Deanna Anderson


Rugrat Entrepreneur

Deanna Anderson has been creating marketable products since before she even attended elementary school. From a young age, she had an entrepreneurial vision, realizing that there were ways she could make money without much cost or risk. (Of course, when you’re 4 and have two parents paying for your supplies, you’ll always make 100% profit, but she didn’t know that at the time.)

When Life Gives You Lemons…

In the backyard of her family’s old apartment there was a lemon tree that provided Deanna with unlimited access to fresh lemons that she could make into lemonade and sell out front of the building in San Francisco. As the saying goes, “when life gives you lemons…” From the age of 4, she regularly held lemonade stands to raise money for herself, and for charity. She always chose a charitable cause to donate a portion of the proceeds, even one time deciding on a man that had lost all of his cash in a motorcycle accident while he was on the way to deliver it to his sick mother.

But Deanna didn’t stop there. Realizing her capacity for sales (especially since she was so small and cute), she began selling things that her family had around the house, holding garage sales for the neighborhood. “I loved taking things that my family didn’t need anymore and giving them a second wind,” says Deanna, who shares that her favorite sale she ever made was of an old bike she had outgrown, which went to a younger girl that really loved it.“ Seeing a product that I marketed go to a better home was a rewarding experience, even though it was just something I already owned.”

Failing Wisely

In fourth grade, Deanna wrote a fashion magazine with two friends called Dress Fab, complete with 30 designs, imaginary advertisements she drew on MS paint, and even word scrambles and crossword puzzles for readers. The threesome sold their magazine to classmates on the schoolyard until the principal told them it wasn’t allowed. “That specific venture wasn’t very profitable, but I did learn about overhead costs, because my mom told me I had to pay for printer ink, which it turns out, is pretty expensive.” Deanna laughs as she thinks back on all of the ways she tried to turn a buck. “I used to shine my dad’s shoes and wash his car on the weekends so I could save up to buy a dog when I was older. I even went to the local hair salon and told them I would dust their shelves for $10 an hour. They probably hired me as a joke; I was so young.”

Though her business ventures weren’t always the most successful, Deanna learned a lot from pushing into the innovation zone, and failing wisely. “I was never afraid if things wouldn’t work out. I just tried things and if they failed, I tried something else. I was really lucky to have a supportive family that never made me feel like I had to be perfect. I could just be creative.” Deanna says she tries to maintain that childhood mindset in her work to this day.

Innovating through Comedy

In college, Deedee founded her most successful venture, Stanford Womxn in Comedy, featured on for the progress it made in female representation in comedy on Stanford’s campus. “When I started at Stanford, I was the only woman in the stand up comedy club. By graduation, we had nine of us, and everyone felt really supported. That was definitely my proudest achievement to date.”

Post-graduation from Stanford, Deanna lives in San Francisco, writes and performs sketch comedy, and runs workshops meant to create discussion around the underrepresentation of womxn in comedy and to inspire others to produce comedic content, no matter their gender. “I hope anyone that comes to my workshops will see that they have the capability to achieve anything they set their mind to — it just takes focus and hard work.”