Author Archive

Why you should apply to MassChallenge TODAY!

If you’re reading this, you probably already know what MassChallenge is. You know the deadline to apply is April 2d. You’ve heard all the “10 reasons to apply to MassChallenge” pitches. But you still haven’t applied – perhaps you’re not sure if it’s worth it, if you should spend the time and energy, if you getting admitted or rejected is really important to your goals.

So let me take 5 minutes of your day to give you a nudge. Trust me, it’s worth it.

I have been honored to be a finalist in MassChallenge in 2012, and invited to “serve” as alumni in residence in 2013, so I have two perspectives on it: as the guy in your shoes, pondering over the application, and as someone who has no vested interest in being a part of it.

I’ve watched roughly 200 people go through the program. Some have since raised millions in funding. Some have failed learned a ton and moved on to even more awesome opportunities. The former of course is great, but the latter is really the most unique part of MassChallenge that I have not witnessed anywhere else, and that I want to share with you: there are no losers here.

MassChallenge is, after all, a competition. Some people win the “finalist” status, but most don’t. Even fewer people win funding, but even more don’t. (I didn’t). And yet there are no losers in MassChallenge! They always say that, and I used to doubt the veracity vs. marketing value of that expression, but it’s totally true. Here’s why:

– No one, literally no one who applies, gets a “thank you but you’re not good enough for unspecified reasons” rejection letter. This is not college admissions. A team of highly qualified experienced business people reviews *every* single application to provide written feedback. The application itself is a template to force you to condense and structure your business pitch, which you will have to do over and over if you run a startup – for investors, customers, partners…etc… This is an opportunity to refine it with no strings attached.

-There is a realistic shot you’ll win a finalist spot. MassChallenge is unique among accelerators in terms of its capacity. By having a more open “self-serve” approach to mentorship, in-kind benefits, and office space, MassChallenge accepts 128 companies in every class. It’s still very competitive, but your time is worth it from a risk-reward perspective. You’re not taking a 1-in-10000 chance.

-If you apply to MassChallenge, consider yourself a winner. You’ve taken a step towards building a business that most people don’t. It will be an actionable step that will, whatever the outcome, give you the feedback to move forward.

If you become a finalist, consider yourself a winner again. Working out of MassChallenge for 3 months will bring enormous resources to your fingertips. Forget mentors and investors for a second. Having 120+ driven, brilliant people work side by side with you every day creates a work environment unlike any other. I often felt that I learned more in a day of MassChallenge than I learned in a month working elsewhere.

Scale and openness creates serendipity. This is hard impossible to plan for, and you don’t believe it until you experience it. But via completely random connections I couldn’t come up with if I tried, being in MassChallenge helped my business grow in the most actionable ways. I literally met our first investor when he was wandering around the space to visit another portfolio company. We ended up raising more funding during MassChallenge with his help than would be afforded by the “prize” we didn’t win in the end.

So go for it. You can’t lose. And if you missed the early application fee discount, ping @goreactor or @mraybman on twitter. I’ll hook you up.







Categories: Uncategorized

Native Advertising vs Content Marketing

A marketer from Switzerland emailed me recently to ask me about the difference between content marketing and native advertising. This was my response:


“{Name Redacted},

Content marketing is, exactly like you said, a way for a brand to tell a story in an editorial format. For example, Toyota could write a piece about a happy family road trip and pay a newspaper to publish that story. (This is also sometimes called “advertorial”).

While content marketing allows a brand to completely control the message, there are two fundamental problems with it: it’s hard to scale, and it can be perceived by many people as deceptive.

So, to broadcast a message at scale, advertisers rely on traditional display networks, which suffer from the opposite problem: they “spray” millions of cookie-cutter ads across the web, usually unrelated to the content of the page they are on, and disruptive to the users’ browsing experience.

Native advertising is out to bridge that gap: deliver seamlessly integrated, relevant ad experiences at scale. Usually that means customizing the ad delivery platform to fit into the design and functionality of every publisher’s site. Sites likes Facebook have this functionality from the start, using “sponsored posts.”

Traditional publishers however, do not, and companies like TripReactor help them create “native” inventory that extends their editorial narrative with relevant advertising. In our case, advertisers send us raw images and text, and we dynamically display it within each publisher’s format in real time.”

(This post is the first in a series about the differences between advertorials, content marketing, and native advertising).

Why Native Advertising Must Live

(Full Disclosure: my company, TripReactor, builds native advertising solutions for travel and lifestyle industries).

Last week, Lori Luechtefeld wrote a post titled “Why Native Advertising Must Die.”  In it, she makes an argument that the term “Native Advertising” is an ephemeral industry buzzword that needs to be avoided, because it leads to a “horrible blurring of the distinction between pure editorial and advertising that’s going to ultimately backfire on publishers and marketers alike.”

