[SaaS & WordPress Series] Powering Membership Success: Tools and Tactics With Blair Williams

Blair Williams is the CEO of MemberPress, a powerful WordPress plugin company that empowers creators and businesses to launch and manage membership sites and online courses. He founded MemberPress after years of custom-building membership systems and recognized a gap in the market for a flexible, developer-friendly WordPress solution. Blair is also the Owner of Caseproof, the company behind industry-leading WordPress plugins like MemberPress, PrettyLinks, Easy Affiliate, Wishlist Member, MemberMouse, AccessAlly, ThirstyAffiliates, and Buy Now Plus.

Here’s a glimpse of what you’ll learn:

• [5:09] How Blair Williams began developing WordPress plugins and what inspired the creation of PrettyLinks
• [12:11] Why Blair designed PrettyLinks’ freemium model to balance free and pro features
• [15:55] The process behind pricing strategy and how customer feedback shaped product evolution
• [20:25] Blair’s must-have WordPress plugins for any serious website 
• [25:43] How MemberPress bypasses theme issues with smart design tools
• [33:51] Common mistakes entrepreneurs make when launching membership sites
• [38:25] The importance of onboarding and how MemberPress helps users get started faster
• [43:11] Blair’s approach to acquiring and integrating membership plugin companies
• [48:42] Examples of thriving membership sites like Over 40 Alpha and The McCance Method
• [56:54] Blair’s favorite business and personal development books that shaped his leadership philosophy

In this episode…

Building a thriving membership business requires more than great content — it takes strategy, the right tools, and a deep understanding of your audience. From simplifying user experiences to streamlining revenue models, entrepreneurs must balance creativity with technical precision to keep members engaged. So how do you create a membership site that actually scales and sustains long-term success?

A seasoned innovator in software and membership platforms, Blair Williams believes simplicity and customer focus are the keys to success. He highlights that many creators overcomplicate their offerings before launching, when the real key is just getting started and refining through feedback. Blair emphasizes the power of accessibility — tools like WordPress and AI have made building profitable membership sites easier than ever. He also points out that success stems from aligning features with audience needs, whether through strong onboarding, smart pricing models, or seamless integrations that enable entrepreneurs to monetize their expertise efficiently.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz sits down with Blair Williams, CEO of MemberPress, to discuss the tools and tactics that power successful membership businesses. They discuss common mistakes creators make when launching sites, how to simplify offers for growth, and what makes MemberPress stand out in the WordPress ecosystem. Blair also shares lessons from building and acquiring top plugins across the web.

Resources mentioned in this episode:

• Blair Williams on LinkedIn 
• Caseproof
• MemberPress
• PrettyLinks
• WishList Member
• Easy Affiliate
• MemberMouse
• AccessAlly
• ThirstyAffiliates
• Buy Now Plus
• All in One SEO
• Awesome Motive
• MonsterInsights
• Formidable Forms
• WPForms
• OptinMonster
• RafflePress
• Pixel Jar
• AdSanity
• SeedProd
• ReadyLaunch™
• Elementor
• Divi
• Beaver Builder
• WP Search
• Heroic Knowledge Base Plugin Documentation
• The Over 40 Alpha Podcast
• The McCance Method
• For Bass Players Only
• 37signals
• The 7 Habits of Highly Effective People by Stephen R. Covey
• Traction: Get a Grip on Your Business by Gino Wickman
• The Bogleheads’ Guide to Investing by Taylor Larimore, Mel Lindauer, and Michael LeBoeuf
• Feeling Good: The New Mood Therapy by David D. Burns, M.D.
• Feeling Great: The Revolutionary New Treatment for Depression and Anxiety by David D. Burns, M.D.

