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Startups

Day 203 and Living Rent Free in Our Heads

There are two kinds of startup teams. The ones that forgive each other, and the ones that don’t. If you are very lucky, everyone forgives each other in time. But for the ones that can’t forgive each other, the pain of the experience is a curse. Your failures and weaknesses live in each others’ heads rent free. And that sucks.

I understand how the curse of the unforgivable startup sins get cast. I understand the pain of having people in your life that you cannot imagine forgiving because their sins against you feel too big. Startups are exactly the kind of place where forgiving seems impossible. Why? Building something new is painful.

New life, new business, new art. It hurts to birth something from nothing. Those laws of thermodynamics seem to indicate that energy doesn’t get made or lost, so sure, getting an idea to come into reality has to have an energy cost that comes from somewhere. I’d argue with startups it comes from our will. Maybe our soul. If you aren’t into that then money and time. It has a cost is what I’m saying and we pay it. And when we feel we’ve paid those costs unfairly it’s hard to forgive those whom we blame.

When you’ve given so much of yourself to make a new reality, the pain of it not succeeding is real. It hurts to realize we’ve failed. To come headfirst at the possibility that your sacrifice was for nothing is existential. That the energy you took to build something was for nothing.

With existential problems you’ve got two choices. Face who you are and your part in it or blame it on someone else. It is a lot harder to own existential yourself. If we are feeling like a victim there are people who we can blame. We hired wrong. We had cofounder issues. We couldn’t collaborate well. We had cultural mismatches.

There are endless reasons our failures are shared. And it’s true. Failure never has a single point. It wasn’t just you. But it’s not your cofounder or your teammates fault either. You have to forgive them. They have to forgive you. If you don’t they will live in your head rent free forever. And no one wants that. Find a way to forgive. Find a way to own your own existential failures. It’s not worth losing people over.

Categories
Emotional Work

Day 187 and Reactivity

I do not back down from a fight. I think quickly on my feet and enjoy pugilist types who are always looking to land a point or a punch. I think it is fun to scrap and throw a hook. But I increasingly find reactivity to be unappealing. The difference between enjoying a fight and being reactive is simple: fighters are in control and reactives are not.

Reactivity comes from emotions. When someone says “I feel triggered” in popular culture it’s viewed as a funny jokey way of indicating that something set you off. But being triggered has a real meaning in psychology. It’s a reaction to a memory, consciousness or unconscious, that is emotional in nature. Generally it’s in reference to something traumatic.

Traumas exist for most of us in our past. When you go back to childhood what we perceived as a trauma when young may not rationally be worthy of the emotional response we have as an adult self, but it is crucial to remember is actually real to the inner child. It’s hard to remember that feelings are not facts. So when you are triggered it’s because you have gone back to a traumatic time where those feelings were absolutely real. But they are not real now.

I used to be intensely emotionally reactive in my twenties and early thirties. I am still physically reactive and likely always will be. That’s a different issue. I’m talking about emotions. When I was younger I was sensitive to being hurt and abandoned. I nurtured codependency and recoiled from those who I perceived as disliking me. Thankfully my godfather noticed this pattern and how it was making me both miserable and unproductive, and introduced me to an old school Swedish family systems psychiatrist.

Now five years into my practice I am finding that I am able to take a beat and assess “why” I am having an emotional reaction. I can track back it’s source to my childhood. I can parent my “inner child” through the reactivity and get back on track. You will often hear me use lots of feeling words. I feel hurt. I feel sad. These help me stop the emotional reactivity. It’s ok to have feelings. It’s ok to express them. But you must be like the fighter. You must as an adult be in control. Your inner child who experiences the trauma as real will never be in control. That’s ok. It is your job to parent your inner child through it.

Obviously this is incredibly hard work. I slip up every day. But I try to work on my self awareness. I try to control my reactivity so my inner child isn’t puking all over the floor. It’s not that I don’t have reactions or emotions. I do. Big time! But I no longer wish to be emotionally reactive. Nor do I wish to be around those who are. We must work on compassion and empathy so that when someone triggers an emotion in you instead of snapping back you work to understand where they are coming from.

Categories
Chronic Disease Emotional Work

Day 186 and Broken

I’m coming up on my two year diagnosis of ankylosing spondylitis. I’ve had two years of feeling broken as I waded though the long haul from being bedridden to now being reasonably healthy. But I’ve yet to let go of the feeling that I’m broken.

Being a productive worker has been a part of my identity for my entire work life. To experience two years of not contributing financially to anything nearly broke me. What value did I have? How could I ever recover?

