Asking the Right Questions: The Thomas Chiang Interview

Thomas Chiang blog

Executive in Residence, Thomas Chiang, wants you to be strategic. Strategic in asking the right questions. Strategic in solving the right problems. “The most successful start-ups are those that value objectivity and that solve meaningful real-world problems, especially when it involves extending beyond their comfort zone and domain expertise.” It’s frank advice like this that makes Chiang an invaluable resource within the Catapult community. Chiang is a seasoned corporate development and corporate venturing executive. With over 20 years of experience in the healthcare, technology, and financial services sectors, Chiang brings a wealth of experience to the entrepreneurial table. Most recently, Thomas led the business and corporate development functions at the Blue Cross Blue Shield Association. As their Executive Director of Business Development, Chiang built a team that successfully analyzed new market opportunities, and also structured and negotiated investments, partnerships, new ventures, and other strategic initiatives.

In other words, when it comes to discussing new business ventures and developing the right questions to ask yourself, your team, and your investors, Chiang is your go-to EIR. We sat down with Chiang to learn more about his time at Catapult and what else it takes to be a successful entrepreneur.

Could you describe your first entrepreneurial experience? 

When I first came to the United States, I lived in New Jersey, where I had a couple paper routes with the New Jersey Star-Ledger. I would MacGyver milk crates and luggage carts to my bike in order to carry it all. The Sunday papers were especially heavy, so I solicited my older brother to help. Getting your older brother to work for free, how's that for lean methodology?

My first job out of college was at a startup group within the Federal Reserve Bank of Chicago. Later, when I graduated from Tuck, it was during the height of the Internet boom in the late 90s, so I found a position with FreeMarkets, in their new Silicon Valley office.

Reflecting upon your own venture experiences, what do you think it takes to be a successful entrepreneur?

Passion, perspective, and execution.

You have to be passionate about your vision and your market, and not just about the prospects of a liquidity event or doing something ‘cool’.

Perspective, in that it's important for entrepreneurs to build meaningful relationships and to surround themselves with people who have different, and sometimes even divergent viewpoints. Absolutely critical are perspectives that represent the target markets and the respective distribution channels— be it corporate, consumer, or both. Often times I see entrepreneurs build for the 1% of the market, mistakenly thinking it’s for the 10% or the 90% of the market.

Finally, the ability to execute is critical. This is probably more important than anything else for a startup, and indeed, for any organization large or small. The ability to transition from ideation to market is ultimately what builds value, and what investors and customers look for.

Can you elaborate on the value of external feedback? 

The exciting thing about building new companies and new organizations is that while you’re developing and changing, so are your competitors, your vendors, and your customers. If you’re not constantly validating, adjusting, and innovating, you will become obsolete.

That being said, start-ups need to know how to ask the right questions. It’s often difficult to evaluate new ways of doing things; therefore it’s important to periodically take a step back to reexamine the fundamental problems you are solving and the value you are bringing to the table. Putting the two sides together is harder than it sounds, and doing it well will help bridge start-ups going from the ideation stage to creating something that has market impact.

What activities do you enjoy in your spare time?

I spend most of my free time chasing and driving around my three sons. My family and I enjoy biking, swimming, hiking, skiing, and going to museums.

When I can find the time, my most recent hobby is woodworking. I enjoy the challenges of figuring out what and how to build, and then actually rolling up my sleeves and getting it done. I guess in that respect, it's not that much different from working with start-ups except for the use of power tools!

Since your arrival in December 2013, what changes have you seen at Catapult? How would you like to see Catapult evolve in the next couple of years?

One of the things I like about Catapult, and one of the reasons I am involved, is that Catapult itself really is a startup. Things are fluid. Over the past year, we've seen a handful of our companies "graduate", particularly in the healthcare-related sector. This has been a good validation of Catapult's model. At the same time, we are seeing a lot more activity around legal, social, and other verticals. We have also added more "shared-space" residents, and that has changed the overall feel of the environment as well.

At the moment, there are a lot of co-working spaces, incubators, accelerators, and innovation hubs in Chicago. Catapult's peer-selection and market traction model has worked well, and is validated by the successful funding and corporate sponsors we've seen. Like most startups, it’s important for Catapult to be strategic about how it continues to differentiate itself from other spaces. Whether this is by sector or stage focus, scaling deep or across, these will be interesting challenges to be solved. Building a culture that successfully straddles the open collaboration value of shared spaces, along with an environment for real companies to get work done, will also be critical. The next year or two will be exciting, so stay tuned!