The Must-Have Web Entrepreneur Checklist

The sky is the limit.

Running a web business is fun and exciting, but it also involves certain responsibilities. Knowing how they might affect you can help you to find the right business opportunity for you.

Your first step in finding the right web business opportunity is to define yourself. It sounds simple … or does it? Here’s a quick checklist of the factors you should consider before you embark on your entrepreneurial journey.

  1. What are your motivations for owning a web business?
  2. What topics interest and excite you?
  3. How good are your technical skills, and in what areas?
  4. How strong are your marketing skills?
  5. How much time do you have available to spend on the site?
  6. How much money do you have to invest in a web business?
  7. How quickly do you want to make back the money you invest in the business?
  8. What’s your exit strategy for the business?

Let’s look more closely at each of these.

1. Your motivations

What are your motivations for owning a web business? Do you want to build a passive income stream, a full-time business, a fun hobby, or one that will provide search engine benefits to another business you already own, for example?

Be honest with yourself. Your motivations may change over time, but you need to know what’s driving you now. Understanding what matters to you is the first step in working out which opportunities are worth considering, and which ones you should pass on.

2. Your interests

Many online business owners admit to having a strong passion for the topics of their sites. What happens if you lack passion? You’ll likely have a hard time finding the energy to work on it, understanding the motivations of the people who use it, or marketing to its audience.

So the second step is to ask yourself, “What are my interests?” Note them down. Think about each one in more detail—what it is about that topic that you really love? What gets you excited about it? And, importantly, is it an interest that you do—or would like to—share with others?

3. Your technical skills

There’s no point investing in a business that has a web presence that’s beyond your technical capabilities—or your budget for hiring help. So it’s important to accurately and objectively assess your technical skills.

Make a list of all the technical capabilities you have, and rate them so that you know which are your strongest skills, and where you can develop greater capability.

Don’t have any technical skills at all? That’s fine—recognizing that now will help you find a business that you can successfully manage, run and build from day 1.

4. Your marketing skills

As we know, web business marketing can take a variety of forms: advertising, search engine marketing, affiliate programs and cross-promotions, social media, content creation and more.

Do you have any experience with online marketing? If so, which aspects? And which are you confident with? Have a think about your skills, and make brief notes that you can refer to as you sift through the for-sale listings.

5. Your available time

Be realistic about the amount of time you can reasonably put into building up the business you buy. But time isn’t just about hours in the day or spots in your schedule. You also need to look at how much work you’ll need to do to make things happen on your new site in timeframes that you feel are reasonable.

Look at your weekly schedule and estimate how many hours you can reasonably set aside to work on your business.

Your available time will help determine what you’re able to achieve with the business in a given timeframe. It should also help you to avoid businesses whose day-to-day running requires more time than you have.

6. Your available funds

How much can you afford to invest in a business?

It’s important to have a clear figure in your head before you start your search. That’ll help you eliminate offerings that are out of the ballpark, and to negotiate with a seller when the time comes.

A spending limit can help you focus on opportunities that represent value—rather than simply having the right price. It can also allow you to make practical, goal-oriented plans for your business, and eliminate options that don’t fit the bill.

Decide on a figure, write it down, and commit to sticking to it.

7. Your payback expectations

Before you invest money in a web business, it’s a good idea to work out if—and when—you expect to make that much money back from it. This question combines a number of the factors we’ve already looked at: your motivations for buying the business, your available time and skillset, and the amount of cash you’re willing to spend.

If you plan to pay others to work on the business once you’ve bought it, you’ll probably add those figures to the establishment cost to arrive at an overall sum you’ll need to earn to break even on that investment. You’ll also likely spend time maintaining, promoting, and building the business you buy, and perhaps you’ll decide that you’d like to make a certain return on that time as well.

Spend a few minutes listing the estimated costs of running your business, and add them up. Note down your purchase budget, too. Then, when you’re researching opportunities, you’ll know how much money you’ll need the business to make in order to cover its running costs. You’ll also be able to calculate when it might return your initial investment.

