Category: Startups

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Finance Media Startups

Day 299 and Hiring An Assistant

I’ve been thinking it is time to hire an assistant. Obviously I need help and the job would be working with me. But I want to train up someone who would like to acquire my unique set of skills. I’d like to mentor someone up on the startup ecosystem that I’ve spent the last fifteen years working through as a founder, operator and now venture investor so they too can take advantage of the incredible network of people that are building today.

I’m looking for someone that would like to get exposure to all the areas where I have expertise. You don’t have to know or even like all areas, obviously this would depend on the candidate, but what makes me an unusual player in startup and venture land is the weird mashup of specialties. So if you want to learn:

1. Angel & seed stage investing analyst skills
2. Media & hype (call it public relations if you must)
3. How one keeps your head on straight in a discourse laden zeitgeist chaos landscape

Then you might enjoy working with me. The goal of this assistant or analyst position would be within 2 years you’d go on to do what I do somewhere else & I’ll sensei you through that journey. I am where I am because of mentors and bosses that taught me the ropes.

As I work closely with my partner and husband Alex Miller you would get exposure to the operational and logistical side of investing as well as startup operations. He’s actually my inspiration for this job. His first job out of college was for Jason Calacanis. Without him none of the other jobs and connections would have been possible. And we owe him big time as without Jason we wouldn’t have Stack Overflow in our life.

I’ve only every met one person who has my particular weird blend of growth, media and investing. I do some traditional public relations and would love to pass that on to someone that could leverage it well for their own startups. But it is entirely in service to my investing and portfolio with the occasional other favor, so it’s much more portfolio services for our investments than a PR shop. But you’d learn our portfolio from the inside out as investment decisions and then figure out how to take these seed stage companies to market with the media. Which is a pretty unique thing so not a traditional gig.

Non traditional backgrounds are awesome. No degree requirements. No credentialism or social signaling. Disabled folks welcome. I’m also disabled so we do accommodations. There is no set schedule as I don’t work one so whenever you work best is great. Any location or geography is fine. Any time zone though I work on mountain. Degen anons with anime avis welcome (encouraged as I’d like someone fluent in crypto). If you are an anon avi who wants to get into crypto investing and figure out how to work the zeitgeist for your meme magic I am here to be your mentor. And then I’m an ideal world I’d be the first check into your startup as this is about the ecosystem. So if this sounds fun slide into my DMs on Twitter and tell me what the one thing you do better than anyone else.

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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 Startups

Day 296 and Under Budget

One reason I’ve been comfortable working in startups my whole life is I’ve never been a big spender. My biggest expense is probably takeout, as I find cooking to be a waste of time. As long as I can afford medical insurance (I’d get a job somewhere with socialized medicine if it came to that) I’m pretty happy with a one bedroom and Chipotle for dinner. Some people get used to their lifestyle as they make more money. I just haven’t yet.

If I go bankrupt (and sadly I lived through that emotional roller coaster as a teenager with my family) I could find a way to live within new means again. I don’t have to be in the top 10% to have a good life. I only need that for health care costs and sorry America but there are other options. I’ve got skills that could earn me stability if I wanted to make that choice. Hear that Canada I’m recruitable!

But I do need to learn to live comfortably with my current means. It’s alright to live within your budget. Sometimes budgets bigger and you can easily spend more on disposable income. And this was a year where my means finally got comfortable. And I’m still sort of afraid to use it. I had to really talk myself into a chair that that was functionally a workplace accommodation. Instead of just jumping at a chair that lets me work comfortably for longer hours I spent several years just not working as many hours.

This tendency to live under budget comes everywhere. I wanted something I considered fairly lavish for dinner. But I thought how ridiculous to spend an extra $15 on dinner. I got a little worked up trying to think of other options that I wanted as much and my husband said “fifteen bucks isn’t going to make a difference get the damn thing.” And so I did and it was fantastic. I’m super happy about my evening and the spending will have no impact on my total budget. Anyone who tells you that money or privilege can’t buy you happiness are lying. Happiness is a choice and it’s an easier choice when you can make the choices you want.

I had mental upper bounds on what I think it is responsible to spend for years. I ran an Airbnb side hustle out of an underpriced two bedroom in Chintatown while I had a six figure salary, because I wanted to live so far under my means I could take risks if I wanted. That under budget mentality let me save up 70,000. It’s also how I met my husband but that’s a different story.

That kind of thinking let me enjoy startup failures for the priceless learning that they are. But now I realize I’m afraid to live on my budget. Unless I’m living massively under budget I’m a little uncomfortable. So I’m going to try to let that one go. I can just live on budget.

