Aaron Stafford


Aaron grew up in Shrewsbury, Massachusetts and later attended UMass where he started his first business, raising $4M+ and driving strong returns to his investors. However, with Boston being a top 5 tech hub, he quickly became interested in venture capital and technology, leading him to a role with Gartner, the largest IT research firm in the world. At Gartner, Aaron worked with executives of SMBs to advise them on their product roadmap and go to market strategy to ultimately provide them higher odds of obtaining venture capital. Gartner gave him the opportunity to evaluate the competitive landscape of technology, and eventually led him to a role at Salesforce where he went on to lead a consulting business which under his leadership, produced two of the largest contracts his specific product had seen with ~$100M in total contract value.


Currently, Aaron resides in Bonita Springs, FL with his wife and two dogs, focusing his effort on building the local SWFL technology community and identifying innovative startups with strong leadership teams and large market opportunities to source venture capital deals for TWO39 VENTURES.