Don’t settle for success, prioritize purpose over giving the people what they want

The Lean Startup methodology has proven to be the most effective and efficient way to build a successful company. But if it’s your only North-star, you risk optimizing yourself into building a company your customers like, but about which you could care less.

The Lean Startup methodology, first codified by Eric Reis and now in wide use by the vast majority of fast growing companies in the US, is the scientific method applied to startups. It’s lessons are many and profound, but first among them is the virtue of building a company by first transforming it into a series of assumptions by a process of abstraction, and then systematically validating those assumptions against actual customer behavior, BEFORE ever actually building anything (to whatever degree that’s possible).

This process saved us $999,400 on an idea I once had.

It was an app that would geofence communication and media sharing into a single experience available to people attending high school sports events. Instead of building that app immediately, we figured the riskiest assumption was that people would actually use it, so we tested that by marketing a Twitter hashtag as a proxy (we thought that if we could get people to communicate and share on Twitter, that would indicate that there might be an appetite for a standalone app dedicated to high schools). After a grand total of 6 tweets over 5 events we killed the app idea, having spent $600 instead of the $100,000+ we might have spent if we built the app on a hunch, only to find out people didn’t want it.

It’s examples like these that have earned the Lean Startup methodology its status as the de facto best way to build a startup. But like so many things, it can be taken too far. Lean Startup enables you to optimize your business for what customers ACTUALLY want, rather than what you think they want. But as potential customers guide you to the business most likely to succeed, you can find yourself losing the spark that made you want to build your initial idea in the first place.

And you’ll need that spark for what comes next.


Customers, on average, want average stuff. That’s why the concept of a bell curve is so pervasive in every industry. If you optimize for what most people want, you’ll find out that they want something pretty close to what they already have, maybe with one little tweak. So if customer feedback is the only thing guiding your business, in the effort to optimize for success you may end up building yet another me-too app in a competitive market.

You didn’t set out to build another me-too app. You set out to change the world.

I’ve spoken with founders who started out passionately chasing an important idea — solutions to climate change, PTSD for veterans, homelessness — only to pivot to more palatable, generic solutions after learning through customer development that the market for their revolutions was weak or immature. And if sacrificing the soul of your company to ensure its success sounds like a fair trade, there’s no guarantee that even that will work, because it turns out you need that soul to build your company.

The greater the distance between the business you’re building and the one you are passionate about, the less resilience you will have to weather the inevitable storms (tempests/hurricanes/tornadoes/gale-force winds, whatever you like) that come with building a company. You need to want it so badly, way worse than your customers ever will, to succeed. So you can counterintuitively optimize your business toward your customers at the cost of the resiliency which is also a prerequisite for success.

At the end of the day, successful companies require both a market in need of a solution, as well as a founder with an unreasonable passion for building that solution. You won’t have that unreasonable passion if you pivot to something that doesn’t inspire you, even if customers want it.


The answer, so far as it looks to me, is to lean into customer validation and Lean Startup as hard as you can, but only at the right time, and only with appropriate constraints.

For example:

  1. Define why you want to start a company
    1. Is it just about building a successful business?
      1. If so, no problem, but maybe stop listening to me.
    2. Or is it about making an impact in the world?
      1. If so, be really clear on the impact that you want to make, so you don’t lose it along the way. Having that crystal clear definition of why you’re doing this will be critical when you’re putting yourself through all kinds of necessary hell.
  2. Setup constraints around whatever it is that really lights you up, and commit to not going beyond them, even if that’s what customers want
    1. For example, if you’re trying to save the world, commit to only building a business that you are confident will drive humans to be more sustainable, even if what customers tell you they want is to look at new dance videos
  3. Then run a Lean Startup process within those constraints

The smartest businesses leverage lean startup to bring all the power of the scientific method to building companies. There’s a reason that science has eaten the rest of the world. It works. Bringing scientific process to startups enables founders to build their companies with an efficiency not otherwise possible, by surfacing customer desires & feedback early in the process while you still have time to pivot.

But pivots change businesses. Mostly for the better, for sure, but if not done consciously with each pivot you risk losing the spark that made the business worthy to build in the first place. You risk building the business people want, but one you don’t care about.

