Robert Reffkin: From Average Student to Compass Founder

Compass CEO Robert Reffkin on Overcoming Obstacles and Inspiring Future Entrepreneurs

In April, real estate technology firm Compass completed its initial public offering, achieving a valuation in the billions of dollars. Following this milestone, TechCrunch Senior Editor Alex Wilhelm engaged with founder and CEO Robert Reffkin to discuss the company’s market entry amidst fluctuating conditions for tech and tech-driven IPOs.

A Childhood Shaped by Resilience

This week, a conversation with Reffkin centered on a different subject: his journey to entrepreneurship, stemming from a childhood marked by adversity – raised by a single mother who faced disownment, and a father who tragically died experiencing homelessness. Reffkin is deeply committed to motivating individuals from unconventional backgrounds to pursue their ambitions, a passion that led him to author a book on the subject.

During our discussion, Reffkin revealed the principles he attributes to his success – emphasizing the importance of active listening – and offered guidance to aspiring young entrepreneurs, particularly those facing systemic disadvantages. This interview has been condensed for clarity and conciseness.

From Teen DJ to Columbia University

TC: Considering I’m a parent to a teenager already exploring entrepreneurship, I’m fascinated by your experience as a teenage DJ. What ultimately sparked your dedication to academics, and how did you manage to complete your degree in an accelerated timeframe?

Reffkin: I believe your son is on a promising path! Please extend my encouragement to him, from one entrepreneur to another.

My mother faced skepticism from other parents for allowing me to launch my DJ venture. However, establishing a thriving DJ business in high school provided invaluable self-discovery and fueled my entrepreneurial spirit. This experience proved pivotal in my acceptance to Columbia University, forming the foundation of my application and the relationships I cultivated with the admissions committee.

I firmly believe that envisioning ambitious goals is the initial step. My aspirations for college took shape during a visit to New York City. Touring Columbia ignited a passion within me, but I recognized the challenges I would face in gaining admission. My high school counselor even advised against applying, deeming the application fee unwarranted. This dismissal intensified my resolve, transforming my desire into a broader pursuit of opportunity for individuals like myself. Consequently, I dedicated myself to SAT preparation, demonstrating my capacity to excel in a rigorous academic environment, and ultimately, my efforts were rewarded.

Throughout high school and college, my academic performance was average, as I struggled to connect the relevance of subjects like calculus or Western Civilization to my life and aspirations. I understood that academic excellence wouldn’t be my defining characteristic. Simultaneously, I was invigorated by my entrepreneurial endeavors and summer internships. I prioritized completing my education swiftly to embrace the real world, which resonated more profoundly with me.

The Impact of Background and Identity

TC: How did your upbringing by a single mother facing hardship influence your development as a person and as an entrepreneur? Furthermore, how did your identity as a person of color shape your trajectory?

Reffkin: My upbringing consisted solely of my mother. She is an Israeli immigrant who was disowned by her family due to my parentage. My father abandoned us and later passed away while experiencing homelessness. The most significant entrepreneurial lesson I learned came from my mother. She exemplified resilience, teaching me that setbacks are inevitable, but bouncing back with unwavering passion is crucial. I witnessed her navigate challenging relationships, bankruptcy, and the constant rejection inherent in her profession, yet she always persevered. Therefore, when confronted with doubt or predictions of failure, I was prepared to overcome them, thanks to my mother’s example.

As a Black and Jewish individual, I’ve often felt like an outsider. In most high school and college classes, I was the sole Black student. Early in my career, I frequently found myself the only Black person in meetings. When seeking funding for Compass, I rarely encountered Black individuals on the opposing side of the negotiating table. However, I’ve been incredibly fortunate to receive guidance from a strong network of Black mentors, including the late Vernon Jordan, Ken Chenault, the former CEO of American Express, and Bayo Ogunlesi, lead director for Goldman Sachs.

The Power of Mentorship

TC: You’ve benefited from the guidance of several influential mentors. How did these relationships evolve, and what value did they provide beyond the obvious?

Reffkin: From a young age, I actively sought advice. Growing up in a single-parent household, I sought guidance and wisdom on building a better life wherever I could find it. My mother connected me with several nonprofits during high school, which broadened my awareness of the opportunities and support available.

The most valuable lesson I’ve learned is that feedback is a valuable gift, even when it’s difficult to hear. My relationships with mentors deepened because I proactively requested candid, honest feedback – the kind others might hesitate to offer. I then applied their advice and shared the results with them. This fostered more insightful and practical guidance, accelerating my growth. It also deepened their investment in my success and the success of my endeavors.

Furthermore, my mentors instilled in me the belief that success was attainable, despite external perceptions. Meeting someone like Vernon Jordan, who advised presidents and CEOs, had a profound impact. He served as a father figure, and his support and advice helped me feel a sense of belonging and envision a path to achieving my full potential.

Paying it Forward

I established a nonprofit organization in my twenties, America Needs You, which has provided mentorship, career development, and college support to thousands of students. I wrote my new book, “No One Succeeds Alone,” to share the lessons I’ve learned from remarkable individuals, donating all proceeds to organizations that empower young people to pursue their dreams.

Advice for Aspiring Entrepreneurs

TC: What advice would you offer to young, aspiring entrepreneurs, particularly those from underrepresented backgrounds?

Reffkin: Here’s my advice for a recent college graduate from an underrepresented group entering their first job:

• Don’t allow anyone to hinder your aspirations. Ignore societal limitations, colleagues’ doubts, and even your own self-doubt. When faced with discouragement, accelerate your efforts.
• Dedicate the next decade to learning from the most intelligent individuals you can find. Seek mentors both within and outside your workplace who will provide honest, constructive feedback. Embrace feedback as a gift, even when it’s challenging.
• Transform negativity into positive energy that fuels your drive. You will inevitably encounter skepticism, doubt, and criticism.

Looking Ahead

TC: What are your plans for the future beyond Compass?

Reffkin: I firmly believe that true success requires unwavering commitment. As a CEO, you must be fully invested, and that’s precisely where my focus lies with Compass – 100% dedicated to our 23,000 agents and employees. A mentor once described the “shower test” – if you aren’t enthusiastic enough about your work to contemplate it while showering, you’re likely in the wrong role. I’m deeply passionate about the company we’re building, and Compass remains on my mind even during my morning routine. We’ve achieved significant milestones in the past eight years, but we’re only just beginning.