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

Continue reading "My New Calendar System"

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

Continue reading "Trust your own mind"

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
Continue reading "The one startup debt you can’t pay back"

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."