The Humbling Hustle
Posts
The Humbling Hustle #2

The Humbling Hustle #2

The Wilkinson Dream with Spring Break Laziness 3/16/25-3/22/25

Humbling Hustle
March 22, 2025

This Week’s Successes

Got deep into books reselling on both Amazon and eBay.
Sourced a couple of new products and made the investment.
Set the foundations for a new email-marketing venture.

This Week’s Business Ideas

I haven’t spent too much time this week brainstorming business ideas, but the one thing I have not stopped thinking about is the book I read. I’ll talk more about the book itself in the reading section, but basically it is about Andrew Wilkinson and how he became a billionaire.

The lessons I took away from him in terms of businesses were the importance of buying back your time, the power of a holding company, and passive income. One of my big goals in the future is to have built up multiple businesses to a point where they run themselves and I reap the rewards from holding majority shares in it. I know multiple people in my community who do this and I will look into it later as I am in no position to learn about it.

One thing I’ve learned about business this week is the beginning sucks. For example, FBA has so many drawbacks and it is such a time draining and money wasting investment. But now that I am so deep already into there is no backing out. The only light at the end of the tunnel for me right now is the success stories of people in Amazon reselling. I would say there is a few more months before the red starts to see a little green.

This Week’s Reading

This week I read Never Enough: From Barista to Billionaire by Andrew Wilkinson. I was gifted this book by my maternal grandfather. The book is narrated by Mr. Wilkinson himself as he takes us on the journey from when he was a curious and ambitious barista to making billion dollar deals with Berkshire Hathaway. He becomes vulnerable as he identifies all of the business mistakes of his past and demonstrates his keen solutions and how they came to him.

“It’s a decision that many entrepreneurs fear making. I was embracing what I came to call Lazy Leadership: the idea that a CEO’s job is not to do all the work, but more importantly to design the machine and systems. Not a player on the field. Not the coach. But the owner, sitting up in a little box at the top of the arena, passively observing until the next critical fifty-thousand-foot decision had to be made.”

Andrew Wilkinson

This quote sums up the main point I took home with this book. I can only imagine how it feels to bring a million dollar company from the ground up and then step back from the daily grind, trusting the systems and people you’ve put in place to keep it running. It challenges the instinct to micromanage and instead embraces a mindset where leadership is about building a self-sustaining machine rather than being the one constantly turning the gears.

For many entrepreneurs, especially first-timers, it’s tempting to stay deeply involved in every detail. But true scalability comes when you transition from being the workhorse to being the architect. Wilkinson’s concept of “Lazy Leadership” isn’t about being disengaged but more about being intentional with decisions, stepping back to see the bigger picture, and only stepping in when absolutely necessary.

This perspective forces me to rethink what leadership actually means. It’s not about working the most hours or being the busiest. It’s about designing a system where your absence doesn’t mean failure but rather proves the strength of what you’ve built.

What really makes Andrew Wilkinson’s story hit home for me is how much he hustled as a teenager—always looking for ways to make money and start businesses. He talks about how he was constantly experimenting, whether it was building websites or flipping random stuff online. He wasn’t just trying to get a paycheck—he wanted to create something of his own.

I relate to that so much. I’m in that same phase of chasing ideas, testing things out, and figuring out what actually works. His story makes me realize that success isn’t about having a perfect plan from the start—it’s about staying obsessed with the process, learning from mistakes, and just going for it.

This Week’s Academics

It was Spring Break, I did not really do anything academics related other than look for internships for this summer. I found a few leads to some law firms that I could hit up next week and try to get one.

This Week’s Struggles

This week was definitely a challenge. I didn’t schedule my time properly over Spring Break, and because of that, it was really hard to stay productive. Without a clear plan for the day, I kept pushing things off, telling myself I had plenty of time. But before I knew it, the day would slip away, and I would get frustrated at how little I actually got done. Not having that structure made it way too easy to be lazy, and the lack of urgency just killed my motivation.

On top of that, my sleep has been all over the place, which just made everything feel more exhausting. It was not a total failure, but I know I can do better by being more intentional with my time.

One thing I have realized really helps is prepping for the next day before I go to sleep. It gives me some structure instead of waking up and scrambling.