David Chang: The Definition of Paying it Forward banner image

David Chang: The Definition of Paying it Forward

David Chang is an entrepreneur and angel investor with product, marketing and software development experience at 5 startups/acquisitions. He has been part of the operating team at some of Boston's most successful companies like edocs (acquired by Siebel), TripAdvisor (IPO), m-Qube (acquired by Verisign) and WHERE (acquired by PayPal).

In the past, there wasn't a very known or active angel community in Boston.  Today, there are many active angels who are not only writing checks, but they are also mentoring entrepreneurs.  David's presence in the Boston tech scene is a great example of this shift and how things have changed since 2010 in Boston.  As you'll notice by reading below, he has done a lot in terms of paying it forward.

The image above is from the PayPal Boston office ribbon cutting ceremony back in 2013 with (starting from the left): Mayor Thomas Menino, Gregory Bialecki, Walt Doyle, and David Chang.

Keith Cline:  Tell us about your background.

David Chang:  My first memory in life consists of a drab green couch against the backdrop of a white room. I was three years old, and I remember sitting in a New York hospital waiting room on the day of my sister’s birth. Since my family had just moved from Taiwan to the U.S., all my subsequent memories are of growing up in a typical suburban neighborhood on Long Island. While still in high school, I spent six weeks in an explorations program at Cornell University, and after that, I couldn’t see spending my college years anywhere else. When the time finally came, I crammed everything I could into a hand-me-down ‘79 BMW and drove the 280 miles to school.

During my sophomore year, I met with my faculty advisor “guidance counselor” to work through the dilemma of choosing a major. Since I wanted to eventually go to business school, he suggested that I focus on a technical discipline since there would be plenty of time to pick up the business side later. For me, it was the best advice ever. I ended up concentrating on computer science since I’d been playing with computers like the Commodore PET, TRS-80, and Apple IIe for almost as long as I can remember.

KC:  What did you do after graduation and why did you go back to business school at HBS?

DC:  After 38 rejections during my senior year, I landed two job offers from very different places. The first offer was to join Oracle, a west coast tech company, as a business analyst, and the second offer was to join Goldman Sachs, an east coast investment bank, as a programmer. Undecided, I spent a week in California during spring break to test the waters to see if I could live there, and I just couldn’t see myself doing it.

Enjoying good company and a drink at the Goldman Sachs Information Technology holiday party (1994)

I joined Goldman Sachs and started in the New York headquarters, just 40 miles from where I grew up, in a role bridging technology and finance. The work brought me around the globe as I packed my bags and headed to Asia and Europe. I never did get my bearings in Hong Kong, but soon felt equally at home in New York City’s Greenwich Village, Tokyo’s Roppongi, and London’s South Kensington. During my seven years at the company, I wore a few hats: programmer, technical architect, database admin, team manager, market researcher, accounting specialist, product development manager, global coordinator, and finally VP of Technology. There were days when I got into the office at 5am because I couldn’t wait to start the day. Although I was thrilled with my job, I never shook my fixation on getting an MBA.

After a painful process of multiple years of applications and rejections, I finally got into a couple of schools on my final attempt. I eagerly sent the tuition deposit to Harvard Business School, but reluctantly submitted my resignation letter. I procrastinated clearing out my office, which looked out onto the World Trade Center. I finally was able to focus when I reminded myself that the relocation to Boston would only be two years of my life. Little did I know that I would be here 17 years later.

Business cards from the 5 startups.

KC:  Can you share your experience from your time at edocs?

DC:  Kevin Laracey, the CEO of edocs, may still remember my complete disruption of his company’s info session during Boston Trek, a multiple-day visit of local tech companies for second-year business school students. I showed up over 30 minutes late - not the best way to make a first impression. I somehow recovered from that initial stumble and convinced Chris Gardner, director of product management, to have a follow up meeting with me. The timing was not good - the 2001 internet bubble had just burst. Although they didn’t have an open position at the time, I just kept hounding Chris until I got a job offer just weeks before graduation.

