Can Aaron Bai Write Better Than ChatGPT? Part 1

Feb 11, 20234 min read

Context

I'll be posting a lot more about my personal career / life experience on my professional site: aaronbai.org. And a lot of this will be repeating what you'll see here. However, I think this will be much needed context for this series. Right now, I'm 18 years old and building Affiniti. But, I was 16 years old and a UC Berkeley dropout when I started my first venture-backed company, Pebble. Venture capital was a sign of gleaming success — full of interviews and announcements of "Pebble Co-Founders, CEO Aaron Bai and CTO Sahil Phadnis, Launch YC-Backed Fintech Startup"! And it was true that we raised one of the biggest seed rounds at that time (and even more for our backgrounds). It was $6.2 million in seed funding from YC itself alongside LightShed Ventures, Eniac Ventures, Global Founders Capital, Montage Ventures, Soma Capital and angel investors. However, those numbers and investor names were just gilding all the work, sweat, frustration, and roadblocks behind building a startup. Within months of launch, we had to shut the Pebble app down due to macroeconomic factors and others. Before we even raised a dime, we spent months trying to figure out how to convince someone like Y Combinator to pick us over the ex-McKinsey, 3X founders they were going to interview. So, that's the overarching context behind my background. Now, diving into my thoughts on ChatGPT. What I've noticed while playing around with ChatGPT is that it fails to give non-well-known details when writing — even when you supply it with details. You know . . . a perfect engine will let you supply it with the exact same story I posted above, and it'll write any prompt from that "character's" (my) perspective. So . . . I wanted to give it a try. If gave ChatGPT my story, and then the prompt to "Write a blog post about how my experience in chess and building my previous startup overlaps." . . . will the output be convincing enough to seem like I wrote it? Part 1 of this series will be what ChatGPT writes, and Part 2 will be what I write myself.

ChatGPT's Take (obviously written by ChatGPT)

ChatGPT Writes About Aaron Bai's YC-Backed FinTech Startup

As an 18-year-old building a new venture called Affiniti, you may feel that the challenges you faced with your previous startup, Pebble, were unique to the world of entrepreneurship. However, there are valuable lessons from your experience with Pebble that can also be applied to other areas of your life, such as your hobby of chess.

One key lesson that both building a startup and playing chess teach you is the importance of strategy. Just as in entrepreneurship, in chess you need to be able to anticipate your opponent's moves, plan your own moves accordingly, and adjust your strategy as the game progresses. You must be able to think critically and make calculated decisions that will help you achieve your goals.

Another important lesson from your experience with Pebble is the importance of perseverance. Building a startup, like learning chess, can be a frustrating and challenging experience. It can be easy to get discouraged by setbacks and roadblocks, but it's important to keep pushing forward and learning from your mistakes. In both entrepreneurship and chess, persistence and determination can ultimately lead to success.

Additionally, your experience with fundraising for Pebble may also have prepared you for the competitive nature of chess. In order to secure funding for your startup, you had to convince investors that your idea was worth their investment, even in the face of competition from other startups. Similarly, in chess, you must be able to outmaneuver your opponent in order to come out on top.

Overall, your experience with building Pebble and your interest in chess share many important lessons, such as strategy, perseverance, and competition. By applying these lessons to your new venture with Affiniti and to your hobby of chess, you can continue to grow and develop as both an entrepreneur and a chess player.

My Takeaway

To be completely honest, I think ChatGPT is on the right direction . . . but just failed to insert enough details in each idea to make it look like I wrote it. Yes, the engine was able to pickup Pebble and Affiniti. But other than that, I'm sure hundreds of other people can describe how setbacks" are the same between entrepreneurship and chess. What would've been a lot more convincing is if they threw in terms like "shutting down due to macroeconomic factors" and others. However, 1 line that I wanted to point out that I really liked was "you may feel that the challenges you faced with your previous startup, Pebble, were unique to the world of entrepreneurship. However, there are valuable lessons from your experience with Pebble that can also be applied to other areas of your life, such as your hobby of chess." I don't think I would've came up with that. It flows into the main bodies of the blog very, very well. See you in Part 2 — where I'll go with my rendition on the topic!