The Slow, Deliberate Process of Making a SaaS Business Work with Jane Portman of Userlist

Courtland Allen: 7s

What's up everybody? This is Courtland from IndieHackers.com and you're listening to the Indie Hackers podcast. On this show, I talk to the founders of profitable internet businesses and I try to get a sense of what it's like to be in their shoes. How did they get to where they are today?

How did it make decisions, both of their companies and in their personal lives? What exactly makes their businesses tick? The goal here as always is so that the rest of us can learn from the examples and go on to build our own profitable internet businesses.

Today I'm talking to Jane Portman, the founder of Userlist. Jane, welcome to the show.

Jane Portman: 37s

Hi, Courtland, it's a great pleasure to be here on your show and to just be talking to your amazing widest audience here.

Courtland Allen: 45s

My pleasure to have you, Jane. You are the founder of a company called Userlist. Tell us a little bit about what Userlist is and how it works.

Jane Portman: 54s

Userlist is a tool for customer messaging and you can use it to send a lifecycle email to your SaaS customers. Unlike other email automation tools, we are focusing entirely on SaaS companies. We are a bit more focused, more streamlined version of Intercom/Customer.io.

We've been out for two years by now, publicly launched in August and have been growing much better ever since. I do this together with my co-founder Benedict and my co-founder Claire Suellentrop. I think she was on your show sometime.

Courtland Allen: 1m 33s

Yes. Big fan of Claire's. It strikes me when I hear you describe Userlist. I've been following your story and I know that if I had asked you a year ago what Userlist does, you probably would have described it very differently. You've had a quite a journey with the evolution of exactly what it is that you're building, but also how you describe it to people.

Jane Portman: 1m 51s

Exactly. Actually what we're building has not changed as much as the way we try to get the point across. What was really helpful this year, I think in the middle of the year we did the positioning exercise and we started using the terms “customer messaging” ever since.

That was super helpful because not only it allows us to explain what we do well but also it allows us to build a much more focused roadmap in terms of what we're going to do next. Before that, we went all over the place with some imaginary features. We can take a deep dive because we collect behavior data of SaaS customers and then send communications based on that.

But behavior data, once you have it in place, it's a pretty powerful thing. You can go into conversion insights, you can go into analytics. All kinds of other things, fancy dashboards, while calling ourselves a customer messaging tool allows us to focus strictly on the communication aspect of that.

Courtland Allen: 2m 54s

Makes sense. Walk me through maybe like a case study or an example. If I am a customer, how would I use Userlist?

Jane Portman: 3m 2s

You would use our API and start sending information about what users do inside your web application. We record this display of users within our dashboards so you can manage, see who users are, what they do. And then you would head over into the automation section of our app and then set up automation campaigns there.

So let's say when the user joins, they are sent this and that. When they convert to paid, they get sent this and that. When they achieve their project number 300, they get send this and that, and all kinds of life cycle based campaigns in a very straightforward and beautiful manner.

Courtland Allen: 3m 46s

If I had this with Indie Hackers, I could say, "Hey, if Jane or any user makes a product page on Indie Hackers and their products surpasses $1,000 a month in revenue, or $10,000 a month, send them this email congratulating them and asking them to come on the podcast.

Jane Portman: 4m 1s

Something like that. Yes.

Courtland Allen: 4m 3s

Very cool. So the idea that you cannot change what your product does and yet completely change the way that you describe it and the terminology that you use to explain it to potential customers and have it still be accurate. It is pretty mind blowing.

It's just kind of illustrative of the fact that a product can be many things to many different people. What motivates you to make a change like that?

Jane Portman: 4m 24s

I think it was not the motivation. It was very straightforward struggling to explain what we do. We've been out for about two years and until just very recently we've been really struggling in conferences and in other situations when we have to do the elevator pitch, it would not be effective.

We would do a behavior based email automation pitch and that meant that people started comparing us to Drip, ConvertKit, Mailchimp, other things. While being powerful in the behavior based component, we don't allow for marketing email at all. So it put us in the wrong league. It was clear that we were doing something wrong, but it wasn't obvious until we did April Dunford's exercise and the spreadsheets, all of this stuff, what we are doing wrong.

What we did was actually listing all the features and all non-existing features like those that we would never build, hopefully never. Then map those to the value they deliver and to the people who can benefit from that. That allowed us to select this messaging component and focus on that.

Courtland Allen: 5m 39s

Ultimately you were finding that people didn't understand what you did even when you told them what you did. And so you went back to the drawing board to figure out a better way to describe your product and your features. Now you've unlocked growth.

You're at the point where you're making, I think, four figures a month in revenue. I want to go back in time and talk about the path you took to get here. I know Userlist isn't your first company. I know you've learned lots of other things from your previous companies that have informed what you're doing now. Where did this whole story start for you?

Jane Portman: 6m 7s

It's a long story. I've been serving SaaS companies as a consultant for ages, basically since 2012, 2013, when UI Breakfast was created as my consulting brand. And I've really enjoyed being in the community of founders. I really enjoyed product work. I did my own products, but they were never SaaS.

I did four books before venturing out to start my first SaaS company. And that was great training, but it was very, very not similar to running a SaaS. Not many of those takeaways were helpful in the SaaS industry. I mean, it was really, definitely an amazing sandbox, but when I ventured out to create my first SaaS, which was called Tiny Reminder in the fall of 2016, I was making all kinds of possible mistakes.

I'm super grateful that I started with a very small SaaS product and that I wrapped it up fast, understanding that it's not really going too far. After that, when I sold it, I ultimately reanalyzed all these mistakes that I did and settled out to recruit co-founders, Benedict and Claire. Then we started Userlist in the fall of 2017.

Courtland Allen: 7m 35s

We spoke a few weeks ago and you said something to me that was really interesting, which is that you wish more founders realize that starting a SaaS business is actually a pretty slow process and it's clearly not the best way to make money online. What is the best way to make money online, as someone who's done it in other ways?

