Investor Alignment

Managing different investor priorities, objectives, and incentives is one of the most difficult things to do when leading a company. I wrote about the importance of understanding your investor's context and incentives a while back. Even at the venture stage, your angel investors and VCs may have very different ideas on how they define a good outcome. Depending on their own situation, some may be taking a very long-term view of the investment; others may want a shorter-term win. This intensifies significantly as you transition into the growth stage and, ultimately, an IPO, at which point you can literally have millions of investors with competing needs and priorities.  

To help manage this, someone once told me that in a board meeting, I should try very hard to step out of my own incentives and not behave on behalf of Brian Manning but instead behave on behalf of the company. The company has no voice. Everyone in the room has their own incentives and that's typically what they represent. It's important for someone to step up and speak for the company. 

This sounds like great advice, but it's almost impossible to do because how does one define the incentives of the company when the incentives are really a bundle of competing self-interests? This makes driving investor alignment extremely difficult. 

As a leader, your job is to maximize shareholder value, but on what timeline? Should you optimize valuation for a year from now or 3 to 5 years from now? Depending on your answer, your short-term goals and actions will vary significantly. You might say your job is to drive value over the long term. But what is the long term? Should companies seek to stay in business forever at the cost of shorter-term returns?

In the early stages, to help manage this, I've found it's enormously useful to optimize around funding rounds — seed, Series A, B, C, etc. Leaders should set specific goals associated with the next raise. As an example, a team at a high-growth startup might say they want to raise their Series A in December of 2025, and by that point, they want to have:

  • $X in the bank

  • $X in revenue

  • $X in monthly burn rate

  • X% growth

  • X in headcount

  • X in number of customers

  • X, Y, and Z in product milestones

  • $X in company valuation (this one will obviously be a loose estimate based on some market-driven multiple)

  • X gross margin, Y operating margin (though these should be prioritized after product/market fit, burn rate, and cash are more of the focus early on)

Leadership should then be transparent with the board and investors about these metrics so everyone knows what the company is chasing. Leaders and even front-line employees should know these metrics and keep them top of mind. While this approach is far from perfect and won't align all of the different competing interests, transparency and disciplined tracking against clear metrics is a huge step forward in managing the day-to-day tradeoffs and difficult decisions that come with running a company. 

Bookings As A Lagging Indicator

Bookings (the value of contracts signed within a specific period) is a crucial metric for companies to watch. Investors watch this number very, very closely. Boards will put enormous emphasis on it. When a deal is booked, the product then gets delivered to the customer, which turns the booking into revenue generated in a specific period, which equates to the top-line growth of the company. Bookings are the tip of the spear. It’s a leading indicator for revenue.

Investors will also look closely at qualified pipeline (the pool of potential sales opportunities that are deemed highly likely to convert into bookings) as that is a leading indicator of bookings.

Bookings and qualified pipeline are watched closely and are heavily scrutinized.

The problem with placing too much focus on these numbers is that a sales and marketing team is limited in how much they can move these numbers one way or another in a specific period. If a company crushes their bookings in a period, it generally means that there was a bluebird deal or that goals weren’t set accurately or that there was an external macro event that caused a large swing. Rarely are sales and marketing teams able to swing these numbers up and beyond expectations in a major way. The reason is that bookings are capped by the TAM (total addressable market) or, more specifically, SAM (serviceable addressable market) available to them. I wrote about TAM, SAM, and SOM a few years ago, find that post here. So, the reality is that while sales and marketing teams can do great things, they are limited by the stuff they have in their proverbial bag that they can sell. To really move these numbers and continue to grow, companies need to create new SAM at a high rate. So, while pipeline is a leading indicator for bookings, SAM creation is a leading metric for pipeline.

To make this point more concise, bookings growth is dependent on product investment decisions that were made 1, 2, 3, or even 5 years ago.

So, while it’s obvious that companies should be focused on in-period bookings and retention and profitability metrics, arguably it’s more important for companies to be focused on in-period SAM creation such that the cap on bookings growth in future periods gets higher and higher. The reason this is arguably more important is that product investments made now can drive far larger swings in growth in future periods than a sales and marketing team can in the current period. If two years ago a company made large investments in new products and new SAM creation, bookings will be high in the future. If two years ago they made no investments in new products and new SAM creation then bookings will be low in the future.

So, while obviously investors should be asking companies how bookings are going in a specific period, they’re really looking at a lagging indicator for good or bad investment decisions that were made in the past. They should place equal emphasis (arguably more) on how much new SAM is being created in that same period, as that’s the number that’s going to drive material and sustainable growth.

