Most research on entrepreneurial failure focuses on the dramatic moments: the collapsed company, the shuttered doors. Andrew Bettinger is more interested in the Tuesday afternoon when a client walks away, a prototype fails or an investor pitch ends in silence.

“These are the setbacks where the firm isn’t failing, but they’re very discrete challenges,” says Bettinger, a Ph.D. student in entrepreneurship and emerging enterprises in the Whitman School of Management and a major in the United States Air Force.

If entrepreneurs don’t see those moments as something they can handle and bounce back from, the cumulative toll can drain their well-being over time, he hypothesizes.

Now, with support from the Institute for Veterans and Military Families (IVMF), he’s testing a way to help using AI.

A Daily Check-In, Powered by AI

Bettinger recently received approval from the University’s Institutional Review Board to launch his study, made possible by the Bernard D. and Louise C. Rostker IVMF Dissertation Research Fund. Participants will use a web-based chatbot, powered by Claude, for a brief daily check-in. They can identify the most stressful event of their day and talk it through. The chatbot, grounded in cognitive behavioral therapy, helps them name their thoughts, validates the emotions behind them, offers a small reframe of the setback and suggests one small coping step within their control before the next check-in.

A treatment group will use the chatbot with cognitive behavioral therapy while a control group uses a chatbot providing descriptive feedback, which will let Bettinger measure whether the daily practice improves entrepreneurs’ well-being.

Entrepreneurs are busy, and carving out time for therapy can be hard. Stigma can be an obstacle too, particularly for some veterans.

“We’re not trying to replace human interaction and replace therapists,” he says. “But we want to test whether a brief check-in could make a difference.”

If the approach works, he sees a low-cost, scalable tool that veteran-serving organizations, accelerators and incubators could adopt.

“This is a timely research project. The field has established that entrepreneurship can take a toll on the well-being of founders, but as researchers we don’t really know what we can do about it,” says Johan Wiklund, Distinguished Professor in Entrepreneurship and Al Berg Chair in the Whitman School, who is Bettinger’s mentor. “This project represents a first step in helping entrepreneurs improve their well-being.”

Built With Care and Concern

Bettinger is clear that this is not a clinical trial. Participants complete a screening questionnaire first, and anyone currently in mental health treatment is screened out so the study measures the chatbot’s effect, not the impact of existing treatment.

Safety is built in at multiple levels. If crisis-related language appears in a chat, resources such as the Veterans Crisis Line pop up immediately. An automated check after each session flags any subtle signs of distress or worrisome trends and the research team also reviews chat logs themselves.

“Testing the effectiveness of this AI-powered chatbot is important because it can offer time-constrained founders a quick and approachable tool that can make a difference,” Wiklund says. “It does not replace a therapist. But using the chatbot a few minutes a day, when the stress is occurring, should prove to be valuable.”

Participants sign up through a survey outside the web app, and inside it, the chats are anonymized. Data stays within the app and is not used to train models. Only in a crisis would the team link a chat back to a person.

Because of the IVMF’s mission, participants must be military-connected, which includes military spouses and family members. That opens a useful comparison: veterans navigating the shift out of uniform alongside spouses who aren’t making that transition and may more closely resemble the general entrepreneurial population.

Bettinger is currently recruiting entrepreneurs who are veterans, military spouses or otherwise military-connected, through IVMF channels and other veteran organizations. The first step is to fill out a short eligibility form.

Serving Through Research

Bettinger has 13 years of service in the Air Force. In his most recent role, he served as a senior instructor at the U.S. Air Force Academy near Colorado Springs, Colorado, teaching finance and directing advising for more than 500 cadets. He previously spent time working with startups and small businesses, which sparked his interest in entrepreneurship. The Air Force is sponsoring his Ph.D., and he’ll return to the academy to teach when he finishes.

It’s the same Air Force–sponsored path Chancellor J. Michael Haynie followed. When Bettinger was weighing Ph.D. programs, mutual contacts at the academy put him in touch with the Chancellor. A couple of summers ago, driving his family from Colorado to his hometown of Albany, New York, Bettinger asked if he could stop by Syracuse University for a visit. That visit ultimately convinced him to choose Whitman.

Why Well-Being Is Personal

Bettinger’s interest in resilience is not purely academic. He is the father of three young sons and his middle child, 6-year-old Brady, was born with a spinal tumor. The family learned of it just two days before his birth. As a newborn, Brady endured five rounds of chemotherapy and is paralyzed from the waist down. Brady’s rehabilitation began just as COVID-19 arrived.

What carried Bettinger and his wife through, he says, was a single question: what’s the next thing we can control? First, it was treatment, then rehab, then mobility. Today, Brady is a first-grade student who uses a wheelchair and, by his father’s account, doesn’t let anything slow him down. That principle, focusing on what’s within your control, is at the heart of the chatbot’s design.