Tech.co logo

Better with Age: Chicago’s Top Ten Startup Founders over 40

August 8, 2016

3:00 pm

The startup world is filled with stereotypes. Whether it’s the casual dress or the unique office perks, every founder knows that people expect them to run their company in a particular way. But what if the stereotype pertains to founders themselves? It’s no secret that when people picture a startup founder, hoodies and flip-flops undoubtedly come to mind. However, the startup landscape is far from littered with twenty-somethings. In fact, some of the most successful founders are middle aged. And whether it’s because of wisdom or experience, we like it that way.

Plus, the data backs us up. The average age of the successful startup founder is around 40 years old, according to the Kauffman Foundation, and the only age group with an increase in entrepreneurial activity over the last twenty years are those between 55 and 65.

Chicago is home to a huge number of these successful founders over 40. From health care gurus to pet industry dynamos, this city has no shortage of talent when it comes to the later years of entrepreneurship. And with a rich history of successful startups, from GrubHub to Groupon, there’s no telling how high these startup founders over 40 will be able to fly in the Windy City.


Star Cunningham is the founder and CEO of 4D Healthware. She is on pace to become the 13th African-American woman to raise more than $1 million after having completed a $710,000 seed round earlier this year. Her startup helps patients and doctors coordinate care for chronic diseases with a platform that incorporates data from hundreds of different wearable devices, like fitness trackers and Bluetooth-enabled glucometers. Star Cunningham has been dealing with multiple chronic illnesses since she was a child. It was her own frustration with the healthcare system’s inability to appropriately diagnose, treat and coordinate her care that led to the creation of this enterprise. Star’s vision is an inspirations to solve this monumental problem.


Jamie Migdal has founded FetchFind along with four other successful pet industry startups. Specifically, FetchFind helps interested parties find jobs within the pet community. Not only is Jamie connecting a previously unconnected and fundamental industry, Jamie is an exceptionally giving mentor and teacher who always has time for the people she encounters, which are many. She is universally respected and well liked. Tech savvy people and other start up CEO’s rarely have time for the human aspect. And the pet world is filled with many who are good with pets but not people. Somehow, Jamie is not only able to create and grow an unimaginably necessary and previously absent tech business, but she helms it with selfless leadership -sharing her expertise, speaking engagements and mentoring – not just other pet professionals but other women run businesses. All as she is learning and evolving constantly. Her passion for people, as well as pets makes her an exceptional force and business leader.


Asif Khan is the founder and CEO of health tech startup, Caremerge, a Chicago-based, award-winning tech company revolutionizing care coordination and communication in the senior care space. Recently, Caremerge secured $14M in funding to better prepare post-acute care providers for the value-based care model by leveraging its transformative cross-enterprise workflow automation technology. Asif’s 20 years of experience in technology have led him to found Caremerge. Before serving as CEO, he spent eight years in various Senior and Global Product Marketing roles at GE Healthcare IT. During his tenure at GE, Asif worked as an entrepreneurial catalyst driving positive change across various businesses. Prior to his leaving GE Healthcare in late 2010 to start Caremerge, Asif was responsible for a portfolio of healthcare products generating $140 million annually with over 3000 clients, worldwide. He loves Chicago. He enjoys the river walk and all the well maintained and manicured parks like Millennium Park with a special nod to Pritzker Pavillion.


Helen Levinson founded Indigo Interactive in hopes of supporting the local tech scene through immersive internship programs. In addition to that, she has been providing clients with custom software development, workflow automation and user experience guidance for nearly two decades. She is a firm believer in empowering all employees to innovate and contribute to the advancement of business objectives through technology. Helen also takes great pride in working with nonprofits that encourage young girls to pursue careers in science, technology, engineering, and mathematics (STEM). She also supports young girls in STEM by volunteering as a Girl Scouts Troop Leader for her daughter’s troop. As a mother, Helen also enjoys collaborating and sharing advice with other entrepreneurial moms on how to strike a healthy balance between life and work.

Jay Edelson is the founder & CEO of 50-employee Chicago-based Edelson PC. Picture a stereotypical startup – workers scurrying about on hover boards throughout an open office, playing ping-pong, making music videos to team-build, playing around with the Oculus Rift, wearing flip-flops and short or jeans and hoodies as weather-appropriate, being entrepreneurial at every turn – and that’s Edelson. It just happens to be a law firm. Edelson’s a consumer class action firm focusing primarily on tech privacy issues, and it’s shaping the way privacy laws – many of them decades old – are being interpreted and implemented in the face of new and evolving technology. The firm has brought suits alleging privacy violations against most of the major tech companies in Silicon Valley (and elsewhere), and has recovered more than $1 billion for consumers.

