Hustler From the Bay: Jessie McGaffie

A-Game Media
3 min readNov 16, 2020

The A-Game Team had a chance to interview J Luda Sir Jess aka Jessie McGaffie, a Real Estate Agent/ Educator / Basketball Trainer.

As a Bay Area Native, Jessie talked about what it was like growing up with adversity and hustling to get to a position of success on your own terms.

In addition to the interview, we had a chance to get to know Jessie on a more personal level.

1). What is your favorite book of all time? Why?

The One Thing by Gary Keller. Focusing on one thing at a time is difficult, and Gary tells you the truth and secret to property wealth! Just remember … the truth is the opposite of coward!

2). Who has been the biggest mentor in your career?

If I had it all over again, I would wish to God that someone told me to sacrifice everything. I really do mean everything! Get to 100,000 dollars as quickly as possible! That’s the very start of Finacial life in California. It may be a little less in other states, but in Cali, you need 100 racks before considering yourself as a citizen.

Once you reach 100 Grand, the game becomes a little different. The world is different, you understand not spending your money on impulse, because you know the difficulty factor in acquiring! I can not tell you the amount of difficultly to achieve this goal, it will take extreme sacrifices … unthinkable!!! But I guarantee you one thing when making my first 100G, it was a lonely club, but people helped me once they knew I would say NO to all the tempting offers, they simply stop calling on me as the chump they could count on to purchase unneeded items.

For young men like you, it will take a hard look in the mirror to see the man versus the identification labeled on you or you preserved to be. Saying “NO” was a habit. People worry about red and blue states, it’s not progress! Everything is in progress! Are we progressing, are you progressing! All said and done, progress will win. After progress comes to power! Sports, news, social media is all about progress.

I’m really sorry to say, but you don’t progress looking at sports, or the news,SSL this is why you peek at it after your business day.

At the end of the day, “it’s your fault” … Fella’s your partner will blame you NO MATTER WHAT! So take it from me, Do what is needed to get that 100,000G’s, you will feel freedom never before (that’s if you never had it). Look in the mirror, get off the f*cking wheel, and go kill those motherf*ckers, regardless of the odds!

Everything is positive! I may be behind… But I’m not out!

3). Where do you draw inspiration from?

My wife … seeing her retire early … Let’s Go! My family .. seeing my kids concentrating on bettering this country instead of paying mortgages and bills such as student loans … etc …

4). What’s next for Jessie?

I am working on expanding my hustle to get Five Streamline of Finacial avenues coming in! Six is the goal for everyone… but I have to concentrate on ONE THING! At a time … I’m also working on diving into stock options! … I was so fearful of the market, and now I’m late in the game!!! But who’s perfect? I’ll just have to focus.

5). Ultimately what brings out your A-Game?

I’m in my third trimester of life! My “A“ has a chance from ‘getting out of poverty to protecting my wife physically and financially, my family physically and financially, and placing my grandkids in the best school my trust can buy. Simple … to me, if your ‘A game (Simon Sinek ‘Why) doesn’t change with age, you’re either a guru or a fool.

Jessie had also recently dived into the Real Estate world, so feel free to ping him for any inquires at!

To learn more about Jessie, tune in to our latest episode on both Spotify & Itunes.