Yakuza 4 Remastered

This achievement can be unlocked any way you wish, but the soonest it can be done is in Chapter 2 of Part 1, when you return Akiyama to his office at Sky Finance, in the same building on Tenkaichi Street where New Serena also occupies one floor below. Once you get through the subsequent cutscene where you first meet with Lily, Akiyama will proceed out of the building and substories now pop up on the map. There are seven substories that can be completed in this chapter, and are arranged as follows:

#2 - Layoff Already
#4 - The Apprentice (Must complete Layoff Already first)
#8 - Gourmet Reporter
#9 - Art of Scouting
#12 - Pimp My Otaku
#14 - How to Spend Money
#16 - Akiyama vs. Hostess Clubs

Description on how to complete these substories (as well as those in Chapters 3 and 4) is in the link below, with credit to CyricZ: https://gamefaqs.gamespot.com/ps4/239456-yakuza-4-remastered...

It should be noted that while some of the substories highlight Akiyama lending money to clients in need as part of his job, you actually don't need sufficient amounts of yen you earn in-game like money and items you can sell in Ebisu Pawn in order to progress and complete the substories.