Protect your spark at all costs, even if your customers don’t yet understand. Building a company is an opportunity to change the world for the better. Don’t let the masses convince you to settle.

Friday Sabbatical

Whatever you’re doing this Friday, I hereby invite you to take a mini-sabbatical from it. Check in with yourself. Feel your breath, the sensations of sitting, or standing, the contact between your body and the world. Notice what’s going on without trying to influence or change it, and simply feel what it is to be alive. This, right now, including everything even COVID, is your life. Be here, just for a second.

The above is way more important than the below.

That said, there are five things below which I think are also pretty important (even one request of my readers), so I invite you to please enjoy:

1. There’s a sense that the world is disintegrating. That everything that was once solid and reliable — life, liberty and the pursuit of happiness, say? — is now falling apart at the seams. This well and truly sucks. This week I refreshed one of my favorite books on the topic: When Things Fall Apart, by Pema Chodron. She articulates beautifully the fundamental reality that things are always falling apart, and our peace is reliant solely on us embracing that fact. This feeling of disintegration is usually a solitary one, so it’s truly unique (and maybe important) that this time, everyone in the world is confronting the reality of disintegration together. The world is dying all around us. And the world will continue afterward.

2. Speaking of, COVID feels like one of those moments in history with a Before and an After. We know what the world was like Before, and here are experts from all over the spectrum predicting what life looks like in their field, After. I hold out hope that the last one is prescient, as I think it makes life much more raw, visceral and ultimately worth living.
And, if you’ve read Yuval Noah Harari’s work, do yourself a favor and read his latest essay, an analysis on the bridge between Before and After, and the two decisions that citizens of America are already making that will reshape our society after COVID (whether we’re aware of it or not).

3. In 1970, Milton Friedman said “the sole purpose of a business is to generate profits for its shareholders.” Based on current events this can now be understood to be demonstrably not true (if it wasn’t already), as business leaders across the globe are stepping up in what effectively amounts to a wartime effort to combat the virus, putting people’s wellbeing at par with or above their own profitability. A personal mentor of mine, founder of Cascade Engineering Fred Keller, who even in peacetime operates by a more complete set of rules than most companies, urges business leaders not to waste what we’re learning through this crisis.

4. The world is changing, and people are feeling tremendous pain, both physically and economically. No matter who you are, you can help.
PHYSICAL: Godspeed to the heroes in the healthcare field right now, some of whom I speak with personally. Even if you’re not in that field, Tim Ferriss has an excellent episode on his podcast about how you can help.
ECONOMICAL: This one is hitting more people than anything right now, as 1% of the US filed for unemployment in the last week alone. There are a few ways to help, including the United Way’s COVID Fund and Humanity Forward’s fund, each helping individual people make ends meet. If you are struggling yourself, findhelp.org and here are good places to start.

5. Finally, an issue near and dear to my heart. The CARES (Coronavirus Aid Relief and Economic Security, the naming of which is probably why it took so long to get passed) act was passed, and includes $350bn in potentially forgivable loans for any small business (<500 employees) to help them get through COVID without layoffs. It’s truly the mack daddy of programs available right now (soon) to business owners.
HOWEVER, in Congress’s efforts to avoid giving undue favors to big business, they have constructed the Act in a way that unfairly penalizes venture backed startups. Check out this Twitter Thread from a leader in the VC community and the NVCA for details, but below is a synopsis:

  • Otherwise eligible businesses <500 employees are subject to something called the SBA “affiliation” rules. Basically, SBA determines the 500 employee test by looking the applying entity, as well as all of its “affiliates”. Unintentionally, a company applying for a loan that has “significant” minority stakeholders – such as one or more VC firms, or a family office, or major angel/HNW investors – will be subject to a requirement that the 500-employee limit be applied *IN AGGREGATE* to all of the *OTHER* portfolio companies in which that minority investor is also a minority shareholder.
  • Let’s use VNN as an example, a company of 70 employees, which you’d think would be well underneath the line. We’re who this program was written for. However, since we have about five VCs with “significant” interest in our company (guessing here as to the definition of significant), as written we would be ineligible for this funding because “VNN’s employees” would include all the employees at those five VC firms, as well as all the employees from all the companies they have invested in, even as those entities are entirely unrelated.
  • The rules weren’t meant to disqualify small VC backed startups from accessing the exact same small biz loans offered to literally every other small biz, but someone missed this scenario so that’s what it does. VC backed startups are the ONLY small businesses ineligible.

