Entrepreneurship books often speak in absolutes: Find your passion, take risks, embrace failure, build a great team.
Unlikely Entrepreneurs: Wins, Losses, and Crucial Lessons on Building Great Companies, by N. Louis Shipley and Patricia Favreau, takes a more honest route.
Rather than presenting entrepreneurship as a predictable formula, the authors tell the stories of founders who built businesses in across very different circumstances.
In many cases, these business leaders stepped outside the traditional entrepreneurial blueprint.
Here are five takeaways that stood out.
1. Identify problems first and second-hand
There is a difference between living through a problem and acquiring enough knowledge to understand a problem you haven’t personally experienced.
Bill Warner’s story illustrates the power of identifying a problem first-hand and finding a way to fix it for yourseld, and eventually others.
Warner is a critically acclaimed inventor, visionary and angel investor. He founded Avid Technology Inc. in 1987 after becoming fed up with the limitations of existing filming and editing technology.
By 2000, more than 100 television shows and movies such as “Titanic” and “The Matrix” were edited with Avid products.
By 2018, Avid’s solutions were used in 70% of commercially published music, 90% of original content from the leading streaming providers and 9 of 10 leading international news networks.
His story is a textbook example of an entrepreneur who identifies and solves a significant problem by living through its challenges.
At the same time, understanding a problem by harvesting information and researching the trials of others is equally effective in starting your own business.
Shipley and Favreau call this secondhand knowledge of the problem. That means getting close enough to customers, their workflows, frustrations, and incentives that the problem stops being an abstraction.
So, an entrepreneur doesn’t necessarily need to be a disgruntled or dissastisfied customer.
The principle is more centered around “getting to know your customer” over simply “know your customer.”
2. Early customers are critical to product design
A first customer doesn’t have to prove that you’ve finished building the business. They can help you figure out what the business should become.
Early sales aren’t merely transactions; they are a source of information about whether your proposition actually resonates.
In the earliest days, don’t ask only, “Who will buy this?”
Ask, “Who can help us learn what this needs to become?”
In 2017, award-winning journalist Katie Couric founded Katie Couric Media., with her NYC financier husband, John Molner.
Unlikely Entrepreneurs dives into Courin and Molner’s founding strategy. The authors illustrate how Couric and Molner wanted a customer who could act as a design partner.
They wanted help developing the media product rather than immediately putting a “finished” product on the market.
They sought out Procter & Gamble to become that first customer, prioritizing the opportunity to learn and build together.
3. A founder’s strengths can become company weaknesses
Shipley and Favreau use the term “flailing founder” to describe an easily overlooked problem.
The skills that help someone create a company aren’t necessarily the skills required to lead the company once it grows.
That idea appears repeatedly throughout Unlikely Entrepreneurs. The book moves from founding and selling into questions of distributed leadership, management, delegation, and entrepreneurship through acquisition.
At the beginning, a founder may need to know nearly everything. They make the sales calls, solve customer problems, make product decisions, recruit people, and personally push the business forward.
But as the organization grows, continuing to be involved in everything can stop being a strength.
The challenge isn’t simply “learn to delegate.” It’s recognizing which parts of the founder’s original job should disappear or merge into the responsibilities of others as the organization changes.
Psychologically, it is a difficult transition. The founder has to accept that the company can improve without their hands dipped in every pot.


