Tag: Startups

Categories
Aesthetics

Day 705 and Impressed

I haven’t bought a new handbag for nearly a decade. While I like fashion I have never been a hardcore accessories person. One generally been of the mind that those are anchor pieces that you keep for years and years. I didn’t see much point in acquiring trends as it just seemed so expensive. I buy more for longevity.

The last handbag I bought was a camel Masur Gavriel bag. I think it was sometime in 2013 but it may have been earlier. I found a photograph dating it no later than 2014 but I can’t be sure. I’d seen a small piece of press about it as it being a kind of super minimalist brand by these two bicoastal pretty girls. I loved the clean look of the tote with a long full leather panel and a bright yellow sunny interior. I found a boutique that stocked it in Los Angeles. I think I paid less than $300 for it.

I’d talked it up to a girlfriend in finance and she bought one. She then talked it up to her friend who happened to be Lauren Santo Domingo and then next thing I knew the nag was absolutely everywhere. It subsequently raided a large private equity round. It’s brand book became so popular a fast casual yuppie food brand called Digg Inn ripped them off. The brand was a genuine hit.

Being ahead on a handbag like that is the fashion equivalent of being in the best series A round in Silicon Valley as the new angel investor. It means a lot but only after it’s been proven out to the IPO. I haven’t felt that kind of kinship with a brand in a while. And certainly not with a handbag. The high conviction I had with Mansur Gavriel should have made me pursue the two designers as I just knew in my gut this bag was fucking it. Really the one that got away for me.

So I am excited that I got a new handbag today. The first one I have purchased since my Mansur camel tote. I’ve literally not purchased a single handbag in that entire time though I did buy a backpack and a suitcase.

I saw this across it across a bunch of fashion blogs over the year. It has hit a lot of mainstream fashion news. So fashionistas are definitely well and truly ahead of me. I am not a market editor or an influencer being sold by fifteen different publicity firms. Though I’d absolutely like to be. There was absolutely a time when I was very much in the scene but let’s be real now I’m an eccentric investor in Montana. I’m cool just in a different way.

Polène Numero Uno Mini in Black Lizard with dust bag.

The bag is called Numero Uno Mini from a French label called Polène. It’s a clean bag. But it’s got a little personality in it’s shape. There were smooth calfskin options but I’d been searching for a modestly dressier bag that would be a bit of a statement for day but also formal enough it could accompany a cocktail dress or make due at a wedding. It works up until you need a clutch because it’s a gala or an awards ceremony.

Polène Numero Uno Mini in Black Lizard with dust bag.

I feel like it’s a bit louder than the bag it’s replacing which was a black calfskin envelope clutch with a gold chain that is bought from Barney’s. I’d got it on sale for like $150 bucks as well it was a house brand I guess. But it was just so damn versatile I used the fuck out of it. I haven’t seen it since we moved to Montana and I’m a bit concerned it’s gone for good. So perhaps this new Mini will find a home in my routine.

I’m very impressed by its quality. The stitching is tight and lean. The hardware is bright and sturdy. The logo is very discretely etched into corners of the hardware and on the feet of the bag. Which is just a nice touch at a $350 price point. Recently it’s felt like everything is a bit shittier and more expensive. So it’s a joy to get something that feels like a great value and genuinely nice. I hadn’t made some dirty compromises with a direct to consumer business. So yeah I’m impressed with a handbag.

Categories
Culture

Day 700 and Focus

I’m noticing a latent fear in the startup management classes. How do we know if people are focused? Maybe it started with work from home skepticism. But now it’s become an all encompassing yet amorphous fear that nobody is focused anymore. And I have a theory.

It’s all projection. The fear is coming from inside the house. The world is so chaotic everyone is struggling to stay focused. This includes your manager. This includes your manager’s manager. Even your CEO is struggling to shake off the clinging entropy that emerges from constant crisis. And because shit rolls downhill everyone is now flailing around attempting to show they are doing their jobs even as they know they are failing. Even though it remains unsaid because it’s impolite to tell your boss he can’t focus.

The constant chaos that is tugging on our collective capacity to focus is quickly eroding our entire social contract. Not because no one does their jobs anymore. But because we want to be set up to succeed. Because “doing your job” is a point of pride for most people. We like to reliable even if we know there are limits to what we can deliver. So collectively we are hyper vigilant for fraud even as we lack all accountability to each other because we’ve got to protect ourselves first. Self care right?

I don’t see how we get out of this state of fight or flight without a significant changes to culture. Surveillance capitalism isn’t very effective at driving value. It is very good at exacting any drops of it from people attempting to maintain their own dignity. See for instance the railroad workers who have no flexibility in their scheduling. Now with added Congressional oversight!

