Tag: cold email

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#unfiltered #22 The Lesson I Learned from Purposefully Replying to Spam Emails – Persistence, The Attention Allocation, and a Little Hack I Use

phone booth, spam emails, communication, cold emails

A few days ago, I watched Yes Theory‘s recent heartwarming and inspiring video, Creating a Subscriber’s Viral Job Application. And if you have a spare 20, I highly recommend checking it out. Yesterday, I chatted with a friend about the influx of spam calls these days. So, I thought; now that’s a start of a #unfiltered blogpost.

As a warning, this post is slightly more eccentric than, admittedly, my average #unfiltered blog post.

Prefacing with spam

I used to write this newsletter, Friday Morning Coffee Break, back in college for one of the clubs I helped lead. (Now that I think about it, coffee seems to be the theme for my content drops.) So if any of you subscribers then are reading this post now, this anecdote will be a momentary skip down memory lane.

So, you see, I’m a huge fan of comedy. And 3 years back, when I first learned about James Veitch, I just had to try it out myself. Replying to spam emails. From Nigerian princes. Cold emails from ‘celebrities’. Confirmation emails that require replying to unsubscribe.

If you’re curious as to how he pulls it off, you can check out his Hilarious (yes with a capital ‘H’) TED talks: here, here, and here.

What I did

When I received:

Subject: Save a 80% Off meds delivered discretely to your door

Don’t miss this once in a lifetime chance to get 80% off of a lifetime supply of Viagra!
GotBanq

… my keyboard was ready.

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#unfiltered #20 You Will Be What You Eat, You Are What You Excrete – Leading vs Lagging Indicators, One of My Relationship-Building/Networking Practices

stars, starry night, networking tips

Yesterday evening, I sat in our backyard, sipping homemade lemonade and sketching out my weekly creative endeavor (why). Between sips and furtive glances upwards, I hoped to catch a glimpse of NEOWISE. But alas, I forgot to pray to the weather gods in the morning.

Disappointed, I packed up to head inside. As if by a stroke of fate, my phone buzzed. You know, this story would be more dramatic if my disappointment was telepathically transmitted to my friends. Tongue in cheek, I apologize if I got your hopes up. But, it was merely the influx of messages after my timed “Do Not Disturb” mode switched off. Yet one of these blips came from a good ol’ swim team pal into our group chat. Lo and behold – an HD cross section in time of the exact comet.

I propped my cell above my head, positioned just north of the horizon. And unable to hold my smile back, I stuck around for a while longer.

So what?

You’re probably wondering: How the hell does yesterday’s smile have to do with “You will be what you eat, you are what you excrete”. As the title of the post so kindly suggests. Trust me it does. Admittedly, probably not the greatest of blog post titles, but, hey, it rhymes. Which might be the lamest excuse you’ve heard this month. But I digress.

You will be what put in your body. You are already what comes out of your body. Literally. Well, I’m sure my cousins who are molecular cell biologists will point out some (or many) of the nuances I missed. But we don’t have to count the cards.

The same is true for your personality. You build your personality based on the inputs in your life from when you’re younger. Your personality is subsequently evidenced by what you say and do.

And, I can say the same for education, biases, and so on. For the purpose of this post, I’d like to underscore one other – relationship-building. Or as most others understand it, networking. But I have a mild allergic reaction to that nomination.

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#unfiltered #18 Naivety vs Curiosity – Asking Questions, How to Preface ‘Dumb’ Questions, Tactics from People Smarter than Me, The Questions during Founder-Investor Pitch

asking questions, naivete vs curiosity, how to ask questions

Friday last week, I jumped on a phone call with a founder who reached out to me after checking out my blog. In my deep fascination on how she found and learns from her mentors, she shed some light as to why she feels safe to ask stupid questions. The TL;DR of her answer – implicit trust, blended with mutual respect and admiration. That her mentors know that when she does ask a question, it’s out of curiosity and not willing ignorance – or naivety.

