Things are Looping Up

Life is about loops.

Sometimes it is easy to make the assumption that life is a series of discrete events and choices. We believe that life is like a stone skipping crisply across the surface of a lake. There is a singular point of contact and then we are just along for the ride until the next point of contact.

This assumption is incorrect.

Life is about loops. The iterative processes and actions that define our life, behavior, and businesses.

Things are rarely as simple as action and reaction. This may occur in science experiments that take place in a closed system. Life is more often a series of interconnected systems where the outcomes have some level of impact upon the next impact.

Think about driving. An action that seems like second nature to most of us is actually a complex loop involving multiple neural and physical systems. You are only able to drive because of the short feedback loops between these systems. Moving the steering wheel causes the car to change direction. This feedback is relatively quick and direct which allows your brain to either A) keep turning or B) stop turning.

A key lesson to be learned from driving and applied widely across our personal and professional lives is that a key to operating a system successfully is to keep feedback loops short and direct.

Shoulda, woulda, OODA

A lot of the modern thinking around loops and systems started by Air Force Colonel John Boyd. Boyd developed a concept called the OODA loop that is still widely utilized in military and business strategy today. It is a decision-making framework whereby decisions are made by constantly cycling through the loop of Observe Orient Decide Act. In aerial dogfighting between fighter jets, the fastest or most heavily armored plane is not who wins, it is the pilot who can react most quickly to changes in circumstances. Utilizing the OODA loop methodology, pilots can cycle through decision trees extremely quickly. Less focus is placed on making the correct decision as is focused on making decisions quickly, examining the results, re-orientating accordingly, and then taking action again.

Sound familiar?

OODA loops and the underlying theory that agility overcomes superior resources serve as the bedrock for modern business strategy and technological development. (For a great podcast and loops about in business, check out this episode of Invest Like The Best)

Why startups win

Agile software development and the lean startup movement are two examples of this kind of thinking. In both cases, the lengths of feedback loops are minimized and decision making is pushed as close to the customer as possible. Resources are front-loaded and experiments are run and re-run so that teams can get feedback quickly and make adjustments as necessary.

This is why startups can go toe to toe against massive incumbents and win. Usually, success isn't a case of simply throwing resources at a problem. Startups beat incumbents because they can act and react so much quicker. By the time that a large incumbent has gotten the ship turned in the right direction, the startup already has such a large headstart that it has captured the hearts and minds of the consumer.

Issues occur when feedback loops are too long. A prime example of this is diet and exercise. We all know eating healthy and exercising is good for us. So why don’t more of us do it? The answer is that the feedback loops are long with these activities. You may not see results from your effort for weeks or months. It is easy to get discouraged while the immediate gratification of Grandma’s chocolate cake is immediately available.

Now, this is a massive issue for my industry.

Why the long pace?

Venture Capital is notorious for having extremely long feedback loops. Those startups that are successful enough to have a positive outcome will often spend 5 to 10 years getting there. And this trend is only elongating as companies are staying private for longer. As such, it will take an EXTREMELY long time to figure out whether your decision to invest in one company or another was the right one. Because the feedback loops are so long, it makes it almost impossible to alter your strategy and adjust.

So how do you deal with these long feedback loops? That is the challenge. Here are some ideas I have come up with.

1) Focus on building a repeatable process

Ahh the classic Erik Berg Process suggestion. You knew it was coming. I’m a big process guy. What can I say? When feedback loops are long, the importance of having a good, repeatable process is magnified. Notice what I said. Simply having a process isn’t enough. First, it has to be a good process. Having a bad process is worse than having no process at all because it will likely either reinforce poor decisions or give you false-confidence about your decisions. Second, it has to be a repeatable process. Your perfect process will do you no good unless it is flexible enough to be applied across different opportunities. It also will do you no good if the process is so cumbersome and painful that you struggle to get other stakeholders, entrepreneurs in my case, to get through it. Having a bad process in venture opens you up for MASSIVE issues. You may find yourself with a due diligence process that is so painfully slow and cumbersome, you aren’t flexible enough to be opportunistic on good deals and, even worse, you may experience adverse selection bias as the best entrepreneurs are unwilling to put up with jumping through your hoops.

What does that good process look like in Venture? Unfortunately, there isn’t a one-size-fits-all solution. What works with one segment or geography may not work for another. But it is something that you should spend significant time and energy being thoughtful about. Don’t do things just to tick a box on your checklist, be purposeful and make sure every step in your process drives tangible value for either you or the entrepreneur (ideally both).

2) Document your decisions

With long feedback loops, it is almost impossible to remember the set of facts or thoughts around a decision months or years later. This makes documentation of the utmost importance. If you won’t know whether a decision was successful or not until years later, you need to have enough documentation to be able to come back to it and review what was going through your mind at the time and how that mapped against how things eventually would play out. Were your assumptions correct? Did you anticipate all the exogenous threats? Was your understanding of internal dynamics accurate in hindsight?

You won’t be able to ask yourself the right questions, much less answer them, unless you are documenting decisions effectively. Note that this does NOT mean that you need to write a novel recounting the most minute aspects of every decision. Remember what I said about having an efficient process? This is definitely a case where more does not equal better. How does the saying go? “It was too hard to write you a letter on one page so I wrote it on four.” As in all other aspects of communication, decision documentation should strive for clarity and conciseness. It is better to write one accurate and poignant page than it is to write twelve that are not. (This is also true in blogging and something that I am desperately trying to get better at.)

3) Audit yourself

Hey, remember when I said that it was important to document your decisions? Believe it or not, that is very much predicated on your willingness to go back and actually look back at your decisions. It is amazing how few people and firms do this. More often the self-analysis only goes as far as: “Decision right = skill. Decision wrong = bad luck”.

Have the courage to look in the mirror at all your mistakes. Go back and try to understand where your head was at the time. Use your clear and concise documentation to figure out where you went wrong and how you can react better in the future. The reasons people don’t do this are two-fold. One, people are lazy and this takes time. Sorry, you are just going to have to suck this one up if you ever want to improve. Two, people don’t like admitting they were at fault for their errors. This intellectual humility is what sets the best from the rest.

4) Measure using an intermittent proxy

If you won’t know if something is successful for a long time, try to find indicators with which to orientate yourself even before something is fully baked. Look at the exercise example I used previously. If you focus on how you look in the mirror, it will be extremely hard to stay motivated. If you instead focus on the energy you feel after a workout or the weights/reps you were able to lift, you will have a much easier time staying motivated. You will see progress all along the way instead of only once you reach your destination.

William at Frontline Ventures has an excellent article detailing how he and the Frontline team utilized the intermittent proxy measure of future financings to measure a company’s success. It isn’t a perfect measure (just ask WeWork), but it was good enough to give a directional indication of whether they were on the same track or not. Based on the data they gathered, they realized that they were missing out on deals because their process was too slow. Accordingly, they adjusted their process to be more nimble so they wouldn’t continue to fall into this pitfall.

Staying in the Loop

Life is about loops.

Observe.

Orientate.

Decide.

Act.

Move nimbly and purposefully. Make sure to pick your head up often enough to adjust your direction as necessary. Design good processes that you can repeat scalably and effectively.

Remember: David beat Goliath.

Speed wins and to be fast you need to be able to design tight feedback loops.

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The Path is a Lie

I am not a patient person.

Never have been and never will be. I think waiting is overrated. In my (occasionally) humble opinion, people who tell you to wait your turn are really just telling you to quiet down and mind your place.

We are living in an age where anyone can create anything, and yet from parents, friends, mentors, and school counselors we still hear the same age-old refrains:

“Wait your turn.”

“Get two years under your belt and then you can do something else.”

“Pay your dues.”

“This is the path for that industry. “

That’s the one that gets me the most.

The Path.

What is the path? The path is the lie that we are told. That to do X we have to do A and B first. And C. And D through W.

The path is a lie. And a lazy one at that.

There is no path to creating music. There is no path to creating art. You are the master of your own life’s work. If you want something, make it so.

The path only exists in hindsight when we look backward and all of the disparate dots line up perfectly.

When looking to the future, there is no path.

Why do we get this advice? Because it is what worked thirty years ago for the people who we look up to. It’s what worked when knowledge was scarce and companies were as loyal to their employees as their employees were to them. It’s what allowed them to slowly but surely climb the corporate ladder.

But the world has changed. We have all of the knowledge and tools in the world at our fingertips. Never in the history of mankind have individuals been empowered to create and pursue what they want in life.

And yet most of us don’t take advantage of this incredible gift. The irony is that we have more power and freedom than ever before and yet we waste it. We go to school with big dreams about changing the world and then go into exactly the industries and companies that we were hoping to change.

And at some point, we get thrown headfirst into the real world.

In the real world, there is no path. At least not unless you make an artificial one for yourself.

You want to create something? Go build it.

You want to experience something? Go make it happen.

Want to live somewhere new? Buy a plane ticket.

Want to get out of a relationship? Leave.

We live inside prisons of our own creation.

We are so afraid of what will happen if we color outside the lines. We are like dogs whose electric collars have been removed but who remain comfortable inside the world of their front lawn.

So what should we do instead?

Think big.

Don’t take no for an answer.

Stop settling for good enough.

Fake it till you make it.

Do something you find meaningful instead of just doing what you think you are supposed to.

Ask yourself tough questions and don’t be afraid of hearing the answers.

And whatever you do, don’t listen to anyone who starts telling you about the path.

What worked for them won’t work for you. And life is too short to waste your time toiling away at something that isn’t worthwhile.

In the word’s of Andry Dufresne, “Get busy living or get busy dying.”

I for one plan on living. And I am sick of feeling like I need to apologize for that choice.

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If it's not one thing, it's Structure

Do you ever feel like you are being led along a very specific path?

That the universe is telling you something or that you are being fed very specific breadcrumbs?

I think it happens to everyone. Humans have an excellent ability to see patterns in information. Even if they sometimes don’t exist. Think about shapes in clouds or constellations. We can’t help drawing lines and seeing fluffy elephants.

I feel like this has been happening to me recently. It feels like every new article I read or topic I learn about connects back to somewhere else. Whenever I learn something new, I am placing a star in the sky and eventually, I can’t help but see the pattern connecting them. One new article or podcast and suddenly 10 stars that had nothing to do with one another line up in a constellation that becomes impossible to ignore.