As a former software engineer, I had a bumpy transition into product management. During my first six months, my hand was repeatedly slapped by an engineer when I fell back into the mode of trying come up with the solution, rather than defining the problem. I eventually settled into a good rhythm of a typical day, and focused on three main parts of the job: product management (being “CEO” of the product and working with the internal team making the game time tradeoffs), product marketing (writing business cases and putting together externally facing materials), and sales support (the raw blocking and tackling of selling - finding the decision maker and closing the deal). In the end, I learned a ton from co-workers like Rob Orgel (COO Quattro/Apple), Jim Moran (North Bridge), Mark Quinlivan (CEO of Confer), Jed Rice (SVP Paydiant/PayPal), Melinda Smith (CFO Paydiant/PayPal), and Mike Massaro (CEO of Flywire) over three years at edocs. I could not have asked for a better first real experience at a venture-backed startup.

KC:  You joined TripAdvisor in 2004.  How many employees did they have then and what was your role?

DC:  I remember how jarring it was to transition from edocs, an internet enterprise software company, to TripAdvisor, a consumer internet company. At edocs, we’d launch a new version of the software once a year and scramble to launch a point release every few months. I was shocked on the first day when Steve Kaufer, TripAdvisor’s CEO, asked me to launch a new feature before the end of the week. It turned out that we’d release new stuff EVERY week. As the company’s first dedicated product manager, I worked on ways to make it easier for travelers to plan their trips: introducing new ways to search for hotels, running A/B tests to optimize the site, getting into the consumer’s head through surveys and focus groups, and negotiating deals with vendors.

Robin Ingle at the TripAdvisor holiday party (2004)

Compared to the juggernaut TripAdvisor is today, the team was very lean when I was there. I recently found my first pay stub, which lists my employee ID number as #33, but I’m sure we were smaller than that. We had one person in sales, Robin Ingle, who is still at the company (contrast that with this recent photo of her sales team). Shortly after I joined in 2004, we needed to hire a merchandising manager and quickly found two great, but very different, candidates: Adam Medros and David Krauter. Steve finally suggested that we hire them both, and I thought that was the most insane thing ever - how could we possibly hire two people and figure out how to define roles that would make sense? It turned out I was wrong (not surprisingly). Twelve years later, they are on the leadership team of the now public company (NASDAQ: TRIP): Adam is SVP of Global Product, and David is the President of several TripAdvisor properties. Steve figured out how to create meaningful roles.

KC:  What brought you to m-Qube, which was acquired by Verisign?  Can you share some of the details from your time there?

DC:  I decided not to join m-Qube. I called Chris Gardner, the hiring manager at m-Qube and my former boss at edocs, to decline the offer but got his voicemail instead. I chose not to leave the message, and by the time I called back later that day, I changed my mind. The combination of working with a great team that I used to work with, but in a new explosive industry, tipped the scales in favor of joining m-Qube. In the year I joined, we did $6M in revenue, then the following year did more than $80M. It was a time of insane growth - it seemed like each week, the new hire orientation got bigger and bigger.

As a product/tech guy, it was unnerving to focus on just product marketing. For the first time in my career, I no longer had a direct hand in deciding what got built. I purposely chose to sit in the bullpen with the 4-person product management team in order to overhear what they were working on. What’s more, we lost our corporate marketing person just before I joined, so I ended up taking on a true marketing role for the first time in my career. It seemed as though every month brought an entirely new challenge due to the explosive growth. When our CEO Jeff Glass announced that Verisign was acquiring the company, I remember thinking that we still had so much to do. My time there was a blur, and I got to work with so many talented people who have gone on to make such a mark on other parts of the industry. Again difficult to name all, but some included Jim Crowley (CEO of Skyhook), Andy Miller (CEO Quattro/Apple), Mike Troiano (CMO Actifio), Jennifer Lum (Co-founder Adelphic), and Lars Albright (CEO SessionM).

m-Qube Marketing Team

KC:  You started your own venture backed company called Mobicious?  What was the idea and what happened?

DC:  I had no intent on leaving Verisign/m-Qube, but when I met George Grey, we saw an opportunity to create for mobile consumers a media app store (an “app store” two years before Apple launched its app store). It was super risky, but it was a unique chance to leverage what I learned at TripAdvisor and m-Qube. Over the course of a weekend, I quit my job at Verisign, joined forces with my co-founder at a new startup without a name, and had a daughter. Lots of change in 48 hours. Over the next couple of months, we refined the business plan, pitched to VCs, and landed a $4M A-round during the summer of 2007 to build out the company. I was so glad to recruit my former m-Qube marketing team Aimee Anderson and Lauren Romeiro and former TripAdvisor lead developer Matt Conway to join the company.

