Ethan Waldman Interview: End The Struggle With Technology!

Posted on October 10th, 2012 by Colin and is posted in Interviews

                                                                  Ethan Waldman Interview: End The Struggle With Technology!                                

Welcome to this next interview in the “Meet the Experts” series. I recently interviewed the multi‑talented and all round nice guy, Ethan Waldman – 

He’s a technology coach, a Mac fanatic and a hot yoga enthusiast. He is building a small house on wheels in his parents’ back garden and, if you give him any instrument, he can pretty much play it!  

Ethan is the founder of Cloud Coach which he launched in February 2011.  His passion is to help his clients become empowered with self‑sufficiency by teaching them some technology skills, usually around things they didn’t think they could learn. He wants his clients to live and work in harmony with technology. We like the sound of that! 

What You’ll Learn:

  • Where the idea for Cloud Coach came from and the service he provides
  • The biggest obstacles he has overcome in becoming a solo entrepreneur
  • How he is making the transition to making Cloud Coach his full time career
  • The 3 step process he has used to go from a business idea to idea execution
  • 3 of the best technology tools to simplify your life   
  • The importance of being in a mastermind group
  • About his Inbox Zero Training programme
  • How he is building a tiny house on wheels (this is a wonderful example of Ethan following his “smile.” It could easily turn into another income stream). 

Phew! I did say he was multitalented!

Enjoy this inspiring interview and if you like it, please “like,” “tweet” and “+1″ it! Help spread the word beautiful people!

Your inspiration. My passion. 


P.S. If you have any comments or questions for Ethan, please leave them in the comments box below.

P.P.S. You can watch, read and download the interview onto your MP3 player. I’ve got your learning style covered! 

(The video takes about 30 seconds to download, so be patient. You can download the audio by clicking on the icon below the video)



Colin: I started following Ethan in June of last year, and for those of you following Maverick, I put a blog post out, “My top 21 awesome bloggers who have rocked my world,” and I had five criteria, and Ethan ticked every single one of these. I’m real pleased he’s found the time today to give this interview to us.

I know we’re going to learn a lot about a couple of things, his journey to where he is today around Cloud Coach ‑‑ it’s becoming his full‑time career ‑‑ and also the service that he provides. So, welcome Ethan.

Ethan:  Great. Thanks, Colin. It’s great to be here.

Colin:  Very good. How are you today?

Ethan:  I’m excellent, I’m out, actually, in the countryside of Vermont, where I’m working on a small house I’m building, so I’ve got a lot of things going on, but it’s beautiful weather here in Vermont this time of year. It’s starting to get a little chilly, fall is in the air, but it’s really beautiful, and it’s great to be here.

Colin:  Fantastic. Well, good. Why don’t you share what is Cloud Coach, and maybe the service that you provide?

Ethan:  Sure. Cloud Coach is a little bit less than two years old now, but it’s really something that I feel like I’ve been doing for a very long time, since a young kid, actually. People ‑‑ usually, first family, and then friends ‑‑ would come to me for help with their computers, for help figuring out what the best technology was to use to sell their photographs online, or how to make a video call, just little things that I would help people with.

I’ve been in the training industry professionally since I graduated from college, but never really felt like I was connecting with the people that I was training on the corporate level. I realized that I really love helping people one‑on‑one, because I can really see the impact of what I’m doing, and I particularly love working with small business people.

The way I see it, a big corporation can afford to have an IT department, they can afford to have a marketing department, they can afford to bring in all these experts on technology, but if you have a small business, it’s just you, or just you and a few other people, you can’t afford to hire a technology person full‑time.

Cloud Coach is really about showing you what you need, teaching you how to use it, and doing it in a way that, hopefully, allows you to continue doing it without my help. I don’t know if it’s the best business to all, but I feel like I’ve done the best job if you don’t need me anymore after we’re done.

Colin:  [laughs] So you make yourself redundant.

Ethan:  Yes, and the idea is just empowering people to be able to do these things themselves.

Colin:  All right. Just tell us a bit of background, then. What were you doing before Cloud Coach?

