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Ken Weiner—self-styled Chief Baking Officer of Fort Myers-based Chloe’s Cookies—is not a baker by trade. But he is an entrepreneur, and that has helped make his business one of the most recognizable cookie baking and delivery services in Southwest Florida.

Weiner has headed a number of businesses in his career and continues to run his own real estate, development and construction companies. Chloe’s is a passion project, one whose emotional upsides are as rewarding as the financial benefits. “When you deliver cookies, everyone’s smiling,” he says.

Weiner launched the company in 2019 with his wife, Sheryl. Today, Chloe’s offers 35 varieties of chocolate chip cookies; each batch is fresh-made to order. He keeps enough cookie dough for 400 cookies in his freezer at all times.

Though Weiner had brief stints early in his career when he worked for other people, he realized quickly that he was better suited for entrepreneurism. “I figured I could go work for somebody else or I could work for myself,” he says. He chose to work for himself, and it was the right decision. “I’ve always loved being in control of my destiny,” he says. “But it’s not always easy. If you don’t succeed, it’s your fault. The buck stops here, and if you don’t like that then you shouldn’t be doing this.”

His entrepreneurial journey has spanned more than four decades, and he’s learned some key lessons along the way.

Don’t underestimate a good hype man.

When Weiner first had the idea to bake and sell cookies, he reached out to friend and restaurateur Harold Balink, owner of Harold’s in Fort Myers. Weiner brought over a few cookies for Balink to try. “Is this a project worth doing?” he asked. “You could sell a thousand of these cookies a day,” Balink said. That was the fuel Weiner needed to launch Chloe’s.

Bank on emotional diversification.

Weiner is the first to admit that baking cookies wasn’t exactly in his professional wheelhouse. “It was so much different from what I’d been doing on a day-to-day basis for the last 45 years,” he says. “It’s not like I suddenly became an electrical contractor, which would have been different but still somewhat the same.”

Instead, he found that making cookies offered a different sort of emotional reward than he was used to. For one, the gratification was immediate. “That’s one of the reasons I love to cook,” he says. “People either like it or they hate it, and you get to find out right away.” With real estate and development, he said, it can take years before a project is complete.

Plus, making and delivering baked goods offers a great serotonin boost. “People are always happy to get cookies,” he says.

Don’t go all in.

When it comes to passion projects, Weiner admitted that it’s good to have another source of income. “Even though Chloe’s is a business and we run it like a business, if I had to shut it down tomorrow, we’d still have a roof over our heads,” he says. “I’d miss it, but I’m not depending on it.”

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