Ode to the VC who passed

Monday, you made a mistake. Today your ignorance is dissolved in confidence. Cocktail goes down easy, hangs over like a bitch. In 3 years, my success will catch in your throat. Unscratchable itch. In 10 years you’ll know what you lost but not why. Broken switch. No relief. No sleep. On repeat. Choking on desiccated birthday cake left out over night. No milk. Can’t eat. Privately peering through fog for meaning in the shadows of your career. Out of time. Obsolete. So close to greatness but out of tune. Your past is bright. Your future is not immune. This one is going to be hell. You “wouldacouldashoulda.” I’ll never tell.

Ode to the VC who passed was originally published in sneakerheadVC on Medium, where people are continuing the conversation by highlighting and responding to this story.


When someone disappoints me, I feel like they did something wrong or failed in an absolute sense, but really they just did something I did not expect. I am disappointed because they have failed to meet my expectations. I set the expectations. They are mine to sit with and tend to; Mine to watch as they change with time; Mine to communicate; Mine to adjust or abandon. When expectations are not met, instead of only questioning the person who did not deliver, taking a hard look at my role is much more productive. Mistakes are the foundation under the learning curve and mistakes should be expected, planned for and embraced by leadership (or in any relationship). Did the expectations allow for mistakes along the way? Did the person know they were failing to do what you expected? Did I offer support the moment I sensed they would come up short?
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Matters of Narrative

I sit in the meeting, engaged in the conversation but not landing my point. I put my idea out there, but no one latches on and the tangled mess grows and tightens. Just as I start feeling like my calendar needs a checkbox for “endless,” someone else makes a point. And, while I am thinking “I just said that 20 minutes ago” and expecting their voice to get lost in the wind too, it doesn’t. It rises above the dust kicked up by clashing factions, catches the light and draws the full attention of the room. The energy of the debate is channeled into consensus and entropy turns to decisive action. Why does this happen? Didn’t I say the same thing that moved the room forward? Why wasn’t I heard? Are you listening? WTF? There are three parts to consider:
  1. The situation
  2. The audience
  3. Me
Young woman or old man? What’s
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Fire fighting and company building

Starting a company is easy. Leading a company is the hardest job in the world. A few founders I work with describe their days as fighting fires. The minute one is out, another one flares up. Exhausting. Perpetual. When I was a CEO, everything was on fire most of the time. Consensus is find the root cause, the match that lights the fire. No matter how painful it seems, blow it out. This is totally logical. A match can cause a forest fire. A match is easy to blow out. Focus on the match. Avoid the fire. But, startups are not logical and the evolution of my company moved fast— the pace of change kept the root cause of most challenges close enough so I could see the flame but never reach it with my extinguishing breath. I chased the flame, rushing through the forest of new hires and new managers, detained
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If it ain’t broke, keep digging

Founders have to be detectives — looking for what is broken and building the solutions that will fix it. Seeing what doesn’t work is easy, asking why it doesn’t work is natural and I get a dopamine hit from solving a problem. I take the first answer that is correct enough...move fast, right? The danger is good enough is usually not the best answer and sometimes the good enough answer makes it impossible to discover the idea that leads to breakout success. Imagine you are a detective. Someone reports seeing a suspicious person heading into the woods with a shovel and a heavy bag over their shoulder. You take a K-9 team into the woods, the dogs start to go crazy over some ground that seems disturbed and you tell the forensic team to dig. After a little while, they find a cat buried in a shallow grave. Disappointed, you close the
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Who is the CEO?

I met with a pair of awesome founders the other day who have worked together for a long time, have been friends for even longer and, now, have started a company together. Their roles were as split as their personalities, one focused on product and growth and the other focused on sales and technology. If I am really honest, as we started talking I didn’t know who was the CEO. One of them spoke fast and frequently, jumping in and around and over every question and each answer his co-founder gave. As his hands painted a picture of the future, the sparks that flew from his fingers were reflected in his eyes and I could see the vision. The other was more reserved, critiquing the architecture of the market and drafting the engineering effort required to withstand the weight of such a massive opportunity. He pointed to strengths in response to
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Celebrate small wins

