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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

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

< Back 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 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 on curiosity January 2025 the underrated skill of not worrying about sounding dumb and just being curious The summer I spent in Barcelona was one of the most important experiences of my life. Like most college students studying abroad, I was excited about a "Cheeta Girls Summer". What I didn’t expect was that what I’d take away would have nothing to do with travel or language but with how to think. My internship at a proptech startup started the day after I arrived. I barely knew the company’s name before walking into the office, jet-lagged and (embarrassingly) late. The moment I sat down, I realized that no one spoke English. I had taken Spanish for years, but the classroom had not done much to prepare me for the speed and complexity of real conversations in a working environment. That first day, I understood very little. I went home, convinced I wouldn’t last the summer. But something interesting happens when you’re forced into a situation where you don’t know enough to pretend. You stop worrying about how you sound. Since I couldn’t talk much, I listened. At first, I asked only the simplest questions - enough to get through the workday. But as I got more comfortable, my curiosity took over. I started asking my coworkers about their lives, their weekends, and their opinions. I stopped filtering for what I thought was “smart” to ask and just asked what I genuinely wanted to know. That’s how I got to know Núria, my boss. She had grown up in the Soviet Union before immigrating to Spain, and I was fascinated by her story. One night before post-work drinks, I wrote out a list of questions I wanted to ask her - big, possibly naïve questions about her past and how she saw the world. I brought that list to our happy hour the next day. When I hesitated, worried that some might come across as uninformed, she laughed and told me to ask anything. That conversation led to a weekly happy hour, and during my last week in Spain, she gave me a journal filled with books to read - her way of continuing the dialogue. I think about that summer often, especially in my work as an investor. The same curiosity that helped me navigate Barcelona is what now guides my conversations with founders, LPs, and peers. Investing is an industry full of pressure to appear certain - to have well-formed opinions, to ask the “right” questions, to never admit what you don’t know. But I’ve found that my best investment decisions have come from doing the opposite. Instead of approaching diligence with a fixed lens, I approach it like my conversations with Núria by setting aside preconceived notions and asking questions that cut straight to what I truly want to understand. Why now? Why this market? What do you believe that others don’t? It's basically an exercise in first principles thinking but from a place of insatiable curiosity. The same applies to my conversations with other investors. Some of the best calls I’ve had with my peers aren’t the ones where we exchange fully-baked theses but the ones where we openly challenge our thinking. How are you looking at this trend? What assumptions am I missing? It’s in these back-and-forths where we’re willing to be wrong, to ask the obvious questions, to push beyond the surface-level consensus that the real thinking happens. What I learned that summer wasn’t just Spanish. I learned that the best conversations and the best thinking come from removing the fear of sounding dumb. Some of the most valuable insights I’ve had in my career have come from simply asking, How do you think about this? The ability to ask questions without hesitation and to be fully present in a conversation without worrying about how you’ll be perceived is a radically underrated skill. Previous Next

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

< 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 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

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