Do Less, Better

Inspiration sparks the best ideas, creative process crystalizes them, and perspiration makes them come to life. Three parts of the value creation chain.

We startup founders are excellent at the perspiration part. We push and push, optimizing for a constant state of busyness, checking off more boxes than we did yesterday. Eliminating more gaps in our schedules in favor of “GSD” (getting shit done).

In doing so, we feel productive. We’ve been conditioned to “do more, faster“. And that’s not wrong, but the question is at what cost?

Inspiration and creativity require one thing: Space. The very thing that our quest for productivity would have us eliminate. We’ve been sold a line that we must hustle ad infinitum, and bought it wholesale with little awareness of the implications.

Nothing happens without perspiration. It is the core characteristic of successful founders, and foundational. But successful founders get that part, and then go too far.

With the way we glorify the hustle as founders and leaders, is it really a surprise that true inspiration and creativity have become so rare? Why everyone is just the “AirBnb for pet crates” or the “Uber for luggage”?

How I learned to feel again

“But I want to be passionate,” my friend said. “I get the whole search for Enlightenment, but I don’t want to be disconnected from life and stop feeling.”

We were sitting in a coffee shop, at a corner table discussing my practice. I had described, to the best of my then current ability, both the work I’d done and the results it had produced. I said that meditation in my experience, when practiced for some time, produces, at least, two results.

First, it teaches you just how little you control. Stare at a wall and try to hold everything still; it doesn’t take long to see that there’s nothing you can really control, not your breath, your heartbeat, and definitely not your mind. If you don’t control your body or your mind, how on earth can you control producing XYZ result in your life?

And second, it creates a space between your Self and your thoughts. Between You and your emotions. With a quiet mind you get to actually see your thought patterns, and see the emotions running through you. And if you can see those things, then you by definition are not those things. You are the viewer, and therefore cannot also be the viewed. You are the awareness within which your thoughts and feelings arise.

It was the second realization that my friend took issue with.

“I don’t want to disconnect from my feelings,” he said. “I want to live, fully!”

It’s a logical concern, but only from the perspective of one who has not yet experienced those things. Once you do the work to create that space between your self and your thoughts/feelings, you realize that actually the opposite is true.

“I do too,” I said. “I didn’t feel, really feel, for about 15 years. I got so caught up in what I was supposed to be, what I was supposed to feel, that I suppressed all of it. But now, I’m crying on airplanes.”

I was referencing a time months ago when I connected so hard with the movie Rocketman that I had to compose myself in the airplane bathroom. But I could have just as easily been referencing today, as I write this on yet another airplane, days removed from Kobe’s death, all nine of those people, three kids, and still tearing up. I’ve never met Kobe, and part of me feels selfish crying over something that other people are so much more closely affected by than I am, but I feel everything, now. In a way I never did before.

“You’ve got it wrong,” I explained to my friend. “Once you realize your thoughts and emotions aren’t you, they are no longer a threat to your sense of yourself. You stop resisting them, and you feel way more.”

Scaling value while also scaling variability

Scaling a business, we’re told, is about establishing processes, procedures and workflows, to ensure that the value that you created when you were small persists as you grow. The goal being to ensure that every experience your new customers have is of the same value as the experiences your early customers had. To do so, it seems, you have to eliminate variability to prevent substandard customer experiences.

But variability drives innovation. Without random variation, single celled organisms never evolve into human beings, and nobody even has the luxury of thinking about scale. Variability is the singular engine driving adaptation, growth, and increasingly, in the rapidly changing world we live in, survival.

So can we scale both value and variability? Should we?

You simply can’t replicate the chaos that permeates an early stage startup as a company grows, and you shouldn’t want to. We all have enough grey hairs from that time. But if we convince ourselves that there is a “right way”, then our teams will hew ever closer to that. Then, innovation stops, people get caught up in dogma, and the company struggles to meet evolving expectations in a dynamic market.

Even though everyone in the company is doing everything “right.”

