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One year later: counterintuitive lessons about people

The past year has been one of change for me. I left the University of Michigan early, raised money for my startup Fetchnotes, and moved to Boston to do an accelerator called TechStars. I spent an extended stay back in Michigan during what would have been my senior year, and then came back to Boston. For me, the most interesting part of the journey has been the human component. A handful of things stuck out as counterintuitive, and given that today is Yom Kippur, a Jewish holiday for atonement and reflection, I thought posting this would be timely.

No one feels as awkward about yourself as you do.

"That girl saw me looking at her, she must think I’m so weird now," "Everyone in the audience can tell how nervous I am standing up here," "I’m saying um and uh so much," "I’m not making eye contact."

We often project our insecurities on other people, when in reality they’re too busy thinking about their own to notice yours. And if it turns out you’re actually as awkward as you think you are, big deal. Awkward people are endearing — go up and say hi to someone anyway. As outgoing and extroverted as I am, I don’t do enough of this.

We’re generally terribleat empathy.

It’s shockingly difficult for people to decouple themselves from their experience. For example, I forget that as the public face of the company, I have a lot more conversations with other people and take in more feedback/advice than the rest of the team. In doing so, my thinking subtlely evolves on how to describe our value, what strategies we should be employing, etc., and over time the difference can be quite significant. If I don’t relay that to the rest of the team, there can be a big gap in how we look at the same information.

Across all sorts of situations, I’ll find myself thinking, “How can you not agree with me about this?” or “How can you be so naive?” I forget that they haven’t had the same experience as I have, nor have I had theirs. It’s okay to disagree.

(For more thoughts on this, research “The Curse of Knowledge”

Our lives look way different on the outside.

We have blinders when we think about others’ lives, too. Every so often, someone tells me, “I’ve been following you on Facebook and it looks like your life is so incredible!” I post interesting stories that happen to me, good news about my company and photos of going exploring around Boston. It probably looks like some fantasy adventure. That’s because I don’t believe in bitching to social networks when something isn’t going well.

Yes, I’m pretty fortunate in my life. But you don’t see the extremely difficult conversations I’ve had to have with close friends, or the nights I’ve laid awake stressed out about any number of things. Like most 22-year-olds, I have the same BS to deal with about making friends in a new city, missing old ones and pretending to be an adult. I try to remember that when I look at other people’s lives with a limited perspective.

Compliments and genuinely giving a shit go further than you think.

For reasons unknown, I’ve always been awkward about giving/receiving compliments. In the last year (especially more recently), I’ve made a concerted effort to change that, and it’s had a very positive impact on my relationships.

Compliments, however, are just flattery if not coming from an honest place. You’d be amazed at how rare it is for people to show that they genuinely give a shit about another person’s well-being. The two nicest compliments I’ve ever received have been when I IMed a friend to see how she was feeling because I knew she was sick, and when I emailed an acquaintance to congratulate her on a new job when I saw her LinkedIN was updated. I had no expectations or motive. Both were floored that I took the time to reach out.

It’s not always words, either. Because families were an interesting market my company was considering targeting, Katie Rae (one of the managing directors of TechStars Boston) made our team “The Five Love Languages.” It discusses how there are generally five ways that people show affection for one another: words of affirmation, physical touch, gifts, quality time and acts of service. Depending on the person and relationship, you might be trying to show someone you value them by saying so, when doing something for them, or spending quality time with them, would mean a lot more. Understanding this nuance can save a lot of stress and turmoil.

There is zero downside to persistence. Err on the side of annoying.

When it comes to trying to get someone else to do something for or with you, there are only two types of people:

1) People who are going to do it
2) People who aren’t going to do it

Without fail, the people who are annoyed by you following up were never going to do what you wanted in the first place. The investor that gets annoyed by you following up was never going to fund you. The person that gets annoyed when you call because they didn’t respond to your text about plans tonight was never going to go out with you in the first place. The reporter that gets annoyed by your follow up emails was never going to write about you.

