Jason Mathew: From Product Manager to Full-Time Founder

January 10, 2024

Meet Jason, an entrepreneur who made a life-changing move from Austin to Tulsa, seeking a sense of community and deeper purpose. If you’re a member here at 36°N, chances are you know Jason and maybe you know a little bit about his startup LeadMeNot. The app addresses destructive digital habits, aiming to revolutionize our relationship with technology. There’s a lot to learn from Jason and his journey of transitioning from product management at IBM to full-time entrepreneurship. Balancing work and well-being, Jason is navigating a healthier relationship with technology as he builds a thriving life and community here in Tulsa. But don’t take it from us- check out his story below!

What motivated you to move from Austin to Tulsa through the Tulsa Remote program, and how did it impact your life?

I was in living in Austin, TX when I decided to move to Tulsa. To be frank, the isolation induced by COVID was slowly killing me, and I was looking for an escape. Since moving here, I’ve experienced a newfound richness in life. Personally, I’ve found community in my church, Tulsa Remote, and 36 Degrees North that have been life-changing. Friendships that have really allowed me to feel loved and known in ways I never have. Professionally, being in Tulsa has unearthed and reinforced my desire to be an entrepreneur.

What has your life been like since moving to Tulsa? How have you made this your home?

Life since moving to Tulsa has been amazing, but also challenging. I’ve experienced a lot of firsts here: my first home, my first tenants, my first layoff, my first car (yes, my first car!). I think that everywhere I lived prior to Tulsa felt temporary not because I lived a temporary life or made temporary decisions, but because my heart never felt a yearning to be fully present. I did feel that in Austin, but after coming to Tulsa, it became stronger.  

Can you share the story behind LeadMeNot and how your personal journey influenced the creation of a digital wellness platform?

It’s never easy admitting that you need change. The very idea of acknowledging you have certain behaviors and habits that are no longer fruitful, that were never fruitful and have crossed the line of being destructive is challenging. To some, it’s near impossible. That’s where I was at the beginning of 2018. Personally, I used dating apps as a way to fill a void. I created LeadMeNot because I’ve realized that it’s not just online dating that can lead to destruction, unhealthy digital habits can take MANY forms. It can literally be anything that consumes your heart, soul, and mind to the point of addiction. I want people all over the world to experience the same freedom that I’ve experienced, by taking their first steps toward understanding the ‘why’ behind their behavior.

How have you seen/ how do you envision LeadMeNot making a positive impact?

My desire is for LeadMeNot to emerge as a trailblazer in digital wellness, profoundly reshaping our relationship with technology. It's not just a product, but a movement, integral to daily life for millions worldwide. I want it to be known for its pioneering blend of AI and human insight, revolutionizing the way we interact with our digital devices, turning potential distractions into tools for personal growth and well-being, helping the world understand the 'why' behind their behavior, in both the digital and physical worlds. In the corporate world, LeadMeNot can be a staple, enhancing productivity and employee well-being, while its community initiatives address digital wellness at the grassroots level. The platform's continuous innovation keeps it at the forefront, adapting to emerging digital challenges and shaping a more mindful, connected, and healthier digital society.

We see a world where LeadMeNot can become an all-in-one digital accountability partner, that knows you better than you know yourself, thanks to the data you produce. That text your mom just sent you? Well, you told us that anger is a trigger, and it seems like she used a tone that could very well set you off. Why don’t you reach out to Jack right now, or go for a walk? We want to know what triggers you, what helps you, and what grows you, and use that information in a redemptive manner.

This is not with the intent to replace human interaction, but to point back to community and relationship for support, healing, and freedom from the behaviors and mindsets that bind us. In essence, LeadMeNot's success lies in changing the narrative around technology—from a story of addiction and distraction to one of empowerment and mindful engagement, creating a legacy that transcends technology and transforms lives in profound and lasting ways.

Transitioning from a remote worker to an entrepreneur is no small feat. What challenges did you face during that pivot, and what lessons did you learn that you think would be valuable for others contemplating a similar shift?

I struggled for the longest time having one foot in and one foot out. I created LeadMeNot as a passion project/hobbyist while working full-time at IBM. I had one foot in corporate America and one foot in the world of entrepreneurship. Toeing this line for 2.5 years made it that much more challenging to give LeadMeNot 100% of my energy, thinking power, love, and envisioning. I believe God made the decision for me by allowing me to get laid off from IBM. Now, for the last 6 months, I’ve been working on LeadMeNot full time and have been working to figure out just exactly where to focus to become an impact-first, self-sustaining, SaaS business.

The strongest lessons I’ve learned thus far would be to (1) surround yourself with a very strong advisory board early on and (2) make sure that you have a keen sense of short, mid, and long-term vision. On the latter, I often prided myself in my ability to formulate long-term vision (where can we be in 5-10 years) while being a strong short term executioner (how do we get from 0-1) but realized, in the last six months, that I’ve been terrible at the mid-term. I needed my advisors’ guidance to help me come to terms with this reality.

You are a staple here at 36°N! Tell us why you've found such value in getting involved here

My favorite aspect of being a member at 36 Degrees North has been the relationships and connections I’ve built over the last 3 years. Folks whom I’ve literally bumped into in the kitchen, or passing by on a walk around the Arts District. It has been these relationships built at 36°N that inspired me to apply for accelerator programs, participate in pitch competitions, and generally keep pushing forward on what I believe in. The staff at 36°N encouraged me to apply for the OCEAN accelerator, which I was accepted into, and eventually led to meeting my current investors. The relationships I’ve built and the decisions I’ve made as a result of the guidance, support and even rebuke I’ve received from my 36 community have been all I’ve truly needed.

Balancing the demands of entrepreneurship and personal well-being can be challenging. How do you manage to maintain a healthy work-life balance, especially given the nature of your work in digital wellness?

I’m still figuring this out. I’ve been able to maintain a much healthier relationship with my phone and technology as a whole (deactivating my Facebook and having my friend change the password, using LeadMeNot to limit access to YouTube, LinkedIn), but I’m still learning how to maintain a consistently healthy work-life balance. Interestingly enough, I don’t think I work as much as I used to, compared to even two years ago, but I do think about work a lot more and am trying not to work for the ‘sake of working.’ I’ve realized more recently that I would often work because I wanted to numb out from having nothing else to do. Now, I have a lot more I want to do, with people I want to do said things with, so my motivation to sit behind a computer screen for as long as possible each day has dropped pretty dramatically.

So, what's next for LeadMeNot? What are you focusing on in 2024?

We're expanding our value proposition to lower our barrier of entry. There's high demand for digital wellness tooling, but accountability as the only option has been a limiting factor for a while. We're finally doing something about that, and are hopeful that making the appropriate changes will grow our subscriber base towards being a self-sustaining SaaS business (at a minimum).

What advice would you give to individuals considering a similar entrepreneurial journey, especially those who are passionate about addressing societal issues through technology?

If you’re going to do this by yourself, as a solopreneur, then surround yourself with a core team of advisors ASAP. Make sure that these advisors are fully bought in and dedicated to your journey. If not, it’s going to be a VERY lonely ride ahead.

Tell us about your favorite spots in Tulsa! What are you doing in your free time??

Anywhere with scotch, cigars, fried chicken, and/or a nice pool table. The Summit Club, Classic Cigars, Chicken and the Wolf, my living room. Maybe I need to build a physical wellness app next :P