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

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

< Back maniacal urgency February 2026 in other words, “super speedy quick” It’s not my natural rhythm to move fast. I’ve always been more methodical, concentrated on outcomes and behaviors rather than the ‘move fast and break things’ ethos of tech. One of the things I’ve come to appreciate about venture is how it forces urgency. Everything is fast, and those who move quickly win. For example, founders often ask at the end of a call what the timeline looks like for a decision. It depends on a range of factors, but for us usually averages around three weeks. The incentive is compression in response. Faster responses mean better odds, especially when we’re competing for allocation in a round that’s moving fast. Speed, in a way, denotes seriousness. This holds true for many things. A quick text back from a friend, response time on an email, and the time it takes for a server to greet your table after sitting down. The necessity of the maniacal urgency has burned out any laziness in me. It’s made me brutally honest about what’s realistic to accomplish within a given timeframe and how to maintain quality along the way. Spend more time thinking, writing, and talking to founders; waste less time elsewhere. Previous Next

< Back chobani on my jeans August 2025 becoming my cultural diet and what it means for founders Nothing screams chronically online more than walking into a grocery store, rubbing Chobani yogurt all over a stiff pair of jeans, filming it, and then posting it on TikTok. why? All because the lyrics in the song “Jeans by 2hollis” sound like he sings “put chobani on my jeans” instead of “put your body on my jeans” – viscerally different situations. Jeans became the song that framed my July photo dump on Instagram as a nod to the fact that I have seen this trend, find it funny, and ultimately, it’s become a part of who I am (in, albeit, some weird way). did this increase sales of chobani or annoyance of grocery store employees? I’ve been thinking about this a lot – how the content we consume every day becomes who we are. Humor, conversational references, restaurant choices, politics, etc. are all profoundly influenced by the content we consume and how long we let it marinate in our brains and bodies. As the internet and its culture have intertwined with our lives, it has changed how I think, act, and operate, as I believe to be true for most consumers. I think Lisa Kholostenko says it best, “consumption isn’t just passive enjoyment—it’s dynamic, it answers back.” It introduces the concept of a “Cultural Diet” that the content you consume becomes a part of you. It can lend itself to an era of your life, a fleeting Instagram photo dump, a phrase you repeat to your friends, or it can transcend chapters, inform your politics, and trickle into the core of your personality. No bigger indicator that more people are becoming a steady reflection of their cultural diets than the dialogue around taste. “Taste” — who has it and who doesn’t — is all VCs, founders, tech people, and performative matcha labubu keychain hipsters want to talk about. As defined by Emma Lou Cogan, Taste is “the byproduct of our worldview, the measure of our exposure to varied newness, & the invisible thread that ties together our emotional, psychological, and cultural instincts.” the tastemaker c.2025 I believe that taste is what evolves from your cultural diet. People focus on manufacturing taste via the content they consume. Except there is no filter for consumption. There is no way to limit the content you read, watch, and react to every day. You can curate your feeds to what you perceive to be high quality, unsubscribe from newsletters, mute accounts, and follow only those you know, but the flood never really stops. Algorithms surface “related” posts, friends forward viral clips, group chats ping with whatever celebrity look-alike contest is happening at your local park this week, and billboards replay the same slogans as you commute. In an ecosystem where the internet and reality are divulging more and more, content behaves like background radiation: it seeps through every filter, ensuring that the endless stream of headlines, hot-takes, and ads still becomes part of your cultural diet whether you consciously invite it to be or not. eating good Vice versa, if you’re always feeding yourself content that feels good, is comfortable, and is familiar, it’s like only eating Big Macs; you feel wonderful when eating it, but slow, sluggish, and left behind in the tides of conversation when those who have tried salads, soups, and sandwiches come around and reference another world of taste. You are what you eat. This leaves a question for founders building their companies today: how do you become a part of people’s cultural diets? It’s a more fun way of saying distribution matters. How you distribute (feed) your product into your consumer's cultural diet (the content they consume) determines how quickly you can move. Distribution is becoming increasingly paramount as certain product features, data, and previously “moats” are becoming commoditized. The company that most rapidly incorporates itself into its customers’ cultural diet, so convincingly that consumers experience the product as an extension of their own identity, unlocks a flywheel in which every operational building block (distribution, retention, pricing power, and brand equity) compounds at an accelerated rate. It happened with Lovable (0 to 2.3M users in 8 months) by making “vibe coding” part of the engineering zeitgeist. Rhode (0 to $1B acquisition by e.l.f in 3 years) by bringing a high-fashion lens to affordable beauty. Ramp (0 to $22.5B valuation in 6 years) by embracing the “underdog” narrative online and making something people hate (expense reporting) actually enjoyable. normalize slapping timothee on a billboard with a logo Each company’s story is now inescapable. Scroll a feed, open an email, cue up a podcast, each touchpoint repeats who they are, what they build, and why it matters. The product becomes a piece of their unique customers' unique diets. Ultimately, distribution is not only a question of reach; it is a matter of incorporation. When a product, message, or idea slips unnoticed into the daily cadence of alerts, shortcuts, and inside jokes, it migrates from the marketplace into the cognitive architecture of our brains and ultimately influences who we are. The push-notification that triggers a reflexive glance, the reference that needs no explanation in conversation, these are signals that a product has been metabolised, not just adopted. In that sense, market penetration is inseparable from identity formation: what saturates our attention steadily rewires our assumptions about efficiency, status, and even community. That realisation imposes a dual responsibility. For founders, the task is to design a product capable of that tenancy. For the rest of us, the question is curatorial: which inputs do we allow to occupy our limited cognitive real estate, and to what end? ___ Building to become apart of your consumers cultural diet? Drop me a line maria@redbud [dot] vc 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? what does it look like to be an "essential worker" in the age of AI? 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 protein 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. 11/25 no thoughts just mexico travel :) 12/25 some 2026 predicitions/thoughts the Series A crunch from 2024 will have permanently reshaped Seed financing: extreme valuation dispersion, hyper-competitive rounds, as investors push to hit ownership targets earlier and earlier with the public markets performance increasingly propped up by a small concentration of AI-native companies, the AI bubble pop is coming openAI’s cash burn, coupled with spending commitments they may not be able to fund, mirrors the behavior of late-stage Enron and will result in a similar outcome nvidia will see a "crash" like Cisco in the 00’s (GPUs is to LLMs as Hardware is to the Internet). Cisco was the hardware powering the age of the internet, similar to Nvidia today. i'm not saying the company is going to blow up, okay, but I'm saying there will be a reckoning in the public markets of some kind (**working on something longer form here) 01/26 global oil sales are denominated in dollars, obviously the US is worried about that changing... the petrodollar keeps demand for USD high (some infiation of value here) Rn capital is currently being funneled into US financial and tech assets rather than physical production. As domestic growth becomes increasingly concentrated in AI, headline GDP is stabilized without rebuilding physical systems, leaving commodities and infrastructure underpriced until failure or geopolitics force a sudden repricing. (a.k.a recession) ** last updated 01/02 Previous Next