Jane Portman: 7m 54s

There is a whole range of options. It depends on how much you want to get and how scalable you want to keep this. Of course, the most straightforward way is to trade your time for money. Being a freelancer, or better, a consultant. That's the most straightforward way.

I think I didn't invent this kind of a letter, step approach. Amy Hoy, Rob Roling [ph], Patrick McKenzie they all talk about the same stuff. First, it's trading time for money, then it's productizing your services, meaning finding a reliable, repeatable format for that.

Then you can experiment with info products and info-products money is much easier to make than SaaS money because books and courses are pretty much impulse buy and you really don't care that much what they're going to do with it. With SaaS, you really have to be useful 100% so that people keep paying a recurring fee for what you do.

It's a different kind of value/money exchange. I've been through this initial phase of a startup twice by now and there's still so much I had in terms of growing it. As for the early stage, I think I can absolutely testify that it's a slow one. Even if you do things seemingly right, it is still slow.

My illusion was that if I fix all these product mistakes that I did with my first SaaS, I am not going to do this silly stuff again, then things will go much faster. What our ambitious goal when starting Userlist was to get to $5,000 MRR in the first six months. That would be great validation, whether we should incorporate and keep doing this.

We barely got a working beta and about a year after getting started and it took us so long to set things up properly, to incorporate to build all this infrastructure that surrounds a software as a service business.

Nobody talks much about it. It's like getting your terms of service in place, getting your knowledge base up and everything like that. Of course that can be a different way. There might be like a way to do this overnight. Like Josh Pigford with Baremetrics. He built it in a few weeks. I'm sure he didn't have a knowledge base running immediately.

But right now these days with the quality bar being so high we just couldn't go live without having proper knowledge base, proper company, being fully legal and things like that. All of that took so long. And then when we had this in place, we thought, "Now we can rocket ship grow.” No, not yet.

And we were just in closed beta and courting more and more early customers and so on and so forth. It was absolutely exciting, absolutely positive. We didn’t fall in the trail of sorrow or anything. It was nowhere close to where we thought we could get provided that knowledge and that quality of the product that we have. So it is definitely a learning experience.

Courtland Allen: 11m 12s

Let’s talk about some of these things that make a business slow to grow versus other kinds of businesses. Because as you mentioned, there are people who've started SaaS businesses that are like up and running in a week. There are SaaS businesses that need a certain level of polish and incorporation and paperwork and documentation.

They need to build a certain level of trust that just can't get up and running that fast. Then you also released, I think you said four different books. You've done "info products" where you can just sell those instantaneously and people are buying from day one.

What are some of the differences you've learned and seen between these things and what are some of the factors that control whether a business can get up and running and start making money quickly versus whether it's going to take a long time?

Jane Portman: 11m 51s

For books and courses you still have to have audience in place and for info products it's more important to have an audience than it is for it for a SaaS. Because the ultimate goal for SaaS is to discover new people in a reliable, repeatable manner. While with books and courses you can have your little pool of loyal fans.

Whatever that means. Five thousand, ten thousand people or even one thousand is pretty much enough and you can keep launching new things to them, keep producing new content and the loyal part of those users who trust you and trust your expertise, they will happily repeatedly buy your stuff.

And that's a wonderful way to make money online without going to any of the technical complications, especially with platforms like Gumroad and many others in place. You don't even have to worry about payment processing that much. It's basically about shipping a PDF in a sales page and having a mailing list to launch it to. That's very much an MVP for an info product business.

Courtland Allen: 12m 55s

How much of the audience building plays into this? Because a lot of times people want to launch an info product but they don't have anybody to buy. They don't have a Twitter audience, they don't have an email list. Does that take years to build or is that something you can build as you're building your info product?

Jane Portman: 13m 9s

I don't know. I did a very slow way, so I also was growing my mailing list over years. It was only of those four books that I did, only the last two were really financially successful. The first one was purely a learning experience. The second one I did for InVision.

They paid me a small sum of money, but they also provided a connection to their amazing audience. So some of those people joined my list and it grew in a way that it could have never grown on its own. The book was called The Fundamental UI design. In addition to just bringing the audience, it's also a cool thing to be an author, to say that I wrote this type of a book.

Courtland Allen: 14m 0s

Yes, you're an expert.

Jane Portman: 14m 0s

The last couple, one was called The UI Audit. I think we have an article here on Indie Hackers.

Courtland Allen: 14m 6s

An interview on Indie Hackers from 2017.

Jane Portman: 14m 10s

That was sort of my signature UI/UX book, which represents my philosophy on building products. The last one in 2017, I believe, or 18, something like that, was called “Your Productized Consulting Guide”. This book appeared because I could just not keep the knowledge to myself on the topic.

Over the years I've accumulated some of the ideas and concepts how to run productized consulting service. I did a talk at Brennan Dunn's conference and I just had so many questions that I was absolutely excited to just sit down and type all of that into some sort of a guide and that's what it became. It's not directly related to my UI/UX profile, but I'm sure it also has attracted some eyeballs to what I do.

Courtland Allen: 15m 4s

I think being an expert is one of the coolest things you can be online where people see that you've written a book and, in your case, not just one book but four books. You know exactly what you're talking about and you build an audience around that. How do you leverage being an expert and having an audience and take that in to building a SaaS product?

Jane Portman: 15m 21s

You know what comes to mind? That video with six red lines and "I am an expert," when you're saying that. I think you don't have to be an expert to teach people stuff. You can share your knowledge and your discoveries even as you learn yourself. That will help both. Will help you to learn and pull up other people to learn. That's totally not a requirement to be 100% expert or anything like that. So what was your question?