What if we aimed instead to scale not only the value creation that we cultivated at a small size, but also the variability that helped us find that value creation in the first place?

As an example, what if instead of a “right way”, we instead scaled a “default way” for our teams (HT: Aaron Dignan), while also giving them autonomy to deviate if it made sense? If we did this, our teams could do what had been proven effective in the past, but they could also change things if they thought it was for the better. They might be wrong, or they might be right, but either way the organization would be smarter having conducted the experiment.

Might we be able, this way, to scale customer experiences better than the ones we first had success with?

RIP Black Mamba. More than that, RIP Kobe Bryant

Sometimes I feel so significant. I’m on top of the world, and sure that I’m doing Important Things, or have Big Events ahead. When I’m significant the rest of the world fades away, and I’m all about me.

I’ve accomplished much through this type of singular focus, but I’ve missed a lot along the way. When I’m significant, my family, my health, everything else gets deprioritized. I don’t miss those things in the moment, as I’ve Important Things to do, but after those Things are done sometimes there’s a quiet, and in that quiet I see the cost of my significance. I see the preciousness of the people around me, the relationships, of Life. But too often I see these things only in retrospect, before inevitably getting caught up in my next significance.

Yesterday something awful happened. 9 people died horribly, including a hero from my childhood and his daughter.

This hero, to me, personified that singularity of focus that has gotten me so far, as his professional career was second to none. The Black Mamba. He was the inspiration for my late nights in the driveway, far beyond a reasonable hour because “somewhere, someone is still working, and someday, when you meet that person, they will beat you.” Mamba wouldn’t be beaten by anyone. Neither would I, but whatever sacrifices I made in the aim to succeed, I’m certain the Mamba’s were greater. He was a transcendent basketball player.

As I’ve grown older, the quiet gaps between my significance have grown larger, and I’ve been able to appreciate the awe-someness of Being, of connecting with what Is in the moment. It’s humbled me, put into perspective my drive to achieve, and I don’t want to imagine the possibility that I might have died before ever having found this peace. Before ever really connecting with the world.

I cried for the Mamba yesterday, for his family, Vanessa, his kids, and for the other 7 passengers on that helicopter. I cried for the little piece of my childhood that died along with them. I wasn’t the only one. It was a sad day. I can’t imagine what the families and friends of those people are facing today. I don’t want to. It’s inexplicably awful.

But I read Bill Platschke’s column in the LA Times, recalling a conversation the journalist had with Bryant recently, and within the overwhelming sadness a new part of me connected with my hero again, for the first time. No longer the Mamba, Kobe, in his retirement, seemed to have overcome his own significance, and found his own quiet.

The edge was gone. The arms were open. He urged acceptance of LeBron [passing him in career points scored]. He preached calm for Lakers fans. He said greatness wasn’t worth anything if you couldn’t share it.

Deep within the grief, I’m grateful the Mamba found his inner Kobe before he left us.

I’m sad. We are all sad. But I’m also committed, as I wake up today, to really paying attention, to really connecting, as it could all be over in a breath.

Why I quit Twitter, and why I’m back after 2.5 years

I’m back on Twitter for the first time since August of 2017.

I don’t remember the exact moment I left, in fact I imagine it had been brewing for some time. In essence it had to do with finding tangible connections between my thoughts and feelings, and what I was reading on social media (I’ve been off all the “social sauce” since about that time, not just Twitter).

Laura noticed it first. Around 2012 I remember lamenting a missed opportunity to her, something I could do instead of banging my head against the wall of building VNN, as I was surfing through my Twitter feed lying in bed. Another Tuesday for us, as VNN was hard work at the time. She ignored the subject of my comment, and said “you have to stop reading that shit.”

With distance, it was easy for her to see the impact that reading about someone else’s accomplishments (so helpfully curated at the time on my feed) had on my feelings of self-worth, and she graciously called me on it. I remember being righteously indignant at the time; it would take more time for me to come around.

