Our Team
Charles Bishop- Founder & Operator
Charles is a native Oregonian with a long-standing connection to the Portland area. He studied Finance and Entrepreneurship at Syracuse University, where he developed a strong foundation in business strategy and a passion for building things from the ground up. During his high school and college years, he launched and ran several small businesses—early experiences that planted the seed for a career in entrepreneurship.
Over the past decade plus, he has built a well-rounded skill set through leadership roles in operations, sales, and management at leading retail and tech companies. These experiences have equipped him with the tools to lead teams, streamline processes, and drive long-term business growth. He now brings that expertise back to small business ownership, combining strategic thinking with a hands-on, people-first approach.
Outside of work, he’s a dedicated sports fan, outdoor enthusiast, and more recently, an active parent—to both his daughter and his garden. Charles finds joy in watching businesses develop, and seeing things grow under his guidance.
Carolyne Bishop- Advisor
Carolyne is a seasoned entrepreneur with more than a decade of experience in the startup world. With a background in sales, marketing, and communications, she brings a sharp strategic mind and a people-first approach to everything she does. Carolyne earned her degree in Public Relations from the Newhouse School at Syracuse University, where her talent for clear, effective messaging first took root.
Raised in Seattle and now rooted in Oregon, Carolyne comes from a long line of entrepreneurs. Over the years, she has owned and operated her own venture, led high-performing teams, and built lasting relationships across industries. She’s known for her ability to cut through the noise, ask the right questions, and offer thoughtful perspective—skills that make her not only a strong leader, but a trusted advisor.
Outside of work, Carolyne is a devoted mother, wife, and friend. She finds joy in gathering people around a table, whether she’s trying out a new recipe at home or exploring Portland’s dynamic restaurant scene. She’s also Charles’s closest collaborator in both work and life, offering wisdom, humor, and unwavering support.
Ian McMilan- Advisor
Ian brings over a decade of entrepreneurial and operating experience, and currently serves as a Vice President at TTCER Partners. He has completed over 20 private transactions and serves on the board of two private companies. A (below-average) former D1 athlete, Ian has always been inspired by unlocking potential and winning with a team.
He began his career in consulting but soon jumped at the opportunity to work at Nike—a brand deeply connected to his hometown and committed to maximizing human potential. During his time there, he held roles across multiple functions and led projects spanning from China to Brazil.
His time at Stanford’s Graduate School of Business gave him a fresh perspective on entrepreneurship and a deep appreciation for the role investors play in fostering leadership and building lasting businesses. That experience inspired him to launch a small investment fund and take on board and advisory roles—work that cemented his passion for championing entrepreneurs.
As an advisor to Charles, Ian brings this same passion and perspective to help him grow as a leader and build an enduring business.
Erin Cobb- Advisor
Erin is a serial entrepreneur with a passion for building things from the ground up. After earning a degree in Finance from Boston College, he dove headfirst into the world of small business—starting, buying, and selling several ventures throughout the Seattle area. Each endeavor has added to a growing toolkit of hands-on experience in finance, operations, and creative problem-solving.
Today, Erin is the co-founder and operator of Cobb’s Gourmet Popcorn, a small-batch popcorn shop that has been located in Seattle’s iconic Pike Place Market for 7 years. Cobb’s is the latest expression of his belief in thoughtful products, great service, and community connection.
Outside of work, Erin is an avid reader, an adventurer at heart, and a curious mind who never stops learning. Whether he’s exploring a new country on two wheels, diving into a new book, or dreaming up his next project, he brings the same energy and enthusiasm that fuel his entrepreneurial journey. His curious mind and dedication to building things make him a trusted advisor to Charles.