Three Thirty Five

I’ve spent some time here talking about just how lucky I am to be able to wake up every morning and go to work at a place where I’m continually inspired by the people I find myself working with and humbled by the mission we’re striving toward. Given the enviable position in which I find myself, in any given week I get a LOT of requests from people looking for career advice on how to break into to the tech ecosystem. And I’m generally happy to help, not least of which because I’ve been the beneficiary of advice, introductions and time from mentors in the past (that I’d note haven’t really had anything to gain by being helpful to me) that have really helped distill the processes I used myself when I was looking for the next step of my career.

Ultimately, this is a fairly simple exercise to help organize your thoughts, understand your own strengths and pursue the opportunities that are most meaningful and likely most lucrative to you. I’ve found that if you’re brutally honest in filling this out, it’ll open up a world of roles (and companies) that you’ve never thought of before, and also help lend some real focus to your efforts.

I’m pretty old school when it comes to process, so while you can whip up a google spreadsheet to do this, I’d really recommend you actually take a piece of paper and a pen and write this exercise out. (NB – this exercise probably isn’t as effective for recent grads as it is for someone that has a few years of work experience for the simple reason that without a few years under your belt, you likely won’t have the context to effectively complete this). (Charlie O’Donnell just put out a great exercise on formulating an idea which you can see here.)

Take your piece of paper and draw out four columns (A,B,C, and D)

A.) Column A’s title is going to be HARD SKILLS. A “hard skill” is something objective/quantifiable, a capability you have using a certain tool/skillset or specific set of experience you might have that adds to your profile as candidate. So, for example:

If you’re an engineer, these might include the languages in which you code and the level at which you can;
If you’re a former banker/consultant/boring, this likely includes Excel, Powerpoint, etc.;
If you’re a salesperson, it’s the processes you’ve developed, the relationships you bring to the table, and so on and so forth….

You should try to find at least 5 of these, and they should demonstrate a sense of self-awareness and excellence/achievement in each domain.

B.) Column B is comprised of your ESOTERIC SKILLS. Esoteric skills are the “soft skills” and things that make you, you. These include those descriptors you pepper your resume with, but that you can’t really measure, like: Leadership, Analytical, Self-Starter, Team Player, etc.

It’s always better to SHOW rather than TELL that these are actually true, so you also want to come up with at least ONE actual story to demonstrate how you’ve exhibited each of the characteristics you list here. That’ll be even more helpful when actually crafting your “story” in an email or interview.

C.) Column C is going to be the CHARACTERISTICS OF YOUR “PERFECT” ROLE. I broke the “core characteristics” of any job/company into a few categories below based on what mattered to me, but you can probably find a few more that make sense:

Minimum Salary you can live with:
Ideal team size:
Compensation structure: Equity/Salary/Bonus
How tied to your own performance do you want your compensation:
Do you want to be in a position to be mentored:
Do you want to be in a position to manage others:
What is the upward trajectory of the role (i.e. – what do you want to see in the next year, three years and five years from a comp, responsibility and growth perspective):
What is your downside threshold (i.e. – how much runway do you need to know the company has in months)?:
What kind of autonomy do you want in your role?
What kind of support/resources do you need in order to succeed in this role?
Do you want to have to meet new people in this role? Describe the “ideal culture” fit in five words:

Those are just a start, but I’ve found have a profound impact on the type of company at which you’ll fit (or need to fit) — including things like stage, type of role and type of company.

D.) Column D is going to be SECTORS of the economy that you find interesting. I break this into three sub categories: “Growth,” “Passion” and “Edge”.

Growth is a level of conviction you (or the market has) that this area of the world will grow at a pace that excites you and that is theoretically at multiples of the economy writ large.

Passion is the level of interest you have in the sector, and the missions therein. After all, this is an exercise in finding a career you love.

Edge is the unique viewpoint, set of skills and positioning you bring to the table. In areas of great technical complexity or regulatory hurdles, prior experience or advanced education can be a huge advantage that you work to yourself.

Whether you choose to do these as percentages or multiples — the triangulation of all three will give you an idea of where you have the biggest opportunity personally, and what you can begin attacking.

