Stacking Cashflow Through Wholesaling and Keeping the Best Deals — Smart Approach?

Question

Hey everyone, I’m 21 and started a business about 5 years ago that’s done pretty well. Overall, I'd say I've been pretty good at making money, but when it comes to investing I have some stocks and crypto, but right now I’ve also got a few hundred grand just sitting collecting dust.

My dad is a police officer but also has a couple rental properties with a partner in upstate New York (college rentals). It’s small scale but they’re very profitable and they have a great manager up there. That got me thinking more seriously about real estate.

Recently I hired someone for my company who used to manage 10 cold callers for a real estate company. My plan is to start small, probably just hire one cold caller to begin with. My guy would manage them and also qualify leads. From there, I’m thinking the setup would look like this:

• Cold caller dials and generates interested sellers.
• My manager filters those leads, and if one looks really motivated, I’ll step in to see if it’s a deal worth pursuing.
• Most leads would get passed to acquisitions/dispo partners to wholesale, where I’d take a cut when deals close. Even if I just break even or make an extra couple grand a month, the real goal is to learn the business and put myself in a position to get better deals than what’s listed publicly.

Cold caller dials and generates interested sellers.

My manager filters those leads, and if one looks really motivated, I’ll step in to see if it’s a deal worth pursuing.

Most leads would get passed to acquisitions/dispo partners to wholesale, where I’d take a cut when deals close. Even if I just break even or make an extra couple grand a month, the real goal is to learn the business and put myself in a position to get better deals than what’s listed publicly.

• The best “grand slam” deals (deep discounts, strong cashflow potential) I’d keep for myself, especially in upstate NY where my dad already has experience with student rentals. For those, I’d buy in cash and then do a DSCR cash-out refi to recycle capital.
•

The best “grand slam” deals (deep discounts, strong cashflow potential) I’d keep for myself, especially in upstate NY where my dad already has experience with student rentals. For those, I’d buy in cash and then do a DSCR cash-out refi to recycle capital.

Long-term, I’d like to build a larger portfolio (5–10 properties in a market I know well), but for now my focus is to start lean, learn wholesaling, and build cashflow while gaining access to discounted deals.

I’d really appreciate any feedback or advice from experienced investors on this approach and pitfalls I should watch out for. Also, in my current business I invested in a mentor who guided me, which was hugely valuable. I know there are a lot of “gurus” in real estate, but if I could find someone actively doing deals (not just selling courses), I’d consider investing in that kind of mentorship.

Benjamin Louie · Answer

@Joe Edelman, Your plan makes a lot of sense—starting lean, learning wholesaling, and keeping the best deals is a smart way to build cash flow while gaining experience. A few quick tips:

• Wholesaling first: Great for learning deal flow without risking too much.
• Keep the winners: Deep discount, high-cash-flow deals are perfect for building your own portfolio.
• Mentorship matters: Find someone actively doing deals, not just teaching courses.
• Watch pitfalls: Compliance, team management, and local market demand are key.

Wholesaling first: Great for learning deal flow without risking too much.

Keep the winners: Deep discount, high-cash-flow deals are perfect for building your own portfolio.

Mentorship matters: Find someone actively doing deals, not just teaching courses.

Watch pitfalls: Compliance, team management, and local market demand are key.

If you execute well, this approach can set you up to scale smartly.

Stacking Cashflow Through Wholesaling and Keeping the Best Deals — Smart Approach?

1 Reply