So a request: We have contacted our local Chamber and Congressman, but we need help. If you have connections to the Senate or the House, please reach out to them and explain the situation. The entire unfortunate situation is due to something called the SBA AFFILIATION RULES. If you don’t have any direct connections, you can contact the Senate Small Business Committee at +1 (202) 224-5175. And if nothing else, please share this info far and wide (just copy/paste. No need to attribute — just get it out there). In advance, thank you.

And as always, please let me know what you think in the comments, or if you stumble upon something excellent I should be aware of let me know that as well.

When quitting is the logical decision

I went to bed crying about business once, years ago, and I remember feeling like the whole thing was fucked.

We were running out of cash, over 70 employees and their families were counting on me to find more cash, and even though the business was meeting its objectives fundraising was going terribly.

The day before it had been going well, funny enough, before the investor who had spent literally dozens of hours with us pulled out instead of offering a term sheet as he had told us he would. He explained that his partners weren’t as excited about the market as they had been, and the $10m that we had been expecting to close within the next 30 days evaporated when I hung up the phone.

I knew the next step was to open my laptop and get back to work, but it all seemed pointless. We were going to run out of money, I was going to let down everyone that had believed in me, and I personally would be branded a failure and run out of town as a response. I forced myself to look up when Laura got home, and her smile turned to concern when she saw me. We talked, and because she’s amazing she tried to mirror me in such a way that I could see my way out of the situation. She talked through alternative options, bright sides, everything, but I didn’t want to hear it. All our options sucked. We had banked it all on one investor, which I knew was a bad idea but had somehow convinced myself would work, and now it was all going to blow up. Our business was gone, my life was over, and I wanted to crawl into a hole and sleep until I died.

So I went to bed at 6:30pm.


When I woke up, the investor was still a pass. I went through my situation logically, evaluating all the options that we had, and came to the unavoidable conclusion that we still didn’t have any options. I hated that reality, but it was fact. We would run out of money, we would fail, and it would be all my fault.


I’ve found that there are choices and decisions in life, and the two are very different.

Decisions are what you make when you know where you’re going and you’re trying to optimize for the best way to get there. There is a right-est answer, so you evaluate all the data and then make a decision based on that data, trying to steer as close to the correct answer as possible. Choices, on the other hand, are what you make when there is no right answer, you don’t know where you’re supposed to go, there is no available data, or the data contradicts. You don’t evaluate anything in making a choice. You make choices based on gut (said differently: based on nothing), and if someone asked you why, you might be able to spin up some logic in support of that choice, but you’d know it was made up as you said it.


At that moment, sitting in my kitchen with everything telling me to simply pack it in, I made a choice to keep going. All the available data said we were screwed, and I maintain that the correct decision would have been to stop, were I evaluating data. If I had done a pros/cons list the piece of paper would have tipped over due to the weight of ink on the Cons side.

But I chose to keep going.

Three months later we’d secured follow on financing from a new investor just in time, and from that were able to launch the 2.0 version of our product which leads the market today. None of that was possible sitting at my kitchen table looking at the data, but all of it happened because I chose to keep going despite its impossibility. We reached second base not because we knew how to get there and were skilled navigators, but ultimately because we were willing to step off of first base despite having no idea if second base really existed.

Running a business means making thousands of decisions every day. You succeed or fail based partially on your ability to make those decisions with a high degree of accuracy. But running a business also means making at least a handful of choices, and in those moments every successful entrepreneur has consistently made the choice to keep going.

In the words of a mentor of mine, Chelsea FC Avram Grant:

If you persist, you may succeed, or you may not. But if you quit, you ensure you will not succeed.


Update: I went to bed crying about business this week, as COVID-19 shut down the economy. I know a lot of founders who did.

I see how you got there, Billy McFarland

I finally got around to watching the Fyre Festival documentaries, two distinct movies (Netflix and Hulu) each chronicling the rise and spectacular fall of what might have been the largest, most exclusive party in history, held by Ja Rule and a frat bro named Billy McFarland, who is now serving 6 years in prison.

