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David is an entrepreneur and angel investor who is currently an EiR at Harvard Business School, Executive Chair at Feelter, and Co-founder of PersonalVC.

David has held product and marketing roles at five Boston-based startups that were acquired. He previously led the PayPal Boston office and co-founded the Start Tank innovation space. Earlier in his career, he held roles at TripAdvisor (IAC), m-Qube (Verisign), edocs (Siebel), SnapMyLife (Exclaim Mobility), and Goldman Sachs.

As a leader in the entrepreneurship community, he holds several advisor/board memberships and has made 40 angel investments in early-stage startups. Recent awards include Boston Business Journal's Power 50: Most Influential Bostonians, BostInno’s 50 on Fire: Investment Winner / Tech Finalist, and Finalist for NEVY Angel of the Year.

David holds a BS with Distinction in Computer Science from Cornell University and an MBA from Harvard Business School.

  • GH

    Glen Harper

    about 1 year ago #

    Thank you for joining us today, David.
    If a company had a product that was used only, say, once to a few times a year (like say home buying or health care or travel), how could they convince you to invest?

    • DC

      David Chang

      about 1 year ago #

      Frequency of use is definitely a key factor to be able to iterate frequently and stay top-of-mind with users. At my last startup, we spent a lot of time thinking about how to increase the number of times a user could interact with the service. Having said that, there are plenty of infrequent, high-engagement products/services (e.g., TripAdvisor) that are successful.

      To invest, I'd like to see how the startup plans on engaging that user (both acquisition and retention) and how that builds a defensible asset over time.

      2 Share
      • GH

        Glen Harper

        about 1 year ago #

        A quick follow-up:
        From your time at TripAdvisor, what lessons do you think other infrequent-use startups could take away when it comes to user engagement?

    • DC

      David Chang

      about 1 year ago #

      For infrequent-use services, I'd look for partners in the value chain (either directly before or after the service) where you get another crack at the user.

  • JF

    Javier Feldman

    about 1 year ago #

    Hola, David.
    1. What makes a good startup pitch according to you?
    2. Has there been a case where the pitch was bad but you still gave the startup an investment? If so, what changed your mind (and was the team an unproven one)?

    • DC

      David Chang

      about 1 year ago #

      On question 1, there are many types of startup pitches to investors, e.g. the 2-minute elevator pitch, the 30-minute coffee meeting, the 1-hour sit-down meeting where the founder walks through a pitch deck. For the 1-hour longer version, the pitch deck definitely needs structure. I'm a fan of the two styles that Next View published a few years ago: http://nextviewventures.com/blog/free-startup-pitch-decks-template/

    • DC

      David Chang

      about 1 year ago #

      On question 2, I've definitely seen raw, unpolished pitches. I don't think those pitches were bad - I think they just needed a lot of work (whether it was flow, content or polish). In these cases, the pitch actually got in the way of the entrepreneur. They were better off simply doing a demo or talking through their experiences.

      2 Share
    • DC

      David Chang

      about 1 year ago #

      As an anecdote, my second angel investment was in @Crashlytics @wayne @jeffseibert. I don't think I ever saw the actual pitch deck :-)

  • AL

    Arsene Lavaux

    about 1 year ago #

    Bonjour David,

    Merci for doing this AMA.
    Great to see that you recently joined Babson.
    I hear it's a great place for entrepreneurship ;)

    Here are a few questions for you:
    1) If you had to pick three things that most influence your angel investments decisions, what would they be?
    2) What makes an entrepreneur great at entrepreneurship?
    3) Is a startup founder a growth hacker without knowing it yet maybe?

    Looking forward to continuous entrepreneurial and growth learning.

    Merci encore!

    • DC

      David Chang

      about 1 year ago #

      On question 1, the three things that most influence whether I make an angel investment are the team/people, opportunity/risk, and alignment.

      For team/people, that's the key thing in the early stages of a startup. The idea almost always morphs, and if the team/people can't pivot and iterate, the startup has little chance for success.

      For the opportunity/risk, I look for criteria that's a bit different than that of VCs - while VCs have to swing for the fences each time, as an angel I have more flexibility to pick and choose in interesting opportunities that may not align with any investment thesis. To minimize risk, I look for opportunities that have low financing risk for the next round.

      On the alignment side, anything where I can help - whether it's because I have unique knowledge or contacts in the space or if I have some sort of functional expertise the startup can use.

      3 Share
    • DC

      David Chang

      about 1 year ago #

      On question 2, I think focus and putting in lots of iterations (where they learn from each iteration) is key.

    • DC

      David Chang

      about 1 year ago #

      On question 3, I've never thought of it that way! There are certainly many common traits, however I think really good growth hackers have a more defined area of expertise, while really good startup founders can have a broader set of skills to pluck from.

      3 Share
      • AL

        Arsene Lavaux

        about 1 year ago #

        Definitely agree with your take on this. GH should be a subset of the hats a founder must juggle to create sustainable growth... Pleasure reading your answers David, thanks for sharing. :)

    • DC

      David Chang

      about 1 year ago #

      Thanks for sending in the first question! Glad to be here, and happy to help however I can. I'm originally from New York and have actually been in Boston since 1999. I got looped into a startup coming out of business school and never looked back. I'll tackle each of the questions separately.

  • RS

    Rishabh Saxena

    about 1 year ago #

    Hi David,

    Great to have you here for the AMA.

    Having been involved actively with startups based in Boston, how would you say the ecosystem is developing in the area? Any particular startups that have particularly caught your eye?

    • DC

      David Chang

      about 1 year ago #

      I'd love to see more marketing/promotion of the good stuff that's happening in the Boston area. Having said that, I'm not sure if investors/operators should be focusing on that. I'd rather see these emerging clusters just knock it out of the park, and that will create the virtuous cycle. Go 100% deep on solving a problem in those clusters and leverage the assets that are already here. It's definitely happening in some fields. An international entrepreneur recently said to a group of us "everyone knows that Boston is the center of the universe for 3D". I didn't know that, but it was so cool to hear the perception from someone outside of the U.S. on that industry.

    • DC

      David Chang

      about 1 year ago #

      I LOVE how strong the Boston ecosystem is in certain industry clusters, e.g., Boston-area as a world leader in life sciences. There are also strengths in clusters that may be less well known, e.g., travel, mobile, payment, where the most experienced people in the world are also running around town.

      As for specific startups, it's REALLY hard for me to answer that. I see several hundred startups each year, and many of them catch my eye for different reasons. Some are already great standalone companies, while others consist of great people that are still fleshing out their ideas.

      • AA

        Anuj Adhiya

        about 1 year ago #

        re: clusters being less well-known.
        Do you think Boston doesn't do a good enough job of marketing its tech ecosystem as well as, say NYC or SV?
        What do think investors and/or operators be doing differently to turn that around?

  • AA

    Anuj Adhiya

    about 1 year ago #

    Hey David - so cool to finally have you on!
    You've clearly invested in a boatload of companies. To follow up on another question you got about what influences your decisions to invest, can you share some of the questions you ask to suss out the information that will help you decide one way or another?

    • DC

      David Chang

      about 1 year ago #

      Thanks for having me on! I mentioned above some of the criteria, and since I see a lot of companies, I try to get a big picture understanding of the key components of a startup within the first 30 minutes. I occasionally use this grid (https://venturefizz.com/blog/advice-entrepreneurs-angel-investors) for my notes. I generally look for startups where all of the components are internally consistent with each other.

      2 Share
  • JP

    John Phamvan

    about 1 year ago #

    Hi David,
    Pretty much every investor has a blog or writes regularly but from what I can tell, you don't.
    Why is that?
    What would make you consider starting?

    • DC

      David Chang

      about 1 year ago #

      I would love to do so, but I find that I take way too much time revising and revising. Writing, especially longer form content, is personally difficult for me. It's always been that way for me. I remember back in high school I had a 200 point split between the math & verbal parts of the SAT. I am still catching up on the verbal side as the math side slides with age :-)

      I think part of the reason why I like social media is that the snippets are so short that there's no time to rethink. It's like beat the clock right now on this AMA!

  • TN

    Tri Nguyen

    about 1 year ago #

    Are there questions you wished you got asked (or asked more) from founders seeking investment from you?
    What do such questions reveal about the founders?

    • DC

      David Chang

      about 1 year ago #

      I'd love to see founders, particularly first-time founders, ask brainstorming type questions about how to grow the business. Nothing engages me more than a founder that is so fired up about his or her startup that they can't stop thinking about ways to accelerate it.

      4 Share
  • MD

    Mark Anthony de Jesus

    about 1 year ago #

    What advice would you give to first time founders that have no inherent domain expertise but are passionate about solving huge problems in such verticals to raise their odds of success?

    • DC

      David Chang

      about 1 year ago #

      It's perfectly fine not to have domain expertise as long as you have a plan to recruit for people who can fill that gap (either through having that experience or having some functional expertise that can be applied in the industry in question).

      I've seen plenty of founders of both types succeed - ones that have experience in a field (e.g., they've felt some pain in an industry and want to resolve it) and ones that are functional experts.

      2 Share
  • DH

    Dani Hart

    about 1 year ago #

    Hey David.
    What does an EiR do? Why did you decide to take on this role (it seems like you have a lot going on anyway).
    What value does this role provide you from a professional/investor perspective?

    • DC

      David Chang

      about 1 year ago #

      At Harvard Business School, the EiRs are resources for student entrepreneurs across the whole university. The primary interaction is holding office hours with students to help them with any questions or challenges that they face. Some EiRs spent more time in class working with faculty and students on course work. In my case, I also serve as a coach for the Rock Venture Program, a yearlong accelerator for student ventures. This interaction is great since I get to work with a small number of teams throughout the year.

      In terms of what I personally get out of it, I stay plugged into the latest ideas, see a fresh group of promising talent, and it's just an energizing way to spend an afternoon!

      https://entrepreneurship.hbs.edu/programs/mba/Pages/entrepreneurs-in-residence.aspx

      2 Share
  • DO

    Danielle Olivas

    about 1 year ago #

    Have you ever invested in first time, unknown entrepreneurs?
    If yes, what did they do to convince you?

    • DC

      David Chang

      about 1 year ago #

      Absolutely. Every successful entrepreneur was once (or still is) a first-time entrepreneur. In these cases, it's important to articulate their vision and plan to achieve the milestones that they set. In many of the cases, I get to see the founder at different points in time (e.g., we first meet in November, then again in late December and see the progress in the business), so I'm able to start seeing trends.

  • JD

    James Dunn

    about 1 year ago #

    I took a look at the companies you've invested in. All of the companies are quite diverse. So what characteristics do you think are common between the companies/founders?

    • DC

      David Chang

      about 1 year ago #

      Since I'm not a professional investor, I don't have a specific investment thesis and have lots of flexibility in the kinds of startups and people/teams I get to work with. I don't actively source deals - my leads usually are inbound and come from my existing network, previous colleagues, or organizations like HBS, Babson, Techstars, MassChallenge, etc. They common attribute is definitely my belief that the founder knows his/her business and has the ability to grow it. Beyond that, many of my past investments are in industries where I have some knowledge (or hopefully insight) or where I think I can help.

  • MT

    Manny Tafoya

    about 1 year ago #

    Hey, David! I have a question. What's the unsexy stuff that no one talks about that people considering angel investing should consider before taking the leap? Thanks!

    • DC

      David Chang

      about 1 year ago #

      First, it's good to be clear what your objective is. Angel investors range from those who are motivated by
      1) financial return (some are good enough that that's all they do)
      2) strengthening industry connections
      3) leverage their own expertise (and giving back)
      4) purely philanthropic

      It's probably some combination of factors, and you'll either love or hate various aspects of angel investing. One big drawback is that it takes a long time (years) to see results to know whether you're good or bad at angel investment (I still don't know for myself). In addition, I personally don't like some of the operational/execution aspects - reviewing term sheets, going through legal documents, etc.

