Black Professionals in Private Equity & Finance – Dealmaker Spotlight: Mike Smith

July 30, 2021

The following series features interviews with Black dealmakers and trailblazers in the private equity and finance community. To help us spotlight professionals making a difference in their career pathways, please email Greg Kilpatrick at [email protected] and Gerald Thomas at [email protected].

Mike Smith

Q: What attracted you to PE?

Mike Smith: My path to PE, specifically venture capital (VC), has been a bit indirect. After business school, I spent about five years exploring a few different roles and industries before I found my footing at in 2003. I joined in a junior operating role when there were 100 people in the division and $150 million in revenue. When I left nine years later, I was chief operating officer (COO) overseeing thousands of people with $5 billion in revenue.

Next, I met Katrina Lake, founder of Stitch Fix. I was inspired by her story and what she was building, so I joined the company when we had very little in revenue and fewer than 10 people on board. At Stitch Fix, I had a very similar experience of hyper growth as I helped scale the company to thousands of people and from almost no revenue to billions in revenue.

Both experiences at and Stitch Fix drew me into VC. I love early-stage, hyper-growth companies and the endless learnings that come with the journey. I also saw the challenges of raising capital as venture capitalists struggled to understand Stitch Fix and I witnessed Katrina, as a female founder, push through the ecosystem with grit and determination.

Given my experiences as an operator and stature as a successful executive, I determined that I was in a unique position to help founders and their founding teams, all while making the VC industry more inclusive to underrepresented backgrounds. Therefore, in 2021, I started a venture capital firm, Footwork, with my co-founder, Nikhil Basu Trivedi.

Q: Why do you actively support providing capital to Black entrepreneurs?

MS: A core value of Footwork is that diversity across every dimension is a competitive advantage. As a Black entrepreneur who worked alongside a female CEO (Katrina Lake), I’ve seen firsthand the power of diverse perspectives, of giving voice to the underrepresented and of backing founders who overcame the odds to pursue their dreams.

As the VC ecosystem currently stands, Black entrepreneurs do not have enough access to capital. If we change this, the diversity reflected in our teams and investments will help us find and support the best next generation of founders.

Q: Why is it important for more Black professionals to pursue entrepreneurship?

MS: I’m proud and fortunate to have had the experiences that I’ve had in the VC ecosystem and e-commerce industry. However, it shouldn’t be the case that I’m the only or one of a few Black professionals at the table. While there has been some progress, there needs to be more. I hope Black entrepreneurs continue to pursue their dreams and that the VC community becomes more inclusive so journeys such as my own are bountiful.

Q: Who is an example of someone who inspired you in PE and why?

MS: Ken Coleman, chairman at EIS Group, has been an inspiration to me ever since I met him nearly a decade ago. Ken is a longtime executive and adviser to venture firms and founders. At the end of our first meeting, I asked him how I could be helpful to him. He said I could do two things: (1) Be very successful, and (2) hire more people of underrepresented groups.

These two points have stuck with me ever since and have influenced how I operate as a Black entrepreneur and now as a venture capitalist.

Q: What is a goal that you have set for yourself in the coming year?

MS: I have a list of 24 values that I operate by both personally and professionally. This year, I’m focusing on one in particular: Measure twice but cut once. An early focus of mine in investing has been on developing a robust decision-making framework to ensure that I make great, consistent investment decisions. At the same time, the pace of VC is very quick. There is a famous John Wooden (former UCLA basketball coach) quote where he said, “Be quick but don’t hurry.” I quickly learned that you need to move with pace while being measured and disciplined. Thus, I’m focused on applying the “measure twice but cut once” value to my new role as a VC investor.

About Mike Smith

Mike Smith is general partner and co-founder at Footwork, an early-stage VC firm. Previously, he was president, COO and interim chief financial officer at Stitch Fix, the online personal styling service, where he oversaw operations, styling, client experience, merchandise and finance.

Prior to Stitch Fix, Smith was COO at, overseeing all operations for a $5 billion division, including one of the most successful multichannel offerings in the industry. He holds a bachelor’s from the University of Virginia and an MBA from the Haas School at University of California, Berkeley. He serves on the boards of Stitch Fix, Herman Miller, Big Sky Growth Partners and Ulta Beauty, as well as private boards such as Food52 and Mayvenn.

To contact Mike Smith, email [email protected].