First, Get Your Act Together
It's funny how the Self-Help section has invaded the Business shelves. The reason is simple: if you take a bunch of chimpanzee-like primates originally evolved for the tribal hunter-gatherer lifestyle and a diet of nuts, berries, and roast beast, and future-shock them into a postmodern global village running on intricate financial flows and constantly changing business practices ... well, if you expect them to cope, they're going to need a little help.
Getting Things Done: The Art of Stress-Free Productivity and Home Comforts: The Art and Science of Keeping House at first glance couldn't be more different, but they both deserve their cult followings, and they work really well together.
How to Communicate: The Ultimate Guide to Improving Your Personal and Professional Relationships teaches us to listen before we speak: that's the single most important communication skill there is, and we all learned it when we were six, but it's been a long road since then. Assertiveness training goes the rest of the way: When I Say No, I Feel Guilty should be enough, though completists may want When I Say No I Feel Guilty, Vol. II, for Managers and Executives. With those skills, you'll have no trouble Getting to Yes: Negotiating Agreement Without Giving In. You may already practice all this good stuff; but you might want to have the books handy to give out to the less enlightened.
"If you build it, they will come" sounds good, but the real world isn't a movie. I meet a lot of inventors who are completely clueless about how to take their product to market. Fortunately, thanks to some brilliant thinking that has emerged in the last twenty years, innovation has become as much a science as it is an art.
Everyone in the Valley has read Crossing the Chasm: Marketing and Selling High-Tech Products to Mainstream Customers. It explains Chasm Theory. Well, I exaggerate. Some haven't read it. When you speak to them, you can kind of tell.
Chasm Theory goes hand in hand with Disruption Theory. If you work in a large company, The Innovator's Solution: Creating and Sustaining Successful Growth explains exactly why you're feeling frustrated by a lack of innovation.
Paul Graham's mantra is: "make something people want." I'd add the word "new" to that: "make some new thing people want." But how do you find out what people want? You apply Customer Development, described by Steve Blank in The Four Steps to the Epiphany: Successful Strategies for Products that Win, and elaborated in The Startup Owner's Manual: The Step-By-Step Guide for Building a Great Company.
If you don't already have a clear product hypothesis, but are still at the stage of being an unreasonable man about to create some progress, Blue Ocean Strategy: How to Create Uncontested Market Space and Make Competition Irrelevant might give you a framework for putting your inchoate intuitions into words.
Michael Gerber reminds us: don't just work IN your business. Work ON your business. Your business builds product, sure, but who builds the business? You do. As an entrepreneur, the business IS your product.
In The E-Myth Revisited: Why Most Small Businesses Don't Work and What to Do About It he describes a brick-and-mortar franchise. In Silicon Valley, you start a dot-com.
Great! Now all you have to do now is start a company, get funded, and you can start building product to sell to users!
Actually, that's not how it works. It's actually backwards. First you sell to users, then you build product, then you get funded.
The Lean Startup: How Today's Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses methodology developed by Eric Ries, and explained in a step-by-step fashion by Ash Maurya in Running Lean: Iterate from Plan A to a Plan That Works (Lean Series), are gospel.
Once you've got to product/market fit, then you're ready to raise money.
Raising money is itself a full-time job. The world of venture sounds glamorous and alluring, but in reality, venture capitalists work in offices and report up the chain to their partners and investors just like anyone else. In fact, they have to raise funds just like you do.
Guy Kawasaki's The Art of the Start: The Time-Tested, Battle-Hardened Guide for Anyone Starting Anything demystifies the process of raising capital and explains how to not waste your time or the VC's.
And it'll help to know your way around Term Sheets & Valuations - A Line by Line Look at the Intricacies of Term Sheets & Valuations (Bigwig Briefs). Brad Feld's Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist is less dry and offers more cultural context.
During the process of fundraising, I can guarantee one of the questions you'll get asked is What's Your Exit Strategy?: 7 Ways to Maximize the Value of the Business You've Built. Better have an answer. And that answer's not just for the investors. It's for you, too. Some people, when they walk into a room, the first thing they do is look for the exits. When you walk into a company, look for your exits. Of course, you shouldn't let the lure of an outcome distract you from building your ideal company, a firm that builds your ideal products, that you'd love to work at every day.
MBA For the Renaissance Man
A friend of mine, in the middle of her MBA, exclaimed: now I know how the world works! And it's true: business is a big part of the modern world, so knowing how business works is a big part of knowing how the world works.
Business is the sort of field where the big picture can only be glimpsed out of the corner of your eye. In the same way that the best childrens' movies are made to be enjoyable by adults on a deeper level, books like What the CEO Wants You to Know : How Your Company Really Works can be understood best by folks who have the right concepts in their heads.
The Portable MBA, 4th Edition offers those concepts: the mise en place, as it were, of business. It's what Heinlein would have wanted: every man and woman should know how to read a balance sheet, launch a product line, explain monetary and fiscal policy, hire someone, fire someone, record a ledger in a double-entry account, choose between debt and equity financing, know when to lower prices, and know when to raise 'em.
