Five Entrepreneurial Lessons From Simon Fletcher

Simon Fletcher is a self-taught software engineer and tech entrepreneur with a career spanning two decades. He sold his second startup to a major tech company, where he quickly rose through the engineering ranks before transitioning to front-end development at a VPN alternative.

Fletcher has also focused on developing his leadership skills by enrolling in MIT classes, significantly enhancing his professional abilities.

Although he has had much success, it hasn't always been easy. Fletcher has learned many valuable lessons that can benefit those who need guidance in their tech careers.

Here are his five essential tips for aspiring entrepreneurs.

Lesson 1: The Power of Networking

The most important lesson, and one that defines Fletcher’s career, is the importance of putting yourself out there and building a network. His position in the industry began at a young age when he found the UK startup scene through online forums and communities. He was particularly drawn to the idea of building things from scratch on his own. This discovery paved the way for Fletcher to become a self-taught software engineer.

At the core of Fletcher’s success is his love of problem solving and being around like-minded people. He was determined to find as many people with similar interests as possible and create his circle. This networking eventually led him to apply for the Y Combinator accelerator program, where he learned the importance of partnering with people who share his ambitions and help him reach higher goals. Being around people with similar ambitions set a great example for Fletcher as a young entrepreneur.

Networking has been a valuable experience for Fletcher, unlocking great opportunities and advancing his career path. His advice to people early in their careers is to concentrate on establishing a network. The early stages of any professional journey can be discouraging, and finding one’s voice and developing a unique identity in tech can be difficult. That’s why networking plays a crucial role in finding the right people to guide and support entrepreneurs on their path forward.

Lesson 2: Tenacity and Persistence Are Crucial

Fletcher’s entrepreneurial journey was far from easy, but it has molded him into the resilient and adaptable leader he is today. His experience began with his very first venture, Time Travel Corp, a video-based social media company that was struck by a severe blow during the pandemic.

Fletcher made the tough decision to shut down the company because people couldn't interact with each other outdoors — a real challenge, as the very cornerstone of his initiative was about users creating content outside. For any entrepreneur, closing their first startup can trigger significant self-doubt. However, as Fletcher discovered, that doesn’t have to be the case. He believes that if you’re serious about building a business, one of the key factors is being persistent, even when things become challenging.

Nevertheless, he encourages entrepreneurs to be mindful of why these companies are startups and when it might be better to consolidate them and exit instead of fighting a losing battle. Time Travel Corp was born out of a solid idea, but he recognized that it didn’t have sufficient free cash flow to survive, especially from his own pocket, without generating profit — a hard yet important fact he had to face.

Lesson 3: When The Time Is Right, Sell

Fletcher’s second company, Minbox, a collaborative file-sharing software, marked another milestone in his startup career that impacted him as a leader. But in 2016, he decided he was ready to sell it.

Eventually, Minbox was bought by Airbnb, where he ultimately pivoted into a role and established himself as a senior engineer on the team. Surprisingly, this marked Fletcher’s first experience working for a corporation. He eventually left to work at Twingate, where he could focus on his passion for front-end engineering. These pivots show that an entrepreneurial journey is rarely straightforward or simple.

Lesson 4: Being an Entrepreneur Isn't Just About Being a Founder — Finding a Place in Corporate Environments

While many might believe that being an entrepreneur ends if you find yourself working for a large corporation, this may not be entirely accurate. Fletcher’s experience has proven that entrepreneurs can also contribute to the corporate world. He took on a leadership role at Twingate, where he applied two of his most important lessons: persistence and a commitment to building great products. This helps in his work as a leader and front-end developer.

His current focus is on building best-in-class web products for zero-trust security. At heart, Fletcher remains a software engineer, and his leadership position has forced him to think at the scale of an entire organization, allowing him to make decisions for the betterment of the team.

Lesson 5: Follow Your Passion

The foundation of Fletcher’s success is his passion for software engineering. If you’d known him in his teens, you would have met a young kid who simply taught himself to code for the fun of it. His first endeavors were simple code pages that demonstrated basic math. He would code them solely because he enjoyed the process.

It was this innate passion that drew him into the world of software engineering — a passion he still carries with him today. Fletcher’s journey and passion for solving problems serve as a lesson to aspiring entrepreneurs seeking to be adaptable and persistent.

Final Thoughts

As the tech scene evolves, Fletcher is always ready to pivot, and he wants to teach others the same adaptable mindset. His five key lessons serve as a great starting point for novice entrepreneurs.

By following your passion with dedication and persistence, you can also achieve outstanding results.

BDG Media newsroom and editorial staff were not involved in the creation of this content.