“When they say ‘be your own boss’ what they don’t tell you is that you’re trading one boss for dozens. Each client becomes your new manager, and some are far more demanding than any corporate supervisor could ever be.”

Opening my company and consulting.

While my Microsoft internships provided structure and resources, I was simultaneously running my own company during college. We created apps, web applications, e-commerce solutions, and various digital products for different clients. The entrepreneurial rallying cry of “Open your own company, be your own boss!” echoed in my mind, but reality quickly taught me otherwise.

The truth I discovered: when you have a company, customers become your bosses. Instead of one supervisor with clear expectations, you suddenly have multiple people with competing priorities, varying communication styles, and different definitions of success.

Our Business Model: Subscription-Based Web Development

Our main value proposition was offering websites on a subscription basis. We’d front the design and development costs, then charge a monthly fee that made professional web presence more affordable for small businesses. Clients would also receive ongoing support and maintenance without unexpected costs.

Traditional Model:

• Large upfront cost
• Additional charges for changes
• Maintenance costs extra
• Hosting billed separately

Our Subscription Model:

• Monthly subscription
• Included maintenance and updates
• Hosting and support bundled

The Failure Portfolio: Learning What Not To Do

Within the lifespan of the company, we attempted and failed at numerous ventures. Each one taught valuable, if painful, lessons:

Onesies Online Store

What happened: We sourced custom-printed onesies from a supplier who promised quick turnaround. Quality issues and delivery delays led to customer complaints and eventual shutdown.

Key lesson: Do not sell something where you can’t rely on your supplier 100%.

Wood Products Online Store

What happened: We partnered with a woodworker to create custom furniture pieces. The craftsmanship was excellent but production couldn’t scale to meet demand, causing fulfillment issues.

Key lesson: Even with quality products, if you can’t meet demand consistently, your business will fail.

Educational Game Development

What happened: We built an educational game to teach basic math concepts. Development took longer than expected, playability issues persisted, and schools weren’t willing to pay enough to make the project viable.

Key lesson: Games are hard to tune, create, and code—especially educational games with specific learning objectives.

Parent-Teacher Social Network

What happened: We developed a platform to improve parent-teacher communication. User acquisition was difficult, schools had complex purchasing processes, and we couldn’t reach the critical mass needed for network effects.

Key lesson: Education is a really challenging market with long sales cycles, tight budgets, and complex stakeholder relationships.

SEO Services & Google Ads Management

What happened: We offered search engine optimization packages, but delivering measurable results took longer than clients were willing to wait. Retention suffered as clients expected immediate ranking improvements. We managed Google Ads campaigns but found that client expectations often exceeded what was possible within their budgets and timeframes.

Key lesson: Don’t sell something your customer won’t be 1000% happy with when it’s finished or where success metrics are difficult to control. Clear expectation setting is crucial, especially with marketing services where results can vary significantly.

Accidentally stepping into management

Beyond these business failures, I faced a more personal challenge: becoming a manager for the first time. I was responsible for 5-6 developers (depending on the project), and I learned firsthand how difficult effective management truly is.

Missing 1:1s became a clear signal of failing my team. I discovered that to get great work, you need to understand each developer’s unique motivations, set a clear vision that enables problem-solving, provide consistent feedback and support and remove blockers.

I made a lot of management mistakes, but the most significant was trying to be both an individual contributor and a manager simultaneously without clear boundaries. When deadlines approached, management duties were the first to be sacrificed, which inevitably created bigger problems down the line.

Despite these challenges, I’m proud to see that all of my direct reports are now working at FAANG companies and have built successful careers. I like to think I was the first step in their journey toward becoming great developers, even if my management skills were still developing.

As a manager, it is really easy to fail your directs. If you don’t communicate clearly and be there when they need you, they’ll slowly lose trust in you. And trust is the most essential thing.

The Hardest Part: Letting People Go

I’ll always remember the first time I had to fire someone. It is a devastatingly difficult emotional process. You try to console yourself with the knowledge that just as this employee wasn’t right for your company, your company probably wasn’t right for them; that they’ll be more fulfilled elsewhere.

But that doesn’t make the conversation any easier. I prepared for days, rehearsing the conversation, consulting with mentors, and trying to ensure the process would be as respectful and supportive as possible. The experience taught me to be much more careful in hiring and to clearly set expectations to give people a fair chance to improve and to avoid reaching this point.

No code MVP?

When clients approached us with app ideas but tiny budgets, I developed a contrarian approach: talk them out of building apps. Instead of selling them expensive software they couldn’t afford, I’d suggest three rapid validation alternatives:

Manual-first operations: “Before automating, try doing everything by hand with Google Forms and spreadsheets.” Pre-sell with landing pages: “Build a marketing site that describes your future product and measures interest.” Use existing platforms: “Test your community concept on Facebook Groups before building a custom platform.”

This approach saved clients thousands of dollars, accelerated their learning, and ironically, led to more sustainable business relationships when they returned for full development with validated ideas.

As a final note here, I was always surprised how hard it was to sell apps for me. People would commonly come to the company with ideas and apps, and ask to pay the minimum possible (not even enough to staff a single person to work on it). Maybe I wasn’t good at making people realize the value of a platform. Or maybe it wasn’t what they needed.

Be your own boss… not the panacea it’s meant to be.