The realization evolved organically into a sort of vague connection between my use of social media and an existential sense of inadequacy, which I was compelled to address through working myself even harder to get the next gold star. It was helping my business (I was certainly productive), but destroying me. And over time, as I got more accustomed to watching my thought patterns, I began to see clearly a causal relationship that looked something like this:

  1. Read about someone else doing something cool =>
  2. feeling of dread in my chest =>
  3. thoughts diminishing my self worth because I didn’t do that cool thing first

I’ve heard it said that “you see your competitors through their press releases, while you see yourself naked in the mirror.” It’s always an unhappy comparison, and at the time I viewed the whole world as competition.

From there, it was like buying a Volkswagon. Once I noticed that pattern, couldn’t stop seeing it. It got to the point at which every time I would check Twitter, whatever mood I was in would persist until I saw something awesome that my mind convinced itself I should have done, and then I’d feel like shit.

Getting off social media was hard, and not entirely because it is addicting. Besides that, in the startup and business world, there’s a lot of practical value in maintaining a broad and deep network, and social media is, by far, the easiest way to manage that. But, like any addiction once you realize it’s causing problems but before you decide to stop, it gets worse, and worse, like an elevator that only goes down, until eventually I quit cold turkey. The process of quitting social was actually pretty similar to that by which I quit drinking, back in 2007.

I didn’t see the pictures of my nephews during my time away, and I didn’t know much of what was going on in the world, but I found a sense of peace that had eluded me before. My tendency to measure my self worth by my accomplishments relative to others didn’t go away entirely, but at the very least it wasn’t triggered every day by a deluge of people humble-bragging.

That sounds awesome to me still, as I write this a day after rejoining the Twittersphere (is it still called that?). So why the hell am I back?

Well, that sense of peace, that space where the noise of the world used to be, gave me an opportunity to do the serious internal work of first solidifying my awareness of, and then slowly letting go of (or maybe even rewiring), my internal thought patterns. I’ve had the opportunity to spend significant time in contemplation and reflection, an opportunity that regrettably not everyone gets, and in doing so there’s been a fundamental change in the perspective through which I view the world. My sense of self has decoupled from my thoughts, and therefore my self-worth decoupled from value judgements about my relative accomplishments. So far as I can see, this realization is both foundational and irreversible, even though sometimes I forget in the moment.

I still catch my thoughts getting hooked by cool stuff other people are doing, but it’s easier for me to now dissociate with those thoughts, let them be just the random noise that they are, and move on. My thoughts have become, in most cases, pretty much irrelevant noise to me, much less capable of inflicting the kind of turmoil they once did.

So the danger that social media once posed for me has been neutered, or in any case lessened significantly, which has changed the calculus for me around participating. The bad aspects which once tipped the scale have decreased to the point at which the good shines through, not only in the human connections that I can build with family and friends, but also in the opportunity to help others; I look around me every day and see people caught in their heads, the victims of their own chaotic, self-focused thinking, and I know first hand how profoundly that can suck.

I’ve enjoyed my time on the mountaintop, away from digital society, and it’s helped me grow immensely. But all that time I was up there, I was sacrificing my one and only opportunity to connect with the other 8 billion humans in the world. From where I stood in 2017, that was a fair trade. But upon gaining that equanimity I sought, or at least some version of it, I feel better prepared to engage, and, hopefully, help.

I’ve missed you all, and I look forward to seeing what you’ve been up to.

The case for the startup psychologist

Cofounders are effectively married, so why do we not invest in couples therapy for startups? It works.

There is no more fundamentally important relationship inside a company than between its cofounders, and no area in which things can get more royally screwed. By extension, that applies with only a very slight reduction to the founding team and/or leadership team, the group of people with varying functional areas who through their relationships guide the direction and success of the company.

Market, strategy, culture, all of these things are important. But none of them can overcome bad relationships within the leadership of a company.

So why do we, as founders and investors, not invest in nurturing and securing those relationships? And in the rare cases where we do consciously, why do we expect success from people without any professional expertise?

