How I Convinced 120 Influential Entrepreneurs to Give Their Advice For Free in Under 3 Weeks and 8 Tips For You To Do The Same

Posted on / by Natalie Sisson / in Entrepreneurs / 12 comments
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Have you ever felt so inspired by something – a speaker, a video, or a movement – and you just had to take action?

You had a compelling vision that you wanted to bring to life in the form of a new project or product, but you knew that in order to make a real impact you’d have to reach out to some key influencers and get them on board.

And when you went to approach these people, there are a couple of things that may have happened:

1.) You stopped short of writing the email at all because you had no idea what to say.

2.) You were scared that this person wouldn’t respond to you.

3) You sent the email and never heard back from the person.

4) You may have even followed up once or twice, but in the end, there was no response.

If that sounds familiar then please keep reading.

I’m going to cover how to make an effective ask to key influencers, and show you real life examples of email pitches I’ve made, as well as 8 key tips on why these worked.

So how do you make an effective ask?

Identifying and partnering with influencers to market your brand or product is an essential way to bring publicity and credibility to you, your brand and your business.

But it’s also really daunting, as you may have already found out for yourself, and receiving no for an answer can really knock you back.

Yet it’s much simpler than you think to get people who seem out of your reach to work with you or be part of something your creating – like a product, service, telesummit, webinar or program.

Start by asking.

That may sound silly to say, but you’d be surprised how many people never even take that step because they’re too scared of rejection, or think there’s no possible way that person would agree.

It can take a while to figure out the best process to connect with key influencers and determining the best ways to engage with them.

Take for example when I was sitting in an airport in Dubai, having just bought my SKRoss World Pro Adaptor, and thinking it was such a great product in line with my brand, that they’d be a great sponsor.

So I went straight to their website and looked for the PR and marketing manager and sent off an email. A few months later they were my first podcast sponsor!

Here are 3 steps you can take right now:

  1. Make a list of the top 10 people you’d love to approach

  2. Craft a message that clearly states why what you’re doing matters and why they should be involved

  3. Send that message – whether via email, postcard, letter, a phone call or in person.

how to make your as and get a yes answer

Whatever you do:  Always make sure when you approach someone and make your ASK that it comes from the heart and just be yourself. [Tweet this]

Most people can spot a fake a mile away, or someone who’s on the prowl to further their own progress, but would do nothing in return.

You can bet that the people you want to reach out to receive pitches every day that they reject.

But how you can make yours different and create a great pitch that really increases your chances of getting `yes’ for an answer?

$100 Change Case Study in Action

These are all questions that raced through my head while I was in the audience at Chris Guillebeau’s World Domination Summit when he gave $100 to every single person in the audience and told them to do something meaningful with it.

100 Change Program Digital Guide

I had this spark of genius that I wanted to offer a program that created change in peoples’ lives with just $100 down, and would also be a non-profit initiative during the launch with 10 scholarships being awarded to those who participated.

After a few conversations with WDS attendees I had refined this even more to become 100 days of wisdom and insight from 100 change makers, delivered via a daily email, and culminating in a book that could be read and referred to forever.

Fast forward three weeks and hundreds of emails sent, and I had 120 change makers giving their valuable advice to a community of aspiring entrepreneurs.

I actually reached out to around 150 in total assuming that I would get rejections or not hear back, and naturally that was the case – these are busy and important people after all.

But as you can see I got way more `YES’ answers than rejections.

Looking back, a lot of the success of the initiative rested on pre-existing networks and a whole lot of hustle to pull this together. I was fortunate to have several people willing to go the extra mile and share the initiative and reach out to other change makers I could contact.

It was also during this creation period that Cher Hale, my now Chief Happiness Officer and Online Business Manager volunteered to help me with the project.

With her field of study being PR and Communications, together we set out to craft a series of `perfect’ emails designed to get the positive responses we were looking for.

Swipe this example template of a long-form pitch email:

Hi __________!

We’ve identified you as a change maker in this world. As a person who inspires others through your work and makes an impact in entrepreneurs lives.

That’s why we would love you to be part of our $100 Change Initiative along with Danielle LaPorte, Michael Stelzner, Amy Porterfield, Jonathan Fields, Pam Slim, Corbett Barr and Chris Guillebeau.

I’m Natalie Sisson, the Suitcase Entrepreneur and adventurer who runs a popular blog that aims to help others create freedom in business and adventure in life. I have a thriving community of aspiring entrepreneurs who want to create businesses they love and can run from anywhere in the world.

As a result of a recent generous act by Chris Guillebeau at his World Domination Summit, where he gave all 1,000 attendees $100 and asked us to do something meaningful with it, I’ve decided to go all out with this:

$100 Change is an initiative designed to change hundreds of entrepreneurs’ lives.

I want people to know that they can achieve major change in their life and others, with just $100 change.

I’m gathering 100 change makers from around the world to provide wisdom and insight over 100 days for $100. The $100 will then be delivered back into 10 scholarships for people wanting to start or create a new project, biz idea or initiative.

Details are here

Those people will then have 100 days to work on making this a reality and receiving guidance and mentorship from some of the change-makers to ensure they succeed.

I would love for you to be one of my change-makers. All it requires is answering a few questions in 150 words or less here by the 20th of August.

Here’s the short and sweet details on the initiative

Thanks so much for your time and consideration!

With gratitude,



3 Key Tips To Learn From This Email Pitch To Influencers

This email pitch was used on people who would not have known who I was, so this was essentially like cold calling. We actually sent this one out much less than the short form too.

1. Display Social Proof

As you can see, I used social evidence in the first few paragraphs, citing big names that they likely would have heard of, who I’d already gotten a yes from.

