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. 

Rule of 40 vs. Real Cash

It seems like whenever we go through a shift in the economy, the fundamentals of finance become increasingly important. During the near-zero interest rate environment we had for more than a decade, growth was rewarded in an outsized way. 10x and 20x revenue multiples were common for startups. Because the risk-free rate of return was near zero, there was no real opportunity cost in investing in something risky. That drove up the value of companies that were investing in big growth. Today, this has changed quite a bit. There is an opportunity cost to investing in something that might not generate cash for a while. So, a lot of the attention has shifted from growth to profitability. Investors want to see cash get generated more quickly. The Rule of 40 (ensuring that a company's operating margin % + its growth rate exceeds 40%) has become a common way of categorizing top-tier startups in this environment. Boards are pushing company leaders to get to Rule of 40 as quickly as possible. Given so many companies are coming out of the grow-at-all-costs approach, the easy thing to do is to pull back on investments, project a conservative growth rate, and drive down costs to make the company's operating margin high enough that it gets the company to 40+ in the next year or two.

This is a potentially short-sighted approach, especially for earlier-stage companies with small revenue. Returning to the fundamentals of finance, we know that the value of a financial asset is the present value of the cash that you can take out of it over its lifetime. Forecasting these cash flows is done using a discounted cash flow model. Revenue multiples and the Rule of 40 are crude proxies for understanding the present value of future cash flows. The danger of the Rule of 40 for smaller companies that aren't generating significant cash flows is that they underinvest in growth to achieve a higher operating margin at a point in time but never get to a point where the company generates high amounts of actual cash.

The Rule of 40 measures a point in time calculated using the % growth rate and the % profit. But companies are not valued on what they're doing right now. And they're not valued on their growth rate. And they're not valued on their profit margins. They're valued on real amounts of cash generated in the future. Rule of 40 can be a useful metric for investors to gauge the health of a business. But that has to be tempered with an understanding of the investments the company is making today to drive future real cash flows. 

One good way to manage this is to classify revenue and cost projections into two buckets. 1/ Core: revenue that will be generated from investments made in the past, and 2/ New: revenue that will be generated from new investments. Leaders need to really understand the future cash flows associated with their core business and whether or not that will produce adequate cash flows relative to expectations. That provides the input needed to throttle investments in new initiatives. The core should get more profitable and the new stuff should drive lots of new revenue. Blending the two and optimizing to a short-term metric runs the risk of severing the company’s execution plan from what’s best for investors over the long term.

The Best Books I Read in 2023

I skipped this last year for some reason. But I’m back with the best books I read in 2023. Some business, history, longevity, investing, and a little golf. View past lists (2017 through 2021) here. Enjoy!

 
 

1/ Killers of the Flower Moon: The Osage Murders and the Birth of the FBI by David Grann. In the late 1920s, the Osage Indians in Oklahoma were the richest people in the United States. This wonderful book chronicles terrible crimes committed against various tribes and the formation of the FBI that ultimately solved and exposed the atrocities. You forget that the FBI (and police departments in general) are a 19th and 20th-century phenomenon. Apparently, they just made this book into a movie. Looking forward to it.

2/ Going Infinite: The Rise and Fall of a New Tycoon by Michael Lewis. The story of Sam Bankman Fried and the collapse of FTX. I knew most of the story before reading this one so I didn’t learn all that much but Michael Lewis is just so good. More people would read if more authors wrote like him.

3/ Greatest Game Ever Played, The: Harry Vardon, Francis Ouimet, and the Birth of Modern Golf by Mark Frost. I’ve been meaning to read this one for a long time. The story of a young caddie who wins the US Open in Brookline, Massachusetts, against all odds. Tremendous read.

4/ Outlive: The Science and Art of Longevity by Peter Attia MD. Sort of a bible for those interested in longevity (we all should be!). He dives deep into what he calls the Four Horsemen, or chronic diseases of aging: heart disease, cancer, neurodegenerative disease, and type 2 diabetes. Fun fact: for every human over the age of 100, there are about nine billionaires.

5/ The Intelligent Investor: The Definitive Book on Value Investing by Ben Graham. I read this because I saw that Warren Buffett said that chapters 8 and 20 are the “bedrock of my investing activities for the last 60 years.” The whole thing is good. Lots of fundamental truths investors need to know.

6/ The Little Book of Valuation: How to Value a Company, Pick a Stock and Profit by Aswath Damodaran. A great primer on how to value companies. It's sort of a textbook, but it doesn’t go too deep and is a relatively easy read on the fundamentals of companies at the earliest stages to post-IPO.

