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writings January 2026 2026 themes ME 2.0, essentially working?, manufacturing cool, IRL FR, and power density read here December 2025 best of 2025 the readings & writings read here October 2025 2nd-hand insights passed along learnings are like hand-me-down clothes read here August 2025 chobani on my jeans becoming my cultural diet and what it means for founders read here June 2025 y2 “self”, obsessive thinking, punching upwards, and not getting lost in the sauce read here May 2025 chewing on a running list of random things, trends and notes read here April 2025 pre-traction thoughts on legitimate ways to display traction early read here January 2025 on curiosity the underrated skill of not worrying about sounding dumb and just being curious read here November 2024 the prepared mind thoughts on generalist v.s. specialist investing read here November 2024 rigorous thinking "what do you think?" there isn’t a day that goes by when one of the GPs at my firm doesn’t ask me this question. read here September 2024 on identity capital more than ever, young people are asking themselves who am I? you already know what you’ve experienced; start defining it. read here July 2024 first calls how I run every first call with a founder. read here April 2024 what I wish I knew my first month in venture the mistakes I made and advice from other young investors. read here March 2024 my tech stack the tools I use every day and the ways I use them. read here January 2024 betting on unseen forces the formative experiences of founders and how they're key factors in forming an outlier. read here January 2024 rejection i’ve spent a fair amount of my life as a young person facing rejection. read here

< Back on identity capital September 2024 more than ever, young people are asking themselves who am I? you already know what you’ve experienced; start defining it. For those of you who don’t know, I spent the last year living in Mid-Missouri. It was one of the most confusing and challenging times of my life to date (and trust me, I’ve had quite a few of those). I spent a lot of time alone, working, cooking, and yoga-ing. Despite the mundane, what came out of my year in Missouri was one of the richest opportunities of my life. The time to truly reflect on who I want to be and the experiences I want to have in the future. Defining Identity Captial Earlier this year, I finished the book The Defining Decade by Meg Jay, Ph.D . It felt like, for the first time, I stopped asking myself, “What am I doing in Missouri?” and started framing the experience as a way for me to build something called identity capital. Throughout the book, Dr. Jay asserts that who we are is built over time, piece-by-piece, by the things in our personal and professional lives that we choose to develop. She describes these as “investments that we make in ourselves, the things we do well enough, or long enough, that they become a part of who we are.” The longer I felt stuck in my current geography, the more it began to shape who I was becoming. What initially seemed ordinary and boring gradually turned into an unexpectedly interesting experience. Living in Missouri became an opportunity for me to invest in myself, engage with a population in the US that I hadn’t interacted with before, gain new perspectives on the investing ecosystem, and apply principles in my job that investors in the Midwest previously overlooked. I was building identity capital. Inflection Points When I began reflecting on building identity capital, it led me to think about the past moments in which that capital was previously built. I distilled both circumstantial and opportunistic moments into what I believe were times of major identity capital building. I grew up in a small town in the Pacific Northwest. My mom was a stay-at-home mother who worked weekend jobs, and my father was a public school principal. I attended a Title 1 high school where 15.8% of my classmates were homeless, and 8 out of 60 students who were in my graduating class attended a 4-year university. At 16, I started working two jobs each summer to begin saving for college. This trend continued throughout my college years, where I worked 80–100 hours a week in the summers, juggling an internship and waitressing at two different restaurants. Plain hard work that afforded me the opportunity of education and travel. In college, I spent two + months studying in Spain, where I worked at a startup where no one spoke English, and many of my coworkers were ex-pats from the former USSR. This environment allowed me to be unabashedly curious while building relationships in a foreign language. Of course, I’m adding the “year in MO” to my running list. Currently, most of my identity capital moments were derived from the circumstantial. (Ex. born to a working-class family, working because I had no savings, and traveling because I did). These moments are neither net negative nor net positive but moments of inflection in who I am. The next step is creating more of these moments through situations I choose to put myself in with the purpose of building identity capital, no matter how uninteresting they may initially be. (Ex. moving to the Midwest for school) Piece by Piece What’s beautiful about identity capital is that it doesn’t always require substantial resources or unique opportunities. It is free to create and can be built through everyday actions — reading books, exploring new places, trying different foods, or engaging in diverse conversations. Personal identity capital is built through your own active development alongside the collective and others’ social capital/relationships, helping you move forward. A fantastic example of this is founder Andrew Rea ’s blog titled How We Got Investor Intros . Throughout the blog, Andrew talks about how he and his co-founder’s ability to get intros was a direct result of 4 to 5 years of putting themselves in a position to build their company (i.e., 4 to 5 YEARS of building the identity capital needed to do so!). Andrew breaks down his and his co-founder’s origins, careers, and network that allowed them to successfully raise. Their identity capital was ultimately “exchanged” for fundraising dollars and a chance to build their company. Source Adopted from: Côté and Levine (2002) It’s this intersection of identity capital and social capital (our own and others) that allows already great people to build something exceptional. Final Thoughts As a young person, it’s easy to feel like you’re floating in the abyss, unsure of which direction will lead you where you want to go. I’ve found that by reframing everyday situations as opportunities to build identity capital, you can start to design a life that is interesting. My year in Missouri provided a chance for deep reflection and helped me start crafting my life around what I found was most important to me (family, friends, global citizenship, etc.) After leaving Missouri in late May, I spent 10 weeks backpacking and working in Europe and have now settled into a new apartment in Chicago. None of these opportunities would have been remotely possible without my prioritization of building identity capital through my past, current, and future circumstances. I am beaming with pride that I formed these experiences, and I sincerely believe that other young people can as well. You know more than anyone what your life has been like. Think about it. Spend time reflecting on what your inflection points are and what you’re doing now to build the experiences you want to have in the future. Previous Next

