Ross SimmondsContent Marketing Strategist & Entrepreneur

Ross Simmonds is a digital marketing strategist who has worked with both startups and Fortune 500 brands. He's also the co-founder of Crate, a content curation tool and Hustle & Grind an online store for entrepreneurs. He's passionate about entrepreneurship, marketing and all things tech.

Recent Answers

You can do it. But I'd recommend talking to an attorney about the North American Free Trade Agreement (NAFTA VISA) - It could save you a lot of headaches in the long run.

I've managed freelancers through my consultancy for the last 3 years. Prior to running my own business, I worked at an ad agency where I also managed a team of freelancers. Last year, my business generated more than $250k in revenue which was only possibly by working with quality freelancers.

I'd say yes, you should work with freelancers. You can refer to them as your "design team" when talking to clients and if they ask if they're employees, let them know they're contractors who you've built a relationship with and trust. You don't NEED to be the middleman between clients and the designer but it's a safe way to show that you're still adding value. I'd keep them behind the scenes and have everything come through you. You should keep the designs under your company name.

Happy to shed more light on this - Drop me a line if you'd like to schedule a call to chat.

I'm not sure of any service for hiring an SEO beyond the standard marketplaces like oDesk & I've worked with a handful of "SEO experts" over the last few years and can tell you that it's important to be careful. I've wasted thousands of dollars bringing in "experts" when things get busy and the results have been everywhere from horrid to exceptional.

For me, the best approach is to take the time to scout out talent as if you're scouting for a professional sports team. Refuse to take the easy approach by putting an ad on oDesk and hoping that the right people respond. Instead, visit communities like,, or even Clarity to begin your hunt!

The community on is likely going to provide you with the easiest route to finding talent. You could upload a post in their community section asking for talent and likely have a decent response. On the flipside, you could also do the heavy lifting on your own by browsing comments and other threads to find people who responded with insightful & high quality information.

I've hired SEO's and marketers everywhere from Europe to Canada - Happy to help out with resourcing or helping find the right talent if you ever want to chat.

1) Identify a list of 20 local businesses who have horrible websites.
2) Reach out to them via email or social media.
3) Send them your portfolio and reference the grant.
4) Line up coffee to chat with them about how it could work for them.

Your target audience is definitely a challenging one to connect with online but it's far from impossible. The first thing you'll want to do is study your audience and truly get a better understanding of where they are spending time online. While they may not be spending as much time online as younger audiences, they've embraced technology and are most certainly consuming content from their social channels and on their favourite websites.

One strategy that would likely make the most sense for this audience is built on the idea of creating and distributing quality content that links to their motivations, challenges and wants. To do this, I would consider what topics are the most relevant to this audience and gather this insight by spending time on the channels they use. Similar to the way Entrepreneurs spend time reading answers on Clarity, these people likely spend time on another website. What is it? What do they talk about? Go there and find out the hot topics. If there's a connection between those topics and your product, you've found a great story that can be leveraged and shared to drive awareness and potential leads to your product.

Identifying these stories and possible messages will then arm you with the ability to craft content that can drive earned media. For example, let's say you crafted an Infographic titled: "How Savvy Baby Boomers Are Navigating The Web" -- You then take this content and share it with a few journalists at outlets that your audience would read and see if they would be interested in posting it. If the content is good, they'll likely consider it and allow you to be placed in front of a highly relevant and targeted audience.

This is just one of the many tactics that could work. If you'd like to discuss ideas in more detail - Line up a call to chat!

This one is challenging because it really depends on what type of college student you're looking to target. A question like this is equivalent to asking, I want to target Generation Y - Ok, that's good and dandy but not everyone in Generation Y resonates with the same message or same applications. You first need to identify who it is you're looking to connect with. I don't have that answer because I don't know your product but let's say you're targeting students at a University that are studying Commerce.

For this audience, I'd start by looking at where they spend their time online & offline. University is still a very offline experience and the internet (social media, email, etc) acts as a facilitator for offline experiences and events. Commerce students are likely involved in things like Case Competitions, Guest Speakers, Networking Events and like every other student - Parties. So how would I get them interested in this app? Focus on one of the three simple motivations of a University student - Help them become made, paid or laid.

