August 28, 2025
I've started five companies over the past decade. Two were epic failures that I shut down after making sales. Three were successes that generated over $750,000 combined. The difference between failure and success had nothing to do with market opportunity, business models, or funding.
It came down to one thing: obsession.
The companies I failed at were in markets I understood and had the skills to execute in. The companies I succeeded with were in areas where I couldn't stop thinking about the problems I was solving. Here's the brutally honest breakdown of what separates founders who push through challenges from those who quit when things get hard.
My first company was a consulting business that started as a simple side hustle. I was working as a W-2 employee but wanted to work more, make more money, and learn faster. Every time an engineer I worked with liked my results, they'd refer me to a founder, and that's how I continuously got work.
That consulting company grossed over $600,000 in additional income for my family over the past decade. It did exactly what it was supposed to do - supplement our income while letting me work on what I loved: helping founders build and launch products.
The third company was an accelerator where I hit six figures in six months helping women take their tech ideas from concept to customers. They'd go through a four to six month program with me, and we'd validate their idea, get customers, build their product, and send them on their way.
Both of these successes had the same foundation: I was working on problems I was genuinely obsessed with solving.
Between the consulting success and the accelerator, I started two companies that failed spectacularly. Both were dropshipping businesses, and both failed for the same reason: I had zero passion for what I was doing.
I chose dropshipping because I had extensive e-commerce experience and knew exactly how the systems worked. I could build websites myself, I understood the operational requirements, and I had all the technical skills needed to succeed. On paper, it made perfect sense.
Both companies started making sales within three to four months. The business model was working. The skills were there. The market was responding. But after reaching that initial success, I realized something devastating: I hated every minute of it.
I had zero passion for e-commerce operations, zero interest in the products I was selling, and zero excitement about scaling these businesses. So I shut them both down, walking away from businesses that were already generating revenue.
My fifth company is Theanna, an all-in-one startup platform for female founders building tech ideas. I launched six months ago, we're at $150K ARR, and this is my favorite business yet.
Theanna combines everything I learned from my previous successes: building products, talking to people, helping solve problems, and pushing solutions to market. It's the natural evolution of my consulting work and my accelerator, but at scale.
The difference with Theanna is that I can work on it without ever getting bored. I'm obsessed with helping female founders overcome the barriers to building tech companies. I think about product features in the shower, I get excited about customer feedback, and I genuinely cannot wait to see what we build next.
Looking back at all five companies, the pattern is crystal clear. The three successes - consulting, the accelerator, and Theanna - all involved the same core activities that I was naturally obsessed with: building products, solving problems for founders, and helping people turn ideas into reality.
The two failures involved activities that I understood intellectually but had no emotional connection to: managing e-commerce operations, optimizing supply chains, and scaling product catalogs.
Here's the test: Can you work on your business idea without getting bored? Not just for days or weeks, but for years? Do you find yourself thinking about solutions and improvements even when you're not supposed to be working? Do you genuinely care about the problem you're solving beyond just the money you could make?
If the answer is no, you're setting yourself up for failure.
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This might sound like feel-good advice, but there's hard business logic behind it. Building a successful company requires pushing through countless obstacles, setbacks, and moments when quitting seems like the rational choice.
When you're passionate about what you're building, those obstacles become puzzles to solve rather than reasons to quit. When you're just chasing market opportunity without genuine interest, every setback feels like evidence that you should move on to something easier.
The dropshipping businesses failed not because the market was bad or my execution was poor - they failed because when challenges arose, I had no emotional investment in pushing through them. It was easier to shut down than to fight for something I didn't really care about.
All three of my successful businesses shared the same DNA: they were extensions of work I was already doing and loved. The consulting grew out of wanting to do more of what I enjoyed in my day job. The accelerator formalized the mentoring I was already doing informally. Theanna scales the problem-solving I've been obsessed with for years.
This isn't about following your passion blindly - it's about finding the intersection between what you're passionate about and what people will pay for. All three businesses solve real problems that people value. But they also happen to be problems I can't stop thinking about.
Starting a business is hard enough when you're obsessed with what you're building. It's nearly impossible when you're not. Before you invest time, money, and energy into your next venture, ask yourself the hard question: Am I genuinely excited about working on this problem for the next several years?
If the answer is anything other than an enthusiastic yes, take a step back and rethink your choices. Market opportunities come and go, but the problems you're naturally obsessed with solving are where you'll find both fulfillment and sustainable success.
The best businesses aren't built by founders chasing the biggest markets - they're built by founders who can't stop thinking about specific problems they're uniquely positioned to solve. Find that intersection, and you'll have the foundation for something that can survive the inevitable challenges of building a company.
Your passion won't guarantee success, but without it, you're almost guaranteed to quit when things get tough. Choose accordingly.
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