I started my online business 23 years ago, and reflecting on that journey, I realized there were five key decisions that transformed me from just dreaming about entrepreneurship to actually building and selling a multi-million dollar SAS business. I'm Rob Walling, and I want to share these decisions with you.
1. Stop Reading and Start Shipping
Many aspiring entrepreneurs get stuck in the "dreamer phase," constantly learning but never actually building. This was me in 2002. I was caught in analysis paralysis, hiding behind constant learning.
Transitioning from Consumption to Creation
The solution was to transition from consuming business books to actually building and launching products. There are no secret guarantees of success in any book, YouTube channel, or podcast. While external input can be valuable, at some point, you have to stop consuming and start shipping.
Overcoming the Fear of Shipping
The terror of public criticism, judgment, and failure is real, but as an entrepreneur, you have to overcome it. Building confidence comes from facing the terror of launching code, blog posts, podcasts, and videos. The more you ship, the easier it gets.
2. Embracing Hard, Boring, Grindy, and Scary Work
Success isn't just about good ideas; it's about what comes after the launch. Decision number two was embracing hard, boring, grindy, and scary work. This may have been the most important factor in my success.
Focusing on Impact
The mindset was to never avoid tasks due to lack of passion, but to rank them by impact on the business. This meant grinding out unglamorous tasks like SEO, advertising, copywriting, bug fixes, and customer support.
Progress Over Passion
Too many people shy away from hard work. It's important to have hobbies for enjoyment, but when building a startup, you need progress, not just passion. Don't avoid crucial tasks simply because they seem boring. Embrace the grind.
3. Learning From Mistakes and Adjusting Course
Just because you're working hard doesn't mean you're working on the right things. Decision number three was learning from mistakes and adjusting course along the way.
Adapting and Evolving
Early on, I learned that B2C SaaS wasn't a good fit for me. I then focused on solving problems for businesses. Other lessons included understanding that low-priced software had higher churn and that acquiring existing apps could be faster than building from scratch.
Avoiding Repetitive Failure
The mistake many founders make is repeating the same actions and not adjusting. Failure is only beneficial if you learn from it. Look at why things aren't working and figure out how to adjust course. Don't beat your head against a wall.
4. Making Increasingly Larger, But Manageably-Sized Bets
As you evolve, you should make increasingly larger, but still manageable bets. This involves progressive investment in software products.
Incremental Investment
In 2005-2006, I spent $11,000 on Net Invoice, money I saved by freelancing nights and weekends. This grew, allowing me to spend $30,000 on HitTail in 2011, and eventually invest almost $200,000 in Drip.
Smart Risk Management
I never bet the house, took on credit card debt, or took a second mortgage. I earned it along the way by freelancing and building products. Each bet was sized so that failure would be a setback, not a catastrophe.
5. Avoiding Impulsive Decisions During Difficult Times
The startup journey is rarely easy. One thing I did well was avoiding impulsive decisions during difficult times.
Weathering the Storm
You'll experience burnout, failure, frustration, and financial concerns. I never acted on these emotions in the heat of the moment. I often waited months before making major decisions when emotionally charged, giving myself a cooling-off period.
Building Cumulative Progress
I never let temporary emotional states change my reality. Instead of getting rid of something that became frustrating, I let each endeavor build on the next, creating cumulative progress. Learn to weather temporary low periods without making big decisions.
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