If You Don’t Learn How to Follow Up, You Won’t Make Any Money Online

Tim Denning

The brutal truth about this overlooked skill — with a practical 7-figure example from my work.


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The one-ask wonder is a fantasy.

Asking once for something you want will almost never get you the result you seek. Ask Will Smith for an interview via email. He’ll probably not respond. Ask a publication to publish your work for the first time. They will probably not respond or say no. Ask someone to be on your podcast. They will likely say they are busy.

If you let the story of your life be defined by initial requests, it’s going to be tough. I hear people complain a lot when it comes to making money online.

They are quick to say “Richard Branson is an a-hole for not accepting my request for an interview.” I can’t be fooled that easily. When I hear these stories I dig deeper. I find out just how hard the person tried. The single defining feature of these complaints is this: the person never followed up. They may have done everything else right, but they didn’t follow up.

Nathan Chan, creator of Foundr Magazine, started creating content around the same time as me (he lives in my hometown of Melbourne too). His entire online business that generates millions in revenue was a result of follow-up. Nathan, too, had dreams of interviewing Richard Branson. He sent a request off to Richard and got a yes when his magazine had almost no traction.

What Nathan did to get an interview with Richard Branson was to follow up. Not once, but many times. That one subtle difference got Nathan the interview and became the catalyst for him interviewing many other world leaders including Jack Dorsey, Mark Cuban, Tony Robbins, and Brené Brown.

If it wasn’t for the art of follow-up, Nathan would still be working for a travel agency doing IT Support and hating life.

Making money online is built on follow up

Whatever idea you choose to execute on to make money online, you’ll be required to deliver “the ask” over and over.

If you want to be paid as a writer, you’ll be required to ask a publication to accept your work — or to ask businesses to pay you to write.

If you want to be paid to sell a physical product online, you’ll need to ask a manufacturer to make it for you. You will also need to ask for a reasonable price so you can make money.

If you want to charge someone for a coaching service, you’ll be required to ask that person if you can help and charge them for it.

If you want to start a podcast and make money from ads, you’ll be required to ask advertisers to pay you, and well-known guests in your field to give up their time and come on your podcast.

If you want to work a four-day workweek and build a side-hustle, you’ll be required to ask your boss to work one day less per week.

Whatever way you decide to make money online, there will be an ask followed by multiple rounds of follow-up. Following up determines who makes money online and who doesn’t.

Following up will test you, and your reward will be some, or lots of money, if you master it.

This week I landed a 7-figure opportunity as part of my more traditional work in sales. Let me share the process so you can see the power of follow-up.

November 12th 2019 — I send a cold InMail to a prospect on LinkedIn.

November 17th 2019 — I send a follow-up InMail to the prospect. “Hey, just wanted to follow up. Any chance you would be free to chat?”

November 19th 2019 — The prospect says, “What is it that you want to talk about?”

November 20th 2019 — I reply with the following message: “I saw what your team was working on and we’re doing something similar. Wanting to see if there is an opportunity to work together. Worst-case scenario, you’ll walk away with a few ideas for your project.”


November 23rd 2019 — I send a follow-up. “So what do you think?”

November 24th 2019 — The prospect sent the message that kills my chances. “Sorry Tim this doesn’t resonate with us. Let’s leave it for now.”

May 25th 2020 — I send a follow-up. “Hey, how’s things? Wanted to reach out and schedule a time to chat. Keen to share with you some of the things we’re doing and get your coaching on an approach to your broader leadership team.”

June 10th 2020 — Prospect sends me an email. “Sure. Things are really busy but can do 30 minutes next week. Will send you an invite.”

June 1st 2020 — I have a quick phone call with the prospect and ask them, this time, for an introduction to the leader above them. He says he’ll pass on a two-page slide deck for me with a short overview but won’t do an introduction.

June 5th 2020 — I follow up with the prospect. “What did he think? Is he willing to chat?”

June 8th 2020 — The prospect writes “I’m sure he will reply. Give him a few days.”

June 12th 2020 — I email back and say, “Still nothing.”

June 13th 2020 — The prospect replies with the worst line in history: “He will contact you if he ever sees an opportunity.”

June 15th 2020 — I write the following: “I was hoping to be a bit more proactive than that and build a relationship first. What would you suggest?”

June 16th 2020 — The prospect emails me and says a Personal Assistant will reach out to book a time with me and the leader I’ve been trying to reach.

June 16th 2020 — Moments later the Personal Assistant reaches out and the meeting is booked. What comes from all of this is a 7-figure opportunity.

This is what follow-up looks like. As you can see, this part of the process is normally invisible. You hear about people making money online but you don’t see what transpires behind the scenes. It’s not a one email pitch, ever.

Here are the keys to a decent follow-up from someone who has made a career out of it and built an online business.

Be unreasonable enough to think you’re important and have value

The whole way through I didn’t give up hope. I followed up and didn’t fall for the lie that my request was silly or unhelpful.

You want to genuinely believe you can be helpful when following up. If you focus on being helpful, your follow-up will cut through in the way you go about it. It’s easy to feel defeated, but don’t be.

Follow-up is nothing more than a feeling of not letting yourself feel defeated.

Take a long pause from following up

Peoples’ lives can change drastically. All of a sudden, your ask can come at the wrong time.

As you can see from the above timeline there was a period of about six months with no contact. Sometimes the best thing you can do is put the follow-up process on dry ice for a while and move on to another opportunity.

Coming back from a sustained period of silence is easy: be like a puppy dog and pretend the past didn’t happen. Pretend you never pitched the person.

A former colleague of mine had a meeting missed by an important person three times in a row. He walked up to the person’s desk one afternoon, pretended like they’d never missed the meeting at all and just had the conversation impromptu.

He told me this: “Move on from rejection and block it out from your mind. Follow-up is not about getting emotional. It’s about getting shit done.

Keep it friendly

At no stage is it a good idea to lose your cool and be angry at someone. The moment you lose your cool, the follow-up will end; you’ll probably get ghosted. Your priorities — may — have no value to the person you’re trying to pitch.

You may not know this

The first ask is a test.

When you ask someone for something for the first time, you’re being tested. Most people will never respond to the first outreach because they want to see if you’re serious.

Serious people who change the world follow up.

You prove you’re serious by following up, politely, and doing so a few times. Every request I get is ignored, unless it’s Tony Robbins or Tim Ferriss. I learned this from people who manage their time far better than I do.

Ignoring the first ask sets apart the wannabes from the people who will create value and use your time in awesome ways.

REALIZATION: People actually love clever follow-up

You’re helping people when you follow up like a pro.

There are so many things to keep track of; there are endless notifications and messaging apps to keep up to date with; the news is terrible right now.

If you can pull off the art of follow-up, people actually respect you.

Humans admire determination and that’s exactly what follow-up over a sustained period of time does. If you can outlast the rejection, you’ll have a good chance of having your ask met.

Final Thought

The brutal truth about making money online is that it all starts with the skill of asking for what you want and then following up to ensure you get it. Money isn’t just going to find its way into your bank account because you have the experience, passion, desire or a goal — or worse, because you think you deserve it.

You earn money online through mastering the art of persistent follow-up. And anybody can do it — even you.

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Aussie Blogger with 100M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship www.timdenning.com


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