2025-03-29 21:44:36
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2025-03-24 21:37:52
I knew I had to meet Molly. That’s what I felt when several friends separately mentioned her to me. It was either a very well coordinated inception or independent validation. Frankly, either would have piqued my interest (I’m pretty sure it was the latter). It only took a few Blue Bottle coffees for me to become an evangelist for her too. Molly is thoughtful, always evolving and an incredible believer in people, whom she backs via Moth Fund. And I recently asked her Five Questions.
Hunter Walk: Moth Fund says it “aims to increase the agency of exceptional individuals.” Say more about what that means (you cover some in your manifesto) and how it influences your investment decision framework?
Molly Mielke: My approach to investing is singularly focused on finding and developing relationships with outlier people. I do this by being weird myself and making myself findable in the right places — namely word-of-mouth from people whose taste I respect and by sharing how I see the world online. This approach was designed around my edge; I have an innate interest in understanding human beings and as a result, have different kinds of relationships with founders than most VCs.
I talk about my investment decision-making framework in detail here — I focus on gaining an understanding of a person’s motivation, spike, commercial aptitude, and how magnetic they are.
I try to think rigorously about people and their potential, in part drawing from my experiences working with top founders over the past five years and the deep relationships I have with entrepreneurs in my cohort class.
HW: You write wonderful essays each quarter – what’s the process which goes into those? And what does ‘success’ look like for you with this energy?
MM: Each quarter I pick a (usually qualitative) “research” topic that I discuss with many of the brilliant investors, founders, and operators I meet with in the context of my investing role. I collect data points in conversation and start building my own theory of the topic, which I then write up and share with the world in the form of my quarterly essays.
I consider my writing a success if I’m able to produce words I can both stand behind/formally weave into my worldview and think are decently original/worth sharing with the world. Success also looks like having better conversations with the people I’m meeting — I find the process of truth-seeking together one that builds a lot of trust and understanding of each other. I am at my most honest and concentrated on the page, so sharing that version of myself online helps me put a stake in the ground about what I believe in and find others who resonate or disagree in interesting ways.
HW: I find you to be a thinker who uses other’s opinions to inform your own. As someone new’ish to venture capital, what’s a piece of advice you received early on that really shaped the way you think about Moth?
MM: While not an answer to your question, I want to first say that learning to relate to others’ opinions in a way that is constructive as opposed to confusing is something that took me a while to figure out for myself. I received a decent amount of advice from people more powerful than me in my first few years in Silicon Valley (mostly because of my Twitter) and while I was lucky to get the attention, it definitely made my head spin. I gradually learned to see advice as merely potent information about how the other person sees the world, which helped me take it much less personally. My goal in asking for advice now is usually in order to refine my internal model of the other person’s brain — the goal being that I could guess how they’d think through a given person/place/scenario without asking them. I like simulating other people’s perspectives in my mind and putting them in conversation with each other as a way of identifying blind spots in my own thinking.
A memorable piece of advice I received from my first LP was that: “the ideal investor is a finance bro with a dash of Engelbart.” While I didn’t change myself to become this, what I did take from this framing was that investors need to be commercially-minded no matter their stage, and that a dash of weirdness can be particularly beneficial at early-stage in order to attract other strange outlier people (hopefully some of them great founders).
Another piece of advice I received from an early LP was to find a great coach who pulls from enneagram in order to better understand your own motivation and become more cognizant of your failure modes. I highly recommend doing this, especially if you’re embarking on anything solo and want to stick to something for a long time.
HW: How has your model changed between your first fund and Fund II (which I’m fortunate enough to be investing in)?
MM: My main learning from Fund I was that the area where I had the unique advantage was pre-seed rounds where I was one of the first checks in and investing with a deep understanding of the person’s potential to be venture-scale founder. The strategy of Fund II was designed around my spending as much time serving founders at this stage as possible, meaning I now write slightly larger checks and devote the majority of my investing time to building relationships with exceptional people who I think might one day start an interesting company.
More qualitatively, I’ve become much more shameless about Moth not being for everyone, while a perfect fit for the right founders (and LPs, you being one I feel especially fortunate to have on board!)
HW: Ok, something outside of work. Give me two places in San Francisco which you find delightful.
