Ask HN: Books giving practical advice on starting a solo SaaS business?

379 points by Dockson ↗ HN
My goal in life (as of right now at least) is to start my own SaaS business so that I can eventually quit my 40 hour work week and have more time for things I enjoy doing. To reach that goal I am first compiling practical advice from people who have already been through that process and are now sharing that advice around ideation and idea validation, marketing, pricing, etc.

I've been looking for book recommendations on this topic both here on HN and also on Indiehackers and while there are many books that are most certainly relevant in some ways and generally just good reads, I would like to start out by asking you if there are any books you've read that specifically give this type of advice. I say books to keep it simple but am of course also open to other types of high-quality resources like blog series or conference talks.

Looking forward to hearing about all the great things you guys have read!

101 comments

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“Start small, stay small” is good (but a bit old)

Definitely check out Indie Hackers though! The whole community and podcast is built around that idea.

I did see "Start small, stay small" being recommended but was put off a bit by its age. But you would still recommend it today then?
Not really. With all due respect to the author, most of the advice there doesn't really apply today in the world we are living (well, maybe after COVID it will again?). I remember reading it a few years ago and it was already dated by then.
I remember it being really good, though I haven't read it for awhile. I thought I remembered hearing a podcast where Rob talked about what he would change if he rewrote it today, but I can't seem to find it (maybe someone with better google-fu can)

Here is one of his podcast episodes where he talks about it though - so you can start here: https://www.startupsfortherestofus.com/episodes/episode-219

If you’re starting a solo saas business (and even if you’re not) I cannot recommend this podcast series highly enough.
The author here.

Startup for the rest of us (podcast) tracks better with my current day thinking.

There’s a major chunk of the book that’s high-level mindset and strategy that still holds up. The detailed tactics do not (unsurprising given we’re 10 years out).

Fellow aspiring solo founder here! Here are a few books/resources I've found helpful:

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The Mom Test by Rob Fitzpatrick

This book stresses the idea of starting with customer interviews before you build anything and how to ask questions of prospective customers to get meaningful information when people's bias is to just tell you, "Yeah, that sounds like a good idea," even though they'd never pay money for it. I spent a long time trying to apply it, and the struggle was that in my experience, customers who don't mind diving deep into their unsolved problems for an aspiring founder are a disjoint group from customers who have serious money to spend.

My notes: https://mtlynch.io/book-reports/the-mom-test/

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Start Small, Stay Small by Rob Walling

This is a bit dated, but I think it has valuable takeaways. The most important for me was the value in marketing to small niche customers. Big competitors are less interested in catering to niche groups, and the more specialized, the easier they are to find and market to (e.g., they all read the same magazine or attend the same convention).

My notes: https://mtlynch.io/book-reports/start-small-stay-small/

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"Designing the Ideal Bootstrapped Business: Jason Cohen, Founder, WP Engine" (https://www.youtube.com/watch?v=otbnC2zE2rw)

A good recording of a MicroConf talk about useful things to consider when building a new Saas business.

Seconding The Mom Test. It's a fast read too, and the author was on a recent episode of the Indie Hackers podcast.

For more of the same, I got a lot out of Lean Customer Development by Cindy Alvarez. Here's a talk from Cindy if you'd like to get to learn more before committing to a book: https://www.youtube.com/watch?v=d5hc7sseHbE

++++ on The Mom Test. The #1 book any founder (solo or otherwise) should read before starting anything.
If I’d had the Mom Test in 2006 I would have saved $1.5 million of my own money trying to beat Craigslist.
Thank you! I've seen that youtube video previously and it was exactly the kind of advice I was looking for. I will put "The Mom Test" at the top of my list as I've seen many recommendations of it elsewhere too.
Start Small, Stay Small did a lot for me.
Start Small, Stay small is 10 years old. A lot has changed since then. The author made an unfortunate decision to write extensively about things that are not perennial. So after reading for a while about software tools and practices that are now dead or outdated, describing the limitations of an iPhone 3G, etc, I decided to stop and return the book.
The author here.

Yep, that makes sense. I’ll say most marketing books I listen to that are 10 years old are brutally out of date.

The focus on detail that made the book a success also made it go out of date relatively quickly.

It needs an update. That is on my to do list most years (between running MicroConf and TinySeed) and one of these days I will circle back and get it done.

Honestly, this weighs on me. It’s something I’ve been wanting to do for years.

