Interview with the Suitcase Entrepreneur Natalie Sission: Getting Started With Your Online Business

Natalie Sisson

Today I share with you an interview I did with Natalie Sisson, who is on of my favorite entrepreneurs online.

I’ve been following her almost as long as I’ve had this blog. She has been awesome enough to interview me on her podcast about developing iPhone apps and asked me to contribute to her project, $100 Change.

Natalie helps women (and some men) start from scratch and build a business online that gives them more freedom in their lives. Today her and her partner Natalie McNeil have opened their flagship course, WE Mastermind, for a limited time.

But first I wanted to asked her questions that I get from readers a lot because she is the expert at running an online business.

I follow you online and you definitely do live out of your suitcase traveling the world. Where are you doing this interview from and where have you been in 2013?

I’m currently in the beautiful and eclectic city of Berlin. Germany. I’m going to be here for around 6 more weeks before further travel for Ultimate Frisbee tournaments in Europe, and onto North America. The first 4.5 months of this year I was in South East Asia (Malaysia, Thailand, Brunei and Philippines) and South Korea!

Can you tell us a bit about how you got to this point? I know for many people having an online business is not something they imagined doing at first, but now they wouldn’t want to do anything else. 

I’d love to say it was a straight line to online entrepreneurship but in reality, like most success stories, it was two or more years in the making. I had a pretty successful career in the corporate world, rising up through the ranks in various brand management, marketing and business development roles for almost 8 years.

But the 9-5 rat race I experienced in London in 2008 pushed me over the edge. So much so that I quit forever and went to Vancouver, Canada with the dream of starting my own business.

Instead I found the next best thing, my business partner who I ended up co-founding a technology company with. That was a wild rollercoaster ride into the world of entrepreneurship – especially in the fast faced tech startup scene and I learned a ton. It was during that time I started my blog, mainly to share my learnings with others in the hope it would help them, and to interview successful female founders (of which there were – and still are – few of in the tech scene).

That blog is now the Suitcase Entrepreneur and it’s changed a lot since then as I’ve found my unique special proposition (USP) and developed my own voice and brand. It’s coming up 3 years this month that I’ve had my business and I love it more everyday.

You had a successful career in the corporate world. What made you shift to wanting to work online?

For me it was never being able to `own’ the outcome. I mean in all of my roles I had a relatively large amount of autonomy which was great. But often I got roadblocked by senior management when I was wanting to launch a new initiative or project. Nothing frustrated me more, especially as that’s what they had hired me to do. I also tired quickly of office politics, bureaucracy and working within pointless constraints. I wanted the freedom to do my own thing at my own pace.

There are lots of people who are stuck in a job they don’t like, and would love to work for themselves. They want more freedom in their lives. They want to do work they enjoy. 

They’re motivated and willing to work hard, but have no idea what it is they want to do. That’s frustrating. 

What are some things they can do to help them figure it out?

I totally understand that. I think there are people with too many ideas, who don’t know what to do with them all, and people with absolutely no idea what to do. I wrote a post talking about that exactly.

In it I talk about finding your sweet spot, something I’m passionate about helping people find, and I think it’s the key to figuring out what you’re meant to be doing in this life.

What if someone is the opposite. They have so many ideas for an online business. They just don’t know which one to choose. How can they sort through all their ideas and choose one to start?

Another great question, and this is actually far more common than you think. Usually what happens is you attempt to make a start on several things at once and end up doing none of them at all, or none of them well.

I hear plenty of people with a gazillion ideas and they never get around to doing any of them. They’re like idea chasers – they love the thought of it but aren’t prepared to implement, are too lazy, to scared or in love with the idea of ideas – not the work behind them.

My biggest piece of advice is to commit to ONE and make a start on it.  What you require is focus and discipline to make a real go of that one idea for at least 3-6 months. During that time you can ship the minimum viable product or service, continue to tweak, test and pivot. But if you don’t even give it a go, or put your all into it, it’s going to end up failing.

One thing that stops people from taking that first step to starting an online business is they’re afraid of failure. What if it doesn’t work out? What if no one buys my stuff? What if I waste a lot of time and money? Lots of doubts run through their mind. 

Then they quit before they even begin. What’s your advice to them to overcome this?