The first 3 columns should really serve to shed light on what type of job you want to be doing, and the kind of place at which you want to build a career. The third in particular will guide you toward a role and a stage of company that can meet your minimum requirements. The last is a tremendous way to galvanize your thinking and efforts around specific companies. And with more tools at your disposal than ever before (between Crunchbase, Mattermark, and Crunchbase, you’ll have pretty close to a 360 degree view of any market at its early stages), you’ll be able to attack the opportunities you’re most intersted in and that are theoretically the best fit. If you’re really a hustler, you’ll go beyond just job postings listed, find the decisionmaker, and be able to reach out to them to communicate all the reasons why you WANT to be there and all the value you WILL deliver.

I went to a very interesting event last night hosted by our friends at Microsoft in their shiny, new Lower Manhattan Headquarters (LMHQ) called Blockchain for Social Good (kudos to John Farmer for organizing). The discussion was led by Brian Forde, MIT Media Lab’s newly installed Director of Digital Currency. Brian made a number of very interesting, immediately digestible comments. If you get the opportunity to read his thoughts or hear him speak, I’d encourage taking it. Among the comments Brian made was what I’ll paraphrase as “the four steps of bitcoin/blockchain awareness”. These are:

  1. I’ve heard of it, but have no real idea what it is or how it works. If you find yourself in this camp, get moving. Blockchain is coming and it stands to disrupt all forms of transaction: financial, informational, contractual, etc. For a primer, I highly recommend reading/referencing Bitcoin for Beginners by GCT’s own
  2. I’m starting to get it, but am still a bit hazy. Welcome to the club. I’d argue that even the lion’s share of technologists fall in this camp. Seek out events. A problem I often see with tech that Brad Feld touched on in a previous post is a reluctance to admit even a whiff of ignorance. Despite massive and constant innovation, somehow we all have to be fully versed in everything. The truth, I fear, is we all have just gotten very good at appearing versed.
  3. Wow, I really am starting to get it; you could apply this technology any number of ways… I’m beginning to find myself in this camp and it really is thrilling. For fun, I’ll try out one of my concepts below. I’d love feedback.
  4. Full awareness = Nirvana. This is more or less a direct quote from Brian’s talk and apropos. May we all find full awareness of blockchain/bitcoin. Feels like a fortune cookie scrawl one might actually see within 5 years.

Before proceeding, here’s a brief definition of blockchain that I find helpful (big thanks to Kevin Beardsley of Elliptic for always helping to pierce the blockchain fog). The blockchain allows for the free and instant creation of an unlimited number of publicly verifiable, immutable and time-stamped tokens. The tokens can represent anything from a financial unit (e.g. a bitcoin or stock certificate), to a timestamped proof of creation (IP or identification of a new fact), to something as silly as “Fan” badges that can prove the provenance of one’s “fanhood”. Importantly, these tokens are independently verifiable (you don’t rely on Facebook or any third party to prove ownership), immutable (no fakes, no copies), and time stamped.

For a hyper-practical example, think of resale markets for concert tickets. We’re all nervous to buy them on Craigslist because, how do we know if they’re real? And even if they are, maybe the seller sold them to five different people and whoever scans first, “wins”. Blockchain technology could force that uncertainty onto a system where the ticket is 100% verified before being listed and can only be sold once. In such a world, I wonder how StubHub and SeatGeek – who charge very high fees in large part to provide verification – will respond.

But there’s a broader notion I’ve had for blockchain that, were it to come to pass, could actually begin to reshape some of the machinery of modern society: blockchain could rewrite the rules for incentivization and acknowledgment (implicit in incentivization) of discovery. This ranges from citizen journalism, to academia, to pop culture, and beyond.

For instance, what if the Associated Press creates its own blockchain? In such a case it might be possible to incentivize intrepid citizen journalists to “own” a scoop by registering it on said blockchain. Were a compensation structure attached to such a blockchain, the citizen reporter could go along for the ride as a story picks up steam and benefit financially from their discovery. If the boom in startups has proven anything, it’s that the Millennial generation wants a stake in the upside of their work. If blockchains can provide this, then people need not necessarily begin their own companies (this may be happening a bit too much) in order to own and profit from their ingenuity.

Similar to an AP blockchain, maybe it makes sense to create a blockchain for academia. Think of it as a peer-reviewed network (as all blockchains are) that wasn’t reliant on publication in academic journals to establish credibility and priority of discovery. That’s a much more transparent, democratic process.

