Is it dark inside me?

I got a very cool card from the team at Pentagram with a bunch of questions from their children. One of them was, “Is it dark inside me?”

When asked by a 5 year old child, I think it’s cute. But, If asked by a middle aged man, I think this question is scary.

The words are the same, but the assumptions I make create different meanings. I would engage the curious child. I would run away from the troubled middle aged man.

In this example, it is obvious that 80% of the meaning comes from me and not from the person asking the question. But, it has me thinking about the meaning I take away from conversations with founders and how much is based on what I bring to the conversation and how much is based on what the founder actually said.

If 80% of what I take away from an interview

Continue reading "Is it dark inside me?"

Is it dark inside me?

I got a very cool card from the team at Pentagram with a bunch of questions from their children. One of them was, “Is it dark inside me?”

When asked by a 5 year old child, I think it’s cute. But, If asked by a middle aged man, I think this question is scary.

The words are the same, but the assumptions I make create different meanings. I would engage the curious child. I would run away from the troubled middle aged man.

In this example, it is obvious that 80% of the meaning comes from me and not from the person asking the question. But, it has me thinking about the meaning I take away from conversations with founders and how much is based on what I bring to the conversation and how much is based on what the founder actually said.

If 80% of what I take away from an interview

Continue reading "Is it dark inside me?"

To achieve your goals be more confident not more disciplined

I set goals to achieve something in the future. I identify daily activity that I think will build toward that goal. I commit to prioritize these daily activities during the time between now and achieving the goal.

Then I do something else.

I know it conflicts with the priorities I set with my long term goal in mind, but, in the moment, the value of the shiny object feels clear and present — and I find myself chasing it.

I used to blame a lack of discipline and wonder why I could not establish new habits. But, after some reflection, I think my problem is not a lack of discipline but a lack of confidence — specifically confidence in the priorities I set and the daily activities I committed to — the belief that these are actually the steps to achieve my goal is the thing that fades — aka confidence.

When I have confidence, the discipline is there. There

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Just listen

The other day I had a really tough conversation with a founder. After an hour, he told me he really appreciated the help, felt ready to go face the challenges we had discussed and had new confidence that he could manage through his current difficulties. I was glad he found it valuable and told him so. Over the course of the hour I may have said 7 words.

In my judgement, he did not need more than that — he just needed me to listen.

I hate the child/parent parallel for the founder/VC relationship for a million reasons however, this listening practice comes from the best parenting advice I ever got — but really it is the best relationship advice I ever got.

When my daughter was a day old, my father saw me worried about leaving the hospital, wondering if I would be a good parent (or even a functional one) and after asking me what

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If I were an NFL owner here is what I would think about the players’ choice to #takeaknee

This group of men, the players in the NFL, have spent their lives on the field working to keep their knees off the turf. They have spent their lives off the field bowing to no one. They have pushed themselves physically, intellectually and socially. That is the only way they could make it to the NFL.

So, what does it take for these strong, intelligent, socially conscious, brave, black men to rest their knees on the ground? Remember what this is about. Understand why these men are kneeling.

Since they were young boys, these players’ ability to stay on their feet has been a ticket to something bigger. From Friday night lights to scholarship Saturday to earning the right to play on Sunday they have kept their feet moving. To get here, they have stood tall through lots of shit. These men were born special. They have unimaginable gifts. Throughout their

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Walk The Ridiculous Path

A startup begins when someone who doesn’t know better embraces a breakdown in the traditional ways of perception — when you understand a customer in a new way or see a solution to a problem people didn’t even know they had. A startup begins with a seemingly ridiculous experiment.

Ridiculous experiments are strangled in a culture that idolizes success and nurtured by one that accepts failure. When you chase success, you try to win at the same game as everyone else. You chase the current big winners by acting like the current big winners. In the effort to look or act like someone else, to be closer to their path, you forget that start up success lies at the end of paths not yet taken. When you chase success you fear failure and forget to do ridiculous things.

When you chase success, you accept that there is “the way” and listen when

Continue reading "Walk The Ridiculous Path"

Walk The Ridiculous Path

A startup begins when someone who doesn’t know better embraces a breakdown in the traditional ways of perception — when you understand a customer in a new way or see a solution to a problem people didn’t even know they had. A startup begins with a seemingly ridiculous experiment.

Ridiculous experiments are strangled in a culture that idolizes success and nurtured by one that accepts failure. When you chase success, you try to win at the same game as everyone else. You chase the current big winners by acting like the current big winners. In the effort to look or act like someone else, to be closer to their path, you forget that start up success lies at the end of paths not yet taken. When you chase success you fear failure and forget to do ridiculous things.

