Chronicle Startups

Day 97 and Socializing Professionally

If you know me well then you know I’m not a natural people person. Despite being both an optimist about the human potential for progress and generally being a happy person, I think a lot of people suck. I know it’s a shitty outlook.

Maybe it’s because I just don’t have the energy for socializing. Big gatherings are not my thing, even though if you met me casually at a party you’d probably think I was an extrovert. If I’m putting my time aside for you it’s because I really enjoy it. The people I spend time with have to be great. They teach me something or have a unique point of view or have great emotional capacity. Most folks just don’t seem to enjoy putting themselves out there. Or maybe it’s that they simply don’t want to offend you so never really say anything of interest. I just don’t care what shit you bought or what your constantly over scheduled activities happen to be (though this has become less true in the pandemic).

I really don’t want to go back to socializing as a professional prerequisite. I hate having to tell people how I am. No one actually wants to know. I don’t really enjoy holding my tongue. Professional events generally require you to keep quiet about how much you think someone is bullshitting.

I’m often a huge hit on panels at conferences because I don’t give canned responses but wow does that make more polished people squirm. I once made the mistake of telling the truth at a Goldman Sachs retail conference. The analysts went wild. The poor CEO next to me looked like she wanted to die. It’s easy to tell when someone is using a script and talking points when the person next to them is just talking without a filter. Humans like truth and honesty it turns out.

I really hope we don’t go back to constant networking and prioritizing people who are naturally socializers. I hope the pandemic broke some of that tendency towards rewarding the constant parade of events, cocktails and ever more exclusive gatherings. But I’m sure there will be a massive correction where everyone loves real life experiences again. But once it reverts to the mean let’s all agree to be a little more judicious in our asks to “meet up” in the future. I’ll send you a Harry and David’s gift basket if we can continue to see less of each other.

Finance Startups

Day 96 and Founders Who Don’t Want to Be CEO

My Twitter has been going viral with reply guy friendly topics like taxing high earners and public vaccine demand so I needed to get some niche startup content in today to clear my palette of the reply guys. So I’m going to think about founders, professional management teams and venture’s role in supporting founders. You know, a topic that won’t have strong feelings.

A non zero number of my founder. friends would probably pay to be extracted from certain stages of startup growth, especially later stage scaling, but somehow being founder friendly has come to mean keeping these founders in charge all the way through. Many excellent zero to one founders have to actively change their entire style, skill set and value proposition once they get a company past about employee 25. Obviously there are many inflection points in startup growth and many founders relish the opportunity for constant skill growth. But plenty of early stage founders hate stuff like Human Resources and operations. Shit a good chunk hate sales and marketing too.

Early stage work is a speciality. It’s a professional niche and hard to train folks for as it’s part personality and part dysfunction. I think we should value early stage founding for its disproportionate impact on value creation instead of forcing these early stage specialists to train to become generalists, great managers or scaling operators. Of course it’s more likely they will fail once you take them away from the stage where they are genius.

Recently a friend of mine who works in venture said of another investor “oh that VC is old school” and clarified it meant they like to bring in executive teams for their B rounds companies. Which honestly sounds like a dream to me. There has to be a middle ground between firing visionary but scattered founders once they’ve raised and trying to coach a mediocre manager into great growth CEO.

I think we should normalize founders being churned in on new ideas rapidly and churned out on scaling quickly. Let them get back to founding. Let them create more faster. Great scaling venture funds can provide more value by bringing in a scaling leadership team and easing the founder out to areas where they can focus on vision and direction. I say let the professionals run your team.

Obviously some founders dream of going from idea all the way to IPO but I don’t know if it’s the dominant path they desire. It could just be one of many. I have very little interest personally in shit like operations, process and scaling. I literally married a COO rather get good at it (insert joke about literally anything to avoid therapy). However it shakes out the “founder friendly” venture firm will remain. What it means to be founder friendly may need to be rethought.