7/ When Money Destroys Nations: How Hyperinflation Ruined Zimbabwe, How Ordinary People Survived, and Warnings for Nations that Print Money by Phillip Haslam. An excellent history of the inflation crisis in Zimbabwe where the government was forced to raise interest rates to over 5000% to bring it under control. So many factors contributed to this crisis, not the least of which was the terrible wars in Zimbabwe that took so many men out of the workforce and forced the government to provide enormous amounts of government assistance, contributing to massive increases in prices.

8/ A New World Begins: The History of the French Revolution by Jeremy D. Popkic. I guess I never studied the French Revolution in school because this was mostly new content for me. Just a fascinating time in history and such an important step forward for liberal democracy across the world.

9/ The Managerial Revolution: What is Happening in the World by James Burnham. A fascinating and important book written in 1941 on the shaping of society that has turned out to be very true. Burnham argues that capitalism is dead and that it has been replaced not by socialism but by a new economic system called managerialism — rule by administrators in business and government.

10/ Principles: Life and Work by Ray Dalio. Really solid insights and perspectives from the founder and CEO of Bridgewater Associates. He talks a lot about truth-seeking, which is so critical to be successful in business. He pushes the reader to be “radically open-minded” and have a genuine worry that their ego might be getting in the way of seeing the world as it is and making the optimal decision. Great read.

 

Selling Software vs. Selling Work

One of the most interesting aspects of AI and how it'll change the workplace is how it might disrupt the large SaaS players and the SaaS model itself. The SaaS business model typically is set up around licensed "seats," where a SaaS company sells an individual seat to an individual employee to give them access to the software. The idea is that the software makes the employee more productive, and that gain in productivity is 2x to 5x the cost of the seat. This formula has led to the emergence of thousands of successful SaaS companies and hundreds of billions of dollars in market cap.

AI changes this quite a bit. Unlike SaaS, AI doesn't just make an employee more productive. It does the actual work of the employee.

As an example, if AI could triage patients coming into a hospital and connect them to the right next step (a specialty referral, an inpatient admission, a prescription, etc.), that's not making the healthcare provider a little more productive, that's opening up a nearly unlimited capacity to triage patients because the Ai can do it significantly faster 24 hours a day. 

This is very different than making an employee 20% more productive. And it's different from replacing an employee with a machine. It's taking ownership of a work product and removing caps on output. Try to imagine doing this across multiple areas of work inside of a company. All kinds of limits to growth and productivity will be removed, and companies could be infinitely more valuable. 

Coming back to the notion of SaaS and selling seats. The AI company would never sell this way. The ROI isn't centered around increasing employee productivity, it's centered around doing jobs with nearly uncapped output. It'll be interesting to see how this impacts the SaaS business model that has become so prevalent over the last several years.

What Artificial Intelligence Is Not

With all the hype around AI, I’ve seen the media and investors get a little bit sloppy with the definition of AI and have been calling things AI that aren’t AI. When there’s a big trend like this one, there’s a temptation to attach things to the trend that shouldn’t be attached to the trend. I’ve heard it’s hard to get meetings these days with top VCs if you’re not talking about AI in some form so founders are certainly incentivized to stretch. It’s worth defining what it actually means and what things are software versus AI.

Software that is not AI is running off of mid-20th-century technology. It effectively acts like a digital calculator. A programmer codes the software to do something, and the software behaves accordingly. The software is not thinking. It can’t do anything it wasn’t coded to do. If the software makes a mistake, that is the fault of the programmer who coded it.

Ai is much different. Ai mimics human intelligence. It can do more than what it was coded to do. ChatGPT describes itself this way:

The ability to learn, adapt, and generate contextually relevant responses based on patterns in data is what elevates it from traditional software to the realm of artificial intelligence. It's a software that, to some extent, can exhibit intelligent behavior and respond dynamically to various inputs.

One way to think about this is that software makes the human mind more efficient while AI mimics the human mind. From an investing perspective, this difference is really, really important. As this technology develops, given the massive productivity gains from a technology that can do the job of a human infinitely more quickly, 24 hours a day with no breaks could cause us to totally rethink how to value companies that create and/or leverage this technology.

Some VC Insights

This recent episode, 20VC Roundtable: Is the Venture Model Broken? was one of the best I’ve heard in close to ten years of listening.

I found myself jotting down a few notes. Listen to the whole thing, but here are some of the highlights:

  • VCs tend to jump to the “next big thing” (Crypto, AI, etc.) because that’s how you get markups on your investments. But, by definition, the “next big thing” isn’t contrarian and, in theory, wouldn’t be where the outsized returns are. There is an interesting conflict for VCs between showing a good markup and getting actual returns.

