Les Winston, Director, President, Chairman, West Aventura – Aventura – Sunny Isles Beach Chamber of Commerce

Invest: spoke with Les Winston, director, president, and chairman of the West Aventura-Aventura-Sunny Isles Beach Chamber of Commerce, about supporting small businesses in a high-demand market while advancing a longer-term focus on charitable endowment and community self-sufficiency. “If communities build the habit and structure of private charitable support, it changes what’s possible over time,” Winston said.

What is the chamber’s mission, and how does it guide your priorities as president and chairman?

At its core, our purpose is to improve the commercial atmosphere and the lifestyle in our communities. We want a strong business environment, but we also want the community to feel healthy, safe, and sustainable for the people who live and work here.

A big part of our approach is encouraging the private sector to support community needs through endowment, rather than defaulting to government funding or taxes. There are needs that matter to quality of life, including medical needs and safety needs, and we believe communities can address more of them when they build long-term charitable resources.

We also spend a lot of time educating people on charitable planning that can benefit both the individual and the community. In our view, charitable giving is often discussed as giving something away entirely, but there are tools that allow someone to contribute in a way that provides tax advantages and supports retirement planning, while still building long-term resources for the community. We encourage people to think about contributing non-cash assets as part of legitimate planning and long-term community support.

We try to keep the idea of self-sufficiency in front of the public. People get used to viewing government as the source of support, and we’ve been trying to shift that mindset. If communities build the habit and structure of private charitable support, it changes what’s possible over time.

From my perspective, we’ve moved from a political era into an economic era, where the question is more about value and exchange. That principle is important to local businesses, and it also shapes how we think about community leadership and community support.

Small businesses make up a large portion of your membership. What are the top challenges they face today, and how is the chamber addressing them?

Exposure is one of the biggest needs. Small businesses depend on local awareness, and it’s harder than it used to be to be found in a complete, organized way. Years ago, you could open the Yellow Pages and see everyone in a category. Now, online searches don’t always show the full picture.

The chamber can function as a trusted local directory where people can research what they need and find local options. We also publish a local directory that we distribute through hotels and other businesses, listing our members. In a visitor-heavy area, that matters.

Our website is a major resource because people all over the world look up Aventura and Sunny Isles Beach. Those names generate interest, and we get significant traffic, so we treat the site as an active platform. We’ve also expanded it by offering licenses that help local businesses use AI and social media more readily, so smaller companies can access modern tools without a large team.

Affordability matters, too. We keep membership accessible with a fairly low basic fee, because many small businesses can’t justify expensive advertising. The chamber is a practical way to get visibility, information, and connection without needing a large spend.

Networking and community events are staples for chambers. How do you design events to foster meaningful connections between businesses, civic leaders, and residents?

We try to do meetings that have an impact. The goal is for members to leave with something useful: a connection, an idea, or more visibility.

Since COVID, in-person meetings have become tougher. People would often rather meet on a Zoom call, but the person-to-person side still matters. Getting to know somebody personally is important, and it’s hard to fully replace that through screens.

We do a monthly breakfast meeting where members come together, introduce themselves, and get to know each other. It works, but members have to work it. Sometimes you hear someone say they didn’t get anything from the chamber, and my question is whether they attended meetings, participated and networked. You have to put something into it to get something out of it.

How does the chamber work with local government, tourism groups, and other stakeholders to promote economic growth in the region?

Candidly, we don’t have the same challenge some places have, where the area needs to be sold or created. Aventura, Sunny Isles Beach, and West Aventura are attractive for business, and businesses flourish here. In many cases, it’s tough to find places to rent, which tells you how active the market is.

Our website traffic reflects that. People know these names, and when they search them, they find the chamber. In that sense, the market often markets itself through the visibility the area already has.

Miami is also a major draw, and we’ve seen strong growth as people relocate for lifestyle and tax reasons. It’s not cheap, but it’s valuable property in a high-demand market. Our role is to make sure local businesses can be seen and supported inside that momentum, not lost in it.

What strategies do you use to ensure members stay engaged and see real value from participating in the chamber?

Renewal is a clear indicator. If members renew, we know we’re providing value. If they don’t, we need to understand what didn’t work.

One major value we focus on is education. Small businesses often struggle with the operational side of running a company, and people form businesses without knowing what they really need to do. We provide resources that support financial literacy and practical business fundamentals, including an academy-style set of materials and links members can use at their own pace.

That includes insurance basics, formation, and the implications of choosing different structures. Many people don’t understand the difference between a partnership, sole proprietorship, LLC or corporation, or whether an S-corp or C-corp makes sense. We also help members think through legitimate tax planning, retirement planning and administrative basics, including how to navigate things at the local level. The goal is to help them operate more effectively and avoid preventable mistakes.

Looking ahead, what are your top strategic priorities for the chamber over the next few years?

The consumer is central to the local business environment. If consumers feel peaceful, comfortable and confident in their community, that supports local businesses. People participate when they trust the environment around them.

We stress a simple set of priorities: safe care, great care; safe streets, great streets; safe homes, great homes; and safe schools, great schools. Those themes are tied to what makes a community attractive and what helps the local economy stay strong.

Endowment remains a focal point of our long-term approach. We’re a 501(c)(6), so we work closely with 501(c)(3) organizations to do some of this work, but we believe building a large charitable endowment to support the community through local nonprofits can do more than almost anything else. Nonprofits need enough capital to run their organizations without relying on government support or constantly raising money.

Chambers of commerce should be the focal point of communities. They are the economic engines of the communities, not the government.