How Brett Gibson Went From Making Pizza to Initialized Capital VC

• Initialized Capital’s Brett Gibson quit his job making pizza to teach himself how to code.
• He became a serial startup founder and then met future colleague Garry Tan at Y Combinator.
• Tan later brought Gibson on to work with him at his startup, Posterous, and then Initialized.

After graduating from the University of California Santa Barbara with a philosophy degree, Brett Gibson was serving pizzas and trying to figure out what to do next. 

Gibson liked to be creative, but also solve puzzle-like problems. He had taken a coding class in college and realized that writing code was a perfect marriage of the two. He decided to start teaching himself how to code by reading online articles and first learned to write ActionScript, the programming language for developing websites.

His accidental newfound love for code changed the course of his career. And learning what was a niche code at the time, paid off. 

“I was able to get into the industry without credentials,” Gibson said. 

In 2004, he landed a software engineering job at Grand Central Communications, a startup that helped people manage voicemails and phone numbers, which was later acquired by Alphabet. He left the startup with some colleagues to cofound DrawHere in 2005, a browser drawing startup, and then DeviantArt bought the company a year later. 

After the deal, Gibson and a friend went on to cofound Slinkset, an online tool that lets users create message board sites and integrate them with their websites. The duo was accepted into Y Combinator’s summer 2008 cohort, and that’s where Gibson met Garry Tan, who was also there for his blogging startup, Posterous.

Slinkset ended up shutting down, but Tan asked Gibson to join Posterous in 2009, bringing him on as a cofounder. 

“It just made sense,” Tan told Insider when reflecting on why he asked Gibson to join his startup. “We just worked very seamlessly.”

Three years later, Posterous was acquired by Twitter and then shut down. Tan went on to start investing as a partner at YC and later asked Gibson to join him there as well, this time as a software engineer to rewrite the application system and its backend system that tracked potential startups to invest in.

“In his code, you sort of see the philosophy major in him,” said Tan. “He definitely has this sort of, like, obsession with the platonic ideal of perfection. There’s something very elegant about that.”

Within a year, both Tan and Gibson left the accelerator. Tan was raising funds for his new firm Initialized Capital, and Gibson took a year off to do research on cryptography and continued learning code, with the intent to continue working as a software engineer at a big tech company like Alphabet.

But his career trajectory changed yet again after having lunch with Tan one day. Gibson was opining about how hard it was to get a job as a software engineer and Tan responded by saying he should work at Initialized.

“Who better than someone who I’ve sat in the trenches with and spent 10,000 hours learning how to make things with,” Tan said.

Gibson knew he didn’t want to go through the coding interview process so he took a leap into venture capital and was hired on as an operating partner at the firm. 

The job turned out to be tailored to his skill set. He wrote software, advised companies on engineering best practices, and helped invest. 

Gibson was first tasked to build the firm’s internal software to make smarter investments. Initialized now uses the software, Folio, on a daily basis for tasks to find potential startups, track data on investments, and set up alerts to respond to founders, which sets Initialized apart from other firms.

Folio keeps the team on the same page and facilitates blind voting on startups, helping the team make deal decisions and ultimately close them. Once a partner is ready to invest in a startup, Folio sends out a questionnaire for the team of partners to decide on whether it’s worth an investment. 

Tan and Gibson said the philosophy behind blind voting is to help partners not play into venture capital politics by removing institutional hierarchy and bias. 

“We really do want everyone on the team to sort of be independently thinking,” Gibson said. “Without worrying what else is going on or playing to politics.”

Gibson has now moved on to investing full- time after being promoted to general partner last August. 

With his technical and startup knowledge, he’s led investments for the firm in crypto companies like Bison Trails, a blockchain infrastructure platform; TRM Labs, a blockchain intelligence company to help crypto-related fraud; and Talos Trading, a crypto trading platform, and earned a spot on Insider’s list of rising stars in crypto investing.

Tan says Gibson’s blend of experience has been his biggest asset pulling in massive returns for new funds.

“It’s been so cool to see someone who I’ve had such a long history with just blossom,” Tan said.