Former Windstream CFO: The Task You Won't Delegate Is The One Slowing Your Company Down | Brent Whittington
By Griffin Blackmon
March 4, 2026
Interview with Brent Whittington
Brent Whittington was CFO and then COO of Windstream before moving into agriculture. He now runs Acrelabs from Steamboat Springs, Colorado. He grew up in Little Rock and studied accounting at UALR. His approach is pragmatic: protect the downside, grow at a pace the business can sustain, and ask more questions than feel comfortable.
Draft built from the interview notes. Answers are summarized and are not direct quotes.
Do not be afraid to fail. Build a strong network early and ask more questions.
Brent Whittington · Advice to his high school self
What was your biggest failure or mistake in your career, and what did you learn from it?
Holding On Too Long
Early on, Whittington mismanaged operational scaling. He kept too much on his own plate and did not delegate tasks soon enough. Growth stalled on his desk until he let go of work that other people could do.
What non-academic skills mattered most?
Effective communication, resilience, work ethic, and adaptability.
How does he stay sharp and relevant?
Industry seminars, agricultural publications, and continuous peer networking.
What problem is he working on now?
Unpredictable weather and fluctuating market prices, the two forces in agriculture nobody controls.
What I Learned from Brent Whittington
Griffin writes this section in his own words after each interview.
The Whittington Framework
- 01
Mitigate the Downside First
Every plan starts with what happens if it goes wrong.
- 02
Grow at a Sustainable Pace
He chooses steady growth over aggressive expansion.
- 03
Delegate Early
The task you hold onto is the one that slows the company down.
Playbook Success Interview Profile
- Interviewee
- Brent Whittington
- Date of Interview
- March 4, 2026
- Primary Industry
- Agribusiness
- Based in
- Steamboat Springs, CO
- Born in
- Little Rock, AR
- Education
- UALR, accounting
- Business
- Acrelabs
- Biggest Career Lesson
- Early on, Whittington mismanaged operational scaling. He kept too much on his own plate and did not delegate tasks soon enough. Growth stalled on his desk until he let go of work that other people could do.
- Advice for Young Entrepreneurs
- Do not be afraid to fail. Build a strong network early and ask more questions.
Griffin Blackmon
Hi, I’m Griffin. I’m a student entrepreneur and the host of Playbook Success. I interview successful entrepreneurs and millionaires, so you don’t have to. During the interviews, I distill their biggest wins and hardest lessons into the “entrepreneurial intel” we need to build our futures today. Join me as I decode what it actually takes to win in business before graduation. Check out the Playbook Success Blog for more interviews and entrepreneurial tips to help you turn your hobby into an empire. Thanks again for reading!