Tag: gmail

May 7 2018

The New Gmail For 2018

Ahhhh. The new Gmail client for the web is finally here. And a lot of things are fixed. The two things I like the best are really simple but dramatically increase my email throughput.

+name: When I add someone to an email thread, I use the shortcut “+name” to indicate to everyone on the thread that I’ve added them. I started doing this around 2008 (I can’t remember where I picked it up from, but I think it might have been Mark Pincus at Zynga.) It started appearing in some Google apps a few years ago (Docs and Inbox) and it is now in the main email client. For example, if I want to copy Amy on something, instead of having to put her email address in the To: field, I now merely need to say +Amy Batchelor in the body of the email and Gmail does the rest. Yay – finally.

Send threading: If you are on a fast internet connection, this won’t matter to you. But, if you do email on a plane or a house in Longmont, Colorado (where I regularly have internet performance that is < 5 MB) you will love this feature. The only annoying thing is the endless (and unnecessary) popup that informs you that Gmail has sent your message (it’s no big deal on a desktop, but bothersome on a laptop.) Either way, I no longer have to sit and wait while Gmail is trying to complete the send process.

My guess is that the combination of these two features increases my email throughput by 25%. And, for someone who processes hundreds of inbound emails a day, this helps a lot.

There are a lot of other fun things under the hood and a nice new paint job on the surface. Nothing is dramatic, but overall it’s definitely an update. If you haven’t gotten it yet, tell your Google administrator to turn it on for your domain. Then click Settings in Gmail (the little gear icon on the top right and select the first option “Try the new Company Name Mail”.

Update: In my ongoing love affair with Canada, it turns out that Google’s new version of Gmail made in Kitchener.

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May 20 2016

Why Do Apple iOS Mail and Calendar Apps Suck?

Before I get into my rant of the morning, if you have a gluten intolerance, or just want less gluten in your life, we just invested in a company called Nima that can help you.

Today, as I was going through my daily reading, I read Fred Wilson’s Feature Friday: GBoard about Google’s new third-party keyboard app for iOS. I clicked on the link to download and try it and, as it was doing its thing, though to myself “why does Apple iOS Mail suck?” And then I thought “why does Apple iOS Calendar suck?”

When I’m using my iPhone, I spend a lot of time in Mail and Calendar. I’ve always been unhappy with Apple’s Mail and Calendar. I’ve gone through using lots of other ones, but in most cases, once the Mail or Calendar app is acquired by another, bigger company, it eventually stales out and vanishes. About a year about I started using Outlook on My iPhone and used it for a long time. I can’t remember what happened, but at some point I abandoned it and switched back to Apple Mail and Calendar.

As Gboard was downloading, I decided to try Gmail and Google Calendar on iOS for a while. I used them when they first came out and they were inferior to Apple’s Mail and Calendar. I tried them again about a year ago and they were good, but for some reason I didn’t stay with them.

I know that if I don’t use something for at least some extended period of time it won’t stick. Some I’m going to try having Google World on my iPhone until at least June 1st. At that point I’ll re-evaluate.

If you have any hints or suggestions, I’m all ears.

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Mar 1 2015

How To Deal With Email After A Long Vacation

Since I’ve had dealing with email on my mind recently, I thought I’d write about how to deal with email after a long vacation. Over the years, I’ve heard over and over again from people who never going on vacation or getting off the grid explaining that they can’t imagine doing this because they would be more stressed out when they return to all the email they have to respond to. I don’t think it has to be that way.

For context, I’m a huge believer on completely going off the grid for vacation. Amy and I have been taking a weekly vacation off the grid for 15 years. No phone, no email. Just the two of us. Given the pace of our lives and the amount of time we spend apart, it’s an awesome way to reconnect. There’s nothing quite like spending a week with your beloved on a periodic basis to remember why you love each other.

Whenever I’m off the grid for a week, I always come back to loads of email. I used to organize my trips from Saturday to Saturday so I’d have Sunday to go through all my email and catch up. That works, but ruins the last Sunday of the vacation. Then I shifted to Monday, so I basically scheduled nothing on Monday and just went through all my email during the day while getting back in the flow of things. That made for a shitty Monday and usually damaged my calm that had resulted from my week off the grid.

When Amy and I took a one month sabbatical in November, I tried something different. Here is my vacation reminder from that trip.

I’m on sabbatical and completely off the grid until 12/8/14.

I will not be reading this email. When I return, I’m archiving everything and starting with an empty inbox.

If this is urgent and needs to be dealt with by someone before 12/8, please send it to my assistant Mary (mary@foundrygroup.com). She’ll make sure it gets to the right person.

