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How to Email Early Stage Investors (themacro.com)
249 points by craigcannon on July 5, 2016 | hide | past | favorite | 68 comments



(I'm an early stage VC.)

I fully agree with this advice -- especially the part about weak warm intros being far inferior to good cold emails. I'd much rather see a good cold email than an intro through a mutual connection that barely knows me and the other party.

One additional piece of advice that I'd add: make your emails personalized. People would be surprised (or maybe not) at how many cold emails I get that start with sentences like "Dear Sir or Madam, let me tell you about my company [which is in a space that you haven't shown any interest in]..."

Adding in one or two sentences about why you emailed me specifically instead of the 500 other early-stage investors is very helpful. I'm not fishing for compliments, but instead some insight about whether I'm a good fit for some particular reason, or if you're just copy-and-pasting the same email template 500 times.


Re: I fully agree with this advice -- especially the part about weak warm intros being far inferior to good cold emails. I'd much rather see a good cold email than an intro through a mutual connection that barely knows me and the other party

PSA for startup founders reading: this is the type of investor you want. Seek out investors willing to do the work.

So many VCs will publicly gripe about inbound messages, unsolicited pitches, etc. I have heard many VCs explicitly say they will not meet with someone who isn't warm intro'd.

They will beg you to follow them on Snapchat or Quora to create brand for deal flow one minute then bemoan the people who want to actually have a conversation.

Leo's POV is refreshing.


A question ...

What is decision your decision process whether to answer or not? Do you answer honestly when opportunity is just too small?


Initially I felt like I ought to reply to every cold email, but quickly realized that that wouldn't scale (replying to cold emails took 2 hours a week, then 3, then 4..)

The litmus test I currently use is that if it seems like someone put more than 5 minutes of effort into an email, then I will reply. Sometimes emails fall through the cracks because I get swamped with work, but I'd say I reply to ~0% of "template" emails and ~75% of emails where the sender spent at least a few minutes thinking about the content and personalizing it.

Replies vary from "let's meet up" to "this doesn't fit my fund's focus areas" to "I'm not sure if the current version of the company is big enough for a VC business." I try to be honest if I have something constructive to say.


Just want to say to those of you who don't have great communication skills, and know it. This recipe pretty much applies to all cold emails, or any email with a party that you want something from and don't know well.

Job interviews, consulting cold emails, VC, someone who has the keys to your destiny and does not know it yet.

The most important things are, in my mind:

1. If possible, make the email actionable for the other party.

2. Don't waste the other party's time.

3. The more you write, the more opportunity you can shoot yourself in the foot. Remove sentences you don't need.

This has been my ticket to opening new doors so many times. Make it easy for people to help you.


These principles apply to ALL business emails.

Short, actionable, respectful emails with precisely the context needed (and nothing more) is what you need. I have received personal replies from CEOs of major publicly traded companies, with some Google-fu and a quick email.


I'm in sales/tech recruiting and I learned long ago that my two to three sentence email will get far more responses than the three-5 paragraph emails most people send.


Any Advice if they don't reply to your first email?

Twitter? Facebook? Find a Mutual Friend to introduce you?


Maybe try once more then assume they are telling you something. Move on.


Don't waste people's time is the kind of advice that is hard to follow, though. How would you know? If you spend two days writing a 2000 word essay to someone you obviously think that it's important.


"Hi, I'm ${ME}. I'm the founder of ${COMPANY}, and we make ${STUFF} that ${IMPRESSIVE}. Would you mind if I sent you a 2000 word essay, or would you just delete it after five seconds?"

Don't waste two days writing a 2000 word essay if there's a significant chance it will simply be ignored. Establish the relationship first. Heck, I'd have a hard time getting my wife to read a 2000 word essay, no matter how important I thought it was personally.


It's important to you but it might not be so important to them.

I completely agree with the parent's notes - keep it quick and clear. The sooner I can find out whether I want to help you or work with you or whatever, the better.


The list of common mistakes includes "Spending a lot of time trying to get a warm intro. You’re better off just following these rules and emailing me directly."

That goes contrary to a lot of advice other VCs say, which is that getting introduced to a VC is the most common way to get funded. Supposedly most cold emails don't turn into VC funding. Is this no longer the case?


Maybe the point is, IF you have to spend a lot of time trying to find a warm intro, then you might be as well or better off just going ahead and cold emailing.

But realistically, there are very few situations where a cold email is better or even as good as a warm email.

A corollary is: if you're not resourceful enough to get a few warm intros, you are going to struggle mightily to found a company.


I hear you, but recently I was doing a thing where I need $5M on a $15M pre-money raise. I called the front desk and was told by the secretary that "we only do introductions".

Fine, good enough, but I was on a clock and I knew who I was and I knew who they were and they could have been a great part.

