Reunited and it feels so good

Abergseyeview Arsenal Lacazette Aubameyang

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

Almost Vested Startup Church Entrepreneurship Zen and the Art of Motorcycle Maintenance

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.


The Score is 0-0

Reuters

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!!!!

Ron Swanson USA

What is your superpower?

Photo by  TK Hammonds  on  Unsplash

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.


The Power of Reading Two Books: Truthspeakers and Toy Story

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

Venture Capital Wilderness

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.

Chief Justice John Roberts graduation speech

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.


Institutional Contrarianism: On Everest, Mozart, and Instinctual Originality

(Nirmal Purja/AP)

(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.

Mount everest venture capital climbs

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.


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

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.

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

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!


Confessions of an Anxious VC

Photo by  Rob Curran  on  Unsplash

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.


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.


Sports, Startups, and the Competition Trap

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It has been an interesting week from a sporting perspective. A week that has made me reflect on my relationship with sport and with sport’s relationship with life.

Now I am a big sports fan in general, but my one true sports love has, and will always be, Arsenal FC. My dad was an Arsenal fan ever since he was a kid and I had little say in the matter with some of my earliest ever memories involving watching Arsenal games with my dad. To anyone who knows soccer, you will know what a long, strange journey being an Arsenal fan so often is. This week has been no exception.

It started last Sunday with a painful tie at home against Brighton. This was a horrible result which sealed our fate to finish 5th in the table and miss out on a coveted top-4 spot and automatic entrance into next year’s Champions League.

But not all hope was lost! On Thursday we played Valencia in the second leg of the Europa League semi-final, winning 4-2 and booking our ticket to the Europa League final at the end of the month. Besides being Arsenal’s opportunity to win our first European trophy in 25 years, the game also represents another chance to get into next year’s Champions League, with the Europa League victor always being granted automatic access.

Today, we won out 3-1 away to Burnley in a game that contained little significance other than helping our star striker, Pierre-Emerick Aubameyang, get the goals necessary to win this year’s Golden Boot trophy (awarded to the league’s top goalscorer).

The rollercoaster week did not end there. This is just covering Arsenal’s exploits on the field! If you are any sort of sports fan at all you will have likely heard of Liverpool and Tottenham’s exploits in the Champions League this past week. Both teams came from huge holes to win their respective semi-finals in spectacular fashion. Their fans and the sports world at large were jubilant. I was crushed. You see Liverpool and Tottenham are two of Arsenal’s fiercest rivals. Especially Tottenham.

And I just could not stand to see them win and their fans happy. It ate me up inside.

Now I am not overly proud of this negative mindset, but rooting against your rivals is a fundamental part of sports. It underlines a certain masochism that comes along with being a sports fan.

You are really only happy when your team wins and, by definition, most teams won’t win trophies each year. So you are setting yourself up for failure right off the bat. Even if you look at the teams who win all the time, expectations are so incredibly high that fans are still miserable when Real Madrid only wins one trophy in a year!

Now I love sports and that isn’t going to change. But being miserable at other people’s happiness was somewhat of a wake up call for me. That is just not how I want to go through life. I think there is a way to be a sports fan without the negativity. Focus on enjoying your team’s journey. The highs and the lows. Try not to focus too much on what everyone else is doing.

And remember, the most beautiful part of sports is that there is always next year.

This competition trap is not unique to sports. It is all too common in everyday life and business. We are so focused on what other people have we don’t appreciate what we have. We look at the 10% of peoples’ lives that they share on Instagram, we assume they live like that all the time, and then we compare it to the 100% of our lives that we are familiar with and can’t help but to feel like we don’t measure up.

Comparison is the death to joy.

Focusing on what other people have will only ever bring you negativity. Either you will be envious of what others have or you will look down on them for not having as much as you.

I think this phenomenon exists in businesses too.

All too often I think businesses get so wrapped up in competition with one another that they forget about the things that made them great in the first place.

Startups are especially susceptible to this. Too often entrepreneurs get overly wrapped up in their competition when that is really an issue for another day. Your competition is not going to matter if you are unable to create a product that solves a fundamental need for your customers. Entrepreneurs, leave competition until you find yourself in a more mature competitive market. No business was ever successful by focusing on what everyone else was doing.

Comparison is natural, but you will lose your way if you give your competitors too much of your attention.

Instead, focus on being the best that you can be. In life and in business.

Focus on the journey, not the destination.

And remember.

There is always next season.

Why Brushing your Teeth is the Secret to Success in Life and Startups

venture capital and brushing your teeth

Brushing your teeth is the secret to being successful in life and entrepreneurship. In this post, I am going to tell you why.

Brushing your teeth is not difficult. It is something we all do. But how many people do it the right way? It’s recommended that you brush your teeth twice a day, every day. There is proper form and improper form. I am sure some kinds of toothpaste are better than others, but admittedly, it can be difficult distinguishing which toothpastes are the best given that each and every one is recommended by 9 out of 10 dentists (I hope I never come across the 10th dentist. Must be a terribly negative person).

The key to dental health is consistency. You need to put in consistent effort day in and day out. Brushing your teeth for an hour at a time will not allow you to skip brushing your teeth for the next month.

Now, as much as I appreciate the importance of dental hygiene, this isn’t really a post about brushing your teeth. This is a post about life and business, two areas where we all too often brush for an hour once a month.

The key to success in life is consistent application of effort. This is true for everything from relationships and startups, to exercise and reading. Very rarely will you find yourself in situations where a single herculean effort is all that stands between success and failure. Much more often, slow and steady really does win the race.

When I was working at Carlyle the head of my team had a favorite phrase, “Do your day job.” It means taking care of the fundamentals of your role and making sure that you excel on the little things. Because if you don’t, it tends to be a slippery slope.

I am a big Broncos fan and our newest coach, Vic Fangio, put it well in his introductory press conference. When asked to explain his famous “death by inches” mantra he said:

“If you're running a meeting, whether it be a team meeting, offense or defense meeting, a position coach meeting and a player walks in, say 30 seconds late, 45 seconds late -- that act in it of itself really has no impact on whether you're going to win or lose that week.

"But if you let it slide, the next day there's two or three guys late or it went from 30 seconds to two minutes. It causes an avalanche of problems. That's 'death by inches.'”

The little things matter. Showing up consistently and putting in the effort is what makes the difference between success and failure.

No place is this truer than with startups.

On the startup battlefield, wars are not won in a decisive moment. Startup successes are a culmination of years of executing on the little things and consistently making progress. In tech, that steady progress tends to grow exponentially. This fact is sometimes hard to see among twitter hype threads and Techcrunch headlines, but the saying “an overnight success, 10 years in the making” really does ring true.

Execution is so, so key. A VC I really respect once told me that he would take a team that can execute in a small market over a team that can’t in a big market every single day of the week. Execution really is what sets apart A+ teams from the rest, and in venture you need those A+ teams to get the outcomes that justify the whole model.

You can bet that this hyper-focus on execution is something that VCs pay attention to.

A great example of this is due diligence. Due diligence is a necessary, but slow, and sometimes painful, process for everyone involved. A secret of venture capital that not many may know is that how an entrepreneur conducts themselves during due diligence, is just as big of a signal about whether the startup will be successful as anything else. An entrepreneur that is organized, prompt, respectful, and who has a masterful understanding of the ins and outs of their business during due diligence will likely exhibit that same attention-to-detail and execution mastery when it comes to running their business. Entrepreneurs who are difficult to deal with and get easily frustrated or are dodgy about direct questions about the business are unknowingly flying a pretty big red flag for all investors involved.

So now that we have agreed that consistent effort is the key to success, what is the best way to go about applying that effort?

In the immortal words of Joel Embidd:

“Trust the process”

The best way that you can ensure that you are properly applying just the right amount of force and using the proper technique when brushing your way through life is to build a process and stick to it. Our culture is far too outcome oriented. We operate on a last-in-first-out basis and optimize based on the outcomes we see, even when those outcomes are often nothing more than luck. If you flip a coin 4 times and get tails every time, you would not conclude that a coin will always land on tails. And yet, far too often our personal and professional actions are the equivalent of flipping a coin once, and assuming that every other time we ever flip a coin we will get the same result.

I have had a big focus on process ever since reading the book Chop Wood, Carry Water by Joshua Medcalf. I can honestly say this book has had a bigger impact on my life than any other. The subtitle says it all, “How to fall in love with the process of becoming great.” I highly recommend this book to any looking to lead a more process-oriented life.

My advice for you:

Focus on doing the little things right.

Fall in love with the process of becoming great. If you are able to truly do this, the outcomes will take care of themselves.

Maintain consistent effort instead of bursts of hyperactivity.

Take care of things like your health, your body, your relationships, your spirituality, and your mindset that only need a little bit of time each day to maintain and yet, are all too often neglected. These are things that are vitally important to your success in life, and yet not one of these things can be maintained by brushing for an hour once a month.

And speaking of.

Brush daily with consistent application of effort.

You’ll be surprised where you end up.

The only thing that is permanent is impermanence

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I don’t like change.

Never have.

Never will.

I am a creature of habit and I get used to having things be a certain way. Life unfortunately rarely works that way.

I saw the final Avengers movie on opening night and it got me thinking about change. Not the movie itself (though it was amazing), but what the movie represents.

When the first Iron Man came out on May 2, 2008, I was 14 years old in Denver, Colorado. I was in eighth grade, the school year was almost over, and after the summer I would be headed to high school.

11 years and 21 movies later, I watched Avengers: Endgame sitting in a movie theater in Columbus, Ohio watching with my wife.

In that time, I went to high school, college, met the love of my life in the library, had internships in Chicago, Portland, New Hampshire, got a job in private equity, lived on my own in DC, got married, moved with my wife to Bethesda, and finally moved to Columbus to take a job in venture capital.

For someone who doesn’t like change, I sure have done a lot of it!

