Back in June, the local Boston tech community together celebrated the ten year anniversary of the Web Innovators Group, affectionately known as ?WebInno.? ?Now Boston?s largest regular tech conference, every few months it draws hundreds of attendees from the entrepreneurial ecosystem ? including founders, software engineers, startup executives, and...

A few years ago I replaced all of the decades-old windows in our home with new ones.? The entire process was horrible.? I used home service lead-gen and recommendation-review sites to identify a half-dozen installers to set up initial in-person consultation appointments.? Only half of them even showed up.? For those who did, I was […]The post...

Tales become legends about founders of exceptionally transformative companies who truly struggled to get any investors? attention early on.? These rejection emails to the founder of Airbnb represent just one of the most recent example of this familiar theme. If a startup were obvious, then everybody would be doing it.? And it wouldn?t be an […...

Today, I?m thrilled to publicly announce NextView?s Talent Exchange, a program helping both top talent and NextView-backed startups connect with each other more easily, beginning with Boston companies?(which make up just over half our portfolio). Below, I?ll quickly explain the genesis of this initiative and share a few more key details. One of my ...

A couple weeks ago my colleague Dimitri Dadiomov published a post on NextView?s ?View From Seed? blog which answered the question ?Should we take Harvard MBAs Seriously as Startup Founders??? The (obvious) answer of ?yes? he supported with comprehensive research about the entrepreneurial activity coming out of Harvard?s business school. We knew tha...

Conventional wisdom says that the best way to meet with a venture capitalist is to get a warm introduction.? (While it?s a good rule of thumb, it?s not entirely true, which I?ve blogged about previously.) However, there?s another way that I?ve seen entrepreneurs use mutual connections that?s even more impactful than a warm introduction: a […]...

As an entrepreneur, if you?re running a venture capital fundraise effectively, you?re treating the process like a sale process: identifying a set of prospects to fill the top of the funnel, cultivating those relationships over a series of meetings, then narrowing down to a handful of contender firms who will ultimately make an offer to […]The...

It?s official: now two months after the IPO, HubSpot has surpassed the $1B market cap threshold and has become that ?pillar? company that the tech ecosystem long anticipated. The benefits have been touted previously: an anchor for attracting and retaining talent in Boston, as well as a breeding ground for the next set of great […]The post The...

When Chad Pytel introduced me to Bryan Helmkamp, CEO/Co-founder of Code Climate, I knew that I had to pay attention.? Chad is the CEO of thoughtbot, a consulting firm that makes web + mobile apps for early-stage startups.? The two companies had been working together for a while, especially as both are deeply embedded within […]The post The Ma...

Mass transportation is the largest single source of travel within metropolitan areas across the globe, but our current fixed infrastructure approach hasn?t changed since the 19th century.? Here in our innovation hub of Boston, the country?s oldest subway tunnel built in 1897 is still in use as part of the MBTA Green Line.? Each day […]The pos...

This is an excerpt from the original post, found on NextView's blog,?The View From Seed, launched this week.?Find the original post?here. As the VC seed market has institutionalized, especially over the past five years, there has emerged a?prototypical seed round?profile:?$1M-$1.5M raised, the first non-friends-and-family capital, comprised of one ...

In every single venture investment I?m involved with here at NextView Ventures, I learn a lot from the Founders of their company. ?But in the particular case of our portfolio company TapCommerce, which yesterday announced its acquisition by Twitter a mere two years after the company?s founding (more details), there have been some key lessons [̷...

It's been five years now since large VC ?signaling? entered the seed stage entrepreneur?s lexicon.? Yet even today, whether or not to take a (relatively) small check in a seed round syndicate from a multi-hundred million or even billion dollar fund is still a decision which takes quite a bit of consideration and sometimes consternation.? […]...

Just about fifteen years ago, Josh Schanker and I, along with our co-founders Elliot Shmukler and Tammy O?Neil Bolduc started Sombasa Media together. ?Our company offered a series of consumer-facing properties, including our flagship property BargainDog, which was an early e-commerce daily deals email newsletter. ?Over the course of a couple short ...

Rob, Lee, and I couldn?t be more excited to share that as of Monday, Jay Acunzo has joined NextView as our Director of Platform and Community. Jay joins us from HubSpot, where he was a senior manager on the marketing team, specifically leading the blog and content strategy. In his Boston-based career, he?s also worked […]

A couple years ago, my partner Lee penned a blog post about the milestone benchmarks for startups raising a Series A round of financing. ?The five conditions for a Series A financing which he enumerated are: a core team ready to scale, demonstrable market size, repeatable cost effective customer acquisition, metric momentum, and plausible monetizat...