But on a wider scope, our conversation got me thinking and reflecting. How can we build psychological safety around questions that may seem dumb at first glace? And sometimes, even unwittingly, may seem foolish to the person answering. The characteristics of which, include:

  • A question whose answer is easily Google-able;
  • A question that the person answering may have heard too many times (and subsequently, may feel fatigue from answering again);
  • And, a question whose answer may seem like common sense. But common sense, arguably, is subjective. Take, for example, selling losses and holding gains in the stock market may be common sense to practiced public market investors, but may feel counter-intuitive to the average amateur trader.

We’re Human

But, if you’re like me, every so often, I ask a ‘dumb’ question. Or I feel the urge to ask it ’cause either I think the person I’m asking would provide a perspective I can’t find elsewhere or, simply, purely by accident. The latter of which happens, though I try not to, when I’m droning through a conversation. When my mind regresses to “How are you doing?” or the like.

To fix the latter, the simple solution is to be more cognizant and aware during conversations. For the former, I play with contextualization and exaggeration. Now, I should note that this isn’t a foolproof strategy and neither is it guaranteed to not make you look like a fool. You may still seem like one. But hopefully, if you’re still dying to know (and for some reason, you haven’t done your homework), you’re more likely to get an answer.

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My Cold Email “Template”

coffee, cold email template

First of all, I should preface. Though I find templates to be useful when you’re shooting for quantity over quality, I default to only using limited elements of one, if at all, when my goal is quality > quantity. The goal with 90% of my emails I have ever sent is where I’m punching above my weight class, be it –

  • Applying to college – writing a letter to the deans of respective schools to get a personal tour,
  • Asking for funding – from top-tier VCs and potential long-term partners,
  • Asking for advice – from VCs and seasoned founders, in the form of tactical and veteran mentorship,
  • Or, exploring perspectives. I’m pretty liberal in my scope here.

If you’re here reading this and are looking for a silver bullet. If you’re looking to be that John Wick walking away from a massive explosion behind you… well, I regret to let you know – I don’t have one. I wish, but I don’t. But to me, that’s what makes this black box of relationship building ever the more fascinating. Had it been easy, I would have gotten bored real fast. Unfortunately, I have a limited mental stamina for things that work because… well, they work.

Inspired and encouraged by my conversations with 4 amazing souls over the past week – a founder, product manager, startup mentor, and my mom, here are the tactics I learned after years of reaching out to folks that inspire me, specifically closing one a week since 6 years ago.

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An Underappreciated Way to Get a VC’s Attention

message, fundraising, investor list, how to get a VC's attention

It’s been a trying time for founders to fundraise in these turbulent times. On one end, you have investors who took a U-turn on plans to invest this year. On the other, you have investors still deploying or looking to deploy capital. The latter further breaks down into: (a) investors who are taking more calculated bets – raising the bar for the kind of startup that gets the capital, and (b) investors who find the opportunity to invest in the down markets. The latter cohort of the latter cohort seems to hold truer at and prior to the pre-seed stages among microfunds and angel groups.

The Tightening of the Market

Disregarding the investors who aren’t deploying capital anymore, it’s been harder than ever to raise. Here’s why:

  1. Anecdotally, more startups are looking to fundraise. Many have pushed up their fundraising schedules.
  2. The standard is much higher now than before. And that includes a stronger consideration for the problem you’re addressing. Is it anti-fragile? Is it recession-proof? If your numbers are down now, will they eventually ‘flip’ back on track post-quarantine?
  3. Valuations are taking a hit. Where before your startup may have been overvalued (especially in Silicon Valley), many startups are facing “more realistic” round sizes. And flat or down rounds are more prevalent.
  4. When investors can’t meet founders in-person, they’re resorting to data, data, data. Investors no longer have the luxury to benchmark a gut check over Zoom/email, as they would have in noticing micro-gestures and other situational context clues. Anecdotally, investors are spending much more time and putting much more weight on diligence than before.

