Day 392 and Deal Flow

I wrote about my general philosophy about the futility of the typical hour long deck based venture pitch two days ago. I explained that I’d rather have a conversation with founders.

So if you want to pitch me just hop on over to a Telegram chat or my Twitter DMs. Let’s talk and learn and share and then I can really see your passion and vision and we can both avoid canned performative shit.

Well since then my Twitter DMs have been filled with amazing chats with founders of companies as diverse as consumer products, marketplaces and web3 games. The stuff people are cooking up in crypto is wild. Thought not enough SaaS tool pitches though so clearly I’ve got to get more mindshare there. Note to self to impress Jason Lemkin or something.

I’ve taken a dozen pitches now through direct messages and chats. It’s worked amazingly well. Maybe I owe a drink to Sam Lessin as he came out strongly against Calendly right after I wrote this post.

So pitch me however you like to communicate. Plus, don’t we all die inside a little every time someone sends a Calendly link?

So I’ve got to say I hope I became known as the slide into her DMs VC as this has been a lot more fun than trying to play calendar sync with dozens of people. That game sucks.


Day 388 and Washing My Hair

When I was a sophomore in high school I lived in France. As part of an exchange program I attended a private Catholic school in Evreux which is a a town midway into Normandy. The family I lived with was almost quintessentially French. The patriarch of the family Didier was a perfumer that worked in fragrances for Chanel. And this is where American bourgeois and French bourgeois diverge. In our washing up.

I was accustomed to showering every single day. I was a horseback rider, as was the daughter in the family with whom I lived. I thought it perfectly reasonable to rinse off the barn smells on a regular basis. This was not a view shared by the family. While they were immaculately groomed, their routines involved wash cloths and eau de toilette. Washing one’s hair was a once a week affair.

I was slow to pick up on this cultural norm. They would politely point out that I showered a lot. I was gifted a number of Chanel cosmetics and fragrance products. Did I perhaps prefer Allure to Number 5? They kept coaxing me. I kept not getting the hint. Finally I was told point blank I was running up the water bill and I needed to knock it off.

Lucky for me the habit stuck. That old joke where a woman tells her suitor she can’t go on a date because she’s washing her hair? That’s me now. Well, sort of. Every Sunday afternoon I set aside an hour for the full scrub down routine. I like to go into the week with freshly styled hair. If you catch me on Wednesday or Thursday you can see my hair slowly getting less coiffed. I’ll typically do a rinse and condition on Thursday but thanks to my French family Sunday remains the only full hair washing day. And I still kind of dislike perfume. But don’t tell Didier.


Day 387 and Travel Routines

I hadn’t done any travel since the pandemic hit until last week. I’ve probably been in a comfortable at home routine for years (if you don’t count the cross country moves). But last week I went to Montana to do some house hunting. And I could tell I was out of practice traveling.

I used to be on the road pretty frequently. So frequently I started a travel cosmetics company. I was really dedicated to fixing the annoyances of being on the road with travel routines. They can be really simple routines. Always unpack immediately. Get yourself settled in with all your cords and charging stations. Bring your workout clothes. Have nutrition plans and exercise routines that can be adapted for airplane food and hotel rooms. Bring a water bottle. Pack supplements in daily baggies. Learn to fast during your flights.

I could go on and on about the routines that helped me prevent the recovery most travel requires. If you are gone for a week and don’t maintain your routines then you lose another week transitioning back.

I sadly didn’t bring enough of my routines with me to Montana. I underestimated how tired I’d be so I didn’t keep up with my workouts and physical therapy (I’m recovering from an injury which compounded the issue). I didn’t have a nutrition plan so I ended up eating whatever was readily available.

It wasn’t all bad to be clear. I remembered my supplements and vitamins. I went to sleep on a consistent schedule. Even if that meant being awake when it was pitch black outside. Montana is far enough north it doesn’t get light out till 8am.

But I think I could have done a better job not letting the excitement and change of environment ramp up my nervous system. One of the best parts of a routine is making sure you’ve maintained some amount of detachment so you aren’t always at the mercy of what is providing stimulus to your system. Remaining in a parasympathetic state can be a challenge in a new environment as everything reads as novelty to our nervous system.

