Twinterview With Chris Lema (GM LearnDash & Founder CaboPress)

Our esteemed guest for today, Chris Lema needs no introduction. Those who are familiar with the WordPress ecosystem already know him as the vice president and product strategist of LiquidWeb & Nexcess. Recently; he has also taken on the new position as the General Manager of LearnDash.

Chris Lema is a popular blogger, coach, speaker, and WordPress/WooCommerce evangelist. Most notably, Chris founded #CaboPress (A refreshing way to get business advice while relaxing in a pool).

It’s an honor for WPExperts to invite Chris Lema for a brief twinterview session. We have asked him several questions related to his professional and personal life that our followers will love to know.


twinterview with chris lema

Let’s get started.

Q1. Everyone knows the name ‘Chris Lema’ in the WordPress community; how did you become the top-most influential and lovable person for people in the WordPress business?

Ans: First, I question the assumption. Nevertheless, I think the reason my face shows up on so many sites is that I write a lot. has something like 1500 posts about WordPress, including a lot of opinions about plugins.

Q2. You have helped startups and businesses grow for more than 16 years now. What are some of the most notable changes you have witnessed in the WordPress ecosystem during this time span?

Ans: That’s a great question. My favorite is that some plugins have started thinking more like SaaS companies. And part of that has been the shift to automatic yearly renewals. I’ve been singing that song since 2010.

Q3. Tell us about your new role as a General Manager of LearnDash and some of the day-to-day activities to grow it furthermore?

Ans:  We’re working on our 3.6 release and our upcoming 4.0 release in Q1 of 2022. Most of my job is supporting the marketing, developers, product, and support folks as they support customers worldwide.

Q4. CaboPress is such a refreshing and unique idea to get business advice. Being the founder of CaboPress, how did you manage to execute it successfully?

Ans: I was unhappy with how tired I was after most conferences. So I started working on a design to make something different. It went thru 3-4 iterations to get it how I like it. But the last few years have been fantastic. The trick is curation and it takes time. But it’s worth it.

Q5. What’s your take on personal branding? Your personal website and social media accounts look consistent; how do you manage such phenomenal consistency for years?

Ans: Consistency is the name of the game in most games. There’s a great line from West Wing that goes, “Decisions are made by those who show up.” So the trick is to keep showing up. Day after day. Year after year.

Q6. Why are you so passionate about cigars? Isn’t it adding more swag to your personality? 😉 Haha

Ans: I love cigars because they create a pause moment in life. When everything else is running fast, a cigar slows it all down. It gives me a chance to take a break, relax, hang with some friends, and enjoy the pause.

Q7. Being a product strategist and an insightful resource, what’s the most frequent advice you usually give to WordPress business owners?

Ans: Don’t try to build your product for everyone.

Pricing is hard and needs to be reviewed often.

Learning to tell stories will help you succeed.

Q8. You’re an inspiration to many, but who inspired you the most? Please mention those names?

Ans: One of the first was Michael Cusumano, the author of Microsoft Secrets. This was in the late ‘90s. He highlighted that MSFT knew how to find engineers and marketing people. But product people, who spanned both spaces, were hard to find. That drove me.

Q9. What do you do at Liquid Web? Being a coach, speaker, blogger, and WordPress / WooCommerce evangelist, how do you manage your busy work life?

Ans: I timebox everything. So about 15% of my workday is focused on Liquid Web and product development for WordPress. 85% of my workday is then about @LearnDashLMS. Outside of those hours, I write or get on a coaching call.

Q10. Give WPExperts followers some insights on your favorite books and hobbies?



Crossing the Chasm
Differentiate or Die
The Fifth Discipline
Thinking in Systems


LPs (Records)


It was an informative and interesting twinterview with Chris Lema. Our followers and readers will surely learn about him more while going through his twinterview. It’s time to say goodbye until the next twinterview. Stay connected!

Share This Article

Optimize your online presence by partnering with WPExperts, your ultimate digital services agency. From WordPress to WooCommerce, SEO to API programming, website development to e-commerce, trust WPExperts for unmatched innovation and expertise.

Elevating Your WordPress Experience to Another Level.