6 Lessons in 6 Years of Building PILOT

6 Lessons in 6 Years of Building PILOT

In some ways, it seems like it was only yesterday when I first had this vague idea about a “thing” that I wanted to build and bring to the world. Of course, as any entrepreneur will tell you, the journey starts not with a dream or an idea, but with action. And so, the very first action I took in creating what would eventually become PILOT was hiring a marketing consultant I’d met on Twitter (thanks Matt Woodruff for being there at such a tender and special moment!). This was 6 years ago, back in September 2014. We met one evening in a Breather (groovy conference room service all over the city), and after a few hours had passed, I could feel the shift; my journey had actually begun. 

Now, as I reflect back on the incredibly insane adventure the past 6 years have been, I wanted to capture some of the more meaningful (and perhaps unexpected) lessons I’ve learned. 6 lessons for 6 years. May we all be insight exporters, sharing what we’ve learned with our friends and colleagues to benefit their journeys - both now and in the future. 

1 - Go Where It’s Warm 

An old sales maxim is “Some Will, Some Wait, Some Won’t, So What, Next!” It applies to who has come and gone, or joined and stayed. Employees, vendors, customers, advisors, and partners. Early on in my journey, I was throwing absolutely everything I could think of at the wall to see what might stick; and while this definitely helped me to learn a lot, it also meant that many people and organizations who came into the PILOT orbit turned out to be false-positives. 

For too long, I resisted the idea that our company, our product, or even I wasn’t something that someone (or an organization) would want in their lives. It all seemed so personal, even as our company quickly switched to a business-to-business model. I’d over-index on charming, trying to convince or influence, or overdelivering in an attempt for them to “get it” or “be feeling it”. 

Insight -- go where it’s warm. Sunflowers do this, rotating their heads towards the warmth and glow of the sun. We should have cycled through far more sales prospects, deals with customers, employees, vendors, etc. That’s something that’s happened over time, and we are increasingly finding the tribe that gets it, wants to be part of it, and celebrates their part in it from Day 1. Our many amazing supporters have also taught us a great deal and made us better. If it takes so much effort to convince someone that it’s quickly draining your soul, move on.

2 - Saying “No” is Actually Saying “Yes”

At first, it seemed to me that I should read every book or article, take every intro, scour every website shared with me, and more. It was exhilarating to do so, as I’d be super stimulated by everything happening in the world, which would set off even more ideas in my mind about what PILOT could do, like microwave popcorn popping after about the two minute mark. 

The problem was that I was getting a sugar high from all of these shiny objects, but at the end of the day, I’d have advanced very little actual meaningful work or output. The double whammy of it all was that I’d have filled up my calendar and mindspace with stimulus which existed outside of my own plans, and I’d have little of either left to focus on what I wanted to do. Sure, scanning an ecosystem and learning from others is great, but the law of diminishing returns actually presents itself far sooner than we estimate. 

Insight -- say “no” to most things, most of the time. Mentally, I find “no” to be a soul-crushing construct, so I play a game with my brain and call it “not now”. That way, I’m still being open-minded to future possibilities, while also staying focused on what matters to me, rather than on what matters to others. Warren Buffet has long been big on saying “no”, because it functions as a way to continue saying “yes” to one’s plans and priorities. BTW, Tim Ferris has also done a great podcast on how to say no gracefully. 

3 - Defining What is Enough 

Nearly 20 years ago, I read Don’t Sweat the Small Stuff, and It's All Small Stuff. I distinctly remember a passage in it which said “when you die, your inbox won’t be empty.” This makes total sense in my head, in the sense that my to-do list and obligations are always going to be larger than my capacity to get them done, thus resulting in a never-ending queue. But my daily experience over the years has been to end the day (often after working 12- or 14-hour days) feeling utterly unaccomplished. 

Some of that was related to Insight #1 and #2 above, certainly - both of which wasted my capacity and spirit at the expense of making more progress. But what I realized is that part of my strength as an entrepreneur, and as being someone with a vision of what could be vs. what is, is also a curse of ambition that leaves me feeling restless and unfulfilled. My yardstick was fulfilling my mega-world-changing vision, and so naturally whatever I had completed in a given day only equated to being a mere speck of sand, standing in lowly contrast to a vast, looming sand dune of desire.

Insight -- be highly intentional in defining what is “enough” for both myself and my company in a given time period. We’ll never be “done” until we are either dead or have left this game, so I’ve found it incredibly helpful to actively define - on a quarterly, monthly, weekly, and even daily basis - what is “enough”. Sometimes I’ll hit that threshold and keep going, just because I want to. But more often than not, I’ll give myself the permission to enjoy my weekends instead, or hang with my boyfriend, or do something else pleasurable besides work, without any sense of guilt or regret. Employees often have decent standards for deciding what “enough” is (job descriptions, measurable goals, or even a fixed schedule), and entrepreneurs need to also define for themselves a yard stick, so that they can actually embrace and enjoy their non-work time.