By the same token, people are busy and have other things going on. The people that were actually going to do something with you appreciate when you follow up, because it means that they didn’t miss out on an opportunity. More often than not, they were just busy and your message got lost. I actually know a non-insignificant number of people that ignore first emails from people because “if they don’t care enough to follow up, they’re not worth my time.”

With this in mind, there’s literally no downside to persistence. The people you piss off were never going to do what you wanted anyway, and the people who were are going to value you that much more.

Be persistent. Be memorable.

Chaos in consumer productivity

It’s an exciting time to be in the business of helping people get organized. 2013, especially this summer, has seen huge news across the consumer productivity software market:

-Astrid, 4M users, $400,000 in funding in 2011 led by Google Ventures. Acquired by Yahoo and shut down. 

-Orchestra pivoted into Mailbox, shuts down Orchestra to focus. Acquired by Dropbox for ~$100M. $5M A round in 2011 consisting of Charles River Ventures, Kapor Capital, SV Angel and Crunchfund.

-Catch Notes shutting down, 3.5M users reported, $9.3M from Excel Venture Management total ($2.3M seed and $7M A). No reason given (hypothesis from TechCrunch is that they’re focusing on the team version). 

-Evernote crossing 66M users. Evernote raised a set of large seed rounds too ($6M and $3M before a $6.5M A round in 2009). raised $3.5M earlier this year, after a 1M round in 2011. Investors include Genesis Partners, Blumberg Capital, Innovation Endeavors and Blumberg Capital.

Unlike the enterprise productivity sector (where revenue comes in quicker), consumer is much more dependent on gaining massive adoption, dominating a market and raising on growth. At first, I thought the shut-downs were related to the “Series A Crunch” (investors moving upstream to seed or downstream to B round or growth equity is creating a vacuum of funding at the A round). However, Catch and Orchestra both raised A rounds in 2011 — it seems that the shut-downs (or pivots) are more related to user bases not being able to break out of the “low millions.” As a result of the halting growth, they can’t raise the follow-on financing they need, or monetize enough to support their team sizes.

But survivors remain, and the attrition of companies is creating refugees that feed back into the remaining services. This creates wider separation amongst the remaining players, who are more likely to raise more money and earn a successful exit with more users. Besides my own company Fetchnotes, Wunderlist,, Springpad, Evernote and many others are still in business (principally focused on funded companies, since that’s where these dynamics matter most) and stand to benefit greatly from the disruption.

This competitive jostling happens in all sorts of consumer app verticals, though, so what’s so special about productivity?


Currently, the to do list industry in particular is immensely fragmented. Not a single app has over 1% market share in the mobile to do list space. That means that as products shut down and see their refugees strengthen existing services (either to do list apps or more flexible note-taking apps), we could be on the cusp of a major consolidation in one of consumer technology’s most competitive categories. Just think of search in 1998 (Google emerging from AltaVista, Lycos, Yahoo, AskJeeves, etc.) and social networking in 2004 (Facebook emerging from Friendster, MySpace, tribe and others). 

Whether we see a “big at the top” dynamic like social networking (Facebook, Twitter, Pinterest, Instagram), or a “gorilla vs. everyone” mentality like search (Google), the abrasion occurring today is going to define the “productivity app” market in the future. I’d also be on the lookout for companies that raised money > 2 years ago. Startups typically raise 12-24 months of capital so if they raised back in 2011 or earlier and still haven’t raised a new round, it could mean they’re having trouble and are likely to sell soon to salvage a return for their investors.

Do you think a king will emerge? Or will it stay fragmented? Email me your thoughts at alex(at)fetchnotes(dot)com.

How to ask startup people for introductions

I ask for and receive a lot of requests for introductions. Whether it’s someone at a company for a partnership or job, an investor, a journalist or something else, it’s an integral part of pretty much any profession. At the same time, such requests often arise in the least efficient way possible for the middle-man: in-person, in the middle of another email exchange talking about the other party, or simply with no details. Once I got involved in the startup scene with Fetchnotes, I found that this crowd has it down to an exact science. I’m sure similar rules apply outside our bubble, but inside it there are a very specific set of expectations, and it was a bit cryptic and counterintuitive to pick up at first. Hopefully this helps you maximize the success of your introduction requests!

