GREGG BROCKWAY

Gregg Brockway stands out as a prominent figure in the technology and e-commerce landscape, recognized for his exceptional track record as a serial entrepreneur and strategic investor. His career is defined by co-founding and scaling multiple highly successful companies, demonstrating a keen understanding of consumer needs and market dynamics.

Brockway's journey began with a strong foundation in strategy consulting at Bain & Company, where he honed his analytical and business development skills. This experience proved invaluable as he transitioned into the entrepreneurial world. He first made a significant impact as a co-founder and President of Hotwire, a pioneering online travel agency that revolutionized how consumers booked travel. Hotwire's innovative opaque pricing model quickly gained traction, leading to its successful acquisition by Expedia, Inc., solidifying Brockway's reputation as a visionary in the travel tech space.

Following Hotwire, Brockway continued his entrepreneurial streak by co-founding and serving as CEO of TripIt, a popular mobile travel organizer. TripIt simplified travel planning by automatically creating master itineraries from booking confirmations, becoming an indispensable tool for millions of travelers. Its success led to its acquisition by Concur Technologies, further cementing Brockway's influence in the travel technology sector.

Most recently, Gregg Brockway co-founded and served as CEO of Chairish, an online marketplace for vintage, antique, and pre-owned home furnishings and art. Under his leadership, Chairish grew into a leading platform for design enthusiasts and professionals, championing sustainability and unique style in the home decor market. Chairish was acquired by Replacements, Ltd. in 2023, with Brockway continuing to lead the company as CEO, demonstrating his ongoing commitment to its growth and vision.

As an investor and advisor, Gregg Brockway primarily focuses on early-stage companies within the consumer internet, e-commerce, and travel technology sectors. His investment philosophy is often rooted in supporting founders who are building innovative solutions to real-world problems, leveraging his extensive operational experience to guide new ventures. While he may not operate a traditional venture capital firm, his personal investments and advisory roles are highly sought after due to his deep industry knowledge and proven ability to scale businesses. His career background showcases a consistent ability to identify emerging trends, build strong teams, and execute successful strategies, making him a valuable asset to any company he engages with.