Several weeks ago, Cobblestone began the process of shutting down. I am beyond grateful to Jack, Jason, colleagues, investors, customers, friends, and everyone else who helped make the past year and a half possible.
While it certainly isn't the outcome anyone was hoping for, I truly believe this was the most productive time of my entire career. Cobblestone pushed me well beyond my previous limits in technical excellence, stress management, balancing personal relationships with work, pure hustle, and more.
I constantly reflect on outcomes in my life to extract as much learning as possible, and Cobblestone is no exception. While I am writing this for my future self more than anything, if you are reading this I hope you find it helpful as well. Many of these learnings are most relevant to someone starting a company or working at an early stage startup, but they should be applicable to anyone looking to perform at their highest level in their personal and professional life.
The good
There are a ton of things to celebrate about Cobblestone. These are a few that I am especially proud of.
Best in class products
We built some truly novel technology at Cobblestone.
Our income verification was the best on the market. No other product could accurately detect pre tax income from low and high earners, and simultaneously support enough verification methods that 100% of users were expected to verify the authenticity of their claimed income. This took months of learning about new user personas, income types, verification methods, and more while quickly implementing new features based on these learnings.
We built the most advanced PMS (property management system) integration in prop tech. In order for a tenant screening platform to be truly end to end, we needed to sync all of Cobblestone's data back into our customers' PMS of choice. Many 3rd party PMS integrations are limited by incomplete public APIs. Cobblestone built PMS integrations that went beyond what official public APIs could support (ask me more about this after I've had a couple of beers 🙃).
Shipped at light speed
My previous job was at a top tier series B startup that shipped at 1/10 the speed of Cobblestone. Before joining Cobblestone, I knew that building in the pre revenue phase requires a higher level of focus and intensity than the growth stage. However, living in the early stages opened my eyes to a speed of execution that I never had imagined.
A great example of this is the number of times we SSH'd in to prod to fix bugs by directly updating our database. The first time I witnessed this happen I was in disbelief. At WorkOS or any other company I have worked at there would've been a highly regulated process of writing and reviewing a script to modify any production data. That is not a luxury we could afford though when we were putting out several fires per day during some of our early go lives.
In many ways this is by design: after all, WorkOS has more to lose than Cobblestone by making a mistake. When I start a company in the future, I plan to push the same (or hopefully even faster) velocity as we did at Cobblestone. While working in larger companies, I plan to flex my scrappiness tastefully by developing an understanding of when velocity can or cannot be increased.
Worked our butts off
I can say with confidence that this is the hardest I have worked in my professional life. We went to the office 6 day per week, Sunday through Friday.
Beyond consistently putting in more time than our peers, we also had many spikes of effort when it mattered the most.
We closed our first 6 figure ARR contract in part because I stayed up until 3 AM building new features for a demo. In our second call with the prospect, it was clear to us that they needed features to support a "centralized leasing" model. The call ended at around 5 PM, and they requested a demo for the next day at 10 AM, but we were missing features we claimed to have! I stayed in the office building this from 0 to demo ready for the next morning, and we eventually got an MSA signed.
That is just one example of our work ethic. The entire team spent many late nights crunching to push out critical features, putting out fires, and managing customer support.
Made life long friends
I spent many hours in the office with Jack and Jason (Ariel, Orestes, and Glenn too!), and am so grateful these incredible people are a part of my life.
We are all quite different, but I certainly feel that this is the most authentic version of myself I have ever shared with my colleagues. I hope to stay in touch with the entire Cobblestone team and cannot wait for the next opportunity to work with them again.
Beyond that, I am so grateful for the support from my network after Cobblestone shut down. Colleagues from Cobblestone and WorkOS, investors, friends, and more were immensely generous in making introductions and lending advice as I navigated where to go next. I was truly blown away by the opportunities I got to consider from startups, AI research labs, FAANG companies, VCs and more. None of that would have been possible without the network Cobblestone helped build.
Working this hard on meaningful problems, grabbing daily team lunches, and having real conversations about personal and professional life are not things you do with mere colleagues, it's something you do with amazing friends.
The bad
Obviously, Cobblestone did not have the level of success we were trying to achieve. There are many things I will likely do differently when I start a company in the future, but there are two that stand out to me.
Went to market too late
When Cobblestone shut down, we had between a quarter and half a million dollars in ARR. Not too bad for a 4 person team! However, this was across just a few customers since our business is fairly high ACV. Ultimately, we did not feel the pull of product market fit when we tried going to market more broadly.
Finding 5 customers that are willing to pay you a few hundred thousand dollars per year is not enough. We very likely could have continued selling Cobblestone and perhaps gotten to $10-20M ARR, but that is not a venture scale outcome either. For a venture scale B2B SaaS business, you are looking to get to a few hundred million dollars in ARR, if not more. That means if we say Cobblestone's ACV is $100k we need 1,000 customers to get to $100M in ARR (and ideally we get considerably further than that).