First, no matter where the request for an intro arises, always send a separate request email. That way, the receiving party can act on it directly (since most intros are over email). You’re asking someone to spend their social capital on you, so your number one goal is make it as easy as possible. Here’s how:

Hey Alex,

Hope all is well! I saw you’re connected to Mark Zuckerberg. I was hoping to connect with him about a partnership (reason), the details of which are below. Do you know him well enough to make an intro (gives middle-man a way out in case they don’t know each other well)?

StartupWithFriends is an awesome new app that lets you start a company with your friends, right on Facebook (what you do). We have 150K+ active users, and on average they’re starting 1,000 companies per day (credibility + traction). We’ve been integrating with OpenGraph already (shows you’ve done work already, otherwise they often point you to their API page) but we think that we can make it a huge revenue driver for them if we get access to some of the data not available in their APIs, specifically the number of times a user looks at the profiles of their ex-girlfriends (basic benefits + needs outlined).

Let me know if you can make the connection. If not, no worries, I can reach out cold. (shows them you have balls and that this is going to happen one way or another)

Networker McAwesome

When I receive this email, I’ll forward it to Zuck (because we’re totally bros), and ask, “Hey, these guys were looking to connect. Can I make an intro?” If he says yes, I make the connection. If not, I say I tried but he doesn’t want to talk. Unless you know someone really well (or know they are looking for such opportunities), you want to give them a chance to say no. Otherwise, they’ll feel obligated to take it and have bad feelings toward the person from Day 1. Not only is it just good etiquette to give them a choice, but it prevents the value of your introduction from being diluted too.

Is it contrived? Obviously. Does the other party realize its contrived? Usually. And yet I write every email intro request in this exact format because it does three really, really important things:

1) Makes it easy for the middle-man to make the intro (just hit forward and type a sentence)

2) Gives the person you’re trying to get connected with a basic overview (so they feel more comfortable taking a meeting)

3) It limits the amount of aggregate back-and-forth

That makes the intro more likely to happen, the person you’re trying to meet more likely to take the meeting, and makes the most efficient use of everyone’s time. Happy connecting!

How To Find Anyone’s Email Address

I’m a biz-dev-minded CEO. That’s what I learned how to do in my time at Benzinga and that’s what I spend most of my time on at Fetchnotes — reaching out to people for advice, PR, investment (though that always comes through referrals), etc. Consequently, I find myself emailing people I don’t know on a daily basis. Recently, I learned about a neat hack you can use to find anyone’s email address.

Rapportive is a plug-in for gmail that gives you social data on the people you email. So when I type in “” it shows my photo, recent tweets, LinkedIN profile, etc. It would be nice if I used gmail’s web interface, but I need a desktop client to stay productive. It looks like this:

The best part? If it doesn’t recognize the email address as real, it shows a ? and no data. That means that you can just guess email addresses until the right person shows up in the sidebar. Again, I’ll use myself as an example. First you try, and see this:

Since nothing shows up, you try again with

Bingo! Now you know that’s the right email address and you can reach out to me about investing $10 million in my company Fetchnotes at a $100M valuation. I have yet to find a person for whom this doesn’t work. Remember, use this power for good and not evil. Or if you decide to use it for evil, just don’t tell anyone you learned it from me.

Note: Special thanks to Cecilia Haig from Box for showing me this hack! 

Why I Switched from Dropbox to Box

Nowadays, ubiquitous cloud storage is an expectation. I have a ton of files, and I want those files with me everywhere. Unsurprisingly due to the prevalence of this need, there a lot of players in this space. I just switched from the very consumer-oriented Dropbox to the enterprise-focused Box.

Frankly, I always thought of Box as the “Dropbox for business”, and usually that conjures up images of bloated software, horrible bureaucracy and outrageously expensive yearly subscriptions. Dropbox is clean, it works, and I’ve been using it for years without ever having to contact support. In fact I don’t think I’ve ever even spoken with someone at the company about anything. So why did I make the switch?

