< Back first calls July 2024 how I run every first call with a founder. One of the largest misconceptions I notice from founders when speaking to them about their companies is the belief that talking to a junior VC can’t do anything for them OR that it’s the main point of decision in the deal flow process. Neither of these are wholly true. It’s critical for founders to understand that what a junior VC needs to move forward with a deal varies by firm, but going into that conversation knowing you have 30 minutes to make someone your biggest internal champion is incredibly important. The Importance of the First Call Every week, I take between 10 to 20 pitch calls. These conversations span from entrepreneurs who are just considering starting a company and don’t yet have a fully developed business idea to founders who are raising $3M in pre-seed rounds with lead investors secured. With such a diverse range of founders, it’s easy to get lost in a sea of companies and details. That’s why it’s crucial for founders to be memorable. Being memorable doesn’t mean having the most energy or constantly wearing a big smile. To me, it means being incredibly candid and honest about your company and its potential and being as well-prepared and disciplined as possible going into that first call. I understand that fundraising is a significant time commitment for founders, taking time away from building their company or talking to customers. Therefore, I make it my job to match that level of preparedness, coming into the conversation ready to share insights about the firm I work for and the value we can provide to them. Starting the Conversation After the small talk and niceties at the start of a pitch call, I always provide the founder with a clear structure for how the next 30 minutes will go. I’ll share a bit about our fund and the value we offer. Then, I’d like to hear about them and why they started their company. Afterward, we’ll transition into a Q&A session. By giving an overview of the call, I am setting expectations. Each VC leads calls differently, and I want the founder to know what to expect once we get on the call. Right away, they knew they will have time to ask me questions about the firm. It also clarifies that I prefer conducting the meeting in a Q&A format rather than a formal presentation. The first question I ask on every pitch call is, “Tell me a bit about your background and why you started your company.” This gives me a general overview and introduction to the founder and divulges insights that aren’t in a pitch deck. The best founders give a quick, high-level overview of their background, highlighting key moments that were crucial when they decided to leave a corporation to start a company. They talk in-depth about the pain points they personally experienced, maybe sprinkling in some customer discovery, but overall, they clearly articulate why they are building their company. This overview lasts no longer than 5 minutes. Building Conviction Quickly I’m constantly thinking about what I need to believe in order to gain conviction as quickly as possible, the areas where I need to do supplementary due diligence, and the priority list for what my partners may want to see. To cover as much ground as possible in the shortest amount of time, I run my first calls in a pretty disciplined fashion while still remaining casual. Here is the structure of my calls and some things I prefer to do when chatting with founders: 1. Have a Deck Before the Call I always try to have a pitch deck before the call to minimize the time spent asking questions already answered in the deck. Sometimes, I ask the same questions about key KPIs like sales cycle or pricing to confirm what’s in the deck or see if anything has changed. For early-stage founders, factors like sales cycle and pricing are often influenced by new learnings and change until key customer contracts are set in place. I want to ensure I have accurate numbers on these key details. 2. Keep It Conversational I try to keep the first pitch call in a conversational format as much as possible. I prefer to ask questions and have the founder answer them without running through a formal presentation. This helps build rapport, softens the power dynamic between a VC and a founder, and provides insight into how clearly the founder can articulate their vision and how deliberate they are in answering questions. 3. Dig Deeper with Follow-Up Questions I believe you get the best answers after the second or third question when digging into a topic. I let the founder’s answers to my previous questions guide the formation of my subsequent questions. This allows me to dive deeper into key risks and highlights of their business. It also helps get founders off script; many are on multiple pitch calls a day answering the same questions. I aim to cover as much ground as possible in that first call. Ending the call I end every call by thanking the founder for their time. If I didn’t have the pitch deck before the call, I make sure to request it, along with any supplementary materials I might need for early diligence. I also provide an overview of the timeline. I explain what the rest of our investment process looks like, the average timeline for each stage, and when they can expect to hear from me if we’re moving forward. Post-Call Follow-Up There are a couple of things I do after a first call. First, I ensure I have all my notes in order. I need to make sure that I have answers to the following categories: founder’s background, problem, solution, sales cycle, pricing, traction, and round terms. If I know I am missing something after that initial first call, I send an email within 24 hours. The hope is that after the first call, I’m excited about the founder, excited about the company they’re building, and curious to learn more. After a particularly excellent first call, I start to pull together a first-page diligence shee (more on that in a future post) to ensure that when I present the company to my partners for a second call, I am as prepared as possible and have the best understanding of the business they are building. 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 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

< 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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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

writings February 2026 maniacal urgency in other words, “super speedy quick” read here 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

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

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