How This Former Teachable Employee Melissa Guller Turned into a Successful CEO

This is an interview with Melissa Guller of Wit & Wire.

Hey, Melissa. How did you end up working for Ramit Sethi?

I was a student in one of his courses (Zero to Launch) and I saw on his website that they were hiring for a Senior Launch Manager. It was a really niche position, but my resume of roles in event production and edTech startups made me a uniquely good fit for the role. 

But what’s interesting is that I had to make the tough choice to either accept the full-time role with Ramit or continue working on my side business.

I chose to take the job because I knew it would elevate my skills, and although I can’t know where that first business would be if I’d continued, I definitely feel like it was the right decision. (Especially since it led me to Teachable and later Wit & Wire.)

What are the most powerful lessons you took away from that experience?

From a business perspective, I learned a lot about what it takes to sell online courses at scale. (It’s an 8-figure course business.) But on a personal level, I was blown away by how many people were willing to pay 4- and even 5-figure amounts for online courses. 

It was eye-opening to realize that online businesses weren’t just possible; they were profitable. And there were hundreds (if not thousands) of students in Ramit’s audience building businesses in industries we’re often taught aren’t lucrative, like music or the arts. 

It’s also when I realized that you could truly have a job working from anywhere, since we were a fully remote company of 50 people long before the pandemic made that the norm.

So working for Ramit was not only crucial in building my online business & marketing expertise, but it also shaped my vision for the type of lifestyle and career or business I hoped to build for myself. 

What was it like to be part of the Teachable team?

Teachable was my dream job. Ankur (the founder) reached out to me at exactly the right time, when I was hoping to transition from working from one large influencer to a software that empowers hundreds of thousands of business owners.

Since I joined when Teachable only had 35 employees, I was involved with projects across the company with all different departments. (As a fun fact, my first title was actually Head of Special Projects before I moved into a Director role in the marketing department.)

So it was energizing to be part of a growing company making waves in its industry, and I loved learning how successful business owners were using Teachable to build their businesses.

I also really enjoyed working with smart, creative thinkers who wanted to experiment, dream bigger, and see how else we could build the business. 

What made you pursue self-employment and when exactly did you start the business?

My grandfathers were both entrepreneurs, and so is my dad. But as a kid, it never occurred to me to go into business. (It seemed a little boring, no offense, Dad!)

But once I started working for Ramit and then Teachable, it really opened my eyes to the possibility of what my life could look like if I built something for myself. Not only did I love the idea of setting my own schedule and unlimited earning potential, but I’m also very mission driven, and I’m at my best when I’m helping others. 

I knew I had a lot of marketing, tech, and teaching expertise to share. So I hit a crossroad in 2019 where I realized that there would never be a good time to start a business – let alone leave Teachable – and so I launched Wit & Wire with the mission to help diverse business owners expand their income & impact online. 

Since I had the stability of a full-time, I was working on Wit & Wire nights and weekends for the first year and a half. I officially left Teachable in May 2021 and I’ve been a full-time solopreneur ever since. 

How did you come up with the idea for Wit & Wire and who do you help?

Since I’ve worked in the online business industry for so long, and since I’ve had a unique mix of marketing, ops, and teaching experience, I knew I wanted to work with online business owners. 

More specifically, I help people create & sell online courses, so my ideal audience typically includes coaches, service-providers, influencers, and solopreneurs. 

What were the main elements of the business that you set up from the beginning?

The #1 priority I had from the start was my email list. I’d worked behind-the-scenes for long enough to know that sales come from email subscribers, so that’s been part of my long-term growth strategy ever since Day 1 when my website went live.

I’ve used different social and content channels over the years to build my email list, and they’ve changed based on my preferences and the evolving marketing ecosystem.

In 2019, Pinterest was my main source of leads, and in 2023, it’s TikTok and YouTube. That happens to be the combo that works well for me right now, but that doesn’t mean it’s right for everyone, or that it’ll work forever.

I think a key to success as a business owner is adapting to change without consistently taking on more. It’s not just about adding more socials or more content creation; it’s about giving yourself permission to temporarily (or permanently) stop doing things that no longer serve you. 

How long did it take you before you made your first money with Wit & Wire?

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Since I had a full-time job in the beginning, I didn’t feel pressured or rushed to earn money right away, which I know is very fortunate. Instead, I decided I’d spend 6-9 months building up a small audience and then pitching them an online course, which is exactly what I did.

While I was audience building, I put up a services page on my website in case anyone did want to hire me. (And it worked!) So it’s definitely something I’d recommend, since it doesn’t take a lot of effort to let people know you’re available for hire, but it can literally pay off.

So from the day my website went live, it was 2-3 months until I booked my first client (without really trying), and 7-8 months until I created and sold my first signature course. 

