Ashley Kenny of Heirloom: “Every experiment is worth it”

Every experiment is worth it. You would be surprised how effective trial and error can be. Little improvements are often revealed when testing different channels, budgets or approaches. The process can have value as long as you have data to review. Few experiments, tests or trials lack value. You may learn that a space or […]

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Every experiment is worth it. You would be surprised how effective trial and error can be. Little improvements are often revealed when testing different channels, budgets or approaches. The process can have value as long as you have data to review. Few experiments, tests or trials lack value. You may learn that a space or approach is simply not right for your business or right now. We have tried a lot of different marketing and advertising approaches and every time, including those that failed to yield a single sale, did yield insight.


As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company” I had the pleasure of interviewing Ashley Kenny.

Ashley Kenny knows firsthand the power of a well-told story. As a journalist, she spent 15 years making ground-breaking, award-winning documentaries for National Geographic and The Atlantic, earning prestigious awards including the Edward R. Murrow and Alfred I. DuPont awards.

Guided by the goal of making staying connected as low-tech as possible, Ashley founded the brand Heirloom. She is proud to manage Heirloom’s overall product development, leads operations, and directs strategic planning, marketing and communications. She lives in Washington, DC., with her husband and two young sons.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I enrolled in the Journalism School at Michigan State University with the goal of becoming an on-air news reporter. After a bunch of local internships and then a summer internship with National Geographic, I fell in love with long-form journalism and documentary filmmaking. I spent nine years at National Geographic working my way up from Coordinator to Associate Producer to Producer. I went over to Al Jazeera America where I was a Series Producer, overseeing their original series. In 2016 I joined The Atlantic as Head of Production, overseeing all the original documentary and animation. When COVID hit in 2020, there was so much pain and sadness. I was presented with a dilemma and knew I had to use my skills and do something for the greater good. And that’s how Heirloom got started.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

My brother Zack and I created Heirloom last year as we were desperate for a way to stay connected to our 93-year-old Grandma, Fran. She was stuck hundreds of miles from us. Due to the COVID-19 pandemic she was unable to have any visitors and lacked technologic skills. She wasn’t even able to watch videos of my two little boys playing, laughing and growing up. One day, I was on the phone with her and she didn’t sound like herself. She was usually upbeat and positive. I realized that the isolation she (and so many other seniors) were experiencing due to the pandemic was detrimental. When I got off the phone I researched different ways to be able to send her videos of my two boys: Liam, 5 and Jack, nearly 2. I learned about the availability of video brochures, a product able to receive a video and be shared with others, typically used for marketing big-ticket items like timeshares and expensive cars. I considered how the recipient can view the messages without their need for technology, including the internet. Perfect for my Grandma Fran, I thought! With significant tech knowledge, equipment and video production experience, I loaded one and took it to my local UPS for shipping. When she received the video book my Grandma was over the moon! She left me a voicemail message in which she was so positive and uplifted. I shared the message with my brother and we talked about how there must be a way to provide this feeling of inclusiveness and joy to seniors and other people during this difficult time. My brother Zack, who is in tech and start-ups, said “I can build an app for that.” That was our “aha moment”.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Early on, when we were testing our app, I had a bunch of focus group candidates giving it a whirl. I recorded those moments. At that point it felt like I had documented so many challenges and needs with the upload process and so many points of constructive feedback on how users engage with the app that I felt our future was incredibly daunting and beyond my know-how. I typed up the notes and walked through them with my brother who took a step back and looked at them as a whole. Through guidance, we were able to group them into a few categories. His experience with designing tech products that are intrinsically intuitive and user friendly really guided this process. At a point where we felt like so many things needed to be tweaked and altered he was a constant and reliable force for keeping us on task and on mission.

So, how are things going today? How did your grit and resilience lead to your eventual success?

Things are going incredibly well. We just reached a huge milestone of 1,000 video books delivered! What kept me going on the way to this milestone was the constant affirmation from customers. Their feedback is what has confirmed that this is a very important and worthwhile endeavor. Through their purchases, watching so many heartfelt personal videos, and the messages of gratitude they sent to us, I am constantly inspired and motivated to keep this channel growing. We know we are supporting families who otherwise would not be staying connected during a time that has been so challenging.

What do you think makes your company stand out? Can you share a story?

What makes Heirloom so special and unique are the ways we can impact people’s lives, especially during some incredibly challenging times. There is one story that was exceptionally meaningful. I sent a simple note to a customer who had purchased six video books from our platform, with the intention of making her order process easier. I inquired if she wanted the same video put on all six books. To my surprise she responded by sharing her personal journey. She planned to make six unique videos, one for each member of her family as a farewell message upon her death. Currently in hospice, Debbie Milam was struggling with a life-threatening disease and prognosis. As she faced her mortality, her intention was to leave a legacy message using Heirloom video books. She wished to share her messages with those that meant the most to her: her husband, children and grandchildren. She directed us to send the finished books to her best friend, to then deliver to her loved ones after she passed. Amongst many versatile uses, I believe Heirloom’s ability to preserve the memory of people with life-threatening illnesses is profound, meaningful and important.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

As a new business owner, with extremely limited resources, I was paying close attention to charges on our business credit card, and noticed an unfamiliar expense. Rather than ask everyone on the team and double check multiple times to make sure this was a correct charge, I instead simply called the bank and reported a dispute. Soon after I realized my mistake. My brother informed me that this was most certainly an appropriate charge. I had literally cancelled shipments to customers. My abrupt action caused a huge debacle, for not only packages awaiting shipment but freezing packages already in transit. I quickly learned an important lesson the hard way about keeping the lines of communication open with everyone on the team and not rushing to judgement and action.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