< Back the prepared mind November 2024 thoughts on generalist v.s. specialist investing Over the last decade, a majority of Venture Capital firms have chosen to define their identities through focused investment theses. As a result, two patterns have emerged: some firms have adopted a generalist approach, spreading investments across sectors, while others have doubled down on specific industries, seeking an edge in areas of deep expertise. So, which is better? The following essay dives into generalist and specialist strategies through an examination of their advantages, disadvantages, and adaptability across different market conditions and investment stages. The Case for the Generalist There are a variety of distinct advantages to being a generalist investor. These advantages can be synthesized into three categories: flexibility, broad knowledge, and access to outliers. Flexibility in investing is one of the most important advantages a generalist investor has over a specialist. Industries, themes, and trends are constantly changing and incredibly unpredictable. By being unconstrained in the industries, verticals, etc., where you can invest as a generalist, you are better suited to invest in the areas where opportunity is emerging. As Will Robins put it in his essay Why generalist investors will always win , “The eternal relevance of generalism in venture comes down to two simple and easy-to-prove facts: (1) Revolutionary tech companies are thematically unpredictable, and (2) transcendent founder talent is still needed even in the most fruitful spaces.” Generalist investors are also more immune to the ebbs and flows of different market conditions. For example, in a high interest-rate environment, a generalist may stay clear of industries negatively impacted or double down on a founder they believe can weather the storm. Specialist investors are often constrained to invest in their chosen vertical regardless of market conditions. A specialist’s capital deployment strategies are limited in flexibility, making it more challenging to adapt to market cycles. The advantages of being a generalist investor extend beyond their innate flexibility and into the scope of their knowledge. Being a generalist does not equate to being a lazy or uninformed thinker; it’s the opposite. Generalists have a broad knowledge source to pull from and can often pull together disparate themes and trends into unique insights because of their exposure to such a breadth of industries. In other words, generalist investors usually know little about a lot. It makes them uniquely positioned to deploy capital in areas where they can see opportunities, patterns, and use cases as they emerge across industries. Navigating uncertain times is generally more challenging for a specialist who draws from a narrow but deep knowledge pool. The final point of advantage for a generalist is access to outliers. The pool of investable opportunities is much more extensive for a generalist investor than a specialist. With fewer constraints, generalists have a larger pool of selection that, in theory, increases their probability of picking a winner. Specialists are expected to hit the same amount of bullseyes on a much smaller target. The Case for the Specialist Specialist investors move quickly; they know what they want and where areas of opportunity lie, bringing radical efficiency to their deal flow. A vital advantage of the specialists is their knowledge. Many specialists have spent years operating within their specified investment verticals. Conviction is high within these selected industries, and they quickly make investment decisions. A specialist knows previous market trends and cycles and who has “been there, done that.” The narrow but profound knowledge a specialist has unlocks the ability of the investor to ask the right questions and be efficient in their dealmaking process. A generalist often cannot get “in the weeds” as quickly as a specialist, leaving them reviewing deals slower in unfamiliar markets and relying on outsider insights. Outside of industry/vertical knowledge, specialist networks provide a considerable advantage to their portfolio companies. The concentrated networks allow specialists to give their founders highly relevant resources, filtered insights, and arguably the best intros to early customers, hires, or other investors. Compared to a generalist, who may be able to offer a portfolio company similar resources, but the network/connection may be different from what the founder wanted. In their specified industry, specialists have a clear case for why they deserve allocations on a founder's cap table. Specialists can point to a clear knowledge base, network, and examples of where they’ve added sector-specific value to their previously invested companies. Examples can be the difference between getting allocation in a round or not; without curated offerings, a founder may choose to add a specialist fund to their cap table over a generalist if there are no specialists in the round. The Superior Strategy Specialist investors have superior access to curated deal flow, a shorter decision timeline, and more targeted networks. It seems logical that they would outperform the generalists equipped with broader but less specialized networks and knowledge. Statistically, though, that is not the case. In 2022, PitchBook analyzed the performance of 451 VC funds across the US with vintages from 1995 to 2015 and found no significant performance differences between generalist and specialist funds after accounting for general market and industry performance. The coefficients (betas) for targeted and specialist funds reflected expected differences in average IRR relative to the generalist baseline. Still, neither significantly differed from zero, indicating performance across fund types once market conditions and fund size were considered. The report concluded that LPs "should be skeptical of any claims that industry specialization leads to superior performance.” While Pitchbook’s findings showed no significant difference in performance between specialist and generalist funds, other studies have gotten more granular on how the specific advantages of each strategy play out. Economists Paul Gompers, Anna Kovner, and Josh Lerner analyzed the performance of over 800 venture capital firms and more than 3,500 individual venture capitalists by examining the IPO and acquisition success rates of over 11,000 portfolio companies between 1975 and 2003. Their findings revealed a strong correlation between specialization and success. Specialist firms outperformed their generalist counterparts, mainly when individual venture capitalists specialize in a single industry. Generalist firms, conversely, showed poorer performance in cross-industry capital allocation and were less effective in selecting profitable investments within sectors. However, generalist firms performed equally as well as their hyper-specialized counterparts when individual investors within the generalist firm were specialists. In other words, the hyper-specialists win in equal proportion to generalist firms with partners who have some specialized perspectives. This is why Tier 1 funds have remained generalists over time. Even as fund sizes have ballooned, these firms recognized that staying generalist thematically while building small, focused teams of specialized investors could continue to drive outlier returns at any stage. Accel coined this trend as the “Prepared mind” approach, an investment method inspired by the Louis Pasteur quote, “ chance only favors the prepared mind.” Accel emphasizes proactive exploration and thorough industry research, enabling the partners at the firm to identify and dig into specific categories, tap into network insights, and track emerging trends to spot potential leaders. By the time Accel invests, the team has developed a firm conviction and alignment with the entrepreneurs, replicating a specialist fund's speed, network, and confidence without becoming one. Does Stage Matter? In 2011, Economists Sharon Matusik and Markus