Aim for the Base Hit: Sifu Edward & Sifu Julliana Armstrong Sit Down With WishList Member's Tracy Childers

Adapted from the recorded conversation; the guest's words are verbatim. The questions are reconstructed and voiced by Sifu Edward and Sifu Julliana Armstrong.

🎥 Video podcast coming soon. The complete interview will play here once published. The full conversation is transcribed below, and the audio edition will be available on sifuarmstrong.tv.

In a new Sifu Armstrong interview, the man behind the membership-site software running on over 100,000 websites explains why the smallest possible start is usually the smartest one.

Tracy Childers was twelve years old in 1982 when his job title was “director of shipping,” duplicating audio tapes for his father’s real-estate seminar business and packing them to mail out. That early exposure to how badly people wanted information, he told Sifu Edward and Sifu Julliana Armstrong, shaped everything that came after, including WishList Member, the WordPress membership plugin he co-built after a friend, Stu McLaren, got frustrated trying to set up his own membership site and couldn’t find software that wasn’t “either cheap and impossibly complicated, or expensive and hand-held.”

Childers is unusually candid about the calls that were hardest to make as the business grew. After a full year spent building a companion theme product, he had to admit it wasn’t working and kill it entirely to protect the core product instead. He describes the harder, multi-year rebuild of WishList Member itself in blunt terms: “It’s like building an airplane as you’re flying it.” Both decisions, he said, came down to the same discipline, recognizing what’s actually driving the business and refusing to keep feeding what isn’t.

That same instinct for restraint runs through the piece of advice Childers said he’d give anyone starting from nothing. He traces it back to childhood softball, where he was never physically built to hit a home run the way his best friend could, a friend who, he said, “a lot of the time he’d swing for the fence and hit it straight to an outfielder,” and be out. Childers took a different approach. “I’m never going to be able to hit this thing over the fence. But I could always hit it right over the first baseman’s head,” he said. He carried that logic directly into business: “Just do something small, because in that small thing, you’re going to learn a whole lot.”

Beneath the software and the strategy, what Childers seems proudest of is the team he’s built: about eighteen to twenty people, all remote, several with him well over a decade. “One of the most gratifying things that’s changed my life is to see them put their kids through school based on the fact that they work for us,” he said, a line that reframes the whole business as something built for more people than just its founder.

Taken together, the conversation lands on a lesson that applies well beyond software. The person swinging for the fence on their very first attempt usually pops out and learns nothing from it. The one who just gets on base (a clean, simple win, repeated) builds the real experience that eventually makes something bigger possible. It’s the exact instinct the Armstrongs drill into a new student who wants to throw the flashiest technique before they can hold a stance: master the small, honest thing first, and let the impressive result show up later, on its own.

In This Conversation

Duplicating seminar tapes at twelve and learning how hungry people are for information
How a friend’s frustration with existing tools became WishList Member
Killing a full year of work to protect the product’s core
The softball story: why aiming for a base hit beats swinging for the fence
Building a remote team where people have stayed a decade or more
Where to find Tracy Childers and WishList Member

The Full Conversation

Sifu Edward Armstrong: Tracy Childers built WishList Member, the software that powers over a hundred thousand membership sites, the exact kind of member community we run with Club Sabernet. So when he talks about protecting content, serving members for a decade, and building a team that stays, he's describing the infrastructure of everything we're trying to do. He's a builder's builder.

Sifu Julliana Armstrong: And he gave us the best sports analogy we've had, which is saying something on this show. He was a small kid in softball who could never hit a home run, so he stopped trying, and just aimed to drop it over the first baseman's head, every time. His big-hitting friend swung for the fence and popped out. That's the whole difference between ego and mastery, and I couldn't wait to talk to him about it.

Our guest is Tracy Childers, founder of WishList Products. Tracy, a pleasure.

Tracy Childers: Well, thank you. Appreciate you having me.

Sifu Edward Armstrong: Your path started young. Take us there.

Tracy Childers: I grew up with a father who was an entrepreneur: automotive repair shops first, then real estate, and then he started teaching people how he invested in real estate. Back then the only things around were direct marketing and seminars. So at the ripe age of 11 or 12, my job was "director of shipping," which meant I duplicated audio tapes and packaged them to send to the people who bought them at the weekend seminar. This is 1982. And I recognised even way back then how hungry people were to buy information, all kinds of information. I was always fascinated with technology, so the internet just became a really good fit for me.

Sifu Edward Armstrong: And WishList Member came out of a friend's frustration. Tell our operators the story, and the formula underneath it.

Tracy Childers: Back in 2008, a close friend, Stu McLaren, and I decided to partner up and build software to run a membership site. He was trying to set one up himself and was really frustrated. The solutions back then were either cheap and impossibly complicated, or expensive and hand-held, and neither had anything to do with WordPress. He said how frustrated he was, and I said, "Why don't you just build something?" He said, "I don't think you heard me. I can't even use the software that already exists." And I said, "Why don't we team up? I've been developing software for a while, I think we could build this fairly easily." Everything back then was going toward themes (how a site looks), and plugins, how it functions, were mostly free. So we said, what if we became the first membership that sold a new plugin every month? To run that, we had to build our own system, and that was WishList Member. We had no idea how important that first plugin would be.

And the formula I'd figured out long before was simple: look at what's popular online and find a hole in what's available. I'd built video software back before YouTube, and people kept saying, "great software, but it's really complicated to use." So if you can find something everybody's talking about, but nobody's meeting the actual problems people are discussing, you have a really good formula. Lots of people were talking about WordPress and membership sites, and the solution just wasn't there.

Sifu Julliana Armstrong: What moves me is your team. You had 35 people under you at 26 and hated it, and now you've built something very different.

Tracy Childers: At 26, my father and I had a company selling information online, and I had 35 people working for me, and man, it was really, really hard. I said, "I never want to do that again." So afterward I worked mostly on my own. But as WishList Member grew, we naturally had to add people, and I realised that at a certain level of success, it's largely based on what kind of team you put together. We're about 18 to 20 now, all virtual, working from all over the world. We've always done it that way, so the pandemic didn't affect how we work at all. We just crossed 13 years, and we have people who've been with us well over 10 years. And one of the most gratifying things that's changed my life is to see them put their kids through school based on the fact that they work for us.

Sifu Julliana Armstrong: "To see them put their kids through school because they work for us." That's the part of building that nobody photographs, and it's the part that matters most. You hated managing 35 people, and instead of swearing off people entirely, you learned to build a small team that stays for a decade. When you build something real, you're not just making a living for yourself. You become the ground that other families stand on. That's the responsibility of leadership, and you clearly feel the weight and the joy of it.

Sifu Edward Armstrong: You made a brutal call. You re-engineered a successful product from the ground up. What did that take?

Tracy Childers: Over time, with all the feedback ("could it do this, could it do that?"), WishList Member had piled feature on top of feature, and it stopped making sense. So we took a step back and said, "We need to re-engineer this thing." We looked at everything we did and everything we wanted to do, and had to build a new structure. Building fresh, a working solution takes about three months, because nothing's distracting you. But building on top of a system that thousands of people rely on, being careful not to break compatibility for all those websites. It took us two and a half years. Much longer than we expected. I've said many times, it's like building an airplane as you're flying it. But once we did it, it put us on a course to open up a lot of new opportunities.

Sifu Julliana Armstrong: And before that, you killed a project you'd worked on for a full year. That's the hard part. Tell me.

Tracy Childers: I'll be honest with you. With all the competition, I kept thinking we also needed to build a theme for our people, and we spent a little over a year working on it. At the end, it just wasn't going the way I wanted. And I had to step back and say (it was a really, really tough decision), "We need to stop. Even though we put a whole year of work into this, we need to get back to our core." Because sometimes it's really important to understand what's driving your whole business. If we kept working on something that wasn't the core, while the core itself needed updating, that was one of the toughest calls I ever made. And it was the right decision.

Sifu Julliana Armstrong: Killing a year of work to return to the core is one of the hardest disciplines there is, because everything in you wants to justify the time you've already spent. But the warrior doesn't defend the wasted year. They cut it loose the moment they see it's pulling them off the core. On the mat, that's the fighter who abandons the flashy technique they've drilled for months because it doesn't serve the fundamentals. Sunk cost is a trap. Protecting the core is everything. You made the master's call.

Sifu Julliana Armstrong: Your top tip comes with the softball story. Give it to our warriors.

Tracy Childers: You have to realise what you're good at, because if you try to do something you're not good at, it usually fails miserably. I played baseball as a kid, which turns into softball as you get older, and I'm not a big, strong guy. My best friend probably had the most home runs in the league, but a lot of the time he'd swing for the fence and hit it straight to an outfielder, and he'd be out. And I thought, "I'm never going to be able to hit this over the fence. But I could decide where I wanted to hit it," and I could always drop it right over the first baseman's head. I just wanted to get a base hit. I moved that into business. I see so many people who've never done any real business swinging for the fence, and that's not where you get your experience. You get experience by doing something small. It doesn't have to be the next thing to change the internet. Just do something small, because in that small thing you're going to learn a whole lot. So many people try to build a site with every piece of functionality. No, make it simple, and just do something.

Sifu Julliana Armstrong: "Just get a base hit." That is exactly what we drill into every white belt who wants to throw the spinning, flying, highlight-reel technique before they can hold a stance. The one who swings for the fence pops out every single time and learns nothing. The one who just gets on base (a clean, simple technique executed well) builds the experience that eventually makes the spectacular possible. Ego swings for the fence. Mastery gets on base, session after session, until one day the home run comes without you reaching for it.

Sifu Edward Armstrong: What are you proudest of, what's next, and where do people find you?

Tracy Childers: What I'm proudest of is hearing someone say, "Your solution really changed my life, now I can do everything I was wanting to." We've crossed over a hundred thousand websites, and when I see our software impacting other people's lives, that's the most gratifying thing over the whole time. What's next: after the pandemic, online training exploded, so we're building a course builder into WishList Member, and we're adding gamification. You can earn points and badges. I just finished a meeting on it right before this. And the reason to use WishList Member is that we were one of the earliest solutions, so we built it to be incredibly flexible, and we have by far the most integrations of any software like ours. The easiest way to find us is wishlistmember.com.

Sifu Edward Armstrong: Tracy, I've loved this, thank you for the background and the wisdom. And the gamification, the points and badges? That's a belt system, my friend. We speak the same language.

Tracy Childers: It's been an honour to be here. I appreciate all the kind words.

Sifu Julliana's closing word: Tracy gave us the base hit, and it's the whole philosophy of learning anything hard. The white belt who swings for the fence pops out every time and learns nothing; the one who just gets on base, session after session, is the one still standing at black belt. And he killed a year of work to protect his core, the master's refusal to let sunk cost pull him off the fundamentals. Ego swings for the fence. Mastery gets on base.

Sifu Edward's closing word: Tracy builds the exact infrastructure we believe in: member communities, protected content, a team that stays a decade and raises their families on it. And he adds gamification: points and badges for progress, which is nothing but a belt system by another name. Build the thing people rely on, guard your core ferociously, and let a hundred thousand small wins compound into something that changes lives. We don't entertain warriors. We create them.

Tracy Childers, founder of WishList Products, creators of WishList Member, the WordPress membership plugin running on 100,000+ websites. wishlistmember.com.

ILLUSTRATIVE RESULTS. Any revenue, enrollment, margin or retention figure in this conversation is either a documented result from one of our own operations, a figure the guest reports about their own business, or an illustrative example, never a projection of your results.

Nothing here is financial, legal or tax advice.

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This conversation is part of the Sifu Armstrong Warrior Intelligence Series: interviews with world-class performers, builders, and thinkers, filtered through the lens of the warrior's path.

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