Community//

Siyan Li: “Each outcome is simply a point along the spectrum of repetitions”

Each outcome is simply a point along the spectrum of repetitions. This idea originally came from James Clean and it took me a long time to truly understand it. Some of my biggest achievements happened without me expecting anything, whereas most of my attempts to become ‘popular’ fell flat. Forget about ‘becoming viral’. That sort […]


Each outcome is simply a point along the spectrum of repetitions. This idea originally came from James Clean and it took me a long time to truly understand it. Some of my biggest achievements happened without me expecting anything, whereas most of my attempts to become ‘popular’ fell flat. Forget about ‘becoming viral’. That sort of thing happens when you repeat your craft day after day. It will happen, just not the way you hoped.


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Siyan Li. Siyan is the founder and Chief Humor Investigator of Talk Witty. Her work currently ranks #1 on Google for keyword ‘how to be funny’. Her work has been featured on Science of People, Humor That Works and Medium magazines. Talk Witty enables anyone to be funny & witty by providing exact lines & actionable strategies based on the analysis of 600+ talk shows.


Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

I have always loved detective and crime shows since I was 6 years old! I was a good girl in the primary school, but the only times I skipped school were to watch a Japanese cartoon, Detective Conan. I would cover my eyes when the dead bodies showed, but I’d peek between my fingers until the scary scene was gone. I was so scared but so pumped…

Investigation, identifying patterns… Those habits are in my blood, I guess.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

I spent more than a year thinking about what my passion really is. I meditate, I ask people, and I do online courses of “Life Purpose” (Yes, such things do exist!) One of the most helpful questions is what are you doing on Saturday afternoons? In other words, what have you been drawn to without you realizing it?

I realized that I had been watching talk shows! Not only do I watch them, I analyze them, figuring out why they’re funny and how I can use some of the lines and tactics in my daily life to make others laugh. I had been doing it for a year before I asked myself that question! That was the “ah ha” moment.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

I use help of others. One of my favorite lines is “Don’t think HOW to do it. Think WHO can do it.” A lot of times, a pain-in-the-neck problem can be easily solved by someone else. I used the help of a successful online entrepreneur I know. He advised me to build up an audience to the size of 1,000 through pitching partnerships. Test and validate my product ideas after.

When I can see a clear road map, I can execute it. The road map is what translated the passion into an actual business.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

The most important question to ask is Why do you want to do this? Because it is very hard. If you are not crystal clear about the why, chances are you will give up. For me, I know this is one of the unique ways that I can bring value — not many people would analyze 600 talk shows over and over again, which is what I have gladly done.

Once you’re clear about the why, allocate some time to do it every day. Don’t jump to making a living out of it right away. Do it as a hobby and see if you can stick with it. If not, you will know that this isn’t the right thing for you and you’ve lost nothing. Do not let the idea of “no idea what the product is” stop you because you only need to worry about it after you’ve built up an audience of 1,000. And you will find out the answer together with your audience.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

It starts with the “why”, it stays fresh from “learning” and I dread less because of the “feedback”.

  1. Why: without a crystal clear ‘why’ before you start, 98% will stop, especially when you just want to make some money or bored with life.
  2. Learning: I have a practice where I learn from 1 video/article every day, e.g. marketing, and apply the lesson to my business. This practice makes the business fun and fresh — I always have something new to experiment with.
  3. Feedback: who am I without my business? I wouldn’t have an identity or a mission. But whenever I talk to people about ‘enabling everyone to be funny in daily conversation’, they remember me. They say ‘wow, what an interesting & special thing you’re doing!’ Their feedback keeps me going — I’m providing value in a fun and useful way. So, tell your story.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

I enjoy sharing my knowledge with people most. I can see how it’s useful or how it can be improved. And trust me — there’s always way more encouragement than discouragement!

Main downside is self-doubt. We’re human beings. We doubt ourselves, especially when running our own business. I do a Twin Heart meditation every morning — it always makes me feel better. It also reminds me of bringing love & kindness to the earth, rather than obsessing over my own interest. A lot of times we just need to put things in perspective, and the problem will gradually become less of a problem.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

I thought I was very confident and fearless. I thought I just needed to keep analyzing funny shows and shared the results.

But I face a lot of fear every day. A few examples: I was so scared to open an email fearing that a partner would accuse me of a shitty execution. I was so scared to produce videos and show my face! Talking about fearless!

The ‘funny business’ isn’t just fun. I have to worry about how to scale, how to handle conflicts…Fear is everywhere in this journey. Overcoming fear becomes a daily practice — this is the most striking difference.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

Absolutely. First, a quote has helped me again and again “Most people ask for clarity before taking action, but clarity comes from taking action.” Facing doubt, just carry on.

