10 years, 10 lessons
It’s been a decade since we spun off from 37signals and became our own standalone company. Biggest lessons I’ve learned as a founder and CEO in that time…
“You’ve been in business for how long?”
This is the most common reaction I get when I tell people that I started Canopy back in 2014, when we were spun-out of 37signals. (We were called “Know Your Company” back then.)
It’s 2024 now. Ten years is a long time.
The tone of voice is tinged with surprise.
Depending on who I am talking to, an eyebrow raise accompanies more questions:
“Do you still like it?”
“Do you ever want to sell it?”
“What’s your next thing?”
On one level, I get it: Skepticism of working on one thing, for a long time. Disinterest in a long-term endeavor.
I’m not sure if it’s because our modern times has engrained novelty as a cultural value. Or if “putting your eggs in one basket” isn’t considered a strategic career move (especially when the Silicon Valley norm is to switch it up every 2 to 3 years).
For myself, personally, I feel oppositely.
I believe everything of quality takes time. Time to think, time to build, time to adjust. It doesn’t matter if you’re working at a company and or starting a brand new venture. It doesn’t matter if you’re growing a garden in your backyard or working on a new painting. If you’re trying to make anything meaningful, it requires discipline, patience, effort, and time.
And for me, time well spent is being intentional with that time. Choosing what feels meaningful, joyful, uplifting, when I can.
So here, I am a decade in. Still choosing the work we do here at Canopy to support leaders. Still loving it. Still wanting to spend more time on it.
As I look back on this time, I wanted to reflect on the lessons learned. Below are the 10 key lessons in particular, from the last 10 years…
Lesson #1: You can do a lot with less.
Constraints breed creativity, or so the adage goes. A cliché because of how true this is.
As a small company, we consider this constantly. Yes, there are plenty of things we’d like to do, but having constraints enable to focus only on what matters and do it with the highest quality.
This was perhaps most true in our recent rebrand. We gave ourselves 3 weeks and devoted only 3 people to the full project. Not because we are masochists 😉 but because we knew the constraints would give us a better outcome.
The 3-week rebrand has since given us a 2X-3X lift in sign-ups – and proves to me how much you can do with very little. You can read all about our rebrand process here.
Lesson #2: Develop a taste for problems.
A friend once told me that company building was most analogous to cycling:
It never gets easier, you only go faster.
In beginning, this used to discourage me. We’d hit a new top-line revenue goal – only to realize that we needed to increase revenue even more, to make sure we could continue to invest in improvements for our newest customers. Or we’d be thrilled that we partnered with a large, prominent company to train all their managers – only to face a level of customization that we’d never done before. One problem solved, another puzzle emerges.
It never gets easier….
But I’ve since now learned: Not only are all these problems normal or expected, there is no alternative state.
As author Oliver Burkeman of Four Thousand Weeks writes: “We seem to believe, if only subconsciously, that we shouldn’t have problems at all.”
Instead, he encourages us to “develop a taste for having problems.” Cultivate patience to encounter new problems day after day, week after week.
It doesn’t make it any easier, but it sure does make the ride more enjoyable.
Lesson #3: Vision is more than a buzzword.
“Vision” is a word so overused it’s become vapid. Yet, it’s emerged as perhaps the most powerful concept for our own company.
I first encountered its true definition in college, as a Learning and Organizational Change major. I read Peter Senge’s seminal The Fifth Discipline, where he defined vision as “a picture of a better place.” A future state that enables the necessary creative tension for a team to go from here to there.
I found this concept unlocking. When your team has vision – a true picture of a better place – it has something compelling, visceral, meaningful to strive for.
Here at Canopy, our vision is to create a world where bad bosses are the exception, and not the norm. That clarity of vision for us has been immensely helpful on multiple levels…
Hiring: How much does this person care about the vision? When there is deeper care for the vision, there is a deeper level of intrinsic motivation.
Decision making: How aligned is this decision with our vision? Having a clear vision helped us make the decision to do the rebrand, for instance.
Client offerings: Will this project or new feature tangibly help us make progress toward our vision? With a well-defined vision, it’s easier to serve our customers and know what they will and will not care about.
For us, vision is more than a buzzword, and it’s served us well.
Lesson #4: People buy from people, not companies.
Early on, when our company was spun out of 37signals, I remember their CEO Jason Fried sharing advice with me I carry to this day. He told me:
“Claire, remember, people buy from people, not companies.”
Jason encouraged me to be open, personable, and accessible as a CEO. To not just hide behind a company logo and parrot corporate speak. He reminded me that it was the relationships that I would build with people that would cause folks to trust us — and then buy from us.
We act on Jason’s advice every single day. I personally write every piece of marketing content we produce, and have for the last 10 years. Every newsletter, every blog post, every Linkedin post, every Tweet, for a decade. I strive to speak to our customers not as “Canopy” but as myself. As Claire.
We’re lucky to have gained an audience with hundreds of thousands of folks as a result. People want to buy from people, not companies.
Lesson #5: Play your game.
I first became the CEO of Canopy (then Know Your Company) when I was 24 years old. I remember thinking to myself: What is “success” for me?
It was tempting to answer that question with “X revenue dollars” or “X headcount.” It was especially tempting to say I’d reach both milestones within a certain timeline…
Since then, I’ve realized how neither of those potential answers were my own answers. They were answers I’d heard on podcasts or read on other founders’ blog posts. It was so easy to conflate others’ definitions of success with my own.
