Garrett Dimon: Hello, we’re here today with Brennan Dunn of Double Your Freelancing and RightMessage. How is it going, Brennan?

Brennan Dunn: I’m doing good, Garrett. How are you?

Garrett: I am fantastic. I’m really excited about this conversation. Can you give us a little bit of history, help us understand the arc in your trajectory that got you to where you are today with RightMessage?

Brennan: Yes, a quick backstory. Started by first startuppy thing at a college back early 2000s. We did regeneration for mortgage purpose and stuff. That was interesting. Taught me a lot about business. Taught me a lot about the basics of doing something like this.

Our whole model back then was doing AdWords to generate leads, doing contract sales, then generating leads for our clients, and making money that way. Mortgage bubble burst. We were out of that business pretty quickly. That led me to eventually consulting. Started off freelancing.

Grew to an agency. Got it to 11 people and saw people like you, Amy, others who had software businesses and really wanted to get out of having a really high amount of fixed overhead with three active clients at any given time paying the bills. I wanted to flip the equation and have a lot of people paying a little bit of money.

I did not like the idea of writing e-books and stuff, but I realized that people were really getting a lot of value out of my free content and there was a lot more I could say.

A big pain point for me, and I was going through Amy Hoy’s course at the time, running this agency, struggling with our own project management concerns, so did what I think a lot of us do, which is scratch your own itch.

I started a company called Planscope, which was – or is, I should say – a project management tool, but it’s targeting freelancers. It’s very budget focused and very focused on a lot of the gotchas that freelancers have when working with clients.

Did that. Realized it’s hard to sell SaaS. Didn’t have an audience of any sort at the time, so I started writing about what I learned building this agency. I wrote about things that were kind of tangential to freelance project management, like – How do you get clients, how do you pitch them, how do you write proposals, and so on. That did well.

The goal was people would find that content and then sign up for Planscope. Didn’t really happen as much as I wanted that to happen, but what really ended up happening was I started to create…I was very concerned doing this because my background is I’m an engineer.

I did not like the idea of writing e-books and stuff, but I realized that people were really getting a lot of value out of my free content and there was a lot more I could say. Because Planscope wasn’t working like I needed it to, I started creating E-books, courses, and so on.

This started to do extremely well, to the point where Planscope was becoming a thorn in my side in that I was still running the SaaS and people were depending on it, but I was basically full-time doing this course info stuff for freelancers.

Got to the point where I, like you, reached out to a FE International to sell the product. I didn’t sell the company. I just did an asset transfer of the product. That got me out of Planscope. Made a small amount of money out of it, nothing huge, but this let me focus all my energy on running Double Your Freelancing.

Double Your Freelancing – which is what the content marketing arm of Planscope became – became my full time. I was really focused on that. Through doing that, I ended up realizing there’s a lot of different types of freelancers, different stages of business, some wanted the agencies, some haven’t even started yet.

I started dabbling in website personalization, which, for me, was fair enough. If you were building a SaaS, if you go to your dashboard, you see your data, not other people’s data. It’s really just a bunch of “if” conditions, usually, that say, “If they have this, then show this.” I thought, “Why not do the same, but on WordPress?”

That got me down this rabbit hole of website personalization. It did really well. It got me on the radar of a few companies, who were considerably bigger, who said, “Can you do this for us?”

That got me down this rabbit hole of website personalization. It did really well. It got me on the radar of a few companies, who were considerably bigger, who said, “Can you do this for us?” I did that for them. I released a course on automation and personalization. It did really well.

I included the source code that I used on Double Your Freelancing, or the basics of it, and said, “Have at it.” People complained, saying, “I want this, but I’m a marketer. What the heck is this job script stuff?” That led me, about a year ago or so, to break ground on a product called RightMessage and partnered up with a guy named Shai, who’s my co-founder.

I’ve been running that while also keeping my eye on Double Your Freelancing ever since.

Garrett: There’s so many layers to that that I absolutely love. One is that it’s so easy for everybody to see, “Oh, he launched a great app, and it’s doing well, and I want to do that,” but none of what you’ve done to get here has been…It’s not like you said. When did you launch Planscope? It was about the same time as Sifter, right?“

Brennan: 2011. It was 2011.

