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Finding partners that can complement you is your startup’s first critical challenge; here’s how to go about it

Brent Grinna knew he had a great idea. It was 2010, the iPhone was quickly becoming ubiquitous, and LinkedIn and Facebook were getting bigger by the day. In this environment, a mobile app would be far better for connecting university alumni than forcing them to call up their alma mater or buy a book that listed everyone's phone number. The problem: while Brent was a Harvard Business School graduate, he didn’t have the technical chops to build the app. What Brent did have was passion, vision, great contacts in the Boston ecosystem and a scrappy can-do attitude.

How EverTrue's founding team came together

With a wireframe he’d put together in PowerPoint during business school, Brent made the rounds of Boston tech meetups sharing his idea and connecting with developers who might be interested in partnering on his project.

At one of these meetups, Eric Carlstrom, a serial entrepreneur with expertise in both iOS development and building engineering teams, was in the crowd. Brent and Eric hit it off that night and drinks quickly turned to long business conversations. After a month or so, the two decided to pursue Brent's idea together. Brent had found his technical cofounder, and it was time to get to work building out the first product.

It was right around this time that I met Brent at an education conference in Chicago. I was there to speak about my experience helping schools increase engagement with alumni and prospective students through Facebook pages. Brent was camping out on the side of someone else's booth, gathering intel and talking to potential customers.

Brent and I also hit it off quickly. We realized we could help each other, as I was looking for a way to make my consulting work more scalable, and he could tap my experience in educational sales — a field that was completely new to him.

"Picking the right business partners takes work more than luck"

After I sent him some leads from a long west coast road trip — where it became obvious that potential customers were excited about the app — Brent insisted that I meet with him and Eric. They walked me through their plans. It was enough to convince me to join the team as EverTrue’s third cofounder.

Perhaps the biggest decision of your professional life

You might think that Brent got lucky — two cofounders just seemed to fall from the sky. But picking the right business partners takes work more than luck. For many founders it’s the biggest business decision of their lives.

Whether he knew it or not, Brent had followed many of the best practices for recruiting co-founders:

  • He had a deep belief in what he wanted to build
  • He wasn’t afraid to acknowledge his weaknesses in tech and go-to-market skills
  • By making himself a familiar face at meetups and regularly asking for help, he acquired a stable of great mentors, who gave him invaluable introductions and feedback
  • He tapped his network to round out his team.
As a founder, you may feel you can short-circuit the process and brush off these lessons. If Jeff Bezos built Amazon on his own, why do you need a cofounder? It’s a fair question.

Data from Crunchbase shows that 46% of startups that raised at least $10 million or more and 52% of startups that had a successful exit had a single founder. And while long-established conventional wisdom in the startup world suggests going solo decreases your chances of success, a 2018 study by researchers from NYU and Wharton shows that single-founder startups survived longer and generated more revenue than those founded by teams.

You don’t want to rush into a pairing or stop your search prematurely

Still, for every Bezos out there, there’s a Page and Brin or a Jobs and Wozniak. And most startup advisors recommend you find a cofounder.

“Being a founder is such a lonely road,” says Kelly Fryer, program director of the Barclays Accelerator, powered by Techstars in New York. “Why make it even more lonely when you can surround yourself with a team? You’ll move so much faster, execute faster, build faster.” It’s a message echoed by Y Combinator. Only around 10% of the companies accepted into its prestigious accelerator program are solo-founder startups, and partner Jared Friedman says “all else being equal, it is a lot easier to start a company with cofounders.” 

The Bachelorette approach to picking a cofounder

So if you decide to forgo the solo approach, how do you find the right cofounders?

Brent’s approach is by no means the only one. Some founders search through online resources like CofoundersLab or the cofounders Subreddit. Then there’s Gloria Lin, a product veteran of Flipboard and Stripe, who, in a widely-circulated blog post, described in detail the process she went through to find a cofounder. Her inspiration? Dating.

Lin tested the waters with six different potential cofounders before settling on Joel Poloney, an engineer and experienced cofounder who worked at Google and Toro. The two launched Timber, whose mission is to streamline payments in the construction industry to reduce costs.

Core to Lin’s process was a questionnaire, which has been making the rounds of the startup circuit. Its 50 questions are designed to spot compatible candidates and eliminate the rest.

"You can learn a lot in a short time by having three to five confidential conversations.”

Some of the questions were time-tested. What are your weaknesses and how do you compensate for them? When have you been willing to take an unpopular stance? Others are probing. Is there anything I should know that may affect your time or legal status as a founder (visa, green card, criminal record)? Is it possible to build a wildly successful company without burning out or damaging other parts of your life (family, health)? Others still get down to the nitty-gritty reality. How many hours a week are you willing to work? For how long? What sounds good? What seems like hell?

If her approach seems like overkill, it’s deliberate. “You don’t want to rush into a pairing or stop your search prematurely,” Lin told First Round Review.

So you’ve met a cofounder candidate. Now what?

Whether you pursue Lin’s exhaustive questionnaire or not, due diligence checks are a critical part of the process. They can be especially fruitful in tight-knit startup circles in Silicon Valley or New York. “The backchannel is really important,” says Hunter Walk, a partner at VC firm Homebrew. “Obviously, the references are going to say glowing things,” says Walk. “But you can learn a lot in a short time by having three to five confidential conversations.”

