★ Rockstar Book Review: “Will It Fly?”

Review of: Will it Fly?
Pat Flynn

Reviewed by:
On March 10, 2017
Last modified:January 17, 2018


Calling "Will It Fly?" a business book feels like doing it a disservice. Pat Flynn gets it and freely shares his insights to help others be successful in both business and in life, all while avoiding the usual business rhetoric.

This is part of our Rockstar Book Review series.
Be sure to check out all previous books we’ve covered!

“Will It Fly?: How to Test Your Next Business Idea So You Don’t Waste Your Time and Money” by Pat Flynn

rockstar rating 4 and a half stars

Who it’s for: Those of us who want to start or improve an online business (which almost seems like a misnomer these days because what business doesn’t have some sort of online presence?).

Readability: MEDIUM. At over 300 pages, it’s inarguably a long book. That said, each section is to the point and includes helpful bulleted lists, images and diagrams to help illustrate what ideas the author is trying to convey.

What I liked about it: I’m going to fess up right now: as an entrepreneur, I tend to dislike entrepreneurship/business “how to” books. “How to” books for technical stuff? Sure, but when it comes to business, they make me shudder because they dehumanize the topic. That’s why I usually put off reading these types of books for months—if not years—after receiving them at conferences or via other means. For some reason, I read “Will It Fly?” within a month of receiving it. And I’m glad I did because if anyone had asked me what I would want out of a “how to” book for entrepreneurs, this would be it.

It’s down-to-earth, no nonsense, informative, proven, and includes the all-important YOU element that is paramount to business success. Without a doubt, this is a book for entrepreneurs by a guy who walks the walk, and who’s in tune with his all-important why. To boot, Flynn is serious about helping readers be successful because he’s included a fluff-free online course to help readers apply the steps he details in the book. I’m delighted to say that he has officially won me over.

What I didn’t like about it: Flynn’s approach gets very specific about halfway through the book (Part 3), which I thought might cause some readers to feel the book had shifted focus in a way that no longer seemed as sticky or as applicable to the majority of readers. It’s not so much that I didn’t like it but that I felt the change in style became somewhat of a distraction, making it harder to concentrate on the material. To my relief, the style soon reverted and the content continued to be of high value until the very last page.

Where to find it:

Amazon @ $11.97 || Free @ the library :)

“Will It Fly?” Uses a Highly-Relevant Metaphor to Help Us Evaluate Our Business Ideas

Pat Flynn is no stranger to the world of entrepreneurship. A quick search online confirms just how many projects he is/has been involved in: he’s started a number of businesses, has authored books on the subject, and has successful podcasts he uses to help both him and his audience explore various aspects of entrepreneurship.

This book contains a distilled version of this experience, complemented by stories and anecdotes from fellow entrepreneurs he has either advised or has learned from—in some cases there is even a clear ongoing relationship between the author and some of the entrepreneurs he features in his book (for more on this, see section #2 below).

Here’s what makes Flynn’s book stand out from boiler-plate-style books on business/entrepreneurship. Using the metaphor of building the perfect paper airplane, ensuring a smooth ride, Pat:

  1. Hones in on matching up what we’re good at as individuals with what businesses we say we want to build
  2. Shares his personal triumphs as well as his blunders
  3. Views a decision not to proceed as a success, that is when the reasons are not fear-based
  4. Systematically explains why the research around fit and feasibility is the most important part of the process of setting up a business, a topic business books often gloss over
  5. Differentiates between useful feedback and noise
  6. Focuses on the customer (understanding the customer, communicating with the customer and nurturing a strong relationship with core customers)

#1. Trying a Business on for Size

Being an entrepreneur sounds sexy. We can easily romanticize the idea of working for ourselves: setting our own hours, making a lot of money with minimal effort, and working towards making ourselves “unemployable”. What we all like to avoid is talking about the upfront cost of setting up a business, the number of months or even years of hard work with little to show for it before our business really takes off—if it does at all—and the fact that most entrepreneurs essentially create a job for themselves that they can’t easily walk away from.

Flynn tackles this issue up front. The first part of the book feels a bit like dating advice. Prior to assessing the feasibility of a business idea, we need to figure out what:

  • We care about most in our lives to ensure we protect it at all costs
  • Type of work we like to do and why
  • Type of lifestyle we feel comfortable with sustaining over the long term
  • Differentiates us from anyone else who could establish and run this business

The above is deemed paramount, because a great business idea isn’t all that great if we’re the wrong person to make it happen. Getting a business off the ground is hard and if we’re not deeply aligned with what it will take and passionate about it, we shouldn’t even start.

It’s important to know what to do, but it’s even more important to remember why you want to do what you do. (pg. 315)

#2. Learning from Those Before Us

Flynn stresses the importance of learning from our own experience as well as the experience of others. Seeking counsel can help us clarify why we think we’re making the right decisions for ourselves and for the business we’re building or intend to build.

And, more important than what others have done well, is what they regret having done. Those insights are worth their weight in gold, and finding trusted advisors who are willing to share these insights can save fledgling entrepreneurs a great deal of frustration, angst and lost time and money.

One of Flynn’s greatest pieces of advice? Talk to others about your ideas and don’t rush the process. Focusing on both helps us clarify what we’re trying to do and enables us to refine our approach before we decide to move forward.

The benefits of this focus can grow exponentially when we take the time to identify the individuals who are influencers in a given space and seek to establish a relationship with them by offering them something of value as opposed to simply seeking advice. (That’s the thing with influencers: everyone wants their advice but few are willing to consider what they have to offer in return that can turn a one-time request into an ongoing collaboration.)