When you chase success, you accept that there is “the way” and listen when

Continue reading "Walk The Ridiculous Path"

My New Calendar System

Over the past few months I’ve been trying an experiment with my calendar. It’s working and a friend encouraged me to share it. Visuals help so I pulled screen shots of my calendar for the up coming week and the same week a year ago. It’s a holiday week, so not the busiest, but absent some typical breakfasts and evening events it is representative and illustrates the difference.

This was my calendar the Week of Labor Day 2016

To avoid burying the lead, my new system is 4 meetings a day and nothing scheduled more than 7 work days in advance. I have meeting slots at 10:15, 11:15, 2:15 and 3:15. The rest of the day is open for internal meetings and work. Lunches are few and far between. There’re exceptions to rules, (board meetings, the First Round Partner meeting etc.) but this system is the guiding principle and it’s

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Trust your own mind

When you are doing something that has never been done before, it can be really hard to trust the stepping stones of your experience to carry you through any decision you have to make. It helps to have someone who is not looking for the answer, but instead is looking for the answer in you and pointing it out so you can see it too.

An advisor’s job is to build confidence and help founders discover their best answer to any challenge. It is not to be a critic.

I have opinions (and work to deliver them unvarnished) but I have found the lack of criticism creates an empty space and founders fill it. They fill it with creativity and incredible execution. To criticize implies I know the answer — that I can discern good from bad. I probably can’t. I probably don’t have context. So the founder (and my investment) are better served

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VC/Founder partnerships and the cycle of destructive deduction and creative induction

I recently read Boyd (h/t and thanks to rands) and it got me thinking about the role of the founder and the VC in a successful partnership. There is a stark difference in the mindset and approach required for founders and VC’s to maximize their contribution to a company. Winning depends on each knowing their role and respecting the role of the other.

The founders I work with know that a critical part of my working style is knowing when to be quiet. I prefer to create silence, even awkward, uncomfortable pauses after a question or a reframing of a challenge because when founders step in and fill the gap in conversation, the quality of the discussion goes up. Every. Single. Time.

My job is to help take a mental model apart. I push founders to pull at the building blocks of the model in an effort to topple the

Continue reading "VC/Founder partnerships and the cycle of destructive deduction and creative induction"

VC/Founder partnerships and the cycle of destructive deduction and creative induction

I recently read Boyd (h/t and thanks to rands) and it got me thinking about the role of the founder and the VC in a successful partnership. There is a stark difference in the mindset and approach required for founders and VC’s to maximize their contribution to a company. Winning depends on each knowing their role and respecting the role of the other. The founders I work with know that a critical part of my working style is knowing when to be quiet. I prefer to create silence, even awkward, uncomfortable pauses after a question or a reframing of a challenge because when founders step in and fill the gap in conversation, the quality of the discussion goes up. Every. Single. Time. My job is to help take a mental model apart. I push founders to pull at the building blocks of the model in an effort to topple the
Continue reading "VC/Founder partnerships and the cycle of destructive deduction and creative induction"

VC/Founder partnerships and the cycle of destructive deduction and creative induction

I recently read Boyd (h/t and thanks to rands) and it got me thinking about the role of the founder and the VC in a successful partnership. There is a stark difference in the mindset and approach required for founders and VC’s to maximize their contribution to a company. Winning depends on each knowing their role and respecting the role of the other.

The founders I work with know that a critical part of my working style is knowing when to be quiet. I prefer to create silence, even awkward, uncomfortable pauses after a question or a reframing of a challenge because when founders step in and fill the gap in conversation, the quality of the discussion goes up. Every. Single. Time.

My job is to help take a mental model apart. I push founders to pull at the building blocks of the model in an effort to topple the

Continue reading "VC/Founder partnerships and the cycle of destructive deduction and creative induction"

VC/Founder partnerships and the cycle of destructive deduction and creative induction

I recently read Boyd (h/t and thanks to rands) and it got me thinking about the role of the founder and the VC in a successful partnership. There is a stark difference in the mindset and approach required for founders and VC’s to maximize their contribution to a company. Winning depends on each knowing their role and respecting the role of the other.

The founders I work with know that a critical part of my working style is knowing when to be quiet. I prefer to create silence, even awkward, uncomfortable pauses after a question or a reframing of a challenge because when founders step in and fill the gap in conversation, the quality of the discussion goes up. Every. Single. Time.