Ethan:  OK, so before Cloud Coach, I was working in the e‑learning industry. So basically, if you’ve ever had a corporate job, you’ve probably taken some e‑learning. It’s computer‑based class, “Our Policy on Workplace Ethics,” those kinds of things. But I was doing that training mostly around software, so I was helping employees at different companies learn the software that those companies had.

I liked what I did. I actually still do some of that on a freelanced basis as well. That training in that industry has definitely helped me with what I do for Cloud Coach. So yeah, so I went from corporate training, and now I’m doing more personalized training.

Colin:  Very good. Was there a particular time for you, or catalytic event, that sparked the idea of actually becoming a solo entrepreneur and running your own business and doing it online?

Ethan:  I’ve definitely wanted to do this…You know, I’m 28 years old, and as soon as I got out of college, I felt like I was following the path, you know? I went to college, I graduated, I got a corporate job, and almost immediately, I felt almost let down, because I didn’t like it, and I didn’t understand what was wrong with me, or like why I didn’t like it. So really, since I started working, I’ve wanted to stop working. I mean, not that I don’t want to work, but that I just wanted to work in a different way and work for myself.

So I’m definitely the kind of person who starts a lot of projects and doesn’t always finish them. So, I have lots of ideas for online businesses and for websites and blogs, but nothing I could really ever commit to.

But I finally, basically I took the plunge and hired a coach, somebody who I really admired was offering a six‑month coaching program, and I just said, I can’t seem to get this going myself, so I need a coach. I need someone to help me like focus and get this started, and I did, and, it’s been…you know, obviously there’s been ups and downs, it’s not easy, there’s no fairy tale ending, but it’s been great.

Colin:  What would you say has been the toughest thing to overcome? You know, sometimes they’re limiting beliefs, negative mindsets, obstacles. What have been some of the biggies as you’ve gone from taking this idea for Cloud Coach and really moving it closer towards it becoming your source of income?

Ethan:  This kind of technology coaching is something that I’ve always done for people for free, so I think one of the biggest mindsets first was “Oh my gosh, people will actually pay me to do this thing,” and then just the belief that I can charge for it. It’s hard to go from doing something for free for friends and family and then saying OK, now I’m going to charge people for it.

You know, honestly, until I got my first client, and the PayPal email arrived that said, “You have received a payment,” I still didn’t believe that it would work, that I could charge for my services, until then. So, that was a big relief.

You know, you’re just constantly…When you’re working for yourself, you’re just, it’s very easy to second‑guess the business model and second‑guess your value, but it’s a hurdle to get over. Sometimes you can’t get over it until someone actually hires you, and then you can start to break it down and say “OK, well, this is valuable.”

Colin:  Yes, yes, very good, yes. I can totally understand that one. Any others? You know, some of the challenges, some of the obstacles, some of the mindset shifts that were in the way for you when you first started out?

Ethan:  Sure. I think that for most people, seeing a young person, who seems to have a great job and a great situation, to see them want to lose that and change that and do something that is a bigger risk definitely upsets people. I’ve had people close to me, kind of express their, maybe their disapproval, or just not understand what I was doing.

That’s a big obstacle ‑‑ the people around you, if they’re not used to working online, which clearly if you’re reading this website, if you’re watching this interview, you understand that people build businesses online and are able to sustain themselves, but for somebody who maybe isn’t familiar with this, it seems very far‑fetched. It seems way out of left field.

So, being able to surround yourself with people who do get what you’re doing, but also…you can’t shut the other people out, you have to figure out a way to kind of deal with them compassionately and still keep your own sense of direction.

Colin:  Yeah, very good. If there is anyone listening to this now ‑‑ and then they, maybe you’ve got an idea for something that they could do a little bit down the track. Because I talk about working your nine to five to bring in an income, and then figuring out your five to nine, what you do outside of that that starts a new track.

