Starting my own business has been one of the most exhilarating experiences of my life. But it is so stimulating, fast-paced, and exhausting that it’s easy to neglect taking the time to pull up and reflect on what I’m learning.

Of course, on a more tactical level, my team and I are constantly discussing what we are learning and making a thousand tiny adjustments and decisions as a result. But it’s these larger insights from what was the hardest working year of my life, 2017, and a pretty intense start to 2018 so far, that I think are most valuable when looking in.

1 - Be Willing to Deliver Less Than Perfect.

I once heard Mark Zuckerberg say, “If you aren’t a little embarrassed by your product, you released too late.” This has been a difficult lesson for me.

In the past, I took on the responsibility of judging the readiness of our products and content before putting it out for public consumption. I wanted to make revision after revision until it was just right, delaying delivery until I’d removed any opportunity of embarrassment about what we were producing.

This was a huge mistake for a few reasons. First, I am too biased to clearly evaluate the work my team and I are doing. Second, it blocked us from receiving crucial external observations,  thus lengthening our feedback loop. The cost was a good deal of money, as well as time and effort on work that didn’t fit with our customers’ needs.  

Being apprehensive or embarrassed about the readiness of our output was actually a good sign. In my corporate days, I’d have been punished for delivering incomplete or hot-off-the-press work product. But in the startup world, we must release those perfectionist or ego-based impulses, and work harder to get a good version of our work out into the world for feedback as soon as possible.

One surprising result has been that what I thought was just “okay” has often been received as “awesome” by customers. What they thought needed to change was often something completely different than what we would devote our attention to had we given it another round.

2 - Focus on Activity More Than the Outcome.

Who ever heard of a coach who doesn’t prioritize results? It might sound silly, but what I’ve learned is that thinking too much about a future state, potential, or result that may or may not come to fruition can easily take me out of the present-- all that I need to accomplish today or even this week-- and leave me full of anxiety over something that’s not even real. Focusing on the behaviors and activities that directly lead to the results I want allows me to retake control-- and lower my anxiety!

Instead of obsessing over sales goals, I shift my focus to what is controllable: setting up sales meetings following up on previous sales calls and getting proposals in front of prospective customers. So much of it is about staying in the present, while still having a “north star” vision of where we’re aiming to go. So when I drag myself home from the office late on a Friday night, I can feel satisfied knowing we are on track, even if we haven’t achieved our outcome--yet.

3 - Delegation is a Mountain With no Top.

I am very good at delegation. I trust my team. But I’ve learned that the practice of delegation isn’t one-and-done. Rather, it is a continual and sometimes uncomfortable process that never ends.

Unlike a stable corporate job, being the founder of a growing startup means that circumstances, including our product, our customers, and our priorities, are in constant flux. When pushed by advisors to delegate more, I’m still sometimes tempted to snap back, “I just delegated all of that work last week!” But the truth is, delegation reduces highly wasteful context switching and it ensures that I spend my time on the things I’m uniquely qualified to do.

Sometimes I resist delegating because even the most trivial of tasks can be a useful distraction from something I don’t want to, and I’d rather just avoid. Other times, I convince myself that the quality of work might suffer if it were outside of my control. Although this may be true in some cases, I refer you back to my first point. Plus, the more I delegate, the more my team grows, which massively raises the quality of the work and gives the added benefit of innovation, adding more eyeballs with diverse perspectives and skills.

4 - Right Now is All That Matters.

While anticipation and planning are good things, it can quickly become overwhelming thinking of everything that needs to be figured out, achieved, and built. In many ways, trafficking in future-based hypotheticals is a form of resistance: an effort to avoid having to be responsible for what’s right in front of me. Sometimes I find myself fixated on some trivial product decision that we need to figure out someday, only to chuckle when I realize I’m just avoiding writing those proposals that are due by the end of the day. Keeping that “north star” vision is important, but I am at my best when I am looking right in front of me and staying in action. My friends in addiction recovery have a saying: “one day at a time.” It’s a mantra they repeat to themselves when confronting the enormous challenge of staying sober for the rest of their lives. It applies to the startup life, too. I just have to focus on what I can and must achieve today.

5 - Treat Feedback Like Gold.

My team and I treat feedback like gold. We intentionally seek it out. We actively plan ways to get more of it. We treasure it. And information like customer questions, complaints, ideas, suggestions, participation metrics, and survey results are golden nuggets. My team has developed a thick skin and a drive to always get better. This is a stark contrast from my corporate days, where most people were feedback-resistant, bristling with any suggestion that they or their work was less than perfect. The culture of a startup is necessarily very different. We make it a point to be transparent with our data, often sharing it with colleagues and trusted friends. We don’t always get back atta-boy affirmations-- nor would we want to-- but the insights we receive are a gift. The feedback we receive is precious because armed with this information, we can nimbly make decisions that propel us forward in ways we couldn’t have conceived on our own. It’s important to note that we don’t act on everything we hear. But constantly soliciting and synthesizing feedback massively accelerates our rate of learning, making us smarter, with fewer resources, in less time.


