Category Archives: Connector

How To Write a Great Cold Email That Will Actually Get a Response

Photo by Kon Karampelas on Unsplash

One of the best-kept secrets in the start-up world is that you can access almost anyone you want to with a great cold email. Well, almost anyone… see more below.   

CEOs are remarkably accessible and easy to reach. 

Most CEOs and VCs personally read every well-formed email they get, even if they don’t know the sender. This means that if you send a great cold email to your favorite CEO, chances are it will get read.

If you don’t know the CEO’s email address, it’s easy to guess. The email address of 90% of company executives follows the company’s normal email convention. If you wanted to guess the CEO of Apple’s email address, for example, you could start with [first initial] and iterate from there. 

When I was in college in the 1990s, I would send cold emails to people like Steve Jobs, then the CEO of NeXT, and Steve Ballmer (then #2 at Microsoft). Both of them would reply within hours… to a college student. And if you’re wondering, yes, I would usually send them from my email address at 3 am while in the computer lab waiting for a program to compile.

But just guessing someone’s email address does not make your email worth sending. 

If you want to start a meaningful conversation with the person you’re trying to reach, you need to write a great cold email. 

There are three things you need to do to write a great cold email:

  1. Personalize and send it to the right person. 
  2. Emphasize how responding will benefit the reader. 
  3. Make it short and clear. 

That’s it. That’s all you need to do. 

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Non-obvious guide to finding a great job

Last week I published an article in BusinessWeek entitled an Insider's Guide to Tech-Job Hunting.  Here I try to expand on this article to summarize all my advice for job seekers in one big post.   I look forward to your thoughts and comments…

Think like
an entrepreneur and be proactive in your job search

Like many
employers that are hiring in this market, Rapleaf receives a ton of
resumes.  Here are some observations and
advice for people looking for a job in the technology industry (but I warn you
that I’ve never actually looked for a job so my perspective might be a little


A jobseeker
is going to more successful finding a position that will be truly satisfying if
she is proactive rather than reactive. 
Reactive job seekers diligently scan job openings and send their resumes
to HR.  Proactive job seekers research
the companies (or teams) they want to work for and send a message directly to
the hiring manager looking to create a position for themselves.  More on this as we go further …


Below are
the ten non-obvious steps to finding a great job.


1. Look for companies you want to
work for … not jobs you want

When you
start your job search, don’t go first to job listings.   Instead, first figure out what you want to
do and where you want to work.  I’m often
surprised how few job seekers have any idea what they want to do next.


Maybe you
want to work in a certain industry, a certain location, or only places that
have a vegan cafeteria.  Whatever your
reason, you should narrow a list of actual companies you want to work for (ideally
to 10-100 companies).


2. Don’t apply to the job … apply
to the company

When you
find a company you want to work for, do your research on that company.  Understand the company and where it is going.  If you are a great candidate, they might
create a job for you.   Don’t worry that
they have or don’t have a job opening that fits your resume perfectly.  Companies often are looking for people that


3. Send your resume directly to the
hiring manager (not HR)

introducing yourself to a company, you want to contact the hiring manager
directly (and not go through the careers web site for the company).  In a really small company, the hiring manager
might be a VP or the CEO.  At a bigger
company it could be a whole host of people. 
It might take some research to figure out who the best person to contact
is and what their email is.


One friend
of mine heard a CEO speak at an event and was really impressed with what he
heard.  So my friend sent the CEO an
email to every permutation (firstname.lastname@, firstname@,
firstinitial_lastame@, etc.) he could come up with.   The next day he got an email from the CEO:
“I got your five emails last night. 
Seems like you are very interested in working here …”   And three weeks later my friend had a job at
the new company.


4. Dumb down your resume

In today’s
market, companies are looking for perspiration, not inspiration.  In other words, most companies are looking
for doers that kick butt and get stuff done. 
They are going to pass on “strategic thinkers” (as they may have fired a
bunch of “strategic” people already). 
Big companies need to do more things with less people – so they are
looking for people that are super productive. 
Small companies looking to grow need doers.


So retool
your resume to show off that you are a work horse who gets stuff done.  And reference this in your cover letter.  Get rid of the “strategy” sounding verbs like
“empower” and “process.”  Let employers
know that you don’t just make PowerPoint slides all day but that you actually
can either create products or drive revenue. 