Categories
Culture

Day 697 and Chivalry for Women

I was having a conversation with one of my girlfriends today about power. We are both exploring the new ways in which we’ve become more aware of our inherent power. Not that we were not powerful when we were younger but rather we have a new consciousness about it’s responsibilities. And it’s relationship to our gender is complicated.

One of the most dehumanizing aspects of Girlboss culture was how it forced female founders into rigid standards of acceptable behavior and emotions. We were surprisingly heavily policed even though we were allowed to use femininity to allure and entice. Girlbosses were empowered. Except occasionally we were only empowered with sex appeal.

Girlbosses looked good on magazine covers and in lifestyle content. It was honestly suffocating even as it was a massive tactical advantage. Imagine being given a cheat code or a level up. Of course you are going to play it but sometimes it takes the joy out of the game.

I am less adverse to the wiles of the feminine as I get older. Now I am able to wield the benefits of mutual viewpoints and seeking common ground. Women are trained to persuade from a young age. We are trained to be accommodating and without hostility or anger. It makes it easier for us to seek out where we might come together.

But those powers of persuasion can also feel manipulative and narcissistic. Men who have felt failed by their mothers can feel particularly hostile towards feminine power. Negative family orientations towards women from siblings to parents can sit in completely irrational and reactionary places for men. I say this because men occupy a similar place for me. Mommy and Daddy Issues can often materialize in stabilizing coping mechanisms. But ultimately it’s not a healthy exchange of power if it’s not consensual.

I dislike having power that I only wield because of my gender. I would prefer to have a less charged environment to pursue my fortunes. But I am also not adverse to playing my hand. You’ve got to play it as it lays. Different women have resolved these power discrepancies in wildly disparate ways. But we are not absolved of the ways in which we hurt men just because we have been hurt by them.

One of the great oversights of the feminist movements may be our lack of a developed gentlemanly style code for women. A theory of chivalry for not playing fair in the gender wars. We certainly expected it of men. If you wield power you must do it responsibly. Peter Parker principle applies to anyone with gifts that can be used for good or evil.

Categories
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.

Categories
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.

Categories
Finance Startups

Day 687 and Winter

It’s cold out there. And I don’t just mean metaphorically. Winter came early and hard to Montana just as the Farmer’s Almanac predicted it would. Driving back in from town last night after grocery shopping it was -3 degrees on the car’s temperature gauge just after sunset at 6pm.

It’s cold out there in the capital markets too. The federal reserve is raising rates to tamp down on inflation and the cost of capital is hitting the technology industry. Frankly I think we’ve all been waiting for an excuse to cut the fat and now we’ve got it.

But it’s going to have consequences for startups. Founders who have never had to live with the harsh realities of a down market are in for a surprise. Those juicy valuations in the private markets don’t work so well when the public markets can find safer returns in a Treasury finally paying out on a t-bill.

Let me play with a tortured metaphor to help you understand the situation. You think you understand how cold winter will be until you realize you haven’t had to work through a chill for over a decade. Sure maybe in your closet you’ve got a nice coat but when was the last time you wore it? If it was for a ski retreat with one of your venture partners then this metaphor is absolutely about to do double duty.

Surviving a bitter cold isn’t just about having a bulky down coat. Think of that as your cash runway. Without adequately rated cold weather gear to keep you alive you may find yourself tapping out. But it’s not just about the coat.

Keeping warm and staying productive requires some technique. Do you understand how to layer correctly? Do you have hats, gloves and scarves? I bet you walk around with ankle socks and Allbirds. That’s not going to go well in a foot of snow. Do you know how to eat for the cold? How about hydration?

Your team will need more than runway. They are going to need motivation to work with less fuel. You have to show them that the climb up the snowy mountain is worth it.

A winter startup team will need the skills and flexibility to work around problems that can’t be solved with money. Shit can and will go wrong on a long cold climb out of an economic winter. Creativity and belief must overlap with intuition if you want to make it.

And it’s important to remember lot of your team won’t have those intuitions. We’ve all been living in Miami and suddenly it’s -3 in Montana. And guess who gets to teach them how to adapt? You. You need to teach your team gently and with empathy what it will take. And they will makeup mistakes. Have you ever watched someone try to lace up boots for the first time? You might need to help them cinch.

I promise it is worth it though. If you are climbing the right mountain, and prepare adequately for your journey, the rarified air of a successful startup is invigorating. And the view from the top isn’t bad. If you need some help thinking all this through as a founder drop me a line Julie (at) chaotic dot capital and I’m happy offer some Sherpa advice. I lived though 2001 and 2007 (I even got laid off during RIP Good Times) so you can rely on me for some elder millennial wisdom. Stay warm!

Categories
Emotional Work Finance

Day 683 and Goverance

I’m not a big fan of early stage venture investors meddling too much in the day to day of their portfolio companies. Asking for too much reporting and too frequent board meetings can be a huge source of momentum friction.

