Idea: Teaching bootstrappers and developers to think like a lawyer

I live simultaneously in two different worlds - I am both a full-time lawyer and a “full-time” bootstrapper/developer. I am constantly learning things in one world that help me in the other.

Law school quite literally rewires your brain to think differently. In addition to learning substantive law, you learn to engage in different thought processes, hone your reasoning skills and write effectively. As a lawyer, my job is to spot potential issues, devise strategies to achieve goals, communicate effectively and solve problems. I think many of you would agree that these tasks sound a lot like some of the most important concerns of a bootstrapper.

My idea is to create educational materials that teach bootstrappers and developers some of the knowledge and skills of a lawyer with the hopes of enabling them to put that knowledge and those skills to work for them. The program would cover argumentation, reasoning and logic, writing techniques, issue spotting and related matters. These skills would be taught in the context of running a small business (or managing your own personal life) to show how they these skills can be deployed in various settings, including outside of a legal context. In addition, the program would cover substantive areas of law that affect businesses and the individuals that run them, including the basics of contracts, business entities, torts, intellectual property, taxes, family law, estate planning, etc. More in depth coverage of these topics, plus deep dives, advanced topics and any “fun” topics requested could be covered as well. The goal of the substantive topics is to allow you to better spot trouble before it comes, help you avoid common pitfalls and, most importantly, allow you identify when you should seek appropriate legal counsel.

The format is yet to be determined based on feedback. I imagine it could take one or more of the following forms: an ebook, blog post series, email course, micro-podcast, etc. There would definitely be a paid component and likely some free component as well.

I would appreciate any feedback you may have, both here on the forum and, if you would like to fill out a short survey for a chance to win some great prizes, over at

Thank you so much in advance for any feedback. I’m hoping people are responsive to the idea because I think it could be a really interesting product.

Disclaimer: I’ve been a developer for almost 20 years, who’s been bootstrapping various side-projects with not much success for about half that time. I also have a law degree, although I don’t practice. So I’m probably not your target audience. Furthermore, I’m a cynical, glass-half-empty old fogey in the body of a not-all-that-old man, so take that in mind when reading the following.

I’m not quite sure what your course would offer. The ‘thinking like a lawyer’ part doesn’t particularly ring any bells. While my law degree has been useful, I don’t see how much if anything of it could be transferred in bite sized chunks to people without a legal background/foundation. The substantive areas you mention are either covered extensively as introductory material across the web, or is too much and complex to teach in a chapter of an ebook. For example regarding contracts, what would you cover that goes beyond a template contract that can be downloaded online? The Bob Walsh book covers those things to some degree, but they’re (imo) the least useful chapters.

Do you have examples of people who have written other ‘thinking like a lawyers for xxx’ books, where xxx is any profession or market? If no, is that because the concept is only applicable to bootstrappers or because there just isn’t much useful to say about it? Maybe something like this exists, I don’t know - I’d be interested to hear about it but I’m skeptical.

Lastly, I think your description as you put it here and how you put it on your website isn’t convincing enough, meaning - doesn’t show the value it brings for your customer. I think you need to make it more concrete to appeal to people. How does ‘thinking like a lawyer’ get me more customers? Or what other problems can it solve, and how does it do that?

I have to agree.

It’ll be hard to sell something people aren’t looking for, and that doesn’t solve any major pain.

1 Like

Roel_V - Thanks so much for your feedback. You may not be the target audience but, for obvious reasons, your feedback is valuable. Regarding the website, I wanted to keep the survey very simple so as to encourage participation, so I intentionally did not go too much into it there. As for similar offerings out there - from what I’ve seen, there are a few things targeted toward other industries, but most of it is very generalized. I haven’t seen many instances of this idea being applied to specific non-law pursuits. I’m still investigating as to why this is the case. I think that general “how to think like a lawyer” materials aren’t helpful because they often don’t give the reader specific contexts in which to consider the concepts.

I hear your point about the substantive law areas. I think the key element is to teach issue spotting. I think the most effective thing a non-lawyer can do is anticipate when it is appropriate to reach out to legal counsel. In my experience, people don’t reach out early enough and only do so once a problem has occurred. Again, I think context matters a lot here, so my goal would be to give fact patterns that you would encounter in the tech world.

Thanks very very much for your thoughts.

I’m hoping that the survey shows that people are looking for this!

Not sure if you’re got it the right way round there. Shouldn’t you be trying your best to disprove your hypothesis? Maybe you need to think like a scientist. :wink:

What you are ‘moot’ (sorry) -ing sounds like a solution, rather than a way to explore the problems developers have. i.e. you are saying that the solution to developer and bootstrapper problems is to think like a lawyer. Or maybe I misunderstand?

You may have an inkling that “thinking like a lawyer” will help, but I’m not sure putting it that way will attract anyone. However, teasing out how thinking in that way may help, then exploring those ideas might glean more information.