5. Send a very targeted email to
each employer

Send a
short and targeted email introducing yourself to each hiring manager.  A good email would be just a 4-6
sentences.  Include a very brief blurb
about yourself (1-2 sentences) that quickly tells them why you are
special.  Also include one really
interesting idea for the company – if you are an engineer you can maybe give
some scaling ideas or if you are a salesperson give a better idea on how to
acquire customers.   Really understand
the company so you can give them a relevant idea.   And, of course, attach your resume (in PDF


One company
I know got an unsolicited email from an engineer detailing the scaling problems
the company was likely experiencing and giving two ideas for a solution.  The engineer’s resume was one where the
company would normally not interview the person.  But the targeted email eventually lead to the
company giving an offer to this candidate.


6. Follow-up at least twice with
everyone you do not hear from

follow-up emails to the person after one week and after two weeks.   Don’t call (calls are just annoying … most
tech companies have an email culture).  
And if you don’t hear back from one hiring manager, contact additional
people in the company until they clear say they are interested or not


7. Don’t be discouraged if they
don’t respond

companies are not right for you.  Often
they are doing you a big favor by not getting back to you.  


8. Do something nutty and unorthodox

Scott Bonds
really wanted to get into the gaming industry in 2003 (when jobs were really
sparse).  After doing a bunch of research
on the industry, he decided that Electronic Arts would be a great place for
him.  But there were no jobs at EA at the
time.  Scott started a lobbying campaign
to work at EA.  He started a blog called (now defunct) and blogged about his quest to find a job
at the company.  The blog became so
popular that tons of hiring managers at EA invited Scott to interview with them
just so that they could meet him.  And he
eventually got a great job at EA and worked there for five years.


Sodera became one of my colleagues at Rapleaf by showing up to his job
interview in a gorilla suit.  That’s
right, a gorilla suit.  And he had made a
“Rapleaf” t-shirt that he wore over the suit as he commuted via BART to the
interview.  It was classic.   He was applying for a marketing job and he
was relaying to us that he would do anything to promote the company.   It worked and he got the job.  



(Rapleaf cofounder Manish Shah with
Vivek Sodera (in gorilla suit) on Vivek’s interview.)


Today you
can start a Twitter campaign praising the company, do something on a social
networking site, or even bake the team cookies.   


9. Get in the door for a company you
want to work for

If you want
to work in a company or an industry, get yourself in the door. If you have to,
take an unpaid internship.  Regardless,
don’t focus on compensation.  If you
prove you are a rock star and valuable to the company, they will take care of
you as great talent is really hard to find. 
And if you don’t end up a good fit, better to use an internship to get
into the door quickly and fail fast.  


10. Interview the company

I’m always
surprised at the number of job seekers that don’t have questions for the
interviewers.  As a job seeker, you want
to make sure you are picking the right company. 
Come to the interview armed with questions (write them down so you do
not forget) and learn everything you can about the company, the employees, the
environment, and more.  Good things to
understand is the detailed company financial situation, its customer relationships,
the corporate culture, how you are expected to work, and more.



A proactive
job seeker will not only be more likely to get a good offer, but she will also
be happier with the company she ends up working for.

Signaling your intentions through talking about time

People are really bad judges of little time.  And they often don't signal their intentions appropriately.  My friend Alexandra Wolfe pointed this out to me recently when she noted that people always say that they are running "5 minutes late" or that they will "be there in 5 minutes."

But what does "5 minutes" actually mean?

My investigation into this mystery has led me to the following answer:  "5 minutes" means anything and nothing.

When you tell someone you will be there in "five minutes," it conveys no information.   It could mean you'll actually show up in 1 minute or mean you will be there in 25 minutes.   The person who gets the message won't know if they should eagerly await you or do a sales call.  

And, by the way, it is the same thing for "20 minutes."  no information is conveyed.  "20 minutes" could actually mean "never."

So instead of saying you'll be five minutes late … tell people that you will be there at 5:06p.   That gives a definite time to the receiver and will ease her anxiety.  Plus, you'll be able to better signal your intentions so that they can follow you.

Also — never say you'll do something "in a sec."   that's likely untrue.   It is possible you'll do it in 16 seconds … but likely you'll do it some time longer in the future.  

