Tag: Psychological Safety

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Finance Startups

Day 348 and Empathic Investing

The best investor I know is Cyan Banister. When I was coming up in the web2 world I got to watch how Cyan handled early stage relationships. She brought total empathy to every interaction I witnessed. The kind of candor, kindness and willingness help her founders eventually set the template for how I wanted to work. I wanted to invest with my whole self like Cyan.

While I doubt it was the primary motivation or even expected outcome, Cyan’s angel investments are some of the best returning of the generation. If you subscribe to Alex Danco’s theory of social capital and angel investing this kind of investing is playing an infinite game. It clicked for me then that the real edge you can bring to the earliest stages of startups is an open heart. An open heart gives you an open mind. And everything else is a matter of tactics from there.

Creativity comes from seeing something in a completely new light. A change in metaphor can lead to tangible physical discoveries and complete cultural revolutions. Science fiction gave us the tricoder and the internet. Imagination literally helps forge the future. So it’s important if you want to spot the catalyzing “this changed everything” moments that you be open to seeing the world in an entirely new light.

While I obviously have an investment thesis on the macro level events shaping market demands, it’s not practically nearly as helpful in the day to day of investing as just being human. Creation is volatility. It’s not usual for a founder to bounce between terror and euphoria on the same day. Imagine how exhausting that can be when your entire life is always fight or flight and fear or famine.

My only job is to show up for a founder in that moment and accept them for who they are. They need to trust me enough to tell me if they are scared. Trust me enough to share their biggest wildest dreams. It’s a delicate and intimate thing to be there for someone no matter what. But I firmly believe that is what it takes to build something worthwhile. It’s never ever clear from the outset if it will succeed. The only thing we can truly have confidence in is our ability to solve the problems along the way. Chances we’ve seen the tactical playbook and can help you solve those more easily. Many of us come with baked-in operator skills like acquisition or operations. We can teach you that.

While this may all sound utopian, or if you are a bit cynical, even maudlin I assure you this is the most competitive way you can approach investing. If capital is simply a commodity you must infuse your work with real value to compete. If you have a lot of assets under management maybe you can add a lot of services. Large prestige funds with billions in AUM can offer that. But now you have to have bigger deals and surer outcomes so that impacts what you can invest in. Scale impacts outcome in all kinds of practical ways.

If it’s all about the capital then you can be beaten not just by a better term sheet (which just makes everything you do more expensive) but also by someone who brings intangibles to their place on the cap table. You know whose pro-rata doesn’t get cut? The person who showed up day in and day out before the round got competitive and every is kissing ass to get in. The founder remembers. And so does the empathetic capital. We win twice over because our deals are cheaper and we stay in them longer.

So founders and fellow investors ask yourself who you want in your corner from the start. You may find the smartest capital is actually the nicest capital as well.

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Emotional Work

Day 345 and Trust

I’ve not always been accepting of my own weaknesses. Instead of focusing on how well I can hone my super powers, I’ve occasionally fixated on where I lack innate talent. I’m not particularly adapt at operations or logistics but I feel bad about it. I am however genuinely top tier when it comes to narrative & attention. Somehow I don’t feel equally good about this.

I’ve tried to work in teams where my talents & weaknesses are balanced out by others. I like teamwork now in a way I didn’t fully appreciate when I was younger. I’ve learned to trust my own value. And I am able to emotionally trust the people around me.

The psychological safety that comes from trusting yourself and others is a lifelong process. Even a few years ago I’d struggle to not compulsively overwork to overcome my weaknesses. When I should have been honing my unique talents.

I’ve got an opportunity over the next few days to really trust one of my teams. We’ve got a deliverable that isn’t in my area but I’d crucial to success. I could spend my extra energy worrying over it and making an attempt to contribute just so I felt useful. Or I can emotionally let go and appreciate the trust I have in others.

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Chronic Disease Emotional Work

Day 330 and Vitamin Not Pill

I was reading a fellow investor’s thesis page and noticed one lens they use for investing is whether a product is a “vitamin or a pill” with the insinuation that pills are inherently better investments than vitamins, as one is a nice to have for a business and the other is a must have. Now I can’t speak to this as an investment thesis, though I largely agree, but I do disagree on a wellness basis.

Preventative medicine is just as necessary as interventional medicine. In some cases more so, as getting ahead of a disease’s inflection point should be the humane way we handle our medical needs. We are just often too focused on short term impacts to see the value of solutions that build over time. Think of it as the quarterly reports of healthcare. Why build for the future when the market judges by each 10K?