Even though I’ve been back for 4-5 days I feel like I’m just finally settling back into a comfortable rhythm. It makes me realize just how out of practice I am with travel. What was once a routine event is now again something that requires time and effort. Journeys will once again be out of time and place. Our lives back home will be different than when we are in the road. Maybe that’s a good thing. But it’s not a reality is considered in decades. It makes me feel as if life is measurable worse.

Emotional Work Preparedness

Day 380 and Decisive

I’ve felt decisive recently. I’ve been confronting significant and life changing decisions the last few weeks and sailing through them. I’ve never felt more at ease making commitments in my life.

It’s not that I’m particularly prone to paralysis by analysis. Generally I’ve been able to move quickly and without undue agony over my choices. But I think within the last two months I’ve simply got my limit with taking the safe course. Maybe it’s a Covid thing and now that I’ve both been vaccinated and had an infection I no longer feel like I can continue with the same safety practices that the early pandemic did. With the election over and the existential threats of insurrections and instability now existing as a permanent worry, I just put off major decisions. I can’t wait for better times or more information. I need to live adaptability now.

So I bought a house. I committed to the process of buying land in another state for a long term resilience based homestead. I’ve planned trips travel. And not nearby regions like travel. I’m going international. I’m meeting people I haven’t seen for years. In some cases I’m meeting people I’ve only ever known online because socializing has been entirely remote for going on three years. That’s an inhumane way to live for extended periods. Even the most introverted person still needs connections. I’ve started making decisions to live my life. I need to live like a future exists or I will never ever escape. As soon as I made the decision to believe in a future again decisions flowed easily.

Emotional Work

Day 375 and Masochism

I recently got yelled at by several people who love me because I was torturing myself over something that wasn’t really important.

My therapist asked me why I insist on being so sadistic towards my own body. I told her I was afraid that if I wasn’t perpetually in a state of self improvement no one would love me. The topic came up because I had allowed myself to get hurt in physical therapy. “Why would you push till the pain was intolerable? That’s insane!”

And I had to answer honestly that everything in my life is headed in the right direction. There was no major crisis or illness or disaster this week, so I felt like I had the bandwidth to add in another “self improvement” project. To which she replied “so you can’t ever just enjoy being yourself can you?”

That kind of floored me because it’s true. As soon as I feel like I’ve got things under control, I’ll add a little bit more to the pile so I can feel like I’m making progress. I am a masochist. Joy is fleeting. Better is always worth pursuing. Maybe you feel compelled to be torturing yourself too.

Chronic Disease Uncategorized

Day 372 and Pace Yourself

I was in an incredible groove yesterday. I’ve been letting go of the awful December I experienced and enjoying the new January energy. If you look at yesterday’s post I was absolutely in the zone. So I pushed myself thinking I can handle full capacity day. Mistakes were made in my enthusiasm. And well I’m probably in need of a rest. I over did it.

I often struggle with pacing and moderation. It’s important for me to remember that I’ve got a history as a workaholic. But I don’t want to feel as if I can’t push myself either. It’s the middle path I must walk. But it is hard to stay on it. I feel like every day I am sliding off the middle path right into the ditch. I’m getting better at getting myself back.

I used to be happy mailing elaborate detours. I’d take every exit on this metaphorical path in the past. But tonight I’m going to remind myself I’ve got a destination. And that is being responsible for keeping myself happy and healthy. So I’m going to get in bed and watch some TV and shitpost on Twitter

Emotional Work

Day 370 and Grindstone

Today felt like the first day everyone was really back at work after the winter holiday. As much as Americans like to bitch about how Europe takes off August or China takes off January or February or whenever the Lunar New Year lands, we take off much of December. Around mid-month folks drop off the radar and nothing gets done till about Epiphany or so. And they say we aren’t a Christian nation.

So while technically we all came back to work on Monday, today is the first day I really felt like I was back. Maybe it’s because December was such a clusterfuck of a month for me. I had Covid, I tore a ligament, Boulder County burned down. I know this is a petty complaint but I didn’t get a Christmas tree because I couldn’t walk and then I was quarantined. So it was going to take a few days to really shake that off and come into the energy of January.

But I felt back today. Like maybe I could fucking do this. Like all the catastrophic nonsense was shit I could mitigate. And all the optimistic stuff was achievable. And I am going all in on optimism. I’m going to Montana soon to check out towns as I’m just ready to own something more rural. I’m wrapping my head around owning something that is a winter seasonal home. I booked a trip to Europe in a really extreme leap of faith that Omicon will run its course by spring. And I am ready to close some deals I’ve been working on for the last month or so. So fuck yeah grindstone. Im ready.