Special mentions:

• Ben Rojas on LinkedIn
• Syed Balkhi on LinkedIn
• Zach Kwarta on LinkedIn
• Steve Wells on LinkedIn
• Jared Atchison on LinkedIn
• John Turner on LinkedIn
• Brandon Dove on LinkedIn
• Jeff Zinn on LinkedIn
• Stu McLaren on LinkedIn
• Tracy Childers on LinkedIn
• Matthew Brown on LinkedIn

Related episodes:

• “WishList Member: Moved to Tears by His First Sale – with Stu McLaren [Sales and Revenue]” on the Inspired Insider Podcast
• “Automation Solutions with Wade Foster Founder of Zapier” on the Inspired Insider Podcast
• “Pipedrive: Brain Surgery, Married, & Moved Company from Estonia to U.S. All at Once – with Urmas Purde [Inspiration]” on the Inspired Insider Podcast
• “[SaaS Series] Tips To Thrive in the SaaS Space With Sujan Patel” on the Inspired Insider Podcast

Quotable moments:

• “People were buying it — that’s a great vote. You know, people are voting with their wallets.”
• “It doesn’t really matter what people are saying about your product. If there’s a market for it, your customers will buy it.”
• “I think the first mistake that they make is they don’t get started soon enough.”
• “We want to see these brands survive. We don’t want to see them just falter and go away.”
• “The reason that we’re in this is for, really, the entrepreneur — for the person who is trying to get some movement and make a living off of what they know.”

Action steps:

1. Start simple and launch early: Launch before things are perfect so you can learn and improve through real-world feedback.
2. Focus on serving a clear, specific niche: Narrow your audience to a defined group to create stronger relevance and easier growth.
3. Keep your offering and pricing straightforward: Use simple tiers and clear value to reduce confusion and increase conversions.
4. Build a supportive community, not just content: Foster member interaction to create belonging and improve retention.
5. Listen to user feedback and continually improve: Use customer input to guide updates and refine your offering over time.

Episode Transcript

Intro: 00:15

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz: 00:22

Dr. Jeremy Weisz, here Founder of InspiredInsider.com where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Blair Williams. Blair, there’s so many sites, I’m going to list them all in your official bio.

Blair. You can check them out. Caseproof.com. It’s kind of like the main hub, but they run MemberPress and PrettyLinks and I’m going to name them all. But before I introduce Blair we’re going to talk about all things memberships. 

Right. And much more software memberships acquisitions. Who knows what we’re going to get into here. Before I introduce Blair, officially, there’s some other podcast episodes you can check out. Okay. 

Actually, Blair owns and runs WishList Member, but a while, a long time ago I had Stu McLaren on who founded WishList Member. That’s a great episode to check out. This is.

Blair Williams: 01:13

Good guy.

Dr. Jeremy Weisz: 01:14

Yeah great guy. This is also part of the SaaS series and so you can check out. I had one of the co-founders of Zapier on Wade foster. That was a really good interview. One of the co-founders of Pipedrive on was a good interview.

One of the founders of Mailshake, Sujan Patel. He talked about how he’s been acquiring SaaS companies. Actually, Blair he has used that playbook as well. You know, his own playbook, but it’s a great episode. He talked a lot about Blair, you’d like it integration and integrating companies, which is, you know, people talk about acquisition and I haven’t heard as much about the integration part into the whole company, and that was interesting to hear his thoughts. So many more on InspiredInsider.com. 

This episode is brought to you by Rise25. At Rise25, we help businesses give to and connect to their dream relationships and partnerships. We do this in a couple ways. One, we’re an easy button for a company to launch and run a podcast. We do the strategy, accountability, and the full execution and production to make it easy. 

We’re also an easy button for a company’s corporate gifting. So if you have great clients, partners, prospects, even staff from a culture perspective, people send us a list of addresses and we do everything else. And usually it’s a campaign of gifts. It’s not just one. It’s, you know, maybe a gift every four months for three years type of thing. So we kind of call ourselves the magic elves that run in the background and make it stress free for a company to build amazing relationships so they could do everything else, you know. And the number one thing in my life is relationships. 

I always look at ways on how I can give to my best relationships, and I found no better way over the past 15 years than to profile the people and companies I admire in the podcast and send them sweet treats in the mail so you can go to Rise25.com or email [email protected]. 

