Tag: Founders

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Startups

Day 468 and Small Moves

One of my favorite movies as a kid was Carl Sagan’s Contact. It’s not a great movie but it’s heart is in the right place. It’s a beautiful story about human curiosity and the long timeline of history. In one of the closing sequences the protagonist is told by alien intelligence as embodied by a representation of her dead father that all next steps are “small moves Ellie.”

I never feel like I’m moving fast enough. Every day presses against me. I long to slog through them with speed and alacrity. It’s almost embarrassing how inadequate I find my progress. But then I remember that I move fast. I live ahead of the mainstream. I get to sit in the future that William Gibson said was not evenly distributed. Even if I don’t think I’m particularly good it’s hard to deny just how much of my life is lived in a tiny sliver of humanity.

Someone recently asked me how I moved so fast when I’m dealing with a chronic illness. I found it to be such a shocking question. I feel like I’m glacial compared to the reach of my desires and imagination. But then I’m reminded that even in shorter hours I’m forced to hone my crafts. I can’t afford to waste energy or focus so I simply do not. I imagine this focusing out of need is similar to what parents of young children operate in. The subtle art of not giving a fuck.

And so what if I am slow on a day to day basis. Rome wasn’t built in a day. I’m not a market trader. I invest in ten year cycles. Everything in venture is actually small moves. But as time adds up so do the aggregate of the moves. Compounding interest is up there with gravity as a force. So even when I yearn for more and for it to arrive faster I have to trust the numbers.

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Emotional Work Startups

Day 466 and A Painting Without Shadows

I take therapy really seriously. I’d put being emotionally capable of managing myself at the very top of my life priorities. Honestly it should be number one and if it isn’t I need to stop and ask myself why. Being an adult requires an intimate understand of one’s emotions and the capacity to share them with others.

To further this goal I do a weekly session as well as group work. It’s meaningful to me and I recommend to all my founders that they find a way to get into coaching as well as therapy. Taking care of your own inner child is the only way you are going to be able to lead a team. If you want to build a billion dollar company and manage thousands of people you better be able to manage yourself first.

Where I think people can go wrong is treating this process as if it’s one of optimization. Do I think founders who have taken the time to understand themselves do better? Absolutely. It’s pretty rare that someone’s coping mechanisms help them reach the heights of their talents. A chip on your shoulder is great but eventually you learn to transcend it.

I think this is because if you don’t understand yourself you are a painting without shadows. It’s flat. Boring. Doesn’t read as true or trustworthy. Maybe you are really good at showing emotions to get your way. Lots of people are but if they just off enough from genuine then it reads as the uncanny valley of empathy. People just know when you are hiding something. And hiding your dark side means hiding your shadows. Without them you are a flat human.

A painting without shadows wouldn’t be any good. You without your shadows wouldn’t be who you are. The best of you exists because of the worst of you. I really do hope more people are able to see that truth and love themselves.

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Startups

Day 452 and A Short Guide on Cold Outreach for N00bs

I have an open Twitter DM policy for founders. I encourage outreach to me via all forms of asynchronous communication. I think the hour long pitch, either zoom or IRL, is a bad way to get to know someone. But that doesn’t mean there aren’t rules and social graces involved in cold outreach. I’ve outlined an FAQ on how to get to know me and what I look for in founders but it seems like people would benefit from more tips on how to ask for help and investment on social media.

1. Give Me A Synopsis

If you are sliding into my DMs remember that I’m probably just glancing at an alert. You want to get across just enough context to encourage me to pop in and take a look. And remember you don’t need to convince me with one paragraph. I want to develop a relationship with you and learn how you think. That’s not possible in a few sentences so remember that synopsis is just the beginning.

2 Use A Social Account With Shared Context

I’m always surprised by people who slide into my DMs with 15 followers and a blank Twitter profile and expect an answer. Use the shared social graph to show your interests and tastes. Follow and be followed by people in common with me. You’d be surprised how much meaning I take from seeing you follow and interact with people I respect. The social graph is now we vouch to each other we’d enjoy spending the next ten years working together.