8. Your exit strategy

An exit strategy is basically what you want to happen to end your involvement with the business you buy. You may want to:

  • sell it to someone else for a higher price than you paid for it
  • merge the business and its customer base with a business you already own
  • develop the business to be self-sustaining within two years, so that it takes you no more than two hours each month to run, yet provides income for the other ventures you’re involved in
  • keep running and improving the business until you die, at which point you’ll will it to a relative or friend…

If you define your exit strategy up front, and give it a timeframe, it can help you to assess how appropriate a particular opportunity is to your goals.

Ready to browse?

Once you’ve worked through this checklist, you’ll have a much better idea of the businesses that might suit you. Why not do a little market research as a next step? Feel free to browse businesses for sale on Flippa, or to search for opportunities with the specific characteristics you’re after.

Flickr photo: Mike Benkhen

Web Entrepreneur & Sidekicker Founder Tom Amos on Startups, Ideas, and Finding Opportunities

Tom from Sidekicker

“Very few ideas are new,” says Tom Amos, Founder of Melbourne-based when I ask him how, exactly, he got the idea for his fledgling but successful startup business.

“I think there’s way too much of a focus [in the startup space] on creating something totally new that’s not being done anywhere else in the world. What’s the saying? ‘There’s nothing new under the sun.'”

Of his own business, he says simply, “We saw an existing market, and we wanted to improve on that.”

But it turns out the factors that let Tom spot that opportunity are pretty complex.

Sidekicker is an online marketplace that connects small to medium businesses (SMBs) looking to increase their project skills or capacity with quality temporary talent–the “sidekicks”.

It was a combination of personal experience, professional experience, industry knowledge, and passion that let Tom perceive that opportunity.

Personal and professional experience

Tom initially saw the opportunity for his business in his own life.

Back in 2010, while he was working at consulting firm Deloitte, he was also studying and playing golf for his local club. Tom didn’t have a lot of spare time, and says he relied a lot on his mum to help him out with errands. But, he says, “I kept thinking, ‘I’d pay someone to do this for me.'”

TaskRabbit had just started operating, so Tom knew there was a business model around that idea of personal help.

But it wasn’t until Tom was working on Sidekicker that he and co-founder Jackie realized that the bigger need was within small businesses, rather than the individual market.

For now, that moment was a long way off.

In the meantime, Tom was working with SMBs through his role at Deloitte and knew how stretched they were. His first-hand professional experience told him there was a problem with the existing temp-agency model in the SMB niche.

Industry knowledge

Did Tom research alternative models within the particular niche he was targeting?

Interestingly, when he talks about temping agencies, he mentions that his understanding of that space is limited. For him, the hands-on experience he gained when working with SMBs–and as a gun-for-hire himself in the world of consulting–gave him the insight he needed.

He knew how much SMBs disliked temping agencies, and began pondering ways to improve on that model.

“Business owners are time poor. We’re dealing with people who have got projects or event[s] and they just need to scale up quickly. They don’t want to be looking through applications. They want to be connected with someone at a reasonable price and without a lot of hassle.”

For Tom, this was more food for thought.


Passion was another key factor in his ability to perceive the opportunity to create Sidekicker.

“One of the things I like is people being empowered and taking control in what they want to do”, Tom says, rather than being told what to do by a placement person or overseer.

This view steered him away from, for example, creating a better temping agency that could outcompete others in the same market. It encouraged him to consider a technical, crowdsourced solution instead.

“Our view is that through technology we can connect the two people that are important: the person posting the job, and the person doing the job,” Tom explains. “There’s no need to have someone else there as a roadblock. Our technology takes care of a lot of those things.”

That passion, he says, is “what keeps you going on the shit days.” Seeing his business make a real difference for others–whether they’re sidekicks or hiring businesses–is immensely satisfying and inspiring for Tom and his team.

The final push

With these ideas swirling through his mind, many of the dots still remained unconnected. What was it that prompted Tom to give his “crazy startup idea” a go?

It was time spent working in Wellington, New Zealand with a friend who’d started his own beer company. “If he can do it,” thought Tom, “I can do it.”

So when he came back to Melbourne, he started talking to people. “I just kept getting myself in deeper and deeper,” he says, “so that I had no choice but to do it.”

Finally, he decided to take a year off work, to focus on Sidekicker and really give it a go.

More opportunities

Tom’s startup idea wasn’t completely new: it was already gaining traction in a different niche, as TaskRabbit.

And as Tom worked on the business, bringing in co-founder Jackie and digital agency Loud and Clear, the idea evolved into the SMB-targeted service you see today.