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Internet Culture Media Startups

Day 295 and Long Game

I think most people dislike media because it’s hard to understand where a narrative came from. If you aren’t in the business of telling stories the natural braiding of emotions, motivations and public opinion can seem foreign. It’s like the weather. It’s completely comprehensible how different patterns emerge but you cannot predict precisely how it will play out. There is a science but the specificity of the modeling isn’t so accurate you can predict the course.

This is why I encourage startups that work with me to think about the long game. Give context about your space and your opinion of how it will change and grow. Don’t be afraid to state clearly and in specific why something is the way that it is when talking to a journalist. No one is out to get you.

Journalists just want to show a story that makes sense to regular people. A cohesive truth that can be proven with outside and objective fact still matters to virtually everyone outside of very specific Murdoch outlets (never give a quote to the NY Post).

So much of being covered in the media is not about having a publicist or being trained but is rather about interacting with the 4th estate as if they are human just like you. A reporter will happily tell your story if you can make a case for why it’s true. And no one is coming to “gotcha” over some secret. The Internet may roast you but that’s just the crowds. No one has control over public sentiment. You too may one day become the main character on Twitter. But that’s probably your fault and not a journalist’s doing.

So if you want to live in public think through what the long game might be. And work on convincing others that the future you see is not only good but inexorable. And repeat it with conviction. It’s ok if you get some shit wrong, cancel culture won’t demolish you. Probably. I mean some of you deserve to be canceled but somehow it never seems to happen to the assholes who really deserve it.

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Internet Culture Startups

Day 282 and Stop & Go

I wasn’t born until after stagflation so I can’t tell you what America or Britain felt like in the 70’s but the chattering classes seem to enjoy bringing up the comparison. But there does seem to be a bit of “stop & go” energy in the air. Everyone is raring to go but the energy cannot quite flow freely as we smack into obstacle after obstacle. Demand is pent up but the reality of supply is uglier.

Obviously this perspective of excitement and demand is colored by working in startups where the bias is always towards the excitement of building new things. Crypto is burning with the fire of millions of zealots, all of whom are confident we are building the infrastructure for a better future. Everyone feels like it’s worth investing and higher prices are a good sign. There is more go than stop here.

Of course, I am one of those zealots. I’ve got the optimism of someone who saw how fast previous waves of web1 and web2 changed my entire world. Wealth and creativity was unleashed twice over for the elder millennials who were lucky enough to witness the dot com boom as children and the social media era as their first jobs.

There were massive crashes and financial implosions too. Stop more than go. More of us got hurt than got wealthy. But we saw the possibility even as failure engulfed most of us. So we believe we might be the lucky ones this time. That we might be the ones to win the game. “Red light, green light” seems fun if you can make up ground when everyone is running. Just don’t get hurt too bad.

I feel this energy in my own body. I am excited to push into everything. My portfolio companies are all riding high. There is no way I can do it all in any given day. So when the go energy pushes me sometimes I find myself leaning into stop and simply taking a nap in the middle of the day. It makes me a little jittery to feel the push-me-pull-me of demand grind up against the limited supply of energy and focus. I’d like to feel fully unleashed but I know somehow there are moments where it’s best to stop before I go.

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Finance Startups

Day 275 and Manifesting

I had a really terrific September. Everything just started going my way. Projects that I’d been pushing on had significant breakthroughs. My deals got hot. My focus and health improved. Even when I had setbacks and failures I was able to execute on quick recoveries. But mostly I didn’t give in to past bad habits. And all of that happened without any additional effort on my part.

I’ve been making a really conscious effort to stop pushing myself to always be doing more. Either I am able to find elegant solutions or I ask myself to take a step back till I can. Rather than brute forcing everything I am finding ways get where I am going without sacrificing myself to costly bad trades on my time and energy.

I asked for something really significant from one of my investments (an additional allocation for an special purpose vehicle). The second I asked for it I started to panic. I didn’t have an immediate or simple path to deliver on what I asked for from this founder. Even though I was confident I had the money for the deal it out I panicked that maybe I had bitten off more than I could chew. Immediately it started going through my head about how bad I’d feel if failed this founder. I relived the guilt, shame and punishment I had felt in previous failures to deliver for people that trusted me. I hated feeling like I’d failed people.

And I just decided stopped the cycle of worry then. Like turning off a switch. I told myself I could do it, I knew I could do it or I wouldn’t have asked, and that there was simply no way I was going to let down this founder. But this is where I felt the frown Instead of going into overdrive, I stuck by my schedule. I didn’t change anything. I didn’t push myself to a frenzy by adding in calls, pitches & emails. I just put down all the steps I could and would take to make the deal available to the right people and I began.

In the past I would have let that fear drive me. I would have gone into overwork and adding in additional tactics that I didn’t even need to insure I would reach my goal. But here I trusted myself to get the outcome. I didn’t exhaust myself. I took care of myself. And the allocation got filled quickly. I checked the commitments this morning and I’ve only got 15% of the deal left.

