There’s only a week left in November so it’s a little late for doing a NaNoWriMo post but I figure better late than never…

For those of you who aren’t familiar with the awesomeness that is National Novel Writing Month, it’s exactly what it sounds like – people from across the US (and now abroad) get together and collectively write a novel. It’s a great experience and I highly recommend it. (So does Lifehacker!)

For those of you going through it now, here’s an email I wrote to a family friend (middle school student) looking for advice on her first NaNoWriMo. Might be just what you need to get across the finish line. Keep writing!

NaNoWriMo Poster

Hey Family-Friend’s-Name,

Thanks for reaching out! It’s great to hear that you are doing Nanowrimo. I tried and failed to do it in 2006 (got to 35,000 words) and tried again in 2009 and was able to do it successfully.

The hardest part for me wasn’t finding the time to write, it was coming up with enough words to actually get to 50,000.

1) Give your story a lot of twists and turns.

I’m not someone who likes to do a lot of description. I’m a dialog and action kind of writer so I really needed a lot of side plots to the keep things going.

A piece of advice I often hear about fiction writing is to make sure your main character is always has a goal in mind and keep throwing obstacles at him/her that they have to overcome. Don’t make it easy for your character to get what they want!

2) Write what you know

My first novel was a modern sci-fi thriller which I found interesting but there was too much I didn’t know to write a good book. For example – if you are a regular person, what’s a reasonably realistic way for you to get a bunch of weapons on the black market? I’ve never done this and would have to spend a lot of time researching it on the internet. I had a lot of questions like this in my first novel and this slowed me down. You gotta keep pumping out words!

My successful novel was a fantasy novel. This worked a lot better because I read a lot of fantasy growing up and you really do get to just make things up as you go a long since it’s your book and your world, things can work however you want (with regards to magic, dragons, trolls, etc)

If you read a lot of a certain type of book, it’ll be easier to write a book in that style. Also it’d probably be a bit easier to have a main character close to your age or younger, than to write about someone who is 50 or 60, since it’s harder to understand what kind of stuff they deal with / think about.

3) Go off on tangents.

This is similar to lesson number one, but more specific. I think I had a couple sections of the book that were totally random. Sometimes I got really into describing something – like the history of an ancient tribe of elves. Almost like a story within a story.

But you can get even more random. I think in one part of my novel some random character starts talking and all of a sudden its a list of stuff I have to for work or a journal entry about how I’m feeling about living in San Francisco. Totally random, doesn’t make any sense.

But again, it’s your book and you’re allowed to do that if you want.

4) Write consistently.

Its 1667 words a day. That’s a good amount, but not crazy. I wrote basically on my train to work, my lunch break and my train home, plus spent time at night and on weekends writing. You will have to spend a lot of time writing, ideally with a keyboard instead of by hand, to get this book done. It’s a lot easier of you just do 1667 a day and not have to play catchup. That’s really demoralizing. So write everyday!

I hope this wasn’t too long and was helpful. Let me know if you have any other questions.


Introductions are a critical part of being a good professional and friend. Do them well and you’ll be seen as a valuable contact and person to know and stay in touch with. Do them poorly and you’ll find people avoiding contact with you, in person and any other channel.

Step 1: Always, always use a double opt-in

Double opt-in means that you first confirm from both parties that they’d like to meet each other before you make the introduction.
I prefer to make introductions only when there’s a great fit on both sides. in which case I’d be more likely to tweet the request or share on Facebook.

In general, when I want to make an intro, I want to maximize the chances that it results in an actual engagement. This means I won’t make an introduction on behalf of someone I can’t vouch for, and I only introduce them to people I know well and who are likely to follow up.

Let’s go through each element one at a time…

1) Subject: This has got to be catchy. Sometimes I make it short and vague (if they’re a busy person and I’m trying to pique their curiosity). Other times I do a more straight forward “Steve meet Joe [starting a blog”. Gotta make sure they open the email in a timely fashion!

2) Quick personal chit-chat: I only introduce people that I know decently well and who knew me. In this case, it was more of a business contact, but I gave them an update on what I was doing and wished their business well.

3) Who I’m introducing you to: This is where I give the background of the people I’m making the introduction for. I usually try to highlight how I know them, (in this case I forgot to) and showcase whatever they’re doing in the best light possible. In this case I included links to show what these entrepreneurs were up to.