3. Tell Me Who You Are

Make sure you’ve got a link to a personal website so I can learn more about you. It doesn’t have to be elaborate. I think LinkedIn is lame but it’s easy and shows your skills and career path. Hate that? Link your TikTok or Tumblr or blog. Are you anonymous? That’s totally fine. I’ve funded anons. Give me the portions of your identity that are on chain or under your pseudonym so I can learn more from there.

4. Rome Wasn’t Built In A Day

You don’t need to ask me for an hour long pitch or even my email right away. I don’t need perfection from the start. Just say you are working on something and want to talk to me about it. Say you will send me a white paper or a blog post and ask me to read it. Then follow up in a few days to see. Don’t get social anxiety about it either. I probably just forgot or got busy and I love being reminded. Truly.

5. Only Ask for Favors After You’ve Demonstrated Rapport & Competence

I cannot tell you how many times I’ve been asked to for advice, help or investment in DTC, CPG or retail type businesses which I have explicitly said I do not do. But what’s even wilder is that the question right after I say no is almost always “well can you introduce me to other investors that do?” This isn’t an inherently bad thing to ask me. I want to help. If you’ve shown me a great product and I’m engaged and impressed with you as a founder and we’ve had a few interactions ONLY THEN do we have enough of a relationship where it’s ok to ask me to spend my social capital to help you. I can’t help you till I’m sure you can help yourself and that means demonstrating you won’t waste the time of my network as well. Favors are big asks and I only want to use them on people who will reflect well on themselves and on me to my network.

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Internet Culture Medical Startups

Day 415 and Accessibility

I don’t think of myself as disabled or requiring special accommodations, though I have a well controlled medical condition that swells my spinal cord called ankylosing spondylitis. But for the first time since my diagnosis I really felt like I was handicapped. And I am feeling so much sadness over the idea that I might genuinely be disabled.

I’m attending ETHDenver and it’s wildly over capacity. No consideration has been given to any kind of basic accessibility. I didn’t think it would effect me though till I got here. I can walk without a mobility aid and if you met me you’d never know I have an issue. But I can’t stand in line on cold concrete for two hours. It turns out I would need a wheelchair for that kind of activity. And even if I had a wheelchair the first two days were in the cold and snow so I couldn’t have wheeled over or around the slush and water.

So I have only attended private parties and small events and group outings. This is great for me as I’m a well networked established member of the startup ecosystem. I’ve got a popular Twitter handle and can easily reach out to people. But I’m noticing just how much a bit of inaccessibility will gatekeep the crypto and web3 community. If you don’t have my heaps of privilege there is no way you could navigate this conference.

And we really need web3 to be welcoming and accessible. To build a better future with infrastructure and economies we all collectively own and benefit from we need an order of magnitude more people participating. But if no one can get in and experience things first hand than web3 will just be a repeat of the oligarchy of web2. It’s honestly my worst fear for crypto. We will accidentally exclude the people who will benefit the most from our innovations.

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Finance Internet Culture Startups

Day 414 and Empire’s End

Being at a crypto convention in 2022 is something else. It’s full jubilee at the end of the world shit. You are surrounded by millennials and gen-zers who know in their gut that their future has been stolen from them. And instead of being pissed they decided to build. And they decided to gamble. And it’s not clear which one is which sometimes.

You’d be forgiven being a nihilist right now. Capitalism looks like an excuse for the oligarchs to consolidate state and private power to enrich themselves. Everyone is soaking in student debt and working shitty interchangeable jobs for corporations owned by private equity. No one can afford a house. No one is stable enough for a marriage and children. Our fucking parents won’t retire and won’t listen to reason when we say their neighborhood needs more housing density.

But if you are in crypto the future looks pretty rosy. You are discussing real estate for your second home and the tax advantages of different jurisdictions. Swapping stories about your friend who accidentally didn’t set up estate planning and his company had a big exit and now he’s got to pay full rate to some expensive Democratic run city and state. If you are at the nice cocktail parties you are building the future and the venture capital is flowing and it’s possible that this is the next big wave of innovation. It’s time to fuck around and find out.

But not everyone in crypto is part of the smart money. Not everyone has institutional backing and the professionalization of long time startup operators coming to build real value. Right right below that success is a teeming horde of brutalized and completely marginalized people who are praying they hit it big on some new coin or hot new NFT project. They saw Bitcoin and then Ethereum go to the moon. So now they are praying to the full moon and hoping they ape into the next big thing.