I am super excited to introduce Blair Williams. He’s created top WordPress plugins. We use some of them actually. MemberPress, PrettyLinks, Easy Affiliate. 

He’s also strategically expanded his portfolio, acquiring key platforms like MemberMouse, WishList Member, and AccessAlly. He has empowered countless creators to turn their passions into profit. So Blair, thanks for joining me.

Blair Williams: 03:39

Yeah, I’m very happy to be here. Thank you.

Dr. Jeremy Weisz: 03:41

Blair joined this call because of PrettyLinks. Okay. And I tell everyone and I didn’t know this before I was chatting. Big shout out to Matt Brown. First of all, Matt Brown introduced us.

He’s awesome. Oh, yeah. And I didn’t know you created PrettyLinks. And there are certain things, Blair, that if they went down, we would want to huddle in a corner. 

Okay. And PrettyLinks is one of those things because. And I tell everyone you need to get PrettyLinks. Not now. Because I know you, I say it even more, but because, you know, Zoom gives you this long URL. Okay. So I’m like, literally everyone should be installing PrettyLinks on their site and pointing that long URL to a pretty link, right? And so you came in and we have rise 25.com/you know, and in the pretty link for our Zoom room. So I could just tell people to go in the Zoom room and I don’t have to remember to go to 6396272 whatever. 

Right. So everyone should be using PrettyLinks. I, you know, wholeheartedly. You know, believe that. And I know early on PrettyLinks, you got it. You got it. I guess in the comments you were getting just slammed because.

Blair Williams: 05:06

I got some heat.

Dr. Jeremy Weisz: 05:07

Talk about that for a second.

Blair Williams: 05:09

Yeah. So I’ll tell you first of all. So like I, I just kind of created PrettyLinks just for funsies you know kind of thing. Back in the day I wasn’t planning on, you know, making it into like a premium plugin. And if you can imagine it, I put it in the WordPress directory, the free version in 2009.

So it was a long time ago. And then I think, you know, six months later I decided, hey, you know, I think I’ll try to launch a pro version of this, just, you know, to see if I can make some money at it. And before you and sure enough.

Dr. Jeremy Weisz: 05:45

Before you launched the full version, were you just getting traction from putting it up on, like how were people finding it?

Blair Williams: 05:51

They found it through the WordPress plugin directory. I mean, WordPress has a very expansive plugin directory, and there were a few other plugins at the time that kind of did the same thing as PrettyLinks, but they would, I think they were made more for like affiliate marketers, which PrettyLinks works great for affiliate marketers as well, but it would always append like a little slug in between. So there was one I think called Go Links. And so it would be like, you know, your domain slash go slash whatever your slug is, you know? And I was like, that’s stupid. I want to be able to just make any link, you know, completely customized. 

And I want it to use my domain name, and I want it to use my brand. And it turns out there were some performance things that we had to work out with because the little slug makes it a little bit easier. But we have got it dialed in at this point. It’s been on the market for many years now. But yeah, I think got.

Dr. Jeremy Weisz: 06:50

Why did you create it in the first place, though?

Blair Williams: 06:52

Well, I just I came from a development background where I was writing Ruby on Rails, so and I had had some other previous experience with other things, but I kind of got into WordPress around 2008 and started helping people with marketing, and, and I was kind of learning as I went, you know, as you do sometimes as a contractor. And I just started, you know, seeing this need, you know, I’m like, oh, these are terrible links. And I saw, I think there were some things like tiny URL and other kinds of things. That was kind of when Twitter was, you know, kind of getting started in link shrinking was a big deal. And so I just kind of was like, hey, you know, I could do that pretty easily on WordPress now that I’m fiddling around with it.

And, and I just felt like it was a really great, you know, utility for me personally. And then I just put it on the WordPress plugin directory. And, you know, one thing led to another. It was actually the first plugin that I ever released. And it was pretty cool. 