  • In venture, patience is an arbitrage.

  • The true outlier investments, in theory, are the cheap investments. That’s because they’re truly contrarian, and nobody wants to invest in them.

  • Pre-product-market-fit, stay as lean as possible. If you get ahead of the market, the team will have built things that aren’t perfectly aligned to the market, and they’ll develop opinions about what the market needs based on what you have and what’s been built. Slow that down and make sure the market is pulling and you’re not pushing.

  • When you have product-market fit, your next customer should be marginally more attractive than the last one. e.g., you shouldn’t have to be straining your offering to get more customers. At some point, everyone should want it.

  • Often, a company’s go-to-market is better than its product-market fit, and you can fool yourself into thinking you’ve found it.

Two Rules For Negotiating

There are two rules for negotiating that are absolutely essential.

1/ Be able to make the other side's argument as effective or (ideally) more effective than they can. If you can't do this, then you’re lacking empathy for the other side which is very dangerous. If you can’t do this, then you likely don't truly understand the issues at hand, which means you won't be as effective as you could be. Never negotiate without doing this. 

2/ Internalize your BATNA (best alternative to a negotiated agreement). A lot of people know what this is, but very few do it, often because they don't even want to consider the idea that they won't get a deal done. You have to go there. If you don't play out the worst-case scenario in your mind, internalize it, and understand that if you can’t get a deal done the sun will still come up in the morning, you are in a much weaker place. Get comfortable with your walk-away position. 

These are two simple things that very few people do consistently. Following these rules will make you much more effective at getting to a deal that works well for both sides. 

Value Chains & Charter Communications Versus ESPN

The recent contract dispute between Charter Communications (the large telecom provider) and ESPN (a Disney subsidiary) is possibly this generation's most compelling business strategy story. It goes back several decades and it hit a tipping point in the last few weeks when Charter removed ESPN from its cable bundle. Ben Thompson from Stratechery has been writing some fabulous stuff about all of this that I highly recommend reading. 

It's complicated and convoluted but the short version is that for years ESPN has been charging the cable companies extremely high per-subscriber rates to allow them to include their content in the cable bundle. Live sports content has always been a major driver for cable subscriptions. You can't really offer cable if you don't have live sports. And ESPN has held extremely lucrative sports contracts with MLB, the NFL, the NHL, and others. This allowed ESPN to keep raising rates on the cable companies. Cable companies consistently passed this onto consumers in the form of increased subscriber rates but that could only go so far. Ultimately it had to be taken out of the cable companies’ margins and they were suffering as a result. ESPN was loving life. They leveraged the cable companies to acquire new subscribers and then leveraged the cable bundle that included content providers like CNN, TBS, Food Network, etc., to lock in their customers and experience near-zero churn (requiring that your product be bundled into a set of other products that appeal to different users with different use cases is probably the #1 way to retain customers). To make it worse, ESPN also went around the cable companies and offered a direct internet-based TV service (ESPN+) that had exclusive content that they wouldn't show on cable. As a golf fan, I know this firsthand. The first two days of major tournaments can often only be watched on ESPN+ and not cable. So ESPN was gouging the cable companies on their distribution contracts and then devaluing their distribution partner and generating even more revenue by going around them. 

The tables finally started to turn when broadband internet became by far the major growth and profit driver for the cable companies. Because of ESPN and other content providers's high rates, and consumers starting to churn and move to the streaming providers, Charter, in particular, started to care a lot less about cable television. This came to a head a few weeks ago when they removed ESPN from their bundle to get ESPN to bring their rates down and offer the cable companies a much better deal. To put the screws to ESPN, when the subscriber tried to tune into ESPN, Charter was planning to include a message that said something like, "We no longer offer ESPN, if you'd like to watch ESPN, please sign up for YouTubeTV or some other streaming service", of course, requiring the consumer to sign up via Charter broadband. This would be really bad news for ESPN, as those companies pay ESPN a far lower per-subscriber rate and churn rates are much higher (ESPN learned the hard way that big tech has a lot more leverage than a regional cable provider). Charter and ESPN finally reached an agreement that was much more favorable to Charter just before Monday Night Football aired on ESPN last week.

ESPN had the dominant position and they took advantage of it and over time they got greedy and ended up weakening their own negotiating position. That's what's so interesting about all of this. They took it so far that Charter just didn't care about ESPN or even cable TV anymore. The value chain that allowed ESPN to flourish for so many years has started to collapse.