Fitza conducted an in-depth analysis of the performance effects of diversification in VC, focusing on 4,583 VC firms and nearly 7,500 VC firm-year observations. The researchers used data from 1960 to 2000 to examine how diversification (defined as the depth of knowledge within the firm) impacts VC performance, particularly in uncertain environments. The findings revealed a U-shaped relationship between diversification and performance. VC firms achieved higher success rates with either low or high levels of diversification, while moderate levels of diversification resulted in poorer performance. This means a super-specialized specialist performed equally as well as a generalist firm composed of investors with diversified knowledge, and those in the middle performed the worst. Matusik and Fitza also found that flexibility is crucial for both specialist and generalist funds, particularly regarding early-stage investments. High portfolio diversification in early-stage investing generated the highest IPO success rate at over 40%, with more flexibility in the early stages and more success than their less adaptable counterparts. In early-stage investments, high diversification (i.e., being more generalist) proved advantageous, allowing firms to adapt to market cycles. For late-stage investments, the impact of diversification on performance was less significant. They also found that firms co-invested with other VCs could achieve similar performance outcomes without needing high diversification, as co-investors contributed additional industry knowledge. Performance results can be manufactured by partnering with a mix of specialist and generalist investors. For this reason, founders are often encouraged to diversify their cap tables to include a mix of generalist investors, who bring wide networks and broad industry knowledge, alongside specialist investors, who offer targeted insights and valuable, niche-specific connections. Why We Choose the Generalist Path At Redbud VC, we have seen the advantages of a generalist approach flourish at the earliest stages. By choosing to be a generalist, we’re keeping our eyes open for the best talent, building solutions wherever they might emerge, whether in fintech, proptech, sustainability, or an area not yet fully defined. It’s not just about being flexible; it’s about having the curiosity and humility to say that the next billion-dollar company might come from a place we hadn’t anticipated. The advantages of being a generalist at the early stages are abundantly clear. The ability for us to have exposure to a comprehensive set of founders building in diverse industries helps increase the chances we invest in a generational company. As a small fund, we leverage the networks and expertise of each of our team members to help us replicate some of the advantages that a specialist firm has. Where we can’t, we help our portfolio companies source funds that can be the specialists on their cap tables. Given our ability to be adaptable as generalists, our team explores different industries or verticals where we want to find opportunities to build or deploy capital. For example, digging into challenges community banks face led to our investment in Braid’s Pre-Seed Round , and investigating sleepy areas in prop-tech led us to incubate Village. As we work towards building a VC brand from Middle America, Redbud is adopting our approach to investing with a prepared mind, equipping us to recognize and support outlier founders in whatever they are building. Previous Next

< Back best of 2025 December 2025 the readings & writings Growing up, the monthly arrival of the print version of Time Magazine was always something I looked forward to. Checking the mail and seeing that iconic red border, Time was a consistent part of my young adult reading. It sparked my love for print media, and I believe it is what made me obsessed with the concept of a "best list." I especially looked forward to the “special editions,” like Time 's Person of the Year (now a piece of American iconography), Invention of the Year, and Photo of the Year. I’ll share more reflections on 2025 soon, but I wanted to start with the readings (essays and books) that stood out most. This list captures my personal bests from throughout the year. What I love about revisiting the work that carried the most weight, sparked the most joy, or taught me something lasting is how it reinforces the pursuit of knowledge as a very human act. It keeps my curiosity in motion and compounds in ways that are hard to predict, but easy to feel. So without further ado...the bests readings and writings throughout the year. Essays American Vulcan by Jeremy Stern A portrait of one of the most quietly polarizing figures in tech & defense, Palmer Lucky. I think it’s easy to write off those who operate best on the fringes of a spectrum, and Palmer seems to only operate on the fringes. Stern details Palmer's life in distinct sections, from a homeschooled tinkerer to the founder of Oculus to the founder of Anduril, the largest manufacturer of autonomous systems for security & defense. It’s a rare snapshot into the fringes on which Palmer operates: work, life, family, media, and politics. “I’m maybe not the crusader for truth that people imagine. I am a crusader for vengeance. And if my vengeance can best be served by covering up the crimes of those who have wronged me, then I’ll probably do that. ” “Remember that I’m not a journalist,” he continued. “I don’t have to be objective. I don’t have to be neutral. I can be a propagandist. ” Curious Times by Aravind Srinivas Ages are defined by work, but what happens in the AI age, where knowledge work is slowly being eradicated? Srinivas poses this question that many of us are asking in different ways and answers it quite optimistically: learning will replace knowledge as our dominant economic output. The ability to pose the best questions, learn, and move quickly will be the human elements that define the AI age. Imo, the future belongs to the curious. :) “ Each time the dominant form of work has changed, prosperity has followed those who re-skilled and adapted. Success went to societies that prioritized immediate learning for affected workers and systems of education for their upcoming generations.” Successful People by Sam Altman A small post from Altman’s blog written over 13 years ago. I believe it’s a small window into Altman’s mindset as he builds OpenAI. “…the most successful founders do not set out to create companies. They are on a mission to create something closer to a religion.” The Art of Understanding What's Going On by Tina He Tina He from Pace Capital is a cut above the rest, and her blog, Fake Pixels, is one of my favorites in the industry. We like to think we understand incentives, truths, and behavior, yet we’re often chasing narratives (especially in AI companies) rather than mechanics. A really refreshing read and clear breakdown of how to actually understand a company by examining its underlying incentives, not the story it wants to tell. “Spotting the gap between surface narratives and hidden incentives helps clarify how these cycles play out and reveals the second- and third-order effects that are often overlooked when abstracting "AI" as a universal fix.” Books The Young VC’s Handbook compiled by Sakib Jamil If you’re a jr. investor and we’ve chatted in the last year, odds are I’ve shown you my battered/well-loved copy of the Young VC’s Handbook. It's the only book that gives you actual tactical advice on how to do your job as an investor, and I reference it incredibly often. Thinking in Bets by Anne Duke A rec from Robbie at mtf . I was initially worried I was about to get knee-deep in some game theory, but what I got was an easy-to-digest guide to choices, biases, echo chambers, continuums, etc. I read this