I started my software career by giving software away.
Then I nearly went broke.
So I stopped.
More than 25 years later, I’ve started giving software away again.
Maybe I’ve learned something.
Maybe I’ve forgotten something.
I guess we’ll find out.
I never knew how to sell software
When I first started, I didn’t have some grand theory about software business models.
I didn’t know how to sell software.
My first attempt failed miserably.
I was unemployed at the time, trying to work out how I could turn the software I was writing into something that might actually pay the bills.
Then a friend introduced me to The Cathedral and the Bazaar.
Open source immediately resonated with me.
Not because I’d worked out some clever commercial strategy.
It just seemed like a really good way to do the thing I actually wanted to do:
Solve people’s problems.
So I created an open-source Java SSH API called J2SSH.
People downloaded it.
People used it.
It became popular.
And through that, people began to know who I was and, more importantly, trust that I knew something about SSH.
There was just one small problem.
It didn’t pay the bills.
We tried selling support for the open-source software.
Nobody really wanted it.
I think we sold one support incident.
Meanwhile, I was running out of money.
So I sold my house.
I used the capital to start my second company and kept going.
Then one day, sitting in my office, I had what at the time felt like a Eureka moment.
What if we took what we’d learned building J2SSH and started again?
Make it faster.
Make it lighter.
Add more features.
Add SSH1 support.
Make something genuinely better.
And sell that.
That became J2SSH Maverick.
And it worked.
We sold our first licence in the same month that I ran out of the money from selling my house.
Perfect timing.
Or just damn lucky.
Either way, I’ve never looked back.
That’s where the gate started
Maverick wasn’t just J2SSH with a price tag attached.
It was better software.
And it came with guaranteed commercial support from people working with SSH every day.
Customers paid for that.
Some of the customers we acquired back then are still paying us today.
So I’m certainly not going to sit here 25 years later and tell you that selling commercial software was some terrible mistake.
It gave me the freedom to continue developing.
I’m still maintaining that API today.
But it was also the beginning of something else.
The gate.
Initially, the gate was pretty simple.
Download the software.
Use it.
After 14 days, it stops working unless you buy it.
Then the company grew.
I employed more people.
We created more products.
And gradually, more gates appeared.
Registration forms.
Licence keys.
Lead capture.
Trials.
Sales processes.
Over the years, people who knew more about sales and marketing than I did told me how software should be sold.
And I listened.
I’ve never considered myself a salesman.
They’d researched this stuff.
Presumably they knew better.
Add the registration form.
Capture the lead.
Control the trial.
Follow up.
Convert them.
Each individual decision probably made perfect sense.
But somewhere along the way, I think I lost sight of the instinct that got me into this in the first place.
I wanted to solve people’s problems.
We’re pissing in a pool of piss
The software industry is very different today.
There is so much fucking software.
Open source.
SaaS.
Cloud services.
GitHub projects.
Apps.
Tools.
Platforms.
And now AI is dramatically reducing the time and cost required to create even more of it.
We’re pissing in a pool of piss.
Yet everywhere I look, we’re being taught increasingly elaborate ways to put barriers around all this software.
Capture the lead.
Offer the lead magnet.
Start the trial.
Book the demo.
Qualify the prospect.
Nurture them.
Convert them.
And I’ve increasingly found myself asking:
Who does all this actually benefit?
Because I know what I do when I encounter it.
I look for something else.
Maybe there’s an open-source alternative that’s slightly harder to configure.
Maybe it’ll require more maintenance.
But if I can actually use it and it solves my problem, that’s often where I’ll go.
So why would I expect my users to behave differently?
Make them users
Imagine someone discovers Nodal VPN.
They download it.
Install it.
It works.
A few people start using it.
Then a few more.
Before long, perhaps 50 people are using it.
Something important has happened.
We have a user.
Actually, we have 50 of them.
Now imagine the traditional gated version.
They install it.
It works.
They start letting people use it.
Everything is going brilliantly.
Then:
Your trial has expired.
Pay us.
We’ve taken someone who was successfully adopting our product and forced them to make a purchasing decision.
And what do people do when they’re making a purchasing decision?
They look around.
They compare products.
They install something else.
The gate that was supposed to create a customer may have just destroyed the user we already had.
There’s an old piece of sales wisdom that says:
It’s easier to sell to an existing customer than find a new customer.
I’d reframe it.
It’s easier to sell to an existing user than find a new customer.
So that’s what I want.
Users.
Optimise for users, not revenue
That probably sounds like a ridiculous thing for the CEO of a software company to say.
Revenue matters.
Believe me, I’ve experienced what happens when it runs out.
What I’m questioning is whether every interaction with a user needs to be optimised to extract revenue from them.
I’m perfectly comfortable with thousands of people using Nodal VPN and never paying us a penny.
Because they’re using Nodal VPN.
They’re not using Tailscale.
They’re not using OpenVPN.
They’re using our software.
They know it.
They’ve configured it.
They trust it.
They might recommend it.
They might take that knowledge into their next job.
And one day they might need something more.
I’ve seen where that can lead.
Someone once downloaded and installed a product I’d created called SSL-Explorer.
They used it.
They put it into their corporate environment.
Eventually, that company acquired us.
Thanks, Sean.
So you’ll forgive me if I’m slightly sceptical of the idea that I need to put barriers between people and my software in order to create commercial value.
Sometimes the best sales strategy might simply be:
Let them use the fucking thing.
