Welcome to Bootstrap the Lighter Side, where successful entrepreneurs share their inspiring stories of startup growth. In this episode, we delve into the journey of Chris Fellows, the founder and CEO of Bold Street. Melissa Widner, CEO of Lighter Capital, joins the conversation to uncover the intricacies of transitioning from a service-based business to a product-oriented venture.

Chris Fellows, a successful entrepreneur with experience in both product and services businesses, wanted to launch Bold Street, a platform connecting real estate agents with residential investors. However, he knew he needed a co-founder to navigate the challenges of building a product company.

After reflecting on a past solo venture that lost momentum, Chris sought a co-founder to provide support, challenge ideas, and maintain momentum. He connected with Clara, a former colleague with relevant experience and a shared vision for Bold Street.

Chris and Clara spent a year vetting the idea, interviewing potential co-founders, and solidifying their partnership. This collaboration proved invaluable:

  • Complementary Skills: Clara’s expertise in product discovery and sales complemented Chris’s technical and business acumen, leading to a well-rounded approach.
  • Shared Passion: Their shared vision and enthusiasm for Bold Street fueled their commitment and resilience through inevitable challenges.
  • Momentum Maintenance: Having a co-founder kept them accountable and motivated, preventing the loss of momentum that had plagued Chris’s previous solo venture.

Key Takeaways

  • Transitioning from Services to Products: While both require strong business fundamentals, product companies demand a different financial mindset, focusing on upfront investment and lean development.
  • Minimum Viable Product (MVP): Understanding the core offering customers value and iteratively refining it is crucial for product success.
  • Co-founder Benefits: A co-founder can offer invaluable support, challenge ideas, and maintain momentum, especially when transitioning from services to products.
  • Finding the Right Co-founder: Shared values, complementary skills, and a strong working relationship are crucial for a successful co-founder partnership.


Are you considering starting a product company? Consider the potential benefits of a co-founder and carefully assess your needs and compatibility before embarking on this journey. Remember, a strong co-founder partnership can be a powerful force in navigating the challenges and maximizing the potential of your venture.

Francis Dimaano