Fairly often entrepreneurs will pitch investing in their seed-stage company, and it starts sounding great? interesting market? great team? notable early traction? until we arrive at the financials + fundraising slide and the projections state that this round of Seed financing is planned to be their last. Sometimes it?s even presented as an addition...

My partner Rob wrote bit more on his blog about our motivations for adding our first new team member at NextView Ventures — a Director of Platform and Community.? All three of us are excited to expand our efforts and are currently in the process of seeking an exceptional individual to fill a unique role […]

I?ve commonly heard entrepreneurs recite some version of ?I don?t want to waste too much time fundraising because it will distract me from building my business, so I?ll only talk to a few potential funders.?? The idea is that a couple of highly-qualified VC conversations will follow the 80/20 rule of a ?good enough? financing […]

My partners and I at NextView talk a lot about how fundraising is about finding the true believers rather than convincing the skeptics.? The energy that it takes persuading someone who starts with a bias not to invest is much better suited searching for additional prospects who want to believe in what you?re building.? We?ve […]

Recently, we surveyed our Boston-based NextView portfolio Founder/CEOs asking them about which service provider firms they've been using. The goal was to assemble data in order to share it back to our portfolio companies (especially the newer ones) so that they didn't have to recreate the wheel in determining a short-list of firms to talk...

Mobile is changing the world. As a startup-tech industry, we?ve been talking about it coming right around the corner for well over a decade. And now, it?s actually happening. Really happening. I am not going to spend time in a blog post detailing figures & charts about this mega-trend which will astound you, despite the

It isn?t a secret that there is a huge platform shift underway as consumers transition from the desktop web to mobile + tablet devices. Yet when you look at actual the figures, it?s truly astounding: this year mobile e-commerce sales will be triple that of what it was just a short time ago in 2011,

Compared to most other areas of finance, venture capital is practiced as more of an art, as opposed to a science. For that reason, it?s often said that VCs learn the business best through an apprenticeship model, under the wing of a more experienced pro. The art of venture capital also means that for entrepreneurs

Posts in the blogosphere, conversation on panels of/about VCs, etc. all talk about the best way for entrepreneurs to optimize their fundraising process with the end-goal of receiving a term sheet. It?s often spoken as if the second that magical term sheet document is in hand, the process is over. Unfortunately, that?s an oversimplification which...

After we sold our startup Sombasa Media just over a dozen years ago, I embarked on two distinct ?journeys.? The first was a month-long 1500+ mile cycling trip from the southern tip of England to the northern tip of Scotland (?Land?s End to John O?Groats?). The second was a trip where we hiked the ?Inca

The web has become increasingly visual. Of course the same broadband penetration trends which catapulted the rise of online video over the previous decade also empowered delivery of image-heavy web pages. But more importantly and more recently, the proliferation of high-resolution screens epitomized by Apple?s Retina display means that today?s web ...

VCs like to give out homework. They won?t call it that, though. But rather they use words like ?diligence? and ?information requests.? Just like in school, the homework can actually be productive, as in this case it can lead to a new customer or advisor. But just like bad teachers did in grade school, VCs

About a year ago, I wrote a post about?how office space is the face of a startup ? it communicates both an outward message and provides insight into what?s going on underneath, as the physical environment in which startup employees work inevitably match the company?s story and culture. Recently I?ve been thinking that it?s not

Happy New Year and welcome to 2013. According to all of the blogosphere chatter over the past month, seed-funded internet startups are entering this year gearing up for the now-near-infamous Series A Crunch. The CB Insights report specifically which came out just before the holidays put a bright light on the supply-demand imbalance of the

Most first and second pitch meetings with VCs are fairly lopsided, where entrepreneurs spend the bulk of the time sharing their businesses, rather than being a true exchange of both parties in developing a relationship. However, there is typically (and should be plenty of) time for founders to ask VCs questions about their approach and

Dharmesh Shah had a great post up last week about the lessons learned from raising a mezzanine round of financing. It?s really interesting, but perhaps only applicable to a more limited set of entrepreneurs. However, there was one gem of a small section in there with a more widely acceptable takeaway: ?It turns out that

There are a couple classic archetypes of internet/software founders, including the genius college student cooking up something quirky but ultimately disruptive in his dorm room who launches his company straight out of undergrad. But the other archetype is a thirty-something entrepreneur who, taking his experience seeing the playbook of success at l...

