The Lull, through Grapevine, Maine and running

The “Lull,” reality or perception

This week, there is no central feature for Utterly Biased. Just a question.

What is your current perception of the Boston startup community, tech ecosystem, or whatever else you may want to call it?

Is it robust and thriving? Are there some incredible companies on the cusp of making national headlines or are there a whole lot of small wins that we are going to be seeing?

Or, as a few people have put it to me lately, is Boston in a lull?

For such a small word, “lull” packs quite an emotional kick. Webster’s defines it thusly: “a temporary pause or decline in activity,” and more specifically, “a temporary calm before or during a stormor “a temporary drop in business activity.” Whichever meaning you choose, it is not something you’d like associated with your business, and, it’s especially not the type of branding you’d want to saddle on an entire region’s innovation economy.

A slew of recent conversations I’ve been having with operators, founders, investors, and service providers have turned at some point to the theme that the Boston startup scene is eerily quiet at the moment.

Is this reality or just perception?

So, I ask you to send your thoughts my way. Is Boston in a downturn, or is this just the belief of a few. Is the ecosystem actually evolving as it should?

Send your thought to I will publish some responses (you can request to have your opinion remain anonymous to the Utterly Biased readership.)



This week, Dave Balter, a man who wears many hats, suggested a local company that he’s tight with that he believes isn’t getting the love it should. Balter singled out Grapevine, saying that the social media influencer marketing platform is “crushing it right now.”

Balter backed Grapevine through Boston Seed, and he is the head of its board of directors. According to Balter, who spends most of his time on his own venture Mylestone, Grapevine has really thrived since partnering with Chinese billionaire Bruno Wu’s Sun Seven Stars. That would make sense, Sun Seven Stars is an international private media and investment conglomerate that can help Grapevine take its social content monetization platform to a global market.

The market for connecting brands with social media influencers has been burgeoning as of late, but there have been two trends to keep an eye on. For one, YouTube, long the king of leveraging influencer marketing, especially with teens, has been seeing some blowback from major advertisers on how much control they have on the branded content that appears alongside their own advertising. While this doesn’t impact the influencers, per se, it is a signal to the marketplace, which has led some brands to look at YouTube alternatives like Snapchat and Instagram.

Second, Instagram has grown exponentially as a place for both branded content and influencer marketing.

Grapevine serves both platforms and should be able to whether changes in consumer tastes better than others in the space.

screen-shot-2017-02-22-at-4-00-23-pmWhat went down this week…

Maine – I met Kerry Gallivan, the CEO and founder of Chimani, a number of years ago at MIT’s VC conference. He looked a bit out of place hawking his outdoor adventure app, surrounded by three-piece suits and overly-eager to network aspiring venture capitalists. Maybe that’s why I was drawn to him and his story. That or the fact that here was this guy building a massive, aspirational project out of Portland, Maine — one of my favorite cities in the US — of all places.

Last year, Gallivan was listed in Outside Magazine as one of the “next pioneers” influencing the future of the America’s national parks. This week, Chimani announced a new product that should help it continue to dominate the national park tourist space.

  • The new Chimani Perks program is a membership savings club program for national park tourists. The program offers discounts on lodging, dining, activities, and more throughout the national park system, both inside the parks and in the neighboring gateway communities. Since its launch, Chimani — which has maps, content, and more for all 59 US national parks as well as those in the UK and Canada — has seen some rapid growth with more than 1.5 million downloads for its niche product. It customers aren’t the hardcore outdoor enthusiasts you might expect, but a large number of families, professionals, and retirees, what Gallivan called ‘windshield tourists’; a classification that makes up about 90 percent of national parks visitors according to the Chimani CEO. The number of active users each year is 750,000 according to Gallivan, and many of those use the park-specific apps to plan their trips rather than navigate them once they are there.  “Customers love our products, but we had to figure a way to make this business sustainable, which is the basis for this new Perks program,” Gallivan said. One thing is clear, its great to see some innovation happening in Portland and a good outdoor-focused business growing in New England.

FitRaceMenu, a platform for road race directors to manage, promote and grow their events, announced that it has sold off its race timing business to Second Wind Racing. RaceMenu, a stalwart of MassChallenge when it was at 1 Marina Park Drive, has quietly built a nice little business in the health and fitness space. Boston is actually a hub for these types of companies with Runkeeper, Inside Tracker, Spartan Races, Tracksmith, and more playing a major role in the active lifestyle and athlete industry.

I spoke with RaceMenu’s J. Alain Ferry, RaceMenu’s founder about the sale and how he is positioning the company moving forward. His response, “It may sound nuts, but it’s to compete against Square and Paypal.” He added that RaceMenu is “playing the long game.” Here’s more from Ferry, who seems to have figured out a way to actually bring innovation to the racing circuit:

  • “As of last week’s sale, we are singularly focused on software, and more specifically mobile payments. The endurance events industry offers a unique (and incredibly lucrative) opportunity for mobile payments. Ever wonder why every half/full marathon and large 5K under the sun has a pre-race expo but no post-race expo? The supply and demand are still there after the race, and even more so in many cases. But there’s no currency, nor will there be anytime soon. While increasing numbers of people run with their phone, that doesn’t really help all the merchants who want to sell to post-race “runners high” consumers. They’re willing to pay for better food, beer, race merchandise, running clothing, running shoes, massages, GPS watches, other race entries, etc. But how do they pay? There’s one thing which every single runner has on them after the race which can help. It’s their race bib. Timing companies use the race bib to identify the runner for scoring purposes. If you can connect their race bib to the credit card they used when registering online, you can also use the race bib for payments. Now you add this currency to an equation where supply and demand already existed and BOOM: you have a new market.”


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Jebbit and startup evolution, Skok on Zaius, UB on Medium

Do young founders evolve?

Last Thursday, Jebbit, an interactive marketing platform that has recently expanded into more data-driven products, held its first-ever customer conference, which featured talks from co-founders Tom Coburn and Jonathan Lacoste, as well as HubSpot’s Kipp Bodner.

The long-planned event, however, hit a bit of bad luck that, in the end, was quite fortuitous.

You see, the Jebbit Customer Conference 2017 was supposed to be held at Fenway. But when one of the Pirates-Sox games was rained out during opening week, that game was rescheduled to Thursday afternoon, and Jebbit’s inaugural event was without a home. With some help from the Sox, Jebbit was able to move its conference to the Commonwealth Hotel in Kenmore —  a spot with a great view of the Green Monster no less. At the event, Coburn and Lacoste unveiled a strategic shift that has been a long time in the making when it announced its Declared-Data Platform to the 100 customers in attendance — folks like Expedia, CBS, Gannett, Sonesta Hotels, and more.

If that wasn’t enough, Jebbit ended up with a whole bunch of tickets to the game up in the Budweiser Deck to bring over the conference attendees for quite possibly the greatest event after-parties ever.

Showing a lot of flexibility, Jebbit made the most of an unexpected turn of events on Thursday. That shouldn’t be a surprise; the company has been quietly adjusting to changes in online marketing for the past few years.

As Jebbit is out raising its Series A, they are dealing with something that I’ve heard again and again in Boston from companies built out of college or by young founders. For whatever reason, there seems to be a belief that unseasoned or young entrepreneurs in Boston cannot effectively scale their businesses.

This is something that has plagued LevelUp, Drizly, VentureApp,, CustomMade, and many, many other young startups. Many in the VC world don’t expect these companies to be able to evolve to the market and grow. And so, they either hesitate to invest, or, even worse, if they are already involved, they push for a change in leadership.

With Jebbit, which was borne out of BC as a way to advertise to students through quick online surveys, shaking what they were, to what they’ve become, has been quite challenging. Now, as Coburn explains it, customers of its products are using Jebbit as an enterprise data tool that allows them to take mobile experiences to capture valuable customer data. “This opens up new use cases that an enterprise can use outside of marketing,” Coburn said.