Maybe it is just a movie and maybe I shouldn’t be so introspective, but in some ways it is hard for me to look at Avengers and see anything other than a monumental shift in my life from adolescence to adulthood.

By the end of 2019, Avengers, Game of Thrones, and Star Wars will all have come to an end. Three stories that have brought me countless hours of entertainment, joy, inspiration, and in the case of Game of Thrones, intermittent spurts of horror (but in the best possible way).

Now I am sure that these worlds will live on in the form of infinite sequels, prequels, add-ons, tie-ins, and everything in between. But it won’t be the same. Because I won’t be the same.

And that is ok.

As much as I don’t like change, I have learned to embrace it.

Life is a story, and if you want your life to be a tale of adventure, you are going to have to put up with a little bit of change here and there. The idea of change will always put a little tiny pit in my stomach, but I can honestly say that I haven’t regretted any of the changes I have made. There have been missteps and pitfalls along the way, but each fork in the road has led me to where I am today, and I wouldn’t trade that for anything.

They say, you overestimate what you can accomplish in a year, but underestimate what you can accomplish in 5.

If my life is any example, that is definitely true. A lot can change over the years.

Especially over the past 11 years and 21 movies.


I know this post didn’t exactly include earth shattering insights about the tech and venture capital world. That’s the beauty of writing a personal blog. Sometimes you can make it just that. Personal. And on a rainy day after my childhood came to an end, I am hoping you can indulge me.

What was your life like 11 years ago? I am sure a lot has changed for you too!

A Game of Venture Loans

Game of thrones venture capital startups entrepreneurship investing

The premiere of the final season of Game of Thrones is tonight. I am sure it will not surprise you to learn that I am a massive fan. I have read the books and watched and rewatched the series. One of the major overarching themes of the show is the zero-sum competition all characters experience in Westeros.

In the game of thrones, you either win or you die.

At a much more benign level, we see this zero-sum phenomenon play out in our world too. One of the reasons I have never been particularly enamored with the public markets is that there is someone “on the other end” of every trade. What this means, is that if you are purchasing a stock, the person who is selling you that stock almost always expects it to go down. If the stock goes up, you win and they lose.

I love venture in part because it is not a zero-sum game. There isn’t anyone sitting on the other end of our “trade.” When done well, there is enough incentive alignment to ensure that no party is succeeding at the cost of anyone else. Investors in funds win when VCs win when entrepreneurs win (say that fast five times). Perfectly in balance, as all things should be <<insert Thanos meme here>> (speaking of Thanos, it’s kinda wild that GoT, Avengers, and Star Wars are all concluding in 2019. I am firmly aboard each respective hype train, but it will be a bit bummer when all is said and done).

The one area that this does not necessarily hold true is getting into a hot round. The dynamics are such that in venture, entrepreneurs are always trying to thread the needle between raising too little (short cash runway) and raising too much (dilution). This means that for a given company, at a given valuation, there is going to be a cap to the amount of money the entrepreneur is going to want to raise. For most entrepreneurs, the worry is getting enough dollars in the door to close out the round, but for the hottest deals with experienced entrepreneurs or in a sexy space, rounds can fill up quickly. This can lead to significant competition between investors trying to get into the round. While not as competitive as Stark vs Lannister, things can heat up pretty quickly.

I should note that I have only ever witnessed this competition second-hand. My experience so far has mostly been centered around investing in the Midwest where the focus is much more on getting enough money around the table than trying to elbow to the front of the line. The simple fact is that there are not nearly the same numbers of investors here as there are in a bay area or a New York. That is changing as more and more people start paying attention to the exciting things being built in cities like Columbus, Pittsburgh, Kansas City and more.

I am thrilled for this increased attention and I think that it will be hugely beneficial to the region as a whole.

My one hope is that midwestern investors can maintain the same collaborative nature that they have cultivated thus far.

Because zero-sum competition is not a ton of fun.

Just ask the Starks.

A Slice of Humble Pie

Photo by&nbsp; Irina &nbsp;on&nbsp; Unsplash

Photo by Irina on Unsplash

This may come as a shock to you, but I sometimes have a bit of an ego problem. Yes, yes, I know. Hard to believe the guy who likes to hear himself talk so much he puts it into written word and blasts it off to the interwebs on a weekly basis has an ego problem.

Point is, I think I am awesome.

And I think that this is generally a good thing. But sometimes it is a bad thing.

Following?

I have a lot of self-confidence. I truly believe that I can achieve anything I set my mind to. I am someone that likes to throw himself head first into whatever roadblocks or hurdles life puts in my way. I am a big believer in the idea that if you don’t like something that is going on in your life, stop making excuses for it and take the necessary steps to change it.

I think this confidence is good. But sometimes it’s bad.

Sometimes I can get a little bit ahead of my skiis and fall down too much on the side of “better to ask for forgiveness than permission.” This approach works well in some settings, and significantly less so in others. One of my biggest weaknesses, my tendency to de-value the accomplishments of others, stems directly from this overconfidence and the related insecurities it can cause.