My job is to help take a mental model apart. I push founders to pull at the building blocks of the model in an effort to topple the

Continue reading "VC/Founder partnerships and the cycle of destructive deduction and creative induction"

The one startup debt you can’t pay back

There are a few lines in the Silicon Valley that have shaped how we build products and companies. They all encourage founders to take on “debt” and find the fastest path to market. “Move fast and break things” “If you’re not embarrassed by your first product, you launched too late” “Do things that don’t scale.” This focus on speed is successful. For the chance to increase velocity, compromises are made around product quality and technical scalability. We delay marketing efficiency and ignore unit economics. Initial pricing in the enterprise space is optimized for adoption rather than margin. In the early days, partnership terms with suppliers may be far from ideal and often a blind eye is the best tool to navigate regulatory hurdles. And, when it comes to hiring, founders take on diversity debt. We fill seats with those we know or at least those we know are capable and accessible. We move
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Different symptom. Same disease.

Reading about how some men treat women in this industry — and hearing about similar, crazy experiences from female friends —reminds me of the Stanford Prison Experiment — when people feel like there is no recourse for those they attack, they do deeply irresponsible things. I believe men are in for a surprise as this subject moves from hidden whispers to full throated roar. Allies will be found. Change is inevitable. The only question is how fast it will happen. Over a year ago Jessi Hempel lit up gender in tech and how we talk about it. The conversation fizzled. Now we are talking about it again. Different symptom. Same disease. Women have long been overlooked despite incredible talent, intelligence, and hard work. But, as society becomes more transparent and inherently networked, everything we do becomes more relationship driven. Talent is harder to ignore, intellectual horsepower gets highlighted, credit more naturally flows to those responsible,
Continue reading "Different symptom. Same disease."

Different symptom. Same disease.

Reading about how some men treat women in this industry — and hearing about similar, crazy experiences from female friends —reminds me of the Stanford Prison Experiment — when people feel like there is no recourse for those they attack, they do deeply irresponsible things. I believe men are in for a surprise as this subject moves from hidden whispers to full throated roar. Allies will be found. Change is inevitable. The only question is how fast it will happen. Over a year ago Jessi Hempel lit up gender in tech and how we talk about it. The conversation fizzled. Now we are talking about it again.

Different symptom. Same disease.

Women have long been overlooked despite incredible talent, intelligence, and hard work. But, as society becomes more transparent and inherently networked, everything we do becomes more relationship driven. Talent is harder to ignore, intellectual horsepower gets highlighted, credit more naturally flows to those responsible,

Continue reading "Different symptom. Same disease."

Stock options vs career options

When someone decides to join your startup, they are betting on the future. Belief in the potential value of their options is one driver of the decision. Most CEOs I work with are very good at explaining the value of options when it comes to equity incentive plans. But options are not just contractual rights to buy stock in the future — people also care about the career options available if they make meaningful contributions at a startup. They want to know where they can go inside the company and how their experience will make them more attractive if and when it is time to move on from the company. As an industry, we forget this and I don’t see enough focus on planning and explaining career paths for employees or describing the career options that are uniquely available to great people who work at startups. This is a mistake. Just like
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A length of rope

One of the most limited and important resources founders have is emotional energy. I think of this emotional energy as a rope. The longer the line can stretch, the further you and your company can go.

Imagine you are given a length of rope and asked to stretch it as far as it will go. What would that look like? You would secure one end, smooth out any ups and downs, kinks or knots that shorten the rope and then pull it tight. A straight line allows the rope reach the furthest.

The job of a founder is to take the emotional rope you have, tie a group of talented people to a vision — and then pull like crazy. When the best leaders begin to pull, the rope gets tight — it rises from the murky depths and creates a straight line between the team and the vision. It may strain and creak, ringing

Continue reading "A length of rope"

A length of rope

One of the most limited and important resources founders have is emotional energy. I think of this emotional energy as a rope. The longer the line can stretch, the further you and your company can go. Imagine you are given a length of rope and asked to stretch it as far as it will go. What would that look like? You would secure one end, smooth out any ups and downs, kinks or knots that shorten the rope and then pull it tight. A straight line allows the rope reach the furthest. The job of a founder is to take the emotional rope you have, tie a group of talented people to a vision — and then pull like crazy. When the best leaders begin to pull, the rope gets tight — it rises from the murky depths and creates a straight line between the team and the vision. It may strain and creak, ringing
Continue reading "A length of rope"

Great cultures are legible, not transparent

At lunch with a good friend (and leader) talking about company culture and the rise of transparency as a cultural imperative. He was very clear that transparency is not the point. He said, “Great cultures are legible, not transparent.” It struck me that the cultural transparency meme is based on the assumption that if everyone can see what is going on, everyone will understand why/how it is going down. But, seeing is not always believing and it is almost never the same as understanding. A simple search offers tons of resources explaining why and how to create a culture of transparency. Being open about decisions and data is taken as a measure of care and respect for members of the team. Access to information is conflated with everyone understanding the process that was wrapped around the information and resulted in decisions and actions. In my experience, what the team
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