A Tech Entrepreneur’s Shift: From Startup to a Corporate Role
It hit me hard when a highly capable tech entrepreneur, whom I admire, told me he was shutting down his startup. Even though I knew he had a lucrative job offer, it still came as a surprise. He had a brilliant concept, so why the sudden change?
After a discussion, I understood his decision completely. He’s a tech innovator, the kind of person I’d readily work alongside. This wasn’t someone who fit the traditional ‘celebrity entrepreneur’ mold but rather someone who has shaped the tech behind numerous products and services over two decades.
As a friend, I’d helped him refine an idea that could transform an industry. He’d secured potential customers and was on track to create a fundable venture. Yet, he opted for a senior position at a well-known tech corporation. I can’t fault him.
The Startup’s First Rule: “You don’t talk about quitting”
Let’s be clear; “Jack” is a top-tier tech mind. He has deep startup experience, achieving significant successes and enduring a substantial failure that taught him valuable lessons.
My involvement with his project was informal, based on shared coffees and beers. We focused on building the service, then automation, and developing a user experience. He was doing all this while still servicing his first subscription for four figures a month before he even had a name for his platform.
This is where he got stuck.
Beyond Security
He assured me that the corporate offer wasn’t about the money or the idea of job stability. “The company is a fixer-upper; it’s probably less secure than my startup,” he said. Many believe corporate roles ensure security, when, in reality, neither world guarantees it.
What people consider secure is often about control. In a corporation, there’s stability, cash reserves, and a customer base. A startup typically lacks these, making corporate life appear more secure, until it isn’t.
Layoffs are common, and when your livelihood depends on others, as an entrepreneur, that’s the worst feeling.
When Things Scaled
Jack ran a B2B service for over a year, primarily on his own. Wanting to avoid mistakes, he decided to integrate AI tools and automate certain parts of the service. “I quickly realized what we’re calling AI these days is more of a nice-to-have,” he stated. Those experiments, which led to customer interaction and primitive UX, were then expanded with no-code and off-the-shelf tools to create a rudimentary user interface.
From that point on, the service morphed into a product. At this stage, Jack had to manage, at a minimum, three full-time jobs: Building a software platform, running a hybrid product and service company, and – oh – doing the work for paying clients.
Jack then realized that he would need investment, which meant a fourth job: raising capital. He faced another problem: a limited venture capital network. Jack had built multiple successful companies without institutional funding.
Chasing “A.I.”
Jack encountered difficulty with investors. They were focused on AI. When he mentioned AI, investors often became more interested. While there could be opportunities, the main purpose that Jack was driving at was a tailored service made easily available for lower costs, which is what I loved in the first place. The concept was stellar, but investors saw it as outdated, not the future.
However, the current investor attitude reminds me of the late 1990s. This behavior is not new. The cause is short-sightedness, driving investors to chase the next big thing.
The Entrepreneur’s Dilemma
Faced with building his startup the hard way or compromising to chase the AI trend, Jack asked: Why? Why not simply deliver the service himself instead of transforming it into an AI-driven product? Then, the unexpected job offer arrived. If he were willing to let someone else pay him to keep doing the service, why not let someone else do the running?
Opportunity in the Startup Landscape
The shift from the all-or-nothing startup game over the past few years is forcing individuals to reevaluate their roles and priorities.
There is an opportunity for smart investors to challenge the status quo by backing people like Jack and their sensible, successful business models.