But I am a big fan of corporate governance. Even right from the very start. You should have agreed upon avenues for settling issues and disputes from the moment you have assets bigger than an Ikea couch let alone a 32 billion dollar valuation company. A lack of governance structures can lead to deeply destructive behavior even if you aren’t a sociopathic rich kid bent on committing fraud.

As much as it may seem irritating to set up formalities like a full board and agreed upon voting rights structures, you will regret not having it if something goes wrong. And something will go wrong. I’d go so far as to say Murphy’s law is an immutable law of the universe. What can go wrong will go wrong.

The intense pressure of a startup is what turns the lump of coal that is your vision into the diamond that will be worth something in the open market. And pressure is often destructive. People who otherwise respect and trust each other can slowly find themselves deeply at odds.

Just think of your worst breakup and imagine that intensity playing out in ways that impact everything you’ve worked to build. If you’ve ever gone through a divorce I’m sure you understand. Let me tell you a little story about one of my breakups to illustrate why you should set up governance right form the start.

My easiest personal breakup was also one of my worst. We’d moved in together and devised an elaborate set of budgets and savings protocols. We’d combined belongings. We even set up a shared bank account. He was a corporate governance lawyer at a very aggressive firm. I was working a lucrative corporate job but preparing to go back to startups.

While he wasn’t a contract lawyer, he did have enough common sense to suggest we write up a relationship contract complete with dissolution protocols. I thought this was absolutely brilliant which I’m sure tells you a lot about how I operate. Absolutely all of our friends thought we were nuts. Including a colleague and friend who would go on to be one of my board members down the road.

I was in Colorado for my mother’s wedding. I’d expected my boyfriend to join me. But we’d been discovering that all our good faith attempts to arrange the perfect relationship structure was nothing in the face of widely disparate personalities and risk tolerance. No amount of mitigating structure could overcome those differences.

When I came home he’d triggered our breakup clauses and moved out. Everything was done by the governance protocols we’d set out. If I’m absolutely honest I was relieved. My biggest annoyance was losing the Vitamix blender that was his property. As furious and heartbroken as I was at the time, I didn’t have any avenue to engage in my worst most defensive reactionary emotions. Neither did he. Which was extremely valuable as I hadn’t at age 26 gone through the therapy that helps me productively channel negative emotions now.

My ex-boyfriend and I are still friends to this day. Sure it took a few years for us to come around but we’d avoided a scorched earth situation despite the significant risks we’d engaged in by moving in and combining our lives and fortunes after a relatively a brief period. The damage was mitigated by a shared understanding of how we’d manage downside protection and whose rules we’d consider binding.

While I’m sure this sounds a bit weird, I do think it’s a helpful illustration of why even the most optimistic scenarios benefit from guardrails and mutually agreed upon avenues for pursuing a dissolution or change in status.

No matter how calm and rational you think you are, there will be scenarios that trigger deep emotional patterns. If you vomit up those childhood coping mechanism emotions, you need to clean it up even if it feels shameful and embarrassing.

I’d also say it probably tells you a lot that I’m telling you a deeply personal story about a breakup in a personal relationship and not my actual board experiences. There are some secrets you take to the grave and how you failed your business partners tends to be one of them. How they failed you is another. I’ve had reason to be grateful for corporate governance guardrails at all of my companies. Because that is human nature.

So no matter how early it is in your startup journey you should be considering how you’d handle tough times. Set up a board to help you work through and arbitrate disputes. I know you cannot imagine it now but you won’t regret it.

No one is ever fully immune from disagreement (or even disaster) and you owe it to yourself and your partners to set up fair resolution issues from the start. Plus if you happen to have partnered with a sociopath you will appreciate the modicum of protection offered by binding contract law or consensus mechanism contract execution. And if you really want a Vitamix make sure you put that in the contract.

Categories
Aesthetics Preparedness

Day 674 and Small Delights

I had a fantastic Friday. My husband was home after a week away. I drove to the airport to pick him up and we decided to make a low key date night of it.

I am focusing so much on little pleasures recently. I’m a teetoler for my health but there was a winter ale on Nitro and I just said fuck it I’d like to experience it. It was creamy perfection. The frothy texture giving way to a smooth dark ale.

We came home to a clean house and fresh sheets. Sinking into our recently improved linens was a perfect moment. Who doesn’t enjoy being extremely pleasant with smooth long fiber cotton? The texture of it alone.

It has been these little pleasures that remind my endocrine system that there is still a life to be lived. It reminds me to be present because if I give myself up the apocalyptic hum I am already living it. The Jackpot has already started. So I am giving myself these absorbing moments of presence.

Without them I’m not sure how I’d be without mindful recognizing the delights I still have. I feel like I’ve been ahead of doomer beat for a while and yet it’s all unfolding within the expected models. Sometimes a little bit worse. You see the scenarios and wonder which will unfold. Which careening variable sets off the Jackpot to a narrowing of humanity we can barely fathom.

