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.

The 10 Best Books I Read In 2019

My wife and I celebrated our honeymoon in the winter of 2019 on the beaches of Thailand. That gave me lots of extra reading time. In 2019, I read some great books on business, history, religion, and lots of books on leadership. I even found a couple of fiction books that I loved. Below is a list of the top 10 books I read in 2019. See past lists here.

1/ Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies by Reid Hoffman. An excellent book with practical advice that tells it like it is. Startups are beginning to get a reputation as glamourous. They aren't. They are really, really hard. Hoffman — an early employee at PayPal and the founder of LinkedIn — describes it this way:

"Starting a company is like jumping off a cliff and assembling an airplane on the way down; being resource-efficient lets you "glide" to minimize the rate of descent, giving you the time to learn things about your market, technology, and team before you hit the ground."

Blitzscaling is a great book, especially for those joining a startup for the first time. 

2/ The Tyranny of Metrics by Jerry Muller. I'm a big fan of metrics. I generally like to use them as the foundation of the work that I do. "If you can't measure it, you can't manage it," the old saying goes. This book is a quick read and gives several real-life examples of the danger of relying on metrics when the people that are reporting them are under lots of pressure. As an example, some cities will tout reduction in certain types of crimes due to pressure from the public. But when you dig deeper, you find that they're merely reclassifying crimes to lesser charges. This book is an entertaining reminder to be very careful about reacting too quickly to metrics. 

3/ Debt - The First 5,000 Years by David Graeber. Debt is a dense and long book that chronicles the history of debt going back 5,000 years before currencies, or even barter were established. It's incredibly instructive on how global markets came to be and what we can learn from the mistakes our ancestors made — highly recommended.

4/ What You Do Is Who You Are: How to Create Your Business Culture by Ben Horowitz. Horowitz's first book — The Hard Thing About Hard Things — will become a management classic. And this one might as well. Horowitz uses some great analogies to talk about modern-day management — including the Japanese samurais, the leader of a prison gang, and the slave revolt in Haiti during the 18th century. The bottom line is that you can put your company values on your website, and you can talk about them all the time, but if you don't practice what you preach, it doesn't matter. Culture is the output of a company's actions. Culture is about what you are, not what you want to be.

5/ Can't Hurt Me: Master Your Mind and Defy the Odds by David Goggins. This is an autobiography by David Goggins, who is the epitome of someone going from a horrible childhood with unspeakable physical and mental abuse and transforming his life into immense success. Goggins is a former Navy SEAL turned motivational speaker. The thing I like most about this book and that he transformed his life simply by changing his attitude, owning his inner voice, and taking full ownership and accountability for his actions and choices. An extremely intense and inspiring book.

6/ Reboot: Leadership and the Art of Growing Up by Jerry Colonna. I've been following Jerry's Reboot podcast for years. He's an executive coach and expert on getting the most out of leaders. This one gets pretty deep but it's one of the best books on leadership I've read in years. It forces you to look deeply at yourself and understanding how you became who you are. This is the starting point to the journey of becoming a better leader. I expect to come back to this one every now and then.

7/ VC: An American History by Tom Nicholas. VC is a great book on the history of the venture capital industry. From the whaling ships of the 1800s to modern-day Silicon Valley, this book covers everything. A great, comprehensive overview of this increasingly important asset class. 

8/ Decisive: How to Make Better Choices in Life and Work by Chip Heath. I think this is a must-read for managers. This book dives deep into the fundamental errors that humans apply to decision making. Confirmation bias, short-term emotion, overconfidence, reliance on our frame of reference can lead to disastrously bad decisions. Heath goes deep on all of these flaws to help at least make leaders aware of the potential mistakes we make.

9/ Regional Advantage: Culture and Competition in Silicon Valley and Route 128 by AnnLee Saxenian. This book discusses the battle between the tech ecosystems of Silicon Valley and Eastern Massachusetts during the 70s, 80s, and 90s. I'm biased because I grew up in the middle of this battle and found it fascinating. But the broader lessons from this book will be interesting to any follower of technology and culture. I wrote a blog post earlier this year expanding on some of my thoughts on this topic.

10/ The TB12 Method: How to Achieve a Lifetime of Sustained Peak Performance by Tom Brady. I was stunned by how much I liked this book. It's really well written, and Brady's approach to health, longevity, and habits is enormously inspiring. The book doesn't tell us all that much that we don't already know (sleep and hydration are immensely important), but seeing the details of the lifestyle of an incredibly committed and disciplined athlete is something we can all take something from.

