I about to do something kind of crazy
You should read this if you are a freelance software consultant or involved in selling software services in any way. I promise you won't regret it. There's also some fun personal history in here...
In about five hours, my MSABundle mailing list subscribers are going to get a pretty crazy email from me. Now some of you might already be members of that list too, and if that’s the case then this is just a little teaser.
However, if you sell consulting services (freelance or agency) and you’re not already on that list then I want to give you a heads up in case you want to go ahead and subscribe now: msabundle.substack.com
I’ve wanted to do this since back in the Hashrocket days, but never quite worked up the nerve to go through with it. I actually feel like it’s one of the riskier things I’ve tried lately, but if it works then it’s going to make generate a good amount of money.
What’s the risk? I’m not actually worried about it failing, What I’m worried about is it being too successful, and what the unintended consequences might be.
I can hear you thinking, what is it already?
I know, I’m doing that thing that Internet marketers do all the time, when they keep you waiting for stuff. Building suspense.
Okay, okay… I’ll tell you.
Part of it anyway, the part that worries me the most.
I’m going to help people write their proposals.
I’ll tell you exactly how I plan to do that in that other email, the one you’ll get access to if you sign up for the MSABundle substack. What I want to do in this email, since it’s a bit more personal, is to tell you why I’m doing it.
I’m awesome at writing proposals for software consulting, so I have this theory that other people will pay me to help them write their proposals.
But why am I so good at writing proposals for software consulting?
Ahh, now we’re getting to my favorite thing to sell, which is myself. Ha!
For starters, I love the art of writing and I write every day. I’m good at it, and constantly working to get better. Takes a lot of writing skill to write a compelling proposal, and not that many people have it.
There’s also the decades of experience I have with sales in general, and specifically with writing proposals offering custom software development services.
I started my first real software consulting company at the age of 21. This was after getting fired from my job as a Series 7 and 63 licensed junior broker pumping penny stocks at Investors Associates, one of the firms that inspired the movie Boiler Room. If you’re curious about that, I write about it in my book How To Eat Nachos and Influence People.
So there I was, young and out of work during the tail-end of a terrible economic downturn. Mostly because I had nothing else to do, my best friend Nate and I started a software company called Bitwise, headquartered in his friend’s dad’s office in Cliffside Park, NJ overlooking the Hudson River and Manhattan. We were writing desktop software to manage pager (aka beeper) customers, which at the time were sold all over the place by little mom and pop shops. This was before cell phones reached any sort of critical mass or big mobile telecom companies existed.
Eventually we were running low on funds and motivation, so we brought in a friend of Nate’s called Tom as an “investor”. This guy was super impressive in certain ways. He was at least 15+ years older than us and a real character. When I say “real character,” I mean it. Trust fund orphan, off the charts IQ, veteran of the Office of Naval Intelligence service with all sorts of spooky stories—sounds cool right?
Problem is that Tom was also seriously bipolar. Between pathological lies, and episodes of inexplicable verbal and sometimes physical abuse, he would also sometimes disappear for days or weeks at a time without telling us where he was going. At least once the disappearance was blamed on getting lost in the desert on a heroic dose of LSD, leaving me alone to work on our biggest project.
The reason I tolerated Tom is that he had three things that I did not, and more importantly, he shared those things freely: money, drugs and connections to important people with important projects. Not necessarily in that order.
As soon as Tom got involved, he persuaded us to drop our silly little beeper project and start an ISP. We installed a T1 line and some servers, and presto, some months later we were running an ISP. Or at least we thought we were, because Tom insisted on managing the customers. That did not matter, because in 1995, nobody had a T1. The speed of a T1 (1.55Mbps) was insanely fast in that era. I remember downloading one of the first versions of the Java SDK and nearly falling out of my chair when it took less than 10 seconds.
And I did mention that Tom had lots of friends with money and important projects, right? That’s where my career in consulting sales began. We morphed into a consulting company, simply because Tom’s friends wanted us to work on their projects.
