100 Books Like Obviously Awesome

I’ve spent my entire life dealing with mental health issues, and overcoming them took me on a long journey of learning about the mind and how to make it work for us rather than against us. I’ve explored almost every modality out there and developed my own hypnosis modality as a result. Books like these were a key part of helping me figure out how to overcome my challenges and live life to the fullest, achieve my goals, and reach success.

I’ve spent my career building products, scaling companies, and leading teams through the highs and lows of entrepreneurship. I know firsthand how challenging it is to take an idea and turn it into something real—whether that’s a product, a company, or a movement. The books on this list have shaped my approach to leadership, innovation, and resilience. They’ve helped me navigate tough decisions, build stronger teams, and think bigger. I’m passionate about sharing these insights because I believe great builders aren’t just born—they’re made. If you’re looking to create something meaningful, these books will push you, challenge you, and inspire you to build something great.

I’m a 3-time B2B startup founder (Flagback, HireVoice, and Highlights). For my 2nd startup, HireVoice, we tried to use The Lean Startup methodology and struggled to get traction on the market. When we shut down the company, I knew I wanted to solve my own pain, and learn B2B. I spent the next 2 years speaking (and learning from) some of the most successful B2B founders in the world. This, eventually led to the publication of my book, Lean B2B. Since then, I’ve been at the forefront of B2B entrepreneurship. The Lean B2B methodology has now been used by thousands of entrepreneurs and innovators to help create successful businesses.

I’m a 3-time B2B startup founder (Flagback, HireVoice, and Highlights). For my 2nd startup, HireVoice, we tried to use The Lean Startup methodology and struggled to get traction on the market. When we shut down the company, I knew I wanted to solve my own pain, and learn B2B. I spent the next 2 years speaking (and learning from) some of the most successful B2B founders in the world. This, eventually led to the publication of my book, Lean B2B. Since then, I’ve been at the forefront of B2B entrepreneurship. The Lean B2B methodology has now been used by thousands of entrepreneurs and innovators to help create successful businesses.

I’m a 3-time B2B startup founder (Flagback, HireVoice, and Highlights). For my 2nd startup, HireVoice, we tried to use The Lean Startup methodology and struggled to get traction on the market. When we shut down the company, I knew I wanted to solve my own pain, and learn B2B. I spent the next 2 years speaking (and learning from) some of the most successful B2B founders in the world. This, eventually led to the publication of my book, Lean B2B. Since then, I’ve been at the forefront of B2B entrepreneurship. The Lean B2B methodology has now been used by thousands of entrepreneurs and innovators to help create successful businesses.

Ever since I was a kid, I’ve always been intrigued by how people make decisions and why the words we use can significantly impact those decisions. After years of conducting customer research and writing marketing messages for clients, my interest in finding and delivering compelling messages at just the right time to the right audience has only grown. I’ve poured my experience in the online marketing trenches into my book, Finding the Right Message, where I reference more than one of the authors on my recommendation list. 

Not many people know that I was so timid as a child; I used to burst into tears if I had to ask for something in a store. Now, I am known for my “out there” presentation style and mastery of words. Since 1982, I have been working with individuals and groups to help them get better at persuading, solving conflicts, and having inspiring relationships. So, how can you be a nice, caring person and still be persuasive, even with the most skeptical of people? These books helped me do this.

Ever since I was a kid, I’ve always been intrigued by how people make decisions and why the words we use can significantly impact those decisions. After years of conducting customer research and writing marketing messages for clients, my interest in finding and delivering compelling messages at just the right time to the right audience has only grown. I’ve poured my experience in the online marketing trenches into my book, Finding the Right Message, where I reference more than one of the authors on my recommendation list. 

I’ve spent most of my career helping companies figure out how to become more relevant to their customers. And the more time I spent understanding what makes a brand relevant, the more I realized it was the same thing that makes a life relevant. Just as a brand needs to uniquely give something to its customers, human beings also need to give in some way to be relevant in this world. So if what I write—and the books I recommend—can even in the smallest way guide some company or individual toward a more important, more meaningful, more relevant life…well then, I guess my job here will be done.

I’m the founder of Purposeful Group, an author, and a multi-award-winning entrepreneur who has started multiple businesses from scratch. I believe that when you have the right mindset, positive things will flow from this. As the designer of programmes for entrepreneurs and digital learners, I have recommended books that I hope will give readers a great foundation to build on to achieve their entrepreneurial goals. From a personal perspective, they have kept me on track, and helped me build a framework of “success behaviours.”