I didn’t set out to become a serial entrepreneur. The first business I started was almost accidental. I was a college kid who wanted to throw cool parties, impress my peers, and (if I’m being honest) possibly attract a mate. I bought some DJ equipment, started practicing, and quickly discovered two things: the equipment was expensive, and the kind of DJing I actually loved doing wasn’t what anyone around here was paying real money for.
But I kept talking about it. Kept telling everyone I knew. And eventually, someone I was talking to asked if I’d DJ their wedding. That’s when I discovered where the market actually was: Weddings (i.e. not warehouse parties). That’s also the story of my first real lesson in how to start a business: the clients tell you what they need. You don’t tell them.
After college, I spent some time teaching English as a second language in Taiwan. When I came back to the States, I tried to build an online ESL teaching business. That one never got off the ground. But again, because I kept talking about everything I was working on, I had posted on social media about the website I’d built for that now-defunct business. My biggest DJ client saw it. They mentioned they were looking for someone to redesign their company website. One conversation led to another, and that’s the story of how I eventually ended up co-founding 2oddballs Creative — what is now a thriving, full-service marketing, PR, and advertising agency — with my wife Kylie in 2017.
2oddballs is now in its eighth year. It still has clients, still makes payroll, and still challenges the hell out of me. These days I’m also running Gabriel Cassady Consulting, an AI consultancy I launched January 1, 2026. I had a signed engagement letter — my first client — the same month I filed the LLC. That first client had actually encouraged me to formally launch the practice, which is about as good an origin story as a consulting business can have.
Three businesses. A DJ setup cobbled together from gear I could barely afford. A marketing agency that survived us literally moving to Ecuador to keep the overhead manageable. An AI consultancy that had a client before it had a business card. Enough failures to fill a memoir; enough wins to keep going.
Here are the four rules I’d hand you if we were having coffee. No hustle-bro platitudes. No “just believe in yourself” nonsense. Just the stuff that actually matters, in the order it actually matters.
Rule #1: Start With the Problem, Not the Idea
Here’s the trap almost every first-time entrepreneur falls into: they fall in love with their idea before they’ve confirmed that anyone actually has the problem their idea solves.
They build the product first. Design the logo. File the LLC. Tell their friends. And then, months or years and thousands of dollars later, they go looking for customers and discover that nobody needed the thing they made. I know this trap well. I’ve stepped in it.
My ESL teaching business is a perfect example. I came back from Taiwan fired up. I had real skills, real experience, and a clear service to offer. But I hadn’t done the harder work of asking whether the market actually needed one more entrant. It didn’t. Online ESL tutoring was already a mature, crowded, and highly competitive space. Plenty of people wanted ESL instruction; the problem was that the problem was already effectively solved. There were too many options, and I wasn’t offering anything different enough to earn attention. I had built a solution to a problem that had already been answered. That business never found its footing.
Contrast that with how 2oddballs started. I didn’t wake up and decide I wanted to own a marketing agency. I looked around at small businesses in Springfield and noticed something specific: they were being overcharged, under-delivered, and treated like line items by agencies that didn’t actually care about them. That was a real, felt, underserved problem. The agency was the solution to that problem — not the other way around.
The DJ wedding story is the same lesson in a smaller frame. I was DJing what I loved. The market wanted something different. When I listened to it (a client asking a question I hadn’t expected), my business found its real niche. I didn’t invent that demand. I just paid attention to it.
With my AI consulting practice today, the problem couldn’t be more obvious: small and mid-sized businesses across the Midwest are drowning in AI hype and starving for practical, honest guidance on what AI actually does, what it realistically costs, and whether it’s even worth their time. The fact that my first consulting client came to me before I’d formally opened for business told me everything I needed to know about whether that problem was real.
The people with the problem have to exist first. Your solution is secondary. Always.
This sounds backwards to most people. It isn’t. It’s the difference between building something people genuinely want and building something you want people to want. Only one of those leads anywhere worth going.
📚 Recommended Reading — Rule #1
The Lean Startup by Eric Ries — The definitive book on validating a real problem before you build anything. Required reading for every first-time founder.
The E-Myth Revisited by Michael E. Gerber — A clear-eyed look at why most small businesses fail, and the core myth — that technical skill equals business readiness — that traps so many entrepreneurs before they start.
Upstream by Dan Heath — About solving problems at their source rather than endlessly treating symptoms. The same upstream thinking that separates great entrepreneurs from reactive ones.
Originals by Adam Grant — How people champion new ideas, and why most original ideas fail not because they’re bad, but because they’re aimed at the wrong audience.
See Gabriel’s full reading list for more.
Rule #2: Know Your Real “Why” — Because the Shallow One Won’t Last
At some point in running a business, things will start to suck. Not might suck. Will suck.
