- mainstreet memos
- Posts
- Painting with Picasso
Painting with Picasso

Picasso started painting at a very young age - around 7 he produced his first work, “The Little Yellow Picador”, under the guidance of his father, a painter and teacher.
Over the course of Picasso’s life - 91 years - he had published 26,075 works.
He lived for 33,402 days.
Picasso averaged 1 new piece of artwork every day from age 20 to 91.
I’m willing to bet a lot of his best work came in his later days.
Consistency leads to compounding, and compounding creates outliers.

The Picasso Effect applies across industries.
Warren Buffett has made hundreds of investments into both public and private companies.
Only 10 of them make up the vast majority of his net worth (GEICO, Apple, Coca-Cola, Bank of America, etc.).
Furthermore, the majority of Buffett’s wealth is due to compounding in the later stages of his life.

Not everyone can be Warren Buffett.
Jason Calacanis started angel investing about 20 years ago without any formal experience at a fund.
Over the course of 300+ investments, a good percentage of the startups in his portfolio went to $0.
But a few of those investments generated $150M+ in personal returns:
Uber
Robinhood
Calm
Thumbtack
Showing up everyday, staying in the game long-term, and never taking risk you can’t handle are foundational keys to excellence.
Pick up your brush and start painting.
One of my favorite trends to track in investing right now is “creator-led businesses”.
Audience builders are teaming up with founders / operators to create products that have distribution from day zero.
Audience builders:
traditional celebrities: Hailey Bieber sold Rhode to elf for $1B
social media influencers: Nelk Boys scaled Happy Dad seltzer to $100M+ in sales
athletes: Tiger Woods teamed up with Mike McCarley, Golf Channel exec, to launch TGL
Not a new development by any stretch of the imagination but definitely picking up heat and starting to attract more capital.
Multiple funds have created dedicated vehicles to back creator-led businesses: Slow Creator, CreatorLed, TCG.
Institutional LPs like the University of Michigan and MIT are getting involved in the space as well.
Never a better time to (a) build community in a specific vertical or (b) find someone with an audience and build a product with them.
Headlines
Cooper Flagg allegedly made around $30M at Duke. Bleacher Report
Roark Capital invests in Dave’s Hot Chicken. CNBC
How flyover country took over the NBA. Washington Post
Speedata, a chip company competing with NVIDIA, raises $44M Series B. TC
Reply