“All ideas start with one thing,” Tom says, “but they lead off into something else as you realize new opportunities.”

Tom is always looking for business opportunities to enhance Sidekicker’s offering. Right now, he’s working on an idea to partner with a training organization to upskill and train the Sidekicker applicants who don’t make the cut.

This opportunity arose from a connection that Tom made months earlier at an industry event with the owner of a training business coupled with data from his own business on applicant rejections.

For Tom, it seems, opportunities are everywhere. So his advice to new and would-be founders is straightforward.

“When you’re starting something new, you can’t hold onto your idea too tightly. Yes, you’ve got to have passion, you’ve got to have a clear vision for where you want to get to, but you also need to be adaptable,” he says.

“If opportunities pop up where you can do something that’s a little more profitable, or it’s going to change people’s lives more, then you’ve got to grab that.”

Recommended reading

Looking for more hands-on interviews with entrepreneurs in the internet industry? Check out these articles:

Photo courtesy: Tom Amos

Listing in the App Store? Avoid the DUNS Delay

When the time came for Melbourne-based entrepreneur Luke Meehan to publish an app in the App Store, he faced a two-month delay in getting it listed.

It was easy enough—and cheap, costing a one-off fee of just AU$30—to register and publish in the Google Play store. But the Apple Store required him to submit a DUNS number as part of the registration process, which costs AU$99 (a fee that recurs annually).

A DUNS number is “a unique nine-digit identification sequence which provides unique identifiers of single business entities,” according to the website of Dunn & Bradstreet, the organization that issues the numbers.

“That might be common to companies in the US,” says Luke, “but it’s certainly not common to companies in Australia, let alone small startups or small companies.”

And, he points out, it’s probably not common for developers in other countries outside the US.

Different Developers, Different Registration Requirements

Importantly, the DUNS number is only required to join the Standard iOS Developer Program if you’re a company. If you’re an individual or sole trader wanting to publish apps, you can join that same program without the number.

It’s free to register for a DUNS number, but outside the US, it’s not quick.

Luke explains:

“If you haven’t got a DUNS number, it takes 15 days for it to be created, then it takes another 15 days for it to actually be replicated across to Apple’s databases.”

“There’s very little communication during the process,” he adds. “The only way to check progress is by emailing support.”

When Luke’s application stalled, he wasn’t alerted to that fact. It was only when he emailed support to find out why the application was taking so long that he was told he needed to provide more information.

A customer service rep from Dunn and Bradstreet told me that the number creation process takes around 4 business days, but updating the DUNS international database, which is used by Apple, can take up to 14 business days.

The information Apple provides on this process suggest much shorter timeframes than Luke experienced, possibly because US DUNS numbers don’t need to be added to the international database before Apple can access them.

But any company outside the US that wants to join the iOS Developer Program needs to know about this lag.

“So when we were starting out, there was a eight-week delay before we could publish an app,” Luke says.

Why Is a DUNS Number Needed?

Apple doesn’t seem to have explained this, though some have speculated that it’s just a simple way of verifying a company’s credentials.

The D&B website explains only that:

“Companies worldwide use the DUNS Number to link information about suppliers, customers and trading partners, providing a more complete picture of the risk and opportunity in their business relationships.”

What It Means for App Owners and Developers

If you’re taking ownership of an iOS app from its original developer, you’ll be needing an iOS Developer Program membership so you can control that app within the App Store, publish new versions of it, add others (if that’s what you have in mind), and so on.

If you’re running a company outside the US, and you don’t have a DUNS number, make sure you allow time for that process to take place as part of joining the iOS Developer Program.

Further, Luke explains that the iOS Developer Program membership registration process really seems to be focused on developers.

“For non-technical sole proprietor small businesses we have to invest a significant amount of time to walk them through the process of obtaining an ID. In some sections, they might as well be reading forms written in a foreign language.”

Will this approach change, as more and more non-technical business people—not developers—are required to gain memberships in order to publish apps they’ve bought (or commissioned)? We’ll have to wait and see.

On the plus side, Luke adds that it’s much easier to publish to the Google Play store where, he says, “the app ID creation process is very simple, very quick.”

