Tag: Startups

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Emotional Work Startups

Day 153 and Startup Families

I’ve worked my entire career in startups. I love it. But the work barely compares to being a member of a startup family. My entire life has been lived, literally from the day I was born, in the ecosystem of families that make startups come to life.

I was “in it” from conception and all my success and traumas are in some way tied back to that luck. And I became a startup founder and eventually a startup wife. This post is about what it’s like to live in perpetual uncertainty of creation with the occasional bout of life changing money.

For everyone that has a payday that changed their lives forever, chances are they have spent decades in the shadow of that system of building, scaling, and selling companies. The paydays are sporadic, completely dependent on luck and often extremely unfair. Most of the time the early team sees nothing. I’ve personally had an exit where I got nothing. I’ve had an exit where I couldn’t afford to exercise my options so when the company that bought mine exited I didn’t see a dime. So I know how fundamentally random startup life can be. How unfair it can feel. Because today it is our turn to be the beneficiary of the unwarranted success.

My husband Alex’s long time home Stack Overflow, sold for 1.8B dollars today. And yes we are one of the 61 families that will see more than a million dollars from it. But it’s not all joyful excitement in our house. Because it’s not about not just about money. It never has been. In my family it’s always been about belief. And it’s really hard to reconcile the many competing emotions that come with a liquidity event. It’s the culmination of much work and time from everyone.

My father proudly reminds me that when I was born, he didn’t have a job as he was pitching an education startup. What a blessing to have the energy of one’s life be aligned with risk from the start. And also what a curse. My family had incredible boom years where money wasn’t a concern coupled with devastating financial and emotional ruin as companies went to zero and markets crashed. My father sacrificed so much for his dreams. He saw the value of software and took his wife and children to the promised land of Silicon Valley. And oh it was glorious. And oh how it hurt.

I have fond memories of Comdex, elaborate company cruises and board meetings during “take your daughter to work day.” I also remember my father not being there for birthdays, for dinner, for milestones because he was busy building the future. I don’t remember my parents getting divorced, because I suppressed the memories. Family trauma can be like that. The good and the bad exist at the same time. When my father went bankrupt in the Web 1 crash, I was so angry at him for not being more careful, I didn’t speak to him for years. And then I made the choice to become a founder myself. Despite my fury and sadness and hurt I too decided to live my father’s path. And then I married a man who walks it too. I guess the Bojack Horseman joke got it right.

You inherit your parents’ trauma but will never fully understand it. Haha the cop is a cat.

The day you get news you made life changing money is bittersweet because all the trauma of being a startup family member catch’s you to you. You remember the sacrifice of your whole family going back years. The long nights and missed time together. The choices to prioritize the company over your family. In our case 10 years but of course for me it’s been my entire life.

The entirety of my marriage with Alex and my entire relationship with him before was spent at Stack Overflow. I’ve seen the hard work and the pride. I’ve also seen the exhaustion and the agony when something went badly wrong. The hurt when teammates left and the fear of leaving yourself eventually. People grow up together at startups. Other more practical logistics show that not everyone wins. The hard decisions you make when it’s time to leave and you cannot afford to exercise your options are a unique pain. We just three weeks ago sold something in secondaries to afford the taxes to exercise ours. That’s timing and dumb luck. Almost absurdly so. We could easily not be in the position we are. Exits are the end goal and yet not everyone gets to make it despite equal sacrifices. It’s all random and no one deserves any of it. But it changes your life if it does happen.

Categories
Chronic Disease Emotional Work

Day 147 and Over My Skis

For a Colorado native (let’s ignore that I was born in Silicon Valley) a number of our most cherished pastimes are kinda “meh” for me. Skiing is a sport that I can take or leave. That apres ski life is much more appealing than cutting it up on the slopes. But one key metaphor from ski culture gets used lot. “I’m over my skis.”

To be over one’s skis is to risk crashing. Being over ones skis happens out of enthusiasm. An inexperienced or unfocused skier lets their center of gravity tilt forward over their knees. Best case scenario, you are simply going too fast and you better “pizza” your skis to slow down. It’s a endearing but slightly awkward experience which is what makes the metaphor so appealing. It’s never a bad faith metaphor merely a goofy oops.

I got over my skis this week. I’ve been so excited for my workload (new investments, new startups to advise) and some new structures forming in my life (chaotic.capital is coming into focus) that I’m leaning in and finding myself going too fast. A friend of mine, who is my favorite person to “over do it” with, was on the phone with me a lot. I was excited to talk to her. But all this added up.