Successful people return calls

I've found that most really successful people return calls much faster than moderately successful people.   So the question is:  are they successful because they return calls OR do they return calls because they are successful.

I'm not sure. 

But I think it is wise not to chance it.  Best bet to return calls and email quickly.  

A lot of inbound emails are for people who are trying to sell you stuff or for things you don’t want.   With those emails, my rule is that if the email is written well, takes my interests into account, and is polite and short (without big attachments), I'll email them back and at least say that I'm not interested.   That way their time can be respected and they don’t have to follow-up with me.

All people should follow this rule.

But more importantly, emails from colleagues, friends, or business acquaintances should be replied to ASAP.  If you are on a call with someone and you agree to get something to them by Wed, then you should definitely get something to them on Wed.  And if you slip, you should let them know.   And if you don’t let them know, you should at least respond to their emails asking you about why you haven't responded.   It is only courtesy.

I personally take notes on everyone I interact with on the following items:
– do they get back to me in a timely manner?
– are they on time to meetings?

For people that respect my time, I give them a star.   If that person is ever in need of anything in the future, I go out of my way to help them.   If the person does not respect my time, they get a minus sign.   I’ll be less likely to respond to help requests from those people in the future.

Being nice to those around you, especially those that are a few rungs down on the ladder, is an essential to being a good citizen.   And of the people you are dealing with, you never know who might be someone that can yield influence over you in the future … so respect their time now.

Art of the Introduction

How to introduce two people so that
they both benefit


Intros are
a science.  Making introductions the
right way will massively increase utility between two people.  And doing it the wrong way can make one of
the parties look bad or alienate one or both parties from you.


following few paragraphs will take you through the best way to make an email
introduction between two people.  Before
we go through the mechanics, let’s first define the objectives.  As the introducer, your objective should be that
you benefit both people you are introducing. 
If it can only benefit one of the parties, you should not even
bother.   At the end of the meeting, both
parties should be happy you made the introduction, glad they met the other
person, and thankful to you.


First, before
you start, take your time.  Good
introductions take time.  If done
hastily, their impact will be minimal.  
Take the time to really think why both parties will benefit from each
other and spell it out in an email.  I’m
sure we’ve all been victims of hastily written email intros (I recently got one
that said “Auren/John – you two just HAVE to meet each other.   You two take it from here.”)


A good way
to go about it is to first email the more well-known person and ask for permission.   Make the case of why they should meet the
other dude and ask them if it would be ok for you to introduce the two of you.  Usually it will work well but occasionally
someone will say that they are too busy. 
If that’s the case, you just saved both friends a lot of trouble.  You never want to make an introduction where
both parties don’t immediately respond to each other … that will make you
look really bad.   When you email people,
you want to make sure that the weight of your email encourages both people to
quickly arrange a time to talk.  


Take the time of each person into
.   Suggest whether they should meet for lunch,
coffee, over the phone, or just exchange emails.  Often people should just have a quick phone
call and you don’t want to waste the time of one or both people by suggesting a
lunch.    Be clear in your email
introduction what the next action should be.


introduce your friend to someone just because your friend wants to meet her.  There needs to be an exchange of value
between the two people … they both need to come away with getting more value
than their time is worth.  Proactively
suggest who they might want to meet.  


Clearly give the location of each person.  If one person is in LA and the other is in NY,
let them know.  Maybe they are going to
be in the same city in two weeks and they can meet in person.  Or maybe they are going to arrange a call and
they will now know what time zone they are in.  


Be sure to
give their first and last name and a
quick bio of the person.  I often get
intros from people to – so
I know the first name of the person is “Jim” but don’t know their last name and
it makes it difficult to save the person’s contact information.  And a quick bio will go a long way in giving


If you know two people have met
before, even briefly, mention it in the intro
.  Often
people forget brief meetings and you don’t want to embarrass one of them.   


Only forward emails that make the originator
look good
.  And, of you have to, edit
the email before forwarding.  I can’t
tell you how many times I’ve been introduced to someone by an introducer who
forwards me a semi-confidential email chain that I probably shouldn’t see.  



If you are
introducing single people of different genders, make sure there is no misunderstanding the intentions of the
.  If it is a business
introduction, make sure you are clear about it. 
You don’t want to create an embarrassing situation were people have
misalign intentions.  