For a deeper dive into economics, read Naked Economics: Undressing the Dismal Science for background and Freakonomics [Revised and Expanded]: A Rogue Economist Explores the Hidden Side of Everything for fun.
Speaking of fun, everybody loves The Tipping Point: How Little Things Can Make a Big Difference, The Wisdom of Crowds, and The Paradox of Choice: Why More Is Less.
You should know why you're getting into the entrepreneurship game in the first place. How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets and The Education of Millionaires: It's Not What You Think and It's Not Too Late might help clarify your motivations.
During the course of your career, you will design products and you will draw diagrams. It will be to your advantage to have read Don Norman's The Design of Everyday Things and Tufte's Visual Explanations: Images and Quantities, Evidence and Narrative (if you take his course, you get all the books).
Now that you've proved yourself a true Renaissance Man, a few totally off-topic recommendations: Schott's Original Miscellany and A Pattern Language: Towns, Buildings, Construction (Center for Environmental Structure) will delight the nerds, I mean, the other smart people in your life.
In Dilbert-land, the verb "manage" means "control". As in "I need to go to the bathroom, but my manager won't let me."
In the real world, "manage" means "cope". As in "I'm responsible for so many projects, I'm barely managing to keep my head above water." Welcome to the cat-herding profession. Meow.
In Peopleware: Productive Projects and Teams (Second Edition), Tom DeMarco explains why cubicles suck, and a whole lot else. This is the number one book for anyone making the transition from engineer to manager.
I recommend two books on how to operate the manager-employee relationship. Remember, that relationship is artificial: we primates are hardwired to deal with parents, siblings, aunts, uncles, children, servants, village chieftains, kings, queens, and priests. We are not born knowing how to deal with "managers" or "direct reports".
First, Break All the Rules: What the World's Greatest Managers Do Differently and Bringing Out the Best in People help you learn what you need to know.
You may say that a lot of what's in these books is common sense, but even so, most of the corporate world doesn't know this stuff: if they did, they wouldn't put their programmers in cubicles. (Microsoft doesn't.) Think of it as a competitive advantage: your startup can arbitrage the gap between your knowledge and their ignorance.
What's the difference between a programmer and a software engineer? A programmer hopes for the best. A software engineer plans for the worst. A programmer loves writing code. A software engineer loves not writing code. A programmer knows how to do things. A software engineer knows how things are done.
O'Reilly's blue books are great for programmers. But programming is to software engineering what your home kitchen is to a restaurant.
I sincerely hope you and your entire engineering team have already read Extreme Programming Explained: Embrace Change, 2nd Edition (The XP Series), Professional Software Development: Shorter Schedules, Higher Quality Products, More Successful Projects, Enhanced Careers, Rapid Development: Taming Wild Software Schedules, Code Complete: A Practical Handbook of Software Construction, Second Edition, and The Mythical Man-Month: Essays on Software Engineering, Anniversary Edition (2nd Edition). Oh, and also The Pragmatic Programmer: From Journeyman to Master and The Practice of Programming (Addison-Wesley Professional Computing Series).
Let's keep going with the analogy. A restaurant manager needs to know about reservation systems (can we seat a table of eight at 7 o'clock?), produce suppliers (if tomatoes are in season next week, where can I get fresh mozzarella?), staff scheduling and shift rotations (who's going to work this Valentine's Day?) ... the list goes on.
In fact, her job is to make it possible for the cooks to focus on making the food, for the waiters to focus on keeping customers happy, and for the bartender to focus on the drinks.
In the same way, a software project manager's job is to make it possible for the genius programmers to focus on writing code. To do that, she has to meet with customers, gather use cases, turn them into requirements, estimate development effort, prioritize features, build a risk model, develop a staged delivery schedule, interface with QA, report to management, organize dependencies, coordinate integration, and run change control.
At work, a restaurant manager may never cook a single meal. A software project manager may never write a line of code.
I recommend pretty much everything by Tom DeMarco, but start with The Deadline: A Novel About Project Management, Waltzing With Bears: Managing Risk on Software Projects, and Slack: Getting Past Burnout, Busywork, and the Myth of Total Efficiency. Scott Berkun is a real nice guy, and his The Art of Project Management (Theory in Practice (O'Reilly)) is a good, if wordy, meditation on his experiences at Microsoft. If you've ever wondered what it means to "baseline a requirement", books like Software Project Survival Guide (Developer Best Practices), Software Requirements 2 and Writing Effective Use Cases will help fill the gaps in your vocabulary. A lot of managerial jargon is actually quite precise; they are not buzzwords, no more than "CGI" and "recursion" are buzzwords; they only seem that way to the uninitiated.
Predicting The Future
As Ray Kurzweil said, an invention has to make sense in the world in which it is finished, not the world in which it is started.
Read all the science fiction you can by William Gibson, Bruce Sterling, Neal Stephenson, Charlie Stross, and David Brin.
If you have what they call a Good Outcome
If you are one of the lucky winners of the startup lottery, please, remember to show some Class: A Guide Through the American Status System.