I left my VP role at 25 to build a startup. Leaving security and a steady paycheck behind was hard, but I have no regrets.
Courtesy of HelloData.ai
- Timothy Gamble left his VP role at Walker & Dunlop to cofound HelloData.ai in 2022.
- Gamble's decision was driven by a desire for continual growth and the opportunity to innovate in AI.
- Despite earning less, Gamble is happy with his decision to leave his 9-5.
This as-told-to essay is based on a conversation with Timothy Gamble, a 26-year-old cofounder at HelloData.ai based in Washington, DC. It's been edited for length and clarity.
I'm a cofounder and the head of data engineering at HelloData.ai, which uses real-time data on more than 25 million multifamily units nationwide to suggest the most relevant comparable properties and analyze real-estate assets.
My career kicked off in 2016 at Enodo, a real-estate analytics company, as a freshman in college with just a few months of computer science under my belt. I gathered and normalized real-estate data, but my role quickly expanded, and I was soon in charge of the data infrastructure that processed billions of real-estate data points daily.
By the time I graduated, Enodo was approached with an acquisition offer, which was accepted. I then joined Walker & Dunlop, a provider of financing services to owners of commercial real estate, as a lead data engineer in February 2019.
I played a key role in incorporating Enodo's technology into Walker & Dunlop's data-driven products. In August 2021, I was promoted to VP of data engineering.
From the outside, it might've looked like I had it all, but inside, something was missing
Although I enjoyed the stability of my role, I reached a point where I felt my growth had plateaued, and I wanted to get back into the startup scene.
At the end of 2022, I quit to cofound HelloData.ai with Nico Lassaux, head of machine learning, and Marc Rutzen, CEO.
Nico left W&D one year before me, but we kept in touch. When I left W&D, we decided it made sense to start a real-estate AI company since we both had an entrepreneurial spirit, strong engineering backgrounds, and real-estate domain expertise.
We started with six separate ideas before moving forward with HelloData.ai. Marc kept in touch with us and decided to join our venture.
Leaving a stable job and cofounding HelloData.ai wasn't a quick decision
Deciding to leave my stable job took a year of wrestling with questions, especially from my family. Security, prestige, and a steady paycheck — why trade those for the unknowns of a startup?
There was no one answer, but I had several realizations I couldn't ignore. First, I craved the startup energy. The constant challenges and rush of innovation lit a fire in me. My job was comfortable, but I missed the adrenaline of pushing boundaries and overcoming hurdles.
Then there was my role at W&D, which had shifted from creating to maintaining. Building new systems and implementing fresh ideas were the activities that fueled my passion. I needed to be challenged, and the corporate ladder didn't offer that kind of growth. Managing a bigger team or getting a "senior" title was less appealing than the chance to learn and innovate in a rapidly changing field.
Finally, there was AI. It was starting to sweep across industries, and I didn't want to be a bystander.
Deciding to leave my VP role was scary but the fear of complacency and the prospect of looking back with regret for not pursuing my passions were far greater motivators.
I knew I needed to challenge myself to grow
Walking away from a role that may seem perfectly set up for you, especially when it feels like golden handcuffs, requires a deep understanding of what you value most. For me, it was about continual growth and not wanting to get left behind as the pace of engineering, especially in AI, began to accelerate.
Don't shy away from the discomfort of leaving security behind. In that discomfort, you'll find the most significant opportunities for growth and innovation. Trust in your ability to navigate the unknown, and remember that the skills and resilience you build through this process are invaluable assets.
I'm now earning less than I was before, but that's because we're reinvesting all profits back into the business. We're very proud to be bootstrapped yet profitable and continue to grow.
I've learned a lot as an entrepreneur
I've made plenty of mistakes in my career, but my most recent one was in January when I built a system and unexpectedly racked up over $5,000 in computing costs.
The issue was resolved after editing a few lines of code, but it showed me just how important it is to forecast what a new system will cost before deploying it.
If I were to distill one piece of concrete advice for people itching to leave their corporate jobs, it would be this: embrace the challenge of leaving a comfortable position not as a loss, but as a critical step toward personal and professional growth.
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