As Coburn told me recently, getting a meeting with a local VC can pose a challenge. “I think they assume that what a young entrepreneur’s company was two, three, or four years ago is the same thing that company is now.”

Just for some perspective, Jebbit is a six-year-old company. HubSpot had been in existence for eight years when it went public. (Although, Jebbit was bootstrapped for three years while most of the team was building the company AND studying at BC.)

The Jebbit CEO told me that during the meetings he has had, he has had to fight to explain that over the last four years, the company’s primary product has matured into a data-driven marketing tool and is no longer a college student engagement program.

“People here in Boston, because they’ve known us, still think of us as a survey company, even thought we abandoned that years ago,” he said. “Could you imagine people thinking that you haven’t changed at all in six years?”

“You can decide to stay the course and build out what you’ve started, and that has worked for some companies locally,” Coburn told me. “Or, if you think it will be better for you, you go in a different direction.”

“What everyone was saying about us back then was true, we were a survey company,” Coburn said. “But as we’ve grown up so has this company.”

From people outside the company, I’ve heard that one or two local VCs have changed their minds about Jebbit as they try to fill out their Series A. The rest of the local VCs might be out of luck if they realize too late that these aren’t kids tinkering with a college student app. Like a few other young, local startups raising funding these days, Jebbit might be heading west to talk to investors who don’t have outdated, preconceived notions of the company.



This week, Michael Skok of _Underscore.VC suggested Zaius, a marketing automation, analytics, and CRM software platform, as a local company that isn’t getting enough attention. According to Skok, Zaius “has built the next-generation B2C marketing platform to address fragmented data and customer experiences caused by legacy marketing platforms and patchwork of point solutions.”

“There is a massive market opportunity — the problem is as big for B2C companies as it is for B2B companies and can you imagine a B2B company without a CRM?” he said.

When I asked Skok why they are under-the-radar, he said that until recently the team has been focused on “building a best in class technology platform.” Over the last year, they have really achieved tremendous customer traction and brought on stellar sales and marketing leadership focused on expanding their Boston team out of their North End HQ.”

“The team is nothing short of phenomenal and they will not stay quiet for long,” Skok added.


Submissions for Utterly Biased on Medium

With a shortened Utterly Biased this week, I thought it would be a great time to reveal a new way that Utterly Biased is trying to help Boston tell its story.

This week I launched Utterly Biased as a Medium Publication. Separate from the blog and the newsletter, UB on Medium will serve as an outlet for anyone in Boston who has a good story to tell or some piece of experiential advice that could be helpful to others looking to be more innovative and impactful in their lives and businesses.

Anyone interested in sharing their stories on the Utterly Biased Medium page, shoot me a note at

This is the first in a series of different products that Utterly Biased will be pushing out to continue to serve as a megaphone for the untold stories and the truly innovative people from Boston’s innovation and entrepreneur community.

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Pillar adds a tech pillar, vision-tech maven, vets of all stripes

Boston technology startups get a new VC booster

It was announced last week that Pillar was adding Russ Wilcox as an investing partner. It’s a big move for the growing (in both size and influence) firm started by Jamie Goldstein last year. Wilcox is best known for his role as the CEO and founder of E Ink, the company behind the electronic ink technology used in Amazon’s Kindle readers. E Ink’s tech was spun out of MIT, as was Wilcox’s most recent venture, Transatomic Power.

As his track record — as a founder/CEO and an angel investor — makes clear, Russ is someone who seems to have a knack for uncovering and harnessing some sophisticated technological innovations and bringing them to market…often before the market is even ready for them.

Wilcox grew up in a family, led by an MIT-grad father, that was passionate about science and technology. He credits that for piquing his interest into the possibilities of innovation. That led him to study applied mathematics at Harvard and later to earn an MBA from HBS.

But while many of his HBS classmates took a career path down the road to management consulting, Wilcox had a realization that put him on a trajectory that led him to multiple chief executive roles and his new career as a VC.

I asked Russ a few questions about his journey thus far, including what led him to seek out opportunities such as PureSpeech (where he first met Pillar’s Jamie Goldstein), E Ink, and later Transatomic Power and Piper Therapeutics.

Utterly Biased: What was the impetus for the shift from management consulting, which you had already started doing some work in, to technology?

Russ Wilcox: I was doing some project management around the time I was at HBS, and I had this one little project that made me look at what I was doing differently. One client asked me to figure out how billionaires get created. So I did a bunch of research, read a lot of biographies on billionaires, and quickly discovered that none had gotten that way by working for someone else.

I realized that it was a smart idea to be an owner of something, so started to try to figure out how to make that happen. As someone who loved science and technology, I thought I could be the founder of a tech company, so I focused on startup founders. I wasn’t sure exactly how to do that, so I was caught in a struggle many MBAs face about working for a larger existing company or going out on your own.

I decided there was a middle road between being part of a big company like Facebook or trying to start my own thing, and that was to go work for someone else’s startup. That’s how I ended up at PureSpeech right out of business school, which was the first time I worked with Jamie.

UB: So after you have this startup experience, you are ready to do your own thing, how did you get involved with electronic ink?

RW:  I started to look for something else and was introduced to Joe Jacobson (E-Ink’s technical founder) at the MIT Media Lab. At the time, he was working on this light gray and dark gray screen technology. It didn’t seem like much on its own, but when I looked at the electric ink under a microscope, there was just this gorgeous jet black and titanium white pixelation.

I fell in love with the technology; it was just an intellectually fascinating idea. So I helped launch E-Ink. It was about six years in the wilderness from the Media Lab to shipping, but we got a huge lift when Amazon launched the Kindle and picked our technology. Just prior to that, I had become the CEO, after various other roles, and we started ramping up to meet the demand. In 36 months, we went from doing $9 million to $160 million for the product. Ultimately, in 2009, we sold the company to Prime View International, and they wanted to have their management team managing E-Ink.

UB: So what did you do next after working on that project for 12 years?

RW: I reintroduced myself to my family. We took kids out of school and traveled around the world for a year. It was a great experience; we visited 32 countries. I had learned so much while traveling for business; I really hoped that the kids would pick up a more global perspective and realized how much is changing outside of the U.S.

Returning to Boston, I looked for new projects, especially one that could do something about pollution. I started looking into nuclear reactors, which are safer, cleaner, and cheaper.

So I co-founded Transatomic Power and helped to get it up and running. Eventually, it was clear that fellow co-founder Dr. Leslie Dewan was ideal to be the CEO, and I moved to the board.

Also, after coming back from our trip, I had begun to invest as an angel. I would only back founders who I thought were spectacular humans. One of the companies that I backed early on that has gone on to do well is Disruptor Beam.

UB: And now you are joining Pillar. What led to the move?

RW: I wasn’t sure I wanted to be an investor until Jamie reached out. I was really impressed by what he was building.

More than anything, Jamie is just the type of guy you want backing you. So that was a draw.

But, I was also attracted to the philosophy; especially, the vision of bringing up the next crop of startups in Boston, that resonated with me.

Pillar is all about becoming highly aligned with founders and entrepreneurs. From the beginning, Jamie built in this philosophy of having founder friendly term and always leaning towards what’s best for the founders. Having been on the other side, I realize how important that is.

UB: What has you most excited about this new role?

RW: I would like to see an impact in terms of bringing together the next generation of Boston startups, more pillar companies. We want to be involved in all of them, but it won’t be Pillar alone that does that.



This week, the company that isn’t getting the attention it should be was suggested by local VC Jeff Bussgang of Flybridge Capital Partners. The interesting thing is that the company he thinks is under-the-radar isn’t a Flybridge portfolio company.