And, that’s why founders, more than ever, should (re)consider fundraising strategies. This was something that I learned when I was on the operating side and at one point, working on the fundraising front for Localwise.

Much like when high school students apply for college, founders should have a three-tiered list – SMR, as I like to call it:

  • Safety,
  • Meet,
  • And, reach.

Safety

Safety investors are those that are definitely going to take the meeting. And will most likely invest in you (i.e. at the idea stage, this mostly comprises of family, friends, and colleagues, maybe even early fans via crowdfunding). Admittedly, they can only contribute small sums of money. Each check also carry little to no strategic weight on the cap table.

Meet

Meet investors are investors that will most likely take the first meeting, but you’ll need to do a little leg work to get them to invest. Many of these will most likely stick to being participants than leads in any round. They carry some strategic weight on the cap table – in the capacity of their network, their brand, or advice.

Reach

Your reach investors will be your greatest sponsors. The people who have the highest potential to get you hitting the ground running. These folks usually have crowded inboxes already. And you’ll need to figure out how to best reach them. Unless they reach out to you, you will most likely fall just short of their gold standard. But once you stget these onboard, your relationship will set you up for reaching your next milestone better than any other individual partnership. At the same time, they will be the ones who are most likely going to have true conviction behind your product, your market insight, and your team. They typically lead rounds, and carry great strategic value to your startup (i.e. top tier investors, SMEs, product leaders in your respective vertical). For lack of better words, your ‘dream girl’ or ‘guy’.

Your Priorities

When pitching (and practicing your pitch), go for a bottom-up approach. Safety, then meet, then finally reach. And ideally, by the time you’re pitching to your ‘dream girl’ or ‘guy’, you’d have refined your pitch that best fits their palate.

When prioritizing time and effort, go top-down. Since you have limited bandwidth, spend the most time doing diligence on your reach investors. Then meet. And if you still have time, safety.

Diligence and Reaching Out

During your diligence process, look at their team, their individual and collective experience. Is their partnership, especially the checkwriters, diverse? Were they former operators? Or career VCs? And based on what they have, what do you, as a founder, need the most right now? Also, to better understand the marriage you’ll be getting in to, talk to their portfolio startups and investors that have worked with them before. Pay special attention to the the venture bets that didn’t work out. Was there a break up? If there was, what was it like? How did the investor help them navigate tough times?

It’s easy to be positive and cohesive when things are working out, but how does that investor react when things aren’t going as expected?

After talking to the (ex-)portfolio founders, if you feel like they have a good grasp on what you’re working on and are excited for you, ask them for an intro. Focus on those founders who have gone through the idea maze in your respective vertical, or an adjacent one. If you’re defining a new vertical, or that investor has just never invested in your vertical, but has expressed public interest of pursuing investments in yours, ask founders who have the same or a similar business model to yours. After all, that’s going to be the kind of solid warm intro you want.

In Closing

Though there are other ways to get in front of investors (some more questionable and/or gutsy than others), including, but not limited to:

  • Warm intros from friend/mutualLinkedIn connection,
  • Cold email/DM,
  • Reaching out to a more junior team member (scout/analyst/associate/principal),
  • Presenting at accelerator/incubator Demo Days,
  • Presenting at a hot conference, like TC Disrupt or SXSW,
  • Volunteering at the same non-profit as them,
  • Auditing their lecture at Stanford,
  • Or, squeezing into their elevator (although most VC offices are pretty lateral)…

… anecdotally, it seems many founders overlook the means of getting an intro from a VC’s portfolio.

Photo by Marvinton from Pixabay

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Drawing Inspiration

drawing inspiration, ideas, eclipse, writer's block

On Tuesday, I had the great honor to jump on a call with someone who is both a brilliant composer and an acclaimed orchestral conductor. Though he was classically trained, he found fame in the world of video games. And I couldn’t help but ask where he draws his inspiration when composing musicality to pair with various mediums of entertainment, even outside of games. He answered simply:

“Everywhere.”