@gravelld Thanks for the thoughts. I should first note that I certainly don’t intend to peddle the idea that everything can be solved by “thinking like a lawyer.” Trust me when I say that lawyers don’t have all the answers. What I do believe is that employing the thought processes and methods that lawyers use can help with many of the things that we experience in the tech/business world.

I already know from my own experience and the experiences of those in my circles what types of problems developers, bootstrappers and entrepreneurs in general face. In the tech space I have avoided problems, identified problems and worked to solve problems using my skills from the lawyer side of my life. I have also helped those I have worked with think about thinks differently. In fact, this idea came to me because my co-founder from a former venture called me a short time ago to tell me how he actually avoided a huge problem at his new job by employing some of the principles and techniques I instilled in him while we worked together.

So I guess my point is that I am confident that the “problem” exists. The key is going to be helping people how they can benefit from this endeavor.

Yeah see - I still don’t understand. Maybe if you have one ‘case study’ like the one you mention as an example, that will explain what your idea is? You say you know the types of problems your audience has - maybe if you list them it’ll become clear? Just thinking out loud here.

1 Like

@Roel_V will take what I have so far and cull together some concrete example. Thanks for continuing to push me on this.

Why not just sell the result from thinking like a lawyer. E.g. sell contracts or contract review.

Kinda dig this idea. I hate anything legal related and don’t understand it. Somehow making that content more approachable and applicable to bootstrappers would be awesome.

Maybe bullet point out some topics that you’ll be covering?

Maybe you could start by collecting pain points from bootstrappers around legal issues.

Hi @madshadow, I’m interested to read some of your blog posts, please give link. It is not clear what you mean exactly, please describe, it would be good to start a blog, see activity of readers, get feedback from them

I think there’s an interesting idea in there, but the messaging feels completely wrong. As a developer / bootstrapper, I really don’t want to become more lawyer-like… and I say that as someone who used to work with a law firm! Indeed, they brought me in because I don’t think like a lawyer.

That said, I can see there are ideas you can bring across from law. The law firm introduced me to FMEA (Failure Modes and Effects Analysis) as a way of prioritizing what needs to be worked on. Their focus on scheduling is 10x - 100x anything I do. They’re so much better at networking & finding leads & quantifying the value of a market. They have systems for automatically monitoring updates on laws & notifying themselves (like Google Alerts but for their own niche).

In my own developer / bootstrapping, I rarely encounter issues that can be solved by lawyers, so “thinking like a lawyer” seems to be a negative. Piracy might be a legal matter, but Australian lawyers can’t help me prosecute people based in Russia, and it wouldn’t be worth my money to do so. Instead it’s a legal solution that I solve with technology (ie DRM, maybe the odd DMCA submission if a pirated copy is hosted on a US server).

Maybe consider reframing your book / course as “business strategy” for developers, rather than thinking like a lawyer. Take the great ideas and ‘lifehacks’ from the law world, and reframe them in ways that apply directly to bootstrapped developers, without even mentioning that the methodologies come from law.

(Lastly, keep in mind that if you’re looking at specific laws, you’ll probably restrict your audience to US only. If you can generalize to strategies & tactics, you can open up your product to a global audience.)

@pjc I’m already a traditional lawyer by day, providing legal counsel to clients. I wanted to try something a bit different as a side project.

@kalenjordan Thanks for the feedback. Some of the main topics I would cover, at least initially, are logic and reasoning tricks, writing tips, issue spotting and substantive law areas like contracts, business organizations, copyright, etc.

I have been working to collect pain points and will continue to do so. Thanks again for feedback.

1 Like

@syneryder Thanks for the feedback. To be clear, I think what I’m trying to do is what you are suggesting- namely, bringing lawyer skills to the non-lawyer. I think the most important aspect will be issue spotting - the ability to identify problems before they occur or as they are occurring. Even if you don’t know the answers yourself, just knowing when to ask a professional goes a long way.

Thanks again for the feedback.

Thank you all for the feedback thus far. I think what is clear to me is that I need to start with a series of blog posts to illustrate my intent. Stay tuned…

Same here. There is so much interesting and/or useful stuff online I can read and I don’t see ‘thinking like a lawyer’ ever making it to the top of that list.

Given you have a background in bootstrapping and law it might be interesting to read bite-sized pieces about the legal issues around:
But I am in the UK, so wouldn’t be interested in anything specific to another country.

Looking forward to reading them.

I think my main objection right now is that I don’t really envisage lawyers at being especially good thinkers, as such, any more than a computer scientist or mathematician is. So to me… meh? I guess I just don’t understand these mystical ways of thinking outside of common philosophy that lawyers employ. I’m looking forward to reading examples.

But then also I suppose a lot of us here aren’t any of {lawyer, computer scientist, mathematician}.

Hmmm… maybe you could approach this like a startup considering a service.

  1. What PAIN or PROBLEMS do you solve for the Entrepreneur?
  2. Do they know they have these problems?
  3. Do they believe you can solve those problems?
  4. Can you solve those problems for less than the problems “cost” them?