Read also: What’s a Signature Product and Why You Need One

What was the first course you created?

When I started Wit & Wire, my long-term vision was always to work with course creators. But since I was still working at Teachable, the thought of talking about course creation nearly 24/7 felt like too much of a good thing. (Plus, I wanted to test the waters selling a course that wasn’t “a course about course creation” to up my street cred.)

So with that in mind, I decided to launch a course that served the same audience – online business owners – on a different topic: podcasting. And for nearly my first 2 years in business, I focused the majority of my content around podcasting to drive warm leads to my signature course about podcasting (Podcast Launch Accelerator).

There were some other podcasting courses I sold as well, but that was my first signature offer. 

How did you go about launching it and how did the launch go?

I launched the Founders’ Round of Podcast Launch Accelerator in April 2020, and I enrolled 20 students into the first cohort. It’s noteworthy that the global pandemic had just hit, so that made it a really unique time to sell online courses since more people were in lockdown.

There are a few elements of that launch that I still teach today in Wit & Wire’s programs, like the strategy of running a Founders’ Round that uses unique teaching and marketing approaches. But there are others that I’ve adapted based on my own subsequent launches and working with clients and students over the years. 

Read also: How This Children’s Book Author Had Her 1st Six-Figure Course Launch

What’s your current product suite like?

Although the Podcast Launch Accelerator is still active and highly-rated, the primary focus of Wit & Wire today is working with course creators so they can create and sell signature online courses that help them expand their earning potential online.

Intro Course: Profitable Course Blueprint

In this starter course, I help students validate demand for their profitable course idea so they can plan, price, and outline their first course with confidence. 

Signature Program: Course Builders

In my top-rated online course, I help business owners create a signature online course and enroll their first paid students in 90 days (or less) without tech overwhelm or complicated marketing strategies.

Advanced Program: Automate & Scale

In this program, I help active course creators create an automated sales engine for their course so they can sustainably scale their revenue to $10k months (or more) on their signature program. 

Do you think every course needs a community such as a forum or FB group?

Great question. I definitely don’t think they’re necessary. I think it’s a misconception that every course needs a community, because not every learner needs a community to reach their goals.

For some programs, I think a community adds value if students would benefit from connecting with fellow students, asking for feedback, or engaging in regular discussion.

But for other programs, communities are a distraction, and if they don’t save students time, then they’re a potential fumbling block on the way to their outcomes.

I also think some courses might start with a community but phase it out as the course scales, or vice versa. (Some courses might only benefit from adding a community when the group is large enough.)

It’s takes work to engage a student community, so my best advice is to think critically about whether or not it benefits your learner. It shouldn’t be the default option.

What’s your take on evergreen vs live launches?

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They both work really well. It’s not a matter of choosing one or the other; it’s more about timing, and when each makes sense for your business. (If your course is brand new, I wouldn’t recommend immediately jumping to evergreen before you’ve validated demand.)

There’s no one-size-fits all answer here, but I’d say it comes down to course maturity, student experience, and instructor preferences.

Read also: Behind The Scenes of a $23K Course Launch

What are the tools you can’t run a business without?

Any course creation platform + any email service provider + any task manager. I think different tools suit different personalities and goals, but that core combo is one my business couldn’t function without.

How has the course industry changed during the pandemic?

Since people are more comfortable being online, the demand for online courses has increased (and continues to grow).

On top of that, students’ expectations of what a course looks like have shifted, so for different buyers at different price points, they may want more personalized feedback or interaction with the instructor (you) or peers.

That doesn’t mean you need to interact 1:1 or 1:many with students. It just means that you might need to consider what your buyer will expect at different price points. 

What’s your advice for course creators who have a good product but aren’t making any sales?

The #1 reason why courses don’t sell isn’t bad marketing. It’s usually a bad offer, meaning that there isn’t demand from your ideal buyer for your solution at the price point and packaging you’ve proposed.

The good news is that it’s often just a small tweak that makes the difference. The bad news is that I often see course creators endlessly trying new marketing strategies and wondering why none of them work (when the marketing was never the problem).

The second most common issue is not enough propects. If you haven’t gotten your offer in front of at least 50 handraisers, you may not have a big enough sample size to know if it does or doesn’t convert. 

What’s next for you and Wit & Wire?

I’m all in on my mission to help more business owners create & sell profitable online courses. So my plan is to expand Course Builders (my signature course) and build out the more intermediate program (Automate & Scale) so I can offer a complete course creation suite for business owners of all experience levels. 

And for anyone who wants to learn more about my programs (or grab some freebies), you’ll find me online at, or on TikTok and YouTube @witandwire.

Want to become a successful course creator? Learn how Melissa Guller, a former Teachable employee, started selling online courses full-time: