Remembering a Founder and Friend

January 5, 2021 Edwin Watkeys

In Loving Memory of Edwin Watkeys— artist, philosopher, founder, and friend of Hire an Esquire

Like many in our network and across the globe, the Hire an Esquire team experienced the upheaval of 2020 in many and varied forms. There was adjusting to work from home schedules coupled with closed daycares and schools, the tolls on our minds and bodies from isolation, uncertainty, and spending too much time in front of screens and not enough time out in the world. Amongst our own core team there were personal COVID diagnosis, COVID diagnosis of immediate family, relatives, and friends... and then there was loss.

And 2020 ended with one final sucker punch. We lost one of our original founders, Edwin Watkeys. Edwin saw the potential for Hire an Esquire and helped me to convince other key people that this idea was worth taking seriously. Hire an Esquire would not be here without Edwin, and he remained an advocate and supporter of Hire an Esquire.

It’s impossible to capture anyone, let alone someone as dynamic as Edwin, in a movie or novel, let alone a simple blog post. So many of us are different things to different people just as different people, situations, and times of our life bring out different elements of who we are. No one can capture the fluidity and depth of another human being and all that is appropriate for me to attempt to draw for our Hire an Esquire audience is a line drawing; a limited and flat perspective that captures the most basic essence of who Edwin was and how that impacted the product that so many of you use every day.

Edwin and Hire an Esquire’s Founding Story

The concept of Hire an Esquire first came to me in mid-2009, but the roots began in Philadelphia in the summer of 2008 when Edwin ended up at the small scrunched table next to me at a coffee shop and struck up a conversation. An hour later I knew I had a new friend. I was not unique, Edwin met and befriended random people everywhere—at coffee shops, quizzo (oh- the aughts!), when they were unlocking a bike that caught his eye... you get the point. When he moved to New York in 2012 I teased him it was because he couldn’t have coffee in peace anywhere in Philadelphia.

Edwin was a lightning ball of brilliant and creative energy. A true artist and product manager, he couldn’t help but get to the root of how things worked, the structures that made them that way, and simple but overlooked or ingenious ways to make things better. His energy was contagious and during and after talking to him about something he was excited about, you’d feel like you’d downed 5 shots of espresso.

As the idea of Hire an Esquire continued to haunt me and I became more compelled that it was worth building, Edwin was the first person I brought the idea to. Edwin’s eyes lit up as he immediately saw the potential and began talking a mile a minute. This would be the first of many conversations that would further refine and define the concept of Hire an Esquire. And as valuable and as defining as these conversations were to Hire an Esquire, Edwin’s role would go far beyond them.

Edwin began racking up his first tech experience in high school and like so many others of the first tech wave, dropped out of college to work at a startup. Edwin’s bets and uncanny intuition paid off. He would begin his stream of early successes while his peers were in college (and I was in middle school) as product manager at Infonautics before moving on to Senior Product Manager of CDNow, and then head of product for through the company’s launch and acquisition by eBay... to name a few of his early career feats. When I met Edwin, he had founded Transmogrify—a design and branding firm he had built to try something new after his multiple successes and time on the startup treadmill. It too was now also successful with multiple employees, partners, and marquee clients and he was in the process of selling it.

Edwin opened his network and credibility to my idea even though, or perhaps because, I was fairly fresh out of law school at the time. Edwin believed with a couple of years experience working as a lawyer my eyes were now focused but still fresh and not yet accepting of the problems in the industry. He felt that habitually dealing with suboptimal situations for too long made it “like a hideous table or couch you stop seeing in your apartment.”

Cobblestone Street in Old City

A side cobblestone street in Old City, a Philadelphia neighborhood were Edwin was an unofficial mayor and artist-in-residence

He rightly identified and arranged a meeting (in yet another coffee shop) with the perfect technical cofounder, Dave Martorana, in late 2009. As usual, his intuition was on point, Dave was looking for a side project and saw freelancing as the future. Shortly after a meeting Edwin arranged where I showed up with a business plan, Dave signed on and by 2010 we were blueprinting the software after work and on weekends. By 2011 we would launch our initial product while still at our day jobs.

Support through the Muddled Middle

Since Hire an Esquire is a network of entrepreneurs whether as freelance legal professionals or law firm founders, our audience probably understands how the idea stage of building a business can be as magical as the actual execution is murderous.

The planning stage of a business, before it gets real and your bills and career depend on it, is like being on vacation in a delightful city, or the beginning of a new year. It’s a fresh canvas that’s new and full of possibilities where your brain selectively forgets that the same problems and realities will follow you into this new reality you imagine in a new year, city, or career.

Hire an Esquire’s beginnings were particularly magical. I met and worked with amazing people thanks to the talent and community centered in Philadelphia’s Old City neighborhood. Within this enclave, pieces seemed to flow together. Still, things got very real in 2012 when we had a basic product, a strong supply of lawyers, and a small number of clients. We were now fully understanding how stubborn the legal industry was to change. To make Hire an Esquire a viable business, it needed to be more than the side project of a small team of people. I quit my law firm job to pound the pavement full-time for Hire an Esquire.