I realized oh shit I need to slow down. I haven’t crashed yet but I’m french frying. There is still time for me to “pizza” or in the immortal words of South Park’s ski instructor Thumper

If you french fry when you should pizza, you’re gonna have a bad time

I love french frying, the food, the ski position and the metaphor for speed. I want get over my skis. But if I don’t pizza “I’m going to have a bad time.” So with true Colorado wisdom it is time to kick back, get some THC and pizza. May this edition of Rocky Mountain wisdom aid you in finding balance on the slopes and off.

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Finance Startups

Day 146 and Gossip

Gossip drive the world. The stories we tell about other people reflect a lot. Even if we claim we don’t care what others think what others think moves the world around us. And I would posit that this actually isn’t a bad thing. It can drive closer bonds and increased connection.

There is a concept in evolutionary psychology called indirect reciprocity. Natural selection favors strategies that base the decision to help on the reputation of the recipient. Social interactions in which one actor helps another and is then benefited by a third party are key to cooperative reputations.

This isn’t just a systemic population level issue either. People who are more helpful are more likely to receive help. It’s uneven obviously and people can obscure their reputation. Depending on if you are up or downstream of helping or being helped, you make different calculations. Some people help more but they feel it’s worth the cost. They are downstream. Others accept more help because they are upstream. We are all making trades based on our position and arguably they are fair market trades.

How we decide to cooperate and with whom is driven considerably by reputations and shared value beliefs. Relaying reputation signals to bolster your capacity to connect to others is actually a key part of empathy. We need to establish psychological safety to partner with each other. Gossip helps us find suitable relationships. This is especially true in disciplines which require creativity. Quoting myself on the topic of psychological safety in venture capital.

If entrepreneurs are solving entirely new problems with high chances of failure feeling like they can trust their financial partners should be a top priority. Yet the atmosphere of distrust is pervasive. Venture capitalist and entrepreneur are constantly managing the information flow between each other.

Managing the information flow is a key component of gossip. Showing you understand their context, their fears and their reputations concerns helps you. An act we denigrate in popular culture actually helps you to deepen the relationships as each signifier breaks down space between two people and builds trust. So don’t knock gossip. It has evolutionary, societal and individual benefit. Just remember the ultimate outcome is about bringing people closer.

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Finance

Day 145 and HODL

If I like something I want to commit. I don’t get folks who get panicked at bumps in the road. Hype cycles for cryptocurrency trading have been unappealing to me. I’ve never been one to watch things like FOREX trades so why would I want to do it but with Bitcoin? Like I have fantasies about being a trader but I am absolutely not. If I believe in an opportunity I am not a short term thinker or investor. I want to see where it goes.

The real excitement to me in crypto is the potential to impact larger more broad based systems. Changes that occur over time and with significant collaboration are more interesting than any narrative blip. A libertarian monetary policy implications was obviously particularly exciting. As business person the potential to change the middle man fee structure that makes financialization and banking a scourge was equally appealing. As a technologist the possibility of building applications on an entire new protocol is enticing.

The bigger picture is the only thing that matters. Go in the right direction over time and ignore the noise. That’s why we’ve slowly moved up our allocation into Bitcoin over the years. And that’s why I’m excited for my husband Alex to be working as the new COO for Hiro.

Any angle you take on the big picture implications for building new systems is an opportunity for innovation and wealth creation. That’s why I’m HODL. HODL is a mindset. Sure it came out of a misspelling of “hold” when someone was drunk but who can’t relate to the desire to really commit to a bigger vision? Participation in the creation of something bigger is the ultimate HODL value. Hold on for dear life or just hold on. Either way you are in for the long haul.

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Startups

Day 144 and Scars

I have significant e-commerce, direct to consumer and retail business experience. I’ve managed multi-million dollar P&Ls, worked on iconic billion dollar brands and started my own direct to consumer cosmetics line. You’d think with that experience I would be deeply bullish on my ability to pick up and coming startups in the space. But I don’t particularly want to invest in digital brands or online retail. And I think it’s scar tissue.

I’m not saying flat out“no” I won’t ever invest in a DTC business or an e-commerce startup (I have and I will again) but a little bit of knowledge can make it hard to preserve creativity and imagination. Many founders can come out of a space where they have dedicated years of their lives and simply want space away from their expertise. They know too much. They’ve seen things. The scar tissue that forms to keep you working during the long dark soul of startup pain is still tender.