The nature of panic may make us inclined to spend heavily on something that has become acute. But that does not make it inherently more effective or worthwhile. It’s just the immediately necessary. It just means we need higher minimum effective doses to see a result.

What we often ignore is compounding effects of wellness interventions are far superior to the mitigation of a pharmaceutical over time. Most of us would prefer to not require the costly (both biologically and financially) medicines that keep us together. This is not to say that I am not deeply grateful for all the drugs I take. But rather that I have seen incredible value in what we deem “lifestyle interventions” and other “nice to have” vitamin style supplements and protocols.

And while it takes much longer to see their effects, the compounding positive effects often wildly outperform anything that might be dubbed a pill. The trouble probably boils down to switching costs and time to pay off. Which is why an investor would prefer a pill to a vitamin. But just because something has a longer lifecycle doesn’t make it inherently less sticky. Or less effective. Or crucially any less profitable. The only way we ever see the deeply positive effects of habitual practice and dedication is to do the work. That work is boring, repetitive and low payoff. Until, most times years in the making, you see how putting your future self over your present self is what is giving you the future you always dreamed would be yours.

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Emotional Work

Day 329 and Thanksgiving

I have so much to be thankful for this year. I don’t have a lot of poetic thoughts on it, though I have written extensively about my feelings on some of the bigger moments of the year. So click those if you want essays as this is going to be mostly a list.

I’m grateful to have recovered my health in 2021. I’m equally grateful I had the money, support and willpower to achieve it.

I’m grateful I have a husband who understands me and gives me the love, support and freedom to be me.

I’m grateful for having a space to share my thoughts daily, and rather than be punished for speaking my mind, I am rewarded for it. That includes WordPress, Twitter and all the people who made the internet possible.

I’m grateful I can live in Colorado and still do the same work I previously thought I would only do in New York or San Francisco.

I’m grateful my mother sent me to Waldorf school. I’m grateful I have a father who supported my development as a full human being.

I’m grateful I can afford to buy whatever dumb shit I like for my hobbies which range from expensive skincare to preparedness.

I’m grateful I can consider buying a home that will have the capacity to provide safety even as the world around me has risks.

I’m grateful to have business partners who share my vision for investing and founders and entrepreneurs who allow me to help them.

I’m grateful I never have to worry if there is enough money in the bank to buy a book.

I’m grateful that the supply chains have held so that I have an apple pie that I ordered online the day before the biggest holiday of the year which I picked up in my car that I was able to buy even as global trade was strained and our currency was inflated.

I’m grateful for the time to pursue emotional capacity and the money to pay for it.

I’m grateful for chemistry and the wide variety of pharmaceuticals and supplements that I take every day.

I’m grateful for my iPhone, it’s applications and games I use daily on it that have connected me to a world of people virtually that I love as truly as the people I interact with physically.

I’m grateful for shitposting.

I’m grateful William Gibson still writes. And I’m grateful that Twitter has let me interact with my favorite writers.

I’m grateful for West End BBQ and Spruce Confections.

I’m grateful for my raw milk dairy cooperative and it’s farmer Daphne.

I’m grateful for sunscreen and for apple cider vinegar.

I’m grateful for Costco.

I’m grateful for my parents making good decisions when I was younger that have compounded into incredible luck and prosperity for me.

I’m grateful to be American and I’d like that to remain a thing for which I am grateful.

I’m grateful for democracy, the enlightenment, free elections, a free press and liberalism.

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Startups

Day 305 and Request for Founder

I was having an emotional conversation with a friend. They were giving me a piece of feedback that was truthful but hurt me. Because I feel psychologically safe with them, I was able to take the feedback in a receptive and open manner. I could incorporate it into my mental framework immediately because I trusted my friend. And I knew that their feedback was important and accurate.

One of the traits that I feel is most central to success in founding a company is the ability to process feedback effectively. Founders are constantly getting feedback. An average day might include angry customers with product complaints, a venture capitalist with heartfelt but partially useless advice, an unproductive strategy meeting where no one can seem to align, and a bunch of smart ass shitposters on social media with job advice for you.

A startup CEO gets a lot of feedback. Every day is a deluge of the stuff. And founders have to be gracious about it. Even when a lot of the feedback is useless, or even occasionally downright bad. You as a founder have to decide what to take and what to ignore. Because learning how to synthesize and integrate feedback; positive, negative or even profoundly unhelpful, is in fact your job. Being good at it matters. It’s the closest thing I have to a litmus test as an investor.

