The Startup Life: Lessons from Small Business Leadership

Throughout my career, I've had the unique opportunity to work closely with founders and leaders at small businesses and startups across different industries—from Transportation to SaaS to Entertainment. This journey has taught me invaluable lessons about adaptability, leadership, and what it really means to be a "full-stack" developer in more ways than one.

The Small Business Landscape

I've spent most of my career in environments where resources are limited, timelines are aggressive, and everyone wears multiple hats. This isn't a complaint—it's been one of the most formative experiences of my professional life.

Transportation Startup

My early experience in a transportation startup was my first real taste of how technology directly impacts operations and customer experience. Working directly with the founders, I saw how every technical decision had immediate business impact—there was no buffer between code and customer satisfaction.

The Challenge:

Building technology solutions for a physical, logistics-heavy industry
Real-time tracking and coordination of vehicles and drivers
Customer-facing applications that needed to be reliable and user-friendly
Integrating with third-party services and APIs for mapping, payments, and communications
Managing data flow between drivers, customers, and operations teams

What I Learned:

Operational Efficiency: Every feature I built had to make operations smoother. A small improvement in routing or dispatch could save hours and reduce costs.
Real-World Impact: Unlike some software, this code directly affected people's daily lives—getting them where they needed to go, on time, safely.
Customer-First Development: I learned to think from the customer's perspective. What seems like a minor bug to me could mean a missed appointment or lost revenue for the business.
Integration Complexity: Working with multiple APIs and services taught me the importance of error handling, fallbacks, and graceful degradation.
Performance Matters: In transportation, delays aren't just inconvenient—they're costly. I learned to optimize for speed and reliability from the start.
Direct Feedback Loops: Working closely with founders meant I got immediate feedback on what worked and what didn't. This accelerated my learning curve significantly.

This experience taught me that in small businesses, your code isn't abstract—it's directly tied to business outcomes, customer satisfaction, and company survival.

Education Company (J Taylor Education)

At J Taylor Education, I experienced one of the most transformative periods of my career—helping a small education company navigate the COVID-19 pandemic. When schools closed and in-person learning became impossible, we had to make drastic changes to move our entire product digitally, and fast.

The Challenge:

Overnight shift from in-person to fully digital
Maintaining educational quality while adapting to new delivery methods
Supporting teachers and students through a massive transition
Building infrastructure to handle increased online traffic

What I Learned:

Adaptability Under Pressure: When the world changes overnight, you have to pivot quickly. There was no time for perfect solutions—we had to build, deploy, and iterate rapidly.
User-Centric Problem Solving: Every decision was driven by the question: "How does this help teachers teach and students learn?" The technical solution had to serve the educational mission.
Scalability Planning: We went from serving a manageable number of users to potentially thousands of concurrent users. I learned to think about scalability from day one, not as an afterthought.
Remote Collaboration: Working with a distributed team during a crisis taught me the importance of clear communication, documentation, and asynchronous workflows.
Resilience: When things break (and they will), you fix them quickly, learn from the experience, and keep moving forward.

This experience was a masterclass in crisis management, rapid development, and maintaining quality under extreme pressure. It also reinforced my belief that small businesses can be incredibly agile when they need to be.

Small SaaS Company

At a small SaaS company, I experienced the unique challenges of building a product that customers would pay for, use daily, and recommend to others. The CEO sat a few desks away, and product decisions happened in real-time conversations—no product managers, no lengthy approval processes, just direct communication and rapid iteration.

The Challenge:

Finding product-market fit while building features customers actually wanted
Balancing feature development with technical debt and infrastructure improvements
Managing customer feedback and feature requests with limited development resources
Building a scalable product architecture while moving fast
Competing with larger companies with more resources but less agility
Maintaining code quality and system reliability as the product grew

What I Learned:

Product-Market Fit: I learned to distinguish between features customers say they want and features they'll actually use and pay for. Data and user behavior became my guide.
Customer Feedback Loops: Direct access to customers meant I could see how they used (or didn't use) features I built. This taught me the importance of user research and analytics.
Technical Debt Management: In a small company, you can't always do things "the right way" the first time. I learned to identify when to move fast and when to slow down and refactor.
Feature Prioritization: With limited resources, saying "no" became as important as saying "yes." I learned to evaluate features based on impact, effort, and strategic value.
Full-Stack Ownership: I wasn't just building features—I was deploying them, monitoring them, supporting them, and iterating on them based on real usage data.
Business Metrics: I learned to think in terms of business outcomes—user acquisition, retention, revenue—not just technical metrics like code coverage or response times.
Agile in Practice: True agile development isn't about ceremonies—it's about responding to change, learning from customers, and shipping value quickly.

