058: Boston Speaks Up with Serial Entrepreneur & Angel Investor David Chang

Zach Servideo
Boston Speaks Up
Published in
5 min readFeb 22, 2021

Boston Speaks Up (BSU) is a podcast owned and operated by Value Creation Labs. Listen to BSU on any podcast platform you choose: SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play.

David Chang is an entrepreneur and angel investor who has held product, marketing and operating roles at six startups and invested in 60 companies. He was most recently the CEO at student loan startup Gradifi, which was acquired by E*TRADE in December 2019. Previously, he was Entrepreneur-in-Residence at Harvard Business School and Director of the Babson Summer Venture Program.

Chang has a successful track record in hands-on roles at both direct-to-consumer and enterprise companies, six of which were acquired or IPO’d. He previously led the PayPal Boston office and co-founded the Start Tank innovation space and the Where Angel Fund. Before WHERE’s acquisition by PayPal in April 2011, he held the role of VP of Product.

Earlier in his career, on the consumer side, Chang was Director of New Products at TripAdvisor. Additionally, he was VP of Marketing and Co-founder of SnapMyLife. On the enterprise side, he was Director of Product Marketing at m-Qube, a pioneer in the mobile content space. He also served as Senior Product Manager at edocs and was a VP of Technology at Goldman Sachs.

As a leader in the entrepreneurship community, Chang holds several advisor/board memberships. He is on the board at MITX, an advisor at Harvard Ventures, Nanigans, CO Everywhere, OpenFrame, and Linkwell Health. He has made 60 angel investments in startups such as Crashlytics, clypd, Amino, Logz, Cuseum, CarePort Health, Dashfire, Mogul, Uncharted Play, as well as through the Where Angel Fund and TBD Angels.

We’re grateful to share our interview with Chang as he’s one of the most sought out speakers on the topics of startups, fundraising, and the Boston tech ecosystem, and he actively mentors countless students and founders.

You can listen to the podcast here or on any podcast platform you prefer (SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play):

Enjoy an abridged version of our interview with Chang below.

Where did you grow up? And how would you describe your childhood?

Immigrant from Taiwan, ended up in Flushing, New York at 3 years old. Moved to suburban Long Island at age 10. Spent most of childhood wanting to fit in, which included not one, but two, legal name changes.

What is the first career you remember wanting to pursue?

Childhood dream was being an astronomer, influenced by Cosmos. In the teen years, I wanted to be an architect and even took a class in high school, but quickly figured I wouldn’t be good enough to make it.

Is there a particular person or event that most shaped your vision to pursue a career in entrepreneurship?

Not a single event, more a series of subtle detours. I think of myself as an accidental entrepreneur. I do recall an early love of technology from one of my first jobs in high school as a desktop publisher (I guess that would now be called a designer) making digital brochures and resumes for other people.

What is the biggest challenge you’ve overcome as an entrepreneur?

Making decisions quickly with imperfect information, taking too long to pull the trigger.

What’s the biggest lesson you share with founders you mentor?

Focus and not boiling the ocean. The more narrow the focus on a target, the higher the likelihood of hitting it. Front-loading risks.

What do you enjoy more — building a company yourself or guiding the next generation of founders to build companies?

Super tough question to answer. I see-saw back and forth (over the course of years) between going deep and building and going broad and guiding others. Hard to do both at the same time.

What’s the most exciting part about your various roles in Boston’s innovation economy?

Love connecting different parts of the ecosystem, killing two birds with one stone. Personally, I thrive on the micro-moments — bumping into someone around town and making connections “six degrees of Kevin Bacon” style.

Do you feel Boston’s startup ecosystem does a good job making tech jobs and entrepreneurship accessible to people from underrepresented communities? If so, can you explain how?

Happens in small pockets. In my network, there’s a core group of 5–10% really focused on it, while another 80% are supportive, but not sure how to make a real change. With a little engagement, they could leverage their own platforms and do much more.

In your view, what are the most important clusters of innovation that Boston is particularly focused on fostering in 2021 and beyond?

Love it when we double down in spaces where there’s a core advantage (a “muscle”) such as life sciences and education.

What sorts of challenges and opportunities have you found in the pivot to virtual business and networking during the COVID-19 pandemic?

Tough time overall, particularly with industries with structural challenges, e.g. retail. Many businesses, especially startups, didn’t miss a beat. For some, the pandemic was a massive accelerant, and the opportunity is how to take the one-time catalyst and make it sustaining.

How would you describe the Boston startup scene in relation to Silicon Valley?

Smaller and much more tight knit. There are clusters of strength vs. pure size/scale. I think Boston is welcoming to new talent/students, but not everyone experiences that. The trick is to get different circles (or “age planes”) to intersect as quickly as possible.

You’re constantly spearheading new entrepreneurial initiatives. What’s something new you’re working on in 2021?

Doubling down on growing TBD Angels, new group of operator angels. Reducing friction between entrepreneurs and investors is something I’ve long been focused on.

What do you believe is the biggest challenge facing Boston in the next decade?

I’m focused on the startup/tech side — how to keep and grow the key ingredients:

  • Talent density: veterans / startups (e.g., 350+ mobile), corp leaders. Intellectual capital: academia, innovation, industries, raw ideas, advisors
  • Capital: angel/VC
  • Ecosystem: pillar companies, accelerators, schools, govt, orgs

What’s the biggest challenge facing the world you’d most like to see solved and why?

Hard to pick one with all the challenges (e.g., climate change) we face. I’ll narrow it to improving health and education, both areas that are strengths in Boston. Social impact in either of these fields would be a good way to leave a positive dent in the world.


You can follow BSU on Twitter at @BostonSpeaksUp, and recommend BSU guests by contacting bostonspeaksup@gmail.com.



Zach Servideo
Boston Speaks Up

Husband+dad. Heart driven leader. Gratefully collaborating with an ever expanding network of bad asses. Creator and host of Boston Speaks Up podcast.