The aim is not to uncover dirt on someone — that rarely happens, Walk says — but to really understand whether a person has the strengths necessary to be a cofounder. “Some people are very established, but as individual contributors,” says Walk. “Have they had experience building teams? There are folks who may be wonderful thinkers but have difficulty convincing others to join them.”

Don’t be afraid to be probing. “Doing good reference checks is hard, so be sure that you get plenty of specific and detailed examples to support the positive and negative things that come up,” says Ariel Poler, a serial entrepreneur and veteran investor. Brent and I did just this after we met in Chicago. Brent played football with some of my best friends at Brown. We both reached out separately to these friends and they unanimously came back with, "we can't believe it took you two this long to connect," which was a great start.

Call a friend?

Some founders prefer to avoid the uncertainty inherent in teaming up with someone they don’t know, and instead choose a close friend. If it’s a friend you know in a professional context, that could be a great choice. “Ideally, you've known your cofounder for a long time and have worked with her,” says Poler.

"You’re going to be making very tough decisions with them and be in very stressful, conflicting situations"

But working with friends has its pitfalls. “I’ve seen it work,” says Frye. “But you’re going to be making very tough decisions with them and be in very stressful, conflicting situations with your best friend. Do you want that to be a part of your relationship? Just because they’re your friend doesn’t mean they’re the right person.”

Delaying is certainly an option

If you remain unsure about whether you need a cofounder, you can undoubtedly postpone the decision. Indeed, it’s never been easier for single entrepreneurs to get started on their dream. There’s a vast network of developers who will take your idea and turn out a prototype or minimum viable product.

Outsourcing the tech, however, will only get you so far, says Fryer. “Ultimately, when it comes to scaling your product and building out great new features and a great UX — building something investors are going to be interested in — then having a technical cofounder becomes paramount.”

It’s not easy, but a strong team will make it easier

Even with the good fortune we had in finding each other, building EverTrue wasn’t easy. There wasn’t a lot of sleeping. We had to deal with stress. We had to figure out how to work together. We had some really tough conversations as we wrestled with the company’s direction.

Nine years later, EverTrue is still running strong, with Brent as CEO. Eric and I have moved on. But it’s clear to me that EverTrue’s success was predicated on Brent finding two compatible cofounders. As a founding team, you’re going to be joined at the hip for many hard years. You need partners who share your values and vision and who are ready to give 250%.

Takeaway: Take your time to find the right match

The most important advice that I give founders today is this: do not rush to enlist a cofounder just to check a box.

Focus first on telling your story, building your product and attracting customers. As you get yourself out there, that early employee or passionate angel investor could eventually become the cofounder you were looking for all along. It may take time. But these things often happen when you take the weight of the cofounder title out of the equation. If you are focused on the things that matter the most, the rest will fall into place. Keep building!

A cohesive and well-rounded founding team is the cornerstone of most successful startups. Cofounders must share values and vision. And they must combine experience, technical chops, business savvy, people skills and leadership qualities into a whole that is greater than the sum of its parts.

That’s not easy to do. But the strategies that experienced founders and startup advisors recommend here will help you devise an approach to finding a cofounder that works for you.

— Jesse 

The views expressed in this column are solely those of the author and do not reflect the views of SVB Financial Group, or Silicon Valley Bank, or any of its affiliates. This material, including without limitation the statistical information herein, is provided for informational purposes only. The material is based in part upon information from third-party sources that we believe to be reliable, but which has not been independently verified by us and, as such, we do not represent that the information is accurate or complete. You should obtain relevant and specific professional advice before making any investment or other decision. Silicon Valley Bank is not responsible for any cost, claim or loss associated with your use of this material.

About the Author

Jesse Bardo is a director in Early Stage Practice for SVB in Boston, where he helps Boston’s early stage founders build amazing businesses in one of the world’s best innovation ecosystem. To this end, he connects entrepreneurs with Boston’s accelerators, universities and partners, as well as internal SVB staff, to help his clients scale. Every day, Jesse sits at the intersection between founders, who are dedicated to what they are building, and the bank’s global network and from this vantage point he gets to help companies and individuals grow.

Suffice it to say that Jesse has been around the deep-tech startup block: He honed his entrepreneurial moxie as one of the founders of EverTrue, a startup that snagged a spot in the 2011 class of Techstars Boston, a mentorship-driven accelerator. A SaaS company catering to higher education advancement teams, EverTrue raised over $1 million in angel investment, then went on to win the MassChallenge, a competition focused on accelerating high-potential early-stage entrepreneurs. After gaining Series A funding with Bain Capital Ventures, Jesse and his team grew the company to 400-plus customers and 50 employees in Boston’s Seaport neighborhood. During his seven years with EverTrue, Jesse held most of the nontechnical roles within the company, including sales, customer success, enterprise customer success and customer experience. Jesse’s accomplishments with and passion for Boston’s early stage ecosystem now inspires his work at the bank, where he serves his favorite kind of customer — the Boston entrepreneur.

Beyond EverTrue, Jesse has also been an investor and mentor for early-stage startups; this includes serving as a Techstars mentor himself. He also volunteers as the Abbot Academy Fund director for Phillips Academy Andover and is chair of the Phillips Academy Regional Leadership Boston team. He holds a bachelor’s degree in American studies from Wesleyan University, Middletown, Connecticut.

Jesse lives in Boston with his wife and two children. Outside of work, he is a diehard European soccer fan. And here’s a word to the wise: Don’t come knocking when the Tottenham Hotspur are playing, unless you’re willing to give Jesse’s favorite soccer team your undivided attention.

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