But what’s scarier is that the prevailing attitude is who cares if it’s risky because no one believes they are going to have a future anyway so you might as well gamble. They might get lucky and build the next Google if they join the right DAO and buidl. Yes I typed buidl. I’m a degen too. I’m a doomer that isn’t convinced the empire is going to hold for much longer. And if I’m going to watch it all crash down I want to be a part of building something better for all of us. Maybe we get lucky and innovative faster than the apocalypse. To be fair, humanity always has in the past.

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Startups

Day 412 and Status Anxiety

I’m attending Ethereum Denver through the weekend. If you aren’t familiar it’s a fairly substantial crypto conference with wide appeal and good credibility across the entire ecosystem. I don’t have any special hookups nor do I have a careful plan of attack. It’s my first time attending a large industry event as an investor.

Truthfully I’m incredibly nervous. I’ve never been on this side of the table before. I’ve always attended events as a founder. Which is an entirely different mix of status and social positioning from a venture capitalist. Founders are the cool ones. The top of the social hierarchy. It’s the hardest job in the business and in exchange we revere them as a kind of messianic class. We all place our belief in the people who start building from nothing. Even if you haven’t yet had a big success it’s the act of beginning that has the potency. Anyone who has the guts and steel to try to make something new is part of that rarified class.

So while I ostensibly have more power than I’ve ever had in my entire career, I also feel a slight sense of social anxiety. This is the first time I’ve not been in the anointed. So in a very real sense I’m walking in without any of the power that I’ve had before. And I’m a little scared.

Will people think I’m cool? Will I get invited to go to the right parties? Will the right people want to talk to me? Will I look good enough? Will I be able to hold my own such that I can capture the attention of other peers?

I’m used to needing to network hard to find the money. I’d roll into events with my team squashed into one room and we’d plan out every single minute to maximize our budget. Now I’m the one teams will be searching for pitch.

It’s this strange blend of gaining new status but missing the old place and position in a culture that has me a little nervous. So if you find me at the conference know that if you are scared to strike up a conversation you are not alone. We are all looking to find each other and connect.

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Startups

Day 406 and Like I’m 5

I welcome pitches through my social media channels. I’ve even gone so far as to put together an FAQ for how to pitch me. I hope I do a good job of welcoming founders at even the earliest stages into conversation. But just because I am happy to shoot the shit with you, doesn’t mean I’m capable of organizing your thoughts for you.

Want me to write a check? When you are getting started with me keep it simple. Ground me in the basics so you can take me into the details. Go from whole to parts.

Now I’m not asking you to dumb it down. I’m asking you to do the work to really clarify what you want to make. Maybe it doesn’t sound as impressive in a few sentences, but trust me you must anchor everything in the basics. If you cannot articulate the core product you need to build how in a few sentences, how do you think you will convince me to support your biggest craziest vision?

Now what I am asking you to do is actually quite hard. If you aren’t sure what I mean when I ask for a basic product description spend some time on the excellent Reddit sub “Explain Like I’m 5.” The premise is simple. If you have a complex technical topic that requires expertise you need a way to get it across to a layperson.

You will hire a lot of lay people in your career as a founder. I am just the first one. Educating me on what you are doing is hopefully the start of thousands of explanations you will give on what your company does. Because we both want you to build a big company right?

So while you are welcome to send me your standard 15 page deck, or in depth Notion documentation, or your favorite Substack blog posts, you know I have to explain it to the co-investors, new hires and LPs in a sentence right?

What I don’t want is to dig through dozens of documents and feel even less sure by the end of my diligence of what you are building than when I started. I want to hear a synopsis that excites me to dig in and then go on a journey with you where I learn just how much you’ve thought about it. But if you can’t keep it simple you probably aren’t ready to be fundraising.

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Emotional Work Startups

Day 402 and The Most Me

I am coming slowly into 2022 in its fullness. Perhaps I am living in seasonal time this year. I am feeling the wholeness of what the moment brings and January is about becoming. So it wasn’t surprisingly that clarity of purpose has been sharpening for me. I am ready to commit to self acceptance as the theme of my year.