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Finance Startups

Day 270 and The Circle of Capital

Capital has evolved a lot in my life. The dynamics have changed so much in the 30 years I’ve been ambiently around venture it’s barely the same business. And yes I mean since I was a kid. The apocryphal family history is that I was born on the poor side of Silicon Valley while my unemployed father was working on pitch deck for education software. Yeah it’s a shitty origin story but it’s mine.

Back then you sold your entire life to some dudes for half a million bucks and gave up a lot of control. It wasn’t really collaborative but it was worth it to create the future. Back then your VCs controlled a lot more than they do now for capital they deployed. Flexibility and collaboration wasn’t really considered necessary. Your VCs actually controlled when you got fired (another childhood memory was a “take your daughter to work day” where a CEO got fired), when you could raise again, if and when you could sell your company, and honestly I wouldn’t be shocked if they had some Rumplestiltskin provisions too. That’s just where the market was at the time.

As it has become clear that non-linear returns come from creative founders and new markets, the structures of capital deployment have changed a lot. Capital cares about helping operators create because creation simply has more value than it did in the past. Venture capital isn’t old dudes optimizing for control and margin anymore (even if sometimes that might be a good idea) because that’s just not what makes money anymore.

Heck it has changed a lot in just half a decade. The last time I raised venture for my own startup, we actually priced the round (no uncapped SAFEs), we had a board from day one, and we were allowed to overshoot our valuation and capital goals by a whopping 300K. I was sure we’d reached the height of founder leverage at the time. Heck I felt certain we’d raised a small fortune on favorable & flexible terms. Six years later that would be considered a charmingly small pre-seed round with very onerous terms. Time marches on! And rightly so. Markets adapt to the needs of the participants and the returns they deliver. If it wasn’t profitable it wouldn’t be so.

This is all a long winded way of saying that I am continuing the circle of life. I’ve got my own venture fund Chaotic Capital with Alex Miller and Jacob Brody. It doesn’t look anything like the funds of my childhood or even the seed stage funds of the last decade. Probably because we as founders and operators lived through the hard lessons of venture in multiple cycles and took a lot of lessons with us. Capital isn’t about control. It’s about collaboration now. Capital starts early. Capital is flexible to generate returns But we also aren’t n00bs.

Rather than spend a year raising in silence and announcing it once it’s all said and done we are building a rolling fund. That structure works for us and my general affinity for building in public. It signals founders we are building like them (even as our other constituents see it as being responsive to the demands of the market). The rolling fund is a kind of flexibility to build at the speed of the market while also understanding that the give and take of responsible deployment must also work at the pace of founders.

While we work on forming our proper fund, we’ve created an AngelList Syndicate for chaotic where we’ll be creating SPVs for our current deals (we already have our first two which feels crazy to me) as well as follow-on deals once the fund is created. If you’re an accredited investor and interested in joining our deals, head on over. Isn’t it cool how these structures morph and change over time? I guess having a couple decades of being an operator has some benefits. You’ve seen what works and hopefully have some capacity to change what needs to be changed.

Our LPs and co-investors are mostly our friends and former colleagues who have spent years working with us at companies as varied and diverse as Stack Overflow, Trello, Easypost, Triplelift, Goop, PopSugar and over 40 different angel investments. Alex Miller, Jacob Brody and I have invested over 4m over the years which seems sort of astonishing.

While we work on forming our proper fund, we’ve created an AngelList Syndicate for chaotic where we’ll be creating SPVs for our current deals (we already have our first two!) as well as follow-on deals once the fund is created. If you’re an accredited investor and interested in joining our deals, head on over.

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Finance Startups

Day 255 and Bias Towards Fuckround

There is a tendency to believe that startups have a bias against older people. While ageism is alive and well, I’d argue what appears to be a bias against older teams is actually a bias against teams with experience. No one wants to invest in a team who don’t fuck around. We want teams that will find out.

One of the reasons I work with early stage startups is because their trajectory is not yet set. Every conversation has a hint of “fuck around and find out” because your vision is far away. You need to experiment, test, throw spaghetti against the wall. Pick your metaphor. The bias towards action and the bias for momentum exist in investor minds because the alternative is death.

This has the second order effect of selecting against teams with experience. It isn’t ageism. It is a bias against a certain kind of professional that knows too much. It’s not that anyone thinks experience is bad. It’s harder to fund teams with no exposure to the industry they are working in. It means that some types of experience will function as negative signaling. We think you know too much to solve the big problems. We are afraid you aren’t flexible enough to do the work of throwing out all existing assumptions.