We built too close to our early design partners and developed for too small of a sample size of customers to effectively test product market fit. Once we tried to sell Cobblestone more broadly we realized that much of what we built was solving for a problem only in common between those few customers. Instead, we needed a product that created value for 1000s of real estate property managers and owners.
Startups that find really strong product market fit will ultimately feel the market pulling at them, the product should feel like it is selling itself. In our case we had to push Cobblestone to the market, and even then we still struggled to sell and deploy it at times.
In the future I would intentionally try selling an incomplete product to see how the market reacts, thus testing product market fit earlier. Customers with a really deep pain point are often willing to pay for a partial resolution. Furthermore, by shipping earlier we can increase from n=5 to ideally n=100 or more early customers so that we are testing our product's fit against a more representative sample of the market and learning about a more diverse range of customer profiles.
Did not celebrate enough
We had a lot of amazing wins at Cobblestone: signing our first customer, winning our first 6 figure contract, shipping hundreds of new features, and more. These wins should be celebrated regularly.
Working 6 days per week can either be a ton of fun or it can become a drag. At Cobblestone HQ we had a fun environment, but I think we could improve the energy even more. The company I start in the future will be a true work hard play hard environment that leaves people itching to get out of bed every morning.
My vision is a team that rings a gong after closing every deal, pours a Guinness after shipping a new feature, and takes champagne showers after closing a new round of funding. Ultimately, I want myself and my colleagues showing up to the office every day not because they simply believe in hard work or discipline, but because it is truly the most exciting and energizing place to be in their lives. Is this a somewhat romanticized, "The Social Network" startup archetype? Maybe. But that won't stop me from trying to bring it to life.
The future
Some takeaways from Cobblestone were neither good or bad, but have considerably changed my perspective on life moving forward.
Live my life with intention
I will never waste another Sunday again in my life, time is truly precious. I'm not saying that I think working Sundays was a waste, in fact I feel it was quite the opposite. We got a ton of stuff done by adding an additional work day to our week, and I think it was right decision for our stage of the business. More importantly, I loved what I was working on in those 6 day work weeks.
That being said, my appreciation for the spare time that I do have has exploded after spending a year and a half with single day weekends. I feel not just a desire, but a responsibility to make the most out of every spare moment I have and spend that time doing things that I love with people who I love.
Take care of myself
I always want to remember that my work needs to enrich my life. When I make sacrifices to my personal life for work I will take them extremely seriously. Am I saying that I should never turn down a social function to grind out a new feature? Absolutely not. Working hard on a startup enriches my life in and of itself. Cobblestone built meaningful relationships and memories in my life with colleagues, clients, investors, and more.
However, there are also times where I neglected my life outside of work, damaging my personal relationships and well being as a result. In the future I will be more mindful of drawing boundaries that help me maintain a more sustainable work life balance that promotes both my best work and personal life.
Final remarks
When I joined Cobblestone, my goal was to learn as much as possible about building pre product market fit to prepare myself to become a founder one day. Now that I've extracted many of those learnings, I most likely would not join a company as a founding engineer again. Next time I want to join a company as an original cofounder with larger equity upside and a board seat so that I can use what I learned at Cobblestone to build the company I always dreamed of being a part of.
In order to optimize for this, I decided to go somewhere that is already clearly feeling the pull of product market fit and has a highly entrepeneurial culture where I can meet my future cofounders. I think I found that place, it's called Clay and week one was already a blast. There's a few reasons I think Clay is the perfect environment.
Remarkable growth
Clay is the hottest startup in NYC, and among a few of the fastest growing startups in the entire world right now. I cannot share revenue metrics but they are absolutely wild, think a similar trajectory to Ramp in 2021.
High leverage role
I am working on growth engineering to start, which is an awesome place to be in a PLG business expanding as fast as Clay. Not only do I have an opportunity to directly improve our revenue trajectory, but I also get to work cross functionally with talented engineers across the entire company due to the nature of growth touching so much product surface area.
Stay close to users
Clay is small enough and the growth engineering role is aligned well enough that I can stay very close to users and continue developing a strong product sense. Much of my time will be spent talking to users, watching session replays, and analyzing usage metrics.
Entrepreneurial culture
An overwhelming number of Clay employees are former founders. Additionally, not a single Clay employee has quit in the past 4 years for any reason other than to start a new company. That speaks volumes to both the incredible place it is to work and the goals Clay employees have. A "Clay Mafia" is beginning to emerge, and I can't wait to be a part of it.
If this is the type of environment you thrive in, drop me a line, we're hiring. 🙂