How To Be Unreasonable: A Conversation

 “Follow up and follow through.”

I met Daniel Epstein this past summer while teaching at the inaugural Bold Academy’s “School For Superheroes” in Boulder, Colorado. Daniel led a jam-packed Q&A session around the art of “The Ask” for new and veteran entrepreneurs and change-makers, and I sat in on the session. He made a number of interesting points and I had a chance to follow up with him and ask him to share a few more insights.

Here’s our conversation.

You focused on a particular topic at Bold Academy: The Art of The Ask, and you talked a lot about why it’s so important to ask for what you want and to get your message out to the right audience. What makes someone successful at asking for what they want?

Daniel: The most important thing is conviction. Don’t be shy about it. If you genuinely believe in what you’re asking for, or what you’re asking for someone to do—then you’ll do a good job. You have to believe in what you’re doing.

It doesn’t matter if it’s a customer, a relationship, or anything—if you actually, deeply believe in your core that this is something that they would love or benefit from, then that makes the ask easier. You need conviction.

A lot of people don’t ask for what they want. Why is it so important to ask for it?

Daniel: You’ve got to ask for so much as an entrepreneur. If you don’t ask, you won’t get it. However, you need to have a solid vision and conviction in what you’re doing. That’s first.

You also mentioned that after you ask for what you need—let’s say you ask for someone’s time, or you reach out to someone for a connection or piece of information—the next most important things are to Follow Up and Follow Through. What does this mean?

Daniel: So many people will ask for something and then never follow up. This blows my mind.

You’ve got to do all of it.

First, Ask.

Then, follow up—if you asked for a meeting in October, reach out to them and schedule that meeting and make it happen.

And then, follow through. Call them when you say you’re going to call them, and if you say you’ll send something to them after the meeting, send it.

The drop-off rate for both seems really high: most people don’t ask; then a large percentage of those people that ask still don’t follow up; and then again, of the people who follow-up, many of them don’t follow through. This makes someone who asks, follows up and follows through somewhat remarkable, don’t you think?

Daniel: Absolutely. If you ask, follow up, and follow through, you are doing something most people don’t do.

There’s one caveat, however: doing all of this requires an incredible amount of energy and time. On a personal level, how do you make time for it all? Is it possible to follow up and follow through with everyone you meet?

Daniel: No – You’ve got to focus on what your priority is at that time. I try to never drop the ball. Do I drop the ball? Of course. It happens. I try not to. So if it’s not a priority, what I say is this:

“Unfortunately at this time that’s not a priority for me so I won’t be able to follow through.”

When things DO matter, however, NEVER drop the ball. We work with a lot of investors in my company—and when they get excited about a new business or an entrepreneur, they will often reach out and the entrepreneur will say, “Sure, I’ll get back to you,”—and then might not follow up. When the entrepreneur doesn’t follow up, well—it’s incredible to me. Don’t do this. Don’t be this person. You have to follow up.

But when you start to have time and pressure demands, you’ve got to know early on not to overpromise. Be genuine. Follow through. When you can’t, don’t say that you will get something done and not follow up–Say you’ll do it, and when you do, follow through.

I can’t stress this enough: Always, always follow through.

And if you mess up—of course you mess up—be genuine about it. Be honest when you make a mistake, and tell them. Say, “Hey, I never got back to you about this in a timely matter and I’m really sorry about dropping the ball. Things have been hectic but I really want to talk to you.”

Here’s the bottom line. When you say you’re going to do something, do it. It’s so obvious and simple and yet so many people don’t do it.

Let’s think about this from another angle: Why do you think most people don’t follow up?

Daniel: I think it comes down to discipline. The difference between a good and a great entrepreneur (or any profession, really), is having discipline.

You can’t create something of real significance unless you really hustle, and going the extra mile when you follow up and follow through makes a difference.

 I think there’s a cultural acceptance of just saying, “Sure, sure, I’ll get it to you,” without really intending to do it that can be a problem. It’s so common that people don’t follow up that doing so makes you stand out. I think you need to have the discipline to say that you won’t when you actually aren’t going to do something, and do it when you say you’re going to do it.

So you have to be willing to say to someone—during that time when you’re meeting—“I wish I could schedule a meeting, but my priorities are laser focused on my current projects and I probably won’t be able to do that.” That can be tough.

Daniel: Right. It’s about discipline.

After working with so many entrepreneurs, are there any key characteristics and traits that stand out to you? What do you see in people who are successful?

Daniel: Three things come to mind right away:

The most important thing we select for in character traits is a paradoxical blend of confidence and humility—the confidence that they can make a difference in the lives of a million people. They need a conviction.

But also, it’s about the humility and realization that they can’t do it alone—that they need teams and partners. The humility to be honest when they don’t know the answer.

They also need the ability to hustle; not just the conviction that something’s important. You need passion, determination, conviction, discipline to make this thing a reality. We work with entrepreneurs that would probably give up their own lives before they see their business or solution fail—that’s how passionate they are.

The last thing—and this isn’t always true, so I won’t say it’s a hard-fast rule—but having a conviction in something isn’t enough; I like to look for why this individual is personally motivated to solve this particular problem. Usually there’s an underlying cause of belief, an experience they’ve had on the ground that has personally motivated them. They have some sort of relationship to the problem set that they are solving.

 Every entrepreneur, after all, is solving a problem—so with my company, we choose entrepreneurs that are solving what I like to call BFP’s (“Big Fucking Problems”) and we like to see that they have a NEED to solve this that is somehow embedded in their DNA.


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