A client will ghost you on an invoice. A month will come where payroll feels uncomfortably close. A week will arrive where you question every decision you’ve made since deciding you wanted to be your own boss. A competitor will undercut you. A technology will disrupt you. Something will break.
When that moment comes (and it will), the only thing that gets you through it is a clear, honest, deeply personal answer to the question: why am I doing this?
My answer has always been, at its root, one word: autonomy.
I have ADHD and depression. I am, by my own cheerful admission, a genuine oddball with beliefs that often diverge sharply from those of many local business owners, managers, and (growing up) even my own parents. The last traditional 9-to-5 job I held was at a place with a culture that was the polar opposite of everything I needed to function and thrive: top-down, command-and-control, my-way-or-the-highway, good-ol’-boys, butts-in-seats regardless of whether the work was done. I stuck it out for three years before finally turning in my two weeks. That’s when Kylie and I left for the teaching gig in Taiwan.
What I needed, and what I’ve spent my entire adult career building, is the ability to control what I do during the day. Not because I’m lazy (ask Kylie). But because my brain runs on genuine interest, not obligation. When I’m working on things I care about, on my own terms, I am genuinely good at what I do. When I’m not, I’m not. That’s not a character flaw. That’s just how I’m wired — and it’s something I’ve had to own rather than apologize for.
That need for autonomy has been the through-line connecting the DJ business, 2oddballs, and my AI consultancy. It’s what kept me going through the hard months. It’s what made moving to Ecuador with Kylie feel like an adventure rather than a desperate cost-cutting measure (though it was also that). It’s what gets me up every morning still wanting to do this work.
Your why doesn’t have to be autonomy. It can be financial independence, or love of craft, or a genuine belief that your community needs what you offer, or stubbornness (which is more useful than people give it credit for). But it has to be real. “I want to be my own boss” as a vague concept is not a why. “I want to be my own boss because every traditional job I’ve held has slowly broken something in me” is a why. The difference matters enormously when things get hard.
Know your why. Be honest about it. Write it down. Make sure it’s the kind of reason that still means something at 6am when everything is on fire.
📚 Recommended Reading — Rule #2
Drive by Daniel H. Pink — The research-backed case that autonomy, mastery, and purpose are the real engines of human motivation. If you’re starting a business for the right reasons, this book will articulate why better than you can.
Grit by Angela Duckworth — On what actually predicts long-term success. Spoiler: it’s not talent. It’s sustained passion combined with perseverance — which requires a compelling why.
The Top Five Regrets of the Dying by Bronnie Ware — A palliative care nurse’s account of what people wish they’d done differently. The number one regret? “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”
Think Again by Adam Grant — On the surprisingly productive power of questioning your own assumptions, including the assumptions that might be keeping you in a situation that isn’t working.
See Gabriel’s full reading list for more.
Rule #3: Grow Slow — On Purpose
The startup mythology says: raise capital, scale fast, dominate the market, go big or go home. I’m going to push back on that, hard, for most small business owners, because that path destroys more businesses than it creates.
My advice is simpler and less glamorous: keep your costs as low as humanly possible, for as long as humanly possible. Add expenses only when you absolutely must. Every new cost is a recurring commitment; a threshold your revenue has to clear every single month just to break even. Those commitments compound fast, and they start making decisions for you before you realize it’s happening.
For my DJ business, I rented speakers and lights for years before I ever bought my own. Years. The prevailing logic might have been “just invest in your gear.” My logic was: if a client wants a big sound system, I’ll rent one for that event and build the cost into the quote. No debt. No depreciating equipment sitting idle between gigs. No obligation.
With 2oddballs, Kylie and I took the lean philosophy further. We worked remotely, used the computers and accounts we already had, and resisted every temptation to “look more like a real agency” by taking on overhead we couldn’t justify. At one point, we moved to Ecuador. Two people can live extremely well in Ecuador, especially if they’re earning U.S. income while paying Ecuadorian bills. Our backup plan, if the agency failed, was to teach English. It didn’t fail. But having that backup plan meant we never made a scared decision just to survive the month.
This isn’t about being cheap. It’s about being patient. A business with low costs and modest revenue can weather almost anything. A business with high costs and strong revenue can collapse in a single bad quarter. I’ve watched it happen to people who were doing everything else right.
There’s a concept in Cal Newport’s writing on slow productivity that maps to this directly: doing fewer things, at a natural pace, with real attention to quality, outperforms the frantic, high-overhead, do-everything-now approach over any meaningful stretch of time. Your business is not a sprint. Treat it like one and it will end like one.
Grow slow. Stay lean. Let your costs be earned, not assumed.
