RightMessage's Origin Story: How We Turned Consulting and a Course Into a SaaS

By Brennan Dunn

Almost exactly a year ago, we publicly launched RightMessage.

Like with just about anything new, there were (and are) plenty of things we're figuring out. We still haven't found product-market fit, and we're still struggling with bringing immediate clarity to the age old question: What does your product do, and why should I care?

But we've done well. We're at about $20,000 a month in monthly recurring revenue.

In this recap post, we'd like to share a bit about what we learned over the last year and where we're going both as a company and a product.

(And our not-so-secret hope is that from our experience you'll take something away that could directly benefit and impact your business.)

How we decided to start RightMessage

Since 2012, I (👋 I'm Brennan, RightMessage co-founder and author of this recap) have been personalizing DoubleYourFreelancing.com.

It started out relatively simple: if someone's on my Infusionsoft list, don't show them the newsletter opt-in.

And then it slowly became more advanced. Headlines on sales pages would change. Testimonials would get swapped out. The way I described different products would be ever-so-slightly adjusted based on tag and custom field data I had about someone.

Why'd I start doing this?

Easy. Ten years ago, I ran a web agency and my primary job was to get us clients. Every deal was closed in person or over the phone, and I became pretty adept at being able to dynamically inject language and case studies based on who I was talking to.

Startup bro who wants to build an MVP? I knew how to sell him on hiring our agency. I could fish out why he wanted to start a company and align what we could do toward that end.

Established CEO? Wants to refine how things are handled internally and commission some custom software? Awesome. My approach and tact would change when talking with her, but the "offer" – me and my team – would remain the same.

How I sold changed from project to project.

So why couldn't my website's sales pages do the same thing?

Try to figure out who someone is and what they want, and then just make the sales page a bit more relevant to them?

I went about writing some custom code (which opened up a wholeeeee can of worms) and linked my site with my email marketing app, and went about personalizing calls-to-action, headlines, and other bits of the website.

...And it worked. Conversions and sales went through the roof, and I wasn't shy to share the results and how I was going about tracking everything on Twitter.

This led to bigger companies coming my way. A 5% increase in sales for me gave me a few additional niceties; but a 5% lift for a much larger company would be game-changing.

I took on about ten consulting gigs over the last few years that all had to do with on-site personalization. I just recreated what I did on their website and ended up writing a lot of custom code and custom sales copy.

Once again, success. My clients were getting results.

But client work could only scale so much, and I didn't start Double Your Freelancing and other ventures to wed myself to client work.

So I created a course called Mastering Drip, which is an advanced-level course on automation and personalization. In the course, I bundled code samples that I'd used to personalize my own site.

The problem with the course? It was bought by marketers. And throwing a bunch of JavaScript at a marketer isn't going to get them far. They wanted something more turnkey. More plug-and-play.


Here I had 10 consulting clients and close to 400 Mastering Drip customers who had effectively validated that personalization was something that they'd pay money to get access to.

The former group wanted done-for-you, and I was able to work 1:1 with them to really figure out what was at stake, why they were interested in personalization, and how my work directly impacted them.

The latter group (course customers) helped me test at scale the selling of automation and personalization through a traditional "Buy Now" sales page. I was able to bake in everything I learned selling personalization consulting into a self-serve offering.

"Shai, want to help me build something to offer these course customers?"

My good friend Shai Schechter had been helping his own consulting clients with marketing and personalization, and they were seeing the same big results I was — but his background was always in software. I asked him to come onboard as the technical co-founder for this thing I wanted to upsell customers of Mastering Drip. We didn't have a name... Personalized Panda sounded good? (After all, I ♥️ pandas!)

We decided to go for it. (And we changed the name to RightMessage.)

This would be a thing I'd funnel people from my course over to, and Shai would turn it into a self-hosted SaaS.

And then Teachable reached out...

Getting our first customers

Ankur Nagpal, CEO of Teachable, reached out and wanted to see if we were willing to help them personalize their site.

For a company with zero customers to be approached by Teachable... yeah, that was a big deal. Shai and I were actually in Las Vegas at the time (at MicroConf), so we both jumped on a conference call to feel out what they were looking for.

"Maybe this is going to be bigger than just a side project?"

I was at a crossroads...

I really, really wanted to get back into software. Friends of mine like Nathan Barry of ConvertKit had given up successful online course businesses to go all-in on software, and I had some (humble) success with running a software company – in 2011, I started a project management SaaS that got up to a few thousand in MRR, which I sold in 2016.

And Shai was looking to escape consulting.

But even with a pseudo-enterprise deal like Teachable, we couldn't replace Shai's income just yet. I figured I'd just split my time between Double Your Freelancing and RightMessage, and that we'd bootstrap our way toward being able to replace Shai's income. And then we'd look at paying myself and then maybe growing a team.

So that's what we did: I worked part-time on RightMessage, and Shai worked part-time.

We put together a very simple sales letter, threw up an opt-in form, had some people opt-in (largely from my incessant tweeting), and then started sending out emails about why personalization was such a big deal.

The first version of the product was butt-ugly but really well developed. Shai did his thing and made an incredibly powerful rules engine that would let you change content on your website based on conditions, like referring domain or UTM parameters.

While Shai built the product, in my spare time I'd do the occasional demo with people on our list. I didn't really expect to sell many people on these demos (the product just wasn't there yet), but – if anything – I'd learn a lot about what was missing and could relay that on to Shai.