This is a trait I prioritize highly in founders. If you yourself are a founder that is working on improving your capacity for feedback processing, I want to hear from you. That mental flexibility is one of the core criteria I look for when I decide on an investment. Do I think you will be able to intake enough information about their market to get to product market fit? Will you be able to adjust your mindset and mental models quickly enough to outrun inertia? How emotionally strong are they that there can hear constant negative input and still hold their positive vision? But equally can you adjust that positive vision when negative feedback that actually matters presents itself.

These are the questions you need to have answers to for yourself. If you can drop me a line on Twitter DM. I’ve got an entire primer on now I like to get to know founders.

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Startups

Day 298 and What You Don’t Know

I work with a lot of first time founders as a seed stage investor. Or rather I enjoy working with first time founders so I slowly became a seed stage investor as moving from advisor to angel investor. When you are a founder yourself, as I once was, you get a lot of inbound from others in the startup ecosystem as the bias has been that “only other operators can ever understand” so it breed insularity.

This has generally meant that there is a significant body of knowledge on best practices in startups that doesn’t get codified in writing it’s passed on as an oral history from one founder to the next. Maybe if someone published their Gchats and emails public we’d have a searchable wiki. But even with the trend towards startup communities, explainer Substacks and operator podcasts there is still a substantial portion of unspoken knowledge that no one will tell you. You literally don’t know what you don’t know. And the people that know have forgotten what it’s like not to know.

It’s easy to forget this as you assimilate norms and conventions over the years. I have been working with a portfolio company’s CEO to prepare some press and go to market work recently. Something I take completely for granted about media outreach wasn’t in fact obvious or intuitive.

But it was so obvious to me I never thought to mention the detail that tripped us up. And of course, the founder being a first timer didn’t know what they didn’t know. Why would they! That’s why they work with more experienced investors and advisors. It was my fault. I knew the thing but in my “water is wet” mindset didn’t even consider that the founder might not realize they were swimming in water yet. And that was entirely on me.

I find it somewhat comforting that startups are constantly introducing new founders who don’t know what they don’t know. Because maybe they will be the one to discover a new way of knowing that changed it for all of us.

The best is old timers can do is pass on what we think we know and the newbies can assess that using their fresh eyes. Sometimes (ok probably most times) we save you from making dumb mistakes that we once made. But maybe what I think I know for sure is just me not realizing I’m a fish in water. You can learn that from experience sure but also from having a totally new lens.

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Emotional Work Internet Culture

Day 293 and A Good Cry

I’m a cryer. I hear the swell of trumpet from the Star Trek theme song and I’ll start welling up. I’ll read a poignant passage in a cheesy airplane novel and my chest will tighten with emotion. My eyes will tear up when I tell a friend that I’m proud of them. I’ve found myself sniffling over a set of emotional text messages. I love a good cry.

I think I’m a cryer because I bottle up my emotions otherwise. I’ll share feelings in public but the real deep down core emotions are harder for me to express openly. The fear and hurt and sadness that make up the core of my emotional unconscious take some coaxing and a lot of psychological safety to get out into the open.

One of the reasons I find social media so much fun is it is a cesspool of emotions. Much of shitposting is just rage and anger expressed with a joke. And the shitposts that are sad are often told with a kind of vulnerability that I more commonly associate with 12 step meetings or group therapy. Internet culture has become an escape valve for emotions we didn’t know we even had.

The more I see the negatives that comes with keeping emotions bottled up the more I appreciate ways to let them out. If it is a good cry then I’ll take whatever brings it on. If you need something stronger than I highly recommend a light dose of Internet emotions. Just don’t let it overwhelm. Ease into the shallow end with an anonymous shitposting account first.

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Emotional Work

Day 291 and Self Control

Self control is a form of self abuse for me. Early in life I learned that I could control others by controlling my emotions. Instead of showing my feelings, I’d distort my emotions into whatever got me attention from adults. That’s pretty clever for a child, but is the road to misery once you’ve grown up.

Alas I’ve kept up the habit of self control. It might not look like it from social media or press narratives, but I self censor a lot. I’m often conscious of what others will like or dislike and I will edit my feelings if I feel it isn’t to my benefit. What can I say, I am still hurting from feeling like I wasn’t loved as a child by my father. Same old story that everyone has in their lives (well maybe for you it was your mother but same idea).

But it hurts to keep your emotions inside. Eventually it will turn into pain or sickness. Not that I’m saying all pain or illness is caused by emotions (that’s some bullshit) but the mind body connection is real. The point is it’s only hurting myself to exert so much control over my emotions.

