Robert Carroll – Interface design and asking, "What do you want to achieve?"

Robert Carroll, successful entrepreneur and product leader, tells Tom about his journey as a father and how he’s approached different stages of his career based on his personal needs. Robert tells about an early digital video product he built that sold for $300,000 a unit, and then discusses how a technical advantage can evaporate quickly. Tom asks if it's better to be consistently bad in software interfaces than to be uniquely good. Robert talks about how markets define standards like the QWERTY keyboard. Robert tells about creating one company to help people with physical disabilities use computers effectively and another one that helped Fortune 500 companies apply principles of product management to their sales processes. Tom and Robert talk about the psychology of pricing and why companies choose expensive options. Tom asks Robert how he decides between self funding and getting outside investors when he starts a new business. Robert talks about how understanding intent when founding a business is critical for knowing how to fund the business. Robert tells about the founding of his three businesses and how different ideas about what he wanted to achieve affected each. Robert tells how product managers need to understand the capabilities and deficiencies of the technology their products use. Tom and Robert talk about learning styles and teaching strategies, managing technical teams, and being a servant leader. Robert tells about defining clear goals for teams and his resistance to "embracing ambiguity" instead of being clear about objectives. Finally, Robert talks about being in the “fourth quarter” of his career and how he's defining what he wants to do next.