When Choosing Your Startup Partner, Opposites Really Do Attract

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When Choosing Your Startup Partner, Opposites Really Do Attract
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When Choosing Your Startup Partner, Opposites Really Do Attract

Conventional wisdom holds that a great leadership team is built by people with similar personalities and complementary skills. When choosing a partner, people traditionally look to others they understand and trust -- their friends, mentors or peers -- someone who aligns with their existing leadership dynamic.

But innovation requires getting outside of your comfort zone, and that means being around people outside of your comfort zone. When you choose a business partner, you want someone by your side who will constructively challenge your opinions and force you to think through every decision. The point of a partner is not to confirm your vision, but to expand it.

Related: Looking for a Partner? Learn These 8 Essentials First.

In the startup world, opposites truly do attract -- by choosing someone completely different from yourself, you can form a force of nature within your company that is strong enough to withstand challenges from any angle. Let me explain why, from my own experience and from the founding stories of a few other fast-growing companies I’ve been watching.

Nothing is the new 20 (or 30). It’s pretty common in startup land for a founding team to chafe at the “grown up” brought on to steer a developing business in the right direction -- particularly in tech. But young entrepreneurs should be wary of overestimating the potential of their digital-native status and underestimating the value of an industry veteran.

I created StudyBlue right out of school because I was frustrated with the lack of education resources. A few years later, I met Becky Splitt. We were an unlikely duo -- I was a novice engineer and Becky was a mom and 15-year guru of the tech industry -- but bringing her on as CEO dramatically transformed StudyBlue for the better.

As a founder, you might know how to create a great product, but you also need someone who understands the challenges of translating a great product into a great company. If it weren’t for Becky’s expertise, I doubt StudyBlue's user base would have grown from just a few thousand college students to 5.5 million.

Partnering with someone who has years of experience with the problem your company faces from a professional, or personal, standpoint adds unique value to the solution you’re creating -- value that someone your own age likely couldn’t supply.

Embrace your competition. Keeping your “enemies” close isn’t just a way to watch your back in the business world -- it’s actually another great strategy for finding the ying to your company’s yang.

Ministry of Supply, a new brand that fuses technology and fashion, was born from two different projects that could have easily become competitors. Instead, the three founders -- Gihan Amarasiriwardena, Aman Advani and Kit Hickey -- decided to collaborate.

Related: Win-Win: Strategically Partner With Your Top Competitors

Joining forces with a competitor allows you to fully contribute your unique skills to the company and avoid spreading yourself too thin as you grow. While bringing together two different projects is never easy, you’re likely to develop a better product and have a stronger leadership team in the end.

Since reaching its Kickstarter goal in 2012 within five days for its flagship dress shirt, “Apollo,” the team at Ministry of Supply has used their combined brain power and manpower to expand the line into slacks, socks, base layers and more.

Adopting competing strategies, and even competitors themselves, can create an unexpected balance within a company. By focusing less on individuals, you and your new team can accomplish more together.

Agree to disagree. Partnering with someone whose opinions greet yours like oil to water may not seem wise, but the best decisions you make for your company are often far from easy.

Matthew Bellows, CEO of email sales service Yesware, and Cashman Andrus, CTO, are practically polar opposites. Bellows, your typical salesman, is a dreamer and eternal optimist. Andrus, your typical engineer, is a practical problem-solver and realist to the core. Their opposing personalities are exactly why they chose to work together.

Deciding to partner with someone who holds a completely different perspective (on everything from breakfast to marketing strategies) means your business will be built upon countless arguments. But, as the Yesware team has discovered, these heated discussions can lead to the right decisions in the end. Bellows and Andrus now have claim to the most popular sales email service, with more than 450,000 users worldwide, and $20 million in funding raised from Google Ventures, Battery Ventures, the Foundry Group and others.

While choosing an executive partner with a different background or contrarian viewpoint has its drawbacks -- and may not lead to the shortest meetings -- the pros far outweigh the cons. A diverse leadership dynamic can provide a well-rounded perspective on your product and the market, and just the right amount of friction to set you up for success.

Related: 5 Tips for Picking the Perfect Partner

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