I’m keeping my limbic system in check. I am working on not setting off my central nervous system into a sympathetic fight or flight pattern. I’d much prefer to be in rest and digest. I see so much energy being dedicated to fruitless ends. And I will not be lending those ends my energy or focus. Neither should you. Your mind is your own.

Categories
Internet Culture

Day 671 and Greatest Show on Earth

I cannot tell if I’m absolutely utterly sick of watching Elon Musk take over Twitter or if I’m having fun watching it all.

Like Musk I am a Twitter addict. I’ve been a power user for the last several years as it was the hottest ticket in town as the media circus around America’s partisan emotional meltdown fomented in the wake of Trump’s presidency. If you were interested in news then Twitter was the place to be from about 2016 onwards.

The funny it is that I’ve had access to Twitter since basically day one but was never a consistent user. A friend was an early employee (so early he went to work for the podcast company) while I got to watch it all play out from the start it didn’t really capture my personal usage for sometime.

I absolutely wasn’t a power user in the early years. I was much more interested in blogging at the time. I ran an advertising network for bloggers and was absolutely obsessed with media. Media was much more interested in WordPress and subsequently Tumblr than it was in Twitter. And I wanted to be where media spent it’s time. Media took a while to really cotton into Twitter.

I was so disinterested in Twitter I didn’t even keep my original handle. I went for years without really being an active participant on the platform as a user. Which was ironic as I did quite a bit of advertising on Twitter.

When I sold my advertising network Coutorture, I decided I needed a corporate job to level up my skills. I ended doing advertising buys and heavy integrations with Twitter as I first went to an agency and then eventually brand side as an advertiser. I was no joke the first brand to live tweet the Super Bowl.

I was a director at an agency that ran digital for Pepsi and I ended up as the voice of Sobe. I was embarrassingly Lee the Lizard during the Super Bowl. At the same time I was also running a second Twitter account for Pepsi based on an SNL skit called PepSuber. We thought it needed to be live tweeted for maximum effect. No joke I was on a conference call with Lorne Michaels at 2am the night before the Super Bowl. The absolute coolest thing I did on Twitter though was probably the first Twitter aggregator. Through my friend I got access to the Twitter API and built a dashboard called Tweefreshing for Pepsi. It was Pepsi integrating all the best tweets of the day for you. It lasted like a day before it got abused. I know simpler times right?

Twitter has gone through a lot of ups and downs as an advertising destination and as a nexus for power and users. It’s always been a circus. It’s never really managed to grow up as a destination for advertisers. I don’t know where it’s going and this is clearly a nostalgia post for me. But over time it won me over. I went from a bystander to an advertiser to a power user. And I remain hopeful it will find a way to remain the greatest show on earth.

Categories
Finance Startups

Day 649 and Build in Public

People love building in public. The universe loves a specific ask. Today for my 39th birthday, I am doing both.

I would like to raise $5m for chaotic.capital’s rolling fund before I turn 40 next year. #5Before40 has a nice ring as a hashtag right?

Chaotic is the first check into founders and companies that adapt humanity to complexity. Personal flexibility, organizational agility, and societal sustainability.

Our founders capitalize on chaos.

You may have noticed I’m a bit of a doomer. I keep close tabs on the opportunities presented by an increasingly unstable world.

Climate change, distrust of institutions, geopolitical unrest, resource scarcity, rising tides of populism. There are founders who can help us address and survive these pressing issues.

My goal is to raise $500K per quarter via a rolling fund. There is 155K per quarter committed from folk like Joel Spolsky of Stack Overflow and Michael Pryor of Trello so you will be in good company.

With a base like that, I want to do the rest in public here on the blog and Twitter. You can read the fund overview here. Building in public has generally been my preference and it has felt weird doing any of this fund work quietly behind the scenes.

You can 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.

I’ve got big ambitions for accelerating into maturity as I have no intention of letting entropy win.

Humanity deserves progress, and I demand growth for myself. I’d like to make us both money with that. 

______________________

FAQ TIMES

Haven’t you been investing through chaotic before? 

Yes but just with personal capital and an SPV. I want to scale it up as we believe our performance warrants it.

Go check out some of our best investments here. https://chaotic.capital/fund-overview

______________________

Why didn’t you raise more during good times? Why the fuck are you raising a rolling fund at the end of the world?

Did you miss the part where I am a Doomer? We are a bad times fund. This moment is where our thesis matters.

Good times return and you’ll appreciate having written a hedge check or two into weird companies that are designed for the power laws of institutional chaos.

Or if the fear of the moment feels overwhelming you can sit back and die the slow death of uncertainty. Trust me I’ve considered it as well.

But personally, I’d write me $10,000 check and come along for the climb back. Entropy only wins if we don’t fight back.