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.

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.

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.

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.

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.

Irreplaceable vs. Replaceable

Here's the story of a company and a founder that has been told many times.

A company has become huge. They've had overwhelming success. But they've become slow and bureaucratic, and innovation has slowed. It's become a boring place to work.

A star employee, let's call her Jane, sees a clear opportunity to improve the company's situation. She has some great ideas on how to breathe fresh growth into the company. Jane's ideas are ignored. Nobody listens to her.

But Jane can't get her ideas out of her head. She needs to pursue her idea. So she leaves the company, raises some money, and builds a product and a company around her idea.

In order to succeed, Jane needs to build a great team. Because there are so many challenges in launching a new company that will beat the incumbents, she needs a team of superstars. She needs to hire people that are amazing. People that are able to run through walls. People that are irreplaceable.

So Jane builds a team full of stars.

And it works. The team of stars is able to take market share and grow rapidly. They have lots of success. They scale and have hundreds of employees. Soon they have thousands of employees.

Now, Jane's burden isn't to disrupt a business or industry; her burden is to protect what she's built. At this point, Jane needs to hire people that are replaceable. If someone is irreplaceable, that's a problem. She needs to build systems and processes and support around her employees so that no single employee is critical to the company's success.

Jane's company has gone from requiring people that are irreplaceable to requiring people that are replaceable. And the cycle continues…

As startups grow, they shift from breaking new ground to protecting their ground. This shift happens gradually and impacts some functions and roles before others. It's very difficult for companies to make this shift. It requires adaptable people, different people, and lots of process building. And you obviously will always need lynchpin employees in some roles.

The irreplaceable vs. replaceable concept is a simple framework for how to think about company building in the later stages of growth.

LTV, CAC, & B2C

Whenever I consider investing in a B2C startup, I immediately ask about the company's LTV/CAC ratio. From the Corporate Finance Institute:

LTV stands for "lifetime value" per customer and CAC stands for "customer acquisition cost." The LTV/CAC ratio compares the value of a customer over their lifetime, compared to the cost of acquiring them. This metric compares the value of a new customer over its lifetime relative to the cost of acquiring that customer. If the LTV/CAC ratio is less than 1.0 the company is destroying value, and if the ratio is greater than 1.0, it may be creating value, but more analysis is required. Generally speaking, a ratio greater than 3.0 is considered "good."

I’m less interested in the actual numbers than I’m interested in how the company is thinking about improving the numbers over time.

You could argue that a startup shouldn't be overly concerned with this metric in the early stages because they're still building the initial product or trying to find product/market fit and get the company off the ground. I disagree. B2B startups can get away with deprioritizing this metric in the early days because a good sales team can reliably acquire large amounts of users and revenue in large batches. And because of the way decisions are made within an enterprise, churn is typically significantly lower.

For B2C companies, LTV/CAC should be a part of the story from the beginning. Acquiring individual users is difficult and expensive. And since Facebook and Google, there haven't been that many widespread and effective ways of acquiring new users. Most of the high-quality channels are saturated. 

Ideally, B2C startups can bake user acquisition into their fundamental product offering; e.g. a supplier in a marketplace might bring their customers to the platform at no cost to the platform. AirBnB is a good example where landlords will often ask renters to book rentals through AirBnB.

Obviously, this won't be possible for every company. But the point remains: user acquisition and churn mitigation are critical considerations for any B2C startup right from the start.

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.

Put A Stake In The Ground

When you start a new venture — a company, a team, a job, a product, a project — setting goals around its success can be stressful. You don't know how fast things will move and how successful you'll be.

Further, lots of people are afraid of being held accountable, much less being held accountable for something that isn't yet understood.

So there's a temptation to just get started without setting goals and see how things go.

For example, I've seen many startups not set sales goals in the early days because they feel like they don't have enough information.

This is a bad idea.

Setting a goal gets you and your team rallied around a target. If you meet or exceed the target, the team will feel great, and you can celebrate. If you miss, you can surface learnings and insights relative to the goal you set.

If you're hitting or exceeding your goals, surfacing learnings is less important. If you're missing, learning is crucial. A learning that isn't connected to a goal is much less powerful and much less interesting than one that is. This will also create the habit of being held accountable and reporting on failure as much as you report on success.

Put a stake in the ground. Set a goal. If you hit it, great. If you miss it, you'll feel a great deal of pressure to surface high-quality learnings that will get you closer next time.