This experience taught me that building software products is as much about understanding customers and business as it is about writing code. The best technical solution is worthless if it doesn't solve a real problem for real users.

Entertainment Startup (AREA15)

Now at AREA15, I'm experiencing the fast-paced world of entertainment technology, where innovation and user experience are paramount. The startup mentality here means moving quickly, iterating constantly, and always thinking about the customer experience. Every project I work on—from ticketing kiosks to immersive games—directly impacts how visitors experience our venue.

The Challenge:

Creating technology that enhances entertainment experiences, not just enables them
Building systems that handle high-volume traffic (8,500+ customers daily) while maintaining performance
Integrating multiple payment systems, APIs, and third-party services seamlessly
Developing for multiple platforms—web, mobile, kiosks, and interactive installations
Balancing innovation with reliability—visitors expect both cutting-edge experiences and systems that just work
Rapid prototyping and iteration to test new ideas and experiences quickly
Managing technical complexity while keeping the user experience simple and intuitive

What I Learned:

Experience-First Development: In entertainment, the technology should be invisible. Users shouldn't think about the code—they should think about the experience. This taught me to prioritize user experience over technical elegance.
Scale from Day One: When you're serving thousands of customers daily, you can't retrofit scalability. I learned to think about performance, caching, and load distribution from the start.
Multi-Platform Thinking: Building for kiosks, web, mobile, and interactive installations taught me to think about platform-specific constraints and opportunities.
Payment Integration Complexity: Working with Stripe, Square, and other payment systems taught me the importance of error handling, transaction management, and user experience in financial flows.
Innovation Under Constraints: Even with tight deadlines and resource constraints, there's room for innovation. I learned to find creative solutions that balance speed, quality, and innovation.
Real-Time Systems: Many of our systems need to work in real-time—ticket sales, food orders, game interactions. This taught me about event-driven architecture, WebSockets, and managing state across distributed systems.
Customer Experience Metrics: In entertainment, success isn't just about uptime—it's about engagement, satisfaction, and repeat visits. I learned to measure what matters to the business.

This experience has reinforced that technology in entertainment is about creating moments of delight and wonder. The best code is the code that disappears, leaving only the experience.

Working Closely with Leaders and Owners

One of the most valuable aspects of working in small businesses is the direct access to leadership. I've had the privilege of working directly with founders, CEOs, and owners, and this proximity has been incredibly educational.

Learning from Decision-Makers

Seeing the Big Picture:

Understanding how technical decisions impact business metrics
Learning to think beyond code to customer experience and revenue
Seeing how resource constraints drive creative solutions

Communication at the Top:

Learning to translate technical complexity into business language
Understanding what metrics and outcomes matter to leadership
Building trust through transparency and delivery

Strategic Thinking:

Participating in product strategy discussions
Understanding market positioning and competitive advantages
Learning to balance technical ideals with business realities

The Fast-Paced Environment

Startups and small businesses move fast. There's no bureaucracy, no layers of approval—just decisions, execution, and iteration. This pace comes with both opportunities and challenges.

The Thrill of Speed

Rapid Iteration: Ideas can go from concept to production in days, not months
Direct Impact: Your work directly affects the company's success
Learning Velocity: You're constantly exposed to new challenges and technologies
Ownership: You feel genuine ownership over your work and its outcomes

The Challenges

Burnout Risk: The pace can be unsustainable without boundaries
Technical Debt: Speed sometimes means shortcuts that need to be addressed later
Resource Constraints: Limited budgets mean making tough prioritization decisions
Uncertainty: Plans change quickly, and you need to adapt constantly

Wearing Many Hats

In small businesses, job descriptions are more like suggestions. I've been:

Developer: Writing code, debugging, deploying
DevOps Engineer: Setting up CI/CD, managing infrastructure
Product Manager: Gathering requirements, prioritizing features
QA Tester: Testing functionality, finding bugs
Technical Support: Helping customers, troubleshooting issues
Mentor: Teaching junior developers, sharing knowledge
Architect: Designing systems, making technical decisions
Project Manager: Coordinating timelines, managing stakeholders

The Benefits of Versatility

Broader Skill Set:

Working across different roles has made me a more well-rounded developer. I understand not just how to write code, but how systems work end-to-end, how deployments happen, how customers use products, and how business decisions are made.

