Tag: Confidence

Categories
Preparedness

Day 324 and Seneca

I was once asked by someone how I can act so quickly on major life decisions when they needed to mull a change over for months. I found the question confusing as I don’t think of myself as being particularly fast or even impulsive.

Well, that’s a lie, I’m impulsive about lots of shit but never anything of consequences. When it’s a major life decision I gather information for years so if the opportunity presents itself I’m prepared to act immediately. I take the bias towards action seriously.

But I only make a move when I believe I’ve crossed a threshold of information where the benefits of action clearly outweigh the benefits of inaction. I’ll make a move when I think I’ve got a better chance of winning than losing. Or when it’s clear that if I don’t act at all I’ll have a losing hand. But I generally only needs the odds to be tilted to a plurality of probability. Especially if it’s an action I can undo later. It’s not always easy to know if you can win. Sometimes the best you can do is recognize that inaction is weakening your position.

Part of my comfort in my process for taking action is I am a researcher by nature. If I’m interested in a topic I’ll begin with exposure right away. I’ll do the light skimming research the internet has enabled through articles and videos. I’ll dive deeper and purchase books. I’ll find experts in the field and begin following them. If I have questions I’ve got a habit of emailing the source. And then I’ll start doing what I can to implement my research with small scale experiments.

Chances are if you see me making a major move it’s because I’ve been considering the possibility of action for years. I like to be prepared to act immediately if an opportunity presents itself. If a situation presents itself I want to be ready. That way I’m positioned for luck. Seneca had it right. Luck is when preparation meets opportunity. But you can only have luck if you are willing to do the work of preparing and be ready to take action if opportunities present themselves.

Categories
Preparedness

Day 309 and Buying Land

Now that the pandemic has fully driven startup land to a remote first culture, I have no excuse to put off buying property. But it’s hard to figure out where to settle and when. Alex and I signed another year lease on the townhouse we have in Boulder last month which means the countdown clock is on.

I’ve been in Colorado a full year and I’ve got another one ahead of me as we ride out whatever the pandemic has left. So while I don’t think I’m headed back to New York City for full time living ever again, I don’t feel ready to buy a home yet either. It’s a big decision with consequences! And I’ve got no idea what to do. We want to invest in a home we can invest in for preparedness.

May the crypto and startup gods bless me with pied-a-terre money on the next exit so I can have access to New York City and live off the grid at the same time! But no seriously I don’t think I can settle in Colorado either. The last summer was unlivable between the extreme heat waves and the ozone pollution that comes from high heat combining with high altitude sun. It’s better in the high country but then you are in fire country. And we’ve had terrible fires in the last year. Apocalyptic shit frankly.

The Colorado of my childhood isn’t surviving climate change. And the prepper in me just isn’t willing to invest in putting down roots in a place with water shortages, drought, fires and the potential for civil unrest. Which frankly pisses me off. I’m sad I can’t just buy a homestead in the Colorado Rockies. I have a whole rant about Boomers and ruining my home but I’ll try not to piss off my elders. I just really wanted to be able to live here.

But that begs the question of where is a decent place to buy a home. Leaving behind civilization for Montana doesn’t feel feasible now either. Alex is too social for that kind of nonsense full time. Being in a small town in the middle of nowhere seems romantic until you want takeout. And frankly I like takeout.

But I also want to invest in more serious preparedness efforts. I want to be fully off grid. I want to invest in our water. I want to do the kind of regenerative agriculture and restorative land work that could lead to a self sufficient life if it came to that. I want a homestead. Heck right now I don’t even have a generator or a fire pit. Because I’m in a townhouse. Which is a lot better than being an urban prepper but I’ve got a taste for more.

But I’m also not ready to leave behind civilization. So I’ve got no idea what to do. Because I’m at the end of what kind preparedness even makes sense in a more urban location. And we don’t own it. So I’m feeling itchy. Should we buy something in Boulder that we can do some prepping on and also a piece of land in Montana? I’m not sure that’s feasible financially. I feel stuck on this one if anyone has got opinions.

