The Grand Master Plan

A Myth Especially in the Age of AI

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If you are new around here, this is a bi-weekly newsletter about IRL events, startups and building products! If you find this useful, feel free to refer a friend or subscribe for future newsletters using this link: Subscribe

Events that I host, will be at or think might be worthwhile to check out

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Toronto

12/28 - Startup, Tech & Business Networking Toronto - Register

01/18 - XRPL x Aceocial // Web3 Party - Register

San Francisco

12/28 - Generative AI Social - Register

01/05 - Silicon Valley Bootstrappers - Register

01/09 - The AI Hustle -  Register

New York

12/29 - Pitch and Run Friday - Register

01/05 - Founder Coffee Huddle - Register

Want to see your event here? Is there something going on that I should be highlighting? Feel free to reach out and I would be happy to feature them!

The Grand Master Plan

Nowadays throughout social media, it’s easy to find this idea of a meticulously charted narrative of a ‘Grand Master Plan’ needed for success. However, after engaging several highly successful people, it’s become more evident that this narrative is a myth, especially in the age of AI.

In a conversation with David Weekly, head of the Capital One Lab and a mainstay in the startup community, he mentioned this: 

“I think there’s a bit of a false narrative that folks have early in their career that people who got to interesting places had this grand master plan that they put together. So they kind of sat down at like 13–14, fought really hard some Saturday afternoon, whiteboarded it all out and were satisfied at 55 like ‘yep, I made that happen.’ It never works like that like ever. The narrative always makes sense in post because you can build what was going on from the beginning after everything happened and you can splice it to make a coherent and contiguous narrative. In the moment, it is never like that.”

If anything is predictable about the world, it’s that the world is very unpredictable. No matter who you are, it is nearly impossible to create plans that execute in the manner that you have planned out. This only increases the value of taking in data and being able to adapt, making it even more important. Especially nowadays, the world, its values, and the technologies that define it are changing at too fast of a rate to not force one to constantly reevaluate.

The essence of entrepreneurship is not in meticulously following a preordained plan but in embracing the inherent unpredictability of our world. This unpredictability, especially pronounced in the era of AI and rapid technological change, necessitates a different kind of strategic thinking — one that is dynamic, responsive, and adaptable.

In my journey, I’ve learned that the real skill lies not just in charting a course but in navigating the uncharted waters with agility. The world today doesn’t just allow for this flexibility; it demands it. With each technological breakthrough and societal shift, new opportunities and challenges arise, often rendering previous plans obsolete or inadequate. The successful entrepreneur is one who recognizes these changes, understands their implications, and adjusts their course accordingly.

This approach is particularly crucial in the current landscape dominated by AI. AI, with its data processing prowess and predictive capabilities, has become an invaluable tool for entrepreneurs. It offers insights at a scale and speed that were previously unimaginable. However, it also accelerates the pace of change, continuously reshaping the market landscape. In such an environment, clinging too tightly to a fixed plan can be more of a hindrance than a help.

In practical terms, this means taking action to get a product out there as soon as possible has never been more profound. It is essential to release an MVP and start iterating based on real-world feedback.

So, my approach is to plan, but plan to adapt. Using AI and other technologies to gather data and gain insights, but being ready to pivot based on what these tools and the market tell you. The true value of an entrepreneur today lies in their ability to synthesize information from various sources, make informed decisions quickly, and then act on them with conviction.

Making those informed decisions also means recognizing that while AI can guide us, it cannot replace the human elements of intuition, creativity, and empathy. These qualities remain at the heart of entrepreneurial success. They enable us to see beyond the data, to connect with our customers on a human level, and to innovate in ways that AI alone cannot.

So it seems that the path to success is rarely linear or predictable. It’s a path marked by constant learning, adapting, and evolving. In this journey, the ability to blend strategic foresight with responsive action, and to balance AI-driven insights with human creativity and intuition, is what sets apart the truly successful entrepreneurs.

To end, I leave you with a quote from a clip I recently saw of Steve Jobs: 

“The doers are the major thinkers. The people who really create the things that change this industry are both the thinker-doer in one person.”


Check out this Podcast Episode!

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David E. Weekly is the head of The Capital One Lab, leading engineers, product managers, designers, and strategists focused on exploring the intersection of emerging technology and finance. He is also a seasoned technical product executive with 30 years of experience building technology for startups of his own creation, mid-sized companies, and international publicly-traded corporations.

David has served as an angel investor and built and run commercial research teams for Google and Meta’s predecessor, Facebook. He brings a global perspective from a range of diverse experiences across the planet.

Earlier in his career, he formed a high performing seed-stage fund backing entrepreneurs from Mexico. In Africa, he worked with the Tunisian government on connectivity, witnessed fiber trenching in Uganda, and taught elementary school students about technology in Ghana. On the continent of Asia, he reported for the Korean press and climbed mountains in northern India to support hilltop community wireless networks. He is a certified PADI Rescue Scuba Diver, a certificated private rotorcraft (helicopter) and instrument-rated fixed-wing pilot, and a Part 107 licensed commercial drone operator. David received his Bachelor of Science in Computer Science from Stanford University.

Thanks for reading,

Daivik Goel