My professional journey

In the summer of 2008 I met a man. We were both painting a fence at a local orphanage in Mexico. He was there in service of God. I was there because I needed something to do for the summer.

He'd been molested by a priest. I'd gotten my ass kicked at school.

He'd persisted through insurmountable adversity.

I'd become a rudderless teenager from a few punches in the face.

As we sat there painting the fence, he asked me why I'd drifted here, in this orphanage, painting the fence with him. I told him that I liked helping people and didn't have anything to do for the summer. I was there to scratch my own itch.

He then asked me what I wanted to do when I grew up. I'd spent the last 3 years of my life avoiding the harassment at school in any way I could and numbing my shitty teenage years with drugs and parties. My GPA was a disaster. I hadn't given what I wanted to do much thought but options were limited for a student with a sub 2.5 GPA.

If the man painting the fence could continue to serve god after being molested by one of His trusted servants, I could get my shit together.

The Plan: Become a clinician

The next 4 years of my life were spent pursuing the singular goal of having an impact on people's lives. I oriented my academic career towards becoming a doctor. I built a school in Africa with the girlfriend that would eventually become my wife and mother of my children. I wrote an undergrad thesis, started a non-profit (where we'd get paid to strip on social media), did research in a bariatric surgery lab and surrounded myself with people I loved and respected.

But 4 years after painting the fence, meeting the man on a religious mission and deciding that I had to do something great with my life, my admission was denied to McGill's medical school.

I'd worked tirelessly for years to get to where I was and yet it wasn't enough.

But the man painting the fence had held onto his love of god even when god presented him what should have been an insurmountable obstacle. I'd decided to pursue medicine because I wanted to have an impact on people's lives. Some bureaucrat, signing a piece of paper, telling me no, wasn't going to get in the way of achieving my goals.

I was going to have an even bigger impact on people's lives than I could have as a clinician. I was going to do everything I could to stick it to this nameless bureaucrat.

Pivot 1: Healthcare Administration

I packed my bags and headed to Ithaca, NY where I'd pursue a healthcare administration degree. If I couldn't be a clinician working in the health system, I'd run the whole thing.

But the more I learned about how fucked up the American healthcare system was and still is, the more I realized that administrative skills weren't going to cut it.

In stark contrast with my Highschool years, I skipped the parties and social events to learn how to program, dabbling in mobile and web development. As I built up my engineering skills and learned more about the health care systems I felt the pull to start a company in the space.

TechCrunch clearly showed us that startups were the way to have a massive impact on the world. Musk was building rockets and electric cars. Bezos was revolutionizing retail. Zuck connected the world while Larry and Sergei organized the world's information. That seemed like a good way to stick it to the bureaucrat.

I explored building a credentialing service for healthcare professionals.

I explored building a service, à la Zocdoc or Healthgrades combined with WebMD, to help patients find the care they needed.

I even explored building a free electronic health record system.

After throwing enough noodles at the wall and realizing that none were sticking, I decided to take a more calculated approach. I was going to go work at a big company for the summer to learn more about the problems they were facing and I was going to focus on building my software engineering skills.

The internship

I eventually weaseled my way into a computer science degree at NYC's newest entrepreneurship focused school, Cornell Tech.

But before I joined the new program I did an internship on Merck's data science and insights team. I worked my ass off during that internship, sleeping under my desk to, in equal parts, try to impress my bosses and avoid my roommate's late night drum sessions in the cockroach infested apartment I'd rented for the summer.

That summer, my bosses epitomized corporate America. They were consensus builders and dreamers. Both had been presidential innovation fellows and knew how to politic their way through any situation.

One ate Thai food late night with me as I planned an all nighter to get something we had planned out the door quickly and the other would mute the multiple simultaneous meetings he was juggling on his desk phone and Webex to answer my barrage of questions. I drank from the firehose that summer and met people who would go on to have an incredible impact on my life.