If the
people use their assistants, then copy the assistants of both parties if



overall, your goal should be that both parties leave the meeting with each
other happy that you made the intro.  
They need to BOTH get value
from the meeting or you have failed.  But
when you succeed, you have the potential to massively increase the happiness of
both people.   An intro can be the best
way to help people. 

airplanes are an efficient place to read

I always try to do the most efficient thing I can do in any location. On airplanes, reading is the most efficient thing to do. Sleeping on airplanes in almost always sub-optimal. Working on the laptop is good (no interruptions) but still doesn’t hold a candle to reading. There is almost no plane I get more reading done on an airplane.

My strategy for a flight is like many travelers I know … first I stock up on all the magazines I haven’t read and a I pack a really heavy bag. I try to also bring a few books along. On the place I devour the magazines first the lessen my weight and then I move to the books … always leaving behind what I finish (United Airlines has had dozens of books donated to it by me over the years).

(I’ve also found that a shady place on the beach is a fantastic place to read … I had time to experience this over the holidays … there is probably no greater vacation for me than reading under a palm tree on a hot day.)

buy time by skipping holiday parties

I thought I’d give myself more time to work in December (we’re releasing some big products) so I consciously cut out holiday parties during the week. This was especially important this year since the holiday season started early due to an early Thanksgiving.

Now I love holiday parties … they’re a lot of fun. But sometimes one has to cut out some hard stuff to buy time.

how much time did I gain thus far? I estimate a gain of 15-20 hours year-over-year (2006 to 2005 comparable). That’s huge. … now I hope I don’t blow it watching all the Christmas spoofs on YouTube …

order your tasks by location

If you are like me and you keep all your home/work/life tasks in one place, you might want to consider ordering your tasks by the location you most efficiently can perform them in. Some tasks you can only do at one particular location (like I can only do laundry or dishes at home).

Some tasks, like business calls, can only be done during the day. other tasks are best done at night. some, like calling, are most efficiently done while you are driving (because you cannot do much else in the car). before driving on trips more than 30 minutes, you can have a call list of the people you want to call. sometimes, if it is a new contact, you can even pre-type the numbers in my cell phone so you don’t have to fumble while in the car.

My personal secret is to have a list of tasks do to when I am on the phone. these are generally low-CPU tasks (like cleaning up my house, reordering my contacts, typing up a business card, and other mindless tasks). Whenever I get a call I immediately switch to my phone task list and start crossing off to-dos while jabbing away.

quick rules for email

some small things i do to increase my productivity and the productivity
of others around me:

– only check email once an hour (and turn off all email reminders) …
sometimes i submit to the guilty pleasure and check email every 30 minutes
– when i get an email, i reply right away.   
– jettison IM
– don’t check email on my phone unless i need to.   
– respond to all emails before i go to bed every day.   never have
anything in my in-box before i fall asleep.   (sometimes i respond to
emails with a "i’ll get back to you on tuesday on this")
– i try never to CC other people unless absolutely necessary.   it is
unfair to waste their time.
– i speed read (or sometimes just delete) emails i am CCed on
– when i reply to emails, i try never to "reply all" as it is a waste
of other’s time.  i try to respond directly to the person were my email is
most targeted.

– i always try to have the minimum number of people from my company in
mtgs.   if only one person is needed, then two never go. 
big waste of time.   sometimes we determine that zero people are
– phone mtgs are often better than in person mtgs.   

to do:
– i to do list everything.   in the last six months i have written
and completed 4358 tasks … that is about 24 tasks a day. 

– jettison TV
– i try to be on-time to all meetings … i want to respect the time of those
around me
– I try to save time of those around you be not giving them things that are
half-baked.   i try to communicate so there is not ambiguity so
they’re not doing double work.

(my biggest pet peeve: when someone does not respect my time)


The Monster is a Mouse

Scott Kirsner writes a great column in today’s Boston Globe:
It’s a scary time for
(two small quotes from me in the article)

with the advent of meta listings sites (like SimplyHired) and more proactive candidate push sites (like WooMeNow and TheLadders) Monster is becomming less relevant to the passive job seeker.

and new services like H3 and KarmaOne are attracting the passive jobseeker that Monster has never been able to get its hands on.