The other day, A Dorm Room Fund partner sent me a small gift with a note. It said,
At MIT we learn to celebrate the small wins of our friends because they won’t themselves.
It was a great reminder that it’s healthy and necessary to celebrate small wins. The startup world is full of big dreams and unbelievable aspirations. The driven people who pursue careers in this industry are focused and thrive on the chase of the impossible. As a founder I moved too fast through successes and validation because the scale of my aspirations perpetually dwarfed the current victory. To do the impossible, I had to believe when no one else did — I had to make it real and pull it forward in my mind, describe it in great detail to anyone who would listen and everyone else who wouldn’t. My company was the one sacred thing I poured everything into and
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Grade Inflation

Everyone does performance reviews. Most performance reviews are a joke. If you have a company under performing by 50% and 75% of employees are rated as exceeding expectations — how is that possible? If you have a company over performing by 50% and 75% of employees are rated as exceeding expectations — what does that teach you? I know there are a few very smart founders working to fix the process of reviews, feedback and management with software products and I am rooting for them so we can all stop wasting so much time on grade inflation.

Grade Inflation was originally published in sneakerheadVC on Medium, where people are continuing the conversation by highlighting and responding to this story.

The fear is real. I listen.

“I honestly have no idea what I am doing. I know a big challenge is coming and it is going to take a lot of resources to overcome it. If I don’t solve this problem, in 18 months we are screwed, but today, I can’t spare the resources or make time to focus here. I can’t balance urgent or important when the answer is both and I can’t hit my milestones and maintain my runway because even if I do, it will just lead to stalling in a year when we are not ready for what I know is coming. I just need to solve this structural issue. Maybe I need better people but I am scared I’m shitty at hiring because my last exec hire is drowning and doing everything he can to pull me down with him. Tripling this year doesn’t matter if we are flat after that…I
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I’m sorry, I can’t

If it’s not a priority, just let me know. Don’t say you’d love to get together…later. Just say no. You might miss something, but you’re the expert on prioritizing your time. You do you. No harm. No hard feelings. But just tell me because knowing I am not a priority for you is very helpful to me and my priorities. When I was just starting to think about finding a role in venture capital, there were a few people, senior GP’s at top funds, that I reached out to ask for time and advice. The first did not respond. I assumed I was not a priority and after one follow up attempt, let it go. Is he disorganized? Bad at eMail? A little arrogant? Not sure. The second wrote back after a “warm introduction” letting me know he was excited to meet, but couldn’t do it for a few months. I was
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Truth or Victory

In meetings where there is debate or a decision must be made, I am tempted to win at all costs. I can get pulled over the edge and work to win the fight — the search for truth can be eclipsed by the gravitational pull of victory.

I know this is happening when the points people are making start to form elements of an argument (to be picked apart) instead of revealing the beliefs that support their point of view. Listening becomes intermittent like coming up for air when you swim the butterfly, but the burning in my lungs is the fireball point I can’t wait to vomit on the middle of the table. The element of surprise carried by a data point yet to be revealed and the words I can wrap around that axle to form the noose of the argument I will hang around their neck deliver heart pounding excitement

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Rollercoaster meetings

Partnering with founders is the art of seeing what someone else is dreaming and placing that dream into a world constructed in your own mind — turning it over and working to make it fit — and hoping to feel the hairs stand up as the roller coaster dives down the back side of the tracks and a new universe of possibility comes into focus because a founder’s dream just shattered my model of how things will be.

Forget finding the next Blue Apron, even that most basic moment of connection, when I clearly see what is in a founder’s heart and know how to maximize their impact as CEO is infrequent. Sometimes I think it is coming, we are going up and up but the clicking of the ratchet never stops and the ride ends with no whoosh.

What could I have done to get to the other side? I wanted to let gravity take

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Luck and my practice of venture capital

In any pursuit where luck plays a huge role, it is hard to find a path to success. The easy thing to do is sit back and let the magic of the universe take over. If I luck my way into a great company, I will be a great VC, but deep down I will know it was just luck. The insane thing to do is spend a ton of effort trying to affect what I don’t control. If I try to control outcomes and companies and founders and decisions I will be seen as a typical VC, but deep down I will know I am just an asshole. These guardrails push me toward a third path, an acceptance of my lack of control and a focus on the actual practice of venture capital. If I am dedicated and the process of executing on the day to day work is

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Good investor communication is like a management 1-on-1

In addition to a simple dashboard and short commentary on the business, one founder I know sends a monthly email with two quick questions:

1. How are we doing?
- Exceeding Expectations
- Meeting Expectations
- Not Meeting Expectations

2. What are the biggest risk factors on your mind?

This requires a 5-minute response with honest and candid feedback.

