How Derek Halpern Helped Me Make Over $500,000

By Sean Ogle •  Updated: 11/17/16 •  9 min read

About 4 years ago I was at SxSW in Austin, Texas.

My business was still relatively new at this point. I’d launched Location Rebel Academy less than a year before and was slowly starting to experience a little bit of success.

For the first time not only were people buying a product I’d created, but they were having really good results with the content – leading many to actually leave their jobs and have successfHow Derek Halpern Helped Me Make Over $500,000ul businesses.

Naturally I started thinking ahead. I started thinking about how to grow my business and what to do next.

But here’s the thing, I didn’t consider myself a marketer. I was just a random dude that stumbled upon some things in his own life that worked pretty well, taught it to some more people, and found it worked for them too.

But I knew if things were going to grow, I had to start thinking differently.

During the conference I was at an event hosted by DIY Themes, where Derek Halpern did marketing at the time.

He was sitting across from me, and I remember asking him: What should I do next to grow my business and my email list?

Then he told me the best piece of business advice I’ve ever received:

“To grow and monetize your list, you need to build relationships with your readers and figure out what they want. The best way to do that is to ask them to answer a question in your first email to them.”

I remember thinking: “Wow, what a novel idea! Why didn’t I think of that!”

So I took his advice. And since doing so, using variations of that same strategy in my autoresponder and in my launches I’ve made well over $500,000 with Location Rebel.

I talk about it in this week’s vlog:

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Who is Derek Halpern?

Let’s back up for a second.

Who is Derek Halpern?

There’s a good chance you already know the answer to this, but for those of you who don’t…

Derek is the founder of Social Triggers website that shows you how to grow your business by marrying pyschology and marketing.

He also founded Zippy Courses which is one of the easiest ways to build a membership site if you’re just starting out.

Bottom line he’s got a big personality, and more than just about anyone else online, I truly trust and value his advice.

What Question Should You Ask?

Now at the time he gave me this advice, I don’t believe he’d talked about it on his website yet. But not too long after he wrote this blog post.

Since that time hundreds of people (if not thousands), have implemented this same strategy successfully.

So for many of you, I’m not telling anything you haven’t heard before. I’m just sharing why it’s worked so well for me, and the spin I’ve put on it.

The question Derek asks (and the one most of the people taking his advice ask as well is):

“What are you struggling with?”

For my audience personally, I expanded upon that.

With Location Rebel, my goal is to help you do more of the things that make you happy through the process of helping you build a lifestyle business.

So for years any time someone signed up for my email list I asked them the same question as above, but I also asked them to reply and tell me “What does your perfect day look like?”

For me, the answers to that question have in many ways been even more valuable both for me and my readers.

It’s worth noting that the “what are you struggling with” question has been asked now to millions of people on various blogs and websites.

So if you’re going to implement, it may be worth mixing it up. However, for the majority of people on my list the responses I get lead me to believe that, for many of them, they haven’t seen it before.

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The Five Reasons Why I’ve Found this to Work So Well

There are all kinds of different reasons why this general strategy works, and as people do it in their own unique ways, different aspects of it will be more valuable.

But here are the five reasons why Derek’s strategy has worked so well for me here at Location Rebel.

1) I’m learning what my reader’s problems are as well as what their solution looks like

By asking these two questions people are telling me what problem they are looking to solve.

They’re also telling me what their perfect end result looks like.

This gives me tons of information that surveys can’t.

Real people, real problems, real hopes and dreams.

And most importantly, it’s an opportunity for me to create real solutions for them.

I can use the information to help write blog posts, create products, craft marketing messages and ultimately help them solve their problems and get closer to that perfect day.

Which for me by the way, might look something like this:

Sean Laptop Vail

And then maybe some of this:

Tetherow Golf Club is a Top 100 Public Course in Bend, Oregon

Me at Tetherow Golf Club in Bend, Oregon

2) It catches them off guard

The second reason why this works so well is because it catches them off guard.

When was the last time you were asked to actually respond to an automatically generated email?

It doesn’t happen very often.

Regardless of whether or not you actually reply (about 20-25% of people who sign up to my list respond), it’s at least triggered some kind of reaction.

With most people receiving dozens of emails a day, it can be hard to show them something different – but much of the time, this does.

LR Email

3) It provides free therapy

As I mentioned, most people won’t respond.

But of the people who do, many of them say something like “I have no idea if you’ll respond to this, but thanks for prompting me to think about it either way!”

Here’s a great example:

Free therapy!

Free therapy!

The reality is, if you ask most people what they want in life or what their perfect day looks like they don’t know. 

How can you work towards something if you don’t know what that something is?

So for the people who answer, or even think about answering these questions, it truly is like free therapy. Regardless of whether we have any interaction after this, helping a reader to think about those two questions is valuable.

4) It builds trust

I like to think I’m a pretty trust worthy, genuine guy. I really do just want to help people build small businesses that let them do cool stuff like travel the world, spend more time with friends, or fly in really fancy airplanes.

Sean Ogle on Singapore Airlines Suites Class

The flight attendant insisted on taking photos of me in nearly every part of the plane

It’s hard to build trust when email is a one way street.

Especially when it’s a one way street with the same email going to thousands of people.

Here’s the real secret sauce in this strategy.

I do something that blows people’s minds every time they reply to an email:

I respond. Thoughtfully.

I read what their issues are, where they’d like to go, and I give them some sort of feedback or direction that might help them get closer to their goal.

Mind blown, right?

But this is rare. Many of the people who employ this strategy don’t respond to everyone for obvious reasons.

It’s a hell of a lot of time, effort, and work.

For years, at least half my working hours have gone to responding to email.

