Tag: garry tan

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Don’t Drop the Ball After the First Shot – Following Up Cold Emails

If you’re a regular on this blog, you’re probably no stranger to my essays on cold emails – whether it’s my cold outreach mental model or lessons from replying to spam emails or how I write longer cold emails as opposed to shorter. Yet, I recently realized I’ve shared my thoughts on the pre-game and the game itself, but I’ve yet to write on the post-game. So this essay is dedicated to exactly that. What do you do after you send that initial cold email?

The short answer: If you want to stand out, always follow up. To quote my good friend, Christen on her TikTok, where she shares amazing soundbites of career advice and networking.

The longer answer

I met a founder once who emailed an executive at Disney every business day for almost one year, minus ten days. The caveat is at the top of every daily email he wrote, “If you want me to stop, I will.” Almost a year after he began, the executive took the meeting. And Disney is now one of this startup’s biggest customers.

I met another founder a few years ago, who retweeted tweets from a Forbes’ Midas 100 VC every week for three months, while including his own constructive commentary each time. So, when this founder began his fundraise three months later, this VC set up a meeting with that founder within two hours of the cold email, first thanking the founder for his thoughts over the past few months.

Garry Tan and Apoorva Mehta have both shared this story publicly. Apoorva, founder of Instacart, back in 2012, wanted to apply to Y Combinator. Unfortunately, he was applying two months late. So he reached out to all the YC alum he knew to get intros to the YC partners. He just needed one to be interested. But after every single one said no, Garry, then a partner at YC, wrote: “You could submit a late application, but it will be nearly impossible to get you in now.”

For Apoorva, that meant “it was possible.” He sent an application and a video in, but Garry responded with another “no” several days later. But instead of pushing with another email and another application, Apoorva decided to send Garry a 6-pack of beer delivered by Instacart. So that Garry could try out the product firsthand. 21st Amendment’s Back in Black, to be specific. In the end, without any precedent, Instacart was accepted. And the rest is history.

So, what is the common thread here?

As my friend once told me, “It’s not hard to be persistent. Most people can easily be. But most people aren’t persistent AND considerate.” Persistence is keeping your promises to yourself. Being considerate is respecting and keeping your promises to others – explicit and implicit. Explicitly, if you say you’re going to do something, do it. Implicitly, understand the social context, their schedule, their cognitive load. One of the lines I always add at the bottom (or sometimes at the top) of my cold outreaches:

“If you’re too busy, I completely understand.”

Or the variation I shared in my cold email “template”:

“I know you get a hundred emails a day, and if you don’t have any time to respond, I completely understand.”

To take that one step further, sometimes you’re reasonably confident they won’t have time to respond. Big life or career events may make it hard for them to respond, like:

  • New baby/paternity/maternity leave
  • New publication
  • Recently did a (podcast) interview
  • Released some version of viral content (i.e. YouTube video, TikTok, Clubhouse, Twitter, etc.)
  • Founder raising a new round
  • Upcoming product launch they’re a key player in
  • VC raising a new fund
  • Shit hit the fan
  • Anything else the press is actively writing about

If that is your assumption, I add in one more line:

“If you don’t have time to respond, I’ll follow up one week [or whatever other timeframe] from today.”

And once you’ve said it, do it. To save you the time to draft up a follow up email a week later, a hack I use is to just write that follow up email as soon as you send the first email. Then schedule it to send a week from the day you sent the first. Make sure that each follow-up email isn’t the exact same. Show updates on what you learned, found, or thought about, as well as additional value to the person you’re reaching out to. While this hack is the bare minimum of what you can do to follow up, this should never be the ceiling. 9 out of 10 times I find myself going back, cancelling the send, updating the email with my learnings, then re-scheduling it.

Follow up at least twice after you send the initial cold email. But be understanding of their circumstances. And of course, never overstay your welcome. Understand the difference between a soft “no” and a hard “no”. In the circumstances of a soft “no”, recognize the variables that led to it. And reach back out when those variables are not in play, or to your best guess.

In closing

I met a brilliant founder years ago who, at the time, scaled his business to 100 employees, and he told me something that resonates with me till this day. “You can only learn from experience, but it doesn’t necessarily have to be yours.” Though I learned of his saying a few years after, it summarizes why I started my 6-year at least once a week cold outreach streak. To learn vicariously through others’ experiences. And if that was and is the impetus, it’d be a shame if I didn’t see it through to the best of my ability. ‘Cause if I was gonna give up after just sending one email, why start?

As Ron Swanson once said, “Never half-ass two things; whole-ass one thing.” So if you’re gonna start with the first email, you might as well send the next two. If the first shot doesn’t swish, catch the rebound and shoot again. Persistence. And ideally rebound thoughtfully.

Photo by William Topa on Unsplash

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Four Signs of Startup Founders Prioritizing Growth Too Soon

scale, too soon, founders, startup growth metrics

Humans are one of the most awe-inspiring creatures that have ever graced this planet. Even though we don’t have the sharpest claws or toughest skins nor can we innately survive -50 degrees Fahrenheit, we’ve crafted tools and environments to help us survive in brutal nature. But arguably, our greatest trait is that we’re capable of writing huge epics that transcend our individual abilities and contributions. And share these narratives to inspire not only ourselves but the fellow humans around us.

