Category: Startups

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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.

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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.

Categories
Aesthetics Finance Startups

Day 390 and Pitches

So I think pitching is bullshit. My husband has a great analogy. He thinks an hour long pitch to an investor is like a white board coding interview. Have any of you ever done developer work that didn’t have access to StackOverflow and Google? Yeah didn’t think so. It’s a completely artificial environment. Real work is collaborative and input driven and not at all tied to your capacity to memorize and perform on the spot.

I think this is pretty revealing. We force intuitive input driven thinkers, our founders, into a situation where they have little to no feedback. They can’t get anything from us as investors for like twenty minutes. They lead an investor by the nose through a narrative but what if it’s a narrative the VC doesn’t care about. Then what you lose the deal? Fuck no.

You should anchor a conversation based on expressing interest and seeing together where the biggest vision might lay. I’ve legitimately talked to founders who can see their way into imploding corporate legal apparatus or building clean energy through on chain gaming. That is some science fiction level shit. But could they tell me that in a 12 page deck? Fuck no they would look insane. But I want to see you for who you are.

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.

You want an investor that sees you for you. I want a founder that is building with such a keen passion it’s all I can do to stop from wiring the money that day. Our incentives can align from first contact. So pitch me however you like to communicate. Plus, don’t we all die inside a little every time someone sends a Calendly link?

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Emotional Work Startups

Day 383 and Good at What I Am

Startups are a privilege. You meet people who are exceptional at what they do. Brilliant qualified people who are so capable you could spend your whole life working and only achieve 10% of their innate capacity by natural talent. But the real differentiator is never the talent. It’s the acceptance of who you are. You can’t just be good at what you do. You have to be good at being yourself.

Be good at what you do. Then be good at what you are. Startups require both.

I struggle with this and watch many others who struggle as well. I am brilliant at connecting and amplification but terrible at details and logistics. I used to hate this about myself. I’d beat myself up when I’d get performance reviews that said I wasn’t detail oriented. I thought it was a moral failing. But guess what? It’s just a regular failing. I doubt I’d be great at my actual natural talents if I also had to be good at my failures. Accepting your light means accepting what cast shadows equally.

It’s hard to do. Our coping mechanisms praise us for our good traits and claim full responsibility for achieving them on our own merits. Equally we disown and assume divine intervention or forces outside our control drive our vices. We cannot be responsible for our failures. We only like to take responsibility for our wins.

And I get it. Accepting your shadows is hard. Our parents and our social circles show us who we are supposed to be. Show us what to strive for in the good life. If we are loud we are told to shush. If we are shy we are urged to socialize. Acceptance oh who we are isn’t encouraged. And for good reason. We must push to grow. To become an adult requires effort and work. But we must always remember the ultimate goal in becoming an adult is to become who you are. If you never accept yourself you will never be truly great. And the road is long so start getting good at being who you are.

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Startups

Day 378 and Greenhorn

I’ve been running around the mountain west as I’m looking to buy a homestead. I’ve got kind of an elaborate master plan involving mountain houses & ranches and finding a set of living circumstances that works with climate change and social uncertainty. It’s a lot.

This means I’m doing a lot of social signaling to show people that I’ll be a good neighbor. Every place has its own social mores and expectations. I’m trying to show folks that I’m a good daughter of the inter-mountain west. But I’m also someone with the means to acquire property and invest in their community. But I’m also someone who appreciates the ins and outs of rural living. And well the list goes on depending on who I need to impress and about what. Every niche has its hierarchy.

It reminds me a lot about the process a first time founder goes through when fundraising. You are frantically signaling to different constituencies that you will fit into their expectations and worldview. But you do this dance while being completely new and naive to what matters. Being a greenhorn is bad for business. Doesn’t matter of that business is ranching or raising a seed round of venture capital. Alas everyone starts somewhere. So first time founders are often distinguished by how fast they can figure out all the shit they don’t know and fix it.