He followed up that to help him frame his ideas around the subject of his piece: “I watch a little bit, not too much to have the show or game dominate in his mind, but enough to start off.” Just a small spark to start the fire. What he said echoed in mind, reminding me of a conversation I had with another friend – entrepreneur, author, and podcaster – prior to self-quarantining ourselves. He told me: “There’s no such thing as writer’s block. It’s that desire for perfection that holds us back from putting our pen on paper. But once we let go of trying to be perfect, we can find inspiration from everything around us.”

In all honesty, when he first told me this, I thought he was being quite presumptive. Especially it was at a point in time I was struggling to find content to put out weekly. But he was right. And, as you may have guessed, that became the kindling for the #unfiltered series.

Similarly, a few weeks back, a college buddy asked me where I find my inspiration for pieces on this blog. Though I am echelons shy of the musical talent I spoke with two days ago, I offered him the path I took to get me here:

  • Practice ideating daily.
  • Talk to people.
  • Meditate and/or write in a gratitude journal.
  • Write an audience of one.

Practice ideating daily.

My brain, like your brain, is a muscle. The more I practice using it, the better it gets. The same is true for ideas. The more ideas I write, the better I’ll get. It can be one sentence. Or, it can be 5 pages. But make sure to dedicate at least a full page to each day, even if 95% of it may be blank. The point is to deliberately do so every day, with no cheat days. Personally, I spent the first 2 weeks, writing one sentence entries.

So, I invested in an idea journal. In fact, probably my best investment I made in the past 3 years. And, I didn’t bother buying a cheap one. It was a Moleskine art sketchbook. At the time, a $17 purchase plus tax. And for a broke college student, that was a sizable amount – two good meals worth. A good alternative and the one I use now is a Leuchtturm1917 sketchbook. Why? Because it forced me to use it. I realized for me, the better the notebook is, the more I’m inclined to not let it go to waste.

Although I wish this was my original idea, my professor at Cal taught me this simple, but effective strategy.

Talk to people.

When I found myself unable to grasp at any ideas (that I thought were good), I talked to people. The more obsessive they were about their passion, the better. The more (positive and negative) emotion they channel into their work, the more insight they’ll have. And, frankly, excitement is contagious.

Talk to at least one of them from this cohort a week. Take notes, follow up, and ask more questions. The last part usually more independently, depending on their bandwidth.

Meditate and/or write in a gratitude journal.

Be thankful. It’s a useful frame of mind to be in. Positive thinking helps with more expansive creativity. Negative thoughts and stress, depending on its severity, narrows down the scope of your creativity.

Write for an audience of one.

Many professional writers are taught to find a target audience and write for them. Focus on a specific segment, before broadening, if ever. My mentors taught me to take this one step further. Instead one specific segment, just one person. It’s much better to write for 1 person who I know will always love my content than to write for a hypothetical many who may or may not even like it. For me, it’s myself. When I’m writing here, I’m merely a hobbyist. I don’t have any grand goal of reaching one million subscribers (not that I’m opposed to it). I’m just here to immerse myself in the joy of writing. And if I am lucky to have affected someone else’s life in a meaningful way, that’s my cherry on top.

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Cold Emails – Addressing Elephants and Rock Hyraxes

cold email, elephant

Amidst this unpredictable pandemic, where people are sheltering in place and social distancing themselves. We’ve reached a new inflection point in the curve of virtualizing our worlds. And it just so happens that this is one of the best times to reach out via cold email.

I want to preface by saying this practice has largely worked for me when I reach out. But is neither representative of the population nor guarantees a reply.

The Lesser-known Rock Hyrax in the Room

When reaching out via cold email, the first thing I do is to address the elephant in the room. Outside of the “why are you reaching out to me” question that everyone has, the second most pertinent question, consciously or subconsciously, often is “how long will this take?” – the rock hyrax in the room.

