Leading From The C-Suite: Andrew Paradise of Skillz On Five Things You Need To Be A Highly Effective C-Suite Executive

An Interview With Doug Noll

Never stop leveling up: No matter how far you get into your career, it’s critical to maintain a constant state of humility when it comes to business building because you’re always learning. Many of the things I got right when building my first two companies I got wrong when building my third, showing how easy it is to mistake luck for skill. No matter how much experience you have, keep a growth mindset. Surround yourself with trusted mentors and confidants who challenge and inspire you to continuously evolve and excel.

As part of our series called “Five Things You Need To Be A Highly Effective C-Suite Executive,” we had the pleasure of interviewing Andrew Paradise.

Andrew Paradise is the CEO and Founder of Skillz (NYSE: SKLZ), the leading mobile games platform for fair and fun competition, and the first publicly traded mobile esports platform in the world. A pioneer of the idea of skill-based competition, under Paradise’s leadership, Skillz has become an industry leader in mobile gaming.

Paradise has been the founding inventor behind companies in technology sectors ranging from eCommerce to image recognition. His passion for innovation and tech started early. At the age of seven he learned to program by hacking a video game. He began his professional career in private equity and venture capital, but in 2008 pivoted into tech when he founded his first business, Double Picture, an advertising technology firm. He sold the company to MPA, Inc. in 2010.

In 2010, Paradise founded AisleBuyer, best known for pioneering mobile self-checkout prior to its sale to Intuit in 2012. That same year, along with his fellow AisleBuyer executive Casey Chafkin, he founded Skillz, with the mission of bringing out the best in everyone through competition. The Skillz platform helps developers build multi-million-dollar franchises by enabling social competition in their games. Leveraging its patented technology, Skillz hosts billions of tournaments for millions of mobile players worldwide and distributes millions in prizes each month.

Paradise earned his B.A. in English Literature from the University of Massachusetts and a Bachelor of Commerce in Economics from the University of Auckland. A sought-after thought leader, he has been featured in such outlets as Forbes, The Wall Street Journal, BBC, Bloomberg, Fast Company, and CNBC. In 2018, he was named to the San Francisco Business Times’ “40 Under 40 Class.” He has also spoken at preeminent conferences including SXSW, CES, and GDC.

Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I am the CEO and founder of Skillz, the leading mobile games platform for fair and fun competition, and the first publicly traded mobile esports platform in the world. Looking back at my journey, my mother didn’t want to see me become an entrepreneur. She wanted me to become a doctor or a lawyer. So, even though I knew that I wanted to create my own business one day, I didn’t pursue it right away. Out of college, I went to work in private equity as an entry-level analyst. I was lucky and the only person at my firm who didn’t have a Harvard MBA — the only person they hired right out of undergrad. However, it wasn’t long before I realized that this ‘dream job’ was not for me. From private equity, I transitioned into venture capital because I thought it would allow me to work in tech, which it did. It was a more professional experience, but it was more of the same. I knew that the only way I could ever feel good about the money I made was by creating and building something of my own. That’s exactly what I did. Since then, I have been the founding inventor behind companies in technology sectors ranging from eCommerce to image recognition, and currently hold a total of 91 U.S. and foreign patents and applications. In 2008, I founded my first business, Double Picture, an advertising technology firm. I sold the company to MPA, Inc. in 2010. That same year, I founded AisleBuyer, best known for pioneering mobile self-checkout prior to its sale to Intuit in 2012. Then, along with my fellow AisleBuyer executive and friend, Casey Chafkin, I founded Skillz with the mission of bringing out the best in everyone through competition.

Can you share the most interesting story that happened to you since you started your career?

When we started Skillz, the idea was to enable players to compete in player-funded video-game competitions. Skillz would offer the digital equivalent of chess tournaments, road races, and golf competitions, all of which typically feature player entry fees and cash prizes. However, as a relatively new form of media, video games still carried a certain stigma, with people treating the term “gamer” as almost pejorative. As a result of these biases, we spent a tremendous amount of time honing both the legal aspects of the business and its branding. We wanted to ensure that the business was never considered gambling or looked at with anything less the admiration our society lauds upon athletes and competitors in traditional sports.

We spent years successfully advocating for the industry, partnering with major app stores, payment processors, venture capitalists and banks to ensure that Skillz was well understood and thought of as the “white knight” of the industry we had invented. We were so invested in this pursuit that we once had a Stanford Business School professor inquire about writing a case study on Skillz as a company built with a culture of compliance. In 2020, our efforts culminated with the company’s IPO on the New York Stock Exchange. The meticulous work we had put into defining the legal and ethical boundaries of the industry meant that people did not ask about the virtues or legitimacy of the space.

