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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.

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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.

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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.

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Emotional Work

Day 137 and Feeling Invaded

The line between feeling abandonment and invaded is thin for me. Being a child that often felt abandoned by my successful but distant father ingrained in me a fascinating pattern as an adult. I fear that I won’t be chosen, but when someone does choose me I easily tip right over into feeling invaded. I suspect this is a pattern many others will recognize.

There is a deep yearning to be the priority. My desire to be the one that gets picked is so strong. Such is the lingering fear of abandonment on the inner child. But because I have more comfort and recognition in the feeling of abandonment, when someone shows up for me it’s a swift inversion to the feeling of being invaded.

How dare this person who I so desperately wished would choose me then actually choose me! I will then become shy, distant, evasive and cold as the feeling that someone has overstepped their boundaries (which they haven’t) makes me retreat. For anyone who has ever been so sure that someone gave them all the signals of desire only to have it feel as if it was yanked away, this is the pattern your desired may be reenacting.

Because the consequence of being wanted is, well, being wanted. They desire something of me. I don’t even just mean this of friends or sexual partners. I can be thrilled that someone has chosen to work or collaborate with me and then when they approach me as if I have committed to them I will seize up with anxiety. The agony I feel at someone wanting something from me even when I gave them every indication that I want to give that thing to them is intense. My chronic fear of calendars is a deeply comical manifestation of this fear. I’ll spend an entire day agonizing over one short phone call in an otherwise empty day.

I doubt I’m special in this pattern of yearning and retreat. One of the most quoted lines from Star Trek is Spock noting “After a time, you may find that ‘having’ is not so pleasing a thing after all as ‘wanting. ‘ It is not logical, but it is often true.” For me it is often true and it is a pattern I wish to break. For when I reach out and offer my time and emotions to others I do mean it. The fear of invasion and patterns of retreat are simply a reactive pattern from my childhood. It is protective, and even in the mind of a child, logical. But children’s logic can only take you so far in life. As an adult I take responsibility for my emotions and through mindfulness can move beyond it.

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Emotional Work

Day 133 and Emotional Shibboleths

When I was a kid I was terrified of drinking. A family member went to daily Alcoholics Anonymous meetings and my reaction to it was “I hope I never become an addict because this seems like a huge time commitment.” Little did I know that it’s one of the best possible uses of one’s time! As a kid I had not yet been initiated into the secret code words of emotional work.

AA and Al-Anon are filled with shibboleths. So many phrases (don’t “should” on yourself) or or even a single word (triggered) that I heard in daily life turned out to be passwords for the initiates into emotional work.

It’s not just AA that uses a these types of passwords to show that you too have committed to to either program work or some other system of working on yourself. Inner child shows that you’ve done family systems or trauma work. Speaking of mindfulness generally means you have committed to a meditation practice.

Once you commit to therapy, performance coaching or program work (which isn’t just for alcoholics Al-Anon is for anyone) you will find yourself noticing the little hints that someone else is also on a path to working though their self limiting beliefs. Wait that was another shibboleth! Entire television shows like Bojack Horsemen and Ted Lasso light up the minds of folks on this path. My favorite quote from Ted Lasso is a classic framing of self love work

Coach, I’m me. Why would I want to be anything else?” Jaime

“I’m not sure you know how psychologically healthy that actually is”. Ted Lasso

If you ever find me using phrasing you don’t recognize it’s quite likely it’s because much to the chagrin of my teenage self I now know that this is the best possible use of an hour a day to work on oneself.

Categories
Chronicle

Day 130 and Smiling When Sad

If you asked me my dominant emotion when I was younger I probably should have said anger. I was a fired up young woman. But as the years have gone by and the social benefits of seeming happy have piled up I’m finding it easier to spend more energy on smiling. This isn’t the same thing as being happy.

We like when people are friendly (even if we actually prefer they be kind) and I seem to have bought into it as a moral virtue over the years. I thought it was a gender thing but now I’m much more convinced it’s part of a family trauma cycle set in motion by my father who is exceptionally good at being liked. Cue Bojack Horseman joke.

You inherit your parents’ trauma but will ever fully understand it. Haha the cop is a cat.

Naturally I rebelled against perception of happiness and likability thing with a lot of anger as teenager. Cue lots of screaming stuff like “why do you care more if other people like you more than family” and you’ve got a pretty good idea of what I repeat to my therapist now as an adult.

And because intergenerational trauma and family systems work actually isn’t bullshit I’m starting to realize I stopped being angry and started smiling at some point not because I’m happy but because it’s a learned behavior from my childhood. And the smiling is papering over a lot.

What used to be passion, intensity and anger is fermenting into sadness over the years. Not because I’m actually sad inherently but because it makes me sad to lie about how I feel all the time. But I’m not entirely comfortable expressing any emotion. So now I smile when I’m sad. I’ve absolutely smiled when crying from sadness and grief.

Thankfully I hasn’t yet started laughing and smiling when I’m angry, but I fear if I don’t resolve this pattern and move on it might not be far off. I’ve still got significant work to actually feel my emotions in any given moment. Anger feels like it’s too reactive. Sadness like it’s a sublimation of something else. And if I actually am happy then I need to feel that. But I can’t force it with a smile.

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Aesthetics Chronicle

Day 116 and Taking Up Space

I take up a lot of space. I spend time on social media because there is so much space you can literally be the President or a celebrity billionaire industrialist and there are still corners of the web you don’t penetrate. There is a lot of room for loudmouths, so much so that even someone like me still has plenty of room. I barely rate on the Elon Musk attention scale. Even when I’m screaming at best I crack into D-list zeitgeist. It’s like the privacy that comes with living in New York City. You can have some notoriety but the web doesn’t care. I like how you can feel alone.