I’ve got a first time founder I’m excited to be investing in that I’m coaching through a fundraise. He knows his field and business, but he is a total greenhorn when it comes to raising a round. Just charmingly naive to the ways a round comes together. Alex and I are both frantically trying to school him on manners and customs before you can accidentally fuck up something that can’t be unfucked. It’s hard work getting someone schooled up on all the little signals that can doom a deal. But it’s also our specialty.

The particularly challenging aspect of a first round founder is just how much social signaling can be life or death for your company. Maybe if I’m up in Montana scouting property I need to show a certain set of mannerisms but the worst that can happen is someone won’t do business with me. If you fuck up a crucial deal point for ignorance or send a social signal you don’t mean, in venture it can sink your deal and your reputation without you even knowing it.

In venture, someone not doing business with you probably means your company dies. Early stage angel and pre-seed venture investors teach their asses off with new founders to avoid this fate. We can’t afford you being a greenhorn because we know it means death for the business. So if it’s your first time as a founder and fundraising, do yourself a favor. Recognize you are a greenhorn. Find an angel investor or advisor who you can trust that will teach you the manners and social signals you need. Good ones love this work. And you can reward them with advisor shares and pro-rata on your cap table down the line. If you are looking for someone like that drop me a DM.

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Startups

Day 360 and Have Fun

I’ve got a friend who is a world class talent in their field. I admire what they do. But their ability is fairly is specific to what they do at a startup and doesn’t transfer easily to different stages. They recently took a job at a different stage and I’m a little afraid for them. What if it breaks them? What if they get burnout? I am projecting a lot onto this friend at the moment as I am also a fairly specific kind of talent. I’m an early stage person.

The reason I’m so sensitive is I’ve been broken by being in the wrong roles or working on the wrong problems. I tried to change myself to fit something I was only a 7 at when I knew I could be working on something where I was a 10. I hurt myself to fit in.

The hardest part about startups is they are genuinely life altering. It’s hard to make something new. Every harder to nurture and grow and sustain it. Creativity is fucking hard. Every time I criticize a project I do it with a hitch in my heart. I know even the shitty failures were the honest best work of people who cared. And often when it’s a success it’s not because any of them were better than anyone else. We are all fighting our hardest battles. Sometimes by the grace of God our work gets lucky.

So in the meantime I think we should all be having fucking fun. I only commit to founders who so clearly want to solve the problems in front of them. That passion cannot be forged. Real interest and focus are such potent forces. You feel it in your bones. Doesn’t have to be a huge world changing problem either. You can just really love your little corner of the universe.

So don’t try to fit yourself into a role for money or status. Pick a startup because it’s going to be a blast with people you love. Make sure as much of the work will be your particular brand of fun. Maybe to someone else it would be hard work. But if you pick right it will be fun even if it takes all of you to do it to the standard of your passion. And if you are very lucky sometimes it works.

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Finance Internet Culture Startups

Day 353 and Wagmi

Gaming is what finally pilled me on crypto. When I took a medical leave a few years ago I felt isolated. I picked up a number of social games as a way to feel connected to other people. What started as fucking off ultimately transformed my perspective on investing. I didn’t know it yet but it was setting the stage for my fascination with web3.

I made friends. Real friendships despite none of us ever spending time together IRL. I made friends all over the world in completely different places, from wildly different social and economic classes, and we all easily collaborated to win together.

And while this sounds obvious I learned just how much talent and intelligence is evenly distributed to my fellow humans. The only difference between me and many of my fellow gamers was that I was born with a good passport. While everyone had the same access to internet as me, what they didn’t have was the same access to to global markets as I did. We could play together but we couldn’t invest together.

Their ambitions were cut short because of geopolitical decisions that had nothing to do with their ability to contribute and accumulate meaningful value. I had always known this intellectually, but never before had I been so deeply emotionally connected to so much human diversity as I was through gaming online.

Frankly it radicalized the fuck out of me. People in the West have no idea how good they’ve got it. And it’s a crime that we are not all actively working for all of our species to have equal access to markets. It’s just fucking time to drop the colonialism and the exceptionalism and combine our ambitions. We’ve got big problems to solve.