Another way that this confidence can sometimes manifest itself is through eagerness to take on more. I am supremely confident in my ability to upskill and do what I need to take on more and more, but sometimes this can be at odds with my choice of career.

Venture capital is not a fire-from-the-hip industry. Or at least, I believe that it is not when done well.

VC is an apprenticeship industry. It takes time to learn the craft. Sometimes that is hard for me to remember. I want to do more and take on more responsibility and have opinions on every company and every sector. But I have been doing this for less than a year. And I have a lot still to learn.

This week I got a reminder of that after hearing more experienced investors than myself talk about board governance. What a huge responsibility it is and all the perils that responsibility entails if its gravity is not appreciated.

After hearing about their trials and tribulations on various boards throughout their career, it really struck me how much more I have to learn.

I am so excited to be in this industry.

I love working with entrepreneurs and helping them build great companies.

But it is important to keep in mind that I don’t know everything. That this industry is a craft and like all crafts it requires reps and experience before you can become a master. Rome was not built with enthusiasm alone.

I write this post not because I am discouraged. Quite the opposite actually.

When I think about how relatively inexperienced I am and how much I still have to learn, I am not demoralized.

I am not daunted.

I am not intimidated or frustrated.

Instead, I am excited to get back to work and keep learning. To keep beating on my craft.

I think that is a pretty good sign.

The Monkey Trap of the Mind

Photo by&nbsp; Go Sourav &nbsp;on&nbsp; Unsplash

Photo by Go Sourav on Unsplash

I am currently reading Robert Pirsig’s Zen and the Art of Motorcycle Maintenance. It is a fascinating book with many concepts that could be the inspirations for future blog posts. One such concept is the idea of Monkey Traps.

In colonial times, monkeys were trapped using a hollowed coconut connected to a stake in the ground. A hole was carved in the coconut that was just barely large enough for a monkey’s hand to fit into. Inside the coconut would be food for the monkey such as a banana or rice.

A monkey would come along, smell the food, and reach his hand into the coconut to grab it. Unwilling to let go of the food and unable to escape, the monkey would be trapped.

Too often we are trapped in monkey traps of our own making.

Our thoughts, actions, and opinions are held on to with a vice grip, no matter the consequences or existence of contradictory evidence. What’s worse, our culture shames those who change their mind as “flip-floppers.” We live in such a constantly changing world that I’d argue that questions should instead be asked of those whose views and opinions never change.

This adherence to our own cognitive biases is damaging and dangerous in all walks of life, but it can be especially fatal in venture capital.

Venture capital is concerned with the cutting edge of what is next. When you operate in this world, things change. Fast. To hold on to your preexisting beliefs in the face of overwhelming evidence is a surefire way to make mistakes like investing in the wrong company, or even worse, passing on investing in the right one. That’s why I so respect VCs who show a willingness to change their mind. A16z and their famous “strong opinions, loosely held” mantra comes to mind.

This is something I struggle with myself. I have blind spots due to my internal biases. I sometimes fall into the trap of minimizing others’ achievements to make myself feel better. I think if we are honest with ourselves, we all have moments when we fall into these monkey traps.

But that does not have to be our destiny.

The first step is to admit that we do these things. The second is to actively fight against them.

Cultivate a curious mind and embrace information that causes you to question your pre-existing beliefs. When the goal becomes learning and moving ever closer to the truth, then evidence that violates your held beliefs becomes something to be celebrated instead of shunned.

Maintain relationships with people who hold you accountable. The most important relationships in your life are the people who are able to call you our on your own bullshit (I know that I need a regular and steady dose of that).

I say all this as someone who often sucks at walking the walk. But I am working on it.

And I try to grow a little bit better every day.

My Investment Checklist

Photo by  Jason Abdilla  on  Unsplash

I like checklists. You can do a lot with them. Help you stay on task. Focus your analysis. Remind yourself about things you might otherwise forget.

Checklists are great when looking at investments. Companies are complicated thing. Checklists can help you focus in on what is really important. I wanted to share my checklist of the things I look for when evaluating a startup.

Is this a hair on fire problem?

The first and the most important question. This one is not optional. If your startup is not solving a real problem for real people, you don’t stand much of a chance. It can’t be a nice to have. People don’t change their habits and make buying decisions for “nice to haves”. You either need to solve a top 2-3 problem your customer experiences every day or you need to create a product that is so incredibly compelling that using it literally creates tangible joy for your user. 95% of successful startups are in the game of solving problems. If your startup is in the 5% that creates unbridled joy in your customers, you can stop reading this article now, you’re probably fine.

The number one reason why startups die is because there is no market demand for their product. They aren’t solving a hair on fire problem. If the answer to this question is no: do not pass go, do not collect $200 dollars. I don’t care if your total addressable market is a million billion trillion dollars (which apparently every market is based upon pitch decks), if you aren’t solving a hair on fire problem for people, you are going to need to spend more time cooking on your product.

Does the founder fit the market?

