Heather Denniston

Heather Denniston is a founding partner leading strategy and operations for LUDEX. As founder and CEO of the human capital and consulting firm Grayson & Graham, she identified and placed executive leadership for PE-run firms and was a part of leadership focused on scaling growth companies. Heather uses her background in strategy as a means to streamline operations and provide better, more efficient tools for card collectors. With a respect for the hobby, Heather hopes to give the power to collectors of all ages and push the boundaries of what was thought possible.

Where did the idea for LUDEX come from?

Our CEO and serial entrepreneur, Brian Ludden, was looking at baseball cards with his son during the pandemic and found it very difficult to know which cards he had and how much they were worth. He began an investigation into the card industry, the technology that existed within the market, and what type of solution would solve the problem. Soon thereafter he identified partners to help build the proof of concept and began to identify key players to help realize his vision. Brian took a simple idea with a very complex solution and built a team of industry experts to change the game for the card industry. I came aboard to help operationalize his
vision.

What does your typical day look like and how do you make it productive?

Is there such a thing as a typical day in the life of a startup? For us, we are constantly pivoting, making decisions as new data comes in, weighing risks, while leading a team of passionate industry professionals. Tactically speaking, we start each day with a stand-up meeting where we review goals, obstacles and opportunities for the day and week ahead. Our days are filled with evaluating progress and meeting on best practices to optimize our results and encourage collaboration. We use the OKR (objectives and key results) model to drive productivity and reflect on how we are performing. We use it now as a weekly indicator of progress and will move towards quarterly goals too as we grow.

How do you bring ideas to life?

There is a practical way to do this. It starts with a simple business plan. Build an outline of the idea first. Identify where that idea fits in the global market, and begin researching all aspects of it. Use the outline as a guide to flesh out the idea. Collaborate with leaders in the space to challenge any biases or assumptions and try to limit areas where there are knowledge gaps. Life is breathed into ideas by hard work, tenacity, and process-oriented thinking.

What’s one trend that excites you?

Although not entirely new, Artificial Intelligence continues to emerge and grow. AI and machine learning have only begun to change the way we work; there is unlimited potential in it. When I think about virtual reality and metaverse dynamics, there too are areas of exciting trends where we are only just beginning to see how it will change our personal and professional lives. In a few years it will be more commonplace and the metaverse will be our new normal for commerce, exchanging and sharing information, engaging in entertainment, etc.

What is one habit of yours that makes you more productive as an entrepreneur?

Setting goals and identifying paths to achieving them is a discipline. It is easy in a startup to find yourself busily working all the time as there is always so much to do. It can feel like a luxury to take time to plan and organize goals. It also feels like a luxury to find space to reflect on performance, but there is so much to be gained from reflection and discussion. Teams work better together when there is consensus and understanding of where we are, where we are going and what it will
take to get there. So I guess the habit here is setting goals and reflecting on performance on a weekly basis.

What advice would you give your younger self?

I heard this question posed years ago, “How do you eat an elephant? You do so, one bite at a time.” When I was younger, I would get overwhelmed sometimes when a goal seemed insurmountable. But now I see everything as attainable if you are thoughtful and willing to focus on each step forward (one bite at a time!). Work hard, learn, and pivot. Any goal can be achieved if you work hard enough. It is important to shift goals if something isn’t working. So an initial goal may not have been achieved, but you learn so much along the way, it is a win no matter the journey. In the end, I would tell myself to take small bites out of whatever “elephant” was in front of me, recognizing the journey itself is a reward.

Tell us something that’s true that almost nobody agrees with you on.

