032 Start Your Side Hustle
I Bought a Corvette in El Paso and Drove It Home as the World Shut Down
April 2020. I'm driving a C7 Corvette back to southwest Missouri from El Paso, Texas.
And somewhere on that drive, the shutdowns start.
I had just launched my first business — a sports car rental — during the middle of a global pandemic, in a small town that had never seen anything like it. Everything in me said this was a terrible idea. And by every conventional measure, it was.
The car rented out all summer. There was literally nothing else like it in our area, and it turned out that driving was one of the only ways people could get out without being around anyone. I more than covered the cost of the car. I added a BMW convertible. Then a McLaren. A high-end Mercedes. We grew to five cars at one point.
None of that would have happened if I had waited for the right time.
The Three Things That Stop People Before They Start
Ashley and I get asked about our businesses constantly — how we started them, how we grew them, what we'd do differently. And when we pull back the curtain, what we find is that the gap between people who start and people who don't isn't talent. It's not resources. It's not even a good idea.
It's three things that show up in almost every conversation: being overly conservative, fear, and perfectionism.
They're related. They feed each other. And they're all quietly telling you the same thing: wait a little longer.
Being overly conservative sounds responsible. It's framed that way. You're protecting your family, being smart, not taking unnecessary risks. And there's wisdom in that — up to a point. But Ashley said something about this that I think about a lot. Risk is a muscle. If you never flex it, it doesn't grow. And the people who have started multiple businesses — genuinely multiple, like ten or fifteen — don't experience the same fear you do, not because they're reckless, but because they've built the muscle through reps. The fear got smaller every time they didn't let it win.
Fear of failure is the loudest voice in the room when you're first starting out. The thought that you need to know everything upfront. That if you don't execute perfectly, it means something bad about you. Our mentor Danelle Delgado says assets always adjust — meaning you don't need a perfect plan, you need a starting point and the willingness to pivot when the data tells you to.
And then there's perfectionism. I call myself a recovering perfectionist, and it is the sneakiest enemy of the three because it looks like diligence. James Clear writes about this in Atomic Habits — there's a point where preparation crosses into procrastination, and most people don't know exactly where that line is until they've been standing behind it for years. Planning is not action. A thousand AI chats about your business idea is still not action. Seth Godin says ship it. We say the same thing on this show in Episode 17. At some point you have to take the shot.
And here's the thing about taking the shot — when you sight in a rifle, you have to fire multiple times. Because you can't adjust what you haven't tried. You see where it landed. You correct. You fire again. Business works exactly the same way.
The Cars That Didn't Rent (And What They Taught Me)
I want to tell you about the Audi R8 Spyder.
It is an incredible car. Beautiful. Fast. The kind of thing that turns heads at every traffic light. I was convinced it was going to be one of the best performers in the fleet.
It rented once. Maybe twice.
Then there was the Toyota Supra — brand new, phenomenal to drive, that go-kart feel BMW is known for. In over a year, it rented maybe two or three times.
I could have beaten myself up over those decisions. I spent real money on both. But each one was data. I learned something about what my specific market actually wanted versus what I thought they'd want. And because I had already started — because the business was already running — I could see those lessons in real time and act on them. I sold those cars and made better decisions with the proceeds.
You can't iterate on something that doesn't exist yet. Failure is only a dead end if you stop there.
Ashley and I also opened a business a few years ago that just didn't work. We ended up selling it. We covered our expenses but didn't walk away with much. And here's the honest truth: I don't regret it for a second, because the lessons from that business informed everything we've done since. You can't buy those lessons. You can only earn them.
Finding What You Actually Have to Offer
Before you pick the vehicle — real estate, a product, a service, vibe coding an app — there are better questions to start with
What are you genuinely passionate about? What do you love doing to the point where you'd probably do it for free? What are you good at that other people would pay for? Where do those two things overlap?
Ashley made a point that keeps ringing true: so many people are sitting on hidden talents and ideas they've never shown anyone. You watch Shark Tank and you see product after product that started as somebody solving a problem in their own life — not trying to build an empire, just trying to fix something that annoyed them. And then other people wanted it.
The businesses with the most staying power solve real problems for real people. Not hypothetical people. Real ones. If you can find a need that exists in your town, your industry, your community, and you can meet it in a way others aren't — that's your opening.
AI is genuinely useful at this stage now in a way it wasn't when I bought that first Corvette. You can feed it your interests, your skills, your constraints, and have an actual conversation about what's possible. Ask it for examples of how people have built businesses around similar things. Ask it what you're not thinking about. It won't hand you the answer — you're the thought leader, it's the thought partner, as we talked about in Episode 33 — but it can get you unstuck and moving in a way that used to require finding the right mentor at the right moment.
Going It Alone vs. Finding Your Person
The partnership question is one of the most personal decisions in business, and I'll be honest — when I brought in my first business partner, a businessman I deeply respect told me he doesn't believe in partnerships. They work until they don't, he said.
I went against his advice. And I'd do it again.
My business partner and I have a dynamic that Gino Wickman describes in Traction — he's the visionary, I'm the integrator. He sees the horizon. I build the road. That combination creates something where one plus one is genuinely more than two. We approach every opportunity from different angles, which means we catch things the other would miss.
It's also, in many ways, like a marriage. Communication is everything. Trust is everything. You can't control what the other person brings — you can only control what you bring. And if you're going to enter one, go in with your eyes open about who you're partnering with, what they value, and how they handle pressure when things get hard. Because things will get hard.
If partnership isn't for you, that's a completely valid answer. Some of the most successful business owners I know run lean, intentional solo operations. The important thing is knowing which path you're actually built for — not which one sounds better.
What's Swimming in Your Head Right Now?
There are things floating around in your mind that never quite make it to action. You know what they are. The idea you keep coming back to. The thing someone asked you about once that made you think wait, is that actually something?
What's stopping it from becoming something real?
If it's fear — that's normal. Flex the muscle anyway.
If it's perfectionism — you don't need a finished plan. You need a first step.
If it's resources — start smaller than you think you need to. We saved our tax return to rent a cabin in Colorado for our first vacation. I walked into my bank and asked for a car loan to start a business. The barrier is almost never as high as it looks from the outside.
More resources exist right now to start a business than at any other point in history. The question isn't whether the path is available. It's whether you're willing to take it.
Growth happens when you take action. Daily anything changes everything.
Resources
Related Episodes
Episode 4 — Progress Over Perfection — The perfectionism trap goes deeper than just business. The whole episode is about replacing it with a pursuit of excellence. → Watch on YouTube
Episode 17 — Just Start — If you've been waiting for the right moment, this one's for you. → Watch on YouTube
Episode 33 — Optimizing with AI: A Thought Partner — How to use AI for brainstorming, business building, and getting unstuck. → Watch on YouTube
Episode 23 — Optimize Stewardship — The financial mindset side of building businesses and managing what you have. → Watch on YouTube
Books Mentioned
📖 Atomic Habits — James Clear (affiliate link)
📖 Traction — Gino Wickman (affiliate link)
📖 The Elite Leadership Blueprint — Brandon Thornhill (affiliate link)
Listen to the Full Episode
This post is drawn from Episode 32 of the Optimizing Beyond Podcast: Start Your Side Hustle ft. Ashley Negron.
🎧 Listen on your favorite platform ▶️ Watch on YouTube
Connect With Josh & Optimizing Beyond
If this resonated with you, share it with someone who needs it.
Daily anything changes everything.