Ahh the much-debated “founder-market fit” question. There is significant debate in the industry about just how important it is for a founder to have first-hand experience with the problem they are solving. I have written about my feelings in depth here. Suffice to say, I am a big believer. Entrepreneurship is hard. Like really, really, really hard. Like trying to write a blog about investment criteria while your wife is watching Season 5 of the Gilmore Girls (it should be easy to to ignore, but it is just so catchy. And I like this new Logan fellow, he is a much better fit for Rory than Dean or Jess.). But in all seriousness, entrepreneurship is brutally difficult and I want to be sure that an entrepreneur will stick with it when the night is cold and the chips are on the table. As much as I like to take founder-market fit into account, it is not a must for me. Experienced entrepreneurs can build excellent businesses. And people can fall in love with their customers’ problems without having experienced it themselves. BUT having a personal connection really helps. Founder-market fit is a nice-to-have, but not a must-have. It is something I always look for though.

Who is experiencing the problem?

Notice this question is not “how big is the market?”. Every single investment pitch I listen to talks about how epicly big their market is. Caring about big markets isn’t that helpful when every entrepreneur claims that every market is enormous. Furthermore, I think investors get too hung up on market size anyways. In venture capital, you are investing in the companies of tomorrow. Markets change a lot in 5-8 years, which is how long it takes a company to mature. Looking at the way that markets are today is less than helpful. What is much more important is to understand who the users/customers are for the product. If you truly understand who is going to use the product, you have a much deeper insight into how big this company can be. You can form an opinion about where the company is today and where it will be tomorrow. Understand the who, and you can develop a thesis on the where.

Is there an axehead here?

This is the most recent addition to the list. I unapologetically got this concept from Fred Wilson at USV (though I think it has its true epistemological roots in Thielism). This question is about a startup’s market entry strategy. An axehead strategy is when a startup enters a niche market (sharp edge of the axe), gains momentum, and then is able to carry that momentum into adjacent larger markets (the wedge of the ace). This along with our prior question on who the customers are is my substitute for “how big is the market?”. I am much more interested in a truly compelling product with a smart market-entry strategy, than a company playing in a market 2.5x the size of the world’s GDP (you laugh, but I have seen some wild assumptions in pitch decks before). Truly transformational startups often seem to conjure a brand new market out of thin air. This is how they do it.

Can this team execute?

Team, team, team, team. When you are an early stage investor, team is everything. Later stage investors may focus on other things, but team is the alpha and the omega of early stage investing. A strong team will be able to drive a mediocre idea to a decent outcome. A weak team will snatch defeat from the jaws of victory even with the best idea ever. At the early stage of a company the team is absolutely key. And this makes sense. Without momentum all you’ve got is the blood, sweat, and tears of your team. And with small teams, each person is responsible for a huge portion of the value of the company. The trick is to really understand if this is a team that can execute on their idea. A great way to do this is to spend time on site with the company and really get to know the ins and outs of the team. The best way to do this is to help fill gaps on the team with operators out of your own network that you know can get the job done. Either way answering the question of whether or not this is the right team is absolutely vital, especially at a company’s earliest stages.

It’s important to know that these items are always evolving. This is what I look for in investments today. I think it is good to memorialize that. If your company checks all these boxes, reach out.

I want to hear from you.

Y u do dis doe?

Motivations behind venture capital and entrepreneurship

In our day and age there is a lot of airtime and energy spent on the “What”. What people are doing in their career. What is going on with the weather (hint: if its early March in Columbus it probably sucks). What movie won the Oscar. What outrageous remarks politicians made yesterday. What is important. What has its place, but I want to use this post to talk about the “Why”.

Because I think Why is very important.

Why is what gets you through the cold nights when your back is up against the wall. Why sets successful people apart from unsuccessful people. And Why sets world-changing people apart from successful people.

Why is important, but it is often overlooked.

Your Why is what motivates you. It’s the reason you are doing or acting the way you are. Too often we stop at the What and never ask about the Why.

There are two instances I see regularly where I think that people need to take some time to figure out their Why.

The first is people trying to break into venture capital. Believe my, I get it. It is a cool job. You don’t have to tell me twice. But there are a lot of cool jobs out there. I think people too often get sucked in by the glitz and glam of working with big name brands in cutting edge industries. As awesome as working in venture is, I can assure you that it is not as glamorous as it appears from the outside looking in (most things aren’t). Behind the scenes, things are complicated, messy, and every deal is closed with blood, sweat, and LOTS AND LOTS of paperwork. There are also better (and easier) ways to make money (especially in finance) if that is what motivates you.

The one thing I can tell you about getting in to venture is that it is hard. Trust me. Firms are often top-heavy and rarely hire outside of fund cycles. And there is always an abundance of people looking to get in to the industry. It can be done, but it isn’t easy to get a job, and once you do, it isn’t as glamorous as it looks on tv. Who is a good fit for VC?

If your Why is that you obsess over being a part of building things that will change the world, venture might be a fit for you.

If your Why is a deep desire to learn by constantly diving headlong into industries you didn’t even know existed the day before, venture might be a fit for you.