Courtland Allen: 15m 53s

What you said is a great point, which is that you don't have to be a world-class, top-tier expert to teach people things. There are so many people who can make a living online by teaching others, by helping others learn things who disqualify themselves because they think, "I'm not the best in the world. So how can I teach this? Somebody knows more than I do."

But your goal as a teacher is not to be the most knowledgeable person on earth. It's to be helpful to the people who are trying to learn from you. Usually that means teaching people who are just one level below you. Even if you're a beginner, you could document what you're going through and help other people become beginners. If you’re intermediate you can help beginners become intermediate. In fact, you're probably a better teacher for beginners if you're not an expert, than the experts are, because they've forgotten what beginners need to know.

Jane Portman: 16m 31s

Absolutely. I'm standing on the shoulders of giants, sort of speaking, because I learned about that from Nathan Barry in 2013 and he talks so much about how you can be teaching just what you're saying exactly. But he also had this great book called, "Authority," that walked the reader through a step-by-step instructions how to get started with your first book.

I was like, "Well yeah, that's a great way to kickstart my consulting career." That's what I did with the first book. I can't be more grateful for it, for that instruction and that learning that he provided. However, there was one important point missing in his book. It was about making this book useful as a product. Creating it to serve somebody's pain.

In that regard, I wish I had known Amy Hoy and Alex Hillman and Stacking the Bricks and all that kind of philosophy earlier. Because with that in mind, I might have been more successful with the first one. However, it did help down the road. I can't complain. Not only do you need to follow the technical steps of creating a proper book and marketing it, but you also need to do it from the product standpoint so that it's useful and it's really closing some burning pain in the lives of your readers, potential readers.

Courtland Allen: 17m 54s

What are some of these lessons that you wished you had learned from Amy Hoy and her philosophy and how to sell a product that you're missing when you're selling your books?

Jane Portman: 18m 4s

I think the Sales Safari approach is a really awesome technique which allows you to, without actively interviewing anyone, go online in forums and other public places and just explore the audience that you want to serve and find out what pains can be solved. If you find repeating patterns, that's a great sign that a product can exist here, be it software or books.

She has plenty of great material on writing sales pages, which is also helpful. That pain, dream, fix scenario and everything like that. All these sales page classics. It's all so great. I did learn most of that gradually. I think there are so many resources these days where you can get this type of knowledge in a condensed way by paying like a hundred dollars for some type of course.

There are so many courses teaching people to make courses. They're not necessarily bad. I mean that's how the knowledge spreads, right? So yeah, that was a learning curve.

Courtland Allen: 19m 8s

So at this point, whether or not you see yourself as an expert, there are certainly many tens of thousands of people who see you as an expert because you've written these books, you've worked as a professional, you're doing consulting and you decided that you're actually going to take a shot at building your first SaaS business. And this is Tiny Reminders?

Jane Portman: 19m 26s

Yes, that was called Tiny Reminder. In plain English it was a form builder with a built in reminder emails. Whether you need to collect some information from people, maybe you are a publisher who needs to collect articles from multiple authors. You just put together form and the system will send them reminders until they submit the form.

I imagined this was such an amazing productivity tool that everybody would be fascinated. They will just instantly sign up and see how useful that would be in my life. Well no, that didn't really happen. I didn't have a clear audience that I wanted to market to. That was one mistake. Another mistake was I was trying to create a product category that didn't particularly exist.

It wasn't a form builder and it was not necessarily project management tool. It was something in between. It would take ages or a few sentences to explain what it does to mere mortals. While, if we were in an existing product category, that would be much, much easier.

However, it's still not a recipe for 100% success because with Userlist, I thought we were playing in the existing category. Guess what? It took two years to figure out how to call ourselves. So, seriously.

Courtland Allen: 20m 49s

Yes, there's no magic bullet. I think for a lot of first time founders, they think the fact that there is nothing that they can compare themselves to, that they are completely unique is a huge advantage. They say, "Oh my God, I've invented this totally new thing no one's ever done before. And that's exactly what you need to do when you're starting a company.

Because isn’t having a company based on having a new invention?” I think a lot of people find out the hard way, just as you did, that if you have to take ages to explain what you do to people, if they're not already searching for what you're building, because it doesn't exist as a category in their mind, then that makes the entire process of growing your company way harder to do.

How did you handle that at Tiny Reminder? How did you even figure out that was what was happening?

Jane Portman: 21m 28s

I didn't handle it well. Somewhere up to launching it to no success. I interviewed Alex Yumashev of Jitbit and what he said would be, "If I were starting from scratch, I would just build another help desk," and he runs a help desk business. Because you don't need to explain a help desk at all.

It's a very established category and it's clearly a necessary product that people clearly need. At that point, ultimately, that resonated with me, not before. With Tiny Reminder, what made me stop trying is that an acquisition offer came along. When you're flipping a coin, what matters is what you feel when it lands, not what it actually says.

With that acquisition offer, I was so relieved that I can take this off my plate and get it into somebody else's loving hands to market it well. So that was basically it. I didn't even wait for the sale to go through that ideas for a new, proper SaaS were percolating already in my head. I talked to Benedict and then it started with Userlist.

Courtland Allen: 22m 38s

So what's the story of how you and Benedict started working together? Because he was helping you build Tiny Reminder.

Jane Portman: 22m 43s

That's correct. We met many years ago in the same founder community, Aligned, so we were sort of friends before we started working together. When I was looking for a developer to build Tiny Reminder for me, we got on a call and I was just looking for some technical advice on how to recruit a co-founder and he – not a co-founder – a developer, and he asked me what my budget was and then he agreed to build the MVP for me for that type of budget, which was, to be honest, smaller than his typical rate.

We did an MVP with him very fast and then I kept hiring him a little bit more for some feature development during the year and that's when we figured it out that we made sort of good cadence working together. When the topic of another SaaS came along, it was obvious that I could not afford this kind of grand plan without having a great developer board. I'm super grateful that he said yes.