Honestly – how do you know if you haven’t even given it a shot. What are you really scared of? People fail every single day. The ones who go on to succeed get over it more quickly and aren’t afraid to have another go at it.

Ask yourself “What’s the worst thing that could possibly happen if this doesn’t work out”. Usually you’ll find it’s not life threatening.

You need to remember that anything worthwhile doing is never going to be easy but the rewards of succeeding will definitely be worth it when you do – personally and professionally.

Another thing to do is to take yourself out of the equation. Sure you’re putting your time and money on the line, but if you quit before you’ve even begun you’ve missed out on a chance to make an impact in the world on others. So think about those people – who needs your gifts and talents? Whose lives can you make a difference in?

There are people working hard on their online business now. They’re putting in the work and making progress, but it’s tough because the sales aren’t coming in as much as they’d like. They’re trying to stay positive, but they wish they could fast forward to the good part when sales are much better. 

What advice do you have for them to stay motivated through this stretch?

Starting and building an online business is so much harder than people think. My advice is to take a long hard look at your current activities and ask which of those are really driving you new leads and sales, and which are just time wasters or `nice to do’ that you’re deferring to instead of putting in the real work.

I mean this in the best possible way. For many months, even close to a year I focused on community building, social media strategy and online marketing. This all helped immensely to build my tribe and online presence. Yet I didn’t put as much work into converting all that goodwill and offering solutions to people that they were craving and that would bring be revenue to keep on investing back into my business and into them.

Realistically I was doing all the feel good things, rather than focusing on building a legitimate platform, business model and sales funnel that worked.

Take a look at your Google Analytics to see what efforts are paying off and start spending more time optimizing those areas to give your business a boost. At the same time get ruthless and drop activities that are just not serving a purpose – even if they are fun. You’ll have plenty more fun things to work on when you start making more money – trust me!

Recently a mutual online friend, Corbett Barr, posted this question at his blog. 

Which approach is better? Is it better to build an audience first, and then a product/service, or should you build a product first and find the audience later? 

What are your thoughts? 

I honestly think you should do, and can, build both at the same time, but you do need a platform from which to launch from – no matter how small. I spent the first 6 months of going into business for myself just building my community – blogging, guest blogging, attending events, being useful, answering questions on forums and speaking to as many people as possible. Without this online and offline visibility, my first product launch at the 6 month mark would not have amounted to much. From there though you have to capitalize and actually build out your products and programs to continue to offer your community what they want – that’s when it gets really exciting.

The success you have now and the lifestyle you’ve created is amazing. It’s what so many people want. However I’m sure it hasn’t all gone smoothly to get to where you are now. 

Can you tell us about the struggles and setbacks you’ve had and what you helped you overcome those?

I think the location independent lifestyle looks glamorous from the outside, and yet, like with anything in life, there are the brilliant bits and the not so brilliant. I feel extraordinarily lucky to have my life. But I’ve worked hard, and still do, to achieve this lifestyle and maintain it.

I went for 6 months without any pay and could barely pay my rent for a few of those when starting out. The first product I launched only had one sale in the first week and I thought about quitting then, and many times before and since to be honest. But I surround myself with good friends and mentors and have learned to reach out to them and ask for help when I need it.

It can also be lonely working by yourself, as many entrepreneurs doing, always having to hustle to make the next dollar. I did that for the first two years at least until I could start investing in having a small team. So once again that support network really helps, as does co-working and being part of a mastermind group.

On top of that, even though I adore traveling, and like the challenge of constantly shifting around, there are tolls that come from that, it requires a great amount of energy and motivation and the ability to hit the ground running wherever you are.

I’ve had no end of frustrations with technology, language barriers and just trying to find Internet when I need it most. I accept though, that this is the life I’ve chosen to lead – so you have to work with what you’ve got and make the best of it. And I wouldn’t do it if I didn’t love it 95% of the time.

This applies to anyone building up their ideal lifestyle business – if you really want it you have to work for it and push through the humps and jump over the hurdles. You also need to celebrate your small wins and congratulate yourself regularly – no-one will and it’s important that you do. This is after all a journey!

WE Mastermind is a course you’re very passionate about. I’ve met people online who have had great things to say about it. Can you just explain what exactly is WE Mastermind and what is the outcome for someone who goes through the course?

