S2E11: Resilience Meets Reality: James Oliver on Mental Health, Hustle Culture & Founders in the Fight​​​

Startup founders love to talk about grit, hustle, and perseverance. What they rarely talk about is what all of that costs.

In this episode of Living Undeterred, Jeff Johnston sits down with James Oliver Jr. – a tech founder, community builder, and the force behind the Kabila Founder Mental Health Fund, which provides free therapy for startup founders who cannot afford it. James is also launching Kabila Ventures, co-founded the ParentPreneur Foundation, and has written books on both entrepreneurship and mental health in the startup world.

James shares how launching his first startup while his premature twins fought for their lives in the NICU nearly broke him, why he now calls hustle culture toxic, and how he is working to normalize mental health support for founders, especially those who are overlooked and underfunded.

This Q&A has been edited for clarity and length, but the voice, stories, and wisdom are James through and through.

Listen to the full episode here:

Q&A WITH JAMES OLIVER JR.

Jeff: When you say "founder mental health," what do you mean?

James: When I say "founder," I am usually talking about someone building a tech or tech enabled startup with high growth and high revenue potential, not just any small business. A founder is someone trying to build a high margin, scalable company, often with investor money and a lot of pressure on their shoulders.

On paper that sounds exciting. In reality, it can be brutal.

There is still a big stigma around mental health for founders. I talk to founders all the time, and almost every one of them is having a hard time. The data backs it up. Around 70 percent of startup founders struggle with their mental health. Yet when I literally say, “We will pay for therapy, just fill out this form,” they suddenly get shy. They say, “Let someone else have it,” even after they just got off the phone telling me how much they are struggling.

So founder mental health to me is everything behind the pitch deck. It is the anxiety, the “I cannot get out of bed,” the constant rejection, and the pressure to look unshakable while you are falling apart inside.

Jeff: What is the story that led you into this work?

James: My story really starts in 2012. I cleaned out my savings to build my first startup, WeMontage, which let you turn your digital photos into removable photo wallpaper. I am a non technical founder, so I paid about thirty five thousand dollars for an alpha version of the site. Right when I did that, we found out twins were on the way through IVF.

The only shot I had to make this company real was to get into an accelerator. I was living in a small town in northeast Wisconsin, far from my family in Brooklyn. I got into gener8tor, which was two hours away in Madison.

The timing was supposed to be perfect. The twins were due at the end of March. The accelerator ended the first week of April. Then life said, “Nah.” Two days before the accelerator started, the doctors told us my son’s blood flow was starting to go backward. If we did not do an emergency C section, he would die. So my twins were born three months early. They weighed about two pounds each. I could literally fit my son in my hand.

So picture this:

• I am a thousand miles away from friends and family.
• I have a two hour drive each way to the accelerator.
• My kids are in the NICU.
• I am out of money.

I was waking up at two in the morning every day from stress. My face was breaking out. I felt like I was aging in reverse, like some messed up Benjamin Button situation. You could have just told me “Good morning, James” and I might have started crying. It was that bad.

Right before demo day, an angel group called and said, “We are going to fill your round.” Back then I was only raising two hundred fifty thousand dollars. That is nothing today, but it was everything to me. I literally dropped to my knees and cried. We raised the money, the kids came home after weeks in the NICU, and I kept grinding.

But then we ran out of money. Everyone quit. It was just me. I got the company on the Today Show three times, Good Morning America, Martha Stewart’s blog, Money magazine, all without a publicist. I thought that would save us, but it did not. One of my investors told me straight to my face, “I am not going to throw good money after bad.” That stung.

Looking back, I was functionally depressed for years. My marriage fell apart. I kept pushing, kept hustling, kept telling myself that was what founders do. Eventually I wrote my first book, The More You Hustle, The Luckier You Get: You CAN Be a Successful ParentPreneur, based on my blog at the time. Ironically, today I believe hustle culture is toxic. That grind almost destroyed my mental health.

All of that pain, plus watching founders around me suffer silently, is what pushed me into this mission.

Jeff: You often say you are incredibly resilient, but also exhausted. What do you mean by that?

James: I joke that I am in the ninety ninth percentile of resilience on this planet. I have had to be. But I also say, “Just because I am resilient as hell does not mean I always want to have to be.” It is exhausting.

We celebrate founders who are “tough” and “relentless,” but we forget they are human. I see people who claim to “hold space” for founders. Investors, accelerator staff, ecosystem builders. Then they will criticize a founder for not showing up as their best self every single time.

Sometimes a founder has heard “no” a thousand times that week, is worried about rent, cannot pay their team, and still has to put on a brave face. They may not answer your email perfectly. They may not nail their pitch that day. That does not mean they lack potential. It means they are going through something.

So I am constantly asking for more grace. If you are an investor or you run an accelerator, remember there is a human behind the deck. Treat them that way.

Jeff: Tell us about Kabila, the Founder Mental Health Fund, and what you are building next.

James: I am building a few connected things.

First, there is Kabila, which started as a co founder matching app and founder community. We help overlooked founders find co founders, customers, and capital. I am now launching Kabila Ventures, a new venture fund that will back overlooked founder teams from diverse backgrounds. The data is clear. Diverse teams consistently generate strong returns, and I have deep access to those founders through years of community building.

Parallel to that, I created the Kabila Founder Mental Health Fund, a nonprofit that provides free therapy for startup founders who cannot afford it. We started with small grants and have already funded dozens of therapy sessions. My vision is simple. If you are a United States based founder who needs help and cannot afford therapy, there should be a place you can go, answer a few questions, attest that you cannot pay, and get support. No shame. No hoops. Just help.