Like, I remember the first day I released it, and I’ve launched other plugins on the WordPress plugin directory since. And somehow with PrettyLinks, I don’t know if it was the name, because I do think the name has always been. I’ve always been happy with the name. It’s a great name and yeah, and the branding and stuff, but it got 184 downloads the first day and I was like, whoa, this is amazing. This is great. 

You know? And so and then we just started getting, you know, more and more kind of traction on the free version. And, you know, I just decided, hey, I’ll try to launch this as a pro version and see where it goes, you know. So it was a pretty early on, you know, kind of premium, I would say plugin for WordPress. I think the wish list actually came out before then. 

I think they were like 2008. But pre links were pretty early on. I didn’t know we didn’t get around so I didn’t get around to launching MemberPress until 2013. So you know four years later.

Dr. Jeremy Weisz: 09:08

So PrettyLinks means you talk about some of the lessons you learned one customer service, right. Talk about that.

Blair Williams: 09:16

Oh yeah. Well, I’ll tell you, there is actually a story about that. Like I started getting like some negative ratings on PrettyLinks and I’m like, what the heck is going on? And they’re like, there’s no way to contact you for support. Like, I didn’t even have like a contact form on my website to do support.

I didn’t know, you know, I was like, oh, okay, I guess I need a form for people to contact me, and then I can help them with the plugin, you know, and so remedied that very early on. And you know, we’re great with support now. Trust me, we have lots of great support. staff members and lesson learned, absolutely. 

Yeah. And so and you know, you have oh go ahead. I was just going to say you were talking about like getting slammed in comments and stuff like that. And you know I told several people about it, I won’t name any names. But there was like a kind of a major internet marketer at the time who I was like, hey, I was just kind of telling him the idea and he’s like, I don’t know why anybody would use that. 

And then, you know, one of the founders of WordPress actually was on a comment thread and was like, this is stupid. I mean, I can do this with like one line of code or something like that. And I’m like, well, there is definitely a use case for this that, you know, maybe you’re not aware of. And I guess the lesson of that is that, you know, like, it doesn’t really matter what people are saying about your, you know, your, your product. If there’s a market for it, your customers will buy it. 

I mean, people were buying it. You know, that’s a great vote. You know, people are voting with their wallets, right? So yeah, 100%.

Dr. Jeremy Weisz: 10:56

That’s the only vote that matters. Someone’s actually paying for it. And, you know, right here on your site, obviously, Blair says maximize your affiliate profits with PrettyLinks, the leading affiliate tool trusted by over 8 million marketers, influencers and content creators. And we use it. This is obviously we’ll talk about some of the use cases.

And I know you know Pat Flynn uses it who I know. But we use it. It’s not even for affiliates. It’s just like to make life easier by redirecting to Zoom or for doing an event. We’ve done events and we’ve hosted them on Eventbrite or Party full. 

And so people don’t have to remember this long URL. We use the same thing, right? It’s just like com slash Chicago 2026 event or something. And it just redirects to that page. so there’s so many use cases for it. 

How do you think about it? Because you have to and I had the one of the founders of Jotform on and he’s got a freemium model and they have like 25 million I think over users. And how did you go okay, what do I include in the pro version versus the free version. Like how did you think about pricing and that piece.

Blair Williams: 12:11

Yeah, it’s really kind of an art, a freemium, the freemium model, because you have to provide enough value that people that it’s a useful, useful tool. In fact, I would say with PrettyLinks, it’s probably like the free version is very useful to the point where, like, not as many people upgrade to pro as we would like, you know, but we but we’re happy. We have a lot of users and we have a lot of, you know, kind of like, you know, we’ve got a lot of great paid users to customers that. But like, you know, we kind of looked at like, you know, I would say, you know, features like that make it easier for like people who are making money, you know. 