For me wagmi is some powerful solidarity shit. And I’m basically a foot soldier to the plutocracy. I am at the top of the food chain. I’ve get every reason to want to rent seek and act a protectionist to preserve my place. But thanks to something so simple as playing with others got me back to the golden rule. Do unto others.

Web3 offers a radical cultural position that everyone should own their work and everyone should compete with the same rules. When we say “we are all gonna make it” it’s an optimism about the kind of future we can build together. Sure the wealth is good. We need those incentives to come together. Markets operate on self interest. So let’s use that slay the beasts of collaboration and make stuff together. Wagmi.

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Biohacking Finance Internet Culture Medical Startups

Day 350 and Web3 Healthcare

Imagine you’ve got a disease with a clear biomarker. I’ve got an autoimmune condition called ankylosing spondylitis. One of the ways to spot it on a blood test is to look for an elevated CRP or sed rate.

Maybe I want to find a way to connect with other patients. I provide proof of biomarker to join an autoimmune discord just like you provide proof of ownership of an NFT like they do in the Bored Ape Yacht Club. Maybe I want to join a group of other patients who are pooling their medical data so they can stop being in an N of 1 and have a chance to participate in new research for my own disease. I could join AutoimmuneDAO and contribute to funding, meme-ing, and researching my condition. If we discover a treatment protocol or drug through our DAO we’d have ownership in it. Imagine a token for your own patient DAO. This isn’t as crazy as it sounds. VitaDAO is doing this for longevity research. This is the future that web3 can bring to healthcare.

Quantified self and biohacking have improved my health significantly. But on its own my personal health data has little value. You would maybe pay me a few cents for my biometrics. The real value of that data is in the aggregate. That’s why I pay Whoop to manage my HRV data and why they won’t offer data interoperability.

The value is in the algorithm. But without me and without my data it wouldn’t be worth anything. They have a product and an algorithm because of my biometrics. And yet we’ve found no way to meaningfully integrate ownership and interoperability in healthcare yet.

Let me give an an example. There are multiple companies that make their money by recruiting clinical trial candidates. Why? Because you need aggregate data to run a study. Those companies have the same basic data analytic team as a marketing team at a direct to consumer product company. They know how much a patient (or customer) is worth and the cost to acquire them. You are worth a lot because you represent a demographic that has value in its totality. And yet most clinical trials fail to recruit people because patients just don’t see a benefit to participating. You’ve got no ownership or upside and the costs are significant. So science suffers.

But what if instead of being valuable to marketing and recruiters you could own a portion of the aggregate? Being a token holding biomarker “proof of disease” validated member of a patient research DAO flips the incentives. A breakthrough on a disease that treats you and you’d also own some of the proceeds of it’s intellectual property. Whoever brings web3 to healthcare is going to be doing a significant good for humanity. Web3 can improve diseases, move forward science and get us all paid.

Categories
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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Chronicle Internet Culture Startups

Day 321 and Distracted

I was so excited for today. For the first day in weeks I didn’t have a single appointment on my calendar. I had finally run the gauntlet of bullshit obligations that has been chopping up my focus and my days.

I went to bed last night sure that’s I’d finally send out all the emails to folks I wanted as limited partners in my fund, follow up with a bunch of founders, and organize all the various materials and research just waiting to be published. I was going to make progress! I was going to pull the future forward with my own willpower.

But what did I do instead today? I sat in on DAO governance calls in Discord. I accepted an invite to a new working group for a stateless crypto project that is being rebooted for its second round. I listened to token and ecosystem rooms on Twitter for projects I’m invested in. I watched some bitcoin maxis fight against some side chain projects. And I read a bunch of newsletters and financial papers. Which all sounds productive but is basically me just fucking off.

The future arrives whether I pull it in on my force or will or not. Distraction probably has no meaning. But I did finally find a house in Colorado that I could see myself buying. So the only appointment on the calendar tomorrow is visiting the property. So perhaps that’s as much progress as was necessary.