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I’ve been attached to the “shareware” industry since the 90’s, providing platforms to software developers to sell their products. It’s given me an angle of the industry that few get, namely, I’ve seem the sales number for literally thousands of different companies in the industry.

The first thing I would say is that shareware (in the classic definition) is not really a thing anymore, but “try before you buy” software (which is really the evolution of shareware) is very much alive and well.

The second thing I would say is that most people would be surprised by how much some of these companies sell. Certainly not everyone does well, but we see small companies selling tens or hundreds of thousands (USD equivalent) per month. Some reach seven figures a month.

I can’t think of a single company that I’ve worked with that had VC-style funding. Most are bootstrapped with a small minority getting small “friends and family” investments.

It is still possible to make a lot of money with try-before-you-buy software. A few tips:

Don’t underprice. If you can provide enough value that they’ll pay something you’ve got more room in your price than you might think.

Feature limitations work better than time limitations.

75% of you sales come within one day of the trial download, and of those, 75% come within the first two hours. It’s important that the product conveys why and how to buy.

Don’t forget about other markets. In the early days most sales came from the US. These days, the US represents about half. When you get traction, consider translating your product and don’t forget to offer your product for sale using multiple currencies and payment methods. Third-party e-commerce platforms make this easy. They’ll also take care of a lot of the regulatory burden for you (taxes, export controls, fraud & chargebacks, etc.).

If your product is targeted at large companies, offer premium support for a fee. Something as simple as a “response by email within one business day” SLA can be enough.

SEO matters a lot in helping people find your product. High quality content about the problem your product solves helps a lot. In the early days find where people who need your solution are talking about their problem. Be transparent, offer genuine, non-spammy help as a solution expert and people will allow you to talk about your product. This can help a lot as you get established.

If someone will donate, they’ll buy. You’ll feel more benevolent asking for donations but you’ll make a lot more money if you sell the product. We’ve seen both models. It’s not even close.

If your product is not targeted to a highly-technical audience, open source might sound cool but means nothing to them. They won’t buy more because it’s open source.

I could go on and on. I’ve said enough but there is still plenty of opportunity here. It takes time - be patient. Most of the successful companies I know started as a side gig.


Here's my programmer cold start algorithm for those interested:

1. Go to indeed.com

2. Type in 'software engineer' or 'data scientist' or something like that.

3. Don't put in a city.

4. Put the money slider all the way to the top.

5. Open a few pages of job postings in tabs.

6. Write down every word you don't know.

7. Repeat the process by searching for each one of those words you don't know and then write down additional words you don't know.

Now you have a list of what technologies are valuable in the zeitgeist and your mission is to determine why each technology exists and what it's use case is. You'll then be armed with a larger and more modern toolbox full of tools to reach for when the time comes to solve that kind of problem.

Rinse, repeat every few years.

Hope that helps someone. :)


> Do you reach out for weekend lunch dates just to chat?

This is not necessarily about ex-coworkers.

In general, weekend time is more guarded and precious so try to meet for a coffee/drink after work. Or you can both go to an event that is related to mutual interest (tech is possible but would not recommend it). Trying to meet more than one person at the same time also leads to scheduling difficulties.

If you want to meet up with more than one person, consider hosting a Tuesday night dinner party. Nothing fancy, do take out if you can't cook that well. Tuesday night is usually an "off" night for most people.

Ideally, you meet with people you would like to stay in touch about every 3 months. A person is not really in your direct network unless they know who you are and can recognize you in person and know what you are currently working on and have seen you in about the last 3 months. But here's the catch, you don't necessarily have to be directly in contact with everyone. A simple "How is Jane doing? Have you heard from her" can keep you updated enough.

There are some people from work that you might think you'll remain friends with after leaving with whom you do not meetup with again. That is ok. People drift off. Maybe it was just the recurring coincidence of time, location, and possibly purpose (going to the office for years) that made you "friends".

Like the saying goes:

Friends for a lifetime

Friends for a reason

Friends for a season.

The most naturally extroverted individuals that I know have many social circles. One friend I know always buys two tickets to a performance and never lets the other person pay for it.

Finally true friends whom are hard to find are those who you can open up and be vulnerable with.

Facebook has bastardized the term friend. Not everyone is going to be your friend, as it requires reciprocity and shared caring.


What about Mark Zuckerberg who has an annual salary of $1.00?

"The only good diff is a red diff"

I know this was half in jest but it speaks to a larger point, that of the "implementation ghetto".

I'm going to get a lot of pushback for saying this, but there are basically three roles in any company: (a) people who do the work, (b) people who make sure the work gets done, and (c) people who decide what work to do.

If you follow the strategy outlined above, you will never rise beyond a pure implementer of someone else's vision.

Empirically, understanding more about the business domain and industry seem to be important if you want to do (b) or (c). If anyone has more tips, I'd love to hear them.

EDIT: When I say "above", I'm talking about in the comment two levels up, not the article.


You haven't lived until you've used Apptivate[0] to map the function keys to your most commonly used apps (I think with them "inverted" so you don't need to hold "fn"). I have F1 -> Finder, F2 -> Postico, F3 -> Chrome, F4 -> Sublime, F5 -> iTerm2, and can touch type each of them. It feels great to easily flip between those apps as necessary. It's like Cmd+Tab but goes to exactly the correct application each time.

I'll still probably get one of these MacBook Pros eventually, but the lack of F1 buttons is a loss.

[0] http://www.apptivateapp.com/


As a security researcher it saddens me that a device like this is being marketed as anything of use in a pen-test. It is at the end of the day a destructive device and nothing more. It's a device to physically destroy computing platforms and is otherwise useless in the demonstration of any threat vector which can be reasonably mitigated. "But wait, it shows a lack of surge protection in USB implementations and manufactures should take steps to include that level of protection" you might say. Well, no. This is an edge case and one which cannot be solved.

In the real world, surges of this nature on a USB buss only happen as a result of a device like this and from nothing else. Yes, there are power surges, but those are typically from the AC power grid feeding your home.

Ultimately, if a malicious actor is willing to plug a device into a USB port which through the introduction of high voltage into the buss will fry the hardware there's nothing that can be done.

Today this device introduces a 200V spike; however, there's nothing holding it back from doing a 2,000V spike or even a 200,000V spike. There are no technologies available today which can stop high voltage from frying computers because at some point, with high enough voltage not only will the MOV or TVS diode burn out, but the voltage will arc to other components.

Making dubious claims that manufacturers can take steps to mitigate the risk is well, dubious. It's like claiming we must all buy protective clothing because we could be tazed while ignoring the fact a tazer proof shirt leaves a fair amount of the body still exposed. This is not a legitimate pen-testing tool, it is a destructive device. Is it good to know that it's possible for someone to fry a computer via the USB buss? Yes it is because that knowledge could be used to catch a miscreant. Is use of this device any different than smashing a computer, kiosk, or point of sales terminal with a baseball bat? No, it's the same.


"When art critics get together they talk about Form and Structure and Meaning. When artists get together they talk about where you can buy cheap turpentine." - Picasso, supposedly

Talking about this stuff is only natural.

As for the rest of the OP, not knocking it (or the book), but it sounds like he just read Catcher in the Rye or something. Employees have been jockeying for status inside firms and across firms as long as there have been employees and firms.


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