Reflections on the Job Hunt and Beginning a New Chapter at Greenfly

There’s something fun about uncertainty. Not knowing what’s next. It allows one to imagine the best of potential realities, believing every day and every small step is closer to some dream being realized.

That was the mindset I took after my last job – which I enjoyed and grew in – ended with the startup company not making it further after a full lifecycle during my four-plus years there. There was nothing but uncertainty ahead. After a trip to Europe – not exactly self-discovery, but a good chance to get away – the journey began.

This is more about moving on to the next chapter in my career, so I’ll keep this short. But first, some of the key life lessons from a path that I traveled over the last months, which included times of unbridled enthusiasm, impostor syndrome, bouncing back enough to consider going out on my own, getting close on really good jobs, getting ignored by other jobs, being ballsy and bold enough to turn down opportunities, reaching intermittent nadirs of despondency, trying to find small wins every day, and all while approaching every day and every interaction with the continued belief that you’re doing the right thing and that nothing can affect Fate more than the actions you take today.

The lessons:

  • Set goals every day. Set thoughtful goals. Have purposeful goals. And be rigorous in setting aside time to accomplish those goals
  • Make your own breaks – fill in the skill gaps for the next job you want, study your industry top-to-bottom because you have time others don’t, give value to others, and, ultimately, be intentionally present
  • Talk to others. Man, there are a handful of people that let me bounce ideas off them, celebrate the good times, talk through the not-so-good times, and seemed to pop in the texts or DM’s right when you need them. Really cool
  • Know what you value – Maybe I’m in the minority, but my jobs and my passions over the years have tended to intersect. It makes getting excited and energized about it easy. But working in and around sports or social is never something to be taken for granted. It requires understanding where money, lifestyle, job function, industry, and location come into play for one’s priorities and life


In the end, it was a combination of Fate and proactivity that led me to Greenfly. A quick story — I always knew of Greenfly, but then I saw an NBA team tweeting to their fans to download the Greenfly app and share content to the team. It was a use of their app that I hadn’t seen before and was introducing a new form of fan activation. So I reached out for a podcast interview and got to meet and interview the founders. And, yadda yadda yadda, I learned more about the company and got excited about what they do and where they are going, learned how I could be a fit to join, and here we are. It feels right.


I can remember just coming up in this sports and social media world, the first times I timidly interacted with players in the room. Eventually, they figured out and came to (sorta) appreciate what I did — helping to tell and share their stories to fans on Facebook, Twitter, Instagram, the website, and other platforms. I used to show them how popular some of the posts featuring them were or told them about how they’re resonating with fans. I’d grab them for quick interviews or ‘reads’, knowing every minute talking to the camera was another minute they couldn’t, well, go home or hit the showers or do anything else but sit in there with me. And the only way to really communicate with them about content was [except for the very rare DM] through PR or Team Ops, who had their ear for requests and needs.

This was early days for player social media, few were active on social and those that were didn’t put too much strategy into it. Now, players are building their brands on social media. They appreciate, especially the non-superstars, the power that content featuring them wields when it’s shared on social to drive fan awareness of them, fans following them, and fans becoming fans of them as individuals. 

So to learn not just about the utility of Greenfly, but also how it’s actually used and how players seem to truly appreciate the value to them was cool and inspiring. The teams/leagues have incredibly talented and creative social / digital / production teams, and an enormous and growing bank of photos and highlights that the players want to get at easily. And the teams want these players [who play the actual games] to amass huge fan bases, who will ultimately buy more merch, go to more games, watch more games and highlights, and talk more about the team on and off social media. Mutual need and mutual benefits. That sounds like a relationship.

And that’s one reason I’m excited about Greenfly – it’s collaboration. It’s collaboration with everyone — players, staff, talent, and even fans or fan ambassadors in sports; in other industries, it’s employees, actors, artists, advocates, customers, and influencers. Content is king and collaboration is how the best kingdoms continue to grow and reign.

Finally, as someone who geeks out about this sports and social space – and how it functions – I’m constantly interested in processes and operations (I ask a lot about that on my podcast interviews). And, while a decade ago social and digital media may have been seen as a side department run by the youngest staffers, it’s now a very sophisticated, multi-faceted, strategic operation. During each season [or even single game/event], there are thousands upon thousands of potential highlights, photos, GIFs being created one click and snap at a time. There are template and graphics, there are personalized GIFs or graphics for players, there are brand guidelines to maintain across accounts, there are tons of short-term and long-term projects to track and balance and prioritize, and there is a staff and brand to manage. And, there is a dizzying collection of software and hardware the team is using every day to make it all happen.

Tired yet? That’s why Greenfly’s approach is so important – the company appreciates how these teams function and designs the product and processes and organization and integrations to help them execute and measure what they do better, faster, more efficiently, and more effectively. Everyone is trying to play Moneyball, to do it better and do it smarter. 

I’m psyched to hopefully inspire digital and social marketers — but, really, anyone trying to activate on social themselves or with their own army – through sharing awesome examples, giving out smart and actionable tips, uncovering insights from studying the incredible customers using this product, and helping brands, businesses, teams, and organizations continue to cultivate and mobilize their own content community. The platforms and how content is consumed will change, but the power of good content, a good story, and an engaged, attentive, invested audience — those things transcend technology and time.

It would be cliche to say I wouldn’t trade the experience of the last several months, since every experience shapes you and everything, err, ‘happens for a reason.’ But I do feel good about the lessons learned and I actually do believe I ended up in the right spot for me. It doesn’t feel like I’m convincing myself, I’m convicted. It feels right and I hope anyone else going through a similar experience can end in such a good place. I look forward to continuing to exercise my passion for this space and learning from the community. The next chapter starts now and there’s nothing but energizing uncertainty ahead.

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