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How to Create Your Own "Salary" Through Recurring Revenue

(6 min read) Jerry Won on building a public speaking business, then turning it into recurring revenue through community and masterminds

Jerry Won

I believe if you get paid well to do something, you should at least one day consider teaching other people how to do it.

Through his podcast, Dear Asian Americans, Jerry Won has interviewed Vice President Kamala Harris, Instagram celebrity “Your Rich BFF” Vivian Tu, and TV/movie star Kal Penn (among many other AAAPI luminaries).

He’s parlayed his relationships and credibility into lucrative speaking, membership, and mastermind businesses - all while helping others in his community succeed in their own creative pursuits.

Jerry’s story is a lesson in Creator business expansion: every new revenue stream sets up the next.

Let’s get into it!


The Business



Creators, largely even the successful ones, suffer from not having constant, regularly expected income.

Jerry initially monetized his content creation through speaking, which then drove his community, mastermind, brand business, etc.

But how did he go from making content to getting booked as a speaker?

His first wedge was content.

He thinks about his content strategy to drive his speaking funnel in 3 buckets:

  1. Subject-matter expertise

One is becoming known as a subject-matter expert on the matter, which for me is broadly “the Asian American experience in the workplace” - so sharing content, sharing studies that come out, sharing my thoughts.

  1. Client work reflections

“Hey, yesterday I spoke at XYZ Company, grateful to so and so for bringing me in.”

But what it actually does is it gives credibility. People see the work that I am doing live.

“Hey, Jerry spoke at Electronic Arts last week. That's a reputable company.”

  1. Direct promotion.

Sometimes, once in a while, I'll post like, “Hey, hire me. It's a month until APAHM” or “Hey, we're in orientation season for business school stuff, hire me”.

I don't want it to feel like I am constantly doing that.

With his content strategy formalized, Jerry then focused on his other wedge: his LinkedIn profile.

I leverage my Byline.

I leverage what they call the Background Banner poster.

I leverage my About section, and I leverage, more than anything, the Featured section of my LinkedIn profile to highlight the fact that I am specifically a paid keynote speaker.

That way, people understand what I talk about, and how they can engage with me.

Optimizing your LinkedIn (or any) profile can simply mean being clear and deliberate about your intentions.

That’s not always easy for Creators.

I think, for most people, they don't do that deliberate part because they either have insecurities or they think that “Well, of course people should know me as a Speaker, as a Creator, as a whatever.”

But you can't assume anything about anybody.

You just have to bluntly tell them:

“Hey, I am a Creator and I am looking to engage with brands who want to work with Creators.”

As Jerry’s speaking business grew, he started to get inquiries from other Creators about how they could build a similar business.

I started getting a lot of requests to “pick my brain,” which is my least favorite word in any business.

You are attempting to learn something from me that will help you generate a lot of money and potentially start a very profitable business, and the value proposition is you offering me a cup of coffee or even lunch for that.

He realized there might be an opportunity there.

If you don't have a way for people to engage with you professionally, it is really hard to say “Oh, yeah, sure. Just Venmo me $500 and we'll talk.” Right?

You need some sort of landing page, some sort of established thing.

And that’s how his speaking mastermind business was born.

A “mastermind” is a small group of people, usually with similar businesses, goals, or needs who participate in group mentorship.

The masterminds Jerry leads are full of people who want to do more paid public speaking. They pay a monthly or annual fee to be part of the group.

Aside from monetizing demand for his expertise, Jerry gets an additional benefit from the mastermind business:

I understood it to be an opportunity to create regular recurring revenue income…to see if I can create a salary for myself as an entrepreneur.

Recurring revenue is the holy grail for Creators, because it creates stability. Jerry is always looking for opportunities to create recurring revenue.

Throughout building his podcast, brand, and speaking businesses, Jerry built relationships with dozens of AAAPI Creators, founders, and executives.

Many expressed the desire for an AAAPI identity-based group to join…sort of an AAAPI ERG (employee resource group) for the Creator Economy.