If you want me to see it, please send it again after 12/8.

My partners covered for me when I was gone and dealt with anything that was important. The three of them had each taken a month off before my sabbatical so we had a nice rhythm around this.

At the last minute I chickened out on archiving everything without looking at it. Instead, I just scanned through my inbox, archiving messages without responding to them. I didn’t save anything, even if it asked me to do something. I archived it just like I said I was going to. But I had some context around what was going on. It took me about three hours to get through the 3,200 emails I had waiting for me. Not surprisingly, when you don’t send any emails, you get a lot less.

On Monday morning (12/8) when I came back to the office, I had an empty inbox except for the emails that had come in since I did the scan (which I did on 12/6 – we traveled home on 12/7). It was unbelievably liberating. I sat down with each of my partners and went through things that had happened when I was away in companies I was on the board of. That took less than 15 minutes per partner. At lunch, I got caught up on the overall portfolio.

By Tuesday I was back in the flow of things and felt very calm and relaxed. My vacation mellow wasn’t harshed at all.

This approach works for any length of time. Amy and I took a five day off-the-grid vacation for Valentines Day week. Same drill, although this time I responded to a few emails that came in when I reappeared and did my scan. But I set the expectation that I wasn’t going to look at anything, so plenty of “resends” happened on Monday and Tuesday, which meant that folks who really wanted to interact with me took responsibility for it.

There’s something about taking control of how email interacts with you that is very satisfying. I’ve heard the complaint, over and over again, that email allows other people to interrupt your world. That’s part of the beauty of a low barrier to communication (e.g. just send something to brad@feld.com and it gets to me.) But it’s also a huge burden, especially if you want to engage back.

I’m always looking for other approaches to try on this, so totally game to hear if you have special magic ones.

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Dec 24 2014

My Recently Erratic World of the Gmail Spam Filter

Let’s start with a brief history of my investment-led fight against the perils of spam and my never-ending love of SMTP.

We were investors in Postini and my partner Ryan sat on the board. It transformed my life – with one minor change of an MX record some time in 2002 all the spam in my inbox disappeared. Well – it disappeared before it got to my inbox. Or even my server. The awesomeness of Postini was that it was the first cloud-based email anti-spam solution. And it was a beautiful thing that Google acquired in 2007 for $625m.

One of the benefits of our investment in Postini is a life-long friendship with Scott Petry. Scott is the co-founder of Authentic8, which we are also investors in. Scott also sits on the board of Return Path, which is run by another life-long friend Matt Blumberg.

Scott worked at Google for three years after the transaction for Dave Girouard (who used to run all of enterprise for Google and now is CEO of Upstart and on the board of Yesware with me) integrating Postini into all of Gmail’s infrastructure. We continued to use Postini as our spam filter (in front of Gmail) until Google transitioned all of Postini into the Google apps service.

You get the picture. There’s a nice thread through all of this SMTP, email deliverability, and anti-spam stuff in my world, both in investment and relationships. So I generally don’t think much about spam since in the past it just disappeared, or well, never appeared in the first place.

When I came home from my one month sabbatical in Bora Bora, I archived all the 3200+ emails in my inbox. If you missed my vacation reminder during that time, it said:

I’m on sabbatical and completely off the grid until 12/8/14.

I will not be reading this email. When I return, I’m archiving everything and starting with an empty inbox.

If this is urgent and needs to be dealt with by someone before 12/8, please send it to my assistant Mary (mary@foundrygroup.com). She’ll make sure it gets to the right person.

If you want me to see it, please send it again after 12/8.

On Thursday, 12/4, Amy decided to scan through her email so I went to the business center at the St. Regis in Bora Bora with her and did the same. I simply started at the top and “read / archived” each of the around 3,300 emails (using the “[” shortcut). I’m a fast reader so I skimmed the emails I cared about. Mostly I just played a video game with the [ key.I might have had a tropical drink while I was doing this.

I didn’t respond to anything and just ran this drill again early Monday morning to finish up. I then turned off my vacation reminder, had Inbox Zero, and got started again.

Yesterday, I had a weird feeling that I’d missed something that I heard about in another email thread. I was procrastinating from working on the final edits to my new book Startup Opportunities (yes – I’m doing that some more right now, but I’ve got a nice empty day in front of me) so I randomly checked my Spam folder in Gmail. I never, never, never do this so I was suprised when on the first page I saw a legitimate email. I opened it, clicked on Not Spam, and scrolled to the next page, where I saw another one. And another one.