Ironically, our success paired with our culture of compliance paved the way for competitors to turbo-charge profits by defrauding consumers. Companies such as AviaGames had a simple scheme: build products that look like Skillz but rig the matches using bots so that the corporation can choose the outcome. No need to prevent cheating by players because if someone wants to cheat, companies like AviaGames can just deploy a bot that can cheat better. No need to match players fairly either because a bot can score any amount, in any game, at any time.

All our investments in compliance, fairness and self-regulation meant that companies such as AviaGames, and many others like them, avoided scrutiny from regulators, payment processors, and app stores. Today, AviaGames has received a grand jury subpoena from federal prosecutors, but they continue to scam American consumers out of millions of dollars per week.

As I reflect on this ongoing battle to keep our industry safe, I consider this perhaps the most expensive and painful lesson of my career: beware of unintended consequences.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

In college, I was profoundly impacted by reading “The Autobiography of Benjamin Franklin”, a narrative that reshaped my outlook on life. Benjamin Franklin arrived in Philadelphia penniless and made himself into one of the most successful entrepreneurs in the history of our country. His famous quote, “I am a strong believer in luck, and I find the harder I work, the more I have of it,” encapsulates my own belief in the power of diligence and perseverance. Inspired by Franklin’s ethos, I embarked on my entrepreneurial endeavors with a steadfast commitment to creating value in the world. His thirteen virtues served as a guiding light for me, eventually evolving into the seven core values of Skillz, the company I founded. These values — honor, balance, collaboration, productivity, willingness, frugality, and mission — have become not only the bedrock of my professional career but also the guiding principles shaping my personal life and leadership style.

Is there a particular book that made a significant impact on your leadership style? Can you share a story or an example of that?

“The Hard Thing About Hard Things” by Ben Horowitz is densely packed with direct and succinct advice on leading a business. As Horowitz acknowledges, there is no recipe or formula for success, but rarely do successful businesspeople write as candidly about their mistakes and challenges as Horowitz does. Since failures tend to be more instructive than successes, first-hand accounts of those failures are invaluable.

What do you think makes your company stand out? Can you share a story?

What makes Skillz unique is its identity as a competition platform, not just a gaming platform. Skillz operates on the belief that everyone is born with skills and deserves a shot at an epic win. It provides a space for game developers to turn their craft into thriving businesses and for players to turn their skills into real-world prizes. Leveling the playing field for all is how Skillz turned esports into something everyone can engage with and achieve more. At the foundation is the ideology of fairness, which is essential for competition to truly flourish. This commitment to fairness ensures that every player has an equal opportunity to succeed, making Skillz a standout in the gaming and competition industry. But defining a whole industry doesn’t come without challenges. Since our inception, Skillz faced immense setbacks that threatened its existence. For example, in 2013, when we had just closed our Series A funding, we found out that Google changed their terms of business, and we could no longer build on their platform. We lost half of our staff and all our customers as a result. We decided not to give up. We rebuilt the team, and customer base and relaunched the product on Apple. I believe that our spirit of winning, coupled with sheer resilience and belief in what we are building, enabled us to fight through and rise above.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

1. Gamer mindset: In many ways, business is like a video game, where navigating challenges and pursuing objectives mirrors a quest for success. Adopting a gamer mindset means your core mission is to win. But just like any game, you must acknowledge that you have multiple chances to overcome obstacles and achieve your goals. This perspective encourages resilience, as setbacks are opportunities for growth rather than insurmountable failures. Staying nimble, humble, and creative throughout the journey enables effective problem-solving, continual learning, and adaptation. Just as in gaming, the ability to pivot, innovate, and evolve ultimately leads to progress and success in the business world.
2. Values-Driven: While winning may be the goal in any game, true success in the game of business lies not in victory at any cost. Like any game, business requires adhering to a set of rules — in business, those rules are your values. As a leader, people buy into you. They are deeply invested in understanding the ‘why’ behind your actions and decisions, not just the ‘what’. This demands a deeper level of meaning and purpose behind your endeavors. Building a thriving business necessitates more than just a product or service; it requires passion, a guiding ethos, and a set of emotional values that infuse the very soul of what you’re offering.
3. Pain tolerance: In building a business, adversity is to be expected, both from the inertia of the status quo and the established business interests that do not want to be disrupted. In the face of this adversity, there is no substitute for simply working your ass off which tends to be easier said than done because hard work is often grueling and painful. I can share with you that I have slept on my desk numerous times throughout my career. As an entrepreneur, there is no way to avoid this pain, you simply grit your teeth and don’t quit.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?

We recently settled a lawsuit against a copycat of Skillz, largely run out of China called AviaGames. AviaGames shamelessly knocked off the Skillz product. Worse than copying our product, AviaGames’ business tricked consumers into thinking they were competing against other people in skill-based competition when really the matches were completely rigged. Players were competing against bots programmed to maximize AviaGames’ profits. Skillz sued AviaGames for patent infringement, copyright violations and fraud.