Categories
Startups

Day 305 and Request for Founder

I was having an emotional conversation with a friend. They were giving me a piece of feedback that was truthful but hurt me. Because I feel psychologically safe with them, I was able to take the feedback in a receptive and open manner. I could incorporate it into my mental framework immediately because I trusted my friend. And I knew that their feedback was important and accurate.

One of the traits that I feel is most central to success in founding a company is the ability to process feedback effectively. Founders are constantly getting feedback. An average day might include angry customers with product complaints, a venture capitalist with heartfelt but partially useless advice, an unproductive strategy meeting where no one can seem to align, and a bunch of smart ass shitposters on social media with job advice for you.

A startup CEO gets a lot of feedback. Every day is a deluge of the stuff. And founders have to be gracious about it. Even when a lot of the feedback is useless, or even occasionally downright bad. You as a founder have to decide what to take and what to ignore. Because learning how to synthesize and integrate feedback; positive, negative or even profoundly unhelpful, is in fact your job. Being good at it matters. It’s the closest thing I have to a litmus test as an investor.

This is a trait I prioritize highly in founders. If you yourself are a founder that is working on improving your capacity for feedback processing, I want to hear from you. That mental flexibility is one of the core criteria I look for when I decide on an investment. Do I think you will be able to intake enough information about their market to get to product market fit? Will you be able to adjust your mindset and mental models quickly enough to outrun inertia? How emotionally strong are they that there can hear constant negative input and still hold their positive vision? But equally can you adjust that positive vision when negative feedback that actually matters presents itself.

These are the questions you need to have answers to for yourself. If you can drop me a line on Twitter DM. I’ve got an entire primer on now I like to get to know founders.

Categories
Biohacking

Day 303 and App Pressure

I refused to give in to peer pressure as a kid. I was way too much of a handful to ever let anyone else tell me what to do. Sadly this led to being constantly on the shit end of the girls in my classes because I didn’t like to play their games. I was terrible at respecting authority, and this included any kind of peer power structure.

Thankfully we moved every two years so I never had the suffer the consequences of being headstrong. Probably why I was so eager to thumb my nose at power. I didn’t think it was going to last for very long. So I never had to solve for it.

It turns out I should have learned to cope with peer pressure when I was younger. Instead of reflexively being against all kinds of authority, I should have learned when to accept (and when not) the input of people and systems who have power over me.

Why? Because now I don’t know when to say no. As an adult I am extremely susceptible to pressure from my applications. I opted into letting them have power over me and I have no idea how to say no to them. I’ve got a problem with application pressure because I didn’t learn how to deal with it as a kid. Ooops!

As part of my quest to regain my health I have become an avid biohacker. I track tons of metrics. I wear both an Apple Watch and a Whoop. I’ve use half a dozen different applications daily. But what I didn’t appreciate until recently is that the nudging state of my wellness apps is functionally just peer pressure.

My “Health” folder on my iPhone

And I give in to it every damn time. Welltory says I need to be active 10 hours today? I better go walk around the house. Apple Watch trends say I have fewer active minutes? Fuck I must be lazy. Gyroscope is reminding me I didn’t meditate? Oh no I am not zen enough! My applications are bullies and because I opted into it I feel like I’m a failure if I don’t say yes to everything. I guess it turns out you cannot escape life lessons.

Categories
Chronicle

Day 300 and Accomplishment

When I first started my practice of writing every single day I had the goal that I would do it for 30 straight days. I started on New Year’s Day and we all know how most resolutions end for people. But I figured one day at a time right? Sure I wanted to start a practice that would go further than a month but I didn’t want to jinx myself so I didn’t set a goal of reaching any fixed number on January 1st.

So today ten months later on day 300 of writing every single day I’ll admit I have ambitions for this space that I don’t want to say out loud. I want to enjoy the moment. I want to note the occasion. And maybe I want to feel a little not accomplished.

Which was a theme I also explored on day 100. And again on day 200. I suspect I’ll say something if I make it to one full year of writing daily. Maybe I’ll have the pleasure of noting every 100 days again. Perhaps it’s human nature to notice the markers but to be a little afraid to make a big deal out of them.