Garrett: OK, so about seven years ago. You launched that. You learn about SaaS. You get familiar with it. You’re writing content, which ends up turning into the bigger business, and start getting to info products, which then, through your scratching your own itch, you’re learning, "Oh. Well, there’s ways I can sell this to other people.”

Then you see the opportunity because you had…You’re famous and I loved it that you used to call the Plinko board for Double Your Freelancing. You got into some productized as consulting there, then some screen casts, and more products that are explaining things to people.

Then, finally, having enough context, both from the SaaS side and from the Plinko board side, if you will, to say, “There’s something here. RightMessage could be a product.” Although I guess it wasn’t RightMessage at that point. “This could be a SaaS product that I can get back to recurring revenue and do that with people.”

Just the circuitousness of it, I think, is awesome because we all want to dive into a SaaS app and just get started without realizing there’s so much to learn and so much background to handle ahead of time so that we have enough insight and understanding to do it well, so I love that part.

I think it’s also easier to start with potentially other mediums of validation versus just saying, “I’m gonna go head first into software”

Brennan: Yeah, the whole thing is just a series of if/thens, right? I like to think that even though RightMessage…We launched publicly January 23rd this year, but, if you go back to, this is 2012 for me.

Wordpress plugin worked with Infusionsoft like you do that Plinko board kind of model. It’s been a long time coming, which I think has made it so the success of it – and, really, our attitude, and building and running it – is much different than when I was just doing my little project management SaaS. Never really done this stuff before.

A lot of people say it’s easier to start with an audience, and I agree with that, but I think it’s also easier to start with potentially other mediums of validation versus just saying, “I’m gonna go head first into software,” and starting it by…People buy RightMessage for the same reason that they bought my consulting. They thought that personalization would increase sales.

At the end of the day, they’re buying the same outcome. How they get to that outcome is different and a different model, but it’s much easier to sell a product as consulting a thing, where you’re saying, “Here’s where I can get you. Here’s what I’ll do.

You give the leg work yourself, and then complete a transaction versus saying, "I’m going to go and build a SaaS from scratch and try to achieve that same thing.” I know SaaS is much sexier. I know the recurring revenue stuff is much cooler than consulting, but I think we would be in a much different position these days with RightMessage if we didn’t start that way.

Garrett: Yeah, having a rough idea is completely different than the things you’re going to learn once you’re getting your hands dirty implementing it for somebody else. The questions they’re going to ask you. The things they’re going to challenge and push back on.

The things they’re going to ask for, all help steer you on the right direction to give you the insight to successfully launch something in a different form.

I want to talk about Planscope for a second. You sold it. You sold it through FE, so you inevitably went through some level of due diligence. In hindsight, what did you learn that you did wrong, that you would do differently, or that you did explicitly do differently this time around, based on that experience?

One of the things I had to do was go through basically a year’s worth of credit card statements and black out everything that wasn’t directly Planscope related.

Brennan: Yes, the big mistake I made was, as I…Planscope was under the umbrella that was my consulting business. I didn’t want to have five different corporations. I wanted a single company that would basically be an umbrella company, which meant that, when selling Planscope, it was an asset transfer. It wasn’t a company sale, first off, meaning I sold the code base and I sold the customers.

That was one thing, but the other thing that had lent itself to was, since I have this one single company, as I started to do things like create courses that were…It’s just me at the end of the day.

If it’s a Planscope charge through the Planscope Stripe account or a Double Your Freelancing – or what became Double Your Freelancing – charge through the other Stripe account, it all went to the same checking account at the end of the day.

One of the things I had to do was go through basically a year’s worth of credit card statements and black out everything that wasn’t directly Planscope related. Now, this got tricky because sometimes, like with Help Scout, I had the Planscope user on that, but I’d also have one for the other stuff. It’s like, “Well, do I treat half of that expense as Planscope?” It got tricky.

I know sometimes it doesn’t make as much financial sense, but now my default is…If this is potentially a separate saleable asset, I don’t care if I could potentially group it under the same billing account as the one I’m using here, I’m going to have two separate accounts. It’s just cleaner. It’s easier.

A lot of these companies, if you write in to support and say, “Can you move this in box from Help Scout into Help Spot?” Anyway, “Can you move this one thing, this one sub-account to a new billing account?” Sometimes they can’t do that. Then you’re running into responses like, “Well, we have an API. Have fun.” It gets hairy.