While being an expert in a field means you have a better sense of how you will get from point A to B, it also means you have a less flexible mindset. You have seen what hasn’t worked. You have opinions about can or cannot be done. Even worse, you have an idea of how things must be done. Simply put a certain kind of battle tested, “expert in their field” persona isn’t trusted to fuck around enough.

If you are one of these founders, you have to fight against this signaling issue. Show investors your commitment to fucking around and finding out. Telegraph that all your experience and knowledge from your past work could very well be bullshit. Show us you will be committed to testing even more rigorously every hypothesis of how your roadmap will unfold. Then your experience becomes an asset.

We will trust that you have more opportunities to fuck around and find out than a less experienced founder because you plan to test what you think you know. Which is a lot! Show that no truism of your space will be held sacred. While a neophyte team will need to discover all the truths of a space to even begin to test. you will be ahead of them running test after test. Jujitsu that shit. Use the energy of your experience to show that you will bring the maximum amount of flexibility to finding new outcomes. The unbiased but experienced mind has the best chance at achieving momentum.

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Startups

Day 250 and Getting to Know You

I don’t really like musical theater (it’s the people sorry) but I’ve been humming a tune from The King and I called “Getting to Know You” as I codify my process for meeting founders and startups. It turns out Julie Andrews through Rogers and Hammerstein lyrics may be a viable strategy for finding out if someone is a fit for Chaotic.Capital. The actual play is racist, colonial nonsense but you know take art for art’s sake.

Getting to know you

Getting to feel free and easy

When I am with you

Getting to know what to say

Haven’t you noticed

Suddenly I’m bright and breezy?

Because of all the beautiful and new

Things I’m learning about you

Day by day

She’s talking about being a teacher and getting to know her pupils but it’s also maybe about falling in love, but I like the sentiment that learning “beautiful and new” things “day by day” feels bright, breezy, free and easy. That’s a good template for relationships of all kinds.

Pitching is none of those things. It’s practiced, formal, and exhausting. It may be a necessary evil for founders as you need concise and clear communications about what you are doing and why it requires capital. But I don’t think it’s the best way to get to know people. Getting to know someone should feel easy.

I like to get to know someone over the course of conversations. My preference is through asynchronous communication mediums like chat, direct message or email. There is something about the volleying back and forth of information that helps me more. I like a back and forth that is informed by revealing thought process but also context and background. I’ll chat with virtually anyone and keep my direct messages open on Twitter because I value conversation so much.

I generally don’t feel that phone or video calls are that helpful to me in getting to know someone initially. I don’t mind short 10 minute bursts. What I do dislike is the planned hour long call for an initial conversation. Rarely am I able to be emotionally and physically present for something like that if I am not already interested or invested in story.

But if we’ve had conversations through Twitter, direct message or email where I have more context and connection then it’s possible I can be present for you. But I wouldn’t recommend asking for an hour synchronous medium as your first interaction with me. I’ll do it as a favor to someone now and again but I almost always resent it.

I’d rather get to know you over time before I’m trapped in a room for an hour to put it bluntly. I promise this is for both of our benefit. You wouldn’t take someone on a two week vacation for a second date so why would you hinge your chance to work or get investment from someone by insistence on spending an hour together right off the bat. Let it simmer a bit. Give me an appetite for wanting to help you. Then you won’t be able to get me off the phone or Signal. I will be your most available investor if you take the time to show me who you are.

So go ahead. Message me. Message a bunch. Send an email. If you don’t hear from me message some more. If I’m being evasive tell me straight me. But the end goal should be that getting to know you is free and easy. And you will be able to tell if I’m excited. Don’t give up. Just keep the conversation flowing like Julie Andrew’s did.

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Startups

Day 243 and Delegation

One of the funniest aspects of hustle culture was its insistence on always being “on!” This maxim fought mightily against that other successful management truism; a successful CEO delegates. But how can you always be working if you have also successfully delegated your workload to a top notch team? Which one is it guys?!?!

I guess the logic was that you should always be working on whatever new horizon you has discovered in your perch as visionary founder but also be continually recruiting the best possible people to take on work as you should never be doing that work yourself. But those two directions are in obvious tension.

I think this tension ended up creating founders who exercise control of their anxiety through constantly searching for new ways to show off they were hard at work. We got addicted to busywork. Or at least the appearance of always being hard at work finding a new problem and then hiring talent to own it.

You’d always be finding new blockers at every turn, justifying it as growth and then you’d balloon your team hiring people for the work that you’d just found. I honestly wouldn’t be shocked if this was the driving force behind the trend of showing off your headcount growth.

“Oh we hired 50 people this quarter!” Sure but like were you actually blitzscaling or were you caught in the hustle/delegate hamster wheel? How many of those people actually materially moved your roadmap forward? I would bet at least some of them were just there to give you the emotional safety of claiming to yourself that you’d satisfied both hustle and delegation culture.