Don’t stay at home. Don’t be that lone wolf. Go out. Go to events. Talk to lots of people. I am surprised how many people find what I’m doing interesting and show huge encouragement — this is the fuel for me to keep going.

When I come back, the doubt and fear isn’t so prominent anymore. I can get back to work.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I didn’t have the courage to ask for commitment from partners in terms of the number of subscribers they will send my way, even after I can present a clear ‘win’ for them. This is funny because the biggest motivation of doing partnerships is to gain subscribers in the first place. Without setting the expectation properly in the beginning, the partnership didn’t work out.

The lesson is to believe in the value of what you’re doing and have the courage to ask for the ‘win’ for myself. I know it’s easier said than done. But it was also just hard initially. The more I do it, the less worried I become.

Who has inspired or continues to inspire you to be a great leader? Why?

My mentor. He’s a doctor turned an entrepreneur who advised Hilary Clinton and Bill Gates. He always says to me that I’m smart and I’m becoming stronger and more confident. On the other hand, he also shares stories of how Fortune 500 CEOs also have doubts about themselves.

He motivates me to never give up and that I’m good enough.

How have you used your success to make the world a better place?

In this fast-paced and techy world, strengthening human relationships is getting more important. By enabling everyone to be wittier, we enjoy interactions more with others. We laugh a little more every day. We have a little more fun every day. Accumulatively and gradually, fun and joy in this world is multiplied.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Each outcome is simply a point along the spectrum of repetitions. This idea originally came from James Clean and it took me a long time to truly understand it. Some of my biggest achievements happened without me expecting anything, whereas most of my attempts to become ‘popular’ fell flat. Forget about ‘becoming viral’. That sort of thing happens when you repeat your craft day after day. It will happen, just not the way you hoped.
  2. The best way to network isn’t going to conferences or networking sessions, it’s doing what you love. I used to attend a lot of networking events. I met lots of people, said hi, but we never met again. I didn’t have a mission or an identity — no reason for us to meet again. But when I talk about what my passion is, people are drawn to me. They are wowed, and they want to help. They introduce me to more people. Suddenly I’m ‘networked’ with all those amazing people
  3. Big influencers may want to work with you, even when you have nothing. When I had close to 0 followers, I reached out to Vanessa Van Edwards (500,000+ followers) — whose content I have loved for years. I thought she may also like what I do. Indeed, she does! Not only did she offer to work with me, she’s the very reason my work took off. I can’t thank her enough. It starts with asking and offering something of value.
  4. Turn every partnership into evergreen. This idea originally came from Bryan Harris. One of the best ways to build a following and grow a business is through partnerships. But ideally each partnership should be evergreen so your business can still grow without you working every day. For example, one form of partnership is hosting webinars to gain followers. But hosting webinars isn’t evergreen because you have to keep doing it. One way to make it evergreen is to turn the webinar material into a bonus giveaway for your partner — people who sign up for the partner’s newsletter see your content too.
  5. Make the first partnership the best they’ve ever had. When talking to a relationship expert about getting on her podcast, I offered to promote her to my audience first. I did more than she expected. I tried to make this the best partnership she’s ever had. By doing more, I’m paving the way for making the partnership evergreen as mentioned above. But that’s not entirely why I do it — people’s appreciation and love is reward itself. Don’t worry too much about when it’d pay off.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I would encourage everyone to start believing that you can be witty and charming. Most people think they’re either born funny or not, but a shocking number of comedians would tell you that they cultivated their humor. Plus, we’re not trying to be comedians. We’re trying to add a little more fun to our life — a few witty comments can do that. Others will also think of you as an interesting & charming person. A few witty attempts can lead to 1 million times more joy in the world.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite quote is “Most people ask for clarity before taking action, but clarity comes from taking action.” Our biggest enemy is self-doubt. The best weapon to slay that enemy is taking action. Any action. When I doubt myself or feel confused, I go out. I talk to people. I write 100 words. Any form of action will more or less help.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I would love to have lunch with Ellen DeGeneres. A lot of materials we use to teach people to be witty come from Ellen. I believe her show is not only entertaining, but also educational. I have started a movement called ‘Talk Ellen, Help Ellen’. We would love to donate some of our revenue to the Ellen Fund, on a continuing basis.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.


The Thrive Global Community welcomes voices from many spheres. We publish pieces written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Learn more or join us as a community member!
Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Wisdom//

How to Lead a Meeting That People Will Actually Enjoy and Benefit From

by Alexandra Hayes
Photo Credit: PepeLaguarda/Getty Images
Well-Being//

How to Know It’s Time to Quit… and How to Be OK With It

by Perrin Drumm

Sign up for the Thrive Global newsletter

Will be used in accordance with our privacy policy.

Thrive Global
People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.

- MARCUS AURELIUS

We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.