Ding Zheng Tries to Find the Right Beat

Welcome to Stepladder, by Todd Dybas, a newsletter about career journeys.

Ding Zheng, 26 | Salesman, Rapper, Entrepreneur | Austin

What to do when you're young and want to be a rapper? Create a YouTube channel, of course. Ding Zheng grew up in his parent's restaurant and among the creator economy. His love of rap drove him to try his hand at performing. His ability to speak Mandarin and be talkative landed him a path in sales. Eventually, he found a way to merge his passion with business ideas, creating "The Sales Rapper" persona for B2B companies. Will his attempts at entrepreneurship work? He's not sure but knows they are worth a shot.

Zheng's answers from a conversation with LinkedIn News were lightly edited for clarity in this as-told-to format:

I was born in southeastern Illinois. Cornfield, soybeans.

I was there for about a month, and then I moved to China. 

There are some redneck tendencies in the vocals here. A lot of people see my name and they're like, what the hell's going on?

I was in the U.S. and then moved to China. My grandparents were taking care of me up until four. Then I came back to the U.S. and grew up in Illinois. Spent my school years in the States and my summers in China. Part of it was because my family wanted me to have that multicultural experience growing up. 

So I speak fluent Mandarin Chinese, and I read and write it as well.

My parents immigrated here early, in the late '80s, early '90s. They owned a Chinese restaurant.

China Capital Super Buffet. The good ol' Richland County Mall. 

This was in a little town in the Bible Belt, the very red part of downstate Illinois. Very small community.

We were the only Asian family really in that space. And because they had that Chinese restaurant, we are pretty well known locally. 

Classic family business childhood growing up. You come to the restaurant and there's little me in the back corner doing my math homework. Once I was around 10 years old, they started showing me a little bit. I wasn't working-working, but after school, my parents would work. So, I would go into the restaurant and that'd be restaurant daycare. 

Eventually, I'm waiting tables and wrapping silverware in the napkins and helping a bit in the background, trying to stay out of the way, stay out of trouble. And I think that was a very early foundation for what set me up for success as a seller down the line, just getting over that fear of talking to people.

I was maybe 12, 13 years old when I first was working. And I made a killing off of tips.

School is a Time For Realizations

Boston College was the best school that I got into. So it wasn't that hard of a decision.

It was between BC for pre-law or [Illinois] for their business school for accounting. I'm like, well, I don't really want to be an accountant, there are enough stereotypes I'm fighting on the daily (laughs).

I was watching "Suits" and all these shows. 'I'm gonna be a lawyer, big law, corporate.' And I'm sure there's some of that immigrant mindset. I grew up doing all the dirty work: mopping floors, cleaning the bathroom, waiting tables, washing dishes. If it happens in a restaurant, I've probably done it. 

That laid the foundation of what hard work looks like. So I've never been the guy later in life during my corporate stint where I was afraid to stay longer hours than everyone.

Compared to what I've seen in the past, I'm in an air-conditioned office, this ain't too bad. We get free food. 

Throughout college, [and] early into my corporate career, I don't think I had my own plan. Well, my own plan this whole time was I want to be a rapper. I wanted to make videos and be creative.

I was born in '96, so my formative years were when hip-hop entered the cultural mainstream. This coincided with the rise of the Internet as a distribution channel for musicians. 

Back in 2008, 2009, when I was starting, we didn't have all these fancy keywords for this stuff. I was just a little kid on YouTube seeing, ironically, this big wave of southern California and Asian creators that gained attention.

I saw people that looked like me. 

So seeing explicit examples of people that look like me doing the type of music I enjoyed and was consuming and growing in popularity in the mainstream, that's where I got that initial idea. 

I also think the timing of it was when video creation at the amateur prosumer level became democratized. 

It was the perfect storm of different environmental factors and personal interests, which somehow impressed upon me that this was possible for me.

I didn't care about being a lawyer. It seems cool. It's prestigious and you make money, yadda, yadda, yadda. But my heart wasn't into it. 

I was just trying to make it as a rapper. 

In college, I'd be making mixed tapes. I remember I had a rule for myself to drop two projects a year. But it never picked up enough momentum or reached a critical mass where I thought it would be financially viable as a long-term career. 

Junior year, summer, heading into senior year, I decided to set down the mic and spend my senior year actually giving a [expletive] and doing well in school, and getting a job and interviewing. 

A very transformative experience for me was I had a sales internship.

I had no real-world experience. So I'm thinking, OK, I need to get this internship. It's so important. Interviewed at like 50 to 100 places. Got one offer from this small startup in Boston. 

The night before I was supposed to start, I see an email in my inbox from their CEO saying, 'Hey, Ding, we were excited, but one of our team members found your SoundCloud page, and we didn't like that you were doing music, so we're rescinding your offer.'

So I lost an internship because I rap.

Nowadays, I know that that's not the best cultural fit for me anyways. Maybe that was a dodged bullet. But at the time it was devastating. I'm like, [expletive]. I really screwed myself over trying to do this music. 