This phenomenon recently happened to me after reading a summary of the book The Path of Least Resistance: Learning to Become the Creative Force in Your Own Life by Robert Fritz. In it, Fritz introduces his theories about how structure defines everything from nature to personal relationships, to organizations. The overriding idea is that all things follow the path of least resistance. In nature, this concept is easy to see as water always travels downhill along the easiest path, but the concept is every bit as true in our lives as well. According to Fritz, the structures of our lives, both implicit and explicit, define a path of least resistance for our behavior. Without changing the underlying structure, we will always revert back to that behavioral path of least resistance irregardless of the amount of energy and willpower we throw against it.

It’s why diets don’t work, means are regressed towards, and people revert to behavioral patterns. Structure defines incentives. Incentives define behavior.

Reading this summary felt like the capstone in an intellectual journey. In some ways, it began 6 months ago when I read the excellent Loonshots. In it, author Safi Bahcall explains why some organizations innovate and others don’t by analyzing the underlying structure of the organization. In other ways, it feels like this is a journey I have been on for the better part of my life.

I’ve always been obsessed with incentives and the idea of structure feels like the missing piece to the puzzle.

In the words of Charlie Munger:

Show me the incentives and I will show you the outcome.

I’ve always thought through this mental framework where actions are explained by incentives and where people, in general, operate rationally based on the information they have. What was missing from this paradigm was a way to explain why people so often act against their own very explicit interests. Structures do this. We may have all the incentive in the world to exercise and eat healthy, but without the proper structures in place, we will never be able to sustain long-term lifestyle change.

I can see this so clearly in my life.

A recent example is working out. I recently wrote about how I have been trying to double down on exercising more. I have been trying to get on a good workout routine for years now and could never sustain anything. Now after two structural changes, getting up and exercising is easy. I went from not being able to get up to exercise more than once or twice a week, to doing it every (work) day. Easily. First, I changed how I was working out. Instead of focusing on becoming a better runner which I sucked at and didn’t enjoy I focused on lifting which I am good at and I do enjoy. The second thing I started doing was preparing my pre-workout drink the night before and setting it next to my alarm. I turn off my alarm and take a sip of caffeine and all the sudden falling back asleep isn’t an option. Two small structural changes to the system and suddenly the path of least resistance is getting up and exercising where it used to be crawling back into bed and going back to sleep.

Another example that has had a big impact on my life is networking. I used to hate it. I thought of it as brown-nosing and avoided it at all costs. It didn’t help that I struggle with social anxiety and just flat out am uncomfortable in many of the environments where “networking” is supposed to occur. Now networking is THE favorite part of my job. Why the sudden shift? Structural change. A former colleague who excelled at networking told me that he doesn’t think of networking as “networking” but simply as trying to make new friends and learn their stories. Suddenly the lens through which I looked at networking fundamentally shifted. No longer was networking some transactional way to climb the corporate ladder, but an opportunity to foster and cultivate genuine, value-add relationships.

That’s the beauty of structure and my biggest takeaway from The Path of Least Resistance. Structure is a powerful force that guides how we think and act.

But at the end of the day, we are the ones who get to shape the sand that the water will flow through.

We are the artists of our lives. Once we are aware of them (not a trivial matter) we can architect structures of our own choosing to pull us towards the actions and behavior we want to practice.

You know me. I’m a big choice guy. Part of everything in life being a choice is that sometimes (often) our choices manifest themselves in the ability to choose how to design structures in our life to get the outcomes we want. Because if your incentive structures are messed up, no amount of hard work or endurance will allow you to get the outcome you want (at least not sustainably).

Next time you are kicking yourself for doing something you know you shouldn’t or going back to bed when you know you should be hitting the gym, think about the structure in your life that is pulling you towards where you don’t want to go.

Believe me, it is easier to change the structure that is defining your behavior than to fight your way up the waterfall of going against your incentive structures.

Personal life. Business. School. Sports.

It’s all just structure.

And the great thing about structures is that they can be changed.

The sad thing about structures is that people almost never choose to do so.

So the question for you and me is, once we are aware of our structures, do we have the courage to change them?

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Tech's Manifest Destiny

In the 19th century, American pioneers expanded across the reaches of the American continent. The driving force behind this unstoppable conquest was the belief in America’s Manifest Destiny. Today, as we witness a new technological Manifest Destiny, we must be careful not to repeat the sins of the past.

The Call of Destiny

Manifest Destiny was the belief that America’s unique virtue not only allowed, but obligated, its citizens to expand and tame the American continent. It was followed with an almost zealous fervor by pioneers and settlers pushing the bounds of the United States’ frontier ever further. Manifest Destiny, perhaps more than any other cultural belief, has created the country we know today. It brought immeasurable wealth, resources, and power to what eventually would become the world’s preeminent superpower. This treasure trove of riches was not won without sacrifice. The secondary effects of Manifest Destiny were the displacement of native peoples, the extinction or endangerment of many natural species, and the fundamental altering of America’s environmental landscape. It’s hard to argue that the benefits of Manifest Destiny, at least from America’s perspective, outweighed the cost, but we are fooling ourselves if we ignore that there was a cost. I will leave the debate of whether Manifest Destiny on a whole was positive or negative to history’s scholars, but what is undeniable is that the phenomenon was more complex and nuanced in its ramifications than anyone considered at the time. Manifest Destiny’s effects, good and ill, have reverberated through time and are still felt today. The modern-day Manifest Destiny will have an equally far reach, but will it be for our benefit or our detriment?

Technology’s Manifest Destiny

The modern equivalent of America’s Manifest Destiny is the seemingly unassailable march forward of technology and innovation. Innovation grows at an exponential scale as new discoveries and technologies open up the door for additional breakthroughs. It has become a cliche critique, but I do think there is truth in the idea that we spend so much time asking if something can be done, that we rarely take the time to ask whether it should be done. As we reach new technological frontiers in mobility, automation, and artificial intelligence, we need to start grappling with the very real questions of not only what should be done, but how should it be done.

Don’t mistake me. I am not out to get technology or break up big tech or regulate innovation away. If anything I am the opposite. I genuinely believe that technology and innovation is the driving force behind a tide that raises all boats. I believe that we live in the single greatest period of time in human history and that tomorrow will be better than yesterday.

I write this post not because I distrust technology, but because I believe in it so strongly. Just as the pioneers of 200 years ago did, I have at times found myself a zealot blindly preaching the benefits of the forward progress of technology with little heed towards its potential side effects. This entrenched bias and lack of nuanced view scares me when I see it in myself and it scares me when I see it at large in our community. I love disruption as much as the next guy, but we shouldn’t worship at its altar. Disruption hasn’t always had the positive connotations that it enjoys today (just ask my grade school teachers…). We mustn’t give in to the temptation to simply assume that what we do is “good” and what others do is “bad”. We can’t kid ourselves that just because technology has created unprecedented prosperity that, left to its own devices, it is destined to continue to do so.

We are better than that.

Innovation is a force and just like any other, it is indifferent in its application. The fire does not hate the wood it burns.

Responsibility ultimately lies with those who wield it.

Us.

The lack of acknowledging that responsibility is one of the things that scares me most in the world of technology today. There seem to be two camps. On one hand, there are people who believe that tech can do no wrong. That it is not just ultimately a force for good, but unequivocally so. On the other hand, there are those who believe that we are powerless to change the course of innovation for better or worse. That innovation is an unstoppable tide that we must be content to merely keep our heads above water as we are swept away.

I reject both of those arguments.

We should not fall into the same trap that the pioneers of yore did by simply believing that because we can do something that it is good. I will be the first to tell you that I believe that technological progress is on its net, overwhelmingly positive, but to outright ignore its downfalls is a path to disaster.

We are not bystanders who lack sovereignty over our circumstances either. We are creators that can exert our will upon our creation. To argue otherwise is an attempt to dissociate responsibility.

Now look, I don’t have the answers.

But I do know that we need to continue the discourse. We need to have the tough conversations about not just what can be done, but what should be done.

We as a community cannot hide behind platitudes of technology’s greatness. We need to be honest with ourselves about innovation’s heights and depths. About its greatness and its shortcomings. Its light and its darkness.

Because if we don’t.

Who will?

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Run like no one is watching (because no one is)

My wife and I have been watching a lot of Friends recently. And when I say “a lot”, I mean A LOT. We were too young to really appreciate the show when it was on tv and we have really been enjoying watching it from the very beginning.

A recent episode left me with something that I have found myself continuing to think back on in recent weeks. At one point after they have recently moved in together, Rachel and Phoebe decide to go for a run together. In short order, Rachel is horrified by Phoebe’s “emphatic” running style. More than that, she is mortified by what other people would think of her running with Phoebe.

Believe it or not, we should all strive to be a bit more like Phoebe

Embarrassed by Phoebe, Rachel avoids her during subsequent runs. Eventually, she confronts Phoebe on her unusual running style. Phoebe says something along the lines of “remember how it felt like to run when you were a kid. Running was fun and you felt like you were going so incredibly fast and the wind would just rush by you. I still run that way.” By the end of the episode, Rachel has adopted Phoebe’s “technique” and is having more fun than ever before.

Too few of us run like Phoebe.

We are so scared about what the rest of the world thinks of us, we aren’t true to ourselves. This is even true (maybe especially true) when our only witnesses are strangers.

It is not an accident that we are status-obsessed creatures that spend an inordinate amount of time focused on what others think of us. Not so long ago in most of our genetic histories, our ancestors were living in small villages with little to no mobility or communication with other communities. In this setting, an obsession with not doing anything to look bad makes a lot of sense.

Do or say too many stupid things and you may just ruin your chances with the few suitable mates in your community. This was a big issue when there weren’t a lot of eligible bachelors/bachelorettes in your community. Make an off-color joke about the blacksmith and Gertrude Smith could just write you off as a compelling candidate for a mate altogether. Congratulations. Your chances at procreating just dropped by 13%.

You can see how this becomes a problem. (With the number of times I regularly put my foot in my mouth I can almost guarantee I would not have continued the genetic line had I been born a few hundred years earlier.)

Unfortunately, our lizard brains are still stuck in this scarcity mindset despite having overwhelming abundance. The internet. Telephones. Cars. Tinder. You literally could offend 99.99% of people you come into contact with and you would still have a decent shot in this day and age! And yet we act as if saying or doing something stupid in front of people we will literally never see again will somehow be the end of us.

But I want to let you in on a little secret.

The only psychological trait that overpowers our incredible fear of what others think of us…

…is our even more impressive self-absorption.

That’s right.

You shouldn’t care about what other people think of you, because they AREN’T thinking about you. They are all too focused on their own life to expend calories thinking about what you just said or the fact that your boots and your belt clash. And you know what, even if they are looking at you, who cares? Chances are your paths will never cross again. Go ahead, live your life.

