So Thankful for the (Hero's) Journey
Welcome to the 14th Edition of Public School Ventures' School Bulletin!
In this month’s ‘Bulletin’ you will find:
The Hero's Journey: An Update on the Yale Prospect Fellowship - Delve into the latest developments of my application to the Yale Prospect Fellowship and the continued path forward despite setbacks, embodying the resilience of the hero's journey in venture capital.
The Call to Adventure: Building the Team - Discover the strategic assembly of our future venture team, drawing parallels between superhero alliances and our ideal partnership structure for a Series A fund.
Trials and Triumphs: Crafting Our Strategy - Explore the strategic blueprint of our high-conviction, lead-only Series A fund, detailing how we aim to navigate and succeed in the venture capital landscape.
The Return: Defining Our Edge - Uncover the core competencies that give our venture strategy its edge, from deep market insight to operational excellence and strategic partnerships.
Partner Highlight: Bottega8 - Learn about Bottega8's revolutionary AI Model Training services, designed to enhance efficiency and reduce costs for financial institutions in the venture capital and private equity sectors.
As we gather our thoughts and gratitude this Thanksgiving season, I am compelled to reflect on our collective journey—a narrative punctuated not just by successes but by the lessons we garner through challenges. This edition marks a pivotal moment in our shared adventure, reminiscent of a hero's journey where every setback refines our purpose and every triumph propels us forward.
1. The Hero's Journey: An Update on the Yale Prospect Fellowship
A Tale of Resilience and Renewed Resolve
Earlier this month, I received the decision from the Yale Prospect Fellowship. While the outcome was not favorable—my application was not selected for this year's cohort—the process was a profound affirmation of our mission and vision. The feedback on my application, especially the personal stories shared, were immensely inspiring and have only strengthened my resolve.
The Yale Prospect Fellowship's selection process was highly competitive, with thousands of applications from across the globe. The rejection letter, while disappointing, is a familiar plot point in any hero's journey—reminding us that every protagonist faces trials. It's these challenges that test our mettle and refine our strategies.
Despite this setback, the essence of our quest remains unchanged. The Fellowship was but one path among many to achieve our overarching goal—to establish a premiere Series A firm. My phased approach, detailed in previous bulletins, continues unabated:
Phase I (birth): Foundation building through roles at Prologis Ventures and GreatPoint Ventures.
Phase II (crawl): Launching Public School Ventures, the podcast, and the advisory firm.
Phase III (walk): Setting up a $20M pledge fund to make strategic Series A $5M to $9M investments.
Phase IV (run): The ultimate goal of launching a $275M Series A-focused fund.
This journey is not just mine but ours together—as mentors, colleagues, friends, and supporters have all played crucial roles. For this, I extend my heartfelt thanks to everyone who invested their time and insights into my application and essays.
The remainder of today's bulletin will unfold the final three essays required for the Yale Prospect Fellowship, completing our narrative arc of origin stories—each entrepreneur, each successful individual traces back to one. Let's delve into these prompts, understanding that they form the bedrock of our future triumphs.
2. The Call to Adventure: Building the Team
Do you have an investor partner(s)? If not, are you looking for one?
I’m actively building a high-conviction, lead-only Series A firm, and assembling the right group of mid-career investors and operators feels like putting together a superhero team. Recently, while reading old comic books with my six-year-old son, I found myself inspired by those characters and began drawing parallels between them and the type of partners I wanted to bring on board.
I envision establishing a team of four partners over the following three funds, starting with two partners for Fund 1. Each partner will bring unique “superpowers” essential for Series A investing. The firm will be an equal partnership where the management company is shared evenly, aligning incentives and fostering a collaborative culture that prioritizes the firm’s success over individual goals.
While I’m in ongoing discussions with top-tier candidates who prefer anonymity until we secure a significant anchor, these individuals represent a blend of the archetypes I’m seeking:
The Avenger: This partner comes from a leading global venture firm and brings the institutional credibility necessary to attract LPs. They have a proven track record of driving significant investments and have the stability, founder brand recognition, and gravitas needed for early fund-raising and strategic relationship-building.