There's a lot more to this story, and ESPN may be the winner over the long term for a variety of reasons. And if you're interested in this kind of thing, I'd recommend following it closely. This is nowhere near over, and in fact, it's going to get a lot more interesting in the coming years.

All of this is such a good reminder that companies need to deeply understand where they sit in the value chain and adapt as the structure of that value chain changes over time. This one is so complex because there are so many important and powerful players with different incentives and varying degrees of leverage: sports team owners, sports leagues, telecom companies, content providers, and now a new and enormous threat from big tech (Prime Video, YoutubeTV, AppleTV, etc.). 

If your business model and your position inside the value chain seems too good to be true, it probably is, and you can be sure it won't stay that way forever.

Making Your Values Real

I sent this podcast from Andreessen Horowitz (a16z), the prominent venture capital firm, to my team last week. I'm a huge fan of Ben Horowitz and his perspective and insights on culture and leadership. It's worth listening to the entire podcast, but what stood out to me was the notion of making your company values real and actionable. As an example, a16z has a value where they require their partners to treat founders with great respect. It's one thing to say that, but many venture capital firms do the opposite because they're the ones with the money, and the founder is asking for the money, so the firm acts like they're the one in control (I've seen this many, many times over the years). To make this value real and actionable, the firm has a policy where for every minute that you're late to a meeting with a founder, you are fined $10. I can imagine some of their partners thinking, "whoa, this is weird, it wasn't my fault that I was late, why do I have to pay this money, my last company didn't make me do this."

And that's exactly the point.

That means that this company has a culture that is actually true to its values. It's distinct from other cultures. The $10 fine is a way to make the team feel this distinctiveness. To feel the values.

All of this reminded me of working at Zocdoc many years ago. Our #1 value was "Patients First." That meant we would always prioritize the patient when making a difficult decision. This was real. I recall a time when an enormous healthcare provider wanted us to build a feature for them that would result in a suboptimal experience for the patient. This organization was willing to pay us a lot of money for the feature and it would’ve made hitting our quarterly sales target a lot easier. It was a tough call. We weren't sure what to do. So we deferred to our values. Patients first. We told them no.

As Ben says in the podcast, culture isn't what you want it to be or what you say it is, it's what you actually do. If the team can't see and feel a company's values on a practical, day-to-day level, that means that values and behaviors aren't in alignment. Which means your values aren't real. They're simply words on a wall.

The Human Element In Corporate Failures

Business media and business school case studies love to cite big business failures (Kodak, Borders, Blockbuster, Blackberry, etc.) and talk about how foolish and incompetent management was for leading the company into the ground. It's fun to look back on management's mistakes, discuss them, and hopefully learn from them. When you review these mistakes in hindsight, a certain comfort comes from thinking you wouldn't have been so dumb.

The thing that these stories and case studies miss is the real-life context surrounding management that contributed to the decisions they made. And to me, that's a lot more interesting. I'd argue that often — perhaps most of the time — these people aren't dumb at all. It's much more complicated.

In real-life corporate decision-making, there are multiple factors that contribute to decision-making that those looking back from the outside can't see.

1/ Incentive structures and timelines that drive short-term thinking, e.g., a CEO who's incentivized to focus on this year's stock price. That incentive is in perfect conflict with longer-term strategic transformation (Kodak investing in digital cameras at the time would’ve been an expensive and risky bet that likely wouldn't have paid off during that CEO's tenure, as one simple example).

2/ The personal motivations of individual leaders. In many ways, a company is just a vehicle to drive individual people's self-interest (investment returns, personal compensation, resume-building, fulfilling the company's mission, having power, etc.), and more often than not, that self-interest isn't in full alignment which makes strategic decision making extremely difficult.

3/ Politics around strategic direction. Related to incentives, leaders, in the moment, particularly leaders who may be struggling in their role, often aren't aligned with the long-term growth of the company. They might be thinking about saving their job this week or this month. With that context, leaders are more inclined to lean towards "people pleasing" versus doing the right thing for the company. So, if a board of directors wants to go in one direction and management wants to go in another, management may defer to the board (to keep their job). Or one leader may defer to another leader to improve their reputation with that leader because that leader has a better relationship with the CEO. There are hundreds of little dynamics like this inside any company that are in conflict with doing the right thing. Put more clearly, “keeping one’s job”, in many cases, negatively correlates with good long-term strategic decision-making.

