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Meet Ashley Akin: Driving Willow & Ivy Press to Stylish Success in Greeting Cards

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As part of the Morning Lazziness series about empowering women who encourage and do incredible things with their ideas in society, I had the pleasure of interviewing Ashley Akin.

Ashley Akin is the Head of Business Development of Willow & Ivy Press – the ultimate stylish greeting card brand with a touch of playfulness. Started as an extension of Leanin’ Tree greeting cards, Willow & Ivy is on a mission to make cool cards that keep people close and connected with fun and feminine images that feature a variety of playful touches like bold colors, glitter, and foil, as well as hints of humor that spread a little love wherever they go. All cards are made in the USA, use responsibly sourced paper and printing materials, and are curated by a team of all female writers, designers, and mentors. 

Here’s what we found out about Ashley‘s daily routine, followed by an exclusive Q+A.

Can you share the story behind your journey as an entrepreneur?

While I have helped create something new at Leanin’ Tree with Willow & Ivy Press, my journey has been somewhat different than a traditional “entrepreneur” as I was working within an established company. I started my career in strategy consulting where I developed a love for helping companies spark innovation, solve problems, and transform business processes. I had worked there for 3 years when I had the opportunity to join Leanin’ Tree and transition from a strategist into an operator role. The team at Leanin’ Tree was fully supportive of me acting as a “mini-entrepreneur” within the company, and I am so proud of the way our teams have come together to make Willow & Ivy Press a reality. 

What challenges have you faced as a woman in the business world, and how have you overcome them?

Early in my career, I once had a mentor point out that it was helpful to amplify the voices of other women in a room. I have found myself in challenging situations where my voice is not always heard. As I have advanced in my career, I try to look for situations where I can support other women and amplify their voices. Often, I find it can change the momentum of the conversation and empower others to share their thoughts. 

How do you balance your professional and personal life as an entrepreneur?

Since my journey has been a bit different than a traditional entrepreneur, I can’t necessarily say what worked for me will work for others, but I have found a few ways to keep a healthy division between my professional and personal life. I try to stay very organized with my daily, weekly, and monthly to-dos. I start each day by creating a list of the most important items to accomplish that day. With an endless to-do list and a finite amount of time each day, I find it important to create space and define success on a small scale. At the end of each day, I can disconnect knowing that I pushed progress forward. Additionally, I try to practice mindfulness in my personal life and stay present around family and friends. There will always be more projects and challenges awaiting me in my professional life, so I do my best to disconnect and enjoy my time outside of work to its fullest. 

What strategies have you found most effective for networking and building connections in your industry?

The greeting card industry is one of the most friendly, supportive, and well-connected industries you could find yourself in. Leanin’ Tree and Willow & Ivy Press is a member of the Greeting Card Association, or GCA, through which I have met countless other makers, suppliers, and retailers. If you are so lucky to find a supportive organization within your industry, I highly encourage you to join. I also find Instagram is a great way to build connections. We have met so many other makers through posts, stories, etc., and I love being able to follow and support their journeys.  

How do you approach mentorship and seeking guidance in your entrepreneurial journey?

I think mentorship is important across all industries. I have had countless mentors who have shaped me into the person I am today, and I am so appreciative of the time they have invested into my career growth. I find mentors by reaching out to senior leaders I have worked with and asking for their feedback and guidance. I also try to find colleagues in similar roles as mine. Peer mentorship is so valuable, and I have learned so much by talking with my peers who have navigated similar circumstances to my own. The team at Leanin’ Tree have been incredible mentors when bringing Willow & Ivy Press to life. I have learned so much from their long-standing experience in the industry and am grateful for their guidance and support. 

Can you talk about a specific setback or failure you’ve experienced in your business, and how you bounced back from it?

There have been many ups and downs throughout the launch journey, it’s hard to pick a specific one. We often reframed setbacks through the lens of a problem-solving framework. Instead of focusing on the issue, our team focused instead on how we could solve the issue. By keeping a forward-facing mindset, we were able to maintain momentum, which isn’t always easy when building something new. I try to continue to practice this mindset shift, looking for positive solutions instead of focusing on negative setbacks. 

In what ways do you prioritize diversity and inclusion within Willow & Ivy?

Ashley Akin Willow & Ivy Press

We try to prioritize diversity and inclusion in both our teams and product at Willow & Ivy Press. When developing our initial collection of greeting cards, it was important to us that our cards reflect a diverse range of designs and messages. We pour countless of hours and thought into our design decisions to ensure we speak to range of experiences in all our sending sentiments. Within Willow & Ivy Press, we are an all-women team of writers and designers with some having over 30+ years of experience in the industry and some having only a few years of experience in the industry. As a team, mentorship is our number one priority. We make it a point to ensure every voice is heard and to mentor the next generation of women. We continually focus on building a welcoming and inclusive team culture, and I am so lucky to work with such a strong, supportive team of women. 

How do you stay motivated and resilient during tough times in your business?

First and foremost, I try to speak honestly when tough times arise. Being honest helps build rapport and morale on teams, and I know I always feel less alone and more motivated when we are facing a challenge as a team rather than individuals. Personally, I try to set small goals and achieve small wins in times of low motivation. Small wins add up to big wins and create the momentum to keep pushing forward no matter how challenging or hard it may be. 

What advice would you give to other aspiring women entrepreneurs who are just starting out?

While I may not have had the traditional entrepreneurial experience, I would love to share what has helped me navigate a new industry and career journey –

  • Ask questions early and often. Don’t be afraid to make it known that you are new or inexperienced. I have found that people are always willing to help and being honest with what you don’t know opens doors for others to help you. 
  • Doing something new is scary, but you can do it. There have been many situations where I felt like I was in over my head. Keep pushing forward, ask for help, and don’t be afraid. You can do it, and once you have, you will continue to move on to even bigger challenges. 
  • Remember, it’s all practice. I often repeat these words in my head when I am faced with a daunting task or challenge. No matter how large or intimidating the next step is, it’s always practice for something greater. 

Can you share a memorable success or milestone that you’ve achieved in your entrepreneurial career?

Launching Willow & Ivy Press on June 3rd was a huge milestone for our team. It was a long journey from initial product development to production to launch, and I am so proud of how we made our dreams a reality. I realize this is just the very beginning of the journey with hopefully many more milestones along the way. I can’t wait for what’s next – we are just getting started!

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