Start Small, Stay Small: A Developers Guide to Launching a Startup by Bob Walling (Book Review)

Start Small, Stay Small: A Developers Guide to Launching a Startup by Bob Walling (Book Review)

Content :

Name: Start Small, Stay Small: A Developer's Guide to Launching a Start-up
Author: Rob Walling
Publisher: The Numa Group, LLC 
Publishing Year: 2010
Pages: 212
Rating: 4.5/5
Purchase Link:

About the Author

Rob Walling is a serial entrepreneur, blogger, angel investor, and a podcaster. He's the author of Start Small, Stays Small: A Developer's Guide to Starting a Start-up, released in 2010. Walling is the founder of the email marketing software Drip that was acquired in a life-changing exitby Lead pages in July 2016. 

In the early 2000s, Walling tried to launch several software products that failed. He has had his first notable success with DotNetInvoice, an application for invoicing applications. Subsequently, he launched another small business and founded an online tech founders group named Micropreneurs.

In 2010, he started a podcast with Mike Taber, which became one of the most popular start-up podcasts in iTunes, called Start-ups for the Rest of Us. The next year, in June, he co-founded MicroConf, a conference for self-funded start-ups, which is held twice a year in Las Vegas and Europe. 

In August 2011, Walling purchased and revamped HitTail, web-based software as a service product that provides long-tail keyword suggestions. Before purchasing HitTail, it had used a freemium business model to market the product.  Walling stopped the freemium model and used traditional software marketing to bring in more paying users. He founded Drip, an email marketing tool that allows a user to send emails to their audience based on user behavior, in 2012. 

Walling has become known as a supporter of self-funding or bootstrapping software companies that turn a profit, instead of raising funding from venture capitalists. Much of his writing focuses on tactics for growing software as a service startup. 

In 2014, he wrote the foreword to Dan Norris' book, The 7-Day Startup: You Don't Learn Until You Launch.  

In March 2015, Walling published one of his best-known essays titled The Stairstep Approach to Bootstrapping where he outlines a potentially safer, more structured approach to bootstrapping a start-up by starting with small, simple product ideas and leveraging the revenue and experience earned from them to tackle more ambitious (and typically more financially rewarding) ideas.
This approach was the focus of a chapter of the 2015 book The End of Jobs: Money, Meaning, and Freedom Without the 9-to-5 by Taylor Pearson.  

On July 26, 2016, his company, Drip, was acquired by Leadpages for an undisclosed amount. He led the Drip marketing squad, from Minneapolis headquarters at Leadpages, through April 2018.

Walling revealed in October 2018 that it was launching the first bootstrapper-designed start-up accelerator, called TinySeed.

About the book

Start Small, Stay Small is a step-by-step guide to launching a self-financing start-up. If you're a developer of a laptop, tablet, or network, this book is your blueprint for getting your start-up off the ground without any outside investment. This book deliberately avoids subjects that are restricted to venture-backed start-ups such as fine-tuning your investment pitch, securing funding, and figuring out how to use the piles of cash investors that keep placing in your lap. This book assumes:

• You don't have $6M of investor funds sitting in your bank account
• You're not going to relocate to the handful of start-up hubs in the world
• You're not going to work 70-hour weeks for low pay with the hope of someday making millions from stock options

Pursuing venture capital and seeking to expand exponentially, like Amazon, Google, Twitter, and Facebook, is no wrong. It just so happened that most people are not in a place to do this. Start Small, Stay Small is also focused on a start-up’s single most critical factor that most developers avoid: marketing. Many great resources are available to learn how to write code, organize source control, or connect to a database. This book does not cover developers already know about the technical aspects or may learn elsewhere. It's focused on finding your idea, testing it before you build it, and getting it into your customers ' hands.


I recently read Rob Walling's 'Start small, stay small: A developer's start-up guide'. The preface states:
"This book is targeted at developers who have no external funding to launch their startup. It's for companies founded by real developers to use desktop, web, and mobile apps to solve real pain points.”
Many of you are probably already familiar with Rob's work, including a blog, a podcast, and the academy of microentrepreneurs. Rob’s approach has been to develop a portfolio of niche websites as a solo founder (for example, funding it with his capital and outsourcing work where appropriate. The intention is to have a business that produces a decent income but allows the founder a flexible lifestyle. He uses the 'micropreneur' portmanteau to refer to the strategy. It is not a word I care about, with its awkward shunting of Greek and French together. Yet I don't think it's worse than 'microISV.' He develops on these themes in the book, with a particular emphasis on the early phases (as implied by the title).

The chapter headings are:

1. The chasm between developer and entrepreneur
2. Why niches are the name of the game
3. Your product
4. Building a killer sales website
5. Startup marketing
6. Virtual assistants and outsourcing
7. Grow it or start over

There is plenty of insight and actionable knowledge based on experience, as with Rob's blog and podcast. Most of the writing is taken straight from the blog but I believe much of it is new. There are links to useful online tools that I hadn't found before. It even includes some of that rarest of commodities – real data. He also dispels a lot of myths – for example: making a software product is a fast and simple way to get rich and Facebook and Twitter are all the marketing you need.

The book is particularly strong on market research – in the context of small software companies, a subject that I haven't seen covered much. This uses a step-by-step approach to calculate market size. It also covers other useful things The paper version of the book is 202 pages long. There isn’t a lot of unnecessary waffling or padding, so you are getting a fair amount of information for your money. An index might have been useful. Perhaps for the next edition?

While the book will have the most benefit for that first starting out, I think even experienced software entrepreneurs will probably find some of it useful. The book is available in paper, electronic and audio formats from $19 at Given its niche market, I think this is good value.

Takeaways from Book

 Marketing is bigger than your product. Let me put it another way: Last Product - Marketing First. It has got to be good for your company. If it is not, then you're going to be out of business.
 When you do it for the money you are not going to hang around through the long months of hard work when there is no money coming in.
 You can't consume and produce at the same time – you have to temporarily step away from your magazines, blogs, and other forms of distraction for some time when you're in high-producing mode.
 Stop doing it if you're not enjoying something.
 There are only two skills you need to learn to sell online: human behavior and math.


I'll say this right off the bat: Out of all the books I've read since my childhood, this book has easily been the most useful. 

The striking thing about this book is just how much it does not focus on computer software. As the book is focused on software engineers who wish to be entrepreneurs, it assumes you know the software and wants to learn about the other aspects of starting a company, such as the importance of product management and marketing. It's also striking for how many hard metrics it provides; you need to launch within six months of having a landing page up and running, your conversion rate may vary between X%-Y%, etc.

If anyone wants to start a company or any business, I will highly recommend this book to have a glimpse ofa more inspirational and effective business.

If this book sold for $100 instead of the $25 on Amazon, it would still have been worth it.