MM: I really like the Fort Mason area — strolling around the Sunday farmer’s market, getting a lemon ginger tea at The Interval, and eating sushi in the park as the sun sets.
Thanks Molly!
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2025-03-19 05:35:47
Read while recovering from St Patrick’s celebrations
The Anti-Social Century [Derek Thompson/The Atlantic] – Is isolation a leading or lagging indication of breakdowns in community, political polarization, declining birthrates and other 21st century American challenges?
Men who watch television now spend seven hours in front of the TV for every hour they spend hanging out with somebody outside their home. The typical female pet owner spends more time actively engaged with her pet than she spends in face-to-face contact with friends of her own species. Since the early 2000s, the amount of time that Americans say they spend helping or caring for people outside their nuclear family has declined by more than a third.
Read it, preferably at a coffee shop, with a friend.
Stay Gold America [Jeff Atwood/Coding Horror] – Jeff’s a cofounder of Stack Overflow and writes here about an admirable decision his family has made: they’re going to give away half of their wealth to “long term efforts ensuring that all Americans continue to have access to the American Dream” such as Planned Parenthood, The Trevor Project, and other humanitarian organizations. Go go Jeff! Tech needs role models like this right now.
How I Used AI to Save My Life in 77 Prompts: A Debrief [Bethany Crystal/Hard Mode First] – My friend Bethany had an incredibly dangerous health scare which could have been much worse if she wasn’t a proactive, informed patient. She didn’t use Dr Google, but instead ChatGPT. She goes deep here on where and how it helped, the prompt chains, and the reaction of her medical care professionals. I
Thinking Through the Future for LLM Companies… and What This Means for B2B AI Startups [Sarah Tavel/Benchmark] – Sarah basically assumes the LLM platforms are going to evolve into competition for most of the B2B businesses built on top of them so she gives her best guess as to how to manage this as a challenger. You need either (a) a network effect, (b) proprietary or hard to access data, or (c) “execute like hell and land grab in an overlooked vertical.”
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2025-03-18 00:11:34
“Be great at the job and proud of how you’re doing it.” That was our rallying cry at the beginning of Homebrew. We figured that if we enjoyed it, but weren’t financially successful, we couldn’t do it for the rest of our careers. And if we made money, but weren’t happy with the work, we wouldn’t do it for the rest of our careers. So why not focus on both. This extended to how we pitched LPs as well, aiming for a very concentrated base of institutional investors. We figured that given their commitment to the asset class, so long as we did our job well and treated them like partners in our business, they would show up each fund to back us.
Years later Satya and I also started Screendoor alongside Homebrew. If Homebrew’s goals were to back exceptional founders building companies then you can think of Screendoor as backing exceptional founders building new venture firms. We’re now four years in, having invested in almost two dozen VCs, which by the way, if you’re raising a fund, let us know. Whereas Homebrew was always meant to be just the two of us, Screendoor is more expansive and now has a team of three running the show.
One of the folks, Lisa Cawley (Screendoor’s Managing Director), recently published a blog post called “Work with your LPAC, not for your LPAC,” which got me thinking about Homebrew’s LPAC (Limited Partner Advisory Committee). Ours has always been small – just like our LP base in general – and we’ve worked with them in ways that are spelled out in our LPA (Limited Partnership Agreement) but also used them for advice, as the name suggests. Lisa’s post – and more coming – goes into depth about what an LPAC is and how it can be helpful for a VC, especially a new firm. To make it really tangible, here are examples of why we’ve gone to our LPAC over the 12+ years of Homebrew.
Standard Asks/Approvals
Situation Specific Guidance We’ve Asked About
Most of these have been ad hoc emails or phone calls, but we make sure to get our LPAC together each year as part of our AGM, usually in an informal lunch or discussion prior to the main presentation. They’ve been invaluable and we feel really fortunate to have a relationship that’s professionally oriented but also supported by care and personal affinity.
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2025-03-11 10:34:47
I’m a believer in the ‘software eats the world‘ thesis, although I often change it to ‘software enables the world,’ which is not nearly as evocative but also not as consumptive. One byproduct of this movement, especially during the blitzscaling era, were new startups in areas such as finance, healthcare, housing, education, using venture capital to acquire customers at accelerated rates. And when these startups failed, the customers might find themselves confronting situations where a product they relied upon ceased to exist with very little notice.
For the investors it’s of course a disappointing outcome, but the failure is built into their model and they knew going in that ‘taking a zero’ was a potential ending – that’s why they’re ‘accredited investors.’ For the human being who is your using your service, quite often they don’t have the same visibility or understanding of the risks – there’s no such hurdle to make sure someone is an ‘accredited consumer.’
In the B2C world, especially when the startup is serving a the bottom of Maslow’s pyramid, a flameout ca leave you without a home, a therapist, or your savings. Because to some people on the org chart and on the cap table it’s better to use the last $500,000 to take one last growth hack swing than to manage a wind down.
I’ve said before this is one reason why we are very very careful about investing in addiction or mental health startups. As I wrote in 2021,
Which leads us to the fundamental difference between, say, a small self-funded online therapy practice and one that has taken millions of dollars in seed capital: the latter can acquire a larger number of patients much faster using investment dollars for both customer acquisition and to subsidize the economics of serving those clients. That’s what always gives me a little bit of pause in this particular area — the scale ahead of the sustainability
And some hopes,
Whether you’re the platform providing the therapy or the software powering the therapist, entrepreneurs in this area should have their own version of the Hippocratic Oath. What I’d ask the investors in these companies is that they share the same values. Push for responsible growth and make sure patients are well-served. Realize that when you look at stats that involve quality of customer interactions, drug prescriptions, etc you’re talking about real people, not just percentages. And perhaps most essential, have a plan for what happens if the company doesn’t succeed. What does client offboarding look like, how long would it take and how much would it cost?
This concept is top of mind for me because we are now seeing the potential for AI products to change the quality and economies of service for addiction and therapy once again. As a recent WSJ article highlights, “When There’s No School Counselor, There’s a Bot,” and one particular company trying to solve for a startling coverage gap in adolescent mental health
The hybrid chatbot is now available to more than 4,500 public middle and high school students in nine districts across the country, many of which are in low-income and rural areas where mental-health services are lacking. The American School Counselor Association recommends schools employ at least one counselor for every 250 students, but says the national average is one counselor for every 376 students. And 17% of high schools don’t have a counselor, according to the Education Department.
This is great! And if you’re founding, building, or funding any of these companies please please please know that you are taking on a responsibility, not just an opportunity. I toast to your success and your efficacy. But know that your customers aren’t taking ‘startup risk,’ they just want some help.
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2025-03-04 09:22:44
Screendoor has now looked at more than 1,500 venture firms raising funds, backing roughly 1.5% of them, often as their first or second largest investor. When I’m scanning a pitch deck I’m basically looking to put it into one of two buckets – Traditional or Different.
“Traditional But Better” means they are basically running a playbook which doesn’t appear too different from existing firms – sourcing companies in categories considered ‘venture scale,’ with a portfolio model that has consistent stage and ownership targets, and ‘value add’ that mirrors the language other firms might use. Of course Screendoor has an eye towards new VCs with identities, backgrounds and networks which are ADDITIVE to the venture ecosystem to better serve founders, so while the structure of the playbook is duplicative, the people running the playbook aren’t – and that’s the key. In these cases we’re asking ourselves, can this individual/partnership execute a ‘known’ playbook better than incumbents, because it’s not very interesting to put people in business who are going to be Traditional But Average. Mediocre VCs get wealthy themselves but they won’t make money for their LPs, and are, at best, just a WITHDRAWALS ATM for average startups.
“Different & Excellent” equates to something that doesn’t exactly look like other VCs. Could be pinning their thesis on a category of technology or type of founder that isn’t yet understood by the investment community. Or contrarian in the number of companies and/or dollars invested per company compared to their peers. Maybe even a strong POV on what value they can add that isn’t typically available to early stage founders. These firms aren’t carbon copies of anything else out there. In fact, they probably aren’t generally replicable. But they take advantage of their unique founding partners, very often the type of people who would reject – or not get hired by – ‘traditional VCs.’ Here we have to torture the models to really understand the quantitative sensitivities around expected performance. And how quickly the firm can process new information and adjust if portions of their hypothesis need tuning once in market. But we’re interested in taking this risk when the person and opportunity warrants it.
If you’re a VC raising your first fund, and you think you fit either of these descriptions, please let us know. I could even ask you directly which one of these you think you are and why.
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