I felt somehow today that the only thing that really mattered for my success in the world was radically altering any perception I had of myself as negative. That I was here to love even the parts of myself that cause me shame and fear. The only thing that will take me where I want to go is loving myself. That self love was actually the key to all troubles personal and professional.

“You know, loving awareness—even if you haven’t heard the phrase before, you know what it is. Those moments of spacious, calm, thorough, tranquil connection with whatever portion of existence you’re currently exposed to, where nothing is being challenged or conceptualized, but rather is just allowed to appear, in radiant suchness, without resistance or fear.”

How I Attained Persistent Self Love

I’ve discussed the emotional work I do on the blog at length. The Family Systems Therapy and it’s exploration of the inner child. The shadow work and integrating of the whole of oneself. But I do often reject the crucial step of feeling like I am fundamentally alright. I am ok. I am enough.

I’ve committed to “a bit” where I lavish myself with self improvement and luxuriate in needing to make every measurement better. I’m obsessed with finding metrics to improve. And so I give myself little problems to fix. Maybe I’ll eat poorly so I can feel bad about my body composition. When instead I could just eat what I like and accept that maybe I’ve made other priorities than my figure. I don’t need to agonize over trivial shit.

But equally I don’t need to agonize over big shit. So I’m not a perfectly credentialed super star. I’m more of an eccentric. I don’t live like other people so I see other things. My existence is the selling point. If what I bring to the table is what you want then I am the right partner for you. If am I not then well tautologically I’m not for you. Partnerships are accepting what everyone brings.

So through the end of this year I am going to bring self love and acceptance to my writing here. In letting myself be seen I can more fully bring myself to my partners. Being a startup investor that means I must be present for my founders, their teams, and my own LPs and stakeholders. I’m bringing the full depth of my being because that’s also going to bring the best returns. Because being ok. Accepting the moment and it’s inhabitants? That brings us the creative potential to solve whatever is in front of us without judgement.

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Startups

Day 398 and Experienced

I spent a part of my day gossiping with a friend of mine who is from the same cofounder cohort as I am. We’ve got a lot of common interests beyond having both been founders at the same time and I won’t list them as I don’t want to give them any hassle. But the two of us have seen a lot of the same things. We are now experienced.

It’s funny what you notice when you are experienced. We were noticing little aspects of how founders we taught or mentored or invested in tended to repeat. How there are certain repetitive patterns you notice in first time founders or folks who are new to Silicon Valley culture. You notice idiosyncratic elements that all n00bs have.

Of course the where it becomes hard is how much time do you put into coaching them. Can you help them level up fast enough to avoid all the mistakes you made? Can they outrun all their faults and weaknesses by adding new strengths where it matters? It’s honest the best work in the world. You find yourself constantly optimistic that big things are possible. That the best version of someone is inevitable with work and love.

Of course founders with battle scars know it best. We know where the sharp turns on the road are. Because we wiped out there. When we yell out to you to watch out it’s because we know the road better than you.

I’d also bet that this is why venture capitalists will stay with founders who are floundering and fucking up and being failures. You’ve seen their bright spark. You know their brightest self and it’s aspirations. And sometimes it’s really hard to accept when someone just isn’t going to make it. Because belief is deeper than facts sometimes.

Categories
Startups

Day 392 and Deal Flow

I wrote about my general philosophy about the futility of the typical hour long deck based venture pitch two days ago. I explained that I’d rather have a conversation with founders.

So if you want to pitch me just hop on over to a Telegram chat or my Twitter DMs. Let’s talk and learn and share and then I can really see your passion and vision and we can both avoid canned performative shit.

Well since then my Twitter DMs have been filled with amazing chats with founders of companies as diverse as consumer products, marketplaces and web3 games. The stuff people are cooking up in crypto is wild. Thought not enough SaaS tool pitches though so clearly I’ve got to get more mindshare there. Note to self to impress Jason Lemkin or something.

I’ve taken a dozen pitches now through direct messages and chats. It’s worked amazingly well. Maybe I owe a drink to Sam Lessin as he came out strongly against Calendly right after I wrote this post.

So pitch me however you like to communicate. Plus, don’t we all die inside a little every time someone sends a Calendly link?

So I’ve got to say I hope I became known as the slide into her DMs VC as this has been a lot more fun than trying to play calendar sync with dozens of people. That game sucks.