6 - Nurture Past Relationships and Weak Ties.

Living in Manhattan, it seems I’m meeting someone new every day. While this can be thrilling in some respects, I realize it’s easy to forget or even neglect relationships I’ve created in the past. No knock on new relationships, but they are top of the funnel, with many unknowns.

This year I learned the importance of tending to past relationships, even with people that I hadn’t spoken to in a long time. I found delightful connections, fond memories, mutual support, the opportunity to make an impact, and even new business opportunities! It all felt so natural, too. And as I now see it, those relationships were always right there, ripe with potential. All it took a reinvestment from me.

But what about weak ties, or people I’m only loosely connected with? Over the course of my career, and in my personal life, I’ve come to know many different people from all walks of life. Thanks to social media and my diligence in maintaining a presence online, I’ve been able to connect with people across the globe. Some of my most unique opportunities have come from people I barely know.

7 - Take Care of the Team First.

I meet many business owners who complain about the talent in their companies. Their attitudes seem as if they think “talent” is something they can find or acquire, as opposed to something they attract and cultivate. Just like dating, swiping right on someone is just the start: the possibility of a new connection, and from there, the work starts. I’m thrilled to have attracted such a diverse, talented, trustworthy, and passionate group of colleagues. But in reality, anyone with talent always has options, so I do my best to get to know them personally. I meet their loved ones, work to understand their backgrounds, and explore their interests. When big world events happen (like a mass shooting), we dedicate the start of our staff meetings to discuss and process together. Many of the team is remote, so these sort of connection points, beyond the tasks at hand, are a critical part of why we’re so collaborative; we see each other as people first, colleagues second. And by taking care of my people, I am enabling them to take care of our customers.

8 - Move it Forward and Make it Better-- Each Week.

In a startup that’s inventing an entirely new category of product, the image of success is murky, at best. Of course, we have our mission, vision, and values, but how do I know if we did a good job this week? I’ve learned that I need to define the yardstick and do the measuring. What seems to be the right measure is, “did we move things forward this week, making incremental progress?” Or, “did we improve something and make it better for our customers?”

People say running a startup is like “building the plane while you fly it.” So we can’t just measure our efforts relative to core operations, like my friends in traditional jobs do. We have to be building capacity in the company week after week. Sometimes it is as simple as making quick adjustments against helpful feedback on sales collateral (one PDF we use frequently is on version 27). But when we wrap for the week, we know we did a good job if we have more than we started with on Monday, or what we have has been improved based on feedback and learning.

9 - Design With Discipline.

In the early stages of a startup, it is easy to get caught up in all of the things a company could do. We get energized by all of the ideas and possibilities. But practically, there’s a pretty limited number of things we can actually do, build, and execute. More is often not better. Doing “more” often creates a disjointed, grab bag, confusing mess for our sales prospects, buyers, and members. Being disciplined as we design products and define how we deliver and interact with our members and avoiding shiny objects that seem like compelling opportunities has paid off. Our members and buyers are happier when we give them fewer, more focused, simpler, and more refined weekly coaching features. Initially, it felt as if we were under delivering or being lazy. But customer feedback has revealed the value of ruthlessly prioritizing and curating their experience, with a great deal of empathy for where we’re meeting them, and respect for their time.

10 - Be Extraordinarily Patient.

Perhaps it is the on-demand nature of our consumer culture that’s warped my expectations of how long things should take. When I first started working on PILOT over three years ago, I had no idea how hard it would be or how long it would take before we made even incremental progress. I hugely miscalculated what it would take, and now, I assume my expectations of what it will take for PILOT to be what I envision are likely off by an order of magnitude. Social media offers a warped view: I think it’s pretty easy to compare our progress to others’, but in reality, I’m comparing my insides to their outsides, capturing only their highlights. It’s enough to leave me feeling behind or inadequate. I started reading Bloomberg on Bloomberg at the end of 2017, a book I’ve wanted to read for some time. It was inspiring to follow the story of Bloomberg LP and Mr. Bloomberg, who founded his company just a week after I was born and take note of the time and effort he put into it. He’s created something incredible, over decades. While the media fakes me out with overnight success stories, I’m learning to slow my roll with my expectations, be extraordinarily patient, and play a long game.


I hope my experiences will lend insight to your own journey. Keep learning!