5 “Boring” Decisions That Made Me a Multi-Millionaire

To achieve entrepreneurial success and transition from dreaming to building, five key decisions are critical. The first involves stopping the endless consumption of information and starting to ship products, overcoming the fear of public judgment. Second, embrace the hard, boring, and often scary work that drives business progress, prioritizing impact over passion. Third, learn from mistakes by adjusting course, shifting from less profitable consumer-facing software to business solutions and from low-priced to higher-priced products. Fourth, make increasingly larger but manageable bets, progressively investing saved or earned capital into ventures. Finally, avoid impulsive decisions during difficult times by implementing a cooling-off period for major choices, allowing emotions to subside before acting.

• Ship it: Transition from consuming business books and endless learning to actively building and launching products, overcoming the fear of criticism.
• Embrace the Grind: Prioritize hard, often unglamorous but impactful tasks like SEO, advertising, and customer support over passion alone.
• Learn and Adjust: Recognize and learn from mistakes, pivoting business strategies like moving from B2C to B2B SaaS and from low-priced to higher-priced products.
• Manageable Bets: Make progressively larger, yet still manageable, financial investments in software products, building capital through freelancing and reinvesting revenue.
• Weather the Storms: Avoid impulsive decisions during difficult times by implementing a cooling-off period, waiting months before making significant changes.

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Stop Reading, Start Shipping [00:49]

• The first crucial decision is to stop consuming endless business books and learning, and instead start building and launching products.
• Analysis paralysis and hiding behind constant learning are common pitfalls for aspiring entrepreneurs.
• There are no guaranteed secrets to success; shipping publicly creates opportunities, but external inputs alone won't ensure it.
• Overcoming the terror of public criticism, judgment, and failure is essential for entrepreneurs.
• Shipping publicly builds confidence and helps overcome the fear associated with initial launches of code, content, or products.

The first time you do these things, they're going to be scary. And the first time you push production code on the internet and try to promote it and have people use it, it's going to be scary. But the more you do it, the easier it gets and the more confidence you build.

This decision emphasizes the importance of action over passive learning, highlighting that real progress comes from launching and iterating, despite the inherent fears.

Embrace Hard, Boring, Grindy Work [02:27]

• Success often comes from embracing tasks that are hard, boring, and scary, rather than avoiding them due to lack of passion.
• Tasks should be ranked by their potential impact on the business, not by personal interest.
• Unglamorous tasks like SEO, advertising, copywriting, bug fixes, customer support, and code maintenance are critical.
• Grounding out on these less exciting tasks for several years builds the foundation for future success and more desirable work.
• A mindset influenced by athletic careers and the necessity of paying bills can foster a willingness to do what's required.

I think in the long term, you probably want to enjoy what you do. in the short term and that short term might be 6 months and it might be a few years as you're trying to bootstrap is that have hobbies for enjoyment but if you're working on your startup you need progress not passion

This point stresses the necessity of diligent, often unexciting work for long-term entrepreneurial achievement, contrasting it with the pursuit of immediate passion.

Learn from Mistakes and Adjust Course [04:46]

• Continuously learning from mistakes and adjusting the business's direction is vital for growth.
• Early lessons included realizing that B2C SaaS is not as favorable as B2B SaaS, and that low-priced software has higher churn.
• This led to a strategic shift towards selling to businesses and offering higher-priced products.
• Acquiring existing apps with traction can be faster than building from scratch, leading to a combination of building and acquiring.
• Founders often fail by repeating the same mistakes without adjusting, making failure catastrophic if not learned from.

The mistake that I see a lot of founders making is they do the same thing over and over and they don't get out of their own way, right? They don't adjust. Failure is only a good thing if you learn from it.

This section underscores the critical importance of adaptability and learning from failures to pivot and improve business strategies over time.

Make Increasingly Larger, Manageable Bets [06:43]

• The strategy involves making progressively larger, yet still manageably sized, financial bets on software products.
• This approach can be funded through freelancing and saving, or by reinvesting revenue from existing products.
• Examples include investing $11,000 in a software product in 2005-2006, then $30,000 in an SEO tool in 2011, and nearly $200,000 to develop a functional software with product-market fit in 2012-2013.
• Crucially, these bets should not risk bankruptcy; if they fail, the impact is significant but survivable.
• This involves earning capital through diligent work and strategic reinvestment rather than relying on debt or external funding.

Over the course of your career, you should be making increasingly larger but still manageably sized bets.

This decision highlights a prudent financial strategy for scaling a business, emphasizing calculated risks and consistent reinvestment to fuel growth.

Avoid Impulsive Decisions During Difficult Times [09:12]

• It's crucial to avoid impulsive decisions, especially during challenging periods like burnout, failure, or financial stress.
• A significant win is to resist acting on emotions in the heat of the moment and instead implement a cooling-off period for major decisions.
• Waiting months before making significant choices, giving oneself at least weeks or months to sit with the decision, is recommended.
• This approach prevents temporary emotional states from dictating permanent, potentially regrettable, outcomes.
• Developing the discipline to weather low periods without making hasty decisions is a key entrepreneurial skill.

I never let my temporary emotional states change my reality or make me make permanent decisions out of temporary problems.

This final point emphasizes the importance of emotional regulation and strategic patience in navigating the inevitable ups and downs of entrepreneurship.