At a February 2024 trial, a jury convicted AviaGames of willful patent infringement, awarding Skillz $42.9 million. With another trial for fraud against AviaGames on the horizon, AviaGames agreed to pay Skillz $80 million to settle the lawsuits, leaving Skillz with a choice. On the one hand, $80 million is a lot of money for our shareholders and to continue our fight for fairness. On the other hand, taking the money meant settling with fraudsters who had no intention of changing their behavior.

We decided to accept the money for two main reasons. First, we recognized that the industry’s only hope for survival was systemic change. Even if we successfully stopped AviaGames’ fraud, other companies engaging in similar practices would quickly take their place. Second, we believed that the overwhelming evidence of fraud revealed during the trial would compel the government, app stores, and payment processors to prevent AviaGames from continuing to deceive American consumers.

We still question whether we made the right choice, because as of today, AviaGames’ apps continue to be heavily downloaded from app stores, cheating consumers out of their hard-earned money. However, we remain committed to fighting for the integrity of the industry we pioneered. Our guiding principles of fairness and honor drove us through this ordeal. As a company dedicated to winning, we prefer to succeed the right way.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a C-Suite executive does. But in just a few words can you explain what a C-Level executive does that is different from the responsibilities of other leaders?

C-Suite leaders bear ultimate responsibility for every aspect of a business. They never have the luxury of saying “that’s not my job,” and measure their success only through the success of the business they serve.

What are the “myths” that you would like to dispel about being a C-Suite executive? Can you explain what you mean?

When people imagine the C-Suite, I think they envision someone in an ivory tower, devising business strategy and not getting truly involved in the day-to-day operations. But the truth is that successful executives stay connected with all levels of the organization. They engage with employees, customers, and stakeholders to stay informed and make better decisions. I have found that there is no substitute for rolling up my sleeves. If you want to better understand your customers, go and talk to them. If you want to diagnose a problem or understand why something isn’t working, get your hands dirty and do the job that you’re trying to understand.

What are the most common leadership mistakes you have seen C-Suite leaders make when they start leading a new team? What can be done to avoid those errors?

Often new leaders feel that they have been hired with a mandate to make lots of changes very quickly. I think this impetus is born out of the desire to validate their hire and compensation. This approach can lead to resistance, mistrust, and disengagement as team members may feel undervalued and overlooked. Rapid, unilateral changes can also disrupt existing workflows and morale, often leading to unintended negative consequences. To avoid this pitfall, leaders should take the time to understand the current processes, listen to the team’s insights and concerns, and involve them in the decision-making process. This collaborative approach not only fosters a sense of ownership and commitment but also leverages the team’s collective knowledge and experience, resulting in more effective and sustainable changes.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

Clear, concise communication is often underestimated. While many people in both leadership and non-leadership positions would agree that communication is important, they underinvest in doing it well. It is easier to send an instant message than it is to send an email and even easier still to swing by someone’s desk and just talk. While informal communication in person or via instant messaging is great for ideation and rapid discussion, it has some major limitations: first, these kinds of communications are open to interpretation (particularly conversations). Second, these kinds of communications are impermanent. Spoken words are easily mis-remembered and instant messages are easily buried and poorly indexed for search. Finally, these communications are not well-suited to retransmission as the personnel in your organization inevitably changes.

From firsthand, painful experience, we now often say at Skillz “If it is not in writing, it did not happen.”

What are your “Five Things You Need To Be A Highly Effective C-Suite Executive”?

1. Define your values: Pursue purpose over titles, money, or power. Every action you take should be rooted in the impact you seek to make on the world. Articulating your personal mission and the values you uphold will provide you with a moral compass, guiding you toward sound decisions and empowering you to navigate the complexities of an ever-evolving landscape. This will also inspire others to follow you with unwavering commitment and loyalty.
2. Lead with optimism: In the dynamic landscape of business, challenges often arise unexpectedly, turning smooth paths into rugged terrain. Ascending to success isn’t a linear journey; it’s a winding road fraught with setbacks, unexpected turns, and moments of doubt. Amidst the trials and tribulations, maintaining an optimistic outlook is essential. When faced with repeated setbacks, it’s natural to feel disheartened, yet it’s precisely during these times that perspective and positivity become your most powerful tool. Belief in a brighter tomorrow has been my guiding light through even the toughest of circumstances.
3. Stay in the game: My journey has been marked by a simple yet powerful mantra: try, adapt, and never give up. If a plan didn’t pan out, I’d tweak it, try again, and keep pushing forward until I found a way. That’s the essence of effective leadership — tenacity in the face of challenges. It’s not about having all the answers from the start, but about the willingness to keep learning and evolving. We all can turn setbacks into steppingstones; it’s the resilience and determination to keep going that truly makes the difference.
4. Make sure you have the right players on the field — The highest executive position on a sports team is the General Manager because everyone intuitively understands that the quality of the players and coaches is what determines a team’s success. Strangely, people ignore this same truth in business. Whether your product is points, runs or wins as it is in sports or if its software and services as it is for Skillz, ultimately everything good and everything bad that your company will ever do is a product of the people that it hires and the systems by which it organizes them. This means that everything comes down to hiring well.
5. Never stop leveling up: No matter how far you get into your career, it’s critical to maintain a constant state of humility when it comes to business building because you’re always learning. Many of the things I got right when building my first two companies I got wrong when building my third, showing how easy it is to mistake luck for skill. No matter how much experience you have, keep a growth mindset. Surround yourself with trusted mentors and confidants who challenge and inspire you to continuously evolve and excel.