Courtland Allen: 23m 48s

Did he feel the same way that you felt about the acquisition offer for Tiny Reminder? Like, "Yes. Can't wait to be done with this. Let's move on to something else?"

Jane Portman: 23m 55s

I don't think it was putting a big toll on his time or productivity because it was more about the moral, mental pressure of the thing being out there and not growing. It was a freedom. Also, the new signups kept coming but they never really converted, which is not a great sign.

He was very supportive. We did chat a bit back and forth. He definitely was more than just someone for hire. He was also pretty supportive of the situation.

Courtland Allen: 24m 28s

I think a lot of founders find themselves in this position where they're super optimistic about something. They think it's the bee's knees and it's definitely going to work and they build it and they're proud of it and it looks great and then exactly what happened to you happens.

Where people might sign up for it and they might be excited, but they don't stick around. They don't keep using it. It's missing some crucial utility factor that just prevents people from being retained. And it just doesn't grow as a result of that, because it's very hard to grow something if people aren't sticking around. How did you feel in that situation? Because I've been there myself and it doesn't feel good.

Jane Portman: 24m 58s

I didn't have that long to feel miserable. I did have some marketing ideas in mind that I would have probably pursued with time. I had a plan to explore certain niches and go after a specific niche. The massive takeaways of building a product in an unknown market category – it's also productivity tools.

So, it's a vitamin type of product, not a painkiller type. You can easily sign up for it, but you can easily let it go. And with all of these factors in mind, I was just confident that this is no way to make good money anymore. Basically, that was the feeling. It was quite a no-brainer to just stop trying and to start something else with all these considerations in mind.

Courtland Allen: 25m 46s

Start something that's not a vitamin, but that's a painkiller. Start something that's not in a new product category, but that's in an existing product category. What are some of the other lessons you took into starting Userlist? Some of the constraints or the items on your checklist that you had to check off for Userlist?

Jane Portman: 26m 3s

Probably that it being an essential business tool is really important. By being an essential business tool, we, of course, put more strain on the product. It's got to be super well-built. It's got to be reliable, so it adds more pressure on the founder's shoulders.

It also means that people who get on board and who are satisfied, they're way more likely to stay and keep it going. Maybe sometimes it's a good thing. I know we all feel locked in some platforms that we don't like. I really hate to say that and I hope that never happens with Userlist, but that, of course, means that the retention is going to be much better than with any possible productivity tool.

Courtland Allen: 26m 47s

I think there's a certain trait that I see in a lot of founders where you don't really want to give up, where you're pretty confident that you can build something that works, that you can succeed.

If you try one product, you try one app and it doesn't work out, you're not like, "Oh man, building a business is hard. I guess I'm done." You think, "Oh wow, I'm not going to make those mistakes again. But on turn number two, I'm definitely going to avoid those mistakes and do it better."

And there's never really a question in your mind that there's going to be a try number two. What do you think that optimism comes from with you?

Jane Portman: 27m 20s

Maybe, I don't know. It's really hard to say. I think all these experiences from previous products combined, it shows that no single product is really a deal breaker and if things are not working out, sometimes it is worth to just keep moving on and see what you did wrong.

I had conversations with friends at the time when I was traveling with Tiny Reminder and they said, "Well, sometimes the businesses failed because the founders, they fail to persist for the necessary amount of time. They just give up prematurely." And I was like, "Yeah, but not." And what we did this time with Userlist was exactly that. We persisted but combined, all my experience combined, all Benedict's experience combined, and Claire's as well.

Because Benedict was also a second time founder and his first product, Stage CMS, and I'm sure he's more qualified to talk about it, but it served the audience of musicians. I bet he learned that serving the audience with musicians is not a great thing to do if you hang out in the audience of SaaS founders. It's definitely much harder to find customers for that kind of business.

I'm sure he took his lessons to our venture and I brought in my lessons and we had a feeling that we were doing things right. We were quite surprised with the pace at which we were doing that. But, on the other hand this time we were more dedicated to just doing the grind and grinding through to the ultimate growth inflection point, which I'm hoping we're at. Let's see what time brings, I'm not qualified to speak of the future.

Courtland Allen: 29m 6s

What about financial and lifestyle considerations of running a business as an early stage founder? Because it's pretty expensive to have to pay your bills and your rent and all that kind of stuff while running a business that's not yet making money because it's in the early stages. How were you able to sustain the fact that you're starting company after company?

Jane Portman: 29m 24s

I've been always consulting on the side, not on the side but probably like my time split in half. Half time consulting and half time doing my own things. Also, with client work, you sometimes get breaks from projects and if the regular freelancer/consultant would just be sitting there desperate for work, I would be happily doing my own stuff.

And I didn't have too many of these breaks though. With Userlist, both myself and Benedict, we've been doing consulting throughout these two years, and Claire as well. And that has helped us to grow in the organic pace as opposed to being desperate for money because that does not lead to any wise decisions.

Generally speaking in life, when you're desperate for something, that's not a great point to be. Be it consulting negotiations, be it product sales, being desperate does not create good vibes at all for marketing and for your customers.

Courtland Allen: 30m 25s

So let's talk about the earliest days of Userlist. Before we even got started working on Userlist, when you were just kind of trying to come up with the idea? What did that process look like and were there other ideas that you considered working on?

Jane Portman: 30m 38s

We were pretty set on what we were going to do. I was quite fascinated that Userlist.io was available as a domain name just because it was like, "Userlist, that's very much what I want." It's such an easy thing to pronounce. How can it be available? We got the domain name and the idea was let's do something for SaaS founders.

We collect behavior based data. We do automated messages. I was basically very inspired by Intercom at this stage because Intercom was, I mean I love them as product desk trainers, amazing (people), everything. At that stage it was super expensive for me as an early stage founder and it was even prior to their redesign.