Garrett: Yeah. It’s a mess, and it’s not even necessarily about selling the company, although it will be exponentially easier if everything is nicely organized into its own buckets. To me, it just makes it easier to run the business day-to-day, handle your own books.

For that matter, see like, “Oh, wow. This work I’m doing here is profitable.” Once you start charging it against its own expenses and looking at it as its own bucket, you can start to have better insights into what’s working, what’s successful, and then say, “I need to have less time there, more time here,” what have you.

It makes everything clearer, even though it’s a little more of a pain to set up different checking accounts, different credit cards. Like you said, separate accounts on the same product. Things like that can get hairy. I think it’s worth it in the long run for sure.

Brennan: Absolutely. Yeah.

Garrett: In your case, too, it’s kind of organic. It’s not like Double Your Freelancing was originally that separate from Planscope, and so it’s hard to see that as it happens because you’re down in it.

Brennan: Correct. In retrospect it’s like, “Yeah, I should have had it clear.” I should have known that this content thing would have been not legion before Planscope, but instead a separate business to itself, but I didn’t. In retrospect, yeah.

I think it’s different now with RightMessage because we did raise some funding from friends. We did do the proper co-founder thing. It’s a little more we had to. If it was just me doing RightMessage, even though I probably, knowing myself, would have kept it under the same umbrella company, but would have opened up separate accounts now. Again, I’d assume it’s an asset sell.

Then I would do…I think Rob Walling did this with Drip, where he had the Numa Group, LLC, which was his little umbrella company. Then, when he partnered up with Derrick and they started to actually do well, he was like, “OK.”

He did an episode on his podcast about this, but he had to go through and basically do IP reassignment for every little thing that seemed insignificant at the time, just to make it so now there’s a clear cut between his umbrella company and Drip Incorporated, which had to happen in legal bills and all that fun stuff.

Garrett: Totally. Let’s switch over and talk a little bit about plateaus. You’ve grown multiple products now. Inevitably, they probably each had their own plateaus here and there.

In plateaus in growth, revenue, customers, were there any plateaus that, in hindsight, stick out in terms of either how long they dragged on and you started to wonder, “Is this going to get growing again?” and/or what was your solution for adjusting the dials to break through the plateaus, and get back on track and feel good about where growth was going?

I wanted something that wouldn’t require forming a habit to make it successful. I guess that was one thing I learned from that plateau with Planscope.

Brennan: Yes, I can talk about…I can give you a few examples. One of them is more recent with RightMessage. We are escaping from a very minor plateau for now. I’ll get to that later.

With Planscope there was really a perpetual plateau in the sense that I was not putting myself the way I think I had to in the shoes of a buyer. What I mean by that is that one of the issues that I had was an adoption issue. You might have had the same issue with Sifter, too.

It’s more than just saying, “I’m signing up for a $30-a-month service.” Instead, it’s saying, “I’m needing to approach my team and say, ‘Hey, we’re going to try…it’s a crapshoot…we’re going to try this new thing.’” There’s the mental friction of, “Well, is what I’m doing now really that painful that I should actually consider switching?”

This was a big challenge that I know I faced with Planscope. There’d be a disconnect between when people would find the product – find the marketing site – and then be ready to actually use it because they’re midway through a project, and no one’s going to switch project management tools midway through a project. There was a lot of that kind of friction.

With Planscope, it’s a mixture of not knowing enough at the time, but also, I think, the nature of the beast. We never had that constant up and to the right. It went up to mid five, six thousandish a month and then just kind of sat there.

Granted, a lot of that could have been mitigated had I focused on it more. I was splitting my time between the thing that actually paid the bills – namely, selling courses – and Planscope, but there was that plateau, and I think a lot of it had to a lot to do with that adoption issue.

That’s why, when I was looking at RightMessage, I was thinking, “What I really like about this” – which I didn’t have with Planscope, but I don’t think people think about this all the time – “is that it doesn’t require forming a habit for it to be successful.”

Meaning, to use Planscope – or Sifter probably, same thing – successfully, you need to make it a habit. You need to be in it daily, using it daily, and so on. Whereas what I really like about RightMessage, which is something a lot like Baremetrics – you go, you sign up – there’s definitely setup work with RightMessage. Baremetrics, it’s a one click, go.