< 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 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 rejection January 2024 i’ve spent a fair amount of my life as a young person facing rejection. I’ve spent a fair amount of my life as a young person facing rejection. As a child getting cut from sports teams, as a teen not making it into elite colleges, and as a young adult facing brutal internship/job passes, I am no stranger to the painful ache that rejection causes. I have a deep understanding of some of the long-standing effects tough rejections can have, and it’s hard not to recall times when I showed up at my best and met with what I deemed to be the “worst.” The complex and burdensome emotions that rejection can illicit are something that I spur in founders every day. I spend a large portion of my time as an investor rejecting founders, and being so familiar with the feelings myself, it is a dichotomy I’m learning to be comfortable with. I sit across the table from founders each day who have put EVERYTHING into their businesses, and 99% I follow up with an email on my firm passing on investment. There are a few reasons in particular why I wanted to write about rejection as my first “soapbox.” #1 I want founders to know that no matter how quickly calls go — I can feel the emotion, time, energy, and capital that they have put into their business and that even though I say no often, I don’t say it lightly. #2 VCs themselves are a business, and that’s not talked about enough. We care about founders, and we deeply want them to succeed, but ultimately, our duty is to our investors called LP’s whom we seek to drive returns for (more on this in the future). No’s are said for a variety of reasons, and most of the time, No’s can be traced back to more arbitrary reasons and things that founders can’t control, such as portfolio construction, biases towards certain industries/verticals, conviction/market trends, other deal flow in the pipeline, etc. Each “No” is rooted in a complex and sometimes uncontrollable combination of events and circumstances, but that doesn’t make them hurt any less. I’ve thought a lot about how I can be more comfortable dishing out multiple rejections on a daily basis. I’ve found that transparency drives clear expectations, and intentionality helps reason with difficult emotions. I’ve learned to start each intro call by sharing a clear background on Redbud ; I leave time for founders to ask me any questions they may have about our process; if there is a perceived conflict of interest, I mention it immediately. My favorite question I’ve started asking is for founders to share thier favorite articles, white papers, or case studies with me. It has allowed me to do a quick dive into their industry, gather my thoughts, and communicate them to my GP clearly. Information drives reasoning. In the midst of my most poignant rejections, I’ve always asked myself, “why?”. Now, I deliver the clearest and most concise ”why” I can to founders in each rejection post intro or second call. Ultimately, rejection is an inherent part of raising capital, and while it may never be easy, my goal is to handle it with respect and empathy. I’m striving to create a culture where the pain of rejection isn’t lessened, but the clarity behind it is increased. I’m starting to view rejection as an opportunity for evolution — both for myself and the entrepreneurs I interact with. It’s a chance to mutually refine our approaches, learn from setbacks, and foster resilience. Something that not many other events/emotions have the opportunity to illicit. Previous Next