This may seem like a pessimistic perspective, but once you accept it, you will find it incredibly freeing. You’ll be able to start living how you would if you weren’t afraid what other people thought. You’d be able to start playing Grand Theft Life.

If I can be honest with you, this is an area where I definitely do not always practice what I preach. I definitely worry sometimes about what others think. This is one of the many (many, many, many, many) opportunities I have for self-improvement. But it’s an area I have definitely improved on. It is something that has been key to overcoming self-doubt and anxiety. And if I can do it, you can do it too.

One of the biggest areas in our modern world where I have seen this obsession with what other people think trip us up is social media. It may seem like everyone and their grandmother have 6 Twitter accounts, 2 Snapchats, 3 Instagrams, and a LinkedIn for their dog (not even the dog still has an active Facebook account though), but I actually think we could use some more people sharing their views and perspectives on the interwebs. Some of the smartest, most interesting people I know refuse to share on social media.

They are worried about what people will think. They are worried that other people are watching.

Here’s what I have learned about sharing content online.

Say something smart and people will find it, share it, and potentially open doors for you.

Say something stupid, and no one will do anything. People won’t spare it a second thought. Now there are limits. You can’t say anything toooo obscene.

But for the most part, sharing content is the ultimate asymmetric bet. Big upside. Minimal downside.

If you are afraid of putting yourself out there, don’t be. People are too busy focusing on own their own feet to notice your missteps. But they will notice your greatness.

My advice:

Run like no one is watching.

Dance like no one is watching.

Tweet like no one is following.

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A Labor of Love

My Labor Day view

Happy Labor Day!

Hope you are enjoying some R&R this holiday weekend. My wife and I are back in Colorado spending time at my family's cabin up in the mountains.

In the spirit of the holiday, I have been thinking about labor. Work. Grinding. I think far too often there is this idea in our culture that work should feel like work. By golly, they don't call it that for nothing. I partially agree with the sentiment in so far as to appreciate the fact that not everything in life is necessarily supposed to be fun or easy.

But if you are working on something that makes you miserable, you should probably reevaluate why you are doing that. In fact, if you are toiling away at something and you can't find any joy or value in it, you should do something else.

In the words of Morgen Housel “something stupid you can stick with will probably out perform something smart that you'll burn out on”

Pursuing your passion is an oft-cited (and oft-derided) cliche. I think the advice is good, but not for the reason people think. It's less about the joy you get from something itself and more from the endurance that joy gives you. Something that feels like play to you and work to everyone else is naturally something you'll be willing to work at when others aren't.

By that same token, one should focus on leveraging their strengths instead of trying to fix their weaknesses.

This has been something I've been trying to do more of. Recently this pursuit has taken the shape of my trying to get in shape. It's something that I've always struggled with and never quite figured out. I've never been in horrible shape but I've also never been in great shape. It's something I'm trying to get better at both for the quantity and quality of life I want to lead. For so long exercising has felt like banging my head against a wall, but recently I've started getting some positive momentum.

The first step when trying to double down on your strengths is developing an awareness of what your strengths and weaknesses are. This sounds easier than it is and requires some not-always-pleasant self honesty. It also can require you shutting out voices around you that push you in one direction or another. When it came to my exercise, cardio has not, nor likely ever will be my strength. For those that don't know me personally, I am a descendant of thousands of generations of short and stocky northern Europeans. My body was built for trudging through the snow not galloping through the meadows. As such, cardio has always been miserable to me. No matter how hard or consistently I try, I can never be better than a mediocre runner and I never enjoy it more than a 5 or 6 out of 10. For the past couple of years, I have been trying to become a runner. And I have struggled mightily to establish any sort of momentum. It always felt like pushing a stone uphill to me.

As weak as I am at running, I have always been quick to build up muscle and strength. A short and stocky frame will do that for you. It's always come easy for me and because of that, I've always enjoyed it. I feel like I am making progress. That I have momentum.

But I barely have been lifting over the past couple of years. When I talked to friends and family that were in shape they all were runners. So I thought I had to be a runner too. But what works for some won't necessarily work for you. What felt like play to others felt like work to me and because of that, I struggled to stick with it.

The past couple of weeks I have gotten a new gym membership and really doubled down on lifting every day before work. It's early days and I have a long way to go to be where I want to be, but already it feels like a world of difference. Instead of pushing a rock uphill, if feels like I am pushing it downhill. What feels like work to others is all of the sudden play to me. And because of that, I can stick with it when others can't.

In our culture we are too quick to praise the grind. Maybe we should ask ourselves, “why does this feel like such a grind in the first place?”

If you can figure out something that comes naturally too you and others struggle with, you will be willing to work harder than anyone else and your advantage will compound. It's not always easy. You might have to ignore what friends or pop culture are telling you and the ideals they expect you to aspire to.

But you will know if you're on the right track because those around you will be dropping out just as you're getting warmed up.

Enjoy the long weekend. Enjoy your family. And enjoy your labor. If you don't you might want to consider doing something you would enjoy.

Life's too short for anything else.

Lets get ethical, ethical

Living a life of uncompromising integrity is as difficult as it is important. As with many important things in life, it is a goal that can never truly be reached. It’s the act of reaching for it that matters.

One of the topics that I have written about most on this blog is the power of little things. Little things done over and over and over again turn into big things. And those big things have a significant impact on your life.

I believe morality is often the same way. In the words of Albus Dumbledore ”We must all face the choice between what is right and what is easy.” Rarely are we met with ultimatums between right and wrong. Much more often it is this simple choice between doing what is right and doing what is easy. Between taking the high road and the low road.

The sinister part of these decisions is that there is often no immediate negative feedback to choosing the easy path. There is no hot stove to teach you not to place your hand on top of it. In fact, that is often exactly why the wrong choice often appears to be the easy one. It is less a question of avoiding some sort of pain as it is a question of delaying it. Wrong choices compound. They come back to bite us at the worst possible times.

The right choices are usually the opposite. They generally involve short term pain. Telling your boss when you messed up. Apologizing to your spouse when you still don’t think you did anything wrong.

But they tend to compound in the long run. They build trust. They build your reputation. They help you sleep at night.

Your character is what you do when no one is looking. I think we all say we want to be high character people, but how many of us actually take tangible steps to do so? I’d wager not many.

I am trying something. I think it has been helping me and I think it may help you too.

It’s called keeping score.

I got this practice from Chop Wood, Carry Water. A book that has had an immense impact on my life and the way I view the world.

What you do is that you make a list of the 5 values that you most respect in other people. That is your new scoreboard. Forget about money or status or fake internet points. Measure yourself against the things you most value and respect in people.

Here’s my scoreboard.

• Uncompromisingly Ethical

• Brave and stands up for what is right

• Hard-working and persistent

• Treats others with respect and compassion no matter who they are

• Maintains a Learner’s mindset (Focused on the process, views the world as an interconnected system, sees every challenge as an opportunity to learn and grow)

• Builds bridges between others. Seeks to connect the world. Always adds more value to any conversation than he takes away

Clearly, I have built upon some of these. They change and evolve over time. Just as I, and what I value, does.

This is how I determine whether I had a good day or not. No matter what else is happening in life, if I am living according to these principles, then I am at least heading in the right direction. And I think it has made a tangible impact on my behavior. It’s like building muscle memory. Grade yourself down for using someone else’s salad dressing in the work fridge or park in a “For customer’s only” space a couple of times and all of the sudden you start thinking twice about doing something you would’ve done without thinking before.

And it is that pause where you think twice that really allows you to make the changes you want in your life.

I made a tool to help me do this, and I think it can help you do.

In a previous post, I shared the personal CRM that I had built in Notion to help me hone my superpower of building and maintaining genuine relationships. I got some great feedback from people who were able to leverage that tool so I decided to add to it and start building a dashboard for others to utilize.

Here is the public dashboard that I have added Personal CRM and Scoreboard templates to. Feel free to duplicate in your own workspace and customize to your liking.

Hopefully this is as helpful to you as it has been for me. Big changes are made up of small changes. And small changes take time. I’ve found holding yourself accountable to even the smallest thing is the best way to enact long-term change.

There is no silver bullet. You won’t magically wake up one day being the person you’ve always wanted to be.

But you can get a little bit closer to being that person.

Every.

Single.

Day.

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Avalon and the Future of Work

This post is inspired by the very interesting twitter thread started by Jeff Morris Jr. He shared the 10 topics that he was interested in at the moment. I responded with my own list and thought it would be fun to go into a bit more detail on each of my topics. Unfortunately, I only made it through the first one by the time I hit a length that is appropriate for a weekly blog post. Especially one started late because your wife invited friends over on a Sunday afternoon. Sunday afternoons are generally reserved for rest, relaxation, and my usual post-church uniform of a Polo shirt and gym shorts. Luckily, being social was great fun and the uniform was a big hit with all. But I digress. Without further ado, the number one topic that I am interested in at the moment (and the one which has been monopolizing the lion’s share of my thoughts and attention recently)

The Future of Work

If I can only write on one topic, it makes sense that it is this one. I am fascinated by how we work and what our work will look like in the future and many of the other topics on this list are reflected as aspects of this one. Outside of your health and your spouse, your work has the greatest impact on how much (or how little) you enjoy your life. If you peel back most of the socio-political problems our society is grappling with today, I would wager that you would find work (or the lack thereof) at or near the center of almost all of them. Nearly every country in the western world has experienced resurgences of nationalist political sentiments in recent years and I would argue that the root cause of this growing political movement is the changing landscape of work. Work today is unrecognizable to what it was even a half-century ago and the rate of change is only accelerating. Workers are no longer staying in one job and slowly working their way up the corporate ladder. Whereas before, a blue-collar worker could expect to support their family, own a house, and send their kids to college in any city in America. Now, you have some cities like San Francisco where someone making $100,000 a year is near the poverty line.

The future of work is the thing that takes up more of my intellectual brainpower than any other. My goal in life is to be a company builder. It's why I got into venture capital and it is why I will be doing whatever it is I do next. I firmly believe that the highest good that you can do for anyone is to provide them with a job where they can find fulfillment and support their family. Teach a man to fish instead of giving him a fish. This belief is the guiding principle behind all that I do.

But what happens when the robots start catching fish faster and better than people can? The future of work is uncertain. No, AI is not coming for your job tomorrow (anyone who tells you that current state AI is anything other than supped-up linear regression is lying), but we are moving in that direction. Slowly, but surely, advances in artificial intelligence and automation will render more and more jobs obsolete. I believe, as with all other technical changes in human history, that this will unlock a myriad of other, better jobs for human beings that we can’t even imagine today.

