Entrepreneur Office Hours - Issue #54

Are you eating dog food? Why not?

The first time I heard a fellow entrepreneur use the phrase “we eat our own dog food,” I remember thinking: “What the heck are you talking about?” So I suppose I should explain it here. Eating your own dog food means being a customer for your own product. As you’ll learn in this issue, it’s also a critical competitive advantage.

Also in this issue, I tackle a hot button topic related to email prospecting: Is it rude/presumptuous/good/bad/other to include a calendar link and expect people to schedule?

And I’ve got a new episode of Web Masters for you. This one features Mark Organ, founder of Eloqua. Eloqua — in case you’ve never encountered it — is a pioneer in the SaaS marketing automation industry. As someone who spent years building marketing automation companies, I admit the interview was an opportunity for me to be a bit of a fanboy. But even if you don’t care about marketing automation, I’m sure you’ll still enjoy Mark’s story. It’s a good one!


P.S. Keep the great questions coming! I’ll answer them as quick as I can… I promise…

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Founder with $1 Billion+ in Exits Explains Why Startups Need to Eat Their Own Dog Food

If you can build a company that allows you to eat your own dog food — to be a power user of your own product — you might just put yourself in the best position possible to defeat the incumbent.

The Neuroscientist Who Automated Emails

You may or may care about all the specific intricacies of marketing automation, but, no matter who you are, you’re  surely someone who’s impacted by it. That's why you're going to love the newest episode of Web Masters featuring Mark Organ, founder of Eloqua, one of the companies that led the marketing automation revolution.

Get the full story on Web Masters:

…or search “Web Masters” wherever you listen to your favorite podcasts.


A Simple Trick To Improve Any Pitch Or Presentation

Sometimes the simplest tactics are the most effective. The trick here may seem simple when you read it, but I promise it’s going to have a valuable payoff.


Office Hours Q&A



Hey Aaron,

You seem like a prospecting email guru. Can you help my co-founder and I settle a debate?

What’s your opinion of including something like a Calendly link in a cold prospecting email and asking someone to choose a time on your calendar? Is it acceptable protocol, or is it too presumptuous?




Honestly, I’m just excited to be referred to as a “prospecting email guru.” I think I’m going to add that to my LinkedIn bio.

As for your question, lots of shades of gray here. Let’s look at the two main scenarios…

Scenario #1:

You’re sending personalized emails to a small number of very high priority prospects that have no clue who you are, but you need something from them. For example, C-suite execs at Fortune 100 companies you’re trying to sell into. Or venture capitalists for your next funding round.

In that case, I suggest proposing specific times to talk. Besides, chances are the person has an executive assistant who you’re going to get passed to, and the EA will handle scheduling. At that point, send the EA your Calendly link to make that person’s (and your) life easier.

You already alluded to the reason you don’t want to send calendar links in these kinds of emails. The links tend to come off as too presumptuous. You’re asking people in relative positions of “authority” to schedule with you, and, as a result, it reads poorly. It’s like saying, “come talk to me,” and they’re going to (mentally) respond by thinking, “Why the heck should I go to you?” while never actually responding to your email.

Scenario #2:

You’re sending cold prospecting emails to a large volume of people. For example, you’re executing a new email campaign like I described in my article from a few weeks back explaining how to send an effective drip email campaign.

In this scenario, a scheduling link to your calendar is still going to be perceived as presumptuous, and it’s going to turn some people off, but that’s OK. It’s still the most efficient way to execute the campaign. Well… it’s that or spend hours navigating dozens of annoying back-and-forth scheduling emails.

The key to this kind of email is having a clear value proposition. Sure, most people aren’t going to schedule. But, assuming you’re targeting your prospects correctly, the small fraction of people who genuinely and urgently need what you’re offering will swallow their pride and schedule directly with you.

Bonus Scenario:

If you’d asked me this question a year ago, I’d probably have ended here. But I’ve recently become a big fan of including calendar links even in personalized emails (both to people I know and in cold prospecting emails) because, quite frankly, they do make scheduling so much easier.

For example, when I try to schedule podcast guests, I include calendar links in my cold prospecting emails. It seems to work fairly well for two important reasons.

Reason #1: I’m offering something of value. I’ve got a popular podcast with lots of other well-known guests. Most entrepreneurs take one look at the guest list, want to be part of it, and so they schedule with me willingly. This, of course, isn’t exactly analogous to Scenario #1 I’ve described above. But the question is: how can you make Scenario #1 more like this bonus scenario? For example, is there something you can include in a cold prospecting email to a VC that makes the VC want to schedule with you?

Reason #2: The other thing I do in my cold prospecting emails to potential podcast guests is explicitly explain why I’m including a calendar link. I’ll write something like: “If you’re interested in chatting with me, but you want to avoid the annoying back-and-forth of scheduling, you can book whatever time works best for you on my calendar [link]here[/link].” In other words, by explaining why I’m including the calendar link and making sure the recipient understands I’m doing it to simplify the work I’m asking of them, it eliminates a lot of the problematic presumptuousness.

Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!