If it’s working on your behalf – which is what I like about this marketing tech stuff – if it’s continuously working on your behalf on autopilot, once you get it set up, they’re going to keep paying the bills if they’re getting that constant ROI. I wanted something that wouldn’t require forming a habit to make it successful. I guess that was one thing I learned from that plateau with Planscope.

Then, with Double Your Freelancing, the plateau was always…It wasn’t as much of a plateau. It was always fun optimizations. I like DYF because it’s a very formulaic business. I know I get this much graphic ADA from Google. This many of them will turn into subscribers. This many of them will make it to the end of the onboarding funnel that leads to a pitch. Then this percentage of them will buy.

Then, if they buy at this point, that means within 21 days of them becoming a lead, I capture this much revenue, and then their lifetime value is X, which means a percentage of them will then move on and buy other stuff. It’s just super predictable. I think it’s because…One thing is it’s all transactional.

I’ve dabbled with recurring or installment things with Double Your Freelancing, but with little success. It’s pretty much all transactional. It’s you pay this, you get a course. That’s it. Then there’s a lot of things behind the scenes that get people to the point of paying, but also get people to then be upsold on other products. I should say cross-sold on other products that we offer.

The plateaus there have always been…The plateau I’m at now is more traffic because I haven’t been focusing a lot on us. I haven’t been focusing a lot on content creation, but the back-end funnels are really dialed in.

The thinking is, “Well, if I’m getting a thousand people a day coming from Google now and this translates to X revenue, well, all things being equal, if I got that to 2,000 a day, would that effectively double the revenue from this company?” Maybe. I don’t know. Those are the fun things.

When you put a value on a unique visitor to your website – and you can put that value from reverse-engineering it from total revenue – how much money do you make? Divide that by how many customers you made. Divide that by how many leads you have that turn into customers. Divide that by how many prospects or visitors you have to your website.

You can have a nice little formula…not formula, but an assignment of monetary value for every stage of the funnel. Then it just becomes a matter of saying, “A lead is worth $20, but a customer is worth 200. If we can make more leads turn into customers, now every lead is worth $25, which means every visitor is now worth much more, too.”

We haven’t really plateaued with DYF. It’s been more about there’s always a list of optimizations I could do with the funnel. That’s really where a lot of the personalization came from.

I was thinking, “What if, instead of showing the normal call to action, if I thought they were a web designer because they got referred to us from a web design blog that sends a lot of traffic, what if I just throw ‘Web Designer, colon, or Designer, colon – Learn how to increase your prices’ as the call to action for those people”?

Then I saw almost a 3X improve in opt-ins. I’m like, “OK, that’s a very nice way of getting that stage of the funnel to be multiplied.” In terms of plateaus, I don’t really think I had…There were business plateaus in terms of, “Do we go for the community subscription model?”

We did a thing called the Academy which was super-popular, but we lost money with it. I think the plateaus were more about trying to push the edge and thinking, “Well, we’re doing really well with just transactional, one-off, self-study courses. What if we made this a group live course? What if we did this, or what if we did that? What if we did conferences?”

The thing that has consistently worked for us has been the super low touch – Google traffic comes in, they opt in to a lead magnet, that lead magnet then ultimately pitches them on a course, they buy the course during urgency window. If they have any issues, they write in to my BA. That’s the model.

Then I just scale horizontally with saying, “This course is about pricing. Here’s one on getting clients. Here’s one on project management. Here’s one on proposals.” Just being able to say, “Well, then, somebody comes in this channel, buys this course.”

Then we can say, “Well, if you’re a freelancer, if you need help with pricing, you probably also need help with sales and marketing. You might even need help with this.” There’s a lot of really good potential for automating cross-selling there, too. I think that the biggest plateaus there were, I was just trying to experiment too heavily with different models.

The other plateau would be the one we had with RightMessage currently, which was…I was super-happy. We were getting 30, 40 percent month-over-month growth since we launched last January. By 30, 40 percent, that’s like 3,000 more MRR a month, but that’s still…We’re happy about that.

Then, over the last month, it basically plateaued. The reason for that was the way we grew early on was doing demos, screen shares, Zoom stuff and everything else. Then we said, “Well, this isn’t scalable.” I mean it is scalable, and we were thinking…

We got that normal thing of like, “We want the website to sell ‘em something. We want really strong inbound channels like I had with Double Your Freelancing. I don’t need to talk to anyone on the phone to sell them a 300-dollar course.”