I had 5,500 messages in my spam folder since I got back on 12/8. I went through all off them – it only took about 10 minutes. I found 39 legitimate emails. Not notifications, not email newsletters – but real emails sent to me by people I often get emails from. Here’s a screenshot of the legit ones.

Valid emails in gmail spam folder

I did my dutiful work and hit “Not Spam” on all of them. I was perplexed and talked to my friends at Return Path who gave me some feedback.

This morning, I had 433 messages in my Spam folder. This time, they all looked like they should.

Screen Shot 2014-12-24 at 7.36.51 AM

I’m hoping that this was only a temporary glitch in the matrix. However, I’ll be checking my Gmail spam folder on a daily basis for a while. Boo.

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Dec 17 2014

Solve Your Gmail Contacts Problem

I live in Gmail. Gmail Contacts has been lame for a long time. Within an email, it’s even lamer on the right side bar, especially since it could be so amazingly useful.

FullContact has just released their FullContact for Gmail product. It’s a free download in the Chrome Store. I’ve been using it for about six months since and it’s just awesome.

I’ve been obsessed about the contact management problem for many years. In 2012 when we invested in FullContact, I wrote a post titled One Address Book To Rule Them All. FullContact has made great progress in the past two years on this problem while building a substantial enterprise API business. At the same time, we’ve been working extremely hard on a wide range of consumer products which are all just now rolling out into production (many have been in beta for the past year.)

I use all of them. FullContact for Gmail. FullContact for iOS. FullContact for MacOS. FullContact Web. All integrate with each Address Books on all my devices and computers. Everything syncs bidirectionally. Everything integrates with my contacts in Facebook, Twitter, LinkedIn, AngelList, and Foursquare. FullContact deduplicates everything so I only have one integrated contact record for each person. It enriches each contact record automatically with new public data that is finding on a continual basis.

This is a really hard problem. We invested in a company called Gist in 2009 – it was acquired early in its life by RIM in a deal that was financially successful for everyone involved, but before Gist rolled out in a big way. At the time, Gist was competing with several other companies, including Rapportive, all which were ultimately acquired and then more or less abandoned.

While we hoped to blanket the world with FullContact in 2014, we knew that waiting until we got the underlying massively large data infrastructure right, at scale, in a way that wouldn’t fuck up any contacts, was price of admission for going big on the consumer side. So we focused on building out our enterprise API business which started the year at a substantial level and tripled in 2014. At the same time, we acquired a company called CoBook and went extremely heads down on getting to a place where we thought we were ready to fix everyone’s address books on Planet Earth.

We are there. FullContact for Gmail is the first product to be released. If you are a Gmail user, quit fooling around, download it, and make your life a lot better right now. And get ready for several more releases in the next few months.

The FullContact team works as hard as any team I know. I’m proud of you guys and glad to be on this ride with you to finally solve a problem that has vexed me my entire adult life.

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Sep 19 2013

Scaling Up Yesware

Yesterday Yesware announced that Battery Ventures led a $13.5m round that we participated in. A few days ago Xconomy wrote a great article about the very first Yesware board meeting on April Fools Day, 2011. When I reflect on the journey of Yesware over the past 2.5 years it’s a pretty awesome example of a company going from a seed investment with three founders (Matthew Bellows, Cashman Andrus, and Raj Bhargava) to a rapidly growing 40 person company.

On 4/1/11 Yesware had a vision, a crappy prototype (that we threw away immediately after the financing), and a huge obsession around a vexing problem that no one was addressing effectively. Today they have over 300,000 users, a broad product set that includes a recently released deep integration with and between Gmail and Salesforce, and a leadership team and culture that is clear about what it is trying to accomplish and is true to itself.

In March, I wrote a blog post about Shifting My Focus To Scaling Up. When I look at our Foundry Group portfolio of over 60 companies, I see many of them in two distinct scaling up phases. The first are companies like Yesware that are rapidly growing revenue and customers, are in the 30 to 100 employee range, are dealing with balancing resources to accomplish their goals, but have an incredible amount of open ground in front of them. The second are companies like Fitbit that are clear leaders in their market, are on the 100 to 500 person ramp, and pacing the innovation in their market segment. Many of them are companies that aren’t overhyped because they are Silent Killers, a particular type of company we love to fund and work with.

Yesware has now shifted from the startup phase to the scaling up phase. There’s an entirely new level of organizational development, different set of challenges, leveling up of leadership and management skill sets, and massive opening of new opportunities given the resources that the company now has.

I find this a particularly exciting time in the life of a company. And a very challenging one. Fortunately, Matthew continues to surround himself with amazing people, such as his first outside board member, Dave Girouard, who recently ran the entire Google Apps business and is now CEO/founder of Upstart and his newest board member Neeraj Agrawal from Battery Ventures.