I love to hear that. I am really proud of the results we’ve helped our members get over the last two years of running this program.

WE Mastermind is a 3-month digitally delivered program designed to take you from zero to launch of your first product or service.

You get 12 weeks worth of killer modules that take you through everything from product launch planning, to social media, list building, affiliate marketing, tools and technology and mindset. These are delivered via video training, workbooks and forums to track your progress.

You also get 12 weeks of group coaching from myself and Natalie MacNeil, my partner in crime and our backgrounds really complement each other well. Natalie has been an entrepreneur since the age of 17 and has gone on to build an Emmy Award winning Interactive Media business, win a bunch of amazing awards, beat out 250 competitors to win a $100,000 investment funding and much more. My background helps me combine all the lessons learned in the corporate world with building my online business, launching products and services and coaching others. It’s a pretty powerful combination.

The unique component we believe set our program apart from others though, is the mastermind. From the second week you’ll be assigned to your own mastermind group of 4-6 other like-minded entrepreneurs who you’ll meet with (online) weekly to get real accountability and make massive shifts – that’s invaluable in my mind.

At the end of the three months we believe if you’ve gone through all the training and fully committed to showing up and doing the work, you’ll either have launched or be close to launching a lucrative product or service. You’ll also have an entire community behind you cheering you on, and most likely some new joint ventures and collaborations as a result.

Finally, what’s one last piece of advice for someone who’s ready to take the leap into online entrepreneurship?

Be prepared for one of the most scary and exhilarating rides of your life and make sure you embrace every twist and turn and up and down – it will make you a better person, and you in turn will make the world a better place. And that’s a fact!

Ready to launch your online business this year?

If the answer is yes, but you have no idea what it should be, where to start, or how to do it, then WE Mastermind can guide you.

The once a year program is open now until May 15th. Only 50 spots are available. Their focus is mainly women, but they will of course accept men.

This 3 month online program is delivered online with 12 step by step modules complete with actionable workbooks and coaching videos. In addition there’s an interactive forum, mastermind groups and monthly Q&A coaching calls as well as interviews with experts and the following modules:

  1. Setting Yourself Up With a Million Dollar Mindset
  2. Choosing Your Perfect Product Niche
  3. Discovering the Right Type of Product to Launch
  4. The WE Mastermind Lucrative Launch Blueprint
  5. Creating a Killer Web Presence
  6. DIY Social Media Sales and Marketing
  7. Rallying a Dream Team to Sell Your Product
  8. Keyword Marketing and Search Engine Optimization
  9. Powerful List Building and Newsletter Marketing
  10. Getting Comfortable With Making More Money
  11. Tips, Tools, and Technology to Streamline Your Business
  12. Putting it All Together

Besides the full program, there is also a digital only option. You’ll get everything above minus the coaching calls, forums, and tech training videos.

Bonuses for Get Busy Living Readers Only

I’m happy to help Natalie spread the word about WE Mastermind because I believe in what she does. I know the benefits about having an online business and the freedom it creates. I want you to enjoy those same benefits with your own online business.

If you join WE Mastermind through my affiliate link, where I will make a commission, I have special bonuses just for you.

  • 1 hour (or two 30 minute) Skype call with me anytime to pick my brain about anything or coach you in any area of your life. 
  • Free access to my Get Busy Living in 30 day course. This course is a great compliment to WE Mastermind because I can help get you in the right mindset, strengthen your beliefs and confidence, introduce habits that’ll take your life and business to the next level, and prepare you for this new chapter in your life. WE Mastermind will definitely help you with a plan to launch your online business. It is the ying and I’m the yang.
  • Free access to my video training course, Develop an iPhone or iPad app with no programming experience ($197 value). If you’re interested in developing apps as one of your online businesses now or in the future, I can teach you how to find an idea, hire the right team, and getting you setup to have your app ready in the App store. You can join the course or offer it free to someone you know.

To get these bonuses, you must join WE Mastermind through my link. Once you join, forward me a copy of your receipt to

There are only 50 spots available and the deadline is May 15th at midnight. If you want to have your online business up and running before the end of 2013, these ladies will guide you with their experience.

Enroll in WE Mastermind by clicking this link




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