Pioneering Innovation: Walt Greenberg’s Journey
SEATTLE, WA – With a passion for turning innovative ideas into impactful realities, Walt Greenberg spent his career at the intersection of marketing, technology, and entrepreneurship. From pioneering early financial technologies to advising and investing in startups, Walt brings decades of experience and a keen eye for recognizing potential to his role as Venture Partner at Mastersfund. In this interview, Walt shares his journey from the corporate world to venture capital, the qualities he looks for in founders, and what excites him most about being part of the Mastersfund team.
Nha: Thank you for taking this time to speak with me, Walt. Please tell me a little bit about yourself and your personal journey.
Walt: I grew up in Chappaqua, Westchester County, New York, about 40 miles north of New York City. I went to Rice University in Houston, Texas, for undergraduate school, where I double-majored in physics and economics. I had no desire to go into teaching or research, so I headed off to business school. Harvard accepted me, but wanted me to wait two years. MIT Sloan School of Business accepted me immediately out of my undergrad work. I didn’t want to wait, so I chose MIT Sloan.
Sloan turned out to be a great choice. It’s much smaller than Harvard. We had 140 people in our class, and we all knew each other very well. Sloan was also the first business school with a concentration in entrepreneurship and technological innovation, which appealed to me because of my physics background.
I initially planned to leverage my physics background into technology and innovation. However, during my second semester, I took my first case study course in marketing and, to my surprise, realized that marketing was analytical problem-solving — something I loved. I ended up making a career by marrying marketing and technology in the financial services sector where I evaluated, implemented and oversaw the ongoing management of new business initiatives.
My career spanned more than 25 years at Citibank, Mastercard International, Bank One, and a couple of startups. I took customer-driven, technologically-innovative products to market. For example, I helped pioneer shared ATMs in the early 80s, and PC banking before the world wide web. At Mastercard, I oversaw the initial worldwide pilot and subsequent rollout of chip cards in Australia, Latin America, and Asia Pacific, 10 years before they were introduced in the U.S. At Bank One, I led a group focusing on the launch of prepaid cards — gift cards, payroll cards, university cards. All of these roles involved taking an embryonic product to market and nurturing its growth. I loved running these as small, standalone businesses within the larger corporate structure. It was intrapreneurship – small startups inside enterprise companies.
Nha: That’s awesome! How did you get into startup investing?
Walt: I retired from the corporate world in 2010, after spending four years consulting in the pre-paid debit card space. Shortly after, a business school buddy in Seattle asked me to advise and invest in a father-and-son startup. I provided a nominal investment but quickly realized they lacked business savvy and didn’t know how to raise money. We needed someone to provide business leadership and help raise funds, so my buddy brought in Gillian, who had just exited from her startup, Moz. Although the father-and-son eventually backed out of the agreement to have Gillian lead the firm to success, she and I stayed in touch.
About a year later, Gillian called to ask if I’d be interested in joining her in investing in and advising brettapproved, an information and booking site for mobility challenged travelers. Gilian and I (with Anne joining in the “fun” shortly thereafter) bankrolled and led the startup for 6+ years until the pandemic hit, forcing us to make the difficult decision to close it down, knowing it would be several years before travel picked up again.
During this time, Gillian introduced me to several other Seattle-based startups. I’ve now personally invested in six or seven startups, some of which failed due to a lack of leadership or capital. Others have done quite well.
Nha: You are Mastersfund’s first investor. Why did you choose Anne and Gillian?
Walt: As mentioned, I had been investing with Anne and Gillian for some seven years when they started conceptualizing Mastersfund. We had become good friends and trusted business partners. I had immense respect for their intelligence, integrity and prior track record of accomplishments. I knew that they perfectly complemented each other. Gillian is the go-getter, she is the visionary who makes things happen. Anne is the grounded, organized, detail-oriented leader. So, when they asked me to invest and get involved as a venture partner, I readily accepted. With the shutdown of brettapproved, I was looking for something to fill the space and keep me in the loop. Mastersfund gave me the opportunity to leverage my background in evaluating and implementing new business initiatives, and overseeing their growth in the marketplace. Throughout my career this is what has given me the most gratification.
Nha: How about founders? What qualities or traits are non-negotiable in founders or companies you invest in?
Walt: I invest in companies and products I can relate to or use — companies where I can bring value. After having now spent over 10 years investing in startups, I’ve learned the hard way, what the key success factors are in early stage investing. More important than the product, or even the market opportunity, you’re betting on the founders. In the end, they are going to make or break your investment. Do they have a support system, the focus, the energy, and the passion burning in their bellies to truly drive the business forward and overcome the inevitable adversity? Do they have a keen knowledge of all aspects of their business and tight control over each aspect, particularly financials, and are they receptive to advice and guidance? Unfortunately, most of these qualities can be difficult to discern during the due diligence process. Probing questions can help and I’ve learned to do that at Mastersfund.
For example, Ashley Selman and Britt Dougherty are the founders of heywell, an adaptogenic sparkling water that is seeing strong market traction. When I first brought heywell to Mastersfund, there was widespread skepticism about whether this was a good match for a Mastersfund investment. Most of our investments are in tech or data-driven companies. None of the partners had prior experience in consumer goods. But Ashley’s and Britt’s passion and business acumen won Anne. Gillian, and the venture partners over. These founders clearly had tight control of their business, which impressed us. The bet has paid off.
Nha: What are you most looking forward to as Mastersfund continues to grow?
Walt: Though I’ve been an early-stage investor for many years now, Mastersfund is my first exposure to the venture capital world. I’m still learning from Anne and Gillian, from the other venture partners, and from our growing list of portfolio companies. Since I am now retired, being a part of the Mastersfund Venture Partner team has filled a void for me. The work feeds my love of evaluating and nurturing new businesses and being a catalyst for their growth and success. Writing larger checks as the fund grows means we will have a greater impact on our portfolio companies. We’re not just investing; we’re helping these companies succeed.
Nha: Thank you so much, Walt. It’s been a pleasure learning about your experiences. All of us at Mastersfund appreciate you taking the time to share your journey with us.
Walt: My pleasure!