Plus, Matthew has a bunch of peers in our portfolio to talk to. We are together with many of them today in another Foundry Group summit – this time for full executive teams across our portfolio right in the middle of Denver Startup Week. Like all of our internal events, our goal is an extremely high signal to noise ratio. We leave the pomp and circumstance to others.

The enormous and powerful conversation around “startups” will continue. But as I turn more of my attention to “scaleups” I believe the next phase is even more powerful.

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Feb 6 2013

A Problem With Gmail When The Machines Take Over

In general, I love Gmail. While Amy likes to complain to me about how ugly it is, I don’t even see the UI anymore as I just grind through the endless stream of email that I get each day. My biggest struggle is figuring out how to keep up, without the email ending up dominating everything I do. In the past year, this has gotten a lot harder, but I continue to try new things.

That's a lot of email young man

Fortunately, spam is almost non-existent for me. We invested in Postini, which Google ended up buying, and it’s been a joy to have flipped a switch almost a decade ago and had spam go from “overwhelming” to “almost nothing.”

Every now and then, I get a flurry of spam from a new attack before Gmail figures it out. Today was one of those days – I had about a dozen things that looked sort of eBay notification like but with Arabic characters. So I hit ! and marked them each as spam as I was going through my inbox. Suddenly, my inbox reloaded and I got the following message.

But but but it's me!

I expect that by the time I finish writing this post I’ll have access to my inbox again. But stuff like this makes me physically uncomfortable – my morning routine was just interrupted and the machines decided I don’t get to access my email for a while.

While plenty of folks complain about the ambiguity and lack of precision around many of the issues surrounding Google apps, and more specifically the general lack of support, I usually don’t worry about this much. However, in the last month I’ve had two issues that caused me to remember that I’m increasingly less in control and the machines are increasingly more in control. This is one of them; the other was that I noticed an incredible slow down of performance of Gmail – just for me. After a week of pressing on it, the response from Google enterprise tech support was “you have too many things hitting IMAP – disable all of them.” A quick look at my Google Dashboard showed around 100 different apps that I’d authorized to access my account. I cut it down to about 30 – and got rid of several that I knew were high traffic that I liked, such as the awesome new Mailbox app – and things sped up again after 24 hours.

I recognize that if as we hand over control to the machines, they will make mistakes. That’s ok. But it’s jarring when one doesn’t have control over it, even for a little while. And yes, my Gmail is back up.

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Jan 5 2013

The Google+ Long Game Is Brilliant

I’m finding myself using Google+ more and more. I recently decided that the long game Google is playing is absolutely brilliant. They are being understated about it but doing exactly what business strategists talk about when they describe the long game as the one to play.

Rather than making a bunch of sweeping pronouncements, struggling to jam together a bunch of random crap in a big bang release, and then worry about staying involved in a feature race with a competitor, Google is continually experimenting with new functionality, rolling it out broadly in a fully integrated fashion on a continuous basis, and providing it as a core part of an ever expanding thing that is getting more and more useful by the week.

By now I hope you are saying something like “What the fuck is he talking about – Facebook is crushing Google+” or something like that. Yeah, whatever. That’s why it’s the long game that they are playing.

Here are some examples.

I live in GmailSuddenly, I found this magical thing called Circles to be useful. When I get behind on my email, I simply go through a few of the circles (Foundry, Foundry Ents) and clear the email from my partners, my assistant Kelly, and the CEOs I work with. I have persistent chat up – I find that 80% of my chats now go through Gchat (the other 20% are Skype, and they are almost always requested by someone else.) And now that there are Hangouts integrated, many of these are videos.

Google Voice is my Phone NumberI used to have desktop phones. I don’t anymore – I have a Google voice # and an iPhone. I give everyone my Google voice #. It works everywhere. I never think about what phone I’m using anymore. And I do many calls via the computer.

Google Hangouts is my new Calendar Invite. I hate the telephone. Hate hate hate. But I don’t mind chat. And I don’t mind a Google Hangout / video call. All of a sudden I can make invites from Google Calendar that are Hangout invites. Done – every phone call / conference call is now a Hangout.

I live in ChromeI have several computers. I never notice the difference between them. I’m downstairs at my place in Keystone right now on my Macbook Air. When I go up into my office, I’ll be on my treadputer with a different Macbook Air (an older one) connected to a 27″ monitor. I switch regularly between the two throughout the day and don’t even notice.

