell your own story based on what you're hearing—and fitting it into your worldview, or using it to learn something new and adjust your worldview—is a great way to ensure you're asking high-value questions.

Be ruthlessly authentic and ask “dumb” questions.

Have you ever noticed that whenever you ask a “dumb” question, it often turns out to be a great one? Dumb questions are wonderful. They typically simplify the topic, challenge assumptions, align the conversation at a high level, and enhance inclusivity. The trick is having the humility and courage to risk showing that you don’t know something that others do. This is definitely a risk worth taking. Try to never hesitate to do this. Be authentic. The best questions are about the things you really want to know. As someone once said, “Not knowing is not ignorance; not seeking to know is.”

Ask what people think, feel, or would do—not what they know.

I almost always find that opinions based on facts are way more interesting than simple facts. Instead of asking a job candidate, “What is our competitor's product strategy?” try asking, “What do you think of our competitor's product strategy?” Similarly, don’t ask your real estate broker, “How can I get a better price?” Instead, ask, “How would you go about getting a better price?”

This tactic encourages the person to really think about the answer and provides you with genuine insights rather than just reciting what they know. Also, give them time to think and express their full answer. Rushing them only leads to less interesting responses.

Risk, Reward, And Working In Tech

The other day, I was chatting with a guy who works at a restaurant down the street in the South End of Boston. He was telling me it was his last couple of months at the restaurant as he had just graduated from college.  He said he wanted to get his money's worth for all the money he spent on college, so he was going to get a higher-paying job in residential property management. He seemed like a sharp guy, so I had this impulse to tell him to get into tech. But I hesitated and decided not to. 

I sometimes forget that tech requires a certain personality. A high tolerance for risk. And I didn't really know the guy, so it didn't feel right to try to direct him one way or the other. 

With the relatively high salaries in tech, flashy products, and nice perks, it's easy to forget how volatile and risky the space actually is. It's definitely not for everybody. And if you're not the type of person who can handle booms and busts, stay away. There are plenty of other less lucrative but far more stable jobs to get into. 

It's worth remembering why this is. Tech companies, by definition, are investing in high growth that comes from new ideas. Investing in new ideas is risky. They often don't work. The greater the risk, the greater the potential reward. In boom markets, working in tech is great. In busts, it's not. I’ve been through 4 of these downturns in my career — the 2000 dot-com bust, the 2008 Great Financial Crisis, Covid in 2020, and the end of the low interest rate period in 2022. None of these were fun, and all of them came with a great deal of professional stress and anxiety.

Because of things outside of your control, such as interest rate changes, investor sentiment changes, geopolitical events, new technologies, government policies, etc., tech markets are inherently cyclical. And the risk takers that are putting capital into new ideas always feel downturns first, because that's the capital that investors will pull out and put into safer, less risky investments.

Before embarking on a new career in tech, make sure you understand this reality and are up for the dramatic ebbs and flows in your day-to-day life that are a natural, unavoidable part of working in this field. 

Company Ambitions & Personal Ambitions

Interesting conversation on the Ben and Marc show on the difference between personal ambition and company ambition. You always want your team to have the company's ambition in mind and for them to get to a place where that's their top priority. Of course, very few people can completely prioritize the company's ambitions over their personal ambitions, so to some degree, this is always a bit of a tradeoff.

When someone asks me the best way to be successful inside of a company, I always point to the notion of putting the company’s ambitions ahead of your own. The irony in this is that this actually propels you forward personally more than the alternative. This is true for a few reasons:

1/ It increases the chance that your company will be successful and you'll wear that brand and benefit from it for the rest of your career.

2/ People will view you as a great leader who puts the company's needs first. You'll be admired and respected and people will want you in the room. These people get promoted.

3/ It makes you a better operator in that you're getting better training by learning how to successfully operate a company more quickly than people that are busy playing politics.

Prioritizing your company’s ambitions over your own always seems to have the ironic outcome of a faster path to achieving your own.

Humility & Truth Seeking

I've always placed a lot of value on people who are humble. I've written about it here. I've always thought about humility in the context of getting better at what you do. If you have the humility to know that you aren't the best at everything, that drives you to improve. And of course it makes you much more fun to work with. 

I had a conversation with someone the other day who pointed out another reason why humility is such a great attribute: it's a signal that you see the world clearly. If you have the humility to see your weaknesses (which we all have) and to understand that whatever success you've had required the support of lots of luck and lots of support from other people, then you see the world more clearly than someone that doesn't. And an undervalued skill in the workplace is the ability to see the world clearly. To seek the truth.

An executive's job is to make good decisions. You can't make good decisions if you're not seeing the world as it is. Being able to see the world as it is might be the most important thing an executive can do. Often once you know the truth, making the decision is often the easy part. Humble people are naturally better at this. and this is just another reason why that value is so important in the workplace. 