When I mentioned this lingering pain others pointed me to other areas they struggled to hear pitches or invest because of experience. Rental businesses and neobanks from Maia Bittner, certain e-commerce verticals from Lee Edwards, fitness from Jason Jacobs. It’s a common phenomenon among founders.

I’ve got lots of opinions why certain kinds of businesses won’t thrive or have business models that won’t make the kind of return my own personal investing thesis demands. But the truth is that I now have enough expertise to simply know more than is good for me. Ironically this means I should spend more time as an advisor or consultant on certain kinds of businesses but it takes a special founder to coax it out of me. Because I do have valuable insights and I want to share them.

But the last thing I want to do is pass on the trauma of my own experiences. Founders deserve to have their psychological safety preserved so they can build the company of their dreams. Some painful insights from a founder that came before them might help them avoid some pitfalls, but if they take our traumas too seriously they may never find their own path. And that kind of backward looking “it will never work” or “trust me kid I’ve been around the block” attitude can really bring creativity down. So I will always share my honest experience with anyone who asks but I’m hesitant to ever let anyone take my lessons to close to heart. You very well may be the one that breaks through where no one has before.

So when someone pitches me their new retail startup or DTC brand or cosmetics concept I try to be honest that I may nit be the best fit. I’ve got scar tissue. And if a founder insists that I can help I will try. But remember not all skepticism, fear, distrust or dislike is about you. Sometimes it’s all about the trauma of having lived it before. Asking someone to live it again is the ultimate act of trust. And maybe just maybe we get to firm new scar tissue together.

Categories
Startups

Day 125 and Working With Startups

One of the most frustrating aspects of startup life is the vendor startup relationship. There are so many pitfalls and disasters that can befall each side. That naturally leads to a lot of dysfunctions as each optimizes for their own needs, a process that unwittingly leads to the disasters we sought to avoid in the first place by trying to prevent issues.

From a startup’s perspective there are two key issues. Established businesses tend to be slow moving. They are slow moving as they have process and documentation. Nothing is more frustrating to a startup than needing a nimble partner that can throw shit at the wall only to get a meticulous vendor that documents all the shit that didn’t work in exacting detail. This isn’t to say that one shouldn’t report (in a remote first culture documentation is even more crucial) but 40 page decks on what happened will send a founder running.

From a vendor perspective startups are frustrating because they never have any of the assets, documentation or processes in place that make your job possible. Anyone who has become embroiled in a mess of half functional SaaS operation software knows what I mean. How are you supposed to deliver on a contract when all the basics you need from a startup are impossible to locate and occasionally contradictory?

The tension between the two workflows is clear. Especially because startups eventually become more process driven and operationalized over time and vendors are always looking for ways to become more nimble and cost efficient. So you’ve got two parties who want to become more like the other, but as they do that risks upsetting the partner that chose them for the opposite virtues. If this were a romantic relationship it would be heading for a breakup. “You’ve changed man!”

My best advice to vendors is to be as flexible as possible with startup clients. The faster you provide an output the more likely it is that the founder will come to rely on you. Most successful startup vendors simply roll up their sleeves and start producing. They don’t scope in too much detail or negotiate contracts that lock them in, no, successful startup vendors know they give themselves security and contract stability simply by giving a founder what they need every day. As you find more needs you act on it. You stay flexible till suddenly you’ve become the crucial partner that gets budget every quarter. As a startup grows becoming the indispensable partner means that you grow along with it. Your goal should be to have your client succeed at the same pace that you are succeeding.

My best advice to founders is to allow your vendors best traits to rub off on you. Paying attention to their competencies allows you to build up teams that support that. That then enables your vendors to perform even better for you as the fluency on expertise develops. Great marketing teams don’t just produce great marketing in-house but rather they allow it to flourish in the entire ecosystem. There is a reason why CMOs have winning agencies and winning agencies have great brands. The truth is that you will always get the most out of your vendors if you respect what they excel at and spend your time and money prioritizing that support.

The danger if you don’t make productive vendor startup relationships is two fold. One startups will waste valuable capital with a partner that was never a good fit. Two vendors will waste billable hours and employee energy on accounts that have a high probability of imploding. It’s a waste of money for both sides. But when it works well lol it’s absolutely money.

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Finance Internet Culture Startups

Day 119 and Status Narratives

I’ve mostly worked inside insular industries. There is something about disdaining a club and then slowly forcing it to adapt to me that I find appealing. My handle on Twitter “AlmostMedia” wasn’t actually meant to be a joke about the ephemeral nature of timeline driven content (though it is now) but was an inside joke about my first personal blog.

