Categories
Startups

Day 1125 and Planting Seeds

I like to get to know founders over time. It’s a canonical piece of advice passed down over venture lore that one should invest in lines not dots. Consider the messenger of course.

I’m sure to founders it can feel a bit self serving of investors to want to see a lot of traction before a commitment. That’s not what I’m talking about. I think as an investor, we have an obligation get to know a founder’s character and their approach to problem solving. Especially if you believe their opportunity to be enormous.

At the earliest stage our responsibility is to assess your capacity to overcome obstacles and to improve your skill sets to match. We need to know you will grow and flourish.

Nurturing a seed is the entire metaphor behind early stage investing. A seed round is such an optimistic name. If we must extend the metaphor that we are planting seeds then the work starts before anything goes in the ground. Good soil, good weather conditions, and the right timing matter a lot.

The anxiety inducing part of this is that my approach years I take time to cultivate potential founders for years. I never quite know when someone will go up for a fundraise. I have to wait and see.

But when it does happen. It’s such a miracle. No finer feeling in the world than having cultivated the right conditions for something to grow.

Categories
Emotional Work

Day 1119 and Capacity for Presence

I trust my ability to be present now. I wish I was less present in some ways. I’ve learned to be present to the ways of the internet in particular as part of my general capacity with the signs and signals of those who communicate with words. I try not to show up in person too much anymore except for my own neighbors.

My capacity to be present waxes and wanes with the attention that I give to the margin. And I like to be present for the weirdos. I am not as detailed as some with effortful thought pieces but I pay very close attention. I diligently note and revise bigger trends here in public. It’s not my job to endlessly footnote it for everyone. That’s thankfully now in the hands of artificial intelligence.

I trust that I notice things when they need to be noticed and that I will curb my attention away from those who do not use me well. I will so rarely take it personally when someone tells me I do not serve them. The favor is usually returned when I say a hard no but I rarely have to give it. The average isn’t that persistent.

I do not wish to be become significantly more scaled than I am now in terms of presence with people. I am picky and I cultivate my taste and I believe I’ve built trust with the people who intend to build things. I will continue to be as widely available to them as possible if they do even a modicum of homework. My experience is not free but I do not horde it.

I believe I’ve shown my capacity to pick not through momentum or hype but early presence. It’s a long road and I’ve got the patience to walk it for decades more.

I leave you with a thing I noticed today from someone who is very effortful and has been for much longer than me. How we distribute our attention matters even in the most intimate of settings.

Attention without feeling, I began to learn, is only a report. An openness — an empathy — was necessary if the attention was to matter

Mary Oliver on Molly Malone Cook in “Our World via Maria Popova at Marginalia

Categories
Emotional Work

Day 1113 and Sorry Can’t

I dislike days where I spend too much of my energy doing stuff as it prevents me from spending time synthesizing stuff.

Of course, and I hope this is obvious, the opposite problem is much worse. If you spend too much time synthesizing stuff then you run the risk that you don’t actually do stuff.

You’ve got to keep your skills sharp with new conditions on the ground but you have to intake as much information in your field as possible.

“Sorry I can’t” is a strong signal. It means you are engaged in the productive middle of focus. Family is a productive middle of focus. Your business is a productive middle of focus. Your friends is a productive middle focus.

Maybe you picked something to focus on that someone powerful wishes you didn’t. Maybe you sold your focus to someone else. Maybe you are on the clock to a wider goal. The calculation of how we do that is best left to market forces in my opinion.

I will redirect my attention for someone that asks and shows me the incentives. I think it’s a worthwhile balance. If I believe my focus being redirected can help someone else execute on taking action I’ll do so. That usually means saying to someone else “sorry I can’t”

Categories
Emotional Work

Day 1105 and Other Writing

For as much fluidity as my daily writing habit has achieved, I can still get caught up in a synopsis. I have relieved any pressure to make a daily dispatch (which took some effort) but a quarterly or yearly one can get me to glitch. I like to add more information to my modeling like any self respecting nerd. As much as information integration looks effortless it is actually a laborious process. I read tens of thousands of words every single day.

Now I do work from a strategy. Which means I only adjust my tactics on a weekly or quarterly basis. And I will not be sped up on assessing the character of individuals or the caliber of their ideas if I can help it. When I need to move fast I have to do it within the guardrails of what I believe to be right.

And it’s important to remember that heuristics some heuristics don’t need regular updating. Moral codes shouldn’t need much updating. Maybe you believed the wrong layer of abstraction and have to change your priors to align with your moral code. That’s totally fine.

But you shouldn’t be changing around your code of ethics. That’s how you get criminals. Arbitrage is never permanent. Criminals can have a stronger moral compass than business people or religious institutions. This fucks with everyone. I cannot account for all sinners nor most demands for purity. I can however hold myself to my own standards and so should you.

I do what I can to telegraph my own belief systems and where I derived them. There are lots of signifiers I leave in my wake. I am a Christian. I am a capitalist. I am a Protestant. I believe in markets and judicial review. I believe some things are beyond market but all things are subject to forces beyond our control. That’s how I ended up picking Calvinism as a sect but it’s pretty niche.

I’ve believe luck is just opportunity meeting preparation and you can do a lot to increase opportunities and even more to increase preparation. I don’t like rentiers but I do like the bourgeoisie. Property rights are good and regulations are only as good as the people that make them. That’s why we I’d prefer we have fewer laws. We must act deference to our own failings as human but never so much that it harms our capacity to organize.

Categories
Emotional Work

Day 1096 and Year Four

The persistence of my daily writing habit has helped anchor a sense of self that I have enjoyed cultivating. I am the sort of person who sticks with things.