But what will those jobs look like? That is the question that I have been spending more and more of my time thinking about. You should always be skeptical of anyone claiming to know what the future looks like. But if I had to guess…

I would guess that the future looks a lot like Avalon.

Avalon is a legendary island in the Arthurian legend. It is where Excalibur was forged and it is the home of Morgan le Fay. Avalon is a land of abundance.

…it produces all things of itself; the fields there have no need of the ploughs of the farmers and all cultivation is lacking except what nature provides. Of its own accord it produces grain and grapes, and apple trees grow in its woods from the close-clipped grass. The ground of its own accord produces everything instead of merely grass, and people live there a hundred years or more.

I believe that the future will bear a striking resemblance to this mystical island. As manual labor and simplistic tasks are automated away what will we do with our newfound abundance?

My guess is that work will look and feel much more similar to the video games of today than it would the work of today. Remote tools and infrastructure will allow anyone to “work” from anywhere. Abstractions enabled by virtual reality, decentralization, gamification, incentive structures, and artificial intelligence will make work more fun and gratifying. Creativity will become the currency of the day as data analysis becomes more and more commoditized. I see futuristic artisans plying their trades and selling digital goods in online markets as world-renowned musicians perform in front of sold-out crowds seated in internet amphitheaters. Status will be definable, measurable, and meritocratic. Communities will be both hype-niche and global in scale. The future won’t be a utopia, but I do believe that it will be a time of unprecedented access. You will be defined by what you produce and create, not by your demographic profile. Anyone, from anywhere, will be able to build their own “job” and support their family doing things they find intrinsically fulfilling, regardless of what other people believe a “real job” looks like.

We’ve got a long way until we are anywhere near this future. I truly believe the potential is there to design the world we always wanted. The transition won’t be painless, but the payoffs will be worth it.

Avalon is coming.

And I think it may be coming sooner than many of you think.

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What it means to end

How you finish matters. A lot.

You can destroy years of goodwill in a matter of seconds if you are careless about how you leave a job or an engagement. I was given a stark reminder of this recently through Arsenal’s recent outgoing transfers.

Two transfers in particular beautifully illustrate the importance of finishing the race well.

Our long-time captain and a key player of 9 years, Laurent Koscielny, just completed a transfer to Bordeaux in France’s Ligue 1. He was an invaluable member of the squad and an absolute key to all of the success we have had during his time here.

Carl Jenkinson, a perennial back-up who has played few games for Arsenal and spent recent seasons either injured, on loan, or riding the bench, just completed a transfer to Nottingham Forrest in the English Second Division.

On face value, one would assume that Koscielny would be thanked for his long years of exemplary service and that Jenko’s time at Arsenal would end with the lack of fanfare befitting a player who never was quite good enough to make an impact.

This assumption could not be further from the truth and it is all down to the way they ended their time.

Carl ended his time at Arsenal with this. Koscielny ended his time with this. And this. And this.

For 99% of his time at Arsenal, Koscielny was beloved. The way he left will, unfortunately, have a disproportionate effect on how he is remembered.

Jenkinson never really made a meaningful impact on the team. But he will be remembered as a humble, team player who gave everything his all and always did right by the club and his teammates.

Impact on the team aside, I think these two transfers do a great job of emphasizing the importance of finishing well.

How you finish matters. A lot.

Let it be Fear

The world recently got an example of the importance of finishing well that you may be more familiar with.

The final season of Game of Thrones was decried as a monumental failure almost universally by fans. Just look at the average episode ratings from season to season.

Look. You will never be able to please everyone. The show was always going to struggle to live up to the massive hype that surrounded it. But I struggle to think of another example of a show that has had so much excitement and hype around it that fell on its face so spectacularly.

I think if people are being honest, the vast majority of their criticism is centered around how things were executed instead of the bullet points of what actually transpired. Danny going crazy and Bran winning the throne could have been done in a way that felt genuine and impactful (the butchering of Jaime’s storyline however was completely unforgivable). Instead, this season was rushed and the decision to abbreviate it only exacerbated what would have been a monumental task no matter what. This led to a cascade of failures and viewers couldn’t help but feel the whiplash.

Finishing is important. How you finish is what will be remembered. Will Game of Thrones be remembered for being one of the most impactful shows of the last two decades. Sure. But more than anything its memory will be colored by its lackluster ending.

Finishing has always been a strength of mine. Unfortunately, that strength has been developed out of absolute and self-inflicted necessity. I have a nasty habit of starting myself out in a hole and being forced to agonizingly claw my way out. In college and high school, my final semester was my strongest academically. When my friends were chilling out and kicking back, I was hitting the books and taking an inflated course load. I had to do this because my first semesters were my weakest. I pretty much trended directly up every single semester. I made it work, but it definitely was learning the hard way.

It’s a weakness of mine that I am constantly working on.

My strategy is to start with the end in mind. Don’t start a new project of freshman year thinking you have all the time in the world.

Time moves quickly.

Visualize the end and work backward to figure out what you need to do at each stage along the way to reach your goals.

Because believe me, it is a lot easier to start well and maintain your momentum, then it is to begin in a hole and be forced to finish in a frenzy.

And whatever you do.

Don’t ever pull a Game of Thrones.

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Alt Valg

I am not a negative person. If anything I fall more on the side of naively optimistic at times. But even I sometimes can find myself caught in the spiral of negativity.

I have found myself inhabiting a relatively negative mind-space recently. I was letting things outside of my control that had little to no effect on my day to day life get under my skin. As with most negative thoughts, this turned into somewhat of a self-fulfilling prophecy as well as a snowball effect. The more negative I was, the more I would notice the negative side of things which caused me to feel even more negative.

And the flywheel turns.

Luckily, I was able to recognize what was going on. I spend a good amount of time and energy on self-analysis/self-awareness and it was relatively obvious that I wasn’t my usual happy-go-lucky self when it came to certain aspects of my life. So I decided to do something about it.

I was feeling negative. So I chose to stop.

Everything Choice

That’s right. I chose to stop being negative. I chose to look at circumstances and events in a more positive light.

I have written about it before, but one of my fundamental core beliefs is that people have significantly more choice in their life than they so often give themselves credit for. This belief has its beginnings in how I was raised. If my family had a motto it would be “Alt Valg” Norwegian for “Everything Choice”. I was raised to believe that everything in life is a choice. That we may not always have control over what life throws at us, but we do always have control over how we react. I love this list of 10 things that require zero talent.

The power to choose is a marvelous thing. It gives us agency and allows us to chart a course through life instead of being at its every whim.

But it is also a scary thing. Because when you have the power to make choices in your life, the buck stops with you.

Our life is the sum of our choices. It is affected by outside circumstances, sure. But over the course of your life, your choices about how you respond to circumstances will have a much greater bearing on your life than the circumstances themselves in all but the most extreme cases. If you aren’t happy with your life, change it. This comic has a somewhat extreme, un-nuanced view of things, but I do believe that it contains a nugget of truth. We have the life we choose.

There is a second meaning to Alt Valg. Not only is everything a choice. But the ability to choose is everything.

The agency to choose your actions and reactions in life is incredibly powerful.

Relish it. And don’t let anyone try to tell you that you can’t or don’t have that power.

Adopting a Builder’s Mindset

One of the most important choices I try to make every day is the choice to adopt a Builder’s Mindset. Doing so was exactly the mindset shift that I needed to escape my very own spiral of negativity.

Adopting a Builder’s Mindset means looking at everything as an opportunity to learn and grow. It doesn’t mean that you are blind to frustrations, but it does mean you look for silver linings and try to figure out how you can make the best of any situation.

It is a positive way of looking at the world and seeing everything it could aspire to become, instead of what it is today. A builder does not waste time complaining and wishing for more resources, they make do with the resources that they have. They roll their sleeves up and make the most out of what they’ve got.

This perspective is heavily influenced by the book Chop Wood, Carry Water by Joshua Medcalf. I have brought this book up before, and likely will continue to do so, because it is the book that has had the single greatest impact on my life and my perspective. At 100 pages long, I can’t recommend it highly enough.

At one point in the book, the main character’s teacher tells the story of an architect. The architect is world-renowned for the beautiful homes that he builds and after a long and storied career is finally ready to retire. When he makes the announcement, his boss asks him to design one more home. Frustrated by the change of plan, he does not put the care and effort he was legendary for into the home and the final product is far below his usually high standards. Once the house is complete he goes to his boss and tells him he is done. The boss then hands him the keys to the house he had just finished.

All this time, the architect was building his own house. If he had known, he would have put just as much, if not more, effort, care, and attention into it as he usually did. Instead, he was left with a home that would be a constant source of regret. The message of the story is that each of us is building our own home through the choices that we make every single day.

I love this metaphor. But I suggest a minor tweak to it.

Instead of building our own house, I think we are building our own ships that sail through the oceans of life.

There will be storms. To a degree, we will always be at the mercy of mother nature.

But we can try to build the most resilient little boats that we can. We can learn from mistakes or tragedies and we can try to use those lessons to make our boat just a little bit stronger every time.

The great thing about thinking of our life as building our own boat is that it is not something that simply surrounds us. It is an experience in and of itself.

You are the captain of your life and you have the power of choice to chart your course through the oceans of life however you would like. With a little bit of care and attention, I think that you can build something that can handle whatever life can throw at you.

And I hope that you learn to catch the wind just right and that it is as wonderful of a ride as it has been for me.

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Entrepreneur's Table

For something that captures so many headlines and national attention, there sure isn’t a ton of entertainment revolving around startups or entrepreneurship. For someone as obsessed with the topic as I am, you have to get a bit creative.

I’ve found my favorite content about entrepreneurship in an unexpected place.

Cooking.

Specifically shows like Chef’s Table that do a deep dive into a chef’s history and the journey that brought them to build the world-class restaurants they preside over today. I believe there is a lot that we can learn about entrepreneurship from cooking and from chefs that are at the top of their own game of creating something new.

Entrepreneur de Cuisine

I love the model for entrepreneurship that a kitchen provides.

In the kitchen, the head chef is the chief facilitator. He sets the tone. He designs the menu. He may even put the finishing touches on certain dishes, but if you peek into the top kitchens in the world, you will find that the chef spends little time doing much of the actual cooking itself. It simply isn’t possible in any restaurant with more than a few tables. Instead, there is a horde of more junior chefs and assistants that take care of all necessary aspects of creating a great dish.