How To Structure A Commercial Organization

There are several different ways to structure a commercial organization. Markets, products, segments, etc. The model I prefer is to structure the teams around metrics. This does a few things:

1/ It ensures that the organization has a metrics mindset. Sometimes people forget what metric their work moves. Building the org around metrics makes this nearly impossible.

2/ It ensures everyone knows they’re contributing. There’s nothing worse than coming to work each day and doing a bunch of work that doesn’t actually contribute to a business objective.

3/ It helps with prioritization. Teams should prioritize their work based on the impact it’ll have on the metrics. Focus on low effort/high return work, and avoid high effort/low return work. It’s amazing how few people have this mindset.

I separate a commercial org into three buckets. If you’re not directly contributing to one of these three buckets or supporting someone that does then you’re on the wrong team. Commercial orgs only do three things:

1/ They sell stuff.
2/ They implement stuff.
3/ They retain stuff.

Everyone should be impacting at least one of those things. Then assign a set of metrics with targets against each. Here are some examples:

1/ Selling stuff (bookings, upsells, expansions, new logos).
2/ Implementing stuff (speed to go-live, quality of implementation, cost of implementation).
3/ Retaining stuff (retention, renewals, net promoter score, user activity).

I’ve found that structuring the team around these three activities and some set of metrics ensures that everyone has clarity on their role, their value, and how they’re impacting the business in a positive way.

The Rule Of 40: Which Side Are You On?

In the early days, a company with solid product/market fit and a great team will grow extremely fast. Revenue growth can be 1,000+%. But as a company becomes established, things come back to earth. Tripling revenue when you have $50k in revenue is a lot easier than tripling revenue when you have $50MM in revenue. Over time, the company will eat up all the low hanging fruit. Competitors will enter the space and apply pricing pressure and reduce win rates. Scaling becomes even more difficult. Things just start to slow down.

This flattening of growth is nothing to be ashamed of. It's a natural curve for any product or company — even the iPhone's growth has flattened.

 
Apple iPhone worldwide unit sales from 2007 to 2018 (in millions)

Apple iPhone worldwide unit sales from 2007 to 2018 (in millions)

 

The way to break out of this natural flattening is to innovate. As Jeff Jordan says, “to add layers to the cake.” But eventually, even the greatest companies will see their growth rates begin to level off.

To maintain a high valuation despite slowing growth rates, companies will often point their energy towards becoming profitable or increasing profitability. One of the biggest challenges of a maturing company is this: should we step on the gas and continue to grow like crazy, or should we shift our focus to profitability?

The Rule of 40 provides an excellent framework for how to think about this question. The Rule of 40 states that a company's growth rate + profit margin (EBITDA) should exceed 40%. Companies that can stay above 40 will continue to be on the high end of valuations — 10x, 20x, 30x revenue multiples. According to a study done by Bain, software companies that are above 40 have valuations that are double those that fall below the line.

So as growth slows, it's useful for executives to ask, what side of the Rule of 40 do we want to be on? That is, are we going to continue to achieve the 40% via revenue growth or do we need to begin focusing on profitability.

The Rule is just a framework; it shouldn’t be taken as gospel. But it provides an extremely useful framing for how to think about one of the most challenging questions high growth companies face.

Slack Connect & The Future Of Business Software

 
slack logo .png
 

Slack recently announced Slack Connect, a product that allows disparate companies to collaborate inside of a Slack channel. They now have more than 40,000 customers using the product.

For those interested in business software, I think there's reason to believe that products like Slack Connect — software that allows users across different companies to collaborate inside the same instance of that software — will lead to a trend that's even more impactful than the shift to the cloud.

Slack Connect users can have a shared Slack channel with their customers, vendors, partners, and prospects. I haven't used the product yet, but I recently collaborated in real-time with a customer to build a presentation using the same instance of Google Slides. It was so much more efficient. Imagine finance teams collaborating on complex invoicing issues inside the same instance of Netsuite. Or project managers at separate companies collaborating inside of SmartSheet. Or a salesperson collaborating with on a customer's buying process inside the same instance of Salesforce.

Moving core, cross-company business activities into a shared workspace will be enormously valuable to the users inside of each company. And even more impactful is the impact on distribution and go-to-market. Suddenly, Netsuite, SmartSheet and Salesforce have native network effects (e.g. their software is more valuable to each user when more users use it). This is why Slack Connect is so interesting. Slack already had network effects inside of a company, but growth was limited to the size of each individual company. Slack Connect enables unlimited network effects.