right after learning I’d passed on a deal that later had a16z lead a subsequent round, and I wish I’d read it sooner. I don’t know if that would have changed the outcome, but I do know my decision-making frameworks are a bit stronger now, thanks to Anne. 1491 by Charles C. Mann A pre-Columbian history of the Americas that I breezed through in a week. Mann challenges long-held assumptions, biases, and “facts” about the Americas, drawing on modern anthropological discoveries to dismantle much of the conventional narrative. The book is broken up into three parts: population, culture, and environment. Because this period is often glossed over (or entirely skipped) in K–12 American history curriculum, most of it was new to me and sent me down some good rabbit holes. The Creative Act: A Way of Being by Rick Rubin I think a Creative Act has been at the top of countless best-seller lists and everyone’s recommendations since its release in 2023. I’m always drawn to books written by people at the very top of their craft, and Rick Rubin unquestionably qualifies. The book is a quiet, grounding reminder that creativity isn’t a credential or a talent, it’s a way of paying attention to what's around you. You don’t need to be a creative to be creative. Previous Next

< Back 2026 themes January 2026 ME 2.0, essentially working?, manufacturing cool, IRL FR, and power density In May, I found myself wanting a place to stick my thoughts. I wasn’t particularly interested in the public forums of Twitter/X or LinkedIn, and while I do a lot of long-form writing, not every idea is ready for that format. I decided to create “chewing on,” a running blog you can read here , which I update periodically with reflections, observations, and opinions. (It is much, much less polished than the below.) Throughout this year, I pulled ideas from chewing on, along with a few others, and shaped them into the themes below. These are the areas where I’ll be spending time in 2026: ME 2.0 Where once our memories lived in scattered notes, photo rolls, and half-recalled ChatGPT threads, personal intelligence systems now promise something more ambitious: continuity. Not just storage, but understanding. Context layered over time, what I’ve read, chosen, forgotten, or avoided, forming a living map of preference and experience. As models move from reactive assistants to ambient companions, the burden of articulation begins to fall away. No more precise prompting. No more explaining what I need, again and again. Instead, systems already know, anticipating intent through accumulated history, emotional signals, and behavioral patterns. A memory becomes less archival and more interpretive. But this raises a deeper question about the authorship of the self. If an external system remembers more faithfully than I do, tracking motivations, inconsistencies, and growth, where does “my” memory end and delegated cognition begin? Does ME 2.0 sharpen identity by reflecting it to us, or subtly rewrite it by deciding what is worth remembering at all? synthesizing the decentralized ( klienklienklien ) essentially working? As AI absorbs more task-level knowledge work, productivity increasingly favors the curious over the credentialed. In this new frame, essential work looks less like execution and more like orchestration. The most valuable operators will sit above swarms of agentic workflows, designing, delegating, and supervising chains of autonomous systems spanning research, operations, and decision-making. Work becomes the management of intent, not the completion of tasks. As agentic tools continue to proliferate across verticals, a second-order layer inevitably emerges: systems to coordinate the systems . Platforms that aggregate, govern, and scale agents–deciding which models act, when they act, and how their outputs compound. Control shifts from individual tools to operating layers. But what becomes of the balance of labor & leverage? When “doing the work” means directing intelligence rather than supplying it, who remains essential, and by what measure? Does productivity accrue to those who command the agents, or to those who design the rules by which they operate? manufacturing cool Can cool be manufactured, or only discovered? For decades, products earned cultural relevance through proximity: who used them, where they appeared, and how slowly they spread. Today, distribution itself has become a creative act. Narrative, placement, and algorithmic amplification now shape what enters the zeitgeist just as much as the product does. As audiences fragment and attention becomes programmable, “cool” is becoming manufacturable. Startups no longer rely on organic adoption alone; they can refine distribution with the same rigor once reserved for product design: aesthetic coherence, influencer adjacency, and cultural timing are levers. This reframes GTM as a form of cultural production (i.e., consumers' cultural diets ). Rather than building for users and hoping for resonance, companies can script relevance, testing, and iterating on taste at scale . Cool becomes less about authenticity in the abstract and more about believability within a specific cultural moment. copy + paste ( charli's substack ) IRL FR There’s a renewed seriousness to the connections, communities, and conversations happening in real life. After years of over-indexing in digital interactions, the marginal utility of online communities is flattening. What’s emerging is demand for IRL FR (in real life, for real). The long tail of Covid-era isolation still lingers, and we know how to connect digitally, but we’re less practiced at reentering community. People want to show up, but there’s a lack of infrastructure to make it easy. This creates space for platforms that don’t compete with IRL interaction, but enable it, tools that aggregate intent, reduce social friction, and make IRL legible and repeatable. The next layer of platforms will scaffold IRL connections. They may sit at the coordination layer owning discovery, scheduling, and identity across offline experiences or at the brand layer, where IRL presence compounds loyalty and LTV. power density As generative AI scales, intelligence is no longer abstract; it is physical. Models, like humans, demand electricity, water, cooling, and land. What once felt like an infinite expansion of software is increasingly constrained by grids, substations, and energy contracts. This has shifted the advantage away from algorithms alone and toward infrastructure fluency. The race to build larger models quietly becomes a race to secure power, driving new data center clusters, stressing local grids, and reshaping how and where intelligence is produced. In response, the stack had begun to adapt. Purpose-built accelerators promise more intelligence per watt. Workloads have been moved across time zones to follow renewable supply. Other projects, like behind-the-meter capacity, private microgrids, and eventually small-scale nuclear, could reshape what “cloud” even means. But how do these tradeoffs resolve? Do we optimize for efficiency, locality, or control? Does access to energy become the true limiter of who gets to build, deploy, and scale the next generation of AI? hungry hungry hippos circa 2025 ( kai williams ) ___ If you are a) building in any of the areas or b) just want to talk about any of these themes, drop me a line at maria[at]redbud[dot]vc Previous Next