Because that’s what I did, I know that’s what you’re doing, it’s what many people do. It’s the safest way of shifting across to actually following your true path and your passion, and what I call “following your smile.” So if you could break it down into sort of steps that you’ve followed, and I know you’ve had a fantastic coach, Jonathan, is that right?

Ethan:  Yes, yes, Jonathan Mead.

Colin:  Yes, so Paid to Exist. I do hope to interview him as well at some point. So yeah, if you break it down for us, Ethan, what was sort of first step, second step, third step, that got you moving in this direction?

Ethan:  I think one of the first things that I did with Jonathan is that we kind of sat down together, and he said, “OK, mail all of your business ideas, all of your ideas for a blog.” I think I had like three or four ideas, kind of schematic ideas. We just kind of evaluated them from the standpoint of is this something that I will enjoy doing on a continual basis, is this long‑term? Is this something that people are willing to pay for, potentially? You know, what is your potential service or products that you could offer? And how viable is it? Is there a market?

I can’t express the importance enough. You don’t necessarily have to hire a coach, but even if you know somebody who’s familiar with business, just to sit down and run by some business ideas with a third party that you trust is really helpful, because for me, I had these four ideas, and I was attached to all of them. It’s very helpful when you can get some ideas and feedback from someone other than yourself getting those ideas. That was kind of the first step.

I would say, once we had decided that Cloud Coach…Actually, it didn’t even have a name at that point, but once we had decided that this technology blog thing would be what I was going to do, then we started talking about a website name, and kind of a tagline. It seems almost like a corollary to what you would think, but having the name and the tagline really helps define everything else that you do.

It’s hard work to come up with a tagline that you like, and I’ve toyed with changing mine before, and it still stuck. Mine is, “Live and work in harmony with technology.” What’s great about that is once you have that tagline, then you can continue to imagine this business, imagine this thing that you’re going to create, and you can ask yourself, “Does this fit with living and working in harmony with technology? Does this fit in Cloud Coach?”

What else did I do? He had me write some profiles of ideal customers, what they like, don’t like, their fears, their frustrations, and that’s something else that you can use to guide your planning and your writing. Then after that, it was really just about then building a website. At that point, I dove in, and I had used WordPress a little bit in the past, but never really that much, so I immersed myself in WordPress and built the website.

There’s a lot that goes into launching a site and doing this, but I would say picking the idea, figuring out your theme, and then building a home for yourself is kind of the three step process, first one‑two‑three there.

Colin:  Perfect. Thank you, that was actually perfect. I realize there are lots of nuggets in that for anyone that’s listening to this and thinking, “That’s something that I want to do there,” and what you provide, I followed you, is really some great ideas, and tips, and tricks around the technology, but one of the words that, when I first saw it, really got me…I wonder what you meant for that when you talk about technology self‑sufficiency. I had not heard of technology self‑sufficiency before. Can you help us understand what you mean by that?

Ethan:  Sure. When I was working in the corporate world, I would notice that our companies would hire tax consultants, or consultants of any kind, to do a job, and then these people would end up paying year‑round. They would end up just being there for months, or long amounts of time, as consultants, billing $200 and hour, and great, right?

It’s just, that’s not sustainable for a small business, you know? If they’re going to hire a consultant, they need to get what they need out of that person and be able to integrate it back into their business. So that’s where the self‑sufficiency really comes in, is that I want you to be able to do these things yourself. I have a pretty good sense of when I talk to somebody and get a sense of what they can do and how tech‑savvy they are, I’m very good at saying like, “OK, this is going to work for you. This is something that you can learn, and let me teach it to you.”

You know, sometimes I’ll have somebody get in touch with me, and I’ll chat with them, and I’ll say, you know, “You can figure this out yourself. You don’t need to hire me.” Sometimes they do, sometimes they don’t.

So it’s just about being able to have me do something for them, and then me teach them how to do it, and then hopefully they’re able to continue doing it.

Colin:  I know that part of what drives you is to really simplify things and to use the least amount of technology, rather than to go in the opposite direction and complicate things. So is there anything you can talk to around tools that we should be using that you used with great effect?