The Mr./Ms. Fantastic: This individual possesses deep operational and technical experience, often from engineering or product roles in scaling startups and now at innovative venture firms. Their operator insights make them invaluable at Series A, where founders need someone who understands growth firsthand and can provide tactical guidance on everything from product-market fit to go-to-market strategies.
The Dr. Strange: This investor is a visionary with a strong sense of market trends and an intuitive ability to anticipate where industries are heading. This individual, who will likely join Fund 2, brings an unconventional, contrarian mindset and knack for seeing the bigger picture and challenging norms. Dr. Strange’s ability to take bold, informed bets will complement the existing skill sets, ensuring we stay ahead of the curve.
The Mutant: The overachieving underdog, this partner comes from a background that may not immediately suggest venture capital—perhaps from a smaller fund, corporate VC, or even from a tech leadership role outside of traditional venture. They have unique, untapped potential and a hunger to prove themselves on a bigger platform. Their grit and tenacity bring fresh perspectives and an entrepreneurial spirit to the team.
My experience embodies The X-Man qualities—I’ve cultivated resilience and adaptability from my journey across Arkansas, Wall Street, India, and Silicon Valley. I bridge multiple worlds, from startup ecosystems to Fortune 500 partnerships, and my network spans sectors, geographies, and generations. This background allows me to create connections and strategic alliances vital at Series A, where relevant introductions and deep industry insight can be game-changers.
For Fund 1, we’ll add two partners who embody The Avenger and Mr./Ms. Fantastic traits, ensuring that we have both institutional credibility and operational depth. While the initial team will likely consist of generalist investors, we are open to building a more specialized focus over time—incorporating expertise across enterprise, consumer, and generalist sectors. The platform we create will enhance each partner’s unique background, amplifying their strengths and allowing us to adapt our focus to market demands and founder needs. The seven individuals I am in discussions with are General Partners at significant multistage funds who embody aspects of both superheroes.
With Yale’s support by Fund 2, we’ll bring on Dr. Strange to strengthen our ability to anticipate market shifts and take bold, visionary bets. This phased approach will allow us to build a solid foundation and cultivate a robust, enduring LP base. We will have an Investment Committee process that encourages rigorous thinking without formal voting, ensuring decisions are based on conviction rather than consensus.
Yale’s involvement will accelerate this process, enabling us to vet rigorously and successfully close top-tier partners and secure an enduring LP base. We’ll build a firm that combines operational expertise, institutional know-how, and a culture of innovation, defining a new standard for Series A investing.
3. Trials and Triumphs: Crafting Our Strategy
Describe the strategy.
Our firm will be a high-conviction, lead-only Series A fund focused on building alpha by providing strategic support, operational expertise, and robust networks to scale companies at this critical growth stage.
Fund Size and Deployment Plan: The fund will target $275M, deploying capital over three years into 15-18 companies, with ownership stakes of 15-20%. This focused approach allows us to take lead positions in each deal, giving us the capacity to influence the strategic direction of our portfolio companies directly.
Why the Market Needs My Approach: Large multistage funds often treat Series A as a call option, underwriting deals only to $5B outcomes. This leaves a clear gap for firms like mine committed to high-conviction, high-touch investing, aiming to underwrite $800M to $4.9B outcomes from the start. By being selective and strategic in our investments, we create opportunities with companies that multi-stage funds might otherwise overlook.
I embody this strategy through hustle, creativity, and a network cultivated from my journey across diverse regions and industries. Early in my career, I started building my brand in the open with a blog called The Importance of Reading Earnest, sharing lessons and insights from breaking into VC and working at Prologis. This content built trust and a loyal following, creating a vast network of pre-seed, seed, and growth-stage investors who continue to share high-potential deals with me. I’ve kept this transparency and generosity alive with Swimming with Allocators, which has grown into required listening for early-stage investors and has become a steady source of referrals for Series A deals.
Investment Process and Underwriting: We will deploy a rigorous, research-driven underwriting process honed from my experience as an equity research analyst. I’ve consistently leveraged this skill to provide tailored support and introductions throughout the diligence phase. For example, even before securing a founder's customer list, I often reach out to my network to create connections, offering founders honest feedback on their market positioning and proving my commitment to their success. I’m known for quickly grasping industry dynamics, whether logistics, healthcare services, or transportation, and for using this expertise to guide founders toward scalable strategies.
