People always ask my Poppy Barley co-founder, Justine (pictured left), and me what it’s like working with your sibling. We usually answer with a quick and standard, “It’s great!”
Here’s the much longer truth.
When Justine first imagined the concept of a custom boot company, she immediately sent me a very long email outlining the idea. I dismissed the idea as “okay” (wrong), “already been done” (wrong), and “likely never going to happen” (wrong).
Justine has a billion great ideas; but like the rest of us, not every brilliant idea actually happens, and Justine had never aspired to be an entrepreneur. I didn’t know this would be the idea to change her mind.
And so Justine started working on the company alone. She spent hours making a case for Poppy Barley. After working all day at her full time job, she’d spend evenings and weekends fully dedicated to the idea of an e-commerce, bespoke boot company. She continued to involve me by asking for my input in areas she felt I was stronger, like marketing, sales and brand development. I listened to her pitch. I read every version of her business plan. I was impressed. The concept was smart; the market was huge; and women loved the idea of made to measure footwear.
BUT… I was still hesitant about working together. My sisters, Justine and Larissa, are my best friends. I really questioned whether I wanted to add “business partner” to the role Justine plays in my life. Plus, being sisters didn’t automatically make us good partners. And so Justine and I had a lot of conversations to evaluate our fit as co-founders.
The foundations of a good co-founder relationship are the same, regardless of if you’re related. Here are 7 key traits to look for before entering into a business relationship with someone, including a few personal ways I believe Justine and I are stronger co-founders as siblings.
1) Good co-founders have a shared vision and passion.
As co-founders, Justine and I have a shared vision for Poppy Barley and, as siblings, never doubt the other’s commitment or contribution. This is critical. It allows our disagreements/discussions to be rooted in a difference of perspective, and not something petty like who’s working harder, or worse, about entirely different end-goals for the company. Beyond an alignment of vision, we share a passion for what we’re building. Our passion drives our discipline to execute our vision—to discuss, debate, argue, and move forward.2) Good co-founders can push through uncertainty.
Entrepreneurial companies are in the business of inventing themselves. Uncertainty hits every part of your business. Constant uncertainty takes an entrepreneur to the edge. You operate day to day in situations that are risky, unknown and stressful. Good co-founders can push through it. As siblings, working together in uncertainty is something we've grown up doing as we learned to navigate "the unknown"—from those awkward junior high years to the myriad of life achievements in sport, education, and relationships. Even more than "pushing through" uncertainty, I believe that excelling in uncertainty is something Justine and I do best. We moved a lot growing up. Every couple of years my dad was transferred for work and we’d be whisked away to a new town, new school, new environment, etc. We braved this uncertainty together. Being in an unknown situation with Justine feels completely normal; it’s something we’ve been doing our entire lives. (A little note for our Dad: All that moving was really hard. So many rages and tears as teenagers! But honestly, it shaped us in ways we never realized. Now, I am very thankful for how frequently moving taught me to be open-minded, flexible and completely comfortable in new, awkward situations. Thanks for pushing us outside our comfort zone, always knowing we’d be just fine. We are.)
3) Good co-founders know how to have fun together.
In order to run a successful startup business, you have to genuinely like your co-founder and have fun with them, because once you start slaving away as an entrepreneur, you’ll spend more time together than you know. There needs to be a high level of personality compatibility. You want someone who shares your expectations of work/life design—including when it’s time to just have fun and go for wine. I think this is true for every early member of your team. As siblings, Justine and I spend a lot of time together outside of work – we run together (and sometimes talk about work); we go out for drinks on the weekend; we plan vacations together; we indisputably enjoy spending time together. This is a must.4) Good co-founders trust each other and know when to be independent.
As co-founders, you should be equally intelligent, capable and hardworking. During this interview, journalist Darren Kraus asked us about our co-founder’s greatest strength. For the first time, we voiced to each other the thing we valued most in each other as a business partner. Our answers were delivered with tears in our eyes. I realized our deep admiration and respect for each other, founded on years of interaction and experience as siblings. We completely trust each other. Based on this trust, one of the best decisions we made early on was to divide our responsibilities within the company, placing full ownership for each area on one person. We can’t do everything together. Independent decisions are made all the time. Sometimes we disagree afterwards, but our shared vision and respect for each other makes it difficult to fault the person for a decision. (In case you’re wondering about the answer to Darren’s question: I said that Justine’s greatest strength is her way of thinking. Justine is the most original thinker I know. Most people take ideas and re-arrange them. Justine actually thinks differently; it makes her a product-designing, problem-solving genius. She’s absolutely brilliant.)5) Good co-founders know the ugly truth and are the ultimate support system.
Being a founder of a company can be lonely. At times you’re trying to inspire others (customers, partners, employees, investors) in moments when you can’t even inspire yourself. Poppy Barley has bad moments, bad days, bad weeks. Having the right co-founder is the ultimate support system. My sister Justine is the one person I am completely honest with; she get’s the full, ugly truth, accepts it, and knows how to provide support.
6) Good co-founders have emotional buoyancy.
Being an entrepreneur means no separation between work and life, and founding a company means investing everything you have. Emotions come with it. A good co-founder knows how to build you up and help you bounce back when you're down. As siblings, I believe Justine and I have a strong emotional investment in each other. Our personalities complement each other. Usually, what’s getting one of us down typically doesn’t faze the other. As best friends, sisters and co-founders, we provide emotional buoyancy across many areas of life. When there’s little separation between life and work, I appreciate working with someone who understands the multiple facets of "me" that go into making decisions.7) Good *siblings* go beyond the business.
This one's for the all the sibling-co-founder relationships out there. There are outright benefits to working with my sister, because she is just that: my sister. Our life values are aligned (hard work, open-mindedness, etc). We have a long history of working together. We were able to leap frog the learning curve of close collaboration. We argue well. We’ve seen each other’s true colours a thousand times. Most importantly, being united beyond our business provides perspective on what makes each of us the best version of our selves. When we’re at our best, so is our company.