We rely on board members, usually business leaders all, and the founding team itself to fix these matters. This is like handing a drill to Mike from Accounting and asking him to fix your cavity. He’s not trained in dentistry, so you don’t hand him a drill.

A board and founding team are not doctors in psychology (much less do they possess the required dispassion to do the job with objectivity), so why in the world do we so unquestioningly trust them with managing the psychological dynamics of the leadership team, the single largest lever in our organizations?


I’m piling on here, as it is definitely encouraging to see groups like Freestyle Capital investing in the mental health of their founders. This is critically important and they are pushing the envelope, far, to do even that, but it’s about more than the mental well-being of the individual. We need to go farther, and invest in the mental well-being of the leadership team (if not the organization).

The forgotten half of leadership

Leadership is to most a matter of doing. People have written reams of books, articles, whitepapers, etc about all the doing that is required of leaders. Setting the vision, building a culture, fundraising, all about doing. It’s a concession to our pervasive culture of productivity that the only part of leadership that is talked about is the part that looks like a bunch of boxes one can check. It’s what’s measurable, so it’s what gets done. But it’s only half of the battle.

Leadership necessarily involves two equally important aspects: the subject and the object. We focus so much on the object, or the output, that leaders should strive for, that we rarely address subject, or the leader herself.

This may seem like another way of saying “sharpen your sword,” but the practical reality of doing that is really just a way of checking another box. Important, for sure, but still in the category of the object.

What is needed is a sincere and equal focus on the leader herself, or more specifically the place from which the leader is coming.

Every box that a leader checks is checked from a very unique perspective, and that perspective includes specific preferences, biases, traumas and neuroses, which together make up the narrative that leader has built to bring order and meaning to her life. These biases, traumas, preferences and neuroses, all the chatter living in her head whether consciously or not, are the overarching framework through which she decides which boxes to check and why, and what it means to check a box. Everything that a leader does in her quest to bring about a result for her team, and the things she decides are valuable to do in the first place, are inextricably driven by the internal discussion going on in her head.

If she has overcome a rough childhood, she is more likely to hire people who persevere. If her parents were members of a labor union she is more likely to prioritize creating a great culture over driving for additional profitability. And so on.

None of this is bad, inherently. It’s just a matter of consciously making these choices, rather than letting unconscious processes make them for you. The problem is that every leader makes decisions based on a set of criteria and influences which are unknown to her, unless that leader has done some serious internal work.

The work, here, is to dive deep into your own thought processes, to see the patterns for yourself. Figure out your own innate biases, and what environmental triggers send you down specific thought patterns. Once you see them, then you have a choice to make: are these helpful to my aim as a leader, or should I work to neutralize them.

This is why the best leaders tend to be meditators, and the best business coaches have backgrounds in psychology.

In becoming the best leader you can be, it’s important to become adept at vision setting, culture building, selling, fundraising and the rest. But as leadership is about making good choices, not only for you but on behalf of all the human beings for whom you are responsible, it’s equally important to do the internal work to figure out why you make the choices you make in the first place, so you can make them consciously.

If you want to help people, start a business, not a nonprofit

At some point most, but not all, successful people figure out that no amount of success or money will actually make them happy, and at that significant turning point, people start to look for meaning in different places. There are a lot of places to turn, as the human animal can make literally anything meaningful, but the best of these people turn to helping others.

If you haven’t done a ton of helping others up to that point, it can look like the non-profit world is the route to take here, as it seems like common sense that helping people is why nonprofits exist. That’s fine, and many great people work in the nonprofit world, but if you’re looking to really help people it’s the wrong direction.

Charity is a very small pond.

If you add up all the charitable giving in the world, including all the endowments, the foundations, the $18 to Bernie Sanders’ campaign, literally all of it, it all adds up to 0.005 of the world’s spending, a number which has been relatively steady the past 50 years. A half a percent.

Bracket out for a second the moral statement that level of species-wide charitable investment makes, and let’s just focus on the practical implications for someone really looking for the best way to help people. Absent running for public office (which godspeed to those souls who jump in that water but I have both no interest and a checkered past) we basically have two choices: business, responsible for 99.5% of all monetary impact in the world, and charity, responsible for 0.5%. Remember the all-importance of market size, and choose to fish where the fish are.