4) “The Ask”: Here is where I ask the person I’m reaching out to for something. I think it’s important to have a specific request in mind. Usually this ask is for advice, perspective, a meeting, a beta invite — just ask for something! In this case, I asked the guy for his perspective on their startup’s contests and whether it would make sense for them to sell it as a product to web publishers. [1]

5) Why I’m asking you: This is where I establish the background of the person I’m reaching out to – both for the benefit of the people I’m making the introduction for, and also to underline why I’m asking this particular person for help. No one wants arbitrary requests – this shows you’ve thought about this.

6) Flattery/Compliments: If I’m making the introduction, it’s because I like and respect this person and I think a genuine indication of my high regard for that person is really valuable. Buttering up your target never hurts =)

7) Fun sign off  or extra personal request: This is optional but I like to do it. I almost always add a PS in my emails because almost everyone reads them and you can add something tangential to the email, like a joke or an additional request. In this case, I’m asking if the guy I’m emailing knows anyone who are going to Burning Man.


So that’s what I got. I think introductions are a super powerful thing – I’ve gotten a lot of benefits from a well-written introduction and I strive mightly to ensure that every introduction I make adds value to both parties.

What do you think? How do you do email introductions? Anything I missed or got wrong? Let me know in the comments.


[1] One of my friends just got back from an internship in Washington D.C. and one of his biggest complaints is that he’d get introductions to meet legit people, but they’d get there and no one really knew what the meeting was for. It was just a “hey you two should meet”, which tend to be really crappy.

Got an email recently from a guy named Scott Balster. He had pinged me on Twitter earlier asking if he could pick my brain about something. [1] I agreed and here’s what he sent me:

I am building a concept called Employtown ( ) where basically the premise is to give job seekers a platform to build a digital billboard of themselves, promote their search among their networks, and receive bids from employers.

I have done some testing and with the signups I have received from the landing page and want to move forward. My hold up is that I have a limited technical background (have used Joomla and other open source programs). Basically, my options are:

  1. I can learn to program to build it myself in phases.

  2. I have a developer who can build it for 10-12K (the complete spec that I laid out)

  3. Or find a technical co-founder who wants to work on the project.

  4. Find a developer who can build it in stages and then test the features and user metrics to know when to adjust.

What are your thoughts in this situation?

I’m glad Scott emailed me. Personally, I don’t find the idea super compelling, but I’ve learned not to get too hung up about initial startup ideas, because they usually change. Plus he is a business cofounder and thus holds a special place in my heart. I spend a lot of time on HN and while the community is great, they tend to enjoy ragging on non-technical people who want to start companies. Though perhaps they just need to be approached the right way.

I want to help Scott – and I think his challenge is more than just how best to build the product, but in fact are three-fold:

1) Customer traction. You said you have some signups. How many? Are people lining out the door to get this? How do you know if this product is what people really want? [I shared with him a copy of The Entrepreneur’s Guide to Customer Development, which readers should really just go ahead and get it. Great read]. I know you didn’t ask for this and perhaps I’m not seeing the vision, but I don’t know if online billboards are going to resonate with hiring managers. Getting proof of customer desire (not just from jobseekers, but HR people) is key.

2) Technical ability. You don’t know how to build what you want to make right now and you’re exploring different ways to do it. This ties very closely to the first point, customer traction, because if you build something no one wants, everyone is frustrated and time is wasted. I would encourage you to outsource the barest MVP – saves money, time and easier to pivot. See a great post by Derek Sivers, founder of CDBaby called “How to hire a programmer to make your ideas happen“. After you build a prototype, use it to get feedback and interest in the product – then you’ll be in a better position to find a real technical cofounder, which I think is critical to building a successful tech startup.

3) Money. It seems like you have enough money to fund some development, but ultimately to really build this out, unless you have a bootstrapped model, you’ll need additional funding. Having traction and a strong technical cofounder will help a lot with garnering the bigger dollars you’ll need to truly build this out. (As will connections to angels and VCs.

There are few things worse that chasing an idea, spending a lot of time and money to build something, and then seeing it go nowhere. That’s why it’s so important to figure out if you’re building something people want – before you go out and kill yourself trying to make it happen. Once you know people want what you’re going to make, it becomes easier to find someone to build it and to raise money (or earn it through product sales) which will help you continue forward.

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I recently met James, a senior studying Human Biology at Stanford, and we ended up spending lots of time talking about about the definition of leadership. After the weekend, he emailed me and I thought it would make another great email/blog post.

I was just thinking about your comment that leadership is bringing people to a brighter place… I actually agreed with your logic. I wonder if leadership might ultimately be about servanthood. Perhaps one imagines the perfect leader being one who truly has the interests of those he/she is leading in mind, such that success is determined by the well-being of those being lead.