First off, if you haven’t seen them, you should. It’s like watching a train wreck in slow motion, in which the people driving the train are smiling and telling passengers they’re safe and are going to go right through an invisible tunnel while at the same moment the train accordions against the mountain car by car. It’s glorious and horrifying.

Second off, after giving some thought to the horrifying manipulation of people, the careless disregard for people’s safety, the blatant misrepresentation of the truth, the wholesale financial fraud and the general nastiness of the whole situation, I’m left with one distinct conclusion:

I see how you got there, Billy McFarland.

In fact, I would go so far as to say that Billy McFarland (and Steve Jobs wannabe Elizabeth Holmes, for that matter — I see how she got there too) is the logical conclusion of some unique characteristics of what we know as “startup culture,” and that if it hadn’t have been Billy and it hadn’t have been Fyre Fest, it would have been someone else. Perhaps you or me.

The best practices of building a startup nowadays are based loosely around the Lean Startup methodology, which I’ve written about before, and specifically the absolute critical importance of validating customer demand before building anything. In the same way that previous cycles threw money at good ideas with great powerpoints (see dot com bubble), today’s entrepreneurs have been instructed to take the old adage, “fake it till you make it,” as gospel and user manual. Because the largest risk to any new enterprise is whether consumers actually want to pay for what you want to build, techniques to test consumer behavior have become dogma.

It’s a general truism that “you can build anything, it’s just a matter of time and money.” So it follows that the only thing that’s really risky is figuring out whether people want the thing you’re planning to build. Figure that out, and you can figure out how to actually build the thing after. Building the thing is “details,” and you should never “let the perfect be the enemy of the done,” are things I’ve actually said before in my career.

The essence of all this is to figure out if people want it, and then after that figure out all the other details. This is key. I’ll come back to this later.

The best example of this I can think of off hand is Dropbox, the file sharing program you probably already use. Before launching their first product, they went out to test the assumption that people would pay for file sharing service that worked like magic, and to do so they created a video, walking through how the product would work (or something close to it), and then asking people to sign up, in advance of the product actually being built. Now, the guys at Dropbox were up front about the fact that the product wasn’t yet available and in fact people were signing up for nothing, yet. So fair play to them, no issue there. And they learned a ton, and are now the posterchild of how an effective MVP (minimum viable product) can be something very different than an actual product.

So what did the startup world learn from that? Well, that we needed to get customer commitments up front, before building the product, to validate customer demand. Marketing is good, but definitely, for Heaven’s sake don’t actually build the product until you know whether people want it, because building it is where all the cost is.

From this, and following Dropbox’s example, an entirely new startup category blossomed, with landing page builders like LaunchRock, Unbounce, Leadpages, and the like. With these, it became easy to stage digital experiments to validate customer demand:

  1. Launch landing page which shows off your tool or technology as if you have already built it and it’s available for sale
  2. Put a “buy now” button on the bottom of the page with a price, just as if your imaginary product were real and available
    1. When clicked, this goes to a dead link, or a page that says “coming soon” and asks people to enter their email address to be notified when it’s ready
  3. Send paid traffic to your landing page
  4. Track conversion % (the number of visitors / the number of people who clicked the button thinking they were buying your imaginary product)
    1. If the number is high enough, then go build that thing, knowing that people want it
    2. If the number is too low, scrap the idea and maybe tell the people who signed up that it’s not coming (but probably not)

It only took me like 30 seconds to type that whole process above because I’ve done it so many times. It’s one of the most effective tools I’ve run across to validate customer demand, and has proved invaluable in ensuring I spent time and money building things that were likely to succeed (and more importantly, didn’t spend time/money building things people didn’t want). Much better than surveys, experiments like the one above allowed me to closely mimic the actual buying process, so that I would get data on consumer buying behaviors in an environment as close as possible to the real thing. Once buyers clicked a button where they thought they were actually buying a thing, then build it.

For that matter, probably the best example of all this is Kickstarter, where you don’t need a product at all, just a compelling story to get people to preorder your product before you make it. And where 9% of all products flame out without ever delivering on what they promise. This is all acceptable and reinforced by our startup culture.

