Toby Zhang of ‘Shop LIT Live’: “Take big risks early on”

Take big risks early on — it is much easier to take risks when we are young and single, than when we are older with family obligations. We can couch-surf when things don’t work out, dust off, and start again when we are by ourselves. This is a lot harder with a family. As a part of our […]

Thrive invites voices from many spheres to share their perspectives on our Community platform. Community stories are not commissioned by our editorial team, and opinions expressed by Community contributors do not reflect the opinions of Thrive or its employees. More information on our Community guidelines is available here.

Take big risks early on — it is much easier to take risks when we are young and single, than when we are older with family obligations. We can couch-surf when things don’t work out, dust off, and start again when we are by ourselves. This is a lot harder with a family.

As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Toby Zhang.

Toby was a partner at CRCM Ventures from 2014 to 2020, leading the firm’s investments in consumer and emerging technologies. At CRCM, Toby helped to grow the VC team from a team of 3 to a team of 28 across 4 offices, and launched 4 early stage funds. During his tenure, his successful investments include (now TikTok), Ripple, Ginkgo Bioworks, Firework, Wink, Itui, Drone Racing League, This is L, (Nasdaq: API) and more. In 2016 he was voted Forbes VC 30 under 30. Prior to CRCM, He was a venture investor at Edison Partners in 2014 leading investments in enterprise solutions. Prior to Edison, Toby led a cross-organizational development team at Microsoft building the 1st generation Microsoft Surface and served as strategic advisor to the president of Server and Tools Business. Toby holds an MBA from The Wharton School at the University of Pennsylvania and a Masters in Engineering from the University of Michigan at Ann Arbor.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I’m an engineer by training and started my first company when I was an undergrad at Michigan, where I launched a marketplace for college students to buy and sell textbooks. The company was later acquired. After that, I spent the next 4 years at Microsoft leading one of the core teams to build the first-gen Microsoft Surface Tablets. After leaving Microsoft, I attended business school at Wharton, where I launched my career in venture capital. I spent the next 6 years as a partner at CRCM Ventures investing in early stage tech startups (, Agora — NASDAQ: API, Orbeus — acq by Amazon, Ripple, Ginkgo Bioworks, Spin, etc.) with a focus on social, commerce, and frontier technologies.

Over the last few years, I’ve noticed social shopping and particularly live shopping has become a major trend in Asia. This has become a dominant form of e-commerce in China. Combining social, commerce, and deep tech, I see the opportunity to bring a similar experience to audiences and shoppers here in North America. This led me to start LIT Live, an exciting live shopping platform that launched earlier this year.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Our vision is to make shopping much more interactive, fun, and community driven.

At LIT Live we bring back the nostalgic “window shopping” discovery experience through authentic user-generated multimedia content and engaging live-streaming sales events. Merchants, sellers, and brands can go live on our platform to share their latest releases and product drops. Shoppers can join a live-stream, comment, co-stream with the host, and make purchases directly through the app. Beyond live shopping events, LIT Live is a community for shoppers to discover new trends, brands and products as well as share their own favorites via shoppable multimedia posts. The platform makes it fun for users by offering many ways for users earn rewards and discount points.

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?

Two of my colleagues have very similar names (in spelling and pronunciation), and I used to incorrectly call them by each other’s names when they first joined us. It was all in good spirits and as a team we agreed to go with nicknames for these two colleagues. They were happy with this arrangement and the rest of the team decided to go with nicknames as well. We then started to nickname everything: product features, engineering milestones, etc. This turned out to be a lot of fun and turned an awkward situation into a morale booster for everyone.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

As a new founder, some of my mentors are other founders I’ve worked with over the years when I was a VC. I’ve received very helpful advice in the areas of talent acquisition, product marketing, team management, meditation, and so on. The best part of it all is knowing I’m not alone in all of this and many have faced similar challenges. Being in a community of founders has really give me the opportunity to receive mentorship from many others.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

Being disruptive can sometimes also lead to businesses operating in the gray area or technologies being used incorrectly outside of their initial intent. While we look to technologies to improve our lives, we should achieve these goals while operating within legal and ethical boundaries.

For instance, telemedicine has made it abundantly efficient for doctors to see patients and prescribe treatments and medication for them. The same technology has also made it much easier for the prescription of certain controlled substances, where remote doctor visits sometimes may not have provided the same levels of scrutiny that is present for in-person visits. This can result in certain patients taking advantage of this technology to abuse these substances that they otherwise wouldn’t have the opportunity to do.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

  1. Take big risks early on — it is much easier to take risks when we are young and single, than when we are older with family obligations. We can couch-surf when things don’t work out, dust off, and start again when we are by ourselves. This is a lot harder with a family.
  2. Mistakes/failures are ok; not learning from them is not — I’ve made many mistakes in my career: made the wrong product decision, selected the wrong vendor, made the wrong investment, spent time on the wrong priorities. Each time when I realized my mistake, I did my best to understand what had caused it and how to not make the same mistake again should similar situations arrive in the future
  3. Be humble and seek good mentors — few are jack-of-all-trades or are experts in many things. While we can be diligent and eventually acquire certain skills on our own, it’s a lot faster (and a lot less potholes to step in) if we learn to acquire insights, skills, and experience from experts who have already done it. A good mentor is hard to come by and can make a big difference.

We are sure you aren’t done. How are you going to shake things up next?

At LIT Live, we want to help every small business (brick and mortar and ecommerce) in the US to leverage live shopping as a dominant channel to reach their customers. Beyond this, we want merchants from countries around the world to also be able to leverage our platform to grow their business.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

Elon Musk once spoke about the time when SpaceX and Tesla were weeks away from insolvency, and when funding ran dry he bet everything he had personally to save both companies. I’m a firm believer in being committed towards a cause or a vision. As entrepreneurs we face challenges every day. We have to stay committed to what we are doing and believe in ourselves and our team, even when others do not.

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

Growing up loving sports, my favorite quote is “You miss 100 percent of the shots you don’t take” by Michael Jordan. In life we have opportunities to take risks, the results of which can define who we are and change our lives. My career thus far has been a fortunate result of taking risks. Whenever possible, I gave up a portion or all of my salary in exchange for a higher share of the upside in whatever I was working on. In the end, by taking these risks, the results were much more rewarding.

You are a person of great influence. 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’m a believer in giving back one’s excess to worthy causes. Everyone, no matter what stage of their life or career, can find ways to give back and help build their community. A wealthy person can contribute to the community financially; an educator can contribute their time; a scholar can contribute their knowledge and mentorship. When world has more people who are generous with their time and resources, magical things happen 😊

How can our readers follow you online?

You can find me on LinkedIn:

You can also download our app on the app store “LIT.Live — Live Shopping” or follow us on Instagram @shoplitlive

This was very inspiring. Thank you so much for joining us!

    You might also like...


    Toby Zhang of ‘Shop LIT Live’: “Take big risks early on”

    by Jason Hartman

    Debra Miller On How To Leave a Lasting Legacy With a Successful & Effective Nonprofit Organization

    by Karen Mangia

    “Know Your Shit Before Walking Into a Meeting” with Chris Cunningham

    by Jean Ginzburg
    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.