Better Communication:

Having experience in multiple roles helps me communicate more effectively. I can speak the language of product managers, understand the concerns of operations teams, and translate between technical and business stakeholders.

Problem-Solving Perspective:

When you've worn many hats, you approach problems from multiple angles. A bug isn't just a code issue—it's a customer experience issue, a support ticket, a deployment problem, and a business impact.

The Challenges of Versatility

Context Switching:

Jumping between roles requires mental flexibility. One moment you're deep in code, the next you're explaining a feature to a customer, then you're planning infrastructure changes.

Depth vs. Breadth:

There's a tension between being a generalist and maintaining deep expertise. I've had to be strategic about where to invest time for deep learning versus where to maintain surface-level knowledge.

Boundaries:

It's easy to say "yes" to everything when you're capable in many areas. Learning to set boundaries and say "no" (or "not now") has been crucial for maintaining quality and avoiding burnout.

Key Lessons Learned

1. Embrace Ambiguity

In startups, requirements are often unclear, and you need to figure things out as you go. This has taught me to be comfortable with uncertainty and to make progress even when the path isn't fully defined.

2. Prioritize Ruthlessly

With limited resources, you can't do everything. Learning to identify what truly matters and focus on high-impact work has been essential.

3. Build for Change

Startups pivot. Requirements change. The code you write today might need to be refactored tomorrow. Building flexible, maintainable systems is crucial.

4. Customer Focus

In small businesses, you're often closer to customers. This proximity has taught me to think about the user experience in everything I build, not just the technical implementation.

5. Learn Continuously

The variety of roles and challenges means constant learning. I've had to become comfortable being uncomfortable, always learning new technologies, processes, and domains.

6. Communication is Everything

When you're working closely with leadership and wearing many hats, clear communication becomes critical. I've learned to be concise, transparent, and proactive in my communication.

The Struggles Are Real

Let's be honest—working in fast-paced startup environments isn't always glamorous:

Long Hours:

There have been late nights and weekends spent debugging production issues or meeting tight deadlines.

Stress:

The pressure of knowing your work directly impacts the company's success can be intense.

Imposter Syndrome:

Wearing many hats means sometimes you're doing things you're not an expert in. Learning to be comfortable with that discomfort has been a journey.

Technical Debt:

Moving fast sometimes means making compromises. Balancing speed with quality is an ongoing challenge.

Why I Keep Coming Back

Despite the challenges, I'm drawn to small businesses and startups because:

Impact: I can see the direct impact of my work
Growth: The learning curve is steep, but the growth is exponential
Autonomy: I have more freedom to make decisions and try new approaches
Culture: The culture is often more collaborative and less hierarchical
Innovation: There's more room to experiment and innovate

Advice for Others

If you're considering working at a startup or small business:

1. Be Ready to Learn: You'll be doing things outside your comfort zone regularly

2. Set Boundaries: Fast-paced doesn't mean you should work 24/7. Protect your time and energy

3. Embrace the Variety: The variety of work is a feature, not a bug

4. Communicate Proactively: Don't wait for problems to escalate

5. Focus on Impact: Learn to identify what work truly matters

6. Build Relationships: Working closely with leadership means relationships matter

Conclusion

Working in small businesses and startups has shaped me as both a developer and a professional. The experience of wearing many hats, working closely with leadership, and operating in fast-paced environments has taught me adaptability, communication, and a deep understanding of how technology serves business goals.

The struggles are real, but so are the rewards. The skills I've developed—from technical versatility to business acumen—are invaluable, and the relationships I've built with leaders and founders have been some of the most educational experiences of my career.

If you're a developer considering the startup path, know that it's challenging but incredibly rewarding. You'll grow faster, learn more, and have more impact than you might in a larger organization. Just remember to set boundaries, communicate clearly, and enjoy the ride.

*The startup life isn't for everyone, but for those who thrive in fast-paced, high-impact environments, there's nothing quite like it.*