Top 5 Books / 2017

  1. The 100-Year Life: Living & Working in an Age of Longevity - our kids have a 50% chance of living to 105 at the same time that many historical sources of financial and emotional stability are vanishing - what are the implications for happiness, employment & society?
  2. The Agony & the Ecstasy - beautiful historical biography of Michelangelo. He was a true creator, pursuing his passion of sculpting marbles despite innumerable obstacles & irrational incentives.
  3. Principles: Life & Work - a phenomenal meditation on self-care and org leadership, & a guidebook for building lasting companies.
  4. Homo Deus: A Brief History of Tomorrow - a darker companion piece to the also great Sapiens & 100-Year Life. How will many of us find meaning when routinized work is automated in the next 30 years?
  5. One Hundred Years of Solitude - in the 'post internet' world, where any question or image can be answered or discovered in seconds, creating a sense of true wonder can be hard. But as parents, & leaders, this is what we should be shooting for.

Leading from the middle

At a breakfast yesterday hosted by Bleeker, we had an in-depth discussion about leadership, & how to lead others. 

Leadership is a word that means different things to different people. We went around the room and no two people had the same definition of leadership. 

At one point the discussion evolved into style metaphors - e.g. servant leadership, leading from the front, leading from the back. Someone said they prefer to 'lead from the middle'. It's the first time I've heard this metaphor, and it really resonated.

The essence of leadership isn't about, on one hand, making a lot of decisions that cascade down through the organization, top down. Nor is it only supporting the team 'from behind' & getting the most out of every individual. It's both of those things. Leadership emerges out of knowing when to lead from the front, and when to lead from the back. When to employ wartime tactics, and when there's enough relative peace to focus on process. Achieving the right balance at the right time - staying fully present to the exact time and place the organization finds itself in - is leadership. In order to recognize this, you need to be in the middle. 

The same is true for team management. A common scenario that founders or senior team members find themselves in: person x just joined the organization and needs a lot of support. How much guidance should I provide? Should I be directive or much more hands off? 

The answer of course is it depends. Specifically it depends on the unique qualities of the two individuals - the manager and the managed. And the core values of the organization, as well as the specific time and place within its evolution. There are no template answers. In light of this, knowing the right way to proceed is leading from the middle. 

This is the danger of personality assessment frameworks (Myers-Briggs, etc.). These frameworks tend to assume a static environment and static personalities. In my experience the real world is much more complex. As soon as a unique individual is reduced to a box of 16 (or whatever), there's too much temptation to oversimplify how its best to interact with that individual. There are about 7.5 billion boxes in the world today. The best a leader can do is stay fully present to the needs of the individual and organization at that time. As soon as decisions are made based non-context specific rules or frameworks, problems emerge. 

This means that our organizations exist in a state of unending change & complexity. Leading from the middle is the ability to keep in balance the needs of the organization at that specific time - which is always evolving - and the needs of the specific individuals within the organization - who, like the company, are also always evolving. 

The Higher Education Question

I enjoyed listening to Bill Kristol interviewing Peter Thiel on his podcast - both interviews are worth a listen. The first interview dates from 2014, around the time Zero to One was released.

Thiel has strongly held and well-publicized views on the value of higher education. The university experience is not dramatically different than it was two or three decades ago - it just costs 400% more than it did in 1980 (post inflation). The student debt curve is very steep and getting steeper:


At the same time, the nature of work is changing. Outside of a few elite programs, university is no longer the best option to learn about cutting-edge technologies that will drive the future of work. It certainly isn't the nimblest. And it's an increasingly expensive way to acquire essentially a generalist skill-set: significant re-education and retooling will be required to keep pace with change over the next 30-50 years.

I would also imagine that the value of a university degree from all but the most elite colleges is quickly eroding. Skills acquired from certification programs like the Flatiron School, cheap or free online courses, or self-education from the proliferation of content, can be immediately applied in a real world setting. ROI is nearly infinite and the cycle time is short. 

We don't know what the future of work will look like, but we know with a high degree of certainty that work will be very different. According to one estimate by two Oxford researchers, 47% of US jobs will not exist by 2033. 

 David Perrell, The Future of Work

David Perrell, The Future of Work

It was one thing to invest time or money in a college education when the employment market was relatively static - the jobs were in military, agriculture, financial services. It's another thing entirely when many jobs we now do won't exist in 30 years, and the jobs we will do don't yet exist. 

This isn't to say a college degree is no longer worth it. For some it certainly is - but I don't think its such a no brainer anymore. The situation is stark enough to call into question on an individual basis whether a 4-year and six-figure expenditure will have the kind of ROI one would expect from an investment of this quantum. 