I reached out to my friend Brad Feld years ago. He is a legendary investor and co founder of Techstars. Brad gave us a grant after George Floyd was murdered to start the ParentPreneur Foundation, and later gave a grant to launch this founder mental health fund. We are now partnering with platforms like BetterHelp so we can scale efficiently and track impact with real metrics, not just stories.

We named the grants after my grandmother, Carmen Reed. She was a Panamanian immigrant, a Black woman, a seamstress, and an entrepreneur. She left an abusive marriage, moved to New York, saved her money, and bought a brownstone in Brooklyn. She died from a massive stroke in her early fifties from all that stress, and I never got to meet her. I often wonder what would have happened if she had access to therapy or an app like Brightn. Naming the grants after her lets me honor her courage and keep her legacy alive.

Jeff: You also founded the ParentPreneur Foundation. What did that teach you about community and mental health?

James: The ParentPreneur Foundation came out of that “Trap Life” blog I started while working from home, caring for my kids, and trying to build a startup. I realized parents who are founders face a unique set of pressures. You are responsible for a company and for your kids, and both jobs are full time.

We used the foundation to empower Black ParentPreneurs with grants, mentorship, and community. One of the most powerful things we did was pay for more than 400 therapy sessions. That may not sound like much at scale, but in the Black community, therapy is not a default choice. Culturally, we are more likely to go to a pastor than a therapist. There is stigma, and some of it is rooted in real mistrust.

So when we dropped the application form, people came. Dozens booked therapy, and the testimonials we got back were incredible. People said it changed their marriages, their parenting, their ability to lead. That was my signal to double and triple down on mental health, especially for Black founders.

Jeff: How do you see AI fitting into mental wellness for founders and beyond?

James: I want to be clear. I am not an AI expert. What I know comes from reading and talking to people like you who are building in this space. Based on that, my take is that generative AI is powerful but can be dangerous if it is not grounded in the right frameworks.

If an AI system that is talking to someone about their mental health is not constrained by evidence based approaches like cognitive behavioral therapy (CBT) and similar modalities, it can lead people down some dark paths. It could make their situation worse instead of better. That is not theoretical. We have already seen some horror stories in the press.

At the same time, I recognize that even human therapy is not perfect. People have terrible experiences with therapists too. So for me, the question is not “AI or humans,” it is “What tools belong in your mental health toolkit, how are they trained, and what guardrails exist?”

I like the idea of tools like Brightn being a bridge in between sessions with a human therapist. When your appointment is next month but you are struggling tonight, having a safe, well designed companion that can help you journal, reflect, and ground yourself is valuable. The key is safety and alignment with real mental health science.

Jeff: You are also involved with The Real. Why is that community important to you?

James: The Real is a movement that focuses on men’s mental health and real connection. I serve as the ambassador for the Johns Creek and Alpharetta area in Georgia. We do weekly walks where men get together, move their bodies, and talk about real stuff. I love that my wife and kids come too. My daughter was out there doing thirty push ups with the guys at one of our walks. That is the kind of normalization I want for mental health.

What I love most is that we skip the small talk. I hate small talk. I am an ambivert, but I do not want to talk about what you do for a living unless that conversation actually leads to a real human connection. The Real creates environments where you can say, “Here is what is going on in my life personally and professionally,” and people actually listen.

Those Zoom “speed friending” breakout rooms Jeff mentioned are powerful. You go deep with strangers in minutes. That is how community should feel.

Jeff: For founders listening who feel alone and functionally depressed, what would you tell them?

James: First, you are not the only one. Everyone you know is going through something, whether they show it or not. Founders are especially good at hiding it, but they are struggling. Remember that and have some grace for yourself.

Second, get help. I resisted therapy for a long time. Now I have a therapist and a toolkit of skills that help me compartmentalize, focus on what I can control, and not be consumed by everything that is on fire around me. Compartmentalization, used in a healthy way, is a beautiful thing.

Third, build relationships before you need them. This game is long. You cannot treat people like transactions. Some of the best breaks I have gotten happened years after I met someone, simply because I stayed in touch as a human being, not because I kept asking for something. That is how Brad Feld ended up reading my book, blogging about it, and later funding two of my nonprofits.

Finally, remember that not all money is good money. If an investor expects you to be a robot and sees your vulnerability as weakness, they might not be your people. Look for investors and partners who believe that caring for your mental health is part of building a successful company, not a distraction from it.

Jeff: Where can people find you and support what you are doing?

James: The best place to connect with me is LinkedIn. Search for “James Oliver Jr” and you will find me. If you send a connection request, please add a note that you heard me on the Living Undeterred podcast so I know you are not just some random pitch in my inbox. I try to keep LinkedIn high quality, not just high quantity.

To learn more about the Kabila Founder Mental Health Fund, you can visit our landing page where we outline what we do, share testimonials, and give you a way to support the work. The grants are called the Carmen Reed Founder Mental Health Grants in honor of my grandmother.

And keep an eye out for my upcoming book on founder mental health, where founders and investors share their stories. All the proceeds will go back into the mental health fund. We are even planning a modern version of a Jerry Lewis style telethon to raise money and awareness.

Conclusion

James’ story is a reminder that even the most resilient founders and parents have limits. Behind every pitch deck and LinkedIn win is a real human trying to juggle ambition, responsibility, and their own mental health. When we normalize therapy, honest conversations, and everyday tools that support our minds, we give people a better shot at “burning bright” instead of burning out.

If you are ready to take one small, practical step for your own mental health, try Brightn. Our AI-guided journaling, mood tracking, and daily check-ins help you process stress, build healthier habits, and stay grounded between those big moments.

Download Brightn today to start your free trial and give your mental health the same focus you give your goals.