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December 08.2025
3 Minutes Read

Unpacking the Kingmaking Strategy in AI Investments: A Guide for Entrepreneurs

Golden king piece surrounded by silver and gold pawns signifying a kingmaking strategy in AI investments.

The Rise of Kingmaking in AI Investments

As the venture capital landscape evolves, a bold new strategy has emerged in the realm of artificial intelligence: kingmaking. This approach involves making hefty investments in select startups at a very early stage, even before they establish product-market fit (PMF), a radical shift from the traditional method where VCs typically wait for businesses to prove their viability. The term "kingmaking" aptly describes the strategy as it enables a chosen startup to gain significant traction, effectively crowning them leaders in a rapidly expanding field.

Exploring the Trend Behind Kingmaking

Notably, the kingmaking tactic has gained momentum largely due to record-high investments in AI startups. In 2025, global VC investment in AI soared to $89.4 billion, with major players like Lightspeed and Khosla Ventures leading the charge. While traditional tech investments remain a safer bet, the allure of rapid growth in the AI space compels investors to take calculated risks. Examples like DualEntry’s remarkable $90 million Series A round highlight this trend: despite a relatively modest annual recurring revenue (ARR) of $400,000, the startup was valued at an astounding $415 million.

Why Invest Early?

The rationale behind this aggressive funding is multi-faceted. VCs believe that investing early in AI startups allows them to claim a larger stake in potentially game-changing companies before they achieve widespread adoption. According to experts, startups that manage to attract substantial funding are often perceived as safer investments by large enterprise clients. A hefty war chest can lead to increased market visibility, creating an illusion of dominance that rivals find hard to overcome. As seen with companies like Harvey in the legal AI sector, this strategy can lead to exclusive partnerships that further fortify a startup's position in the market.

Risks and Opportunities

While kingmaking presents numerous opportunities, it is not without its challenges. Historically, heavy capitalization does not guarantee success—many startups, such as Convoy and Bird, have struggled despite significant financial backing. VCs are carefully assessing each investment, balancing the excitement of potential returns with the reality of varying success rates in pre-PMF scenarios. Interestingly, the landscape of AI reflects an increasing number of back-to-back funding rounds within narrow timeframes, suggesting a trend towards rapid serial funding even among early-stage companies, such as the AI ERP sector.

Investing in the Future of Michigan Startups

For entrepreneurs and small business owners in Michigan, the rise of kingmaking offers a dual lesson: the importance of securing investment while also optimizing for sustainable growth. Understanding investor sentiment and market trends can empower local businesses to position themselves for visibility in a competitive landscape. Resources like the Michigan Entrepreneur Learning Hub can provide valuable insights for small business owners looking to navigate the complexities of funding and growth strategies in the age of AI.

Conclusion: Bold Steps Ahead

As we analyze the trajectory of kingmaking in AI, it is clear this investment strategy is redefining what it means to grow and collaborate in the tech sector. For small business owners, understanding these market dynamics can not only fuel entrepreneurial ambitions but also prepare them for future investment rounds. The interplay between capital and innovation is only becoming more intricate, and for those in the Michigan entrepreneur community, there’s no better time to become informed and engaged in this flourishing industry.

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