Bussgang sent a note about Cognex, the Natick-based machine vision company that has been kicking around since 1981. The reason for Bussgang’s interest is that he thinks that Cognex is one of Boston’s hottest tech companies, and yet no one talks about them.

According to Cognex‘s website, they have shipped more than 1 million of their vision-based products, including barcode readers and other laser vision devices, which represents more than $4 billion in cumulative revenue since its founding.

While it is a great story about long-term value, Bussgang is right that the company is currently “hot.”

It now has a $7.3 billion market cap and its stock price has increased more than 125% over the past year.

The reason for the company’s sudden success is most likely due to the evolving demand for the automated manufacturing processes and the increased use of machine learning in an array of industries. The company is already working across the globe, using its machine vision readers to improve all parts of manufacturing and assembly. It is also being used by the automotive, solar, biotech and life sciences, electronics, and semiconductor industries for automation and product quality optimization.


What went down this week…

Drones – Brandon Tseng is a former Navy Seal who is a co-founder and the CFO of Shield AI, a company that has developed AI software for military purposes; specifically, for guiding reconnaissance drones during ground combat. Currently finishing up at the Harvard Business School, Tseng is leading the east coast arm of Shield AI, which just raised a $10.5 million Series A from Andreessen Horowitz.

  • With contracts already in place with the Department of Defense and the Department of Homeland Security, Shield AI has the potential to play a major role in reducing the number of US ground casualties in the theater of war, which is it’s primary, stated mission. While it has had a small presence in Allston, the company and Brandon will soon completely be headquartered in San Diego, where Brandon’s brother, CEO Ryan Tseng, and the majority of the team is located. The company was on the radar of a lot of VCs in Boston but ended up finding it was most aligned with a16z.


Player Personnel – I had the pleasure of working with Eric Trickett during my day’s at VentureFizz, where he was an advisor to the company through its sister business Dissero. Trickett, who was most recently the Head of Global Engineering Recruiting at TripAdvisor, just move to a role at Wayfair as the company’s Director of Talent Acquisition.

  • While I have stated that people moving from job to job isn’t really newsworthy, in this instance, it actually is and not just because Trickett is one of the best guys in Boston tech. From what I have heard, Trickett played a vital role in TripAdvisor’s growth over the past year as it expanded into its new campus in Needham. More than that, word was that Trickett quickly became one of CEO Stephen Kaufer’s most trusted advisors. The reason for that has a lot to do with Trickett’s track record with high-level hiring and talent placement, something that many companies screw up often, sometimes with disastrous results. The move to Wayfair is an indication of two things: One, that Tripadvisor is now in a great place with its leadership going forward and that Trickett’s expertise is no longer needed; and, second, that Wayfair is about to grow exponentially.

CarGurus follows the plan…the TripAdvisor plan

Choose Industry. Build Product. Grow. Exit. Repeat.

It was reported this week that CarGurus, the online car shopping platform, has selected banks in preparation for an IPO at some point in 2017.

CarGurus is one of Boston’s most successful private consumer internet companies, and yet, it fails to garner the same attention as some of the area’s very early-stage startups. One reason for that may be that it never took funding from a venture firm, and therefore doesn’t have a need to send signals to the “market” about how much it is “crushing” it.

Nevertheless, CarGurus should have everyone’s full attention now. In searching for a takeaway, startup founders and executive teams shouldn’t be asking “How the hell did they bootstrap and pull this off,” when it comes to CarGurus, but “How can WE do this too.”

Well, there is a playbook, and it’s not that hard to find.

CarGurus has never had to deal with pressure from VCs. That’s due to the plan of founder and CEO Langley Steinert and his leadership team who emphasized a focus on…wait for it…profitability, above all else.

But that isn’t what ultimately led to the success of the business.

No, the key to CarGurus ten-year march to an IPO is that all-along, the company just mimicked TripAdvisor.

A couple of years ago I interviewed Sam Zales, CarGurus’ president of international and dealer operations, and he was very explicit about how Steinert, who was a co-founder of TripAdvisor (one of the highest-valued Internet companies in the US), was specifically trying to follow what he called the “TripAdvisor model” with CarGurus.

TripAdvisor, you see, not only figured out how to best mix business-generated content with consumer voices, but they created a trustworthy brand on an international scale at the same time.

As Zales explained at the time, “The foundation of [CarGurus] was replicating an incredibly successful model for the consumer around creating transparency, relevancy, and quality…doing the same thing done with travel search to the car buying experience.”

If you think that this is simple, it is not. The execution thus far for CarGurus has been impeccable.

Also, if you are wondering why more companies don’t just apply an existing business model to a different industry, know that they have, and, for the most part, they too have been successful.

Take for example David Blundin, of Link Ventures/Cogo Labs. Blundin, you see had a few VERY successful startup exits before founding CourseAdvisor, which was acquired by The Washington Post in 2007. The thing about CourseAdvisor is that, beyond just its name, the company owed an enormous debt to TripAdvisor. With Cogo Labs, Blundin took what he learned about TripAdvisor’s search engine optimization mastery and spun into businesses in an array of different industries.

That plan worked masterfully with CourseAdvisor, so then Blundin and a cohort of executives figured out the process and replicated the same model again and again, including in the car shopping space with Autotegrity, which sold to ADP. Since, they’ve applied their model and learning to companies like EverQuote, which just raised $17 million.

Blundin and Steinert aren’t alone, mind you. Finding a model that has worked, making a small tweak, and replicating, has been done to great effect by folks like Chris Lynch, Rodney Brooks, Walt Doyle, Paul English, Helen Greiner, and many others.

So, the lesson for anyone looking to build a startup — or to do anything creative or innovative for that matter — is a truth known by everyone from Shakespeare to Quentin Tarantino: Copy from the greats that came before you, but make it your own.

For CarGurus, following that strategy is about to pay off handsomely.



Ash Egan, Principal at Converge Venture Partners, couldn’t pick just one company in his firm’s portfolio that isn’t getting the attention that it should, he mentioned three: Nift, RocketVisor, and

RocketVisor seems like a company out of the Drift/InsightSquared mold that could become an integral service to a specific niche of the business world. In RocketVisor’s case, it has a chance to evolve the sales process by integrating machine learning capabilities.

But there is something truly intriguing about Mainly, the company is looking to make headway in the very underserved construction technology space. combines photo and video with machine learning to assess for “industrial-grade problems” to do everything from making sure a worksite is safe to evaluating the progress of a project.

Founder and CEO Josh Kanner has an excellent construction tech track record, having led Vela Systems to an acquisition by Autodesk in 2012. Something that also bodes well for


What went down this week…

AI Maven- A few weeks ago, we talked about Talla’s tourney add-on for Slack. It was a cool feature that aligned perfectly with the company founder’s love for hoops. Since, both Talla and CEO Rob May have been on fire. First and foremost, Talla has expanded beyond being primarily an AI solution for Slack with its new integration for Microsoft Teams. Beyond his own company, May is stepping into a role as the leading voice on everything artificial intelligence related.

  • May is a tour-de-force in Boston, as an AI thought leader as well as an investor. But take note of how much more prominent May is becoming in the national discussion of AI. First, May is quoted at length in a recent Xconomy story about DataRobot’s recent $54 million fundraise…a company with which he has no affiliation. Second, May’s weekly AI newsletter, Technically Sentient — which was picked up as part of Jason Calacanis’s constellation of Inside newsletters — is truly a must-read. This week, May’s commentary in Technically Sentient is fantastic: “One of the big arguments in A.I. is whether or not we need to understand the brain to build intelligent, self-aware machines,” he begins as he delves into what the endgame for autonomous vehicles might be. His closing point is great: “…if humans and our environment, at least, the part of the environment that requires intelligence, have co-evolved – if the environment is largely designed by us – then the right way to build an intelligent machine for that environment may be to copy humans. Otherwise, by providing an open-ended highly flexible intelligence to run in that environment, we may never be able to test all the possible edge cases to our level of satisfaction. Getting that last 2% of autonomous vehicles could be harder than we think.”

