10 Years, 10 Lessons — Key Insights From a Decade of Entrepreneurship In honor of my business's 10-year anniversary, here are 10 lessons I've learned about entrepreneurship and leadership along the way.
By Hope Horner Edited by Chelsea Brown
Key Takeaways
- Reflecting on a decade of experience as a CEO, offering insights gained from building and growing a successful business.
Opinions expressed by Entrepreneur contributors are their own.
On the heels of my business's 10-year anniversary, I've been reflecting on the journey and the many lessons I've learned in my decade as CEO. Below, I'll share the ten most profound takeaways — the ones I wish I'd known in the early days of entrepreneurship. Apply them to your journey if you're on a similar path!
1. Have clear expectations and consistent accountability
In my mind, these two factors are the foundation of successful leadership. Without clear expectations, your team members might not understand what you actually want from them, and their definition of success may not align with yours. Without consistent accountability, they won't meet those expectations and will have a harder time learning how to improve.
Establishing clear, consistent communication ensures everyone is on the same page and moving towards the same goals.
Related: I Wish I Knew These Four Things Before Starting My Own Business
2. Understand evolution vs. revolution for leadership hires
When it comes to hiring for leadership roles, make sure you understand the roles you actually need. My best advice is this: Hire a manager when you need evolution and an executive when you need revolution.
I've learned (the hard way!) that all leadership hires are not created equal. A growing organization will eventually need both, but understanding whether you're looking for evolution or revolution will help you make more strategic hiring decisions.
3. Know that company culture runs deeper than "fun"
Fun is an element of company culture, and I do believe you should invest in it — whether that's through team breakfasts, team outings or other activities beyond just work. But true culture is about creating an environment where everyone feels valued and supported, and that goes beyond just having a good time together.
If you want to foster a company culture that doesn't rely on throwing parties or catering lunches, be mindful of the little things, too: how your leadership team answers hard questions, how you balance transparency with protecting your team from hard truths and how you treat people day-to-day. Your employees will notice all of these details, and they really add up.
4. Expect everything to cost twice as much and take twice as long
Over the years, I've come to expect everything — from new projects to hiring decisions to new products — to take longer and cost more than I expect. And even when I try to apply this lesson ahead of time, I'm still likely to underestimate.
Planning with this principle in mind can help manage expectations and reduce frustration when things don't go exactly as planned. A buffer is a good thing!
5. Hire a coach
My two co-founders and I started working with an executive coach about eight years into running the business, and I wish we'd done it sooner.
Coaches help you find your leadership blind spots, offer an impartial sounding board when you face challenges and help other members of your team level up alongside you. It may take time to find the right person for your needs, but in my experience, it was worth the effort.
Related: 8 Important Lessons From Leading Entrepreneurs
6. Co-founders are everything
Co-founders are the people with whom you can share your truest experiences: your deepest fears, your most outlandish concerns and your greatest triumphs. A strong co-founder relationship is crucial for enduring the highs and lows of entrepreneurship.
Find the right people to hold you accountable, balance out your skill set and make the experience of running a business a little less grueling.
7. It sucks, but it gets better
In Lemonlight's early years, I was regularly working 14-hour days, putting out constant fires and feeling like my to-do list was never-ending. Today, the company runs pretty smoothly with the structures and people we have in place, allowing me to focus on big-picture thinking and finding areas where my expertise is helpful.
I won't sugarcoat it: Starting a business is hard. But if you just take it one day at a time, it really does get easier.
8. A little progress every day is impactful
Speaking of taking it one day at a time, little progress every day adds up. We've had days where the wins and milestones were especially noticeable, but most of the last 10 years has just been moving the needle forward a little bit at a time.
Ten years later, somehow that amounts to 20,000+ videos, 5,000+ clients and 150+ team members. The progress isn't always noticeable, but it's always there. Consistency is powerful!
9. Financial acumen is important
Having solid finances is a major component of entrepreneurship, and while it's important to find experts you trust to support you, it's also essential to have some personal understanding of your business's finances.
Being able to read and understand your primary financial statements, track your key performance indicators and move the needle towards your financial goals is invaluable. Don't just trust someone else to get it right, especially early on when you probably can't afford world-class help.
Related: 4 Lessons That Most Successful Entrepreneurs Had to Learn the Hard Way
10. You don't save money if you spend it elsewhere
In the early years at Lemonlight, we were conscious of every dollar we spent, but we had a bad habit of "saving" money in one area only to spend it in an unproductive way elsewhere. We'd pat ourselves on the back for cutting costs, but that money wasn't actually helping our bottom line.
If you find an opportunity to save money, make sure those savings stay saved — or, at the very least, they're spent on something with real value. Don't fall into the trap of thinking you've done a great job just to waste that money somewhere else. Real savings should strengthen your business, not just get shuffled around.
Entrepreneurship may be framed as a solo effort, but the reality is you don't have to figure everything out on your own. I hope these lessons from my business can help you skip some of the uncertainty in yours, making progress without quite as many roadblocks.
