The Other Side of Enough

You spent years building—your business, your wealth, your reputation. You did what most people only dream of. And then… it happened. You hit your number. You got the house. The freedom. The status. But instead of pure satisfaction, there’s this nagging question you didn’t expect: Now what? Welcome to The Other Side of Enough —a podcast for high-achievers who’ve made it, but aren’t done yet. Hosted by entrepreneur and investor Drew Haney , this show explores the unspoken side of success: fulfillment, identity, and purpose after the grind.

The Other Side of Enough is a arts podcast hosted by Drew Haney, with 23 episodes on record and a Required Pod Score of 80.

Drew Haney hosts The Other Side of Enough, a arts show with 23 episodes published.

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  Episode #23

  Clint Turner on Obsession, Burnout, and Building Beyond Millions

  Sep 5, 20251h 21mS1

  <p><b>You can flip phones at 14, land at 21, and close million-dollar deals before 30—and still wonder if it’s enough.</b></p><p>In this conversation, Clint Turner shares how his obsession with deals took him from iPhones in a school cafeteria to complex distressed real estate plays. But the story isn’t just about scaling profits—it’s about facing burnout, chasing stimulation, and learning to slow down when success itself becomes unsustainable.</p><p>We talk deal junkie highs, the hidden costs of coaching, why “flow state” matters more than spreadsheets, and how fatherhood reshapes what achievement really means.<...

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  Episode #22

  From Peru to Profit: Jason Wollbrink on Faith, Marriage, and Enough

  Aug 27, 20251h 16mS1

  <p><b>What if the life you built wasn’t the life that built you?</b></p><p>Jason Wollbrink left the Midwest to plant churches in Peru—only to discover that success isn’t about the house you flip or the money you make, but the presence you bring to the people you love.</p><p>In this episode, Drew and Jason go deep on the questions high-achievers rarely ask out loud:</p>Can you lead in business and at home without burning out either one?Why does financial freedom often feel hollow without identity rooted in something deeper?What d...

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  Episode #21

  ADUs, Airplanes, and the Weight of What’s Next with Alan Underwood

  Aug 20, 20251h 5mS1

  <p><b>What happens when selling cars turns into building communities—and facing yourself along the way?</b></p><p>In this episode, Drew sits down with <b>Alan Underwood</b>, whose path runs from managing pizza buffets to scaling an $16M car dealership, and now transforming single-family homes into multi-unit investments through San Diego’s ADU laws. But this isn’t just about spreads and construction, Alan opens up about grief, depression, and the day he nearly ended it all, before aviation and purpose gave him a new reason to keep climbing.</p><p>You’ll hear:</p>How Alan bui...

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  Episode #20

  Joshua Sun on Redefining Success Beyond the Mortgage Game

  Aug 13, 20251h 3mS1

  <p><b>You can crush it in your career and still feel the pull toward something more.</b></p><p>For 20 years, Joshua Sun built a thriving mortgage business. By all external measures he had made it. But when he saw how quickly the industry could change and how little fulfillment he felt in the work, he knew it was time to climb a different mountain.</p><p>In this conversation, Joshua opens up about the pivot that took him from comfortable routine to high-stakes purpose: raising capital for creative real estate deals, keeping families in their homes, and funding...

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  Episode #19

  When Success Feels Heavy: Joe Roberts on Faith, Fire, and What Comes After the Climb

  Aug 6, 20251 hourS1

  <p><b>He built a 7-figure land business, launched a top-tier cold calling company, and co-owns a recession-proof service brand. But Joe Roberts isn’t chasing more—he’s asking better questions.</b></p><p>What anchors you after the grind ends?<br/> For Joe, it’s faith, family, and a quiet refusal to let his identity be tied to titles—even the ones most men would kill for.</p><p>In this episode, we explore what it means to lead from conviction in a world obsessed with scale. Joe shares how his years as a Marine shaped how he builds team...

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