Collect money related items like the NFT and Financial Stress. Some other items may include Spending Frenzy and Mysterious Purse.
I have some unsureness about some of the items as I can only gain this achievement once and I had some additional items in my inventory. In the case that more items are needed than the ones I listed above here was my full loadout when I got the achievement: Mysterious Purse, Big Ego, One Canvas, Slippery Paint, Jerk Award, Yummy Cherries, Spending Frenzy, Brick, Airbrush, NFT, Financial Stress, and Wall.
I doubt a lot of these items being a part of the set but I could see reasons for many of them to be related to a "Grizzled Entrepreneur"