The Intersection of Investing, Writing, and Founders: Not Boring Capital's Unique Approach

Kazuki Nakayashiki

Hatched by Kazuki Nakayashiki

Sep 23, 2023

3 min read

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The Intersection of Investing, Writing, and Founders: Not Boring Capital's Unique Approach

Introduction:
Not Boring Capital, an $8 million venture fund, has a unique approach to investing in companies with compelling stories. Led by Packy McCormick, whose investing prowess is amplified by his writing skills, the fund focuses on Seed through Series B companies in various sectors, with a particular emphasis on fintech. This article will explore the common points between Not Boring Capital's investment strategy and the qualities they look for in founders, highlighting the importance of determination, imagination, and strong relationships.

Investment Strategy at Not Boring Capital:
Not Boring Capital divides its investments into three categories based on their potential returns. The core investments, comprising about 75% of the fund's total dollars invested, have the potential to deliver substantial returns. These are carefully selected companies that could potentially return the entire fund in the best-case scenario. The explore investments, accounting for 5-10% of invested dollars, are smaller bets aimed at securing a seat in the next funding round or increasing deal flow. While the upside is high, these investments individually are unlikely to return the entire fund. Lastly, the growth investments, constituting approximately 20% of invested dollars, are safer, later-stage investments with a lower ceiling and higher floor. Collectively, this 20% should be able to return the fund once.

The Power of Writing and Investing:
Packy McCormick's dual roles as an investor and writer create a powerful flywheel for Not Boring Capital. His writing enhances his investing abilities by providing a platform to share insights, knowledge, and stories. Through his writing, McCormick attracts a large readership, creating a network of 60,000 people who can potentially contribute to the success of the fund's portfolio companies. This symbiotic relationship between Not Boring Capital's portfolio companies and readers helps foster a thriving ecosystem.

Qualities of Founders:
Not Boring Capital places great importance on the qualities of founders when making investment decisions. While intelligence is a baseline requirement, determination stands out as a vital characteristic. Startups face numerous obstacles, and founders must possess the resilience to overcome them without losing motivation easily. The ability to adapt and modify dreams on the fly is crucial in the unpredictable world of startups.

Imagination is another quality that holds significance for Not Boring Capital. Rather than focusing solely on problem-solving skills, the fund values founders who can generate surprising new ideas. In the startup realm, initial ideas often appear unpromising, but successful founders possess the vision to see their potential.

Additionally, strong relationships between founders play a pivotal role. Not Boring Capital has observed that most successful startups have two or three founders who genuinely like and work well with each other. While disagreements are natural, unresolved tension can hinder progress. It is the founders' ability to maintain a healthy and productive dynamic that contributes to their success.

Actionable Advice:

  1. Cultivate determination: As a founder, it is essential to develop resilience and not be easily demoralized by obstacles. Maintaining a determined mindset will enable you to navigate challenges and stay motivated.

  2. Embrace imagination: Instead of relying solely on predefined solutions, allow your imagination to flourish. Think outside the box and generate innovative ideas that may initially seem unconventional but hold significant potential.

  3. Foster strong founder relationships: When building a startup, prioritize finding co-founders with whom you share a genuine liking and can work well together. Nurture open communication, resolve conflicts, and maintain a healthy dynamic to drive success.

Conclusion:
Not Boring Capital's unique approach to investing, coupled with the qualities they value in founders, creates a synergy that sets them apart. By investing in companies with compelling stories and leveraging the power of writing, the fund cultivates a network of engaged readers who can support their portfolio companies. Determination, imagination, and strong founder relationships are the ingredients that contribute to the success of both Not Boring Capital and the startups they invest in. By incorporating these qualities and taking actionable steps, founders can increase their chances of building thriving and impactful companies.

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