I need to get more comfortable with being uncomfortable with other people and how they feel about me. The control I have is largely a fantasy. It’s not that it’s not possible to change how others perceive you. Hell I’ve picked professions where that’s practically the main skill set. I love the perception game. Public relations, fashion, even venture capital are all games you win by building a good reputation.

Having a good reputation doesn’t mean turning off honesty. If anything reputations are built on being trustworthy. And that generally means saying what you mean and meaning what you say. So I’ve got to stop abusing myself by choking off emotions I don’t think others will like. Maybe it’s a gender thing. I learned pretty quickly no one likes an angry woman. But sometimes I get angry. Whatever excuse I’m using for hiding unpleasant emotions has got to go.

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Media

Day 281 and Villains

This is a post that will have spoilers about the end of the second season of Ted Lasso. Do not read any further if you have not seen it. I’ll put an extra paragraph to keep it from your eyes and we can meet again tomorrow.

SPOILERS BELOW

The first season of Ted Lasso may be one of the most perfect seasons of television ever made. It’s like being inside the best session of therapy you’ve ever had. The kind where you have a breakthrough so profound that the hurt and agony of your worst childhood trauma suddenly feels not only bearable but also the reason to fully love yourself. It’s just that good on the emotional truth scale. The warmth and safety and growth is beautiful.

But season two leans into tropes and villainy where it used to rely on nuance and kindness. Rather than feeling the pride and hope of emotional truth that has been hard gotten (the truth will set you free but first it will piss you off), we are given the obvious end of Nate betraying Ted and Rebecca by going to coach for Rupert’s new team West Ham.

Nate makes a massive accusation that Ted abandoned Nate emotionally but we are given roughly thirty seconds to wrack our brains for these betrayals before it is revealed that Nate has chosen to abandon Ted. How do we feel about this? Wouldn’t we normally explore how both people contributed to the feeling? But nope it’s send Nate right into insecure narcissistic reactivity rather than mine for the potential nuance.

We could have been given a story where we see Nate and Ted equally participating in the traumas they each carry and how it affects their relationship. Ted with his fear of abandonment brought on by his father’s suicide very well may play out that pattern of abandonment on Nate. But that’s left largely unexplored. Perhaps it could have shown us how Nate intuitively sees that because of Ted’s unresolved pain with his father, Ted in fact isn’t fully there for Nate in his new role as a surrogate father figure coach.

The struggles of a young man coping with a new position and unexpected authority granted by father figure like Ted juxtaposed against Nate’s own issue with his father who doesn’t show him respect would have been an empathetic story in the hands of this show.

There was so much fertile ground for how each character could trigger emotions in the other and for how they could own and resolve these feelings. But instead it’s straight to villain don’t pass to don’t collect 200 dollars. By the end I wasn’t even sad about the loss. I’d resigned myself to the conclusion. But they could have done so much better by everyone. Even if Nate must experience his darker impulses we would have been wiling to see the full journey of how he arrived there and the pain other’s traumas has inadvertently wrecked on Nate.

I guess I’m not sad. I’m just disappointed. And that’s how you know it really mattered to me.

Categories
Emotional Work

Day 269 and Pacing

I’m very defensive of my time. While I work at curtailing reactivity in my emotional growth, it’s still easy for me to feel invaded by obligations to others. Taking video or meeting in person was among my least favorite activities even before the pandemic. That’s one reason I’ve written extensively on how to communicate with me asynchronously. But another deeper reason is my fear of misusing my time. And tempting as it may be to project it onto others, I know that this fear is entirely about me.

I am very fearful of anyone needing things from me. I don’t mean things like money, favors or advice; though it is harder to say no than you’d think. My fear is deeper. I’m afraid friends and family will start to count on me for their emotional needs when I’m still figuring out how to be present for my own. I’ll deliberately put distance between myself and others to avoid feeling needed.

So what does this have to do with pacing? I’m not very good at giving myself enough space to be challenged and recovery. And when every encounter with another person is an emotional challenge, I need to be careful about pacing myself.

Maybe there is some latent autistic spectrum issues or maybe I have more trauma than I can consciously dig up but it’s a rare human that doesn’t make me anxious about the energy required for maintaining my own boundaries. It’s not about other people to be clear. It’s about me and my fears of being emotionally invaded.

As I build up more systems and accommodations to allow me to work effectively I need to figure out better pacing. How do I connect with others without emotional fear while still respecting my needs for down time and rest? Giving myself enough recovery has been an ongoing challenge that I write about extensively. But putting it into writing also serves as a valuable reminder to course correct before a crisis emerges.