Undercover Billionaire Season 2 Episodes

Episode 1

Three Million Dollar Bet

Wed, Jan 6, 202183 mins

With just $100 in their pockets, three business titans are dropped in unfamiliar cities, stripped of their names, money, and contacts and given a simple challenge - to build a $1 million business in just 90 days.

Episode 2

Hustle Up

Wed, Jan 13, 202183 mins

Grant hustles for a big score to kick-start his business and get out of the RV, Monique needs work and pressure tests her concept, and with her back against the wall, Elaine lands on a million-dollar idea.

Episode 3

Pressure Tests

Wed, Jan 27, 202145 mins

After a catastrophic setback, Grant struggles to regain his footing. Monique goes all in on her $1 million idea. Elaine races full steam ahead to expand her team and land a critical business partner.

Episode 4

Fist or Finesse

Thu, Feb 11, 2021

Grant receives a shocking call that could mean game over. Monique's plans go up in flames just before her big investors pitch. Elaine comes up with a unique plan for acquiring renovation funds for the inn.

Episode 5

The Closers

Wed, Feb 17, 2021

Monique doubles down when her fundraising deadline passes. Grant launches two $1 million business ideas. Elaine rushes ahead with renovations to land a major investor.

Episode 6

Be Afraid, But Do It Anyway

Wed, Feb 24, 2021

Elaine is stopped dead in her tracks when an investor pulls out. Monique lands a side hustle at an iconic Tacoma business that could score her a big payday. Grant struggles to gain traction with his marketing company.

Episode 7

Turning Points

Wed, Mar 3, 2021

Monique's rent money rides on rebranding a local business. Grant faceplants in front of a room full of potential investors. Elaine creates another money-making tranche and taps into a new source to fund her $1 million idea.

Episode 8

Cocktail of Chaos

Wed, Mar 10, 2021

Grant seeks redemption when a $10-million deal implodes. Just as Elaine gains momentum transforming the inn, the ceiling caves in. Monique turns down a big pay day and bets on herself.

Episode 9

Dumpster Fire

Thu, Mar 18, 2021

Grant builds his marketing team, but after a series of failed pitches threatens to quit. Monique opens Rooted to the public and starts making money. Elaine and her team host an event at Shep's Club, but struggle to work under pressure.

Episode 10

Wake Up Call

Wed, Mar 17, 2021

With less than a month to hit the $1-million mark, Monique gambles on a new revenue stream. Grant hunts for a Wake Up Pueblo HQ and faces the team about their suspicions. Elaine makes big changes to her team and accelerates renovations.

Episode 11

The Manifesto

Wed, Mar 24, 2021

Elaine secures a big partnership but miscommunications within the team could derail her soft open. Grant issues a manifesto to set his company on a new path and start producing. Monique steps up her game with a new sales tactic.

Episode 12

T-Minus 7 Days

Wed, Apr 7, 2021

Pressures intensify when Elaine's soft open is derailed by an unexpected disaster and a lack of funds. Monique races to create her first official Rooted truck for her debut. Grant has a breakthrough as he hustles to close two more deals.

Episode 13

Camel Meet Straw

Wed, Apr 14, 2021

At day 90, the entrepreneurs make a final push before valuations.

Episode 14

Judgement Day

Wed, Apr 14, 2021