all of my favorite readings: blogs, books, and blurbs ​ readings some of my favorite blogs, books, and blurbs thinking fast start right before you get eaten by the bear how things get done the great mental models: volume one rigorous thinking: no lazy thinking cultural curiosity same wavelength ‘ugh, i’m so busy’: a status symbol for our time the strength of being misunderstood successful people "insecure vibes" are a self-fulfilling prophecy corporate ozempic the socially-conscious mean girl the META trending trends: 2024 you don't need to document everything the virtue of vice how we built the internet american vulcan discipline + process 15 principles for managing up finding the courage to be disliked how to become insanely well-connected vc what they don’t tell you about making it in vc a few things I’ve learned about brand building in venture capital “the grass is always greener”…aka the circle of envy the puritans of venture capital always run an auction

the quick on my background: life, early career, hobbies, etc. maria heyen. on me: I hail from astoria, or where my childhood was spent on the cold beaches, visiting farmers markets, and riding bikes around the cul-de-sac. I moved to the midwest for school and lived in nebraska for 4+ years where I studied international business and studied in barcelona for 3 months where I worked at a proptech startup. TDLR: moved to missouri, backpacked europe, and now live in chicago. things I'm doing: learning/improving my spanish tutoring with tutoring chicago (here ) cooking my way though trader joes clifton strengths: competition, arranger, individualization, significance, input personal portfolio : maazah - middle eastern inspired sauces & dips

< Back my tech stack March 2024 the tools I use every day and the ways I use them. About a year ago, when I began transitioning into full-time employment and venture, I realized I had a steep learning curve ahead of me with adopting new tech workflows. I quickly discovered that Google Docs and Gmail weren’t going to cut it, nor did I really know where to start when it came to tech. :( Working at a small firm means I've had the opportunity to build my own “tech stack.” Over the past few months, I took some of the firm-wide software and added a few of my own tools to build a tech stack that houses all of my work and, frankly, my life. :) These tools allow me to clearly communicate, align priorities, execute, and stay organized. Below is the current lineup/roster of tools that I use every single day and my current favorite use cases and features. Hopefully, you find something that you’ll enjoy. Notion https://www.notion.so/product • $0-$15 per user per month Notion is the most used (and favorite) tool in my tech stack. It is where the big things/initiatives/projects live at work, and it serves as the hub of my personal life as well. Below are 2 of my favorite ways I use Notion. Work: Weekly Standup Agendas Every week, I have a standup with one of the GPs at the fund I work at. It is my responsibility to run through what happened the previous week and share current priorities. Below is a snapshot of the notion view Work: Personal CRM Part of being a VC is meeting a lot of other VCs, and it’s always hard to keep track of who invests in what. I love to meet new people, and my favorite investors always Are hyper-focused on sending deals that meet my firm's thesis Remember something about me/that I enjoy :) I’m getting better at this (still a work in progress), but tracking all the little details in Notion has helped me be more intentional about meetings and deal sharing. Superhuman https://superhuman.com/ • $30 per user per month If you’re not using Superhuman, you should be. Prior to Superhuman, I felt like emails were always getting “lost in the sauce,” and I was always frantically missing something. Since using Superhuman, I haven’t missed an email; it’s cut down my time in my inbox by 75%, and I am able to triage my inbox in the most efficient manner. My favorite features of Superhuman are split inboxes , keyboard shortcuts , snippets , and read statuses . Notion Calendar (frm. Cron) https://www.notion.so/product/calendar • $0 with Notion subscription Calendar management is still a work in progress for me, but Notion Calendar has been an absolute lifesaver. I used to be a die-hard calendly user but had a hard time blocking calls. I found I was wasting a TON of time in random 30 breaks between calls. I use Notion Calendar to send personalized meeting times in time blocks where I am open/want to take calls. It has helped me stack my calls better, avoid calendly reverse engineering/rebooking, and make the most of my daytime. Flow Club https://www.flow.club/ • 7-day free trial, then $33.33/month billed annually or $40/month Flow Club is expensive, but the results/productivity are worth every penny. Flow Club facilitates virtual co-working sessions where you can drop in and get things done! I usually do 1–2 flows per day so that I have dedicated time to work on the tasks that have no end or stuff I've been actively avoiding. It’s great to have small and welcoming groups of accountability partners. Previous Next

< Back rigorous thinking November 2024 "what do you think?" there isn’t a day that goes by when one of the GPs at my firm doesn’t ask me this question. "What do you think?" There isn’t a day that goes by when one of the GPs at my firm doesn’t ask me this question, and honestly, I used to hate it. I’m often bad at articulating them clearly, not because I don't have opinions. It’s not that I don’t have ideas about a company or initiative we're working on. My opinions were usually a mix of gut feelings and bias, but I hadn’t dug into why I thought a certain way. I’d never stopped to ask myself, "What do I think?" Over time, I noticed a pattern in my responses to this question. I’d ramble about my general impressions of a company when asked what I thought. I’d sprinkle in details from founder conversations or some diligence I’d done, but mostly, I’d speak in broad strokes, unstructured thoughts that even I struggled to make sense of. Unsurprisingly, this approach was not only unconvincing but often left me more confused about my perspective (ironic, right?) Over the past few months, I’ve started diving into becoming a more rigorous thinker. I’m sure my approach will evolve, but I wanted to capture how I’m beginning to build a more robust framework for thinking through decisions. In startups and VC, it’s easy and often incentivized to ignore truth for speed in the short term. However, you can move faster and make better decisions by developing structured pathways for clear thinking. One of the best ways to become a rigorous thinker is using mental models. This concept isn’t new, and it’s been discussed by countless others for centuries, but I wanted to share how I’m applying two models, Circle of Competence and 2nd Order Thinking, to build more rigor in my thinking. Circle of Competence: A circle of competence is an area where you have knowledge or expertise. When you operate within your circle of competence, you have a competitive edge because you understand the history, trends, attitudes, and behaviors within that space. Over time, you can expand this circle, strengthening your understanding and intuition. Shane Parrish describes it well in The Great Mental Models : "When we are within a circle of competence, we know what we don't know. We can make decisions quickly and accurately, define problems precisely, and identify additional information we need. We have a proven track record and can adapt our language to different contexts, zooming in and out seamlessly on what is knowable." For a long time, I struggled with the concept of a circle of competence, often dismissing it by thinking I didn’t have enough experience to be competent in any area. And while I may not be Mark Andreessen (not close…yet), I’ve realized that I do have emerging circles of competence rooted in my own life experiences. Right now, these circles are shaped by the industries that influenced me growing up, the work of the adults around me, and my background as a student. Circles of competence are built gradually and adapt as environments and dynamics shift. To establish and maintain these circles, you