Valuation Fundamentals

The 10+ year period of near-zero interest rates caused a lot of investors and leaders to deemphasize the fundamentals of valuing companies. As I’ve written many times, we know that a company’s value is equal to the present value of the amount of cash you can take out of it over time. That is, the amount of cash you can take out of the company over time discounted to present-day dollars. When you’re in a zero-interest environment, there is no discount rate. When there’s no discount rate (or no risk-free way to make money), investors take more risk to find a return, thus the overflow of money into venture capital and other high-risk investment vehicles during that period. When there’s no risk-free bar to clear to find a return, an investor is more open to non-traditional investments. When interest rates are high and low-risk treasury bills are paying out 6%, in order to invest in something risky, the investor has to be comfortable that any investment will exceed 6%, causing money to flow out of venture capital and other high-risk investments.

When the risk-free rate is very low, investing gets hard because there are no guarantees, so you start to use proxies and benchmarks for future returns. This was particularly true in SaaS which really emerged in a big way during the 10+ year period. Things like Rule of 40 and 35% EBITDA margins and 70% gross margins became solidified as proxies for investable software companies. We needed those proxies because they provided guidance for what to invest in in a world where almost anything “could” be a good investment.

Now that investors have raised the bar on what they’ll invest in and there are real questions about the future of SaaS margins due to the emergence of new pricing models and pricing pressure from AI duplicating SaaS products at a far lower cost, it’s time to return to the fundamentals of valuation. Remember:

Growth is just a proxy for future cash flows.
Gross margins are just a proxy for future cash flows.
Operating margins are just a proxy for future cash flows.
Net income is just a proxy for future cash flows.

None of them alone can tell an investor the amount of cash they can take out of the company over time.

Now that we’re back to desirable risk-free rates, and CIO budgets have tightened, and high interest rates have squeezed company margins, it’s time to be more flexible and get back to the fundamentals of valuation. There are numerous ways to get there that might not fit with the traditional SaaS benchmarks we’ve used as a reliable guide over the last decade.

Good Conversations & Good Selling

As a sales leader, I’ve often told my teams that, while I want to close every deal we can, it’s perfectly fine if we don’t, as long as we understand exactly why the buyer didn’t buy.

As a seller, I used to have this mindset during sales conversations: I wanted to be sure that if the buyer didn’t buy, I could explain why in great detail to anyone who asked.

The trick here is that forcing yourself to understand why a buyer didn’t buy also forces the right sales behaviors. You have to do a bunch of good things to be able to do this well. You have to:

  • Talk to the right people.

  • Understand their role.

  • Understand their decision/buying process.

  • Understand their incentives and priorities.

  • Understand their problems

  • Understand what other solutions they have.

  • Understand what they like/don’t like about the product.

  • Understand how they view the competition.

  • Understand how they think about ROI for the product.

You can’t understand these things if you’re not having good conversations. And good conversations are the thing that drives sales. Sellers should be less interested in making the sale and more interested in deeply understanding the mindset of the decision maker, regardless of the ultimate decision. This mindset, repeated over time, leads to better and better high-quality conversations. And better conversations = higher win rates.

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. 

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+.

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

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. 

Discipline In Company Buildling

I love this Tweet from Dan Hockenmaier.

It's very common for early-stage startups to over-title people to get them in the door. Often they don't have the clout or the cash to get great people, so they use a senior title as a way of convincing someone they like to join the team. This is a mistake and causes all kinds of issues down the road. When the company is finally able to recruit people that are legitimately at the Director or VP level, those people are going to look at their peers and demand a higher title.

The company will then have a similar problem at the VP or C level. It will result in a disjointed and confusing org chart that will need to be blown up. And if the company wants to hire above the person they over-titled, they may have to let that person go or give them a demotion (which will likely cause them to leave). The hard work will have to happen at some point. Over-titling people in the early days just kicks the can down the road. In his book, the High Growth Handbook, Elad Gil points out that, in the early days, Facebook and Google gave employees the lowest titles possible (VPs that came over from Yahoo! or eBay came in at the Manager or Director level).

With all of that said, the much more significant implication of Dan's Tweet is less about a decision around what title to give someone, and more broadly around the topic of discipline in building a startup. Startups are so hard to build and there will be all kinds of temptations to cut corners, delay hard decisions, and take the easy way out. Some examples:

  • Give away free pilots.

  • Build one-off features to close a deal.

  • Agree to overly flexible payment terms.

  • Hire an experienced person even if they're not the right fit with the team.

  • Delay terminating an employee that is damaging culture.

  • Partner with a well-known brand even though it doesn't align with the company strategy.

  • Raise more capital than is needed.

  • Pivot product roadmap based on a few customer requests.

I could add 100 more things to this list. The startups that consistently resist these temptations are the companies that win. Eventually, a lack of discipline will catch up to the startup and will make success even harder than it should be.

When joining a startup, look for signals of good discipline. You might not get the title you want, but that’s a small price to pay to get a seat on a rocket ship.