From Freelancer to Enterprise: 5 Books to Help

by / ⠀Entrepreneurship / July 30, 2013

Entrepreneur Reading
One of the quirks of the start-up culture is that it includes everything from Mom and Pop to the Death Star (actually, this one may not be scalable yet, so let’s replace it with another well-known titan. Insert name here ______). What’s always difficult is the transition from small business to scalable enterprise, particularly if you don’t want venture capital. And yes, it is possible to scale without venture capital, though such funding can probably expedite the growth stage and ease its pains.

Often neglected in the start-up culture discussion are books that will tangibly help your business, aside from the standard collection of books addressing sales or how great companies succeeded. Don’t get me wrong: these books are valuable (though rarely invaluable), but they don’t always address specific things that will assist you as your company grows. Dreaming’s cool (check numbers 3 and 4 on our list, or this great compilation), but it’s also nice to know that you’ll be able to deal with lawyers, contracts, PR, and all the other random junk that piles up on a start-up’s owner.

Sure, you can pay people to handle that stuff for you—and sometimes you should—but wouldn’t it be nice to at least know you can evaluate their work intelligently? Or, if you’re like me during my first three years running a start-up, wouldn’t it be nifty to be able to do some of this stuff effectively when you can’t afford to pay someone else? The list below is intended to guide you in every stage your company might take: these books can grow with you and your company. They’ve certainly helped me as I’ve built my own company and consulted with multiple other startups.

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Fundamentals of Critical Argumentation – Douglas Walton

If someone told you that you could learn many of the critical skills necessary for leading any company from an individual who largely created a new field of philosophical research and whose research has found extensive application in computer science, would you be interested in learning from him? This book is easily accessible and is broken into tiny segments that are perfect for an entrepreneur who may not have even an hour at her disposal. And, you’ll come away from studying the book with a level of comfort with reading contracts, asking applicable questions at meetings, and preparing for negotiations (angel, venture, merger, service, etc.) that will be invaluable to you for the rest of your endeavors.

They Say I Say – Gerald Graff and Cathy Birkenstein

Whether you are pitching investors or media, they’ll only respond if you give them a reason to care. This widely celebrated book (note: get the version without the extra readings) will help your writing skills shine and show you how to pitch people more effectively. When I was hoping to be included in a CNNMoney gallery article, I put the skills I learned from They Say, I Say to work. When you present investors or media with a tantalizing story already in hand, they’ll be thrilled to pursue where the story goes. This book will help you to elicit that thrill, and as an added benefit, it will help when you’ve reached writer’s block with your content marketing or advertising (or when you’re evaluating someone else’s writing for your company).

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50 Great Short Stories – Milton Crane, ed.

In order to keep our imagination going, we have to find some stimulation other than day-to-day work, at least if we want to build something new or figure out what additional elements our product (s) should have. This compilation of short stories will inspire you, make you uncomfortable, cause you to chuckle, and expose you to the oddest assortment of people you could find. There are similar compilations out there, but I’ve yet to find one more eclectic. And for an entrepreneur, that eclecticism might just initiate your next idea or help you improve your present one.

The Autobiography of Benjamin Franklin

If you follow the very first link in this post, you’d find that author listing 6 types of startups. Well, if we include building a country as scalable startup, Mr. Franklin was a major part of 4 of those 6 types—lifestyle, small business, scalable, and social. Whether working as a publisher, inventor, or social innovator, Franklin failed and succeeded in a life that defines serial entrepreneurship. If you need inspiration alongside practical insights, look no further.

Oh, and make certain you read the excerpts from Poor Richard’s Almanac. Epigrams like “Diligence is the Mother of Good Luck” never lose their vigor.

The Wild Card

You’ll note that I haven’t listed a specific book this time. That’s because I recommend finding your own nook to grow in—how else can you develop individual thoughts? But I won’t leave you empty handed. Sites like Brain Pickings, Quote Investigator, A Way with Words, or Project Gutenberg should provide you with some excellent leads if poking around libraries or flea markets isn’t your thing, though I highly recommend those too. Find an area of interest and dig in!

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Kreigh Knerr is a factotum. He invented the critical thinking and literacy enhancement app, QuotEd Reading Comprehension. When he isn’t dreaming up new mobile apps, advising startups, or mentoring students, Kreigh will likely be found researching online in a coffee shop or offline in the bowels of a musky library’s basement. You can reach Kreigh on Twitter @QuotEdapp.

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About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.