Mike Justice launched Naperville-based Grid Connect in 2003. Initially, the company distributed networking products but, as engineering talent grew, they began to design and manufacture their own wireless smart sensors for the industrial market. Recognizing the growth IoT, in 2013 Grid Connect launched a series of smart sensor products designed for consumers using existing wifi in the home. These products were designed to measure changes in temperature, humidity, water, etc. and notify the homeowner by text. Based on this success, Grid Connect partnerd with Apple and the ConnectSense Smart Outlet is one of the first products to be built on the Apple HomeKit platform. You can control any traditional product plugged into a smart outlet using text or Siri. That’s right, now you can stay in bed when you need to turn off the lights, all thanks to Mike!

Michelle Smyth and Kristen Holman are cofounders of PayYourSelfie. These two childhood friends decided to leave their lucrative marketing and sales careers to start a selfie-app-that-pays. In less than a year, they have found themselves not only with more than 500,000 selfies uploaded to their app from their duck-pout users, but loads of Fortune 500 companies eager to see what these selfies ‘say’. Proctor and Gamble, InBev, Johnson & Johnson, just to name a few ask Pay Your Selfie to deliver consumer trends as seen through these selfies. Smyth was hit with the idea after Ellen took her infamous celebrity selfie at the Oscars a few years ago. “I thought, everyone should be paid for their selfies!” The two took a lot of risks going into business, but felt strong that they needed to do it. Both say if they didn’t do it now, they would have regretted it their entire lives. To boot, their entrepreneurial move shows their children that they can truly pursue anything if they have a passion (and a great partner!).

Julie Roth Novack is the mastermind behind the event-inspiration website PartySlate. An amateur event planner turned event-inspiration and tech guru. Julie also had a lucrative career in marketing, but her passion for throwing memorable parties made her leave it all behind. Julie is partnering up with the country’s best event professionals to show off the best, most memorable, and most gorgeous parties. “Think of it as Houzz for party hosts,” says Julie. “When it comes to throwing a wedding, a gala or even a 50th b-day party, there wasn’t ONE site that helps you find JUST event ideas.” PartySlate currently has over 30,000 high-resolution event photos uploaded (only since May, mind you) and hundreds of top-tier event professionals from the famous Debi Lily to venues like the Ritz-Carlton. Julie has helped plan more than 50 parties herself, and always help hopeless when searching online for new, innovative party ideas. She created a site she personally would use to help her throw the best events — and she’s sharing it with the rest of us party hosts that could desperately use the help.

Sridhar (Sri) Deivasigamani is the founder of Intellihot. Sri didn’t set out to create the first on-demand hot water heater. But, after returning home from a 30-hour flight only to find his basement completely flooded from a broken water heater, he knew a worthy challenge when he saw it. After mopping up the basement, the robotics engineer immediately started troubleshooting his water heater. By sunrise, he had the idea for what would become the first on-demand, tankless water heater. Today, Intellihot boasts several large-scale clients including Levi’s® Stadium, home of the San Francisco 49ers, 340 on the Park, Chicago’s second tallest residential building, and Hilton Hotels. The success of Intellihot continues to flourish, with revenue growing in excess of 100 percent year-over-year. The company now employs 50 people in both Galesburg and Peoria, and continues to secure key partnerships nationwide. Recognized for its innovative and state-of-the art design and sustainability, Intellihot’s suite of 13 water heaters are the most efficient and sustainable choice for commercial properties who are looking to reduce carbon footprint and impact their bottom line. Intellihot heaters are the first to provide endless hot water only when needed, eliminating waste and environmental impact, cutting down greenhouse emissions by 37 percent. Unlike other tankless water heaters on the market, Intellihot water heaters scale to large commercial properties, saving 20 to 40 percent on energy bills.

Adam Robinson is the founder of Hireology. Robinson turned 40 this past June. He is truly passionate about mentoring others and being vocal about issues impacting Hireology and its customers. As CEO of Hireology, Robinson has led the company to year-over-year growth, driving a 140% increase in revenue in 2015 and bringing its total customer count up to 3,000-plus clients this year. Hireology is breaking new ground and moving the HR/tech industry forward with its user-centric approach to hiring and selection. Adam is passionate about entrepreneurship, donating time to a number of organizations that support the entrepreneurial cause. Through multiple leadership roles at Entrepreneurs Organization, he has helped to develop and launch programs that teach core business skills to early-stage entrepreneurs around the world.

Photo: Flickr / Roman Boed

Did you like this article?

Get more delivered to your inbox just like it!

Sorry about that. Try these articles instead!

Conor is the Senior Writer for Tech.co. For the last four years, he’s written about everything from Kickstarter campaigns and budding startups to tech titans and innovative technologies. His extensive background in stand-up comedy made him the perfect person to host tech-centric events like Startup Night at SXSW and the Timmy Awards for Tech in Motion. You can email Conor at conor@tech.co.