Tag: Competence

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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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Preparedness

Day 325 and Preparedness Reading List

Since I’ve been yakking on about being a prepper recently I thought I’d take a moment to share my recommendations for thinking about a more resilient life. They range from the extremely practical to the oh shit I hope I never need this information.

Homestead & Practical Skills

Escape the City by Travis J Corcoran is literally pound for pound the best value in preparedness. It focused largely on folks who want to build up a piece of land or otherwise want to homestead. But it’s extremely practical advice on everything from planning a home to what tools and skills you will need.

Encyclopedia of Country Living by Carla Emery: an absolute classic with everything from recipes to practical how to guides. If you want to see what practical skills might be for you this is a great start.

Back to Basics edited by Abigail Gehring: it’s not as comprehensive as Carla’s encyclopedia but it’s a bit more accessible if you want to think about gardening, food preservation and the like.

Land book by Neil Shelton: a very specific little book on how to evaluate and buy rural properties for families.

Emergency & Disaster Preparedness

Beginners Guide to Emergency Survival Preparedness by Jeff Kirkham and Jason Ross: these dudes write the Black Autumn series which is a weirdly racist but packed with surprisingly good detail fiction series. Their beginner guide is actually short and reasonable information on preparing for the 3-10 day emergencies.

Urban Preppers with Pets and Kids by James Mushen: exactly what it claims. I used to be an urban prepper and it’s one of the first books I read after Hurricane Sandy got me prepping. Likely the first place to start for most of you.

Philosophy

Lean Logic by David Fleming: it’s subtitle is a dictionary for the future and how to survive it. This isn’t practical so much as a deeply comprehensive look at a world that isn’t flooded with cheap oil and requires a more decentralized approach.

First Aid and Medical

The American Red Cross First Aid & Safety Handbook: pretty self explanatory. This is the text everyone uses when they get certified.

The Survival Medicine Handbook by Amy and Joseph Alton: preppers love this doctor and nurse husband and wife duo. The book is super practical and frankly you should pray you never need it. But if you are outdoorsy you appreciate that medicine looks different if a doctor isn’t on the way to help.

Categories
Preparedness

Day 323 and Fantasyland

I’m very open about being a prepper. I think it is a moral imperative to be resilient if you have the means to do so. When disaster strikes, which it inevitably does, being able to support yourself and your neighbors frees up first responders to care for the genuinely needy.

Because of this belief I’ve been investigating homesteading seriously for the past two years now. I’ve got concerns about the typical issues someone with exposure to finance has; worries about inflation, the social impact of labor being a poor store of value with currency debasement, & widening inequality. I am also deeply concerned about the rise in populism and the predatory graft of the far right. Add in supply chain worries and the effect of the pandemic on living standards and you can see how I’d prefer to have more control over my own basic needs.

But my plans to go off grid has always had a bit of a fantasyland element to them. While I would love to move to northern Montana and invest in a large property I didn’t expect I’d be able to do that immediately. I needed to get to know the towns, watch an illiquid market over months if not years, and also remain proximate to civilization as I still plan to maintain a career in startups and finance.

But yesterday my husband and I came across a property outside of Boulder Colorado that met many of our criteria for more prepared living. An unobtrusive property on an acre just outside of town that I jokingly called greyman as you’d never guess it was built out for resilience. It has 100% solar with insulation & a wood burning stove for backup, there is a working well that irrigates the garden & orchard, its got a hothouse & a chicken coop, it’s on a reservoir, it has a workshop & an artist studio, and well I could go on. Now I’ve got no idea if it will pass muster on an inspection but as you can see I’m already dreaming of the possibility. It’s not something I’ve absolutely got to do so we can very much walk away from a deal but I’m interested. Enough that I’m looking at mortgages and bringing in a contractor to take a look.

Now I don’t need all of those things right now. The reality of maintaining a vegetable garden and making it through a canning and preservation season isn’t lost on me. Actually building the muscles for true resilience is something that happens over years. But that’s also why I want to start now before it becomes a must have. Learning how to feed yourself when you’ve got no choice isn’t a situation I’d recommend.

We underestimate the work that goes into maintain a healthy, comfortable, warm and well fed life. Mostly because capitalism breeds specialized labor. Which is good in my book. We’ve achieved so much with it. But any complex system is less resilient. So you’ve got to acknowledge that the tail risks are there and real. So if I’ve got a chance to begin on 70% of my ideal preparation while still keeping within my budget and also staying within civilization for the time being then I’m going to consider it. It’s time to move out of fantasyland.

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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.

Categories
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.

Categories
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.

Categories
Emotional Work

Day 256 and Helplessness

When I was a child I hated being helped. I was a “Mary quite contrary” type except I wasn’t yet in a profession where that was considered a sign of intelligence. I’d ignore the advice, aid and help of teachers. I preferred to figure things out on my own.

A story that I’m sure will eventually turn apocryphal as I get older involved a horse trainer and needing to be left alone. I was was having trouble with a jump in a group less. My horse kept throwing me and ducking the obstacle. My trainer did his best to give me advice on how to keep my posture and encourage my horse. He kept piling on advice and kept his focus on me. And I kept not making it over the jump.

I probably fucked it up over a dozen times. Eventually my trainer gave up and went to help another pupil. Without the glare of a professional, I finally gathered myself up, held the horse firmly in hand and soared over the jump on the first try.

Holy shit was my trainer pissed. “Julie didn’t need my help at all! The second I turned my head she just handled it herself.” From then on my trainer learned that I’d happily internalize his training but if he kept too close of an eye on my I’d develop a kind of learned helplessness. I’d get worse and not better.