Changing course slightly, maybe we can use the blockchain to disincentivize the consumption of culture by social media, and reincentivize the search for new art? Today I can find out about a band’s secret concert by following the right Twitter handle. It doesn’t take any skill or devotion. It doesn’t take being a snooty hipster to see how that reality can erode the quality of experience of investing in a band / artist / movement. But what if I was only notified of this secret concert if I’d been following the band since 1997 or earlier — a fact which could be verified via blockchain (assuming it existed then). I know a whole swath of Pearl Jam fans who would love such an experience, and I bet Pearl Jam would love it, too (on occasion).

If ideas like the ones I mentioned here, or ones even vaguely similar are adopted, they would have the knock-on effect of reincentivizing the pursuit of the vanguard. Put differently, if the value of a thing is inherently wrapped up in its rarity and transferability, and blockchain enables us to prove the rarity and transferability of any range of things, then new mechanisms for demonstrating value – financial, societal or otherwise – are sure to follow.

Tweet This.@GCTech proudly welcomes 19 impressive startups to its second class. Check them out here:

We couldn’t be more proud to announce the 19 companies who have been accepted into our 2015-2016 program. As we mentioned in an earlier post, we had a tough job this year, parsing down a list of ~1,000 program applicants to get our second class of companies. To help us make our decision we focused on five key criteria, and we feel that these 19 startups exceeded our expectations in these areas.

Our mission in starting GCT was to generate a diverse community with technology and education at the core. The first year was a resounding success, placing us at the forefront of innovative accelerator initiatives and securing the commitment and support of global technology leaders with a likeminded vision. We saw 18 startups graduate last year, which have collectively seen a ~30 percent job growth rate and ~$33 million in funding.

Each of the companies in our second class are on a clear path to make a positive impact in the New York tech community and contribute to innovation in the industry as a whole. As was the case with our first class, two-thirds of our 2015-2016 class of startups have female, minority or veteran founders.

So what do these 19 companies do? More on our new class:

