chicago

(269)
Legend
Aji Abraham's case for keeping the day job
Founder · Engineer · Operator

Aji Abraham's case for keeping the day job

A decade at Motorola helped Aji Abraham learn how to build. With Armia and CodeVentures, he has made a business of helping other founders begin before they have a technical team of their own.

aji-abraham · armia-systemsRead →
Legend
David Schreiber and the People Behind the Numbers
Founder · Executive · Operator

David Schreiber and the People Behind the Numbers

He co-founded Compass Health Center with a team of 11. As the organization spreads across states, David A. Schreiber’s story keeps returning to partnership, parenthood, and the people behind the numbers.

david-schreiber · david-a-schreiberRead →
Legend
Catherine Kleinmuntz and the business of what happens next
Founder · Investor · Operator

Catherine Kleinmuntz and the business of what happens next

She started Strata Decision Technology in a Champaign basement and led it for 15 years. Her next chapter asks how other people’s ideas make it out into the world.

catherine-kleinmuntz · strata-decision-technologyRead →
Legend
Tony Svanascini and the business of changing your business
Founder · Operator · Executive

Tony Svanascini and the business of changing your business

A fax-machine repair call is an unlikely starting point for a digital agency story. For Tony Svanascini, it helps explain three decades of following customers into whatever comes next.

tony-svanascini · americaneagle-comRead →
Legend
Don Kleinmuntz and the problem of putting good ideas to work
Founder · Investor · Operator

Don Kleinmuntz and the problem of putting good ideas to work

From a Champaign basement to the business analytics classroom, Don N. Kleinmuntz has kept returning to one question: how do you turn a sound analysis into a decision someone can use?

don-kleinmuntz · strata-decision-technologyRead →
Legend
Tony Olson and the secret life of a shopping basket
Founder · Executive · Operator

Tony Olson and the secret life of a shopping basket

He spent more than two decades helping brands understand what people buy. Now the former SPINS CEO is backing businesses built around what customers remember.

tony-olson · spinsRead →
Legend
Jared Golden’s bet on the shop next door
Founder · Operator · Investor

Jared Golden’s bet on the shop next door

Before Leap, Jared Golden helped community groups find sponsors. Then he and longtime business partner Amish Tolia took on a different matchmaking problem: getting brands from a website to a working store.

jared-golden · leapRead →
Legend
Dhruv Saxena and the business at the back of the queue
Founder · Executive · Operator

Dhruv Saxena and the business at the back of the queue

A photo-mailing side project kept sending Dhruv Saxena to the post office. The people waiting beside him helped reveal the business that became ShipBob.

dhruv-saxena · shipbobRead →
Legend
Wendell Jisa and the lesson in the rearview mirror
Founder · Executive · Operator

Wendell Jisa and the lesson in the rearview mirror

His first job involved delivering legal copies. His father’s gift was a warning to watch who was catching up. After building Reveal through years of acquisitions, Wendell Jisa is choosing a different seat.

wendell-jisa · revealRead →
Legend
Edward V. Szofer and the value of saying no
Founder · Operator · Executive

Edward V. Szofer and the value of saying no

From Chicago’s West Side to teams across the U.S. and India, SenecaGlobal’s co-founder has built a career around a practical conviction: good software starts with people who can listen, question and take responsibility.

edward-v-szofer · ed-szoferRead →
Legend
Matt Maloney and the trouble with getting dinner
Founder · Engineer · Executive

Matt Maloney and the trouble with getting dinner

An apartment-search programmer helped put takeout online. Two decades after co-founding Grubhub, Matt Maloney is back with familiar colleagues, applying lessons from dinner delivery to drivers waiting for roadside help.

matt-maloney · grubhubRead →
Legend
Frank Gaspari and the business of starting over
Founder · Executive · Operator

Frank Gaspari and the business of starting over

He sold two Chicago businesses, moved to Arizona, and built FlexPrint around the work that happens after a printer is sold. At FlexTG, Frank Gaspari has kept returning to the same question: what needs to change next?

frank-gaspari · flextgRead →
Company
Conversant and the art of remembering you
Enterprise · Media · Ecommerce

Conversant and the art of remembering you

One shopper. Several screens. A very expensive case of mistaken identity. Conversant built its advertising business around joining the dots - and making the resulting sales count.

adtech · personalized-advertisingRead →
Company
PriceLabs knows every night is different
Saas · Ai · Enterprise

PriceLabs knows every night is different

A rental calendar looks like a row of identical boxes. PriceLabs built a business around the money lost when hosts treat them that way.

dynamic-pricing · revenue-managementRead →
Company
Aim starts with the empty appointment.
Saas · Health · Ai

Aim starts with the empty appointment.