Please read Lori’s entire article here. It raises valid concerns, and builds a compelling argument for caution in resurrecting failed practices under a new buzzword.

I believe technology has progressed to a point where we can deliver highly relevant advertising in a way that’s truly valuable and engaging to the user, at scale. Advertorials and banner ads cannot do that for all types of content. The term “Native,” however, can provide a name for this emerging class of ad technology, if used properly.

Native advertising, at one point defined by Dan Greenberg, CEO of Sharethrough, as “a form of media that’s built into the actual visual design and where the ads are part of the content.” The term didn’t gain wide exposure until last year’s AdTech conference, and being so new it sill lacks a ubiquitously accepted definition. Therein lies a problem – it’s hard to analyze a term when people don’t agree on what it means.

If we imply that “native advertising”  is native to Content, then we may indeed be conflating native advertising with deceptive versions of content marketing. (Lori refers to that as “The Misdirection” in her post). Content that’s masked to appear editorial when it actually comes from a third-party source is a poor practice that must, indeed, die.

However, as an engineer, I approach this definition with an engineer’s vocabulary. According to Wikipedia, “In computing, the “native” adjective refers to software or data formats supported by a certain system with minimal computational overhead and additional components. This word is used in such terms as native mode or native code.”

In the context of advertising, I take it to mean that “native” applies not to Content, but to Design and User Experience. A banner ad for a particular product, for example, looks exactly the same on every single site it appears on. People get so allergic to looking them that  “banner blindness” is actually a term!

I believe that a display advertising unit can be called “native” if it fits the following two criteria:

1. It extends the editorial narrative by offering products and services contextually related to editorial content.

2. It extends the design language and user experience of the site it is on.

If we can satisfy these conditions at web scale, users will find more value on publisher sites, publishers will earn more money, and brands will be able to reach consumers via efficient, measurable display channels.

Is it possible and probable that this terminology will be abused by some? Sure. But it is incumbent upon us as an industry to own innovation, and create meaningful terminology as needed. Native Advertising must not be confused with “content marketing” or “deceptive advertising.” Native Advertising must live.

I am going to space!!

I am excited to announce that I will be joining the Inspiration Mars Foundation to travel to Mars in 2018.

It has been phenomenal getting to know all of you fellow inhabitants of Earth, and I feel that the next five years will be a perfect time for me to transition onto new, exciting projects. I believe the Space Exploration market is ripe for disruption, with entrenched competitors and high costs.

The Marsian startup scene has stagnated over the past ten million years, and it is now experiencing a true Renaissance. Inspirational Mars foundation has been selected to join the elite YMarsinator startup incubator and will look to turn the Mars entrepreneurial and venture community on its head over the next decade.

Our endeavor will attract widespread media attention over the coming months as casting heats up for Bravo’s newest show: Hustlers, Mars Edition. Please join me for our actual, physical, launch party aboard the International Space Station five years from today.

Please  tweet with the hashtag of #MarsRaybman to get my personal discount code to the party. Hope to see you all there!

Categories: Uncategorized

How to prepare for MITX-UP

November 16, 2011 Leave a comment

[tweetmeme source=”mraybman” only_single=false]

Yesterday, I had the pleasure of participating in MITX-UP marketing hackathon at Critical Mass (pronounced “my-tex-up”).

The event was totally awesome and if you are a startup, you should particiapte next month, hands-down. The process is simple: you fill out a questionaire, get matched with 4-6 marketing experts, and spend 3 hours with them discussing your project. Awesome.

Since this was my first time at the event and I didn’t know what to expect I thought I’d jot down a few notes for entrepreneurs participating in the next one:

1. Give detailed context

The first 10 minutes or so should be spent on you pitching your startup. The mentors probably read a paragraph they were sent about you in advance, but they don’t know the stage you’re at, the nuances of your industry, or the details of your product.

2. Come with questions

Figure out your top 3 marketing/branding/bizdev challenges and state them clearly up front. Be as specific as you can. This way, the experts know exactly how they can help, and you have anchors to build much of the discussion against. The more diverse these points are, the more likely there is someone in the room who can help you on each one. (Alternatively, figure out which topic everyone is an expert on, and do a deep dive on it)

3. Talk about messaging.

It’s great if one of your questions is about branding and messaging. Mitxup experts are branding and messaging rockstars and they can probably help you a lot here regardless of your spccific industry. This point can be broad (“what image do we project”) or specifc (“how do I craft this biz dev email”).

4. Bring materials, even if they are raw.

A product demo, an email newsletter, advertising copy, logo ideas: anything you have, bring it and give it up for people to criticize. (Remember they’re here to help you).