But I’m not broken. I’ve got more limits on my time as I just focus on health and wellness to avoid a repeat of my medical leave. But I doubt most people would know or care. I’ve been doing some of the best work of my life recently. So why does this feeling of brokenness persist?

Some of it is tied to me making some mistakes as I transition back to workout full time. I feel I owe people my time and work as I let them down. I feel I have a debt to pay off (not a literal one but more emotional for having stuck with me when I wasn’t useful). So I’ve been tolerating some people and work that I should probably let go. It takes as much energy to work on small potatoes and worry oneself about as it, as it does to aim for the big projects and goals.

Categories
Emotional Work

Day 185 and Small Potatoes

I’ve been stewing on something for the whole day so I’ve not felt I had the mental focus to write. Plus it’s 4th of July and I was busy eating BBQ and watching Roland Emmerich movies. I’ve watched Independence Day every single year since it came out and that’s as traditional as Die Hard on Christmas.

The reason I was stewing this morning is I feel like I’ve been wasting my energy on something. It didn’t start as a waste but it’s dawning on me that I’m not the best at protecting and preserving my limited reserves. I say yes to say too much.

I’ve got to stop fucking around with small problems. If I’ve got the capacity to manifest shit into reality 20% of the time why am I using that up on small potatoes when it’s just as much work to do it at scale?

Why put my energy into solving smaller problems when I can swing for the fences? Why do I think small potato problems are worth an iota of my energy. I am the type of woman who refuses to cook because it’s an inefficient use of time when industrial society has packaged foods. So why the fuck do I keep saying yes to people and problems that I don’t think are worth my time when I won’t even boil water? What the actual fuck is wrong with me.

I just feel too much social pressure to say yes to asks. If someone gets me excited to help I’m terrible at stepping back. I got convinced I was a mean bad person when I said “no” as a younger woman. I was told I wasn’t being accommodating. I was told I wouldn’t be well liked if I wasn’t nicer. Now I’m beginning to realize this was potentially poor advice. Might even be a function of gender (got to be a good girl). Either way I’ve got to stop saying yes to shit.

I’ve got limited energy and time. We all do. But it’s especially true for me as I deal with a disability in my ankylosing spondylitis. A chronic disability means saying yes like an abled person is terrible strategy. I’ve got to play the game smarter, budget my energy and time like the limited resource that it is and get over any past perceptions I cling to about “being nice.”

You know what isn’t nice? Saying yes to something you don’t want to do because you don’t want to hurt someone. Then you hurt two people. And one of them is yourself.

Categories
Emotional Work

Day 179 and Invasion

As a child I felt that I wasn’t always wanted. Whether or not this is true is somewhat beside the point. What we feel as children lingers in our emotional profile for the rest of our lives. The flip side of feeling unwanted for me is feeling invaded when someone wants me. Ironic right? Talk about a “careful what you wish for” situation.

To overcome feeling unwanted as a child I developed the capacity to draw attention. Despite wanting nothing more than to be wanted, now as an adult I can negatively when people do in fact want me. It’s a perverse double edged belief system born out of a child’s logic. Because I so badly wanted to feel wanted for so long the hurt and fear of that experience lingers.

I’ve written in some detail about the complex relationship I have with being wanted and the expectations I feel when I am the center of someone’s attention. It’s not an emotional pattern I’ve cleared yet. But I’m trying to notice how it impacts my life. Because if you get what you want you also need to want what you get. I want to be learn to be comfortable being wanted.

If I don’t break this pattern I’ll he caught in the same cycle of attraction and repulsion for the rest of my life. Because I’m not actually feeling invaded in many cases. I am feeling the memory of the hurt of being unwanted. Rather than accept the closeness I said I wanted it feels safer to push it away. But that’s no way to live. We can all break our childhood trauma. So I’ll keep at it.

Categories
Emotional Work

Day 165 and Somebody Wants You

Yesterday I asked why I wasn’t doing anything to cultivate an audience. I asked for feedback on why I wasn’t seeking attention when, well, writing in public leaves open the possibility of getting attention.

As it turns out I have a complicated emotional relationship to attention. Because I’m really good at it. I get paid to get attention. But I resent it. And I resent it because I felt unwanted as a child. Which is how I got so good at getting attention.

I have to remind myself feeling wanted as a child isn’t my fault. I didn’t do anything wrong. I was a kid. It’s not even really my parents’ fault. Kids just pick up on shit and then they learn how to get what they want. And I wanted to feel wanted. So I developed a knack for being the center of attention.

Which is a long winded way of saying the second I put on external expectation on this writing from others, especially the expectation of having the attention of others, I’ll put myself into a cycle of feeling unwanted. I’ll perform to get attention. Then I’ll resent the attention. Then I’ll feel pressure to keep the attention.