Not only did they not do fantastic job, but it was not even pretty for the company of their size. They did redesign and they did add amazing features and they did get funded with less, like some billions of dollars of course. They're not our direct competitor, however, there was a product up in front of our eyes that was great, but it was definitely an overkill in terms of the features.

We basically deconstructed the essentials of that platform and we set out to do something, which has a Userlist, behavior-based data, some messages outgoing, be it email or in-app messages. Then we figured that we can iterate from there because nobody really knows what the future will bring in terms of customer development.

Initially, we wanted to do both in-app messaging and email as channels for delivering messages. We quickly focused on just being email and only now we're bringing back the idea of in-app messages and we hope to launch that soon, probably in early 2020. We're going a little bit back in terms of the features.

Courtland Allen: 32m 37s

So, when you decided you're going to build a product that's entering an existing category where there's other apps that are kind of doing similar things to what you're doing, you usually have some idea for how you're going to be different.

And in your case, it seemed like you're going to be more affordable than Intercom and you're going to have a much better UI because theirs, at the time, was pretty rough. How else were you planning to differentiate and what was kind of your overall strategy for what would set Userlist apart?

Jane Portman: 33m 1s

You don't say things like, "We are affordable" out loud. Because competing just on price, it's not a fantastic strategy. However, yes, we were intended to be affordable as in our peers can afford this. They cannot afford Intercom for a few hundred dollars but they can afford Userlist and we started as low as $29 a month.

We quickly figured out we are not going to go anywhere with that price. So right now our baseline price is $49 a month for the first thousand users. So, the price/value delivered ratio was supposed to be good, because not everyone needs all these complex enterprise features as you can see in advanced automation, like customer.io provides or Intercom provides.

Well, actually, Intercom was a different story because they are behavior based email. It's not super advanced. Their strategy is more like trying to do everything under the same roof, which is a viable strategy and we can see how they're making money.

We were going to do it in the opposite way to make a focused set of features and make it really clean and much simpler to use. And I hope we have succeeded, but there is still so much to go in that direction.

Courtland Allen: 34m 26s

What do you think are the biggest challenges in the early days that you didn't really anticipate when you were coming up with the idea and that ended up biting you in the end?

Jane Portman: 34m 34s

It's very hard for us to get people on board because it does not only depend on us, but it depends on their team effort. And it depends on the stage of their business. They might think they're launching in a week while in fact, they'll be launching in four months and we all know how it works.

So, they will sign up for a trial now. Then they will figure out, "Oh, we don't need it just yet," and they will go and then they will come back in six months and we will happily welcome them. But, that doesn't provide good metrics when you look at them. So, things like that being dependent on the customer's business, we thought it's going to be smoother to sell it.

It just depends on so many external factors that, of course, we try our best to provide education, hand-holding, materials, templates, still not enough to just get everyone to jump on board like that. There are a lot of stages to adoption in our case.

Courtland Allen: 35m 37s

It seems like, for what you're building, you're helping businesses talk to their customers basically and react to their customer's behavior. And so, generally speaking, these brand new businesses who were just first launching might be some of your best customers.

But there's a lot of uncertainty there like you're mentioning where they're not even sure when they're going to launch and they might get the launch date wrong. You have this very small window of time where you can, sort of, be their customer messaging tool of choice, but that window of time shifts and it's hard to predict.

Jane Portman: 36m 4s

We're still not 100% positive what type of founder is our idea of founder. We are positive it's not an enterprise scale SaaS, but whether that is a day zero kind of founder or is it a team of a few people who are a little bit farther in the journey, we're still not sure. Because the second group is definitely more grateful. They are more experienced.

They've seen some bad tools, so they will come in here and appreciate a new tool. However, the mission that we started this product is to provide both types of people with quality, affordable tool for running their SaaS. Because there are so many problems running your SaaS that you don’t need another one in the form of complex things.

This was the intended home page that you can go to. You can see your Userlist, you can segment them, you can send them on-boarding email. So it's like a little hub for your software company.

Courtland Allen: 37m 2s

I think one of the feelings you have when you first start your company is wild optimism. Every single time I've started anything, it's everyone I talked to, "This is 100% going to work. It couldn't possibly not work." And I've sort of shifted over the course of being a founder to be a little bit, I don't want to say pessimistic, but a little bit more realistic.

I'm always looking for reasons why things might kill my business. Reasons why I might be overlooking certain things and I think one of the things that's easy to overlook as a founder is just these customer conversations, talking to people and actually getting out of your own head and your own predictions of how things are going to go and actually talking to your customers and figuring out the reality on the ground.

You at Userlist, all three of you, have been really good at that. I've read a lot of your blog posts on it around the customer conversations you've had and the fact that you've done so many customer interviews. You're just good at talking to customers in a way that I am jealous of. I wish I could talk to customers as much as you did.

Describe to me some of the insights you've learned through talking to your customers over time and some of the methods that you've used for learning who your customers are and what they want.

Jane Portman: 38m 4s

Thanks so much. This means a lot coming from you. But indeed, essentially customer interviews are the primary source of truth, at least in our world when it comes to product development. Before even getting started, Claire did a huge round of potential customer interviews, just jobs-to-be-done style kind of research, of whether the problem is worth pursuing at all.

So, that led to some optimistic results. We did collect pre-orders, which helped (speaking of validation). However, pre-orders are also not a recipe for 100% success. It's a little bit of sidetrack of this conversation, but a lot of people who would buy your pre-orders, they won't use the app.

As far as 50%-70% won't use the app, because it's an impulse purchase to pre-order something from the founders you like. It's a different story to actually be using it. But, going from there, we started doing demo calls, first, with those early pre-order customers, then with more and more.

It was super intimidating, first, to get on the phone, to discuss, it was Zoom or Skype, to get on the call live to discuss the product. Especially the early stage, when your thing to demo was really embarrassing. It barely does what it should do and everybody was asking questions and you would be like, "Oh no, not yet. Not yet. Not yet."