Chronicle Internet Culture Media Startups

Day 84 and The Thursday Styles Problem

The Thursdays Styles problem is about zeitgeist, wealth, perception and power. The New York Times publishes its “styles” section on Thursdays and Sundays. Generally speaking if you work in media, public relations or culture, you are aware of the general trends that will emerge on Thursday ahead of time. For the sake of argument let’s say I know directionally on Tuesday in private what will be featured on Thursday in public.

If you know “what everyone knows everyone else knows” ahead of time, there is a lot of money to be made as Tuesday person. For more on the second derivative issues in zeitgeist I highly recommend Epsilon Theory. If you can sense the zeitgeist ahead of time & move to take advantage of it you can be a Tuesday person.

Alas it’s not as lucrative as you may imagine to be a Tuesday person. A Thursday person who lives exactly on the zeitgeist can take advantage of “in the moment” culture moves. Good entrepreneurs do this well. Most consumer companies hit “right on time.”

This is why venture capitalists will ask “why now” as they may have invested in a Tuesday Person who hit the zeitgeist too early and couldn’t capitalize on it. It really pisses off the founder who knows “but I was first.”

As a Tuesday person, I hate when this happens. I loathe seeing people I perceive as less capable or intelligent than me hit a zeitgeist moment exactly on Thursday. The trouble is they are right. They won. They got the timing right. I didn’t.

And yes being a Thursday mover is good. But it’s crucial to understand who can win this game. The only way to win the Thursday Styles problem is to be in finance, media or culture work that can place a call option on the Thursday future on Tuesday. You have to be able to hold an opinion on the future zeitgeist long enough for Thursday to get published.

If you cannot hold your zeitgeist long enough for Tuesday to become Thursday when “everyone knows everyone knows” being right early serves no benefit. You need diamond hands. And yes, you will be wrong 9 times out of 10.

So you need to ask yourself if the New York Times cuts a piece and it takes another week to run can you hold out? If the markets don’t make a Tuesday idea hit, can you wait till it becomes common knowledge on that metaphorical Thursday? It’s a question for all long holds to ask themselves.

It requires patience to be a Tuesday person. And it takes resources. Knowing you will look wrong for a bit. Knowing that you will lose money when Tuesday knowledge takes longer to become Thursday Style’s common knowledge. If you can hold it’s the ultimate form of future leverage. That’s alpha.

And better yet, it’s “possible” to influence. Publicists make their clients on Tuesday shine on Thursday. And capture the upside. Folks who are extremely online spot how market makers make zeitgeist hit. Cathie Wood at ARK Innovations has been playing the media in exactly this way. The largest experiment in making Tuesday thinkers hit before Thursday is Margit Wennmachers at a16z.

Centralizing zeitgeist and monetizing it with future calls with narratives they tell on platforms they own stakes in has massive potential. The smart money is turning their Tuesday zeitgeist into Thursday Styles and taking it to the bank.

Chronicle Startups

Day 75 and Expertise

I’ve been slowly ramping up advising, investing and consulting work into startups. Initially I was quite hesitant to do any type of consulting as I was fearful that I would not be able to produce enough work in a quick enough time. I thought advising and investing was a safer and higher leverage activity than consulting. I might have been wrong.

My expectations for work are high not because I’m a perfectionist but because I’m addicted to the feeling of reaching beyond my limits. As a workaholic I struggle to let go of work that is “good enough” as work functions as my dopamine hit. I can always do more, produce more, refine more…more more more. This means I often will find myself in situations where the expectations of the person I am working for do not align with my own. I regularly over produce. I’ve got a classic, and telling, story from my first year in prep school that says it all.

I attended Waldorf Schools as a child. One of the core pedagogical tenants is to teach to the child not to the classroom. This manifests in unique ways, including making your own textbooks. Teachers will put a lesson on the blackboard and students are expected to fill this into their own “main lesson” books which function as your textbook for reference later. A child is welcome to add as much depth to their book as they desire. Main lesson books are often elaborate illustrated affairs with extensive reference materials all completely done by hand. This is great for pushing beyond personal limits and the stagnating effect of teaching to the mean. It also happens to suck if you have a tendency to overwork yourself.

