November 12, 2014

We held an awesome Angel Bootcamp yesterday at MIT. It was an amazing collection of speakers sharing their experience and wisdom around angel investing. It including folks like David Tisch, David Cohen, Paul English, Diane Hessan, Katie Rae, Andy Palmer, and many others. The full speaker group was here:

Even though we are a seed-focused VC fund, we were very excited to help organize this event because of our belief that increased angel activity is critical to keep propelling the Boston startup ecosystem (and the local economy) further. More and better informed angels allow more founders to pursue ambitious companies, not just by providing dollars, but by doing so in a way that is as helpful as supportive as possible.

The content presented during the day was unique and amazing, and I’m still processing everything. But I took some notes along the way of my top takeaways from the talks. Here they were below:

1. Focus on founders that just won’t give up.  This is something I’ve seen in my own investing experience.  Of all of our investments, a large percentage will not work out. The founders that we are most likely to back again are the ones who just wouldn’t give up, and keep fighting. I remember personally a friend of mine giving a reference for a founder he had worked with, and his response was “he will fight to the death like a cornered badger”.  That’s a good trait to look for.

2. You don’t necessarily need to like a founder to want to invest in their company.  This is somewhat controversial, but a number of speakers talked about how some founders were amazing, even though they weren’t necessarily the people they’d want to have dinner with.  Founders tend to be extraordinary people, which often makes them quirky, unusually aggressive, or awkward in other ways.  If the founder is committed, effective, honest, and capable, does it matter whether or not you particularly “like” the person vs. just being confident you can work together?

3. SAFE docs are on the rise. These are financing docs that were pioneered by YC and is apparently starting to see some level of acceptance in Silicon Valley. There was fairly heated debate about these during the afternoon, with some very experienced angels (who spend more of their time in SV) saying that there was “no F*cking way” they would invest in one of those. The benefit of a SAFE is that it isn’t actually a convertible note.  Which means no maturity (and thus, no ticking clock for a payback), no accrued interest (since it’s not actually debt), and preferences that are equivalent to the dollars invested vs. some multiple of that (for a discussion around this, see this from Mark Suster).  Personally, I’m not a fan of notes and very much prefer equity financing. I think there is probably innovation to be found in simple equity financing documents that:

  • simplifies the documentation required and keeps cost in line with that of a convertible note
  • allows founders to close on cash quickly and sequentially
  • establishes clean, fair terms for future financing rounds

Some of these docs exist, but for whatever reason hasn’t been adopted in a way that allow for low friction similar to notes or SAFE documents. But in my mind, if a founder and investor can agree on a valuation cap, agreeing on the simple terms for a plain vanilla equity financing shouldn’t be that hard, and aligns interest much better. That said, I’ve never been that dogmatic about this topic – I have a preference, but I think some of our objectives can be achieved through different instruments. It just ends up being more trouble that it’s really worth, typically.

4. Back founders who like talking about the hard parts of their business.  This was suggested as a major lesson learned from my friend Eric Paley at Founder Collective.  The idea is that you want to back founders that engage honestly, and with great depth on the biggest challenges of theirbe business.  This is good because it shows that the founder has an appreciation for what is hard, embraces the challenge because they see it as a long-term competitive advantage, and is intellectually honest about the difficulties they are likely to encounter later.  More specifically, founders that are able to do this well are a) able to have specific hypothesis that they are testing to address these challenges b) able to distinguishes between challenges that they feel can be overcome by sheer will or because it plays to their strengths vs. those that are more uncertain, and c) able to show vulnerability and uncertainty to investors while still earning their confidence.  I think this is a great lens through which to think about founders.

5. Platforms on the rise. Two of our speakers were Jeff Fagnan and Alex Mittal. Jeff is a seed investor and founding board member of Angelist, and Alex Mittal is the co-founder of FundersClub. Both spoke a bit about the development of these respective platforms, how they have performed, and how one could get involved on them. What struck me overall was the scale of these platforms, and how successful they have been. Both platforms boast really extraordinary companies coming through their platforms and really impressive performance.  In the early days of these platforms, there were major questions about adverse selection, essentially that “only the crappy companies would resort to a platform for their fundraising needs”.  Given the progress so far and the direction these platforms are headed, I think those concerned are pretty far in the past.

6. Pro rata rights – much ado about something (and nothing). There were a number of heated discussion about pro-rata rights and what to do with them. Some investors are religious about insisting on them and capitalizing on them, others were much less dogmatic. At Nextview, we like to have pro-rata rights, because we want to be heavily invested in founders we believe in and companies that are outperforming. In our opinion, it’s reasonable for founders to make sure that the investors that believed in them early and were supportive from the beginning can continue to invest.  On the flip side, the reality is that these right end up being somewhat helpful, but only partially so because allocations end up being negotiated at the next financing round pretty much independent of these rights.  But again, I think it’s reasonable for seed investors to be put in a position where their ability to capitalize on pro-rata will be driven by their ability get a founder to fight for their rights, which usually means that they were supportive, responsive, and added a lot of value along the way.  So in short, I think this is much ado about nothing. I think it’s right to offer these rights to your earliest investors and to put it into financing docs so that there is mutually agreement about expectations post financing. I also think it’s right for investors to have to show that they deserve their pro-rata based on how they behave post financing.