But it’s also not that different from what Billy McFarland did. Billy basically ran a lean startup experiment at massive scale, figuring he’d figure out how to deliver the party once he was sure people wanted it.

Then when he learned that people were into what he was selling with those orange Instagram tiles he made the mistake of going waaaaay overboard on marketing the shit out of it before he bothered to figure out how to deliver the actual party. Of course it would have been better if, once he had learned that people wanted to party on a deserted island with models in bikinis and Blink 182 (imagine), he had taken a beat and simply asked himself “ok, Billy boy, are we sure we can pull this off? How are we going to do this?” But I’m sure he believed in his own hype and ability to pull off the impossible (sound like anyone we know and admire?), so instead he doubled down on scale and scope. Then, when he had built it into the biggest party in history, he finally looked around and figured hey, we can make this happen, right? In the Netflix documentary you can see him trying to create his own reality distortion fields at that point, channeling his inner Steve Jobs.

This whole thing was a mistake, sure. But more on the lines of a tactical error than a moral travesty. And an error I could have absolutely seen myself making with my own customer development experiments. And if his reality distortion field had worked, if he would have pulled off the party, he’d be just another in a long line of Silicon Valley all stars, proving the primacy of the American spirit over all odds. But it didn’t, and he found himself deep in the shit.

Granted, once there he made some stupid and indefensible decisions on how to dig himself out, which is where the real fraud came in (not to mention some seriously uncomfortable situations for his coworkers). I can’t explain or defend his decision to do such brilliant things as cook the books, or try to sell discounted tickets to other shows that he didn’t have, while on bail during the trial for selling tickets to Fyre festival. What he did once he was down at the bottom of the hole I have a hard time relating with (but it’s worth remembering he was 26 years old, an age eight years younger than I was when I figured out how to work a wash sink), but I can certainly empathize with all the steps down the stairs.

Billy McFarland simply went for it at a massive scale, in a way that had it worked people would have been singing his praises (for the outcome AS WELL AS THE PROCESS), and failed to deliver. This whole thing is different from 9% of Kickstarter campaigns only in scale and publicity, and because some dumb kid didn’t know when to quit.

Leave it to America to crucify the logical outcomes of the cultures we create, especially when they don’t win.

I finally grew up enough to read “Fail, Fail Again, Fail Better” by Pema Chodron

“Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”

Samuel Beckett

I was putting away our Christmas lights (finally), when I ran across a book in the storage area of our basement that made me pause and look closer. It’s called “Fail, Fail Again, Fail Better,” by Pema Chodron, with a forward by Seth Godin.

I’ve owned this book for several years, having bought it in a frenzy of Seth Godin consumption, but the spine was still uncracked. It was one of those books that I’d like to HAVE read, but not enough to go through the trouble of reading it. Like learning Spanish. I want to know it, but don’t particularly want to learn it. That was this book.

But this time, looking with different eyes, the book was simply right for me. I had to read it.

I still admire Seth Godin greatly–his is one of the three blogs I subscribe to–but more importantly I’d had the opportunity to read two of Pema Chodron’s books as a part of my re-introduction to myself after leaving the CEO role at VNN. It was her name on the cover that called out to me, to that human and vulnerable part of me that is playing a much greater role in my life these days. Seth’s name then complemented that call, justifying the read with an assurance that I would be better at work for the investment. It was an utter flip flop from when I had first bought the book, funny enough.

FFAFB is for the most part a transcript from a commencement address Pema did at Naropa University in 2014. Between that and “This is Water,” by David Foster Wallace, it’s fair to say that I’m a fan of reading commencement addresses. As I think about it, they cover some of the same ground, albeit from very different perspectives. The type of advice on how to live a meaningful life that we so often simply skip in our Western education’s rush to tell us how to get and perform jobs.

I won’t spoil the read, as I highly recommend the book whether you’re a vulnerable human or a professional optimizing for results, or some combination of the two. But I will say my favorite part was Pema’s intentional use of the word “forward,” rather than “positive,” in describing the power of being intentional about your attitude on life.

“Let’s use the word forward, instead of positive, because that includes whatever might happen. Instead of going backward into trying to find these little islands of security that keep giving out on you, you learn instead to fly or float and be okay in the formlessness or the groundlessness or the open-endedness of things, which is who you truly have been all along.”

