Darrin Murriner and the trouble with playing it safe

Darrin Murriner’s first business had a clear exit strategy: buy a Nintendo. In fifth grade, he sold pen samples from his father’s specialty advertising business to classmates. A week’s proceeds covered the original Nintendo Entertainment System. For an enterprise with a school-age proprietor, that was a satisfying return. The customer was nearby, the inventory was available, and success came with controllers.

Then came the sensible career. Murriner went into audit, a profession whose relationship with excitement is usually adversarial. He moved through risk, finance and operations, accumulating the experience that would eventually make him a technology founder with an unusual preoccupation: the damage people do to a business when they become too concerned with protecting themselves.

Today he is co-founder and CEO of Cloverleaf, which brings coaching into the calendars, inboxes and messaging tools people use at work. The journey between those two businesses, pens and people, involved a collapsed employer, an earlier venture that required different expectations, and a former colleague who initially declined his invitation to start a company.

01 A respectable career, with questions attached

The conventional route had appealed to him. He earned good grades, went to college and expected a long tenure with an employer, followed by retirement. About four years into professional life, that picture began to feel unsatisfying. Reading Jim Collins’s Good to Great helped change the way he thought about what he might build himself.

His education crossed business and technology. He studied at the University of Kentucky, then completed a weekend MBA at the University of Cincinnati between 2002 and 2004, concentrating on international finance. Work and study overlapped. The foundation of his later company would include a fairly thorough acquaintance with the machinery of established organizations.

That machinery could fail spectacularly. At Arthur Andersen, Murriner experienced the firm’s collapse following the Enron scandal. He has described the experience as an early lesson in integrity, leadership and culture. He went on to work at Fifth Third Bank and in the insurance business, including the Munich Re group. His corporate career lasted roughly 15 years.

Risk management gives a person reasons to be careful. Murriner became interested in what happens when caution spreads into decisions about everything else. A workplace can become very accomplished at avoiding embarrassment while making it difficult for anyone to try something useful. His later writing kept returning to the opportunities that disappear under those conditions.

02 An ambition with room to change

Before Cloverleaf, there was BabysitEase. Murriner and his wife Peggy started an online service connecting parents with childcare providers. It was a practical business rooted in family life, rather than an abstraction discovered on a whiteboard. It also taught him that an enterprise and its founder’s original ambition can turn out to be different sizes.

He had imagined a venture-backed company. As the business developed, he came to see that it suited a lifestyle business better. Accepting that meant changing the picture he had carried of its future. There is a particular difficulty in revising an ambition when the underlying work still has value. The business does not have to vanish for the expectation to go.

That experience gives some substance to his later interest in self-awareness. A founder has to distinguish what the work needs from what he wants it to prove about him. The same question can sit inside a much larger corporation: is this decision serving the organization, or preserving someone’s preferred version of events?

In 2015, he published Corporate Bravery: Eliminate Fear-Based Decision Making. Its subject grew out of the corporate behavior he had observed. He was also writing publicly about leadership, trust and workplace culture. The former auditor was developing an argument for giving people more room to act.

“We really want to change how the world works.”

Darrin Murriner

03 A brewery, a rejection, a better question

At Epipheo, a Cincinnati video company, Murriner had worked with people who would become Cloverleaf’s founders. They had seen teams produce very different results and wanted to understand why. The work was collaborative; the quality of the collaboration varied. That was a problem they could recognize before they knew exactly what to sell.

In 2015, Kirsten Moorefield ran into Murriner at a former colleague’s leaving party at Rhinegeist Brewery. He invited her to join the business he was starting. She initially said no. After thinking about it for a couple of weeks, she joined him. A useful partnership began with enough independence for one person to decline the pitch.

Their first application to OCEAN Accelerator was rejected. Feedback and potential-customer interviews followed. The early product had been conceived around recruiting, helping people find a company where they could fit. The conversations pointed toward another use: helping people who already worked together understand their teams.

There was no instant reward for this discovery. Moorefield recalled a rough early product, built by an overseas developer, that crashed and sometimes produced Ukrainian error pages. People nevertheless began paying for it. The founders applied to OCEAN again and were accepted. Fundraising then stretched from April 2017 into February 2018. The product had found interest; building a sustainable company still required a long stretch of work.

These stages explain why a founder’s beginning rarely fits tidily into one date. An idea, a working product and a full-time job can arrive in different years. For Murriner, the interval contained something valuable: repeated opportunities to learn that people wanted a different version of what he had first proposed.

04 The report in the back seat

Cloverleaf’s premise becomes easier to understand when you picture the aftermath of a workplace assessment. Someone learns something interesting about a strength or communication preference. Then ordinary work resumes. The report has to compete with meetings, messages and everything due by the end of the week.

Murriner has written about the “backseat effect”: detailed assessment reports being set aside before their insights become part of daily behavior. His interest is in the small prompt that arrives when a person can use it. A reminder before a conversation has a different job from a lengthy explanation delivered weeks earlier.

The company uses behavioral assessments as a starting point and brings guidance into tools including email, calendars, Slack and Microsoft Teams. The intended beneficiary extends beyond the executive who can arrange regular coaching. Murriner wants development to be available across a team, in the midst of its actual work.

The appeal is quite ordinary. Consider two colleagues who interpret questions differently: one hears an invitation to examine an idea, the other hears a challenge. Guidance that helps them recognize the difference has a practical purpose. It might give the next exchange a better chance. The usefulness depends on whether someone acts on the observation.

05 Taking his own advice

A coaching company gives its founders plenty of opportunities to be examined by their own principles. Murriner has discussed making a deliberate effort to talk less and listen more. In conversations with Moorefield, he has explored the difficulty of leading without having every answer. Leaving room for another person’s contribution can require the leader to stop demonstrating how helpful he is.

He has also acknowledged a specific commercial weakness: pricing. His inclination to give things away can make him too ready to offer a discount. Naming the tendency gives colleagues something concrete to work around. It is a more useful admission than a general declaration that everyone has room to grow.

The writing continued alongside the business. In 2024, Murriner, Moorefield and Cloverleaf chief research officer Scott Dust co-authored Thrive: A Collaboration Manifesto. The book brought their shared focus on working relationships into a longer form. Murriner’s first book had examined fear in organizations; the later one explored the collective work people can do together.

There were business milestones, too. Cloverleaf announced a $7.3 million Series A extension in 2024. That June, the company said it had made Inc.’s Best Workplaces list for a second consecutive year. For a business selling help with teamwork, its own workplace belongs in the conversation.

06 What the machine needs to know

By February 2026, Murriner was writing about how buyers should evaluate AI for leadership development. His framework centered on three kinds of context: behavioral assessment data, the organization’s own leadership expectations, and information about roles and teams from its people systems. He wanted buyers to ask what an AI actually knows about the people it is advising.

The question follows the same concern that runs through his earlier career. General advice becomes more useful when it meets a particular person and a particular decision. His argument asks buyers to look beyond a pleasant conversation with software and examine the information that makes its guidance relevant.

Murriner has described his approach to persistence with a modest phrase: “we just keep hitting the nail”. It suits a career made through repeated adjustments rather than one immaculate plan. The fifth grader had a week, some pens and a game console in mind. The adult has taken on a slower transaction: helping people understand one another well enough to do their work together.