(She also notes that if an investor feels they don’t have enough information to give quality feedback, they should reach out to her with specific questions.)

This pattern of investor communication feels like a 1-on-1 and that makes sense because it serves the same purpose.

Good managers avoid surprises. They make sure people know how they’re performing (generically exceeding expectations, meeting expectations, not meeting expectations). The goal of regular 1-on-1’s is to create an ongoing, open conversation about how people are doing, where they can improve and the resources that are available

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What are we NOT going to do

the best part of our 2017 planning process was being clear about what we are NOT going to do
A founder said this in a meeting the other day and I think it is exactly right. But, being curious and to make sure they highlighted it for the reasons I hoped, I asked why it was the best part and how it would change the way the company worked. Summary follows:
  1. We are scaling quickly and attracting amazing talent — people who are ambitious and creative and highly motivated — this is a huge benefit, but coordinating their efforts to focus on initiatives that move the needle on company goals is critical. I want them to be creative and to try new things, but to do that within the context of advancing one of the annual goals for the business.
  2. I found that clearly saying no to broad opportunities / potential growth areas up front saves
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Trump Cards and Crossing Lines

The recent new yorker cover shows the torch atop the Statue of Liberty snuffed out — fuck this. There is no way the Trump administration will put out this flame. They will not diminish America as a beacon for the tired, the poor, the huddled masses yearning to breathe free because the vast majority of Americans will fight back. Don’t get it twisted, there is no mandate for this shit. Everyone who voted in the election in November was an American — and there are even more of us who didn’t vote. Americans all know, deep down, what is happening in Washington today is not only anti-american, it is demeaning to basic human dignity and we recognize that our president is creating instability on a global scale. Every American who loves this country and what it stands for knows what Trump is doing is wrong — we are a country founded on religious freedom and made great by
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Mental framing and word choice

The other night we held an autonomous vehicle salon at First Round (we do about 90 dinners a year on specific topics from tactical stuff on company building to general areas of curiosity). I learned a ton about the autonomous landscape but was really struck by two things that are more about language than about self-driving cars. As the roads move toward autonomous, the number of crashes and fatalities should drop a ton —there are about 35k people killed every year in car crashes each year in the United States — and it would seem that a decrease of a factor of 10x to 3500 fatalities would be amazing. But this is the wrong framing. When cars sustain or create physical damage today due to a collision, we call it an accident — a mistake was made by a well intentioned human actor. When an airplane sustains or creates physical damage due to a collision, we
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baby steps

I want to be better and every year I set goals or make resolutions and, most of the time, the only consistent part of my resolution, the “habit” I have established at year end, is abandoning the resolution. Read more books, exercise more, manage my calendar in a more efficient way…by year end, I can recycle my resolutions and hope next year is better. Last week, a founder I work with told me about a guy he knows who believes in the power of habit. This is not unique — but the approach he takes to creating the habits is worth sharing. He believes in setting big goals but then working back to the daily minimum effort that will deliver the big long term personal gain. The key is to pick a minimum requirement that you can do daily — no matter what — and focus there. Don’t say, “I want to read more books” or even a book
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Break and reset?

Founders who believe they are chasing the largest prizes understand how much has to go exactly right (in addition to lots of luck) to achieve the victory they are looking for — and with this in mind, their tolerance for noise in the system is lower and their perception of short term pain vs long term gains is heavily skewed toward the very long term. They demand more and react with more intensity to “small” challenges. They don’t blink at decisions that would give most of us ulcers and insomnia. They are more willing to walk away from a flawed process or failing teammate and start again. The best founders I know are more willing than most to break and reset. I think part of this comes from confidence in their ability to move quickly and catch up after starting over. But, the other part that feels deeper to me is the potential they see
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What goals did you miss?

The board meetings I have been in the past week all included an annual review of the business and laid out the goals and milestones that were hit in the last year. In one of these meetings, after the company walked through the goals they had hit, another investor asked, “What goals did you miss?” This was not asked to cut the founder down or to focus on the negative rather than the (significant) progress the company had made over the year. It was asked as a way to frame the thinking around goal setting at the company and to help improve the process for 2017. If the answer to this question is none — and you met or exceeded all your goals, you didn’t set them high enough. You need to expect more, think bigger and reach further next year. In this case, and I think for most founders, the answer was a few
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