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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

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

< Back what I wish I knew my first month in venture April 2024 the mistakes I made and advice from other young investors. I grew up incredibly isolated from the tech world. My parents worked as teachers, there were no corporate jobs in my community, and no one around me spoke the language of “business.” In starting my career in Venture, I've had to get up to speed on corporate and venture courtesies simultaneously. I’ve found that working in VC isn’t a learning curve; it’s a learning rollercoaster. When you think you’ve grasped a concept or nailed a best practice, there’s another one waiting for you around the bend. It’s a cycle of learning that can leave you feeling like you’re stuck on a ride with no one telling you where to exit. So don’t worry, I’ve punched my ticket on the rollercoaster many times when I didn’t have to (and I know there’ll be more). There are way too many things that I wish I had known in month one, but below are the key learnings I’ve had, along with insights from other young VCs who’ve navigated similar challenges during their inaugural month in the venture. 1. Taste takes time It’s incredibly difficult to know what you think of a company when you have no baseline for comparison. Knowledge of large markets, comps, and knowing what questions to ask can all be accelerated by talking to as many founders as possible. Knowing what you like to see in a startup and what your partners like to see takes time and practice. On another note, having conviction is not an overnight phenomenon, and being able to communicate it to a GP isn’t either. Learning time can be shortened through repetition. “Developing your own taste and pattern recognition takes time. Before narrowing in too much on what you like, first focus on learning what kinds of companies and business models your partner/firm likes”— Georgina McMillian , Investor at Headline . 2. Always double opt-in When introducing two people who don’t know each other, ask each of them to opt-in to the introduction before making it. I was completely unaware of this common courtesy when I started in VC (sorry to all those who got intros launched into thier inboxes from me) . Emails without opt-ins don’t set up either party for success, they increase the likelihood of the connection never happening, and they make people aware that they may not want to spend the time on intros that come your way. Here’s my favorite breakdown of how to facilitate a strong intro email from Chris Fralic, Partner at First Round Capital. 1. VC fundamentally is about people and the art of relationship building, so strong interpersonal skills are crucial 2. FOMO is a REAL thing 3. Conviction is key- Michelle Rogoff , Investor at Hyde Park Angels 3. Listen more. Talk less. There’s a lot of ground to cover in an intro call with a founder. Asking concise questions to get the answer you need and listening is critical. Sometimes, what a founder doesn’t say is just as important as what they do say. Noticing the missing pieces of information helps formulate the next question. Listening to the full scope of an answer helps you decide where deeper into the aspects that are missing or transition to the next topic. Previous Next

< Back pre-traction April 2025 thoughts on legitimate ways to display traction early Lately, I’ve been thinking a lot about what traction really means at the pre-seed stage, particularly before a fully built product, paying customers, or hints of revenue. This stage is incredibly nebulous. As a founder, how do you de-risk your idea in a way that creates conviction, not just for yourself, but in the eyes of investors? It’s a tricky balance. Founders want to raise capital off the strength of their background, a 10-slide deck, and maybe an MVP. But the reality is, real traction is leverage. If you have people paying for what you’re building, even in small amounts, the path to closing a round gets dramatically easier. Still, I think there are legitimate and strategic ways to display traction that don’t rely on traditional revenue. These “pre-traction” signals can tell a compelling story about market demand and founder execution, even before a wire hits the bank. At Redbud, we back a handful of pre-seed companies each year. Almost all of them have something built (i.e., some version of an early product) and often, a few design partners or test users. But 90% of the time, there’s no meaningful revenue. Maybe a couple hundred dollars in MRR. And yet, when a company is compelling at this stage, it can come down to a strong pre-traction narrative. To me, pre-traction means early, often scrappy signals that people are willing to pay for what you’re building or at least are highly interested. If you’re launching a consumer product, maybe it’s a waitlist of 10,000 people. If you’re building a B2B SaaS tool, maybe it’s a warm pipeline of three or four design partners who’ve agreed to test and eventually buy the product. When I evaluate companies like this, I’m constantly asking: how long will it take before these early users convert into paying customers? If a founder has thought through that timeline and is willing to hold themselves accountable to it, that’s a massive indicator of clarity and conviction. It gives investors something tangible to pull on, but more importantly, it shows the founder is operating with honest constraints and urgency. Sometimes, pre-traction is rooted in lived experience or a unique domain insight. A founder might say, “I know product managers will buy this tomorrow, because at my last company, we spent $25K a year trying to solve this exact problem.” That’s not a paying customer, but it is a signal. It reflects a deep understanding of the pain and a credible path to solving it. There’s nothing more compelling than a founder who says, “I know this is real. I know people want it.” And then backs that up with a waitlist, a pipeline, or even a series of customer conversations proving demand is bubbling beneath the surface. The best founders don’t just hope people will buy; they have early evidence that someone is already leaning in somewhere. Ultimately, pre-traction is about accelerating the speed of iteration. If a founder understands how they’ll acquire users, when they’ll start paying, and where the early friction lies, they can build faster, learn faster, and adjust quickly when things don’t go as planned. The advice to “build and ship quickly” is universal for a reason. But if you’re raising capital while doing that, think deeply about how you communicate the friction you’re feeling, the conversations you’re having, and the early signs that what you’re building matters. Previous Next

