Reflecting on an unusual year and looking ahead with excitement!

2020 was an unusual year, to put it mildly. It was a year of massive change to the way we live, work, and socialize. We had to contend with unnatural things like isolating from the people we love and staying in-doors for weeks and months on end just to survive. We took life and work to the digital realm and continue to do so to this day.

Through all of this crazy change, the team at UpKeep, where I head up Product and Engineering, managed to pull off a very impressive year. We delivered over 5,000 pieces of value to…

The Ultimate Tale of Cause and Effect

“People are rendered ferocious by misery; and misanthropy is ever the offspring of discontent.” — Mary Shelley

I struggled to formulate this review. There’s so many gems worth noting I simply didn’t know where to begin. To me, the myth of Frankenstein in pop culture has completely disfigured this deeply human story told by Mary Shelley.

For the longest time, I thought the name, “Frankenstein,” referred to the mute creature at the center of the story. I was wrong. For the longest time, I thought the creature was a primitive abomination deserving of its perilous fate. I was wrong. For…

Change is a Stranger That Never Ceases to Show

Five years ago, I wrote about the lessons I learned along the way to 40. Today, as I reflect on my 45th journey around the sun, I’m realizing that the past five years have taught me more about people, life, relationships, and myself, than all the previous 40 years combined.

A lot has happened over the past five years. I traveled the world many times over––from the leas of Scotland to the savannas of Africa to the glaciers of Iceland. …

A year ago, I joined UpKeep to help make the lives of the the underserved labor around the world better. Up to that point, I never really saw myself working at a B2B SaaS startup building maintenance and reliability software. Coming from Ticketmaster where I ran Consumer Products and Open Platform, this was a big change for me.

I took the job because I believed in the team, the mission, and the business. Also, taking on both Product and Engineering at a fast-growing B2B SaaS startup was an interesting challenge for me, both personally and professionally.

As I reflect on…

The crisis of character in a post-truth world

In the age of Trump, social media influencers, reality TV celebrities, and the success-at-all-cost mindset, the subject of character has become increasingly urgent. In his new book, Sailing True North, Admiral James G. Stavridis posits that we live in a time where character is dying a slow and painful death. Classic values––humility, honesty, commitment, resilience, accountability, moderation––are looked upon as mere suggestions, if not downright disparaged. In a world where privacy is dead, building character is a challenge:

“We have lost the ability to hone our character in private, and our lives are on display seemingly from the moment we…

Focusing on Customer Needs and Long-Term System Health

In 2019, UpKeep delivered over 2,397 pieces of value to our customers in the US, UK, Canada, China, Australia, South Africa, Germany, France, Kuwait, UAE, Japan, Iceland, Brazil, and beyond. We’ve seen our user base grow by +105% and engagement soar to an all-time high.

We provided our customers with everything from minor usability improvements to major features and security overhauls that have helped them do their work better and have the peace of mind they deserve, respectively.

Every single task our team worked on in 2019 either solved a customer pain point or delivered on a customer need. We…

Reviews of the best biographies, fiction, and non-fiction I read in 2019

I read a ton of great books in 2019, many of which were biographies for some reason. Looking back on the year, a few gems stood out to me. Here they are:

There’s an ancient parable about a farmer who lost his horse. That night, the neighbors gathered around to mourn his loss. “We cannot believe this. What a terrible thing to have happened to you,” they said. The farmer responded, “maybe.”

Days later, the farmer’s horse returned with seven wild horses in tow. Right away, the neighbors exclaimed, “what an unexpected good fortune!” The farmer shrugged, “maybe.”

The next day, the farmer’s son rode one of the wild horses, fell off and broke his legs. The neighbors cried, “what terrible fortune to land on your son!” The farmer replied, “maybe.”


Back in July, I closed my second chapter with Ticketmaster to join a startup called UpKeep. Here’s why I believe this is one of the best career moves I’ve ever made, and why I couldn’t be more excited to be part of this amazing team!

What drew me to UpKeep were the following five distinct factors:

#1 The Purpose

At UpKeep, we believe in making the lives of the underserved labor around the world better through technology. Now THAT’S a transcendent purpose and an admirable quest rife with possibilities. The way the company’s driving toward that purpose right now is by focusing on…

Today is my last day at Ticketmaster, closing my second tour of duty at the company. After four incredible years working with some of the best talent in the world, the time has come to start a new adventure.

I still remember my very first day at Ticketmaster like it was yesterday, and I leave today with a strong sense of gratitude and pride of everything the amazing team I leave behind has accomplished.

Together, we went on to accomplish many great things, not least of which is the team culture we created to value empathy and respect for each…

Ismail Elshareef

I think in stories, and sometimes I write them down.

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