During the design process of our video book covers, I was told it is important to bring on a professional designer. I was told it was important to have someone who could use industry standard vector illustrations and designs to illustrate different covers. I heeded this advice and was consistently disappointed with the designs. Their presentations didn’t match my vision and voice. In the end, I worked on the designs myself with our social media coordinator. I learned that sometimes if you have a strong vision the best approach might be to take a stab at it yourself before trying to engage with a third party.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

I possess a strong commitment to showing up. I have learned that on the days that you feel inspired and motivated it’s easy to show up and deliver. But on the days when you feel less enthusiastic or lack motivation to work, my advice is to develop a pattern for tradition that becomes second nature. For me, I know that every morning, regardless of how enthusiastic or passionate I am, I do four or five things which get me going, get me immersed. This effort seems to reliably excite me and call upon some energy that I simply didn’t think I had that day. So my lesson here is to find some consistent traditions that you do regardless of how you are feeling because everyday you bring a different level of energy and excitement.

I have developed the ability to question our approach at the beginning, middle and even the end of projects and planning processes. I think too often people begin a task, partnership or develop a project and don’t question the course or approach throughout. Something I have learned through training, and also by doing and failing, the general importance of questioning why we are doing something a certain way. I try to exercise this approach even after some costs or considerable amount of work has been expended. It is never too late to adjust course or pull the plug on an idea altogether if it is not working. The better approach is to figure out what specifically is not working. I think the ability to always question or be critical of yourself or past decisions will prove to be, in the end, worthwhile.

Lastly, having a sense of humor and not taking things too seriously is something that has served me well. A positive attitude, wherein you are consistently able to have fun and joke, prevents burnout and helps maintain a positive environment and energizing team spirit. On phone calls or when submitting designs, my brother and I are constantly inserting jokes and laughing at ourselves or our ideas. This level of comfortable familiarity keeps things lighthearted and silly. And it keeps us coming back to each other because we know it won’t be a dreaded interaction.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

One means of thriving and avoiding the dreaded “burn out” is to stay flexible, keeping your eye on the mission and the overall “why” you are doing this. Don’t let small things that might feel like failures weigh you down. Rather, I suggest you should expect them and plow past on to the next. If you get too hung up on what was a non-win you are already spending energy that you could have used toward the next potential gain.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

I have seen people forget their overall goal. I think it is really important to go back to what motivated you at the very beginning to do this work. I have also seen leaders neglect to consider ideas from everyone on the team. You might hear a voice from someone who doesn’t traditionally work in that space; i.e., marketing ideas from your social media coordinator. Consider that every idea or piece of feedback is valuable because, even if it is not something you end up acting upon, it is someone’s interpretation of a challenge they are seeing. These comments are gifts and very worthy of consideration and attention. This form of welcoming ideas and feedback creates an open door environment, with the potential of uncovering the next genius idea.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

Running a company, as the question says, requires the art of keeping moving parts moving. I see my key role as a responsibility to the parts, including all stakeholders from my staff and consultants, to suppliers and vendors, to my prized customers, both present and future. I envision each day as one requiring that I need to know how the parts are running while restraining myself from taking over the work. I try to act as an informed consultant to my running parts rather than as the sole operator.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading My Company”? Please share a story or an example for each.

  1. Every experiment is worth it. You would be surprised how effective trial and error can be. Little improvements are often revealed when testing different channels, budgets or approaches. The process can have value as long as you have data to review. Few experiments, tests or trials lack value. You may learn that a space or approach is simply not right for your business or right now. We have tried a lot of different marketing and advertising approaches and every time, including those that failed to yield a single sale, did yield insight.
  2. I wish someone told me I was going to think about this business as much as I think about my kids. I have two children and in some ways Heirloom is my third. As an owner and founder, you are never quite able to turn off your brain as employees in some industries may be able to do. For me, Heirloom is constantly on my mind and seems to come up in every conversation. It is important to create distractions. Soon I am headed to the beach with my family and I think leaving my dedicated Heirloom physical desk and space will create this needed turn-off time.
  3. How long the growth of a business takes and how important consistency is to performance. As long as you are growing at a steady rate, your product or service is seen as vital and successful. Growth into a big commercial business can take years. Don’t expect things to happen overnight. You really have to be okay with playing for the long-game and really committed to what can end up being a long timetable.
  4. You are going to have to get comfortable calling in favors with friends. There is never enough money nor time for all the things you want to do. So, you are going to have to get scrappy and strategic and call in favors. Get over yourself and realize that you have been helping friends and doing for others for years. A business startup may require you to get some returns on the investments you made years ago.
  5. Had I known how much fun business development can be, I probably would have done it sooner. I really always knew that there were many potential benefits of business ownership. There is outright joy and excitement when you see your product get featured on a national platform or hundreds of sales coming through. Taking on a concept, building a product and putting it out there is a daunting and often perilous act, but the big risk can potentially bring equally big reward. The gratification and appreciation I have seen is truly not like anything else I have done before.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

We all hope to become an elder. We also hope to become an elder with a high quality of life and providing meaning to others. If I could create a movement, it would be to inspire more people to care about seniors. Knowing my Grandmother was feeling alone and not stimulated by the joy she gets from seeing her family really broke my heart. If Heirloom could start a movement, my hope is that it inspires more people to think about this generation and come up with innovative ways to positively influence their lives.

How can our readers further follow you online?

Visit SendHeirloom.com and follow us on social media through the handles below:

Instagram: @sendheirloom

Twitter: @sendheirloom

Facebook: @sendheirloomofficial

This was very inspiring. Thank you so much for the time you spent with this!

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