Investor Context & Incentives

The best managers prioritize giving their teams as much context as possible. When employees lack context, it leads to an enormous amount of unnecessary friction and uncertainty. It’s crucial for managers to give context around the work they’re asking employees to do, the decisions they’re making, and the priorities they’re driving. At the same time, employees should play a role here as well. If they’re not getting the context they need from their manager, they should ask. Employees should empathize and push hard to get in the head of their manager and understand their manager’s incentives and the context they’re operating in. It’s a partnership.

While this is fairly well understood, often, I find that managers don’t understand the context and incentives of their boss’s boss or even their boss’s boss’s boss (the company’s investors). I’ve found that deeply understanding how investors think is an essential part of being an effective operator. It’s even helpful to understand the content and incentives of a company’s investors’ bosses (the investors’ limited partners).

Here are four books that have helped me get inside the heads of the individuals that invest in the companies I’ve worked with, both venture-backed and private equity-backed. Understanding the history of these industries, their investment strategies, and how investors are measured and managed has made me a much more effective operator and leader.

Venture Capital

The Power Law: Venture Capital and the Making of the New Future by Sebastian Mallaby

Angel Investing: The Gust Guide to Making Money and Having Fun Investing in Startups by David Rose

Private Equity

The Private Equity Playbook: Management’s Guide to Working with Private Equity by Adam Coffey

Two and Twenty: How the Masters of Private Equity Always Win by Sachin Khajuria

Refusing To Fail

I heard Phil Mickelson, the legendary golfer, tell a great story the other day.

He was asked what makes the best golfers the best golfers in the world. He told a story about how a long time ago, he really struggled with short putts. One day his coach recommended that he try to make 100 three-foot putts in a row. If he missed one, he'd have to start all over again. And he should keep practicing this until he can reliably make 100 in a row. He claims that one time he made it all the way to 99, missed the 100th, and started over. 

Years later, he was mentoring an up-and-coming amateur golfer who was struggling with short putts, and he gave that golfer the same advice. Several months later, he checked in on how the golfer was doing with his putting, and the golfer said, "yea, that was really hard, I got to where I could make about 50 in a row, and I gave up.”

This golfer never made it in the PGA.

This is a great analogy when thinking about startup investing. Often, in the early days, you're really investing less in the idea or the product or the market; you're really investing in the founder themselves and their willingness to persevere and navigate through the idea maze and do what, in some cases, seems impossible. Some people work on some projects where for whatever reason, they will absolutely refuse to fail. Elon Musk is a great example. Both SpaceX and Tesla should've failed multiple times. But he persevered and forced it to happen through sheer will. Of course, he's incredibly smart and talented, but that wouldn't have been nearly enough. This quality doesn't exist in everyone, and even for those that do, it doesn't exist for every project at every time in their lives, given changing life circumstances and priorities.

This golf analogy is a good one to consider when you're investing at an early stage where you don't have much to go on other than the talents, skills, and dedication of the founder and founding team.

Learning How To Learn

Perhaps the most valuable skill one can have today is the ability to learn new things. The world is changing so fast. Static, top-down learning and development programs are quickly becoming outdated and irrelevant. 

The good news is that there is so much information available for free. Any self-motivated individual can learn almost anything on their own — assuming they know how to learn in a self-directed way.

In my mind, there are three steps to being proficient at self-directed learning:

1/ Identify what you don't know that's important to learn.

2/ Find resources to learn about the things you don't know.

3/ Do the work to learn about the things you don't know. 

Identify what you don't know. This is the hardest part. Because often you don’t know what you don’t know. This is where it's helpful to have mentors that can help identify your blind spots. It's also helpful to have a network of other people who are doing your job or the job you want to do. 

For an aspiring sales leader, here’s a list of things they should be learning as they climb the ladder from individual contributor to a sales manager to an executive.

Individual Contributor:

Sales tactics (discovery, outreach, access, presenting, proposals, objection handling, creating urgency, closing, etc.).

Understanding your buyer and your buyer's industry (business model, competitors, motivations, priorities, org chart, decision framework, regulatory, etc.).

Sales Manager:

Management (hiring, firing, employee engagement, giving feedback, setting priorities, territory management, performance management, etc.).

Sales strategy (forecasting, OKR management, customer segmentation, prioritization, leadership reporting, etc.).

Executive:

Management against industry metrics (e.g. in SaaS - CAC/LTV, Rule of 40, Payback period, growth rates, gross margins, etc.). 

Company strategy. Setting mission and vision. High-level qualitative goals and financial goals. 

Thinking like an investor. Understanding how financial metrics, storytelling, and a long-term plan connects to a company’s valuation. Understanding the mindset and motivation of investors that would invest in your company. 

Find resources. This is relatively easy these days. Use Twitter to follow experts in your areas of interest. Setup a Feedly account to get a feed of blog posts related to the interest area. Setup your podcast feed to receive daily podcasts on the topic. Read the best books on the topic. Join communities (such as Pavillion or SaaStr) to interact with peers. Leverage your investor networks (First Round Capital has a great one). Find a coach. Find a mentor.