I wasn’t as comfortable being an outsider when I was younger so a common theme on my blog was about how I “almost” achieved insider totems and status but never quite did it right. I never felt like I was stylish enough, cool enough, rich enough or had enough status symbols. Now I kinda laugh at myself as I realize semiotics is as driven by the out group as the in group. I always had the power to be enough.

But thanks to this insecurity about being “almost” but not quite right I’ve achieved a pretty valuable skill set. I’m able to see what is coming, what will resonate, and most importantly what will have status. I’m not always great at the timing (I’m often too early) but I am very good at nudging narratives into the popular conception. I call this the Thursday Styles problem. Timing what is next is as much about knowing what is coming as when it will hit and doing what you can to control the pace.

I particularly like fashion and startups as as success is often a Thursday Style problem. Status narratives are driven by people who like to show off that they knew something cool was coming. Think of the trope of venture capitalists publishing a post about when they first met a founder timed with a company’s IPO. Music used to be like this too with snobs insisting “I knew them before they were cool” when a band blew up.

Status narratives often revolve around being first. Much of crypto is obsessed with showing off how early they were while also insisting to everyone that “it’s never too late” as they need to drive a status narrative that brings in more adoption. Being early generally only matters if you are also still around when it’s “late” and you always need more people to push you further into early. Even if most of the benefits are seen by late adoption we all want to feel like we won the status game of being early. But it’s important to remember we are all a little too early or too late. We are almost right. Which is enough for plenty of success.

Categories
Chronic Disease Chronicle Startups

Day 114 and Resistance to Change

Crash landing my life into a medical sabbatical really fucked up my headspace. Around two years ago I was beginning to realize I didn’t have a choice in accepting that I was sick. My identity as an always on, gets things done, reliable, entrepreneur got replaced by an entirely new self conception as “ill person” in a matter of six months. In August of 2019 I disclosed that I was officially sick. I sold my company and was going on leave.

It wasn’t a pretty adjustment. And I’m probably lying to myself when I say it took months to accept. I hated the new me. I felt weak and out of control. Willpower and muscling through did very little to help an autoimmune disease. If anything that mentality of “working on the problem” made it worse as I needed to rest and let my doctors do the work. I was resistant to change.

I think I’m going through a similar transition now as I did in 2019. I began seeing a new doctor in Colorado in October of 2020 and I made more progress in six months than I did in the previous two years. I’m beginning to face a new identity change as it becomes clear that I won’t be “sick” forever. While autoimmune diseases aren’t like an infection, there is no “cured,” it is beginning to look like I will be healthy enough to live normally. You won’t be able to tell I’ve got anything wrong with me soon.

And I have to admit to myself it’s a mindfuck. The emotional and psychological work I had to do to accept losing my entire identity is happening all over again. Who the hell am I if I’m not sick?

You see for the past two years I got used to explaining to people I was a sick person. I was disabled. I needed accommodations. I couldn’t work in ways I felt I would be reliable. I came accept my identity as someone with physical limits. And I slowly figured out ways to communicate that new reality others who has previously seen me as this abled person.

I guess you could say I was at peace with my situation. The pandemic helped. I know it probably sucked for you but I really enjoyed having a year of my recovery coincide with others having to live the way I did. I know it’s selfish but it helped! I felt less alone.

And yet just as I’m finally feeling like I really got a handle on my new identity it’s not my reality anymore. I’m not going to be a sick person. And while I thought I’d be overjoyed it turns out it’s a little more complex emotionally.

Let’s try a comparison. Imagine you broke your arm. You keep it in a brace and you can’t use it while it’s healing. And then the cast comes off and you are unsure if you can go back to using your arm like you did. You used to move your arm without thinking. You don’t worry about applying pressuring or picking things up before the break. But after it’s scary. You don’t want to set yourself back. You are scared to lift things and scared to apply pressure. I am in that place with myself. I know that the break is healing. The cast is off. But the muscles are atrophied and I’m not sure I trust that everything is knit back together. But the reality is that soon I’ll have the all clear.

But who I am now? I’m not the entrepreneur I once was. That workaholic Julie won’t be coming back. But the disabled sick Julie won’t be with me forever either. And I’m a little scared about it what’s coming. Who am I going to be next?