Ethan:  Well, I mean, it’s hard to make generalizations about, you know, what tools everybody use. I mean, I agree about using the least technology possible. It’s kind of a dated book now, kind of a…I guess maybe it’s a classic business book, called “Good to Great” by Jim Collins, and he talks in that about using technology for technology’s sake never makes a business great, that companies that embrace technology and have a reason for embracing that technology are the ones who get ahead, and the ones who say, “Oh, my God, we need to embrace technology for technology’s sake,” don’t succeed, they’re not great companies.

So, that translates into maybe me recommending that you not get on Google+ or maybe don’t get on Twitter. If your clients aren’t there, if your people aren’t on Twitter, they don’t need to embrace that platform just for the sake of being there.

Now, of course, there are always opportunities to expand into new places, but that’s just an example where, if you’re already overwhelmed with Facebook, why add Twitter to the equation?

As far as tools that I like to use, I mean, my browser is Google Chrome, I think it’s fast, I think it’s the best browser. I love Evernote, that’s a tool that I use to really save web pages, write down ideas. I’ve written about it a bunch on Cloud Coach. I’m a huge fan of Gmail. I think that in this age, where we’re just inundated with email, Gmail gives you the best tools for managing that and being able to handle that flow.

So those are definitely three, you know, Evernote, Gmail, and Google Chrome, those are kind of three things that I’ll usually recommend to people no matter what, especially if they, you know, if they’re having trouble with something similar.

But beyond that, you know, I try not to…you know, I definitely have a large body of tools that I lack. I don’t push them people as their tool. If somebody needs something, then I’ll make a recommendation but I definitely don’t want to end up leaving someone with a whole lot of new things that they might not really need.

Colin:  And using Gmail leads us on to your training program which you’ve called Inbox Zero training program. Tell us a little bit about what that’s about and how it could help anyone that’s listening to this.

Ethan:  The Inbox Zero training program is a technique that I’ve developed over the last few years for automating a lot of the organization work that you’re probably currently doing by hand. Gmail, again, it’s suited for Gmail.

The course does talk about if you need to switch to Gmail, there is that section of the course that will help you there. But it essentially walks you through creating the filters that help you automate your inbox. What I mean by that is say that we decided to work together and you were going to be my client, Colin. I would set up a folder for you so that way I could save our correspondence.

I would go one step further and I would tell Gmail to automatically label any mail from you to be in this folder. That’s an example of automation where now when I receive an email from you, I no longer have to worry about organizing it because it’s already organized.

So that’s just a very basic example. That’s kind of the system that I teach in the course. It’s a self‑paced course that, you know, it’s all video and PDF checklists, so basically you can go at your own pace and learn how to do this yourself.

Colin:  Very good, very good. And as we come to the end of this interview, what do you have around you in terms of support, both in terms of mentors, you talked about coaches and Jonathan, and do you see that as an important part of doing what you do in terms of a solo entrepreneur?

Ethan:  Yeah, I mean, having a support network, having just a network of other people doing what you’re doing is fantastic. I mean, I have a mastermind group that I formed. It’s been going for about two months now. These are all people that I was kind of, every month or so, we would just jump on Skype and just, you know, “How’s it going with you?” “Great. How’s it going with you?” share ideas, but a group of five of us have kind of formalized it, and that’s been really fantastic, to form a group of people who understand what you’re doing. I also, you know, I have no shame about hiring people.

You know, I think that you have to be willing ‑‑ and even I have to be willing ‑‑ to recognize when my expertise isn’t strong enough, or maybe just where…A perfect example is the Cloud Coach logo. I recently got a new logo designed by a professional, and when I launched the site, I made the logo myself.

It was good enough at the time, but I was never really happy with it. I’m not a graphic designer, I just decided…Sure, I’ve always wanted to learn Adobe Illustrator, but is it really worth my time to learn that right now, and try to design a logo, or should I just hire someone? So I hired someone, and it’s great. I’m so happy with it. His name is Dustin Hoffman by the way, I’ve got to send a shout‑out to him.