need a desire to learn, a commitment to monitor and test your assumptions, and regular feedback from those outside your circle. As I work to build a circle of competence in venture capital, I'm consistently putting myself in situations where I can learn from those with much more experience in the industry. Understanding how they think, combined with my own experiences, time, and practice, is helping me improve at assessing companies—and, hopefully, becoming a better investor. It’s not about being written or being wrong. It’s about having exposure to multiple ways of thinking and understanding the context and nuance around them. 2nd Order Thinking: Second-order thinking is about pushing your mind beyond an action's immediate cause and effect. It’s the ability to consider the second and third layers of consequences resulting from a single decision. Take dinner, for example. I have two options if I'm hungry: make a balanced meal at home or grab Raising Cane’s down the street. The first cause and effect for each is straightforward: the home-cooked meal will not be satisfying taste-wise, while Raising Cane’s satisfies my cravings because I love tenders and Cane’s sauce more than anything else! Based on first-order thinking, Raising Cane’s is the obvious choice. But if I think in the second and third layers, things look different. Eating at home may not fulfill all my cravings, but I’ll nourish my body correctly, sleep better, and have fuel for tomorrow’s workout. If I choose Raising Cane’s, I’ll enjoy the meal immediately, but my tummy will inevitably hurt, I’ll have inadequate nutrients for my workout, and I'll feel sluggish all evening. First-order thinking often favors short-term decisions, while second-order thinking encourages us to consider the longer-term consequences of our actions. Second-order thinking can sometimes slow decision-making as people evaluate all possible adverse outcomes. I use it as a tool to make more informed choices without expecting to foresee every result. It’s about challenging myself to think more deeply about the effects of my decisions. Second-order thinking is a critical tool when evaluating companies as an investor, where there’s a constant stream of companies to assess. Thinking through the second and third outcomes of my choices helps me look beyond the immediate attraction of a company or its initial traction to consider how it aligns with our firm’s investment goals and thesis. Second-order thinking also guides my decision-making when choosing which companies to spend more time on or push forward in the pipeline. It keeps me mindful of my blind spots and helps me consider the potential downstream effects of my choices. Conclusion: Building a more rigorous approach to decision-making has changed how I handle the dreaded “What do you think?” question. Using tools like the mental models above, I’ve gone from rambling through gut reactions to articulating clearer, more thoughtful perspectives. I’m learning to dig into why I think a certain way and what effects my decisions have in the long term. While there’s still much more to learn, these mental models are helping me tackle decisions with greater confidence and thought. Previous Next

< Back betting on unseen forces January 2024 the formative experiences of founders and how they're key factors in forming an outlier. In this essay, we explore the formative experiences of the founders in the Redbud VC portfolio and why we believe these moments, often found at the intersection of circumstances and opportunities, are critical in a founder’s journey to success and key factors in forming an outlier. In 2014, Marc Andreessen sat down at Stanford University to candidly share what his firm looks for in founders, “The venture capital business is a 100% game of outliers- it’s an extreme exception.” Simple as that: great founders are outliers. Chasing these outliers has since become a common trend in Venture Capital as firms boast and argue what makes them the best at choosing who has these “extreme exceptions.” The irony is that no one truly knows, but as VCs, we do our best to build reliable frameworks around who to choose, and we wait, on average, 7–10 years to see if our assumptions are validated and if we successfully chose the outlier. Emerging frameworks designed to capture outliers fall into a few categories: education, geographic area, professional experience, motivational factors, personality traits, network, and challenges. Many VCs rely on “pattern recognition” in those areas, i.e., checking boxes on key points such as prestige or pedigree. The dependence on attempting to replicate previous formulas for success has arguably led many VCs to invest only in certain areas or within specific groups, e.g., Ivy League alumni or ex-FAANG. VCs tend to place bets where opportunity and privilege are plentiful; often, a belief exists that entrepreneurial success is directly correlated. In other words, although VCs are driven to search for outliers, they end up falling into the trap of pattern matching to the median. At Redbud VC, we are betting that entrepreneurial talent is evenly distributed even though opportunity is not , an idea that is not original in thought but is in practice. Education and Pedigree Education is the easiest box to check for VCs, as there is clear data on how founders from top-tier universities have the resources and networks that are robust enough to support them as opportunity comes. Recent PitchBook data showcases that the vast majority of VCs prioritize founder and executive team pedigree first when evaluating an investment opportunity. In 2022, McKinsey conducted a study on commonalities between the founders of Unicorn companies, finding that 95% of unicorn founders completed an academic degree and over 70% have an advanced degree such as a master’s, MBA, or PhD. Educational statistics have led VCs to deploy a third of their capital in their university alma mater when 40% of the VC industry is dominated by Harvard and Stanford alumni. Acceptance and completion of a higher educational program is a statically strong signal towards entrepreneurial success but is once again a pattern, not an outlier. VCs tend to place bets where opportunity and privilege are plentiful; often, a belief exists that entrepreneurial success is directly correlated. We asked the founders in our portfolio to share details about their educational background and significant experiences or learnings that happened throughout that time. One founder shared, “ I was a terrible student in undergrad, especially the first 2 years. I had to take a lot of classes over and had to fill my final semester with over 30 credits of classes to boost my GPA. It taught me to manage my time and push myself to work harder than I had ever worked before.” Another founder shared, “ I worked as an auxiliary campus police officer while at [University]. One of my duties was to stand at an intersection for 8–10 hours directing traffic on home football game days. A lot of days it rained or snowed, and I’d just be out there completely soaked, freezing my ass off. I learned a lot about toughing out the unpleasant parts to get to the other side.” A common thread across many responses in this category was remembering a specific experience that shaped the lens through which they approach being a founder rather than a person or connection. These small but defining moments early on have the biggest influence (or impact) on present-day principals. The prevailing belief that prestigious universities serve as reliable predictors of entrepreneurial success is flawed. While a substantial number of founders emerge from institutions like Harvard and Stanford, this correlation does not guarantee outlier achievements. In fact, founders who studied or worked at the University of Cincinnati are 