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Cathryn Lavery of BestSelf: “Women have a way of working that’s flexible and adaptable”

Women have a way of working that’s flexible and adaptable. I know lots of founders who have children or other interests outside of work that demand their time and attention. I love how these women have created a way of working and doing business that has room for all the things that are important in […]

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Women have a way of working that’s flexible and adaptable. I know lots of founders who have children or other interests outside of work that demand their time and attention. I love how these women have created a way of working and doing business that has room for all the things that are important in their life. These examples of work-life harmony are powerful because they prove that a new way of working [and living] is possible for more people.


As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Cathryn Lavery.

Cathryn Lavery is an entrepreneur and creator. As founder and CEO of BestSelf Co., she took the company from zero to 8-figures in less than two years. BestSelf won Shopify’s Build a Business Competition in 2016 and the Build a BIGGER Business competition in 2017 — making BestSelf Co. the only company to win both awards consecutively. Selected for Forbes 30 Under 30, Cathryn and her work have been featured in Fast Company’s 2017 Innovation by Design Awards and numerous other reputable outlets.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I grew up in Northern Ireland and went to university in England and Scotland, where I trained to become an architect. After graduating in 2011, I secured my dream job as an architect in New York City. I was super excited to emigrate to the US and start a new life.

But, things didn’t work out as planned! I’d already interned for the company I was moving to New York City for. They knew my work, and I’d accepted a salary of 40,000 dollars. A couple of months before moving over, I got an email to say my pay was being cut by 25% to 30,000 dollars because there wasn’t enough work.

It was a blow, but I felt reassured by their promise to increase my salary once the workload increased.

But that wasn’t the only goal post to move…

I arrived in the US with just a few hundred dollars to my name and two weeks to find my feet before starting my job. But one week in, my new employer rang with the news that they still didn’t have enough work for me. They were pushing my start date back a further six weeks.

It was at that point I realized that I couldn’t trust a job to look out for me. So, to help me get through those first six weeks with no income, I started to hustle and do things on the side. I launched my first Shopify store and continued working on it alongside my architecture job after I started. About two years in, I realized architecture wasn’t for me. Besides, my Shopify store was generating more income than my paid job — and I was only putting a couple of hours into it each week. At that point, I quit my job to become a full-time entrepreneur, and I’ve not looked back.

Can you share the most interesting story that happened to you since you began your career?

2020 was a big year for most of us! For me, it was the year where my business partner and I decided to part ways, in addition to problems created by COVID. Choosing a business partner could be the second most important relationship you ever choose [the first being who you marry]. In 2020, I found that ending a business partnership can be more challenging and more expensive than a divorce.

The business divorce stemmed right back to the beginning of our partnership when I didn’t know what I didn’t know. If we’d had hard conversations earlier on, dissolving our partnership could have been smoother. Everything from our agreed equity split to our operating agreement created problems that took a lot of time and effort to resolve and became a very tiring process.

I wrote an extensive article about the expensive lessons I learned from my experiences on www.littlemight.com because I wanted to give other people the benefit of my hindsight.

Figuring out terms for the business divorce almost broke me and my business. I lost a year of creativity and positivity. It was tough, but this experience also showed me how resilient and strong I am. I discovered new depths to my character, and I learned a lot of new skills and lessons in the process, which I know will be invaluable in the future.

It felt incredible to finalize the divorce because it meant I became the sole owner of BestSelf Co. This transfer of ownership has been so liberating and has created a whole new space for new opportunities to show up in my life. Full ownership also unleashed a new spark of creativity in myself and my team, and I’m excited about all the new ideas and products that are happening as a result.

Life’s gifts don’t always come wrapped. Sometimes it’s not until you have the benefit of hindsight that you see the blessing in the hardship. But as long as you extract the lesson and grow, challenging events can be the making of your best self.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

There was a time when I went to the wrong job interview and ended up getting the job! As part of becoming an architect, I needed to spend a year in an office. To increase my chances, I secured six interviews with different firms on the same day. I had two in a row, and the first company kept me longer, joking that they were doing it because they wanted to hire me! It meant I was in a rush to get to the next interview.

And that’s when the mistake happened…

There are two firms in Belfast with very similar names. I ended up going to the wrong one. When I walked into the office and announced that I was here for my interview, they said they had nothing scheduled. They assumed it was their fault so they looked through my portfolio and interviewed me anyway. 30 minutes later they offered me a job.