The irony of course is that I think no one is paying attention to me. I think I’m an average Joe nobody that no one ever notices. This despite the fact that I am paid to be an expert in getting attention. No literally I cost a fortune (I’m worth every penny) but I’m somehow convinced I’m invisible personally. I can feel lost in a lonely world where I’m not even sure the people that love me the most can see me. I’m stuck in some lonely portion of my childhood where I felt abandoned so I’m replaying it out now as an adult. It’s not great but I get something from it.

Except this is a fantasy that is not true. I’m not that child anymore and I know how to get attention. I’m not alone. Even when I’m not consciously drawing energy to myself, people do see me. I can simply be myself and be seen. I command attention. It’s who I am.

You always think as a kid you will get some cool superpower like laser eyes or flying but nope you are going to get a super power like public relations or brand marketing. And honestly, when I’m not a self pitying victim I know those to be awesome super powers. You can make money and direct business and politics with those super powers. I just though I’d get something a little more aesthetic you know? It’s dope but also like adult superpowers are a letdown for your inner child.

I just need to remind adult me that I am seen. That even my normal personality not exerting her will force onto the universe is actually still quite visible. I can just exist and I’ll be holding space for myself. And it’s a good space with plenty of room for all of me. And still intimate enough to feel the love around me.

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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
Chronic Disease Chronicle

Day 106 and Perceptual Drift

I often find it easier to talk about the darker parts of my journey from chronic disease once I’m already through the worst of it. If you are hearing about my long dark night of the soul it’s probably because I can see dawn breaking.

Maybe it’s because it’s hard to discuss the challenges when you are in the thick of them. Having any amount of perspective when life is at its worst is a skill reserved for religious scholars and internet advice gurus. The rest of us just try for hindsight being 20-20 at best. I admire the stoic philosopher types but I’m generally just happy to be able to survive rough days with a minimum of pain and angst.

It’s likely this tension between a better current reality and the heaviness of past challenges that made me so confused by the reaction when I posted about the envy I felt towards people who live healthy normal lives. A number of people checked in on me worried or concerned about how I was doing. I didn’t get it. I had just been discussing how well I’d been doing so why was everyone offering to pray me me?

I’d come to terms with some of the sadness and anger I’d felt during the worst days of my illness because I was doing well. I’d been posting about how excited I was that I felt great, had clean bloodwork, and was seeing better days. It was because I was doing so well I decided it was best to ruminate on the challenges I’d experienced. I was on the other side of it. Feeling well and energized meant I had the capacity to explore the dark places. When I’m actually in a dark places usually all I can do is survive the experience.

But I get that others didn’t see that now. They saw darkness and sadness and reach out to me with kindness. The love and support from people close to me and the messages and prayers from my internet friends all added up to me feeling like the good times will just keep getting better. If you are reading this I encourage you to share your journey. You just might get back the same love that I got. People are great that way.

Categories
Chronic Disease Chronicle

Day 105 and Envy

I didn’t have hobbies for a long time. People would ask me what I did in my free time and I’d give them a confused look and try to come up with a plausible activity like reading. I was embarrassed. Everyone else constantly doing shit. In reality, I didn’t have the energy for anything but work and taking care of life basics (and for a few years spare energy was dedicated to sex and dating but that’s different post).

I’ve been an on and off entrepreneur my whole working life. And if I’m totally candid I’ve had health issues that impacted my energy since I was a child. So while I have had things in my life other people would consider hobbies, they were slowly stripped from me. I stopped horseback riding somewhere between 16-17 when I dropped out of school. I told people it was allergies (which was true) but much of it was exhaustion. I was fighting just to keep up with obligations to education like taking tests for college and to prove I had learned enough to be considered a “graduate” by my school.

In college I was blessed to go to a school that wasn’t cool to have have parties. That made it easy to hide being too tired to socialize. Other students were in clubs. I didn’t join anything. I was thrilled to make it to my job (as a research assistant to a medical ethicist) and get home to my roommate and boyfriend to watch tv at night. I didn’t realize this wasn’t normal at the time.

Once I started my first company all I did was work. I had to socialize professionally so I spent a lot of time at fashion parties. While this is fun it wasn’t a hobby. I partied because it’s how I made my living. For a while I thought this meant I had a hip social life. Which was a nice lie. I had a glamorous job.

It started dawning on me around 24 or 25 after I sold my first company and had to relocate to San Francisco for the acquisition that other people didn’t live like I did. In San Francisco people hiked, did yoga, took classes, and all the other “bullshit” I looked down on. I looked down on hobbies not because I think work is better but as a defense mechanism. I was jealous.

All these people had energy at the end of the day. They wanted to do things! That was unfathomable to me. I could barely do work. How the fuck was I supposed to do stand up paddle boarding on the bay? I was not kind to people that had hobbies. I told myself (and they could tell) I thought they weren’t as good as me. Of course, now I realize this was the trauma of illness manifesting it. I couldn’t do what they did. Rather than feel sad or angry or some other productive feeling I decided I was better. All to avoid letting myself feel how angry I was that I couldn’t have that life.

I’ve come to accept that I still live more than most people even with limitations like illness. I don’t have to prove a good life with status markers like hobbies. Though I’m still fighting to get to complete functionality and control with my autoimmune disease. But even if I do get to a place where I can live normally I might still skip the hobbies. I’ll go straight for the pleasures like work. I’ve only got so much time so I may as well enjoy each moment with what I actually like.