Mixing business and friendship is challenging because it requires balancing two distinct relationships—personal and professional. Friends may assume mutual understanding and commitment, but in business, clear expectations and boundaries are essential. Conflicts can arise when personal dynamics interfere with professional decisions, such as having to fire a friend if they no longer contribute effectively to the business.
Will Guidara learned that his identity was too intertwined with being a restaurateur. After selling his stake in Eleven Madison Park just before COVID, he faced an identity crisis. This experience taught him the importance of stopping to reflect on what he truly wanted next, leading him to write his book 'Unreasonable Hospitality' and transition into a new career phase focused on teaching hospitality.
Vulnerability leads to confidence by allowing individuals to admit their mistakes and insecurities without fear of losing respect. Taking risks to be vulnerable in relationships—whether in friendship, business, or marriage—builds trust and understanding. Over time, this practice makes it easier to have honest conversations, admit faults, and strengthen connections.
Compartmentalizing friendship and business relationships is crucial to maintaining respect and effectiveness. In a business context, friends must switch roles to act as colleagues, ensuring professionalism and clear decision-making. Conversely, in personal settings, they revert to their friendship dynamic. This separation prevents conflicts and ensures both relationships thrive without undermining each other.
Friendship breakups require effort because they involve deep emotional investments and shared vulnerabilities. Unlike romantic or business relationships, friendships lack formal contracts, making it easier to avoid addressing issues. However, intentionally ending or addressing a failing friendship is an act of respect and generosity, helping both parties move forward with clarity and closure.
Setting clear expectations is vital when starting a business with friends to avoid misunderstandings and resentment. It ensures both parties understand their level of commitment, responsibilities, and goals. Without clarity, assumptions can lead to conflicts, especially if one friend is more invested than the other. Open communication helps maintain both the business and the friendship.
Respect is essential in maintaining dual relationships because it ensures that both parties honor the boundaries of each role. In a business context, respect means treating the friend as a colleague, avoiding over-familiarity that could undermine authority. In personal settings, it means prioritizing the friendship over professional dynamics. Balancing these roles fosters trust and mutual support.
COVID gave Will Guidara the gift of stopping and reevaluating his life. After selling his stake in Eleven Madison Park just before the pandemic, he faced an identity crisis. The pause forced by COVID allowed him to reflect on his next steps, leading him to write 'Unreasonable Hospitality' and shift his career focus from owning restaurants to teaching and writing about hospitality.
Differentiating between public and private personas is important because it shows respect for the context and the people involved. In public, individuals may need to adapt their behavior to fit societal norms or professional settings, while in private, they can be their true selves. This balance ensures that relationships remain authentic without compromising professionalism or social expectations.
The key to successfully working with friends in business is maintaining both the friendship and the professional relationship separately. Clear communication, mutual respect, and setting boundaries are essential. Friends must be honest about their expectations and commitments, and they must be willing to switch roles depending on the context—acting as colleagues in business and friends in personal settings.
They say business and pleasure don’t mix. But what about business and friends?
My dear friend Will Guidara is the perfect person to dive into this question because we're actively trying to get into business together. And, let's just say, it requires a lot of effort.
In addition to being someone I love, Will is a renowned restaurateur, known for owning and operating Eleven Madison Park, once named the best restaurant in the world. He’s also the author of the brilliant book* Unreasonable Hospitality *and a co-producer of the HBO television series The Bear.
Will and I have worked together before, so I was excited to chat with him about turning friends into colleagues, the reality of friendship breakups at work, and why sometimes showing respect means we have to change the way we treat a friend.
This…is A Bit of Optimism
For more on Will and his work, check out: