Jan 142010

Jump Starting Start Ups



As I mentioned in some recent posts, I’ve really enjoyed sharing the Return Path story with the tech start-up community in New York through groups like the NYC Lean Startup Meetup .  


Next week I’m taking the Return Path story on the road to Silicon Valley where I’ll be presenting to Startup2Startup.  Startup2Startup is a group of Silicon Valley geeks, entrepreneurs, and investors dedicated to educating and helping the next generation of Internet startups. They meet monthly over dinner to discuss relevant topics in technology and entrepreneurship, connect with new people and companies, and share our knowledge and experience.


You’ll not only get to hear about Return Path’s 10 years in business but I’ll also be sharing some best practices to diagnose and resolve email deliverability problems.

Interested? Request an invitation here.

Stay tuned for more on this post-event.

Dec 282009

Learning How to Stop

Learning How to Stop

This is my last post about thoughts I had coming out of the NYC Lean Startup Meetup that I spoke at a couple weeks ago.  Being lean, the discussion went at this event, means not doing extraneous things.  While it’s true for startups that it’s important to make great decisions about what to do up front, it’s also true — especially as companies get larger and more important older — that organizations and individuals have to be vigilant about stopping activities that become extraneous over time.

This is HARD.  Once things — product features, business processes, reports, ways of communicating or thinking about things — get ingrained in an organization, there’s never a natural impetus to stop doing them.  Even the smartest and most thoughtful individuals often find themselves doing things that once made sense but no longer do. 

We encourage people at Return Path to create space to work OTB (on the business), not just ITB (in the business).  Take time not just to perfect what you’re doing and do it, but take time to reexamine what you’re doing and ask whether or not it needs to be done.  My staff is going to start doing an exercise at least quarterly around pruning/simplifying activities.  

Focus is not just about saying “no” to new tasks.  It’s also about saying “no longer” to old ones.

Dec 212009

Innovating in New York City

Innovating in New York City

Last week I wrote about speaking at the NYC Lean Startup Meetup.  One of my other key takeaways from this, which I’ve known for a while and have been meaning to blog about, is just how vibrant the tech startup community is here in New York.  I know others have been blogging about this like mad – Fred has some thoughts here, here, and here, and Charlie has some here and here.  Chris Dixon’s seminal post on this is here. (I even blogged a bit about why NYC is a good place to start a business back in 2006 here.)

I’ve had a little more time for networking and speaking in the past year than the prior year, and I’ve been blown away by how many startups there are here.  Like most things, New York City is such a massive and diverse place that it’s easy to “get lost in the crowd,” and there’s a lot going on.  So startups don’t tend to get the same level of social buzz that they do in Silicon Valley.  But Fred’s stat in one of those links above that over 150 startups were founded in NYC this year compared to over 300 in the Valley is interesting when you consider the geographic density here.  There are many more per square mile in New York.

Despite the geographic density to the startups, the New York startup scene is a long way from being a community.  There are some encouraging signs of late.  Charlie’s establishing a physical presence for First Round Capital is one. NextNY, with over 2500 members, is another, along with various Meetups.  I am learning more and more every day about local incubator-type organizations as well (take that term with a grain of salt).  I thought John Borthwick’s Betaworks was the only one until Charlie told me about Sunshine Suites, TechSpace, and the NYU/Poly program.  But something is still missing.  Some glue to hold it all together.

In the Valley, the startup community is  a cultural thing — plus, startups are part and parcel of a larger tech community.  Most of the big acquirers of internet companies are out there, so the ecosystem keeps cycling through companies and talent and investors.  In smaller cities like Denver/Boulder and Boston (and soon to be Seattle), TechStars fills a good void by providing a high profile “lure the talent here” combined with “meet the money” program. Seedcamp does that nicely in London, which, while it’s a big city, has a much smaller and more dispersed startup community than New York.

Since we’re unlikely to suddenly sprout a bunch of Fortune 500 tech companies in NYC, where’s our version of one of those programs in NYC?  Or is there some other “glue” lurking out there to tie it all together?

Dec 172009

Pivot, Don’t Jump!

Pivot, Don’t Jump!

I spoke last night at the NYC Lean Startup Meetup, which was fun.  I will write a couple other posts based on the experience over the next week or so.  The Meetup is all about creating “lean startups,” not just meaning lean as in cheap and lightweight, but meaning smart at doing product development from the perspective of finding the quickest path to product-market fit.  No wasted cycles of innovation.  Something we are spending a lot of time on right now at Return Path, actually.

My topic was “The Pivot,” by which the group meant How do you change your product idea/formation quickly and nimbly when you discover that your prior conception of “product-market fit” is off?  I talked a bit about the pivots we’ve done over the years here, not just the corporate ones, but some of the essential product ones as well.  One of the comments a member of the Meetup made that really stuck with me was that you have to “Pivot, Don’t Jump” when making changes to your business or product.

This has been true of Return Path’s pivots over the years.  Our pivots have all had two very solid foundation points — the company’s deep expertise in email, and our customer base.  Every pivot we’ve done has been in some way at the request/urging of our clients, and the new directions have always been in line with our core capabilities.  While we have a talented team that probably could execute lots of different businesses well, it’s hard to see us being successful in other areas that are farther afield.

People over the years, for example, have suggested that we should get into SMS deliverability — isn’t that going to be a hot topic?  We don’t know.  We don’t spend our lives immersed in text messaging.  What about getting into measurement of social media messaging — isn’t that related?  Maybe, but it’s not in our wheelhouse.  Expanding from email deliverability software and analytics, into services, into data, into whitelisting on the other hand – those were pivots, not jumps.

One other note of course, is that the larger your business is, and the more investors have a stake in it, the harder it is to make BIG pivots or any kind of jumps.  Innovation is still critical, but innovating from a well-protected core is what it’s all about, not chasing new shiny objects.

Oct 212009

Why I joined the DMA Board, and what you can expect of me in that role

Why I joined the DMA Board, and what you can expect of me in that role

I don’t normally think of myself as a rebel. But one outcome of the DMA’s recent proxy fight with Board member Gerry Pike is that I’ve been appointed to the DMA’s Board and its Executive Committee and have been labeled “part of the reform movement” in the trade press. While I wasn’t actively leading the charge on DMA reform with Gerry, I am very enthusiastic about taking up my new role.

I gave Gerry my proxy and support for a number of reasons, and those reasons will form the basis of my agenda as a DMA Board member. As a DMA member, and one who used to be fairly active, I have grown increasingly frustrated with the DMA over the past few years.

1. The DMA could be stronger in fighting for consumers’ interests. Why? Because what’s good for consumers is great for direct marketers. Marketing is not what it used to be, the lines between good and bad actors have been blurred, and the consumer is now in charge. The DMA needs to more emphatically embrace that and lead change among its membership to do the same. The DMA’s ethics operation seems to work well, but the DMA can’t and shouldn’t become a police state and catch every violation of every member company. Its best practices and guidelines take too long to produce and usually end up too watered down to be meaningful in a world where the organization is promoting industry self-regulation. By aggressively fighting for consumers, the DMA can show the world that a real direct marketer is an honest marketer that consumers want to hear from and buy from.

2. Despite a number of very good ideas, the DMA’s execution around interactive marketing has been lacking. The DMA needs to accept that interactive marketing IS direct marketing – not a subset, not a weird little niche. It’s the heart and soul of the direct marketing industry. It’s our future. The acquisition of the EEC has been one bright spot, but the DMA could do much more to make the EEC more impactful, grow its membership, and replicate it to extend the DMA’s reach into other areas of interactive marketing, from search to display advertising to lead generation. The DMA’s staff still has extremely limited experience in interactive marketing, they haven’t had a thought leader around interactive on staff for several years, and their own interactive marketing efforts are far from best practice. Finally, the DMA’s government affairs group, perhaps its greatest strength, still seems disproportionately focused on direct mail issues. The DMA should maintain its staunch support of traditional direct marketers while investing in the future, making interactive marketing an equal or larger priority than traditional direct marketing. We have to invest in the future.

3. Finally, I think the DMA suffers from a lack of transparency that doesn’t serve it well in the hyper-connected world we live in here in 2009 – that’s a nice way of saying the organization has a big PR problem. The organization does a lot of great work that never gets adequately publicized. This whole proxy fight episode is another example, both in the weak response from the DMA and also in a lot of the complaints Gerry lodged against the organization, many of which the organization says are untrue or misleading. Senior DMA execs or Board members should be blogging. They should be active thought leaders in the community. They should be much more engaged with their members to both understand member needs and requirements and more aggressively promote their agenda.

In short, I will be an independent voice who advocates for progress and change in the areas that I consider to be most important, and I will be transparent and open about expressing my views. I’ve already been clear with the existing DMA Board and management that I do have this agenda, and that I hope the organization will embrace it. If they do, even if only in part, I think it will be to the DMA’s benefit as well as the benefit of its members. If they reject it wholesale, my interest in long-term involvement will be fairly low.

That’s the story. As I said up front, I am taking up this new role with enthusiasm and with the belief that the DMA is open to change and progress. We’ll see how it goes, and I will blog about it as often as I can.

Do you have thoughts on the future of the DMA? I’d love to hear from you. You can leave a comment below or email me directly at matt at returnpath dot net.

Filed under: Business, Email, Marketing


Sep 182009

How Deliverability is Like SEO and SEM for Email

How Deliverability is Like SEO and SEM for Email

I admit this is an imperfect analogy, and I’m sure many of my colleagues in the email industry are going to blanch at a comparison to search, but the reality is that email deliverability is still not well understood — and search engines are.  I hope that I can make a comparison here that will help you better understand what it really means to work on deliverability – they same way you understand what it means to work on search.

But before we get to that, let’s start with the language around deliverability which is still muddled.  I’d like to encourage everyone in the email industry to rally around more precise meanings.  Specifically I’d like propose that we start to use the term “inbox placement rate” or IPR, for short.  I think this better explains what marketers mean when they say “delivered” – because anywhere other than the inbox is not going to generate the kind of response that marketers need.  The problem with the term “delivered” is that it is usually used to mean “didn’t bounce.”  While that is a good metric to track, it does not tell you where the email lands.  Inbox placement rate, by contrast, is pretty straightforward: how much of the email you sent landed in the inbox of our customers and prospects?

Now let’s come back to how achieving a high inbox placement rate is like search.  If you run a web site, you certainly understand what SEO and SEM are, you care deeply about both, and you spend money on both to get them right.  Whether “organic” or “paid,” you want your site to show up as high as possible on the page at Google, Yahoo, Bing, whatever.  Both SEO and SEM drive success in your business, though in different ways.

The inbox is different and a far more fragmented place than search engines, but if you run an email program, you need to worry both about your “organic” inbox placement and your “paid” inbox placement.  If you are prone to loving acronyms you could call them OIP and PIP.

What’s the difference between the two?

With organic inbox placement, you are using technology and analytics to manage your email reputation, the underpinning of deliverability.  You are testing, tracking, and monitoring your outbound email.  Seeing where it lands – in the inbox, in the junk mail folder, or nowhere?  You are doing all this to optimize your inbox placement rate (IPR) — just as you work to optimize your page rank on search engines.  One of the ways you do this is by monitoring your email reputation (Sender Score) as a proxy for how likely you are to have your email filtered or blocked.  The more you manage all of these factors, the greater likelihood you will be placed in inboxes everywhere.

With paid inbox placement, you first have to qualify by having a strong email reputation.  Then you use payment to ensure inbox placement, and frequently other benefits like functioning images and links or access to rich media.  With this paid model, there’s no guarantee to inbox placement (don’t let anyone tell you otherwise), just like there’s no guarantee that you’ll be in the #1 position via paid search if someone outbids you.  But by paying, you are radically increasing the odds of inbox placement as well as adding other benefits.  There is one critical difference from search here, which is that you need good organic inbox placement in order to gain access to PIP.  You can’t just pay to play.

Like SEO, some organic deliverability work can and must be done in-house, but frequently it’s better to outsource to companies like Return Path to save costs and time, and to gain specific expertise.  Like SEM, paid deliverability inherently means you are working with third parties like our Return Path Certification program

As I said, it’s an imperfect analogy, but hopefully can help you better understand the strategies and services that are available to help you make the most of every email you send.

Filed under: Email, Marketing

Tags: ,

Aug 262009

What if There’s No Reason to Eat the Dog Food?

What if There’s No Reason to Eat the Dog Food?

There’s an expression in software about producing a product and market testing it — “seeing if the dogs will eat the dog food.”  I’ve heard it mangled many times around the employees of a software company using the software their own company produces as “seeing if the dogs will eat their own dog food.”  This is always true in consumer software and service companies. 

Employees are often the best users, the power users, and the source of the best feedback to the organization about the product and competition.  We certainly saw this phenomenon in spades at MovieFone, where I used to work before starting Return Path.  There was no more of a power user to be found than Andrew, the CEO, and there was a frenzy every Thursday and Friday as employees called into 777-FILM to buy their own tickets for the upcoming weekend.

But what if there’s no reason to eat your own dog food?  What if your software company develops a specific business application that only one or two people inside your company even care about?  Our services are a great example.  One or two people in Marketing, maybe one or two people in Technology, are users.  When I think about some of the web applications we as a company use, the same must be true of their companies as well.

If this is the case with your company, how do you make sure you get that same level of raw feedback from passionate users inside the four walls of your office, and not just from user groups, which are ok but have some inherent problems in terms of their objectivity and representation. 

