I recently spoke to Erin Flynn, CEO and co-founder of the personal styling app Cladwell.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth?

Erin: Cladwell wasn’t originally started by me. In fact, I wasn’t even here when it was officially named Cladwell. But if there was ever something that was created with me in mind, it is this business.

When I joined in 2015, Cladwell was predominantly a men’s personal shopping tool. We had just launched a website for women called Capsules and had fallen head over heels with the idea that better style could be discovered through removing clutter and owning fewer clothes. In other words, less but better.

But Cladwell like every business has gone through many ups and downs from being predominantly venture-backed to most recently being acquired by my husband and I this past August. Personally, this process has taught me far more than I could ever gain in going to business school.

I have gone through many failures and setbacks including my first startup company which ultimately shut down and left me having to move back in with my parents tagging alongside my husband and dog. I think on the outside it can look as if everyone has it together, but I think it’s important that we give people the benefit of the doubt and assume good intentions verse bad. Most people don’t have a straight-line journey to success, and certainly, my own journey has been no different.

It’s not just business for me. It’s personal. We have a simple belief. Business should be a force for good. This is meaningful work. Work that serves people. Work that stewards the earth. Work we were made to do. While I don’t know what the future holds, I do know one thing. I’m so grateful for this season of life, for the late nights long after everyone is in bed and for the ability to continue working to bring Cladwell to as many people as possible.

Adam: How did you come up with your business idea? What advice do you have for others on how to come up with great ideas?

Erin: Five years ago, I woke up, rolled out of bed, walked to my closet and said they very same thing I’ve heard a thousand women say, “I have too many clothes and nothing to wear.” That weekend instead of going to the mall for refuge. I stayed home (wine in hand) and embarked a “capsule wardrobe approach” where I de-cluttered my entire closet filled with 450 items. It was vulnerable, stressful, and quite honestly… it changed my life, forever.

This was the foundation for the idea and why we not only help you get dressed at Cladwell, but we help you change the relationship with your clothes as well as help you love and wear everything you own.

I think it’s much bigger than personal styling. Because as it turns out, the problem isn’t our messy closets, it’s our messy relationship to style, the fashion industry, and ourselves.

Great ideas often solve a problem whether that be functionally or emotionally and if not a problem, they at least highly entertain us. When it comes to finding what that is, think about your biggest pain points and when you find one or two, ask others if they also feel the pain. This is a great starting point to whether or not an idea is just that... an idea, or if it’s a business with a model worth pursuing.

Adam: How did you know your business idea was worth pursuing? What advice do you have on how to best test a business idea?

Erin: We use a process called Design Sprints. It’s a way to rapidly iterate and test an idea without ever writing a piece of code. Not only did we use this to test the concept of Cladwell and our daily outfit recommendations, but we continually use it to roll out new features.

Adam: What are the key steps you have taken to grow your business? What advice do you have for others on how to take their businesses to the next level?

Erin: We’ve had a lot of ups and downs but we’ve been able to grow by continually creating a brand that resonates with our audience. Through that, we’ve consistently developed content and relationships on social media that have helped grow our business beyond just paid advertising.

Adam: What are your best sales and marketing tips?

Erin: Seth Godin says it best, “Marketing is the generous act of helping someone solve a problem. Their problem. Marketing helps others become who they seek to become.” When it comes to tips, you must know who your audience is, go to where they are, and tell them a story. Marketing is doing a lot of little things that add up. Not one big growth hack that goes viral.

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Erin: I think a huge part of being an effective leader is in being vulnerable, compassionate, and courageous. These are typically things that “sound weak” but in actuality, the best leaders I know or have “read” about having embodied so many of these qualities that have led them to ultimately some success at the next level.

I think when you’re able to have vulnerable conversations you’re more apt to have better team dynamics and culture. I think when you fire someone out of having compassion for a person (and their teammates) whose skills weren’t up to par vs. talking about them behind their back it’s better for them and the business, and when you have the courage to do the hard thing, even when it’s not easy it determines the success of a business and a healthy team.

These aren’t weak skills, they are skills we need more of in the world of business and amongst leaders today.

Adam: What is your best advice on building, leading and managing teams?

Erin: The best way to lead is to be an example yourself. You can talk all day long but if you’re not upholding the values that you preach then you can’t expect your employees to act, work or as you’d like. Also, one other side note, is I think so many business owners expect their employees to act as they do… but they don’t give the employees any stake in ownership. As a leader, you either need to have the right perspective, in that a lot of employees aren’t in the same position as owners - and that’s okay. Or, give them the ability to act as an owner if that’s what you want, but you should back it up with true ownership.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?

Erin: My three best tips are:

• There are no silver bullets.

• Lead with empathy, compassion, and courage.

• Be diligent.

Adam: What is the single best piece of advice you have ever received?

Erin: Be unhurried.