  • Maven Clinic – Maven is a new health technology platform, designed exclusively for women, that provides easy and affordable video appointments with health and wellness practitioners. Maven gives women near-instant access to practitioners focused on prenatal and postpartum care, children’s health, and other women’s health concerns. This platform helps to prevent avoidable trips to the emergency room and provides peace of mind to women in the privacy of their own homes.
  • Common – Founded by Brad Hargreaves (co-founder of General Assembly), Common is a membership organization building a network of social, flexible, community-centric accommodations for shared living. They partner with property owners and local organizations to create residential communities appealing to a new generation with monthly terms, shared services, and active community management.
  • Project September – Project September is a currently-in-stealth social commerce startup founded by Alexis Maybank (co-founder of Gilt), Leah Park, and Dustin Whitney.
  • Source3 – Source3 is the one-stop enterprise licensing and rights management platform for distribution of 3D content. Source3 aggregates 3D content from brands and designers, and distributes licensed designs for use within the broader 3D ecosystem, including retail and manufacturing marketplaces. They aim to emplower the 3D economy by solving ecosystem-wide intellectual property pain.
  • Ziel – Founded by Marleen Vogelaar (co-founder of Shapeways), Ziel is building something where Athletics meets Technology + Design.
  • Code to Work – A key blocker in improving diversity statistics across numerous industries is awareness of and access to pools of vetted, diverse talent. Code To Work connects industry leading employers with the young people from diverse backgrounds they want to engage and hire while providing piece of mind in their abilities via a proprietary skills evaluation mechanism.
  • Sage – Sage makes the food labels of the future. Both the Web and mobile app show consumers everything they wished a food label showed them, personalized to what they actually care about, annotated by food experts (nutritionists, dietitians, food scientists), and with all the data broken down and visualized in ways that are easy-to-understand and approachable by all.
  • Toymail – Founded by Apple and MIT alums responsible for multiple popular products in connected hardware, Toymail creates fun, IoT-enabled toys that facilitate two-way messaging between adults (e.g. mom, grandpa) and children.
  • Backtrace I/O – Founded by the lead engineers from AppNexus, Backtrace I/O is fundamentally improving the state of software debugging. Their flagship product is an advanced crash report generation and analysis platform that helps software engineers working across industries to pinpoint, diagnose, and resolve their crashes with unparalleled efficiency.
  • BAMx – BAMx is the first ever exchange to connect merchants with premium editorial opportunities through real-time bidding. It gives retailers the ability to control and optimize how they drive traffic and sales from organic content, making it possible for retailers to bid for the link-to-buy associated with each product in editorial lists.
  • – is a payments company that focuses on providing bitcoin payment solutions to forward-thinking companies and consumers. Leading with their Payment Processing Services,’s technology enables businesses to accept bitcoin from their customers, yet receive US dollars into their bank accounts.
  • Concord – Concord is a real-time distributed stream processing framework that is 20x faster than Apache Storm. They empower users to process and react to their data in real-time, whether they’re doing fraud detection, ad bidding and serving, content recommendation or algorithmic trading.
  • Iobeam – Iobeam is a data analysis platform for the Internet of Things (IoT). The promise of IoT is a future where everything is connected and sending data for useful analysis, but the companies that build these products need infrastructure to organize, store, analyze, and build on top of all of the disaggregated, non-normalized data these IoT devices will yield. Iobeam provides that platform.
  • LiquidText – LiquidText is a platform to help professionals read, understand, and make connections across all their digital content. On the front end, they offer a radically different interaction model that allows consumers to dynamically manipulate text through annotations, excerpts, highlights, and scaling. On the back end, they leverage associative metadata to offer unique search, content recommendation, and trend analysis tools.
  • Innovatively – Innovatively is building the Bloomberg for research. The platform makes sense of public research data to help enterprises and SMBs find out what they are missing in their market, competitors, and customers. Innovatively’s first paid pilots are in the healthcare and life sciences, where they’ve been able to turn around information 10x faster than traditional consulting firms.
  • Senvol – Senvol helps companies fully leverage the opportunities and benefits that additive manufacturing (i.e. 3D printing) can provide. Through a proprietary algorithm, they are able to analyze and quantify how the implementation of additive manufacturing can increase business profit.
  • Wheelhouse – Wheelhouse helps developers, engineering leaders and business stakeholders to build better software through technology enhanced training. It delivers customizable learning solutions to improve the skillset of enterprise engineering teams by leveraging GitHub and other popular platforms, and offers community based certifications to make learning social and effective.
  • Havenly – Havenly provides online interior design services by connecting users with their own personal interior designer for a flat fee of $185. Users are algorithmically matched to a designer matched exclusively to their style, who works with them to virtually arrange and decorate a room.  Through Havenly’s technology, designers can reimagine a room without existing furniture, and users can purchase all furniture through the the app at a designer’s discount.
  • Boom Shakalaka – Boom Shakalaka is an in-game fantasy sports company that helps sports fans better engage with the games they are following by pushing real-time bets (e.g. will Adam Vinatieri make this 50-yd field goal?) to their phones while also allowing them to compete against other fans around the world.
Follow us here and at @GCTech to stay updated all year on all things GCT.

Matt + Charlie


This weekend I’ll be getting married to my best friend and fiancee, the Boss. I couldn’t be more excited to embark on this journey for the rest of our lives (and to take a much needed honeymoon). I am without a doubt in my mind the luckiest guy in the world to be able to marry the love of my life, as well as to have the world’s best job and an unreal team alongside me.

So now that all of that’s out of the way, let’s get to it: the process of getting married is an expensive and exhausting process. (NB – yes, it’s possible to get married without the hullabaloo, but I’m from a huge Italian immigrant family and she from an Irish one, so that’s not an option in the world I live in). Now, Kathleen has done close to 100% of the hard work here so I shouldn’t complain, but given my background as a consumer analyst and where I currently sit , the whole process struck a few notes to me that I think are pretty instructive on the dynamics of any B2C sales cycle.

I like to think that I’m a pretty good negotiator but even I’m pretty susceptible to the overtures of these vendors. And I think what I’ve narrowed down on is three or four key elements that necessarily influence the pricing power (and margins) for any given service or product:

Stakes, Frequency and Transparency. And along the x axis let’s say “emotion” or longevity acts as a multiplier on this effect.