5. Leave time for open discussion.

Your mentors will have some ideas you haven’t even thought of. Make sure you leave time to listen. Brainstorm ideas with them even if you don’t find all of their ideas immidiately applicable – you might discover something new in your own startup!


Can Microsoft be a lifestyle brand?

[tweetmeme source=”mraybman” only_single=false]

When people mention a “lifestyle brand,” companies like Apple,  Sony, or Calvin Klein come to mind. For many of us web geeks Google has become a lifestyle brand, and I would even throw “Open Source” into the mix. (I’m talking about that friend of yours who runs a Linux distro on his iPod, netbook and smartphone while arguing that eMacs is a better IDE than Vim). In my life, however, Microsoft has carved out a niche product-by-product over the past few years, so I thought I’d share the “other” point of view on the big brother of software. (Oh wait, John Stewart says that’s Apple these days).

First: I’m not a platform purist. I use whatever devices and software are most convinient for me, within my budget. I’ve used Microsoft software since playing Prince of Persia on DOS, but I also worked on MacBooks, sent Gmail messages, and dual-booted Ubuntu with Windows. At times, Microsoft products almost completely vanished from my desktop (think Vista + old Hotmail), but they are now back in force.

Here’s the setup:

  1. Windows 7
  2. Hotmail with @waysavvy domain
  3. MS Office 2010
  4. Internet Explorer 9
  5. SkyDrive
  6. Windows Phone 7
  7. Visual Studio 2010 + SQL Server

How much do you think this setup cost me? $10,ooo? $5,000? How about $0.01? How about $0.01 legally?! Let’s dig in.

Windows 7.

There are books’ worth of OS debate online, so I won’t go into depth here, but in my experience it’s stable, fast, has great productivity tools,  a solid set of development APIs through .NET and still dominates the amount of applications available for it. (Comes pre-installed on most off-the-shelf PCs. I have it running on a dell Latitude E6410, which is a really powerful comp for about 1/2 the price of a comparable Mac).


Many people think of Hotmail as retrogate email service that attaches ads to every message. That’s ancient history – it’s a well-performaing feature-rich email service with a conventional timeline layout. Some people prefer Gmail’s “conversation” view, but I personally don’t. Someone will disrupt email soon in a major way, but so far it hasn’t been Google, at least not for me. Lack of IMAP support in Hotmail is the only thing that irks me, but I use the Outlook Connector in Outlook 2010, which brings me to…

Office 2010.

I think you can agree with me on this one – no other piece of software today, on any platform offers the full functionality of Microsoft Office. Thunderbird or OpenOffice just aren’t there in terms of polish and features, and are not paired well with any one OS. For Excel, there’s simply no match in terms of the raw table-crunching power. Across the board, it’s really easy and to deliver rich documents, and there’s great interoperability among elements of presentations, text documents and spreadsheets. Office 2010 can get pretty expensive with all the bells and whistles, but for now I use it for “free” under my Microsoft BizSpark subscription.

Internet Explorer 9

To say this browser is better than Firefox or Chrome would be a stretch, especially if you’re into plugins. But this is the first version of IE about which I can honestly say that it’s just as good. Plugins aside, it mostly matches Firefox in features, is visually polished, supports “application” windows nicely, and has greatly improved speed and security.


If you use Office, especially Office 2010, integrating with SkyDrive is really easy. I can save and open documents from there without opening my browser, I can selectively share documents with different groups of people and give each one different permissions, and I can edit them inside or outside the browser. I wish the web interface was just a little snappier, but it’s no slower than Google Docs in my experience. If you like Dropbox (which I love), it works nicely side-by-side. I can sync a doc across all of my computers with Dropbox, and share it with someone via SkyDrive. With an upcoming update, I’ll also be able to view and edit documents from SkyDrive on my…

Windows Phone 7.

I’ll admit – I never saw this one coming. Microsoft kinda botched Zune (although it was a good product), it botched Kin (that was a terrible product), and Windows Mobile 6.5 was never really that popular. So, I wasn’t excited about anything mobile from Microsoft until I tried my Samsung Impression. And it rocked. So I bought it. For $0.01 from Amazon Wireless. The phone is really powerful, has tons of apps (not nearly as many as iPhone/Android but growing really quickly thanks to a nice SDK), has all the hardware bells and whistles except  a front-facing camera, and did I mention? It costs $0.01.

Visual Studio.

Finally, the geeky part. My startup’s product, is written in .NET, so we use Microsoft’s tools provided to us through BizSpark. If you prefer writing code in a text editor – have it your way – but if not, I do not believe there is a better IDE than VisualStudio. This post isn’t about IDE features so I won’t go there, but I think VS’s feature depth and productivity tools are unrivaled by any other IDE for any langauge.