The chef will orchestrate the incredibly complex process of coordinating multiple dishes so that everything comes out at exactly the same time. His role is vital, but it is not sufficient for success. Even the best chef in the world will fail if he doesn’t have a team that can execute and works well together.

A founder is not so different. Even with all the talent in the world and an amazing idea, entrepreneurship at any sort of meaningful scale is a team sport. If a leader doesn’t create an environment where their team can be successful, their venture will be as doomed as the most dysfunctional kitchen. My wife and I recently watched the movie Burnt, starring Bradley Cooper as a troubled chef working his way towards the redemption of his third Michelin star. Without spoiling too much, the main character only begins to attain success when he learns to trust the other chefs on his team and stops trying to do everything himself.

Founders take note. Your success will depend every bit as much on your ability to manage, lead, and create an environment where the best and brightest can flourish as it will on your talent, grit, or world-changing ideas.

If changing the world was easy, everyone would do it

Something that becomes abundantly clear for anyone who spends much time learning about the culinary arts is just how brutally difficult it is to build a restaurant that truly makes a significant impact. Chefs train their entire lives for a shot and every single successful chef will have their fair share of scars and near-death experiences.

The path to success is just so brutally difficult.

The hardest part of all?

You can never rest on your laurels. The second that you stop innovating, creating, and moving your craft forward, the world will pass you by. The thing I am most consistently amazed by while learning about the world’s greatest chefs is just how relentless their drive and passion is. They never give up and they never stop pushing the envelope forward. If they did, they would no longer be great. They are only able to do this by creating from a place of genuine Instinctual Originality.

These observations ring every bit as true in kitchens as they do in the hip co-working spaces or innovation centers that startups call home. Entrepreneurship isn’t easy. If it was, everyone would do it. It is a daily knife fight where if you let your guard down for one second, someone younger, faster, and hungrier will come along to replace you.

Companies need to constantly reinvent the wheel to stay relevant. It takes all the running you can do, just to keep in the same place.

Sears. Polaroid. Xerox. Blackberry. Nokia.

Each at some point was absolutely on top of the world.

And then they stopped moving their craft forward.

And the world passed them by.

Entrepreneurship for all

The last thing I love about examining entrepreneurship through the lens of cooking is that it expands the definition of what entrepreneurship could look like. In the startup tech world, I believe we too often paint entrepreneurship into this little box that we like to call “Venture Fundable”. Look, I will be the first to tell you that venture capital is not for everyone. To conflate a company’s funding mechanism with its identity is dangerous at worst and short-sighted at best. Just because the venture model is not right for someone or their business does not make them any less of an entrepreneur!

In a recent post, I called startups Churches of Entrepreneurship and claimed that the only real requirement for a company to be a startup is that the Spirit of Entrepreneurship resides within it.

Restaurants are a great example of the truth in that. At the highest level, a chef uses their restaurant to create things the world has never seen before. They utilize familiar ingredients and techniques bring something into being that is completely new.

If that isn’t entrepreneurship, I don’t know what is.

Acknowledging the entrepreneurship inherent in world-class cooking opens your eyes to see the myriad of other businesses and entrepreneurs that capture this same spirit. Just because a company doesn’t look like a startup doesn’t mean that it is any less entrepreneurial. Viewed through this lens I believe that the question must be asked of whether we are doing enough as investors. Is our current conception about how to build businesses broad enough? Maybe there are gaps out there? I have found myself increasingly fascinated by the accelerating trend of permanent capital and how it might be applied to the world of tech startups. If fund structures are a prime source for incentive misalignment, what happens when you get rid of them?

Anyways, these are questions for another day.

Founders, learn the lessons that chefs can teach.

Build a team that you can trust to get the job done.

Innovate by creating from a place of Instinctual Originality.

Acknowledge that there is more to entrepreneurship than twenty-somethings in thick-rimmed glasses and hoodies drinking nitro cold brew and discussing the finer points of C++.

And most of all…

Keep on cooking.

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Reunited and it feels so good

For the first time in Arsenal’s 133 year history the club is having their preseason tour in the US. So that’s where I am! My wife and I are meeting up with the rest of my family in Charlotte, NC to watch the Gunners take on Fiorintina before flying up to DC to watch Arsenal play Real Madrid.

I love sports. And I love Arsenal most of all.

Two months ago I was absolutely miserable as the team’s, at one point promising, campaign sputtered it’s way to a disappointing close. Think less train wreck and more getting one of those sad purple participation ribbons in summer swim league.

And yet here we are. The pre-season is upon us and I could not be more excited. I have gotten myself the brand new home kit (GORGEOUS) and am brimming with potentially misplaced optimism.

That’s what I love about sports. No matter what happened last year, hope springs anew this season. Sport is the one place where we can put aside rationality. It’s a relatively harmless outlet for tribalism and bias (FOYS). There is something escapist about that.

But I also think there is something poetic in it. Sport is something that brings us together. It’s something where we get up again no matter how hard we got knocked down last year. For me sports is the ultimate memory generation machine. The reason I love Arsenal so much is because whenever I watch I’m connected to the times my dad and I would wake up at 5 in the morning to watch Fabregas and van Persie play.

What actually happens is far less important than who you share it with. And I think there is a lot to be learned from that.

Journey before destination. Come On You Gunners.

Until next week.

Churches of Entrepreneurship

One of the most thought provoking books I have ever read is Zen and the Art of Motorcycle Maintenance by Robert M. Pirsig. Even many months after completing it I still find myself pondering several of the ideas explored.

One of the concepts I keep coming back to is the idea of the Church of Reason and how it relates to startups.

The Church of Reason

To explore the concept of the Church of Reason first we must discuss what exactly a church is. At its face, this seems an obvious question to answer. A church is a building in which people worship, predominately in the Christian faith. But what if the building is no longer used for this specific purpose, is the church still a church?

Pirsig gives the example of a roadside sports bar located in an old church. My wife and I for our last anniversary visited a vineyard located in an old church. Whatever example you use, the question remains, are either of those buildings really still churches?

Pirsig contends, and I agree, that the answer is no. The object of a church is defined by its purpose. If a church is not being used for worship, it is just a building. We may continue refer to the building as a church because of its familiar architecture or because that is how it has been known historically, but it no longer is a church. Not really. There is a deeper meaning to something being called a church. There is a required ‘spirit’ of the physical object. As that spirit leaves, the purpose and very essence of that object leaves with it. It becomes something else entirely. A simple building. A husk.

Pirsig draws a parallel from this line of reasoning to modern universities which he dubs “Churches of Reason.” Similar to religious churches, Pirsig argues that these Churches of Reason are intrinsically defined by their use or purpose. In the case of universities that purpose, that spirit, is to pursue truth through learning. To expand the boundaries of knowledge itself.

Just as with religious churches, these Churches of Reason become simple buildings as soon as the Spirit of the University leaves. As soon as the pursuit of truth and expansion of knowledge stop becoming the purpose for the endeavor, the buildings become nothing more than a mausoleum to their former holy endeavor. Husks.

Pirsig observed this loss of the Spirit of the University in the 60’s and 70’s when he was a professor himself writing Zen and the Art of Motorcycle Maintenance, his part auto-biography part philosophical treatise magnum opus. It saddens me to admit that this trend of the departure of the Spirit of the University not only continued, but has accelerated in the modern day.

But that is a discussion for another time. Next we will turn our attention to a different type of church.

Churches of Entrepreneurship.

The Church of Entrepreneurship

Startups are Churches of Entrepreneurship. They are the altars at which we worship the gods of technology and innovation while hoping that our sacrifices of blood, sweat, and tears change the world.

Just like other type of churches, the object is defined by its purpose. A fundamental part of any startup’s identity is the Spirit of Entrepreneurship that resides within it. The Spirit of Entrepreneurship is the driving passion to change the world through the creation of something new.

Really, the word “startup” is just a name for young companies in which the Spirit of Entrepreneurship resides. They are vehicles for the Spirit of Entrepreneurship to hopefully live and thrive. Just like with churches or universities, if you take the spirit out of the building, it is just a pile of bricks.

Startups are no different. Just because a company is young or small or technology-focused does not mean it is necessarily a startup. Without the driving passion to change the world through the creation of something new, they are just small, risky businesses. Bars within an old church. Husks.

This passion to exert one’s will on the world can come in many different shapes and sizes. There are mission driven founders. There are financially driven founders. There are rage driven founders (this was a new one for me that I heard about this week. Basically someone that is so infuriated by the status quo they say “screw it, I will change it myself”.) But while the prime motivating factor changes, the passionate drive of all strong founders is nearly identical.

This spirit of entrepreneurship can inhabit the halls of older incumbent companies as well, though it does so rarely and often in the places you would least expect. Be wary of large corporations touting their innovation groups and “startup culture.” The spirit of entrepreneurship does not reside somewhere simply because someone wishes it to. It can be born in a moment when a group of mavericks suddenly decides try to change the world against all odds. It can die just as quickly if not properly nourished.

Viewed through this lens, providing a nourishing environment that is ripe for the Spirit of Entrepreneurship to inhabit becomes of the utmost importance.

Doing so successfully is easier said than done. My favorite road map to doing so is laid out in Loonshots by Safhi Bahcall.

But even with help. It’s not easy.

And it shouldn’t be.

Things worth doing rarely are.

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The Score is 0-0

Reuters

I had the pleasure of watching the US women’s national team win the world cup today. It was an entertaining, if somewhat inevitable, match with the Dutch rarely looking threatening. The score was tied 0 - 0 at half-time before Team USA scored twice in the second half to defend their crown and walk away the victors.

Newspapers around the globe tomorrow will sing the team’s praises and tease out the insights and lessons from their performances over the past few weeks. For my part, the game reminded me of a recent quote and the powerful lesson it represents.

Petr Cech played goalkeeper for Arsenal for the past few years before retiring at the end of last season. A couple of months ago he did an AMA on the Arsenal subreddit and one of his responses has really stuck with me ever since.

When asked how he mentally resets after conceding a goal, Cech responded “In my head, every single second of the game the score is 0-0. I literally do the same process for 90 minutes all over again regardless of if we are winning or losing. I just concentrate on my job. That’s all I Do. Every. Single. Day.”

I love this attitude and think there is a lot to learn from it. People (myself included) too often let the cloud of recency bias hang over their actions. If the last time they tried something it was successful, they will think that this time they are invincible. If they were recently defeated, they will believe they’ll never even have a chance.

The much better approach is to think of the score as 0-0. No matter what has happened before. Play as if it’s all tied up.