The lever for nearly all consumer businesses is the delta between customer acquisition cost and lifetime value of a customer. Often times, that second part is exacerbated, or most often generated by repeat customers. When a customer acquisition event is extremely infrequent, the vendor has little to no economic incentive to take a loss in order to encourage future visits or purchases. In fact, it’s quite the opposite — a lifetime of a customer experience needs to be squeezed into a single transaction, so the “upsells” and “add ons” that you might get over the life of a subscription business or in app game purchase manifests itself into a 9th piece in the band, chrome handles on a casket, a clear undercoat on a car or (still pulling for this one) a buffalo sauce fountain at the cocktail hour. It’s why you can get a free training session or a week trial at almost any gym: the conversion rate to paid and average customer lifetime way way way outweighs whatever costs are in the upfront. It’s also probably why spending on every child after one’s first drops so precipitously.


The stakes of the customer event likewise adds to the potential for absurd margin capture. My own personal sleuthing suggests that the all things being equal, calling something a wedding instead of a summer party tacks on an automatic 30% extra. That’s precisely because a captive audience is one with little leverage in his or her favor. This is probably one of the biggest reasons that healthcare costs are so high. Facebook spent $2.7 Billion in R&D last year alone. That’s more than what it costs to develop and bring to market a new drug. The difference is that if you don’t take facebook you won’t die or get very sick, and there’s no built in payer to leverage for payment.


Any kind of efficient marketplace has some balanced knowledge set for both sides of that market about relative pricing and costs. That’s why when you go to buy something at a store, on eBay or Amazon the prices will usually be pretty close together. That kind of widespread and readily accessible market information translates to some degree of demand elasticity for customers — and a baseline for retailers. Karmax is a great example of a company that sets the market in this way.

Throw that out the window when it comes to areas with some degree of specialization required. When a supposed “expert” is selling to an “amateur”, the opportunity for misaligned incentives is too high. Kayak eliminated that imbalance in travel. But try to find wedding costs somewhere. You can’t. It’s not online, you can’t just call and ask, and emails will come pretty close to demanding an in person meeting. Without some baseline of knowledge, the “experts” are incentivized to be opaque and to keep prices relatively high together.

Combine this with a fragmented, highly local market, and it starts to make more sense.


The final part of this equation as I see it is emotion or longevity. When something is emotionally charged, or expected to last…forever, the extent of that emotional pull (either extremely happy or extremely sad) dictates the opportunity for a premium. You buy organic, handmade diapers for your first kid because you are terrified of making a mistake. You buy whatever’s on sale for your second kid because you realize you are literally flushing your money down the toilet.


The best upstart businesses aim at eliminating at least one of these elements. At the heart of it, that translates to saying “opening a reasonably priced wedding hall” has a limited ceiling while creatin the kayak for wedding venues is likely a tremendous platform with a lot of scale. And that’s the fundamental difference between a service and a platform.

In the end, the stakes couldn’t be higher, the frequency lower, the transparency more confusing and the range of emotions more volatile…but I couldn’t be happier to be getting married in a few days. And I couldn’t be more grateful for all of the help, love, and support we’ve received from our families and friends.

I’m off for my honeymoon, and when I get back we’ll be announcing our next class of GCT. It’s going to be awesome. Talk about being a lucky guy.

As you read this, we at Grand Central Tech are in the midst of reviewing (more like re-reviewing) applications and conducting interviews for next year’s class of companies. It’s a thrilling process, but it’s also painful in a way. So many of the companies we’re reviewing are truly remarkable. The “who are we to judge” notion occurs to us routinely. But we do have to make our calls.

In making those decisions we rely broadly on five key criteria: (This language is cribbed from an Interview we did with BreakOut Labs. For even further background on our thinking at GCT, I’d encourage you to read the full interview here.)

1. The team. How long they’ve known each other, whether they’ve worked together before, whether any of the founders has done anything notable in the space before etc.

2. The quality of the engineering talent on the team. We want to make sure the team can independently build their vision and has the skills to pivot if necessary.

3. The importance and the scope of the idea. Does the idea matter? Are they attacking a big market with a novel “way in”?

4. The traction. Is the idea/business in the market? If so, is it generating users and/or revenue? If not, what’s the path to market? How likely is it?

5. The community fit. Does the business buy into the broader GCT mission to address issues of diversity and inclusivity in the tech ecosystem?

This evaluation criteria is reflective of where we like to position ourselves on the “startup maturation curve”. While we believe in not taking equity from our companies as a matter of philosophy (and explained in detail here), we also want to capitalize on that decision strategically. Our criteria, and the manner in which we deploy it, helps us find companies in the “GCT sweetspot.”