< Back 2nd-hand insights October 2025 passed along learnings are like hand-me-down clothes One of the first lessons in venture “pattern matching” is to back founders with domain expertise. These are people who have lived, breathed, and worked in the problem space they are building in. A former HR leader at Facebook building a payroll tool, for example, starts with a sharper reference point than if I started cooking up the next Rippling competitor. That said, great companies are often built by outsiders. With AI lowering the cost of building, the goalposts have moved. I’d argue there’s little lasting “moat” in tech today (more on that another time). What matters is speed and distribution, and this domain knowledge functions like seeing the puzzle before everyone else. You move faster from A to B because you already know which pieces click. spencer bledsoe from survior, who memorized most likely puzzles prior to his season. he solved this one in 15 seconds. When founders build in an unfamiliar space, they often try to close the gap with “second-hand insights”: advice and patterns borrowed from people who’ve been in the industry. Helpful, yes, but second-hand insights are like hand-me-down clothes: a step behind the trends and a bit ill-fitted. Seond-hand insights carry the original owner’s context and what worked under one set of constraints, incentives, and market timing may not "size" to the present. Relying solely on second-hand insights keeps founders working at a constant disadvantage. You’re waiting to learn the hard way or chasing someone else’s lessons. There’s already enough learning the hard way in startups. The thoughts of others (advisors, investors, etc.) can’t substitute for the founder’s own lived context; without it, those insights don’t compound. he was an advisor with more equity than the CTO for "insights" This is why, as VCs, we hesitate to back teams without a unique angle or background, not because those without the domain experience can’t win, but because at the pre-seed stage, proprietary insight is usually what creates founder conviction. And founder conviction is what creates our conviction that the company could derive a billion-dollar outcome. 1st Hand Insights: “At X, I saw/learned X, that influenced X, which I am now building with X” Second-order effects: Clear articulation around early vision & product “I want to move from X GTM to X GTM just like I did at my previous company/employer.” Second-order effects: Speed to market, robust pipeline of prospects or pilot customers “What most don’t understand is X, because I know this, I am able to do X thing 10x better than X.” Second-order effects: Speed of iteration, revenue ramping post launch 2nd Hand Insights: “Our advisor shared that X was their experience, and so we are trying/doing/experimenting with X.” Second-order effects: Slow speed to launch, multiple versions of product (V1,V2,V3) “The sales cycle is long in X, so we are doing X, because it is how X person did it at X.” Second-order effects: Quick no’s from prospects, prolonged sales or implementation cycles, customer feedback that the problem isn’t “urgent” enough to solve for at this time. “X industry has been historically slow to adopt X, because X” ( when broad, non-specific** ) Second-order effects: Lose to the incumbent or new solutions, slow growth, no customer network effects All of the above is not new – but the gap is widening. I’m watching it in real time. The world is stochastic, and it's better to have your own framework to build on than wait for someone to share theirs. 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 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 chewing on May 2025 a running list of random things, trends and notes some of the ideas/insights i'm currently chewing on **work in progress 5/25 superior product wins in the late stage - distribution wins at all stages (esp. early) distribution is only becoming more and more paramount as software sunsets and AI becomes more commoditized (i.e. AI voice products, AI travel planners etc.) distribution will most likely win here as we move closer to AGI - what will the human experience/purpose be? 6/25 we are moving towards a fully agentic world, there is no stopping it. i don't think the next generation of $B companies will be agent service providers it will be the raw materials + manufacturing + build ecosystem that powers them. i believe there will be a regression towards "traditional" businesses with agents fixing issues that have previously inhibited these businesses from reaching scale or being too capital intensive. how do i get conviction in a company that may be completely replaced by AI? 7/25 original ideas (i.e. creativity) are more powerful than ever ideas used to be cheap not anymore can "cool" be manufactured? 8/25 the 2nd order effects of more and more agentic AI tools hitting the market will be a 2nd wave of tools to help people manage, deploy, and scale the agentic tools from the first wave working on a hypothesis for wave #3 is it possible for a software to bring us back to being human? or is that just too ironic? 9/25 why does everything need protien in it? net new (no rev, no product) > company that has been alive 8+ months with no breakout momentum ^^ this phenomena is new for me only types of deals getting done are "net-new" or expensive + hype seed-ish co's last 2 investments were one of each 10/25 in may the bar was crazy high to be a vc-backed funded at the early stages, rn it's a founders market -- feels like these cycles are tightening and compounding. doesn't feel corrective at all just inflated, but i guess it always feels this way? building in areas where you have operated is paramount, empathy isn't enough. getting second hand insights from advisors, peers, investors, etc. is like getting hand me down clothes -- late to the trends and they never quite fit right are there any truly new thoughts or ideas anymore? i think there is an argument that this is only getting worse as ai responses are all derived from a prompt will all content, media, product, ideas, etc. just eventually become a cheap derivative of something prior? i believe "ai slop" is the early innings of this. ** last updated 10/21 Previous Next