Jerry knew communities have similar recurring revenue models to masterminds…so Always Be Creating was born.

It's about the community of like-minded people who have similar backgrounds, who have similar challenges.

Does that exist today? No.

And if we're all trying to make money, it's got to be a business.

Always Be Creating is a brand that lives beyond Jerry and his partner, Justin Nguyen.

The plan is to build it into a community that stands alone, even when he’s moved on.


If you can't sell, it's not a business.

I was, quite literally, his very first member.

Enjoying these insights?

If you refer a new reader, I’ll send you Mrs Poindexter’s Guide to Marketing on Reddit!

The Stack

True independence is owning everything up and down the value chain…but I think a monthly recurring revenue-based membership program or subscription business is as close to independence as you can get.

Podcast Production - Zencastr + Audacity + Blue Encore 300 + FocusRight Audio Interface

Podcast Distribution - Transistor.fm

Podcast Website - PodPage

I am not a paid spokesperson, but it is the coolest thing in the world. If you put in your RSS link, your Really Simple Syndication link, to Podpage, it will generate an automatic web page for you in about 12 seconds.

…Morning Brew uses them, reputable media companies use them, because it gives you the ability to have a public facing, very professional-looking website, and you don't have to know a goddamn thing.

Writing - Part-Time Editor

Newsletter - MailerLite

Given the investment, Mailerlite was the most user-friendly and low-cost option for something we wanted to invest in and continue to grow.

If I were to start another newsletter from scratch, I would probably heavily consider beehiiv as my primary option.

Funnel - BrandYouFunnels.com

The reason why I really like using BrandYouFunnels is Connie has a team of copywriters and people who've done this for many other clients, who help with the crafting of the words on the page and the website creation…

So really trying to minimize the excuses or the fear or the lack of technical knowledge in creating something to allow us to have a wonderful customer-facing digital experience.

Community - Circle

Some of the other very popular and good choices for those business models, like Mighty Networks or Kajabi, weren’t the right choice for us, because Circle in and of itself was built for entrepreneurs who wanted to build community as the product, not the community being the byproduct of a course or a boot camp or something else that existed outside the ecosystem of a community.

Video - Zoom + Streamyard + iMac Camera (no external)

Editing - Part-Time Editor using Adobe + Descript

Design - Canva

Content Distribution - Later.com + Manual uploading

Project Management - Figuring it out

Most Creators don’t think about process and project management, because it’s just them. They’re the business.

Jerry’s perspective is a bit bigger picture:

If you can't sell it and be a non-participating owner in the business, it's not a real business.

So my speaking business is not a business. I have to come and perform. Nobody's going to buy that revenue stream.

Somebody might buy my membership business…somebody might buy our events business because I am not a part of that.

If making sure his sellable businesses can operate without him is a priority, then project management and process development is a boring-but-necessary effort.

We've used Trello. We've used Asana. We've used Notion. I am not very good at it…

But building out processes is a part of the business, as I evolve from a solopreneur to a multi-business unit CEO, that I need to learn how to get better at.

Asset Management - Google Drive

Communication - Text + Circle + Email + WhatsApp

Representation - BigSpeak.com (non-exclusive)

I don't want to be exclusively represented by anybody. I don't think that benefits up-and-coming speakers who source a lot of their businesses personally, because being exclusive means they take 20% off everything that you do, and I still source most of my business by myself.

It's both an art and a science, one that might not have an objective answer. If you can bring $200,000 on your own, the bet with an exclusive agency is that you'd be pulling in at least $240,000 through a combination of new business they get, better negotiations, and repeat business.

Personally, for up-and-coming speakers, especially those working within a specific community, much is built on rapport and relationships. So, at least for now, while my opinions might change in the future, I want to be the primary relationship-holder throughout the process of booking me as a speaker.

Finances - Traditional CPA + Quickbooks + First Republic + AmEx

Payments - Stripe

Operations - He does it

There's a wonderful book, it's called The Power of One. I love reading that book, because I think being independent allows us flexibility.

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Reach out anytime - [email protected].

See you next week!Recurrin

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