4/ Distractions. When a company is operating at scale, there are always fires to put out and urgent threats to the existing business. This can distract management from spending adequate time on larger, longer-term threats that are harder to see. Of course, the answer is to focus on both. But depending on the complexity and severity of the urgent threats, that’s a lot easier said than done and inconsistent with human nature. These distractions and their importance rarely make their way into case studies or the business press.

I could go on and on.

Leading companies at scale is extremely difficult. It's easy to say that Kodak should've dropped everything and invested in digital cameras. Or that Blockbuster was too late on video streaming. That's easy and, frankly, not that interesting. Identifying that gives you a C+ or a D-. It's much more interesting to try to understand the context that makes doing what seems like the obvious thing so incredibly difficult. Learning from that and creating an environment where leaders and leadership teams can make the best possible decisions is a much more challenging task. Leaders and leadership teams that can do that deserve an A+.

Capital Allocation Inside Companies

I loved this Tweetstorm from The Secret CFO on capital allocation.

You should read it in full, but the key point for me is that if a company has capital to invest, the default position should always be to return it to shareholders via a stock buyback or a dividend.

There are three things a company can do with capital:

1/ strengthen their balance sheet (hold cash or pay down debt)
2/ invest in growth
3/ return capital to shareholders.

The default position should be #3.

There’s an old saying that “profitable companies have run out of ideas.” Meaning that if you make a profit it means you’re not investing in new products and services that will drive future growth. This is a fun saying, but it sort of implies there’s something wrong with being out of ideas or taking a profit. Of course, there’s nothing wrong with this. Companies are designed to create shareholder value. Generating profits and giving the cash back to investors so that they can go out and spend it or invest it as they please is the definition of creating shareholder value. Apple, the most profitable company in the country, had a net income of just under $100 billion last year and paid out a large part of it to shareholders in the form of dividends. They’ve created a high hurdle for new investments in growth. If they don’t expect a new initiative to create a huge amount of value, they default to returning that capital to shareholders.

Obviously, in the early stages of a company, the priority has to be building something such that generating profits is even possible. In these cases, all available capital goes towards growth. But later-stage companies that are generating a material amount of cash through their core business should default to giving capital back to shareholders. Using this as the default position creates a very healthy discipline, ensuring that new investments in growth are fully thought through and approved with the proper amount of analysis, rigor, and skepticism.

Tech Company Layoffs

There’s been quite a bit of news over the last several weeks of tech companies freezing hiring and laying off employees. Perhaps most notably, Meta (formerly Facebook) recently laid off 11,000 employees or 13% of its workforce. I thought I'd write a post about what tech companies are thinking about and the factors that are contributing to these unfortunate announcements. First, some history:

Until about a year ago, the stock market had been on a bull run for about 13 years. There are several reasons for this, but the primary reason was that, during this time, we had zero or near-zero interest rates. When interest rates are near zero, companies can borrow money almost for free, allowing them to invest heavily and grow, grow, grow. In addition, when interest rates are so low, money flows out of fixed-income investments and into riskier equity investments (the stock market). More money in equities means higher stock prices for public companies. Public company stock prices are a proxy for private company valuations, so private companies have experienced the same dynamics. This enabled companies to raise enormous amounts of money with little dilution for founders and shareholders. Due to classic supply and demand forces, more money in equities means that the same company with the same financial profile could be valued at 2 or 5, or 10 times what it would be worth in a less bullish market.

It was a great ride until COVID hit, and the economy stalled because people couldn't leave their homes and go to work and buy the goods and services they had been buying in the past. To get us through the crisis, the federal government rightly provided a massive economic stimulus to businesses and consumers by pushing more than $6 trillion into the economy. Again, more money in the system means higher prices for everything (including stocks). Due to COVID, we also saw major global supply chain issues and price spikes across nearly every category (again, the effects of supply and demand; reduced supply of products drives higher prices). Thankfully, the economy quickly recovered and Americans had surpluses of cash that they were anxious to go out and spend. And they did. As a result, we're now seeing historical levels of inflation. The inflation rate for the period ending in September was 8.2%; the average is closer to 3%.

This level of inflation is very dangerous. If prices increase faster than wages, it can literally topple the economy. And there have been lots of examples of this happening in the past. Luckily, the federal government can contract the money supply to slow inflation (less money in the system leads to lower prices). This has the effect of raising interest rates. And that's exactly what has happened; the federal funds rate sits at around 4%, the highest since 2008.

As a result, money has poured out of equities, particularly tech equities. The broader S&P 500 index is down about 15%, and the tech-focused NASDAQ is down about 30%. Tech companies get hit much harder in these cycles because they're investing in future growth and often carry a lot of debt. Because the profits from these investments won't be realized until further out in the future, increased interest rates discount the values of these future cash flows by an excessive amount (more on this soon).