We know in our hearts the accomplishments we seek but we dare not same then out loud. No inviting in evil spirits right? Even though I suppose we might be inviting in the angels just as easily. So maybe I’ll just say that I would love to make it day 1,000. The idea of having a record of my thoughts for years seems like a heady ambition.

I don’t want to opt myself into something that may not serve me in the future. One reason I’ve loved this exercise is because I felt like I opted into it every single day. It was always a choice and I always made it. It has been an enjoyable experience and a daily discipline. So I hope it’s one that continues to serve me. And I’d it doesn’t that’s ok too. May we make all choices in freedom.

Categories
Startups

Day 298 and What You Don’t Know

I work with a lot of first time founders as a seed stage investor. Or rather I enjoy working with first time founders so I slowly became a seed stage investor as moving from advisor to angel investor. When you are a founder yourself, as I once was, you get a lot of inbound from others in the startup ecosystem as the bias has been that “only other operators can ever understand” so it breed insularity.

This has generally meant that there is a significant body of knowledge on best practices in startups that doesn’t get codified in writing it’s passed on as an oral history from one founder to the next. Maybe if someone published their Gchats and emails public we’d have a searchable wiki. But even with the trend towards startup communities, explainer Substacks and operator podcasts there is still a substantial portion of unspoken knowledge that no one will tell you. You literally don’t know what you don’t know. And the people that know have forgotten what it’s like not to know.

It’s easy to forget this as you assimilate norms and conventions over the years. I have been working with a portfolio company’s CEO to prepare some press and go to market work recently. Something I take completely for granted about media outreach wasn’t in fact obvious or intuitive.

But it was so obvious to me I never thought to mention the detail that tripped us up. And of course, the founder being a first timer didn’t know what they didn’t know. Why would they! That’s why they work with more experienced investors and advisors. It was my fault. I knew the thing but in my “water is wet” mindset didn’t even consider that the founder might not realize they were swimming in water yet. And that was entirely on me.

I find it somewhat comforting that startups are constantly introducing new founders who don’t know what they don’t know. Because maybe they will be the one to discover a new way of knowing that changed it for all of us.

The best is old timers can do is pass on what we think we know and the newbies can assess that using their fresh eyes. Sometimes (ok probably most times) we save you from making dumb mistakes that we once made. But maybe what I think I know for sure is just me not realizing I’m a fish in water. You can learn that from experience sure but also from having a totally new lens.

Categories
Emotional Work Internet Culture

Day 293 and A Good Cry

I’m a cryer. I hear the swell of trumpet from the Star Trek theme song and I’ll start welling up. I’ll read a poignant passage in a cheesy airplane novel and my chest will tighten with emotion. My eyes will tear up when I tell a friend that I’m proud of them. I’ve found myself sniffling over a set of emotional text messages. I love a good cry.

I think I’m a cryer because I bottle up my emotions otherwise. I’ll share feelings in public but the real deep down core emotions are harder for me to express openly. The fear and hurt and sadness that make up the core of my emotional unconscious take some coaxing and a lot of psychological safety to get out into the open.

One of the reasons I find social media so much fun is it is a cesspool of emotions. Much of shitposting is just rage and anger expressed with a joke. And the shitposts that are sad are often told with a kind of vulnerability that I more commonly associate with 12 step meetings or group therapy. Internet culture has become an escape valve for emotions we didn’t know we even had.

The more I see the negatives that comes with keeping emotions bottled up the more I appreciate ways to let them out. If it is a good cry then I’ll take whatever brings it on. If you need something stronger than I highly recommend a light dose of Internet emotions. Just don’t let it overwhelm. Ease into the shallow end with an anonymous shitposting account first.

Categories
Internet Culture Startups

Day 282 and Stop & Go

I wasn’t born until after stagflation so I can’t tell you what America or Britain felt like in the 70’s but the chattering classes seem to enjoy bringing up the comparison. But there does seem to be a bit of “stop & go” energy in the air. Everyone is raring to go but the energy cannot quite flow freely as we smack into obstacle after obstacle. Demand is pent up but the reality of supply is uglier.