This approach allows us to:
Verify customer traction and market fit.
Identify critical areas for growth through strategic partnerships.
Engage industry experts early in the process to mitigate risks.
Strategic and Operational Support Post-Investment: I have a long track record of actively supporting portfolio companies in ways that extend well beyond capital. From Prologis to GreatPoint Ventures, I’ve helped founders secure critical commercial relationships and navigate complex go-to-market strategies. My efforts include:
Introducing companies like Flexport and Airspace to major transportation players such as JB Hunt, DHL, and Daimler led to multimillion-dollar agreements and invaluable commercial validation.
Working directly with COOs and CROs on GTM strategies, often advising on specific approaches during industry downturns or shifts, as I did during the supply chain disruptions of 2020.
Creating the “Next Gen” engagement program at Prologis, offering venture-backed companies prime warehouse space in exchange for equity, which secured allocations in deals like Sendoso and forged lasting ties within the Fortune 500 logistics ecosystem that wanted more access and insights from technology companies.
These efforts demonstrate my ability to win deals against Tier 1 firms by being hands-on, strategic, and relentless in adding value. Whether it’s advising on fundraising, securing introductions to strategic customers, or providing industry insights, I am deeply invested in my portfolio’s success from Series A to Series D. I also understand the importance of rolling off boards strategically, ensuring I can recycle my time with new companies core to our mission.
Distinct Network and Approach to Winning Deals: My network is one of my greatest assets. By bridging worlds—from startups to Fortune 500s and between both coasts and industries—I offer founders a unique pathway to growth that few other Series A funds can match. Over the years, my hustle and creativity have helped me access deals earlier than traditional Sand Hill Road firms. I have leveraged my background in equity research to engage across sectors, identifying trends and building relationships that translate into strategic advantages for my portfolio.
While building Public School Ventures, I’ve developed a syndicate of over 800 angels, family offices, and emerging VC professionals who provide additional insights and support to our investments. By continually building in public, I’ve built a reputation for authenticity and generosity—qualities that have created a flywheel effect in deal flow, allowing me to source deals from early-stage investors who view my involvement as a valuable next step for their top-performing companies.
Building a High-Conviction Team: My partners will also embody the values defining my venture capital approach—communication, collaboration, and conviction. They will each bring complementary strengths that enhance our ability to execute our strategy effectively. The equal partnership structure will ensure that everyone is incentivized to prioritize the firm’s success over individual goals, fostering a team culture where ideas are freely exchanged and collective decision-making thrives.
While we start as generalists, our partners will eventually bring their industry focuses, be it enterprise, consumer, or generalist investing, with the flexibility to evolve with market demands. Yale’s involvement will support this team-building process, enabling us to vet top-tier candidates and rigorously secure an enduring LP base. We will build a firm that combines operational expertise, institutional know-how, and a culture of innovation, defining a new standard for Series A investing.
Why Now & How Yale Amplifies the Strategy: With my background and track record, I am well-positioned to capitalize on the gap in Series A investing by creating a firm that offers more than just capital. We are here to set a new standard for high-conviction, lead-only investing and to be the go-to partner for founders who need more than just a term sheet.
Yale’s support will be instrumental in accelerating this process. With access to their network and resources, I can further enhance our team-building, secure an LP base with long-term alignment, and refine our institutional approach to service and governance. Yale’s reputation for backing visionary, high-impact fund managers fits perfectly with my vision, providing the resources needed to rapidly scale a firm that embodies the same principles of hard work, deep commitment, and strategic foresight that have guided my career so far.
4. The Return: Defining Our Edge
What is your edge?
My edge as a venture capitalist lies in three core strengths: adding meaningful post-investment value, leveraging an expansive network, and executing a deep diligence process. These elements create a competitive advantage that drives success for my firm and the companies I partner with.
Adding Meaningful Value Post-Investment
“Earnest added more value than anyone on my board. He was knowledgeable, thoughtful, and truly cared about the success of the company. Anytime I needed him, he was there, and he always added a ton of value at board meetings.” — Nicholas Bulcao, Co-Founder & CEO of Airspace, a leader in time-critical logistics that has raised over $70M.