      2 Share
  • GC

    Gary-Yau Chan

    about 1 year ago #

    Hi David,

    You have a tremendous career, starting from Products --> Product Marketing --> Startup Founder --> COO.

    1. What is your advice on continuing to grow and learn?

    2. How did you seek out opportunities to further your career?

    • DC

      David Chang

      about 1 year ago #

      Appreciate it, but it was a big mix of luck and being in the right place at the right time. I have a LOT of thoughts on this, but running out of time. Let me see if I can find a post/talk I've done in the past that covers this.

    • DC

      David Chang

      about 1 year ago #

      I found a snippet that covers some of this (slides 36-40): https://www.slideshare.net/secret/g7Y4wXRzIbuIxX

      On expanding your skills, I really liked one bit of advice I got from a career counselor while I was school. If you picture yourself at the center (represents today) of series of concentric circles, there are many paths to the final destination (outer circles in the future). Any given transition is relatively easy to make, but it's hard to traverse that outer ring in the future if the sum of all your previous decision have been on one path. Takeaway is to be open to multiple opportunities and don't stress out over a single decision (since most decisions are 51 one way/49 the other way).

      On finding your next role, in general, at any stage in your career, think about four levers: location, function, industry, size of org. On each of these four, you'll have either narrow criteria or be agnostic. Together they form a fingerprint of the kinds of company to seek out.

      • GC

        Gary-Yau Chan

        about 1 year ago #

        Quick note: the above Slideshare URL is in private btw

        <><><><><

        Thanks, David.

        One of the biggest contemplation I had recently is how do you improve on skillsets while preparing for the next career trajectory.

        Previously I run product at my own startup, now growth (which I believe is product 2.0) at another company, and then how to build a path to product lead a bigger strategic organization.

        Similar to your advice above: One of the conclusions I have so far, while counter-intuitive, is focusing on executing at my current role as best as I can. It will be the preparation I need when the next opportunity presents itself.

  • SK

    S Kodial

    about 1 year ago #

    Hi David
    What inspired the idea for PersonalVC?
    How will this matching between investors and founders happen?
    And why is it free (not that i'm complaining)? Are there any plans to monetize this in the future?

    • DC

      David Chang

      about 1 year ago #

      After years of working with founders and investors, I got to see firsthand how inefficient the process is of finding a good match. After Start Tank Boston got acquired by MassChallenge, the thought of having to sit down with hundreds of startups, one at a time, was so daunting. My co-founder and I believe that there should be a way to use data, software, AI, and social signals to match founders with investors. PersonalVC started as a passion project, and it's free for founders since we really want to help startups accelerate. If we get good at doing these matches, we'll monetize on the investor side by providing them with personalized, highly qualified dealflow.

  • PD

    Porus Daruvala

    about 1 year ago #

    Hi David
    If I can ask you the Peter Thiel question: What is it about startups/investing/fundraising that you believe to be true but almost no one agrees with you on?

    • DC

      David Chang

      about 1 year ago #

      Hmmm. I've never thought of this. Maybe that I believe that the fundraising process can be broken down into a very discrete series of steps that anyone can follow. Many feel that it's a mystifying process, but it's really not.

  • AA

    Anuj Adhiya

    about 1 year ago #

    One more from me.
    Was there any startup that you didn't invest in for whatever reason that then went on to become a huge success?
    What was it at that time about the company that didn't make it appealing?
    What lessons did you take away from that experience about how you evaluate prospective investments?

    • DC

      David Chang

      about 1 year ago #

      Ah, so many misses. I remember seeing (and missing) an email about the first DraftKings seed round. I had an upfront view of Wanderu (I was a judge at MassChallenge during their pitch, stayed in touch since it was in travel, pulled them into the first cohort at Start Tank). I didn't invest in Placester even though I got to see them early. On the job side, there was an opportunity to join Waze (but didn't want to pursue something on the west coast).

      With hindsight, I might wish now that I made a different decision, but as a general rule, I still think it's best to have some discipline on what's a good fit and what's not. You just can't look in the rear-view mirror and feel bad!

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