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Sounds like you started small* and stayed small :-)

* in the niche sense

Seems we’re on the same wavelength, so I’ll as “Running Lean” and “Nail It then Scale It” as books you’ll likely find useful.
Good one!I suppose the insights apply to not just bootstrapped businesses. Great clarity of thought.
Traction by Gabriel Weinberg.

This book is really amazing and filled with a lot of practical advice. Can't recommend this enough.

Having done this a few times, the biggest advise I can give is that time is your most valuable resource. So look to maximize this resource with each decision you make. For example, in buy vs build situations you should err on the side of buy. You can find affordable services that will handle close to 100% of your generic SaaS needs. So don't reinvent the wheel, and go with as much off-the-shelf as possible.
Absolutely! This is something I've seen many people emphasize so it is something I will keep in mind for every decision I make.
With a mere 40-hour work week, you want more free time? We're clearly dealing with a serious customer. If more free time is your goal, starting your own business is the one thing you should not do.
It depends on what your business is. I know multiple folks who are comfortable with an $80K/year net business who work maybe twenty hours a week.

With managed expectations it's very doable.

I do indeed have high aspirations for my life. Given my career of choice and what I've read so far regarding other people's experience starting a SaaS, I definitely feel it can be a viable way of achieving those aspirations.
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Company of One by Paul Jarvis is a nice short read. Not SaaS-specific, though.
A SaaS-specific version of "Company of One" would be awesome. I liked that book, but it was a bit generic in its recommendations (which PJ acknowledges as a limitation of the book upfront, so that's not a criticism).
If you are reading a book instead of talking to and connecting with people to find out what they truly personally need, does it really matter what book you are reading?

Sounds rough, but I'd recommend weighing any recommendation against this.

I don't think talking and connecting to your customers tells you about how file taxes, stay in compliance with labor laws, etc. There is the product and there are the mechanics of the business. You have to do both, and books are probably a good jumping-off point for the latter.
So you're recommending that instead of the book, they read these two sentences from you and start from there?

How about a book that motivates people to do that, like four steps to the epiphany? It isn't an either-or proposition.

I hadn't thought of it that way, but yes, I would go so far as to guarantee that my previous two sentence comment is more valuable than %99 of all business books.

You can conclude the above after absorbing the opportunity cost and burn of reading a few thousand pages of anecdotes from newly wealthy people post-hoc moralizing their luck, or you can start with it as an axiom that provides the only demonstrable path to success.

However, it's the only advice I have.

No no no. Most SaaS nerd founders make the same set of mistakes. Reading just “the mom test” or “running lean” can potentially save those people years of wasted time making the mistakes.
The E-myth / E-myth Revisited.

I’d argue anyone in business - as either an employee, entrepreneur, manager, etc - should read it because the basic lessons are universally applicable to every business, regardless of size or industry. Especially as a solo practitioner, there’s value in understanding the dangers of doing everything yourself.

As someone who recently launched a SaaS business, I'd say your rate of learning increases dramatically after you launch a business, however successful it is. It's certainly helpful to learn about other's experiences, but nothing beats launching the business on your own. Even reading books after you launch feels different: you tend to appreciate the advice more, and start noticing all the nuances you were glossing over before.
Make book from Pieter Levels.

From my point of view, he is very productive, successful, willing to give ton of advice.

He has few good websites (or call it startup or whatever).

I started my own SaaS business on the side and quit my 40 hour work week a couple years later to work full time on it (and have been loving doing so ever since).

You'll probably get a lot of practical suggestions on processes from others here, but I really enjoyed Peter Thiel's Zero to One book. It's not 100% relevant since he rambles pretty hard throughout and a lot of it needs a pinch of salt since he's so contrarian, but there's a lot of really good gems in there about how to build something legitimately new to create your own pie of income (including chapters on marketing, pricing, etc), instead of building something to get a small slice of an existing market.

This guy seems to know a great deal about starting a new IT business:

https://www.joisig.com/

Might be worth it checking that out.

EDIT: As a software developer, I also second Basecamp books and their organizational culture (that is explicitly and publicly divulged on their materials - some of them are free).

"quit my 40 hour work week and have more time for things I enjoy doing"

Given that basically everyone would like to do this, I suggest it's a rather challenging thing to do in that it's highly competitive, and that the vast majority of Entrepreneurs, bootstrapped or otherwise, work longer hours than average.

If you calculate risk into the equation, it does not look good.

