Posts from Email

Gmail Meter

I tried out a new service this past week called Gmail Meter. It's a free analytics service that tells you stuff about how you use Gmail. It is brought to market by the folks at ShuttleCloud, which does archive and data migration for cloud services. It's a way for them to get to know folks who might become ShuttleCloud customers in the future.

I learned a few things. I get 6,470 legit emails a month from 1293 different senders. I send/reply to 2,676 emails to 777 people. So the send/receive ratio across my inbox is 41% which is higher than I thought. I feel a tad better. But there are also at least 516 people who sent me an email last month that did not hear back from me. That makes me feel a bit worse.

The single highest send/reply ratio in my world is the Gotham Gal who sent me 133 emails of which I replied to 100, for a 75% return rate. I've got work to to do there. Sorry Jo. My partners Albert, Andy, Brad, and John get between a 50% and 70% reply rate. Sorry USV folks. The one cohort that I send more mail to than I get replies from is my three kids. I get a worse response rate from them than all of you get from me. Not sure how I feel about that.

This chart will not surprise anyone here at AVC but it does show that the one time I reply to more email than I get is the 5am to 7am time frame.

Daily traffic

Here are a few more interesting charts:

More gmail meter charts
The first chart shows that I get to most of my email within 24 hours but there is certainly a meaningful percentage that takes longer.

The second chart shows that I send a ton of short emails. 80% of my email is less than 30 words. Whereas greater than 50% of the emails I get are longer than 100 words.

I've asked the Gmail Meter folks to add a chart showing reply ratio on emails less than 30 words versus emails greater than 100 words. When I get that chart I will publish it here because I think that is single best secret to getting a reply from me.

Anyway, I found this data valuable. Maybe you will to. You can try it out at Gmail Meter.

#email hacks

Help Wanted: A Gmail Hack To See Only Replies To My Sent Messages

I get behind on email a lot. I am right now actually.

At times like this, I often want to use gmail hacks to make sure I am seeing the most important email. I have some that showcase the messages from my most important contacts (my wife, my kids, …).

But another super important cohort of email messages are the replies to the emails I have sent in the past few days (or up to a week).

I'm wondering if anyone has a good hack that will reveal only those messages in the inbox. I'd be super appreciative.

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#email hacks

Email Intelligence

I am in my second decade as a board member on several companies. It doesn't happen often in the VC business, at least my VC business, because I get off the boards of companies that go public or are headed there shortly. The percentage of portfolio companies that don't shut down, sell, or go public within a decade of their initial VC investment is low. But the ones that make it into their second decade without an exit are special in many ways. They have staying power, an ability to evolve and grow, and a culture that is built to last.

The company in that group that this community is most familiar with is Return Path. Executives from Return Path, including its founder and CEO Matt Blumberg, have written guest posts here a few times. Return Path has reinvented itself three or four times in its history. And yesterday they did it again. They are now the global leader in email intelligence. They actually have been that for quite a while. But they gave themselves that label yesterday.

What is email intelligence? Well in Matt's words, it is:

[Emailers] are struggling with two core problems that complicate their decision making: They have access to so much data, they can’t possibly analyze it fast enough or thoroughly enough to benefit from it; and too often they don’t have access to the data they really need.

Meanwhile they face new challenges in addition to the ones email marketers have been battling for years. It’s still hard to get to the inbox, and even to monitor how much mail isn’t getting there. It’s still hard to protect brands and their customers from phishing and spoofing, and even to see when mail streams are under attack. And it’s still hard to see engagement measurements, even as they become more important to marketing performance.

Our solution to these problems is email intelligence. Email intelligence is the combination of data from across the email ecosystem, analytics that make it accessible and manageable, and insight that makes it actionable. 

In connection with the new reformation of their company's mission and position in the market, Return Path launched or relaunched three products yesterday. The one that is truly groundbreaking in my opinion is called Inbox Insight. Think of its as ComScore for Email. If you want to know how your mail is doing compared to your competitors across a number of key metrics like engagement, inbox placement, spam complaint rates, etc, you can learn all of that and more with Inbox Insight.