The USWNT was the most talented team at this year’s world cup. By a mile. Their greatest challenge was not defeating their opponents. It was playing like the score was 0-0 despite the fact that they were defending world champions.

Adopting this mindset is harder than it sounds. Unconscious biases are just that, unconscious. The greatest tool in your toolkit to fight against the power of recency bias is process. Develop the right process and you will be able to train your sights on that process, no matter what the score is.

Every. Single. Day.

This lesson is especially important in the world of investing. Investors are humans too, and just like all other humans are susceptible to recency bias. A recent successful trade can breed feelings of invincibility on all future trades. A startup with a young founder that flamed out can lead you to believe that all startups led by young entrepreneurs are doomed to fail.

Investors need to practice the mindset of thinking and acting as if the score is 0-0. Try to maintain your mind’s neutrality during both the highs and the lows.

In venture capital, this can often be especially tricky. Given the nature of technology startups, companies often require multiple rounds of funding in order to be successful. This means that recency bias rears its ugly head, not with some uncorrelated trade, but with prior funding rounds of the very same company you are currently considering for investment.

It is almost impossible to avoid letting a company’s past performance, actions, and outlook color the way you think about another investment. Some investors even claim that this inside access gives them superior signals by which they are able to make their decisions. And there is likely some truth to that. But there is also the danger of allowing past occurrences to obfuscate current decisions.

When evaluating an investment in a company, it is absolutely essential that you act as if the score is 0-0. Do everything you can to determine whether the company’s current attributes and trajectory warrant an investment based upon their own merits, irrespective of past funding rounds in which you may or may not have participated.

As in life, the best way to do this is to develop a process. And then stick to it.

Every. Single. Day.

Oh.

AND GO TEAM USA BACK TO BACK WORLD CHAMPIONS BABY!!!!

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What is your superpower?

Photo by TK Hammonds on Unsplash

We all have our strengths and our weaknesses, but what is your one superpower?

This is a question I have spent a considerable amount of time thinking about. I am a big believer in the idea that doubling down on your strengths leads to more powerful results than shoring up your weaknesses ever will. My recent musings on this idea of superpowers was prompted by this twitter thread (for the record I think Brent Beshore had the best answer).

The first time I tugged on this thread was after one of my mentors told me that the most surefire path towards success in life is to become the world’s best at something. Whatever that something is, if you are the best at it, you are going to do alright.

I think there is a lot of truth to this. It echoes Naval’s advice to become “Be the best in the world at what you do. Keep redefining what you do until this is true.”

I am not saying we should just ignore our weaknesses, but I believe that far too much emphasis is placed on fixing them when your time and effort would be much better placed on learning to leverage your strengths. The hidden benefit of this focus on leveraging your strengths is that it is a lot more fun. Strengthening your weaknesses can often feel like shoving a square peg into a circular hole. It can be done, but it isn’t a super fun exercise.

When you focus on leveraging your existing strengths, you can create powerful and motivating flywheel effects. As you get better at something, you see better results. This in turn motivates you to continue putting in the time and effort. And so you get better. And so you see better results. And so on.

So what is your superpower? What is the one thing that truly differentiates you? Is it something you already have, or is it something you are building towards?

I know mine.

I want the ability to develop and maintain relationships with others to be my absolute superpower. Relationships are hard to maintain, but I never, ever want to be the source of one falling unintentionally into disrepair. I want to always pour more into my relationships than I get out of them and I will never treat them as transactionary in nature.

This is easier said than done. It means a lot of prompt responses to emails and a LOT of following up with people. I am only able to do this because I have made it a very intentional priority in my life and built systems that allow me to manage my relationships in as efficient a manner as possible.

My ability to do this has taken a huge leap forward since I started using a tool called Notion.

Notion is basically what you would get if you combined Evernote, Google Docs, Excel, and Airtable. It has been a total game changer for me and I have built myself a personal dashboard using it that covers everything from my notes to my goals to my habit tracker to my personal CRM.

It’s this personal CRM that I especially wanted to highlight since I believe that it is an incredibly powerful tool that you can easily make use of as well. Here is a link to it if you would like to give it a try. You can duplicate it into your Notion at a click of a button if you think it might be useful.

A brief explanation. The guiding principal for this was to be able to set a cadence for how often I wanted to stay in touch with people and then to surface their contact information at the appointed time. On one end of the spectrum there are coinvestors that I don’t want to bother more than once a year. On the other hand are my brothers who I make sure to text at least once every three weeks. I wanted my CRM to be simple, flexible and allow me to easily search for people and sort by particular categories. I use it to manage my relationships with other VCs so it is super helpful to be able to sort by seed investors who do SaaS deals for instance by utilizing the Tags column.

The table is sorted in ascending order based on the To Contact column which means that the “oldest” To Contact date will be at the top. This is my to-do list. Any one whose To Contact date is prior to today is someone I need to reach out to. If I don’t want to reach out to someone for whatever reason, that is simply a signal I need to beef up their frequency value so that I contact them less frequently (you can also chose to not have a frequency value at all if you want to maintain someone’s contact information, but not necessarily reach out to them on a set schedule.) Each contact is a page in and of itself you can access by clicking on somebody’s name where you can take notes about your various interactions.

Using this tool may seem like a lot of work, but it has had a transformational impact on my ability to stay in touch with people.

No one said developing a superpower would ever be easy.

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The Power of Reading Two Books: Truthspeakers and Toy Story

Photo by Mikhail Pavstyuk on Unsplash

I love to read. It is my true happy place. No matter where I am or what I am doing, I know zen is only as far away as my current book.

I am in the habit of always reading two books at any given time, one fiction and one non-fiction. I think to neglect either does you a huge disservice. I truly believe that your imagination is like a muscle and that reading fiction is one of the best ways to exercise that muscle. And maybe it is just my learning style, but I learn through stories and for me, a good non-fiction story is the absolute best way to consume and learn new information. I generally read my fiction book before bed every night and I listen to my non-fiction book throughout the day on runs, my commute, or while doing the dishes.

The act of reading, just in and of itself, is rewarding, relaxing, and helps me expand my intellectual world. The beauty of reading two books at once is that, every so often, they align in the most magical sort of ways.

The fiction series I am currently reading is the Wheel of Time and I can honestly say that it is among my favorite fantasy series ever. The world, the magic, and most of all, the characters. All serve to paint an incredibly rich and compelling world across the course of 14 books (just started book 10, The Crossroads of Twilight).

What starts as a seemingly generic fantasy trope (a group of teenagers from a small village has greatness thrust upon them by a mysterious woman and embark on an epic quest where the fate of the world hangs in the balance) turns into so much more across the various twists and turns of the series. One such surprise is the Seanchan, who are the returning descendants of an army sent to a far off land thousands of years ago. They are as culturally unique as they are powerful and they have many interesting customs.

One custom that I found especially compelling was the role of the Soe’feia or Truthspeaker in the Seanchan’s imperial order. A Truthspeaker is a servant who is the trusted adviser of the Empress and the Imperial family. Despite their role as a servant, their purpose is to speak truth to their masters, no matter how harsh or unwelcome. Multiple times throughout the story characters are shocked by the brutal honesty displayed by these Truthspeakers to the most powerful of Seanchan royalty.

We all need Truthspeakers in our lives.

People who can hold a mirror up to ourselves. Even the ugly parts that we don’t like admitting we have.

I am lucky to have Truthspeakers in my life through friends and family, which is important because I need to be called on my own bullshit. A LOT. (my wife is seriously a saint I have no idea how she puts up with me).

Just as important to having Truthspeakers in our personal lives is to have someone who can tell it to you like it really is in our professional lives. This can be a boss, co-worker, or mentor, but it is vitally important to have someone that can help you see around the corners of your own bias and emotion.

How do you do this on a company level?

Enter book two.

The non-fiction book I am currently reading is Creativity, Inc. by Ed Catmull, the president of Pixar and Disney Animation. Creativity, Inc takes readers insides the halls of Pixar throughout its, at equal times, tumultuous and triumphant history. The book’s focus is not simply on presenting the facts that occurred over that time but exploring what sets Pixar apart as an organization and how other companies can break down similar barriers to creativity and success.

One such secret to success for Pixar has been the Pixar Braintrust, the company’s ace team of directors, operators, and creatives that are brought in to fix problems when they inevitably arise as part of the production for each movie. The only membership requirements for the Braintrust are a knack for storytelling and a willingness to be candid with one another. Ed view’s his primary role, not as a leader of this group, but as more of a facilitator whose focus is on maintaining the integrity and honesty of its process. Some of the absolute key changes made to the movies we have come to know and love over the years like Woody being a lovable cowboy to WALL-E being saved by EVE were hatched during braintrust meetings.

I love this concept and found the parallels between Pixar’s Braintrust and the Seanchan’s Truthspeakers simply too delightful to not write a post on them.

In the world of startups and venture capital, being an entrepreneur can feel isolating. I believe it is absolutely essential to any company’s success to develop a culture where the CEO has Truthspeakers around them that they can be relied upon to tell it like it really is. As a venture capitalist, I see my role as doing just that.

I haven’t run a company before.

I haven’t developed a world-changing technology.

But if I can do just one thing to add value to a company, I hope it is that I can speak with truth and candor when an entrepreneur needs it most.

Into the Wilds

The suck will happen. It will happen to you and it will happen to me. We don’t have any say in this.

But we are not powerless.

We get to choose how we react to this time in the wilderness.

The Wilderness

Being outside is awesome. I am a firm believer that time spent outside with people we love is the best way to build lasting and impactful memories. That is not the sort of wilderness I am talking about in this post. I am talking about the wilds of life. Times when things get tough. Times when you feel lost and your lack of direction starts making you question if you will ever find the trail head.

I am willing to bet you have spent at least some time in this wilderness. I know I sure have. For most, it is a question of when, not if. This time in the wilderness can be precipitated by a variety of things. Relationships. Career setbacks. Struggles with health. The hallmark of all of them is that you find yourself struggling through without a clear path forward.

I wish you nothing but the worst of luck

A couple of years ago Supreme Court Justice John Roberts gave an unconventional speech at his son’s high school graduation that picked up some attention. I recently read through it for the first time and it really struck a chord with me. I have highlighted an especially impactful section below.

I think Justice Roberts does an excellent job capturing the idea that our reactions to life define us even more than our circumstances do. I am a big believer that people have a lot more agency in life than they often believe. The Berg family motto is “Everything in life is a choice”. When something bad happens, you can choose to let it define you. Or you can choose to view it as an opportunity for learning and growth.

