In this interview segment, James Wedmore recounts a pivotal moment around 2009‑2010 when he almost gave up on his entrepreneurial path. While attending a marketing conference, he ran into a former conference attendee who had recently sold a truck, built software, and earned $90,000. Seeing this rapid success triggered a deep sense of inadequacy and devastation for James, prompting him to tell his then‑girlfriend that he wanted to quit. Her encouragement—that he needed to endure the struggle to gain experience that would later help others—kept him moving forward, ultimately leading to his breakthrough about 18 months later. The conversation highlights the emotional toll of comparison, the importance of a supportive partner, and the perseverance required before success arrives.
Can you remember a moment when you almost left it all, when you almost quit? What was that? And what kept you still going?
Yeah, I remember. I remember the moment I had gone to a marketing conference. This is back in like 2009, 2010. And then six months later, I went to another marketing conference and I saw someone there that was at the front first marketing conference. And you see someone you know and you're like, oh my gosh, hey, good to see. I didn't know you were going to be here, blah, blah, blah. You do all this stuff and you're like, how you been? What have you been up to? And they went first and they said, well, since I last saw you, I sold my truck, took the money, built a piece of software, and I've made $90,000.
First I was like, that's really cool. And then they said, what if? What have you been up to?
I had nothing to share. I had no news, no updates, nothing exciting. I went home so devastated. I remember I called my then girlfriend at the time, now my fiance, and. And that's when I told her, I want to. I'm. I'm quitting. I'm done. I did it. I tried it. I did my best. I'm done. And it helps that she believed, always believed in me. And she's like, really psychic. She's like, no, I will not let you quit. And what came to her, she said, you need to understand, you need to go through this. You need to go through all of this so that you have the experience and you log the hours so that you can help other people in the moment when they want to quit. So it's not going to come easy to you, but it will come. So that was the day I almost gave up and almost quit. And it honestly wasn't probably for another 18 months before anything really popped. But that moment, I specifically, I was like, in my mind, I was done because people around me were seeing success, but I hadn't yet.