TV Future – This week, Clypd‘s VP of strategic development Jason Burke published an entertaining outlook for what he believes the next ten year’s or so will look like in the television/Internet media industry. Before diving into that, I need to do a major Utterly Biased statement of biases on this one here: So, I’ve known Jason for a loooong time…like baby pictures together, crushing Miller Lite’s at age 13, getting kicked out of Fenway as adults type of history. So, I’m going to break down the good and the bad of this prognostication while being as fair as possible.

  • Overall, this is a cool what-if examination of the media landscape, both as it exists and where it will be. Clypd (pictured above) is in a good position to make some of these assessments as their insights. As a leader in bringing Internet-style, on-demand targeted marketing to TV, they know what is happening at the crossroads of the Internet and television better than anyone. However, some of these predictions are hopeful and don’t do enough to dig into some of the more important questions, like whether or not we will have TVs strapped to our faces in a few years. And while no one knows what might happen with Netflix, which Jason says will be part of the Verizon stable soon, I would imagine that the company aspires to be acquired by someone bigger (and with a greater legacy) than Verizon.


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Investing in a few key startups alone won’t save struggling American cities

Beyond Boston

Earlier this week, it was announced that Steve Case, AOL founder and chairman and CEO of Revolution LLC, would be bringing JD Vance into Revolution in a special role.

Vance, a principal at Mithril Capital Management, is best known as the author of Hillbilly Elegy, a highly-regarded account of life growing up in the Rust Belt.

The move to add Vance, who will reportedly “focus on the firm’s initiative to identify and back infant companies in cities far from the tech capital of Silicon Valley,” aligns with Case’s current thesis about where innovation can be found. Basically, Case believes that the non-traditional tech towns —Detroit, Cleveland, etc. — are where the most impactful next generation companies will be found; this is something he touches on in all his public appearances as well as in his book, The Third Wave.

Supporting non-traditional tech centers can have two outcomes. One, an investor could find the proverbial “diamond in the rough” startup that has less overhead and greater long-term potential — think Shinola in Detroit (image above) or Zappos in Las Vegas. Second, is the other, more meaningful impact that supporting startups in places like St. Louis, Austin, Milwaukee, and others, could have.

The reason Vance’s book has garnered so much attention has been the focus, after the election of Donald Trump, on how to support these struggling — and often ignored — working class communities across America. People like Steve Case and others believe investing in a few companies in these cities could turn around the downward spiral caused by the loss of manufacturing jobs.

Well that is all well in good in theory, the reality is a bit more nuanced.

If the focus is on building more startup-centric communities, investment in the top tier companies in these locales sounds like a positive shift, but from folks I’ve talked to who are working on projects to support entrepreneurship outside of New York, Boston, and Silicon Valley, that approach is a bit short-sighted. While finding — and supporting — a few winners in places like Baltimore and Cleveland could start a chain-reaction of innovation, the argument is that to create more employment and more opportunities in these developing clusters it takes a wider community of startups.

Which is why CIC St. Louis and whatever new initiatives MassChallenge is quietly undertaking could be better and more meaningful in the long run to helping solve the issues Case and Vance seem to be targeting.

Arguments have been made that it is not worthwhile to build a company outside of Silicon Valley (and New York/Boston to a lesser degree). This argument is built off the idea that only established tech and innovation clusters can be beneficial to founders and growing companies. Which is exactly why Tim Rowe’s CIC expansion and Scott Bailey’s stealthy work to grow MassChallenge’s programs in North America are so necessary. It will not be by the establishment of “pillar” companies alone that will make or break the next wave of growth in non-traditional innovation centers, but by the creation of thriving and supportive communities.

Beyond programs and investment, another opportunity rests with the initiative of a few individuals to bring what I’ll call “grassroots” innovation community building to non-traditional areas. A great example of this would be what the former leadership of Dyn, and, more specifically, what Jeremy Hitchcock and Grey Chynoweth are trying to do to support entrepreneurship in Manchester.

Closer to Boston, another example of this is Ben Pleat, a Harvard student and the founder of a community building startup Doorbell, wrote a long treatise about why he is working with Worcester to jointly test his company’s product and support innovation as that city tries to shift from its working class roots to a more innovation-fueled economy.

As Pleat puts it, “Worcester presents not only an exciting city expansion for our real estate technology startup based in Boston, but also an opportunity to work directly with some of the largest stakeholders in the city’s urban revitalization initiative, ranging from local business owners to energized political leaders looking to transform the Downtown landscape.”

The success of all these initiatives is vital to the continued growth of the US economy, especially in the Rust Belt and former manufacturing centers. However, there are two competing lines of reason on how to do that. There is the Steve Case model of investing in a few potential winners and hoping that there is a trickle down effect. Or, there is the community building and municipal partnership approach that the CIC, MassChallenge, and others are taking.

After observing both the CIC and MassChallenge‘s impact on Boston as well as the potential that individuals can have to make change on a city-wide scale, I’m not so sure if the “spray and pray” method favored by investors is the best way to impact change where it is most needed.



This week, I reached out to Peter Boyce II, VC at General Catalyst and the co-founder of Rough Draft Ventures to find out who he thought wasn’t getting enough love.

The company he pointed me to is LogRocket, a “customer experience platform that helps companies build better online experiences for their users.”

Co-founded by recent MIT and Columbia graduates, LogRocket enables development teams to playback user sessions to identify any issues and bugs that are causing problems with applications.

“They’re testament to what talented young technical founders can build here in Boston as a solution for enterprises and SMBs,” Boyce said. “They are focused on product and helping more of their community go deeper in understanding how UX and software decisions influence impact their businesses.”

All the while, Boyce added, LogRocket is “Quietly learning and building.”


What went down this week…

Bi-Coastal – Matt Brand is one of the top startup tech guys in Boston. After making his bones at Tabblo, the photo printing company founded by Antonio Rodriguez and acquired by HP, he has gone on to play an integral role in various other local startups. Most notably, he was the tech head (and often the lone leadership in Matt Lauzon’s absence) for Dunwello. Now, Brand has a new gig as the CTO of MoveWith, an active lifestyle application that is based in Boston and San Francisco.

  • According to Brand, MoveWith recently launched audio classes in addition to its in person classes in Boston and San Francisco. “Teachers love it because it allows them to spread their brand and skills far beyond their physical studios while still being able to offer in person classes and connect with their students,” Brand said. “And the rest of us get a way to workout how/when/where we want with great teachers from all over the place.”From what I gathered, Brand is really enjoying his new gig. “What I think is cool and different from a lot of the other players in the space,” he said, “is that we’re not just yoga or just meditation or just running.”

Heard of these companies?


The Quiet

Each week, I like to feature one company that a local VC feels is not getting enough attention. This week, we’ll take a break from digging into the Boston venture capital portfolios and check out a few companies that you should be hearing a lot more about, but haven’t yet.

The way I see it, some of these companies could be the next major employers in Boston. A couple even have raised money far greater than some of the startups that seem to draw outsized attention from the local media (cough, cough…food delivery companies and social media add-ons).

GreatHorn – Headquartered on a nondescript side street in Belmont, GreatHorn deserves to be mentioned among the other top emerging cybersecurity startups in Boston.

The company has raised $2.25 million from the likes of ff Venture Capital, SoftTech VC, RRE Ventures, Techstars Ventures, Zelkova Ventures, V1.VC, and Walter Winshall.

I sat down recently with CEO Kevin O’Brien, who has worked for Contact Networks (acquired by Thomson Reuters), Cloudlock, and Conjur, among others.

