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Millenial Youtubers

first posted: 2021-02-13 11:13:45.134713

Celebrity Youtubers are filling every niche of the spectrum.

We will review successful YouTubers talking about personal finance and real estate: a boomer and 3 millennial

  • Dave Ramsey, a bible belt boomer
  • Graham Stephen, a cheapstake Californian realtor
  • Meet Kevin, an aggressive Californian realtor
  • Investment Joy, a distressed trailer park investor

Dave Ramsey: Ok boomer

Dave takes calls from financially inept people and tells them to stop paying stupid rates on credit cards and car debt. The callers finances are complete wrecks and this program is probably more clickbait, giving entertainment and Shadenfreude to its viewer, rather than sound advice.

The advise given is financially suboptimal:

  • avoid all debt (rather than take on low rate debt to invest with high expected returns)
  • prefer mutual funds to ETF (not looking at tax issues) and recommend performance chasing

but then, Dave is not dealing with rational beings.

Graham Stephen: the Cheapstake

Graham is a charismatic millennial. He started to work during the GFC as an estate agent and worked first on rentals, then he started to sell houses to his rental customers.

He is a cheapstake, insisting in never paying more than 20c for an iced coffee. His youtube fame increased as he reviewed millennial money videos. He is rational about budgeting, accepting large spending especially for self-improvement, arguing that return on investment is likely to big good.

His videos on finance topic including complicated topics such as tax are well explained. Contrary to Ramsey, his advice is to optimise every credit card miles programs, and leverage debt provided that investment returns more than debt.

He is a smart and handsome Californian and tries to cultivate an image of the nice guy: he explains that he never raises rent on tenants.

He accumulated a portfolio of $13m LA properties. 2 years ago, he started to complain about property becoming too expensive despite his searching them full time, and as his youtube income exceeds that from real estate, he started to invest in stocks.

He recently bough a Mc Mansion in Vegas to move from the 13% income tax state to the 0% tax state.

Meet Kevin: aggressive investor

Kevin is another handsome and even more energetic millennial who is a California real estate agent and made money earlier than Graham. He is more risk taking and actve than Graham as he now has 20m of real estate and 20m of stocks, with 17m of mortgage and 4m of margin debt.

His real estate portfolio is also concentrated in Cali, and his stock portfolio got overconcentrated in Tesla due to the stock rising during Covid.

Kevin comes out as much more aggressive than Graham. He sells courses on becoming a landlord and does not hesitate the more difficult aspects of tenant relation such as eviction.

Investment Joy

Brandon invests in "trashflow properties" in Ohio. He publishes video with dramatic clickbait titles.

One year later, it seems that he gave up and hired a manager:

Watching is a video, along with watching the movie the "interruptors" is a very good introduction to america's more difficult neighborhoods. As he has a wife and kids, I am a bit worried for his safety..


The Graham and Kevin see their wealth growing quickly due to their starting investing after the GFC and using debt while mortgage rates go down. Kevin is particularly aggressive and likely to go bankrupt if the economy turns. Brandon is a fascinating product of his own mindset: he grew up in those hood and appears naturally attracted to handling petty cash rather than large bank balances.

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