So, it takes some guts but it's also a muscle that you can train and you should definitely start early and often. Written in a little bit about that and, in our books, a demo is not about the product. It's, most times, about the customer's business, about their struggles, about their needs, what they want to accomplish with the product.

And we've heard, lately, Steli Efti talking about how demos should not be longer than half an hour, ever. But then the part when you are showing around your product, it should be small. But the part where you are talking about your customer's business, that can be endless and you can’t learn enough while you are doing that.

It's always very helpful. And founders, they're super glad to share and if there is a pain point, you're going to learn about that. So, talking about their business, not about our product, was probably the number one secret, if we were to share anything from those calls.

Courtland Allen: 40m 34s

What are some things you came away from those calls, knowing about your customers, that informed what you did with your own business?

Jane Portman: 40m 41s

We didn't discover anything revolutionary, but it helped us to understand their world better. When we were doing those first, not the initial validation interviews, but actual product demos, and we did a bunch of them.

We were also building the product and when we started seeing that the feature requests, they repeat each other, the people are showing the same trends, that was, in our books, a great sign that we are actually moving in the right direction and that we understand what we're doing. Not necessarily 100% product market fit, but when you start seeing the same repeatable trends, then it's definitely a great.

We came on most of these calls together, at least two out of three. Typically, it was me and Benedict. In addition to being super full of customer insights, we also shared these insights together in real time. So, it's a great team building opportunity and it's a great way to have all these insights right there in real time from the source. That was really awesome for us understanding the product and understanding the customer.

Courtland Allen: 42m 5s

So how did you go from understanding the customers so well and having all of these conversations to the point where you realized that the way you're describing your product and what you'd built wasn't really resonating?

Jane Portman: 42m 18s

I think the difference there is the setup, the environment in which this understanding happens. When you have a whole hour of the conversation, then of course you have all this time to ask proper questions, to explain a way. But when you are at a conference and you're doing your 30 second elevator pitch or on your landing page, when somebody, out of the blue, just lands on your homepage and they have 1.3 seconds to grasp what you do from your headline, H1, that's a different setup.

So, finding those striking words, it's much more difficult. When it comes to H1, I'm pretty sure we can still do better than that. So, these are different things to do. But as a SaaS business, your major property is your marketing website. So you've got to be able to do both and that H1 out of H1 is also necessary.

Courtland Allen: 43m 21s

So, at the same time, you're basically trying to figure out how to describe your product. You're trying to sell your product to people, you're trying to build your product and design it. You're working a consulting gig. I can only imagine that you're also trying to learn, you're reading books, you're trying to figure out how to be a better founder. How do you juggle all of this time and what does your life look like as an early stage founder?

Jane Portman: 43m 42s

I also had my third child last year.

Courtland Allen: 43m 45s

You just have like 36 hours a day, apparently, that I don't have. How did you juggle all these things and actually be a productive human being?

Jane Portman: 43m 55s

I don't think I'm a super productive human being, really. My productivity is definitely not linear, so sometimes it will be a huge spike that would do something great, we'll launch a new website or refactor or email communications or something like that or prepare for the launch.

On the other days, I will be missing from work a lot or getting my child from school, going shopping or something like that. So, the key is to delegate as much as you can when it comes to household activities and it's just mostly a matter of managing these people and making enough money in that regard and just realizing that you cannot be perfect 24/7 and doing your best in all kinds.

When you have that many friends in your activities, when you have children, when you have consultants, when you have your SaaS, then there is no unhealthy obsession with just one of them. You suddenly understand that you have limited resources and these limited resources cannot go into just one place.

No, they should probably be wisely distributed and that necessary amount of resources is going to make it all right. A good example would be when you have one child, you can get really obsessed with them and that might lead to unhealthy parenting decisions. A lot of first time parents are really over caring or something.

When I have three, you just realize that, by no means, mother nature intended us to overprotect just one because your attention is suddenly all over their place. So, with the businesses it's a little bit like that. You are not super eager for results on the SaaS front for example. You’re not desperate. You just try to show up whenever you plan and do your best. I guess, something along those lines. I still don't have a recipe.

Courtland Allen: 45m 54s

Do you think having kids and a rich family life and having a consulting gig on the side forces you to be more productive with the limited hours that you do have to work on your business?

Jane Portman: 46m 3s

Definitely. So, for example, as someone who goes to an office, sometimes you would just come there because you have to and sit and stare at your screen and eat chocolate and browse social media. Well, in my universe there is not much time for that even though I do browse from time to time.

But still, you come to your computer and there is always something that you can do to move your business forward. With consultant work, it has really helped me to avoid stressful deadlines. When you're 16 and you have your first client you would think that if you don't ship it by tomorrow, the world's going to end and you would stay up until 5:00 AM, and I'm one of these people, and ship that work.

But most likely the world is not going to implode if you don't. It's much better to be healthier and more sustainable in everyday life.

Courtland Allen: 47m 6s

What do you think it is about Userlist that has kept you motivated? Because it seems like there are a lot of the same troubles you had with Tiny Reminder that you ended up happening with Userlist, but in a very different way. And yet, you're super excited to work on Userlists and I can tell you are very optimistic about the future and you've lots of plans. Whereas, Tiny Reminder, you were kind of just waiting to get rid of it or to sell it or move on to something different.

Jane Portman: 47m 27s

One major difference is that I didn't have an audience in mind firsthand, but right now, I do very much. We do have a very clear audience in mind and that is the audience of fellow founders. We understand that audience very well and their pains and their struggles. So, we are very inspired to build a quality tool for them.

Both myself and Benedict, we love product work, but we also like it as a meaning in life. It's also pretty rewarding to be working just in that direction together. We will make a very nice team in daily communications and in our approach to life and to product. It's also enjoyable in the process, not just in the results.

This size journey is about the process anyways. You're probably never going to be satisfied with the results and sit back and do nothing.