I didn’t realize my mistake until I got an email from the company I was supposed to interview with. They wanted to know where I was! This experience taught me that if you’re confident in yourself, you can still win — even if you make a mistake.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Andrew Warner who hosts the Mixergy podcast.I used to listen to this podcast back when I was working 90-hour weeks as an architect. The podcast used to frustrate me! I’d hear stories about all these people doing cool things in business and with their lives that, at the time, I couldn’t imagine being able to do myself — even if I wanted to.

Over time, after hearing stories from people with a variety of backgrounds, I noticed that my beliefs started to shift. I found myself thinking, “I can do this too”.

I’m grateful to Andrew Warner and his podcast for the exposure it gave me to a different way of being. It was a piece of the inspirational puzzle that I needed to start my own business.

Andrew interviewed me for Mixergy in 2018. It was cool to get the chance to be on a podcast that had inspired so much in me.

Is there a particular book that made a significant impact on you?

The 100 dollars Startup by Chris Guillebeau.

Can you share a story or explain why it resonated with you so much?

At the beginning of my entrepreneurial journey, reading was a big catalyst for me.

In January 2013, I made a list of 22 books I had to read before quitting my architecture job. By this time, I was itching to leave the corporate world and start a business so I had plenty of motivation to consume my list as fast as I could! I’d read every morning and evening during my commute, and this time became my alternative to an MBA — equipping me with the basic principles of running and growing a business.

The 100 Startup dollars by Chris Guillebeau was one of my favorites because it proved that I didn’t need a lot of money to begin a life of adventure and purpose. I quit my job in November 2013 and launched my first business — Calm The Ham — with an investment of less than 500 dollars.

BestSelf Co. didn’t begin until 2015 — a reminder that your first business doesn’t have to be ‘the’ business. Instead, it can be your vehicle to freedom as you figure out what you really want to do.

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

“Not getting what you want either means you don’t want it enough, or you have been dealing too long with the price you have to pay.” — Rudyard Kipling

For me, this quote captures the idea that you can get anything you want if you’re willing to commit to it and work for it. This quote reminds me that I have control over my life, and my results are down to me.

Often, people fall short of where they want to go because they stop too soon. They want something big but don’t take the necessary daily actions, which means they don’t see sufficient progress, so they get disillusioned and disinterested.

This quote is a reminder that you have to do the boring stuff too. It’s a reminder to stick to your habits instead of continually switching up or trying something new. Taking the right actions over a long period of time is what gets results because that’s when the compounding effect kicks in.

How have you used your success to make the world a better place?

I’m proud that our products inherently make the world a better place because they empower people to become their best self. Every time someone achieves a goal, improves a relationship, or starts a new good habit, there’s an incremental shift. When people are their best self, they feel better about themselves and their lives — and that means they show up differently. They feel happier, more connected, and more loving. They desire to make more impact and contribution too. This good energy and positivity change the atmosphere for all of us.

In addition, we support Feeding America.

You can’t be your best self if you’re hungry — it’s one of our basic survival needs on Maslow’s Hierarchy. Did you know that 1 in 8 American’s struggle with hunger? That’s around 12% of the population. We partnered with Feeding America a few years ago to donate one meal for every order.

So far, the BestSelf Co. community has donated over 370,000 meals — something of which the team and I are incredibly proud.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

I think the biggest barriers are confidence and self-belief. I saw this for myself when I launched BestSelf Co. In retrospect, I can see that I opted to launch with a co-founder instead of by myself out of my insecurities around marketing and selling myself.

In general, I think men are bolder about their skills and abilities. They’re more likely to say they can do something and then jump in and figure out how! In comparison, women tend to play down their abilities, wanting more evidence or reassurance before they’re willing to go all-in. Even if a woman is highly qualified and very experienced, if she doesn’t think she fits the bill, chances are she’ll hold back. A man may react differently.

There’s a social narrative too that compounds this.

One piece of feedback we had about the first Self Journal (one of our products) was how the quotes were predominantly male. This wasn’t intentional; it was merely a reflection of how motivational quotes are skewed towards men. In response, subsequent journals were more representative after we searched for quotes from women and minority groups.

The same applies to business, where there are more men in the field than women. It’s the same story in books. One of my good friends launched a Kickstarter for a book called Good Night Stories for Rebel Girls featuring a collection of stories where the woman is the main character. For her marketing, she created a great video showing a full bookshelf and gradually removing all the books that didn’t feature a female lead. By the end of the video, the bookshelf was virtually empty.

Role models are essential because they challenge your perception of what you think is possible. If women can’t see themselves represented in business, it takes a bigger leap of faith to believe they can make it.

Can you share with our readers what you are doing to help empower women to become founders?