If you still think a nonprofit is the way to go, consider that since there is not enough money to go around, and since there are over 1.5 million registered worthy causes in the US alone, in order for you to make the impact you want to make with your nonprofit, you have to literally take funding from another nonprofit with another well meaning mission to change the world. People or organizations with money and a conscience tend to organize their giving by first setting a budget, and then choosing where to give or which cause to support from that budget. So if your neighbor wins and gets funding, that actually in reality lowers the chances of you getting the funding you need. Charity is literally a zero-sum game, so there’s a tangible human cost to any success you have in that area. Not the case in business, in which there is absolutely such a thing as a win/win/win situation (despite, admittedly, some confusion).

So far as I can tell, the only way to create lasting meaning for human beings is to help other human beings. For those of us who have learned the emptiness of self-serving success and want to create meaning by helping others, start a business, not a nonprofit.

Seeing the wave

“We need to talk,” my Controller said. A controller never does that when it’s good news.

He had knocked on the doorjam and waited by my open office door for me to give a signal. When he spoke I felt a rush of dread wash over me. A tangible feeling of all the times we’d almost run out of cash, cresting over me in a wave of heat and adrenaline. My heart beat in my ears. My face flushed.

In the wave were all the people who were counting on us, our investors and employees. In it were all my secret doubts as to my own sufficiency in managing the business. My core belief in the imperativeness of saving every penny, juxtaposed with the burn rate we’d been keeping up at the instruction of the board. I couldn’t believe how much of a failure I was that I had let it get to this point. I knew better. And now everyone would know how misplaced their faith was in us.

Whoa, it occurred to me as I considered the wave. That’s intense. And a bit over the top. Does this happen to me every time he wants to talk?

And then as quick as it came, it was over. Upon seeing the reaction clearly for what it was, a skill I’d been cultivating through meditation for about 6 months at the time, the wave dissipated on its own.

I invited him in, and we discussed how we didn’t have enough cash. And we made the decisions we had to make.

Paying attention

I’ve been on a lifelong chase for happiness, and until recently defined that as the feeling that I’d get from a peak experience. But I’ve chased and attained enough peak experiences at this point to have thoroughly convinced myself that none of them will ever match up to my expectations. I’ve put myself through hell for the chase, in business, relationships, sports, all of it. And while chasing something unquestionably serves as fuel to drive me to push harder, always harder, and achieve things that people respect and admire, attaining that thing at the end universally feels like a let down.

I can no longer convince myself that attaining that next gold star will bring me lasting happiness. I see the machinery working behind the scenes in my mind, and I know how to play the record all the way to the end. Everything around me, everything that is America with a capital A, tells me I should want that next thing, but I mostly don’t much care.

These days I’m finding that happiness comes from paying attention.

Learning to pay singular attention to the entirety of the present moment (all six senses: sight, hearing, taste, touch, smell, and thought), through consistent practice for going on 5 years now, has unlocked a different type of happiness for me, one I didn’t even know I wanted, as caught up as I have been in the chase. A contentment, awe and gratitude that is accessible at any time and maintainable for sometimes hours.

The paradox is that there is only one sure way I’ve found to lose that contentment, and that’s by chasing it. Trying to pay attention in order to see something profound is a sure way to lose the thread. In fact, trying to get anywhere or become anything is the opposite to actually being where you are, and paying attention. The only way to really do that, totally, is to stop doing anything and simply observe.

Much of my life has been living my perception of the American ideal. Work your ass off, sacrifice the present for the future, take risks, make money and buy stuff, and reap the rewards in a stockpile of unique and impressive experiences. A war chest of memories and stories. I played that game for a long time, and have quite the collection.

But it wasn’t until I stopped chasing that I finally realized the profound, awesome beauty of the random tree on the side of the road.

Copy link
Powered by Social Snap