Let's Buy The World

8: How Jacob Went from COVID Era Loan Officer to Building a Real Estate Funding Powerhouse

Evan Darnell Season 1 Episode 8

In this episode of Let’s Buy the World, Evan Darnell sits down with Jacob Winters, the powerhouse behind Winvestment, a full service real estate company combining wholesaling, lending, flipping, and investing under one roof.

Jacob shares how he went from being a loan officer during COVID to building a company that helps investors find off-market deals, funds their flips, and closes long-term DSCR refinances.


They dive deep into:

1.The million-dollar flips that went sideways and the lessons learned

2.Why wholesaling today is more of a marketing system than a business model

3.How a follow-up lead turned into a 6-figure novation deal

4.The mindset shifts and market pivots that kept Jacob from drowning in high-interest chaos

5.Why grit, communication, and problem-solving are what private lenders actually bet on

If you're an investor, flipper, agent, or wholesaler trying to survive and thrive in today’s shifting market, this episode is pure strategy, real talk, and undeniable proof that your biggest deals often come from follow-up and persistence.