An additional challenge is that as the Federal Reserve contracts the money supply and interest rates rise, it's not very predictable how quickly that will temper price inflation, so there's no way to know how long this drop in the markets and company valuations will persist. And there are reasons to believe it could get worse before it gets better. 

For companies trying to navigate all of these changing conditions, their worlds have become much more difficult. Valuations are way down. As recently as 10 days ago, Facebook’s stock price hit $88, down from a peak of $378. Stock options granted to Facebook employees over the last 6 or 7 years are likely worthless.

Further, the cost of capital (both debt and equity) for companies has significantly increased. This hits technology companies, which, as I mentioned above, typically have higher levels of debt because they're investing in new growth, particularly hard. The cost of running these businesses becomes much more expensive because the cost of debt increases (increased interest expense). In addition, some of these debt covenants have requirements around growth and profitability that companies need to meet. 

Moreover, and this is probably the most important part of what's going on that should be well understood, is that because tech companies are investing heavily in new growth, the profits from those investments won't be realized for several periods. And higher interest rates hit growth-oriented companies very hard because of the discount rate of future cash flows (more on that here). This is a very important economic concept that many in the tech ecosystem don't understand well enough. Said simply, a company is valued on its ability to generate future cash flows. And increased interest rates lead to a discount in the current value of these future cash flows far more than for companies that are profitable now. When interest rates are zero, there's no discount applied to future cash flows, so the market seeks high-growth companies that are making big, bold bets. When interest rates rise, investors look for companies that have profits now. Again, this is simply because of the discount applied to future cash flows.

Finally, and more broadly, businesses are seeing what's happening and are concerned that jobs will be lost, spending will slow, demand for their products will decrease, and a recession (two consecutive quarters of negative GDP growth) might be on the horizon and bookings and revenue may decrease.

That's the situation tech companies find themselves in today. So how are they responding?

Well, it's important to remember that a company's primary purpose is to maximize shareholder value (for external investors and employees holding stock options). Management has a legal duty to its shareholders to operate in a way that maximizes the value of the company, regardless of the changing markets and the lack of predictability around when things will get better or worse. So in a market where near-term profits and cash flows are very highly valued, companies must pare back longer-term growth investments and find ways to cut costs to realize profits more quickly. And, because, typically, the vast majority of expenses of a tech company come from human capital (employees), the only material way to do this is to slow hiring or decrease headcount.

And this is exactly why we're seeing all of the news reports of tech companies freezing hiring and laying off employees.

Of course, some will criticize these companies for hiring too fast and overextending themselves, and voluntarily getting themselves into this situation by investing too heavily too fast. In many cases, this criticism is fair. But it's worth noting that, while cost reduction has rapidly become very important, in a bull market, growth is inversely and equally important. Facebook, as an example, is taking a lot of heat for overhiring engineers, but should they? I’m no expert on Facebook, but it’s an interesting thought exercise to think through for any company. Again, the job of a company is to maximize shareholder value. And when capital is cheap or free, the companies that invest heavily in growth will receive the highest valuations (again, refer back to the discount rate applied to future cash flows). At scale, had Facebook and the other tech giants chose not to make those hires, those individuals would've been unemployed during that period or would've received lower wages from other companies during that period, possibly displacing less talented engineers. If a company has viable ideas and areas to grow, and capital to invest in that growth is freely available, it must pursue that growth. It must maximize shareholder value. Companies with high growth potential have to play the game on the field. They have to pursue growth if they believe it's there. This is an unavoidable cycle that innovative companies are subject to. And individuals that work in the tech ecosystem will inevitably be the beneficiaries – and the victims – of these realities. Other industries experience far less dramatic highs and lows.

Of course, it should be noted that these highs and lows seriously impact people's lives. And I've been glad to see many companies (though not all) executing these cost reductions with humility, empathy, and generous severance packages.

With all of this said, inevitably, at some point, inflation will slow, interest rates will decrease, companies will invest in growth, companies will start hiring again, we'll be back in a bull market, and everything will seem great. In the meantime, it's important that all stakeholders that have chosen to work in and around tech understand and plan accordingly around the macroeconomic cycles that have a disproportionate effect on this industry.