If your Why is building relationships with people doing exciting things and providing them with value without any strings attached or expectation of return, venture might be a fit for you.

If you want to work in a sexy industry and become rich, I’d look elsewhere.

The second area where I think the importance of Why is severely understated is when evaluating founders. I have talked about founder motivation before, but I really believe its importance cannot be overstated. If you thought venture capital was hard, wait until you see entrepreneurship. I like Brent Beshore’s description of entrepreneurship as a “daily knife fight”.

I, like many others, watched movies like The Social Network and read books about the great tech titans and thought to myself “hey I could do that.”

After almost a year working as a venture capital investor, my tune has changed to “hey with a great idea and a lot of super smart people around me, I could do that. But would I ever want to?”

I have seen first hand how hard company building is. And I sit in the privileged seats. I get to grab my 6-1/4” 7.5oz heavy duty utility knife (I spent a summer as a knife salesmen before college and still geek out about kitchen cutlery) and hop into the trenches every day. But when my day is done, I climb back out and get to set my knife in a regulation bamboo knife block (a well sheathed knife is a safe knife).

Entrepreneurs are not so lucky.

Their whole life is the trenches. If their company is successful, they could spend more than 10 years down there before they get a real breather. If they aren’t so lucky, their stay will likely be much shorter.

Kitchen cutlery brawl metaphors aside, building something out of nothing is never easy. It requires 100% commitment. There are going to be times where nothing is working. There are going to be times where things are working but a seemingly “better” opportunity comes along.

A lot of entrepreneurs like being entrepreneurs more than they like being founders.

They like the accolades and admiration more than the accountability and the brutal decisions.

They like the business cards more than the business.

Rare is the entrepreneur that is able to see it through to the finish line.

And every single one of them has a Why that gives them a fire to preserver. Whenever I meet an entrepreneur, I am looking for that Why. I want to see a founder starting a business because they think that if they don’t build this company, no one else will.

And the world needs this company too much to risk that happening.

Due Diligence: How Much is Too Much?

Venture Capital Technology Startup Due Diligence

A big part of my job is due diligence. This is a fancy bit of jargon that gets thrown around a lot in finance. All it really means is doing research to back up whether things that someone has claimed about their company are true. My boss is fond of reminding us that in our job we need to “trust, but verify.” Due diligence is that verification.

Spend a little bit of time in venture capital and you quickly discover that the rigor of different firms’ due diligence processes vary greatly. Some firms spend an incredible amount of time and resources digging into every small detail of a company. Others run light processes that can be completed quickly. At Rev1, we have what I believe to be a relatively robust process compared to other investors at our stage.

This spectrum makes sense.

Firms with more specific sector-focuses are likely subject matter experts on the spaces they invest, cutting down on time necessary to get themselves up to speed.

Firms that invest across a series of stages will likely have leaner due diligence processes for their earliest investments and more in-depth processes for their later investments. The idea here being that the effort per dollar of investment remains relatively constant. More dollars. More effort.

There is no right answer on what is the perfect amount of due diligence.

But there are wrong answers.

Conducting no due diligence can’t be correct. But doing too much diligence makes your life miserable (and the entrepreneur’s life you are working with even more so).

When I was at Carlyle, one of our founders was fond of saying “you should never focus on conducting the most complete, perfect due diligence. By the time you will have completed it, the investment round will no longer be open and it won’t even matter because you will have talked yourself out of doing the deal anyways.”

I think there is a good amount of truth in this. Venture capital is a risky game. You will never be able to conduct such a thorough due diligence process that you are able to remove ALL the risk from a deal. If you were able to, they wouldn’t exactly be able to call it risk capital investing now would they?

So the correct amount of due diligence lies somewhere between 0 and 100. But where?

I have been thinking about this question a lot recently. The answer (as with most things in business) is that it depends. It depends on the characteristics of your firm and the demands of your stakeholders.

My views on the optimal amount of due diligence have recently been informed by my reading of Fooled By Randomness by Nassim Nicholas Taleb. This is an excellent book which I highly recommend. The author is a veteran options trader and a foremost expert on probability and randomness.

Two concepts from his book have especially informed my views on due diligence.

The first is the idea of satisficing.

Satisficing is a decision making strategy where someone analyzes different alternatives until they find one that reaches a minimum acceptable threshold. And then they stop. I believe this concept should also be applied to investment due diligence.

Your goal should be to reach the minimum required confidence threshold necessary for you to make an investment while expending the least amount of effort and resources necessary to get there. Any additional due diligence past that point is a waste of your, and the entrepreneur’s, time.

This minimum required confidence threshold will change from person to person and firm to firm, but I do think there is value in understanding the idea of satisficing to help avoid using unnecessary time and effort. As with many things in life, due diligence follows the law of diminishing marginal return. Each additional level of comfort you can reach in an investment requires exponentially more and more effort. This is why it is so important to reach your required confidence threshold and to go no further. Even pushing on just a little bit can require a colossal amount of energy.

Not only is too much due diligence a waste of time, money, and energy, but it could actually lead to some pretty large cognitive blind spots.

