10 lessons from 10 years of entrepreneurship
Today’s a special day. Today marks ten years since I became an entrepreneur.
The last decade brought highs and lows, wins and losses, and two different companies that are both thriving today. This anniversary has given me a chance to step back and reflect on the things I’ve learned. These lessons are not prescriptive to success, but I hope you can gain something valuable from these reflections.
Ten Lessons in Ten Years
1. Get Niche
My brother and I started our first business in 2009. We really didn’t know what we were getting ourselves into, but we knew we wanted to be in business. As a result, we provided nearly any digital service to anyone who would pay us for it. We did fine, but we lacked focus. It wasn’t until I started Lemonly, my second company, that I realized there’s a smarter way to approach entrepreneurship.
Get niche. In today’s world, there’s an industry or service for everything under the sun. You won’t survive long as a business if your mission statement is too vague or too broad. When I started Lemonly, I learned the value of specifying your work. I went from providing a dizzying array of digital services to doing one thing — infographics — really well. You don’t have to do everything to stand out (you can’t). Instead, just be specific — and be excellent.
2. Document the Journey
Every entrepreneur knows the importance of creating a personal brand through quality content. But we struggle with a different question: What should I say? After all, the world doesn’t need more content; it needs better content.
If I were to start a new company, I would take Gary Vee’s advice to value documenting the journey over creating content. Instead of stressing about every Instagram post, why not just take photos and videos as you go? Document your ideas, your experiments, your journey. Sure, some of this content may never escape the dark, forgotten corners of your iPhoto Library, but in the process you will build an audience interested in what you have to say, and you will create a story.
In fact, documenting the journey means learning to tell stories. And whether you’re a new entrepreneur or a seasoned veteran, that’s something worth learning.
3. Do Things that Don’t Scale
When Airbnb started in 2008, they knew they needed top-notch photos of the rental homes that would drive their business. Rather than relying on hosts for these photos, Airbnb flew professional photographers all across the country to photograph rental homes for their website. Obviously, they couldn’t sustain such a practice for long. But this seemingly impractical decision jumpstarted what would quickly become a $30 billion company.
It’s a perfect example of the third lesson I’ve learned: Do things that don’t scale. In the rush to automate, outsource, or streamline our work, we often overlook the power of those simple gestures and personal touches that delight our customers, even when they aren’t scalable.
When Lemonly starts a relationship with a new client, we send lemon bars. When your project is complete you get a handwritten thank you note. It’s not the most pragmatic practice, and only scalable to a point, but it surprises our clients—which means it’s worth it. Pursue efficiency and growth, but remember things that don’t scale.
4. Build Your Village
Entrepreneurs fly solo. At least, that’s the impression we sometimes get. In truth, however, no one succeeds in business (or in life, for that matter) without support from others. That’s why the fourth lesson is to build your village.
Building your village, or investing in your support system, begins by recognizing that you can’t make it alone. Behind every successful entrepreneur stand accountants and lawyers, friends and other founders — people who too often go unrecognized, but whose influence remains nonetheless vital.
Remember the conversation over coffee with that acquaintance who tipped you off to that career-defining idea? Remember the mentor who taught you so much when you were starting out? If we forget these people, we forget the humbling reality that our success is always the fruit of another’s toil. No one is only self-made.
Never burn bridges — it’s not worth your time. Or rather, it’s always worth investing in your village. Surround yourself with people you can trust when the going gets tough, because things will get tough. You will face failure and discouragement. And that’s exactly when you’ll need friends and colleagues who will continue to root for you. It takes a village to raise a child; it also takes a village to build a company.
5. Learn to Learn
For as much as our society values formal education, few people these days finish high school or college with a firm grasp on how they learn. For better or worse, school trains us how to pass exams and get good grades. But life isn’t a bubble test, so once we leave school, many of us need to re-calibrate how we think about learning. We must learn how we learn.
Everyone learns differently. What get your gears turning might not work for me. Over the years, I’ve discovered that I learn best through listening. I like to absorb and process as much audio information as I can. So, naturally, when I discovered Audible audiobooks, I went from reading four to forty books in one year. Do I remember everything about all those books? Not a chance. But that’s okay, because along the way I also learned that, for me, anyway, “done” is better than “perfect.” Life isn’t a test, remember? Learning doesn’t have to mean memorizing all the textbook facts. Learning is about gaining new insight, knowledge, or skills through whatever means work for you.
Entrepreneurship demands learning. We can’t grow or improve without it, so figuring out your learning style is indispensable to succeeding in business. What have you been learning lately? When did you discover how you learn best?
6. Set the Table
One goal I set for 2019 was to drink more water. Sounds simple, right? The means is the end — just drink water. And yet there are days, whether due to busyness or sheer absence of mind, when I forget to hydrate. What gives?
Perhaps there are no shortcuts to success in life, but there are ways to make winning easier. (Pop culture now refers to these as “life hacks.”) Lesson six is one such hack: Set the table. Setting the table means controlling and preparing your environment. At the end of the day, humans are largely the byproducts of our surroundings — but this doesn’t render us mere victims of circumstance. Why? Because humans also have the power to shape our surroundings.
If you want stronger relationships, better habits, or greater efficiency from your day, don’t just try harder; set yourself up for success by manipulating your environment in ways that simplify your decisions. For example, if you want to watch less Netflix, get the TV out of your bedroom. Want to start eating healthier? Keep a bowl of fresh fruit out at home. (Now you’re literally setting the table.) Then, when it comes time to decide, you will find that half the battle is already won for you. As James Clear puts it in his book Atomic Habits, “Be the designer of your world and not merely the consumer of it.”