I am too much of a consensus builder to continue to believe in something where no one else sees value or agrees with me. Sometimes just having one person acknowledge your vision is enough to spur innovation and change, but an area where I am in the minority (at least in my company) is that I need an orderly working environment, free of clutter, for optimal productivity. Here is the divide: we are a tech company that works with trading cards; our office is FULL of all types of cards…like… literally cards are everywhere! Cards are stacked and spread out across large boardroom tables. There are cards spilling from boxes, bins, and binders. They seem to fill every square inch. I love cards, but I would strongly prefer a more organized way of maintaining them at work. In that way, no one else agrees with me.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I lean into learning and embrace tough conversations. We foster an environment of humility and check egos at the door. We also decided early what our values were going to be as a company. We use them as our “rules of engagement” and talk about them often. As we are creating our organizational culture this is super important: know who we are, identify our north stars and reinforce them often. I like to say that “whether or not you are paying attention to your culture, it is being created anyway.” So why not create something awesome and game-changing?

What is one strategy that has helped you grow your business?

We rely on data-informed decisions. We look at case studies and evaluate best practices but are not beholden to them. Our strategy is to use data but also carve our own path, fostering our own creativity and identity as a business and a team. It is important to step outside of the status quo and take risks that may even at times appear radical, but there is always a method behind each calculation. It is a little early to say how this strategy has worked for LUDEX, but it has helped us assemble an excellent team poised to scale, with an infrastructure to support sustained growth.

What is one failure you had as an entrepreneur, and how did you overcome it?

I guess that depends on how you define “failure.” As I mentioned earlier, you can set a goal and not achieve it, even though you learned and pivoted and reassessed. I would not characterize that as a failure. Some might not agree. Every closed door opens us up to another opportunity. That is not a novel thought. Let me explain it differently….. I recently read former Hindu monk, and life coach Jay Shetty’s book, Think Like A Monk. In it he describes learning not to judge life events that appear positive or negative, but to simply say, “Is this good, is this bad?, I don’t know…” Because we don’t know what ultimately will happen; so I try not to ride successes too high nor am I too disappointed by perceived failures…. I stay steadily in the middle, as you never know what will come next.

What is one business idea that you’re willing to give away to our readers?

I wish there was an app that could sync with my electric company, waste management and gas company and provide suggestions daily/weekly on simple ways where I can help minimize my carbon footprint. I am likely one of many who wish they could be more green but are often overwhelmed by it and stay stuck in consumption mode and not in preservation mode. Perhaps that app exists, but if it doesn’t I would like someone to create it!

What is the best $100 you recently spent? What and why?

I recently gave $100 to one of our employees who was running a triathlon for a charity that was close to her heart. I was inspired by her training and passion for making a difference and was happy to support her. But outside of altruistic spending, I recently bought a Mark Grace autographed Relic Upper Deck 8/10 that I am pretty pumped about.

What is one piece of software or a web service that helps you be productive?

We use 15Five, a software that schedules a weekly check-in with our employees. It sends five questions to each employee that should take no longer than 15 minutes for them to answer before the end of each week. It is a great way for employees to express themselves, identify strengths and weaknesses, ask for help in different areas, giving managers the opportunity to address challenges early and often. We are building a company that offers “high touch” to the members of our platform, but also to our employees. We want every employee to thrive and to view their role at LUDEX as the best job they have ever had.

What is the one book that you recommend our community should read and why?

I like reading the stories of entrepreneurs. I recently read Founders at Work by Y Combinator’s Jessica Livingston. I learned a lot and found that many of the stories are relevant to where we are in our journey at LUDEX. One thing that stood out was how often companies iterated early on, changing their strategies, products or processes. Oftentimes they evolve into totally different entities by the time they sell. It has caused me to think more about, “What else? Where else? and How else can we make a difference in this industry?”

What is your favorite quote?

I love a good quote and recently shared this with our team. Amelia Earhart said, “The most difficult thing is the decision to act, the rest is merely tenacity. The fears are paper tigers. You can do anything you decide to do. You can act to change and control your life; and the procedure, the process is its own reward.”

That perfectly encapsulates life as an entrepreneur for me.

Key Learnings:

• Use data to make informed decision in your business but also carve our own path, fostering creativity and identity as a business and a team.
• It is important to shift goals if something isn’t working.
• Learn to embrace tough conversations.
• Take small bites out of whatever “elephant” was in front of you, recognizing the journey itself is a reward.