3.3x more likely to achieve unicorn status than other founders. Admission to elite universities is often influenced by socioeconomic privilege, family networks, academic coaching, and other factors unrelated to entrepreneurial talent. The bias toward graduates from prestigious colleges triggers an influx of capital into said founders, creating an inaccurate perception of reduced risk. In other words, as a founder, having the “right” educational institution associated with you can erroneously signal safety to investors, perpetuating this cycle of bias. Professional Experience Professional experience is another key determinant of securing VC funding and evaluating founder backgrounds. Founder pitch decks often flex points of operational, technical, or prestigious work experience and are quantified by products shipped, revenue increased, etc. It’s hard for investors to ignore startups founded by ex-Meta, Twitter, Uber, or any top tech company talent. A founder’s professional experience undoubtedly contributes to a founder’s credibility , yet is not always directly correlated to quality. When speaking to our founders about key moments in their professional experiences that shaped them, many spoke about pivotal moments of opportunity: “ I spent 15 years as a civil engineer, eventually getting to a position normally occupied by people with 15+ years of experience more than me. I was really lucky; the companies I worked at needed someone organized, and I could step up; otherwise, no one in their right mind would hand a multibillion project to a 30-year-old.” Challenging moments of opportunity are essential to developing empathy for a problem. Another founder stated, “I was previously a Legal Officer at eBay, conducted due diligence at an angel investor group, analyzed the status of international contracts at the Court of Justice of the EU, worked at a community legal center, and have some law firm experience. My legal professional background absolutely equipped me to build the venture I founded, as it couldn’t exist without it.” Robust experiences with moments of opportunity often outweigh flashy company names or titles. At Redbud, we listen to these learnings and believe they can happen at any organization regardless of prestige. Geographical Influence Geographical influence is arguably the most explicit line drawn by investors — narratives about the coasts vs. Midwest and SF v.s. NY, etc., are a continuous topic of VC blog posts at all stages. It’s no secret that founders historically flourish in places like Silicon Valley, New York, Chicago, and other bustling urban hubs brimming with venture capital and abundant opportunity. A prime illustration of this phenomenon is when investors assess the “quality” of founders. Take, for instance, a founder hailing from the heart of San Francisco, a city synonymous with technological innovation. Investors instinctively place these founders higher on the scale of talented entrepreneurs. In stark contrast, investors may scrutinize a founder emerging from less tech-centric geography like Nebraska or Missouri and question, “What do they truly understand about being a startup founder?” Again, a seemingly inherent bias is in fact, the manifestation of pattern recognition rooted in geographical bias. Living in a traditionally overlooked area can instill unique traits in founders that are cultivated through the experience of building a company where there are limited examples of past success. In contrast to coastal cities with plentiful examples, opportunities, and blueprints for success, small, less VC-populated areas have the potential to breed founders who are grittier and more resilient. As one founder in our portfolio put it, “I and others frequently felt like we were alone on a remote island fighting for basic things that coastal startups enjoyed in abundance.” Resilience can be a formidable asset in the entrepreneurial world. It encourages founders to be resourceful, adaptable and focused on problem-solving. Founders from such overlooked areas often have a deeper connection with their local communities as they have had to first look locally for support and resources. “I was born and raised in the midwest and believe, after living on both the West Coast and East Coasts, there is definitely an aspect of community, helping your neighbor, and holding honesty and transparency that is deeply embedded in my approach to life, business, and people.” While building a company or hailing from an overlooked area can bring founders with strong traits and principles forward, the limits of said geography can restrict founders to operating within the confines of what they’ve seen. There often becomes a point where thinking outside of one’s community is discouraged, and founders retreat to the patterns of what has been locally “successful.” “[I’ve lived in] London/Ireland/Frankfurt/Lagos [and] living in multiple places made me realize how big the world is and how much opportunity there is however, there are (real but often over publicized) statistics surrounding my community who are always portrayed as ‘under’ served/estimated/funded so you’re mocked or actively discouraged for thinking big or outside the norm.” Founders often feel a tension between what they are striving to create and an existing mold of “success.” We believe providing these moments of exposure to our founders is important as they often prove to be essential learnings that deeply influence future decision-making and the shaping of an outlier. Exposure to top-tier ecosystems and thriving markets can push founders to think outside of the norm. Accessibility to examples of outlier founders can help others avoid mistakes, create relationships, and iterate alongside an individual who has done it before. More than one founder in our portfolio wrote about the moments that pushed them to embrace their strengths while simultaneously thinking big: “I have always had big goals for myself, and I knew that I’d eventually build something big on the world stage. I grew up in an environment that encouraged ambition (albeit, traditional). Having access to a variety of TV channels (specifically, [shows in the] US like Disney Channel — I’m serious!) and the internet made me be more extroverted and think bigger than most of my peers.” Exposure to diverse media, people, things, and places, no matter how big or small, is critical in a founder’s journey toward perspective. We believe providing these moments of exposure to our founders is important as they often prove to be essential learnings that deeply influence future decision-making and the shaping of an outlier. By recognizing how to nurture such experiences, Redbud is able to identify founders that would typically be overlooked if evaluated against an investor’s traditional framework for success. Motivating Factors The motivational factors that propel founders forward are the unseen catalysts of creating outliers and are unique to each founder. It’s difficult to dissect motivation and place it into distinctive categories. Unlike education with statistical ties to “founder success,” motivation cannot be statistically grouped, and therefore, it is difficult for investors to drive patterns and assumptions around it. When we spoke with our founders about what motivated them, some attributed defining moments in forming a “chip on their shoulder,” while some founders spoke of the circumstances that provided the privilege and opportunity for them to build a company. As we dissect the formative experiences of our portfolio founders, it becomes apparent that motivations are not just personal narratives but powerful drivers influencing the trajectory of their entrepreneurial journeys. One founder shared: “Being immigrant founders, our success impacts our visa status, intensifying our drive to excel. My motivation is