Garrett: Maybe you should’ve optimized it using a tool like RightMessage.

Brennan: I should have, yeah.

Actually, we have. One of the things we have done…One of the things that fixed it, because we’re out of that plateau, is we have more of a dynamic home page, that depending where you are in the awareness funnel…We still are optimizing for the high-touch stuff because that’s what’s working.

I think it’s such a new tech and all this stuff that people really need to see, “How could this actually help me in my unique business?” but, if they’ve done that already, then the home page becomes more about getting them to buy.

We are using it for what level of awareness they are, but we’re still finding and, until there’s more, frankly, competition and more people know implicitly…No one needs to be sold on, “Does email marketing work?”

Companies know it does, but we’re at, I think, email marketing circa mid-2000s right now with this stuff, where it’s like, “Will this stuff actually work? If so, what do you do? What are the best practices?”

That’s why we’re really optimizing now for getting case studies in. I’ve been reading a book called “Crossing the Chasm,” which is all about going, if you’re in a new market, from innovators and early adopters to mainstream appeal, and it’s all about social proof and seeking in the wild.

We’re doing all these things like RightAsk and all these tools that put our branding and make it more turnkey than the way we started. It’s always just a bunch of putting your ear to the ground, seeing what’s working, what isn’t. If it’s not working, instead of saying, “This sucks, this won’t work,” try to figure out exactly why it’s not working.

Make some hypotheses about what I could do differently. Then do it differently and see if it works. It’s just a bunch of if/thens.

Garrett: There’s so much to pull out from all this. I think on one hand, as most of us get into this – I say most, many – we’re products people. We hit a plateau. The default assumption is not, “I need to fix my marketing, or my funnel, or whatever, I think we get there.”

It’s, “If only I had this feature,” or, “After I launch this feature, it’s going to take off.” I have yet to talk to somebody where that’s the case. I talked to plenty of people where adding a feature enabled them to change their messaging or helped them see something and identify an opportunity, but the feature itself was never it.

It may have been a stepping stone, but it was almost always marketing, adjusting messaging, and changing how you sell instead of expecting the website to do the work, doing a lot more hands-on, or changing the audience you’re targeting, that kind of thing. Those were the things that moved the needle and got through plateaus, not some random feature launch.

Brennan: It’s a lot easier. It’s a lot easier to change your marketing site than it is to make…

Garrett: As a developer or designer, that’s not the work most people want to do. There’s this mental block and this hurdle. I think one of the other things…Almost two parts, and this is back in the beginning of Planscope because I related to it so much.

One is, I think we all underestimate the amount of social capital that anybody puts on the line to try and convince a team to switch collaboration software. Whether it’s a bug tracker, a project management tool, what have you, I might try it – say Trello or something – by myself.

I’m using it for my own task management and I love it. It’s like, “Hey, we should use this for the team.” It takes a lot of usage for an individual to…It’s subconscious. Nobody’s thinking, “I’m gonna spend some social capital and try and sell my team today,” but that’s what’s happening in the background.

I’m not gonna present this to my team until I’m 100 percent confident it works for me or that it will solve the problems we have. That dynamic is a really hard thing to help people get through. For me, the biggest plateau and the most interesting breakthrough I had was with onboarding.

I didn’t change a feature. I just spent some fixing onboarding. The product did evolve. The onboarding never really evolved with it. I changed the onboarding in such a way that it made it lower pressure to invite teammates and to poke around, very low commitment.

That made a huge, huge difference just by adjusting onboarding in a way that took into account the fact that a team doesn’t just all six people sit down one day and go, “Hey, guys. Let’s sign up for Sifter.” It’s one person signs up, pokes around.

They need to invite somebody else to just poke around. Then after the course of a month, maybe something else, they’re like, “Hey, remember that time? We should go try that out. It looked like it was promising.” Then that’s the sales cycle. It’s so easy to overlook that.

With collaboration software, once you get the whole team on board, you’re in a good spot as far as churn and all that goes, but you have to understand that you’re winning over a team, not just slapping up a marketing site, and everybody’s just going to sign up, sit down and have a Sifter sign-up party. That’s never going to happen.

Basically, it wasn’t until I started to think of the person that I needed to really sell and convince is the other users to get at it, namely the clients.

