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Life as a founder | Jason Cole on entrepreneurship and technology start-ups

Founder and CEO of Da Primus, Jason Cole discusses his experiences with being an entrepreneur.

There are always rough moments in time as an entrepreneur. When outcomes aren't successful and you begin battling against your idea everyday hoping that one day, it will pay off. The process is excruciating at times with unexpected results. But that shouldn't mean you give up. The difference between those who succeed and those who give up, is perseverance. The ability to keep going without losing enthusiasm and effort in order to achieve goals which you have set yourself, results in success. 

It is often intimidating to start your own company or business; it's only just you and perhaps your laptop, with an idea and vision stuck in your head. You know the odds are extremely low but you give it a go and learn. They say you can't do it, think you're crazy but you know inside, that the vision in your head sings louder than those who say 'no'. 

With 20 years of experience within the technology industry, Jason Cole is the Founder and CEO of Da Primus which aims to aid small to medium sized start-ups with allowing them to seek valuable advice on how to move forwards and also access to useful resources for growth. Jason is also a lead mentor at Boomtown Accelerator where he is involved in creating their CTO track. He has joined us for an interview where he discusses his daily routine of being a founder along with advice for those wanting to create their own start-up or follow a path as an entrepreneur. 

The Interview

1 | Describe what you do on a daily basis as founder of Da Primus.

It all starts with one idea

Mainly, I work with early-stage technology companies to help them bring their products to market. This covers nearly everything in the business, not just building software, since the success of a software company relies on finding the right market, building a product that fits that market, finding customers to use the product, supporting those customers, and having enough money to pay for all of it. Since most entrepreneurs have deep expertise in only one or two of these areas, my team and I can help fill in the gaps until they’re ready to hire a full-time team to cover everything.

I also work with larger companies who are trying to make the transition from a small founder-led team to a larger, segmented organization. Many companies that execute really well at small scale stumble when they get big enough that the founders can’t manage everyone directly anymore. At that point, they have to put strong leaders in place in each discipline (marketing, sales, finance, development, customer support, etc.) who can take responsibility for their part of the company. Likewise, the founders have to shift from telling everyone what to do to communicating a vision, pointing everyone in the right direction, and trusting them to figure out the details. Many founders struggle with letting go, so they become a bottleneck when the company’s growth accelerates. I’ve taken several companies through this kind of growth, so I help them avoid the traps hiding on the other side of that big Series A raise.

2 | What made you start your own company to help technology start-ups? What do you love most about helping out entrepreneurs and new start-ups?

I’ve spent over 20 years building software products, teams, and companies, and when I left my last job I found that I wasn’t excited about jumping into another place where I had to fit into someone else’s vision again. What did get me excited was working with early-stage companies and founding teams. I was mentoring around ten different companies in all kinds of industries and several different cities, and I really enjoyed helping them achieve their dream of building a company and bringing a new product to market. I decided that I wanted to do it full-time, so I founded Da Primus Consulting.

Keep pushing when times are hard

One thing that separates Da Primus from other consulting companies is that we offer mentoring and general coaching for free, with no limits on the number of times that we’ll meet with someone. Our name means “give first,” and it’s at the heart of everything we do. If a company just needs an hour or so a week to keep them on the right course, then I or someone on my team will gladly help them. I never want someone to stop seeking help because they’re afraid that they’re going to be “sold” or the meter is going to start running. Once we start talking about leading a significant effort, then we’ll get to a billable engagement.

I love the opportunity to work with many tech startups because I get exposure to so many different industries and technologies and I get to meet so many extremely smart people. While I’m helping them learn how to run a business and build a solid software product, they’re teaching me about artificial intelligence and machine learning, data science, blockchain technologies, or building a customized book subscription service. I get as much out of the interaction as they do, and I get to keep learning every day.

3 | Where did your passion of entrepreneurship originate from?

I realized early in my career that I preferred working in small companies for two reasons:

First, they moved quickly. What could take weeks of meetings, presentations, and consensus-building in a large corporation can take 15 minutes in a startup.

“Here’s the idea, what do you think?”

“Sounds great, let’s do it.”

This speed lets you try new things, see the results, and quickly optimize successes or learn from failures. In larger companies, the perceived risk of failure is so high that everyone needs to sign off before you move. Many good ideas have died in committee.

Second, I wanted to have a big impact on my workplace, even when I was still young. I knew that I had a gift for breaking down complex problems and solving them much faster than other people, and I wanted the freedom to make life better at work whenever I saw the opportunity. I didn’t want to have to “put in my time” before I had the right to make improvements.