I didn’t realize this was an unusual method for years. So when our town didn’t have room for me in the single Waldorf high school, my mother enrolled me in the town’s private prep school for 8th grade. My history course was American History. On the first day the teacher passed out a map of the United States and told the class our homework was to “full it in” for tomorrow.

I went home and spent 3 hours illustrating geography relief maps, sketching in local points of interest, labeling each state and capital in cursive with my best penmanship. I started crying around 10pm as I had other homework for other classes and I wailed to my mother that clearly I wasn’t academically prepared for prep school. I imagined my other classmates with better illustrated maps with more creative ways of showing base relief mapping.

I got to class the next day and my teacher looked completely baffled by what I turned in. I panicked. What had I done wrong? I started laying out all the detail work complete with my methodology for measuring altitude. The teacher seeing me spiral out said “Julie, when I said fill it in I meant label all 50 states with their name.” I was dumbfounded.

That the assignment was so simple never occurred to me. What the fuck was even the point of assigning something that was so rote? To 8th grades no less! What kind of bullshit low grade busy work was this! I was furious. What a waste of time if this was the standard of work.

How little did I know at the time. While I was spending 3 hours on work to the best of my ability straining to extend my understanding, most kids were smart enough to realize their homework should be working to the “mean” of the classroom not to their own standards. I really was not prepared for prep school. Just not in the way I imagined.

This is all a very long winded way of saying that I still tend to do this. Someone may ask my opinion on how to run an advertising campaign and I will launch into extensive detail on demographics versus psychographics and the importance of building out multiple permutations of creative in your funnel to determine the most effective content for the best return on investment. I will give you as textured and nuanced an wander as possible. You won’t just get “Colorado” on the map I will show you the trail over the pass. This is often great for founders of startups who swear the small stuff as much as I do.

If anything I should agree to more consulting work as you will get so much more out of my three hours than someone who can sense the parameters of the work you’ve assigned them. They mat give you exactly the map you asked for even if you need more and didn’t know to ask. I will draw you a geographic relief map so you can navigate the treacherous mountains of paid advertising. Or any area where you happen to be interested in my expertise. I know an astonishing amount about narrative, branding, public relations, user acquisition and revenue growth. And I should stop convincing myself that I cannot produce work that is of value in a consulting framework. What I wonder work product may be more involved than someone else but that’s not my call. Anyone who hires me can decide if it’s worth a consulting fee or not. And if this story has any lesson it’s that I’ll probably give you well over the median or mean expectation for the job. This is also why I don’t charge by the hour. But that’s another story for another time.

Chronicle Internet Culture Startups

Day 72 and Isolation

I’m an introvert. I do not draw energy from crowds or socializing. My energy comes from within. I like to socialize with individuals, in fact I enjoy one on one conversations quite a bit, but can easily be overstimulated by them and require a quiet period afterwards. Engagement with others draws down on my energy whereas with extroverts that engagement sustains and builds their energy. If you are curious about this framework visit the work of Carl Jung.

Despite the skill set being heavily weighted towards people skills, I suspect leaders in startup land tend to lean towards introvert. My suspicion is that it is a function of the heavily generative nature of the work, you are bringing something from nothing. To be able to consistently bring something new about you need quiet mindful time to yourself.

Sadly society, particularly professional society, is weighted for extroverts.

Open office plans, meetings, collaboration and buy in, managing up and down, all assume that that extroverted behaviors are the default positive positions for a team. Add in after office cocktails, team dinners and off site events and you start to see a pattern that privilege people for whom social interaction is enjoyable (not even considering if it’s possible or a family strain like parents).

Modern work is a battle between extroverts and introverts and the extroverts have definitely won. Which is weird as despite the Jungian tradition it may turn out that ambiverts, balanced personalities who exhibit both traits, are actually the largest group.

I’ve always loathed conferences as it depleted my energy stores for at best dubious content benefits. During the pandemic I’ve been much more willing to engage with events as instead of arranging for transit, getting polished for a professional environment, moving my productive work hours around the event, I can simply show up and learn. It’s miraculous and frankly I’m sad so many people want to move on from these accessible events as it probably means I’ll drop attendance entirely. I can say yes to a lot more if the accessibility of an event remains geared toward remote, introvert and disabled. You don’t have to be any of those things to prefer it either. Maybe you have kids and appreciate participating in the culture all those child free extroverted wealthy twenty somethings enjoyed all this time.