So there you have it – my answer to Apple fanboys for a grand total of $0.01 (until my BizSpark subscription runs out). So far, I really like it. What do you think? How does it compare to your digital lifestyle?

Categories: Uncategorized

Advice for students looking to get a job in the tech industry

April 8, 2010 1 comment

[tweetmeme source=”mraybman” only_single=false]

Scott Kirsner posted 5 great tips earlier today to students and recent grads looking to work in tech. Inspired by his post, I decided to add my 2 cents here.

First of all, where am I coming from? I graduated from Brandeis last year in computer science, and am currently working on a startup I co-founded, WaySavvy. While at Brandeis, I went through an internship at IBM,  and worked for a year developing epidemiology modeling software at Brigham and Women’s hospital. I was later admitted to IBM’s Extreme Blue program and offered a job at a local software company, but turned both down to work on WaySavvy. I don’t have decades of experience and thousands of resumes behind my belt, but I know what it’s like to enter the fray first-hand. Hopefully, I can offer some insight to people who are one or two years behind me in the process.

So, without further self-aggrandizing/deprecation, here goes.

1. Start networking TODAY.

Literally, right now, go to a site like Greenhorn Connect, pick out some free events this week, and go. If you’re in Boston, great startup-themed events happen here all the time: WebInno, MassInno, Tech Tuesdays and PokinHoles are some of the must-sees, among lots of others. Networking carries value pretty much at any stage of your career. If you’re not sure what you want to do, you’ll glean ideas from conversations with people. If you are, you’ll get valuable feedback and connections. There are lots of resources out there on  effective networking techniques, but ultimately everyone has their own style so the best way to learn is to do it a lot.

Besides third-party events, don’t forget to browse your alumni network (I do it on LinkedIn). Most alums like helping out recent grads, as long you’re respectful and not pushing an agenda. Ask them for advice, and if they can help you get your resume in somewhere, they will.

Also, make friends in your school’s computer science department if you can. These exist even in humanities-focused liberal arts schools and most likely people there have ideas and resources to help you. Computer science professors often serve as advisers to startups or even larger companies, and many are generous about making introductions.

2. Find a problem you would like to solve.

This advice is given to startups a lot, but I think it’s just as true when you’re looking for a job. When you’re passionate about something it will show. Skills are important, but if you show passion and talent, skills become secondary. Few things are more attractive to a recruiter (I think), than a candidate who is eager to change the world and wants to do it from their company. How do you show such aspirations? Find something that bugs you such as a product, a process, a market gap, and start trying to make it better TODAY. Start blogging about it, tweeting about it, telling you facebook friends about it. Then, being hired by a company that has a similar goal is very natural – you are already doing what they need you to do, they will simply enable you to be more effective at it.

3. Get a campus job/research position in the tech field.

Most people think of summer internships as the best time to get hands-on experience, but the school year is your best time to get an edge. Talk to professors and administrators, and find an assistantship (event if its unpaid) where you can get exposed to the field that interests you. Working at an academic lab as an undergrad doesn’t mean you have to get a Ph.D. It’s a way to learn the challenges of a field and learn new skills. You don’t have to be an engineering major to work in a technical lab – psychology, economics, sociology and anthropology all have cross-pollintation potential with math and computer science. Talk to your academic advisers, keep an open mind, and they will help you set something up.

Not only will you gain professional experience, but you’ll pick up presentation, communication and teamworking skills that every manager wants to see. In the end, you’ll make yourself more competitive for those lucrative summer internships and might even pick up some course credits.

4. Polish your online image.

Techies Google things, and when we find out you want to work with us, we will Google you. When we do, your ultra-polished resume will have no effect if your linkedin profile hasn’t been updated in 3 years. To prevent that from happening, make sure you’re on top of your social media game – update your linked in profile, make your embarrassing Facebook pictures private. You don’t HAVE TO blog and tweet, but if you do, make sure you have filled out the “about me” pages.

5. Consider entrepreneurship

There is no better time to start a company (in my brief experience), than out of college. You don’t have to worry about living expenses, family, or even failure! That’s right – if you start a company the summer before your senior year and it fails by the end of the following summer, guess what – you still win! You will have learned a tremendous amount, demonstrated initiative, and took a shot at changing the world – I doubt there is an employer who doesn’t find that attractive. You can go back to a traditional job search and when you’re ready again, take another crack at fame and fortune with all the experience you’ve gained. There’s tons (really, tons if you print it out) of information out there on how to launch a company, but the basic idea is the same – solve a problem, network, build an image. To get inspired, read blogs by Dharmesh Shah, Scott Kirsner, Larry Cheng, Brad Feld, Dave McClure, VentureHacks, Guy Kawasaki, and others.

These are the top five things that come to my mind- what are yours?