Just one month after we landed our funding, we discovered that consumers were gravitating towards free media and creating their own content. As a company, we soon pivoted to create SnapMyLife, a mobile photo sharing service where people could quickly post pictures and discover images from around the world. By mid-2008 (two years before Instagram’s launch), SnapMyLife users from 190 countries around the world were sharing photos, but we couldn’t figure out a way to monetize. We waffled back and forth between different use cases - should we focus on private sharing (e.g., sending pictures of your kid to your mom) or public discovery (strangers sharing photos with each other)? Switching back and forth, going from guardrail to guardrail, between these extremely different features was a killer. Never do that.

As we struggled to find a new direction for the company, we had to significantly cut the burn rate and switch gears. I ended up laying off half of the team, including myself, to give the company a shot to succeed in pursuing a B2B strategy selling to media companies. Long after I left, we found an acquirer for the company, but for pennies on the dollar. Not the brightest day as an entrepreneur, but such valuable lessons for me during this journey.

KC:  What brought you to WHERE, which was acquired by PayPal, as the company’s VP of Product?  How did your role evolve over time?

DC:  As I wallowed for a week in the summer of 2009, wondering if I could get a job again, I blanketed my network and sent emails to about 30 former colleagues, a dozen VCs, and a handful of headhunters. One of them included Noam Bardin, the CEO of a little known, but cute app called Waze. It sounded like a fun opportunity, but I didn’t want to move out to California. David Beisel, who I first chatted with when he was career soul searching as a grad student, connected me with Walt Doyle. We chatted about a VP of product role that combined a number of things in my past: B2C and B2B, mobile and web, and location.

Joining WHERE was like joining a new family. Unlike my previous startups, I really didn’t personally know anyone on the team. But what a team it turned out to be! I got to work alongside Dan Gilmartin, Ivan Mitrovic, Doug Hurd (Co-founder clypd), Niall Hawkins (CFO Evertrue), Ron Braunfeld (VP Pingup), and Jerry King (COO Vets First Choice) all under one roof. We had a super talented product team of Joshua Summers (Co-founder/CEO clypd), Arik Keller (CPO Confirm.io), Jim Caralis, and Nataly Kogan (CEO Happier), each of whom has since launched his or her own company. With superstars like them, my product role quickly morphed into other areas, and I took on corporate development to focus on the growth or acquisition of the company. I took on a general operating role after the PayPal acquisition, and led the Boston office after Walt’s departure.

WHERE/PayPal closing dinner (2011)

Soon after, I co-founded the Start Tank innovation space, which brought me closer back to the world of early stage entrepreneurship and startups. I look back fondly at some of the earliest startups at the Start Tank and how they’ve grown: Polina Raygorodskaya (CEO Wanderu) and Amanda Curtis (CEO Nineteenth Amendment). Things came around full circle just as I left PayPal in a public way and the Paydiant acquisition was announced. Paydiant’s founders were none other than Kevin Laracey, Chris Gardner, and Joe Paratore (who passed away in 2012) who I worked with at both edocs and m-Qube, and it was so exciting to see their success and continue Boston’s leadership for a major tech company.

KC:  How did you get into angel investing and what are some of the first companies that you backed?

DC:  My first angel investment was an accident. During an interview with a startup I was considering joining, I ended up writing a check rather than pursuing a job offer. You’ve got to love the unpredictable nature of these chats over coffee - you never know who’s selling and who’s buying. Shortly after the WHERE/PayPal acquisition, I wrote my second angel check in Crashlytics, which Twitter later acquired. I still have my meeting notes during my deep dive with Wayne Chang and Jeff Siebert over lunch at Neptune Oyster using my checklist/framework. WHERE actually sponsored the drinks night at the Beehive where Wayne crashed the event and met Jeff, so the ROI on that night is off the charts.

From 2012 to 2015, I made a slew of angel investments, many of them alongside extremely knowledgeable operators and investors. Today, I’m lucky to share ideas and leads with Shereen Shermak, who has discovered some incredible founders.

KC:  What sectors of technology, industries, or trends are of interest to you?

DC:  My startup experiences have been in web/mobile software ventures in both B2C and B2B, so I try to stay in that lane. I prefer investing in startups in fields such as software, digital media, travel, or payments where I have deep knowledge and/or contacts to give the founders a competitive edge. In the early stages, it’s so beneficial to have frequent contact with founders, so I tend to stick to local startups at the seed stage.