Now you are thinking “Ok Brad, but other than the Hangouts, Circles within email, and Hangouts within Calendar, what are you using Google+ for?” Just those three things have completely changed my workflow massively for the better. And they just showed up for me one day – I didn’t have to do anything.

In 2012 I used all the normal Google+ stuff. I reposted content there. I followed people. I occasionally chatted, commented, or +1ed. Facebook-like features. But I didn’t care that much about that stuff – yet.

All of a sudden I’ve got Communities. I’ve got Events. I’ve got Pages. And Hangouts, and Circles integrats seamlessly with each of these things. And they are nicely integrated with Gmail and Calendar. And suddenly I can do On Air Hangouts. And, I can record them automatically and save them to my Youtube channel. Keep playing for another few years, user by user, company by company, integrated feature by integrated feature.

Yeah, it drives me batshit that Google still things I’m brad@feld.com, brad@foundrygroup.com, brad@startuprev.com, and brad.feld@gmail.com. Some day they’ll integrate these. And as I approach 25,000 contacts, I’ll probably start bitching about how this limit is ridiculous, just like I did at 10,000. But I can deal with all of that.

Google – thanks for playing the long game here. I wish more companies, especially other tech companies, did this especially when they have massive resources. Sure – some think they are playing the long game, but they are really playing the short game with a bunch of things that take a long time for them to get out the door. Different game.

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Jan 30 2012

Connect to Facebook, LinkedIn, Twitter, and G+

I noticed something when I tried out two apps (Mingly and Cobook) this morning – they each immediately asked to connect me to Facebook, LinkedIn, and Twitter during their onboarding process. And, by using my Gmail as the starting point / authentication, they connected me to G+.

Microsoft is conspicuously absent from this. I’ve noticed this many times in the past but when you onboard yourself in two contact-related apps in the same morning and there is no Microsoft anywhere, there’s something going on that’s important. I wonder if this will change with Office 365 – I hope Microsoft is building a trivial to use oauth to O365 so it’s easy to connect to, along with a good sync API.

I was trying to think of other authentication that would be helpful to me in the context of my contacts. Almost everything else I use is based on either my email address or auth with one of these four services. Hmmm.

So far Mingly feels basically the same as Gist but Cobook seems different than anything I’ve used. I have no idea if I’ll keep using either of these, but like many things in the themes we invest in, I love to play around with new apps for a while and see if it sticks.

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Dec 12 2011

Google Apps Marketplace Ecosystem

Recently my partners and I spent some time discussing three of our recent investments – Spanning, Yesware, and Attachments – which are each applications built on top of Google Apps. Specifically, they are built for Google Apps and available in the Google Apps Marketplace or the Chrome Web Store.

Each company is going after something very different. Spanning is all about cloud backup. Attachments is all about getting control of your email attachments. And Yesware is “email for salespeople.” However, they have one very significant thing in common – they are all deeply integrated into Google Apps. In our thematic definition, they are in the Protocol theme.

The Google Apps ecosystem snuck up on us. We have all been hardcore Google Apps users for the past year and are psyched and amazed about all the easy integration points – both into the browser and the various Google Apps. In the past, we would have been more focused on “email as a datastore”, which would have resulted in multiple platforms, including of course Outlook / Exchange and IMAP. However, the pace of iteration on top of Google Apps, and the ease of integration is spectacular when compared to other platforms.

Notably, when the choice of building for Outlook vs. Google Apps comes up, many people who I know comes down strongly on the side of building for Google Apps. Their mindshare for cloud based business apps far outpaces Microsoft. A decade ago, Microsoft made a huge push with Visual Basic for Applications and the idea of “Office as a Platform” and – while plenty of interesting tech was built, something happened along the way and the notion of Office as a Platform lost a lot of visibility.

Theoretically Microsoft’s huge installed base of Outlook / Exchange users should drive real ISV integration interest, but the friction associated with working with Microsoft seems to mute the benefit. And – if you’ve ever built and tried to deploy an enterprise wide (say – 100,000, or even 1,000 seat) Outlook plug-in – well, I feel your pain. It’s possible that with Office 365, Microsoft will re-energize focus on Office as a Platform, but I haven’t seen much yet.

While Google has been building this all very quietly, I’m extremely impressed with what they’ve done. Companies like Yesware are able to release a new version of their app to all users on a weekly basis. For an early stage company that is deep in iterating on product features with its customers, this is a huge advantage. And it massively simplifies the technology complexity to chose one platform, focus all your energy on it, and then roll out other platforms after you’ve figured out the core of your product.

I expect to see versions of each of these products expand to work with Microsoft – and other – ecosystems. But for now, the companies are all doubled-down on Google Apps. And I find that very interesting.

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