I Know A Guy Shady Life Simulator Achievement Guide — All 32 Unlocks

Short Answer: 32 Achievements, Three Groups

I Know a Guy: Shady Life Simulator ships with 32 achievements, confirmed by the Steam store page. The tracker grouping used below is SteamHunters' split: 14 achievements in the base game, 6 added by Update 1 in June 2026, and 12 added by Update 2 in September 2026. TrueSteamAchievements describes the same total as a 14-achievement base game plus DLC packs holding the remaining 18, so the two sites disagree only on how the groups are labelled, not on the count.

The practical read is that 14 achievements come from simply playing the intended loop once, while the other 18 are either grind milestones or feature unlocks added after launch. Nothing in the list requires a second save file, but several entries do require specific hardware: the vending machines, the automated pizza oven and the skateboard are all purchased unlocks rather than story rewards.

Base Game Achievements (14)

Achievement	What it asks for
Find out why you're here.	Movement through the opening story beats
Survive the first day.	Finish the first in-game day
Serve a pizza for the first time	Complete one customer order
Complete the first shady trade deal	Finish one back-room favor
Punch an NPC for the first time	Throw a punch at any character
Serve pizzas 25 times	Repeat the front-counter loop
Trade Bitcoin for the first time	Buy or sell Bitcoin
Complete 20 shady quests	Work the back-room favor chain
Serve 19 pizzas to CaseOh	Fulfill one large single-order request
Decorate your shop for the first time	Buy and place furniture
Buy a costume for the first time.	Purchase an outfit at the computer
Get killed for the first time	Die once
Earn 100,000 from business	Reach the money milestone from shop income
Pay half of your debt	Reach the midpoint of the debt goal

Most of these fire within the first few hours because the tutorial walks you through the pizza line, the dark web order flow, a costume purchase and the first sleep cycle. The two that take planning are the large single-order request and the debt milestone, since both depend on how efficiently you can produce and stock pizzas.

Update 1 Achievements (6, June 2026)

Achievement	What it asks for
Hire an employee for the first time.	Purchase your first staff member
Unlock the vending machines.	Buy the vending machine unlock
Collect money from a vending machine for the first time.	Take income from a vending machine
Serve a pizza from the automated pizza oven for the first time.	Use the automated oven for one order
Buy yourself a skateboard.	Purchase the skateboard
Unlock every talent in the dark web skill tree.	Complete the full skill tree

Three of these six are pure purchase steps, so they are gated by money rather than skill. The skill-tree completion achievement is the long one, because talents are paid for with shady progression rather than cash, and the tree is where the forgery station, incinerator and washing machine unlocks live.

Update 2 Achievements (12, September 2026)

Achievement	What it asks for
Complete 50 shady quests	More than double the base-game quest count
Serve three pizzas to the strange people in the sewers.	Deliver to a specific customer group
Earn 1000 BTC from shady quests	A large crypto milestone
Collect 3 different mushrooms	Gather three distinct mushrooms
Cook a Lucid Pizza	Produce one special recipe pizza
Dig ground to find chests	Use the digging mechanic on a dig site
Personally deliver 5 different Dark Web items to customers	Hand-deliver five distinct dark web orders
Buy 100 shady items	Purchase milestone on the marketplace
Crash your skateboard for the first time	Crash while riding the skateboard
Overcook pizza 10 times	Let ten pizzas burn
Serve 10 Shady Pizzas	Complete a run of shady pizza deliveries
Complete the main story	Finish the story arc

Two of these are deliberately counterintuitive: crashing the skateboard and overcooking pizza ten times both reward failure, so if you are chasing completion, do them on purpose rather than avoiding them. The mushroom, Lucid Pizza and digging entries are the ones players ask about most in the Steam forums, alongside a thread titled "Treasure Chest Achievement bugged."

Timing, Co-op and Patch Notes That Matter

Patch note	Effect on achievements
1.0.4 buried-chest fix	The buried-chest achievement now unlocks for every player in the session as soon as a chest or cash bag is looted, and players who already emptied a dig site receive it when they next load that save
1.0.4 quest tracking	Procedurally generated forgery jobs now update their quest card immediately, which removes a common source of stalled favor chains
Earlier hotfix	Item-dependent Quest Reset added for washing machine jobs, incinerator jobs and item-specific quests, including the chest quest
Achievement removal	With Great Pizza Comes Great Responsibility was removed until it is reworked, so it is not part of the current 32

Achievements that depend on buying something first, rather than on playing well:

• Vending machine unlocks and vending income need the machine purchased.
• The automated pizza oven unlock requires the upgrade.
• Buying the skateboard is its own achievement, and crashing it is a separate one.
• Decoration, costumes and the full dark web skill tree are all purchases as well.

A sensible completion order:

• Play the tutorial loop once to bank the 14 base-game achievements, including the first-sale, first-costume and first-death unlocks.
• Buy the vending machines, automated pizza oven and skateboard to close out three of the six Update 1 entries.
• Push the skill tree to completion, then use the machinery it unlocks for incinerator, washing machine and forgery favors.
• Chase the grind counters last: 50 shady quests, 100 shady items, 1,000 BTC and the debt midpoint, since all four progress at the same time while you work orders.
• In co-op, agree on who loots dig sites so the chest achievement lands for everyone in one session.

Because the achievements were extended twice after the April 2026 Early Access launch, older guides list only 14 or 20 unlocks. If a checklist looks short, it predates the two update packs.