My primary motivation for angel investing is strengthening connections and leveraging areas of existing expertise. The potential financial return is obviously a factor, but it’s not the first criteria I use when deciding which founders to work with.

KC:  You are a very active investor in Boston companies, having invested in over 35 companies.  What excites you about the current market in Boston?

DC:  Jeff Bussgang has a great presentation of the Boston startup ecosystem, which includes clusters of excellence and emerging microclusters. I’m excited about these industries and feel strongly that we should double down on areas where we have a competitive advantage. It’s an interesting time to be in startups since the venture capital industry is also changing. Not only has the amount of capital required to launch a company been slashed, there are more kinds of capital available through syndicates and how VCs are embracing a network-model by involving skilled entrepreneurs/operators as part of their firms.

Lately, I’ve been fascinated by how founders get matched with the right set of investors and been thinking about ways to help hundreds of startups, not just the handful that I personally invest in. That’s one of the drivers behind PersonalVC, a passion project that I’m working on with Dan Deac and Stipe Ivan Latkovic.

Mobile mafia members from WHERE, m-Qube, Quattro, Millennial, JumpTap, Skyhook (2015)

KC:  What companies in Boston, outside of your portfolio, do you find interesting?

DC:  I love that Boston has leadership in fields like life sciences and healthcare, and I wish I knew more about other strong areas such as ed tech and robotics. I recently spent two hours with Helen Greiner of CyPhyWorks and was blown away by what they’re working on. Like many others, I’ve been paying attention to the next wave of startups where software meets hardware: iOT and artificial intelligence. It’s impossible to predict where it will all go, but with drones in the air, self-driving cars on the ground, and Terrafugia flying vehicles, it promises to be an exciting future for startups in Boston.

KC:  Greatest misses - what company(ies) have you passed on that you wish you hadn’t?

DC:  Investors circles are small, and we end up seeing a lot of the same opportunities. In the end, founders need to find the best fit, so I’ve passed on a number of great entrepreneurs where I didn’t know the space and felt I couldn’t help. Matt Barba and Frederick Townes of Placester gave one of their earliest pitches at the WHERE office, and I didn’t invest. My former board member Ryan Moore led the seed round for DraftKings, and I still have the original email of the drumming up interest for them.

It’s hard to fight FOMO, but as an investor, you have to stick to your investment thesis and feel fine when you pass on what turns out to be a great opportunity.

KC:  What are you personal interests or activities?

DC:  I have always loved photos and digital media, as my 450GB Photos Library has forced me to upgrade my Mac multiple times. My dream room in the house would be a media room with a ridiculously big screen and great sound. Outdoors, I’m a big fan of biking to get around town, and I’ve been biking to everything lately. In fact, in the first half of the year, I did two dozen workshops, events, and speaking engagements that were within biking distance of home - weather notwithstanding. Lastly, I wish I got onto the ski slopes more often. I somehow squeezed in 25 ski days one year while maintaining a full-time job. That’s not going to happen again.

KC:  What type of music do you like?  

DC:  My music playlist is embarrassingly skewed to 80’s new wave “alternative.” Growing up, I spent a ton of time making mix tapes on cassettes, which are probably sitting at the bottom of the closet. I am so excited that almost all these songs are now available in a digital format. Love live the 80’s!

KC:  Are you involved in any charitable organizations?

DC:  I spend about one day per week devoting time to non-profit and industry organizations that intersect with my professional passions. In my role as Rock Center Entrepreneur-in-Residence at Harvard Business School, I mentor college students and graduate-school level students with their ideas and careers. I quickly forget that I’m twice the age as many of the students that I work with (note to self: do not buy beers at lunch with college students). As a longtime committee member for The Ad Club’s Brandathon, where Silicon Valley meets Mad Men, I get to witness the collision of two different worlds. My longest tenure has been with MITX as a board member, which gives me a unique opportunity to work with people across the innovation ecosystem.

This past summer, I was host committee co-chair for the BUILD Boston Entrepreneur Games along with John Barros, the City of Boston’s Chief of Economic Development. BUILD is an amazing organization that changes the trajectory of high-school students from under-resourced communities, using entrepreneurship and experiential learning to do so. If you’ve met any of the 14-17 year olds that are part of the program, you’ve experienced firsthand how much you can help with just a little effort. If you haven’t, would love to see you get involved!

Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.