In your opinion, what are a few ways that executives can help to create a fantastic work culture? Can you share a story or an example?

Own the tradeoffs that make your company unique. Most situations are about pros and cons rather than one option that is strictly superior to another. This is absolutely true of corporate culture. To over index on certain things, you must be willing to trade others. For example, Skillz offers an immense opportunity for employees to have an impact on the world, through the size of industry we are creating and the ownership that we entrust to each hire that we make. However, the opportunity for that impact is not free. Doing impactful work is typically harder than work that does not really matter, and it is definitely more stressful because there are consequences to your every action or inaction. For proof of this point, consider why every American president looks so visibly aged after just four years in office.

Similarly, Skillz is a company that delivers exceptional opportunities for learning and personal growth. But again, the acquisition of knowledge is not free. Instead, it requires time, effort and a willingness to push yourself beyond your comfort zone to the point of failure. Consider, by analogy, the ways that you can learn a foreign language. You can immerse yourself in a country where you do not speak the language and learn incredibly quickly. However, in doing so, you will trade the comfort of being able to converse with those around you and the security of not embarrassing yourself by routinely misspeaking. Alternatively, you can use a language course app for an hour a night. This method will take years, but you will never feel uncomfortable or embarrassed.

At Skillz, we foster a culture rooted in performance and ownership where merit takes precedence over hierarchy. We empower each individual to embody an entrepreneurial spirit, treating their function as if it were their own independent business unit. While it’s not always the simplest path, cultivating these skills and mindset is crucial for driving meaningful change and making a tangible impact on the business.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Sports — whether in the digital world or the physical world — exist as a celebration of excellence. But sports cannot exist without the concept of fairness which forms the bedrock of competition. The need for fairness in the offline world is well understood and explains why major sports leagues invest so heavily in drug testing and the impartiality of their umpires, judges and referees. However, in the digital world, the rise of AI left unchecked by companies that prioritize short term profits over equal opportunity is imperiling not just an emerging industry, but the very American ideals of competition and achievement.

I hope that we can turn the Skillz fight for fairness into a bigger movement in gaming. Fairness levels the playing field, allowing skill and strategy to prevail over fraud and exploitation. We need a groundswell of help to make this a movement that will drive better legislation and policies putting an end to unethical practices by ‘bad actors’ who deceive players for their own gain. Otherwise, I believe the future of sports to be in real jeopardy.

Are you ready to join me?

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Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Douglas E. Noll, JD, MA was born nearly blind, crippled with club feet, partially deaf, and left-handed. He overcame all of these obstacles to become a successful civil trial lawyer. In 2000, he abandoned his law practice to become a peacemaker. His calling is to serve humanity, and he executes his calling at many levels. He is an award-winning author, teacher, and trainer. He is a highly experienced mediator. Doug’s work carries him from international work to helping people resolve deep interpersonal and ideological conflicts. Doug teaches his innovative de-escalation skill that calms any angry person in 90 seconds or less. With Laurel Kaufer, Doug founded Prison of Peace in 2009. The Prison of Peace project trains life and long terms incarcerated people to be powerful peacemakers and mediators. He has been deeply moved by inmates who have learned and applied deep, empathic listening skills, leadership skills, and problem-solving skills to reduce violence in their prison communities. Their dedication to learning, improving, and serving their communities motivates him to expand the principles of Prison of Peace so that every human wanting to learn the skills of peace may do so. Doug’s awards include California Lawyer Magazine Lawyer of the Year, Best Lawyers in America Lawyer of the Year, Purpose Prize Fellow, International Academy of Mediators Syd Leezak Award of Excellence, National Academy of Distinguished Neutrals Neutral of the Year. His four books have won a number of awards and commendations. Doug’s podcast, Listen With Leaders, is now accepting guests. Click on this link to learn more and apply.