Unlikely Enneagram Duos That Actually Work in Startups

According to Business School professor Noam Wasserman, conflict between founders kills 65% of startups, even the high-potential ones. That’s because, unlike a lack of funding or a bad product, it destroys the business from the inside out. 

If you’ve ever tried to start a business with someone else, that probably doesn’t surprise you. But sometimes, the “right opposite” personalities collide just in the right context, and that clash is exactly what’s needed for the business to thrive. 

In this article, we’re looking at some of the real-world founder pairings where the very differences that should have pulled them apart became the engine behind their massive business success. We’ll explore those dynamics through the lens of the Enneagram.

Two and Eight: Justin Mateen and Sean Rad (Tinder)

These types have direct opposite vibes. Enneagram Twos want to be liked and needed as everyone's go-to person, while the Eight doesn't mind hurting feelings if it means getting the job done. But as it turns out, that exact friction is sometimes the secret sauce for a business. We saw this play out with Justin Mateen and Sean Rad, the founders of Tinder. Yea 

In a 2014 interview, the pair described Mateen, a classic Two, as the “social butterfly” of the operation. According to the Tinder origin story, he seeded the dating app with early users by hitting up university sororities and throwing parties where the “invite” was having the app downloaded.

Rad, meanwhile, brought the high-intensity energy and forward momentum that defines an Eight. Within the first three months, he was already pushing for rapid global expansion, insisting on having feet on the street in multiple countries to gather feedback and scale the app. He also led the charge in Tinder’s legendary legal showdown with parent company IAC, where Tinder accused the corporation of manipulating financial data to undervalue the company. 

The duo worked because they compensated for each other's blind spots: Mateen marketed the app by leaning into his Two relational energy, while Rad provided the combative Eight grit needed to bulldoze through the corporate world.

Four and Nine: Jack Dorsey and Biz Stone (Twitter)

A Four and a Nine often clash because the Four is all about individuality and self-expression, while the Nine prefers harmony. However, in a team dynamic, the Nine’s non-judgmental presence can work well with the eccentricity of the Four—as was the case with Twitter (now X).

Jack Dorsey, who came up with the 140-character concept of Twitter and coded the site's original version, exemplifies the Four’s preoccupation with authenticity and finding deeper meaning in the mundane. As a teenager, Dorsey spent hours listening to emergency service scanners, which sparked his fascination with how short, coded bursts of communication could connect people in real time.

But while Dorsey birthed the idea, he wasn’t exactly taking things seriously when it came to its implementation. He was reportedly leaving the office at 6:00 PM sharp to attend yoga classes and fashion design courses, which drove other founders (especially Evan Williams, an Eight) mad, leading to the famous ultimatum: “You can either be a dressmaker or the CEO of Twitter. You can’t be both.”

The reason the whole thing didn't burn down immediately was Biz Stone. As a Nine, Stone brought the peacemaking energy that allowed Dorsey’s “Four antics” to exist without breaking the company. As he explained in a 2014 Guardian interview, “I decided one day that I was going to be nice all the time and see if that got me anywhere. And it was fantastic... [Jack] is a sweet person and I couldn’t imagine him doing [malicious things].” 

By the way, plenty of people argue tech titan Dorsey is a Five, and he could be. But the yoga classes, fashion design courses, and carefully curated vibe all read a lot more “moody Four artist with a Five wing” than “detached investigator” to me!

Six and Five: Warren Buffet and Charlie Munger (Berkshire Hathaway)

When you put two Head types together, it often results in paralysis by analysis. They can spend forever spiraling over data and “what-ifs” without ever actually launching anything. But in the right context, this personality pairing is a superpower. There’s no better founder example than the legendary partnership of Warren Buffett and Charlie Munger.

For Buffett, the quintessential Six, the business of investing is all about trust, security and predictability. He’s known to have walked away from many massive deals if he didn't like the person involved, saying, “We do not wish to join with managers who lack admirable qualities, no matter how attractive the prospects of their business.” His biography The Snowball, says that he kept original managers in place for decades, preferring the security of known people over up-and-coming talent.

As for Munger, he brought the intellectual rigour of the Five. As Janet Lowe writes in Munger’s biography Damn Right!, he was obsessed with developing models and systems (like his “latticework of mental models” framework) that allowed him to understand every moving part of a business before he ever made a move. Buffett summed up their dynamic perfectly in his 2015 letter to shareholders, saying that “Charlie shoved me in the direction of 'not just buying bargains' ... He is the architect, I am the general contractor.”

Six and Seven: Richard Branson and Nick Powell (Virgin)

In this pairing, you get the classic “gas and brakes” dynamic where the Seven wants to leap into new ventures for the sheer thrill of it and the Six refuses to move until every 'what if' has a backup plan. For a real-world example, look at the early days of Virgin Group, founded by Richard Branson and Nick Powell. 

As a textbook Seven, Branson’s entrepreneurial career has basically been one long exercise in corporate FOMO. He’s jumped from record shops and airlines to trains, telecommunications and, most recently, stratospheric balloon travel—just for the fun of it. As he puts it, “Fun is one of the most important ingredients in any successful venture. If you're not having fun, it's probably time to call it quits and try something else.”

However, Branson’s urge to jump into new ventures and trust that things will just work out likely would have led to financial ruin if it wasn’t for the stabilizing energy of Nick Powell, a Type Six. 

According to Branson’s autobiography Losing My Virginity, Powell was the one who reminded him of the reality of their bank balance when Branson was ready to blow everything on a new venture. As he wrote in a tribute blog post to Powell after his passing, "He helped us through financial crisis after crisis and was willing to take the tough decisions to reduce costs... Famously – to make a point – even rationing tea, biscuits and lavatory paper!”

One and Three: Kim Kardashian and Jens Grede (SKIMS)

In this pairing, you get a classic clash of standards: the Three wants the brand to look perfect on the surface, while the One is obsessed with making sure it’s actually perfect all the way through. SKIMS, the shapewear brand cofounded by Kim Kardashian and Jens Grede, is a great example where this clash has led to massive business success.

Kim Kardashian is a textbook Three. She shines at building a polished, aspirational image that gives the brand that high-end allure and cultural gravity. Jens Grede is a classic One—objective, a stickler for excellence, and much more attuned to practicality and functionality rather than just the aesthetic. 

When Kardashian shared with Grede her early ideas about SKIMS, he realized that it wasn’t just another celebrity product, but an opportunity to fill a massive gap in the market. As he explained, big brands like Victoria’s Secret “tend to be too focused on what they’re doing”—i.e. producing garments designed to compress and contain. However, “We don’t want to live in a world where there’s only one option,” he said, pointing out that customers need shapewear that offers both high-level hold and all-day comfort, along with a greater range of sizes and colors. 

The magic of their partnership is how Kardashian creates the “soul” and the feeling of the brand, while Grede builds the engine that makes it run. In Grede’s words: “She’s unbelievably involved every single day in making the product experience exactly what she wants it to be, and my role is more to facilitate that.”

Final Words

Most startups fail; there’s a rough statistic that two-thirds of them never deliver a return to shareholders. But if you’re building something of your own, paying attention to these personality dynamics could be the difference between a brilliant partnership and a slow-motion car crash. If you’re curious about your own role in the mix, you can explore your type with an Enneagram assessment. It won’t guarantee startup success but it might just help you build a founding team that avoids the worst co‑founder fallout.