Personal Contact

I like doing business with people that I have a connection with. Whether that’s because I’ve met them in person, or they’re a fellow entrepreneur,  or they’re a user, or something else, it makes a big difference to me as a startup CEO. At Box, I was introduced to the company by developer relations extraordinaire Cecilia Haig, who discovered us after our “TechCrunch initiation.” She reached out about working with Fetchnotes for the upcoming Android OneCloud release, among other things, and came to our first phone call armed with ideas about what integrations our users would enjoy most. She actually continues to use our product actively, and we share notes with one another on occasion (most recently a tomato juice based drink that I’m convinced will taste terrible, but she insists I try).

Not once did she pressure me or even suggest that I try out Box. I did so because I wanted to make a user of ours happy. It just so happened that this coincided with me hitting my storage limits on Dropbox.

More Space, Still Free

I took a lot of random footage of our team to splice together for a documentary of what it’s like “inside a product launch.” I have yet to put it together because, you guessed it, I’ve been busy (and I suck at video editing). But this added well over 1GB to my file library and I kept getting an angry red X on my Dropbox icon when I tried to sync. I found that it was because I had hit my limit (2.5GB since I had invited someone), and I’d have to start paying if I wanted more space. 

Cecilia had given me a Box account to play around with for our integration, so I shoved all my documentary footage in there to make more space in Dropbox. Not to mention that I was able to get in on one of their promotions (they are WAY more generous with these than any other company) and get more space than I would ever know what to do with. So I moved everything in, and I now have 7GB of stuff in my Box account right now and I don’t pay a dime. What the hell am I going to do with another 43GB of space? I don’t know, but I have the luxury of thinking about it thanks to Box.


In elementary school, I tried to get my dad to buy a military-grade firewall for our computer. What was the most sensitive thing I had on my computer? My Starcraft account credentials. So telling me that my documents have the same level of security as companies like Proctor and Gamble and MTV hard-core appeals to my inner nerd, even if I don’t need it.

But I’m not just storing college essays and random photos anymore. I’ve got contracts, operating agreements, partnership documents and more stored in the cloud. Box is indisputably the company for security in this space, and I’m happy to support them. 

Link to discuss on Hacker News:

Why email is broken and what we can do to fix it

A few months ago, I read Paul Graham’s essay on “Frighteningly Ambitious Startup Ideas.” The section on “replacing email” got me thinking a lot, but it came out a month before Fetchnotes had opened up our beta. We were still laser-focused on the problem of personal productivity through easier, more flexible note-taking. 

In mid-June, however, we released our sharing features with with the goal of getting all those “do this”, “check this out”, “read this” and “what’s the status on this” out of our inboxes and into a place we can actually act on it. While only a portion of our user base activated it (since right now you can only share with other Fetchnotes users), we could tell we were on to something. We had already been using a Facebook group for conversations, but getting all that transactional “to do” communication out of our inboxes cut down on our internal email by something like 90% — and we started hearing the same from some of our users. Despite us not being a “replace email” startup, it caused us to take a step back and look at why this was happening and what opportunities it represented.

Over the years, email has evolved into the central hub of our workflow — it’s where things enter our lives and where they leave it. That means your inbox no longer represents communication. It represents what you currently have to deal with in one way or another. Each email embodies something you need to do (even if it’s just read this), otherwise you would have deleted it already. And since people crave consolidation, they end up using their inbox as their universal to do list — how many times have you emailed yourself something you need to do, an idea to follow up on, or a link to check out for later? Or told someone else, “Yeah, can you just email that to me so it’s in my inbox?” This. Is. Not. Okay. 