Obviously this perspective of excitement and demand is colored by working in startups where the bias is always towards the excitement of building new things. Crypto is burning with the fire of millions of zealots, all of whom are confident we are building the infrastructure for a better future. Everyone feels like it’s worth investing and higher prices are a good sign. There is more go than stop here.

Of course, I am one of those zealots. I’ve got the optimism of someone who saw how fast previous waves of web1 and web2 changed my entire world. Wealth and creativity was unleashed twice over for the elder millennials who were lucky enough to witness the dot com boom as children and the social media era as their first jobs.

There were massive crashes and financial implosions too. Stop more than go. More of us got hurt than got wealthy. But we saw the possibility even as failure engulfed most of us. So we believe we might be the lucky ones this time. That we might be the ones to win the game. “Red light, green light” seems fun if you can make up ground when everyone is running. Just don’t get hurt too bad.

I feel this energy in my own body. I am excited to push into everything. My portfolio companies are all riding high. There is no way I can do it all in any given day. So when the go energy pushes me sometimes I find myself leaning into stop and simply taking a nap in the middle of the day. It makes me a little jittery to feel the push-me-pull-me of demand grind up against the limited supply of energy and focus. I’d like to feel fully unleashed but I know somehow there are moments where it’s best to stop before I go.

Categories
Finance Startups

Day 275 and Manifesting

I had a really terrific September. Everything just started going my way. Projects that I’d been pushing on had significant breakthroughs. My deals got hot. My focus and health improved. Even when I had setbacks and failures I was able to execute on quick recoveries. But mostly I didn’t give in to past bad habits. And all of that happened without any additional effort on my part.

I’ve been making a really conscious effort to stop pushing myself to always be doing more. Either I am able to find elegant solutions or I ask myself to take a step back till I can. Rather than brute forcing everything I am finding ways get where I am going without sacrificing myself to costly bad trades on my time and energy.

I asked for something really significant from one of my investments (an additional allocation for an special purpose vehicle). The second I asked for it I started to panic. I didn’t have an immediate or simple path to deliver on what I asked for from this founder. Even though I was confident I had the money for the deal it out I panicked that maybe I had bitten off more than I could chew. Immediately it started going through my head about how bad I’d feel if failed this founder. I relived the guilt, shame and punishment I had felt in previous failures to deliver for people that trusted me. I hated feeling like I’d failed people.

And I just decided stopped the cycle of worry then. Like turning off a switch. I told myself I could do it, I knew I could do it or I wouldn’t have asked, and that there was simply no way I was going to let down this founder. But this is where I felt the frown Instead of going into overdrive, I stuck by my schedule. I didn’t change anything. I didn’t push myself to a frenzy by adding in calls, pitches & emails. I just put down all the steps I could and would take to make the deal available to the right people and I began.

In the past I would have let that fear drive me. I would have gone into overwork and adding in additional tactics that I didn’t even need to insure I would reach my goal. But here I trusted myself to get the outcome. I didn’t exhaust myself. I took care of myself. And the allocation got filled quickly. I checked the commitments this morning and I’ve only got 15% of the deal left.

Categories
Internet Culture Reading

Day 271 and Correspondence

I love writing to others. I had some pen pals as a child but it wasn’t until as a teenager that the Internet gave me the chance to correspond with practically whomever I liked. And it’s been one of the great joys of my life to reach out to others for conversation.

I developed a habit of writing to journalists, authors and academics whose work I admired. Many of them maintained email addresses and personal websites even back before social media. If you are ever worried that someone will find it odd or unsettling to receive a note from you, don’t fret. I can share that if you are polite and sincere outreach is almost universally appreciated. Most people want to be seen. If you feel you’ve seen someone then you should share it with them. It’s a kindness to you both.

While I particularly like short form correspondence like Twitter, there is no substitute for a more in-depth and layered letter. I’m personally a fan of the threaded twenty response deep email chain. I think of it as like the letter writing of our forefathers. Maybe it’s a bit less satisfying to our heirs than discovering a box of letters but I’ve got a fantasy that the Ken Burns of the future will make excellent use of email and chat logs.

If you aren’t convinced of the benefits of reaching out through writing feel free to test it out on my before you write a letter to your favorite author or thinker. We just might become pen pals.