Obviously you can’t do this unless you already have people on board, so just remember to keep your ask evolving as you get closer to accomplishing what your goal. It’s all about forward motion.

This is so critical, as it instantly introduces an element of trust, that’s why you’ll see people doing this often. Just like when John Lee Dumas was first starting his now super popular podcast, Entrepreneur On Fire (this links to our interview).

When he approached me to be on his show, he told me he had been working with my friend Jaime Tardy who’d recommended me – a great start to an email as now I was listening (by the way they’re both upcoming guests on my podcast!).

Then he went on to cite a few more examples of people who he was interviewing, which was also impressive. So naturally I said yes.

Using this technique worked for John, and it helped me to customize each email to the person I was approaching based on who I knew they knew and respected.

2. Provide Calls To Action

As you can see in the above example, I had several URL links to the program for them to click on throughout, just in case they missed it the first time.

I recommend having at least 2 calls to action within an email so people don’t have to scroll back up to click.

3. Give A Deadline

I am forever surprised how many email requests I get asking for something, with no indication of when they need it by. Most people have a lot on their plates so you need to give them ample time to review, support or provide information for your project.

In addition, you must give them a deadline and a clear request for what you need. As you can see I sent them the direct link to fill in the survey and told them I just needed 150 words or less by August 20th.

Swipe this example template of a shorter pitch email:

Hi ______ !

I know you get a gazillion emails. So I’ll keep this one short and sweet. In my mind, you’re a change maker. That’s why I think you’d be the perfect fit for the $100 Change Initiative.

If you want to know what the project is – in a nutshell Natalie Sisson (aka Suitcase Entrepreneur) is gathering 100 change makers from around the world to provide wisdom and insight over 100 days for $100.

The $100 will then be delivered back into 10 scholarships for people wanting to start or create a new project, biz idea or initiative.

Details are here

Thanks so much for your time and consideration!

All it requires is 10 mins of your time to answer 1-2 questions here in this form by August 20th:

That’s it. That’s all you have to do.

Over 75 change makers are already on board including Pamela Slim, Michael Port, Julien Smith, Michael Stelzner, Danielle LaPorte, Jonathan Fields and Chris Guillebeau, plus many more.

<insert personal note that shows you’ve been reading, watching, listening or learning from them>

With gratitude

Cher Hale
Outreach Coordinator, $100 Change Initiative

5 Key Tips To Learn From This Shorter Email Pitch

This email worked really well as by then we had a number of people on board and a lot of momentum. We also had an even shorter version to break the ice taken from this above email.

When you break it down, here is what made the ask really effective:

1. Recognise that their time is valuable

By saying “I know you get a gazillion emails. So I’ll keep this one short and sweet.”

2. Summarise the concept

Twitter is a brilliant tool for the very reason that it teaches you to be concise and say what you have to in just 140 characters or less. We condensed this initiative into just 1-2 sentences.

3. Be specific about how much time it will take

By saying “All it requires is 10 mins of your time to answer 1-2 questions…” we were far more likely to have them provide their answers on the spot.

I also made sure to:

4. Follow up within 7 days

Sometimes emails really do fall through the cracks, and people appreciate the follow-up. I sent a few people three emails and when they finally answered they’d realized they’d completely missed the first two. So don’t think radio silence means they’re not interested.

Reminding people with just 7 days left also works well for creating a sense of urgency, as people usually work better under a tight deadline, but appreciate the initial timeframe you give them in which to soak up the idea.

5. Add a special touch

In many of the follow-up emails, I added one specific reason why I would love for the change maker to be on board with the initiative.

Here’s an example of one sent by Cher:

P.S. I loved this article that you wrote for Positively Positive (link here). It seriously helped me to choose what’s most important on my ever expanding to-do list AND you gave me more justification for going MIA for a little while to focus. Thanks!

The Results and what you should do next

At the end of these three weeks, 120 change makers from all over the world had come on board my $100 Change Program, offered their advice to aspiring entrepreneurs, and helped me to create an incredible program and guide.

In addition I went back to many of these change makers at a later date to ask if they’d contribute one product or gift to a giveaway I was running for all the people who had joined the program, and to entice more people to get involved and have a shot at the scholarship.

In just 10 days I had incredible products to the value of over $12,000 and I was only aiming for $10,000.

This quite frankly blew my mind. The generosity and support once I started reaching out to ask people for help was really overwhelming – in a totally fantastic way!

The side benefit that I hadn’t considered was the relationships I’d strike up with many of these people as a result and the continuing friendships I now have with them.

I know that you can achieve the same result, even if you don’t have a list, a big network or much credibility yet.

It’s all in the way you ask, the people you connect with and the way in which you craft your message. Remember, like I said, it needs to come from the heart and have a clear benefit to the person you’re reaching out to.

For further reading I suggest you check out Erin Giles `Amp Your Ask’ with scripts and templates to swipe, plus James Clear’s `How To Email Important People’. Or read my article on how to become a media darling and sponsorship magnet.

Proud to disclose

I am blogging on behalf of Visa Business and received compensation for my time from Visa for sharing my views in this post, but the views expressed here are solely mine, not Visa’s. Visit to take a look at the reinvented Facebook Page: Well Sourced by Visa Business.

The Page serves as a space where small business owners can access educational resources, read success stories from other business owners, engage with peers, and find tips to help businesses run more efficiently.

Every month, the Page will introduce a new theme that will focus on a topic important to a small business owner’s success. For additional tips and advice, and information about Visa’s small business solutions,  follow @VisaSmallBiz and visit

Any questions? Write in the comments below what you’ve done in the past to make an effective ask.