While Zero to Sold is my personal take on starting, running, and exiting a bootstrapped business, I learned a lot while running my own business, and so have many others. I’ll share all the resources that helped me along my own bootstrapped journey.
If you’re interested in listening to my experiences and learnings, you can subscribe to my podcast The Bootstrapped Founder and listen to my appearances on dozens of podcasts such as the Indie Hackers Podcast with Courtland Allen, Startups for the rest of us with Rob Walling, or Built to Sell Radio with John Warrillow.
There are thousands of books about starting and running a business, and I have tried to read as many of them as I could over the last decade. Some were extremely helpful, some were not. I’ve created a list of recommendations and reviews of the books that I found to be insightful, actionable, and helpful. That curated list is available at The Bootstrapper’s Bookshelf.
Another bookshelf that might interest you is curated by Patrick Collison.
The Indie Hackers podcast is one of the most impressive collection of mindblowing interviews with bootstrapped founders from all over the world.
Started in 2010 by Rob Walling and Mike Taber, Startups for the Rest of Us might be the longest-running podcast that focuses on giving bootstrappers actionable insights founded on decades of experience.
The founders of Transistor.fm, themselves bootstrappers, have devoted a whole page to bootstrapping podcasts that are worth subscribing to. At the end of that list, they even list those who are not hosted on their platform.
In addition to running Transistor.fm, Justin Jackson publishes a newsletter that is full of actionable insights for bootstrappers.
There is one guide that always stood out to me: Clifford Oravecs “The Epic Guide to Bootstrapping a SaaS Startup from Scratch.” It is a strongly worded, somewhat offensive, yet delightfully honest look at the life of a bootstrapped founder. It makes you take off your rose-colored glasses and focus on the hard-to-swallow truth of entrepreneurship: there will be struggle, there will be mistakes, and there will be hardship. If you can handle this guide, you can handle building a bootstrapped business.
Neil Patel has started a few companies in the past, and he has been both a bootstrapped and a VC-funded founder. His insight into bootstrapping is extremely valuable, as he points out the pitfalls and risk factors of funding a business yourself from scratch.
The team at Jotform has created a well-designed guide that talks about many core questions that come with a bootstrapped business, from co-founders to keeping your sanity. The guide asks the right questions and gives a few suggestions without being preachy and is full of links and examples.
Tyler Tringas, the founder spearheading Earnest Capital, wrote a fantastic guide called Building Micro-SaaS Businesses. His personal experience building small SaaS businesses is apparent in every paragraph, and it’s a dense source of insight and information.
Abdo Rianis Step By Step Guide To Startup Bootstrapping By Self-Funding And Pre-Selling includes a delightful breakdown of startup expenses and actionable tips on how to get through all the stages of bootstrapping a sustainable company.
There are a handful of reasonable resources that describe the inner workings of successful businesses without being an obvious marketing play. Most of those take the form of employee handbooks and are usually very specific to the businesses that issue them.
The biggest and most renowned bootstrapped player in this field is Basecamp, with its open-source handbook. It offers an in-depth glimpse into the social fabric that makes Basecamp the well-oiled sustainable machine it is. From product explanations to who does what, the handbook shows a level of detail and operational awareness that is very admirable.
The Gitlab employee manual is just as detailed. It spells out every role, names the responsible people, and expands what they do, and why. It’s a living, breathing document that shows how a remote-first company spreads its culture and keeps knowledge and processes aligned. Every section clearly communicates how feedback is supposed to be presented, leading to a remarkable clarity of communication: a must-have in a remote company.
Netflix has an extensive Culture document (and a Reference Guide) that highlights how interactions between colleagues are expected to happen. Core concepts are explained in detail, while company goals and aspirations are made manifest through the behaviors that employees are expected to exhibit.
HubSpot’s Culture Code comes as a slide deck. It’s a fun, aspirational document that makes it clear from day one that HubSpot is passionate about their customer’s success. The empathetic self-awareness of this document shows clearly that they expect employees to have their heart in it.
Trello uses the ultimate dogfooding approach to their employee manual: they offer a template as a publicly available Trello board. While their internal version is private, the structure of the template alone is exciting and thought-provoking.
While much more corporate, the Atlassian Team Playbook contains a multitude of step-by-step plays ranging from conducting customer interviews to mind-mapping an idea. It is process-focussed and can be applied to any team. It seems to have grown from Atlassian’s internal practices. It’s an excellent resource for later-stage businesses, but even a newly created business might benefit from many plays there.
If you’re interested in looking into more of this kind of handbook, I recommend checking out Tettra’s Culture Codes section. And of course, an honorable mention goes to the handbook that came before all the others: the Valve employee handbook.
The software engineering community has aggregated a few exciting link collections:
Y Combinator offers Startup School, a collection of videos and resources that aim at helping startups getting started. Assume that most of the advice will be aimed at creating a VC-compatible startup with all the growth and scaling expectations.
Special Interest Series on The Bootstrapped Founder
On the blog, there are a number of thematic series that deal with particular topics. These series are receiving updates on an irregular basis.
The Emotional Journey of a Bootstrapped Founder deals with challenges and issues that come up in the day-to-day operations of a bootstrapped business. For every emotional state I encountered, I wrote (or will write) an article.
The Tales of a Bootstrapper series shines a light on the real-life experiences of other founders and entrepreneurs. Every article is centered around a person or a business, what they did well, where they may have failed, and what can be learned from their experiences.