I sometimes wonder if this tendency remains a part of me. I like attention so I’ll accept help if someone is willing to give it to me. The upside to this is I am always learning and questioning. But if I’m not careful I’ll just keep enjoying the benefits of helplessness. But I can’t linger there. Because I know moment I’m left to my own devices I’ll gather up the knowledge and willpower and make it over the jump. But it can be temping to wallow in helplessness.

Categories
Internet Culture Startups

Day 236 and Founders Who Write

A heuristic I’m playing with for assessing founders is how good they are at writing.

And while this approach to vetting a founder is a practical method (everyone writes) it’s obviously limited. But I think it is nevertheless sufficient for reaching an approximation of founder capacity in a swift and asynchronous way. I like to see examples of founder writing whether it is Tweets, blog posts, technical documentation or a Notion document.

It’s my belief that we’ve overweighted salesmanship, pitching & synchronic communication methods (remember reality distortion fields) which has led to prioritizing messianic style founders. A rousing keynote speech used to be the gold standard. But this may be less relevant as teams go fully remote and more work is done asynchronously. Your capacity to document and communicate meaning at scale is crucial as a founder.

The canonical example of a founder who telegraphed competence and meaning through writing was Joel Spolsky. The Joel on Software blog established him as ur technical writer and gave us documentation culture which blossomed in Stack Overflow.

A more recent example for me is Devin Finzer who I discovered through his technical writing. Long before OpenSea was a clear winner in the NFT space, Devin’s writing caught my attention as his crisp clear articulation on the basics non-fungible tokens was legible to everyone.

My guess is this heuristic of focusing on writing instead of showmanship will improve overall diversity of founders & companies in a portfolio as less bias creeps into asynchronous documentation whereas mirroring & social cues easily tilt pitching in favor of certain classes of people

I’m also keen on folks who like messaging culture. Being able to hop in and out of conversations is crucial to team building & scaling. Those that are happy to DM & chat to build rapport in distributed fashion more easily will succeed at building relationships in a remote first world.

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Emotional Work Startups

Day 230 and Punishment

I wish I understood why we feel the need to punish ourselves sometimes. What is it about human nature that makes us abuse ourselves? Oh we deserve it. It apparently has a social purpose as well according to Psychology Today

Self-punishment tends to serve a dual purpose as it not only relieves internal feelings of guilt but impacts how others perceive us as well.

I’ve been feeling guilty. This month is the two year anniversary of me selling my last company Stowaway to a private equity firm and pursuing a medical leave to diagnose and treat my spinal condition ankylosing spondylitis. It was a happy ending, at least mostly, with the company being put into better hands than mine. But I still felt guilty.

I felt bad I didn’t live up the expectations of our biggest dreams. I felt guilty I didn’t 100x the capital for my venture investors. I felt guilty that my colleagues had dedicated so much to me and I had failed to deliver on the outcome we had dreamed of in our early days.

So punishing myself seemed like the right thing to do. I deserved to be sick. I deserve to be in pain. I deserved for the whole world to read about my experience and my failures. I deserved to be shown in public as a weak sick woman. It sounds so abusive when I write it out. Like I thought I deserved to be tortured. But maybe that’s exactly what I felt.

I am trying to unearth why I have the self limiting belief that punishment is what I deserve. As it’s more than just the circumstance of selling a startup and not seeing the results I wanted. It’s got to be deeper than the rationalizations I’ve given.

I’ve practice family systems therapy. The basic premise is that our childhood informs how we react as adults. And by healing the rough patch’s or even traumas of those times we can live the life we choose. For me I felt abandoned as a child. I wanted my father in particular to be emotionally available. But it just wasn’t to be. But I held on to the idea that I must have deserved to be abandoned. But of course it had nothing to do with what I did or did not deserve. It wasn’t about me at all.

Now I remember that I am a capable, brilliant and above all reliable person who needs to accept what I can be and not be bound by what I learned in failure. Finding that and turning it into your superpower is where the real success comes from.

Categories
Finance Startups

Day 202 and Show Me Anything

I’m lucky to see work from founders at the very earliest stages. If you have a problem you are solving for chaotic world I’m generally interested in seeing it even if it’s just in the idea phase. But you have to show me you’ve got a plan to build a product. Any product is fine. Just show me something! Show me how you have the capacity to build even if you suck at it.

Bobby Goodlatte captured some of the sentiment I feel on the subject well with this exasperated Tweet.

What’s a “builder”? Show me something. Anything. Just show me one pixel you’ve created. That’s what a builder is. That’s why PM’s don’t qualify.

Sometimes it can feel hard to build something, anything, when you are very experienced. This is a problem I’ve seen across all kinds of impressive people. Academics, government folks and higher end finance folks, former c-suite executives. They know what good looks like so anything they can physically make with their own two hands will all look like crap.

I’d even go so far as to suggest there is an inverse relationship between how much you obfuscate your lack of existing product and your credentials. There are other corollaries on that basic theme. How comprehensible your product is right now is inversely related to how extensive your service layer is at the moment.

I see a lot of brilliant, extremely credentialed people solving big problems, but because making money is important they will pitch what amount to service companies without an existing product. But they will use extensive jargon and hand waving visionary opportunities to hide the fact that there isn’t any product layer yet. Which is weird because like eventually I’ll find out right? You wouldn’t want to trick your investors on the state of play.

I’d encourage you to stop trying to hide that fact. Don’t be embarrassed that you can’t make things to your standards. None of us can. New things always look like shit. Just own up to that reality and you will find more help from folks who will want to help make it better. Stop showing me CAGR and TAM and possibilities as a way of hiding that you haven’t built a product yet. It’s ok. You don’t need to have built something great yet.

Admit it. Show me some wireframes and a roadmap. I’ll take that way more seriously. In fact, I’ll probably overweight you showing me exactly what you do have and how you plan to use funds to improve it. That’s how much startup people value just building the damn thing.