For the first couple of years running my auto body shop, I used to budge on price. A customer would come in, hear the quote, and say something like: “The garage down the road is doing it for less.” And more often than not, I’d adjust the number to keep the job. I’d win the […]
I get a version of this conversation almost every week. Someone pulls me aside at an event, in my messages, or over coffee and says, “I have this business idea I’m exploring.” What do you think?” For a long time, I’d tried to give a thoughtful answer on the spot. Ask a few questions, nod […]
In the last piece, I asked a question worth sitting with: how many real options do you actually have right now? Not hypothetically. Right now. If an opportunity appeared tomorrow, could you move on it? If you needed to walk away from something that was draining you, could you? For most people, the honest answer […]
For most of my life, I chased a feeling. Not a number. Not a specific asset.A feeling. The feeling of being free. Free from stress, free from limitation, free from the kind of financial anxiety I grew up watching my parents struggle with. I came from humble beginnings. I know what struggle looks like up […]
At one point, I thought I was doing well. Not rich, not where I wanted to be, but at least moving in the right direction.Businesses running, bills paid, building something. By most measures, I was ahead of where I started. That felt like enough. Then I sat down one day and actually tried to answer […]
Most people are living someone else’s definition of a good life, and they don’t know it. Not because they’re lazy or uninformed. But because nobody ever asked them to define it for themselves. Life moves fast. The defaults kick in early. And before long, you’re optimising hard for a destination you never consciously chose. I […]
Most first-time founders learn these lessons the hard way. You don’t have to. Someone tells you they want to start a business and follow their passion, and my first instinct is always the same: unless you’re willing to go broke, don’t do it. That’s not pessimism. That’s the conversation no one has with you before […]
Paths to Prosperity Prosperity means something different to everyone. The question is: do you know what it means to you? There’s a question I ask a lot of people, whether they’re just starting out or well into their careers: “What does a good life look like to you?” The answers are always different. Some people […]
Here’s a thought experiment: what if we stopped talking about entrepreneurship like it’s a personality type and started treating it like a career in professional sports? Because the more I think about it, the more the analogy holds up. In sports, you don’t go from rookie to head coach overnight. There’s a progression — player, […]
If you’ve been in the small business or entrepreneurial spaces for some time you’ve probably heard about Simon Sinek’s famous TED talk: Start with Why. If you haven’t, go check it out here now, and then come back to this post. If you’re already aware of the concept, you may have an idea of what […]