And what if you want to drink more water? I personally hacked this goal by asking our wonderful Office Manager, Emily, to fill my (Lemonly-yellow colored!) water bottle before I arrive at the office each morning. Now, when I sit down to work, my environment encourages me to win, in this case to drink more water. Simple, and effective.
What goals are you currently striving for? Consider ways you can take hold of your environment to help you get there. Set your table for success.
7. Ask More Questions
Because, as you know, there are no dumb questions. This lesson expands on Lesson #5. If you want to learn — i.e. if you want to grow as an individual or company — ask more questions.
Sadly, many buy the lie that asking questions only reveals ignorance or naïveté. This couldn’t be further from the truth. We need more questioners because, in reality, questions don’t disclose ignorance: They reveal curiosity. People who question crave knowledge, understanding, truth — which is exactly why asking more questions leads to growth.
It’s also the reason hiring managers frequently conclude job interviews with the deceptively innocuous, “Do you have any questions for us?” Answering “no” here hardly reveals your qualifications for the position, nor does it look smart. They want to see that you care enough to ask genuine, well-thought-out questions. They are looking for curiosity.
Don’t content yourself with confusion — that only leads to chaos and insecurity. When we dig deeper through inquiry, we do everyone a favor. Ask more questions.
8. Know the Value of Your Time
Not all work is created equal. Tragically, many entrepreneurs become workaholics, constantly consumed by their business with little (or no) work-life balance. Some, as a result, adopt a work-for-work’s-sake mentality: It doesn’t matter what I’m working on so long as I’m “working.” Not only are such lifestyles unhealthy and unsustainable — they’re also a flat-out waste of time. Let me explain.
Lesson #8 is to know the value of your time. Simply put, some tasks are worth more than others. At Lemonly, I think about my work in terms of $10, $100, and $1,000 tasks. Here are a few examples.
- $10 task: depositing checks at the bank
- $100 task: managing my email inbox; replying to clients
- $1,000 task: client phone calls; researching, reading, and planning for company vision and culture
There’s no virtue in managing your inbox for 80 hours a week. Knowing the value of your time means knowing the value of your tasks—all the possible things you could accomplish in a day — and planning your schedule by prioritizing accordingly.
By the way, this is why you should value an office assistant. You can’t buy more time in life, but you can delegate tasks to create more margin. If you believe, as an entrepreneur, that you are the best in your niche service or industry (and you should), cloning yourself, so to speak, is a resourceful move. Do meaningful work by knowing the value of your time.
9. Bang the Drum
The most unexpected role I’ve embraced as a CEO is “cheerleader.” Most entrepreneurs begin their journey with a particular passion: coding, company culture, design, photography, etc. As you advance and build a team of employees and partners, however, your role will evolve. Now you must care for them, too. One way to rock this? Bang the drum.
Banging the drum looks like celebrating company success and praising employees for a job well-done. “Hey, I love how you did _______!” Or it looks like lauding your hometown, a local school or sports team. Spark optimism and positivity; galvanize those around you.
As a leader, you have a unique power (and responsibility) to rally others around common causes — not the least of which is your company. Banging the drum for your company means consistently reinforcing its vision and values both through explicit communication to your team, and leading by example. I’ve also learned it entails a kind of steadfastness. When business spikes, leaders keep their cool; when business slows, they keep team spirits soaring.
How are you banging the drum in your company or community? Start by looking for reasons to celebrate, because there are reasons to celebrate. Then take the time to point them out through praise, encouragement, Twitter, whatever. Don’t just be a leader. Be a cheerleader.
10. Better Every Day
Maybe now more than ever, our world engenders an unhealthy “comparison game.” Thanks to new social media technology, much of modern life is spent scrolling through the curated and filtered lives of family, friends, pop stars, and even strangers we happen to follow online. Next to such picture-perfection, we can begin to feel lonely, insecure, and less-than.
Worse, the comparison game eventually gets inside our heads: “You’re not good enough, smart enough, pretty enough. You don’t do enough. You do too much. You don’t have what it takes.” Platforms like Twitter, Instagram, and Facebook, which were created to connect us, have increasingly severed us from others as we try to measure up to an impossible standard.
In this context, what does it mean to improve as individuals, entrepreneurs, or companies? How do we free ourselves from the Sisyphean struggle of comparison? You might think my answer is to drop comparison all together. Just let the rock roll.
It’s not.
Instead, my philosophy is this. Do compare yourself with one (and only one) person: who you were yesterday. Then make it your goal to get 1% better today. At Lemonly, we call this “Better Every Day.”
Why just 1%? Change is hard, especially if we’re preoccupied with the opinions of others. But all of us can look in the mirror each morning and commit to being 1% better than we were yesterday — a better entrepreneur, spouse, parent, friend, reader, runner, eater, a better person. I’m not asking for overnight transformation here, but compound interest amassed over a lifetime — a life well-lived.
So stop comparing yourself with others; no one wins that game. But you can win today. I challenge you to be 1% better today (just 1%!) than who you were yesterday. It could be the difference of one decision, one word, or one minute — whatever it takes. Better every day.
Looking Ahead
Truthfully, I can’t count on two hands the number of lessons I’ve learned in ten years as an entrepreneur. But these ten stand out. I trust that ten years from today I will look back with greater insight and more words of wisdom gleaned from the rough and tumble of entrepreneurship. But for now, I’ll celebrate.
Which of these ten lessons resonated with you the most? Tweet me at @johntmeyer — I’d love to hear from you!
