10 lessons from a decade of entrepreneurship


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On the eve of my business's 10th 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 top ten tips—ones I wish I'd known in my early days. entrepreneurship. Apply them to your journey if you are 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 may not understand what you really want from them, and their definition of success may not match yours. Without consistent accountability, they won't meet those expectations and will have a harder time learning how to improve.

Establishing clear and consistent communication ensures that everyone is on the same page and moving toward the same goals.

Connected: I wish I knew these four things before I started my business

2. Understand evolution versus 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 a leader when you need revolution.

I've learned (the hard way!) that all leadership jobs 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 goes deeper than “fun”

Fun is an element of company culture, and I believe you should invest in it – whether it's through team breakfasts, team outings, or other activities outside of 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 catered lunches, be mindful of the little things: how your leadership team answers tough questions, how balance sheet transparency by protecting your team from hard truths and how you treat people every day. Your employees will notice all 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 new product hiring decisions—to take longer and cost more than I expected. And even when I try to apply this lesson ahead of time, I'm still likely to underestimate it.

Planning with this principle in mind can help manage expectations and reduce disappointment when things don't go exactly as planned. A tampon 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 had done it sooner.

trainers help you find your leadership blind spots, provide an unbiased sounding board when faced with challenges, and help other members of your team rise alongside you. It can take time to find the right person for your needs, but in my experience, it's been worth the effort.

Connected: 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 strangest concerns, and your greatest triumphs. A strong one co-founding relationship it is essential to weather the highs and lows of entrepreneurship.

Find the right people to hold you accountable, balance your skill set, and make the experience of running a business a little less exhausting.

7. It sucks, but it gets better

In the early years of Lemonlight, I regularly worked 14-hour days, putting out constant fires and feeling like my to-do list was endless. Today, the company works quite well with the structures and people we have in place, allowing me to focus on big-picture thinking and finding areas where my expertise is useful.

I won't cover it: Starting a business is hard. But if you just take it one day at a time, it really does get easier.

8. A small progress every day makes an impact

Speaking of taking it one day at a time, little progress every day is added. We've had days where victories and milestones were particularly notable, but most of the last 10 years have just moved the needle forward a bit.

Ten years later, somehow that amounts to 20,000+ videos, 5,000+ clients and 150+ team members. Progress is not always visible, but it is always there. Consistency is powerful!

9. Financial literacy is important

Having strong finances is a key component of entrepreneurship, and while it's important to find experts you trust to support you, it's also essential to have a personal understanding of your business finances.

Be able to read and understand elementary financial statements, track your key performance indicators and move the needle towards your financial goals is invaluable. Don't just trust someone else to do it right, especially early on when you probably can't afford world-class help.

Connected: 4 lessons the 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 unproductively 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 that these savings remain saved – or, at least, they are spent on something of real value. Don't fall into the trap of thinking you've done a great job only to lose that money elsewhere. Real savings should strengthen your business, not just mess around.

Entrepreneurship can be defined as a solo endeavor, but the reality is that you don't have to figure it all out on your own. I hope these lessons from my business can help you through some of them INSECURITY in yours, making progress without so many obstacles.



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