Fun fact: Apparently, the rock hyrax is the elephant’s closest cousin. Frankly, I didn’t know that until I began writing this piece.

Most people who’ve spent some time honing their skills for cold emailing can answer the first question rather well. But, many miss the second.

Close cousins include:

  1. What does the time commitment look like to respond to the email? To address the ask meaningfully? What is my opportunity cost?
  2. How long will this relationship like?
  3. Can I get along with this person?
  4. Will this be an extension of work?

The most important frame of mind is to be honest. If it’s a sales call, it’s a sales call, not “expanding my network.” If you think it’s going to take half an hour to chat, say it. Don’t be nebulous. Set expectations and be forthcoming and candid from the get-go.

“So… why are you reaching out to me?”

And, I’ll leave no stone unturned. If you know the receiving end is busy, also address why they are the best candidate to answer your ask. Be specific. Whether you’re trying to close the first few clients in your pipeline or reaching out to learn, consider the answers to these questions:

  1. How did you find them?
  2. What about them makes you insatiably curious to reach out?
  3. Why they’re the best fit? What’s in it for them? What’s in it for you? (Note I ask “What’s in it for them” before I ask “What’s in it for you”)
  4. Have you spent time doing diligence? On the person? Industry? Topic?
  5. (Optional) Are there inflection points in their life/career/public presence that are unrelated to your ask, but you find oddly fascinating? Pick 1-2.
    1. Note: You should be approaching this question from a point of admiration, fascination, and/or genuine curiosity. If you have any malicious intent, don’t bother.

It just so happens that the same holds for rekindling old flames. Although it’s, by no means, a replacement for social interaction, hopefully it’ll keep the pan hot, when you do sautée after we start mingling at dinner parties again.

Photo by Geran de Klerk on Unsplash

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#unfiltered #6 The Quantum State of Advice – The Marriage of the Schrödinger Equation and Cold Emails

quantum, schrodinger's cat, advice
Photo by Danilo Raphael Reyes on Unsplash

“The rearview mirror is always clearer than the windshield.”

– Warren Buffett

Although Mr. Buffett said that in relation to business, I find it equally true everywhere else. Just like the rearview mirror and the windshield, I want to denote the dichotomy between feedback and advice.

  • Feedback – given post-mortem, after-the-fact, help after peering into the rearview mirror
  • Advice – given “pre-mortem” or in an ad-hoc sense, help offered proactively, looking through the windshield.

As this title suggests, for this post, I’ll just be focusing on advice. And well, that may be as profound as this post will get, the rest is just a trip down my nerdy shower thoughts after watching this video about parallel worlds my equally nerdy friend sent me.

You have been warned…

The world right now

Well, you see, I work in an industry that thrives off of giving advice. Especially in these trying times when businesses are not only trying not to lay off their staff, many are working around how to stay afloat. My friends in culinary projected a 50% decline in occupancy rate, but at this point, have shifted entirely to to-go options and lowered their own salaries anywhere from 35% to 100%. My pals in D2C (direct-to-consumer), transportation, or travel have been punched in the gut. And, my entrepreneurial buddies are doubling down on cash preservation, rather than growth. The rule of thumb we’re telling founders to have at least as much runway to weather the next 18 months. So if that requires pushing up your fundraising schedule, then time to re-prioritize.

The nerd comes out

But after decades worth of receiving advice and years worth of giving advice, I learned something that seems like a no-brainer now. You see, the thing is advice is both right and wrong simultaneously. You can say it’s in a superposition of being right and wrong… at least until that advice is observed by its subsequent application and result.

Let’s take it a step further. Can we predict the probabilistic effect of advice on a given situation? Sure. So, let’s take a look at the Schrödinger equation.

