Rob never imagined that rock bottom would become the foundation for the life he was always meant to build. Newly married and full of plans, Rob was managing properties for top developers—until the 2009 crash pulled the rug out from under him. Laid off, broke, and forced to move back in with his parents, Rob found himself facing a painful question: Now what?

In this honest and hopeful conversation with host Teko Bailey, Rob shares how losing everything sparked a total reinvention—from mindset to career to faith. Through long runs, early podcasts, library books, and deep spiritual reflection, Rob rebuilt not only his confidence, but a life rooted in leadership, purpose, and family. Now a successful real estate broker, husband, and father, Rob reflects on what it takes to grow when everything falls apart.

If you're navigating uncertainty, questioning your next move, or searching for meaning beyond the hustle, this episode is your reminder: rock bottom isn’t the end. It’s the beginning of the climb.

Major Themes & Concepts

✅ Reinventing yourself after failure

✅ Marriage, fatherhood, and showing up with intention

✅ Building confidence through habits and discipline

✅ The power of mindset, mentorship, and asking questions

✅ Learning to pivot when the plan falls apart

✅ Faith, prayer, and trusting God through uncertainty

✅ Leading with ownership—even before you’re the boss

🕰️ Chapter Breakdown

00:00 – Losing the job, the house, and hope

01:46 – Meet Rob: Cuban roots, new marriage, new struggle

04:03 – The crash of 2009: moving home and hitting bottom

06:54 – Library cards, podcasts, and running toward growth

09:25 – From employee to owner mindset: stepping into leadership

13:48 – The spiritual rebuild: prayer, presence, and daily action

17:50 – Calculated risks, conservative fears, and breaking the ceiling

21:32 – Family first: redefining ambition with fatherhood in mind

25:14 – Men, burnout, and the trap of distraction

27:42 – Creating momentum when you feel stuck

29:38 – Final encouragement: your next chapter is possible

About Teko Bailey

Teko Bailey is a husband, father, coach, and guide for men walking the path of faith and purpose. Through The Climb, he’s building a brotherhood of men committed to living fully, leading boldly, and climbing with intention.

Instagram: ⁠⁠⁠⁠⁠⁠@IamTekoBailey⁠⁠⁠⁠⁠⁠

Website: ⁠⁠⁠⁠⁠⁠tekobailey.com⁠⁠⁠⁠⁠⁠

Production, Distribution, and Marketing By Massif Studio & Production and The Tallawah Group

Massif Studio & Production

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The Tallawah Group

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