Meet Daniel B. Silvers, a forward-thinking investor, board leader, and builder shaping the future of fan engagement and corporate leadership. As Founder and Managing Member of Matthews Lane Capital Partners LLC and Executive Chairman of Winventory, Inc., Silvers is helping modernize the season ticket model through technology, innovation, and a more equitable experience for fans. His career includes senior roles such as CEO of Leisure Acquisition Corp. and Executive Vice President and Chief Strategy Officer at Inspired Entertainment, Inc., in addition to serving on numerous public company boards across the technology, media, healthcare, and entertainment sectors. He was recognized by the National Association of Corporate Directors as part of its “A New Generation of Board Leadership: Directors Under Age 40” list.

Previously, Silvers led SpringOwl Asset Management, worked at Fortress Investment Group, and began his career in investment banking at Bear Stearns. He holds a B.S. in Economics and an M.B.A. in Finance from The Wharton School of the University of Pennsylvania, along with Corporate Governance certification from UCLA Anderson. Beyond his corporate work, he remains deeply involved in not-for-profit organizations, including the Horace Mann School, the University of Pennsylvania, and UJA-Federation of New York.

Now, let’s dive into our Q&A with Daniel Silvers to explore his path, perspective, and vision for what comes next!

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Before we dive in, our readers would love to get to know you a bit better. Can you share your backstory? What led you to your career path – both early on and now?

Great to be here with you. I grew up in New York City and have basically lived here my entire life – other than while I was in school. I did a combined Undergrad/MBA Program at Penn/Wharton and then went into investment banking at Bear Stearns where I focused on the Real Estate, Gaming and Lodging industries. I then was at an investment firm called Fortress, again focusing on the same industries. Since 2009, I have been involved in a large number of entrepreneurial ventures and have served on a number of corporate boards across a wide range of industries including Media, Technology, Business Services, Industrials, Real Estate, Food Services, Gaming, Hotels and Natural Resources.

You’ve had an extensive career across investment management, corporate governance, and now as Executive Chairman of Winventory. How has your experience serving on so many boards shaped your leadership style as a founder and executive?

I have definitely learned a lot about when to speak and when to listen – when in doubt, the right answer is normally to listen! Perhaps more importantly, over time you learn when to allow someone to make a mistake because the value of the learning experience will be greater to the business than the “cost” of the mistake. It’s easy to know an answer and to take over when you know that someone is about to make a mistake; it’s a lot harder to let the person make the mistake because you realize that the mistake won’t be the end of the world and that the person will learn and grow from making it.

When you first stepped into your leadership role at Winventory, what was one major challenge you faced, and what lesson came from it?

When our Co-Founder and CEO – Alex Warner – asked me to join Winventory as Executive Chair, we spent a lot of time talking about his path in operating the Company to-date. When he and Sam (Walderman) founded the Company, they pretty much did it on a shoestring, and so they were literally doing EVERYTHING themselves. I think the biggest challenge has been working with Alex to help him think about the necessity of delegating and prioritizing, otherwise, there just aren’t enough hours in the day. It’s something we still confront as we work to manage the business.

Winventory sits at the intersection of technology, sports, and entertainment. What excites you most about bringing innovation to such a traditional space like season ticket ownership?

Knowing that you are helping real fans (as both buyers and sellers) to enjoy a team that they love is incredibly rewarding. The season ticket ownership model has definitely changed, and without Winventory, a lot of our customers would have moved on from their season tickets because it has become so difficult for fans to do on their own.

What do you see as some of the key factors that contributed to your success?

Definitely hard work and perseverance. These are things I constantly try to impart on my kids who are both in high school.

What advice would you give to fellow leaders to help them thrive and avoid burnout?

You are going to spend an immense amount of time living and breathing your business. Without question, make sure that you absolutely love what you will be doing. If you don’t love it, and aren’t passionate about it, you most likely won’t be good at it or successful.

Who are you most grateful to for helping you get to where you are today?

I think there are two places where that support comes from. First, is family. My wife allows me to keep my focus on business goals and without that focus, you just can’t be successful. Second, is having senior-level resources from early in your career that you maintain close relationships with and can just bounce ideas against for sanity checks and pressure testing.

You were recognized by the National Association of Corporate Directors as part of a “New Generation of Board Leadership.” What do you think next-generation board members and executives must do differently to meet today’s business challenges?

The “old school” governance model was to show up four times a year, have lunch, don’t say a lot and pick up a check. I think it is now pretty widely acknowledged that the old model is broken. In today’s corporate environment, the Board and Management need to have a lively, but constructive, dialogue where the Board challenges Management’s thinking to drive to the best outcome. The need for diverse skills is also obviously highly important in our constantly-evolving world – a board needs to have experience managing global enterprises and all of the technology and human capital issues that come with it.

When you think about the impact you want to have, what guides the decisions you make as a leader?

I’m not sure I think about that a lot. I try to focus on making good decisions for the present and future states of the companies I’m involved in. I think legacy is for someone to explain when you’re gone and they have the total picture to draw upon.

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