Mistakes are expensive in the moment but priceless long term. This is why failed founders are so respected and sought after in the startup ecosystem. Their advice is the best money cannot buy. Money literally cannot buy the experience that comes from having utterly fucked yourself.
Sure maybe you lost a couple million bucks but you will never make the same mistake again. And because it hurts so god damn bad you will go out of your way to help others to avoid your fate. I’ve found that founders with failures are generous. They have seen the ways even the best laid plans can implode and want to help you from doing the same.
This is why it’s all the more frustrating for these operators watch a startup struggle to take advice. Speaking as a founder with failures, I know when someone else is about to make the mistakes I’ve made. I feel it in my bones. But it’s not always easy to help people help themselves.
I have a theory that it feels safer to hear a hard piece of advice when it comes from someone you know is delivering it without ego. Someone who never seems to have struggled a day in their life tends to evoke our own feelings of inadequacy. Their advice could never work for us because we aren’t as smart, rich, connected or sexy as they are. But someone with scars? Sure maybe they get why this is so hard for us.
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.
I’ve been writing this blog with complete disregard for whether I’m building an audience. I come every single day and I put down my thoughts on this metaphorical paper and sometimes it’s worth reading and sometimes it’s shit. The rule is simple. I write every single day. And I’ve been enjoying it for six straight months. I value this habit and this space for codifying my thoughts.
Because of the personal nature of the insights and the daily routine pace of the content, I’ve been hesitant to do anything to build an audience. All the strategic things one does – have a theme, give them value, cater to their interests – will force structure into my writing. I’m not sure I want structure. If I add in rules like stick to valuable content on a broad theme I’m not sure I can do that everyday.
This means I’ve stayed away from any of the tactical audience building tactics as well. I don’t encourage signups to read this in your inbox. I don’t have any pop-ups to capture your email. I don’t promote my writing anywhere but a single link on my Twitter account once a day. I rarely out older links to past pieces even if I think it’s a terrific post with insights worth sharing. There are dozens of ways I could be increasing my reach and growing my audience that I am just not doing.
I think it feels like too much pressure. As soon as I make any promises about what content you can find here it will add friction to my one simple writing rule. And friction eats eat away at momentum. I don’t want to do anything to slow or break a successful streak. I’m proud that I’ve written something every single day for 164 days. A lot of it has been genuinely good too!
And maybe I think that my one rule isn’t good enough for anyone but me. Why should anyone else care that I write every day? Daily content that must adhere to rules is practically a guarantee for regular “meh” posts. Sometimes I just won’t be inspired. That happens. I accept that as part of the process but if I cultivate an audience will they?
Of course I could do more to promote the content with the caveats that it’s a personal site with a rule that means you will get a variety of content. If you know what you are getting into than I’m not breaking any promises. I could post to more platforms with clear indications of what I do here. That wouldn’t put any pressure on me and would be transparent with any potential readers. But I’m still hesitant. I’d love to know why.
A meme came across one of my group chats yeh other day that my friend said contained “strong Julie energy.” My response was oh yeah “phone calls are violence” and promptly turned it into a tweet.
Obviously I’m leaning into another extremely online joke with “thing is violence” which made for a good viral moment. But I really do hate having phone calls on my calendar. Not everyone agrees with me. I heard a lot from folks who insist that the human connection of one to one phone calls is superior to the written word.
Unless I’m speaking with an entrepreneur (or my mother) I try to encourage folks to communicate with me asynchronously. Voice communication is slow and lossy. It lets you ramble and insist that tone and human emotion are more crucial than you being a crisp thinker. Which is maybe true in certain situations. Emotions and tone and context are important. But it’s not a substitute for you being a shitty communicator.
I’m not going to waste 30 minutes on something that can be communicated in a few sentences if you just think ahead and collect your thoughts. Call me an asshole but it’s not worth me slowing down my day so I can listen to someone struggle to organize their point.
And I get it, folks want to think things through together in a group. You know how much that sucks if you are the one pulling all the weight in the call? A lot! It’s exhausting. Stop expecting other people to think for you. It’s a dick move. Honestly fuck that noise.
I’m not getting on a damn phone call until I’ve exhausted all over ways of communicating and organizing a topic. Only then is all this nuance and emotional context shit a worthwhile endeavor. Do your homework before you insist on scheduling a call. It will be more productive and take less time.
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 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.
I feel like I need a break from having daily obligations for a day or two (it was a big week) but I’m also a creator of routines and rhythm. When you’ve got a chronic disease you don’t get to skip stuff like your medication or healthy habits without some consequences.
One reason I don’t find myself burdened by writing something long form everyday is that I see it as a habit like taking vitamins, taking a daily walk or brushing my teeth. It’s just something you do.
But I can chose how much time I put into writing or how long I walk (though it seems prudent to let the electric toothbrush run it’s full 2 minute cycle). So I’m reminding myself today that it’s alright to keep today light. If you want something good to read I recommend the Thursday Style Problem.
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.
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.
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.
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.
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.