A $500-a-month virtual marketing associate, a calendar with room to fill, and a doctor who only has to say yes. Inside Aim’s 2021 proposal to make healthcare marketing a smaller job.

healthcare-marketing · social-media-automationRead →
Company
Vitality Group makes healthy habits pay
Health · Enterprise · Saas

Vitality Group makes healthy habits pay

A walk, a screening, a smaller bill. Vitality connects everyday health decisions to immediate rewards - and is building a business around what happens next.

behavior-change · employee-wellnessRead →
Company
Plan B® finds the buyer before it buys the ad.
Enterprise · Media

Plan B® finds the buyer before it buys the ad.

A kitchen designer. A supercar dealer. A family choosing care. This Chicago agency builds campaigns around the people who can actually move a decision.

advertising-agency · marketing-agencyRead →
Company
Attain keeps the receipts.
Enterprise · Saas · Media

Attain keeps the receipts.

A cash-advance app became the foundation of a purchase-data business. Now Attain wants advertisers to follow the sale all the way back to the ad.

purchase-data · advertising-measurementRead →
Legend
Andy Rubenstein and the business of being nearby
Founder · Operator · Executive

Andy Rubenstein and the business of being nearby

A liquor retailer saw an opening in Illinois gaming. Seventeen years after founding Accel Entertainment, Andy Rubenstein has handed over the CEO job - with a national business built around the neighborhood.

andy-rubenstein · andrew-rubensteinRead →
Legend
John Holmes and the two-year job that kept going
Executive · Operator

John Holmes and the two-year job that kept going

He arrived at AAR to work on acquisitions and expected to stay two years. A quarter-century later, John Holmes is reshaping the aviation services company around parts, repairs, and software - with a few DJ sets along the way.

john-holmes · john-m-holmesRead →
Legend
Jesse Singh and the second life of ordinary things
Executive · Operator

Jesse Singh and the second life of ordinary things

At AZEK, Jesse Singh pushed to turn more discarded plastic into decking. Now the Fortune Brands Innovations CEO is bringing a career spent between factories and familiar brands to the doors, taps and locks of everyday life.

jesse-singh · fortune-brands-innovationsRead →
Legend
Timothy Fitzgerald and the art of a smaller kitchen
Executive · Operator

Timothy Fitzgerald and the art of a smaller kitchen

He helped assemble Middleby through decades of acquisitions. Now Timothy Fitzgerald is reshaping the company he helped build, with a familiar conviction: the people and the kitchen have to work together.

timothy-fitzgerald · tim-fitzgeraldRead →
Legend
Dan Zortman and the business of staying close
Executive · Operator

Dan Zortman and the business of staying close

After 24 years at Roche, Dan Zortman took the top job at Sysmex America. His next chapter connects expansion across the Americas with a closer look at the people who make a company work.

dan-zortman · sysmex-americaRead →
Legend
Aaron Erter and the distance between a wall and a deck
Executive · Operator

Aaron Erter and the distance between a wall and a deck

After a career in tools, paint and manufacturing, Aaron Erter brought siding and decking under one roof. Now the James Hardie CEO has to turn an acquisition into something that works for the people building the house.

aaron-erter · james-hardieRead →
Company
Huron makes the complicated work.
Enterprise · Health · Education

Huron makes the complicated work.

Hospitals and universities run on systems few people see. Huron has built a business fixing the machinery behind the mission.

management-consulting · healthcare-consultingRead →
Legend
Doug Waggoner and the eight-minute experiment
Executive · Operator · Founder

Doug Waggoner and the eight-minute experiment

Echo’s CEO has spent four decades bringing software into the freight business. An eight-minute coding experiment offers a window into what still keeps him curious.

doug-waggoner · echo-global-logisticsRead →
Legend
Gary Bhojwani and the business of small promises
Executive · Operator · Founder

Gary Bhojwani and the business of small promises

He left engineering without a grand plan, built an insurance business, and eventually took charge of CNO Financial Group. His case for growth begins with the Americans who have little room for financial mistakes.

gary-bhojwani · cno-financial-groupRead →
Legend
Mark Hussey and the arithmetic of belonging
Executive · Operator

Mark Hussey and the arithmetic of belonging

Huron’s CEO learned business through balance sheets, retail technology and years in operations. His case for growth keeps coming back to the people who do the work.

mark-hussey · huronRead →
Legend
Tim Drehkoff and the business of staying longer
Executive · Operator

Tim Drehkoff and the business of staying longer

Before he became Rush Street Gaming’s CEO, Tim Drehkoff spent a decade as its CFO. His next chapter stretches from a former Philadelphia power station to an eight-story hotel taking shape in Portsmouth.

tim-drehkoff · rush-street-gamingRead →
Legend
Susan Flinn Cobian and the case for a smaller room
Founder · Executive · Operator

Susan Flinn Cobian and the case for a smaller room

Susan Flinn Cobian built SFC Group around close client relationships and a team that could work from anywhere. Her career offers a practical argument for fewer layers, clearer ownership, and paying attention long after a pitch ends.

susan-flinn-cobian · sfc-groupRead →