O’Brien sees an enormous opportunity to combine AI and human oversight to the growing susceptibility of the cloud communication and collaboration spaces. For O’Brien, the greatest threats for breaches rest in the third part apps, add-ons, and other potential loopholes with services like Slack and cloud document sharing and collaboration programs.

Examity – A Boston edtech startup raised $21 million recently. And, you’ve probably never heard of them. And you might have a hard time finding them as well.

Examity is based above a bank (“You have to walk through the ATM to get to the office, which is kind of cool,” CEO Michael London told me) by the MBTA station in downtown Natick.

While it is not being run out of some “hot” Boston property, the company is on the cusp of making waves in the test-taking and online education spaces on a global level.

As London explained, the company offers a full complement of processes to identify and verify people taking tests online. Whereas the rest of the industry focuses on singular methods, for the most part, Examity offers clients a full suite of ways to confirm the identities of online test takers.

While many college online education programs and skill assessment clients are using Examity, London believes they are just dipping their toe in the water for what has the potential to be a truly massive space as more tests, including college entrance exams one day, come online.

NewStore – There were two Boston companies named on a recent Bloomberg list of the “50 Most Promising Startups You’ve Never Heard Of.” One was Accion Systems, the space propulsion company started at MIT. The other…NewStore.


NewStore, started by Demandware founder Stephen Schambach, raised $38 million in funding in a single round led by General Catalyst when it launched in 2015.

A mobile retail platform, NewStore works for a wide array of luxury and big name brands to help them stay ahead of technology and social trends and reach more potential retail customers. Instead of using multiple services, NewStore has an all-in-one solution to acquire and sell to mobile users.

The company says it employs more than 140 currently, but should continue to grow massively, and, most likely, quietly, as its mobile shopping solutions gain further market traction.

Parlor Skis – With the season winding down, you might think this is a bad time for a New England-based custom ski maker. Not so, says Parlor CEO Mark Wallace.

You see, not only does Parlor have a ton of orders for its skis for next season to fulfill, it is also offering unique DIY opportunities for those who really want to get involved in the building process.

From April to August, the company will be holding custom ski making classes where attendees will make their own new skis start to finish. It’s a pretty cool way for the company to keep momentum going at a time when things can tend to lag.

But be aware, spaces fill up and Parlor has already quite a few people who’ve made deposits to build a pair this summer.

Know of more under-covered companies in Boston? Send a note my way at



What went down this week…

A Hard $4M – Just one quick note as VentureApp, the company started by two groups of young entrepreneurs who had exits with their previous companies, announced that it had closed a $4 million round of funding earlier this week.

  • There are a lot of peeps with some startup experience involved in the company started when UMass/Amherst guys Boris Revsin and Jared Stenquist, co-founders of DailyBreak (which had some sort of strategic partnership/acquisition from Connelly Partners) joined forces with the founding team from Bostinno/Streetwise Media including Chase Garbarino, Kevin McCarthy, and Greg Gomer (who all had an exit when the American City Business Journals bought Streetwise). Recently, Chase Garbarino told me that raising this round was one of the most difficult challenges he has faced as an entrepreneur. The outcome: He managed to get Boston Seed onboard, as well as Ryan Moore from Accomplice, whose office the company had been working out of while getting off the ground. The other investor? FullStack Ventures, the fund started by…Revsin, Stenquist, Garbarino, and Gomer.


Utterly not related, but a must watch nonetheless

“Do What You Love?” The advice has become so ubiquitous and overused that it is now the tagline for a company that has raised almost $6 billion in funding in WeWork. Although very motivational, the saying is getting a bit tired.

Well, this guy here, John Shocklee, is actually the living embodiment of “Doing What You Love.” It’s messy and not always glamorous, but if you can find something you love as much as this guy loves touring people in the Rockies, you’re onto something. Watch for the quirky story, enjoy for the breathtaking images.

  • The passion quote: “Money doesn’t matter to me, never has. It’s not that I’m rich, I didn’t come from money, I still don’t have money.” Shocklee, a 52-year-old ski guide from Colorado says after a tour of his one room abode.

Age versus Experience

Age Ain’t Nothing but a Number…

The two companies in the national spotlight the last couple of weeks, Snap (aka Snapchat) and Uber have some things in common. Chief among them has been a constant questioning of whether or not their leadership is qualified to run what could be Fortune 500 companies.

Both have faced calls to add “experienced executives,” insider parlance for adult supervision. Both have seen execs come in for short spells before departing. This has also happened to company’s such as Twitter, as well.

The problem in many of these instances is usually viewed from the outside as an issue of age difference. You hear this sometimes from people who either make a bad hire, and try to excuse it, or from those who move from a corporate or established entity to a hot young startup.

But there is something a bit more complex going on here. And so I spoke with a bunch of CEOs who are on the young side, younger than 35, to dig into how they’ve felt in these situations.

Most admitted that figuring out how to work with older more experienced employees had less to do with a difference in age than it does with a gulf between the experiences of CEOs and their charges. And there seems to be no way to avoid this very challenging part of running a startup.

Whether it is a VP or C-level employee hired to help in a new stage of growth for a venture or whether it is someone put in place by a board of directors or VC, this seems to always be a thorny situation.

As VentureApp CEO Chase Garbarino described it, “I fucked this up multiple times.” And he’s not alone. Almost everyone I spoke with said some version of the same thing.

One reason, as Garbarino explained it is that hires who typically come from corporate world don’t realize that the title they hold in their former established companies is not comparable to what might be described as the same role in a startup.

And this can cause confusion for both a young CEO or an experienced new hire. As Garbarino described it, “The CEOs don’t understand from day to day what they want and what this person has been doing.”

Tom Coburn, CEO of Jebbit, says one of the issues between young founders and experienced execs working together can be cultural. As his company has grown, he said he’s made some mistakes but learned from them to change how the company works.

An Coburn knows well how a vast cultural difference can slow a company. In its early days, the entire Jebbit team, all in their early twenties, lived in a single house together. When they made a few older hires as they grew, they made mistakes they didn’t even realize Coburn said. “We’d work all day and then go home, have a beer, and then start talking strategy again to late in the night,” he explained. “We would make key decisions.”

Later, another member of the team who didn’t live in the house pointed out how that type of operation could lead to issues. Some folks who were supposed to be key stakeholders, but who might have other responsibilities (part-time jobs, families) felt left out of process and started to get upset. “They were right,” Coburn said, “we just didn’t realize the impact of the way we were working together at the house.”

So Coburn made changes. The only time they have tactical meetings is at 4:00. No more decisions made in casual environments. There had to be a strict separation of home and work.

This can be hard for young founders for other reasons. As Drizly CEO Nick Rellas told me, “When you are 23 or 24, you want everyone to be your friend. It takes time to realize that you need to be the steward of the business and what it means to be the boss.”

“I had to figure out how to be an asshole,” Rellas added. “But I wasn’t ready for that at first.”

“People don’t want to talk about this because it’s sensitive,” Chase Garbarino told me. “The difference in culture thing is real even if people don’t want to talk about it.”

As Garbarino explained, he feels like, after having run Bostinno/Streetwise Media and now VentureApp, he’s had the experience of being the young CEO and now has a bit more experience to avoid some earlier mistakes.

He’s 32. And has already built two companies, raise venture funding, and sold Streetwise. Experience is the key, and only comes with time, whether that be 10 years in business or 25.

Boston’s younger CEOs will continue to screw up. But, they are getting older and wiser. Should be fun to continue watching their development.


Who is under-the-radar?

In this week’s under-the-radar, we dig into a company that is under-the-radar from a VC firm that has been under covered as well.

I recently sat down with Vivjan Mytro of Hyperplane VC, who is leading one of the next generation VC firms in town. Hyperplane is involved in some major deals in Boston that are heavy on tech and long on potential impact including Talla, Indico, TellusLabs, and the previously mentioned Vesper, among others.