I was depressed for like two weeks. Then I said, something's got to change. This isn't working out for me.

I had developed some notoriety and brand, at least among my peers at Boston College. Most of my class and the years above and under me knew who I was on campus: I was that rapper guy.

It didn't translate to overall success whether in the city scene of the music or on the Internet. But I had some notoriety. And that led to some opportunities when I told my story on social media.

Messages like, 'Hey, we see you have some skills. You're running your own social media brand accounts and doing all that stuff and you're getting some good traction.

'I know a guy who owns a restaurant and he is looking for help on the social media side.' 

'Our friend is part of a band. They're looking to expand their social media presence.' 

So I ended up taking the lost internship of that summer and translating it into my first freelance business.

It re-energized me.

Selling The Dream

After college, I saw all my friends get these investment banking consulting jobs. Very stuffy.

I knew at that point law was probably not for me. I don't want to go to law school for three years after just doing undergrad, pretty much giving up on music at that point.

I made my first song in '08. I graduated in '18. I spent roughly a decade [on music]. And at that point I'm like, writing's on the wall. I put 10 years into this. I gave it my best shot and didn't work out. OK. I can't be mad at that.

I have to go out and be financially independent. So I'm like, what's going to make the most money? It's investment banking or it's management consulting. 

Didn't love it. And maybe that showed through in the interviews.

I applied to hundreds of jobs during my senior year. I got one offer: to go do sales at Yelp. Well, I know that Yelp is a tech company. I didn't realize it'd be like the most "Boiler Room" sales environment of all time. But that ended up being good for me because I'm quite intense and I'm extremely extroverted. I like to talk.

And man, I was trash when I first got in. I was so bad.

I didn't know what sales were. I was watching "Boiler Room," "Wolf of Wall Street" and all these different movies. 

Later on, I learned that's not the way you sell things. There has to be a problem you're solving. You have to come up with a solution. I didn't know at that time. I wasn't that great. And then eventually I figured it out.

What helped me in corporate was Yelp has a lot of Chinese-speaking customers. So they sell to every [small and medium-sized business] in the U.S. that is Chinese-owned, AKA the environment I grew up in. 

I was able to translate linguistically by speaking Mandarin and was able to send over contracts and do all the translation of marketing materials into Chinese as well. 

That's one advantage I had that no other Chinese speaker in the company did because I could read and write. [Yelp] also acquired some startups. Once they realized I spoke Chinese, they redirected my efforts. I became one of the top reps of the company, just from a sheer numbers/volume game.

I had 300 times the amount of accounts that I could potentially sell to as the average rep. So it wasn't fair. And I was putting in 70, 80 hours a week at that point because I wanted to prove to the senior execs that I'm taking it more seriously than everyone else. 

I think that's why more opportunities came to me at the time. I was living in New York, I embraced that hardo mentality.

They acquired some startups and I internally got moved to their SaaS team.

Their global clients started opening up franchises in the West, and then I would be one of the main Yelp contact points for them because I could translate. 

I made President's Club and was a top rep at the company for a few years. I started to gain confidence. And started forming this identity of myself. 

I had some great leadership over at Yelp. One thing they always told me was, you gotta be yourself. You know, don't try to be too much of a corporate stiff, it's not gonna serve you in terms of results. 

So I became the guy that I'd leave funny voicemails, I'd do little poems and raps in my emails. I'd cold call someone and I would start rapping.

They're like, no one has ever called me like that before. Who are you? What do you do? 

I'd buy a little time to get my business. 

I think that's what taught me later on that something like this could work. To be like, music isn't bad, or being entertaining and human and creative isn't bad, right? Because I saw them get me results in a very tech, corporate environment.

Finding a New Beat

I was at Yelp for, for a little over two years, and then I made the brilliant, super-smart decision of leaving and starting a new job in March of 2020.

Impeccable timing. 

I got a job selling lead generation to financial advisors. I went over to this company, spent three days at the office, and was excited.

Thursday of that week, we internally had a test work-from-home day just in case this virus thing got really bad. Following Monday, New York City issues the ordinance that everyone's locked down. I never went back to the office. Within four months, my whole hiring class was gone.

That's when I hit the mean streets of LinkedIn.

Something interesting happened when I went on LinkedIn: I saw all these folks post content and I'm like, this looks like Facebook. What's going on here? 

People are doing videos and one or two people were being a little goofier. Everyone else was buttoned up.

I saw all these people talk about personal brands and how you make content that goes around your area of expertise. Show me that you can do the job before even applying or when people are researching you, there's that body of work that shows that you're credible. 

I started making, frankly, boring-ass content about how I'm a good salesperson. Because I wanted to show these hiring managers that even though the climate's iffy right now, I'm someone that's a cut above. I was a former top performer. 

Former top performer. That's a good rhyme.

It didn't quite work to get me the full-time offer, but it worked enough to get me networked with some of the other influencers. 

