The Contrarian: From 0 to 20 MILLION Users

Michael Houck

James Evans' Contrarian Approach to Startup Success

James Evans challenges the conventional startup wisdom of 'don't do things that don't scale.'

His startup, Command AI, achieved 20 million users in four years by modernizing an existing industry.

He advises founders to spend less time planning and more time working on their product.

He discusses the importance of being okay with looking dumb and learning through experimentation.

His parents being business school professors exposed him to entrepreneurship from a young age.

He initially aimed for a meaningful startup idea, delaying his entrepreneurial pursuits.

He later realized that starting something, anything, is crucial to finding a successful path.

A previous startup's closure freed him to fully focus on building his own venture.

CodePost, an EdTech project, taught him the pitfalls of over-featuring a product.

The failure of a previous venture led to the formation of Command Bar.

They transitioned from EdTech to Command Bar by focusing on a search bar feature.

They applied to Y Combinator with the Command Bar idea.

The Overrated Nature of Creating New Categories

He disagrees with the notion that competition is for losers, advocating for iterative improvement.

He emphasizes reaching 'base camp' (early product-market fit) before focusing on disruption.

He suggests improving existing products before attempting to create entirely new categories.

He encourages founders to target large industries instead of solely focusing on novelty.

Identifying and Disrupting Existing Markets

He points out that many software markets have weak incumbents ripe for disruption.

The challenge isn't identifying the market but knowing how to effectively disrupt it.

He contrasts the 'build it and they will come' approach with a more sales-focused disruption strategy.

Markets with indifferent customers are easier to attack than those with universally hated leaders.

Rethinking "Don't Do Things That Don't Scale"

He refines the advice to 'do things that might not scale,' emphasizing iterative improvement.

He suggests delaying scalability concerns until achieving product-market fit.

He advocates for continuing non-scalable activities until they become truly painful.

He prioritizes strong customer relationships, even if it means sacrificing initial efficiency.

He stresses the importance of open-ended questions to extract information and understand perspectives.

He suggests variations of 'How's it going?' for team, customer, and investor interactions.

He recommends questions that elicit emotional responses to foster genuine conversation.

He contrasts extracting information with influencing, preferring the former for authenticity.