Entrepreneurship has come a long way toward being a better-understood and accessible way of life. But it will never be completely mainstream, because it's not for everyone. Consider the temperament and skills required. Entrepreneurs need a broad skillset and, equally important, a high degree of awareness about their weaknesses. It's a lonely, difficult, risky, frustrating, and sometimes scary path to choose.
Do you have what it takes? To help figure that out, I've assembled a list of critical reading every would-be entrepreneur should digest. The list is not comprehensive--I have purposely tried to make it as short as possible. This core set of thoughtful materials will help immensely with decision making about your path and execution of it, if you decide to pursue it.
What's It Like? What Does It Take?
The first question to resolve is whether you have it in you. Heart, Smarts, Guts, and Luck by Zappos founder Tony Hsieh (et al) is a very readable exploration of the psychology and temperament of the successful entrepreneur. A good resource for understanding the massive scope of skills necessary is the simply titled Entrepreneurship by William D. Bygrave and Andrew Zacharakis. This book will give you a nuts-and-bolts overview of virtually all aspects of the process (and will serve as a useful desk reference later). If 90 percent of the material in Entrepreneurship seems uninteresting or overwhelming, it's time to write a résumé.
There Is No I in Team
It has been said that all startup problems are people problems. I view that as accepted wisdom. Starting a fast-growth company is too broadly taxing to tackle alone, even if you want to. Building a team is critical, and startup team building requires great people skills, networking skills, self-awareness, and critical evaluation skills. People with a low EQ (emotional-intelligence quotient) will struggle mightily.
Two books top the list for essential reading on networking. Never Eat Alone by Keith Ferrazzi teaches that your power is your network. Like the title says, you should build it as part of everything you do. A second resource highly worth reading is by LinkedIn founder Reid Hoffman (et al) titled The Start-Up of You. Although it has some information on traditional careers, it offers excellent networking advice (including how to be a LinkedIn power-user). It will help you understand that managing your personal growth and professional development is the ultimate act of entrepreneurship.
Given that building a team is so important, it's critical to figure out how to hire A players. There is no better place to start than Who by Geoff Smart and Randy Street. This book helps you figure what you are looking for and teaches a rigorous method for hiring those people. It helps to avoid the most expensive mistake in business--hiring the wrong people.
As your team comes together, there are bound to be frictions. Even after hiring well, a fast-growing organization can quickly outstrip and burn out its key people. Harvard Business School professor Noam Wasserman's book Founders' Dilemmas and insights by leading venture capitalist Ben Horowitz (of Andreessen Horowitz) in The Hard Thing About Hard Things are both required reading and, fortunately, tremendously rich and readable. Once you put them down and realize you've got to make some changes, pick up the indispensable managers' guide to making personnel changes, Firing at Will by Jay Shepherd.
Finding Your Product Epiphany
Dialing in the right product, business model, and strategy is job one of every newly formed startup team. Stanford Business School professor Steve Blank's excellent Four Steps to the Epiphany provides excellent learnings for what's involved. To avoid overlooking one of the most commonly missed areas of innovation, your business model, take a run through Business Model Generation by Alexander Osterwalder and Yves Pigneur.
Product idea in hand, it's time for a good overview of strategy, including the choices and eliminations required. I strongly recommend Understanding Michael Porter: The Essential Guide to Competition and Strategy by Joan Magretta. In terms of setting your ambition level and figuring out whether you have something special, the Heath brothers' Made to Stick: Why Some Ideas Survive and Others Die also provides very helpful perspective. If you're still thirsting for more, Guy Kawasaki's classic Art of the Start has a few getting-off-the-ground nuggets, as does Eric Ries's widely cited Lean Startup, including "innovation accounting" concepts and key metric concepts.
Chief Extraction Officer
A teaching colleague and friend sometimes jokes that CEO stands for chief extraction officer, as in the person who extracts and collects the resources needed to grow the company. As you define the product and raise money to pay for development, extraction quickly becomes a pressing problem. The fundraising topic is so large and so varied and so regional, I hesitate to even broach it, but I can offer a couple of fundamental resources. VC and Tech Stars co-founder Brad Feld's Venture Deals is a very good primer on how risk capital investing deals work. And Brian Cohen and John Kador's What Every Angel Investor Wants You to Know does a good job providing orientation toward what the investor audience needs to hear about your business. However, keep in mind that some of the best and most current material in this space can also be found in blogs.
Basic Literacy: Accounting and Finance Fundamentals
Raising money requires a basic grasp of accounting and finance concepts and how they tie to your key metrics. Without these skills, you certainly wouldn't be able to manage funds properly even if you did raise them. Aspiring CEOs take notice: You can have a CFO, but you cannot delegate basic competence--you must know and understand your company's numbers. Bygrave and Zacharakis's Entrepreneurship is a good overview, but The Accounting Game: Basic Accounting Fresh from the Lemonade Stand by Judith Orloff and Darrell Mullis covers the basics in a way anyone can understand. When you have made it through that, move on to How to Read a Financial Report by John A. Tracy and Tage Tracy. It's an excellent guide to how financial statements are supposed to work and therefore a great guide to how to present your company's financial narrative.
As you begin to move beyond the early adopter customers, it becomes necessary to scale your sales and beef up marketing. Marketing genius Seth Godin has written a number of truly excellent books on the topic, but All Good Marketers Tell Stories is a good place to start. To further understand today's world of content marketing and online customer interactions, the treatise you'll want is Inbound Marketing: Attract, Engage, and Delight Customers Online by HubSpot founders Brian Halligan and Dharmesh Shah.
Once your initial launch-oriented marketing efforts start to fizzle out and your promising growth stalls, and decisions such as whether to quit, shift gears, or revise strategies loom, you will find insight and solace in Seth Godin's The Dip: When to Quit and When to Stick. Geoffrey Moore's classic, Crossing the Chasm, is also still relevant. If your gut tells you to forge ahead, it is time for a second close reading of both Ries's Lean Startup, which will really help you dial things in and create a workable set of metrics, and Magretta's Understanding Michael Porter, to fine-tune the strategic tradeoffs.
Life's Not Up on the Shelf
Can you learn entrepreneurship from a book? No. Mostly, you have to just get out there and try. Some things in life are best learned by doing. But getting grounded before you head out is common sense, and when you fall down really hard, a good book can provide great comfort. Most important is to keep your perspective and remember the old joke: Experience is what you get when you don't get what you want.