The Invest and Roam Podcast with Dear Ngo

How Keeley Raised $29M Without Pitching — And Built a Vineyard Legacy That Prints Cash for 40 Years


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In this episode of Invest & Roam, Keeley Hubbard shares how she pivoted from a high-level corporate sales career to managing a 1,000-acre vineyard syndication, raising $29 million, and building long-term passive income — all while doing business with heart and authenticity.

Here’s what we explore:

  • How Keeley raised millions without being “salesy”

  • Why Texas vineyards are exploding — and how to invest in them

  • How mindset, self-awareness, and joy can unlock your next big leap

If you're craving both financial freedom and personal fulfillment, this episode blends real estate investing, alternative assets, and personal growth into one powerful conversation.

Guest Bio:

Keeley Hubbard is a capital raising coach and Managing Partner at Texas Legacy Vines, overseeing one of the largest mechanized vineyard syndications in the state. Known for her authentic relationship-driven sales approach, she has raised tens of millions in capital across real estate and tech and is passionate about helping investors build wealth through legacy-driven strategies.


📌 Episode Highlights:

00:00 – Why Keeley ditched traditional sales forever

01:00 – From corporate VP to capital raising entrepreneur

05:45 – Texas wine vs. California wine: what's the real opportunity?

08:20 – What investors must know before investing in vineyards

11:00 – Raising money without pitching — Keeley’s anti-sales method

15:45 – The mindset shift that helped her raise $29M

21:00 – How Keeley finds investors everywhere (even floating in the ocean!)

24:10 – What "joy" taught her about business and burnout

30:30 – Success mindset

33:00 – Building legacy through long-term vineyard investing

35:00 – Rapid fire: overrated advice, happiness hacks, and saying YES

39:00 – What’s next for Keeley + how to connect with her


🔗 Resources Mentioned:

🌐 Texas Legacy Vines

📥 Connect with Keeley on LinkedIn or email: [email protected]


🎯 Join our investor waitlist and stay in the know about our next investor opportunity with Remray Equity → ⁠www.remrayequity.com/invest⁠


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The Invest and Roam Podcast with Dear NgoBy Invest and Roam