That summer taught me two things that would go on to define the next five years of my life. The first was the realization that finding and accessing the data you need for any data driven project is incredibly painful in the enterprise setting.

The second came from meeting VCs and entrepreneurs trying to solve incredible problems at the intersection of medicine and pharmaceuticals... healthcare is FUCKING hard.

Summer had flown by, the internship was over and school was about to start.

Pivot 2: Engineering @ Cornell Tech

A couple days before school started I met up with two classmates at a brewery in Brooklyn.

We stood around a barrel sampling local brews. We nerded out so hard that I could barely follow the conversation. Both were incredible engineers.

One of them kept pulling my attention with his receding hairline, his leftover hair sticking out in every direction, his cargo shorts worn above the hip line and an undersized faded t-shirt sporting a tech company's logo. He knew his shit. I'd have to work a lifetime to achieve his level of engineering prowess.

If love at first sight could describe a working relationship, that's what I felt. But it wasn't reciprocated. On that day, I asked this classmate to found a company with me. He said no.

I'd been rejected once again.

As the program started we were encouraged to use what we were learning academically (I was studying deep learning) to solve problems we were familiar with and start companies to commercialize the innovation.

At Merck, I'd experienced the pain of finding and accessing data in the enterprise which made it a natural fit for me to solve.

The main players in this space were old school dinosaurs like Informatica and Teradata, companies that hadn't innovated since the 90s. There was something romantic about being David going up against dormant Goliath.

The start of my professional career came into focus. I'd build a company to challenge Informatica and I'd use everything I could learn about machine learning to make the experience of our users painless.

I'd dethrone this giant first and then find others to dethrone. I'd do all that while getting my graduate degree and ensuring I had a visa that enabled me to avoid deportation.

Datalogue

I'd been rejected by the first true super star engineer I'd met in my life.

I'd met someone else though that I'd love working with. We'd met during a hackathon the year prior to joining Cornell Tech, a hackathon that we ended up winning out of sheer obstinance and work ethic. We both shared a passion for hacking, drinking and opinionated conversations about technology.

If the experience I had with my classmate was unreciprocated love at first sight, this was more of a love each other the more we learn about each other kinda thing. The kind of love that leads to great, lasting marriages. Everyone around me kept telling me that co-founding a company was like getting married and everything about this relationship felt right.

The friend I'd met at this hackathon eventually quit a high paying job at Classpass to become my co-founder and create the David that would take on Goliath.

First order of business was to generate revenue because... you know... money makes the world go round and... we had no idea how to raise money. We bootstrapped the business by doing consulting for Fortune 500 businesses and using the revenue we generated to fund product development efforts.

We quickly spread ourselves thin and failed to generate enough margin to fund the product and kept falling into spending the majority of our time on consulting. The model didn't scale. We therefore decided to raise venture capital, starting with a small friends and family round, to focus our efforts on building product rather than consulting for customers.

After a rollercoaster fundraise we ended up closing a financing round from incredible investors and angels while I was a full-time student.

To this day, I have no idea what investors saw in me. I was a 25yr old building a competitor to one of the oldest enterprise software companies and I planned on attacking them on their turf by serving their existing customers better.

We eventually built a team, that super star engineer classmate that had turned me down eventually joined us as VP of Engineering. It took convincing my wife to moving in with him, another roommate and our dog while doing what I could to help with his other company and being ready to pounce with an offer if things didn't work out.

As we grew, we hired our friends, built teams in Montreal and NY. If there's a mistake to be made, we made it. But the obstinance that led to that hackathon win, paired with a relentless pursuit to learn, helped us win over customers and build a viable business.

5 yrs later, two product pivots, millions in revenue generated from Informatica customers, $18M in venture capital and dozens of jobs being created in the US and Canada, we sold Datalogue to Nike.

We failed to conquer our Goliath but in the process built an awesome team and burgeoning product that we eventually sold. Every investor that believed in us made a positive return. I'm incredibly proud of the fact that the person who saved the company from bankruptcy in its early days with a $15,000 check walked away with $300,000 in proceeds from the sale.