7. The best angel investors hunt. There is a misconception that as an angel, your job is to evaluate opportunities based on the companies that come across your table. But the best angel investors hunt. David Tisch mentioned that something like 80% of the investments he makes comes from some sort of proactive activity, and he’s an angel that gets a huge amount of inbound deal flow! Other angels talked about “not dabbling” and being “committed” to angel investing, which I think are some other versions of this. Being an angel can be very rewarding, but it’s more rewarding if you are involved in more interesting companies and more impressive founders. That doesn’t happen by accident.

There were many other nuggets of wisdom, but there were the first ones that came to mind when I got home tonight. It was a great even overall, and I learned a ton. Thanks again for our terrific Sponsors, Wilmer Hale, Jones Lang Lasalle, and Silicon Valley Bank for their financial support, and for Jon Pierce (the godfather of this event) and Jay Acunzo for their help organizing. And again, huge thanks to all the amazing speakers for donating their time and efforts to the day. It was really rewarding to help put it together, and hopefully we’ll see some great fruit for our labor in the years to come.

October 21, 2014

I’m pleased to announce that NextView is co-organizing an event on November 11 called “Angel Bootcamp” along with the event’s original creator Jon Pierce.  The event will be held at MIT from about Noon – 7PM.

The first Angel Bootcamp happened several years ago. The goal was to mobilize and educate the angel community in Boston to become more comfortable and more active investing in early stage internet, mobile, and software companies. Both then and now, our belief is that there is a dearth of high-quality, angel and seed stage capital in the Boston market, and that it would be a huge benefit to the economy as a whole to motivate some of the capital sitting on the sidelines to participate in the innovation economy.

After a short hiatus, Angel Bootcamp is back! The content will be unique – consisting mostly of quick prepared talks on some specific aspect of angel investing or sharing personal stories. We have a packed schedule, and one of the most outstanding speaker lists I’ve seen in a long time. These are people who have been successful entrepreneurs and angel investors in companies that have touched hundreds of millions of people and created billions of dollars in value like:

Uber, Warby Parker, Instacart, Blue Apron, Kayak, GrabCAD, Angelist, Crashlytics, Coupang, Opower, and many others.

For angels or potential angels, this is a chance to hear some of the best in the business share their perspective on investing in the most raw but most exciting companies. For entrepreneurs, this event provides a unique lens into the way angels think and how and why they might get excited about a particular company.

Among the topics I’d expect we hear about:

  • How David Tisch, one of the country’s most prolific angels got started investing at the very first Angel Bootcamp
  • What to make of crowd funding, from the founder of Funders Club and a board member of Angelist
  • How angels can make any money in hardware, from the founder of the best hardware accelerator in the country
  • The perspectives of those who have been on both sides, like Andy Palmer, Diane Hessan, Paul English, Wayne Chang, David Cohen, and others.

It’s an amazing group of both local and out of town guests, and I’m super excited. You can see the full speaker list and further details here:

Because of space constraints, the attendee list with be curated to manage an effective mix of angels, aspiring angels, founders, and students. Click the link above to request an invite, or shoot a note to myself, Jay Acunzo, or Jon Pierce.

Of course, this wouldn’t be possible without some terrific sponsors – many thanks to Wilmer Hale, Silicon Valley Bank, and Jones Lang LaSalle for generously offering to sponsor our efforts, and MIT for providing a terrific venue.

October 16, 2014

I’m excited to be able to unveil our recent investment in PaintZen. The company is a technology-enabled service marketplace for the home and commercial painting industry. They have gotten off to a torrid start in New York, and just announced their launch of San Francisco today. Check out more details here and here. What I think is really notable about Paintzen is that coupled with their rapid growth, their quality standards and subsequent referral activity is extremely high. Check out their yelp reviews here, and just contrast them to the reviews of other service marketplaces in some other categories, and you’ll see that the reception has been night and day.

A couple weeks ago, an essay was going around by Paul Graham that talked about how many entrepreneurs “play house”. The article describes entrepreneurs that go through the motions, read all the blogs and online resources about building a company, say all the right things, but are more interested in “imitating all the outward forms of a startup”  vs. being deeply committed to building a great business. Mike, Justin, James, and the team at Paintzen is one of the most stark counter-examples of “playing house” that I have ever seen. No unnecessary flair or pretense. Insanely deep understanding of their vertical, as well as deep understanding of service marketplaces generally (the Mike and Justin previously co-founded MyClean in NYC as well, which is growing at a great clip). And simply building a great business with nicely developing economics, scaleability, and increasing returns to scale.

We were excited to join a number of previous co-investors in this round, including the good folks at Lerer Ventures, Quotidien, and others. Thanks in particular to Sean Black who re-connected us with the team and also joined us in this round.

Congrats everyone – onwards!

October 1, 2014

It’s the eve of Wayfair’s Initial Public Offering, and I’m so excited for the company.  Big congrats to the entire team there, especially NextView Venture Advisors Niraj and Steve (who were among the first people to get behind NextView in the early days).  Congrats also to my wife Nancy, who is VP of Brand Marketing at Wayfair, and was the first person to believe in me in the early days too :)  And congrats to my friend Alex Finkelstein who led Spark’s investment in the company several years back.

Wayfair stands in stark contrast to so many other tech companies you read about.  Where other companies chase hot sectors, Wayfair started in the midst of a burst bubble selling speaker stands online.  Where others raised millions and millions of venture money before they had a business, Wayfair built a business on its own cash flow, and only raised money after they had profitably grown to hundreds of millions of dollars in revenue.  While others chased the wealthy, or the hipsters, or the fashionistas, Wayfair eclipsed them all by focusing on mainstream consumers. While others loudly beat their own drums about vanity metrics, lavish perks, or bold claims of grandeur, Wayfair has allowed their results and execution do the talking.

What an amazing company.

As I said a week or so ago in a tweet, I think that the best years are still ahead for this business.  The company is going after a near limitless market in home goods that has been very slow to transition online, and they have built a highly defensible moat around their excellence in logistics and operational efficiency at scale.  And this is all bolstered by a humble, scrappy, and hungry culture that pervades the entire company.

Congrats Wayfair!  I hope every employee and alum feels immense pride about having reached this milestone.  But contrary to how I feel about most tech companies that go public, I think the future holds even more potential.

The best is yet to come.


October 1, 2014

Today, we’re excited to unveil the official Hitchhiker’s Guide to Boston Tech — a comprehensive overview of what tech entrepreneurs and professionals need to navigate and succeed in our local community. Special thanks goes to Jay Acunzo (director of platform here at NextView), Ariel Simon (senior designer, SapientNitro), and Keith Frankel (Chief Digital Officer, Tablelist) for creating this bigger, more comprehensive, and more beautiful edition of my long-running blog series.

In case you’re new to the Hitchhiker’s Guide, there’s a bit of history behind it. In 2009, I published a simple link roundup titled A “To-Do” List for New Entrepreneurs Arriving in Boston. It contained the basics like who to follow on Twitter, where to meet people for coffee, and what events to attend. In 2010, I coined a name that stuck — Hitchhiker’s Guide to Boston Tech — and published every six months since. It focuses specifically on the web and mobile startup ecosystem locally (though it’s worth noting the great work in biotech, robotics, healthcare, and energy here in town too).

Fortunately, the community response to these blog posts has been positive. It’s been great to see entrepreneurially minded newcomers to Boston turn to these posts as a go-to resource. Even other VC’s, angels, and prominent local entrepreneurs have referenced the guide or pointed their friends towards it, which is exciting.  As always, the Boston ecosystem has been really friendly and open to navigate, and I’m glad that these guides have been helpful.

But Boston is a transient and dynamic town, and can feel somewhat intimidating to newcomers.  Even for locals, the startup world has exploded since 2009, making it increasingly difficult to navigate.

So when Jay approached me a couple months ago with the idea of turning this into something more substantial — something that would stand alone as a more beautifully designed “front door” to our ecosystem — I was instantly on board. Historically, the link roundup has been very useful, but this would be a chance to design something that felt more special, more worthy of our amazing local ecosystem. It’s also a good reminder that while there’s a lot listed on the guide, there could be a lot more. We’ve got a lot more work to do in Boston tech.

I’m also excited that we’re now able to crowdsource additional submissions to grow this over time and keep it as fresh as possible — to participate, look for the links to submit new items beneath the various sections of the Hitchhiker’s site.

Boston has grown an amazing startup ecosystem over the last decade, and we want to help both new and existing community members better navigate and succeed right here in town. So, without further ado, I invite you to explore, expand on, and share the Hitchhiker’s Guide to Boston Tech.

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  • Rob Go
     - 2 days ago
    @alexcalic in a market where deals happens so quickly, there is often not enough time to discern. Too easy to get snake charmed
  • Rob Go
     - 2 days ago
    @christophmccann yes, but I think it is way way over-emphasized
  • Rob Go
     - 2 days ago
    I've been asking myself this a lot: Is this person really a great entrepreneur? Or just really great at talking about their company?
  • Rob Go
     - 2 days ago
  • Rob Go
     - 2 days ago
    @nickducoff I have