Like for many entrepreneurs, there was rejection everywhere. I cold-called small law firms, learned DIY email marketing, snuck into/ talked my way through security in buildings in Philadelphia packed with small law practices to hand out glossy one-pagers and explain the business, met with any law firm partner who would agree to a meeting, and made a big (and worthwhile) investment in sales training from my quickly dwindling savings. There was progress but it was excruciatingly slow. I was grateful for the middle-class privilege that allowed me to get as far as I did as an entrepreneur—a sister and brother-in-law who let me crash in their 750 square foot condo to further stretch my 6 months of savings and my parents who promised that my childhood bedroom was always available. Still, moving back to my childhood bedroom or continuing to wear out my welcome in a small apartment was not my dream for the future. Most told me to give up, that the legal industry was too resistant to change. Many backed away as they could no longer relate to me or my lifestyle.

After leaving my job, it would be 2 grueling years of working without a salary as I closed our first major AMLaw clients and a more recent cofounder and I got our first term sheet and small round of funding that would jumpstart the business, dramatically increase our revenue and show that Hire an Esquire had potential once again. Edwin was there through all of it.

Having moved to New York in 2012, Edwin not only kept believing but doubled down as New York became my part-time home as the early stages of fundraising and meetings at major law firms began. My then home of Philadelphia was no place for success with such things—but it was a quick train ride to New York which was. Edwin offered up one of the regular couches I would crash on in New York and gave me free rein and the keys to his apartment during his frequent travels. He was a true artist and talented photographer and his various apartments—usually in one of the villages, sometimes in Brooklyn—were always filled with beautiful photography and a great fiction collection which, like everything else, he was generous with. I would escape by viewing Edwin’s latest photography or combing through his book collection. I still have a small stack of books yet to be returned that were borrowed from his library and finished on planes and trains.

Edwin and Moko Founder Monique Mason

Edwin with his friend and Moko Founder Monique Mason (center), at the eco beauty hotspot’s opening, in Old City Philadelphia. Edwin had designed the logo and all branding for Moko

But more than a place to crash with welcomed distractions during the toughest years, Edwin offered unfailing moral support and care to confront the challenges head on and to keep Hire an Esquire going when everything seemed bleak and impossible. We traded stories from our days out and about in New York at the end of the day or in the morning over the perfectly poached eggs and grits that Edwin was a master at preparing, Edwin would be more indignant than I was about the legal industry’s resistance to change and the sexism I faced while fundraising—which he observed and acknowledged first hand when attending fundraising meetings with me and reading follow up emails. He never gaslit me about these experiences and acknowledged the additional challenges women and minorities faced in tech without seeing this as an affront or discounting his own achievements.

Not (and Anything but) Another Privileged Tech Bro

Edwin Photography

Edwin was not that brand of white man (that I’ve met too often) who has had some success in the tech world and is smug to outwardly arrogant about this success. This type of man initially seems forward-thinking and data-driven... until data shows he may have an advantage through his gender, race, and economic status. Then they transform from worshipping aggregated data into anecdote machines, countering hard data with stories of women or men who weren’t from affluence who achieved success, of women who said their gender gave them advantage in tech and/or raised massive rounds of funding. Their underlying tone and implication is that women and/or minorities have some kind of affirmative action advantage and the struggles they face as a group are because they are doing something wrong or just can’t cut it. If you’re straight with them about how you’re really doing or share your own experience authentically, you will be tone policed and will have to hear a soliloquy about how they actually had it harder. You realize behind their cool, relaxed, and friendly tech façade, they’re part of the problem. You stop bothering with them and stop getting angry as you realize that with their limited perspective and limited lives, they don’t have the capacity to understand the perspectives of other people or the world outside their little bubble. Edwin was the complete opposite.

Edwin grew up with a front-row seat to the grind of his parents sustaining a small family business. We joked that “lifestyle business” (an au courant term of the 2010s that became an umbrella term to describe any small business) meant that you gave your life to a business just to survive and get by. This and other formative life experiences expanded Edwin’s compassion far beyond small business owners and entrepreneurs.

Edwin was one of the only people I knew who hadn’t worked in food service, but who was a hopeless over-tipper. And while my other friends and I who logged our time in food service were generous tippers, Edwin regularly tipped as much (or more) than his bill. And Edwin’s excessive tipping says a lot about who he was.

Despite his successes, he never developed that Silicon Valley-Tech sort of Libertarianism that so many of his peers evangelized. A philosophy that their place and success was the rightful order of things, achieved solely because they had done some hard work (who hasn’t?) and that others who hadn’t achieved their level of economic stability just hadn’t worked hard enough or weren’t quite good enough. In contrast, Edwin was actively disgusted by this perspective. A philosophy major, he noted the irony of these tech-Libertarians who fancied themselves such independent thinkers and “disruptors” of (corporate) structures while subscribing to the oldest tropes and structures of Predestination and Karma. Edwin believed that rather than championing self-determination and merit, such conventions were designed to force people to accept their destiny and not question wealth and other inequalities.