Starting, building, and running companies is hard work. I know this because I see it in the eyes and wrinkles of the people I work with every day. But building a lasting, evolving, growing, and market leading company is a terrific feat. I want to congratulate Matt and the team at Return Path, most of whom have been there as long as I have, on a big day yesterday and a great new tagline, mission, and market position. Well done.

#VC & Technology#Web/Tech

The Black Hole Of Email

I have never ever been so behind on email as I am right now. I believe I am seeing about one third of all email that is sent to me. If you have sent me an email that I haven't replied to, don't be offended. You are not alone. You are in the majority.

I write these posts occasionally to let people know. The result is hundreds of comments about how I can make email work better for me. Please don't leave those comments. I don't want to make email work better for me. I don't want to hire an assistant to do email for me. I don't want to try some new magical app that will make email better for me.

I give email an hour in the morning, an hour in the evening, and I dive into it throughout the day. The result is probably three hours a day in total. That's all I'm going to give email. And it is not enough to manage the inbound flow.

So I'll do what I can and I'm not going to do more. And if that means I will miss your email, then so be it. Please send it again. That will increase the chances I will see it.

#Random Posts

Feature Friday: Mark Unread In Gmail

This post will explain a lot about my disorganized organization system. I am not very organized. I am a brute force type. My desk is a mess. My computer is a mess. But I somehow power through things and get the important stuff done.

I manage my email via the inbox. I label some messages but rarely use the labels as a place to read and reply to email. I star some messages but only visit my starred messages about once a week. Mostly I attack my email from the top. In reverse chronological order.

So one of my favorite features in gmail is "mark unread." I'll open an email, see it has something important in it, and then mark it unread so I make sure it stays in my priority inbox and that I get to it. I use that feature at least 10-20x per day.

But I can't for the life of me find that feature in the current gmail for android app. I do more email on my phone than anywhere else so I badly need this feature. I'm wondering if its in a place that I haven't looked or it google left it out of the app.

If anyone out there knows how to "mark unread" in gmail for android, please let me know in the comments.

And I'm sure there will be all sorts of great suggestions for getting more organized with email in the comments too. Just don't count on me doing any of them. It's like meditating. I know I should do it. I just can't bring myself to spend the time on it.


How To Get Your Emails Read

Last night I did my annual "fireside chat" with the InSITE Fellows followed by beers at a local bar. This has become a tradition and one that I enjoy very much. We ended up at Amity Hall where we drank beer, hung out, watched the Knicks do a late game fade against Orlando, and talked a bit of shop. Nishta asked me how to get to her email read. We had some fun with that and turned it into an experiment (yes, she automatically got into my priority inbox) and then a test. I'll let her tell the story:

I men­tioned some­thing and he said, “send me an email”. I instan­ta­neously and quite uncon­sciously replied, “oh come on, you don’t check your emails.” And he said, “I do”. After 2 mins of back and forth, he took out his [Android] and showed me his inbox — sorry, his pri­or­ity inbox. He said, “see that email, now thats a nice sub­ject, I will check it.” “But what if my email gets stuck in your reg­u­lar inbox?” was my imme­di­ate ques­tion? “Then, noth­ing can hap­pen. So you need to at least make it to my pri­or­ity inbox, can you?” “I will find a sub­ject inter­est­ing enough for you then” He smiled and said, “lets try”. I did and both of my emails even­tu­ally showed in his pri­oir­ity inbox few mins later!

She's right. First you need to get into my priority inbox. I am not entirely sure how you do that but Nishta and I have never exchanged emails before and she got into it on the first try.

But second and way more important, you need to get me to open your email. Subject line matters! Use a name I am familiar with in your subject line. Or something else that will get my attention. Here are six subject lines from yesterday, along wtih comments.

"Had lunch with Alexander Ljung" – that works. Alex is the founder of our portfolio company Soundcloud

"Two things" – that doesn't work. Two things is worse than one thing. And not descriptive.

