Undercover Billionaire - Season 2

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Three Million Dollar Bet

1 - Three Million Dollar Bet

Air Date: January 6, 2021

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: build a $1 million business in just 90 days.

Hustle Up

2 - Hustle Up

Air Date: January 13, 2021

Grant hustles for a big score to kickstart 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.

Pressure Tests

3 - Pressure Tests

Air Date: January 27, 2021

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.

Fist Or Finesse

4 - Fist Or Finesse

Air Date: February 3, 2021

It could be game over for one of the entrepreneurs.

The Closers

5 - The Closers

Air Date: February 10, 2021

The entrepreneurs double down in the face of adversity.

Be Afraid, But Do It Anyway

6 - Be Afraid, But Do It Anyway

Air Date: February 17, 2021

Elaine loses an investor, Monique gains a side hustle and Grant struggles.

Turning Points

7 - Turning Points

Air Date: February 24, 2021

Grant faceplants during an investor pitch. Monique rebrands a business.

Cocktail of Chaos

8 - Cocktail of Chaos

Air Date: March 10, 2021

A deal implodes for Grant. Elaine faces a crumbling ceiling at the inn.

Dumpster Fire

9 - Dumpster Fire

Air Date: March 10, 2021

Grant threatens to quit. Monique opens up Rooted. Elaine hosts a big event.

Wake Up Call

10 - Wake Up Call

Air Date: March 17, 2021

Grant faces his team about their suspicions.

The Manifesto

11 - The Manifesto

Air Date: March 24, 2021

One entrepreneur issues a manifesto to motivate the team.

T-Minus 7 Days

12 - T-Minus 7 Days

Air Date: March 31, 2021

With only seven days left, pressures intensify for all three entrepreneurs.

Camel, Meet Straw

13 - Camel, Meet Straw

Air Date: April 7, 2021

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

Judgement Day

14 - Judgement Day

Air Date: April 14, 2021