also deeply rooted in Chinese familial values and my academic achievements. However, another chip comes from my passion for architecture.” The intertwining of visa status, familial values, and a passion for architecture forms a unique blend of motivations that extends beyond the conventional markers of success. It’s the blend of diverse and very real motivational factors that are the tipping point in propelling founders outside of the binary success and into outlier status. Another founder shared: “I am the underdog and have been told I always have had a chip on my shoulder. I love solving problems, and there are so many [customers] that I have come across where I have been able to solve their problems [through my company].” The motivation to solve problems and create a company where both customers and employees genuinely love doing business is deeply rooted in the founder’s identity as the “underdog.” A sense of challenge can be a powerful driver for founders, fueled by the times when they’ve been overlooked. Such heart has the potential to serve as fuel to break an existing mold, thought, or perception of success and prevent them from becoming disheartened. It’s the blend of diverse and very real motivational factors that are the tipping point in propelling founders outside of the binary success and into outlier status. The absence of a chip on the shoulder doesn’t diminish or lessen the potency of motivational factors. For instance, one founder with a stable family life was inspired by dissatisfaction with a predetermined career path. “No chip. I had a good family life. I have a supportive wife. I wouldn’t say that I faced any adversity other than the usual ‘that’s not how you do life’ unsolicited advice. I went to school thinking I was going to be a cubicle engineer my whole career, and after a while, it started to scare the hell out of me.” This revelation that life could become more than a routine ignited a spark, pushing this founder to break free from the expected and embrace the excitement of the unknown. Motivational factors are incredibly diverse in nature and collectively underscore a crucial point: the journey to outlier status is not solely paved with external markers of success. Instead, it is inspired by the deeply personal internal fires of passion, ambition, resilience, and a commitment to self-improvement. Recognizing and understanding these motivational forces is integral to Redbud VC’s approach. It informs our strategy in identifying founders with deeply rooted motivations regardless of the driving force. Conclusion Throughout our interviews with our portfolio founders, we found that the seemingly small moments often play much larger roles in a founder’s journey toward success. Thus, there is no neatly packaged pattern that can guarantee the manifestation of an outlier founder, nor is there a combination of factors that can be matched. While many VCs continue to align with inherently flawed frameworks to find outlier founders, we at Redbud look to our founders for context on their experiences. We understand the journey to success is not a linear trajectory attached to your alma mater, geographic area, professional exposure, motivational factors, etc.; instead, it emerges from a tapestry of life experiences that have the propensity to cultivate an outlier founder. Taking a note from Malcolm Gladwell’s book Outliers, we are betting that investing is about recognizing the unique blend of advantages, inheritances, and experiences that make each founder who they are. “In the end, the outlier is not an outlier at all; their success is a product of a web of critical elements deserving attention, understanding, and appreciation.” At Redbud, our commitment lies not in adhering to rigid patterns but in embracing the richness of individual stories and fostering the connections that propel outliers into existence. 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< Back rejection January 2024 i’ve spent a fair amount of my life as a young person facing rejection. I’ve spent a fair amount of my life as a young person facing rejection. As a child getting cut from sports teams, as a teen not making it into elite colleges, and as a young adult facing brutal internship/job passes, I am no stranger to the painful ache that rejection causes. I have a deep understanding of some of the long-standing effects tough rejections can have, and it’s hard not to recall times when I showed up at my best and met with what I deemed to be the “worst.” The complex and burdensome emotions that rejection can illicit are something that I spur in founders every day. I spend a large portion of my time as an investor rejecting founders, and being so familiar with the feelings myself, it is a dichotomy I’m learning to be comfortable with. I sit across the table from founders each day who have put EVERYTHING into their businesses, and 99% I follow up with an email on my firm passing on investment. There are a few reasons in particular why I wanted to write about rejection as my first “soapbox.” #1 I want founders to know that no matter how quickly calls go — I can feel the emotion, time, energy, and capital that they have put into their business and that even though I say no often, I don’t say it lightly. #2 VCs themselves are a business, and that’s not talked about enough. We care about founders, and we deeply want them to succeed, but ultimately, our duty is to our investors called LP’s whom we seek to drive returns for (more on this in the future). No’s are said for a variety of reasons, and most of the time, No’s can be traced back to more arbitrary reasons and things that founders can’t control, such as portfolio construction, biases towards certain industries/verticals, conviction/market trends, other deal flow in the pipeline, etc. Each “No” is rooted in a complex and sometimes uncontrollable combination of events and circumstances, but that doesn’t make them hurt any less. I’ve thought a lot about how I can be more comfortable dishing out multiple rejections on a daily basis. I’ve found that transparency drives clear expectations, and intentionality helps reason with difficult emotions. I’ve learned to start each intro call by sharing a clear background on Redbud ; I leave time for founders to ask me any questions they may have about our process; if there is a perceived conflict of interest, I mention it immediately. My favorite question I’ve started asking is for founders to share thier favorite articles, white papers, or case studies with me. It has allowed me to do a quick dive into their industry, gather my thoughts, and communicate them to my GP clearly. Information drives reasoning. In the midst of my most poignant rejections, I’ve always asked myself, “why?”. Now, I deliver the clearest and most concise ”why” I can to founders in each rejection post intro or second call. Ultimately, rejection is an inherent part of raising capital, and while it may never be easy, my goal is to handle it with respect and empathy. I’m striving to create a culture where the pain of rejection isn’t lessened, but the clarity behind it is increased. I’m starting to view rejection as an opportunity for evolution — both for myself and the entrepreneurs I interact with. It’s a chance to mutually refine our approaches, learn from setbacks, and foster resilience. Something that not many other events/emotions have the opportunity to illicit. Previous Next

maria heyen's writings, readings, and thoughts on vc welcome. welcome to the website here are my sticky notes, bookmarks, readings and writings, basically a collection of trends, behaviors, ways of thought, and actions that I have that I want to track/think about over time. somethings I write about: identity investing influence somethings I read about: thinking fast cultural curiosity discipline + process