Don't get me wrong, like the move to the cloud, there are enormous challenges for software vendors that pursue this strategy. There's a reason I don't collaborate on Google Slides with the majority of customers. Most large companies aren't using Google's applications, and thus users don't have a log-in and aren’t authorized to use their personal one for work purposes. There are significant privacy and adoption challenges that need to be overcome.

Slack has an advantage here in that their core customer base is still startups, small businesses, and tech companies (though they’re rapidly moving upmarket). This core allowed Slack to get Connect into market much more quickly than Microsoft could've with its Teams product.

The irony of Microsoft being behind on this is that they own the one asset that could've accelerated the growth and adoption of cross-company messaging — LinkedIn.

LinkedIn already knows most professionals’ "professional social graph." These social graphs are the underlying infrastructure that enable a network to grow. Consider Whatsapp, who built a nice messaging app and then tapped into your phone's address book (your social graph) to seamlessly build out its network. They went from 0 to a billion users in just a few years. They never could’ve done that if they didn’t have access to people’s personal address book. LinkedIn is the world’s professional address book.

LinkedIn messaging could've been a far better and faster-growing version of Slack Connect. But LinkedIn underinvested in its messaging feature to the point that it's almost unusable. The spam is overwhelming, and the poor user experience makes it impossible to use productively.

This miss isn't really a surprise, and I'm not playing Monday morning quarterback. Microsoft hadn't built its initial software around connecting disparate companies. In fact, it was quite the opposite. And turning the tide isn't easy. Also, LinkedIn's core customers are recruiters and marketers; use cases where the value of cross-company collaboration isn't obvious.

So, all of this is to say that there's an enormous opportunity for emerging SaaS companies to build native cross-company collaboration tools into their code, use cases, and culture from the outset. It's hard to predict that any trend is business software will be as impactful as the shift to the cloud, but if there's one out there, this might be it.

Working For Jeff Bezos

I’m reading Amazon’s Management System by Ram Charan and Julia Yang. I absolutely love this excerpt:

As former Amazon executive John Rossman put it: “If you want to succeed in Jeff’s relentless and fiercely competitive world, you cannot:

• Feel sorry for yourself

• Give away your power

• Shy away from change

• Waste energy on things you cannot control

• Worry about pleasing others

• Fear taking calculated risks

• Dwell on the past

• Make the same mistakes over and over

• Resent others’ success

• Give up after failure

• Feel the world owes you anything; or

• Expect immediate results

The most successful are those who can excel in the pressure cooker, week in and week out, shaking off the occasional failure and the subsequent tongue-lashing, put their heads down, and keep on driving.”

This is a near perfect description of the best people I’ve worked with over the years.

Hiring Your First Head Of Sales

By far, the most frequent question I get from founders is this: How do I go about hiring a Head of Sales? I've literally received this question four times in the last six or seven weeks.

Hiring a Head of Sales at a startup is a very difficult, important, and scary thing for a founder. Making a mistake on this hire can set the company back several quarters. I try to avoid making declarative statements to founders because context is so important and each situation is unique. That said, here are a few things that will help reduce the risk associated with hiring a Head of Sales for the first time:

1/ Ensure the candidate has been an ultra-successful individual contributor. I know, I know, the best salespeople aren’t necessarily the best managers. You don't need the best salesperson in the world, but you do need someone who has done it before. In startup sales, you can't lead the calvary if you can't sit in the saddle. Strong sales capabilities (both to sell direct and to sell salespeople on joining the company) are crucial in this role. If this candidate can't sell, they likely can't recruit. It’s not worth that risk.

2/ Ensure the candidate has sold into (roughly) similar-sized organizations in the past. If you're selling to large enterprises, don't hire an SMB expert, and vice-versa. It's not impossible to make the transition, but it's relatively unlikely that it will be successful. Often, the things that make people good at SMB sales make them bad at enterprise sales. Also, do consider the candidate's experience with the vertical you're selling into. Ideally, you will be able to find someone who has sold into that vertical in the past. I wouldn't make this a requirement in every situation. The importance of this is industry dependent. But if the industry has a steep learning curve, optimize around that set of experience.

3/ If you have the capital, hire a headhunter to help. Doing this search right requires an expertise and time investment that most founders can't afford. This is a good opportunity to outsource.