So what do we sell?
This is where the phrase I’ve been using needs a little qualification:
Software is the gift. Expertise is the paywall.
Expertise is certainly part of it.
But it’s broader than that.
The principle is that you should be able to download our Community software, deploy it and solve the problem without paying us.
We’re not going to deliberately cripple it to force you into becoming a customer.
But if our software becomes valuable to your organisation, there will naturally be things you need as you scale.
Take Nodal VPN.
Active Directory integration is available to Community users.
Want Entra ID or Google integration?
Those are commercial features.
Your organisation is already paying Microsoft or Google because those services provide value and convenience. If integrating our software with them provides additional value, I think it’s reasonable to ask you to pay us too.
Need detailed auditing and SIEM integration because your organisation has SOC 2 or ISO compliance requirements?
That’s commercial.
Need site-to-site configurations because Nodal is becoming part of a larger network infrastructure?
Commercial.
Community support happens publicly through r/Jadaptive.
That means the answer to your problem becomes part of the community knowledge and can help the next person too.
Need to discuss your infrastructure privately with one of our engineers?
That’s technical support, and that requires a commercial relationship.
Even the free appliance asks for something in return.
Anonymous Telemetry.
You get uncapped use of a fully functional appliance. We get information that helps us understand how it’s being used and improve it.
Can’t or won’t provide telemetry?
That’s fine.
Buy a licence.
The principle isn’t complicated:
You have found value in our product, and now you’re scaling the use of that product. Now it’s time to invest in that product.
That’s not a punishment for becoming successful with our software.
It’s an exchange of value.
This isn’t freemium
There’s an important distinction here.
I don’t want the free version to be deliberately irritating.
I don’t want to create artificial limits whose sole purpose is to eventually annoy you enough to pay me.
The software should solve the problem.
The commercial relationship starts when your organisation gets additional value from going further.
Integration.
Scale.
Governance.
Compliance.
Private support.
Expertise.
That’s where I think the line belongs.
Not between someone with a problem and the software that can solve it.
Maybe this is a bootstrapping strategy
There’s another reason I’m interested in this model.
The modern SaaS merry-go-round is expensive.
You need marketing to generate leads.
People to qualify them.
Salespeople to convert them.
Systems to manage them.
More marketing to nurture them.
More people to retain and expand them.
Then you need to sell more software to pay for all the machinery you’ve created to sell more software.
We’re bootstrapping.
Maybe we need a different game.
AI is already dramatically reducing the cost of building software.
What happens if we reduce the cost of acquiring users too?
Build something useful.
Remove the friction.
Let people use it.
Earn their trust.
Then create a commercial relationship when the value they’re receiving gives them a reason to have one.
Maybe that’s not the future of software.
Maybe it’s just a better way for us to build a software company.
I’m fine with that.
I don’t have a crystal ball
Do I know this is going to work?
No.
If I could see the future, I’d be a Bitcoin millionaire.
I was messing around with Bitcoin when it was worth about a dollar.
I was actually generating the bloody stuff.
Why the fuck didn’t I buy $1,000 worth?
So no.
I don’t have a crystal ball.
I have a gut.
And my gut tells me this approach will resonate with developers, DevOps engineers and sysadmins.
The people who actually need the software.
I don’t want my first meaningful interaction with an organisation to be persuading its CTO to let their engineers trial our product.
By the time it gets to the CTO, I want it already to be part of their infrastructure.
Let the engineer solve their problem first.
The commercial conversation can come later.
Build it and they will come
I’ve always liked the Field of Dreams idea:
If you build it, they will come.
I’ve realised there’s a slight problem with that over the years.
You still need a fucking signpost.
That’s what I think marketing should be.
I’m not rejecting marketing.
I’m writing more than I have in years.
I’m talking to people on LinkedIn.
I’m making Bob videos.
I’m sharing what I’m building and what I’m learning.
The signpost matters.
It tells people:
There’s something over here that might solve your problem.
What I’m rejecting is the manufactured process and friction companies put in front of their software that prevents users from actually solving that problem.
I don’t want the signpost to lead to a locked gate.
Back to where I started
There’s something else I didn’t expect from all of this.
It feels liberating.
I’m working on things I love.
I’m writing.
I’m making Bob.
I’m talking to people about things I genuinely believe.
I’m building things I actually want people to use.
Rather than spending my time trying to persuade someone to buy software they haven’t used yet.
I’m not a spring chicken anymore.
I could probably retire and have a reasonable life from what I’ve earned.
Assuming I can ever sell that fucking property.
Kelly tells me I’ll never retire anyway.
She’s probably right.
My mind works at a thousand miles an hour. She sometimes describes living with me as being on the Ludup Rollercoaster.
There will always be another idea.
Another problem.
Another thing I want to build.
Another song I want to write.
I’m not writing this because I think everyone should stop selling software.
I’m not selling you a methodology.
And I’m certainly not claiming I’ve discovered the next great software business model.
I’m just sharing what I’ve observed after more than 25 years of doing this, and what I’ve decided to do about it.
If there’s something useful in that for you, take it.
That can be a gift too.
Twenty-five years later, I’ve somehow ended up back where I started.
Someone has a problem.
I think I can solve it.
Here. Use this.
If it becomes valuable enough that you need more from us, we’ll be here.
Maybe it works.
Maybe it doesn’t.
But for the first time in a long time, I’m listening to my gut.
And I’ve fallen in love with what I do all over again.