For me, what “success” truly means is to build a company that is helpful to others on my own terms. To have a meaningful impact in a way that I believe is meaningful. To have autonomy and flexibility in our decisions.
It’s because of this that I realized that we weren’t right for traditional VC – but potentially right for alternative models of support. As a result, in 2019, we partnered with indie.vc, an unconventional fund that Bryce Roberts founded. Keen on supporting revenue-focused companies, Bryce’s belief in helping founders build independent, sustainable companies was a good fit for us and has helped us grow to the company we are today.
Focus on the things you want to focus on. Play your own game, and no one else’s.
Lesson #6: Trust is earned.
Trust is table stakes. We know this inherently. Yet, something I’ve seen play out time and time again in the past decade as CEO of Canopy has been not how important building trust is with your team: But how that trust is earned and not automatically given.
Trust is built from the small things you do every day to be consistent:
Your behavior matches your words.
You follow through.
You’re willing to be vulnerable when needed.
You’re transparent with a purpose.
Perhaps the starkest example of how I try to practice this: New hires at Canopy are always shocked to find that everyone in the company knows our bank balance and revenue numbers. We openly discuss this, and we use it to align our priorities as a team together.
Our team is comprised of responsible adults who are committing a significant part of their lives. They are giving me their trust. I want to give them my trust, in return.
I don’t take my team’s trust for granted, or assume it will be there. I do all I can to earn that trust, in every way possible.
Lesson #7: Listen, really, listen to your customers.
Conventional wisdom says: Talk to your customers.
Yet, I’ve found this to be the undervalued cheat code for almost everything in a business. It’s been the answer to possibly every question we’ve had at Canopy.
Almost all the marketing copy, for example, on our marketing site are phrases heard straight from the mouths of customers. Leaders looking for “lightweight learning” to “meet them where they’re at.”
In another example: We designed our pricing plan directly based on customer feedback. When managers told us that they didn’t have any budget for resources or L&D, we decided to create a free plan for Canopy. We believe leadership learning shouldn’t be restricted just to those who can afford it.
Every answer could be found in what our customers are saying. We just had to listen.
Lesson #8: Do the things that don’t scale.
Paul Graham famously wrote, “Do things that don’t scale.” We’ve relished in that idea here at Canopy. Especially because the work we do is helping leaders – a very personal task already – we focus not necessarily on “how well will this scale?” but “how well does this solve the problem for leaders?”
Likely the best example of this is our On-Demand Coach Feature, which is powered not by AI, but by a real life person.
That’s right. Any request you send, a member from our Canopy coaching team will answer. All within 72 hours.
Sometimes that’s me personally, as the CEO, answering.
Deep, personalized, nuanced. It’s the equivalent of executive coaching, but on-demand and asynchronous.
Sure, it’s tedious at times to have all these requests come in and answer… But, boy does it solve them problem well for our leaders! Every day, we get feedback like this from our leaders who use our On-Demand Coach feature:
This non-scale version laid the groundwork for our scale-version of coaching as well: Our Canopy AI Assistant. We saw firsthand the pain points and topics our leaders wanted covered, then built a scaleable solution – after we’d done the manual version.
Scale shouldn’t always be the priority. Solving the problem well should be.
(P.S.: Our AI Assistant is in alpha, if you wanted to sign-up and try it here.)
Lesson #9: Let the voice of growth be louder than the voice of fear.
Change is always scary — especially if you’ve been doing something for a while.
Whenever we’ve launched a new product (our leadership training product) or evolved our ideal customer description (from just CEOs to all managers), I’ve always hesitated for a moment.
Is this really the right move? Will I rock the boat too much for folks who are already happy? What might we lose with this change?
All valid questions to answer. But I think we often forget that those questions are the voice of our fear – the fear of unknown, the fear of reprisal, the fear something will go wrong – rather than the voice of our growth.
What I’ve found in my 10 years building Canopy is that you can’t let the voice of fear dictate your decisions. You’ll never grow or evolve your business in any way otherwise.
Focus on the impact that you’re trying to create. Weigh the trade-offs of the change. But don’t let the voice of fear be louder than your voice of growth.
Lesson #10: Life is big. Bigger than work.
I love to work. I love the act of thinking deeply on things, building things, and helping others. But I also know that attachment to doing-doing-doing and building-building-building hasn’t always been most additive to my life.
I’ve canceled dinners with friends or turned down meaningful trips because “I’m too busy with work” — and each time, I’ve regretted it. Deeply. Looking back, it’s never made a positive difference to trade the time with family and friends for my work.
Of course, it’s not a zero-sum game. When I am happily spending time with friends and family, turns out, I perform and show up better in my work as well.
Now older and wiser, I realize this is possibly the greatest thing I’ve learned in the past decade: How big and beautiful life is. Life can encompass so much light, buoyancy, and richness, if you let it. Work can absolutely be a part of that. But it all becomes lighter, more buoyant, and more beautiful the more I’m able to see the full picture – the bigness of life, how much bigger it is than my work – and can retain that perspective.
I write these lessons here to remember them for myself as much as I do to share them with others. I look forward to the process of learning more, in the next decade to come.
Thank you for reading!
To the next 10 years…
-Claire