I’m not sure I have a good answer to this – it’s more of a question to my readers than a prescription.  I’ll happily reblog the best responses!

Filed under: Email


Aug 072009

Techstars Roundup: Why I Mentor Other Entrepreneurs

Techstars Roundup:  Why I Mentor Other Entrepreneurs

Yesterday was Demo/Investor day at Techstars in Boulder, Colorado.  A lot of people have written about it – Fred, Brad, and a great piece by Don Dodge on TechCrunch listing out all the companies.  My colleague George and I co-mentored two of the companies, SendGrid and Mailana, and we really enjoyed working with Isaac and Pete, the two entrepreneurs.

I posted twice earlier this summer on the TechStars experience.  My first post on this, Where do you Start?, was about whether to be methodical in business planning for a startup or dive right into the details.  My second post, One Pitfall to Avoid, was about making sure you don’t create a whizzy solution looking for a problem, but that you start with a problem that needs solving.

Rather than rehash what others have written about yesterday — yes, it was great and fun and energizing — I thought I’d focus on why I spend time mentoring new entrepreneurs.  I did it this year at TechStars, but I’ve done this informally for probably a dozen different entrepreneurs over the years in the community in general. 

Anyway, there are four main reasons I spend time mentoring other entrepreneurs (in no particular order):

It sharpens the saw.  This is Stephen Covey’s language from both The 7 Habits of Highly Effective People and The 8th Habit:  From Effectiveness to Greatness, and it simply refers to an activity that puls you out of the day to day and refreshes your brain because it’s different.  Running, playing guitar, mentoring sessions with entrepreneurs — they all clear the head and are just plain fun.

I get good specific ideas for my own business.  I think I came away from every single meeting I had with either entrepreneur this year with at least one new “to do” for myself and my team at Return Path.  There’s nothing quite like seeing how another company or entrepreneur operates to spur on good thinking, and in this case, both teams we worked with were working in the email space, so they were very relevant to our day-to-day.

I crystallize my own thoughts and ideas.  Much like writing this blog, problem/solution sessions with other entrepreneurs forces me to take a cloud of ideas down to a simple sentence or paragraph. 

I learn a lot about my colleagues.  This is a specific case for this year because I co-mentored these companies with George, although I guess bits and pieces of it have come up over the years as I’ve roped other colleauges into other situations.  George and I brought different ideas and frames of reference to our sessions with SendGrid and Mailana, and it was fun for me and a good learning experience as well to see how George approached the same problems I did.  Call it a “peek inside George’s brain.”

Hopefully I will get invited back to TechStars again next year as a mentor – it was great fun, and I’m incredibly proud of Pete and Isaac and their teams with how well they presented their companies yesterday!

Jul 282009

Book Short: Worth Buying Free

Book Short:  Worth Buying Free

The cynic in me wanted to start this book review of  Free: The Future of a Radical Price, by Chris Anderson, by complaining that I had to pay for the book.  But it ended up being good enough that I won’t do that (plus, the author said there are free digital versions available — though the Kindle edition still costs money).  At any rate, a bunch of reviews I read about the book panned it when compared to Anderson’s prior book, The Long Tail (post, link to book).

I won’t get into the details of the book, though you’ll get an idea from the paragraph below, but Anderson has a few gems worth quoting:

  • Any topic that can divide critics into two opposite camps — “totally wrong” and “so obvious” — has got to be a good one
  • Free makes Paid more profitable
  • Younger players have more time than money…older players have more money than time
  • Doing things we like without pay often makes us happier than the work we do for a salary
  • It’s true that each generation takes for granted some things their parents valued, but that doesn’t mean that generation values everything less

While Free is s probably not quite as good as The Long Tail, it does a good job of organizing and classifying and explaining the power of different economic models that involve a free component, and I found it very thought provoking about our own business at Return Path.

We already do a couple forms of Free — we practice the “third party” model, by giving things away to ISPs but selling them to mailers; and we practice Freemium by providing Senderscore.org and Feedback Loops for free in order to attract paying customers to our testing and monitoring application and whitelist.  But could we do others?  Maybe.  They may not be revolutionary, but they’re smart marketing.

As some of the reviewers write, the book isn’t the be-all-end-all of marketing, it overreaches at times, and it is more applicable to some businesses than others, but Free was definitely worth paying for.

Filed under: Books, Business, Email


Jul 232009

A David Allen nightmare

Originally uploaded by heif

A David Allen nightmare

The comments on Flickr are almost as funny as the picture, but for those of you who can’t see the detail, I believe this is Esther Dyson peering over an inbox that has almost 4.3 billion emails in it.

Filed under: Current Affairs, Email