I’m not just an investor but an active, hands-on partner throughout a company’s journey. My involvement doesn’t end with a term sheet—I provide guidance on growth strategy, fundraising, and operational decisions. For instance, I invested in Platform Science and Flexe at the Series A stage and Flexport at Series B. These companies have grown significantly with the operational support and strategic guidance we provided in their early growth stages. My portfolio has generated over $17B in enterprise value, including acquisitions by top-tier companies like Project44, Databricks, and VMware.
Founders often tell me I ask questions that push them to think more critically about their business, their challenges, and their strategy. This curiosity allows me to delve into their business in a way that helps reveal areas often overlooked. My dedication to post-investment support ensures I am not just offering capital but adding value that drives their growth trajectory.
Leveraging a Robust, Multi-Layered Network
“Earnest introduced us to our lead investor without us even asking—his network and support were instrumental in closing our round.” — Charu Thomas, Founder & CEO of Ox, an AI-powered supply chain tech company.
One of my unique strengths is leveraging an expansive network spanning industries, stages, and geographies. I’ve built relationships with leading technical operators, growth specialists, and strategic partners, many of whom provide critical insights and resources to my portfolio companies. When Flexport needed to forge strategic partnerships, I introduced them to J.B. Hunt, facilitating a collaboration that streamlined global shipping and supply chain management.
My network is broad but also deep, cultivated from my journey that took me from Arkansas to Wall Street, India, and Silicon Valley. I’ve consistently built connections across the tech, finance, and logistics sectors, allowing me to source deals and win competitive rounds. I am in frequent contact with pre-seed, seed, and growth-stage investors who bring forward opportunities that they believe align with my strengths in Series A. Through Public School Ventures, my syndicate of 800 angels, LPs, and VCs, I’ve helped deploy capital into Series A companies.
Unmatched Diligence and Expertise
“Earnest goes through the effort of asking every question needed to fully comprehend each aspect of the business, and it’s incredible to witness.” — Matthew Vega-Sanz, CEO/Co-Founder of Lula, an insurtech startup transforming the gig economy.
Founders often comment on my thoroughness when evaluating investments. Unlike many VCs who skim the surface, I take the time to truly understand a company’s market, team, and potential. My diligence process was honed through my early career in equity research, where analyzing industries and challenging assumptions was paramount. This background gives me an edge at Series A, where deep dives uncover the non-consensus alpha opportunities others might miss.
For example, when investing in Flexe and Platform Science, I immersed myself in the logistics and supply chain spaces, helping them identify and secure critical partnerships and customers. I also advised them on go-to-market strategies to help them scale. By committing to a deal, I know the business inside out, enabling me to make high-conviction, lead-only investments. Furthermore, my best anti-portfolio companies—Turing, Lula, Roofr, and Assured—were all Series A opportunities I recognized early on before they each took off. My approach works exceptionally well at the Series A stage, where my diligence and market foresight can unlock tremendous value.
My career journey, from my parents’ influence as community investors in Arkansas to navigating Wall Street, launching a startup, and ultimately investing globally, has given me a unique perspective on Series A investing. This combination of personal resilience and professional experience enables me to execute with a balance of rigor and empathy. It’s a commitment to finding alpha and supporting founders with the dedication they deserve.
Conclusion: A Comprehensive Edge
Ultimately, my edge lies in combining deep post-investment involvement, expansive network leverage, and rigorous diligence—all powered by a relentless curiosity. This approach positions me as a valuable partner to founders and allows me to deliver superior results for my firm and LPs. Success in venture capital isn’t just about finding the right bets; it’s about being the right partner every step of the way. By focusing on high-conviction, lead-only Series A investments, I’m dedicated to guiding founders through this critical stage and achieving transformative growth.
5. Partner Highlight: Bottega8
This month, we spotlight Bottega8, revolutionizing AI Model training service for the financial sector and sponsor of Swimming with Allocators. Their approach slashes development costs while maximizing efficiency and security, offering essential tools for non-native AI startups and investment firms looking to harness the power of AI without incurring prohibitive costs.
Thanks again for taking time to read this edition.
With gratitude,
Earnest Sweat
Public School Ventures