"Pleasure speaking with you" – that doesn't work. I speak to so many people ever day. Not descriptive.

"Twitter board date change" – that double works. Portfolio company name plus very descriptive.

"I know you are a busy man" – that doesn't work. Not descriptive.

"ECB violation" – sadly that works. but please don't send me emails with that subject line.

The point is this. I scan all my mail many times a day and open and reply to all of it that I can. Senders matter. Subjects matter.

And there is mail that gets opened that doesn't get replied to. If the message is super long or the ask is not obvious, I will just sigh and move on. So be brief and specific with the message and the ask.

I like to reply to your emails. But I get so many of them. Make your emails distinctive and easy for me to reply to. Let's start a conversation and a relationship. Like I did with Nishta last night. She's getting her emails replied to now.

#VC & Technology

Super Priority Inbox

I love gmail priority inbox. I can't imagine doing email in an email client that doesn't have this feature. For those who are not familiar with priority inbox, it's a feature that splits the gmail inbox into three sections.

The top section is your "priority inbox." Google tries to figure who are the most important mail senders to you and it puts their mail in the top section. You can and should train it by using the +/- buttons to identify who is actually priority and who is not.

The middle section is the emails you have starred to return to later.

The bottom section is "everything else." For me this is mostly mail I don't want or need but it not technically spam. I do a quick scan of my "everything else" mail every day or two and pull the one or two emails out of it that I want and then delete the rest.

Now that we've gotten through what priority inbox is and why it works so well for me, I'd like to suggest a new feature to the gmail team. I'd like a "super priority inbox" which would be a fourth section on the page and above everything else. I'd enter the email addresses of a couple dozen people who I always want in my super priority inbox.

I know you can do this with filters and labels. I've done it. But the layout of the main inbox page in gmail is powerful. If I have to click over to a label to get to a filtered view, I just don't do it regularly.

One last thing about priority inbox and super priority inbox – it is even more awesome on mobile. The gmail client for android supports the priority inbox and ideally would support the super priority inbox when this feature is rolled out 🙂

UPDATE: Seems like this may be supported already. I got this comment below. I will try it out later. So excited.

Hi Fred – you can do this now..

goto settings, select priority inbox

There is a section called priority inbox sections:

1. Important and unread Options
2. Starred                              Options
3.                   Options
4. Everything else              Options

You can set the first to be the label that you have predefined, second to be important, 3rd starred, and 4th everything else.


M&A Case Studies: WhatCounts

We continue with our M&A case studies on MBA Mondays. Last week we saw the impact VCs can have on your exit. This week we are going to look at the opposite situation: what happens if you've entirely bootstrapped your company. AVC community member @daryn introduced me to David Geller who, over ten years, bootstrapped, built, and sold an email company called WhatCounts. It's a great story, but a bit long for one blog post. So we've cut it in two. This week, the events leading up to the sale. Next week, the sale itself.

As always, the comments will be the most interesting part of this dicussion. Make a point to stop by, check them out, ask a question, or answer one.


Daryn Nakhuda, a friend, Fred Wilson groupie, former colleague and my co-founder at Eyejot before he left to become CTO at, suggested to Fred that I write about my company WhatCounts. WhatCounts was bootstrapped several years ago and was recently acquired. I agreed to accept the invitation knowing that bootstrapping is a sometimes under-appreciated funding path that startups often dismiss too quickly. Why is that? What's the attraction for new businesses, particularly technology-focused ones, to seek VC funding?

Iʼm a believer in self-funded companies. When I started WhatCounts it was seeded with $50K of my own money. It grew organically to be successful and was acquired in late 2010. With my co-founder, Brian Ratzliff, we were able to operate the company autonomously. Initially, I did all the product development and Brian orchestrated our sales and marketing programs. We jointly pursued new clients. Brian had more formal business training, including an MBA, but we both shared the same pragmatic approach to operating and growing a business. We liked the independence that came with self-funding and knew that the success, or failure, of our venture would hinge entirely upon our ability to win and keep business. Instead of VC funding we used customer funding. Our exit event was successful and the transaction benefitted the companyʼs original shareholders without any dilutive effect.

