As an executive coach, I’ve had the privilege of working with some incredible leaders who’ve faced challenges that would make most people throw in the towel. One of the most inspiring conversations I’ve had recently was with Jamey Edwards, a seasoned founder who’s building his third company with hard-won wisdom from the prior two.
Jamey’s story isn’t just about business success or failure—it’s about personal transformation. It’s about learning to advocate for yourself, valuing your own contributions as much as others, and having the courage to build differently after tough lessons.
When Trust and Karma Aren’t Enough
Jamey shared with me that he used to believe hard work and treating others well would naturally lead to success and reciprocity. It’s a comforting belief, but as he discovered, the real world doesn’t always operate that way.
“I’d spent years taking care of others, assuming they’d do the same for me when it mattered most,” he told me. “But when the chips were down, I learned the hard way that I wasn’t advocating for myself—and I paid the price.”
The cost wasn’t just financial, though that was significant. Jamey described the emotional weight of feeling let down by people he trusted. He admitted to losing tens of millions in value during a business sale and to grappling with self-doubt as he tried to process what had gone wrong.
Building Differently the Next Time
Jamey is now leading his third venture, and this time, he’s doing it on his own terms. The lessons from his past efforts are guiding him as he builds with intention and integrity.
Here are some of the changes he’s made:
Advocating for Himself
Jamey told me that advocating for himself felt selfish at first. “I grew up thinking that asking for more—whether it was equity, compensation, or recognition—was greedy. But now I see it differently. Advocating for myself is how I ensure I’m in the best position to serve others and lead effectively.”
This shift has led Jamey to negotiate equitable ownership structures and fair compensation for himself upfront, setting the foundation for a healthier partnership, aligned expectations, and more balanced team dynamic.
Learning to Say No
“As a people pleaser and optimist, saying no used to feel like shutting a door,” Jamey said. “Now I see it as a foundation, opening the door to a better conversation.” By setting boundaries and focusing on what matters, he’s avoided costly distractions and stayed true to his vision.
Choosing the Right Partnerships
One of the most moving parts of our conversation was Jamey’s description of his new co-founder. “It’s the first time I’ve worked with someone who looks out for me the way I look out for them,” he said. “We’ve made decisions that cost us individually because it was the right thing for the partnership.”
This trust and mutual respect are the bedrock of their venture, and it’s clear Jamey is prioritizing these qualities in all his business relationships now.
Rebuilding Self-Worth
Jamey admitted that after his second company, he questioned his own abilities. “There was a moment where I thought, maybe I’m not that good at building companies. That was a hard thought to face.”
Through therapy, reflection on his track record of value creation, and surrounding himself with the right people, he’s rebuilt his confidence, step by step.
“I realized that over the last decade or so, I had created over $500 million of equity value, and while it went to others, there was a lot to be proud of there. More importantly, I took a lot of pride in thinking about the millions of people helped by the companies I had the honor of leading.”
Jamey’s also mentoring other founders, helping them avoid the mistakes he made, which he said has been both healing and energizing.
A New Approach to Leadership
Jamey’s story is a reminder that leadership isn’t just about the outcomes—it’s about how you show up for yourself and others. He’s more intentional now, recognizing that advocating for himself doesn’t detract from his ability to serve his team, investors, or customers.
“As founders and leaders, we need to accept that it is ok to take care of ourselves. Advocating for myself is how I make sure I’m in a position to advocate for others,” he told me.
The Big Takeaway
Jamey’s journey speaks to a challenge many leaders face: the fear that standing up for yourself might make you seem self-serving. But as he’s demonstrated, advocating for yourself isn’t just about securing your future; it’s about modeling integrity, setting boundaries, and leading in a way that’s sustainable for the long haul.
If you’re struggling with putting yourself first, take a page from Jamey’s book: Learn to say no, choose your partners wisely, and don’t let fear or guilt keep you from claiming your seat at the table.
What’s one way you can start advocating for yourself today?
Let me know in the comments.