I’m afraid that post pandemic the extroverts will win work culture norms again. Even though we are all sick of the over scheduling and the exhausting nature of office and event culture, we miss it a little. And the boomerang back is likely to make it seem more appealing than ever. But I can’t shake the feeling that the pandemic is a bit like a societal hypochondria moment. We needed to be sick to heal our culture. Prioritizing one kind of person and their needs (the extrovert) has led to all kinds of inequalities and tensions. I hope we can come back with a little more respect for the culture and desires of introverts. I know I’ll be coming out swinging for more balance.

Chronic Disease Chronicle Startups

Day 64 and Addiction

I’ve been working through unconscious mindset issues and self limiting belief systems as an active exercise the past few months.

I’ve been really hung up on the value of pain and discomfort. Somewhere along the line I became convinced that working hard is morally good. And over time that developed into an addiction to work. I got off on being seen as someone who never quits.

This workaholism eventually had the consequences of forcing me into quitting everything in order to survive my addiction. I didn’t have a choice at a certain point as it was stop being a workaholic or quite literally die. My health failed me so I could have a second chance. I’m still grateful that I chose life but not a day goes by where I don’t wonder if it was the wrong choice. What is living if I’m not killing myself?

Realizing that rock bottom was a choice was a bit of a shock to me. I always thought it was an external forcing mechanism that finally freed you from your addiction. I had a very Augustinian “make me good but oh not just yet” understanding of my addiction.

And because my addiction is considered virtuous I’ve had a lot harder time seeing the value of letting it go. We look down on drinking, drugs and other sins. Work isn’t on the list of seven deadly sins. Sure I get pleasure from working but I can’t separate it entirely from the external validation I got from being “good” especially from people I perceived as my betters. And because I had a challenging relationship with my father as a child (he is also a workaholic) this put me in a precarious position when dealing with older white men. In other words, anyone who will ever finance me or mentor me, as technology and finance has an extreme demographic skew. I was constantly in a place where I wanted validation from these elders to soothe my inner child. I would do anything to show them I was good and worthy. I’m sure there is a Biblical or Greek tragedy angle to a child so deeply committed to being sacrificed for their father.

All this was compounded by the feeling I got when people who were my peers put me on a pedestal. They wanted me to be a martyr as much as I wanted it. And some of them will likely never forgive me for not being their own personal Jesus.

This all leaves me with very mixed feelings as I know I hit my rock bottom and it’s time to leave behind my addiction. And it’s very much time to rid myself of enablers who pleasured and profited off my disease. But it’s so much a work in progress. I feel the desire to jump back in to work and say yes to everyone who wants my work. I love it and they want it. But I need to find a way to only ever commit to those who want me to be well and thriving.

Too many people profit off of the deep desire workaholics have to always be producing. Capital and eager teammates can easily see a workaholic as a better bet for making money. I’m sure most don’t realize it is predatory because they assume we can stop. The sad truth is I’m not sure I would have stopped. I just got lucky I became too sick to carry on. So this is me committing to only working with those who want me on their team if I’m healthy and “sober” because I’m not going back on the “bottle” ever again. I just hope it means my work will be better for it. I think it will but it’s one day at a time.

Aesthetics Chronicle Finance Internet Culture Media Startups

Day 62 And Who Can Make Art

My ego dislikes debate, but my heart leaps at tension.

Over the weekend, my friend Phil and I decided to make a functional art installation called Illegal.Auction. The premise is simple: we are selling Fungible Tokens (or NFTs) of Culture. 

Unsettled ideas of generation and representations colliding with abstractions like finance are important issues both culturally and practically.

Art is for itself, so who cares either way. A certain dogmatic insistence that “medium is the message” is pervasive in the critiques. Are movies different than books? I don’t think they have anything to do with the price of milk. It reminds me of the classic Annie Hall scene (speaking of artistic intent and harm) where Marshal McLuhan explodes on a chattering group “you know nothing of my work.” Woody Allen’s character concludes the scene if only real life were like this. Well on Twitter you can recreate this scene everyday!