Pema Chodron — Fail, Fail Again, Fail Better

How leaning in to my greatest fear enabled me to make better decisions

Fear drives much of our lives. Neutralize your fear by leaning into it, and free yourself to make better decisions.

I’m convinced that everything I do is either to A) steer myself toward feelings that I interpret as positive or good, or B) avoid feelings I interpret as negative or bad. There really isn’t more too it than that.

I will go to incredible lengths to curate the feelings I’m exposed to. I have ended relationships rather than face my own failings within them. I have blamed others or the world rather than confront something I’ve done wrong. Most often, I will imprison myself and everyone around me in my own personal tunnel-vision, diminishing everything that is not the Goal with a wave of dismissal in an effort to avoid my deepest fear: shame, stemming from my deep recognition that I’m Not Good Enough.

Usually this means making knee-jerk, fear based decisions in reaction to feeling Not Good Enough, that seem right in the moment but that I often regret later on. I’ve sent so many emails that enabled me to check a box, get that dopamine hit of productivity in the moment, but that actually did more harm than good in the long run (sometimes I see this as quickly as 5 seconds after hitting send–#grateful for the ability to un-send these days).

It took me forever to realize what was going on, and develop an alternative.


I learned that I wasn’t good enough early in life, sometime before I can remember, and when I learned that I made the decision that I would do anything, literally anything, to prove otherwise. My whole life from that point forward has been one long series of achievements without end, each one seeming like the most important thing in the world until I attained it, at which point it was and had always been irrelevant. I was still not enough, and only the next achievement would prove otherwise. Etcetera, ad infinitum.

It wasn’t until I stopped achieving, forced through failure (providence?) to slow down, that I had the amazing opportunity to really take stock of the operating system through which I was living. I wouldn’t have chosen to stop achieving, because frankly it pays well, offers tons of positive feedback (the US consumer culture reinforces your worth as a function of your possessions / achievements), and it was painful as all hell to confront the feeling of my own inadequacy head on, rather than continuing to run away from them with the next gold star. But I’m so glad I gutted through it because through that process I was able to see the pattern of my mind’s machinations in a way that demystified it, and offerred me a choice I never knew I had:

Rather than achieving to run faster away from my own inadequacy, I could simply stop. I could stop putting myself through such ambitious hell, and simply deal with what was there.

Moreover, by dealing with what was there rather than running, I could avoid making the kinds of fear-based decisions that I usually regretted. By simply looking at reality without trying to fix it, I could see more clearly what there was to do, and make better decisions.


The thought of confronting my fear and my shame was terrifying, but so was the prospect of jumping back on the treadmill of achievement and simply pretending that I still thought hitting that next milestone would make me happy. So I did it. I simply stopped, taking two months off of work (not all of us are so fortunate, I recognize), and confronted it.

And crazy enough, I didn’t die.

Oh it hurt, for sure. There’s a reason I was subconsciously pushing so hard to avoid these feelings. Swimming in inadequacy was a kind of exquisite torture that I could never have prepared for, but thanks to many psychological and spiritual tools and mentors I was able to stay with the emotions, negative as I perceived them to be, and simply be. And in that, there was a freedom.

I didn’t have to reflexively jump into action and check an item off my to-do list. I didn’t have to mentally diminish myself or someone else in an effort to right-set some mental social hierarchy to make myself feel better. I didn’t have to do anything, in fact. I could just do nothing, and as Trungpa Rinpoche says, “Lean into the sharp points.” Feel what there was to feel, what I had been running from for so long, and let it pass.

By sticking with the feeling without succumbing to the intense urge to do something productive in response, I was able to develop a familiarity with it.

For me, fear of not doing enough feels like:

  • Tight chest, like when I smoked too much. I can’t get a full breath
  • Eyes feel wired, like I haven’t slept
  • My heart beat is audible, particularly when I see success in others
  • My mind spins, playing a loop of how my achievements compare to those who are more accomplished than me
  • Intense feeling that there is something wrong

I have no way of knowing if that’s the feeling for others, but now that I’ve stuck with it a number of times, really made it a point to taste the flavor of the feeling rather than running from it, I know the characteristics of that particular fear for me. I can recognize it when it comes, enabling me to actively avoid jumping into action as would be my reflex. And I know from experience that it always goes away, even if it feels like this time it’s going to last forever (it always does).