One of the most important things I do is share my stories of what it takes to be a founder and what it’s really like behind the scenes. Research has found that if a woman knows someone who’s started a company, then she’s more likely to do it herself. I’ve seen this in my own life. I occasionally hear from people I knew in high school who want to tell me that they’ve started something. I’m proud that I am that female example for some people, which gives them the belief that they can do it too.

As my company has grown, so has the size of problems that I need to tackle. When BestSelf Co. first started, some of our biggest concerns was getting inventory shipped on time. In the last year, I’ve had to deal with a business divorce and a 6-figure embezzlement as well as COVID. I’ve been open about these challenges to show other people how resilient you can be when things go wrong. Somehow, you do find a way forward and eventually come out the other side stronger.

I also share my stories to show how your capacity grows with your business — especially when you invest in your own development and growth.

I also remind people of my start point frequently.

I was an architect with zero business experience! The trajectory of my life wasn’t supposed to head in the direction that it has. I share my start because it’s proof that as long as you have the drive, passion, and desire to build something meaningful, you can.

This might be intuitive to you but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

I have three examples…

  1. In business, women bring a different set of skills and a perspective on life. They spot different problems and visualize other solutions too. What’s more, they understand these problems because they experience them in their own lives in a way that men can’t. This perspective must be represented in business. It’s the catalyst for innovations and startups which grow the economy and create jobs and opportunities for others.
  2. We’ve come a long way in recent years, but we still need more equality. As more women take on leadership roles and become examples of what’s possible, we’ll continue to redress the balance. It’s also important that young girls have more role models and examples of success in business.
  3. Women have a way of working that’s flexible and adaptable. I know lots of founders who have children or other interests outside of work that demand their time and attention. I love how these women have created a way of working and doing business that has room for all the things that are important in their life. These examples of work-life harmony are powerful because they prove that a new way of working [and living] is possible for more people.

Ok super. Here is the main question of our interview. Can you please share 5 things that can be done or should be done to help empower more women to become founders?

  1. Be aware of the labels that get attached to women in business. Terms such as ‘mompreneurs’, ‘boss babe’ or ‘female entrepreneur’ aren’t always helpful or empowering. After all, we don’t say ‘dadpreneur’ or male entrepreneur. We just say entrepreneur — which is the label I also choose for myself.
  2. Share more stories of successful women. The more positive examples that women and young girls can access, the more women will feel encouraged to start their own businesses.
  3. Support each other. The success of one woman doesn’t mean another can’t be just as successful. We don’t have to pull one woman down to build another one up — something we often see in the media. Women thrive in collaboration. It’s essential to make a stand for that support-driven environment inside which more people can succeed.
  4. Drop the myths. Remember that being pro-women does not mean you’re anti-men! It simply means you believe women should be successful too.
  5. Take action. Don’t be silent on the sidelines. Don’t assume someone else will do the work or say the things. If you have something to say that can help women in business, or other minority groups get started, take action.

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

I want to inspire people to invest in personal development so they can become their best self — not just for personal gain, but because of the ripple effect it has on everyone around you.

Your best self is personal… it’s whatever it means to you.

But when you improve yourself, other people see it — and that transformation inspires others to seek out the best version of themselves too.

You shouldn’t stop learning just because you left school. Learning needs to be a lifelong commitment. Self-education is that tool, which empowers you to keep growing, expand your comfort zone, and raise the standards and aspirations you have for your life.

Best of all, you never know the impact your personal ripples make as you become a better person.

Looking back, if I hadn’t committed to personal development when I did, there would be no BestSelf Co. In turn, we wouldn’t have impacted the people we have — both our customers and the team. My life would be radically different too. For example, I’d probably still be working in a job and industry that wasn’t for me.

Personal development and a desire to be your best self opens a door for a more successful and fulfilling life. It’s why I’m passionate about creating products, tools, and resources that can guide people along that path.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Sara Blakely (the founder of Spanx).

I’m inspired by the way Sara Blakely has been able to build an incredible business while maintaining a great work-life balance. What’s more, she did all this at a time when it was difficult to start a business.

I imagine it would have been extra challenging because not only is Sara Blakely a woman, but she chose to create a product for women, which likely made a problem when seeking funding. A lot of the time, men have the investment dollars and if they don’t understand the business or the need for the product, it’s harder for them to say yes.

To me, Sara Blakely is a tenacious badass who just got on with what needed to be done. I imagine she would have had a lot of BS to get through, but she totally crushed it building Spanx into an extraordinary brand.

If she wasn’t who she is, Spanx wouldn’t be the business it is today.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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