Finally, a couple of fiction recommendations. The first is from my cousin Tom. I love all of his books, and his most recent one, The Perfect Liar, was as good as it gets. The second one that I absolutely loved was Goodnight Stranger by Miciah Bay Gault. 

I hope you enjoy some or all of these.

Business Models & Tech

This somewhat dated (2015) but still highly relevant essay by Alex Danco offers an insightful overview of the state of software in healthcare. If you care about this sort of thing, I highly recommend reading it.

The most interesting aspect of the piece for me is the reminder that when tech impacts or “disrupts” an industry, the tech isn’t necessarily the interesting part. The interesting part is the business models that change or emerge as a result of the tech.

Here are a few examples of what I mean:

Spotify leveraged technology to change the business model of music from $10 per album to 40 million songs for $10 a month.

AirBnB leveraged technology to change the hospitality business model, listing 6 million rooms and homes while owning zero properties. 

Uber leveraged technology to change the taxi business model, doing 4 million rides per day, while owning zero vehicles or taxi medallions.

As we consider how much software has impacted (or not impacted) healthcare, we shouldn’t be looking for the flashy, healthcare-specific, transformational technologies. We should consider the new and emerging business models that are enabled or enhanced by technologies. Those aren’t hard to find.

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.

Some Notes on Managing People

Earlier this week, my team went through a day and a half management training. It surfaced a bunch of things that I've learned about managing people over the last several years. I made some notes and thought I'd share them here.

1/ Some managers see their role as being the one that needs to smooth things over. This is the wrong approach. As Karl Marx said, it's best to "sharpen the contradictions." Bring the conflict up to the surface so everyone can see it and deal with it.

2/ When managing managers, sometimes the most important thing you can do is help them make the hard decisions they already know they need to make. Give them the support, safety, and clarity to execute on the hard stuff.

3/ Self-awareness and general awareness are two of the most crucial attributes of a leader. You have to know how you're being perceived and you have to know the issues on the team. You have to be in touch with the 'water cooler talk'. You have to make sure people understand that you know what's going on in their worlds. A clueless leader is the worst kind of leader.

4/ Create a habit of regularly expressing unsolicited gratitude to your reports. This is rocket fuel from an engagement and loyalty perspective.

5/ Use the writer/editor analogy when thinking about how much leverage you're getting from your reports. If you're doing a lot of writing, you're not getting enough leverage.

6/ Giving feedback is a muscle. When you do it a lot, it's easy. When you don't do it a lot, it's hard. Make giving feedback a regular part of the way you interact with your team.

7/ In a conflict, try to understand the other person's argument so well that you can make their argument for them with more clarity than they can. Don't make your argument until you can do this.

Collaboration & Enterprise Software

Kevin Kwok wrote a must read piece a few weeks ago about how crucial it is for collaboration to be a fundamental, “first party” aspect of enterprise software.

People think of Slack as a collaboration tool. But Kevin makes the point that a major reason Slack is so necessary (and valuable) is that other applications and business processes are fundamentally broken. You need Slack to fill in the gaps. You switch out of a productivity app (Salesforce) and move to a collaboration app (Slack) because Salesforce doesn’t have collaboration as a primary aspect of the product.

As an example, a sales manager might be in Salesforce and notice that a revenue number on a particular deal is inaccurate. The manager will go to Slack and send a message to the rep. The rep will respond in Slack and go fix the number in Salesforce. If Salesforce was truly collaborative, all of this communication would’ve happened inside of Salesforce. But it’s not. And that’s where Slack picks up the slack for non-collaborative business applications (pun intended). From the piece:

The dream of Slack is that they become the central nervous system for all of a company’s employees and apps. This is the view of a clean *separation* of productivity and collaboration. Have all your apps for productivity and then have a single app for coordinating everyone, with your apps also feeding notifications into this system.

But productivity *isn’t* separate from collaboration.

.…

It’s not that Slack is too distracting and killing individual productivity. It’s that your company’s processes are so dysfunctional you need Slack to be distracting and killing individual productivity.

For the first 10 to 15 years of my career, I used Microsoft Office applications. I didn’t consider anything else. They had a total monopoly. In the last five or so years that has completely changed. I never use Word or PowerPoint (I still use Excel frequently). For word processing and presentations I almost exclusively use Google Docs and Google Slides. I’ve made this change for one reason and one reason only: collaboration. G Suite (Google’s suite of productivity applications) is fundamentally built on collaboration. It works really well. Collaboration in Microsoft Office applications is clunky and was clearly an afterthought. It’s very difficult to start with productivity only, run that playbook for several years and then back into collaboration. Collaboration from the outset makes things a lot easier.

