Adversarial Thinking in Entrepreneurship — The Bootstrapped Founder 299


Dear founder,

Earlier this week, I was inspired by a clip from an interview with Rick Rubin. He discussed that art should be created primarily for the artist's satisfaction, placing the audience second. Art truly resonates with others only when it authentically represents the creator's best effort. He contrasted this with commerce, often prioritizing the audience's needs over the creator's vision. This resonates with me as both a creator and an entrepreneur, navigating the balance between artistic expression and commercial products.

And frankly, I fall on the side of the commercial approach.

Instead of creating art, let's talk about a few somewhat non-obvious ways of thinking about and securing our businesses.

The advent of AI has led me to consider adversarial strategies in business, using tools and frameworks to challenge my ideas and sharpen my writing.

In my day-to-day, this process involves considering potential weaknesses in my arguments and business strategies to build more resilient systems. I want to understand the external challenges and prepare for competition. This is crucial for any entrepreneurial journey, whether building an audience, a software business, or a YouTube channel.

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So, now we need to expect business predators around every corner?

Well, I wouldn't go that far.

Adversarial thinking is valuable, but it's just as important to maintain a positive outlook and focus on creating meaningful contributions. It is a sharp blade that can cut you if you're not careful. Well, let me share just how I apply it safely. I've extensively used adversarial thinking, especially in product development, to anticipate potential abuses and secure valuable data. For instance, as I built an API, I had to take a few precautions against abuse.

I implemented rate limiting and data obfuscation to prevent unauthorized data scraping and ensure that access is controlled and secure. It's not that all my customers want to overwhelm my server with their API requests. But I have to assume that through negligence or malice, someone might do just that eventually.

So, I put myself in their shoes and thought about just how they could access data they shouldn't see. And then, I build proper gateways and authorization checks into the most basic prototype functions. Security has to come first when customer data is involved.

But I expect this respect to be two-sided, which is why I also limit who can sign up. Email verification and checks against disposable email addresses are other measures I took to maintain the integrity of my user accounts.

I want to build a relational business, and that starts with knowing who I'm serving. If the user signing up doesn't allow me to do that, they can't use my platform.

This concept extends to content creation and personal branding, too. I don't just have a database to protect: managing my public persona and minimizing potential backlash are essential. My personal platform is likely the most valuable asset I own. People resonate with my work; they enjoy my virtual company, which attracts opportunities, collaborations, and —let's be honest— money! Controversy will attract the controversial, which impacts my relationships with friends, peers, and sponsors.

This isn't about censorship, though. I still say what I want to say. I just ensure I don't rush into saying things that might undermine my long-term goals. And here's an extremely practical tip for those who write either tweets, books, or anything in between. Email comes to mind, too!

I've learned to use AI as a 'fictional enemy' to critique my writing. Telling ChatGPT to take a draft and attack it as my worst enemy would has been a transformative approach. The AI looks at my work through the eyes of someone who would want to attack me, which in turn helps identify weak arguments and logical fallacies, thus refining my content. I even found that ChatGPT can reliably suggest good counter-arguments or even ways to prevent criticism from coming up in the first place.

We all knew that AI would end up being the enemy. But take this literally, and it will help you strengthen your own writing.

Adversarial thinking, or rather "externalized perspective setting," offers a bird's-eye view of one's work, be it a business, an article, or a project, which allows us to consider the motivations and needs of our potential audiences and adjust accordingly.

This perspective is crucial for navigating the competitive landscape of entrepreneurship, where understanding and preemptively addressing the challenges posed by competitors and the market will significantly impact how quickly you find success.

So, take a proactive and critical approach to entrepreneurship by going adversarial. This helps balance your creative integrity with the realities of commerce and competition. It's about preparing for and mitigating potential challenges by looking at yourself from an external perspective.

Adversarial thinking makes for a more resilient founder.


I'll share a few updates about my SaaS on the pod, and I'd love to know what you think about them! Please leave a voice message at podline.fm/arvid 🥰

And if you want to track your brand mentions on podcasts, check out podscan.fm!

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Arvid Kahl

Being your own boss isn't easy, but it's worth it. Learn how to build a legacy while being kind and authentic. I want to empower as many entrepreneurs as possible to help themselves (and those they choose to serve).

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