Jeff Wiener Profile Story: Entrepreneurial Success Post-retirement

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Jeff Wiener Flippa entrepreneur
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After running a successful telecom company for 27 years, Jeff Wiener sold his company to private equity and stepped down as president in 2017.  

His day-to-day responsibilities of managing a team of over 60 employees left him feeling exhausted. By the time he retired, travel had halted due to the pandemic.

Jeff and his wife found themselves hunkered down in an empty nest in Canada, their kids away in school. Boredom quickly set and Jeff knew it was time for something new.

For the past few years, the successful entrepreneur had spent his time doing consulting work. He knew he wanted to steer clear from this former path and embark on a new adventure.

“I wanted something that wasn’t going to be nearly consuming as the business that I ran for 27 years,” Jeff says. “ I didn’t want to get back to my [telecom] business. My intention was to get back to semi-retirement once the border was up and running again and I could travel and live life again.”

When it comes to entrepreneurship and growing a business, Jeff is no stranger to the craft.

As a successful entrepreneur and businessman himself, he has written and sold a book about entrepreneurship and runs a successful blog teaching entrepreneurs how to become successful in their careers.

It only made sense that he would use this expertise in the next chapter of his life.

Discovering Flippa

Jeff knew he wanted to pursue something passive in nature. After searching online, he came across Flippa and purchased his first website. Quickly, he grew his portfolio of websites to 11 assets and hired additional support.

“I like the way Flippa works. They’re pretty transparent. Right at the face of the site with all the information you need and you can make a decision whether it’s a go or no go,” he says. 

When it comes to first-timers looking to purchase a site on Flippa, Jeff has some advice:

“Understand the intimacy of the business at a deep level. Pick an industry and understand it really well. Understand what makes it tick and put a team behind you as quickly as you can to scale the operations. That is easier said than done for many entrepreneurs — the whole idea of leadership, management, and scaling and building a business.”

An acute business strategy and ROI

Jeff has purchased content sites geared toward entrepreneurs and technology, to more niche websites like a yorkie content site and a bike blog.

This conglomerate of sites may seem random, but for the entrepreneur, having an understanding of business has led to this success.

“The ideal strategy that I’m concerned [about] is not to be too dependent on any one source of traffic so that if something were to happen to traffic from that source, I wouldn’t want to see my revenue completely dry up,” Jeff says. 

When it comes to making a site profitable, Jeff sees the potential to quadruple an asset in revenue.

For example, the first business he purchased on Flippa was generating $3,200 a month, purchased for $72,000, and now brings in $10,000 monthly. Another techblog site that was purchased for $10,000 with a monthly revenue of $150 now makes $4,500 a month.

“We bring in traffic from social media, email lists, and through Google — we monetize across probably 12-15 different channels,” says Jeff. “So the revenue is distributed and the traffic is distributed. Frankly, that’s the ideal scenario.”

At the time of this interview, Jeff hadn’t written a blog in over a year. He hires writers who have expertise in each blog niche and has additional support in other areas of his business.

An employee-led organization

Unlike previous endeavors, running his current business is employee-led with teams across the country in the U.S., England, Philippines, and India.

Currently, there are team members who are in charge of social media, SEO, content, monetization, traffic, and security. Jeff’s involvement with the business is limited to about 7 hours a week, an intentional choice that allows him to attend to other aspects of his personal life.

“I’m able to run a small team and reap the rewards of this asset class without having to feel like I’m actively involved in a business that’s consuming me like it was in my last business,” Jeff says.

For the entrepreneur, an open, transparent working culture is a top priority. Ensuring basic necessities like healthcare coverage for his employees is essential, as some staff members in the Philippines came from unfair labor rates and restricted employee benefits. 

“I was always cautious and conscientious of being an amazing employer but always aware of having to be at the top of my game to make our business a great place to work,” Jeff says. “It was a case of me asking, ‘what can I do for you?’”

By incorporating the same leadership and guidance principles to his current business as he did in the past, Jeff is finding that managing a team this time around is much more rewarding.

“I value my time more than anything,” says the successful business owner. “I’m fulfilled because I have my time and I can do what I want how I want.”

 For Jeff, this fulfillment goes beyond just running a business. The rewards have been fruitful. 

If you’d like to learn how you can expand your online portfolio, visit Jeff’s website at

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