It is funny because commentary is distinct from creation. And a lot of people have takes on McLuhan that he himself doesn’t agree with. But who cares right? Interpretation of art is ostensibly art.

It’s very interesting to see just how angry people get about the worth and value of culture in particular. As if it’s some monstrosity to comment on the abstract financial value of some creation with worth that cannot be extracted.

If it were so easy to make value judgments about art then we would trade it on the Chicago exchange like pork bellies and orange juice. Not that we don’t already sell art and trade it and frankly it has been a massive tension through the history of human creation how we value that work, but now many have decided to insist that art is non-fungible. Not interchangeable on a one to one basis like an apple. And yet we are acting like everything can be valued and traded so easily with NFTs. By making art tradeable on exchanges, we have made some thing inherently non-fungible, fungible.

This is ultimately where Illegal.Auction came from. These conversations are important and transformative. That we choose to represent the tensions with representations of reproductions of jpgs of art is part of the art installation. That it is a functional sale is in inherent to the tension.

There is a part of me that is really worried that because I am not a practicing artist that is paid for work or represented in a gallery, that I don’t have a right to comment on these issues. I am a technologist and I do work in finance and the overlap of disciplines makes this an inter-disciplinary question in my mind. It seems like some people disagree with my right to create art (and certainly the morality of remuneration).

But if we insist that only artists can make art I don’t have any right to make installations remixing software and representations. But I’m not sure anyone reading this is comfortable with that world. I am not.

I think people want there to be simple yes no questions to these things. Is it legal? Did you steal? Is it a transformative remixing of a cultural artifact? Is it worth $1 million? And the truth is is that there is no easy answer to what political system is best or how much some thing is worth. Trillion dollar industries are based around the fact that we don’t have clear answers. Irate commentary doesn’t help any of us understand the infinite questions of worth and creation. It is good to do and helps further understanding but its crucial to remember indignation and moralizing is a function of ego.

Personally I don’t think that wealth has any moral value. I don’t want to have to be wealthy in order to be valuable. Or if a piece of art I make does make money do you have a right to tell me it is objectionable because this isn’t how you make money? I guess you do. Whether you can stop me from doing it is a central questions for the ages and also literally why it is important to create pieces like Illegal.Auction in the first place.

This commentary I think is worth having. Not whether speculative infinite land grabs with financial instruments make you worth more to billionaires. They probably do. That’s fine! I think people are mostly offended by the idea that non-artists can make art. Especially if a transaction takes place. If we had stamped illegal on the jpgs and blocked out NOT ART on them would it have made it better? Conceptually I’m not sure that that’s true and probably reflects the viewer’s own sense of value and worth more than a legal, political or moral reality. Also I personally think it cheapens the point just to make concessions to dogmatic insistence on ownership in a space that isn’t settled because frankly it cannot be.

Much of the narrative and coverage around NFTs is that they delineate ownership, value and origination more cleanly. I’d argue that they are actually having the opposite effect. NFT’s are ripping away edifice and abstractions that we use to assign value and worth. And that makes people uncomfortable.

Internet Culture Startups

Day 59 and Throwaway Days

The worst part of being in your thirties is no one tells you that won’t be able to sleep past 7am.

So this morning, right after sunrise, I’m plotting all the ways I’ll get to work on new projects today. Never waste a good Sunday. As if time has any meaning in the pandemic.

Here I am sliding back into workaholic ways, excited by the pace of change. But then you are reminded that routines and nutrition and supplements need to be done. So the tension between the allure of work and the practicality of needing to care for your body split. So I stop to mix a supplement smoothie and take some stuff. Then the sun is out so a hike up the front range trail is a must. Nutrition and exercise keeping the tension in check.

Maybe somedays it is ok to prioritize the long haul. The body that need to be strong for the next big shifts. That chaos is coming at us so fast a firm anchor for mind is a must. Techno-progressives need to believe in the positive outcome because we must cheerlead for a better future.

