20VC: How To Do a 10x Seed Fund in 2025 | Three Frameworks to Evaluate Startups an Founders | Lessons from Losing Billions Missing Airbnb and Pinterest & Investing Lessons from Charlie Munger with Mike Maples @ Floodgate
Jan 6, 2025
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In a captivating discussion, Mike Maples, co-founding partner at Floodgate and veteran seed investor, shares his insights from two decades in venture capital. He tackles the effectiveness of seed funding as an asset class and lays out strategies for achieving a 10x return. Mike reflects on valuable lessons learned from missing out on Airbnb and Pinterest, while revealing three frameworks for evaluating startups. He also addresses challenges posed by overfunding and the critical importance of product-market fit in today’s investment landscape.
To achieve a successful 10x seed fund, investors must strategically drive their investments to yield high returns despite market challenges.
Identifying market inefficiencies and discerning investment opportunities is crucial for navigating the complexities within the seed funding landscape.
Evaluating startup founders for their vision and future market understanding is essential to enhancing the likelihood of investment success.
Deep dives
Risk and Reward in Seed Investing
Investing in the seed stage involves understanding the risk-reward balance that must be navigated to achieve success. It is essential to receive compensation for the risks undertaken, and the strategy is built around the principle that a small percentage of investments can yield outsized returns. Specifically, achieving notable returns requires that 5% of investments generate 100x cash returns, while 10-15% need to yield about 20x returns. This approach underscores the necessity of strategic decision-making and finding market inefficiencies to capitalize on investment opportunities.
The Challenges and Dynamics of Seed Funds
The landscape for seed funds currently presents several challenges, particularly for those under $100 million. While it is still possible for smaller funds to thrive by making targeted investments, the competition and capital requirements in the market dictate that funds must be strategic about where and how much they invest. Larger investments in companies often lead to a dilution of returns unless there is a clear path to significant growth. Thus, determining the right funding size and strategy is crucial for navigating the complexities of venture capital.
The Importance of Follow-On Investments
Follow-on investments are a critical part of the strategy for seed funds yet are often overlooked by many investors. It is imperative to consider how much capital to allocate to these follow-ons while retaining the ability to invest in future opportunities. A successful approach includes maintaining the advantage of existing knowledge about companies, which can inform better follow-on decisions. Ultimately, how funds handle pro-rata rights and follow-on allocations can significantly influence overall investment success.
Market Inefficiencies and Strategic Investing
Identifying market inefficiencies remains fundamental to successful venture investing, particularly in the competitive seed stage. Investors must not only recognize when the market is overvalued or when unrecognized opportunities exist, but also be willing to remain patient and discerning in their decision-making process. In today's rapidly evolving market, particularly within tech sectors like AI, it is crucial to develop specific frameworks for evaluating investments while avoiding the pitfalls of overvaluation. This strategic thinking can ultimately distinguish successful firms from those that fail to capitalize on emerging opportunities.
Evaluating Founders and Their Fit
The evaluation of startup founders plays a pivotal role in the investment decision-making process, as it influences the likelihood of success. Founders who demonstrate a clear vision and deep understanding of future market dynamics are better positioned for success, particularly when they possess what is termed 'founder future fit.' Understanding the unique attributes each founder brings to the table can help investors discern their potential effectiveness in navigating challenges. Therefore, investing in founders who are both visionary and capable of driving their companies towards long-term success is essential.
Mike Maples is one of the OG seed investors of the last two decades. As a co-founding Partner at Floodgate, Mike has been on the Forbes Midas List eight times in the last decade. Some of Mike’s investments include Twitter, Twitch.tv, Clover Health, Okta, Outreach, Chegg, Demandforce, and Applied Intuition.
In Today’s Episode with Mike Maples We Discuss:
04:02 Does Seed Even Make Sense as an Asset Class?
05:16 Fund Size and Strategy: How to Do a 10x Fund?
08:12 Follow-On Investments: Are they BS?
16:41 Finding Inefficiencies in the Market
26:31 Exit Strategies and Liquidity Events: When to Sell?
35:14 How Floodgate Lost Billions Missing Airbnb and Pinterest
35:43 3 Frameworks for Evaluating Startups
36:23 Case Studies: Zoom and Okta
43:34 How to Truly Analyse Product-Market Fit
45:22 Challenges with Overfunding Startups
50:02 2024 in Review: Company and Fund of the Year
54:25 Predictions for 2025
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