Pay Attention to What Rieva Lesonsky Knows About Entrepreneurship

You hear a lot of opinions about starting a business. Some people tell you to be bold. Others tell you to wait for the right moment.

In the latest episode of The Unsure Entrepreneur Podcast, Rieva Lesonsky cuts through the noise with practical advice based on decades of her work in small business journalism.

Rieva spent twenty-five years as SVP/Editorial Director at Entrepreneur Magazine, one of the most respected publications in this field. She's a best-selling author of several business books, including Small Business Hacks: 100 Shortcuts to Success. Unsurprisingly, she's received recognition from the US Small Business Administration, SCORE Business Mentors, and was inducted into the Business Journalists Hall of Fame.

Today, Rieva runs SmallBusinessCurrents.com and reports on emerging behaviours and shifts that affect how you start and grow a business.

She has seen every cycle, every trend, and every mistake entrepreneurs tend to make — and our interview was a golden opportunity to hear her unique perspectives on entrepreneurship and starting-up.

Fear is a research tool

One idea from the conversation lands with particular force. Rieva believes fear is not the enemy of entrepreneurship and is one of its most useful signals. As she put it on the podcast, “Fear tells you what to look at. Fear is not there to stop you. Fear is there to say, is this right?”

You may see fear as a sign to stop. But Rieva reframes fear as a signal to research. She sees it as a prompt to learn, test, and improve your plan.

For example, an aspiring entrepreneur who is afraid of losing their savings in a new venture can mitigate that fear by carefully doing more market research to make damn sure customers will actually buy what they intend to sell.

Leverage business trends & opportunities

Want the scoop on hot business trends so you can catch the wave? These data points stood out from the podcast.

For starters, Rieva talks about how big events can pump millions into local economies. For example, Taylor Swift’s tour generated more than $220 million in revenue for Los Angeles during five days of shows. That spending spills into restaurants, hotels, transportation, and retailers. Entrepreneurs who watch these patterns can position themselves ahead of demand.

Beauty remains a strong market. Rieva says that beauty brands often aim to be acquired by major companies after proving traction. She tells the story of an entrepreneur who created one product to help manage rosacea. The business grew quickly and sold for more than a billion dollars. And she doesn't stop there, pointing to rapid growth in male skincare and grooming.

Social media trends are especially relevant to new entrepreneurs. Rieva speaks about Pinterest returning as a reliable driver of product sales because the platform avoids political noise and focuses on buying behaviour.

She also shares long-term opportunities in home improvement, driven by rising housing costs and the desire to age in place. “People remodel their homes, so you need contractors. Then they need furniture and decor,” she says. One project creates demand for many others.

AI is a helper, not a replacement

Rieva offers an important caution on technology. Entrepreneurs hear a lot about AI. Some embrace it without thinking. Some ignore it completely.

She takes a balanced view. “You can let AI create something for you, but you must edit it,” she says. She encourages entrepreneurs to read their content out loud to make sure it sounds human. AI can save you time, generate ideas, and accelerate work, but credibility still depends on judgment, editing, and presence. Technology should support entrepreneurs, not replace their thinking.

We also talk together about the impact of technology on entrepreneur education. As a former magazine editor and lifelong small business journalist, Rieva has seen firsthand how entrepreneurship education has changed. Founders no longer sit down with magazines. They search for answers in the moment. As Rieva puts it, “You have a question. You go online. You get what you want to know.”

That shift matters. Tools, markets, and expectations now change at speed, with AI accelerating the pace even further. Rieva argues that understanding how people consume information is now a competitive advantage, because it shapes how you educate, market, and connect. Learn how people search, she says, and you learn where growth begins.

New entrepreneurs have some grey hair

She also challenges common myths about who starts businesses today. Many people assume startups belong to twenty-year-olds but that isn’t the case.

"People look at the Mark Zuckerbergs of the world or Michael Dell and think, oh, all these tech bros are dropping out of college and starting businesses. But when you look at the typical age of a startup, they're in their mid 40s to mid 50s," she says.

Forbes agrees with her, publishing about the mean age of startup founder in the U.S. now being 42 years old. These are people with experience and savings who want control over their work and income, she explains. If you’re in that age range, you’re not late — you’re right on time.

To hear the full conversation and enjoy Rieva’s thinking in her own words check out this special episode of The Unsure Entrepreneur Podcast.

[Photo: Rieva Lesonsky]