4/ Hire a “stretch VP.” A stretch VP is a rising star (generally Director level) that needs to level-up a bit to become a sales leader at a larger organization. This type of candidate will generally lean towards execution but will have the potential to recruit and run a team. This is a good hedge. If the candidate levels-up and can run the whole sales organization, that's great. If they can't, it'll be easier to “level” them with a more senior candidate. If you hire someone too senior, you run the risk that they won't be execution-focused, and it will be difficult/impossible to level the candidate if things don't work out. A stretch VP is a good way to reduce risk.

5/ Overinvest in intrinsics. This candidate is going to be accepting a very difficult job. Make sure they have the intrinsics that will make them successful in a high-pressure startup environment — grit, humility, adaptability, and curiosity. More on that here. Also, this is hard to do, but make sure the candidate is someone that is at a stage in their life and career they simply aren’t willing to fail. Some call this “personal exceptionalism” — more on that here.

Things That Don't Scale

I recently started using Superhuman, the popular $30 per month email application, that's getting lots of buzz. It's a wonderful product. It solved my email overload problem.

I would've started using it sooner, but before they would grant me access, I had to complete a thirty-minute consultation with one of their staff members to configure my email and learn how to use the product most effectively. That seemed unnecessary to me, so I passed.

I eventually got desperate and agreed to the consultation. I now see why they force this — they go deep on how you use email, do some real-time customizations, and make sure you know how to use the product. All of this makes users much less likely to churn.

That said, it's surprising that Superhuman, an application with thousands and thousands of users, would make this kind of investment in onboarding new users. For a $30 per month consumer email application, this seems like the definition of something that won't scale.

I recently came across an interview with Superhuman's co-founder, Rahul Vohra, where he talked about the importance of these consultations and was asked if he thinks they can scale. He responded by saying that organizations need to identify the things they do that won't scale and decide which of them they should keep on doing. These are things that, from the outside, may seem small and wasteful but are actually core differentiators consistent with the heart of the organization's strategy and competitive advantage.

I've been thinking about this a lot lately. As an organization scales, the things that aren't scaling start to become really obvious. And smart companies find ways to outsource, automate or completely stop doing them.

The hard part of all of this is identifying those things that, on the surface, seem like they obviously won't scale but actually drive big value.

At the Ritz-Carlton, every single employee (even the maintenance folks) has a budget of $2,000 per guest to make things right. On the spot, without asking.

Zocdoc, the medical appointment booking service, sends a $10 Amazon gift card to users every time a doctor reschedules an appointment.

Zappos maintains a 24/7 call center, posts their phone number on every page of their website, and doesn’t have a phone tree.

In the early days, most startups will tend to overinvest in high-touch and high-cost activities. They have to do this because they're forcing their way into a market. They can't cut corners and scale isn't an issue.

One-on-one product training. High-touch recruiting and employee onboarding. Ultra-fast customer service response times. Even small things like sending hand-written holiday cards to every customer. These are obvious and easy to do in the early days. But many of them won't scale and there’ll be pressure to stop doing them over time.

The easy part is dropping things that don’t scale. The hard part is continuing to do them.

How Silicon Valley Became Silicon Valley (And Why Boston Came In Second)

When I was a kid growing up in central Massachusetts, I remember that a bunch of my friends' parents worked for super high growth tech companies like Digital Equipment Corporation (DEC), Data General, and Prime. While some people reading this may not have heard these names, these companies were behemoths. In the late eighties DEC alone was one of the largest companies in the world and employed more than 120,000 people. These companies were booming at the time in an area known as the “Route 128 Corridor”. Route 128 is a highway that runs south to north about 10 miles to the west of Boston. The area was a hub for technology companies — mostly focused on semiconductors, microprocessors, and minicomputers. It seemed like almost all my friends' parents worked at one of these companies or a company that provided support to these companies.

I also remember the bust that came in the early nineties when many of these companies downsized and thousands of people lost their jobs. It was a rough time for many people in the area.

What I didn't know at the time was that there were a set of competitors based in Santa Clara County, California, in the area now known as Silicon Valley, viciously competing with the Route 128 companies. Companies like Hewlett Packard, Intel, and Apple.

Most people now know that the Silicon Valley companies came out on top and that the tech scene in the area outpaced eastern Massachusetts significantly. Massachusetts remains one of the top 3 tech hubs in the U.S., dominates biotechnology, and is well on its way to becoming the country’s Digital tech hub. But outside of healthcare, the Silicon Valley area is far ahead and sees about 3x the number of startups and venture funding than the entire state of Massachusetts.

