Jason Pressman is a Shasta Ventures investor who brings an unusual operator background from helping grow Walmart.com from zero to nearly $1 billion in sales, and he's known for his contrarian view that VCs should maintain price discipline rather than following the common belief that "you never regret paying a high price for a great company." He has swum with sharks around 200 times, reflecting a personal approach to calculated risk-taking that he connects to his venture investing philosophy, and he's developed a distinctive thesis that there are essentially only two price points that work in SaaS businesses. Jason Pressman is a Shasta Ventures investor who brings an unusual operator background from helping grow Walmart.com from zero to nearly $1 billion in sales, and he's known for his contrarian view that VCs should maintain price discipline rather than following the common belief that "you never regret paying a high price for a great company." He has swum with sharks around 200 times, reflecting a personal approach to calculated risk-taking that he connects to his venture investing philosophy, and he's developed a distinctive thesis that there are essentially only two price points that work in SaaS businesses.