Brennan: With Planscope, they had to salvage their client. I focused a lot – I think a lot of us do – on onboarding the person who signs up, so that first user. Then they have blank data, so we have empty state stuff and all this good stuff.

What would typically happen is they would load in like a project and a bunch of tasks and so on, invite a client, client gets in, dumped in headfirst, no onboarding and in an account full of data. What ended up happening would be the ones that stuck were the ones where the freelancer would sit physically next to their client and sign them up in person.

Basically, it wasn’t until I started to think of the person that I needed to really sell and convince is the other users to get at it, namely the clients. If they don’t use it, then the whole thing’s moot. That is one of the reasons that I like…Like I said, the thing I like about RightMessage is we don’t really have that issue anymore.

There’s really not a need for – not only need, just get, I should say – for sub account or other user onboarding just yet, but it will be eventually.

The good thing is, for us, the success or the value of the product is not dependent on collaborations. It’s dependent on collecting results and bubbling them to the service. That’s been one nice thing, I think, about the difference between Planscope and RightMessage.

Garrett: Yeah. That echoes so much of my experience with Sifter in so many ways.

Let’s talk about acquisition. With RightMessage, obviously you all have been very hands-on – doing demos, helping people get set up, helping people transition. Like you mentioned before, in and of itself, the way you’re doing it precisely now is not truly long-term scalable.

Talk a little bit about the tradeoffs and understanding. Obviously, you’re not just selling. You’re learning as you’re talking to people.

Brennan: Yep, exactly.

Garrett: Talk a little bit about how you’re using that, leveraging that, turning that into a feedback loop to how you sit there and sell, and try to automate some of the site selling itself.

Brennan: I think there’s two components. One of which is the communication of the outcome or the offer, which is the marketing site. That, we found the benefit of doing the high-touch demos, which the goal of the marketing site, really, now is just to pique somebody’s interest and get them to book a demo.

Then, at the demo is where we dig into things like who is this company, how do they make money, what role does their website currently have. Based on what we know and data we’ve seen from our customers, what are some things they could probably do to make an impact?

It becomes more of a conversation, a discussion, instead of us throwing that all front and center on the marketing site. We tried doing that. It didn’t work that well because I still think it’s…We’re still trying to figure out exactly how do we do this best.

We can do it really well in conversation. We can do it really well by saying, “Here’s your website. You have this type of person going to it and this type of person going to it. What if we change this and this?”

Now, we’re getting to the point, with rolling out tools like RightBar and RightAsk, that it’s much more self-obvious. The difference is, earlier on and we were going after personalization. People intuitively get it, but they don’t know where to start. They don’t know what to do with it. They don’t know a lot of these different things.

Now, what we’re doing is we’re going more against…We’re like Sumo, but really smart in the sense that, if you’re a marketer, you already know about how effective opt-ins, sticky bars, and all that kind of stuff are, these different CRO tools, but what if you can make it?

Depending on where somebody was in your overall funnel, you’re promoting changes, which a lot of people don’t do. A lot of people optimize for anonymous traffic. That’s been much easier to sell than saying, “Hey, we’re like an if-this-then-that engine for your website where if this is true, then change that.” The big question was always what is that? What are we changing?

We’ve also realized that people have a lot of issues with segmentation. A lot of people don’t segment. They know if you’re a customer or not. Beyond that, a lot of people don’t really have any data.

We’ve built tools like RightAsk, which let people do these unobtrusive surveys on their website that not only collect high-level data about breakup of audiences, but also let you assign individual responses with the person viewing.

I don’t know. If I go to Beanstalk’s site and a little thing pops up saying, “Are you more of a…What’s your job role,” I click I’m a marketer or executive, let’s say. That allows you to profile people over time.

Then you know, “OK. Well, I have half executives, half business owners, half more IT developer types. We need to sell to each of these two types of people differently.” Before we rolled out something like RightAsk, a lot of companies couldn’t do that.

How would you know if this person’s a developer or this person’s more management? That’s been helpful. We’ve been really using that to help sell it over these demos that we’ve known. That’s the one component.

The other component is once they’re in. We’ve actually intentionally left off a lot. We don’t really have much onboarding to speak out. What we’re doing now is we’re basically saying, “When you sign up, we’re gonna get on a screen share. We’re basically gonna consult with you.

