Interview with Matthew Smart of Smart Software Solutions, Inc.

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The Guru Blog spotlights members who are pursuing their passions through independent work. Meet Matthew Smart, President of Smart Software Solutions, Inc. Read on to learn more about how Matthew grew his business to become the highest-earning Guru Vendor and the second-highest-reviewed.

How did you get your start working independently?

I started consulting for clients in 2004 while I was writing my Master’s Thesis. I wanted to break the monotony of writing my thesis and make some extra money to pay off my student loans at the same time.

Has running a business come with any obstacles or challenges? How have you overcome them?

Building a solid reputation was the most challenging obstacle when I was just starting out. I knew that I was capable of providing an excellent level of service to my clients but I had no way to prove that to them. I overcame this obstacle with a mixture of perseverance and cost reduction incentives. I put together a large number of proposals and I discounted my rates in order to maximize my chances of getting the contracts. This was risky since I was performing work for less than cost but I leveraged these initial contracts to build a reputation that allowed me to go after larger and better-paying contracts.

Looking back, what do you wish you’d known as a beginning freelancer?

Over the years I have refined my ability to gauge the quality of a contract and potential client from very little information. Finding the good clients is the most challenging aspect of online consulting and there were a lot of difficulties and losses that I incurred by choosing the wrong clients.

What do you consider your specialty?

I started in 2004 as a one-person firm with a specialization in enterprise software. Since then, I’ve grown my company to forty engineering employees and we now have expertise in every major technology across pretty much every modern industry. We have the technical and market experience to work for pretty much any client we choose. Our true specialty is providing the highest quality software with an unmatched level of customer service to each and every one of our clients.

What do you find the most rewarding about freelancing?

I like that we get to build personal relationships with our clients. We truly see ourselves as employees of each of our clients’ companies and act in the best interest of them at all times. We treat our clients and our employees as members of a family instead of as “profit centers.” This is something that drove me away from the corporate environments in which I was employed before starting Smart Software. Additionally, we get to work on project across every industry and in every technology, which means we are always challenging ourselves and broadening our horizons.

What is your favorite thing about Guru?

I like that Guru does not publish the bids of competitors. This places less emphasis on overall cost and keeps the bidding process from becoming a race to the bottom. This has allowed me to compete on quality of service and not purely on price.

What is one thing you’d like to change about Guru?

For a company my size, it is difficult to manage the invoicing process through With dozens of invoices a week, I wish that there was an API I could interact with that would allow me to tie my accounting software to guru to automate invoicing. Additionally, I really miss some of the filtering options on the project search. I used to be able to filter by budget and hourly rate in a more granular fashion than I can now.

What other sites do you use to find and manage freelance projects?

Guru is by far our most used site. We have utilized Elance and oDesk in the past but find Guru to be much more inline with our company’s business model and values.

What assurances do you ask for before beginning work with a new client?

Very few. We sign a NDA (nondisclosure agreement) with the client and a basic development agreement that outlines terms but we do not require any kind of upfront payment from the clients. Our philosophy on this topic is very simple: If I am uncertain enough about a client’s trustworthiness that I need a deposit, then I will not do business with that client. Everything in this industry hinges on trust and keeping one’s word.

What are your usual work and payment terms?

Our standard payment terms are weekly invoicing and Net 14 due dates, so clients must pay us for our first invoice within three weeks of project commencement and all work ceases on a project any time an invoice is overdue. This limits our exposure while still allowing us to form a basis of trust with our clients. Clients are provided access to their source code and a functioning development site from day one so that they can continually review the quality of our work and provide timely feedback that allows us to deliver a better product. They are also given access to our state of the art project management systems and encouraged to use it to provide feedback and clarification on a daily basis. We try to incorporate them into the project like any other member of my team.

Do you have any tips for getting insurance in the U.S.?

Get professional and general liability insurance from the very first day. The cost of this insurance is based on your company’s payroll so it is quite affordable for one man and small team operations. It is worth every penny.

What has been the most unique or memorable project you’ve taken on so far?

That is really difficult to answer. Every project has had something novel about it that has made it memorable and challenging. The key to a successful career in software is to find fulfillment in the act of pure problem solving. If you have that prerequisite, then every time you implement a feature or fix a bug you feel that sense of joy that one gets from a job well done.

What is one thing you’ve learned above all else about freelancing?

It is hard work. Finding a job somewhere is much easier. However, the sense of personal freedom and self-actualization brought about by freelancing is well worth all the challenges.


  1. Pingback: Interview with Matthew Smart of Smart Software Solutions, Inc. | Freelance Flux

  2. Your story is inspiring and helpful to someone who’s starting out as a freelancer. Thank you for taking the time to share. 🙂

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