Category: Startups

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Politics Preparedness Startups

Day 799 and Black Friday

I suppose it’s now quite clear why I felt like I was driving through a snowblind yesterday. For someone who spent the year telling everyone to watch Margin Call you’d think I’d be pretty prepared for the inevitability of pricing affecting risk.

I am, of course, discussing the collapse of Silicon Valley Bank. We’d discussed in our household scenario planning around what would happen if we saw banks forced to compete on better interest rates. Perhaps the same old story of mis-pricing your risk would play out. Discussions of contingency planning and multiple accounts and insurance policies both personal and professional. I really didn’t expect for any of the emergency use cases to manifest as to even contemplate it is simply too horrifying.

But horrible things happen every day and I am skeptical of my capacity to judge my own need for a comfort in a situation in which there is none to be found. I do however believe that in the wake of the Great Recession we’ve come to believe that money always gets bailed out. And why would Janet Yellen (of all people) hang out the singular shining star industry that keeps the lights on in the hollowed out shell of post-industrial American capitalism.

That said humans have been known to do spitefully stupid things that hurt themselves so long as it also hurts someone they dislike. Cut off your nose to spite your face. I don’t know if the drive for vengeance is strong enough for some populist reactionary spill over. I’d want to at least offer up a scapegoat and I’ll be curious to see who has this fate.

This seems like the crumbles to me. The logic of the Jankening is that we cannot always predict the downstream effects because this is a complex system. All I know is that to let a large chunk of the wider technology ecosystem fail would be catastrophic.

However, we have now effectively put in the minds of a new generation that banks do stupidly silly things occasionally (Lmao) and you have to be careful who you trust with risk. Everyone is running to the big banks and that will have its own consequences. I am curious to see what the downstream consequences will be.

Be careful who you trust, use some common sense and don’t be overly sure of the value of powerful people telling you want to think. They might not have your best interest at heart.

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Emotional Work Startups

Day 792 and Level Ups

I know I am courting a bit of a crash tomorrow because I can feel just how much energy this week took. But I am feeling emotionally like I leveled up. I looked at a few of my emotional patterns this week pretty head on and redrew some boundaries. And this always improves my work performance.

The upside of journaling your thoughts and emotions is you have a back catalog of your own thoughts to compare against your eventual conclusions. You can look back and spot patters in your thinking and tie them together. Writing everyday can be excruciating but I never regret having done it.

I have to always remind myself that it takes a fair amount of effort and a high tolerance for being wrong in public. You have to get used to people disliking you and finding you distasteful. People want to put their emotional response onto you and the hard work of being an adult is not accepting what isn’t yours.

If you can tie that kind of self reflection into your professional life you get all kinds of unexpected level ups. You tell people about your own responsibilities and they trust you with theirs. You get to build great things together by building on shares humanity. The best business relationships I have are the ones where we understand what value each of our personal lives brings to counteracting of own limitations and blind spots. I’ll always work with someone who leads with their humanity first. Big visions get worked out together by trusting each others talents.

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Emotional Work Startups

Day 785 and Not Overwhelmed

Life feels pretty nonstop for me at the moment. I’ve got three deals I’m working on that are about to go out for fundraising, I’ve got my own fundraising to do, and I’ve got eyes on me from press. Normally this would be a full plate for me but I am taking a trip to celebrate my father’s 80th Birthday this week.

Normally I’d be panicking about packing. And I did have a few little moments of anxiety about getting everything done today. But I’m actually looking forward to the trip even as I have all this professional excitement.

My father loves startups. He just lives for everything about technology. He never missed a Comdex when I was a kid. He still goes to CES even now just to see what might be out there. His enthusiasm for this world is clearly where I got it.

So I think I might be looking forward to bringing all of the energy around chaotic.capital to his birthday. My father wasn’t a particularly demonstrative father but I know he’s really proud of the career I’ve pursued. So it seems fitting that for a celebration of his life and this major milestone that I get to bring some of the world he loves so much with me.

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Startups

Day 761 and Calls

Yesterday ended up being a big day for me. A couple projects that have been in the works for months for final confirmations. That meant I spent a lot of time on phone calls yesterday.

I hadn’t planned for Monday to be so busy. I have therapy in the late afternoons so I tend to back my mornings but I still leave enough breaks to come down from the energy and excitement of a big call. I find synchronized communications to be a little overstimulating so I like to meditate and do Wim Hoff breathing to break down my cortisol levels.

But I couldn’t make it happen yesterday. It was too much back to back. I went from an hour long fact checking media call right into my two hour group therapy session. I’d had a few other smaller calls before it as well.

My earbuds were the first to note the issue. With about fifteen minutes left in my two hour Zoom I got the 10% battery left warning from my AirPods. My technology realized it was time to recharge before I did.

And boy was the decay quick. The AirPods went bwoooop and went dead. I could feel myself getting a little dazed myself. As soon as I was off the call I checked my HRV using Welltory and found all my systems were drained. Too many calls has called on too few resources.

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Emotional Work Startups

Day 719 and Step By Step

I was discussing my goals for 2023 with a friend today. They wanted to know if I was planning on making any New Year’s resolutions. I told them that I wasn’t in the habit of using a new calendar year for making big changes.

Generally speaking if I want to do a thing I just start. I honestly feel like it’s far too intimidating to declare yourself to be some kind of fundamentally new person that will, as of a certain arbitrary day, make huge life changes. It’s too much pressure. One of my rules for biohacking is to only change one variable at a time. And I don’t make big changes to it either. 10% a week is good enough for most goals. Anyone familiar with the magic of compounding knows that small changes add up to big numbers.

Which isn’t to say that I haven’t started big life changing projects on January first. If you count back from 719 you will notice I first began writing on January 1st 2021. I did indeed resolve to write every day. But I hadn’t intended it as something I’d keep up for a specific amount of time. I’d hoped I’d practice my writing for thirty days and I allowed myself a little fantasy about how amazing it would be to write for a thousand days.

A thousand days seemed like an impossibility at the time which is why I allowed the fantasizing. My pragmatic side said just get started and see if you can keep going. And I did. I put one foot in front of the proverbial other for two years. Now I’m relatively confident that if I want to do so I’ll make it to a thousand days.

I approach most goals like this. I had a fantasy that I could make it as an investor. I was a founder so I thought let’s wire some small angel checks. We were already committed as a family to being startup operators so why not combine our skin in the game with a little more capital risk with our network.

I never envisioned myself raising a fund and making some big announcement about how I had a venture fund. I just started learning by doing. I cut checks. I ran some special purpose vehicles. And this year I decided to one-step-at-a-time go about raising a rolling fund. I am just doing the thing one day at a time. And it’s going well. Amazing people are coming on board. I am confident I’ll reach my goals just by putting one step in front of the other.

If you’d like to join me my goal is to raise $500K per quarter. I’ve got folks like Joel Spolsky of Stack Overflow and Michael Pryor of Trello so you will be in good company. You can read the fund overview here. Yoican sign up on Angellist through the above link or get on a call with me and we can discuss the fund, our portfolio construction and my thesis. Because I intend to work through the holidays because it remains one day at a time.

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Aesthetics Startups

Day 714 and Cosmetic Organization

I used to be the CEO of a cosmetics company called Stowaway. We were a direct to consumer brand that manufactured and retailed our own line of travel sized makeup. Alas I got too sick to work and we sold the company to a private equity holding firm who shuttered it during the pandemic. I’m “shocked” that travel sized red lipstick wasn’t popular during two years of masking and lockdown.

I don’t particularly want to work in cosmetics again, even though I have arguably priceless experience that could be put to good use helping other brands. Startups are are traumatic and it’s not unusual for founders to find it challenging to work in spaces they know well. You don’t want to undermine the enthusiasm of founders. Also you’ve probably taken enough risks for a lifetime in a given space to never want to touch it again even if you made money.

But I do still enjoy being a consumer of cosmetics. I’ve got what might be the most comprehensive library of travel sized makeup in existence. I moved all of it up to Montana this year where it lives in a modestly organized vanity. For some reason I decided do a little reorganization of it today.

A very messy cosmetics vanity littered with makeup bags, travel sized packaging and a Sephora advent calendar.

Instead of finding a new schema for where I plan to keep all my products, I made it much worse. I let myself get a little bit of tunnel vision and instead of playing around for half an hour I spent an ungodly amount of time making it much worse. I’ve got drawers that are bursting with tiny mascaras, tiny lipsticks, tiny eye shadow palettes and thousands of other items.

I was surprised to find myself enjoying it. I did some comparisons of packaging and formulations and found that I was still quite pleased with what we had built. Many new brands have emerged since then but the promise of a minimalist purse friendly brand remains elusive. I see all the ways I failed but I also saw all the ways in which our team succeeded. And it was nice to feel like perhaps I’d learned something. But now I’ve got to clean it all up before my husband steps on an eyeliner.

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Startups

Day 710 and Holiday Work

Working on a Wednesday is expected. Working on a Sunday is a transgression. And like all modern transgressions, working when you aren’t supposed to be working is now a desirable thing. When work becomes a rebellion, strange things happen to your life. I think magic happens.

I’ve excited for the dead time that the end of the year brings for work. Because it’s secretly one of the best times to get shit done. I am never more productive than when I’m expected to be at rest.

In America, there is an expectation that we take some of the time off between Christmas and New Year. But the time off grows and suddenly no one is expected to get anything done for two whole weeks. And then it’s just a mess of resentment where we are at work but not getting much out the door. It’s such a waste. But as soon as people are actually off the clock. That’s when the entire energy of the situation changed.

When everyone is out of the office, is the best times of the year to sprint ahead. Maybe it’s that when people are off work officially they are more receptive to new ideas. They are less on the clock and can take more chances. It seems fun to check your email after too many hours with family where no one shares your interests.

But trust me people are looking for an excuse to do deals when it’s taboo to be working. It’s as tantalizing as getting a message from someone you want to bone. Look at you doing this thing that is a little bit naughty. What a secret you have getting work done when social convention demands we be with family.

So if you get an email from me during the holiday season know it’s because I’m having a blast. You might enjoy responding. Who knows what kind of cool deals we get done when no one else is hustling.

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Medical Startups

Day 696 and Edge

I’m enjoying a migraine this weekend that was both strong and as of yet unbeaten. Perhaps I overdid things on Thanksgiving and Black Friday. But I’ve been stuck in bed in a dark room for the last 48 hours or so.

While this sounds a bit miserable, I can assure you it is also part of my edge. When my physical works shrinks my cognitive capacity unfurls. I very much liken it to the traditional super hero dilemma of being gifted with something that makes living a normal life a challenge.

I may be stuck inside struggling with light, noise and smell but I can still do most of my core deep work. I can’t take calls or go to meetings but I can be on my phone and my Kindle. I can intake information and I can synthesize that information when I’m in darkness.

And that is 90% of my job. Be informed and make the best decision you can. Those decisions are generally done when you are calm and fast. And I get the benefit of being in rest and digest as often as possible as it’s what keeps me alive.

I’ve got a generalized theory related to finding one’s edge. It’s pretty simple. If other people perceive it as a weakness but you understand how to wield it as a strength then your got an edge. People dismiss you sure. But being underestimated is one hell of a way to get on the better end of a trade.

And so while I’m here looking like I might not be worthy because of some set of heuristics that’s have typically worked well for you I’m actually the one that has a leg up on you. You would do well to think about all the ways in which you can leverage talent and insights that trade below their value. You can make a lot of money betting off of truly underestimated viewpoints.

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Startups

Day 692 and Managing Founders

I spent the first decade and a half of my career as a founder. I am very good at certain parts of the job like creating momentum and getting attention. I am less competent at operations and logistics management. Fortunately I’ve always had incredible teams who managed me.