Tracking

Our times in the wilderness are brutally hard when we are in the thick of it. But these times also present a potentially life-transforming opportunity. Times in the wilds are an opportunity for learning, exploration, and self-discovery. When I am unsure of my next step or direction, I often think back on the philosophy of Tracking espoused by Boyd Varty. These tough times often will have clues about what your next step should be, they just often require some tracking to find them.

Look for signals in the noise.

What aspects did you like about your old job versus dislike? What were the attributes of your recently ended relationship that were healthy? Which were toxic?

Use this time to dig in and understand the things that give you energy, joy, intellectual stimulation and purpose. Double down on those things.

I recently finished David Epstein’s latest book Range. I (along with basically every person on twitter) found it fascinating and very informative. There are a lot of excellent takeaways in this book and I highly recommend giving it a read, but the one message that came across strongest to me after putting it down was the importance of “Sampling Periods.” Sampling periods are times of exploration and discovery before someone narrows their focus and specializes. I won’t go too deep into arguing the benefits of this as David does a much better job than I ever could but, suffice to say, study after study demonstrates the benefits of having a period of exploration before specialization in sports, business, science, and life.

That’s what these tough times can be. A sampling period for self-exploration and discovery. Figure out where your talents overlap with your interest and then double down on whatever that is. Keep an open mind and focus on optimizing for learning and growth over the long-term as opposed to performance over the short-term. Use these trying times in the wilds as a sampling period to discover the best fit for your skills and personality.

I know it is difficult. I offer this advice as much to you as myself. I don’t act in this way nearly as much as I would like to. But I am working my way there.

You can too.

All you have do is to remember that whenever you find yourself in the wilds of life, you are being handed an opportunity.

An opportunity to learn and to grow and to track your way to the life you have always wanted.

All there is to it is to choose to do so.

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Institutional Contrarianism: On Everest, Mozart, and Instinctual Originality

(Nirmal Purja/AP)

You’ve probably all seen this picture. The 2019 Mount Everest summit season has become famous for a high amount of deaths and reports of long lines of climbers waiting to complete the final summit.

Too often investors act like these climbers. Instead, they should act like Mozart. In this post, I will tell you why.

Institutional Contrarianism: When climbing the world’s highest mountain enters the mainstream

The summit of Mount Everest was first reached in 1953 by Edmund Hillary and Tenzing Norgay. This success came almost 70 years after it was first suggested the feat might even be possible. Unsurprisingly, the summit of Mount Everest captured the world’s collective imagination in a way that few endeavors had before, or since.

And there was no putting the genie back in the bottle.

A line of hundreds of climbers waiting on the summit is what happens when climbing the world’s highest mountain enters the mainstream. What was once the domain of a chosen few lofty dreamers has become the world of Fred from El Paso. And Mo from two neighborhoods over. Now, that is maybe a little bit of an exaggeration, but a Sherpa guide has reached the summit of the mountain 24 times (the most a non-Sherpa has reached the summit is American David Hahn who has reached the summit 15 times).

Venture capital bears a striking resemblance to Everest. Everyone claims to be trying to operate on the edge of what is possible, but when everyone is swimming against the current, is anyone really?

Contrary is the biggest buzz word in venture capital today. No, the irony is not lost on me. The cult of contrarianism was seemingly started by Peter Thiel and his oft-posed question of “what is something you believe that those around you disbelieve?” In his book Zero to One, Thiel encouraged people to come up with fundamental insights about the world by looking at it through a different lens than others. I am a big fan of this way of thinking.

But it has warped into something different altogether. It has become the very evil it sought to destroy.

It has institutionalized.

At some point, everyone trying so hard to go against the crowd just becomes a herd moving in the opposite direction.

Everyone pays lip service to being a contrarian, but how much of them actually do it? From what I have observed, some. But not many. This Institutional Contrarianism becomes the very thing it claims to oppose. There are few leaders in a new space, but many followers. People are interested in latching on to the work others have done and seek exposure to hot spaces without necessarily having a strong perspective on them.

How do you break out of the trap of Institutional Contrarianism? How do you strive for true originality?

We look to great creators of the past for answers.

Create like Mozart: Tapping into the power of Instinctual Originality

A book I have learned a lot from is Impro by Keith Johnstone. This book is ostensibly about improvisation in theater but actually has much more far-ranging lessons. You may recognize it from the annals of FinTwit where it is oft-cited for its teachings on physical presence and interpersonal positioning. These lessons are great, but I have found that it has just as much, if not more, to teach us about learning and thinking.

Recently while reading I came across a section on originality that I think offers some striking insights towards solving our problem of Institutional Contrarianism.

Johnstone on originality in theater:

Anyone can run an avant-garde theatre group; you just get the actors to lie naked in heaps or outstare the audience, or move in extreme slow motion, or whatever the fashion is. But the real avant-garde aren't imitating what other people are doing, or what they did forty years ago; they're solving the problems that need solving, like how to get a popular theatre with some worthwhile content, and they may not look avant-garde at all!

Similar to the avant-garde movement, venture capital investors too often find themselves pursuing what is fashionable instead of what is truly differentiated. By definition, a space cannot at the same time be fashionable and contrarian. One need only look at any tech news site to see the dynamics of fashion trends at works. Entire sectors and technologies fluctuate between golden child one moment and untouchable the next. Blockchain. VR. AI. Greentech. All have had, or are having, their moment in the sun. All likewise have at some point been cast aside.

The crux of the issue is that you cannot generate abnormal returns in any asset class by acting the same way as everyone else. When a “contrarian” trend becomes the fashion and everyone starts flooding into the space, you can guarantee that valuations will skyrocket even as the number of quality opportunities diminishes.

As Johnstone says above, truly original ideas will often hide behind a sheen of the mundane. In hindsight, it is easy to craft a narrative around why companies like Uber and Airbnb were so transformative, but at the time they seemed anything but. Plenty of incredibly smart, successful investors passed on some of the greatest investments of the past decade (for proof just check twitter any time a tech company goes public).

So how can we tap into this true originality of thought? When asked where his ideas come from, Wolfgang Amadeus Mozart replied:

Why my productions take from my hand that particular form and style that makes them mozartish, and different from the works of other composers, is probably owing to the same cause which renders my nose so large or so aquiline, or in short, makes it Mozart's, and different from those of other people. For I really do not study or aim at any originality

Therein lies the secret. One cannot be original by trying to be original. Striving to be contrarian leads you to follow the popular fashions of the day and will inevitably lead to mediocrity. The path to true originality in life and business can only be found by accepting yourself and leaning into the things that make you unique and different. I call this Instinctual Originality.

Ok, Erik, great. Just emulate Mozart. No problem.

It is not as hard as it sounds.

First, accept who you are. All your faults and all your greatness. Be aware of them and honest with yourself about them.

Next, ignore the mainstream. Easier said than done, but possible all the same. Don’t buy the hype. Always ask why and act from principles and fundamental thinking.

Finally, create from a place of Instinctual Originality. Originality is not some external mountaintop that we can scale, it is inherently inside each of us. Let it flow from you. Don’t pursue it. Listen to the voice inside of you. There is a reason that our best ideas often come in the shower or on a run. We already know the answers.

We just need to listen.

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Lessons (and Books) from Camp

Credit: ME! Yes, that is right! This is the first time I have ever actually used one of my own pictures for the blog. This was a picture from the working farm where we had our final dinner on the last night of camp

Last week I had the opportunity to attend the first Capital Camp hosted by Brent Beshore and Patrick O’Shaughnessy in Columbia, Missouri. Over the course of three days, we listened to speakers from all corners of the investment landscape, ate delicious food, experienced some (incredibly) unique activities, and just had a fantastic time. It truly was an amazing experience and I really feel honored to have been included. We had to sign an NDA as a prerequisite to our participation, so I can’t go into too many details about the presentations themselves, but I did want to list a few of my big takeaways from the experience alongside some of the book recommendations that seemed to be a part of almost every conversation.

The Value of Going Niche

A common theme that shone through a lot of the presentations during camp was that there is a lot of value in going niche. Many of the presenters were working in under-explored niches within the investment world and this willingness to go against the grain had compelling results. Going niche allows you to be a standout within a smaller pool. If there is an interesting opportunity in the space you are playing in, competition will inevitably flow in, but by being at the forefront of the trend, you will be among a handful of go-to people in the space. There is A LOT of value in being “The _______ Guy”. If you are among someone’s first couple of calls when they are in a very specific industry or if they are looking for a never-before-created financial product, you are going to be able to capture a lot of value.

The Ugly Premium

Similar to the above, there seems to be a premium placed on work that requires one to get their hands a little dirty. A willingness to go down into the weeds and tolerate extreme complexity or uncertainty can be a true differentiator when competitors are more than happy to stick to harvesting low-hanging fruit. Being a pathfinder in difficult or unexplored terrain is rarely easy, but the results can be truly spectacular if you develop a reputation for handling ugly situations with effectiveness and grace. People are also all too willing to overlook diamonds covered in a few layers of dirt. If you do the digging, you will have them all to yourself.

The Power of Place

I believe that the decision to host Capital Camp in Columbia, Missouri was absolutely key to the event’s overwhelming success. Place is a powerful consideration for any event or gathering and its effects should not be overlooked. By having this event in Columbia, Brent and Patrick immediately differentiated it from the plethora of other investor conferences that occur every year. They were able to build a completely differentiated ethos that was pervasive throughout the entire event and which led to a much more memorable experience than if it had been hosted somewhere like New York. I also think the location served as a strong tool for self-selection. Hosting a AAA investor conference in the middle of Missouri self-selected for people with a wide variety of interests who were open to new things and not too good for small-town America. By design or by accident, I think the location of the event was an incredibly powerful Asshole-Filter.

Interesting People Lead to Interesting Results

As awesome as the presentations, food, and activities were, they paled in comparison to the joy of simply interacting with the other attendees. I am a big believer in the idea that any time that you can get interesting and intellectually curious people together in a single place, something positive will inevitably happen. I know I wasn’t the only one that felt completely out of my depth at times, but the humility and curiosity of the other attendees ensured that I never once felt out of place. I can honestly say this was the first investor event I have ever been to where people were genuinely more interested in learning about you and what you did than they were interested in telling you about themselves. I don’t believe this was an accident, and I am sure both the location and the interesting/expansive variety of Patrick’s podcast both played their part in attracting high-achieving, yet humble, people with intellectual curiosity as varied as it was deep.

