Undercover BillionaireSeason 22021 · 14 episodesEpisodes1Three Million Dollar BetWith 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.2Hustle UpGrant 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.3Pressure TestsAfter 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.4Fist Or FinesseIt could be game over for one of the entrepreneurs.5The ClosersThe entrepreneurs double down in the face of adversity.6Be Afraid, But Do It AnywayElaine loses an investor, Monique gains a side hustle and Grant struggles.7Turning PointsGrant faceplants during an investor pitch. Monique rebrands a business.8Cocktail of ChaosA deal implodes for Grant. Elaine faces a crumbling ceiling at the inn.9Dumpster FireGrant threatens to quit. Monique opens up Rooted. Elaine hosts a big event.10Wake Up CallGrant faces his team about their suspicions.11The ManifestoOne entrepreneur issues a manifesto to motivate the team.12T-Minus 7 DaysWith only seven days left, pressures intensify for all three entrepreneurs.13Camel, Meet StrawAt day 90, the entrepreneurs make a final push before valuations.14Judgement DaySeason 1