DraftKings Alumni Launch 186 Ventures, A $37 Million Early-Stage Fund

In a capital-flush market, founders are looking for backers that can bring more than just money to the table — or they would just call Tiger Global. Boston-based 186 Ventures — named after the speed of light —  hopes to attract entrepreneurs with its founders’ extensive networks, operating backgrounds and ability to move fast in today’s hyperspeed market. The firm founders, Giuseppe Stuto and Julian Fialkow, met at DraftKings in 2018 after Stuto’s startup Fam, a platform hoping to innovate how teenagers communicate with each other, was acquired by the sports betting platform. The pair were introduced at an office happy hour and immediately hit it off before bonding over martinis and oysters at nearby Boston landmark the Barking Crab. 

The friends began angel investing in 2019 and quickly amassed a portfolio of 31 investments including AI company UiPath, which went public at a $35 billion valuation in 2021, and blockchain data startup Chainalysis, which was last valued at $4.2 billion. “We did that for about two and half years and we both came to similar career inflection points, in our own regard, and recognized that we had built up a bit of a track record,” Stuto tells Forbes. “Founders were saying that we were adding value relative to the check size and that was the ‘aha moment.’” Stuto and Fialkow knew it was time to formalize the endeavor. They both quit their jobs in July 2021 and went all in on venture. Due to their track record and network, they were able to raise their first fund in four months.  

The $37 million vehicle will focus on pre-seed and seed stage companies, as originally reported in Midas Touch newsletter. “We both really love to roll up our sleeves and help build and that’s why we started to start our fund as a pre-seed and seed stage fund,” Fialkow says. The firm is geographically agnostic and is looking to invest in sectors including media, fintech, web3, and the future of work, among others. The fund has already made six investments including in NeighborSchools, which matches parents with home-based childcare. 

The firm intentionally raised the fund from a mix of backers including institutional investors like fund of funds and endowments, but also from more than 30 operators including the founders of developer platform Alchemy, Nikil Viswanathan and Joseph Lau, and fintech Digits, Wayne Chang. “It adds an amount of expertise,” Fialkow says on being able to tap the firm’s limited partner network. “Even though we are a small team, it allows us to have a much bigger, broader stroke.”

In addition to its LP base, the firm founders hope their backgrounds bring value too. While literally every investor says their experience benefits their portfolio companies, the 186 founders actually have the resumes to back it up. Stuto successfully founded a startup, raised venture capital, and scaled the company to an exit before joining Fialkow at DraftKings while it was a fast-growing unicorn company. Fialkow also worked at Drive by DraftKings, a multistage venture fund anchored by the sports betting site, as an investor. After DraftKings, Stuto took a role as a mentor at startup accelerator Techstars and as a COO at local early-stage AI startup Pison. 

“The fact that we are able to meet at a company, collaborate and work there, those backgrounds allow us to bring a unique skillset to the founders,” Fialkow says. Stuto adds that they think they can add further value by being able to move quickly and by putting their egos aside. They know they can’t lead the Series A or B rounds for a company, but plan to tap their networks to help founders craft their own intentional cap tables, even if it means 186 Ventures ends up with a lower ownership stake. “You would think I want all the ownership, and mathematically that’s what helps us, but in a market that is so competitive, companies deserve to have the best in class investor syndicate,” Stuto says.