I’ve been in the process of excavating and rebuilding my sense of self over the last few years. Many others have gone through similar journeys during the pandemic years. I feel lucky to have captured some of mine in writing. I like who I have become as a result of it.

I like seeing that I have reinforced positive and optimistic aspirations for myself year over year. I hope it shows who I am to other people through my revealed preferences. My actions speak louder than my words even if some of my actions are shown through words.

I do not have any New Year’s resolutions for 2024 that I didn’t already have for myself in 2023. I’d like to keep the good things in my life, pray for willingness to improve upon the bad things, and remain steadfast in the commitments I have.

Categories
Chronicle

Day 1090 and Winter Breaks

I would very much like to take an extended break to restore my mind and my body. I feel as if I could use a week or two offline.

The holy nights have held a place in my heart and mind as the season for introspection. I like doing fasts during this time, but it’s not been physically wise to take an extended fast recently.

I expect 2024 to be a big year. I had lots of little things to wrap in 2023 which is impacting my capacity to fully check out for the remainder of the year. Duty calls I suppose. I am keeping my obligations to others but I may need to find a way to keep obligations to myself.

On that note, I’ll keep this short. It’s better to get back to reading and resting when my capacity is diminished.

Categories
Emotional Work

Day 1080 and Hard Feedback

Ego protection is innate. Humans have quite the capacity for engaging in defense mechanisms. As I do my end of year reviews to see what I have accomplished and where I have failed I see my ego everywhere.

The types of ego protection that plague me tend to be with those all too human relationships that are closest to me.

I had to admit to myself that I’d been engaging in entirely unproductive approaches in a close partnership. I wanted more from my partner and I’d express it again and again, but I didn’t seem capable of demanding the outcomes I needed. This was unproductive obviously.

Hard feedback was given to my partner. I had to look into my own motivations for enabling a cycle of letting outcomes that didn’t match our goals occur. My own part in it mattered. We had enforced errors, self doubt, fear and all the other typical buggaboos you might expect in a hard situation.

It can be hard to simply address the hard things head on.

Emotional reactivity is part of our autonomic nervous system. It’s not always right. It’s only sometimes right. And learning to tune it is part of the fun. You want to improve your heuristics over time. You will get more clarity on the world and your place in it. If you wish to persist in feeling anxious and uncertain being passive will have that effect. It literally hurts you. You have agency in deciding to address how you feel head on.

Day 1072 Head-on

Categories
Emotional Work

Day 1079 and Flowing

I try to direct my attention to where I have natural advantages. I’m sure you’ve seen variations on the theory that if you are gifted with a talent then honing those talents with hard work is the rational path.

If you are a 5/10 perhaps you can’t reach beyond 7 of 10 with effort, but if you are a 7 you can probably put in the effort to be an 8 or 9 and achieve great things.

I don’t mean this as an argument for not putting in the hard work to improve where you lack talent, but rather that hard work can compound for even greater rewards when applied to your talents.

No one ever enjoys being bad at anything, but it’s worth remembering that aptitude can and ought to be honed. I don’t always love seeing the areas of my life where I suck. I was in the past very inclined to beat myself up over it. That is the path to not improving anywhere in your life.

Categories
Emotional Work

Day 1074 and Go Go Go

I feel as if I had a lot more trepidation about the future before the pandemic. I wasn’t so sure if I had a clear view of how my own personal philosophies were meant to engage with the scramble of building, and then surviving, my own life. That seemed like a luxury for people higher up the hierarchy of needs than I was.

I feel like I got a lot wrong even as I see how I was equipped with so many tools that I used clumsily. I wish, in some ways, that I’d been surer of my own knowledge earlier. I didn’t trust myself. I felt like a Cassandra doomed to see dire outcomes.

And yet I retained some sense of optimism. You can see my doomer arcs clearly across the written records as systems failed me and then failed others. Natural disasters and chronic illness in very real ways forced me to overcome any inclination towards a culture of nihilism. I found that I couldn’t give up.

There was no comfort to be found in saving myself but I did. And now I find myself simply done with trying to muddle along. I am getting much louder about my own alliances and beliefs. I am updating my priors and throwing myself into fights. I am choosing sides even when I don’t care for all my compatriots. Neutrality is easier to maintain at the edge of an empire surely but I hard limits on what I find to be acceptable compromises in a free society.

Categories
Community Emotional Work

Day 1057 and Grateful for Disappointment

Thanksgiving is one of America’s strangest and most utopian holidays. We take a day at the end of the fall harvest season, just as we head into the darkest time of the year, to give thanks for having survived the last the cycle.

Everyone who makes it to the Thanksgiving table is symbolically finding a place of security, abundance, friendship and family. Even if it’s just for an hour.

It’s within this bittersweet context that I think being grateful for disappointment is a worthy objective. I say the serenity prayer with that thought in mind.

God, grant me the serenity
to accept the things I cannot change,
the courage to change the things I can,
and the wisdom to know the difference.

Serenity Prayer

While I am grateful for all of the things that went my way this year, I am as glad that I have been able to accept the things I cannot change.

The disappointments in life are endless and personal. Our own family stories are shaped by the intimate family dynamics of feeling loved, secure, safe and empowered. No childhood is without some emotional ups and downs.

If you feel disappointment it’s a privilege. You extended enough empathy and love that you could be hurt. The trust required for this is one of life’s most human experiences. To love people that have disappointed us is to find peace with forgiveness. May we invite that forgiveness into our lives.

I give Thanksgiving for being able to feel connection with full knowledge of its risks and rewards.