What other possibilities might exist for 4 years of time and (if you are fortunate enough) that kind of money?   

The Smartphone / Vacation Paradox

Today feels like the real start of the work year, back in the saddle after August. I spent two weeks on the west coast with my family - one week working in LA, and another week off in Las Vegas. 

Technology - specifically smartphones and wifi - has permanently altered vacations. Our habitual checking is hard to switch off when we go away for relatively short periods of time. It’s tempting to ‘unplug’ or take an extended ‘digital sabbath’ - however practically speaking smartphones are so ingrained in how we communicate with each other, this can end up a serious inconvenience. Try meeting up with extended family different hotels without text messaging - it can actually be inconsiderate to be unplugged! 

It’s tempting to vilify the iPhone and what its done to the modern family, nostalgically looking back at smartphone-less vacations. However, the same device provides unprecedented flexibility for where work can happen, which in turn can giving back us much more time with family & friends. Remote work has been normalized. Even if we don’t want it, our colleagues or stakeholders expect us to be available at short notice. 

So what’s the answer? On one extreme there’s the ‘airplane mode’ holiday - I see many people do these, although they don’t work for our family. And expecting to create real value as a growth company unplugging for multiple weeks a year isn’t realistic. 

On the other extreme, reflexive email creep can lead to your body on vacation while your brain is still at work. I’ve experienced starting a vacation week barely checking email, but by the end losing all discipline and falling back into normal checking patterns. 

I think we’re experiencing a paradigm in what it means to really be on vacation. Being conscious about this can lead to the biggest work-related lifestyle improvement in the past 100 years - the ability to work effectively, remotely, for far more time than the typical US worker currently takes off as vacation time. 

However we need common sense rules of thumb - its hard to imagine value created in a company where employees are at remote locations simply responding to each other for several weeks or months a year. And we need to shift our mind patterns - just because we can see the ocean or are deep in the mountains doesn’t mean the work stops. 

Remote work is here to stay. But work means proactive work - kicking off new initiatives, selling, driving results. I can imagine personally being effective for 2 months or more in this pattern. 

True vacation is something else. It’s reactive work. Whether this means its possible to unplug fully depends on many factors. Personally, I like to ensure value is building in my absence, which means responding to the occasional email or even ensuring a project stays in track. 

In true vacation mode the key lies in conscious choices. If I need to check email, I do so consciously rather than reflexively. I am making a choice. I also take a few breaths before checking, to ensure that I’m centered. I also try to not engage in debates that can turn emotional and therefore spill into my subconscious throughout the time away - I stick to the basics. 

I think solving the remote work / vacation / office time equation can allow us to live better lives, with more time experiencing and bonding with loved ones and friends. But if we’re not careful, we can sleepwalk into never really being on vacation, or potentially worse, work for companies where no real work is getting done. 

The Clean Organization guide to org structure and employee roles

What to call an incoming member of the team causes much heartache in growth organizations, both at the onset as well as years down the line. I’ve seen organizations where titles convey very little about the experience or responsibilities of the person who holds it, and organizations where titles have been carefully crafted with precision and carry much signaling weight. 

There’s no one right answer, and even the Silicon Valley elite debate the point. Ben Horowitz details the philosophies of the Marc Andreessen and Mark Zuckerberg in The Hard Thing About Hard Things

Andreessen argues that people ask for many things from a company: salary, bonus, stock options, span of control, and titles. Of those, title is by far the cheapest, so it makes sense to give the highest titles possible. The hierarchy should have Presidents, Chiefs, and Senior Executive Vice Presidents. If it makes people feel better, let them feel better. Titles cost nothing.

At Facebook, by contrast, Mark Zuckerberg purposely deploys titles that are significantly lower than the industry standard. Senior Vice Presidents at other companies must take title haircuts down to Directors or Managers at Facebook. Why does he do this? First, he guarantees that every new employee gets releveled as they enter his company. In this way, he avoids accidentally giving new employees higher titles and positions than better-performing existing employees. This boosts morale and increases fairness.

I like clean org structures as its a great tool to create the right accountability within an organization, as well as identify any mismatch in expectations between the employer and the employee at the onset. It also creates a milestone based framing to revisit at future review periods. 

It’s too easy not to invest the time upfront in setting the right expectation about layering, future promotions, and responsibility spans. This inevitably leads to organizational function and disappointment a year or two down the line. 

Matters regarding founders specifically

What is a co-founder?

Early on in a company’s evolution, there’s a hazy line between who is called a founder and who isn’t (e.g. the ‘first employee’, etc.). I myself was a ‘first employee’ at onefinestay, not upgraded to the founding team until several months after joining. 

