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Hi, I’m Brad Feld, a managing director at the Foundry Group who lives in Boulder, Colorado. I invest in software and Internet companies around the US, run marathons and read a lot.

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Scaling Up Yesware

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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.

Go Fill Up Some Gas Tanks Today

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I’m spending the day working at Yesware. I’ve been an investor from inception and love what this company is doing. I also love the culture – I wrote about it in my post The Monastic StartupIf you use Gmail and Salesforce and are not also using Yesware, take a look at email for salespeople right now.

It’s an atypical day for me. I was supposed to be in DC all day today and tomorrow. I had full days of meetings, including two Startup Communities related events – one with the World Bank and one with a Congressional Caucus on Innovation. I had a few company meetings along with some stuff I was exploring. And I was going to drop in on 1776 and check it out.

Congress decided to shut down for the week because of the pending snow storm so the two events I built my trip around (the World Bank and the Congressional Caucus) were cancelled. So I decided to punt on going to DC and stay in Boston. I decided to have a “work at one of the companies I’m an investor in” day and get caught up on some stuff.

Last night before dinner I had a phone call with someone who gave me a great metaphor about “filling up your gas tank.” We were talking about the introvert / extrovert dynamic and how always being in “give / support mode” drains an introvert like me. He suggested that I make sure I do things on a daily basis that fill up my gas tank. Yup – that makes sense. But then he said something that was a new thought to me.

“Encourage everyone you work with to put some gas in someone else’s tank every day.” 

It’s totally consistent with my give before you get philosophy, but it’s got a nice twist. Rather than being random, be deliberate about doing it, but random about how you do it.

For example, when a friend of mine had testicular cancer last year, I called him every day for 60 days during his chemo regimen. While I only talked to him every two or three days, I always left him a message. I was filling up his gas tank a little each day.

Another example is that I try to randomly call a different CEO of a company I’m on the board of every day. I don’t manage to do this every day, but I try. These are short calls, often voice mails that just startup with “Hey – thinking of you – no need to call me back.” I then often offer up an observation about something positive I see going on.

I like to be impulsive when I’m on the road. After lunch (I took out the Yesware team and yes, I paid) I stopped by Kinvey‘s new office on 99 Summer which is around the corner from Yesware. Kinvey went through TechStars several years ago and while we didn’t participate in their venture financing, I love the company and especially the CEO Sravish. I surprised him, gave him a hug, got a tour of the place, grabbed a few tshirts and some stickers, and headed back to Yesware. He sent me a link to a new post they just did titled The Boston Startup Map: Visualizing the City’s Tech Scene so I could do more random drop ins if I wanted.

bostonstartupmap

These aren’t programmed, scheduled calls in that I’m being deliberate in advance. They are just me filling up someone else’s gas tank with some random positive feedback in the midst of an otherwise chaotic life. And it makes me feel good.

So – go fill up some gas tanks today. And tomorrow.

Yesware Is For Salespeople

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Yesware just announced a $4 million financing. I’ve joined the board. If you are a salesperson who uses Gmail, go download and try it now.

I’ve been using Yesware since the first alpha release. While I’m theoretically not a salesperson, I believe every CEO and professional plays the role of a salesperson. And many people, especially in young, fast growing companies, are salespeople even if that’s not their title. As far as I’m concerned salespeople are the unsung heros of most US companies.

The brilliance of Yesware is that it was conceived and built by salespeople, for salespeople, from the perspective of living in email. Most salespeople I know live in email, hate their CRM system, and are constantly switching between the two while bemoaning the idiocy of the whole thing. The whole CRM thing is for sales managers who want to actually track what the salespeople are doing. But it’s all about email for the salespeople. And that’s what Yesware is focused on.

As a seed investor in Yesware, it has been pretty awesome to watch the product evolve and and the user growth spread to over 40,000 users through word of mouth only. As a result of our word of mouth approach, the product has to be great and responsive to the users.

As an investor, I’ve encouraged the team to push a new release once a week, focus on both registrations and daily active users, and instrument every aspect of the product so we can see what’s happening at a very granular level. While Yesware is only available for Gmail, it’s been an outstanding platform to iterate aggressively on and get this kind of feedback. Now that Yesware has nailed the use case with the seed financing and has a serious user ramp happening, it’s time to go after Outlook.

I’m psyched for the Yesware team and proud to be involved with them.

The Monastic Startup

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Last week at our Yesware board meeting, we talked about the idea of “the monastic startup.” This was a phrase that Matthew Bellows, Yesware’s CEO, came up with, and it characterizes the culture they are creating at Yesware. It embodies two concepts:

The monastic startup is a place where engineers do the best work of their lives. This place involves work with long stretches of uninterrupted time.

This idea sung to me. As I sit here in front of my 30″ monitor, working away in the peacefulness of my office in Boulder, surrounded by 10 of my favorite people (the gang I work with), listening to Lady Gaga, and connected to thousands of others via the computer in front of me, I realize that I long for more “monastic startup” time.

When I think about the culture of many of the companies we are an investor in, the definition of the monastic startup rings true. Oblong immediately comes to mind for me. Kwin Kramer, Oblong’s CEO, wrote an awesome guest post on TechCrunch over the weekend titled The Next, Next Thing. Oblong is one of the most monastic startups I’ve every encountered (using the definition above) – even Kwin and his partner John Underkoffler still spend long stretches of time writing code as they do the best work of their lives.

In my networked world (vs. hierarchical world) a monastic approach works amazingly well. I’ve started experimenting with more non-in person tools to increase the quality of communication across my network, while preserving a level of “monasticness.” The Yesware guys use HipChat for persistent chat. I’m looking for others – suggestions? I’m especially interested in things that work well across organization and communities.

If the phrase “monastic startup” rings true to you, what are the other characteristics that you’d expect to have in this environment? And what tools would you use?

Google Apps Marketplace Ecosystem

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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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