Edwin never stopped questioning these (and all types of) structures and respecting people generally and seeing the importance and humanity of their jobs. Where other tech bros saw how service jobs and the people who performed them could be turned into robots and revenue per user, he recognized how the food server, the bartender, the delivery person, and the owner of the small corner business were not just people, but vital to the fabric of a community and how they dispensed everyday humanity.

This great empathy and intuition that exceeded his life experience was part of his genius for designing products beyond the general anemic tech bro repertoire of “gimme” products, that largely helped the affluent get things faster and easier whether it was food, a date, a new apartment, a cab, things from a vending machine, etc. And his convictions and our philosophical alignment on these things also helped and supported designing Hire an Esquire as it was.

In the 2010s, investors were enamored with the Ubers and Grubhubs of the world. They did not like Hire an Esquire’s structure that classified our workers as employees, provided full health insurance and professional liability insurance. They would say “this is all too complicated” and suggest that we go for a more “lightweight’ structure” like other gig platforms that put the expenses and risk on the contractors.

From our initial conversations designing and conceptualizing Hire an Esquire through building it, our goals had been to make sure that contract and freelance lawyers were treated like humans, not cattle, had autonomy and more than the bare-bones health insurance benefits offered by staffing agencies that all but ensured bankruptcy from a serious injury and illness thanks to their low “lifetime” maximums. Neither of us saw the point in dedicating time or energy to another exploitative gig platform or staffing agency that looked right through attorneys and saw them as widgets.

As we struggled to fundraise with many other strikes against us and keep a compliance heavy business running with few resources, others around me suggested that perhaps I should consider this advice and try to add in more benefits and support for our contractors when the company was bigger and had more leverage and success. This is probably why I so fondly remember how relieving and refreshing one particular walk through Union Square in New York was after a meeting where an investor had dispensed similar advice; Edwin serenaded me with one of his signature expletive-laden monologues about how wrong this was.

Unfinished Business and Non-Definitive Endings

Edwin at L’Express

Edwin at L’Express one of our favorite Union Square spots reviewing a Hire an Esquire pitch deck

Edwin thought that Americans were set up for failure by always chasing happiness and some imagined, perpetual joyful high. This was not only unsustainable, he would tell me, but set us up for constant disappointment. The best we could strive for was contentment.

Edwin was there for that too.

Of course, there continued to be regular ups and downs. Edwin was the first to respond to investor updates almost instantaneously with words of encouragement when we had a not so great quarter and enthusiastic cheers for the good times.

I would continue to rely on his advice, perspective, his impeccable intuition and eye. His small tweaks where he often saw the obvious and simple that no one else did took things from blah- to wow. For instance when we had our first professional designer for Hire an Esquire’s branding, we all liked the logo and it meshed with the extensive branding exercises and review we had gone through. Still, it wasn’t wow-ing us and felt like it needed a tweak that we couldn’t put our finger on. I sent it to Edwin and within an hour he sent it back, slightly tilted and showing motion. Suddenly everyone was in love with it.

Hire an Esquire first logo

The previous Hire an Esquire logo that Edwin tilted ever so slightly to perfection

As the company progressed and I moved to San Francisco and my quarterly New York trips warranted AirBnBs or last minute hotel deals, Edwin was the first person I booked for dinner. We were always the last ones to leave the restaurant and even then leaving only because we understood that we were holding up the restaurant team from closing up and going home.

I left our dinners with new insights and ideas for Hire an Esquire that helped to keep me energized, the product fresh as well and toplow through the inevitable mild hangover the next day (we learned early on it made sense to just buy the whole bottle of wine). We both dreamed of moving back to Philadelphia and the non-scalable businesses we wanted to start that emphasized and honored all of the greatest parts of Philadelphia.

Our last dinner together, in February 2020 in New York was so much like the others. We thought there would be another reunion the next quarter and so much time to continue to dream. Little did we know we wouldn’t be seeing each other again and that the world would shut down soon after.

The next month Edwin would contract a severe case of COVID. In our last exchange, he apologized that he wouldn’t be able to swing by San Francisco for a visit on his epic motorcycle ride to L.A. around Thanksgiving and told me about the lingering “long hauler effects” of COVID he was still experiencing.

Shortly after this, he would be returning from one of his regular motorcycle rides and collapse in front of his building before passing away from a heart attack. Connecting with Edwin’s many friends has been like a warm weighted blanket, especially being on another coast and not being able to attend any of the many outdoor memorials and gatherings that have sprung up in his honor in New York and Philadelphia. Together we’ve tried to make logic and sense of all of this, as humans often do, we’ve conjectured about the after-effects of COVID, told classic Edwin stories, and shared how much we will miss him. We’ve echoed what an honor and privilege it was to have Edwin in our lives and how our worlds will be paler and smaller without him.

While many in our network will never understand the man, the artist, the philosopher, empath, and legend that was Edwin Watkeys, I hope I have provided a small glimpse into who he was and how he impacted and formed Hire an Esquire for the better.