< Back y2 June 2025 “self”, obsessive thinking, punching upwards, and not getting lost in the sauce Today marks two years at Redbud VC . Whenever a big “milestone” or marker rolls around, I catch myself feeling both nostalgic and reflective. It’s so easy to get lost in the day-to-day of the calendar; there’s not much time for quiet thinking on patterns, behaviors, and decisions. That said, I have been deliberating on what I want to share here, and I decided, in lieu of being tactical, I’m going to be a bit more spontaneous. My candid thoughts on a few themes across my 24-month tenure as an investor below. ___ “Self” I think Emily Herrera, former VC @ Slow & Night, said it best : “You made it - which means you’re starting to think long-term about What you like Who you like Who you are” This is the perfect summation of what it means to have worked in VC for two years. It is frankly exactly where I stand today. I spend a significant portion of my time thinking about those three things, and oftentimes, it feels like they’re always changing. As you start to build a circle of competence in an area, you inevitably become increasingly jaded about the value or outcome of a particular industry or trend. Candidly, it’s weird to be expected to be a pseudo “expert” on 10 million technologies at once. Like I’m supposed to know about “application layer AI, trends in food for consumers, emerging SaaS categories, defense contracts, etc.” I think that's why Emily’s three categories are so important – they allow you to narrow your aperture for opportunities. It takes a bit of the industry-imposed pressure off. While I’m still working on answering the above, one thing I have figured out is how to ask the easy questions. I think that good founders can smell BS a mile away, they know if the VC they are talking to gets their business or not. I want founders to know right off the bat if I understand. I often ask “easy questions” (i.e., explicitly asking “how does this work?”) and repeat information/process as I understand it for founders to correct my understanding of their companies. The questioning, coupled with the regurgitation of information, helps me not only understand the company and founder sitting right in front of me, but I believe it will help me answer Emily’s questions above. ** (Will check back to see if this is really how it goes down next year) Obsessive thinking In my opinion, the best and worst thing about being an investor is that you are always thinking. I feel always on, in a way. I like to spend my weekends taking long walks on the lakefront in Chicago. As I was walking early last week, I saw a sad little Lime scooter that had been tossed into the lake. I counted 3 Lyft bikes and 2 Lime scooters during my walk. All I could think about was how the company deals with damaged or unusable bikes/scooters: “It’s not super scalable to try to send a technician out to see what's wrong with them.” “This has to be written off.” “What percentage of inventory is written off like this?” “I wonder if anyone is building a better fleet management system for these bikes?” “Is that market even big enough, though?” Yep, always on. The great part about this is that venture rewards unfiltered curiosity. The not-so-great part is when you’re Googling what startup makes the QR code checkout system on your restaurant table, and your friends are discussing weekend plans without you. Punching upwards I love being overlooked. It’s a quintessential part of my intrinsic motivation. I’ve spent my entire life being overlooked and proving out. It would be radically uncomfortable (in a bad way) for me to be in 1st place from the start. I prefer to work to win. For two reasons: There’s no pressure when you are the underdog. You’re not expected to be great. The wonderful part is that you get to work hard, hustle, and ultimately, if you're competitive, you win. No one gave it to you, and it wasn’t expected. Winning when standing at a “disadvantage” sets a precedent that you have the grit and determination necessary to win in any environment. When you’re junior on a team or at a small firm, you need to produce. It’s all hands on deck to do a bit of everything. Where you spend your time is critical. I realized this as I spent a better part of Year 1 getting bogged down in non-high-value tasks and the day-to-day. I’ve found the best ways to produce for your firm and your portfolio companies are: Sourcing a new company for the firm to invest in Making customer, investor, or talent intros for your portfolio companies Diversifying your firm's network of investors, founders, and LPs spoiler: all this takes is hustle and a bit of shamelessness At Redbud, sourcing a customer for a portfolio company is an equal win to sourcing a company for the firm to invest in. It’s easy to sell why a founder should take your money when you have examples of real value you’ve been able to add (i.e. customers). Lost in the sauce There’s a lot of noise in venture and startups. People are constantly sharing what they’re doing, how they’re working, and what they’re working on. (Ironically, as I do here) There’s always pressure to be doing something, which, when everyone is always talking, creates noise. If you’re not careful, you can get lost in the sauce . As I see it, the sauce is the lethal combination of natural noise, a myriad of weekly events, your day-to-day calendar, firm expectations, pressure of never missing an opportunity, the list goes on…see how easy it is to get lost. It’s essential to limit the amount of sauce you are in at any given time. I do this in 3 ways: Staying focused – remembering that my job is essentially the three bullets on producing above Being honest – combating the constant culture of flexing with kindness, honesty, and vulnerability, where I can Having a community – a handful of investors that I share my failures and successes with, and text multiple times a week ___ It’s been a wonderful 2 years at Redbud. To the companies in our portfolio that I’ve had the chance to be an early believer in or finder of – thank you for your trust, connection, and conviction that our small/early check would make a meaningful difference on your cap table. To all the founders I’ve spoken with across time zones, stages, and industries this year, thank you for your vulnerability, openness, and courage in building something new. To Brett and Willy, thank you for taking a chance on me. 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 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