For many founders, mental health support is often the last thing on their laundry list of to-dos as they focus on scaling their businesses. And the barriers to care don’t help—whether due to cost, time, stigma, or simply not knowing where to turn. Much of that strain goes unaddressed. James Oliver Jr. sees the issue as a systemic gap. After experiencing the toll firsthand—including a failed startup, divorce, and raising twins—Oliver set out to build something he wished existed when he needed it most. “In order to go to heaven, you’ve got to go through hell,” he said. In March 2025, Oliver launched the Kabila Founder Mental Health Fund. Through the fund, US-based founders can receive four free virtual therapy sessions, or be reimbursed up to $300 for therapy if they already have a provider, and are connected with other wellness resources. According to Oliver, the fund has supported nearly 70 founders to date and its website notes the fund has raised over $90,000 in donations. This month, venture capitalist Brad Feld, who also provided a seed grant, said he will match up to $25,000 in donations to Kabila. Over a conversation and emails with Founder Brew, Oliver shared his vision for the fund, the challenges of scaling it, and what still needs to change to address founder mental health challenges. This interview has been edited for length and clarity. Why do you think it’s so difficult for founders to ask for help? A lot of the time, they see it as a sign of weakness. In some cases—and they’re probably right about this—they feel like they will be judged by investors and deemed as uninvestable, unstable. Do you think loneliness is a common experience among founders? Absolutely. “Why?” is your next question. Because if you’re a founder, 99% of the people in your circle—unless you’ve got a bunch of founder friends—don’t understand what you’re doing, why you’re doing it, why you would choose to put yourself through the meat grinder every day. They don’t get it, so it’s lonely.“Oh, why don’t you go get a job?” Because I’m the world’s worst employee, that’s why. Aside from money, what are the biggest barriers right now to expanding this kind of help for more founders? It's money, it’s awareness, it’s people talking about it, people being willing to lead…We need more people willing to lead in the conversation, willing to lead by expanding access to information and resources to their founders in their communities, and just being willing to talk about it and to normalize the conversation. We simply need more people, more awareness, and more money. Read More.—JH | 
