Avoid costly business mistakes by applying practical thinking strategies to improve decision-making, cash flow, and profitability.
Most teams grind for growth, but the best ones systemise it. In this step, you’ll see why a structured approach always beats random tactics. You’ll follow Random Rick, Specialist Steve, and Solid Sarah to understand how a system-driven growth approach can double revenue without doubling workload.
"The Road Less Stupid" is a practical guide for business leaders and entrepreneurs seeking to minimise mistakes and optimise decision-making. Keith J. Cunningham, a successful businessman and mentor, emphasises the importance of avoiding the "dumb tax"—avoidable financial and business mistakes caused by impulsive, poorly thought-out decisions. Through structured thinking time, actionable insights, and a disciplined approach to leadership, the book offers a framework to enhance clarity, improve business outcomes, and create sustainable success.
Cunningham introduces the idea of the "dumb tax," which refers to the cost of poor decisions made due to a lack of thoughtful analysis. He argues that avoiding mistakes is often more valuable than pursuing additional opportunities. Success, according to Cunningham, comes not from doing more smart things but from doing fewer stupid things. By identifying and mitigating risks through deliberate thinking, leaders can preserve wealth, reputation, and growth potential.
Cunningham advocates for "thinking time," a structured practice designed to improve clarity and decision-making. This involves dedicating uninterrupted time to deeply consider business challenges, opportunities, and strategies. The foundation of this process lies in asking better questions. Cunningham provides examples of high-quality questions that uncover root problems, challenge assumptions, and stimulate innovative solutions. He encourages leaders to adopt a disciplined, unemotional approach to thinking, which allows for rational analysis over reactive decision-making.
Cunningham outlines five key disciplines to guide thinking time:
By mastering these disciplines, leaders can improve their ability to diagnose challenges, craft solutions, and achieve sustainable results.
Cunningham explains the four roles every leader must play to build a successful business:
Balancing these roles allows leaders to shift their perspective and approach challenges with a well-rounded mindset.
Culture plays a central role in business success, according to Cunningham. He argues that culture is not about perks or superficial benefits but about accountability, trust, and high standards. Leaders are encouraged to establish clear expectations, address mediocrity, and foster a results-driven environment. By creating a culture where excellence is the norm, businesses can achieve extraordinary outcomes.
Cunningham identifies several common pitfalls that entrepreneurs face, including:
He offers practical strategies to overcome these challenges, such as implementing clear dashboards, leveraging expertise, and focusing on fundamentals.
Execution is highlighted as a critical component of success. Cunningham stresses the importance of creating systems that enable consistent performance and scalability. By measuring results, identifying inefficiencies, and refining processes, leaders can drive progress while minimising waste. The "machine" of a business should be designed to operate independently of the owner, allowing for sustainable growth and flexibility.
"The Road Less Stupid" is a pragmatic guide for leaders who want to achieve success by avoiding avoidable mistakes. Cunningham’s insights are grounded in real-world experience, making this a valuable resource for entrepreneurs, executives, and anyone looking to improve their decision-making.
If your marketing and sales teams are too busy firefighting — fixing tools, chasing data, and dealing with messy handovers — you’ll never have time to focus on real growth. The Growth Operations Programme fixes your operations first, so you can finally work on scaling up.
Solid Growth helps B2B service companies scale — not with random tactics, but with clear systems that align marketing and sales into one predictable growth engine. Built on 13 years of hands-on experience — helping teams move from firefighting to predictable, repeatable revenue growth.
15 years experience
1,500 marketers trained since 2015
Exited 6 companies
My name is Ewoud Uphof, a marketing strategist with 15 years of experience. I've been fascinated by growth since 2010, and I created this guide out of a passion for sharing what I've learned. These guides are a way for me to give back to the marketing community and are also linked to my video course, which covers these topics in even greater depth.
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Find and fix what’s slowing your team down. This free scan assesses your marketing, sales, and automation setup, giving you clear recommendations to improve efficiency and eliminate bottlenecks.
Free up a full day every week to focus on growth. We'll fix the systems, tools, and workflows holding your team back.
Master the Solid Growth System at your own pace — perfect for individual marketers and consultants who want to upgrade their skills and apply the system themselves.
Find and fix what’s slowing your team down. This free scan assesses your marketing, sales, and automation setup, giving you clear recommendations to improve efficiency and eliminate bottlenecks.
Growth isn’t random—it’s engineered. A done-with-you programme that turns growth into a structured, repeatable process—so your team can execute with confidence and revenue compounds over time.
Avoid costly business mistakes by applying practical thinking strategies to improve decision-making, cash flow, and profitability.
Find and fix what’s slowing your team down. This free scan assesses your marketing, sales, and automation setup, giving you clear recommendations to improve efficiency and eliminate bottlenecks.
Free up a full day every week to focus on growth. We'll fix the systems, tools, and workflows holding your team back.