“You create an app publishing ID. It costs you $30 as a once-off fee. It’s not recurring like the Apple one, and it’s just a much easier process. There’s no app ID for type A and app ID for type B, and for type B a four-week process to have a credit agency review your application.”

Just as well! App marketplace registration may take time for the new app owner or developer, but once it’s done, it’s done. Have you joined either the App Store or Google Play recently? Share your experience with us in the comments.

Photo credit: Matthew

A Daily Podcast and a Blog. How the Heck Does John Lee Dumas Do It?

Every web entrepreneur loves John Lee Dumas—or at least that’s how it seems to us.

John’s blog hosts a seven-day-a-week podcast, in which he personally interviews entrepreneurs and experts from all over the web. He also publishes a blog, produces ebooks and other resources, and manages the passionate, inspired and inspiring Fire Nation Elite community.

It’s exhausting just to think about! What the heck is his secret? This week, I got the chance to find out in a quick Q&A session with the man himself.

John, you’ve interviewed more than 300 entrepreneurs. You produce a weekly podcast, you’ve created a dedicated EntrepreneurOnFire app, and you also create ebooks and other resources for your followers. Where on Earth do you find the time?!

I am an extremely efficient person, and I’m a big believer in the idea that “the task will expand to the time allotted”. Therefore, I allot my time wisely and make the most of what I’ve got!

An example is my batching method for the podcast. With a seven-day-a-week podcast, some might think that I’m literally on the line with a new Entrepreneur every single day recording one more episode. Truth be told, I have about 30 episodes scheduled out in LibSyn right now. That’s because every Monday I do eight interviews, starting at 8am, and ending at 5pm.

I then spend the rest of my Monday night editing every one of those episodes. Come Tuesday, my week is free of the “episode portion” of the business so I can concentrate on the other things you’ve mentioned like ebooks, social media, Fire Nation Elite (my elite mastermind group) and other resources.

Wow, that really is efficient! I know you also have a team, which must help with that too. Can you tell us a bit about them and what they do?

I currently have one Virtual Assistant working for me from the Philippines, who I found through Chris Ducker’s VirtualStaffFinder. She’s awesome. I pretty much delegate anything to her that is a repetitive task. So, she does a lot of the scheduling for our social media posts, helps me create the skeleton for my show notes pages, and creates things like the pretty links for every guest’s page on the site.

I also have a partner in the business, Kate Erickson, who is the Content and Community Manager for EntrepreneurOnFire. She writes our blog, creates all of our content for the website (our giveaways, for example), manages our marketing campaigns/CRM and is the lead on Fire Nation Elite, our mastermind group. She’s also my girlfriend, so finding her was pretty easy!

Aha! Well, it sounds like you’ve got a pretty smooth-running team there. I’m getting the impression that process is really important to your ability to get things done, but also to the quality of your output. Is that true?

Yes, it’s absolutely important in terms of getting everything done. Without the batching of the interviews, for example, I wouldn’t be able to accomplish all that I do.

But just because I batch doesn’t mean I slack on quality—that’s number one for me.

I’ve ensured that I have the best possible set up with the best possible audio, and I do every edit myself. Quality is very important to me. The process supports my goals in that it affords me the time during the rest of the week to get other important stuff done for the business, like creating resources and products for my audience.

Well, let’s talk about audience. Your business is pretty heavily niche-focused. How important do you feel it is to have deep experience within one niche in your success?

Niching is so important—it’s required. If you don’t know exactly who you’re speaking to, then you’re speaking to no one.

I think that dedicating yourself to becoming better at what you do every day is the most important thing—always be ready to learn. When I started EntrepreneurOnFire I didn’t know how to conduct an interview. I didn’t even know how to record a podcast. It was through my relentless dedication to, and passion for the process that both interviewing and podcasting have become skills of mine.

So I think it’s more about the depth of your skill (knowing exactly what you want to be known for, and dominating that) rather than breadth.

Wow, it’s difficult to believe that you started out without knowing how to interview people, or how to create a podcast. What’s been your biggest challenge in growing your business to the point it’s at now?

I think for me, the biggest challenge is maintaining quality while continuing to scale. I mentioned earlier than quality is very, very important to me, and so it’s definitely been a challenge to continue to bring myself back to that when there are opportunities all around me that I could go after. I will not go after those opportunities at the cost of quality.