When I was about 25 and looking for a job, I had a choice between Andersen Consulting in Hartford, CT, or a small software startup in Harvard Square. Even though Andersen was the safe choice, my wife and I agreed to take the risk and move to Boston. That choice has made all the difference in my career and I’m grateful every day that we made it.

4 | What advice you would give to upcoming, young entrepreneurs who are just starting off with building their first idea?

Persistence. Vision. Passion

First, be persistent, but be smart. You’ll face all kinds of obstacles as you try to turn your idea into a reality, and you’re going to have to decide up front how far you’re willing to go to make it happen. Be willing to ignore the naysayers as long as you still have evidence that you’re on the right track, but make sure that you’re actually looking for that evidence as you go. Set tangible milestones for yourself and track your progress so that you can decide if the company is viable. These could be based on revenue, cash, or progress with product development, but whatever they are they should be objective measures that address the fundamental question, “Are we becoming a healthy company?”

Second, don’t be afraid to quit if it doesn’t work. If you see consistent, objective evidence that you aren’t able to do it, then don’t be afraid to quit. The smartest move many entrepreneurs ever made was cancelling a product that wasn’t working and shifting their energy to something else. Sometimes this means building a new product or company, sometimes it means going back to work for someone else until you have the money and the energy to try again. I’ve seen too many founders struggle with depression and anger because they were afraid that they would let everyone down by closing the company. All they did was drag out the pain. Better to know when to retreat and marshal your energy for another try.

5 | Technology is an industry which has seen incredible growth in the past decade. Where do you see the future of technology and how should young people feel about the future?

We’re already seeing hints of how computers can help us solve both complex problems and tedious ones, and I think that we’ll continue to see amazing advances there. AI and machine learning will help us sift through incredible amounts of data to make better choices and offload detailed work so that we can be more creative. We’ll also continue to find more interesting and unique ways to harness this power in industries that have never considered it before. There’s a lot of fear that “robots will take our jobs,” but I think that the reality is that the machines will take on the jobs we don’t want, freeing us up to do more interesting and creative work.

I’m also really excited about the intersection of agriculture and technology. Living in Colorado, I’m getting to observe an interesting phenomenon in the cannabis industry, where the combination of lots of potential revenue and protection from the “big boys” who don’t are afraid of federal regulations is creating a unique space for entrepreneurs. Suddenly, it’s profitable to spend thousands of dollars increasing the yield of a single plant, and we’re seeing cool applications of IoT, software, and agritech to help plants grow better both indoors and out. These advancements will have huge implications across both the food and medical industries, giving people more access to fresh food even in large cities. I’m excited to see what develops.

A great company starts with great people.

6 | What have you wished you had learnt when you were young, which would be useful for you now?

I wish I had learned to work with different kinds of personalities and temperaments earlier in my career. Technology is full of interesting personalities, and leading a team of brilliant introverts and extroverts all together is a serious balancing act. I feel like now I can work with just about anyone, and I’ve realized that just because someone doesn’t have the same depth of knowledge as I do in a certain topic, that doesn’t make them slow. Usually, they’re a genius somewhere else, and that’s usually an area that I don’t know at all. When I was young, I would get very impatient with people if I had to explain things to them more than once. Now I realize that it’s my job to put things in their frame of reference, not drag them into mine.

7 | Do you recommend any resources and tools for young entrepreneurs to use and gain valuable information from?

Medium is full of great articles written by experts on just about every topic. That’s often where I go to learn about general business or technical topics, and I find that there are usually plenty of references to help you go deeper if you want. The best resource, though, is other people who’ve been there before. Figure out what you need to learn and find someone who does it well, then ask them to share their own experience and resources. Most people are happy to help if someone asks; the problem is that people are afraid to ask.

I also like to read history books to get a larger perspective on trends in society and the world at large. It’s easy to get wrapped up in current events or technologies and think that no one has ever seen these kinds of problems before. When you expand your time horizon to centuries instead of months, you realize that everything moves in cycles. The specifics of the current problem might be different, but the general pattern tends to be the same. When I’m feeling overwhelmed by work, it’s very comforting to know that people have faced far bigger challenges than this and prevailed.

For further information on Da Primus | Da Primus website

Jason Cole on Twitter | Twitter

Follow his Medium account for compelling works regarding entrepreneurship | Medium