Entrepreneurs, Is It Time for You to Resign?

After 13 years as CEO, I’m no longer running my company

Earlier this year, I made a big decision. After 13 years at the helm, I chose to step down as CEO from the company I founded. My entrepreneurial friends saw this as a benchmark moment — the end game! Passive income has arrived! But here’s the truth: the needs of our business were no longer my areas of strength.


“We bootstrapped to nearly $10M in annual revenue.”

Brothers Mark (left) and Brian Roland (right), 6x INC 5000 Entrepreneurs of Abenity.com


Our Story

You see, in 2006 my brother and I founded our business with a social mission and a radical remote team model that we bootstrapped to millions of members and nearly $10M in annual revenue.


Our first customers included the U.S. Army, Oracle, and The Walt Disney Company. It was a lot easier in those days to get a SAAS product in the door with these big name companies, and there was a lot of momentum to leverage. My brother and I like to say that I was always the “idea guy” and he, as a software developer and graphic designer, would shape my crazy vision into reality.

I had a new “big idea” every 15 months or so, and while my brother was developing these ideas, I’d launch the sales, marketing, and support infrastructure required to sustain them. This rhythm produced a fast-paced and creative culture within our budding start-up where there was always something new to celebrate. This was a fun season for our business, but the demands of our continuous growth began to constrain our ability to innovate.


Understanding The Business Lifecycle

Entrepreneurship is a roller coaster, and my entrepreneurial journey has been no exception. Without fail, a “win” in one area of the business is met by an obstacle in another area (tax requirements, compliance obligations, customer expectations, process limitations, etc.). At a certain point, I no longer had the time or energy to be creative, build strategic partnerships, or even connect personally with my team. I was stuck in a cycle of managing and maintaining.

An Entrepreneur.com article on the 5 Stages of Your Business Lifecycle outlines the hidden complexity that I didn’t realize we were up against.

Stage 1: Seed & Development Stage 2: Startup Stage 3: Growth & Establishment Stage 4: Expansion Stage 5: Maturity and Possible Exit

In hindsight, we learned to thrive in Stages 1–4 and, when the business was ready for Maturity (Stage 5), I wasn’t. As a result, I unintentionally ignored our need for Stage 5 leadership and plunged us into the pursuit of my next big idea.

In 2016, we made our first big mistake. We pursued an idea that didn’t fit squarely within our brand. If we had already implemented Stage 5 leadership for our company, I think we could’ve pulled this new idea off. However, we decided to split my focus and develop a new product, with a new team, under a new brand.


Unlike previous creative cycles, within 24 months our team was less motivated and our vision was less clear. Our team was more fragmented and our resources were more divided. Our newest brand was at odds with our original company and I was burned out. Without clear vision, we lost focus on why we started Abenity in the first place, and it felt like we were on a 20-mile march to nowhere.


Recognizing Our Need for New Leadership

It was time for us to reset our goals and focus our resources on the areas of the business that mattered most to our customers. It was time to invest more in professional development, expand our infrastructure, increase internal accountability, and audit our processes. With this new perspective, it became clear that my entrepreneurial leadership style was no longer connecting with the needs of our team. Instead of regular check-ins, our team was asking for performance reviews. Our vision-driven meetings now required an agenda. Our diverse geographic footprint demanded state-specific policies and our insurance providers wanted to see an official employee handbook.

In short, we made it! We beat the odds that many companies don’t. We were no longer a budding, bootstrapping, entrepreneurial organization. We were mature.


While this may sound like a dream come true to some of you, the following words literally make me cringe… schedules, insurance, accountability, audit, compliance, demands, handbook, performance reviews, and policies.


In an honest moment, I realized that I was no longer the kind of leader we needed. I was holding us back. It was time for a new CEO.

It was time for me to resign. And I did.

Today, I carry the title “Founder” and I’m focusing my time and energy on the creative aspects of the business that I love. I work full time and I’m still 50% owner of our businesses. My relationship with my brother / business partner is healthy and I’m more involved in social entrepreneurship than I’ve been in five years. I’m happy, but in a surprise turn of events, I’m no longer running my company after 13 years as CEO.

This photo features a few Abenity team members at a recent get together in Brentwood, TN.


Let’s Talk! I have two questions for you...

Your company’s needs probably aren’t that different from mine. Ideally, your mission, vision, and values remain the same, but growth requires change. 1) What would it look like for you to examine your company’s current needs? 2) Are you willing to look yourself in the mirror and answer honestly, “Am I still the leader my company needs?”


About the Author: Brian Roland is a social entrepreneur and Founder of Abenity, the 6x Inc. 5000 company that’s powering corporate perks for top brands like U.S. Bank and Mastercard. While Abenity provides millions of subscribers with private discounts, the company’s social mission is fighting extreme poverty with every program they deliver. Abenity recently exceeded $1 million dollars of total giving and hired a CEO to accelerate growth with their fully remote team. Brian lives in Scottsdale, Arizona with his family and enjoys roasting coffee, flying drones, and helping impact-driven entrepreneurs establish a social mission of their own.