We actually had a few people from these demos convert. And by dangling the SaaS in front of the 400ish customers from Mastering Drip, we decided to try to raise a bit of money by selling ten customers on an annual deal and we brought in $6,000 (truthfully, we just picked a random number – $600 – and made that the Early Access discounted annual price.)

And then I got an email...


Raising a seed round

I've always bootstrapped. I'm a dyed-in-the-wool Amy Hoy acolyte, and am deeply suspicious of venture capital, founders being fired from their own company, and placing investor demands over customer needs.

But we really weren't growing as fast as we needed to – our attentions were split between RightMessage and our other companies.

And we were early. Hardly anyone was doing what we were doing, and there was a tremendous amount of work ahead of us: we had to both convince prospective customers of what personalization is and why it matters, and then we had to sell them on the product.

The more we looked into seed funding, the more it seemed like it might work out for us.

We found out about this financing model called SAFE (Simple Agreement for Future Equity) developed by YCombinator.

Basically, it allowed us to easily raise money from angel investors and we wouldn't have to give away any equity until there was a liquidation event (like selling the company.) It was super lightweight and easy to setup, and we ended up raising $500,000.

Having half a million in the bank can be dangerous.

But as a fully remote company, we were able to hire a team for a fair price from all over the world (Australia, Canada, and the US) and we didn't need to deal with pesky expenses like rent or furniture.

We did get a bunch of high-priced consultant types reaching out to do work for us, but the bootstrapper instinct stuck with us and we kept things in-house.

We hired 3 people: a marketer to help me, a developer to work with Shai, and someone to help us with customer support but, more immediately (we didn't have that many customers), creating help documentation for the product.

And we were off...

Over the coming weeks, we'll be sharing everything with you:

  • How we botched up our pricing
  • Why our marketing site and our messaging was broken – and the importance of focus
  • Enterprise or self-serve?
  • Why RightBar wasn't the hit we thought it would be
  • And why RightAsk completely changed everything for our company
  • How we're securing partnerships (and why our early partnerships floundered – hint: it's all about the offer!)
  • RightCTA and why you need an "offer funnel"

So stay tuned! We have a lot in store. (And we'd love to hear from you. Let us know on Twitter what you want us to cover.)

Lesson Learned: Validating A SaaS Through Consulting And/Or Courses

At the end of each of these articles, I'd like to share a bit about how I think our experience can help you.

Validation is one of those things that gets talked about a lot, but often times – especially for something as involved as writing software – causes founders to freeze up and never actually ship anything.

We could have started RightMessage with the assumption that "well... it worked for Brennan, so maybe other people want this too?"

Lots of products start this way: founder has issue, founder scratches issue with something built for themselves, founder then tries to sell this solution to others.

This can work, sure.

But it requires making a lot of assumptions about what people want and how to go about selling it to them.

Before any company was formed, money was raised, or code was written, the value proposition of RightMessage (segmentation and personalization increases conversions and sales) was tested.

If you think about it, there are solutions that exist on a spectrum. Consider the problem of "how can I make my website get more search traffic?"

Solutions include...

  • Hiring a SEO consultant who has the knowledge and the implementation ability to do that all for you.
  • Buying software (like Yoast) that does a lot of standard things out of the box and entirely turnkey. Requires some, but not much, SEO know-how.
  • Buying a book (like this one) off Amazon and acquiring the knowledge needed to do it yourself

All of these options could eventually help you get more site traffic – but they go about solving that problem in different ways.

Hiring a consultant is "Done-For-You" – you use your expertise to do it all for me.

And reading a book or buying a course is "Do-It-Yourself" – teach me how to do what you do.

And, often times, software sits in the middle.

Before creating RightMessage, a tremendous amount of experience and validation (in the form of $$$) occurred by selling personalization consulting (Done-For-You) and then, later, by selling personalization instruction (Do-It-Yourself).

Selling consulting requires you to converse. Dialogue drives the sale. You discuss the client's needs, you talk about what you're going to do, and you negotiate what it will cost. You hear all objections first hand – whether it's about personalization itself or the cost – and you're able to then counter them ("here's why personalization is so valuable...") by responding directly to people's questions.

All this dialogue eventually leads you to being able to create a killer monologue – a sales page.

By the time I was ready to write the sales page for Mastering Drip, I already pretty much knew what to say. I just had to rehash dozens of conversations I'd already had with clients, both prospective and actual, and incorporate it all onto a web page.

Now I could turn the high-touch experience (selling consulting) that I had into low-touch sales (selling a course.) I was able to sell my course more effectively because I wasn't just shooting in the dark – instead, I had turned a wealth of first-hand experience selling this stuff one-on-one into a sales page.

This meant that by the time we were ready to seriously consider "should we build software?", we started with a tremendous amount of wind at our back:

  1. People had paid a lot of money hoping that personalization would help increase their sales.
  2. There was already a number of case studies I had at my disposal, both from the course and consulting, that I could use to bolster the value prop of RightMessage.
  3. 400+ people had paid for the "Do-It-Yourself" equivalent of RightMessage, and those people were primed to buy RightMessage.
  4. I had a lot of experience selling personalization both high-touch and low-touch, which helped us get our first customers.

Did this solve all of our problems? Nope. We still struggled (and struggle) to sell something as new as personalization.

But every day, the room gets a little bit brighter and we have a better understanding of who we're helping, what they need, and how to best describe how we're able to solve that need.

And by validating through consulting and courses first, we were able to start in a slightly brighter room which helped us have a more successful launch.

Next week I'll be sharing everything about our launch. A lot of things went right – but plenty went wrong. Stay tuned!