I’ve become familiar with my primal fear, that I’m existentially Not Good Enough, and will never be Good Enough. Certainly I’m not friendly with it, but I’m acquainted enough to recognize it for what it is. The fear that I’d jumped through hoops of fire to avoid, when you really boil it down, is simply a series of bodily sensations combined with a reflexive urge to achieve.

For a long time I’d unknowingly let that feeling drive so many of my actions, forcing me into suboptimal, fear-based decisions, and unproductive, repetitive patterns (and also, to be fair, into some success, albeit at the cost of relationships and consciousness).

The feeling still comes up regularly, but now when it does I’ve learned that there’s a choice. Most of the time, when I’m at my best, I simply sit with the feeling and appreciate how its intensity reminds me that I’m alive.

Then look at the situation with a clarity of mind that used to be inaccessible, and do the next right thing (HT my 3 year old).

The search vs the grind

“If I had an hour to solve a problem and my life depended on it, I would use the first 55 minutes determining the proper questions to ask, and 5 minutes thinking about solutions.”

Albert Einstein

We love being productive because productivity is a drug. Our neurochemistry gets juiced with dopamine or seratonin every time we check that box.

We do the same thing at scale — at the end of the day we measure our contribution based on the volume of boxes we checked. Sometimes as leaders we measure this based on the boxes our team checked, but even though the scope is distinct the unit of measurement is the same. We naturally place premier value on output, because our brains are wired that way.

This isn’t wrong, it’s just incomplete.

Diligently executing our plans is an important part in running our businesses, or our careers, or our lives. That steady pace of production is the engine that steadily moves us forward. We need to grind to get anywhere, and so it’s useful that nature gives us happy drugs for doing this hard work.

But we tend to level up, as individuals and businesses, in an entirely different way. We make steady progress by checking boxes, but when people or businesses take huge leaps forward it’s more often due to a change in our internal operating system (a new skill, a new direction, a new connection) which only comes when something new is introduced.

Searching for these revolutionary new elements is therefore important work, but it runs counter to our nature. The problem, as anyone who has lost their car keys will attest, is that whatever you’re searching for is always in the last place you look. So until you find what you (often didn’t know you) were looking for, this type of searching work does not give us any of the happy neurochemical feedback that we get from staying the course and producing.

We’re chemically wired to stay busy, even if we’re solving the wrong problem.

Think about how abnormal it is to read a book about your field or discipline in the workplace. Books are someone’s considered attempt to provide the most valuable information possible in the best package possible, and so are one of the highest-probability searches one can undertake. But we too often see reading as much less valuable than executing the next task.

Success, whether personally or in business, is necessarily built on a combination of producing (steady box checking against the work that we know needs doing) and searching (constant exposure to potential improvements to our internal operating system, even if no such improvements are guaranteed). Both sides of the coin are necessary if we’re to reach our potential.

Given that, it’s worth remembering that production places our brains under the influence of drugs, begetting a need for more production, and if we don’t make it a point to invest in the search we risk drastically limiting our ability to revolutionize our companies or ourselves.

How to build a sandcastle (or anything)

1990

I woke up slowly to the sun shining through the sheets, and pulled my blanket up over my face to bring back the darkness. I was settling back into my dream when I remembered. I jolted awake.

The sandcastle.

My dad and I spent all day building it, while my mom sat on the beach reading her book. My dad said the trick was to start by making the sand wet so it was strong. We filled my blue bucket with water and sloshed it over the sand, making a wet spot partway up the beach. Then we went back to the water and filled the bucket with wet sand. We packed it down tight and brought it back up to the wet spot, and when we flipped the bucket over on its head the sand that came out was shaped like a castle. But you had to lift it up so quietly. Otherwise the sand falls apart and you have to do it again.

We made four castles like this, and then my dad showed me how to make the walls connecting the castles. We smooshed sand into tall walls, and then we carved windows in them so the sand soldiers could shoot arrows at the bad guys. We had to make sure that the walls were flat on the top, too, so the people could walk across them without falling down. I did a wall all by myself, but it wasn’t as flat as the other ones.