4 - Filtering Inbound Feedback 

One thing I found myself entirely unprepared for was the amount of feedback that I’d receive as a founder. Perhaps part of that is that PILOT is doing something that really has never been done before, in a space that many people are interested in. Not managing Insight #2 would also contribute to a huge surge of feedback coming down on me like a brutal rainstorm. 

I’d often receive feedback about things that I didn’t even care about, or things that I understood far more deeply than the person sharing their opinion did. Most of the feedback was unsolicited, and most of the people who gave it thought they were being helpful. Something I noticed over time about the feedback from other entrepreneurs was that it was uniform, advising me to repeat their moves and to follow their pattern of success (if they were successful), even if it had been under entirely different conditions. And naturally, those who were employees also seemed to delight in getting to play the role of armchair Founder or Product Manager. 

Insight -- be highly intentional about what, and who, you listen to. First, work upstream by being explicit with what you want or what would be helpful. Most people out there are just trying to help, and ideas are an easy thing to provide that gives them pleasure. Simply stating “here’s what would be really helpful to me” can totally shift the conversation in a way which still enables them to help, but in a way that’s useful to you - and not just to them. Second, “consider the source”, when it comes to feedback. If it isn’t coming from someone who’s already a paying customer, then it carries far less weight. Prospective customers definitely seem like a good source of feedback, but until they’ve made an initial commitment to what you have (vs. what they wish you were), it should also be discounted. And third, while people love to be creative and solve problems, you’ll obtain the best feedback when you probe under the ideas to get more insight into the problem they think their idea would solve. Chances are, you and your team will have more clever, faster, easier ways to solve the problem than the idea first presented - so understanding more about the problem it's trying to solve (or if there even is a problem) is crucial. 

5 - Separating Company Health from Founder/CEO Health

For the longest time, I collapsed how PILOT was doing with how well I was doing as CEO. After all, my job was to make the company successful, right? But what I realized is that this is a venn diagram that’s actually only got limited overlap. Early on, the company wasn’t going to be killing it, knocking it out of the park, crushing it, or whatever a startup bro might say after his third IPA. But oftentimes, I was doing quite well as the CEO, given where we were at on the current stage of our journey.

The problem was, because I collapsed the two, I was always left with a feeling of inadequate dread about how “we” were doing. Down the line, as we began to grow, gain market traction, and move closer to product-market fit, there were stretches of time where the company would be doing quite well, but I’d know I wasn’t personally being as effective in my role and responsibilities. Sometimes it was failure to delegate, lack of prioritization, or even (at times) me personally being down. And as a result of my collapsed circles, I wouldn’t allow myself to ever feel good or celebrate (more on that in Insight #6) how well the company was doing, because I knew I wasn’t bringing my best to my role.

Insight -- separate out how well the company is doing vs. how well I am doing in my role as CEO. The company can have various strategic objectives and KPIs to hit, which are certainly things I help to impact, but they are really the sum total of the efforts of our incredible team (we use the term “crew”). Conversely, in my role as CEO, I have various goals which shift over time, as the context of our company changes. I’ve felt far better at the end of a day, month or quarter when I’ve evaluated each one distinctly, including setting the bar for what was “enough” in advance.

6 - Continuous Celebration is Critical 

Perhaps due to the fact that I’ve chosen to pursue an entirely self-funded, sustainable model for building an enduring business (in contrast with a short-term R&D experiment; the Venture Capital model), it has been extra hard to feel good about our progress. There is a desert of validation. Some of it can be created with investments in PR or social media, speaking at events, etc., but that’s mostly just vanity metrics. 

Public companies have their stock price, public financial statements, industry analysts, and board meetings to help assess how well they are doing. Conversely, as a private company that’s in its earlier stages, growing at promising-but-realistic rates, we’re not yet on the “radar” of everyone in our industry. So often, I’ll wonder if this is what it is like to be a fine artist, toiling away in a studio somewhere and not really knowing what will become of the work that they’re creating. 

Insight -- rather than look outward for validation, we must instead look inward and celebrate continuously. About two years ago, we started tracking monthly accomplishments as a crew. We haven’t missed a single month since, and we’ve implemented a giant virtual Mural whiteboard, to all contribute to the wins and accompaniments that we’ve made in each department of PILOT. Separately, we track insights from what we’ve learned, which represent another excellent predictive proxy for progress; our “company’s rate of learning” as our advisor Kut says. Now, each and every damn time we do this 20-minute exercise, we’re blown away with just how much we’ve gotten done, how proud we are of ourselves, and how energized we are about taking on the next proverbial hill. In fact, next year, I’m going to make it a priority to explore how we can celebrate even more often as a remote-first company, so that we all feel the boost of endorphins like an NYC marathon runner going past each watering station, gaggle of supporters, or mile marker.

****

I hope that this has been both useful and inspiring. 

I’ve never been more proud to be a resident of New York State, and to build PILOT from New York City than I have been in 2020, and I’ve decided to adopt our state motto, “Excelsior”, which means “Ever Upward”. 

B2