Is bootstrapping your business and funding it without outside capital a good idea? It was for us, but I have to admit that we arrived at that position more out of necessity than prescient planning. We actually tried to attract outside funding, without success, when we founded WhatCounts in 2000.

A brief introduction to WhatCounts may be useful.

WhatCounts developed a SaaS platform for creating, managing, deploying and analyzing mass email campaigns for transactional and marketing applications. It grew from the two of us to 50 employees and attracted clients like Costco, Alaska Airlines, Virgin America, MSNBC, FOXNews, Ziff-Davis, Pandora, REI and many other, well-known consumer-facing brands and media organizations. Many of you received emails over the years that were generated by our platform. WhatCounts became known as a technology innovator (later releasing an on-premise appliance solution to compliment the SaaS offering) and a company that did a surprisingly good job (for its size) attracting prestigious clients and providing them with exemplary service.

Thus far, so good.

We decided to do some informal investigating to see if WhatCounts could get VC funding. Using contacts Brian and I had established during our time working at Paul Allen's Starwave (me running an engineering team and Brian a marketing team) and later at other startups, we setup informational interviews with a few Seattle VC firms. Not surprisingly, our few meetings failed to generate a lot of excitement. Weʼre both good communicators and present strong messages, but I suspect the VCs we visited knew that we didnʼt believe in the hockey stick growth story – for us or anyone else in our space.

As cool as we thought what we were doing was (or was going to be), we also came to realize that the email industry, in the 2000-2001 time-frame, was not an overly attractive investment space for VCs. This was certainly true for pure email service providers, of which we were one. Other businesses involved in email were still garnering excitement from investors. Fred mentioned the 2002 merger between Return Path and Veripost in his Dec 6, 2010 post. He highlighted the fact that both of those firms had received VC funding. When we started we were confident weʼd be successful operating a small business but didnʼt believe we were going to turn the company into a $100 million juggernaut. We became convinced that we would not be able to grow to that level in the time horizon we believed VCs were typically interested. We also looked suspiciously at some of our competitors that were making VC-friendly (and overly optimistic) growth projections.

Now, we could have retreated and tried to retool our business model and presentation materials in preparation for a new round of meetings. We could have created a more exciting story or twisted things to appeal to our potential investors. But we liked our business model. Our customers did too. We were making money! We knew that if we decided to ignore outside funding opportunities weʼd potentially be jeopardizing our chances of growing the company at an accelerated pace. But the benefits we saw and were experiencing running things ourselves seemed to out-weigh the potential value and overhead VC funding would deliver.

To recap, the facts Iʼve described, so far, are the following: (1) we started a company; (2) we had some early VC meetings; (3) we didnʼt gain much traction from those meeting (admittedly we didn'tʼ try very hard);  and (4) we settled back onto our original plan of utilizing a customer funded growth strategy.

One of the most obvious benefits to a simplified, self-funded growth strategy is that if youʼre lucky enough to grow the business and get acquired youʼre going to gain all the benefit from that transaction without sharing it with outside investors. Calculate your ownership position and compare it with a diluted position after one round of funding. Then identify the intersection where they deliver the same benefit to you. Now consider a second round of funding and further dilution. Or a third. Of course, building simplistic models like this is for illustrative purposes only. Yet, itʼs important to know that a bigger piece of a smaller pie, at some point, is the same as a smaller piece of a much larger pie.     And, donʼt let anyone tell you that baking a bigger pie isnʼt a whole lot more difficult.