Healthcare software is suffering greatly from the fact that the software clinicians use didn’t have collaboration as a fundamental part of the code. Most medical software was rushed to market in response to government incentives and collaboration across different organizations wasn’t important. Now, like Microsoft Office tried to do, many of these applications are trying to back into collaboration as a fundamental feature and it’s not working.

This is one of many reasons that PatientPing exists and is growing so quickly. Our software puts collaboration first. Our entire platform is built around collaboration and allowing disparate healthcare organizations to collaborate on shared patients. We’ve tapped into a desperate need because of the way healthcare software was developed. If collaboration had been build into healthcare software from the beginning, our product wouldn’t be in such demand.

Similarly, Slack is widely touted as the fastest growing business application in history. Not to take anything away from their success, but much of the reason for their success is that Slack picks up the slack of so many other widely distributed productivity applications across nearly every industry. The lack of fundamental collaboration in productivity apps created the conditions for Slack’s massive success.

Some Thoughts On Enterprise Software: Increasing Consumerization, A SaaS Bubble & Cross-Company Network Effects

Here are some thoughts related to enterprise software that have been rolling around in my head for the last few weeks.

Consumerization’ Of Enterprise Is Accelerating

Aaron Levie (founder of Box) tweeted this the other day following the Zoom IPO:

I’m not sure we’re fully there yet, but the tectonic shift Aaron refers to is absolutely happening faster than I had thought.

Back in 2011, Chris Dixon wrote a blog post discussing why consumer tech is so much better than enterprise tech. I posted this comment:

In a [B2B] transaction, one good salesperson (the “seller”) only has to sell one person (the “buyer”) on the value of the technology. Once the product is sold, the buyer forces their 50,000 employees to use that technology whether they like it or not. A good salesperson with a good deck can do this fairly reliably.

And a good account manager can typically retain the client for a while; employees usually get used to the product and rarely complain enough for the buyer to cancel the contract and force the seller to improve the product. As a result, an enterprise product can suck and still flourish.

With a B2C product, this is much, much more difficult. The seller has to sell 50,000 individual “users”, one by one, on the value of the product without the luxury of a face to face meeting or 18 holes on the golf course. The B2C model forces the seller’s product to “sell itself”. As a result, a consumer product can’t suck if it wants to flourish. It has be good. Much better than the enterprise product needs to be.

In light of the Slack and Box IPOs, things are looking a lot different than they did back in 2011. There are a few trends causing enterprise software to look more like consumer software.

1/ Bottoms-up enterprise distribution is expanding. This is where an employee within an organization signs up for a service and tells a few colleagues. Soon, when enough employees are using the product, a sales call is triggered and the salesperson tries to sell the product into the organization top-down. Unlike the old days, this strategy only works if the product is really solid.

2/ Micro use cases are increasing the number of buyers inside an organization. The purchase of a CRM or ERP system will likely always be a complicated, top-down decision. But because of the emergence of SaaS products with narrow use cases that require relatively small budgets, the purchase of a SaaS product that, say, improves the efficiency of making sales commission payments to salespeople, will lie with a middle manager in the sales operations or finance function. When buying responsibilities are spread more widely and the decision maker is closer to the user (or is the user), the quality of the product has to improve.

3/ Buyers are getting smarter and products are getting more transparent. The internet has enabled thousands of micro trade groups and private communities to form, allowing professionals to share insights and best practices and advocate for one another. I recently joined a collective of revenue leaders from all over the world. We have a Slack account that we use to share information, ask one another questions, etc. There’s a #techstack channel where we discuss different SaaS products focused on sales and marketing organizations and our experiences with them — Outreach, Gong, Troops, Docusign, etc. I’ll never buy another sales-oriented SaaS product without consulting this Slack channel. At some point, nearly every buyer within a company will be a member of one of these groups (if they aren’t already). This only accelerates the transparency of information for buyers and makes product quality and delivery equally important — and in many cases, more important — than distribution.

There are still a lot of old school industries where top-down purchasing is a requirement because of outdated buying practices, the need for legacy system integration, security concerns, etc. But in the coming months and years enterprise software will continue to look a lot more like consumer software.

A SaaS Bubble?