About the time I am signing the paperwork (2.5 weeks later?), I get a call from one of their partners: they heard about it and want in.

No can do. Unfortunate, because I still think two of their partners could/would add value.

But I always wondered: why do VCs make founders jump through hoops that don't matter? Are they to prove the founder can sell? I remain baffled.


> why do VCs make founders jump through hoops that don't matter?

Depending on the celebrity of the VC, I can imagine a truly massive deluge of cold emails mostly from supremely unqualified companies.

I can understand their desire to be insulated from that.


VCs are idiots if they outsource screening to the front desk receptionist. They can at least get an intern to do the screening - who knows they might actually not miss out on all non-warm opportunities.


Seems like "I've raised X of Y and I thought we might make a good fit", would be a pretty good filter.


There is a really big company nearly everyone in the world has heard of for decades. I know the founder, COB, CEO, and saved his company twice.

Once I asked the founder for an introduction to a VC, and the founder turned me over to his also famous CIO. We chatted about old times and my startup.

He gave me a warm introduction to a Silicon Valley VC.

Did it help? Nope. Did the VC seem to care about the introduction? Nope.

So, for a VC, what might be the role of a warm introduction? Sure: Keep down the e-mail traffic.

Next, given a warm introduction, what does an information technology VC really want to hear? Sure, an easy way to make a lot of money quickly, i.e., an information technology company with some good barriers to entry in a huge market with significant traction growing very rapidly and with founders desperate for some cash and ready to sign an onerous term sheet?

I never imposed on that very busy founder or his CIO again.

Yes, some VCs regard a contact without a warm introduction as something contemptible from "over the transom". Well, sounds like the VC is so rich they don't want any more money, is having trouble handling their e-mail, or would be a total pain to have on a BoD.

And, just what is the VC going to bring except fungible cash? Do they know how to manage high end sites of Windows Server and SQL Server, grow a large server farm, manage software development with 100 developers, protect against nuisance law suits, do well with publicity, etc.? What do they really know?


They're "The money guy." They don't need to know squat except how to squash ideas that don't turn out hockey stick growth. Most websites don't need funding, it's a misnomer, and ruins what could be a perfectly good life style business.

People need to get over the idea that they're building the next big thing.. Because they're not. Turn out profitable business and then if the growth is there push on till the day. Otherwise enjoy what you have or sell it and try again.


Right!

E.g., suppose a Web site starts to take off, that is, has number of users per day increasing rapidly. Then, a crucial number in the growth is how soon can one server computer generate enough revenue to pay for a second server computer? That is, we're talking about a start on exponential growth.

Well, long the M. Meeker KPCB reports said that can get paid about $2 per 1000 ads displayed. Okay, maybe now that's down to $1.

Okay, suppose send just one ad per Web page. Get, say, a server with an 8 core AMD processor at 4.0 GHz for $1000 and send on average 24 x 7 just one Web page per second. Then the monthly revenue would be

     1 * 3600 * 24 * 30 / 1000 = 2,592
dollars.

So, in two weeks, get another server. So, we have essentially exponential growth with a doubling time of a little less than two weeks.

So, we have, in the history of (legal) business, about the fastest growth, the best business opportunity, of all time.

But we were talking 8 cores, right? At 4.0 GHz, right? If the Web pages are relatively simple, then we're talking being able to send maybe 8 Web pages a second. And we may have more than one ad per page. Okay, assume as above but 8 pages a second with 4 ads per page and get

     1 * 8 * 4 * 3600 * 24 * 30 / 1000 
     = 82,944
dollars a month in revenue. That was one server. So, in a spare bedroom get a wire rack shelf unit at Sam's Club for $100 and put 12 midtower cases of such servers on that rack. Have an electrician upgrade the house circuit breaker box and run 240 V to the spare bedroom for the computers and a big window unit A/C. Also put a propane powered backup generator on a concrete slab in a small hut out back. Now we're up to ballpark $1 million a month in revenue.

So, we're talking ballpark $10 million a year in pre-tax earnings. At a P/E of 40, we're talking a company worth $400 million, from a spare bedroom.

Is the Internet a great opportunity or what?

Sure, the issue is getting the users.

But with the users, there's only a small window of time when even a dirt poor founding entrepreneur would take equity funding. And without the users, still there would be not equity funding.

Net, it looks like equity funding and Web sites mix like oil and water. If the site grows, if it doesn't, in either case, there's little or no role for equity funding.

Of course, if have just a Web site, may have only a lifestyle business. Okay. Not so bad.


But advertising slows growth. Both because of focus and not as good of an experience.


I'm not clearly understanding what you wrote:

What about "focus"? User's focus when the look at the screen; my focus when I have to work on all the issues in the startup and, then, in addition the ads and, thus, lose my focus; something else?