Self-funded businesses, by their very nature, involve fewer outsiders. So there are control benefits that can be enjoyed in their absence. Fewer outsiders dictating (or strongly suggesting) direction means that you will be able to pursue your goals more closely and with less friction. Back in 2001 Brian and I knew we had a great platform. Our customers told us so. Slowly, but surely, we started gaining traction by winning new customers. Weʼd hire additional staff whenever we had a large enough financial buffer to keep them employed even if our growth were to slow or even regress a little. Itʼs the model we had been told Microsoft had adopted early on. We both felt personally responsible for every person that trusted us and trusted our vision enough to join the firm. Many of the people that joined WhatCounts had sacrificed potentially higher salaries from larger companies to work in an environment that was smaller, people and pet friendly and somewhat more lifestyle-oriented – with the belief that we would grow. So, we tried to make sure there was always enough in the bank to cover payroll for approximately six months. We also disbursed bonuses to everyone each year.

Despite our early success, we were still aware that we were a relatively small company. When new competitors began appearing we decided to consider additional sources of funding. We had about $1 million in the bank but, with an increasingly growing employee base, considered a large portion of it to be part of our special payroll reserve. That led us to apply for an SBA loan that was quickly approved and provided us with an additional $500K in the form of a line of credit. We never needed to draw on the credit line and turned it off within the first year.

Throughout the years WhatCounts continued to grow. New engineers were hired. Our support and account management teams grew. New leadership for engineering, sales and customer service all helped the company to mature and appeal to larger, more sophisticated clients. The business continued to invest in our technology and the infrastructure required to support ever-increasing client expectations and requirements.

Two events in 2010 proved to be important for the company. First, after operating the business for almost ten years Brian and I decided to see if we could find a buyer. We had started to see consolidation in the space and M&A activity appeared to be increasing after an almost two year lull. Second, a few weeks after inking terms with a banker we were approached, literally out of the blue, by another firm about the same size as WhatCounts asking if weʼd consider being acquired. They had the backing of a large PE firm and quickly delivered an LOI. The process that began with their first phone call and ended with their acquiring our company was complex, challenging, long and, at times, nerve racking.

Next week Iʼll share some of those details with you.

#MBA Mondays

Email Pain

My partner Albert wrote a post about email today. In it he says:

I just don’t see a way anymore of answering everything that hits my inbox and theoretically should get an answer.

It's a familiar tale and I sympathize with Albert. I have been struggling with this issue for years. I've blogged endlessly about it and you all have been very helpful with suggestions. I moved to gmail which has helped. I use labels and shortcuts which help. I use priority inbox which helps. But everytime I make a productivity gain, the volume eventually overwhelms me.

One of our portfolio CEOs told me an entrepreneur complained to him that "fred wilson never returns my emails." That hurts to hear but I suspect it is more true that I want to admit.

Like Albert, I am sorry. I wish I could return every email I get. But I can't and I don't. In the past I've suggested everyone out there just keep trying. I'm beginning to wonder if that is good advice.

I've thought about getting an email assistant. But I am worried that putting more capacity into the system will simply create more volume that will eventually overwhelm the increased capacity.

So I've decided to adopt other approaches to be more available to entrepreneurs, like office hours, meetups, more skype chats, more blogging, more events. I'm not sure if that is better either, but it's where I'm headed at the moment in my never ending effort to solve this problem.

#VC & Technology

The Impact Of Priority Inbox

I've been using Gmail's Priority Inbox for a while now. I like it very much. But it has one impact that is worth pointing out.

If your email gets into the third section of the main page, called "Everything Else", I most likely won't see it unless I see it on my Android phone. And hopefully Google is working on bringing Priority Inbox to Android. When that happens, I won't ever see it.

Everything Else is like the spam folder with one exception. The email will come up in the search results.

This may not be everyone's use case. I get a lot of email and I can't get to all of it regardless of what email client I use. Other Priority Inbox users might actually read through Everything Else. But I don't and can't.

Google has solved a huge problem for me and potentially created a huge problem for emailers.

The email deliverability business, where we have an investment in the market leader Return Path, will be impacted by Priority Inbox and related services. Deliverability will increasingly mean getting into the Priority Inbox. And that's a hard thing to do.