📚 Recommended Reading — Rule #3
The Lean Startup by Eric Ries — Applies here too: the minimum viable product philosophy is, at its core, a philosophy of doing less, spending less, and learning faster.
The Great Game of Business by Jack Stack — One of the most honest books ever written about the financial mechanics of small business. Stack teaches you to read the score of the game you’re actually playing.
Four Thousand Weeks by Oliver Burkeman — A meditation on finite time and why our compulsive need to do more, faster, is often the thing standing between us and meaningful work.
Smarter Faster Better by Charles Duhigg — On the real science of productivity, which turns out to look a lot less like hustle culture and a lot more like clarity, focus, and strategic restraint.
See Gabriel’s full reading list for more.
Rule #4: Show Up Everywhere. Never Shut Up About What You Do.
This one sounds like advice your dad gives you. I know. But it’s the rule that has done more tangible work for my businesses than any of the others. And it’s the one most people are too self-conscious to actually follow.
Go back to the wedding DJ story. I didn’t find that client through a marketing campaign or a Google Ad. Someone I was already talking to happened to need a DJ for a wedding. They knew I DJed because I’d never stopped telling people I DJed. That’s it. That’s the whole story.
Same with 2oddballs. My largest DJ client saw a post I had made on social media about the website I’d built for my failing ESL business. They weren’t looking for a marketing agency specifically; they just needed a website. One conversation led to a project. That project led to a retainer. That retainer eventually became one of our anchor clients during the early years of the agency. None of it would have happened if I’d stayed quiet about what I was working on.
The mechanism here is simple, even if the execution requires some nerve: people can only hire you, refer you, or connect you with someone who needs you if they know you exist and know what you do. Most people are not loud enough about their own work. They worry about being annoying, or salesy, or presumptuous. That fear is reasonable and also very expensive.
Mention your business to everyone. Your dentist. The parent you ran into at your kid’s soccer game. The stranger behind you in line at the coffee shop. You genuinely have no idea who knows who, who’s been quietly looking for exactly what you offer, or who will become your best referral source because you said five words in passing: “I just started a business doing X.” That’s not a pitch. It’s a human sentence. And it plants seeds in more places than you realize.
Show up in person, too. Physically. In the same room as other human beings, as often as possible. I can’t overstate how much this matters, particularly in a Midwest market like Springfield. Relationships here are still built face-to-face. Trust is still established over handshakes and coffee and showing up reliably, repeatedly, over time. Digital presence matters. In-person presence matters more.
People remember people who show up; especially people who show up to help, without an obvious ask attached. They remember you when they have a need. They refer you when someone else has one. That is how word-of-mouth actually works, and it is still, in 2026, the most powerful form of marketing a small business has access to.
Show up. Be helpful. Keep talking about what you do. Repeat. This compounds like interest.
📚 Recommended Reading — Rule #4
Give and Take by Adam Grant — The research is clear: over time, givers outperform takers and matchers. Showing up helpfully and consistently, without a running tab, is not just a nice personality trait. It’s a business strategy.
Connected by Nicholas Christakis & James Fowler — On the surprising and measurable power of social networks. Who you know, who they know, and how information and opportunity actually travel through those webs.
Magic Words by Jonah Berger — The specific language choices that make people more likely to listen, remember, and act. Practical and immediately applicable.
Building a StoryBrand by Donald Miller — On why most business communication fails (it’s too focused on the business, not the customer) and how to fix it.
See Gabriel’s full reading list for more.
So, Where Do You Actually Start?
Here’s the notecard version:
- Find the problem first. Build the solution second.
- Know your real why. The shallow version won’t survive.
- Grow slow. Every cost is a recurring commitment. Earn it first.
- Show up everywhere. Talk about your business to everyone. Never stop.
These aren’t shortcuts. They won’t make you a millionaire in eighteen months or get you on a Forbes list. But if you follow them with patience and consistency, they will help you build something real; the kind of business that actually lasts long enough to matter.
One last thing. The businesses that worked for me didn’t succeed just because I followed these rules in isolation. They worked because I was solving real problems, in markets that actually existed, for reasons that were genuinely mine. The rules are the frame. Your specific situation fills in the picture.
If you’re working through the early stages of a business (or trying to figure out whether to start one at all), and you want someone to think through it with you honestly, that’s a big part of what I do as an AI and business consultant. I work with Midwest small and mid-sized businesses, and I promise you’ll get the direct version of every answer, whether it’s what you hoped to hear or not.
Gabriel Cassady is a serial entrepreneur, AI consultant, and co-founder of 2oddballs Creative, a full-service marketing and PR agency in Springfield, Missouri. He writes about AI, technology, and business for the Springfield Business Journal and at gabrielcassady.com.