Image result for schrodinger equation

There’s a few elements that stand out. |Ψ(t)> denotes a time-dependent function. And, H(t) denotes the sum of the kinetic and potential energies for all the particles in the system. In relevance with advice, the timeliness ( |Ψ(t)> ) of the advice matters – in relation to both where you are now and where you’re heading. The eigenvector of you. At the same time, it’s important to factor in your velocity now and everyone and everything else’s involved in the situation.

You might be wondering how come I didn’t analogize to the classical mechanics version of this equation: F=ma. Excellent observation! The reason is that the classical mechanics version doesn’t account for wave-like probabilistic outcomes. And advice and its relative observation by application doesn’t have a guaranteed outcome. Rather, it plays a hand in either increasing or decreasing the outcome of an event.

Here’s an example

One of the first lessons I learned, if not the very first piece of advice I got, when learning about ‘Cold Emails 101’ was:

“Limit your email to 3-5 sentences.”

Makes sense. I didn’t want to bombard the person I was reaching out to. I want to make it easy for them to read and reply to. But over the years, I learned that the real answer to email length is ‘It depends’. If you’re reaching out to someone who:

  • already has a lot of clutter in his/her inbox,
  • has expressed disdain or annoyance in reading emails,
  • doesn’t check his/her inbox often,
  • has a succinct personality (person-of-few-words),
  • or anything else that suggests they’re not going to bother with a long email,

… then send the 3-5 sentences. But if that person:

  • wants to see that you’ve spent your time doing your diligence (not a generic spray-and-pray email),
  • has a more extreme sense of self-worth,
  • is curious/open to flushed-out new ideas/perspectives,
  • enjoys a tale,
  • is a comedian,
  • or anything to suggest that a longer email may stand out to them,

… then craft a longer message. I was able to get in touch with some of the people I really admire by crafting lengthier emails. That said, there’s always a bit more nuance in all of this. Here’s a piece I wrote last year that may provide some context. And this is only probabilistically higher, holding all other variables constant.

Even so, there’s always more than two options. DM them on their most active social media platform. Get an intro. Send them meaningful content. Send a hand-written note by messenger hawk. Visit them in person, without unwanted trespassing. Go viral by making a lollipop with their face on it. Buy an extrasolar star and name it after them. The list is endless.

In sum, the advice of limiting the verbage of your emails is right and wrong at the same time. It merely depends on where the person you’re reaching out to is at and where they might be headed, as well as your own goals in life. And of course, as with any advice, limiting your sentences may boost or detract from the likelihood of a reply.

The disclaimer

As is the nature of an analogy, it breaks down when you get more granular. I should mention that I’m no astrophysicist (dealing with the macro) nor am I a quantum physicist (the micro). And I’m sure if any relevant occupation were to look into my analogy, there’d be tons of holes. I am merely a peripheral enthusiast.

quantum advice
My scribbles on paper which turned into this post.

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

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Pre-gaming Cold Emails

It’s the holiday season again – my favorite time of the year! From Glühwein to Christmas lights and decorations, it’s the perfect time of year to tackle on many things that bring us cheer. When it comes to the people around us and in our lives, the holiday season is my favorite excuse to catch up with old friends and meet new folks.

‘Tis the Season to Reach Out

Outside the exciting, but tough world of venture capital and entrepreneurship, I enjoy spending time meeting brilliant individuals outside of the technology sphere. To the point, I made a New Year’s resolution half a decade ago that I’m going to meet one new person I’m crazy passionate about every single week. I’ve stuck with that resolution ever since. Obviously, it required me to find a way to get in contact with these amazing folks every week. From cold emails to calls to handwritten letters to knocking on their front door, whether it was going to be a success or not, each week provided me with a new challenge I get excited to embark. And I’ve found that I get the highest positive response rate out of my 52 weeks a year, the five to six weeks starting from Thanksgiving week until the first week of the new year – or in this coming year’s case, the new decade. Over the holidays, it’s true that people don’t check their inboxes as frequently, but it seems that most people who plan to reach out believe that too, and often stall until the new year, at least many of my friends and coworkers do – a sort of New Year’s resolution. Of course, I’m not saying there’s any guarantee in a positive response, but chances do seem higher.