That said, back in the mid-1980s, you would've had no idea which region was going to come out on top. It could’ve gone either way.

AnnaLee Saxenian wrote a phenomenal book about all of this titled, Regional Advantage: Culture and Competition in Silicon Valley and Route 128 that examines the differences between the two regions.

Having lived in and worked in both areas, here are some of the key differences between the regions that I think allowed Silicon Valley to outperform. Certainly some of the takeaways are isolated to these regions at that point in time. But as lots of cities across the country try to increase the number of tech startups launched in their communities, many of the lessons from the battle between Silicon Valley and Route 128 can be applied by policymakers and tech leaders today.

Cultural differences

Massachusetts had a much more traditional, risk-averse approach compared to the Valley. A big reason for this comes from the parochial and puritanical cultural history of Massachusetts. But, more practically, it also comes from the fact that most people that worked in Silicon Valley weren’t from California. They were from the east coast or the midwest. You can’t underestimate the impact this has on a region. People aren’t spending time with their high school friends or church friends or summer camp friends. They’re spending time with the people they work with. And what do they talk and think about during that social time? Work. They’re bound together by their work. And they're much less worried about trying something new and failing at it because their friends and family back home may not even know about it. An executive that worked on both coasts described it this way in the book:

“On the East Coast, everybody’s family goes back generations. Roots and stability are far more important out here. If you fail in Silicon Valley, your family won’t know and your neighbors won’t care. Out here, everybody would be worried. It’s hard to face your grandparents after you’ve failed.” —William Foster, Stratus Computer

This meant that people in the Valley were much more willing to take risks, start companies and jump from job to job. As they jumped from job to job and made friends with people at work, they created networks centered around their work across several companies in the region. It was common for an engineer to quit their job on a Thursday and show up at another startup on Monday. These new experiences led to more friendships and led to a ton of collaboration between companies and an openness to sharing with one another for the greater good. It was common for Silicon Valley competitors to call one another for help with technical problems. This kind of collaboration created a rising tide for everyone in the area. The power of this kind of environment is enormous.

By contrast, in Massachusetts, most of the people working in tech were from New England. From the book:

”The social world of most New England engineers, by contrast, centered on the extended family, the church, local schools, tennis clubs, and other civic and neighborhood institutions. Their experiences did little to cultivate the strong regional or industry-based loyalties that unified the members of Silicon Valley’s technical community. Most were from New England, many had attended local educational institutions, and their identities were already defined by familial and ethnic ties.”

There was a separation between work and social life for Route 128 workers. For workers in the Valley, it was much more of a grey area. Workers in Route 128 tech often went right home after work and immersed themselves in their local towns, where they had ties that went back generations. Workers in the Valley didn’t have these ties. Instead of driving several miles back to their town, they were more likely to go out to dinner or to a bar in the area to talk about technologies and markets.

Job hopping

As mentioned above, workers in the Valley would jump from job to job growing their network and gaining new experiences. Route 128 had a much different culture where loyalty was highly valued and if you left you could never come back. Workers often stayed at their jobs for 10+ years. This was unheard of in the Valley. Workers felt that they were working for the Valley — the community — rather than for an individual firm. If they decided they wanted to come back they were often welcomed with open arms. As I've written in the past, this impact is felt today as California has banned the use of employee non-compete agreements while Massachusetts has allowed them to persist.

Collaboration with universities

Stanford actively promoted startups by offering professors up to help with product development and created several funding mechanisms for new ideas. MIT took a far more conservative approach and was very reluctant to invest dollars or time into things that were too risky. This created artificial walls between the best tech companies and the best technical research. Many of the east coast companies claimed they had better working relationships with Stanford and Berkeley than they did with MIT and Harvard.

Dependence on government contracts

Because of its proximity to Washington, Route 128 companies had lots of reliance on government contracts that had long term obligations that restricted innovation. It also (appropriately) led to a secretive culture that stalled collaboration with associations, competitors, partners, and other organizations in the local ecosystem. By contrast, by the early seventies, Silicon Valley companies were receiving far more financing from venture capital investors than they were from government contracts. The east coast's dependence on government contracts made widespread collaboration nearly impossible.

Geography

Silicon Valley companies started around Stanford and expanded to cities like Mountain View and Santa Clara but couldn’t go too far as they were locked in by the Santa Cruz mountains to the west and the San Francisco Bay to the east. This led to a very dense community of tech companies. By contrast, the Route 128 companies were spread far and wide. DEC, the largest of the companies in the eighties, was based in Maynard, with more than 20 miles of forest separating them from the hub of Route 128.

