Why I Fired Myself as CEO of Win BIG Media

Phillip Stutts
3 min readMay 19, 2023

I’m out as CEO at Win BIG Media.

* You can learn more about what happened this week on the Undefeated Marketing Podcast, where I talk in more detail about what happened that changed everything for me.

Running a company is challenging as hell, and being a CEO is the most demanding role in business. However, sometimes, the best decision you can make for your company is to fire yourself as the CEO.

It may sound counterintuitive, but in some situations, this can be the best decision for everyone involved.

Here are 3 reasons why I fired myself as CEO of Win BIG Media:

  1. I wasn’t the right fit for the job anymore:

Although I founded the company (and built it to a high seven-figure business with no outside investors and no debt) and I’m still passionate about its data-driven mission, I recognized that my strengths did not necessarily align with the responsibilities of a CEO. I realized that my strengths lay in creative and strategic thinking, and I struggled with the day-to-day management tasks required of a CEO. By recognizing my limitations, I was able to make the difficult decision to step down and allow my #2, Brandon McKee (who has a much better skill set as CEO to grow our clients’ bottom lines) to take over.

2. Win BIG needed fresh leadership:

As the company grew, I realized that it needed fresh leadership with new ideas and perspectives. I recognized that the company had outgrown my leadership style, and that it needed a new CEO who could take our culture and our clients to the next level. By stepping down, I was able to make room for Brandon to bring a fresh approach to the company and our clients — thus helping it continue to grow and succeed.

3. I needed to rebalance my work life

By stepping down as CEO, I was able to take a step back and re-evaluate my priorities, invest in and help grow my other four companies and spend more quality time with my family.

In summary, firing myself as CEO of Win BIG Media was a difficult decision, but it was ultimately the best move for the company’s success. By acknowledging my limitations and recognizing the company’s need for fresh leadership, I was able to make room for Brandon McKee to take the company to the next level.

I’m still involved (as Executive Chairman), I’m still obsessed with Win BIG’s data-driven marketing and I will still be available to help clients grow. I just need to focus on my core passions and strengths going forward.

If this feels like something you struggle with at work (not being able to solely focus on your strengths), then CLICK HERE to learn more on how I made my decision and let me know how I can help you with your challenge.



Phillip Stutts

Founder/CEO: Win Big Media | Founder: Go Big Media | Repped by Vayner Speakers & Keppler Speakers | Author: “Fire Them Now: The 7 Lies Digital Marketers Sell…”