Why? Email is an awful to do list. It’s just a dumping ground of unorganized crap. Let’s look at what makes a good to do list:

Context when it enters: The only context you get in email is the subject line, which is woefully inadequate. I can’t immediately glean whether this is something I need to do, read, look into or anything. The sender has all the context until the receiver reads the entire message. Email grade: D+

A way to prioritize and categorize in a meaningful way: Having no context means you have to do all the work to figure out where things should go (either within your inbox or in other tools). Everyone knows that “Gmail ninja” who has hacked their email to such an absurd degree with tagging, filtering and priority inbox that it makes you think the only way to solve email overload is to develop a very progressed case of obsessive-compulsive-disorder. But no matter how advanced the system, it still fundamentally relies on you, the receiver of the communication, to figure out what to do with it. Email grade: C-

Curation about who adds to itAnyone who has my email address can add things to my inbox. We’ve been programmed to be okay with giving out our email address to every person we meet (do you really care about any other information on a business card?) and every website we visit, so we end up with a completely unfiltered mess of people we actually need to communicate with and random websites and strangers angling for our attention. You wouldn’t let some stranger add “meet with me on Thursday” to your to do list if it was in a separate app or on paper, so why should they be able to just because they have your email? This was my biggest takeaway from the essay. Email grade: F

That’s a solid D for the tool we probably use most in our lives. That is not sustainable.

Email has a fundamentally flawed paradigm for communication. It assumes that tasks come from communication, whereas communication is actually rooted in the context of what you’re already doing. With e-mail, you sent me this, now I need to act on it. But in real life, I’ll tell my co-founder Chase to get me some metrics from our server logs because “send jake the metrics” is on my to do list. The “what you are already doing” is held in whatever you’re using to keep track of the things in your life, whether it’s Fetchnotes or something else, and communication must be an outgrowth of that rather than the other way around.

We need to stop building improvements to email. All the cool plugins, new clients and other innovations on the inbox itself are like building ways to make a candle wick burn longer instead of inventing the light bulb. I’m not sure we need a “to do list protocol” as the essay suggests, or what that would even look like, but we need something that is platform-agnostic and that gets communication out of your inbox into a place you can act on it. It must work with email but it must not be inside email. I suspect that rather than one “email killer,” we’ll find that email is slowly eliminated by a couple of specific tools that in aggregate take care of our electronic communication. We’ve got a lot of work in front of us, but we want to make Fetchnotes one of them.

Alex Schiff is the co-founder and CEO of Fetchnotes

My Weekends Look Like My Weekdays

Last Sunday night, I went to a Father’s Day barbeque at my girlfriend’s dad’s house. I had been working all afternoon on writing a guest blog post for LaunchRock (which you can read here), so it was a welcome break. Around 8:30PM, I got up and said, “Thanks for having me, but I’ve gotta get home for our design session.”

My weekends look a lot like my weekdays. I sleep in a little later, and I try to go to the gym, but for the most part I’m still working four hours or so during the afternoon and typically another few hours at night when I get home. The funny thing is, I don’t mind at all. In fact, I really like it.

My family will be the first to point out that I’m terrible at relaxing. I just get really antsy and unhappy when I spend too much time away from my work. Sure, I screw around on the Internet or go out with friends from time to time, but the work/play algorithm in my brain is severely dysfunctional.

That’s probably because the work part is tightly integrated with the fun part. I love what I’m doing. Seeing “Power Design Session with Ben and Loui” on my calendar on a Sunday night makes me excited in a classic nerdy entrepreneur sort of way. I also feel kind of guilty when I don’t work on the weekends since I know that Chase is coding nearly every Saturday and Sunday (and Monday…and Tuesday…well you get the point). I’m really bad at “checking out.” As I wrote in, I’m Terrified of Being Normal, I was running financial model projections in line for a roller coaster a couple weeks ago.

Eric Stromberg recently wrote a post about joining a startup that sums me up perfectly:

A nice way to tell if you have a passion for what you are working on is to ask this: Do your weekends look a lot like your weekdays? When you get home from work, do you find yourself wanting *more*? Do your ears perk up whenever someone talks about a certain subject? Do you feel compelled to ask questions and really listen to the answers? That’s passion, and it fuels a competitive advantage that can’t be faked. It’s what drives you to work when you don’t have to, to think about new solutions to old problems when everyone else is spending the weekend flipping the “work” switch off.

Yup, welcome to my life. I’m the type of person that wishes every weekend was like a Startup Weekend. It’s a little sad, but it’s the competitive advantage us scrappy entrepreneurs have over the big guys.

And hey, if you’re going to dedicate an obscene amount of hours per week to something, you might as well have fun with it right?