And that’s not why I started writing. I did it for me. I’m afraid if there are days where I don’t have something to offer then I’ll revert back to being a useless kid who isn’t wanted. Then I’ll dive into ways to get attention. I will make content that is wanted. I’ll resent it when I get it because I should be wanted without performing. And well you see where I’m going with this.

Nothing ever fills the hole of those early childhood emotions. And I absolutely do not want this space to turn into something performative to get love and attention. If it gets attention just for existing then that’s ok.

But the pressure to give something to others is work. I can make spaces for work. Twitter is half workspace for me. But this blog isn’t for work. I talk about things I work on but that’s not the point really.

This is a space for the somebody that wants me. And I’m the somebody that wants me. And if you want me too that’s great. I’m glad you are here. I want you too. But no pressure or expectations. We can just have fun with it.

Categories
Chronic Disease Emotional Work

Day 158 and The Mondays

I feel like Garfield but I don’t like Mondays. After two glorious days of reprieve, on Monday I restart the constant parade of medical appointments, biohacking activities and other habits and routines I maintain to keep my body healthy. And even with all that effort, my health is still bottom decile. The routine I lay out below can feel overwhelming with the amount of time it takes and yet if I don’t care of my body…well it won’t take care of me.

Garfield the grumpy cat falling out of his bed as he realizes it’s Monday

I woke up at 730 and made myself a breakfast of berries and homemade yogurt from raw milk. I used to be an intermittent faster but now I have to take medications with food so breakfast is back.

At 830 I read the news headlines and top articles from Bloomberg, New York Times, and the WSJ as well as listen to NPR’s morning edition. Then I need to do my physical therapy and stretching.

At 9 I go for an hour long walk. In order to keep inflammatory conditions under control, it’s recommended that I do at least an hour of low impact walking to keep limber. During my walk I will listen to more financial news and podcasts. Today I treated myself to Exit Scam by Aaron Lammer. Normally I listen to Odd Lots or something more specific to my corners of finance like Flirting with Models. I decide to go with Exit Scam as Aaron Lammer impressed me so much in Odd Lots a few weeks ago with his episode on yield farming.

At 10am I organize my supplements for the morning. I take Ray Kurzweil levels of stuff that is monitored by not one but two functional medicine doctors. This doesn’t include the slurry of powders I drink in water, just the nice easy pills.

Then I am hooked into a EEG for an experimental “brain training” protocol called dynamic neurofeedback. The best metaphor I’ve got is to defrag your mind and reorganize your pathways. It’s basically CBT with an EEG. The session lasts for 33 minutes I also sneak in a meditation during this time.

Electrodes hocked up to my head for an EEG as I do dynamic neurofeedback

11am means it’s time to lift weights. I can’t do much and I need long rest intervals but I did a full squat cycle.

1130 has me showering and doing doing cold therapy. Yes I stand under a freezing shower for 5 minutes and do Wim Hoff breathing. Somehow I also manage to wash my hair.

At noon I have a banh mi (the pork and short rib from Daikon are quite good) and finish an episode of Mythic Quest. It’s wonderful and I recommend you get Apple TV just for this and Ted Lasso. I needed the break to just hang with Alex and do nothing for a minute.

Finally at 1pm I am able to get some work done. Getting emails out, checking on deals, reading some pitch materials and checking in on portfolio companies. I should have a straight shot through to 3pm to work before therapy but my mother and I ended up on the phone.

3pm is a full hour with my therapist. Arguably the most important hour of the week, especially for getting my mind right for Tuesday’s productivity.

4pm I have a brief break to take more supplements before I go back for two hours of group therapy.

Yes you read that correctly. On Monday I have 3 hours of back to back therapy. What else can I say? I’m committed to my emotional growth. We do family systems work and group work is particularly helpful for seeing your reactive patterns and how they are or are not mirrored back. As much as I sometimes resent how much time I sink into this work I do believe it’s the best ROI on time. We repeat the patterns of our childhood unless we clear them.

Finally at 6pm l have time to do things that are not explicitly for my mental or physical health. So yeah I’ve got mixed feelings on Monday. I want to live life beyond treatments and working on myself. I wish I could live without meds, supplements, physical therapy, walking, lifting weights, meditation, and therapy. But I guess that is what Tuesday’s are for. Monday is just Monday. And yes I repeat some of those activities every single day.

Categories
Internet Culture Startups

Day 154 and Mixed Feelings

I’ve been in a hazy “did that happen place” emotionally after the news that Stack Overflow, where my husband spent 8.5 years, sold for $1.8B. Obviously it’s a lot of money to just appear into our lives. It’s not the first exit for Alex Miller or me. I’ve had 2 acquisitions for companies I have founded & he’s had an IPO for a company he was early to join. I also lived through multiple exits, financings IPOs & bankruptcies as a kid as I’m the child of a startup family. So why does this hit different?

I think part of it is that our other wins tended to come from “faster” companies. My first acquisition came within 2 years of founding. It wasn’t a lot of money but let me pay off student debt & get more stable. Alex was with Yext for a comparably shorter period and when it IPO’d he’d long ago left for Stack Overflow. And that was only a win because he was lucky enough to be able to borrow money to exercise his Yext options or it would have meant nothing. That happens a lot to early stage employees. They cannot afford to exercise and get nothing when a big exit happens. It happened to me when the company that bought mine exited to someone even bigger. I couldn’t afford to exercise. I never had the heart to calculate how much I would have made.

We’ve had secondaries over the years. Sometimes equity gets taken off the table in later stages financings and it benefits early employees. Those changed our calculus a lot when it happened to us. We put together a financial plan and a future as a family with our startup earnings. We made decisions based on whose turn it was to risk & who to run downside. Being a startup spouse means a constantly balancing act of supporting years of low salaries, long hours and stress. And while it’s not easy to be the wife of an early stage employee it’s probably even harder to be the husband of a founder. Startup families live through a lot together.

Stack Overflow was “the” company in many ways for Alex where he spent the better part of a decade and the majority of our marriage working to build the company up. He was employee 32 when he joined as chief of staff. When he left it was over 300 employees and he was the GM of the SaaS business.

When he left Stack we didn’t expect a payday beyond what salary he had earned and perhaps a bit of secondaries. He’d done good work and built amazing things but when you leave you don’t want have the emotional capacity to think about things like big acquisitions or IPOs. When Alex left Stack it was a deeply emotional process for us. A lot of therapy for both of us. Because startups aren’t just the person it is their family that consents as well to these long journeys. Remember that every executive team member or founder has a family that will live through this startup experience too.

After 8 years I knew Alex needed a change. He had given Stack his all. His absolute best. But leaving was hard. In order to leave a company where you invested your whole self (and your family’s) you have to come to terms with how you feel. We cried. We worried. But Alex made the choice. And we didn’t look back. It’s too painful in some ways. You love your startup

You keep in touch with everyone. Alex remains friends with the entire team. We share hobbies & interests and a million group texts with topics as varied as hydroponic tomatoes m, our crypto portfolios and hunting season. We stay at each other’s homes. The bond is deep in startup teams.

Given that bond it’s almost funny how when you leave your imagination on big outcomes can stop. The thing you dedicated yourself to for years is now growing and thriving without you. It never leaves you even if you need some distance.

When we got the call the number was overwhelming. The distance we had created suddenly evaporated. Alex burst into my room where I was meditating and told me the strike pierce. We did some calculations. We checked them. It couldn’t be? It was. The startup had finally delivered the check. We’d done it. Another startup made it.

I want people to know that this kind of largess is mostly random. Everyone works hard in Silicon Valley. Startups are a choice & a state of mind and those of us that chose to do it willingly go into ideas doomed to failure. Or meant for the stars. And it can feel like a crap shoot. Idiots get enormous paydays and brilliant innovators barely make enough to scrape by. The meritocracy isn’t as real as we think. This isn’t to suggest that the Stack Overflow team doesn’t deserve every penny. They do. We earned the payout. The bad years were hard. Miserable. But everyone believed in the community & the power of software developers. But also no one earns these big paydays. It’s a gift. And we are grateful for it.

Categories
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
Emotional Work

Day 148 and Ted Lasso

As I’ve written about before, I like shibboleths and secret codes. And Ted Lasso is my go to show for the language of emotional empathy.

It’s touched a nerve for a certain corner of the internet. The folks yearning for positivity. It shouldn’t have worked. And yet the show’s curiosity opens up your heart. It was a tonic for a tough year. So much of its magic is about learning to accept others as they are and love yourself for you.

Jamie Tartt: “Coach, I’m me. Why would I want to be anything else?”
Ted Lasso: “I’m not sure you realize how psychologically that is

I’ve written about the concept of psychological safety in building partnerships, most recently in venture capital. If you have a desire to improve your bonds with others try Ted Lasso. It will teach you much about feelings you never knew you had.

Whenever someone special is going through something in their life or if I just really love them I’ll rewatch Ted Lasso. I’m having an afternoon off and doing just that.