OFF THE RECORD

Greg Wolfe
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  • Entrepreneurship
  • Updated Weekly

Greg and his guests talk through their experiences: building a business, navigating setbacks, making difficult choices, and learning from mistakes. Success is part of the conversation, but so is what it took to get there. Alongside guest interviews, episodes feature conversations among the hosts that can move from business to personal experience or head somewhere nobody expected. You don’t have to be an entrepreneur to listen—just interested in how other people think, live, and approach the challenges in front of them.

Episodes

  1. 1d ago

    The Business Move That Forced Us to Start Over

    Our agency was growing. Then we followed people we trusted—and ended up having to rebuild. For the first full episode of Off the Record, Greg and Chelsey Wolfe share their experience leaving Family First Life (FFL), making a move they thought would help their team, and eventually deciding to return. They reflect on the promises that shaped that decision, the warning signs they brushed aside, and the strain of trying to keep a business moving when the support they expected wasn't there. The conversation also turns to family, the pressure to work constantly, and what they wanted to do differently as they rebuilt. In this episode: • Trusting mentors without doing enough independent research • The gap between the opportunity they were pitched and their experience • Losing agents, chasing payments, and questioning the next step • Building a business without missing their kids' childhoods • The difficult decision to leave and return to FFL • Rebuilding the team with clearer expectations and simpler systems CHAPTERS 00:00 Welcome to Off the Record 01:28 Building the agency and gaining momentum 02:26 Following people we trusted 09:59 The warning signs we wish we'd questioned 17:12 What happened after the move 23:26 Chasing payments instead of building the business 28:43 Family, work, and what success should look like 31:55 Deciding it was time to leave 37:54 Returning to FFL and starting over 40:38 Rebuilding the team, month by month 45:54 What we'd tell someone who feels stuck Watch this episode on YouTube: https://youtu.be/IU-HyeeMT4g Follow Off the Record so you don't miss the next conversation. Instagram: https://www.instagram.com/off_the_recordpod/ Facebook: https://www.facebook.com/otrpodshow

  2. Sep 4

    Welcome to Off the Record | Official Trailer

    Welcome to Off the Record—a place for real conversations about business, family, failure, success, and everything in between. We want the wins, but we also want what it took to get there: the struggles, the mistakes, the hard decisions, and the parts that never make it onto social media. Some episodes will feature Greg and his guests. Some will be about business, some about life, and some will go completely off the rails. Nothing scripted. Nothing polished for social media. Just real conversations, wherever they take us. Follow Off the Record so you don’t miss the first episode. Instagram: @off_the_recordpodFacebook: @otrpodshowYouTube: @off_the_recordpod

Trailer

About

Greg and his guests talk through their experiences: building a business, navigating setbacks, making difficult choices, and learning from mistakes. Success is part of the conversation, but so is what it took to get there. Alongside guest interviews, episodes feature conversations among the hosts that can move from business to personal experience or head somewhere nobody expected. You don’t have to be an entrepreneur to listen—just interested in how other people think, live, and approach the challenges in front of them.

Information

  • Creator
    Greg Wolfe
  • Years Active
    2026
  • Episodes
    2
  • Rating
    Clean
  • Copyright
    © Greg Wolfe
  • Show Website
    OFF THE RECORD