OFF THE RECORD

Greg Wolfe
  • 5.0 (1)
  • 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. Conversations 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. 6d ago

    I Took It Personally When People Quit | Off the Record Ep. 4

    The first person who left Greg’s business was a relative. His first thought was that he must have failed them. In this solo episode of Off the Record, Greg Wolfe talks about the personal side of building a team: taking departures to heart, setting honest expectations, and learning that enthusiasm in an interview does not always turn into follow-through. He also breaks down a pattern he had to change—recruiting a group, pausing to develop them, then feeling the gap months later—and why finding people who can build with you matters. No guest this week. Just Greg, a microphone, and a few things he had to learn by doing. Have you ever taken it personally when someone left? Tell us what helped you see it differently. IN THIS EPISODE• Why Greg took his first team departure personally• The difference between poor fit and personal failure• Giving people the full picture before they commit• Interview confidence versus follow-through• The delayed cost of pausing recruitment• Finding leaders and partners who can build alongside you 00:00 A solo conversation with Greg00:25 Off the Record intro01:02 Meet Greg and the solo format01:47 Why the opportunity doesn’t fit everyone03:40 The first person who left04:56 Rethinking the “quitter” label06:15 The pitch versus the reality07:20 Everybody interviews well08:18 What an independent role requires11:55 The cost of pausing recruitment13:03 Find people who can build with you13:39 What Greg is doing differently now Watch Episode 3 on YouTube:https://youtu.be/StcWv531u54 Follow the show on Instagram: @off_the_recordpodFollow the show on Facebook: @otrpodshow

    I Took It Personally When People Quit | Off the Record Ep. 4

  2. Oct 1

    Why Does Everyone Post the Same Thing? | Off the Record Ep. 3

    Same trends. Same videos. At what point do we stop sounding like ourselves? Greg sits down with Matthew Doering, the man behind the camera at Off the Record, for a conversation about AI, finding work that actually fits, and why everyone's social feed is starting to look the same. Matthew shares what it's really like building with AI agents, why being good at sales didn't mean it was the right job for him, and how he's finding his lane through technology, filming, and editing. They also get into ChatGPT versus Claude, the pressure to follow trends, and why showing up as yourself matters more than copying another creator's formula. Plus: rapid-fire questions, an airport detour, and a few very questionable life tips. Where's the line between inspiration and copying? Tell us what you think. CHAPTERS 00:00:00 The Cold Open 00:02:45 Meet Matthew Doering 00:04:54 AI Hype Versus Reality 00:12:22 Rapid-Fire Questions 00:15:26 Finding Your Lane 00:20:52 Hey Matt 00:25:16 Make Your Own Trend Follow Off the Record for more conversations with Greg and his guests. Watch on YouTube: https://www.youtube.com/@off_the_recordpod Instagram: https://www.instagram.com/off_the_recordpod/ Facebook: https://www.facebook.com/otrpodshow Spotify: https://open.spotify.com/show/5fMgU8ub79Vhp3FCm3JGUu Apple Podcasts: https://podcasts.apple.com/us/podcast/off-the-record/id6808746667

    Why Does Everyone Post the Same Thing? | Off the Record Ep. 3

  3. Sep 24

    Bumble, Ghosting & How We Ended Up Together | Off the Record Ep. 2

    They met on Bumble. Getting together was the complicated part. Greg sits down with his wife, Chelsey Wolfe, to tell the story of how they met—from a late-night first date and a car deal gone sideways to mixed signals, a pros-and-cons list, and the moment things finally clicked. They share who said “I love you” first, the surprise proposal disguised as Greg's 30th birthday, and the everyday habits that still drive each other crazy. The conversation also turns to communication, raising their family, and what they want life to look like ten years from now. Who takes longer to get ready—and who starts rushing an hour too early? CHAPTERS00:00 Welcome to Off the Record01:05 How we met on Bumble04:36 The car deal that got complicated08:24 A Florida trip and a pros-and-cons list11:25 The date that brought us together14:48 Who said “I love you” first?15:56 A birthday party turned surprise proposal19:15 Couples rapid-fire questions22:24 Our biggest pet peeves24:36 Being late vs. being rushed26:02 What we hope never changes27:09 The life we want ten years from now Follow Off the Record so you don’t miss an episode. Enjoyed the conversation? Leave the show a rating—and tell us who made the first move in your relationship. Spotify:https://open.spotify.com/show/5fMgU8ub79Vhp3FCm3JGUu Apple Podcasts:https://podcasts.apple.com/us/podcast/off-the-record/id6808746667 Instagram:https://www.instagram.com/off_the_recordpod/ Facebook:https://www.facebook.com/otrpodshow

    Bumble, Ghosting & How We Ended Up Together | Off the Record Ep. 2

  4. Sep 17

    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

    The Business Move That Forced Us to Start Over

  5. 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

  • 1 Trailer
    4 Episodes

Trailer

Ratings & Reviews

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. Conversations 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
    5
  • Rating
    Clean
  • Copyright
    © Greg Wolfe
  • Show Website
    OFF THE RECORD