Building A Startup That Can Punch Above Its Weight–And Win

In competitive sports, you are typically matched up with opponents based on age, size, and weight. Most of the time, these matchups are fair (or close enough), but occasionally you are matched up against someone twice your size and experience. Life’s not fair sometimes. And yes, this is exactly like the startup world.


I used to do full-contact competitive karate (I also auditioned for the part Macaulay Culkin played in Home Alone, but that’s a different story for another day). I was very young then and the competitive fighting taught me a lot–unbeknownst to me at the time–about hiring a world-class startup team.

In karate, like with other competitive sports, you are matched up with opponents based on age and, especially in the case of contact sports, your size and weight. Most of the time, these matchups were fair (or close enough) but occasionally you were matched up against someone twice your size and experience.

Life’s not fair sometimes. So instead of complaining, I learned that fairness and equality aren’t always something I can rely on in a competitive environment. And yes, this is exactly like the startup world. 

If you have enough of these unfair matchups, you learn about persistence, resiliency, and resourcefulness regardless of your circumstances. These are the same qualities we now look for when building out our own team. We look beyond experience for people who can fight and win above their weight class in any situation. 

Startups are addicting in part because they are unpredictable and full of interesting challenges. You have to make sure your team is prepared for anything and ready to fight even when the odds of winning are not in your favor. At ReadyForZero we use these principles religiously.

Ambition and resilience.  


When you are outmatched and win, you become a little more fearless next time. When you are outmatched and lose, you should be better prepared, more resourceful, and resilient the next time. Ambition can sometimes be dangerous, but in a startup environment it’s critical to learn from mistakes quickly, early on, and go back for more, regardless of the outcome.

The easiest way to figure this out is to ask about failures and see if your potential startup comrade went back harder and stronger after failing once or twice. If they can’t think of a colossal failure, that’s a serious problem–that’s like hearing a startup tell you straight-faced that it has no competition.

For technical people, this might be an open-source project that they started or worked on that might not have caught on as expected. Is this person willing to fail and get back up for more punishment? What happened when they failed? Can they articulate the learnings and clearly communicate what they would do different next time? Was their next attempt even more audacious, or was the effort minimal because the fear of failure was still on their mind? The key isn’t to find reckless ambition but rather to find a willingness to learn and adapt quickly.

Learning curve? Steep, please. 

If your startup is doing something worthwhile and building something people want, then you are constantly forging new ground. Navigating new technologies, new industries, new regulations. In most cases, you don’t know what you’re doing, so you admit it and move on as fast as possible. You learn what you can quickly then take action on the learning.

A good plan today is better than the perfect plan tomorrow (quoting George Patton). Can this potential hire think clearly and act on new, incomplete information as it comes? You can figure this out by giving them a real problem you and your startup are currently having then expand the scenario as they come up with possible solutions. No need for hypothetical situations–your startup surely has plenty of challenges that could use an outsider perspective. Things like “How would you go about getting our startup new customers?” or “What resources would you need to create X-big-feature on your own?”


Realistic, yet confident.  

Startups can be tough on your ego, so you need a healthy ego that’s strongly rooted in the real world to get you up to fight another day. Creative, big ideas are great but you need to know yourself and your team’s limitations well enough to execute and/or know when to pull the plug when thing’s aren’t going as planned.

A good way to figure this out is to ask your prospective team member about a time when they had to stand their ground in the face of strong opposition. Regardless of whether they succeeded or not, what was the outcome and how did they make their case? 

Getting stuff done while working well with others.  

Startups aren’t for everyone. People who get things done are far and few between. In a startup, you have a great deal of ownership and accountability. It’s hard to hide in a startup the way many do within big companies. You’re always on and there is always something that needs attention.

This is the hardest thing to figure out without having worked with the person in the past. References are the next best thing, and when in doubt it’s likely not a good fit. As CEO, I fix buggy code, make coffee, take out the trash, and do whatever else it takes. This is where executives without entrepreneurial experience often fall short.


Early-stage startups seem appealing and sexy, but the reality of the work is often unlike anything they’ve done before. Remember: Small startup teams are particularly vulnerable to bad apples that can ruin the bunch. Culture matters (a great deal) and getting things done as a team is a big part of that culture.

Startups are hard in part because finding people who work well together for a common cause is exceptionally challenging when you are faced with what seem to be insurmountable challenges everyday.

These are the qualities we look for at ReadyForZero. Our hope is they help other startups and entrepreneurs build world-class teams that can fight and win above their weight class; it’s a good way to put the odds in your favor.

Author Rod Ebrahimi is the cofounder and CEO of ReadyForZero, an online program that helps people manage and reduce debt. 

[Image: Flickr user Brian Auer]


About the author

Rod Ebrahimi is the CEO/co-founder of ReadyForZero, an online software program that helps people manage and reduce debt. Rod started his first technology company while still in high school at age 17 before moving to Silicon Valley. He holds a B.S., with Department Honors, in Cognitive Science with a specialization in Human-Computer Interaction and has completed coursework at Stanford's Graduate School of Business SIGM.