Nike

Today, we're coming up on 2 yrs after selling Datalogue to Nike.

The main thing I'm proud of as I look back at these past two years is the fact that the team that we brought into Nike shares my same relentless pursuit to have an impact. They've helped keep a critical, multi billion program on time with their work, they're part of building Nike's new .swoosh digital experience, they've introduced customer centricity to IT and they are helping Nike evolve Nike's internal product model as the company continues its multi-year digital transformation.

As for me, this experience has taught me incredible lessons. The first is that 29 yr olds are ill equipped for navigating big company politics. I made my share of mistakes putting my chips in the wrong baskets and believing that everyone wanted to affect the change that we were asked to bring into the organization.

I learned early on that I sucked as a teammate and an employee. I've since spent the vast majority of my time learning how to not suck and fixing the first impressions that I made.

There's nothing that I'd trade for these incredibly painful lessons. I've become a better leader and the experience has taught me several frameworks that I'll cary with me into the future.

Before Nike, I'd always sold products into large companies, I'd never bought them myself at any meaningful scale. I've since seen how large companies buy, at scale and at massive contract values, from inside the belly of the beast. I've seen the stakeholders on the inside that help get deals done and those that successfully block them. I've been coach, an economic buyer, a champion for our vendors, jargon that will be familiar to those of you in go-to-market roles.

As I look back on what generated shareholder value to Datalogue's investors, our ability to sell was up there as one of the most valuable attributes of the team we'd built. The things I've now learned at Nike can catalyze even better go-to-market strategies for up starts of my own or those that I advise.

There's a long tail of other important lessons like the "subtle sell", humorous swagger, executive presence and much more that I've learned from my boss, my peers and Nike's incredible executive team.

Looking ahead

On July 31st 2022, Noah, my sister's second kid was born. Forty eight hours later Noah was dead. Two days earlier my sister and her husband learned that their child had a severe brain anomaly. They were presented three choices: terminate the pregnancy in utero, bring the child to term letting him pass naturally or bring the child to term to live a life of suffering unable to eat, speak, move or breath unassisted.

They chose to bring the pregnancy to term and love baby Noah with everything they had and let him pass naturally, having lived a life of love, embraced by everyone in our family.

I watched my sister and her husband love their new baby with intensity and strength. I watched a staff of dedicated nurses and doctors craft a patient experience centered around love and compassion. We took turns holding baby Noah and gave him every ounce of love we could muster.

A few months later Sam, my baby girl, was born.

Losing Noah days after we got to meet him and welcoming Sam has lit a new fire in me. One that burns out of love and compassion instead of vindictiveness.

I don't need to stick it to the bureaucrat.

Instead, I want to continue my journey to have a massive impact on the world at large. I want to leave my dent in the universe. A dent that honors Noah's memory and makes my daughter proud.

As I look at the road ahead there are three main areas I'm going to focus on.

I'm going to start investing in companies looking to take on their own Goliaths and in companies building the tools that others need to take on their Goliaths. On one hand, I'll be investing in companies that go up against large, digitally stagnant incumbents that haven't delivered innovations for their customers and with the other I'll be investing in businesses that are building developer tooling, enterprise infrastructure, applied machine learning and analytics capabilities.

I'm going to patiently plan to take on my next Goliath. I'm honing in on food distribution as a space that I'd love to disrupt eventually disrupt but first I'm going to dive deep into why putting data intensive applications into production is still so hard. Sysco and US Foods, here I come but first, let me take on those big cloud providers.

I'm going to be building up a philanthropic fund to invest in healthcare institutions that provide the types of patient experiences that St Justine's Hospital provided to my sister and her husband. I'll be doing everything I can to make sure that I can write a $100M check in Noah's honor before I die.

All three of these goals will take decades to accomplish but you know...

Just do it, they say...