If your real objective is 'work-life balance' then there's probably an opportunity for you to contract and consult x-hours a week that has considerably lower risk dynamics.

But if your actual goal is really to start a business, then obviously that's what you want to do.

By all means, read the books mentioned in this thread.

And then drop it and just start working.

There is a large swath of self-branded Indie Hackers who cling to books, blogs, conferences etc. but are too paralyzed by all the advice and input to actually do the one thing they need to: get customers.

Disclaimer: I run my own SaaS and visit Indiehacker meetups and stuff. I’m not a nay sayer, just stay skeptical.

I've found this to be true in a lot of subjects. When I started really getting into machine learning a few years ago, I did all the courses, refreshed on my college math, followed tutorials to learn things like tensor flow. But despite all that, I was totally flummoxed on my first day as an ML engineer at work. It wasn't until I started building things to solve problems and learned practical lessons by doing that (with messy data vs toy prepared datasets) that I really excelled. I wouldn't be surprised if this tactic of just starting working would help here too.

So, even though I haven't specifically built a saas business by myself, though I have a bunch of experience growing small startups to medium to large companies, I would echo this advice.

Did you work on any projects before getting the ML job? i try to learn by myself but never seems to me any employer would hire me on the basis of doing online courses. So how did you end up crossing that gap?
You need to find an employer who is hiring based on potential or potential + a track record in a different area. I wouldn't hire an ML practitioner with no practical experience. I would hire someone who's produced in other areas and is looking to make the move to a junior ML practitioner (or who has domain expertise in our corner of the world).. It's like the rest of engineering... just because you've taken a course in Python doesn't make you a software engineer or proficient in it. Now show me that you've done things in other languages and we can start talking. Like, courses in ML don't _really_ teach you about things like:

* reproducing model training * deployment of experiments in a CI/CD pipeline * observability of models * discoverability and governance of results * versioning of data / models * optimizing for latency vs throughput * when to use batch vs real time etc

Just like a course in a computer language wouldn't necessarily teach you about CI/CD, horizontal vs vertical scaling, or domain-specific bits.

Just seeing this. This is exactly right ime, I had years of senior full stack SWE experience /track record of SWE at my employ and was able to get myself on a RNN project initially, then expanded from there. I didn't get hired at a new company as an ML person out of the gate.
I found my friend Jason Long’s book to be very useful:

https://www.howtokicksaas.com

The SaaS Build section focuses on building with a team, but other sections don't make assumptions about team vs one-person business setup.

Lots of specifics which certain other books lack. The book is not 100% finished.

I'm stuck on your opening statement rather than your question. I did the 40hr week and now do what you aspire to do.

Your life will be more challenging if you start a SAAS business. It will not be easier. The only people in SAAS I know with an easy life poured their life into their company and things came good. Investors are starting to see SAAS as a 10yr investment, to give you a sense of time. Ironically those I know who have done well are some of the busiest people I know. I guess they are driven and love their work.

I think what you are describing is working part time. Maybe this is a valid option if you want to have more time doing your own thing?

The startup world likes the approach of make a plan and work backwards which is what you are currently doing. I would just suggest you re-frame your expectations. Read Peter Thiel's books but talk to the average SAAS Joe as well as we are not all SAAS rock stars :-)

Thank you for your insight, it is great to get to hear from someone in the trenches and an "average SAAS Joe" as you call it. The keyword in my opening statement is "eventually" as I do understand the need to hustle initially, potentially for a long time. When work is fun it is no longer work, as someone smart once said. What is hard to motivate for me is doing all that work for (mostly) someones else gain and for a product that I personally wouldn't work on on my own time, like I do now in my day to day. Thanks again!
I was part time for a few years working on my saas product before I gave in my notice. I hadn't planned to but got a place on an accelerator programme. You should maybe factor this into your thinking. I'm very glad I just didn't strike out on my own as I had planned. There is a lot to learn about doing business and accelerator programmes are great. You get to work alongside people in the same boat and get access to some of the biggest names in SAAS. My last thought is that sales is one of the toughest areas. As a founder you are the sales person. So read up on that if it's not your area. I think the days of build it and they will come is over. You will find yourself spamming people and maybe cold calling. Words from the trenches as you say.
Sales is hard. It’s 10X harder than development as it’s a new skill we’ll be acquiring. At-least true for me. It’s also heartbreaking when you pitch your idea to potential customers but they don’t resonate. You think people will jump onto cold emails but very few reply. It’s really really brutal going day in and out and being lucky enough to find customers who are willing to take a chance and pay.

