Joining a mentorship/ mastermind - is it worth it?

[Sean Bramble]

I'm considering joining a short term rental development mentorship/ mastermind (i.e., building, not buying STRs) that helps students through the process of picking a market, finding land, navigating zoning & permits, and working w/ an architect/ GC to complete the project. I've never developed real estate, and see the value in having someone to guide me who has done it before so I can avoid unnecessary mistakes. I know I can learn the "theory" for free on the internet, but the one-on-one coaching with an actual human when I'm running into real issues along the way is what I'm after.

I'm noticing a lot of these "mentorship" businesses pop up (many led by Youtube gurus), and am concerned about signing up for something that focuses more on marketing/ new student acquisition/ standardized teaching than actually providing the specific, one-on-one coaching I'm after. What questions do I need to ask to make sure the group I'm joining is actually going to provide me with value that justifies the price they charge?

[Rick Albert]

I find it difficult that someone can put together a program that goes through city permits for every municipality in the country. 

Wouldn't it be a better experience just to work under a developer? That's what I did and learned way more than I could possibly imagine. Plus I developed connections with great vendors.

For example, if you don't have the experience, ask a developer where you could help them in exchange for education. Maybe it is bookkeeping or running errands.

I agree with John, be skeptical. 

If you really want to join one of those programs, I would ask the following:

-Show me a track record of properties that they personally own.

-Ask how they are able to teach navigating through various cities.

-What guarantees do they provide?