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

Consensus vs. Non-consensus

I recently heard a technology investor say that if most of his friends don’t laugh at him for investing in a company, then he knows it’s not a good investment. While this is a little strong, there’s definitely some truth to the statement, particularly in venture capital, where your big winners drive most of the returns. If you’re investing in a company that everyone believes will be successful, then you’re investing with the crowd, and your returns are limited. To maximize returns, you have to bet against the consensus and be right when everyone else is wrong.

Consensus and wrong — you lose your money
Non-consensus and wrong — you lose your money
Consensus and right — small ROI
Non-consensus and right — big ROI

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.

First Principles Thinking & Product Design

Will Ahmed, the founder of the Whoop, a popular fitness tracker, wrote a great Tweetstorm the other day about the wearables space. In it, he demonstrated an excellent example of first principles thinking around building a product. I wrote a post about the importance of first principles thinking in company building a couple of years ago. I found this Tweet inside of the Tweetstorm from Will to be the most striking.

 
 

This is a perfect example of first principles thinking in company building that sets out a framework for product managers to make literally thousands of small (and big), follow-on design decisions. The increase in efficiency and speed of decision-making is nearly infinite when leaders think and communicate this way.

Not to mention, it’s also a great strategy. Very few products can remain “cool”, for everyone, for many years. Whoop knows this and from day one (it seems) they’ve been pushing to get closer and closer to invisible, while most of their predecessors have tried to be cool and stay cool. A strategy of being cool while working towards invisible seems like a far more sustainable approach.

The 10 Best Books I Read In 2021

 
 

2021 was another year that was largely dominated by COVID, which meant lots of time to read some great books. I continued my near-obsession with books about Navy SEALs and books on surviving in the ocean. Not sure what that's about. Anyway, here’s this year’s list. Find past lists here.

1/ The Company: A Short History of a Revolutionary Idea by John Micklethwait and Adrian Wooldridge. This is a great book on the history of the corporation. It tells the story of how and why humans formed LLCs and joint-stock companies from ancient Mesopotamia to the multi-national corporations of the 1980s and 1990s. In short, without these structures, we'd have very few of the innovations we enjoy today. Entrepreneurs need legal protection to be able to take risks and innovate. This is a brilliant summary of the history of how we organized ourselves around these ideas. I only wish it was longer and went a bit deeper.

2/ A Speck in the Sea: A Story of Survival and Rescue by John Aldridge and Anthony Sosinski. I'm not sure what it is about these survival stories, but I love them for some reason, and this one was great. It tells the story of a fisherman thrown off a boat in the middle of the Long Island Sound in the middle of the night while his friend was sound asleep below deck and the subsequent search-and-rescue mission. It's a well-written, enjoyable read. I can't imagine what he went endured out there alone at night in the middle of the ocean in complete silence. 

"You forget that you hear waves only when they ride up on the shore; in the middle of the ocean you hear nothing. The silence is deafening."

3/ The Art of Impossible: A Peak Performance Primer by Steven Kotler. I really enjoy Kotler's books. Really interesting, motivating, and data-driven research on human performance and people accomplishing things they never thought they could through what he calls a quartet of skills — motivation, learning, creativity, and flow. The book talks a lot about meaning and purpose at work, which is so important for leaders to remember. From the book:

Once people feel fairly compensated for their time—meaning once that number starts to creep over $75,000 a year—big raises and annual bonuses won't actually improve their productivity or performance. After that basic-needs line is crossed, employees want intrinsic rewards. They want to be in control of their own time (autonomy), they want to work on projects that interest them (curiosity/passion), and they want to work on projects that matter (meaning and purpose). 

4/ Finding Ultra: Rejecting Middle Age, Becoming One of the World's Fittest Men, and Discovering Myself by Rich Roll. I've been listening to Roll's podcast for a while now and finally got around to reading his memoir. A well-written account of his transformation from an out-of-shape 40-something to an ultra-endurance athlete living a plant-based lifestyle. 

5/ Shoe Dog: A Memoir by the Creator of Nike by Phil Knight. I've been meaning to read this for a few years now, but I didn't expect how great it would be. Awesome book. A really enjoyable story, even if you're not interested in shoes or business.  

6/ Principles for Dealing with the Changing World Order: Why Nations Succeed and Fail by Ray Dalio. In this dense and somewhat disturbing book, Dalio studies the repeating patterns of the major underlying shifts in wealth and power over the last 500 years. A very, very important book for investors to internalize to have a point of view on how things might play out in America and other highly developed countries over the next couple of decades. From the book:

I've learned that one's ability to anticipate and deal well with the future depends on one's understanding of the cause/effect relationships that make things change, and one's ability to understand these cause/effect relationships comes from studying how they have changed in the past."

