The Existing Market Trap: (a Primer) Escaping The 13 Deadly Sins that Destroy Companies, Careers and Portfolios

The Existing Market Trap: A Prequel to Play Bigger

Most companies don’t fail because they build bad products.

They fail because they don’t build belief.

They build something new—and the market compares it to something old.

They follow the classic playbook—and end up playing a game they didn’t design.

They’re misunderstood, miscategorized, and eventually… they stall.

This is the Existing Market Trap—the invisible force that kills companies, careers, and portfolios.

In this sharp, founder-first Primer, the authors of Play Bigger return with the missing chapters—the prequel to the Category Design movement. They name the problem, map the 13 Deadly Sins that cause great companies to get stuck, and reveal the escape route: a bold, proven system for building belief in new markets—and becoming the only.

Markets are people. Categories are beliefs.

A market is just a group of people who share a problem.

A category is what they believe can solve it.

It’s not about products. It’s not about features. It’s about belief.

Belief that the problem matters.

Belief that your solution is the answer.

Belief that you are the only one who can deliver it.

Legendary companies don’t fight for shelf space. They build the aisle.

They don’t out-feature the competition. They redefine the game.

They don’t chase demand. They create it.

And belief is the most powerful thing you can ship.

Inside, you’ll learn:

• Why the Existing Market Trap is so dangerous—and so hard to see
• The 13 Deadly Sins that sabotage companies at every stage of growth
• The Market Creation & Category Design playbook: how to frame the problem, claim the category, and launch with force
• How companies like Qualtrics, DocuSign, and ClearMetal broke free—and what changed when they did
• What this shift means for your company, your career, and your cap table

Whether you’re a Founder, CEO, Executive, Investor, or Board Member—if you’ve ever felt stuck, sidelined, or like the market just doesn’t get it…

This is your book.

And this is your way out.

Al Ramadan is the co-author of Play Bigger and a founding partner at Play Bigger, LLC. With a background in mathematics and early programming, Al began his career as a Fortran developer before rising to executive roles in technology. He led Quokka Sports through its IPO during the early digital media wave and played a key leadership role at Macromedia through its acquisition by Adobe. Today, Al works with business leaders on category design and market strategy. Outside of work, he's an avid surfer and passionate about helping teams reach their full potential.

Christopher Lochhead is a co-author of Play Bigger, Snow Leopard, and other books on business strategy and category design. He is the host of the podcast Follow Your Different and has served as Chief Marketing Officer for three public tech companies. Christopher is also a founding partner of Category Pirates and Play Bigger Advisors, where he works with entrepreneurs and executives on category design and go-to-market strategy.

Jason Wellcome is a partner at Play Bigger, LLC, where he works with founders, CEOs, and enterprise leaders on category design and market strategy. He is a longtime strategist and former agency executive, with experience helping define go-to-market positioning for both high-growth startups and global technology companies.

Mary Grice is Partner and Chief Operating Officer at Play Bigger, LLC. A Silicon Valley native, she has worked alongside founders, CEOs, and investors to help companies design and lead new market categories. She plays a central role in client engagements and company operations. Outside of work, she helps run a small urban orchard with her sister.