Do the work. Once you've identified the learning area, start to obsess about it and immerses yourself in content. You'll quickly identify areas that you didn't know you didn't know. Learn about those things. Create habits that force you to keep learning. Listen to one podcast per day. Read 50 pages per day. Set a goal of having coffee with at least one mentor or person that does the job you want to do each month. Repeat. 

Employee Stock Options & Funding Rounds

A friend of mine sent a link to a press release about a company that just closed a huge funding round at a huge valuation that expects to go public over the next few years. He wanted my thoughts on other companies that he could join that have had similarly successful funding rounds. His thinking was that he could make a lot of money on the next few financing events, even an IPO.

I think job searchers need to be careful with this kind of thinking. A successful funding round with great investors is a very positive signal. And it's always tempting to jump on the latest rocket ship. But there are a few things potential employees should consider before joining a company following a large funding announcement:

You're not going to get credit for the company's past success. If a company raises a Series B round at a $100M valuation, following a $10M Series A round, the company's valuation has grown by 10x. That's a lot of value creation. But if you join the company after the Series B has closed, you've missed out on all of it. The stock options you receive will be priced at the post Series B valuation. So you're starting from zero. You'll only get credit for the value you create going forward. You have to place a bet on the company's ability to continue to build value on top of what they've already created. A small caveat here: there's often a difference between the valuation investors paid and the company's fair market value, as determined by auditors. So employees that come in after the round might not pay as much as investors paid.

Valuations are super high right now. Because private company valuations are typically marked against the public market, and the public markets are on a 12-year bull run, valuations are arguably inflated at the moment. If the bull market continues, this isn't a problem. But if prices come back down to earth, valuations could come down, and you may find that your options are underwater (meaning they're worth less than the price you'll have to pay for them). 

The later you join, the less equity you'll get. Startups reward early employees with lots of equity (potential upside) in return for taking the risk of joining before anything has been built. As time goes on, this risk decreases, and so does the amount of equity the company needs to grant to attract great people. Less risk typically means less equity.

The less senior you are, the less equity you'll get. Generally, the really material stock option grants (.5% to 2% of the value of the company) are reserved for the most senior executives. Employees at lower levels will receive a fraction of that.

Your options have to vest. In most cases, you won't just get an equity grant. You'll have a vesting schedule. Typically over four years with a 1-year cliff. Meaning you won't have the right to buy your options unless you've been at the company for more than a year. 

Your vested options aren't liquid. Not only do you have to create value on top of the last funding round, but you also have to find a way to cash out at some point. Generally, this is only done through an acquisition, a secondary offering where an investor buys some amount of employee shares, or an IPO. While IPOs have made a resurgence, it's enormously rare that a startup makes it that far; of the tens of thousands of startups out there, less than 200 companies went public in 2019. 

With all of this said, don't get me wrong, funding rounds are an exciting thing. And they're absolutely a signal that the company is onto something. And I’m a huge fan of investing in private companies as early as possible. My point is that potential employees should act like an investor and dig deep on how much value they believe can be created following the big announcement, and what share of that value they'll receive, and the likelihood that that value will be liquid within a reasonable time frame. 

This is particularly important for salespeople as they negotiate job offers. There's a tradeoff associated with optimizing for your own success (cash from commission) versus the success of the larger organization (equity). Depending on the circumstances, one can be a lot bigger than the other. The above considerations are important inputs into how to think about the company you might want to join and the compensation plan you want to advocate for as you negotiate an offer.

Leverage

Over the weekend I read the Almanack of Naval Ravikant. Naval is an investor and entrepreneur and the founder of AngelList. The book gives his unique perspective on building wealth and enjoying life.

I flew through this book. I literally couldn’t put it down. The part I enjoyed the most was his perspective on leverage. He believes that leverage is the thing that leads to wealth. You can get leverage from people working for you. You can get leverage from investing your money. But the highest form of leverage — the new form of leverage — is to spend time selling or building products with no marginal cost of replication. This is easy to do in the digital age. You can write some code that can create infinite value, well beyond the time you put into writing the code. You can create a podcast that millions of people can listen to. These are things where the output is disconnected from the input. This blog post is a form of this leverage. It only took me a few minutes to write, but it can be read by millions of people for years to come.

As Naval points out in the book:

A general contractor has more leverage than the person that repairs the house.

A real estate developer has more leverage than the general contractor.

A money manager of a real estate investment fund has more leverage than the real estate developer.

Zillow has more leverage than all of them.

You see that as you climb the ladder, the value created gets more and more disconnected from the input. Zillow, in addition to having labor-based leverage (employees) and money-based leverage (venture capital), also has code-based leverage (leverage that can scale infinitely with near-zero marginal cost). Whereas the person repairing the house has none of that. That person is paid an hourly wage that is tied perfectly to the amount of time he or she puts in.

I really like this way of thinking about modern-day wealth creation. Spend your time on high leverage activities and projects, particularly those that are digitally-oriented. This is one thing I think people miss when they point to tech stocks being overvalued. These companies can get really big really quickly. That can be hard to wrap your head around.

The full excerpt on leverage can be found here. I highly recommend giving it a read.