We are looking for points of proof that, by their virtue, diminish the risk inherent not just in their business, but in ours as well, namely the year-long nature of our program. No accelerator program wants their bets to not pan out, but we really don’t. Were we just trying to build promising companies for their investment potential, a slightly higher level of risk would be attractive insofar as it might warrant the equity fee baked into the standard accelerator positioning. We’re trying to build something a bit different though, a bit bigger. This is not to say we don’t have every interest in our companies gaining notable investment and becoming tremendous, lucrative businesses; because we do. But we’re also trying to build a long-lasting, vibrant community around, and via, our companies. This is how we build a “single-point of density of New York’s premiere startups” as we often put it.

Companies that fall in the “GCT Sweetspot” have demonstrated to themselves and others the initial indications of product market/fit, or a well-honed aptitude for finding it. They’ve often raised a bit of funding, too. You might then be asking yourself, “Why are they participating in an accelerator?” I think the simple answer is that, even with this much worked out, it still ain’t easy. Having the opportunity to leverage the collective know-how of a best-of-breed community, as well as top-flight corporate partnerships, can provide the final solutions that truly transform promising businesses into proven ones.

What proof do we have that this works? 100% of GCT’s inaugural class of companies is graduating into our coworking space elsewhere in our building. It is the case that we ask our companies to commit to doing so as a condition of their entry into GCT, but we give them every opportunity to avoid this commitment if they view it as an encumbrance. None has. Furthermore, our companies have requested to be seated alongside each other in our coworking space. You can’t force community like that.

One last thought, in case it’s occurring to you, “accelerator” might be the wrong term for us. Maybe we’re a “finishing school for proven concepts.” We happen to not be the biggest fans of startup jargon ourselves. “Accelerator” is close enough for us, so we’ll stick with it. But we are different. And we like being different. We think our positioning in the “GCT sweetspot” lends us the highest likelihood of checking the last boxes for startups poised to become job-creating, economy-improving businesses and imbuing in them a sense of community and corporate citizenship that will have lasting, ripple-effect benefits throughout the tech sector.

Last Friday at Midnight EST the application window for Grand Central Tech’s 2015-2016 class officially closed. The level of response we received was humbling, and, in aggregate, a bit terrifying — our applications doubled from last year! (Of course, true to entrepreneurial form, a frightening percentage of that response was received in the final 24 hours!)

Once we’ve had time to comb through all of the applications thoughtfully we’ll likely produce a report detailing some of the insights and industry trends we’re observing. In the meantime, we’ll be enjoying reading more about these amazing businesses, and getting to know some of them even better via our interview process. Our goal is to have the 2015 – 2016 class selected by mid-June at the latest in time for a July 1 start date. To all of our applicant companies, thank you for your thoughtful, diligent responses. It’s an honor to review them, and to be considered as your ideal mechanism for accelerating your business. Again, we’re humbled.

We’re also incredibly excited to announce that Goldman Sachs has come on board as Grand Central Tech’s eighth corporate partner. To quote from the press release: “Together, Goldman Sachs and GCT will work to further establish and support the local entrepreneurial technology community, focusing broadly on professional development, mentorship, networking, and events.

In addition to building relationships with startups in the GCT community, Goldman Sachs will support GCT’s corporate social responsibility efforts, including their summer internship and STEM-focused programs through local partner schools and educational organizations. “Goldman Sachs is passionate about embracing innovation, nurturing talent, and supporting the communities where our people live and work,” said Lance Braunstein, global head of Client Platforms and Investment Banking Technology for Goldman Sachs. “Engineers at Goldman Sachs build and deploy the innovations that drive our business and the financial markets worldwide. We are pleased to partner with GCT to support the continued growth and success of tech-enabled entrepreneurship in New York and beyond.”

We could not be prouder of our first class of GCT companies as they prepare to move upstairs. We’re also excited to continue to grow the GCT family with amazing corporate partners like Goldman Sachs, and what is shaping up to be another incredible class of entrepreneurs for 2015-2016. It’s precisely because of this committed, and growing group of stakeholders that we feel particularly excited to continue to support the NY tech ecosystem and ever more confident in our ability to do so together.