According to Mytro, the company in Hyperplane’s portfolio that is not getting enough attention is Volta Networks.

The reason? It might be that Volta, officially a “Routing-as-a-Service” platform for the cloud, is an old school-type of Boston tech company. What that boils down to is that its tech is complex — bringing routing to the cloud and distributing routing intelligence between processes — in a way that could improve networks and infrastructure for the booming spaces of machine learning, the Internet of Things, and sensors.

“These guys have had some major validation recently from their big customers,” Mytro said. “This could be pretty revolutionary.”


In it’s eleventh year, TUGG’s annual celebration, TUGG Makes Boston (FKA the TUGG Wine and Tequila Party) presents the best opportunity to meet all the people who are pulling Boston to the forefront of tech and innovation. More than that, it is the best chance to support the local non-profits working with those in the community most in need of help, support, and access to more opportunities.

Read more here…


What went down this week…

An Odd $100M – That’s the new amount of funding DraftKings announced this week. It’s a bit of an odd move, as many have pointed out, coming as the company is expected to merge with former rival FanDuel.

  • The best reasoning behind this new funding comes from Dan Primackwho seems to know everything about DK, including the weekly lunch schedule and the password for the bathroom. You can check out Primack’s take at Axios, but his reasoning, that FanDuel is raising the same amount of funding as well and both rounds are meant to buffer the companies if for some time if anything goes sour with the proposed merger.

Madness – I’m convinced Rob May doesn’t sleep. The Talla CEO and local AI guru is at it again, leveraging Talla’s technology to help Slack users keep track of the NCAA brackets this year.

  • All this is in addition to running the great AI newsletter, Technically Sentient and serving as a venture partner at Pillar. Methinks that the Talla Bracketbot pet project serves a dual purpose: Getting Talla’s great Slack capabilities out there to the general public, and allow May and co. work on something close to the heart with the hoops tourney. You see, May, originally from the Bluegrass State, is a hardcore Kentucky Wildcat fan. I wonder who he had going all the way this year?

Let’s Get Fired Up About Coverage – So Veracode is being acquired for a reported $600M by CA. While not in the stratosphere of the Dell/EMC deal, it is a major merger and a win for the Boston technology community. Other than some of the IPOs over the past few years, it is one of the largest liquidity events.

  • And yet, The Boston Globe throws a sliver of coverage, from its device expert no less, at this news. And you’d be hard pressed to find other coverage out there about this as well. Veracode is one of the better homegrown startup stories, having been started inside the old Atlas Venture and led by Jeff Fagnan and Maria Cirino of .406 Ventures, who once served as Veracode’s CEO for a spell. (The image above is one that hangs up in Accomplice’s office and was included in a piece Fagnan wrote after the acquisition was announced…CEO Bob Brennan is in the middle with Cirino to the far left and Fagnan to the far right.) This isn’t the only news that has been neglected this week. There is news from Vaxess Technologies, Examity, NewStore, Digital Alloys, that just don’t seem to be important to some and yet could all be major employers in the area for years to come. Just saying…


Utterly not related, but a must read nonetheless

If you have some time, check out the profile of Jack White in The New Yorker: “Jack White’s Infinite Imagination.”

  • The money quote: “Pushing myself into corners, identifying with the underdog, becoming the over-dog, being punished for that, retreating, advancing, learning to live in modern times, all the while creating at every turn. That’s the life path I chose long ago, and I couldn’t derail myself now if I wanted to.”


Utterly shameless self-promotion

Please, lease share the Utterly Biased sign up, which can be found here.

As I continue to build out the strategy for this thing, many have asked what the goal is. Well you know the scene at the end of “The Departed” when Marky Mark shows up and surprises smug, “I-got-away-with-it” Matt Damon. As I see it, Silicon Valley is Matt Damon and Boston is Wahlburg. So, I’m here so that everyone doesn’t end up too surprised when things flip.

Send any tips to

And any other feedback you may have, don’t hesitate to send my way as well.


Screwed the pooch

There were some doozies last week.

The major mistake was splitting the credit and confusing two Harvard biz scholars. Clayton Christensen wrote the Innovator’s Dilemma, while Noam Wasserman wrote the Founder’s Dilemma. My B.

Also, here’s a link to the paper that features Nick Ducoff and Northeastern.

Snap, Pop, Next…KB is an Inspiration and a Badass

Snap, Pop…and Then?

Snap, Inc., the parent company of Snapchat, went public this week. Opening at $24 (initially priced at $17) it has continued to rise to $27.01. There are quite a few takes being thrown out there relating to Snap’s debut on the public market.

Like the one that examines the interest from millenials looking to get a piece of the company that they perceive as their version of Facebook.

While that’s cute, not everyone is so keen on the future prospect of actual stock on the public market.

But one thing is clear, a lot of the optimism surrounding the Snap IPO is that, FINALLY, a high-potential private tech company has decided to test the public market. As I said before, this could be a major signal for companies who have been waiting on the sideline to jump into the IPO game.

I reached out to Maia Heymann, General Partner at Converge Venture Partners, to get her take on the potential opening of the IPO window following Snap’s pop.

Her response is great:

  • “I can’t predict the public markets or the buy-side’s receptivity to IPOs after Snap, but I sure hope the window stays open so that more tech companies can access the public markets. We need more tech companies to get public, grow into bigger companies, and keep the industry strong and diversified. If you end-up only having a few large trees in the forest, and too many saplings are bought-up, it ends up not being a forest anymore, and those few big trees cast a shadow that prevents new growth. The tech industry is getting that way. We’ve largely lost that mid-tier of mid-cap tech companies, who were buyers of smaller companies.  We’ve gone from about 8,000 publicly traded companies in the U.S. in 1996 down to around 4,000 in 2016. When investment banks couldn’t publish research on the companies they took public (circa 2003), that was the huge blow. It’s not SOX compliance, or the cost of being a public company that keeps companies from going public. It’s the lack of research coverage on new tech companies; no coverage, no float; no float, no buyers (of the stock). Who wants to go public only to be an orphaned stock. If smaller tech companies could access the public markets, they would. The loss of mid-tier investment banks who could cover smaller tech companies, published research, and provided coverage and analysis on a mid-cap tech stock post IPO, has hurt. I’ve always maintained that the loss of the boutique investment banks devoted to tech—the Four Horsemen: Robertson Stephens, Hambrecht & Quist, Montgomery, and Alex Brown—has dampened the IPO window for tech stocks more than any SOX ever did.”

That’s some great insight, especially the lesser discussed issues that have slowed both the IPO and M&A markets. It does really feel like more and more, companies, Snap included, are hitting the market with a lot of uncertainty.

Hopefully, whichever way Snap goes, some other tech companies on better standing (like say, being profitable) will hit the market soon to build more confidence to go public.


Who is under-the-radar?

According to Eric Paley, the most under the radar company in Founder Collective’s portfolio is BookBub.
Paley says that BookBub — which has raised $10.8 million in funding —  gets about 10 million daily users. That makes it one of the largest independent eBook sales platforms on the web, but it still doesn’t seem to get as much attention as others in the online publishing space.

He didn’t dive into the reasons why BookBub wasn’t more in the spotlight, but you don’t have to read Inside Book Publishing to know that there is one MAJOR reason why you don’t hear much about the company, and that is Amazon.

One major threat to BookBub’s success has been the launch of Amazon, the clear eBook leader, and its Prime Reading product. Prime Reading aims to serve as a launchpad for lesser known authors, which has been a major draw for BookBub.

But BookBub does have some advantages, its model is cheaper, for one. Also, it has a bit more of an independent book store culture and brand. If you can believe that such a thing could exist on the Internet, BookBub is the indie neighborhood book shop to the corporate Amazon. This attracts a niche of authors working in outlier genres that seem to get lost in the colossus that is Amazon.