Founders need not be the most senior people in the organization, but they do need to be the most emotionally vested, and the most committed for the long haul. Unless something goes wrong founders are expected to see the company through - even if it takes 10+ years. This is not the same expectation for everyone else. 

Founders are also the ultimate embodiment of the company in human form - the standard of of conduct and behavior internally and externally. They set the tone and culture and live the company values. 

Companies survive and fail due to trust issues in the founding team. 

And even if not organizationally senior, founders should be part of strategy setting and decision making for the duration of the company’s life. 

Proceed accordingly. 

The location of founders

Perhaps I am old school, but I think founders need to be co-located for a significant amount of time. This is because the business you end up building is rarely the business you intend to build at the onset (see Fred Wilson’s recent post about this topic), and defining the product and operating model is typically a multi-year affair. 

Before the operating model is 90%+ set, cycle time & speed of execution is hugely important. The problem with remote working relationships is inevitably cycle time for iteration increases, and humans are conditioned to have these breakthroughs by the ‘water cooler’, not the Slack channel.

That’s not to say remote co-founders can’t work, but a ton of proactive work needs to be done to offset this effect. Co-location is also the easiest way for norms around values and behaviors to solidify. 

Over time, founders based in different locations can become an asset rather than a liability, as a foundational, deeply trusted member of the team is on point to help with expansion, business development, etc. 

Broader company organizational & role considerations

Companies are hierarchies

As an old boss once told me, everyone has a boss. I would add that all companies need one CEO. Co-founders should have reporting relationships between them. 

I personally love the Fred Wilson / Jerry Colonna framework for what a CEO’s job is - here’s a video of Jerry describing it 


The top level functional leader for a number of conventional functions and critical component of steering the strategic direction of the overall business. If the functional org below the executive isn’t performing, the buck stops with them (and the CEO). 

I prefer to keep C-titles as conventional as possible (e.g. CEO, COO, CFO, CTO), although given the importance of the broader sales & marketing function a CMO / CRO / CCO could also make sense. 

Beyond this, we’re inventing C-level roles. In edge cases this may make sense to land a world-class individual, or due to the specific context of what the company does (e.g. a company where HR strategy is a critical strategic piece of the offering may want to have a CHRO or chief talent officer). However its ideally to be avoided as it sets a precedent for other senior members of the team to feel slighted and/or argue for their own diluted C-titles. 

Your C-levels should also be your executive team.


I don’t like this title for the same reason as I don’t like less conventional C-titles. Suddenly a critical layer of the team (VP) feels slighted once there’s an SVP in the room.


The leader of a function of great importance to overall business impact. This can be either because a large number of people work within the function (e.g. operations), or because the function greatly influences the strategic direction of the business (e.g. product). The intention and expectation at the onset is that this individual will not be layered if things go as planned - they are expected to be the most senior representative of a function. 

Your VPs & C-levels should be your broader leadership team. This may include the director/head of layer depending on its absolute size and company stage. 

Is it a C-level or a VP? 

I have a simple construct for settling this debate that’s most easily illustrated with the common ‘is this person a CTO or a VP engineering’? CTOs drive the strategic technology vision for the organization, VP engineering contribute to the direction but the vision is originating elsewhere. CTOs tell the company ‘here are the new strategic opportunities we can pursue with technology’, whereas the VP Eng role tilts more to execution. 

Number of VPs / C-levels

As companies scale, after the founding period, they should be pyramids, otherwise not enough work gets done and the environment becomes overly political. Limit the number of Cs or VP after the establishment of the foundational leadership team. Too many Cs or VPs in a small organization is a red flag for org dysfunction somewhere. 

Directors / Head of

The leader of a sub-function - common cross company examples are PR, e-commerce, regional sales. They may roll in to a VP, or have a line straight into a C-level. 

It’s critical to set expectations when hiring at this level. Are the individuals expected to rise to VP within x years? Is the organizational ideally looking for a VP to lead the function? What experience is necessary for the next step up in the organization? 

It shouldn’t come as a surprise that a director or head of is layered in the future with a VP - however this relates to the expectation setting exercise at the beginning and on an ongoing basis. 


The leader of a small to midsize team (4+), OR an individual contributor with an outsized impact on company results. 

Team leads

The leader of a small team (as little as one direct report)

Everyone else

Over time, most employees will fit in this group. I’ve seen many titles for entry level staff or individual contributors. My only advice would be not to use any of the above titles due to signaling. 

And finally I would offer a disclaimer. Your organization may not fit into the above mold, or perhaps you have a different view of titles & roles. That’s all fine - however make sure that you have an explicit view. All organizations face challenges as they scale - title drift, politics, accountability gaps. Setting up a clean organization from the beginning helps mitigate these effects to set the company up for maximum output and a higher probability of success.