That’s right, I said teams who managed me. One of the dirtiest secrets my husband kept from me is exactly how experienced operators like him manage high octane founders like me.

“ We don’t take an action until the third time an ask is made.”

Alex Miller

Alex has had to manage some of the quirkiest personalities in startup land so he didn’t just develop this strategy with me. He has been using this three asks technique for a while.

Initially I was extremely insulted when he revealed this was standard operating procedure for dealing with founders. How dare he not do what I request. I did a little ego protection. But then I realized he was right. Founders have to be managed carefully.

Momentum machines without any friction can quickly spiral out. Knowing exactly how and when to apply friction is the real trick. Too much and nothing will get built, but too little and your team can’t get a grasp on where to focus.

Many founders are extremely charismatic people. Their entire job is to get you excited about doing the impossible. And because sometimes we discover that the impossible is indeed possible we often wrongly assume if someone tells us “no” we’ve absolutely got to prove them wrong. We are always trying to generate momentum towards what excites us most.

Alex wisely doesn’t ever tell founders no. He actually encourages you to figure out if you really want what you asked for through his three asks technique. He gathers information. He asks what you are really trying to accomplish. He asks about specifics and technicalities and details. He gently coaxes out the underlying reason for an ask. He gathers information better than anyone I’ve ever known.

And what really drives me nuts is that this system works. If through the process of information gathering the founder continues to insist that something should be done Alex will organize all the details he has gathered in diligence. He will present the information and wait for the founder to ask a third time. If that third asks comes, only then with all the information will he organize the executive team together decides to proceed and make sure the founder is ready to accept the plan.

The genius in this method is that founders have an excellent gut sense for direction and momentum. But because it isn’t our jobs to actually make it happen we can often be total idiots about the resources required and the hidden land mines. By managing both the founders desire for an outcome with the realistic needs of the business, you almost always avoid pursuing the bad ideas.

If you work at a startup, especially directly with a founder, I’d strongly advise implementing the three asks method. You won’t go on nearly as many wild goose chases but so long as it’s done with empathy and tact you will still benefit from your founder’s natural momentum.

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Startups

Day 688 and Hardcore

My generation of founders came of age during the peak of hustle porn. We were young and dumb, and even without the use of stimulants and nootropics like our Gen Z younger siblings, we got a lot done. Probably because we were well young and dumb. And it’s easier to do things with brute force when you don’t have better tools. Being hardcore made sense for some of us.

Alas if you burn the candle at both ends you may find yourself with an astonishing array of healthcare issues in your thirties. Which is astonishingly common in my cohort. I’m just one of the rare examples that is public about the dangers of overworking yourself. Hustle porn’s legacy is mixed. We lost founders to workaholism and occasionally much worse. A generation learned that mental and emotional health are just as important as physical health.

Hustle culture coincided with a lot amazing companies getting built but it’s not entirely clear to me if being hardcore is the only factor at play. Tempting as it may be to look for simple mono-causal relationships in life, the math of success is never that simple. Life isn’t an engineering problem. And even if life was an engineering problem, applying more force doesn’t solve all problems. It might even make a few worse.

I don’t want to knock hard work obviously. Im a firm believer that the basics never go out of style. Hard work is a given. Most of the greats are working hard because once you discover you have a natural talent then maturity generally encourages you to hone it.

Success is built from many fathers even if it’s mother is hard work. Proper resourcing, adequate incentives, teamwork and an effective hierarchy of respect within it are all factors. And let us not forget just plain old good luck matter just as much as being hardcore.

So tempting as it may be to give in to Twitter discourse narratives don’t get fooled into thinking someone that is successful has it all figured out. You don’t know what it took to get there and who brought it together. Don’t overweight success on its own. Nothing is ever that simple. Expect that the team you want to be a part of will demand that you demonstrate all of the above virtues and along with the necessities of hard work. But if it all comes together it is worth the sacrifice.