"You’re gonna drive, but we’re gonna be there to give you ideas on what to do, and basically do what no software on-boarding could ever do. Namely, actually be a human being who sees this stuff day in and day out. It’s going to tell you, based on your circumstances, what you should probably be doing.

Now, automated onboarding can get close to that, but there’s going to be a downgrade in our onboarding once we make it more automated. Right now, we’re doing it this way, which does have some resistance.

The kind of clients that we want to get, more of the ones who have real businesses who want real results and aren’t just tire kickers, they’re very OK with this because this is actually better for them.

Garrett: The one thing about demos that obviously you all are getting and doing well that I feel like most people miss is people sit out and say, "We’re gonna start doing demos.” They think, “We need a script, and we need to walk through this, and do this exact thing.”

Really, with a demo, a demo isn’t so much a demo as an interview. You’re interviewing the customer and then showing them things in response to their own issues and challenges so that, in effect, no demo should ever be the same.

They should share similarities, but they should cater completely to whatever pains your potential customer’s feeling. I feel like that’s something that…I don’t know at what point I realized that and learned that, but it was one of those epiphanies of don’t just walk people through your software.

Walk them through their software. Treat it as their account and really interact with them in that way. Ask them questions. You should barely do any talking. Let them do all the talking, and you’re just answering their questions by showing them things within the software.

Any kind of onboarding, it’s about them again. It’s not about your product. It’s totally about them, their needs, their interests, and their challenges. It makes it so much easier to demo things, too, because you don’t have to do all the talking. You’re not going to lose your voice. I think that’s just a huge, huge epiphany that I had.

Let the monologue emerge from the dialogue, I guess, is what I’m getting at.

Brennan: I think for me, the problem, I think, is the name – demo, demonstration. It’s a, “Here’s how it works. I’m gonna to walk you through A to Z of the product.” When you realize it sells, any salesperson worth their salt knows that the more you shut up, the more likely it is to work.

The more you can say, “Well, tell me why…” If I’m going to get a car and I’m just getting a demo of here’s this feature, this feature, this feature, to be frank, that’s going to work better for somebody like me. That’s what I go for. I go for what are the features, what are the technical.

What good salespeople will do at a car lot, will ask you things like, “So, why do you want this car? Is it going to be your daily driver? Is it going to be more of a date-night car? Do you need to go on a road trips? Tell me about your family.”

They’re going to ask you questions and listen to you. Really, I think good sales is aligning this is a need with this is an offer. It’s just the alignment of the two. A good salesperson, their whole job is a matchmaker between need and offer.

That’s why I really respect companies that say…I’m looking at car stuff now and talked to somebody yesterday who was like, “We’re not gonna be a good fit, and here’s why. Here’s what I would do differently,” and so on. It didn’t align well with them.

That’s the kind of stuff that I think, if you look at your demos as you saying, “I’ve got a tool,” people don’t want a tool, they want an outcome. How can I translate the need that I’m hearing, the thing that somebody needs from us? This is where they are right now. They want to get over here.

They think that our tool can help them maybe get from A to B. Now it’s my job to show them what route they would take using our tool to get there, and that’s it. You start with where do they need to be, where they are right now, and, using our software, how can they go from here to there?

It’s the same thing you do whether you’re selling consulting or whether you’re selling software or whatever. It’s the same formula, but, like you said, I think a lot of us we think of it as, “I’m gonna walk you through the product,” but that’s not necessarily what…That should happen to a degree, but it’s not what people really want.

They want to know, “How can this get me to where I need to be?” That’s where the whole benefit focused marketing site stuff comes up. I think there’s a balance between this. This, I think, has to do with knowing your audience. If you have technical people buying from you, you can’t just be super high level abstract because that’s not going to potentially help them.

If you’ve got executives buying from you who are non-technical, you need to speak to them differently. It’s just, again, knowing your audience. I think the best way is having a lot of discussions, conversations, and then codifying it into a monologue. Codifying it into sales copy as a result of conversations, not as a preemptive way of explaining, right?

Let the monologue emerge from the dialogue, I guess, is what I’m getting at.

Garrett: Yeah, totally. We’ve got two closing questions. They’re similar, but I feel like it’s been the best way to wrap up. The first is, through all this, any of the products, really, what’s been the single most difficult day or week and experience that you’ve gone through where you were like, “Oh, crap,” and just completely deflated you? Then how did you recover from it?

