In 2023 I left my acquirer just two years into a three year contract – forfeiting millions.
Was it worth it?
First, a bit of context.
In 2021 my cofounder Nick Elledge and I sold DataFleets to LiveRamp for >$100mm. Within about a month of joining the acquirer, I realized the integration was going to be extremely difficult. Over the next two years, DataFleets relaunched within LiveRamp and found commercial success, but it was more painful than I had ever imagined. A portion of my compensation was paid out over a three year period, contingent on me staying with the company. But I left after two years – hence leaving a significant portion of it behind.
M&A integrations are hard. And of course, running a startup is also hard. But when running a startup you have complete control over (1) the people you hire, (2) the culture you build to glue those people into a team, and (3) the way you spend your time. When I was thrown into the world of M&A integration, I lost those three critical levers. I was unprepared for the challenge of integration, and though our integration fared better than most, it was taxing.
You may be thinking, "Boo hoo - you had an exit and the M&A integration was hard. Get over it."
I fully recognize the privilege I have and I'm grateful for the life changing outcome I experienced. Notwithstanding, walking away from a sizable portion of my compensation was a huge deal for me. It was compensation I felt I had earned through the risks I had taken, years of 80+ hour work weeks, and the value I created.
Ultimately, a combination of six factors motivated me to move on early.
👪 (1) Family
My wife and I were thrilled to welcome a baby boy to our family in 2022. Spending time with them is one of my greatest joys. But in corporate life, I felt my time with them was robbed. I had little control over my calendar at work, and despite being constantly busy we were moving a fraction of the pace I would find acceptable in a well functioning startup. I was sacrificing some of my most meaningful family moments on activities that were a poor use of time.
🧠 (2) Mental health
Though not diagnosed with it, I’m pretty sure I was depressed. I’m an inherently optimistic person. Even amidst 100 hour work weeks and near death experiences with DataFleets, I felt energized, driven, and optimistic. But my inherent optimism was waning. The vision I had for where our acquirer should go was different than where the company wanted to go, and watching the window of opportunity close for my vision to materialize made me frustrated, cynical, and irritable. No exaggeration – I felt like the worst version of myself I’ve ever been.
🚀 (3) Hunger for impact
About a year into our M&A integration I realized something: the thing I was most proud of in my career was not the company I had just sold. Instead, it was the work I had done at Digital Reasoning to get its healthcare vertical off the ground – which has since been spun out as Azra AI. That work helps save lives across the United States to this day, and though I aspired to multiply that level of impact with DataFleets, I had a greater commercial impact without the same level of societal impact. I had to try again.
⛏️ (4) I missed the grind
It seems counterintuitive– on the one hand, I wanted more time to spend with my family, but on the other hand I missed the “grind” of a startup. But for me, it’s not about the quantity of hours worked. It’s how those hours are spent and the flexibility of when those hours are worked that matter. Running a startup, I can aim to make a lasting impact on the world and bend consistent 60-80 hour work weeks around my family life ... e.g. making sure I’m there for bath + bed time before heading back to a long night of work.
🤝 (5) I missed setting the culture
If I were to summarize the type of culture I like to create, it’s one of deep thought, speed, peer-to-peer accountability, functional excellence, and ambition. Setting that culture has many levers: chief among them are hiring/firing, promotions, and intentional behaviors from leadership. There were cultural aspects of my acquirer I wanted to change, but changing such things from the middle of a company is a herculean task – and I failed.
🤖 (6) AI Opportunity
I first fell in love with AI while I was studying ancient greek in undergrad. I found myself spending more time learning computational linguistics to translate my homework than actually doing the work myself. Thereafter, I took a course on AI and felt for the first time I had found something I could spend my life working on. I read Russell and Norvig’s textbook cover-to-cover – I could hardly put it down. I subsequently spent the first half of my career researching, productizing, and selling deep learning solutions for analyzing unstructured data. I published on language models at ICML and productized them. The early days of DataFleets were all privacy-enhanced machine learning focused, but the market need was a privacy-enhanced SQL engine, so we pivoted to that instead. Then, when Stable Diffusion and ChatGPT were going viral in 2022, I felt like I was sitting on the sidelines as I watched AI take off.
❓Was it worth it ❓
Setting the foundation of a lifelong connection
Some dads speak of a near supernatural experience when their child is born – as if a bolt of lightning hits them and they immediately feel connected with their child. That was definitely not my experience. I felt a sense of duty to provide for my son, but I did not feel a sense of connection. He was like a little alien that pooped and cried. But now I feel deeply connected with my son – and I know he feels the same way towards me. That connection has taken a huge time investment to build, and I’m so proud and grateful that I was able to make that investment. What’s more, it’s allowed my wife and I to grow even closer after 8 years together. After I left, we traveled all across the US in our Airstream for two months straight – unplugged and spending time together as a family.
Finding fulfillment at work
It’s a challenge to have a toddler and start a company in a highly competitive market. Transitioning from a roadblock at work, to a meltdown at bath time, to a long night of more work is a grind. But having gone through the pain of a startup and the pain of an exit, I feel so lucky to be living through the former right now. I was speaking with my coach and advisor David Pann about how things are going. The best word I could find to describe it is “fulfilled”. It may sound cheesy, but since starting this next venture six months ago, I’ve reflected daily on the feeling of fulfillment I have and how grateful I am for it.
It’s not all gravy and roses. But the last few weeks in particular have been fulfilling and fun since we’ve transitioned our MVP to an alpha. Watching the uptick in companies using it over the past few weeks has been thrilling – and getting feedback on all the things users wished they could do feels like a mountain of (fulfilling) work …
Since launching our alpha, we've been pleased to see a number of companies start using it
The verdict
One year in, the decision to leave early and forfeit the money was one of the best I’ve made. The connection I’ve built with my son was well worth it in its own right. And the fulfillment I’ve found in jumping back into the unknown and aiming even higher with a new venture has been the icing on the cake.
If you’ve made it this far in the post – thanks for reading! And if you happen to be a data scientist (or any type of scientific professional), I'd love to chat! We're working on a product to help scientific professionals 10x their productivity.
Feel free to contact me directly or join our discord - we’d love your feedback!