Competing with Costco: How these startup CEOs take on the big names — and win

September 14, 2017

For a small startup, competing with a major company seems a lot like getting in the boxing ring with a pro who’s twice your size: They have tons of experience — and muscle mass — that you haven’t quite developed yet.

But these days, that’s not a fair indication of who’s stronger. It’s no longer about mastering what’s always worked, but inventing new ways to do it better. We caught up with executives who took on this challenge themselves, and they shared how they were able to give giant corporations a run for their money. 



If you think moving is a disorganized, insufferable task, Updater has three words for you: Hold my beer. Founder and CEO David Greenberg told us he used to think moving was a painful and time-consuming process, and that’s why he set out to change it. Updater took all of the steps associated with moving — changing your address, canceling your utilities and transferring and installing them appropriately — and unified them into one platform.

How did you crack the industry?

I pitched the concept to close family and friends, and generally, everyone seemed to think it was a great idea. Who wouldn’t want a more pleasant moving experience?

One challenge I faced, that I’m sure many entrepreneurs also face, is determining how far and wide to go with outreach to investors and experts to source feedback. My original instinct (as a former lawyer) was to protect my idea instead of sharing it openly. Early on, I missed valuable opportunities to get feedback from potential users and early adopters. Over time, I found that by talking to more and more people, I was able to continuously refine my approach based on the feedback I received. Engaging experts in different industries provided me with invaluable perspective — there are a ton of folks I often thank who helped me along the way.

I recommend tapping into the resources around you throughout your entire journey — don’t be scared to share, because success is as much about execution as the idea itself. The reassurance I continue to receive from experts and advisers gives me confidence and fuels my tenacity.

What’s your advice to other brave entrepreneurs?

Don’t worry about “how we’ve always done it.” Improving an industry requires you to challenge assumptions that have been in place for decades.




The bulk wholesale industry is, as its name implies, gigantic. Costco, Sam’s Club and BJ’s are just some of the major companies that have been connecting consumers and warehouses for years. But none of that intimidated Boxed CEO Chieh Huang. He noticed that, while the industry was huge, it wasn’t mobile — and that’s where Boxed saw its opening. The company now provides consumers with packaged goods that are delivered straight to their homes without any delivery or membership fees.

How did you crack the industry?

My co-founders and I had previously started a different company that we ended up selling, so we were lucky to start with the advantage of knowing a number of venture capital folks. Having a good track record with them helped open doors for us. Early on, people bet on the leadership team and their vision, and our past success helped people get comfortable with the concept of Boxed.

There was a ton of hesitation, though, don't get me wrong. A lot of people felt our concept would be dead on arrival and many VCs had been burned by similar concepts back during the tech bubble in the early 2000s. But we managed to get the seed funding we needed. And very quickly, we saw that there was an interest in what we were selling.

What’s your advice to other brave entrepreneurs?

Don't seek to disrupt an established industry just because — make sure it’s an industry and idea you are personally passionate about.




If you asked most business owners to explain how to procure and manage insurance, you probably wouldn’t get a straight answer. Areas like carrier supply, distribution and educational resources for the business insurance industry are fragmented and stressful — and that’s what Coverwallet is working to streamline. Co-founder and CEO Inaki Berenguer told us how his own experience fueled the fire to make changes and take on the giant (and outdated) industry.

How did you crack the industry?

Rashmi Melgiri, Coverwallet’s co-founder, and I dove headfirst into all things commercial insurance, aiming to soak up any information we could get our hands on. It started with taking a licensing course, meeting with insiders and reading popular subject matter works. We also did a bit of mystery shopping to further understand the pain points as customers and the value propositions proposed by each respective broker.

I built two startups that were acquired, which helped open the door to many conversations that would've been a harder sell otherwise. Still, while this gets your foot in the door, it’s not a guarantee of investment. In our pitch, we focused on showing clearly the customer needs, current solutions, opportunity, market size, growth and distribution. We established a clear mission and target: Help small businesses to easily understand, buy and manage insurance. We don't try to be all things to all people.

We also made sure to attract the right talent needed to build best-in-class development and marketing teams, which was a great but necessary challenge.

What’s your advice to other brave entrepreneurs?

Be passionate about the problem you are trying to solve and never lose focus. You’ll find hurdles and bumps along the way. Those who remain focused have a greater probability for success.



Images via featured companies.

Know of a company that deserves coverage? Let us know or tweet us @builtinnewyork.

NYC startup guides

Best Companies to Work for in NYC
Coolest Tech Offices in NYC
Best Benefits at NYC Tech Companies
Women in NYC Tech