Greg has been an angel and venture investor for over 20 years. He began his career at Endotherapeutics, a medical device company that was acquired by U.S. Surgical. He then founded Rembrandt Venture Partners. Greg co-founded two venture-backed companies: Alter Ego Networks, a cloud-based web transcoding company acquired by Macromedia (MACR), and MetaLincs, an enterprise e-mail search company that was acquired by Seagate (STX).

Prior to founding Cheyenne Ventures, he was a co-founder of Harmony Partners, where he focused on consumer tech and enterprise-focused companies. He thrives on partnering and discovering expansion-stage opportunities with visionary founders and aligned VCs that seek an advantage with the Cheyenne structure. Known for his ability to build strong trust and meaningful, longstanding relationships, Greg works closely with founders and CEOs to help them navigate growth and success.

Greg is an avid art collector who enjoys spending time in the mountains, fly-fishing, and skiing with his family. He is active in philanthropy with the Idaho Ballet and the Boise YMCA. Additionally, he is an active member and advisor to the Idaho Youth Ranch, which focuses on the rehabilitation of troubled teens through equine therapy. Greg is also on the Board of Regents at Santa Clara University and a board advisor to the Bronco Ventures Accelerator.

Jay has a proven track record as a leader in both public and private technology companies. He began his career at SAP and PeopleSoft before beginning a nearly 20 year career as a CEO. In 2021, Wiley published Jay’s book People Operations: Automate HR, Design a Great Employee Experience, and Unleash Your Workforce which became a five-time bestseller.

Prior to joining Cheyenne Ventures, Jay was CEO at Zenefits where he orchestrated an impressive turnaround of one of the most disruptive HR companies in history. Before that, Jay was CEO at Ooyala, a ground-breaking online video company that ushered in the personalized cloud TV era. Jay’s first CEO role was leading Agile Software, an enterprise software company that pioneered product lifecycle management and distributed engineering. Jay has an extensive track record of delivering great returns for stakeholders and for leading high growth, high value businesses that are transformational and category-defining. He believes in the power of building strong cultures that reinforce the importance of people, inspiration and purpose.

When he isn’t spending time with portfolio companies and doing the mentoring work he loves, Jay spends his time at his home in the mountains. There he is an avid outdoorsman and enjoys horses, golf, fly fishing, skiing, hiking, and biking — usually with his dog Django alongside.

J.R. brings 20+ years of experience at the intersection of venture capital and company building, with a proven record of scaling companies and leading four successful exits—including Liftoff Mobile’s sale to Blackstone in 2020. He’s held leadership roles across Tech, Media, and Telecom, known for turning strategy into execution and driving results.

Before joining Cheyenne Ventures, J.R. advised founders and led Go-To-Market and Ops functions in high-growth startups, helping teams navigate scaling, category creation, and commercialization. His dual perspective as an investor and operator gives him a hands-on, empathetic approach to working with leadership teams.

He’s passionate about building mission-driven companies with strong cultures and sustainable growth. A former collegiate golfer at UCSB, J.R. is also an avid fisherman and mountain biker, spending his free time outdoors with his two sons. He serves as Chairman of College Golf Fellowship and sits on the board of Dream Machine, a global collective of award-winning visual effects studios.

Rachel brings a dynamic background in e-commerce, entrepreneurship and business development to Cheyenne VC. Before joining the firm, she spent five years at Walmart eCommerce, where she played a key role in category management, strategic partnerships, and digital expansion. As the lead for the premium beauty space at Walmart, she managed an $81M portfolio, successfully launching Walmart’s first premium beauty omni-channel partnership and optimizing digital merchandising strategies to drive growth. She also co-founded WalmartStart, the global megaretailer’s first and only beauty accelerator program, designed to identify and scale high-growth, early-stage brands across the U.S. She later transitioned to Walmart’s Health & Wellness division, where she led various initiatives focused on expanding consumer access to digital health solutions and elevating health equity, including the launch and scale of the nation’s first COVID-19 at-home test for any major retailer.

Rachel also works as an OpenAI Fellow, where she explores the intersection of AI innovation and startup ecosystem building, deepening her commitment to enabling responsible, transformative technology. Rachel brings a strong operator mindset to her work, with experience supporting early-stage startups across AI, e-commerce, fintech, and SaaS.

Rachel holds an MBA from the MIT Sloan School of Management, where she focused on entrepreneurship and venture capital. During her time at MIT, she co-led MIT’s first student-founded and led accelerator, MIT Momentum, where she supported over 50 pre-seed and seed-stage founders. She also holds a BA from the University of Pennsylvania, where she was a Division 1 athlete on the women’s varsity rowing team.

Rachel currently serves as a co-lead of the MIT AI Conference—one of the largest AI events in the country. She is also a founding member of Women Who AI, an organization aimed at supporting and elevating women building at the frontier of artificial intelligence. A Pacific Northwest native, Rachel enjoys hiking, skiing, and traveling with her pug, Penelope.