Going From Broke

Season 2

Dan Rosensweig, CEO of student services business Chegg, meets millennials with big dreams but are swimming in debt. Together, Rosensweig and his team advise and guide the subject of each episode to turn their financial situation around and move toward freedom from debt and student loans.

6 Episodes

Big Heart, Big Debt
E1
Big Heart, Big DebtIsabel Cervantes is the first in her family to graduate from a 4-year college, but her $200k of student loans is dragging down her free spirit. Join our financial team as they help Isabel get creative and out of debt!
Pandemic of Love
E2
Pandemic of Love]Enam and Carlin Jordan have created the loving family home that they never had growing up. But medical expenses for their baby and a moneypit of a house have put them into massive debt. In this tearjerker of an episode, the Jordan’s break generational curses and reinvent their lives.
The Debt Diet
E3
The Debt DietSingle Mom Tina Dierna is a social worker, hockey player, and shopaholic who recently lost 116 pounds. Our financial team knows the lessons she learned from losing weight will get her far, as she works her way to financial freedom.
Mr. Charisma
E4
Mr. CharismaRyan is a handyman with entrepreneurial dreams, but he’s in massive debt from purchasing boats, cars, trucks and motorcycles. Fortunately, Ryan’s hero Dan and Tonya are here to give this confident kid some tough love!
Love in the Time of COVID-Debt
E5
Love in the Time of COVID-DebtChelsea and Jake Flaming are an adorable couple with a baby, and another on the way. But this baker and musician's businesses need a little tweaking to get out of the red and into the black. Our financial team is here to show that getting out of debt is a piece of cake!
Absolutely Broke & Fabulous
E6
Absolutely Broke & FabulousThe Donovan is a classical pianist who is always dressed up, but since the pandemic has nowhere to go. When live performing stopped, he decided to “wait it out,” volunteering to help others even as he fell into debt. But now our remote team is here to teach The Donovan that the show must go on!