During the batshit insane 18-month period that followed, I wrote at least half a dozen significant proposals. I’m not talking about the 9-10 page form that my proposals usually take these days. Remember this was long before agile software was a thing. These were big proposals, sometimes with hundreds of pages, full of use cases and technical specifications, and diagrams galore. Waterfall at its finest.
The ones I can remember the best:
1-800-SERVICE We actually won this deal and worked on it for awhile. It was a dispatching system, implemented in Smalltalk. They were planning to plaster the number on billboards all over the country. A one-stop call to get pretty much any kind of on-demand service that you needed, from plumbing to babysitters. It failed because once the dot-com boom started, anything to do with plain old telephone lines was BOOOOOORING.
Robotic Security System for Sensormatic Amazingly, even though this project was absolutely ridiculous, it’s not the most off-the-wall project we got involved in, that would be…
Internet Porn Site Tom was friends with the operators of a notorious strip club in Upstate New York, and brought them down to the office one day so that we could pitch them on starting a porn site with us. This is one of many episodes in my past that might have set my life’s path on a completely different directly. The main reason it didn’t is that I was terrified that my wife would cut my balls off if she found out. I was also terrified about what the mob would do to us, well, for any reason at all. Tom didn’t help my motivation either—when the mob guys left the office that day, he shoved me around and punched me in the face for contradicting him in front of his buddies about the meaning of www in a website’s URL. The guy was a piece of shit, is what I’m trying to say, and I rage quit the company the next day.
Consulting Proposals
Where was I again? Oh that’s right, talking about why I’m offering to help people with their proposals.
One of the main reasons is that I’m obsessed with this idea of selling your byproducts. I’m pretty sure I got the concept from the 37Signals guys; in a nutshell it means monetizing byproducts of your normal, day-to-day work.
I’ve been doing exactly that for almost 10 years now, via my ecommerce website MSABundle. It generates a few hundred dollars a month, with little to no effort. But it’s static, and decaying. I’ve wanted to do something fresh with it for years, but what?
The answer arrived recently, when I took over business development at my 50-person web design and development agency. I’m spending at least half my days doing sales. A lot of that time is spent writing proposals and contracts. So now I have a steady stream of new byproducts to sell and draw inspiration from for new educational content.
Wait, didn’t you say you were going to do something crazy?
Yeah, I did. And you’re going to have to sign up for the MSABundle newsletter to find out the exact details, but I’ll give you the gist.
I’m going to sell a monthly subscription to my proposals and contracts. Once a week, I’ll pick an interesting proposal from my backlog, write up my thoughts about it, maybe add some context and results, and send it to the paid mailing list members.
The idea is that if you sell software consulting and projects, the information I provide will serve as interesting educational material, inspiration and also a source of pricing data. Cause the only thing I’m going to strip out of the documents is client name and confidential information, if any. I’m leaving dollar figures in there.
For an extra fee, I’m giving paid mailing list members the option to retain me as their personal proposal consultant. Meaning they can send me copies of their proposals at any time for review and suggestions.
If the plan is wildly successful, it might be too much work. Or what if my potential clients figure out that I’m monetizing their proposals and don’t like it.
But hey, there’s also upside. Money! And exposure for myself and for my firm. When I ran Hashrocket I’d literally travel around the world showing off how we ran the company (including contracts) at conferences. I had a talk that I delivered at least a dozen times over the years called The Hashrocket Way. People ate it up, and it gave us a ton of prestige. I’d get incoming leads, referred to by other development firms that we had never even heard of. Because they were convinced that we were awesome, not by working directly with us, but by being consumers of all the material we put out talking about how we did what we did for our customers.
So anyway, that’s what I got. It’s past my bedtime here in Colima, so I’m going to call it a night right after I hit this little publish button.
Before I go, let me remind you that I also have my personal paid newsletter, where I write all sorts of life musings and stores that I’m afraid to share publicly. If you enjoy my writing, it’s a good way to get a taste of what I’m like unfiltered.
Check it out here.