How to quit your job to start an IT business: Advice from techpreneurs

Insureon Staff.
By Insureon Staff
April 28, 2016
We ask techpreneurs for advice regarding starting your own IT business.
A young man with glasses smiling at the camera.

Ready to make the big jump? Quitting your day job and starting your own IT business might be the hardest thing you do – but also the most rewarding, if the several techpreneurs we talked to are any indication.

Learn from those who’ve done it before and find out if you’re ready to make the leap of faith.

Tip 1: Transition when you have enough demand

For many entrepreneurs, a full-blown business doesn’t just come out of nowhere. Start working on the side, build up a client base, and quit your job when it looks sustainable.

Brandon Howardfounder of internet marketing and web design company , started out working full-time for a company that needed a lot of IT help and began getting referrals from other employees of the company for freelance work on the side.

“One day it clicked for me that I had so much demand that I could start my own business and go full-time with that instead,” Howard says.

Since then, he says, the demand just kept climbing to the point where he now has a team of 10 people – all from a humble freelancing beginning.

Brandon’s advice for techpreneurs: Get sales people and project managers that can speak in easy-to-understand terms for clients. “We've done that now, so clients feel more like they understand what's going on and that's been a huge help,” Howard says.

Tip 2: When the going gets tough, keep going and watch for risk

Sometimes business planning doesn’t go as smoothly as you might like.

Joshua Erdman was the IT department manager at a web development company when he decided to start a network administration business on the side. Erdman says his employer found out and he was quickly let go.

Erdman found himself unemployed, without the proper licensure to run his business, and without any training in running a business to begin with. On top of everything, his wife was pregnant.

So what happened next?

Erdman’s network administration business…

  • Went from two to 44 clients
  • Became one of the largest IT firms in the area
  • And was bought by a larger IT service provider after 11 years

He now works as a senior consultant for TekTegrity, which purchased his firm.

Joshua’s advice for techpreneurs: Often in IT, clients blame you for things you have no control over, Erdman says.

He describes an example where a client’s computer kept crashing, and they started to question his ability to run their network. Finally, he brought in a voltmeter, and found out that the client’s building had an electrical problem. The computer wasn’t getting the proper voltage.

In similar cases, an IT business might be wise to have errors and omissions insurance, which covers claims and lawsuits over professional work – whether the business is actually at fault or not.

Tip 3: Find a way to stay on track

Nicky LettiniCEO and founder of , a cost-allocation software company, says it always takes more money and more time than you anticipate to get up and running. “As you grow, you also need to be able to scale, and all of that takes funding,” she says.

Her company focuses on cost allocation, so it’s somewhat ironic, Lettini says, that the biggest hurdle she had to overcome in launching CostTree was ensuring she was adequately funded not just for operating today, but growth tomorrow.

Nicky’s advice for techpreneurs: “I was not experienced in starting a business, and certainly not a technology platform or company,” Lettini says. “So I hired a strategic planning consultant early on to help me stay on track.”

Tip 4: Don’t assume you can prepare for everything

Matt Dorman worked 18 years for other companies before becoming the founder of his own IT consulting firm, , with two partners last summer. He says he finally had enough confidence in his domain knowledge to make the leap, but uncertainty remained.

“My biggest fear was simply having to go back to a job after going out on my own,” Dorman says. But that soon changed. “As we started to grow the business and then hired employees, the fear quickly shifted to maintaining the company for them rather than just my ego getting hurt.”

Matt’s advice for techpreneurs: “There's really no amount of preparation one can do that can equate to the real experience of running the company,” Dorman says. “For me, the faster I got that experience the quicker I could adapt some of my original roadmaps.”

Tip 5: Look around – you might be ready right now

Fear, uncertainty, and hesitation might be present when you decide to quit and start an IT business your own, but don’t use them as an excuse to wait. You may be closer to an entrepreneurial opportunity than you realize.

Randy Downs describes how he worked on the side for a few previous employers while looking for a new full-time job. “When I interviewed at other companies, I mentioned my work on the side as my business and most were curious why I would want a job with an employer,” he says. “It was as though folks saw my business as real before I did.”

So Downs made it official and started , offering a wide range of IT services.

Randy’s advice for techpreneurs: Don’t wait. “The only thing I would do differently is start my business a few years earlier,” Downs says.

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