Then we did a trick. We took wet sand in our hands from the water and ran so fast back to the castle and dribbled the sand in our fists and made spikes on the top of the castle. Every spike we did special like this. These were for protection. We made little windows in the spikes too with a stick, just like the castle in the beginning of movies. This way the townspeople could see out.

My dad never made a sandcastle with me before. It was perfect.

I threw on my clothes from the floor, dirty from last night but that’s ok, and ran downstairs. My dad was eating breakfast. He was usually gone when I woke up, but at our vacation house he didn’t have to go to work so he was there and he smiled when I came down. I told him I wanted to see the sandcastle we made, and he said he’d come with me down to the beach. We ran down the stairs and took off our shoes and ran onto the sand. My dad couldn’t keep up with me because I’m so fast.

But it was gone. Our sandcastle was gone, and the sand was wet everywhere around where it was, not just in the one spot. I cried and cried, and my dad hugged me. I hated the sandcastle. It was perfect, but it was gone.


2020

I thought of that day so long ago with my dad, when I built a sandcastle with my son at the beach in Northport last summer. We wetted the sand and used a bucket that looked almost like the one I remember to create the turrets. We crafted the walls just so, and added the spikes that were my favorite part when I was young. My son lit up when he saw how the dripping sand stalagmited into spikes on the corners of the castle. That was the best part. Well, that and when I showed him how to draw the windows. I told him we had to make it just perfect, so the townspeople could live there. He found two pinecones and put them inside the castle, and said they were the mayors. He was so proud. It was perfect.

I told him it wouldn’t last, that it would be gone by tomorrow, but even though he acted like he understood then, it still hit him hard when the tide came in and washed everything away. He said he hated it, and he wished we had never made it. He cried so hard, I almost wished we didn’t make the sandcastle. Well, maybe not, but at least I understood.

I’m so glad we made the sandcastle, but I’ve stopped caring about sandcastles long ago. I’m so glad because I got to spend time with my son, and see the gleam in his eye when we dribbled those spikes for the first time. I can still see it now.

It’s gone, but it was perfect.

Focus on the road, not the wall

Running a venture-backed startup before profitability is like flying a plane you can’t steer toward a thick, steel wall. The only option is to throttle up faster and faster, accelerating to take off with enough distance to clear the wall (reach profitability), or somehow find a way to move the wall backward before you hit it (raise follow-on financing).

There is precedent to this wacky situation, out of which has come best practice.

Professional NASCAR drivers are trained to focus solely on the road, because history has shown that if they allow themselves to look at the wall, they’re likely to hit it.

It’s so difficult when running a startup from a balance sheet to not fixate on that wall, but Jeff Gordon might tell you your life depends on it.

When to stop “crushing it”

I’ve been “crushing it” for almost as long as I’ve been running a startup.

That’s not to say that things have always been up-and-to-the-right. We’ve had more than our share of WFIO moments along the way. But to most anyone I spoke with, we have always been crushing. I made sure of it.

I have always kept the key metrics by which we actually were crushing it at the ready at all times, because you never know who you’ll talk to and you need to be on your game when opportunity knocks.

There’s tremendous value to this. I have literally been in an elevator with an investor of limitless resources, and needed to position my company in the best possible light in less than 30 seconds to pique his interest enough to take an actual meeting with me. If I didn’t have that highly packaged version of our story at the ready, I legitimately would not have closed that round of financing. I certainly don’t mean to diminish the importance of presentation, as it’s critical to startup success.

That said, it’s worth knowing when to turn it off, too. And doing so can counterintuitively be a path to success.

If you’re always “crushing it,” you risk sugarcoating real problems that need attention, and prevent the outside perspectives that may actually help solve those problems from having a clear way to engage. In “crushing it” you present the image of success, but you may unwittingly do so at the cost of real, actual success.

Startups are hard. Over time we’ve cycled through periods of legitimately crushing it, and periods where I didn’t think we would make it. That up and down ride is the nature of the game, and the secret is that EVERY startup hits highs and lows, even though most don’t talk about the lows.

That’s for good reason. Talking about the lows will never get you funded. But on the other hand, “crushing it” communicates that you don’t need any help.

And sometimes we all do.