Brit+Co. has called the company the “Kayak for eBooks,” and the “interweb’s best open secret on where to score books for a fraction of the cost.” With growing readership and the type of indie cred that can’t be drummed up by a marketing team, expect BookBub to gain more and more accolades and users. Oh, yeah, and more profit and funding as well.


What went down this week…

HubSpot’s Katie Burke, the company’s Chief People Officer, published a blog post on Medium this week that is a must read. I shared “Because I’m a Girl,” on a couple social media platforms and got more feedback from folks outside of my “tech/startup” circle, to use the old Google+ nomenclature, than anything I’ve ever posted. I also got calls from my sisters who were fired up by Burke’s message.

  • Burke’s post struck a nerve. While having her qualifications questioned because she is a woman is the impetus for this piece, there isn’t likely anyone in Boston, or beyond, who has the legit experience that Burke does. Not only did she play an integral role in keeping HubSpot culturally grounded during its IPO, but she was key in weathering the PR nightmare the company faced last summer with the Dan Lyons thing. While it totally sucks that someone is so blind to the work done by Burke to question her in this manner, it did push her to create this rallying cry of a blog post. And, I believe, it definitely empowered more than a few women in the workplace.

NU – Nick Ducoff and the work he is doing at Northeastern with the Level Analytics Bootcamp. Level got some praise from none other than the original Innovator’s Dilemma scribe Clayton Christensen, who said of Ducoff and the program in a recent paper on higher education innovation, “Leaders looking to build disruptive models under the traditional university umbrella can take a page from Ducoff’s book.”

  • Why this is good? While Harvard and MIT tend to pump out the most innovative thinkers and business leaders, it is vital that the other institutions in town push the two so that they don’t become complacent. Ducoff’s work at Northeastern, the job William Brah has done at UMass-Boston, Debi Kleiman’s work at Babson, and John Gallaugher’s impressive innovation leadership at BC have made an impact in the number of young startups popping up all over Boston. With Harvard’s i-lab (totally biased), the Rock Center at HBS, the MIT Media Lab, and the recently announced The Engine, expect a boom in the next few year’s in student-started companies coming out of Boston. Boston VCs, if they are paying attention, have a more innovation potential within a short drive than almost anywhere in the country.

M&A – Word is that there is at least one MAJOR move happening in the next couple of weeks with a well-known Boston company. The question is will they be the acquired or the acquirer?

The Anti-Travis, Nasuni and EverQuote, Next Move NextView

The Anti-Travis Kalanick

This has been a very, very bad week for Uber.

One of the most valuable private companies in the world, Uber was the focus of a blog post earlier in the week from a former engineer, which describes a culture of rampant sexism within the company. If that wasn’t enough, it was revealed later in the week that Uber is now the target of an IP lawsuit about self-driving trucks from one of its biggest investors, Google/Alphabet.

The eye of any Uber hurricane seems to always center on its CEO Travis Kalanick. Some believe that his bullish attitude has run its course. Exemplified by comments like, “Stand by your principles and be comfortable with confrontation. So few people are, so when the people with the red tape come, it becomes a negotiation,” Kalanick doesn’t shy away from controversy. But that approach doesn’t seem to be working anymore. Some are even saying it’s time for him to step down.

Take the constant swirl of trouble that seems to follow Kalanick and compare it to the how one local CEO — whose company is also pushing up against powerful industry incumbents and government regulations — has handled himself in the face of adversity. If you will, compare Kalanick’s approach to that of DraftKings CEO Jason Robins.

While DraftKings has faced a fair amount of criticism, I cannot think of a single instance of Robins leadership being called into question.

Word is that the culture inside DraftKings is intense, but I’ve yet to hear murmurs of anything like the widespread issues that are currently dogging Uber. Friends and investors have long praised Robins’ humbleness and his grace-under-fire during the most challenging days for DraftKings. And, while Uber and Lyft are undertaking a seemingly never-ending battle to the death, Robins (at least publicly) never attacked DraftKings competitor FanDuel. In fact, from what I’ve heard, Robins and FanDuel chief executive Nigel Eccles worked closely together, pushing for the companies to combine.The merger, currently in process, is something that would never happen with Lyft and Uber for an array of reasons.

While it’s possible there is another side of Robins that doesn’t match his public persona, I find that highly unlikely from my own interactions with him.

With all the negative focus raining down on Uber, which doesn’t seem to be going away time soon, it’s nice to have an anti-Kalanick in the world. And it’s also a good thing for the future of DraftKings/FanDuel and Boston.


Who is under-the-radar?

Jeff Bussgang, general partner at Flybridge Venture Partners, points to cloud-storage company Nasuni, as one of the companies in Flybridge’s portfolio that isn’t garnering the attention that it should.Based not too far from Utterly Biased headquarters in an office park hidden amongst the rolling malls of Natick, Nasuni combines virtual and on-premises storage controllers with cloud storage for enterprises. As Bussgang describes it, the company is “Revolutionizing cloud storage.”

“Not sure why they’ve been under-the-radar,” Bussgang said. “But no one talks about them and they’re doing great and building a big company.”

Nasuni is an interesting company for a number of reasons. Its founder and CEO is Andres Rodriguez, who was a founder and the CTO of Archivas, an enterprise cloud storage company acquired by Hitachi Data Systems in 2006. Rodriguez was also once the CTO of the New York Times, and just happens to be the big brother of Matrix’s Antonio Rodriguez.

He’s put together a solid squad of old school and new school cloud and storage folks, including Scott Dussault, who was the CFO of Demandware when it went public.

Elsewhere, I hear that the company is doing about $20 million in revenue, with a solid and consistent SaaS customer base. If I were a betting man, I’d say that in regards to Nasuni, Dussault might have to dust off his IPO playbook soon.


What went down this week…

The NewDrift just launched a new product, called LiveView which is a sales tool that can let you know who is on your website (including potential leads) in real time. Drift is probably the first company mentioned when you ask any insider in Boston which of the early-stage companies has the potential to be huge. This new product drop seems like a major step to achieving that success. Basically, the company is bringing the habits we use to communicate in our personal lives to our business dealings. But I’ll let Dave Gerhardt, the company’s head of marketing, explain:

  • “Basically it boils down to this: The tools that most businesses are using for sales and marketing are going to break. As consumers, we all expect answers in real-time. And if we don’t get them, we move on to the next product, the next business, etc. But then we go to our jobs and when it comes to sales and marketing, we do all of the things that drive us nuts as consumers: We force people to fill out long forms in order to contact sales, we put content behind lead forms because we only want “qualified” people to be able to access it, and then we chase people down via phone and email. But in our personal lives, we’re all using messaging to communicate with each other. So at Drift, we’re focused on changing the way sales and marketing work by helping them match the real-time behavior of buyers today. And that all starts with giving sales teams tools like Live View so they can see who’s live on their website and reach out in real-time — instead of waiting until someone submits a form only to follow up hours, days, or weeks later.”

$13 M – That’s the additional funding announced this week for EverQuote, the Cambridge/Woburn online insurance marketplace from SecondAlpha and Link Ventures, as well as Stratim Capital, Savano Capital Partners, Oceanic Partners, and T Capital Partners.

EverQuote could have been mentioned in the IPO window chat from last week’s newsletter, as it too has been talking about a potential initial public offering since 2015. The new funding is the last money in a round in which they had already raised $23 million.

By the numbers, EverQuote has over 5 million consumer visits per month according to data from October 2016. It also has 200 employees between its two offices and plans to add 80 more by the end of 2018.

Like Nasuni, EverQuote is an under-the-radar company that you will be hearing a lot more about in the coming year.

