Inspiration & AdviceThree Lessons Entrepreneurs Can Learn From Rappers

Emma McIlroy, CEO of WildfangEmma McIlroy, co-founder and CEO of Wildfang shares lessons learned the hard way at OEN’s 2014 Entrepreneurial Summit.

From the outside, the tomboy fashion startup Wildfang looks like a string of impressive successes—from the 20,000 people who signed up for its mailing list before it had a single product to sell, to its $2 million fundraising round, to its first-place win in our 2013 Tom Holce Entrepreneurship Awards.

But like any startup, pull back the curtain and you’ll see a history of struggles, failures, and uncertainties. Wildfang co-founder and CEO Emma McIlroy shares a honest glimpse of what it’s like to be at the helm as a first-time entrepreneur. As she outlines the three key lessons she’s learned and the 9 pieces of advice she has for budding entrepreneurs, she calls upon some of the more famous graduates of the School of Hard Knocks—that is, rappers Run DMC, Brother Ali, and Gang Starr.

Lesson #1: You are going to do some sh*t that you don’t want to do.

Lesson learned from Run DMC’s “Hard Times”: 


You’re going to do so much stuff that feels so not good and is so hard. Most people in life try to avoid that stuff. CEOs don’t get that luxury. And I’m not talking about hard things like budgets. Three-year budgets are not my favorite thing to do, investor reports are not the most enjoyable thing to write up every month. But I’m talking about the really hard stuff.

In my first year of business, I’ve given out bad performance reviews. It sucks. It sits with you all day, you know you’re doing to do it, it doesn’t feel good. I’ve fired people. I fired at least one very good friend. I fired someone who left a very well-paying job somewhere else to come work at Wildfang. I have disagreed with my senior advisers and investors and made really big decision that they were in disagreement with. I’m talking about the things that bring so much anxiety and stress to your life, that push you to your absolute edge, that push you so far outside of your comfort zone, it’s unbelievable.

So what can I tell you guys, what’s the advice? It doesn’t seem super helpful to tell you all that you’re going to face some really hard times.

1. First, accept it and expect it. You’re not a bad person, it’s going to happen. Be kind to yourself, give yourself a break. Being a CEO is probably the hardest thing you can do with your life and if you don’t know how to self-soothe, if you don’t give yourself a break occasionally, it’s going to be a really rough and rocky path.

2. Try to address every situation of conflict with empathy and professionalism. Even the people that I have had situations of conflict with, after time has passed, they are still very good friends and supporters of our business and our family. Try to put in place processes that make things less subjective and less emotional. I’m talking about things like defining your cultural values. Once you define your cultural values, it allows you a filter as to what you should and shouldn’t do and who you should and shouldn’t hire. Make feedback processes very explicit, make time for them.

3. Lastly, remember the why. Remember the big mission. Everyone on our team knows what the big mission is, so even in the darkest times I find that we know we’re doing something for a greater cause and for something outside of ourselves.


Lesson #2: There’s always a way and there’s always a play.

Lesson learned from Brother Ali’s “Chain Link”: 


The thing that I find is a common trend among the most successful startups is even in the most grim and dire situations, they find a way.

I could tell you about our first private label collection, which arrived two weeks before launch in Portland… Maine. I could tell you about a very well-known celebrity – I won’t name names – who decided that she didn’t like the photos we’d taken of her and didn’t want us to launch our marketing campaign 72 hours before it was due to go live. I could tell you about when we told everyone, including The Guardian and The New York Times, that we were going to be live in five weeks, and then our developer went AWOL with the site we’d been building for 5.5 months and left us with no code and no front-end or back-end, and we had to rebuild it in five weeks. Here’s what you need to do:

1. Find a way under, over, around, and through those walls. I can guarantee you with a startup that people are going to continue to put up walls for you. That is literally the one thing I can guarantee you.

2. Motivate your team to find solutions. The relentless belief and refusal to quit starts with one person. That person is the CEO. That’s your job. You do not have an option to quit. The belief and positivity must stem from you.

3. Verbalize the hard stuff. When the really hard stuff happens at Wildfang, and it happens there on a weekly basis, I call the team together and I quite literally say, “This is one of those times. This is one of those times when the bad stuff has happened, and we always find a way through it. So we’re going to sit here until we find a way through it because that’s what we do.” Those are the times when we actually come up with the best stuff. We find our moments of genius in those times.

Lesson #3:  The key to your success is in motivating other people.

Lesson learned from Gang Starr’s “Moment of Truth”: 


Entrepreneurs have something in common, which is that they’re hungry, ambitious, and by and large intelligent, talented, and successful. Here’s the kicker: your success in your startup has nothing to do with what you can do. It has everything to do with what you can get other people to do for you.

Every single day you will be forced to convince other people that what you’re doing is right and powerful. That could be vendors, that could media, that could be staff, that could be investors. Quite literally, the fate of your company no longer rests in your hands alone. For many entrepreneurs, that’s quite an interesting thing to get your head around.  Some advice that I would offer up, for what it’s worth:

1. Number one, assess your team. Know why they show up to work every day. Know what motivates them. Some people on my team are motivated because they’re young in their career and they want challenges and mentorship, and we give them access to world-class advisers. Some people are motivated by the fact that they came from a very senior position at a big corporation and didn’t have a lot of control over their function. Work out what keeps your employees high because when they’re high they move mountains.

2. Become a great salesman and a phenomenal storyteller. You are going to tell stories and sell every single day. I was in Seattle for a conference, and I was there for 24 horus, and in that time I managed to convince three baristas and one bartender that they needed to shop at Wildfang. So get real good at it. You’re going to become a salesman very quickly.

3. Focus on the win for your partner. It’s phenomenal how many startups show up and say, “Can I have… give me this… can you tell me this…” You’re going to spend so much time with people who are more important than you, who know more than you, and whose time is more precious than yours. I try to go into every one of those meetings, whether it’s a celebrity or an investor, and the first thing I do is try to create a win for them. Why should they care about my company? What can I do for them? What’s the win for them?

See Emma’s full story at OEN’s 2014 Entrepreneurial Summit. Video produced by 10 Bridges Media, LLC

Visit our Summit Playlist to see other stories from OEN’s 2014 Entrepreneurial Summit.

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