Categories
Startups

Day 112 and Unknowability

Human minds seem to prefer predictably. The back brain craves knowing what is coming even as our flighty consciousness seeks novelty. Talk about a tension that sucks. We’ve all seem just now much this is a recipe for misery when you live in a world with no predictability but easy access to low stakes novelty during the pandemic. We are twitchy, bitchy and miserable as we have no idea what our world will be like but we can dopamine drip our pleasure seekers with social media, food and substances for an enjoyable now.

I’ve written at length in this experiment about my frustrations with unreliability especially when it comes to my own body. It’s one of the hardest aspects of managing a recovery from an autoimmune disease. I need to be mentally strong enough to not let bad days shake my routines so I keep building towards the wider goal. I can’t be distracted by one data point. It’s about movement towards the goal. Ironically this is a skill I learned from startup life.

While the entire planet is getting a crash course in unpredictable futures now, startups are defined by their desire to solve problems that don’t yet have defined solutions. No one in a startup knows if the predictions will be right. If they are working on something that will have the intended outcomes is unclear. You work on faith. You trust that over a longer time frame the daily tasks and routines you push (sometimes we give them dumb names like OKRs to fake a sense of control) will actually get you where your mind’s horizon sees.

I sometimes wonder if those with religious faith would do better on average in startup life. We have some degree of comfort with the inscrutable. Mysteries are sources of joy rather than fear. We trust that there are things beyond our knowing and our control and yet we must live on despite that.

The obsession with data and trend lines and the potential for prediction, surety or knowing amuses me. Sure sometimes you can plan a lot. You should plan. You have some inputs that consistently deliver the predicted outputs. Your best guess are better than other people’s facts (thanks Spock!) But if it were all so neatly defined there would be nothing new to create. We wouldn’t be able to build value. It’s the undiscovered country that we seek.

In faith, in life, and in startups you must manage your squishy human mind that is constantly tortured by its own biology. We want to know and we want it to be predictable. But we also love the tickle of a new experience against our dopamine seeking biology. The spike of pleasure we find pleasure in the newness. That’s why we do it. And it’s on us to balance the tension between our need to predictably build and our addiction to novelty. Manage that and you may get far in your journey. Or it’s a miserable sine-wave that makes you nauseous as you go up and down trying desperately to bring the future forward between impulse and planning. It’s usually both if I’m honest. So if you don’t enjoy roller coasters I wouldn’t get on this ride. But if you do well you just might see God.

Categories
Internet Culture Startups

Day 101 and Closed Ecosystems

The One of the most important novellas in the formation of my technical philosophy was actually written by a science fiction author Neal Stephenson. “In the Beginning there was the Command Line” should be taught in every history of computer science course. Go download it now for free and enjoy 70 pages of riffing on the utopian possibilities of open systems, the accessibility of closed systems and who is the ultimate winners of computing becoming a closed system (surprise it’s Disney).

The premise of the essay is simple. There are two core tensions in how computing has been distributed: open versus closed. The basic manifestations of which philosophy you pick have significant impact on what your users can build but also how accessible your machine or application will be to users. Stephenson focuses on the GUI or graphical user interface, perfected by the closed Apple computer universe, and how it has made computing infinitely more accessible to the masses while also taking away some of the power and flexibility of the original command line interface of prior generations.

In the battle for powerful and hard versus easy but more limited, Americans chose easy and the rise of the GUI began. Dicking around with your computer, let alone your phone, almost isn’t possible without graphical representations of computer programs. Even though said programs are ultimately manipulated several systems down on a command line (you know the “hello world” text interface you might have seen on some NCIS dad cop procedural hacker show) most of us have thoroughly bought into the desktop metaphor of the original Apple GUI. And yes this is old news. This problem of the GUI got won in the eighties. But the basic problem of open versus closed still rages on with us.

The current debate is most vivid on in the financial world with crypto, Bitcoin and decentralized finance as we all yammer on about DAOs and NFTs. But you see it in social media as creators become locked into closed platforms from which export of their content is almost not an option as without distribution and audience access their work means nothing. Creator economy businesses can make money from individual closed platforms but struggle to build businesses as they are too tied to one type of revenue stream. If they are big on say YouTube or TikTok but can’t take their audience elsewhere that’s an issue. Imagine a world where they could take their business with them not be locked into one revenue stream for a platform they cannot change.

What I’ve written here is more like an appetizer course for the philosophy debate and not an argument. I have an opinion in the debate which is that open ecosystems are better for more types of people but I’m also writing this on an iPhone. But I’m writing using WordPress on my own domain rather than choosing a closed platform like Substack. So it’s not exactly a simple binary outcome for anyone ever. Which is all the more reason to go read the novella now.