Six Counterconventional Entrepreneurial Mindsets That Can Change the World

In 1995, graphic design teacher and aspiring entrepreneur Lynda Weinman took a bold step. She purchased the domain Lynda.com — not because she foresaw a massive business opportunity, but because she needed a sandbox to explore the new digital tools emerging at the time, such as Photoshop and Illustrator. More importantly, she wanted a place where her students could showcase their work to the world.

This modest beginning grew rapidly. By 2002, Lynda recognized that her website could become much more than just a portfolio platform—she moved all her teaching online. Years later, her business was acquired by LinkedIn and transformed into LinkedIn Learning, selling for an astounding $1.5 billion.

Lynda Weinman exemplifies what I call the counterconventional mindsets of entrepreneurs—mindsets that break away from traditional corporate thinking. Today, I want to share six such mindsets that can empower you to innovate, grow, and perhaps even change the world.

1. Say “Yes, We Can”

Traditional business strategy often advises sticking to your core competencies. If something falls outside your expertise, the expected answer is usually a firm "No."

But Brazilian entrepreneur Arnold Correia defied that. He had a company specializing in event management but when a customer asked if he could broadcast training to 260 stores across Brazil using satellite technology—something he had no experience with—Arnold said, "Yes, we can." He delivered.

Later, Walmart asked him to place screens on sales floors for advertising. Again, he said yes, reinventing his business four times over. Entrepreneurs embrace possibility—even when it defies conventional wisdom.

2. Problem-First, Not Product-First

Big corporations often obsess over product lines and incremental changes (think “New Coke” or changing detergent speckles). Entrepreneurs focus on solving problems.

Jonathan Thorne developed a new alloy for surgical forceps because the old ones stuck to tissue, causing complications in surgeries. Instead of focusing narrowly on plastic surgeons, he explored other specialties with greater need, like neurosurgery, eventually building a successful business that sold to medical giant Stryker.

Innovation begins with a problem to solve, not a product to sell.

3. Think Narrow, Not Broad

Large companies chase big markets. Entrepreneurs often start with a narrow, well-defined niche.

Nike’s founders, Phil Knight and Bill Bowerman, began by solving a specific problem for elite distance runners who needed better shoes for rough terrain—not sprinters on tracks. By focusing on this niche with tailored innovation, Nike became a global powerhouse.

Narrow focus can be a powerful advantage.

4. Ask for Cash Upfront, and Ride the Float

Big corporations often have plenty of cash, but entrepreneurs understand the critical importance of upfront funding.

Tesla, under Elon Musk’s leadership, sold 100 Roadsters at $100,000 each before building a single car—earning $10 million in cash to fund production. Later, they collected nearly half a billion dollars in deposits for the Model 3 before manufacturing started.

This “ask first, build later” approach keeps entrepreneurs nimble and solvent.

5. Beg, Borrow, But Don’t Steal

Entrepreneurs often creatively leverage resources without owning everything.

Tristram and Rebecca Mayhew built Go Ape, a treetop adventure business in the UK, by partnering with the Forestry Commission. They used existing trees, facilities, and parking lots, adding only their course infrastructure.

Entrepreneurs find ways to use what’s available and build partnerships rather than insisting on full ownership.

6. Don’t Ask Permission, Just Get On With It

Big companies are bogged down by regulations and approvals. Entrepreneurs often bypass permission to innovate.

Uber’s founders, Travis Kalanick and Garrett Camp, launched a taxi service without taxis, operating despite regulatory hurdles. While their path had ethical controversies, their approach illustrates the entrepreneurial mindset of action over permission.

Final Thoughts

Entrepreneurship isn’t about following business school playbooks. It’s about mindset—habits, attitudes, and ways of thinking that shape how you respond to opportunities.

Ask yourself:

Which of these mindsets do you already embody?

Which can you learn and cultivate?

Can you teach them to colleagues or collaborators?

Is there a current challenge where one or more of these mindsets can help you break through?

Lynda Weinman’s journey—from a teacher needing a digital sandbox to a $1.5 billion business sale—is a testament to the power of counterconventional thinking. The six mindsets above could be your guide to changing the world next.