I’ve overcome that by hiring amazing people to help me. I wouldn’t be where I am right now without their help.

That’s a great point. Is there any other advice you’d give to someone building a web business?

Just start. You can’t let fear and doubt keep you from following your passions. It doesn’t matter if your product or your website or your podcast isn’t perfect—you have to get it out there. You can correct course, pivot, improve along the way, but if you never start, then you’ll get nowhere.

Want to read more about how amazing people manage to get so much done? Read our interview with affiliate extraordinaire Rae Hoffman

Just How the Heck Does Web Entrepreneur Rae Hoffman Do It?

If you’ve ever had any dabblings in affiliate marketing, you know the name Rae Hoffman, and the site

Rae’s an affiliate marketing guru. But that’s not all. She’s also a web marketing maestro, SEO specialist and oh, she does speaking gigs too. And she does it all with a fun, positive, action-packed attitude.

Rae makes it look easy, and that drives more than a few of us crazy with envy. Sure, she says “I’ve busted my ass to get here,” but come on. She must have some kind of knack to be able to do all that—and do it so well. Mustn’t she?

This week, I decided to find out. Just how the heck does Rae Hoffman do it?

Rae on Productivity

Rae, you do a lot of stuff. And you do it so well. What’s your secret?

Coffee. Lots and lots of coffee! Well, that and just knowing that to achieve my goals, certain things have to be done. There’s no room for excuses, for inaction or for letting a setback have an impact on the future.

You just have to get shit done.

Well, from the outside, it looks like you’re getting a lot of shit done. From blogs and affiliate sites, to consulting and speaking … yet when we emailed you for this interview, you answered right away. How do you even get through all your email, let alone prioritize the actual work you need (or want!) to do?

Ha! You actually caught me on an evening when I was catching up on my inbox while watching my football team lose. I am pretty busy, but I guess I’m used to it. I’ve always been the type of person who has to be doing twenty things at once. But, that doesn’t mean I don’t get overwhelmed at times.

2013 has actually been a year of consolidation for me behind the scenes — preparing to absolutely own things in 2014. I sat down early in the year and made some tough decisions on which projects would get my focus, now that it’s a bit more difficult than it used to be “in the old days” to manage and market my numerous affiliate sites.

We’re in the process of closing down my website publishing company, MFE Interactive. I loved those sites and loved what we built with that company, but both myself and my partner have had a lot change in our lives—and goals—since we started the company in 2006. It was simply time to move on.

Sugarrae still owns a lot more affiliate sites than I have time for, but I’m in the process of paring them down. I’ve sold some, shut some down, and have picked a few others to move forward with in the future (including a new one that I am creating behind the scenes now).

The Sugarrae site itself is going to have a lot more of my focus in the future whereas it’s always been a “back burner” site of mine in the past—believe it or not.

PushFire gets the bulk of my business attention these days and I really love where we’re heading with it. I’ve been accused more than once of having an addiction to building companies—an accusation I really have no defense for.

Also, I have an amazing partner in PushFire. He handles all of the PPC services as well as managing operations, which leaves me free to focus on my strengths in regards to SEO strategies as well as building and managing the company.

As far as prioritization goes, I have a huge cork board in my office. All of my main initiatives are on it and I use old fashioned pen and paper to tack up todo lists of things that need to get done to move them forward. It may not always happen seamlessly or on time, but I usually find a way to make it all happen. Archaic, I know, but it works for me.

When you fully commit to achieving something, your mind has an amazing way of ensuring it gets done.

Rae on Experience and Experimentation

That’s an interesting point. How important has a breadth of experience—of getting things done—been in getting good at what you do? Have you become more efficient as well as more capable over time?

Hands down, yes, experience is important.

I’ve been doing this for over 15 years now. Which means I’ve been able to learn each change as it happened—in bits and pieces—versus coming in ten years after the fact and having to learn it all at once.

And as with life, knowing the history of how the engines used to work, what they did to combat problems (and why) and improve the overall experience is extremely useful in helping you predict where they’ll be going long before they actually actively head in that direction.

I’m not saying you can’t enter the industry today and become amazing at what you do—not by a long shot. But I think that experience is a definite asset in this industry. As is having your own sites to test things and push limits with.

So experimentation is an important part of that experience?

