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Matt Jaffe: Story behind a Successful Tech Entrepreneur

As one of the successful tech entrepreneurs in Denver, CEO Matt Jaffe has empowered dozens of clients disrupt their industries as well as won some precious awards.
By Anne Nguyen | EnvZone Staff
on November 05, 2019 | 5 min read
Image credit: EnvZone

"Most of my work as CEO centers around vision, strategy, growth, and culture. I plot the course; my team navigates to the destination. Along the way 303 Software has helped dozens of clients disrupt their industries and launch new businesses."

-Matt Jaffe, CEO at 303 Software

Together with an experienced and dedicated team, an adept tech entrepreneur, Matt Jaffe, found 303 Software, guiding his clients through strategic consulting, design, development, implementation, post-launch support, measurement, and scaling. From just a small startup idea, 303 Software has gradually evolved into a full-fledged tech consultancy – and there must be good reasons for it!

Earlier this week, we luckily grasped a chance to have a short yet motivating conversation with Matt. His first impression was filled with friendliness and self-confidence. From such a strong and idealist figure in tech area, there’s a hidden story on his road to current success. So, let’s go explore!

ENVZONE: Why did you decide to pursue the career path for a tech entrepreneur?And what are the first challenges that you faced at the very first beginning of your business?

MJ: I decided to start my career on technology when I was young and my father brought home an Apple II computer, which was a modem. Actually, it was one of the first desktop computer that wasn’t available in United States. I started to learn how to program it, and how to use the modem to connect my computer to other computers…. it was even before the arrival of Internet. When I learned to do that, I decided that was something I want to do for the rest of my life.

For your latter question, actually the obstacles that I faced when I started my business was as the same with one that other start-up company faced, which are around the people, customer and cashflow. These three things were challenges from the very first days - and remain challenges today 14 years later.

ENVZONE: Could you share the journey of 303 Software? What ups and downs you had?

MJ: We have several ups and downs; the company has grown into contracted over the years. We now have many employees and it’s huge as tank. We can only grow as fast if we are in contact. We’ve always been focusing in writing custom business software. As the projects we work on are very large in scale and very long in time, we sometime get into trouble in terms of cash flow management.

For instance, some projects that we undertook lasted 12 to 24 months, meanwhile other projects also needed to be carried out, which put us under stressful and challenging situations. To handle them, we have to ensure the projects lined up and people can work effectively.

ENVZONE: Could you share some of your strengths as well as some significant achievements that you've proudly got with your business?

MJ: Actually, what I mostly proud of is we are an employee-owned company. We have a philosophy of generating well our business for the users and the employees. And I think that’s the thing we’re mostly proud of.

ENVZONE: Can you share one failure that you have faced and how you overcome it?

MJ: The challenge that I’ve managed to overcome is that in my personal life, I try to remain balance. Thanks to that, I am calm, and present at all time. When I face stressful challenges, I don’t panic, mess up or jump into the decision too quickly. I try to keep my body fit and meditate to keep my mind fit as well. And that helps me to remain steady, patient and not panic when things start to go wrong in my business.

Teamwork is also one thing that is very important in my company. One of our company’s core values is to solve problem together.

ENVZONE: With all the ups and downs you've been through, what advices you think tech entrepreneurs should keep in mind?

MJ: The first is to not worry too much about the long-term – thinking “how thing should be?”  - but focus on what you can do today. Instead of “imagining” all the possibilities of how things could go, you’d better off getting started to achieve and keep going!

The second thing is that, as entrepreneur like myself, we have several ideas all the time that we want to execute on.  But the key is not to start many things at the same time; rather, let’s seek through from the beginning to the end before you start the new thing. Stop starting new thing before you finish what you do!

ENVZONE: As a successful CEO in tech area, what criteria and factors that you need to observe before making a decision?

MJ: We have worked with many companies, and the most significant factor to contribute for the success in technology that I see is that you need a crew including those who are good at managing a company, a market, or a field, rather than with an individual just good in technology.

Having good computer skill is of great importance, but it’s also imperative to find someone - who has a very good business sense in the market that you’re going to operate in. I have observed a large number of technology companies’ failures just because they don’t really understand the market and the customer. Even though they might have the best tech products, if they don’t really understand the market that they’re in, their businesses will be not going anywhere.

So, I always advise people to find an expert and cooperate with them when they start a new venture.

ENVZONE: Can you give an example from your real life?

MJ: When I get started with a Healthcare company, I consulted two gentlemen who had a consultant company in health care - they knew the health care industry very well, of course, but they knew nothing about technology. When cooperating, we created a very successful business.

In fact, I am doing again now in the legal space. I partner with one of my friends who has been a lawyer for about 30 years, thereby he knows the industry and the customer so well. That is also the reason why we’re able to combine and develop our products so successfully.

After all, I see that many technology companies nowadays, they don’t understand the market, even if they have a good idea, or maybe they have a new solution for a problem, without knowledge of business circle, they eventually turn to failure.

ENVZONE: What value does your business deliver to the clients?

MJ: First of all, we would like to bring very high level of expertise but not at a very high price, that’s about the value that we bring. So, we determine to bring some of the best software developers’ products and then help people to easily approach for much less than high-end software developers.

The second is, as we work with various industries, we haven’t specialized in one industry, so we don’t just work for e-commerce, we do all kind of software application. Thus, we’re able to bring out many values to the industry

ENVZONE: Who are your favorite clients?

MJ: Our favorite one is always about outdoor retail industry like skiing or hiking. We also like to work with local government because we really love Colorado.

ENVZONE: What’s your business strategy?

MJ: The strategy that we are working well on is to well manage, to “succeed” in workforce. That strategy we started to implement since 2017 and it works very well because it allows our business to extend in contracts that we need to. Actually, at the present, half of our employees come from 303 Software and the other half are contractors.

What’s more, because of our nature of business, we have a lot of time to focus on the projects that we’re working on. Since there’re many constrains that happens, this strategy helps to pretend the business and keep all thing on process.

ENVZONE: What do you consider the main differences between those people who have been successful and those who have failed?

MJ: My answer is luck! Actually, it’s hard to say the differences between those who succeed and those who fail. It’s not that they don’t work hard or map out clear plans. I see some who does work very hard but eventually they fail. Sometimes, the reason for such failures is they don’t understand the market, the other time is because they are too optimistic about how fast the business will grow, so they ran out of money before they can get to the reasonable scale.

I think the entrepreneur sometimes have the hard time not knowing which to pay attention to, so although working hard, they can’t deliver an appropriate value equal to what they invest. And for some, they don’t really understand what’s going on with the business, so they faced difficulties when they have to make decisions.

ENVZONE: Which books, magazines do you read?

MJ: I don’t spend time reading much business books, but I read all kinds of books which give me interest and inspiration, from fiction book, to historical books. But I see that reading is such a helpful habit that you should keep as daily.

Matt Jaffe Story Behind A Successful Tech Entrepreneur-Fig 1
Image credit: 303 Software

ENVZONE: What is your favorite activity?

MJ: I love skiing, I even accept a job for $12 an hour to teach ski over the weekend.

Matt Jaffe Story Behind A Successful Tech Entrepreneur-Fig 2
Image credit: Mike Arzt

ENVZONE: Who should we talk to next?

MJ: With my network, there’s so many people that are suitable for you to meet and have a talk. I believe their stories will be as meaningful for your audiences. Let me follow up with you via email!

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