My background was being a rapper, video creator. And they're like, man, you have all these skills to add something that's very underserved and lacking, especially in the B2B space.

There's venture money, there's private equity, there's big companies and average contracts are massive.

I was doing this stuff, Zooms, the town hall networking calls, what have you. And I was rapping. They're like, damn, this is cool. We've never seen anything like this in our space before. 'Ding, please do more of this.' All right, let me figure out what that'll look like. 

You know the song "What's Popping" by Jack Harlow?

There's that motif in sales where they ask what's cooking. The sales manager would be like, Hey, rep, what you got cooking up for me today? 

So I remixed the Jack Harlow song, and I called it "What's Cooking?" And then made a little lyric video. This was before I went way into the deep end with all my equipment and gear. 

I just remember it was like a terrible lyric video that I made in, I don't want to say Windows Movie Maker, but you get the gist, right? 

I got more views on that one video on LinkedIn than I ever did over a decade of being on YouTube.

It resonated because no one had ever seen stuff like that before. They're used to white papers and gated eBooks in webinars where a bunch of people sit around talking about nothing. 

So that struck a nerve. I doubled down. I kept making music. Shooting little videos on my phone. And eventually, company's marketers started inbounding me.

I would get DM'd, people would send me emails, 'Hey, Ding, we like what you're doing. We thought it was very entertaining. Can we pay you to do this for us?' 

I'm like, wait a second. I can make money doing this.

Had more conversations, talked to people, asked them what is the actual business problem that you're solving for? 

'Well, our top of funnel is slow.' 

'No one cares about our brand.'

I formulated my own offerings around the sales experience that I got in corporate. Was trying to have that business-person mindset versus I'm trying to be a rapper. 

And ironically, that all came full circle. Now I do more music, I record more, I sing more, I write more, I perform way more now that it's in that tech, or software or a B2B setting than I ever was able to do as an independent musician. So I'm just grateful a lot nowadays.

Trying to Pull Everything Together

More often than not, you'll find that if you go out and you do the work, what was a closed door in the past can be opened.

You just give yourself more optionality the more work that you do. I think it's been very true for me. 

As I've gotten more into entrepreneurship and learned more about business, I started to dislike the model of my business. 

I couldn't take myself out of the business and I couldn't scale it. Also, the way that the economic structure was, those were all one-offs, single-project-based pricing.

I cannot for the life of me ever move that to a retainer or recurring revenue model. So I've never been able to grow past a certain point.

I needed something that would be scalable because I think at this point I find as much joy and interest in business as I do in performing and being creative.

Don't get me wrong. I still love to rap and all that stuff. But I love the challenge of entrepreneurship in scaling a business. 

As The Sales Rapper, I've done a lot of work where I've closely collaborated with marketing teams at these B2B companies. And, these companies will spend massive amounts of dollars.

They'll get the private box at the sports game. They'll buy out a bar and give everyone drink tickets; spend all this money to maybe close one deal, maybe get eight leads for the sales team. 

And, that's when they'd hire me to go and freestyle and perform. And that was lovely. The problem is you have all of your subject matter experts, all your leadership, your partners, your customers, all your people in one space. AKA the people that you would want to be on your marketing materials. 

So why is no one there capturing them in content? It's like now you're killing three birds with one stone.

You're saving money on your content production cost, and you're maximizing the ROI at your events. So that was the initial idea: if they're already paying me to do all this stuff, how can I add more value to my customers? 

I bought a camera, I got all the mics, all the gear lights. Eventually, I showed up to an event, I performed for them, and then now I'm shooting their content and as The Sales Rapper making all my creative stuff.

One thing I've had to do is build a team around me: video editors, designers, producers. I already have the infrastructure from doing rap, music, the creative business. Can I apply this to something more wide-ranging and more widely applicable to most companies?

Most companies, frankly, with their brand, they're probably not gonna hire a rapper. I have a very niche target. 

But if I'm able to turn in-person events into a major content pillar for B2B companies, that's something that the CFO is going to smile more commonly upon in 2023. 

And the other piece of that is where the market has been, where tech has been. We're in the land of layoffs. A lot of these layoffs have been marketers and salespeople. And the past two quarters have been tough. 

So I can either sit on my thumbs and worry and cry about it. Or I can go out and try and build another business where I know that there is a gap in the market and I can bring some value. So that's why we were starting a venture [called Event Shark].

Luckily for me, I think we are in the age where that personal brand is important. And I'm glad I had an early introduction to that through trying to be a rapper. 

I've found a better fit for my personality, who I am. I'm the guy that can be entertaining and fun and rap and whatnot, but if you put me in front of a CMO, I can have a business conversation with them. 

I know that as long as I continue building my personal brand, even in the worst-case scenario, I'm going to have an easier time finding a marketing job or another sales job. 

If I have to give this up and, and it really just explodes in my face, I know that because of all the work that I've done up 'till today, I'm going to have a bit of an easier time transitioning back to a 9-5 than if I hadn't done all these things. 

Hopefully, that never happens.