#3. Saying “No” Can Be as Important as Saying “Yes”

The author considers a decision not to proceed to be as important to success as choosing to move forward with a business idea when:

  • It’s not a fit for the would-be entrepreneur, or
  • Research indicates that it’s unlikely to be successful

That said, fear should not be what guides a go/no go decision, only a true assessment of our strengths, abilities and preferences, along with a business’s proven feasibility.

#4. Fit and Feasibility Matter

After assessing the fit between a business idea and the would-be entrepreneur, the bulk of Flynn’s book is around fleshing out an idea by figuring out exactly what it is we think we want to offer and doing the appropriate level of research to validate or refute our assumptions.

What’s this business idea anyway?

It’s funny how we sometimes think we know what we’re thinking and then, when it comes time to articulate it to someone, we can’t explain it worth beans. It’s even truer when it comes to larger projects. There’s just too much to it to easily wrap our heads around it without some form of organization.

That’s where mind maps come in. They’re a wonderful way of capturing all our thoughts about a project, product/service or potential venture, which we can then organize in a way that makes sense to us. This subsequent organization is key in enabling us to remember the key aspects of the idea and communicate them effectively to others.

I’ve long been a proponent of mind mapping but had not done it in a while. As soon as I’d finished reading this section, I mind mapped a project I was working on and I found it tremendously helpful both in helping me get all the ideas out of my head, and then iteratively organizing them into a much more usable reference and guide.

Research stinks, but avoidable failure stinks more.

Traditionally, feasibility research would be focused on a SWOT analysis (an entrepreneur’s/business’s strengths & weaknesses and opportunities and threats associated with a given business or idea) and revenue cash flow projections.

The author has a different approach. He certainly advises his readers to evaluate current market players, but he also focuses a great deal on the customers of the products and/or services we’re considering offering, including substitutes. First, he suggests using Google searches to identify what customers like and, more importantly, their pain points. He stresses the power of stories in learning about what customers care about most (which make forums a great place to lurk and learn).

Next, he stresses the importance of engaging customers or would-be customers in conversations to better understand what they like/don’t like about the products and/or services in the space we’re thinking of entering. The key here is that it’s a conversation, preferably one that’s open-ended because it’s toward the end of a conversation that we can garner the best information. Why? The person we’re talking to has had a chance to think out loud about what we’re asking and, given enough time, summarize their thoughts and preferences.

Finally, he points to a truth we know but don’t often want to admit: what people say they want or say they will do often differs from what they really want and do. We need to trust actions more than words. We need to ask people to put their effort and their money where their mouth is early on and seek early adopters. These individuals can help us refine our solutions and our pricing and their feedback is just about the most valuable step in the entire process.

#5. Useful Feedback vs. Noise

I mentioned in point #4 that actions speak louder than words when it comes to what customers really want. When it comes to feedback, Flynn also says that we also need to be wary of overly positive or overly negative feedback:

  • Overly positive or negative feedback (1/5 or 5/5 ratings) usually mean that the reviewer is not objective and is likely to be a competitor, an overly negative customer whose assessment is clouded by strong emotions, or friends, family and/or colleagues trying to help the seller’s ratings. For Flynn, the value is in reviews in the 2 and 3-star range, where the reviewer needs to offer an explanation of why the rating is the way it is and who has likely given his/her views some consideration.
  • Negative feedback also has a characteristic that positive feedback does not have: it sticks. Negative feedback causes a visceral reaction in the business owner. It stings and that can have a lasting impact on us that crowds out much of the positive feedback we receive. Flynn stresses that, while we should listen to negative feedback, we should also consider the disproportionate mindshare we give it and be cautious about how much it influences our business decisions because when we do something that matters, we’re bound to tick some people off.

#6. Focus on the Customer

Any business book will tell us ad nauseam that customer service matters. What makes this book different is that Flynn bothers to explain which aspects of the customer relationship matters most:

  • Seeking feedback from people who have concerns and addressing them (but not to bother with the haters, they’re not likely to be worth listening to)
  • Nurturing the relationship by surprising our customers with unexpected bonuses and extras
  • Ensuring we understand who our true fans are and making them happy and/or seeking their input as we evolve our product or service offerings

The most important point Flynn wants to convey when it comes to the customer relationship is this: if an entrepreneur worries about solving a customer’s problem—about truly serving that customer—success and money is likely to come, and that the reverse is rarely true.

When you extract the pain, the marketing almost takes care of itself. (pg. 192)

Bottom Line

Calling “Will It Fly?” a business book feels like doing it a disservice. Pat Flynn gets it and freely shares his insights to help others be successful in both business and in life, all while avoiding the usual business rhetoric.

Where you can find the book: Amazon @ $11.97
Where you can find the author: PatFlynn.com

Other suggested books in this realm: “Born for This” by Chris Guillebeau, “The Element” by Ken Robinson (can help with the self-assessment work suggested in “Will It Fly?”, “The Power of NO” by Claudia and James Altucher, “Start with Why” by Simon Sinek and “The War of Art” by Steven Pressfield (quoted in this book, and a very good read for anyone trying to practice a solitary craft).


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Hélène is Rockstar Finance’s Curator of Books, and Blogger at FreetoPursue.com. A perpetual student, speaker, writer and coach, you’ll often find her reading, researching or writing. She also likes travelling and hanging out with her husband and their greyhound Belle.

Last modified: January 17, 2018

2 Responses to :
★ Rockstar Book Review: “Will It Fly?”

  1. I like this approach. A lot of businesses fail because they blindly plow forward without noting reasons the business could fail. It’s worth putting your business up to a stress test and to ask the hard questions first.

    1. Agreed. That and doing a cash flow statement. It’s amazing how many businesses with great products or services have to close just because they ran out of cash! I’ve seen it too often. It’s so unfortunate, and unnecessary (though I know first had how hard it can be to get a small business loan–the few times we’ve tried, the bank always wants to secure the loan with an asset, such as your home).

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