It’s nice to feel like even on throwaway days, you can cheer for all the outcomes


Day 55 and Promoting Your Loved Ones

I love doing little projects and hacks for my friends and family. I always have a pet project or two on the burner for my nearest and dearest. My favorites are typically leveraging my talent for getting attention. Promoting the work and talent of your loved ones feel great. And it benefits everyone.

My husband Alex Miller has decided to more formally put himself on the job market. Both of us make a living through the wonders and vagaries of start up life. This includes angel investing, advising (which pays in equity), freelancing for the companies we advise (that usually means cash and equity) or if we are very lucky full time work making the rocket ship fly.

It’s hard to capture how someone’s life path qualifies them for a startup job. Typically you are taking on workloads that aren’t fully defined. You bring about whole departments and revenue streams. So Alex and I decided to put together a cross between a resume, a cover letter, a reference check and a compensation package into one website to give founders and startup executives a better sense of what he can help on.

Part of what makes startup life so challenging is that you often have problems more than defined roles. It’s just messy all around. So someone like Alex can say he’d like say operational lead roles or is best with series A to B startup COO roles that doesn’t really capture the full range of problems he can effectively tackle or the types of companies where he would be happy. Nor does it really help founders get a sense of what kind of value he can bring.

So we thought fuck it lets put together a site that can hold as much context as possible and make it easy to share. We put it together in a couple of hours so technically my long form writing for the day was writing up stories on how Alex got into startup work,

The best bit that I’m quite pleased with is a little growth hack to make it easier for venture capitalist or friends of startups that want to help source talent to just hit the email button and send off a referral without having to write a word. So go head and take a look. You might help a friend make some money.

Chronicle Startups

Day 53 & The Process

Startup land can feel exclusionary and clique driven. Looking in from the outside it can seem as if all the power and money is concentrated into a few groups that only fund and hire their friends. Less charitably it looks like a circle jerk.

While this isn’t an incorrect perception, I believe why we think it is exclusionary is very different from the reality of why it is exclusionary.

Startups are tight knit because successful companies have high psychological safety. We all tend to work together again and again and back each other’s plays because we have built up a high trust environment in order to survive. Even if we don’t exactly see the vision someone else has we trust that they will find a way to make it into a reality.

We don’t trust that this is true for everyone. Ideas are like assholes in that everyone has got one. It’s the ability to turn a formless expanse of ideas and hopes into a company that makes a product it’s customers like. It’s extremely hard to make something new. Harder than you can ever imagine if you haven’t tried it. So people who make a living out of making something from nothing have developed a set of heuristics that let us determine if someone outside our circle is capable of making “a thing” to prove their ideas can become reality.

We tend to overweight people that build tangible things. Even though many of the most crucial skills in business are the less quantifiable ones. We tend to overweight people that have demonstrated any kind of success in zero-to-one work even if what they want to build isn’t remotely related to what was done in the past. This is how despite most of my experience being in advertising tech and e-commerce I was backed to make cosmetics. People had faith that I could flip the bit from off to on.

While this may make it seem hopeless if you are currently not inside the system that’s not what I hope you take away. Startup people love watching newbies make the leap. I cannot overstate the fondness we have for someone gathering up the courage to spring into the unknown. I used to hate the phrase “I’m rooting for you” till I realized everyone actually did want me to succeed. They just rightly realized I needed to learn the hard lessons in my own time. They could give me all the advice in the world (and believe me they did) and sometimes I just needed to make the mistake in order to learn the lesson. The mistakes allowed me to succeed.

Of course, we always hope people will learn from our advice and not require the pain of a fucked up cap table or a growth plan that missed target because we burned our cash position down to three months runway. But most people that are genuinely good at startup work appreciate that only the person actually “doing it” can make the choices that lead to success.

So startup folks will always be excited to give back and encourage those that want to try “doing it” too. If I have a clear ask I find I get an answer from even the most successful and prestigious. Literally CEOs and world famous developers of entire languages will just email you back. It’s honestly miraculous. I have invested in cold emails. Championed them to my nearest and dearest. Because we believe that the process of making something from thing doesn’t exclude anyone. You just have to show someone that you will try to make your vision a reality.