Made: Facebook penetrated University with an exclusive angle. They started at the prestige universities making people feel as if they "made it" if they were allowed on the site. I can remember people creating second university email accounts just so they could set up an account for their friends. People wanted to feel a part of it and they felt elite by the network starting without letting people in who weren't in college or university.

Paid: Why do students sign up for LinkedIn in their last year? Because they want a job when they graduate. The people on LinkedIn can possibly help them find a job or at least give them an introduction to the right person. Focusing on this story when talking to students was an easy way to onboard a student market in the early days of LinkedIn.

Laid: Tinder and Facebook both did this very well. Let's talk about Tinders approach as it's the most recent story that demonstrated how to do this right. Essentially, their co-founder approached sororities and onboarded their members. From there, she went to fraternities and told them that all of these sorority girls were on the app and they of course, signed up immediately. From there, they held parties at different campuses and invited the most influential people from the various campuses. The word spread, the app spread and success seemed overnight.

So those are the motivations.. Spend some time to dive into the early days of these apps to understand how they grew a bit more. Another app that spread like wildfire in Universities was LikeALittle. It was an app that was focused on the Laid/Made motivation. People wanted to see if they were being talked about (made) and people were trying to flirt with people anonymously (laid) - The growth of that app was magical to watch..

If you want to dive into some actual ideas for your app, give me a ring some time. Happy to help!

Two years ago, I quit my full time job as a digital strategist at an advertising agency to focus on a startup. The startup was consuming the majority of my time but prior to quitting my job, I bought a new home. To suggest that money was tight would be an understatement. Either way, I had to do it and I was going all in for this new business. That said, I had to ensure the house didn't get taken from us before we got into it.

I decided that I would leverage my knowledge in consulting and bring that to the market. For me, I think consulting is an effective way for any entrepreneur to make some cash on the side. Whether you're a developer, designer or marketer - selling your services is a great way to generate side income. In fact, the majority of the revenue I made from consulting was put right back into the business. A few things that you should keep in mind when taking this approach:

1. Don't offer ongoing, loosey goosey consulting agreements. You don't want your clients to expect that they can call you any time of the day to have you run and put out a fire. Instead of working on a retainer or on an hourly rate - Work with specific deliverables & a fixed rate.
2. Bill 50% up front. Remember, C.R.E.A.M = Cash Rules Everything Around Me.
3. Ensure that your clients are aware of your time commitment and other obligations.
4. Don't be afraid to say no. You might get to a point where your consulting business is booming and your startup is slow at growth. Instead of turning your focus entirely to the service side, remember the long-term goal and limit yourself to taking on enough projects to cover your basis.
5. Never, ever sell your services on Fiverr.

Hope this helps - If you have any questions about the consulting thing and how you can do it effectively while running your business - Give me a shout!

I've been working with funded startups for a couple years as a content marketing consultant and my business has grown significantly year over year.

Relationships are the king of generating new business in this space. It's important to become a key part of the startup community in your area and attend events whenever possible. Meet people, grab coffees, provide value through follow up emails and speak on the value of content creation as often as conference managers and planners will allow.

The second approach that truly has helped me grow my business is the creation of content that helps startups do these things on their own. For example, I've written a Content Marketing Guide for Entrepreneurs ( along with a series of blog posts & Slideshows highlighting how content marketing works for startups. Last year, I wrote a blog post specifically about B2B Startups and how content marketing can help them and then emailed it to a handful of marketing executives at a couple startups. I ended up getting meetings with each of them and working with 4/5 of them.

Finally, you need to develop a trustworthy brand. I couldn't count on my fingers how many times I've heard of marketers lose opportunities because they didn't manage their own accounts appropriately. Whether it's the language they use on their website or the way they carry themselves on social media - It's the little details that differentiate the best from the rest.

If you have any other questions - Feel free to give me a ring! Always happy to help fellow entrepreneurs achieve success.

I've been using and found great success. It's very easy to use and the results have consistently been above average. It's Facebook specific but where are most people spending their time? Facebook.

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