Aesthetics Emotional Work

Day 362 and Round Ups

I’ve only got three more days before I can officially say I’ve written something every single day for a year. I had it in my head I would go through everything I’ve written and tease out some themes. Maybe I could find a few sections and label “best of” posts. But I haven’t done it yet.

Partially I’m too lazy. Digging through tags and trying to make something coherent out of an exercise that has always been about being in the member seems like a stretch. I’m sure there are probably analytics I could look at but I’ve actually only ever glanced at what posts get read and who shares the content. One of the reasons I’ve loved this space is simply because I’ve done so little to cater to anyone but myself. It’s a journal that’s public but with little actual public input.

I know that sounds a little crazy. Clearly I’ve got to be writing this for someone or else why wouldn’t it be in a private journal? I’ve never had a good answer to that. I feel accountable to some kind of existential audience. That by commuting to hit publish every day I’ve promised some “other” I will abide by my commitment. But it never extended beyond the daily discipline of actually doing the writing. I need an outside world to feel the pull of obligation but I’d rather not go further than that. That somehow invokes readers & optimization or god forbid fans.

So I’ve yet to find the roundup post topic that feels like me. But I also feel like I might owe myself some kind of synthesis. Some learning or insight that comes from having engaged consistently and steadily in an endeavor. But it’s on my mind.

Chronic Disease Emotional Work

Day 330 and Vitamin Not Pill

I was reading a fellow investor’s thesis page and noticed one lens they use for investing is whether a product is a “vitamin or a pill” with the insinuation that pills are inherently better investments than vitamins, as one is a nice to have for a business and the other is a must have. Now I can’t speak to this as an investment thesis, though I largely agree, but I do disagree on a wellness basis.

Preventative medicine is just as necessary as interventional medicine. In some cases more so, as getting ahead of a disease’s inflection point should be the humane way we handle our medical needs. We are just often too focused on short term impacts to see the value of solutions that build over time. Think of it as the quarterly reports of healthcare. Why build for the future when the market judges by each 10K?

The nature of panic may make us inclined to spend heavily on something that has become acute. But that does not make it inherently more effective or worthwhile. It’s just the immediately necessary. It just means we need higher minimum effective doses to see a result.

What we often ignore is compounding effects of wellness interventions are far superior to the mitigation of a pharmaceutical over time. Most of us would prefer to not require the costly (both biologically and financially) medicines that keep us together. This is not to say that I am not deeply grateful for all the drugs I take. But rather that I have seen incredible value in what we deem “lifestyle interventions” and other “nice to have” vitamin style supplements and protocols.

And while it takes much longer to see their effects, the compounding positive effects often wildly outperform anything that might be dubbed a pill. The trouble probably boils down to switching costs and time to pay off. Which is why an investor would prefer a pill to a vitamin. But just because something has a longer lifecycle doesn’t make it inherently less sticky. Or less effective. Or crucially any less profitable. The only way we ever see the deeply positive effects of habitual practice and dedication is to do the work. That work is boring, repetitive and low payoff. Until, most times years in the making, you see how putting your future self over your present self is what is giving you the future you always dreamed would be yours.

Emotional Work

Day 328 and Cultural Pause

I love America’s big holidays. Thanksgiving and the week between Christmas and New Year’s are my favorite. But not because I am particularly attached to any festivities. Though I do love everything about Christmas. I love holidays because I feel like it’s finally ok to pause.

Having an moment where it feels culturally acceptable to be at rest is deeply comforting to me. I feel it slightly on the weekends. It’s like the ambient environment around me lifts the expectation of being “on” and everything I do is a bonus. I finally let myself relax. And more crucially I don’t beat myself up for feeling relaxed.

It’s a fairly profound feeling for me. Normally I have something in my gut that says I must be productive if other people are working. It’s hard for me to shake honestly. I struggled with vacations and I initially hated sick leave (even though I needed it badly) because I felt I should be accomplishing things along with everyone else.

I’m working on it and it is getting better as I do more emotional work on myself. But I still relish the feeling of rest that comes with a holiday.