Yeah, hire people when you need to hire people. You don’t always have to do everything yourself as a solo entrepreneur, and that’s important to remember. You have expertise, and you should be spending your time doing as much of what you’re good at as possible, and letting other people do the stuff you’re not so good at.

Colin:  That’s a great lesson, and one that I think any entrepreneur would understand. I certainly understand that, trying to do too much, and then you’re doing things you’re not very good at, and you’re using up valuable time when you could find someone who could do it in a third of the time, and probably 10 times better than you.

Ethan:  Yeah.

Colin:  Lastly, I know it’s a real passion of yours, that’s what you’re doing at the moment, one of your sidelines is you’re building this little house with wheels, as you’re calling it. Just tell us a little bit about that.

Ethan:  Sure. I became inspired by the tiny house movement about a year and a half ago, and I just fell in love with the idea of building a really small house that I could move, if I ever move, and something that I could own outright. I actually really made it a part of my whole transition from a full‑time employee to a solopreneur.

For the last year, I was just putting away money as much as I could, and I started construction, actually, the weekend after I quit my job, and I’ve, hopefully, saved up enough to complete the whole project.

But it’s something I’ve always wanted to do. I’ve always wanted to learn how to build a house, so I’m doing it, and it’s going well. It’s moving slower than a professional would take to build a house, but it’s a great learning experience, and I actually have a little website where I post just pictures of the construction progress. It’s, if anybody’s interested in checking it out.

Colin:  What was that?

Ethan:  Nope, just

Colin:  It’s, yeah. What’s really interesting about a project like this is that once you’ve built it, you’ve become a bit of an authority, and then, others then, say, “Well, can you help me?”

And this is how it leads to another income source for someone like yourself that loves to do a number of different things rather than be tied down to one thing. That’s something I’ve seen time and time again with others and even myself, my own experience. It comes back to that really following your passion and trusting that it will all make sense at some point.

Ethan:  Absolutely.

Colin:  As you rightly say, as long as there is a need out there and someone is willing to pay to have that need sorted out for them, then you have a business, you have a viable business, so.

Ethan:  Absolutely.

Colin:  All right, last question, then. This is one that I asked every single individual that I interview. It’s quite an open question, just always interesting to see where it takes you. So, here’s my question. What’s becoming clearer to you?

Ethan:  What is becoming clearer to me? Wow, that is a very open question. What’s becoming clearer to me is that, and this is related to the tiny house, I think that looking at the world from an environmental standpoint, population standpoint, it’s becoming clear to me that the way that we’re currently living on the planet isn’t necessarily sustainable, and that I would like to get more in line with what is sustainable. That’s where I’m coming from, from this small house, smaller footprint, owning less things.

It’s becoming clear to me that we can’t necessarily afford to keep up the way that we’ve lived the last 30, 40 years.

Colin:  Thank you for all of the great advice that you’ve given us, Ethan. There have been a number of little nuggets around one, starting your own business and steps to do that, two, around the service that you provide and how you can help individuals with that service, and then three, with this project that you’re running that right now is moving forward but who knows where that might lead for you, as well. You will end up with a little house that you’ll be living in. That’s for sure. A big plus from that.

Thank you from me to you for your time and your inspiration today.

Ethan:  Thank you. It was great being here.

Colin:  Bye for now.

Ethan:  Bye.

This entry was posted on Wednesday, October 10th, 2012 at 8:16 am and is filed under Interviews. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.
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    Take a look at some of the responses we have had to this article.

    1. Oct 13th

      Hey Colin,
      I listened to the interview with Ethan and enjoyed it. I did a similar interview with him a couple of months ago and he knows his stuff. I like the approach you take to the interview which is very brief transitions between questions and an almost exclusive focus on the person you’re talking to.
      I’ll be checking out more from you in the future.
      Joel Zaslofsky recently posted..On Being Weightless, Intensely Relaxed, and Experiencing NothingnessMy Profile

    2. Colin
      Oct 13th

      Thanks Joel. Funny… I’ve not really though about my interview style!!! Thanks for dropping by.

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