A few days ago, a friend who works at a growing startup emailed me with the following question (in which I?ve masked just a few of the identifying details): I caught up with a friend of mine from high school that has started a new company where my skills are very pertinent. He wants a

After completing a long process identifying the right venture firms to pitch, running an exhaustive fundraising process, finding a mutual fit, and successfully negotiating terms? at last, the term sheet is signed. So at this point it?s OK to just hand the process over to your lawyers, sit back, and let them work out the

Like a lot of students, I went into business school a decade ago with a set plan to start a company coming straight after graduation in co-founding an internet startup (? again). During the following two years I did a number of things which prepared me for that endeavor, but then also in retrospect, I

You?ve just closed your seed round.? Other than starting to build, hire, and take over the world, there are a bunch of mundane things to do right away.? The following is a first pass at a checklist of items for Founder CEOs to take care of in the first couple weeks after they?ve closed their

I've always wondered why funding begins with fun.? Those three letters.? F.? U.? N.? Fun.?? For entrepreneurs, seeking seed capital means meeting with numerous VC firms and sometimes dozens of angels? fun?? Telling the same pitch over and over again?? taking time away from more immediately impactful endeavors like recruiting and customer developmen...

One Jackson?is a new online children?s clothing retailer which is surprisingly fresh ? all of its designs were created by independent designers and then curated with love from its community of parents.? The results are high-quality fashionable creations at an affordable pricepoint – which look great and are uniquely different from mass clothi...

As more transparency to seed-round funding transaction details have emerged, especially with the advent of Angelist and accelerator programs (which both educate and even sometimes set terms & structure for graduating companies), I?ve noticed an increasing number of entrepreneurs signal pricing expectations much earlier in the seed fundraising p...

In the past few weeks, we?ve seen extremely positive headlines about the surge in VC fundings like ?Venture Capital Hits Highest Level Since Dot-Com Bubble.?? It must be the best of times for the industry with $8.1B invested in startups during the second quarter of 2012 (the highest in a decade!) along ??with seed-round venture

Personal networking is a key business skill.? And as a VC, I get plenty of practice doing it.? As one of my former high school coaches used to put it, ?Practice doesn?t make perfect.? Practice makes better.?? While I guess you could develop a ?strategy? to networking successfully (? with many a book written about

There are essentially two distinct basic strategies for startup entrepreneurs to raise a seed round of capital: Subscription approach ? An entrepreneur sets a structure (usually a convertible note) and recruits individual angel investors who subscribe to the round, all without a term-driving lead investor. Term-driving investor approach ? An entrep...

One of the things that surprised me most about venture capital when I got into the business is how much VCs seem to like to meet for breakfast. VCs usually typically reserve dinners for portfolio companies? CEOs and board members. And ?doing lunch? doesn?t happen that often because VCs don?t like going out of the

A few weeks ago, a very good friend who works at a growing startup emailed me with the following question (in which I?ve masked just a few of the identifying details): What does it mean when almost all of a startup's early employees have left the company? By almost any measure, [our company] is doing

A lot has been written about a formal ?VC Pitch? meeting with advice about how to handle those interactions with venture capitalists.? But not all conversations with venture capitalists are formal pitches, nor are they expected to be.? And sometimes it?s unclear if it?s a pitch meeting or not. Of course it?s productive to follow

As a VC, I end up meeting some amazing people of many different backgrounds and profiles.? But there are two categories of people which are tightly correlated, but distinctly different.? The difference between what I?d call an ?Inventor,? someone who has many ideas for businesses to start, and a ?Founder,? an entrepreneur who starts a

When was the last time all of your startup?s management team came together to take a step back from day-to-day minutiae and think big picture?? I think it?s actually incredibly valuable for startups to occasionally, and regularly, have offsite planning sessions.? Unlike at ?big companies,? a startup offsite isn?t about a boondoggle, it?s not about...

VCs rarely go into an entrepreneur?s pitch meeting with a completely open mind. Of course they have biases given their past experiences, like with any human interaction. More importantly, though, they have biases about whether or not they are going to find the opportunity attractive even before a word of the dialog has been spoken.

People ask us at NextView all of the time: ?What is the typical profile of an entrepreneur in your portfolio??? Subtly behind that question is often one about the experience-level of the founders.? The answer, however, doesn?t fit into a neat soundbite.? We have and will continue to fund young entrepreneurs in their twenties –