Name That Job – When NextView Ventures brought on Jay Acunzo as its head of platform, it was something different in the world of Boston VC. Since then, many other venture capital firms have added people to manage content and marketing, a position which has become known in some circles as the “Jay Acunzo Role.”

A recent blog post from NextView’s Rob Go shares the news that the original of the species, Acunzo himself, is moving into a different position in the firm, creative-in-residence, with Ginny Mineo taking over Jay’s role. The new position will allow Acunzo to focus on some of his other projects and will also see him working out of NextView’s NYC office.

  • I asked Acunzo about leaving a role he kind of made famous, and this is what he said, “All I’ll say is Ginny is gonna crush it running platform and I’m gonna crush it running the podcast and various creative experiments.” Modest as always. Good luck Jay.

Series A – There are at least two companies tied to Boston that have signed term sheets for Series A funding rounds that you’ll likely be hearing about in the next couple of weeks. Because the ink is still wet on these deals, names can’t be mentioned without potentially screwing up some of the last-minute deal refinement. But:

  • Some of the bigger names in VC are the leads, one East Coast, one West Coast.
  • One of the companies will soon be giving up its presence in Boston to consolidate at a central office that makes more strategic sense for its industry.
  • The founder of the other, someone who’s already achieved quite a bit of entrepreneurial success, told me it was the hardest process he or she has ever been through.


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The end of IPO limbo?

Snap Inc., set the price for its expected IPO this week — with a valuation in the range of $18 billion to $20 billion — and judging by how ALL the angles of it are being covered by media outlets from Variety to USA Today to the usual suspects like Fortune, ReCode, and TechCrunch, it is clear that everyone is fired up for a return to the days of yore when the companies everyone expected to go public actually did hit the NYSE and Nasdaq.

Since 2014, when Wayfair, HubSpot, and CyberArk locally, and Alibaba, among others, went public, there have been few IPOs, save for outliers like Rapid7, Acacia Communications, and Everbridge. Most of these have seen a rise in their initial stock price since going public. But the state of the market has left others weary of leaving the private market for the much more unstable public one.

Back in 2014, I remember clearly sitting across a far-too-large conference table with Tom Erickson, Acquia’s CEO. Erickson was fired up, we were at Acquia’s first major conference, taking place in Boston, and he was excited for 2015. Acquia had set its sights on an IPO, which Erickson felt was an inevitability, so much so that he had pushed hard for the company to join HubSpot and Wayfair in the late 2014 IPO surge.

A few years later, that still hasn’t happened.

Companies like Veracode, Acquia, Actifio, and Carbon Black (formerly Bit9) might feel compelled to join the IPO party again after sitting in the wings for years.Jeff Fagnan of Accomplice may have two portfolio companies go public if the window reopens. Veracode and Carbon Black, both under S-1s, and both have been mentioned as IPO candidates since 2014, When I asked him about missing an opportunity before, he acknowledge that, “Yes, it was probably a missed window.” But he added that, “Going public is just a stop and not the final destination though.”

That “stop” is a big one, however, and, as seen by the growth of all the companies that have gone public since 2014, having a successful public company can impact the entire market.

So let’s dust off the NYSE badges and get ready for some long awaited IPOs here in Boston post-Snap. They’ve been a long time coming.


Who is under-the-radar?

Speaking of Fagnan, I asked who in Accomplice’s portfolio was not getting the attention they should be. His answer, Hopper.

As he explained, Hopper is, “Absolutely on fire and will be one of the biggest consumer companies in Boston.”

Why does he feel that way? He told me that it’s the #2 downloaded travel app in the US with approximately 1 million downloads per month (half of them organic), that they have sold almost 100,000 airline tickets last month, and that Hopper will be adding three times as many people in Boston this year.

But Hopper is a known entity around here, already having raised $60 million.

So for a real under-the-radar company, let’s turn to Sarah Downey, Fagnan’s partner at Accomplice.

The company she likes in the portfolio? Acoustic sensor company Vesper.

“They are one of the most stealth companies in Boston, yet doing some of the craziest shit I’ve ever seen. The lab equipment in [at Vesper] alone is wild,” she said.

(If you know of a VC portfolio company that should be getting more attention, shoot a note to


What went down this week…

The One – The big news in Boston this week is Katie Rae taking over MIT’s The Engine fund (great profile from Scott Kirsner here). There has been almost universal praise for this move — truly, everyone I spoke with believes it is a win for Rae and a win for MIT. With the addition of Rae, MIT gains something it has been quite lacking for some time: A well-known and beloved figure with outstanding venture and accelerator chops, who excels at motivating and evangelizing for startups. For far-too-long, MIT’s quiet technological dominance has been overshadowed by Stanford’s more, shall we say “marketable” entities. This will help change that. The VCs, operators, and Techstars alums and mentors I spoke with raved about Rae. However there were one or two voices in the wilderness who wondered about Rae’s experience with the type of “tough tech” mentioned in The Engine’s announcements for this move. So I reached out to Katie, and here is what she said:

  • “The good news is that I will not be the only person at The Engine. I will build a team with deep understanding in specific areas of technology that we find interesting. At the heart of The Engine, we are investing into and helping entrepreneurs and there is lots of overlap no matter what area of technology you decide to tackle. People may not realize that as an investor at Techstars and Project 11 I have had a soft spot for tough tech as shown by investments in companies such as Neurala, NBD Nano, and Sandymount Technologies. I have lots to learn and an incredible network to help me learn faster.” Sounds like she’s ready for the mission.

C-Suite – As a bunch of outlets reported on Thursday, Dyn CEO Colin Doherty is taking the chief executive role at Cambridge-based Fuze, the cloud-based communications company that started life as Thinking Phones.

  • The coverage of this has been that Fuze is adding Doherty in anticipation of an IPO. Doherty (taking over from Steve Kokinos who is joining the board) JUST stepped in for Jeremy Hitchcock at Dyn and within a month had closed a sale to Oracle. While this is being sold as a final pre-IPO move, Doherty’s stints prior to Dyn include Arbor Networks (Acquired by NetScout in 2015), BTI Systems (Acquired by Juniper Systems in 2016), and Mangrove Systems (acquired by Carrier Access Corp. in 2007). That’s four acquisitions with a one sale per year streak for the past three years, which is quite impressive. There are all sorts of different types of CEOs, and Doherty seems like an “acquisition CEO” not an “IPO CEO.” That could change, and many folks I spoke with really expect an IPO, but I forsee Doherty’s acquisition streak staying alive in 2017.

$2.5 Million – That’s the funding number for Dave Balter’s Mylestone, which dropped the “d” from Mylestone(d) and made a shift in its product. The new investment was led by True Ventures, with involvement from initial backers Founder Collective, Boston Seed Capital, and Converge VP.

  • There are two ways to look at this news of Mylestone making another pivot, this time from a post-death digital remembrance product to an AI-powered digital memory application accessed through Amazon’s Alexa via voice command. One could say that its a bad sign that the company is making another drastic change in what it does, which is by my count the third such pivot. Or, this can be viewed as Balter and company taking all they’ve learned from their Mylestoned experiences to bring a complete vision of the original thesis behind the company to life. I bet on the latter. From what I’ve heard, the Mylestone team has been heads down and hard at work on this product for months. The Mylestone team are deadly serious about this new iteration, although Balter’s recent Startup Grind post might hint otherwise.


No names, just stories

There are plenty of local stories that don’t get talked about much, but should find the light of day.

First, many of the major so-called “secrets” of Boston tech aren’t very salacious. (At least the majority of them are not; we won’t dig into the nonsense people have done foolishly intermingling their personal and business lives, a good mirror does work enough.)

Second, there are some damn entertaining stories out there that feature the larger-than-life characters who helped build Boston into one of the world’s first hubs for technology as well as those developing the next generation of innovative companies.

We’ll be starting this feature next week, but, in the interim, send any good tales you have to


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