When you’re solo, you are the chief everything officer. You are the sales person, the account manager, the customer support, the product manager, the designer, the developer, the always on-duty SRE, and the business admin who keeps up with all the paper work and legalities.

Going solo is hard. But it’s also very rewarding. The learning curve is off the charts.

100%. Running a SaaS is a ton of work. You will get far busier. If you are successful even more.
Glad someone mentioned this. I fell hard for the idea of the mythical SaaS that just produces monthly recurring revenue and magically grows month-over-month. Boy was I wrong.

The reality is lots and lots of customer support, constant development of new features to stay competitive, new (cheaper) entrants cloning your product once they see you're successful, ever-evolving privacy regulations, sleepless nights over security concerns, long payback periods on the cost of acquiring a customer (depending on your pricing), etc.

And Dont forget customer churn .
Not to say "You have this backwards", but starting a company (especially SaaS) is really for people who love to work and want to work some more, not people who want to get out of it. You will take more risk and work harder for potentially more income, eventually.
> My goal in life (as of right now at least) is to start my own SaaS business so that I can eventually quit my 40 hour work week and have more time for things I enjoy doing.

How does it feel knowing you are going to die and get buried and probably never accomplish that goal? Because it’s time for you to open yourself to that grim reality.

A one man SaaS will take a lot more of your time than your 40 hour a week job. Do you plan to have a wife and kid(s)? Those will also take more of your time. Your time is going to get eaten up between your one man SaaS, your family, maintaining yourself (food, sleep, exercise). After all those things have been attended to, then maybe you will have some time to spend on things you actually enjoy.

Be straight with what you want man and don’t beat around the bush. Do you want a SaaS business, or do you just want a way to make great money with as little effort as possible so you can trade work time for fun time doing whatever you want?

Because there is plenty of advice that can be given for the latter, and none of it involves SaaS. The first step to living a life of productive leisure is to admit that you simply want a life of leisure, and go straight for it. Don’t come up with indirect paths like building a SaaS that you think will sound more acceptable or noble to the rest of society or your parents.

But if you’re hellbent on a SaaS because you just want a SaaS, good luck to you. Hopefully building a SaaS is how you want to spend the majority of your time.

> go straight for it

What does this mean, though?

Before you earn the success that affords more free time, prepare for 100+ hour work weeks.

It's a paradox that in order to obtain more free time you'll likely have to spend years handing over hour upon hour to your business.

If you pull it off, however, the business will give you back that time with freedom as interest.

I don't have a book to recommend but this guy's comments are usually gold: https://news.ycombinator.com/threads?id=jasonkester. He offers good advice and seems to live the life that you aspire to. Note the ten years of work though:

> The entire goal of building a business, in my mind, is to get the point where you can lounge on a beach or travel the world and not need to actively engage in anything except the pursuit of happiness. I personally averaged out at a little less than four hours of work per week in 2017, running the sort of low maintenance, feature complete, Software-as-a-Service business that the author spends a paragraph explaining is not in fact a "serious company".

> But look at the product and you'll see craftsmanship. Ten years of work, in fact as of roughly today. But never at the author's pace. Always at mine. Those two things are not mutually exclusive. That's the great thing about building a business. You can do it any way you like.

>If you pull it off, however, the business will give you back that time with freedom as interest.

That's a wonderful way to put it. I will definitely check out his comments. Thank you!

any recommendation on how to do sales?
Ready, Fire, Aim by Michael Masterson is a good read. I got this and read through it. Teaches how to prioritise sales over everything else. If You want to listen to his talk; https://www.youtube.com/watch?v=RvVSVe57gV0

Moral of the story, its way important to start selling even before You write a line of code!. Sounds totally non-intuitive but without actual sales, how will Your MVP be funded.

This is maybe a meta-suggestion, more focused on chunking down problems and the process of working and shipping, but Amy Hoy’s Just Fucking Ship is full of useful advice on how to actually get things out the door. (I’ve taken their 30x500 class too, which is also excellent)

https://stackingthebricks.com/just-fucking-ship/

Here are the things that lead to my startup's success:

Get a mentor who's already been there

Read Traction by Gino Wickman

Read Traction by Gabriel Weinberg

Identify and engage a big enough channel that will sell your product for you.

Build the product that they want. You build what they want, and they'll enthusiastically sell it for you.

Thank you! If I may ask, how did you go about finding a mentor to help you on your journey?