Courtland Allen: 48m 24s

I have a little sticky note I put on my monitor sometimes. It's the most cliche thing ever, but it says it's about the journey, not the destination.

Jane Portman: 48m 31s

It’s so true.

Courtland Allen: 48m 32s

Whatever you're doing right now in your job, that's the whole point of your job. It's the actual act of doing it.

Jane Portman: 48m 38s

And human happiness. You don't just have to be happy at this moment, but it's the perspective, that exciting vision of the future that makes you half-happy. It makes up for the 50% of your happiness.

Courtland Allen: 48m 53s

Fast forward to the point where you say you've had enough. You're going to read April Dunford's book because you're going to figure out, once and for all, how you can better position Userlist in a way where customers can understand what you're doing and hopefully you can start growing.

What does that process look like? We talked about it briefly at the beginning of this conversation, but what are the actual details of what you ended up changing about how you describe Userlist?

Jane Portman: 49m 15s

I don't think it's worth describing in full here, because it's going to take 20 minutes and we have a nice blog post written about all of the steps. Coincidentally, there was one of the most successful blog posts I've ever written by complete accident, to be honest.

We did this exercise: We listed our features and we mapped them together, listed out benefits, we map them with a value and the audience. We did these value clusters and based on those value clusters, we figured out what it is that we are going to do, like how it can be called and who our competitor is.

What we took away from that is that “customer messaging” phrase that we've been using. That took place in April of 2019 and I think that we have already arrived at improving that, so I don't think it works perfectly. We have added the word “lifecycle” since then because we think that from our observation, people use that word a lot when describing what we do.

So we added that. Right now it’s “life cycle customer messaging”, not just “customer messaging” per se. We still struggle with identifying our self as a competitor to Intercom, because we are a competitor to Intercom. But Intercom is a help desk in the minds of many people and we're not anywhere close to a help desk.

There is still ambiguity there. We're not sure whether we should be calling out Intercom by name or not. At that point, in May, it seemed like calling out Intercom by name was a great step, was to have it on the website. So, there's still learning in progress. But I should say that this October, myself and Benedict, we went together to MicroConf Europe.

For the first time, when we were in our circle of peers, we didn't have to pitch what Userlist is and what it does. To be honest, it was not because we hit the right phrasing with the positioning, but it was mostly that the product itself has gained some popularity in the community. We have appeared in some podcasts, we've been publishing stuff, and it's actually their reputation as a whole, not just that H1 positioning statement, that made us not having to explain what we do. To be honest, that felt magical to be finally acknowledged for what we created. We were kind of very close to being on top of the world this time.

Courtland Allen: 51m 57s

I think it's a really good point that because you've been working on it since, I think October of 2017, and you've also been very public about it. You're going to MicroConf, you're talking to people, you're all on Twitter, you're tweeting about it, you're writing blog posts about how you change your position and you're not doing all of this and secret saying, "Once everything's perfect, we'll start talking about it."

You're sort of revealing all of your struggles and your successes and your challenges to the world. So, it's very easy for people like me to follow along with your story and see what you're up to you. Then, I kind of do understand what it is that you do and I do understand why I would use it, who would use it, etc. So, I think that's kind of a cool roundabout way to educate your customers, especially if they're in the same social circles that you are when you're tweeting online.

Jane Portman: 52m 40s

Absolutely. As bootstrap founders, you don't have too many resources to spend on marketing. Writing those updates about what you're doing right now, trying to explain your reasoning, not building out in beta. Of course, it requires certain persistence and stamina to keep showing up and doing that.

But that's super easy compared to advertising or other ways when you struggle to get traffic on top of your funnel and all that traditional marketing route. So that's a very easy, very organic way to build real friends and even if they don't really convert, they can still have you in their mind and maybe recommend you to other people.

Courtland Allen: 53m 19s

That's such a great point. You don't have to be this Don Draper, copywriting expert constantly thinking of like new creative things you're write about. You just write about what you did today and what you did last week and what you're working on and you don't have to be super creative to figure out how to market what you're doing.

Jane Portman: 53m 32s

The hardest thing is showing up. A lot of founders, they're super overwhelmed with daily activities and I totally understand that. They don't have time or energy to show up. In our case, we were lucky to be a team of several people so we could distribute those duties. I was the one writing the updates and Benedict was building the product. If it was just one person, I can imagine how part of that could have been easily overlooked or boot as secondary activity somewhere else.

Courtland Allen: 54m 2s

So you guys have had some pretty cool successes in the process of building this. One of them is that you were the number one product of the day on Product Hunt, which is not an easy feat to accomplish. You get, I'm sure, hundreds, and maybe thousands, of people visiting your website and signing up.

How did you become the number one product of the day on Product Hunt and what were the results of that for you?

Jane Portman: 54m 25s

There are two answers. One is we were super wise and we orchestrated this launch very well. Number two answer is that thankfully nobody, like Intercom or somebody else, launched their thing on the same day because if they did, our efforts wouldn't really matter because we would be outnumbered.

But, from the resources that we had on hand, based on our experience, we've tried to organize the most appropriate launch and we have a blog post about that, too. We had a sequence of things that we were going to do on the launch day and how we were going to approach our own mailing list with things they could do to help us and how I would write to my own UI Breakfast mailing list so that they can also go out and support us.

Things like that. It just it comes down to producing certain assets and then getting in touch with your audience in the most delicate and proper way so that they don't feel abused, but rather feel supportive. And it's our motto throughout our marketing. We never want our friends or our audience to feel abused because what we want is, once in a blue moon, to get their support in not very hard activities, like tweeting out or upvoting us. So, that's basically the gist of it.

Courtland Allen: 55m 49s

How do you get your audience to help support you and tweet you and upvote you without making them feel abused or sold to?