For user experience, with my Web pages, the ads are fairly easy to ignore. The pages are dirt simple with essentially no JavaScript -- so that pages don't jump around. And all the layout is just via tables so that I know to the last pixel where everything is.

The content the user wants is on the left, and some ads 300 x 250 pixels are on the right. Simple.

So, I'm guessing that the ads will not be very distracting, e.g., won't hurt the ability of the users to focus on the content, i.e., won't yield a poor user experience.


My take on this. This is advise for early stage investors (e.g. mostly angels and micro VCs). For A-round investments I think a warm intro is still needed.


Why?


Most VC's get approached a lot, they use this as a filter. Most angels get less dealflow. Some famous ones (Ron Conway) have set up a team (SV Angels) to deal with it.


He's not a VC, though. He's an early stage investor which I would put pre-VC. A VC may still require warm intros since he may get 1000 cold emails a day, not 100. And the warm intro is also more meaningful, since yo already should have some angel investors and partners in his area of activity.


It may be a matter of degree. My experience is that warm intros do help for early stage investors, but they aren't a requirement. Maybe a simpler way to look at it is that a warm intro often helps any introduction no matter who it is, but if you're polite, direct, and charming, you'll be fine either way. Since it was qualified as "a lot of time", I'd suggest spending "a little time" trying to get a warm intro, if that doesn't work quickly, just email cold while keeping the posted advice in mind.


I think he was referring specifically to himself. However, he isn't that wrong. There are a few that want warm intros, and one that actually won't even talk to you without one [1]. But if you view your fund raising strictly in terms of dollars raised per hour spent, you'll find that simply contacting more people is the vastly more productive route in most cases.

[1] https://lowercasecapital.com/prospecting/


Maybe it makes more sense from an ROI perspective. Is it really beneficial to try to establish that warm intro with a 50-80% response rate vs. in the same amount of time, sending 20 cold emails with a 10-20% response rate?

The respondents to a well-constructed cold email are also likely to self-select!


Also: email from a founder, don't use a "investment banker", or other intermediary.

Don't insist on a phone call or in-person meeting as the next step. If you can't explain it with email, video, etc. to an investor, you'll have a hard time explaining it to customers.

Use bios, Angellist, Crunchbase, etc. to profile investor prospects. Don't email a tech investor a movie pitch, unless you have a very unique connection to that investor.

Don't insist on an NDA (yes, it still happens)


Most importantly you should research your investors before you just email them. It's better to reach 20 interested investors than 200 people with money who won't invest in your company.


Huge point, I think. Instead of crafting a huge email, spend a lot of time finding the right investors to approach first.

"This is the only guy with money I know of" is not really a successful starting point to write someone.


The first sentence should always be the ask.

Give the recipient enough information in their [iOS alert | Gmail excerpt] to read it when they're in the right frame of mind to think it over.

Professional email is not flirting. Guys flirt by first trying to get your attention and interest, then follow up with an invitation. I assume this gives him an opportunity to bail if he's not getting a welcome vibe, but that doesn't apply here.

See how much information you can pack into the first few words, so they can open it when they're ready. Follow that with the context and data they need to keep reading when they're ready to consider it. End with your own introduction, because you're the least interesting part of your letter (except insofar as you're a part of the venture).


Applies equally to all forms of communication. I pay a conscious effort to put the most important point in the excerpt.

"Hi $name, interested in grabbing coffee? Bla bla bla I met you bla bla, bla bla talk about bla bla."


Except in some very particular situations (maybe you're looking for investors in your coffee roastery tech startup), getting coffee is a means to an end, the "end" being the same thing as the "ask" that DelaneyM is referring to.

"Hi $name, interested in grabbing coffee?" buries the "ask" until during the coffee chat.

It can be tough to do, but I think a lot of very busy people would actually appreciate you just coming out and asking for what you want, even in the first sentence.


I think he meant: Even if you are flirting, tell her what you want in the first few words.

Makes sense to me.


> Not using your @company.com email.

Really? Who the fuck cares? If I reach out on twitter nobody bats an eye - but use zachaysan@gmail.com and everyone loses their minds. I used to use my @company email for my startup that was acquired. Now I can't find any email exchanges I know I remember having. I'll use zach@venn.lc for stuffy clients, but I thought YC partners were kinda above this kind of outdated thinking.


You can make your @company.com email forward to your personal gmail, you know.

Like Michael, I find it convenient, when receiving a lot of email from people I don't know well, to have the domain name of their company right in their email address. For example, if I later remember something I want to tell them or someone to connect them to, having their email address autocomplete is nice.


Yeah I do it, but then when I search I'm missing emails I sent.