I’d like to start off by saying that in the context of reaching out to individual people that I can imagine becoming friends with, I don’t have any holistic templates for cold emails, outside of a few sentences, which I’ll share in this post. To me, writing a cold email is a labor of love, and it really pays off when I make the content as relevant to the addressee as possible. On the flip side, if the purpose is to spray-and-pray or to gain leads in a funnel, this post may not be entirely pertinent, though there may be sprinkles of fortune scattered below in how I explore the mental maze in sending a cold email.

The Warm Up

Having spent almost a decade in competitive swimming, the first, and probably the most rewarding, yet most underappreciated, exercise I learned was visualization. Visualization comes in two parts: 1) Seeing myself win the race and get my desired time, and 2) Being prepared for any possible resistance or friction to winning. Don’t get me wrong; the race itself is important, but about a year into my swimming career, I started competing increasingly with athletes that were of a similar caliber as I was, where the margin between our best times existed in the milliseconds. And arguably, what makes or breaks the race is how mentally prepared you are before your race even begins – what all the 30-40 hour training weeks will amount to.

It’s the same when I send cold emails. I used to think I was special, having gotten into an amazing university, some of the most competitive and “elite” organizations on campus, and so on. Truth is it was all bullcrap! And sending those cold emails was one element that grounded me. A cold email is nothing but another tick in their inbox – nothing more, nothing less. I’m not allocated more real estate on the virtual battlefield. In fact, in some ways, you could even say I can’t even pay-to-win. If I’m punching above my weight class, then I was and am another competitor, competing for a limited, finite resource: attention.

Jeff Bezos once said:

“If everything you do needs to work on a three-year time horizon, then you’re competing against a lot of people. But if you’re willing to invest on a seven-year time horizon, you’re now competing against a fraction of those people, because very few companies are willing to do that.

“At Amazon we like things to work in five to seven years. We’re willing to plant seeds, let them grow and we’re very stubborn. We say we’re stubborn on vision and flexible on details.”

Although he said this in relation to building a company, it’s equally true in the competitive landscape of sending a cold email. You have to be willing to push your time horizon beyond any of your competitors. Or in other words, be prepared to go the distance – to play the long game.

What does that mean? Any permutation of creativity juices, like letters sent via messenger pigeon (or turtle doves for this time of year), and recurring emails works. The most important thing to keep in mind, when playing the long game, is cadence and commitment. My default is usually one email a week, usually Monday or Tuesday morning, up to three weeks, with each one showing the positive delta in knowledge acquisition compared to the past week, but still need help in their respective expertise on a particular topic.

Some of my friends and founders I met have tried more extreme versions of what I do. For example, one persistent founder I know once sent the same email every day at 9AM for three months to finally get a meeting with an executive at a major entertainment studio. Another sent the same pitch email to a well-renowned investor every week for a year, and now they’re best buds and play pick-up games every month. The disclaimer is that these may be edge cases, but do be cognizant to never overstay your welcome. If you’re asked to stop, stop.

When should I send a cold email?

On a macro scale, two overarching themes that run in my head are my personal resource availability and timing.

Personal Resource Availability

Outside of the obvious answer of trying to get in touch with someone outside of my immediate network, the question would be better phrased as: When can I not get a solid warm intro? I used to think all warm intros were the same, and that a warm intro is always better than a cold email. Truth is: it’s not always. There’s a huge spectrum to how great (or not) a warm intro can be.

Let’s think about it from the perspective of a Net Promoter Score (NPS). We may all be familiar with the question:

One a scale of 1-10, how likely are you to recommend this product to your friend?