Jane Portman: 55m 56s

I guess every person has their own sense of balance and boundaries and there are many popular influencers out there who are on the hard selling side. We are not on the hard selling side, but on the same side, we're not in the shy cohort. So, we know that every email should have a call to action, so people cannot just guess that they need to help you.

You need to think of the ways and write down the ways people can help you. You can include the links to Tweet, you can include a proper call to action to visit Product Hunt, etc., all these basic conversion classic instruments. We do use that to provide a way for people to support us.

Courtland Allen: 56m 44s

I gave a talk a couple of years ago at ConvertKit's conference, and I think it was called, "How to Get Lucky" or something like that, but a huge part of the premise was that a part of luck is people helping you and people don't necessarily know how to help you unless you help them help you by doing exactly what you're saying, by telling them, "Hey. This is how you can help us. Could you Tweet this?", etc.

Have a call to action. It's so obvious when it's said, but I spent many years in my life never telling people what I was working on or telling them how they could help me, and when I changed that, just like you did, I saw a huge increase, a huge result and people basically being on my team and helping me do the things that I was doing.

Jane Portman: 57m 24s

One more mental model that helps is that people who are on your audience, you are not the center of their world. They most likely know close to nothing about what you do, most likely. So, whatever you do, you've got to provide context and maximum clarity for what are these passages about. If it's a launch email, give them links where they can read on about your product, give them some more context.

If it's a Tweet done, or things like that, that everyone knows what you're talking about, give them an idea of what's going on, etc. So, at each point of the communication, make sure that it's super clear who you are, where you are at, what stage you're at and what do you want them to do. To do that, you've got to use the classic methods, good copywriting, nice clear design, and anything else you can do in your arsenal.

Courtland Allen: 58m 20s

What’s at the top of your mind nowadays? You're continuing to work on your positioning and improving it. What does the near term future look like for Userlist?

Jane Portman: 58m 29s

It looks brilliant, of course. The big step that we have decided to take is, both myself and Benedict, we are going full time on Userlist, starting January. So, we have a new rep for online work.

Courtland Allen: 58m 42s

Oh, wow. Congratulations.

Jane Portman: 58m 43s

Yes, thank you. We're absolutely thrilled. We took this decision when we were at MicroConf together, having dinner on the top of the mountain in Croatia, and was literally-not-literally on the top of the world, just feeling great about what we've done and that we can finally be positive that it's worth our full-time investment. So, that's big news.

Courtland Allen: 59m 12s

What goes into making a decision like that? Because so many people are struggling to figure out, financially, "Is it smart for me to go full time with my product? Does it have the kind of growth that it needs to be able to support me in a reasonable time frame before I run out of money and things get uncomfortable?" How did you know that it was time to go full-time?

Jane Portman: 59m 27s

There were clearly signs that we're doing the right thing. However, the metrics were, as we discussed, growing not even close to what we wanted to do and it became apparent that we're moving in the right direction. Benedict desperately needed more development time to build a few more features that we think would be deal breaking for some of our potential customers.

For example, that very in-app messaging and so on. On the other hand, I could definitely use more time to just start pulling marketing levers forward and start filling out that top of the funnel because over the last year in particular, we have really fine-tuned the middle of the funnel and the bottom of the funnel.

We have proper assets in place, proper on-boarding for the email list, proper on-boarding for the users. So, it took us so long to build those assets and now it was just a matter of real labor to start hustling and filling out the top of that funnel.

That, combined with the confidence that we got from the community, the support from the community, the fact that we got, we didn't have to explain what we do anymore, it all played together into a decision that we've built something worthwhile together and that we need to double down on growing it.

So, we build it and then we need to grow. I think that phase from going from building an MVP to growing your actual product, it's where it makes sense to go full time.

Courtland Allen: 1h 0m 58s

Well listen, Jane. I'm excited that you're both going full time on this and I think it'd be really cool to have you on later next year to check in and see what the results of that are.

Before I let you get out of here, I really would love to get your advice as somebody who's been building startups for years, who is working on your second business. What would you say to somebody who's just considering getting started with their very first business? What do you think they should take away from your story and your lessons that you've learned?

Jane Portman: 1h 1m 20s

Start with something smaller. It's great if you have info-product experience because it helps you practice all these launches and everything. But, even if you go straight to SaaS, build something smaller so that your stakes are not building something for five years and then killing it.

Because the chances of success are not very high for any SaaS. If you're doing it for the first time, they're even lower. So, pick an existing market category, build a simple product and do the drill and then see where it takes you. It might be that you succeed, but it might be that you don't and then you'll be very well familiar with the process so you can start over and build something else, correct your mistakes and everything like that.

Courtland Allen: 1h 2m 5s

Jane Portman, thank you so much for coming on the show. It was my pleasure to have you. Can you let listeners know where they can go to learn more about what you're up to at Userlist?

Jane Portman: 1h 2m 14s

Absolutely. It's been a pleasure to have this meaningful conversation with you, Courtland. Thank you. Userlist is at userlist.com. By the way, we bought the ".com" domain and we're thrilled about it. So, it's at userlist.com and we have also put together a deal for the listeners, in case you'd like to have a special discount, head over to userlist.com/indiehackers and you're going to have 30% off for your first three months at Userlist. Hope that's helpful if you're just starting off the ground with your SaaS.

Courtland Allen: 1h 2m 46s

Very cool, thanks so much Jane.

Jane Portman: 1h 2m 47s

Thank you for having me. It's been a pleasure.

Courtland Allen: 1h 2m 50s

Listeners, if you enjoyed this episode, I would love it if you reached out to Jane and let her know. She is on Twitter, @UIBreakfast. Also, if you're interested in hearing my thoughts on this episode and other episodes of the Indie Hackers podcast, I send a newsletter with each new episode where I just share my thoughts and reflections and takeaways. So, you can find that at indiehackers.com/podcast. Thanks so much for listening and I will see you next time.