I don't think everyone or many people cares, but some people might. It's such a simple effort ($10.69 + $5/mo for Gapps) it's silly to not do it.


I have my priorities right - I spend my time writing code.

During the early stages of the company email does not get my attention, despite the fact that I know how to set it all up and configure it.

To me this is wise use of time. It would be a waste of time to get properly configured email addresses when the real priority is to get code out there.


Using company.com makes for better metadata, in two directions.

It makes it easier for them to immediately look up your company just from scanning their inbox. If they later come across your company separately, it makes it easier to find your message and to follow up on the email thread (they probably don't remember your name).


Some people care, some don't. I personally prefer to use @mypersonaldomain.com, that way it looks professional and at the same time, it belongs to me as long as I own the domain name (not tied to a company).


I can see the value of using your mail from your company but I'm really afraid it would get treated as spam by the filters, and for that reason I tend to use gmail for contacting someone for startup related reasons.


I suggest emailing up-and-coming VCs who are more eager for any kind of dealflow.

Look for people/funds who just raised their first fund. They are hustling, likely not drowning in leads like Michael Siebel is, and willing to do just about anything to make their LPs happy including spending countless hours evaluating investment opportunities from complete strangers.


I would disagree. Yes, this way you get "easy money", but what you actually want is "smart money". It's like with building your unfair advantage. It shouldn't be too easy, otherwise it won't have the required value.


I think Michael Seibel says it himself somewhere else - yes you do want smart money. But the reality for 95% of the time you just need money. The founders make or break the company, and optimizing for just the best investors is optimizing for the 5%.

The other reality is that majority of startups will fail to raise money. So unless you're truly hot s*, raise from anyone including so-called "dumb money" as long as they dont add negative value by pestering you or doing something similar.

Startups die cuz they can't raise or run out of money. Usually a symptom of something else, but don't die cuz you only chased smart money.


I would assume that if you need money you don't want to take it. Starting a company is also investing, but something more than money: your health, your time, your personal relationships. I wouldn't do that if the money I need wouldn't come to me easily enough. Really, if you can't focus on finding the smart money, better have a main job and treat the business as your side project, at least for now.


So, how do you find such people?


Look up recent funds and cold email them.


Maybe I'm old, but why not call them? "I'm looking for 5 on a 25 pre - can I have 15 minutes of your time face to face?"


Calling requires them to be free to talk at the time you call, and interrupts whatever they're doing. Emailing doesn't.


Unless you're a hot company, the power imbalance favors the VC.

This means you should be communicating on their schedule, not yours. Email is async and hands down beats phone calls (which are synchronous).

Also, a lot of people really just hate phone calls. I won't even talk to recruiters on the phone—if they try to call me, I tell them to send me an email.


A lot of people would find that annoying:

- it forces them to stop what they're doing

- it puts them on the spot forcing some kind of response


Your point is that the answer to the $5M ask is "no"?

Fine, I guess. Do I care? I've got a company to build.

Or is your point that I might hurt somebody's feelings?


What does 5 on a 25 pre mean?


raising a $5M equity round on a $25M pre-money valuation


I wrote up these tips on emailing to help my friends and relatives email better: http://dtrejo.com/how-to-email

Summary:

    - Keep it under 250 words.
    - Ask only one question, directly before your signature.
    - Ask a single yes/no question.
    - Extra Credit: Show you did your research
    - If you really want a reply: follow up in a useful way.  
      NOT: "Did you get my email?"


Aside from subjective or "trust me, this works!" commentary, what does the data say about getting replies from investors? A better title for this would be "How to Email An Early Stage Investor."

It would be interesting to mine emails from well-known investors and see what the data shows for first emails from individuals who were ultimately funded.


Michael has also talked about how to pitch investors in a similar, clear way. [0] It's part of the "how to start a startup" series.

[0] https://youtu.be/SHAh6WKBgiE?t=1227


If the recipient only sees the subject line, what increases chances of having your email opened? For people that habitually open and read email OR use a preview mode for efficient scanning, subject lines may not be as important.


Anybody have similar advice for cold emailing professors/researchers?

I never had any luck emailing professors whose lectures are on youtube for book recommendations or researchers in a field where I'm looking for something similar to what they study.


The best advice for very busy professors is to find the correct researcher working on their team (scan papers for the one that seems to be coauthor in the field you want to ask about). Most of the time it'll get delegated to them either way and if it's interesting enough it'll eventually reach the professors.


Professors, like VCs, don't have the time or the inclination to help you out of their good will. You need to give them a reason to help you, i.e. make them feel like you are helping them.


This is awesome. I love quick, succinct communication.

I have thought of early state funding as more "who you know," and it's good know I can email people!


There are many articles like this, but I think it's often hard to follow the guidelines. This one is really clear though.




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