The second concept from the book that applies to due diligence are the negative side-effects of conducting too thorough of an analysis.

Too thorough of an analysis?

Yes, that is right. Taleb points out that one of the major cognitive biases exhibited by people is that their confidence in the likelihood of a given outcome increases linearly with the amount of effort they expend analyzing the chances of its outcome. It’s the effort people put in to an analysis more so than the analysis itself that tends to influence people’s expectations around an event.

People trick themselves into thinking that more analysis = more certainty, when nothing could be further from the truth. The wrong kind of analysis will be a red herring that increases your confidence in, without actually increasing the accuracy of your predictions.

Venture capital due diligence is an environment ripe for this sort of error. In early stage VC, the risks are so incredibly high for every company. Conducting an excessive amount of due diligence doesn’t change this fact. But it does make us feel better about the investment. This dislocation between the actual risks of an investment and someone’s perceived risks can lead to incorrect decision making and overconfidence in those decisions.

The true danger is not in the risks itself, but in conducting so much analysis that we convince ourselves that the risks no longer apply.

With the ideas of satisficing and the dangers of over-analysis in mind, I believe the best way to conduct due diligence is to seek the no. “Seeking the No” is a cool sounding phrase that I just made up on the spot. The concept is to figure out the few things that would immediately make you say no to an investment and try to validate whether they are true or not. Work backwards from biggest things that would immediately make you cut bait with the company. If you find out any of these hot button issues are true, you can pack up shop right then and there. No more analysis necessary.

Assuming you can attain some comfort that the company does not breach any of your “DO NOT INVEST” red flags, then you can proceed with seeing if they fit what you actually want to see in an investment. What exactly those attributes are that you should be looking for is a topic for another post, but following this strategy of seeking the no should help you focus your efforts on only the investments that truly warrant your time.

Venture capital due diligence is a tale of modern day Sisyphus. You will never be able to truly understand all the risks inherent in a business. Trying to do so wastes precious resources, while giving yourself a false sense of security. Conduct the minimum amount of due diligence necessary to reach either a no or a yes. You will thank yourself for it. And so will your entrepreneurs.

Pink Dragons, Serendipity Vehicles, and Mentos

Serendipity Startups Tech Venture Capital

When I was a kid one of my all time favorite things to do on friday nights was to have a movie night (who am I kidding, that is still one of my favorite things to do). My mom and I would go to Blockbuster to pick out a movie or two and then we would skip next store to Papa Murphy’s to pick up some pizza (I will contend till my dying breath Papa Murphy’s is by far the most underrated pizza on the planet. So good). One of the movies I distinctly remember watching during multiple movie nights was Serendipity The Pink Dragon. Serendipity was a pink sea dragon who lived on a magical island with all of her friends learning life lessons about friendship. I have no idea why we ever picked this particular movie out, but I do remember watching it more than once (to this day, my go to nickname for a Lapras in any Pokemon game is Serendipity).

I was reminded of Serendipity the pink dragon while listening to this interview from Sara Dietschy with Nik Sharma and David Perell. This episode is definitely worth listening to. They cover a lot of ground from influencer marketing to direct-to-consumer brands to their own stories and how they got where they are today. As part of this last part, they spoke about the role that serendipity had in each of their lives. They drew a line in the sand between serendipity and luck. Luck is something good that just happens to you. Serendipity is something good that happens to you because your hard work and patience put you in a position where it could happen to you. I love this distinction.

If you talk to anyone with a modicum of success in life, the vast majority can point to a handful of “lucky” events where they caught a break or were given a chance to take on a project they were woefully underqualified for. Rare, however, is the successful person who had this happen to them while watching Netflix and eating cheetos on a Thursday afternoon.

Luck is a factor in everyone’s story. What differs is how prepared people are to take advantage of the situation when the dice start rolling their way.

That is where Serendipity Vehicles come in.

Serendipity Vehicles are a concept coined by David Perell in this post. He talks about purposefully building structures that increase the likelihood of both serendipitous things happening to you as well as increasing the chances that you are able to take advantage of them when they occur. Serendipity vehicles can range from simple structures like attending a dinner party to more much more complex things like writing books.

This blog is one of my serendipity vehicles. Twitter is another. Both require relatively minimal, but consistent, effort to maintain. Both have lead to significant outsized opportunities far and above what I would’ve ever expected.

Now all of this talk of lifestyle design may sound complicated, but I think the most important thing is simply the way you approach it. I think the best way to think about designing your serendipity vehicles is to make yourself into a Mentos. Mentos are a type of spherical candy that are sold all across the world. To be perfectly honest, I think they are pretty average. What is not average are the explosive effects they have when combined with any sort of carbonated beverage (but especially Diet Coke). There is a whole lot of science behind why this happens, but the short of it is that even though Mentos looks like smooth spheres, on a microscopic level their surfaces are very rough. This increased surface area acts environments where bubbles can form, launching soda up into the air. The key is the surface area.

