The pickleball industry is booming — but despite the rapid growth, securing the right real estate remains one of the most difficult challenges for new and expanding operators. What looks like a simple sport to house is anything but. Ceiling heights, column spacing, zoning, parking ratios, competitive timing and lease complexity can make or break a location long before the doors ever open.
At the 2025 Pickleball Innovators Summit, Will Richards, the CEO and co-founder of Dill Dinkers, shared deep insight into the realities of modern pickleball site selection. Having evaluated hundreds of properties and opened a growing portfolio of clubs, his experience provides a clear roadmap for operators trying to navigate today’s market.
Here’s a look at the biggest challenges — and the most effective strategies to overcome them.
1. Prepare for Delays, Because They’re Inevitable
One of the biggest lessons from Dill Dinkers’ journey is that site selection rarely follows a linear timeline. Early locations may come together quickly, but as operators expand into new jurisdictions — often with less pickleball awareness — the process slows dramatically.
Permitting requirements, zoning questions, fire code reviews and traffic studies can stretch timelines into year-long processes. Richards shared that some of their later locations took 12–15 months to open, even with a strong operational track record.
How to overcome it:
- Build extended timelines into your expansion strategy.
- Start scouting multiple sites simultaneously.
- Expect speed bumps, and don’t pause your pipeline when you think a deal is “certain.”
2. Choose Local Brokers — and Avoid Exclusivity
A consistent challenge throughout Dill Dinkers’ growth has been working with brokers unfamiliar with the niche requirements of pickleball facilities. Industrial column spacing, court layouts, ceiling heights, ingress/egress and acoustic concerns make many seemingly “great” sites unusable.
Richards emphasized that national brokers often fail to understand these nuances, sending operators to properties that will never work. One regional developer found that their broker simply gave up, convinced that the client’s requirements “didn’t exist.” Yet within a week of ending that agreement, they found a viable space on their own.
How to overcome it:
- Rely on local brokers with deep neighborhood knowledge.
- Work with multiple brokers rather than signing exclusivity agreements.
- Educate brokers on your core requirements upfront (court dimensions, spacing, noise mitigation, etc.).
3. Don’t Get Fooled by Big-Box Closures
As major retailers close — including national chains — many operators assume these large-footprint spaces are turnkey options for pickleball. Richards cautioned that this is often a trap.
Big-box spaces come with:
- High rents
- Restrictive covenants
- Anchor tenant approval rights
- Neighboring tenants with veto power
In one case, an attractive big-box option stalled for nearly a year due to outside approval requirements — and ultimately no longer made financial sense by the time a response was received.
How to overcome it:
- Conduct a covenant and lease restriction review early in the process.
- Don’t assume that a large retail space equates to a good pickleball space.
- Consider that industrial flex space may provide superior column spacing and layout flexibility.
4. Right-Size Your Facility (Bigger Is Not Better)
It’s tempting to pursue large facilities with 12–15 courts, but Dill Dinkers learned that bigger footprints don’t automatically translate to profitability. Richards noted that some of their early big-box targets would no longer fit their model today.
The lesson? Right-sizing is essential. The market has matured quickly, and the economics that made huge facilities appealing in 2022 or 2023 don’t necessarily hold true in 2025.
How to overcome it:
- Focus on profit per court, not total square footage.
- Prioritize operational efficiency over total capacity.
- Avoid oversized leases that require “perfect-case scenario” utilization to justify rent.
5. Be Strategic About Market Timing
Opening at the wrong time can undermine even the strongest facility. Richards shared the example of launching two new locations during peak outdoor season, which resulted in low early traffic and prolonged financial lag. What looks like a strong market on paper can behave very differently depending on weather, competition and seasonality.
How to overcome it:
- Avoid opening during summer in regions where outdoor play dominates.
- Stagger openings in multi-location markets so they don’t cannibalize one another.
- Model seasonal dips into your cashflow planning.
6. Use a Rigorous, Multi-Step Evaluation Process
One of the strengths of the Dill Dinkers model is its structured approach to evaluating real estate opportunities. Richards outlined a process that includes architectural feasibility, demographic analysis, pricing model projections and line-by-line legal review by experts who understand the nuances of commercial sports facilities.
This process ensures that no franchisee signs a lease the corporate team doesn’t believe can succeed.
How to overcome it:
- Build a standardized site evaluation framework for every potential property.
- Evaluate factors such as demographics, projected utilization and revenue potential before negotiating.
- Engage a commercial leasing specialist who has negotiated dozens, if not hundreds, of retail or industrial leases.
7. Walk Away From “Hail Mary” Deals
Nearly every operator encounters a space that looks perfect — until you see the rent. Richards advised against thinking you can “tweak the pro forma” to make it work. If a location only works when everything goes exactly right, it’s not the right location.
How to overcome it:
- Stick to your financial model’s guardrails.
- Avoid deals that require optimistic assumptions to break even.
- Remember: the rent is the No. 1 factor that determines a facility’s long-term health.
Real estate isn’t just one part of the pickleball business — it’s the foundation. And as operators learned firsthand during the Summit, the process is far more complex than many expect.
But with realistic timelines, disciplined evaluation, local market expertise and a willingness to walk away, operators can dramatically improve their chances of selecting locations that thrive.
The 2026 Pickleball Innovators Summit will take place October 12–14, 2026, at The Westin La Paloma Resort & Spa in Tucson, Arizona. To reserve your spot at the 2026 Pickleball Innovators Summit as an attendee or sponsor, email rachel@peakemedia.com or visit peakemediaevents.com/pbisummit to learn more.
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With over a decade spent covering the business side of sports and fitness, Rachel Chonko brings a wealth of experience and a true passion for active communities to Peake Media. As Editor-in-Chief, she’s focused on helping pickleball clubs and fitness facilities thrive, from guiding growth strategies to showcasing the latest industry trends. Rachel also hosts the Club Solutions Magazine Podcast, where she interviews leaders in fitness and pickleball to share insights and success stories with the wider community to give her listeners a competitive edge.
After taking up pickleball herself, Rachel has come to appreciate the sport’s unique blend of social connection and active living — a mix that’s perfectly in line with her editorial philosophy. Connect with her on LinkedIn, or check out her articles below for a deep dive into the energy and culture driving pickleball’s rapid rise.