7/ The Attributes: 25 Hidden Drivers of Optimal Performance by Rich Diviney. Diviney is a former Navy SEAL commander that argues in this book that we need to evaluate people on attributes rather than skills or experience. Things like grit, drive, teamability, mental acuity, and leadership. I've become really interested in Navy SEAL training and how they weed out candidates. This book gives a glimpse into how it works. SEAL's go through a training period called 'Hell Week' where they weed out the majority of candidates. They keep recruits awake for most of the week. They'll make them carry huge logs across a wet sandy beach for hours in the middle of the night and then tell them that they can rest once they're done with the log training. But then they change their mind and tell them to do a 2-mile swim in the cold ocean in the pitch dark. I'm fascinated by the type of person that doesn't just quit but instead wades into the water to complete the swim. What do those people have in common? The book doesn't fully answer that question, but it does give some great insight into what separates the highest performers from the rest of the pack.

8/ The Death and Life of Great American Cities by Jane Jacobs. This is a very dense and masterful deep dive into the ingredients involved in successful urban planning. As someone that has lived in big cities for the last 20+ years, I found myself nodding in agreement at the endless insights inside this book. Really well done.

9/ How Innovation Works by Matt Ridley. This is a book about the conditions that drive innovation, from antibiotics to automobiles. He argues that innovation doesn't come from top-down, corporate or government programs. Instead, it comes bottom-up via entrepreneurial capitalism through relentless tinkering and iteration. An easy read with countless useful examples. 

10/ Angel Investing: The Guide to Making Money and Having Fun Investing in Startups by David S. Rose and Reid Hoffman. This is the bible on individual investing in startups. A really comprehensive guide that covers every topic you need to know related to this extremely risky investment category. Written in 2014, the book is somewhat dated given the madness surrounding venture investing over the last few years, but all the fundamentals are covered with some great frameworks on how to manage risk.

Finally, I didn't read a lot of fiction last year, but I did get around to reading Angela's Ashes by Frank McCourt. Obviously not the most uplifting book, to say the least, but the writing is just phenomenal. Highly recommended.

Hope you enjoy some of these.

DoorDash’s Empathy Policy

I read the other day that DoorDash is requiring all of their employees (including their CEO) to make at least one food delivery per month. A lot of engineers were less than thrilled with the idea.

I love this idea. One of the challenges in building b2b software is that your product/engineering team is often very disconnected from the user and the user's problems. DoorDash is lucky that many of its employees likely use the product from the consumer side. That's a massive advantage because they have built-in empathy for the user.

But they're also building for the business user (the Dasher), and many/most employees at DoorDash likely have little to no experience delivering food to a customer. Forcing them to do it once a month drives business user empathy and, likely, a much, much more delightfully built business-facing product.

Throughout most of my career, I've worked with companies that build software products for business users. So I've experienced this challenge first hand. If you're building software for, say, police departments, it's highly likely that most of your engineers will never have worked at a police department. There's nothing wrong with this. Their job is to build software. You want people that are great at building software, not great at enforcing the law. But that means that there is an inherent lack of empathy for the user that has to be dealt with proactively. That's why I love DoorDash's decision to get product managers and engineers out in the field to really feel what their Dashers feel. There's no doubt this will result in a better product.

One exercise I'd challenge b2b software companies to work through is to take stock of how many employees they have that truly have been in the user's shoes. Using the example above, it's worth asking how many employees inside the company have worked for a police department or have had a job where they "could've" used the product they're building? Lots of companies wouldn't have a great answer to that question. And that's ok. But those companies have to make proactive moves to drive empathetic product development.

DoorDash's policy is an excellent step in that direction.

The Operator Shortage

Howard Lindzon described the current state of startups really well the other day on the Animal Spirits podcast. I’m paraphrasing, but he said something like:

There are lots of good ideas. There are lots of founders that want to pursue those ideas. There’s lots of cheap capital for founders to raise and build companies around those ideas. But there’s an extreme shortage of qualified operators to go and execute on those ideas.

There aren’t enough high-quality operators that have actually built companies from the ground up. As a result, we’re seeing significant wage inflation across almost every function inside of startups. The ability to recruit and retain top talent is more important than it has ever been in tech (Apple just offered $180k bonuses to engineers to get them not to leave and go work on the metaverse or crypto). Good companies won’t have a problem raising capital, but almost all of them will struggle to hire the best people.

Build a brand that attracts both customers and potential employees. Hire managers with high levels of followership.

Be a company that people want to work at with leaders that people want to work for. Nothing is more important in this market.