Organizational structure

Related to the dependency on defense contracts and its proximity to established political and financial institutions, Massachusetts companies were more formal and created organizational structures that had a strong resemblance to the military. This kind of organizational design can slow innovation as the lower rungs of the ladder are less reluctant to offer new ideas and there's far less cross-functional learning. Executives had their own parking spaces and executive dining rooms. Stock options were only offered to those at the highest levels of the organization. This even applied to work attire — the uniform for 128 companies was a jacket and a tie, in the Valley it was jeans and a t-shirt.

Today, something like 75% of all venture capital funding goes to three states -- Massachusetts, California and New York. As governments and entrepreneurs across the country try to expand the number of tech companies that emerge and grow in their communities, it’s important to remember that ecosystems create a lot more jobs than companies. The key is less about funding and micro-incentives and more about creating the complicated environment that allows an entire ecosystem to thrive.

Quick Decisions

Whenever I interview someone that recently worked at a startup that went out of business I ask them why it failed. How analytically someone answers this question says a lot about them. But the truth is that I'm mostly asking because I'm curious. I want to know what to look out for.

More often than not, the answer comes down to one thing: dysfunctional leadership. More specifically, for some reason, leadership didn't communicate well and couldn't make quick decisions. 

Tomas Tunguz had a great blog post on this topic recently, titled the Challenge of Uncertainty. From the post:

The management team of a company is a decision-making and productivity chokepoint. Critical decisions flow through them. If the management team ruminates on most decisions, the company’s progress stalls. In a 100 person startup, five slow-to-decide executives limit the productivity of 95 employees. In a 1000 person startup, the ratio might be 10:990. There’s enormous leverage in a hierarchical organization if the leadership moves quickly. The converse is equally true. Sluggish decision-making halts all progress.

The cost of deciding slowly seems small. Just a day or a week of more research; one more experiment. But a day’s delay in a 1000 person organization costs the company more than $400k in lost productivity.

Slow decision-making can be paralyzing for a company.

Management teams should check themselves occasionally on the speed and quality of their decision-making. It will almost always deteriorate over time. There are dozens of little things that can weigh down management and cause them to slow the pace -- too many direct reports, too many meetings, not enough meetings, new personalities, fear of telling the truth, personal issues, different communication styles, poor prioritization and on and on. All of these things will come up at some point. How well a leadership team weeds through this stuff and finds a way to continue to make good, speedy decisions might make the difference.

Personal Exceptionalism

Harry Stebbins had a great interview with venture capitalist Michael Dearing on the 20 Minute VC Podcast a couple weeks ago. Michael talked about a trait that he looks for in founders and startup teams that he refers to as "personal exceptionalism". This is the idea that a person believes that they are special and that their outcomes are going to be "outside the bounds of normal". They’re not arrogant, they just strongly believe that they can produce results far greater than the mean.

This idea really resonated with me; not as an investor but as a person that hires a lot of people and builds teams and is constantly trying to scour through candidates to find the best of the best. The notion of personal exceptionalism really captures what I look for. Rather than try to explain the concept myself I've transcribed Michael's comments on it below. Spot on.

I think my radar for personal exceptionalism has evolved over time but I think the constant is that I’m looking for people who have broken out of the bounds of normal for their peer group. Now that does not [necessarily] mean in business or as technicians or technical talent. It just means that whatever the circumstances were in their lives, that that was not the determining factor. They were able to break out either because they took some crazy personal risk, they took some very sharp left-hand turn, they ended up accomplishing more and seeing more and building a much better experience base because of that risk-taking. So that personal exceptionalism that says that they are special that they are destined for really unique outcomes relative to their peer group. I think that shows up early in somebody’s life and it’s quite independent of pedigree or brand name work experience. In fact, sometimes those things are negatively correlated. But the distinction you make between arrogance and personal exceptionalism is an important one. Personal exceptionalism just means that they see themselves as special and their outcomes are going to be outside of the bounds of normal. I think that they a lot of times are some of the most self-critical people I know and they beat themselves up when they do miss a goal or they fail in a venture they beat themselves up far harder than any third party could so the arrogance piece is easy to suss out. You see it in the form of the people they attract around them and the kinds of networks that they build how much are they are a taker versus a giver in those networks. So I actually have found over the years it’s relatively easy to separate the sheep from the goats.