Entrepreneur Office Hours - Issue #72

Sharing the secret to a great sales pitch

Just in time for that long, boring drive to visit your in-laws this Thanksgiving, I’ve got a very special episode of Web Masters for you featuring Sabeer Bhatia, founding CEO of Hotmail. Yes… that Hotmail.

Also, as you’ll read in this issue’s featured article, by referencing Thanksgiving, I’ve just made the exact mistake lots of venture capitalists made when they initially rejected Sabeer and his pitch, ultimately missing out on a startup that exited for an incredible $400 million in just 18 months. Could VCs be making the same mistake when evaluating your startup pitch?

While I’m on the subject of pitches, this issue’s Q&A touches on the secret to making great sales pitches. If you aren’t good at selling things, I can almost guarantee this is the reason. In fact, I’m so sure, my (free) advice comes with a money back guarantee. What a bargain!


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Why a Company That Exited for $400M in 18 Months Had Trouble Raising Its First Round of Funding

Sometimes, investors just can’t appreciate a great startup idea even when they’re staring right at it.

The Engineer Who Made Email Free

Who still has their old @Hotmail email account? Or knows someone who still uses one? (I'm looking at you, Mom!) If you do, you're especially going to love the story of everyone's favorite free email service featuring Hotmail's founding CEO, Sabeer Bhatia.

Listen to full episode on:

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


What Bad Drivers and Bad Entrepreneurs Have in Common

My biggest pet peeve when driving is also great way to explain a common mistake I see lots of founders make when trying to pitch their startups.

Office Hours Q&A



Dear Aaron,

I think I like your articles about sales most of all. I wish you’d write more of them.

In the meantime, would you mind sharing your favorite sales technique?

Thank you very much,



No… thank you very much, Omar. You’re probably one of the few people who actually like reading about sales strategies. Everyone else seems to want to read about fundraising since fundraising articles are always my most popular.

However, I’ve written it before, and I’m sure I’ll write it again: If you’re really good at sales, you don’t need to worry about fundraising. So focus on sales!

As for great sales strategies, I’m by no means a master salesman. I’ve certainly gotten better over the years, but be sure to also look other places for great techniques.

In the meantime, the strategy I’m going to share is simple: Ask lots of questions.

I told you it was simple. It’s also incredibly effective. Most people think sales is about being great at talking, but that’s not true. Being great at sales means being great at listening. You need to learn to listen to the people you’re selling to in order to understand what they need so you can know what to sell them.

Because of this, questions are like a salesperson’s secret weapon. All you have to do is ask the right questions, and your prospective customers will literally tell you exactly what they’re looking for. If the thing you’re selling fits their needs, then the sales process becomes simple. You just explain how what you’re selling solves the person’s problem, and the sale will mostly take care of itself.

I promise, selling really is that easy. Most people struggle with their sales process because they think selling is about explaining what your product/business does before finding out the customer’s problem. In other words, as soon as the sales pitch begins, they immediately start talking about and explaining the thing they’re trying to sell.

Don’t do that!

Instead, ask questions and listen carefully to the answers. That’s the secret to being a great salesperson.

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