I’ve heard many people refer to the explosion of SaaS as “the unbundling of Microsoft Excel”. That is, Excel used to do everything for us but now a bunch of companies have peeled off use cases and have built SaaS products around those use cases. This is really true in many ways. Fifteen years ago the companies I worked with did just fine without many of the SaaS applications we have today. We just did all of it in Excel. Sales pipelines, expense reports, commission payments, time tracking for consultants, project management, OKR management, etc. Now all of these things are managed by products like Salesforce, Expensify, Exactly, Harvest, SmartSheet and 7Geese. Companies today use so many SaaS products that Parker Conrad, the founder of Zenefits, raised $60MM to start Rippling, a new SaaS company that helps organizations set up and manage access to all of these applications. Largely due to bottoms-up distribution, the number of applications being used inside today’s companies has gotten way ahead of many system administrators.

Related to all of this, we’re due for an economic slowdown. Recessions seem to come around every ten years; we had the oil price shock recession that started in 1990, the tech bubble recession that started in 2000 and the mortgage crisis recession of 2008. We’re just about due for another one as we head towards 2020. When economic growth slows, it’ll be interesting to see the impact on many of these SaaS products. Many of them seem like ‘nice to haves’ rather than ‘must haves’. If that’s true, you have to wonder how many CFOs will cut back on some of these products and force their teams to go back to using tools like Excel. ‘Bubble’ is a strong word. And those that are bullish on SaaS will tell you that the market share of enterprise software that sits on the cloud is still a small fraction of total enterprise software spend. But it does seem logical that the boom is SaaS is supported by the bull market we’ve been in.

Enterprise Network Effects

Perhaps the most exciting thing happening in SaaS these days is network effects across companies. Network effects happen when you have a product that gets more valuable to each user as more users use it. Facebook is a classic example — the more friends you have on Facebook the better your experience is on Facebook. But now we’re seeing cross-company network effects all over the place. Box.com allows companies to share files with their customers. Companies can invite their customers to Slack channels. My company, PatientPing, is a classic example of how this happening in healthcare. It will be interesting to see how far this goes. Competitive and privacy concerns cause companies to be hesitant to share and open up their data troves to competitors and even vendors in many cases. If a company like Salesforce could find a way to get their customers to open up their data it would change the world of enterprise software. The use cases would be infinite. A fun trend to watch in the coming years.

It used to be that employees would sit around the water cooler chatting about systems and processes that don’t work as well as they could or complaining that they’re spending too much time doing low-value work that could be automated with software. This is still true. But now that it’s so easy and inexpensive to launch a software company, many of those same employees are realizing that other companies have the same set of problems and they’re building companies around solutions to those problems. As we’ve seen with Slack, Zoom, and others, some of these solutions can be multi-billion dollar companies.

Enterprise software used to be considered the boring part of tech. It doesn’t seem so boring anymore.

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.

The Sales Evangelist Podcast

Several weeks ago I had the chance to appear on Donald Kelly’s Sales Evangelist Podcast. The topic of the podcast was How To Deal With The Pressure Of Hitting Your Quarterly Number.

We discussed how to project sales results, how to be analytical about what’s working and what’s not, empathy, transparency and a bunch of other things related to working in a high pressure environment.

Check it out below on Stitcher or on iTunes.

I’ve done a bunch of these now so I’ve added a Podcasts category to the archive.

The Second Most Important B2B Sales Metric     

As a sales leader, your most important metric is top-line revenue.

But a very, very close second is the percent of sales team members that are attaining quota. Ideally, this number should be around 60% to 70%

If you’re hitting your top-line number but only 10% or 20% of reps are hitting quota, you have a couple heroes but you don’t yet have scale. That’s a problem. You’re placing all your cards on a small number of individuals that could stumble. And you’re also wasting a lot of time and money on reps that aren’t carrying their weight.

Some reasons why you might have this problem:

  • Product/market fit isn’t yet validated (broadly, or in specific markets or product segments).

  • Inequitable territory allocation. 

  • Quotas too high.

  • Lack of training. 

  • Inadequate management or coaching.

  • Ramp-up times are too aggressive.

  • Lack of quality sales talent.

  • Low employee engagement. 

One caution: be careful about the time period that you’re using to measure this metric. For SMB sales teams, it’s fine to look at quota attainment over a month or a quarter. For enterprise sales teams you probably want to look at this on a rolling 12-month cycle. 

Finally, view this metric as a journey that never ends. When a company starts, generally the founder is the only one that can sell the product, then a couple more can do it, then a few more and so on. As you grow, you’ll need to continuously evaluate and solve for the problems listed above. When you solve for these things and get quota attainment up to 60% to 70% it’s time to increase your quotas and do it all over again. 

The hardest part of building a growth machine is that it’s never finished.

The 10 Best Books I Read In 2018

I’ve started writing year-end book lists rather than summer reading lists. See past lists here.