You can make your life resemble Mentos by increasing your surface area so you have a lot of different places where serendipity bubbles can form.

Say yes to thing even if they are outside your comfort zone.

Cultivate curiosity in a broad range of subjects and areas.

Go out of your way to go to new places and meet new people.

Jump at opportunities even if the timing is not always ideal.

Create excuses to talk with interesting people.

Provide value to people instead of just asks.

At the end of the day, your goal should be to have as many areas in your life where serendipity can form as possible The challenge is to recognize serendipity and then make sure you are able to take advantage of it.

This advice is equally true for both individuals and startups.

Well designed startups are a lot like giant serendipity vehicles. A lot of work goes into designing them so that they are in a position to shoot for the stars as soon as a serendipitous customer connection or technological development breaks their way. As a founder you need to balance the need to stay focused on what you are building with providing yourself as much surface area as possible in order to take advantage of connections with investors, talent, customers, etc.

I can’t tell you what the right balance for that is. You will need to figure that out for yourself. But I can tell you what the wrong balances are. There are two.

1) Ignoring any thought of the outside world to focus solely on your business.

2) Ignoring your business to focus solely on hoping something happens in the outside world.

Everything in between is fair game.

No matter where you land on the spectrum between focusing your time and energy on building your business and increasing your surface area to optimize for serendipity, there is one lever that you can pull to maximize your chances for success.

Burning responsibly.

Responsibly managing your burn rate as a startup is one of the most important things you do as a founder. Burn too fast and you won’t get enough at bats to have something serendipitous happen for your business, no matter how much you optimize for it.

As an individual and as a business, design your life so that you can take advantage of serendipity when it comes knocking at your door.

That is how you and your company achieve success.

Board to Death

Photo by  Drew Beamer  on  Unsplash

Photo by Drew Beamer on Unsplash

The world of Venture Capital is very different than it appears from the outside. I have been surprised by many things since becoming an investor, but none more so, than the difficulties surrounding boards. From the outside looking in, boards appear simple. Incentives are aligned. Everyone wants what is best for the company. Experience and expertise are leveraged to make the company the best it can be.

If only it were that simple.

Properly managing boards as an entrepreneur is a dance. Defer to them too much and you will lose the magic that made board members want to support you in the first place. Don’t heed them enough and you will make avoidable mistakes and miss out on opportunities.

The biggest mistake I see entrepreneurs make in respect towards their boards is that they think about their boards with the wrong mindset. The second you grow mistrustful of your board and start thinking of them as antagonists trying to put up hurdles in the way of your company, the chances your company is going to become successful with you at the helm plummets to almost zero.

Alright, Erik chill out. Classic Berg exaggeration.

No I am serious. A toxic board relationship is THAT deadly. It may not happen that day. Or that month. But eventually allowing the relationship between you and the board to fester will come back to bite either you or the company. Or both.

I believe the best metaphor for a well run board is to think of the board as your boss. Because that is exactly what they are. The keys to a healthy relationship with a board are the same as with a healthy relationship with your boss.

Communication

As with most relationships in life, the most important thing when managing a board is communication. Regularly update your board (even, and especially, outside of official board meetings) on your successes, failures, and any ways that they can help. I maintain that investor updates are one of the highest leverage activities any entrepreneur can do. Keep your board in the loop with what is going on with your company and they will be able to leverage their experience to help you make the best possible decisions. Note that I am not saying to do whatever your board tells you to. If they knew what was best for your business in every possible scenario, they would’ve started your company themselves. Rely on your intuition. It got you this far. But your board has many lifetime’s worth of additional experience than you do. Use it. Take it into account and leverage it to make the best possible decisions. To do otherwise is simply foolish.

Coaching

Just like all good bosses, boards have a responsibility to develop the CEO. Most startup entrepreneurs have not built a business before. Those that have, in all likelihood, have done so in a different sector or space. The board has a responsibility to coach and mentor the CEO to be the best that they can be. This means giving your CEO the tools they require to be successful. Equip them with resources and connect them with mentors who have been successful in this space before. A board’s fundamental job is to protect the interests of a company and its employees. The best way to do this is by making sure that the CEO performs at their absolute peak. If you as a board member believe your duty is to provide oversight without nourishment, advice without mentorship, you are neglecting your responsibilities to the company.

Accountability

Communication is a two way street. Yes, the impetus lies squarely at the feet of the entrepreneur, but at the end of the day, they will only feel empowered to bring everything to the attention of the board if the board knows how to give appropriate levels of feedback. Successful boards design structures where they can hold their CEOs accountable in a constructive way. I think Fred Wilson has the best approach for ensuring that feedback loops are tight and honest. Entrepreneurs, don’t get defensive when the board gives you feedback. Every single one of their incentives is aligned with the success of the company. So are yours. Remember that they trying to help you make the company the best that it can possibly be.

From the outside looking in, no one will know how healthy your company is. You can survive with a bad board relationship for a little while. But, if you are consistently neglecting your relationship with your board, eventually it will blow up in your face. The key is to leverage their experience and remember that they are on your side.