This told essay is based on a conversation with Jason White, a 46-year-old startup founder who lives in the San Jose area. Business Insider has confirmed his previous employment in writing. His words have been edited for length and clarity.
I’ve spent half of my 20 years in the tech industry working at Google and Meta. I was able to work on some great projects with these companies, but I have now left both of them.
I joined Google in 2016 as head of technology for the Gmail division and moved to the Google Search team in 2020. By 2024, I wanted to lean more into AI. I didn’t think my position at Google would give me that opportunity, so I opened myself up to other opportunities.
When a recruiter at Meta contacted me about the AI Machine Learning Engineer position, I decided to pursue it and ultimately received the offer. I left Google in July 2024 and joined Meta a month later.
I had a good experience with meta. I worked with great people in a resource-rich environment and learned a lot. It also allowed me to focus on AI products and work on AI as I had hoped.
But in the middle of 2025, I started thinking about quitting my job to launch a startup. Specifically, it is a venture that uses AI to help ordinary households with their finances.
I was thinking about whether or not to quit Meta.
Deciding whether to resign from Meta was a complex decision.
My passion for this startup was growing. I know what financial pressure is like. I was a low-paid graduate student trying to support a newborn.
Many people don’t have access to good financial planning and management tools to improve their financial situation. I didn’t have an idea of what a business would look like yet, but I felt like I had an opportunity to help people, and that was very motivating for me.
I connected with a potential co-founder, a friend of a friend, and we spent a lot of time talking through that opportunity. That made me more comfortable with the idea of leaving Meta, but there were still a lot of factors to consider.
It’s hard to leave a world-class team with people you love, not to mention a reliable source of income.
Read more about people at corporate crossroads
I made sure my family was prepared to lose my income.
I know some people start a business on the side while still working a full-time job, but I just couldn’t do that. Because I was already juggling two demanding roles as a Meta employee and a parent.
My other concern was legal. Outside business had to be disclosed to Meta, which could create non-competitive issues. Especially since my business idea was related to AI, as was my role at Meta.
I wanted to make sure my family had enough savings to cover at least a year’s worth of recurring expenses without touching their retirement accounts. My wife works and wanted a cushion in case she lost her job. I figured that would give me at least a year to get my business up and running, and if things were really bad, I would have enough time afterwards to find a job.
We were already in a good place in terms of savings, so we were able to take vacations, hire tutors for our kids, and order DoorDash. With about six months left before retirement, I made some adjustments, including reducing my 401(k) contributions and putting more money in a liquid savings account.
This financial planning process for my family was extremely helpful in crystallizing the direction I wanted to take with my startup. I retired from Meta in September 2025.
When I broke the news to my colleagues, I received a mixture of surprise, support, and a lot of jealousy. Many people would like to leave here and start something on their own, but are unable or unwilling to do so for various reasons, such as due to visa status, financial constraints, or greater fear.
I am now focused on my business, Bear Financial. My co-founders and I plan to open it to the public later this year. We may seek external funding, but for now we are bootstrapped and are tracking our spending very closely.
Advice for people in similar situations
I have some advice for people who are thinking of quitting their jobs and starting their own businesses. First, organize your financial situation. Second, make sure those who depend on you, such as your family, support your decision. I was lucky to have a supportive partner who understood my limitations working in Big Tech.
Third, Choose ideas that you deeply believe in. In a startup, you have to be the one who brings energy, enthusiasm, vision, and gets others involved.
Address knowledge gaps. Startup founders often need to be generalists. This means having a basic understanding of many areas.
I also recommend imagining the worst possible outcome and asking yourself if you’re okay with it. I thought about what would happen if my business failed a year from now. I will continue to cherish everything I have learned over the past 12 months.
If I eventually decide to return to a corporate job, I believe I will find something, even though it is difficult to predict what the job market will look like.
I’m happy with the direction of the startup so far
However, there are many potential barriers to success. You have to deal with changing regulatory goals, you have to figure out how to convince potential customers to give it a try, and there are companies with very deep resources that could be your direct competitors.
At the end of the day, I want to take a swing.