I can feel the simultaneous cringe from more successful business owners.

But it’s that personal relationship and the trust I’ve built with my readers that is what has gotten me to this point.

It’s also part of the reason we’ve hit a bit of a plateau with our business, but we’ll save that conversation for another day.

Building this trust is the absolute best way to not only build your brand and get customers, but it’s a fantastic way to grow friendships and real relationships as well.

And that’s the kind of business I want.

Recently Robert Cialdini came out with a new book called “Pre-Suasion” that talks all about how to build trust before asking for the sale.

I hadn’t necessarily realized that’s what I’ve been doing for years until I read about it in this book.

5) It encourages engagement

Eventually after receiving a bunch of emails from you, some people will become disengaged.

So I try to employ this strategy beyond just that initial email.

I ask people to reply to questions in my newsletter. During launches I’ll ask people to respond to a particularly thought provoking question (and then spend two days straight answering, while getting into some of my own personal goals as well.)

In most of my emails I try to illicit a response of some sort.

The more you engage your audience the more they will see you as a real person (because you are, just like they are.)

I try and have as many conversations with my readers as I can. So to facilitate that, I give them every opportunity possible to engage with me.

It’s not the most automated or the best way to scale a business, but it’s a way that has allowed me to live a better life than many, and build a lot of really meaningful relationships in the process.

Thank You, Derek

Derek, I have no idea how you’re going to respond to this. But based on the last post (read the comments) where I mentioned you, you may have some epic take down for me haha.

But bottom line, thank you.

That one piece of advice you shared with me (and now thousands of others) has ultimately led to better relationships with my readers and customers, a more successful business, and the ability to live the life I really want.

So thanks for that.

And if there’s one lesson or piece of advice I’d impart to anyone else reading this post, it’s the following:

Be real. Treat your readers and customers like real people. And be genuinely interested in helping however you can.

If you do that, good things will happen.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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10 comments on "How Derek Halpern Helped Me Make Over $500,000"

  1. Great Title! Do you have a summary or a post about the breakdown of the $500,000? I think that would be fascinating.

    I’ve been trying to encourage my readers to think bigger and highlighted a janitor making $270,000 a year and it elevator technician making $284,000 a year in one of my latest post on abolishing welfare mentality.

    Anybody can do it. When will people start writing their own story?


    1. Sean says:

      Sam, good to hear from you! We’re long overdue for a tennis match 🙂

      I’ve haven’t done any income breakdowns in like 5 years, but I’ll consider it. As I agree, I always think it’s interesting to see. Just shied away from doing it for pretty obvious reason.

      Will keep you posted if I do!

  2. Gillian McAtee says:

    Hi Sean!
    Thanks for this post; as it happens the topic is really apt for my situation at the moment, as I’m in the process of starting my online business, and finding out about engaging with prospective clients!

    This has just reaffirmed my thought process and double confirms all the top advice and info I’m studying!
    Love your work and your style- down to earth and real 🙂
    thanks! 🙂 🙂

    1. Sean says:

      Thanks Gillian! Congrats on getting the new business going, and glad you got some value out of the post. Keep me posted on your progress!

  3. Sean,

    I’m thinking about starting an e-mail subscription list and this is some great advice. Asking a question to start out is a sure fire way to drive engagement. Asking the RIGHT question is what I will have to figure out. As I am a generalist when writing posts in my blog, it will take some time to get it down.

    Thanks for sharing.

  4. Alan says:

    Great post. This strategy was a game changer for us as well. I changed our first automated response email to ask, “Can I ask you something?” and then all of a sudden started getting these GREAT emails from our community members, which ultimately has lead to our paid products and some significant partnerships once I learned more about our average community member. With Internet businesses, it’s too easy to hide behind the computer, to press publish, and to hope to make money. But 1:1 communication, even picking up the phone like I did for several weeks last summer to chat with folks about how they found our website, what they’re looking for, etc. helped us immensely.

  5. Thank you for the article. I found that it was inspired, and put some ideas in my head. Thanks again.
    Richard Benchimol

  6. Kate says:

    Thank you for this post, I am 1 month away from my last day at my 9 to 5 job!!! So, I’m gearing up for the time I will have to build my business and really figure out what I am going to offer to people. Your post will help me with that, I will simply ask my audience a question or two to start. I like the simplicity of what your questions are as well, most people don’t have a lot of time for a lot of questions and for those who do have the time, I’m sure they elaborate on their answers.

    Thanks for keeping it real and personal! It encourages me to VLOG too, in the future….

  7. Charles says:

    Loved the “It provides free therapy” section 🙂
    I always get very personal in my emails, and my readers usually reply with a lot about their personal lives as well. While it might not directly provide answers about what they need or what kind of product I could create, it’s a great way to start a conversation and get to know them better.

    Here is the start of an email I recently got:
    “I didn’t expect to receive personal e-mail from a blogger that I subscribed to.
    They usually don’t send personal e-mails at all.”

    So, don’t be shy and share personal stuff!

  8. Timothy says:

    I was sitting in a webinar this morning for web professionals who build websites. There was one part of the process when meeting with clients called “discovery” meetings. It’s basically trying to find out their needs and if it is something that can be and would be provided.

    After reading this article this morning, I realized that listening is actually more important than trying to present and sell (novel idea huh?). That’s why all the professionals don’t have to talk so much and they tune in to exactly what people want/need. It’s like hitting the rights buttons in a good way.

    So when I go to meet my next website client, I will try to listen to them more about their goals and what they need. In my mind, they just need an online business presence but am I truly listening to what they’re saying? This will open doors for possible revenue or even recurring revenue.

    Appreciate your thoughts, Sean! Have an awesome day.

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