What happens when selling cars turns into building communities—and facing yourself along the way?

In this episode, Drew sits down with Alan Underwood, 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.

You’ll hear:

• How Alan built and sold a dealership doing $16M in annual revenue
• The unique San Diego ADU play turning houses into multifamily cash flow
• His raw story of loss, suicidal thoughts, and the unexpected power of flying
• Why he now measures success with two words: be there

Alan is the managing partner at Momentum Capital. To learn more, visit mmtmgrp.com or connect with him on Instagram, Facebook, and LinkedIn at @thealanunderwood.

This is real talk about money, meaning, and the choices that define us.

You’ve built the life everyone else wanted. Now it’s time to ask what you want.
Thanks for being with us on The Other Side of Enough.
This isn’t the end of the conversation—it’s the beginning of your next summit.