Steve Unger, a wealthy powerful CEO, falls from grace when he's brought down on charges of fraud, obstruction of justice and racketeering. When Steve cuts a deal to get out of prison, he realizes that his old life no longer exists - his wife and daughter don't want to live with him, his former colleagues shun him, and the whole world seems to despise him, even his parents refuse to help him and take him in. He visits his friend and lawyer Neil to retrieve his precious luxury sedan (to protect the car from creditors Neil has put it in his name). With nowhere else to turn, Steve meets Carol, a unique woman who has chosen to live in her car and who convinces Steve that his best bet while trying to get his life together is to do the same.

After spending his first night living in his car, Steve wakes up in an impound lot, his car having been towed while he slept in it. If he wants his car back he needs to raise $200 to cover the tow. To raise the money, Steve sneaks into his wife Lori's house and steals it from his daughter Kate's room. When Lori discovers what Steve has done, she is livid. To repay Kate, Steve takes a job as a day laborer, picking worms. But when he tries to negotiate a collective bargaining session on behalf of his worm picking colleagues, he gets them all fired. In retaliation, they attack Steve and damage his car.

Steve pays Karl, a possibly deranged local car dweller, to "fix his car". To raise the money to fix his car (and to pay Kate back the money he owes her) Steve agrees to do errands for Neil's mother. He sub-contracts all of his manual labour to Julio, one of his former, now un-employed worm picking colleagues, a decision that somehow leads Steve into a brief career as a porn star agent.

Steve's latest effort to "get a foot back in the corporate world" finds him taking a job as a bike courier, delivering documents to his former colleagues, armed with a fast deteriorating designer suit and his un-diminished business acumen. When a fall in traffic lands Steve in the comfy confines of a hospital's ER ward room, Steve realizes he's found a good place to finally get some rest. While trying to convince the doctors to keep him around longer than necessary, he decides to help a possibly dying man change his will to keep his kids from inheriting his wealth.

Steve and Lori are told by Kate's principal that their daughter has been caught running a sports-book on her high school's intramural teams. Despite being proud of his daughter's "entrepreneurial spirit", Steve convinces the school's janitor (who longs to produce and direct the semi-autobiographical teen slasher script he's written) to give him access to the school's records so Steve can destroy any evidence of Kate's wrongdoings. Kate is annoyed by her mother's new-found obsession with on-line dating. Steve visits Lori's father, a once-shady businessman who is responsible for teaching Kate how to run a sports-book. Steve dispenses some ill-fated corporate advice to Scott, a twelve-year old kid who lives in a van near Steve's car.

Exasperated by the perils of car-living, Steve moves into a rooming house where he meets an aging jazz singer who was once Steve's favourite musician. A skeptical Steve agrees to help the musician reclaim her soul from the man she says she sold it to, who promised her "the blues skills of Robert Johnson" in exchange and delivered what appears to be a raw deal. While trying to prove to this woman that she never actually sold her soul, Steve is arrested for a break and enter.

Caught on a break and enter in the previous episode, Steve finds himself back in jail, where his lawyer Neil arranges for Steve to be subject to a mental fitness examination. Transferred to the medical wing, Steve meets some fellow inmates who are in the throes of planning a coup. The doctors examining Steve have more interest in reclaiming the money they lost in Uncor than actually helping Steve. Steve must somehow make sense all of these elements to spring himself from jail and in the process accidentally incites a riot.

Kate steals her mother's "wampum", a cherished family cultural artifact, and gives it to Steve to sell for food money. When Steve tries to sell the wampum, he is disturbed to find himself beset by comically unexplainable hallucinations and nightmares that cut deeply at Steve's many anxieties and insecurities. Steve wonders skeptically if the wampum has somehow cursed him or if he actually feels guilty about taking it from his family. Steve is seemingly more afraid of feeling guilty than he is of being cursed.

Garreth, the night janitor from Episode 5, returns with the demand that Steve make good on his promise to finance Garreth's independent slasher-horror film. When Alex the protester decides to move on with his life, Steve finds something else for Alex to do with his time.

The police descend upon the car community to hassle Steve and search his car because his luxury ride screams drug dealer. They find no drugs but tell the car-dwellers they are illegally parked and need to leave the abandoned parking lot on which they have settled. When Steve takes it upon himself to get permission to stay from the owner of the lot, he is drawn into a winding adventure in the form of an increasingly murky series of favors.

Kate is caught trying to sabotage her parents' divorce. When Steve's mother breaks her rib, Steve offers to move in with his parents and help out. Steve's old assistant Fawn gives him a job in an office mail room, inspiring him to try "working his way to the top" in one day.

On the day of Kate's 16th birthday, Neil informs Steve that the government believes that he's been hiding money in a secret bank account. Although Steve denies having done this, bailiffs arrive at Lori's house and begin seizing all of her assets and Steve is told that he could be heading back to jail. A possibly shady business venture of Kate's goes awry.

Steve is under house arrest in his parents' home, falsely accused of hiding money, set up by his former partners Gordon and Liev.

Steve takes a job selling knives door-to-door, then teams up with an inventor on the cusp of changing the world who may or may not be wanted for murdering his neighbour. Neil and Toby seek to exploit Steve's predicament by building a new reality show around it. Steve furthers his revenge plot against his former partners by sending Oscar (from Episode 111) after the stolen Uncor money controlled by their wives.

Steve is asked by Judge Puddicombe to apologize to a couple whose lives were ruined by Uncor's collapse. Steve asks Oscar to help the rival inventors from Episode 202 resolve a dispute over a mutual girlfriend. Steve involves his old assistant Fawn in his plan to steal Gordon and Liev's money. Lori learns that her new boyfriend has some bizarre sexual proclivities.

An appointment with a back-alley dentist leads Steve to a brief career as a small time private eye and a series of conflicting business arrangements.

Steve takes a job for a crooked businessman who may be a dangerous criminal.

Steve takes a job in Bruno's new restaurant, which is being overthrown by the vegan anarchists who work in the kitchen. When daily life in the car community starts getting fraught with petty disputes, Steve seeks to become its political leader.

Everybody spends the weekend at Lori's horse farm, at an "investment retreat" for Lori's new business. When Lori's business partner suddenly dies, trouble arises over the contents of her will and the 'seed' of a horse.

Steve's friends Kendra and Peggy want him to help them conceive a child. Steve takes a job working for a real estate investor who is only looking to exploit his reputation as a criminal.