Brennan: First time I had to fire somebody, I think. That was more recent with RightMessage. It’s one of those things where it just wasn’t working out. I think we both knew it, but it’s always hard.

I think that’s this weird idealist that, in a perfect world, everyone just gets along, everyone does her job, everyone we’re just all kicking, but with every business that comes, I’m realizing more and more that it’s much more than just the thing you’re selling. It’s the culture, the atmosphere of the company, and so on.

You always feel like, “This is my fault. This was something I should have done differently to make it so I’m not in this position.” I think that would be it. That was definitely it for me, recently.

Garrett: The one thing from talking to others about firing people is that a lot of times, too, you realize and you avoid it because you really don’t want to do it, and it’s going to be miserable and unpleasant, but if you do it right and with empathy, the truth is it’s better for both parties.

They’re not in a great place. There’s probably a better role for them somewhere else. The key is to just do it with empathy and understand that, yes, it’s going to be crummy, but it’s not necessarily crummy.

It’s not about how it’s going to be crummy for you as an employer, but how do you help them find their footing to get that next role, whatever it is, and that can change the dialogue and the conversation in thinking about how do we help you get in a better place that just happens to not be here for whatever reason.

Brennan: Yep, yep.

Garrett: The next one is really simple. If you could go back seven years, whatever, and give yourself one piece of advice and know that even though it’s a younger you, you’re actually going to follow the advice, what would that advice be?

Yeah. I think the thing, again as a software developer, I had an undue attachment to software. At the end of the day, if you start to think, what people really want are just a better outcome. There are easier ways of delivering that outcome in different ways.

Brennan: Don’t start with SaaS.

That was easy.

Garrett: I think I can read between the lines there, but can you expand on that?

Brennan: Yeah. I think the thing, again as a software developer, I had an undue attachment to software. At the end of the day, if you start to think, what people really want are just a better outcome. There are easier ways of delivering that outcome in different ways.

If you think about it on the spectrum, on one end you have consulting, which is, “I have the knowledge and I have the experience to do it all myself and to guide you in the right way. You pay me a lot more but it’s all done for you.”

On the other extreme, you have information that’s, “I will teach you how to do this based on what I know, but it’s much easier to develop,” typically, but it’s up to the buyer, the customer, to implement. Then, in the middle, you have software which is turnkey-ish and that it’s this hybrid approach, but it tends to be very hard to get off the ground.

All things being equal, if you could say…It’s people want to use personalization to increase sales, which is what people are attracted to. It’s much easier for me to teach doing that. Maybe, ideally, originally in a workshop or one-on-one consulting, and get an idea of what are the objections people have.

What kind of pain points really are people saying in their own words, and test this out through other forms of achieving that same outcome versus going ahead first and saying, “I’m gonna break ground on a new app, do this, build a marketing site. Figure out how we get people to the market.” It’s much easier to start from those other channels and then go into software later on.

Garrett: The best approach to starting a SaaS app would be to have, say, a two-year plan where you start out. The first six months, you’re just pure straight blogging, building an audience, promoting the content. Then you start transitioning that into some info products.

Then maybe just more productized consulting, where you’re selling and learning. Then you’ve hopefully built up a little bit of a revenue stream to help offset and help bridge a gap between maybe quitting a job and starting it or ramping up your SaaS revenue.

Then you take all that knowledge, you apply it to the SaaS app, and you’re going to be infinitely better off because you front-loaded all of the learning in a much more low-risk environment. Heck, it could be that once you get the info product, you could find, “Man, there’s not an app here. I thought it was a great idea, but it’s not.”

You validated it, hopefully made a little bit of money through the process of validation, and then realized it before you went headfirst into a SaaS app, which has…Ideally, it scales really well revenue-wise, but you’re definitely front-loading a lot of costs in terms of server setup, building the app, all that stuff.

It feels like a great way to de-risk it both learning-wise and financially to help be a stepping stone instead of just diving in headfirst.

Brennan: Yup, exactly.

Garrett: Right on. This was awesome and incredibly dense, I think, in terms of covering ground. Thanks so much for being on. I’ll keep you posted when we get this published.

Brennan: Yeah, thanks for having me, Garrett.

Garrett: All right, thanks.

Brennan: Mm-hmm.