Get Started

Sandeep Rajan is the Founder and CEO of Grandstand, a pioneering platform akin to Patreon for athletes, designed to forge direct connections with fans. With a history that spans from aspirations of being the next Tiger Woods to making his mark in the tech world, he led product teams at notable companies such as Patreon and Dropbox. Before founding Grandstand, Sandeep was at the helm of Wiser, a startup at the crossroads of machine learning and news aggregation. His passion for both sports and technological innovation has positioned him as a key influencer shaping the future of athlete-fan engagement.

apple podcast
amazon music

Here’s a glimpse of what you’ll learn:

  • [1:55] Sandeep Rajan discusses his journey as a cricket and golfing fan and leading the frontier of fan experience enhancement
  • [8:07] How the Grandstand platform works and the unique value it brings to athletes and fans alike
  • [13:51] Sandeep reflects on valuable lessons from Patreon influencing Grandstand’s trajectory
  • [17:26] Tackling leadership challenges in the startup world and the shift from an established company
  • [23:02] Building a strong, empowered team within a startup by finding talent that surpasses your own skills
  • [30:23] Why establishing clear, measurable goals can dramatically influence startup success rates
  • [41:00] Anticipating the launch of Grandstand’s v3 and setting ambitious goals for athlete and fan engagement

In this episode…

The relationship between athletes and their fans has evolved dramatically in the digital age. How can athletes foster deeper connections and create meaningful engagement beyond the field?

According to Sandeep Rajan, a visionary in sports tech, the key to enhancing athlete-fan engagement lies in leveraging technology to create authentic and interactive experiences. He highlights the limitations of traditional media and social platforms, which often fail to capture the full spectrum of an athlete’s journey. By offering exclusive content and creating community spaces, athletes can share their stories more intimately, providing fans with unprecedented access and involvement. This approach not only strengthens fan loyalty, but also opens new revenue streams for athletes.

In this episode of WRK & WIN, host Corinne Milien sits down with Sandeep Rajan, Founder and CEO of Grandstand, to discuss the future of athlete-fan engagement. They explore how Grandstand is transforming the way athletes connect with their audiences, the importance of building a strong team, and the role of innovative features like interactive live events. Tune in to discover how technology is driving athletic engagement beyond the field and reshaping the sports industry.

Resources Mentioned in this episode

Special Mentions:

Related Episodes:

Quotable Moments:

  • “We’re tapping into a lot of content about the athlete, whenever they compete, to create this site-finished video and editorial content.”
  • “We make it really simple for an athlete to have a dedicated space — extending what Instagram and content products leave off.”
  • “I really think about it as elevation. What can you do better than me?”
  • “Identifying failure as early as possible is actually liberating and most correlated with success.”

Action Steps:

  1. Start with simple goal-setting: Establish where you want to be weekly and track progress. This method fosters a habit of constant reevaluation and adjustment, which is essential in a rapidly changing startup environment.
  2. Delegate tasks to people who perform better than you in specific areas. Doing so can elevate the quality of work and free you up to focus on strategic direction and growth.
  3. Create and nurture a company culture that emphasizes rapid learning and iteration. Fast-paced learning helps identify what works and what doesn’t, pivoting efficiently towards success.
  4. Engage in direct market research to understand the pain points of your targeted users. Direct insights ensure the product or service meets actual needs, increasing the likelihood of market fit and adoption.
  5. Build intellectual honesty within your team, emphasizing the value of acknowledging shortcomings to pivot effectively. This attitude helps teams stay grounded and agile, preventing wasted effort on ineffective strategies.

Sponsor for this episode…

This episode is brought to you by WRK.

Managing a successful business is about more than just the bottom line — it’s about the people who make it happen.

WRK is your go-to partner for people-powered HR and staffing solutions, designed to overcome your toughest workforce challenges.

From fostering employee engagement through positive employee relations to developing future leaders with their Leadership Development programs, WRK‘s services are designed to maximize the performance of your team and ensure a vibrant, inclusive work culture.

This isn’t just HR — it’s HR reimagined.

Go to to learn more.