I recently heard someone say that they only read books that are more than ten years old. His thinking is that if the book is still getting good reviews after all that time then it must be really good. I think I like that idea. A lot of newer books that get good reviews don’t end up standing the test of time. This past year I read a lot of new books. I’m going to change that in 2019.

Here are the best books I read in 2018, in order:

  1. Atomic Habits by James Clear. I’m such a believer in the power of habits. Motivating yourself every day is just too damn hard. This book offers a very actionable guide for creating them. A fast read with great advice that you can put into action right away.

  2. Empires of Light: Edison, Tesla, Westinghouse, and the Race to Electrify the World by Jill Jonnes. Business history is my favorite book genre. This one gives the reader all the detail on these three amazing entrepreneurs and the competitive dynamics they faced in trying to commercialize electricity and light. Not much has fundamentally changed in entrepreneurship since the 1800s. Success in new ventures requires the ability for the founder to see the crazy big opportunity that most can’t see. Most people thought electric lights would only be used to replace gas street lamps. These three saw so much more than that.

  3. Bad Blood: Secrets and Lies in a Silicon Valley Startup by John Carreyrou. The story of the rise and fall of Theranos. Even if you don’t care about tech or healthcare or startups this one is just a great read. It reads like a great fiction novel. Carreyrou was the Wall Street Journal reporter that exposed what was really happening within the company and this book lays out all the troubling detail.

  4. Tribe of Mentors: Short Life Advice from the Best in the World by Tim Ferris. This is one of the best books I’ve ever read. The only reason it isn’t first on the list is because it isn’t really a book; it’s a series of short interviews with dozens of world-class performers (writers, entrepreneurs, athletes, etc.). It talks about their habits, morning routines, secrets to success and other philosophies on life. I made more highlights in this book than any book I’ve ever read. After reading nearly 600 pages of interviews with high performing individuals, if I had to summarize their secrets to success I’d say it’s two things: they read a lot and they meditate daily.

  5. The High Growth Handbook by Elad Gil. Gil has been through it all at several high growth startups (Airbnb, Twitter, Google, and others). This book is basically a technical handbook on growing a startup. It offers extremely practical and actionable advice and gets really, really specific. I’d call this a must read for any first-time founder.

  6. The Wealth and Poverty of Nations: Why Some Are So Rich and Some So Poor by David S. Landes. The title says it all. A fascinating and detailed look at the way societies have evolved and why some have done so well while others have struggled (hint: it’s mostly about climate). Despite the heavy topic, Landes keeps this one pretty readable.

  7. Tribe: On Homecoming and Belonging by Sebastian Junger. I think I’ve read everything Junger has written since the Perfect Storm (one of my absolute favorites). He’s such a great writer. Tribe is a quick read and covers the topic of PTSD for veterans returning from war and the irony that so many troops are happier at war than they are when they return home. The reason is that war-time creates such strong bonds between platoons regardless of race or ideology or other individual traits. It creates enormously strong ties and loyalty and there’s a strong human desire to belong to a tribe. All that seems to fall apart when troops return home. A troubling but really interesting topic.

  8. Shackleton's Way: Leadership Lessons from the Great Antarctic Explorer by Margot Morrell. This is a classic leadership book that I can’t believe I hadn’t heard of it until someone recommended it to me a few months ago. The book chronicles Sir Ernest Shackleton’s leadership of his crew through a failed 1914 Antarctic expedition. Shackleton’s boat got stuck in ice and sank in the middle of the Antarctic and he and his crew survived for two years before being rescued. The story itself is amazing but Morrell lays out really interesting and classic leadership lessons from Shackleton along the way.

  9. This Is Marketing: You Can’t Be Seen Until You Learn To See by Seth Godin. I’m pretty sure I’ve read all of Seth books and I rarely miss his daily blog posts. Seth’s books are always a little idealistic and aspirational and this one is no different. This one is sort of a summary of most of Seth thoughts on marketing. If you haven’t read anything by Seth this one would be a good place to start, though I think Permission Marketing should be required reading for business school students and is one of the best business books ever written. So read that one too.

  10. Behind the Cloud: The Untold Story of How Salesforce.com Went from Idea to Billion Dollar Company and Revolutionized an Industry by Marc Benioff. The story of how Benioff flipped the enterprise software business on its head. This is a great read for anyone that works in enterprise software. Someone recently made the point that every 1% of Salesforce.com’s market cap represents a unicorn. I think this company is going to be really interesting to watch over the next several years. There are literally hundreds of startups trying to unbundle this massive CRM. Benioff is an outstanding salesman and a great leader and for anyone that works in enterprise software this one is definitely worth reading.