Like tags and categories and that sort of thing. Advanced redirections I mean, you can redirect, you know, based on a country, you know, the country that the visitor is in, you know, you can, you know, there’s more. You know, I would say reporting the developer tools are a huge kind of it’s a really cool thing because you can hook this right into Zapier, or you can hook it into your own custom code, and you can just create links on the fly, you know, that show up in your WordPress, you know, admin, and you can manage them that way. You know, QR codes, you know, it’s all listed right here. And so really, I would say kind of the way that we looked at it was that if somebody is looking at it like the free version, they’re using it, you know, kind of they’re just like, hey, I have a blog and I want to just create links. 

Fine. That’s great. You can use this. This is a great tool for that. But if you’re making money at it and you’re like, really? 

Look, I mean, we have people that are managing tens of thousands of links on PrettyLinks in their WordPress admin, you know, like serious affiliate marketers who are making a lot of money on this thing. And they really appreciate the ability to, you know, really organize what they’re doing and, you know, really organize their links. And so that’s, you know, we also have some new innovative features. I would say one of them is called product displays. So it allows you to create, you know, like ads of your links and that sort of thing. 

And they’ll show up right on your WordPress admin interface or on the front end, and we have a couple of other kind of cool features that are going to be launching pretty soon. One of them, I’ll tease here, is that we’re a link in bio feature. So if you look at like a company, you know, product like Link Tree, you know, where you have, you know, your link on like LinkedIn or on Instagram. And they go and you can see all of your different catalog links. You’ll be able to do that same thing with PrettyLinks soon as well.

Dr. Jeremy Weisz: 15:05

Yeah, I’ve seen people LinkTree and you go to it and it’s like, here’s my website, here’s my LinkedIn, here’s my Instagram, here’s all these things. 

Blair Williams: 15:14

Yeah.

Dr. Jeremy Weisz: 15:15

How did you determine that, like when we’re looking at in here like they have a free version but they have it’s interesting you looked at the people who are making money from it. You’re like, okay, they’re making money. They can, you know, obviously afford to pay something. I mean, listen, the beginner version is $99 a year, right?

And $150 a year. I’m sure there’s people who are like, oh my God, I’d pay so much more than that. And there’s people like, that’s perfect. But how do you decide on when you were evaluating it? Did you just go out and talk to the customers, or did you look at their usage on certain things, like how did you determine these.

Blair Williams: 15:51

Like pricing?

Dr. Jeremy Weisz: 15:52

Yeah, the pricing and the features.

Blair Williams: 15:55

Yeah, I mean, we listen to our customers for one. You know, I think initially the pro features were just kind of advanced redirect types and that sort of thing. But like over time we have we’ve added, you know, features that, you know, basically our users have have told us and of course we look at the market as well, like what are other kind of competitors doing in the space and what are other, you know, kind of, you know, affiliates and what are the affiliate marketing trends? You know, so we look at all of those kinds of things to kind of come up with a feature set and, you know, and if you look at like, I think this is a huge value. Just basically, you know, you look at like any of the competitors in the space and some of them charge vastly more money than this, you know, and, and PrettyLinks is a very well proven tool.

It’s been around for, you know, 16 years basically. Well, actually it has been around for over 16 years now. And, it just works. You know, the thing works.

Dr. Jeremy Weisz: 17:01

So yeah, I’m curious. No, thanks for pointing that out because the free version is very robust, you know. Yeah. And even if you look at the beginner marketer and super like the bigger plans, it still includes a lot of stuff. It’s more like the sites that they’re using on is the main difference. And obviously you mentioned the product display stuff.

Blair Williams: 17:26

Yeah. If you look at the super affiliate, you know, we’ve got some differentiation there. And you know, you get the product displays, you get the developer tools, the QR code generator, that sort of thing. So there is some differentiation there.

Dr. Jeremy Weisz: 17:41

You mentioned, you know, obviously a big market is affiliates because they’re using redirects to go, okay, hey, I recommend, do people have a pretty link for pretty link. That’s kind of meta right. Like if we for their affiliate.

Blair Williams: 17:56

We do. And there’s a lot of people who use. Yeah.

Dr. Jeremy Weisz: 18:01

You know, hey, I recommend this hosting company go to you know.

Blair Williams: 18:05

Yeah.

[Continue to Page 2]