Yes. I happily do things to small affiliate sites I own simply to see what happens to them as a result that I would never, ever do with a client site or one of my own flagship (high-earning or high-value) sites.

Without testing and experience, you’re left with theories and hypothesis. So, if you’re just getting into the industry, start a few of your own small sites to help you gain that experience instead of testing your theories out on sites that pay the mortgage (be it your own site or your client’s).

That’s a great tip. But experimentation also takes time—often more time than the stuff we know and understand. Would you say you work hard, work smart, or work on things you’re passionate about?

All of the above.

I always say that one of the best compliments I ever received was from John Andrews when he said in a 2006 post, “I don’t believe Rae Hoffman is as much of a genius as she is hard worker”. Because I am a hard worker. Always have been, always will be.

My former business partner in MFE taught me a lot about working smart. Prior to getting involved with him I was very successful at what I did, but I did it all—I was a one (wo)man show.

Early on in our partnership, he told me I should read The E-Myth Revisited. That book changed my life in regards to how I thought about business, and my role within that business. I didn’t want to be the forever “lynchpin” to my companies. So I started combining working hard with working smart.

Delegation was not a task that came easy to me—and shelling out money for people to do things I could do myself was a bit of a mind shock. But I got used to it and seeing the benefits of it— on my time and my companies —made it easier to accept as my new norm.

In regards to passion, if you’d asked me ten years ago if I’d pick something (like an affiliate site niche) based on profitability or passion, I would have told you I can learn to become passionate about anything that makes me money. But as the game of being visible online gets harder and I’ve “grown up” a bit from a business perspective, my answer would be to find the nearest intersection of money and passion in your life.

I’m passionate about online marketing, about entrepreneurship, about making a difference in the world, and about my hobbies. Those are what I tend to focus my various business efforts on nowadays.

Find a passion that you can make profitable. Work hard to get it off the ground and then transition to working smart to keep it growing without continuing to put in a ridiculous amount of hours.

Speaking of ridiculous hours, obviously you don’t get to be a web marketing mogul without facing some challenges along the way. How did you stay focused and positive in the early days, when you were less experienced, and the industry was less mature?

Ha. I definitely wouldn’t call myself a “mogul” by any means. I simply do what I love to do—and I’ve busted my ass to put myself in the position where that is what I get to do each day.

A lot of my drive and focus came from my oldest son (he was actually how I fell into the industry). Giving him the best opportunities I could was always my driving force (he passed away this past November).

I think part of how I stayed focused back then is also due to the fact that I loved (and still love) the “game” of promoting sites online. Winning was a high, and losing was a challenge to be won.

The Early Days of Affiliate Marketing

For all of my early career, I was an affiliate. Back in the day, Google “danced,” which meant that every four to six weeks or so, they’d update their rankings. The search results bounced all around during the dance, but where you ended up was where you would stay until the next update.

You knew a dance had started when your IM windows started lighting up from colleagues, and it wasn’t uncommon for us to stay up through the night, constantly refreshing the results until we were confident the dance had ended.

If you had a top ranking, you could revel in knowing the revenue from your sites would be rock-solid for the next few weeks. If you got whacked, that was unfortunately how it was going to remain until the next dance. And then the game began—either maintaining or regaining your rankings—all while building new sites to increase your pieces playing the game.

It’s amazing how far Google’s algorithm has come when you think about it. Deciphering that algorithm is a game I love to play, plain and simple. The day that statement isn’t true will be the day I retire from playing it.

So passion mattered even way back then. Is it still your main motivator today? What keeps you on track?

Nowadays a big portion of my drive comes from living up to the examples my son set for me during his life.

The second thing is continually raising the bar. A long time ago, a colleague said to me one night at a conference “Never get comfortable with what you’ve achieved.” I’ve never forgotten those words.

Her Two Most Important Lessons

It’s amazing how those kinds of moments can stay with you. What’s the most valuable lesson you’ve learned that you can share with others who are facing the mammoth task of starting or growing their own online businesses?

I’d have to give two answers.

First, always have any business agreement—no matter how large, small, formal, informal or with “who”—in writing.

Second, you and you alone determine whether or not you’ll be successful in your business goals. There are no acceptable excuses in life. There’s only action and inaction—and your choice of which road you decide to take.

Photo courtesy of Rae Hoffman