Christopher Bossola

Christopher Bossola is a Growth Consultant at Crews & co. and a seasoned entrepreneur with more than 25 years of leadership experience across retail, real estate, and technology. He helps companies scale with clarity and discipline while strengthening profitability and long-term enterprise value.

Chris built his career leading high-growth private equity backed ventures through complexity and transformation. As Founder and CEO of Need Supply Co. and Totokaelo, he scaled a single storefront into a global retail platform featured in Vogue, GQ, and The New York Times. He later co-founded The Endowment Project, an education technology company that created sustainable funding systems for public schools across Virginia.

Combining strategic vision with operational rigor, Chris has secured over $100M in capital, led successful mergers, and developed teams known for accountability, creativity, and measurable results.

He earned his degree in Corporate Finance from the University of Alabama and served as Chair of the Virginia Chapter of the Young Presidents’ Organization (YPO).

Experience

• At Need Supply Co. and Totokaelo, Chris grew a single storefront into a global fashion brand generating over $50M in revenue. Under his leadership, the company earned multiple Inc. 5000 honors and was featured in Vogue, GQ, and The New York Times.
• As co-founder of The Endowment Project, he built and deployed more than 300 alumni funding platforms that generated over $1M for Virginia public schools, pioneering a sustainable approach to public education funding.
• Through South Bank Ridge Development, Chris led an urban infill real estate project along the Richmond riverfront, delivering a 2x equity return with a full sell-through achieved in just 30 days.

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