Penn Little

Earn the trust of your team.”


Penn Little is a living testament to the power of financial smarts, feverish drive, and second chances.

Today, Little is a thriving, 33-year-old entrepreneur. He helped lead finance and clinical operations for Peak Consulting Partners, a management-consulting firm for behavioral and mental health care providers, which enjoyed 400 percent growth before merging last September with another company. He simultaneously co-founded Crestview Capital Partners, whose rapid growth and scaling returned more than 40 times his investment when the team exited the business earlier this year.

And now, with Bar Nothin’ Capital, Little’s commitment to the health sector is leading his unprecedented effort to reform the effectiveness and practices of one of America’s most vital industries: the exploding sector of treatment for substance abuse and other behavioral health disorders. He believes strategic finance and private wealth can finally produce the quality necessary to break the stigma in mental health care.

A third-generation entrepreneur, Little draws from his passion for finance and leadership, devotion to helping people, and the lessons of painful experience.

Nearly a decade ago, succumbing to alcoholism, addiction to cocaine, and compulsive gambling, Little passed fraudulent checks. He was caught, sought treatment, cooperated fully with authorities, pled guilty to one count of bank fraud, served 14 months and emerged determined to make the most of his new start**.

Little turned that experience into a positive and is driven every day to use his business skills to make sure facilities can provide good, quality behavioral health care to everyone who needs it. He knows the business from the inside and outside, and from the clinical and finance perspectives. Little wants to use strategic finance and operations to change people’s lives.

Little completed a long-term regimen of treatment at Hazelden, Prescott House, and the Federal RDAP program. Once complete, management at Prescott House, one of the most respected recovery programs in the United States, saw Little’s potential and hired him to learn every aspect of the behavioral health treatment industry. Little rose to Director of Business Development/Admissions for Prescott House, and worked there even while earning his MBA in Finance at the University of Arizona’s Eller College of Management in 2014.

During graduate school, Little joined Peak Consulting Partners as a consultant in every aspect of operations. He assisted dozens of providers in building programs with an equal emphasis on clinical care for patients and a deft understanding of the industry’s rapidly – and uniquely — changing financial landscape. The Mental Health Parity and Addiction Equity Act (often called “Parity”) required insurance companies to provide the same level of benefits for mental-health treatment and addiction services as they do for more traditional medical care; with the subsequent Affordable Care Act, this treatment suddenly became accessible to everyone. Little became an expert in the market for care, insurance pay and trends, and the role of Private Equity, while also performing market research for notable public consulting firms.

Little invested his life savings to co-found Crestview Capital Partners, LLC and was integral in directing its spectacular growth over two years. He led community-based counseling centers through the complexities of the changing industry landscape. This involved due-diligence, physical operations on site, and strategic development of Crestview’s buy/sell side. In that time, he was the CEO of KP Counseling, building a more robust team, and making Illinois his new home. The impact expanded the quality of care from 1 to 7 sites in the midwest.


A native of Carter County, Okla., Little attended Culver Military Academy before graduating from the University of Oklahoma with a BA, in Economics. An avid triathlete and Ironman finisher, he co-founded Shatter Our Silence, a program that provides education and tools to help young adults have intimate conversations about depression and suicide. Now living in Chicago, Illinois, Little supports growth in young leaders with financial need through his work with the Culver Educational Foundation, and in 2017 funded the Wilkinson-Dorrel Scholarship at the University of Oklahoma Foundation. Penn also has over 500 hours of aviation expertise, as a Private Pilot.

Where did the idea for Bar Nothin’ Capital come from?

The long term vision – Deana Wilson and I crafted it over the time we knew and worked as peers in different organizations. The short term vision, a bailout to save mental healthcare — on my couch in a rabbit hole on August 19, 2017. I became Mike Burry 2.0.

What does your typical day look like and how do you make it productive?

I get up at about 6:30am, go to boxing class on the days they offer it, punch the crap out of anything I can prior to quiet morning briefing. I avoid the office until about 10:30 to have peace and quiet. I go at 10:30am, then leave generally between 9pm and 11pm. I am completely immersed each day, when starting a new venture, you must be, or you will lose.

How do you bring ideas to life?

I visualize them and play the tape out to others.

What’s one trend that excites you?

Impact Investing.

What is one habit of yours that makes you more productive as an entrepreneur?

I don’t quit. I finish.

What advice would you give your younger self?

None, if I had taken any other path, I would not have been here.

Tell us something that’s true that almost nobody agrees with you on.

I don’t forget anything I ate for lunch on any day.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Thank those who got you here.

What is one strategy that has helped you grow your business?

Earning trust of your team.

What is one failure you had as an entrepreneur, and how did you overcome it?

My first acquisition, I botched the transition big-time, had to pivot, and re-energize and garner trust. With new teams, trust comes first. I just rolled up the sleeves and focused on being a part of the team, the family. It was night and day difference a year later.

What is one business idea that you’re willing to give away to our readers?

A drill bit that can puncture granite. Trust me.

What is the best $100 you recently spent? What and why?

Oh, $100 of the $400 for that flu fighting IV.

What is one piece of software or a web service that helps you be productive? How do you use it?

Evernote – I use it for everything, lists are amazing.

What is the one book that you recommend our community should read and why?

Unbroken. Laura Hillenbrand. It will teach you to never give up.

What is your favorite quote?

“Confidence is the Invisible Cement that binds a team together.” – Bud Wilkinson –

Key Learnings:

  • I learned I’m resilient
  • I learned that my girlfriend is right, I’m stubborn
  • I care about others so much, it’s amazing I’m just like my mentor.

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