The decision to leave your startup is never easy.
When I made the decision to leave the company I co-founded, I had spent eight years, along with my business partners, turning our company and flagship property Swagbucks.com, into a loyalty and rewards powerhouse. When our story began we were a couple guys bootstrapping a business on the top floor of a community center and when I left we were well over 100 employees, posting over $50 million dollars in revenue annually and consistently recognized as one of the best places in Los Angeles to work.
Things at Swagbucks were awesome but when I began to feel the itch to get back to the lean start up days I knew it was my time to leave. After speaking with other entrepreneurs who had been in similar positions, I learned my reasons for stepping aside were pretty common.
1. The A-Team is in place
The most exciting times on an entrepreneurial journey are the earliest days in which being a generalist -- someone who is competent in multiple specialties -- is not only encouraged within the framework of a startup, it is required. Without the contribution of every individual filling in gaps where needed, and on the fly, no startup can succeed.
My partners and I thrived in this environment and had tremendous success. We were also smart enough to know that in order to compound success we’d need to surround ourselves with specialists with deep expertise. Over the course of several years we filled in personnel gaps until the current CEO helped us narrowly focus our needs and recruited some of the best and brightest leaders in Los Angeles.
In time, the reins to teams I created and oversaw were transitioned to new leaders who had their own vision, and rightfully needed the space to run free with that vision. It’s easier to let go when you have belief and trust in your teammates, and this transition where the startup team is augmented by seasoned specialists is part of the natural order of scaling.
As an entrepreneur, however, it’s in our nature to want to keep active in all aspects of the business and get your hands dirty anywhere you see an opportunity to lift some weight. At a certain point though this not only becomes difficult, but also counter-productive toward building the strong culture and relationships that any founder wants to instill within their organization. And why fight it anyway? If you have the right people, doing the right job, taking the business in the right direction, then you’re doing the right thing.
The Swagbucks ship has a new captain -- one who is very capable of steering her to even better horizons.
2. Yearning for those break-neck startup days
I’ve never met an entrepreneur whose quest to turn ideas into action didn’t motivate him or her through the ups and downs of startup life. The early days of a startup consist of throwing a lot of ideas against the wall, quickly examining the results, pressing forward with what sticks and repeating this process. There is never a shortage of ideas, only a shortage of resources.
Before we arrived at the current iteration of our flagship product, Swagbucks.com, we had spent more than two years building and pivoting incessantly. Whether it was smarts, scrappiness or the need to survive, we developed and executed at break-neck pace. In those days, failure was a lesson and the bounce back was simply to learn and apply more elbow grease.
Today, Swagbucks hasn’t lost its agile business and technical abilities, but it is certainly beyond the startup phase. The company has more than 100 employees and serves more than 12 million members. Swagbucks leadership is now more measured and focused with decisions.
As an entrepreneur who lives to turn ideas into action, I longed, deep down, for the days in which we launched a product we only just brainstormed the night before.
3. A need to start giving back
Before Swagbucks, my first company was a social venture that utilized musicians to fundraise for non-profits. I always admired the people I worked with -- many of whom were sitting atop the highest levels of the music industry -- and how they found time and creative ways to help others. I had always hoped that one day I would be in a position where my experience, connections or time can have either a social or business impact.
The Swagbucks story is one that is steeped in giving back. Throughout the history of the organization we maintained a strong focus on doing good business by doing good. I was always proud of the collective good we as a team were able to accomplish, and through the success of Swagbucks -- along with the rise of the so-called Silicon Beach scene in Los Angeles – I found myself in a position where my experience, connections and time could make a material impact socially and in business.
And since I left Swagbucks I’ve been doing just this: Spending much of my time advising entrepreneurs. Yes, I will launch another startup, someday. Perhaps with an entrepreneur I mentor and brainstorm with. For now, though, doing what I can to help the Los Angeles start up scene thrive feels like the natural place on my journey.