A member of the our proud race, founders are no different. They are some of the greatest forecasters out there. To use Garry Tan’s Babe Ruth analogy, founders have the potential of hitting a home run in the direction they point. They build worlds, universes, myths and realities that define the future. They live in the future using the tools of today. In fact, there’s a term for it. First used by Bud Tribble in 1981 to describe Steve Jobs’ aura when building the Macintosh – the reality distortion field.

Yet, we humans are all prone to anxiety. A story nonetheless. Simply, one we tell ourselves of the future that restricts our present self’s ability to operate effectively. Anxiety comes in many shapes and sizes. For founders, one of said anxieties is attempting and worrying about the future without addressing the reality today. In the early days, it’s attempting scale before achieving product-market fit (PMF). Building a skyscraper without surveying the land – land that may be quicksand or concrete.

Here are four signs – some may not be as intuitive as the others:

The snapshot

  1. Your code architecture looks beautiful.
  2. You’re onboarding expensive experienced talent.
  3. Your cultural values lag behind the talent you hire (plan to hire).
  4. You’re bundling the market before you unbundle the needs.
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How to Build Fast and Not Break (As Many) Things – A Startup GTM Playbook

The tech world, particularly Silicon Valley, in the past 2 decades, has accelerated its growth ’cause of one mantra: “Move fast and break things.” Some of the most valuable products we know today were built because of that. Facebook, whose founder coined the phrase. Google. Amazon. LinkedIn. Uber. The list goes on. In sum, be “agile”. Simultaneously, I see founders, on the regular, take this mental model too far. They move fast, but they rarely give enough time to test their hypotheses.

Equally so, some companies cannot afford to “break things”. Take Dropbox, for example. Ruchi Sanghvi, founder of the South Park Commons Fund, former VP of Operations at Dropbox, and Facebook’s earliest female engineer, told VentureBeat in 2015, “Quality is really, really important to Dropbox, and as a result we needed to move slower — not slowly, but slower than Facebook.” Ruth Reader, who wrote for VentureBeat at the time, further extrapolated, “What was right for Facebook — fast-paced iteration and fixing bugs in real time — didn’t work for DropBox, an application people entrusted with personal documents like wedding photos or the first draft of a novel. What was valuable to DropBox was the details.”

On the other extreme, there are founders who spend day after day, week after week, and sometimes year after year, pursuing the “perfect” product before launching. If they were right on the money before, by the time they launch 6 months later, they might be 6 months off the money. Take the situation we’re all in today for example – the pandemic. No one could have predicted it. In fact, I had many a few predictions before the pandemic, which all proved to be unfortunately wrong.

  • The Marketplace of Startups, written on February 24, 2020 – I alluded to an opinion I held that consumer social was almost dead. The consumer app market had become so saturated that it was hard for new players to play in.
  • Myths around Startups and Business Ideas, written on October 12, 2020 – Pre-COVID, I was more bullish on Slack than Zoom as a public stock investment. History proved otherwise.

… and more to come. Mistakes are inevitable. And “the rear view mirror is always clearer than the windshield”, as Warren Buffett would describe. Seth Godin said in his recent interview on The Tim Ferriss Show: “Reassurance is futile because you never have enough of it.”

At the end of the day, as a startup founder, your raison d’être is creating value in the world where there wasn’t before. As Bill Gates puts it: “A platform is when the economic value of everybody that uses it, exceeds the value of the company that creates it.” Analogized, your startup is that platform.

So, in this post, using the lessons from other subject-matter experts (SMEs), I’ll share how startup teams can balance speed with intentionality in their go-to-market (GTM) strategy.

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On Scale – Lessons on Culture, Hiring, Operating, and Growth

flower, scale

One of my favorite thought exercises to do when I meet with founders who have reached the A- and B-stages (or beyond) is:

“What will his/her company look like if he/she is no longer there?”

The Preface

While the question looks like one that’s designed to replace the founder(s), my intention is everything but that. Rather, I ask myself that because I want to put perspective as to how the founder(s) have empowered their team to do more than they could independently. Where the collective whole is greater than the sum of its parts. Have the founders built something that is greater than themselves? And is each team member self-motivated to pursue the mission and vision?

It reminds me of the story of a NASA janitor’s reply when President Kennedy asked: “Hi, I’m Jack Kennedy. What are you doing?”

“Well, Mr. President,” the janitor responded, “I’m helping put a man on the moon.”

From the astronaut who was to go into space to the janitor cleaning the halls of NASAs space center, each and every one had the same fulfilling purpose that they were doing something greater than themselves.

And if the CEO is able to do that, their potential to inspire even more and build a greater company is in sight. Can he/she scale him/herself? And in doing so, scale the company past product-market fit (PMF)?

For the purpose of this post, I’ll take scale from a culture, hiring, operating, and product perspective, though there are much more than just the above when it comes to scale. Answering the questions, as a founder:

  • How do you expand your audience?
  • How do you build a team to do so?
  • And, how do you scale yourself?

And to do so, I’ll borrow the insights of 10 people who have more miles on their odometer than I do.

While many of these lessons are applicable even in the later stages of growth, I want to preface that these insights are largely for founders just starting to scale. When you’ve just gone from zero to one, and are now beginning to look towards infinity.

The TL;DR

  1. Build a (controversial) shocking culture.
  2. Hire intentionally.
  3. Retaining talent requires trust.
  4. Build and follow an operating philosophy.
    • Create, hold, and share excitement.
    • Align calendars.
  5. Upgrade adjacent users as your next beachhead.
  6. Capture adoption by changing only 1 variable per user segment.
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