We’ve most likely seen it when filling out a survey after you used or bought a product or service. It’s how businesses measure your satisfaction of their product or service. Although one might think that five is average, anything greater than five is above average, and anything less is below average, the truth is most people regress to filling out ‘7’. ‘7’ is a proxy for not offending anyone but at the same time, saying the the product or service was “okay.” Businesses usually measure 7’s and 8’s as okay, where the real breadwinners are the 9’s and 10’s. Similarly, when I seek or decide to give warm intros, it really comes down to: Can I get or give a 9 or 10-score warm intro? In my head, it subsequently creates a binary scale: a solid warm intro (score = 9 or 10) and a weak warm intro (score ≤ 8).

Subsequently, when should I send a cold email is answered by… whenever I can’t get a solid warm intro.

Solid Warm Intro > Cold Email > Weak Warm Intro

Now, it begs: what are the characteristics of a warm intro? This is decided in two parts: content and matchmaker.

I characterize content in three parts: the subject, the introduction, and the ask. The subject is meant to attract and describe the purpose of the email. The introduction is to explain who I am. The ask, and probably the most important bit, which has to be clear from the beginning, is what I want out of the introduction. With the first introduction, and also for the cold email, I keep it simple to one of two things, depending on the other person’s bandwidth:

  • A 20-minute call or in-person chat (Note: If I go with this option, and the person accepts, I follow up with 2-3 questions I plan to ask during the chat)
  • One burning question

To make it easier for the matchmaker, I often send them a short two to three sentences that summarizes the above, and can easily be forwarded along. My goal is to make it as easy and simple for both the matchmaker and the person I want to get in touch with.

The matchmaker, or the person referring me, is any one or a combination of the following:

  • A subject-matter expert (SME) in my respective field, defined by having a track record for success and external validation by other thought leaders;
  • Someone who knows me (and my work) well, capable of succinctly describing what I’m working on and me, and is excited for me;
  • And/or, someone who knows the person I want to get in touch with well, where the matchmaker is either the first 100 names the person receiving the introduction thinks of, or the first five names in that given field.

Timing

Timing is crucial. And to measure it, I ask myself four questions:

  1. Where are they (in life)?
  2. Where am I (in life)?
  3. What is my purpose?
  4. How can they win?

Where are they (in life)? Is the person I want to get in touch with busy tackling a new project? Preparing for a new baby? Switching careers? On a holiday vacation? If the person has a large presence on social media, most of these can be found online. Take special notice of the inflection points and outliers in their life. Some are more obvious than others. Of course, they’ll be willing to talk about the moments in their life when their second derivative was positive, but I think there’s a bigger story behind the moments when second derivative was negative. Of course, it may be something I bring up later in the conversation depending on how openly vulnerable the person I’m reaching out to naturally is. If the person has a limited presence online, it’s best to ask the matchmaker or mutual friends and connections. Sometimes, I just can’t find evidence of his/her bandwidth anywhere, so I preface my cold email ask with:

I know you’re extremely busy as is. If this does surface in your inbox and you have the time to reply, I’m grateful if you could [insert ask]. Otherwise, I’ll reconnect in one month.

Leaving room for people to not feel bad to say no, and making sure to follow up have been the two hallmarks for me to potentially get a “yes” in the future. A “no” now isn’t a “no” forever.

Where am I (in life)? Have I done all the diligence I could possibly do before I reach out? Anything that is “Google-able” is not worth asking another individual, especially if I’m looking to punch above my weight class.

What is my purpose? Why am I reaching out? What makes this person special? Why might this person be the only one in the entire world who can answer my ask? If I’m reaching out in the networking sense, can I be this person’s friend for at least the next decade?

How can they win? Always give before taking. There’s plenty of literature online, explicitly and implicitly – on social media, in the news, in their public appearances – that would help arrive at what they might need. If I have to ask him/her how I can help him/her, then I’m already wasting that person’s time.

In closing

In a saturated market of information, product-market fit is defined by attention. So keep it personal. Keep it direct. And have some fun.

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