In some ways that does seem correct—the entrepreneur is a leader insofar he enables those around him to engage in a fun project, or insofar she serves people in the world who are looking for this particular product.
In some ways of course, that concept is also somewhat flawed. Some of the best “leaders” in the world, at least nominally, are hardly thinking of others. I don’t know if Warren Buffet is thinking about serving his staff or his customers so much as getting rich sometimes. Doesn’t mean he’s necessarily a poor leader? Or does it?
Meh. Just food for thought. I really enjoyed talking with you, and I respect your will to action that’s so well tempered with a penchant for thoughtfulness. That’s something I will try to learn from you/emulate.
Haha :). Now you’re sorta my role model. Better do a good job ;).


Hey James,

Thanks for the email and bringing up the connection between leadership and service. It’s a great point: there is a reason why we often say someone “serves as the” CEO/Executive Director/Managing Partner of XYZ organization.

I believe that all leaders must think of those they lead because in the end, true leaders have followers that volunteer to be led. If you are the best computer programmer in the world, then you can choose to work at any company you want – you choose the leader/manager you want to serve under. So you’ve got to give that programmer a great work environment, exciting challenges and strong compensation to keep him. A bad boss isn’t a leader, (s)he’s a dictator.

If you are interested in the concept of service you should read more about “Servant Leadership” which says that leaders exist to help others grow as persons while they are being led.

The definition I gave of leadership, which I think makes the nebulous concept more clear, comes from a really great book called The One Thing You Need To Know by Marcus Buckingham, which you can see the extensive book notes for here. A taste:

  • Great leaders rally people to a better future
    • “You are a leader if, and only if, you are restless for change, impatient for progress, and deeply dissatisfied with the status quo.”
  • Leaders may be pessimists or even depressive (see Lincoln), but nothing, not their mood, not the reasoned arguments of others, not the bleak conditions of the present, can undermine their faith that things will get better.
  • “Properly defined, the opposite of a leader isn’t a follower. The opposite of a leader is a pessimist.”
  • “Despite their realistic assessment of the present challenges, they nonetheless believe that they have what it takes to overcome these challenges and forge ahead.”

It was great meeting you James and I respect your dedication to service and the young adults you worked with as well as your ongoing questions about how you can contribute more effectively to your issues. You’ve got some really good stuff going on – and hopefully I’ll live up to your expectations.

Warm Regards,

PS – Warren Buffett is actually a pretty thoughtful guy – I know you were using him as an example, but check out some of the things he’s said about management and money –

  • (When speaking of managers and executive compensation) “The .350 hitter expects, and also deserves, a big payoff for his performance – even if he plays for a cellar-dwelling team. And a .150 hitter should get no reward – even if he plays for a pennant winner.” (Link)
  • “I was wired at birth to allocate capital and was lucky enough to have people around me early on – my parents and teachers and Susie – who helped me to make the most of that … we agreed with Andrew Carnegie, who said that huge fortunes that flow in large part from society should in large part be returned to society.” (link to FORTUNE interview discussing why he gave $30B to the Gates Foundation)

I find that while I rarely get the urge to blog, I love responding to emailed questions with extensive answers. Hope you find this useful.

My friend’s email:


Noticed through some social media-stalking that we share an ambition in saving newspapers. Difference is, I’ve been wavering and translating my journalism skills to a public sector institute, whereas you have entrepreneurship experience and have been applying that to the business side of collegiate journalism. So I’m interested to know. what do you think about the future of journalism and what kinds of competing business models do you think it needs?

My response:

I’ve learned a lot about journalism since starting my job (which isn’t saying much since I knew about zip before April 09) and what I think is becoming clear to me is this:

  1. It’s more about the journalist now than the publication. A strong writing brand is going to mean a lot more than before – especially since distribution on the web is essentially free.
  2. Journalists need to connect to their audiences in more ways. It can’t just be a one way broadcast of printed words. Engagement means multimedia (audio/video/graphics), and it means listening to and responding directly to the public (easier now than ever with blogs, twitter, comments)
  3. Journalists need to learn business skills. My mentor from home told me to major in a hard science because “you can always learn that business stuff later”. Journalists are scared of business but shouldn’t be – they ought to carve out their own future rather than just depending on “the suits”
  4. Multiple Revenue streams: successful publications/content-based organizations are making money from many sources – ads, sponsorships, conferences, paid content, branded 3rd party products and donations. All of this means that journalists and companies and consumer/members of the public need to work closer together (see pts 2 & 3).

Wow – writing that email was a learning process for me too! You should think more about the business side – it’s a way of thinking and doing that I think is quite valuable and doable. It was good meeting you and going out last night – hope you make it back to DC safely and perhaps we’ll hang out again sometime!