The Books of Capital Camp 2019

Interesting people from all over the world attended the first Capital Camp. Every conversation was different from the last. The one constant is that I left almost all of them with a new book on my reading list. Amazon affiliate links included for each book.

Here are all of the books that were recommended to me throughout the course of the week:

• Loonshots: How to Nurture the Crazy Ideas That Win Wars, Cure Diseases, and Transform Industries by Safi Bahcall

  • Ok, I am cheating a little bit on this one. Loonshots was actually the recommendation that I gave everyone who shared a recommendation with me! The book describes how to foster innovative thinking inside of organizations and explores what separates nimble, innovative organizations from slow, political ones. This is by far one of the most entertaining “business” books I have ever read and one that I am sure I will refer back to for some time to come

• Think Twice by Michael Mauboussin

  • Michael Mauboussin was one of the presenters at Capital Camp and I am not exaggerating when I say that his was one of the most interesting and thought-provoking sections of the whole camp. Two of his books were highly recommended and many attendees talked about how influential his writings have been on them

• The Success Equation: Untangling Skill and Luck in Business, Sports, and Investing by Michael Mauboussin

  • Essay highlighting some of the findings from the books

• Titan: The Life of John D. Rockefeller, Sr. by Ron Chernow

  • Tim Ferris has an interesting heuristic about focusing on reading stories that have been around over 100 years. Chances are if they are still being talked about, there is something of value in there. Few names have persisted as long as Rockefeller’s and his biography was recommended by an attendee who makes sure to read it every couple of years

• Steal Like an Artist: 10 Things Nobody Told You About Being Creative by Austin Kleon

• The Fifth Discipline: The Art & Practice of the Learning Organization by Peter M. Senge

• Thinking in Systems: A Primer by Donella H. Meadows

  • Systems thinking was a topic that came up in multiple presentations and conversations at Capital Camp. It is one of the topics I am most looking forward to learning more about!

• Powerful: Building a Culture of Freedom and Responsibility by Patty McCord

• Principles: Life and Work by Ray Dalio

  • This book is probably the one that has been recommended to me most even from before and after camp. I have had it sitting in my kindle for some time now, but it has vaulted to the top of my list based on some of its recent recommendations

• Making Things Work by Yaneer Bar-Yam

• Zen and the Art of Archery by Eugen Herrigel

• The Overstory: A Novel by Richard Powers

  • The only fiction book that was recommended to me at camp. I love reading fiction and always make sure to be simultaneously reading one fiction and one non-fiction book at any given time. Not only is fiction generally more entertaining but I truly believe that imagination is a muscle that needs to be exercised just like any other. Reading fiction books is a great way to do just that.

• Confessions of the Pricing Man: How Price Affects Everything by Hermann Simon

• HBR Guide to Buying a Small Business: Think Big, Buy Small, Own Your Own Company by Richard S. Ruback and Royce Yudkoff

  • Search Funds and Permanent Capital Private Equity were two of the asset classes with the most buzz around camp. This recommendation (and the next two as well) are what I was provided when I asked where a novice should start learning about these asset classes

• The Messy Marketplace: Selling Your Business in a World of Imperfect Buyers by Brent Beshore

  • This was the first book from this list that I picked up after camp and I can happily report that I am thoroughly enjoying it (and I am not just saying that since Brent hosted!) You can tell that it is written to be a reference guide to sellers, but it has been enjoyable and insightful to me as an investor as well!

In addition to the books above, I also received recommendations for a few other mediums:

• Adventur.es Writings

  • Another shout-out to the Adventures team. Brent and Co. are the leaders in the Permanent Capital Private Equity world and they have put out a huge number of thoughtful pieces about the space on their website.

• Anything written by Matt Levine

  • I was told that reading whatever Matt Levine writes is basically the equivalent to an MBA. I subscribed to his newsletter not long after…

• The Business of Innovation: An Interview with Paul Cook

• Dealbreaker

• Econtalk Podcast episode with Jerry Muller on the Tyranny of Metrics

  • I listened to this episode earlier this week and it was a fascinating discussion about the dangers of an over-reliance on metrics without using one’s judgment. I really appreciated Muller’s thoughts on the subject and thought they sync up nicely with my previous post on venture capital due diligence

• My Dad Wrote A Porno Podcast

  • This recommendation was definitely a little bit different than the others. I was told not to listen to it while driving since laughing so hard on the road would be unsafe!

• Sam Hinkie’s Resignation Letter from the 76er’s

  • Just as Sam Hinkie closed out the show at camp, the recommendation to read his resignation letter from the Philadelphia 76er’s closes out my list. Sam’s presentation was one of the more interesting and entertaining presentations I have ever seen and this letter gives a fantastic window into how he views the world.

Thanks again to Patrick and Brent for hosting such a fascinating and fun investor event!

Can’t wait till next year!

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Confessions of an Anxious VC

Photo by Rob Curran on Unsplash

My whole life I have suffered from social anxiety.

It’s something that would surprise a lot of people. I am a social extrovert. I am often the loudest (sometimes obnoxiously so) and most outgoing person in most rooms. I get my energy from interacting with others. And yet those same situations cause me anxiety.

Talk about a catch 22.

I have had social anxiety ever since I was a kid. It used to be bad. Outside of a few best friends, I wasn’t able to spend time in social settings with friends outside of work. The first time I hung out in an unstructured group setting (not a birthday party or a sports practice etc.) was my freshman year of high school.

The weird thing was that it was never the act of being social or the event itself. It was the anticipation of being in a social setting that caused the anxiety ahead of time. Once I got there, I was fine. In fact, I was more than fine. Being social is when I am at my best.

Luckily, I was able to get help. My parents had the resources to pay for me to see a psychologist when I was in middle school. Vocalizing my internal thoughts made a huge difference. Often my own self-talk sounded laughable when said out-loud. By talking about my feelings with an objective third party, I was slowly able to shift the way I talked with myself. I am so grateful I had the opportunity to get help and it breaks my heart that asking for help with mental health still seems to be so stigmatized by our society. I can honestly say that I would not be where I am today without it. Healthy, happy, and (mostly) well-adjusted.

But that doesn’t mean I still don’t get anxious sometimes. Anyone who has dealt with anxiety will understand what I am talking about. The anxiety never really goes away. You just learn to deal with it.

For me, the best strategy was “faking it till I made it”. Every time I threw myself into a social setting I was anxious about, the little voice in my head telling me I wasn’t good enough whispered a little bit more quietly. I acted like I was confident and before long I started to actually feel confident. Over time that little voice went away almost completely.

But it still crops its head up every now and again.

Especially when it comes to networking.

I don’t know what it is, but networking has always given me a spot of trouble. I guess it is just the fact that I generally don’t know anyone at all. True or not, I have this idea in my head that everyone else knows each other and it is easy to get intimidated by that.

Now, you can see why this is a problem.

As a venture capital investor, networking is a big part of my job.

Cultivating a network of relationships with entrepreneurs and other investors is one of the keys to success in this career. It’s not always easy, but I have come up with a few strategies that help me and that may help other people.

Learn someone’s story

The biggest improvement in my ability to network came after re-framing the entire activity. A former colleague of mine was always getting drinks with people after work or meeting up with people in his network for lunch. Most of these connections were people he had met briefly or only a couple of times previously. I had no idea how he did it. When I finally asked him how he was able to network so effectively his response was to tell me that he just liked “hearing people’s story.” As soon as I heard that it was like the clouds parted. I love meeting new people and learning about their story. Ever since I reframed networking as getting to hear people’s stories, instead of focusing on how to present my own, it has gotten exponentially easier and more fun!

An inch wide and a mile deep

Another big key has been focusing on quality over quantity when it came to social connections. I would get overwhelmed by feeling like I would never be able to talk to everyone at an event. So now I don’t even try. I focus on trying to make a smaller amount of deeper connections. I would rather have two 20-minute conversations than eight 5-minute conversations. Aside from just taking the pressure off, I also think this is just a much more effective way to network. If you have a superficial conversation with someone for 5-minutes, you will get lost in the noise. Talk to someone for 20-minutes about the harmonica or the frequency of lightning strikes around the globe and you can be sure that you will stand out.

Go with a friend

When in doubt, guilt-trip a buddy to going with you. Just knowing that you know at least 1 person in a crowd makes a ton of difference. Even if you split up once you get there, it is comforting to know you have a security blanket of someone you already know to talk to in case you need it. And if the event sucks, at least you have someone to laugh about it with.

Nobody cares what you say

This may sound a little depressing at first, but I actually think it is really empowering. The beauty of being in a social setting where you don’t know anyone is just that, nobody knows you. If you say something stupid or put your foot in your mouth, guess what? Chances are that you never have to see those people again if you don’t want to. Maybe you aren’t quite as prolific in putting your foot in your mouth as I am, but the logic even works for boring superficial conversations. Don’t stress about making an impact on every person you talk to. See point number 2 above. If you aren’t jiving someone and you just can’t get them to bite, don’t stress. They won’t remember.

**For the record, I think this tip has a ton of applications outside of networking, especially when it comes to creating content online. People are too afraid of what other people will think about what they say. The truth is, if you say something dumb (like I have many times), no one will care (unless you say something really, really dumb or offensive). On the flip side, make some interesting points and people will take notice. Minimum downside. Maximum upside.

Pick a color, any color

This is a fun one that I picked up from a podcast. If you are anxious about a networking event, pick a color. When you get to the event, talk to everyone there who is wearing that color. It’s that simple. I don’t know why, but for some reason having a mission when you walk into an even (talk to everyone wearing green) really helps. I enjoy this one so much I even went as far as to buy 6-sided dice on Amazon that have different colors on each side. Before any networking event, I roll the die and try to talk to everyone wearing whatever that color is. I don’t know why this one works, but it does. Give it a try.

Go against the grain

I picked this one up from Tim Ferris. When you get to an event, look where everyone is focused. It may be the food table or a celebrity whose attention everyone is trying to get. Ok now see that group focus? Head in the exact opposite direction. It is tough to stand out in a crowd. Give yourself the best possible opportunity you can by going against the grain and doing stuff other people aren’t. This means going to the more esoteric info sessions. It means doing the weirder activities. If you are doing things differently than everyone else, people will take notice. And even better, you will see the other people who are doing the same. Those are the people you want to talk with.

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Hopefully this post is as helpful for you to read as it is for me to write. Mental health is hard. Talking about it makes it less so.

As with most things, overcoming anxiety is a slow and painful process.

Each step feels like you aren’t making any progress.

It’s only when you look back that you see how far you’ve come.

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