Apu Gupta | Crain's

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Apu Gupta


Philadelphia-based tech startup Curalate, launched in 2012, helps companies market their brands through its visual commerce platform. The company currently has 125 employees working out of offices in Philadelphia, New York and Seattle, and recently closed on a $27.5 million Series C funding round. 

The Mistake:

Before we created Curalate, we launched a company called Storably. The idea was that it was going to be the Airbnb for parking and storage. Our investors were all invested in that idea. But here I was, a first-time founder and CEO of a technology company, and frankly, I had a case of imposter syndrome going on. I didn't know if I was worthy of the investment, and this money came from tier-one investors and venture capitalists who are paid to know what's going on. So they had provided us with this funding and I'm thinking, "Oh, I don't want these people to see through me; I've gotta fake it to make it," — and that's truly the definition of imposter syndrome. I felt like I really had to look like I knew what I was doing, and I think that made us a get a lot wrong.  

When we started building Storably, we were looking at Airbnb pretty closely -- looking at how they used the web and figuring that we had to make our site just as beautiful as theirs. Now, mind you, Airbnb's site is beautiful because they are taking photos of beautiful houses in beautiful locations. We were taking photos of parking lots and storage facilities. And you know what? No matter how good your lighting is, those things are still going to look terrible. But we were dogmatically following the lead of Airbnb and we were convinced our site had to be amazing.  

I ended up going down to South Carolina to hire this firm to do design work for us. They went ahead and created some stuff for us —and it was really nice, really good work. So we put this all up on our site and pretty much everything bombs. We never got more than 2,300 people to come to the site. I mean, it was an unmitigated disaster.

Eventually I was talking to one of our investors — and this guy is a legend in my mind — and I'm showing him this great ad copy and our design work, and we've printed it out on a beautiful poster-looking thing. He looks at it all and goes, "This is probably a little bit too slick for your audience. Why don't you pass out something that looks like a hand-written note, asking, 'Can I rent out your basement? Can I use your driveway for parking?'"

He said we needed to make it look like it came from a real person. So we did it — we put little brown envelopes on windshields and in mailboxes, and just like that, we got a 10 percent response. I felt like a complete idiot. This guy in about 30 seconds came up with something that invalidated everything I had worked on for months.  

We never got more than 2,300 people to come to the site ... It was an unmitigated disaster. 

The Lesson:

A lot of people today talk about MVP — "minimum viable product." But even still, I don’t think people think small enough. And that was the whole lesson for us: you can think much smaller than you might assume you can. What our investor demonstrated for us was that, no, we didn't need all of that stuff. It was completely unnecessary, because you can think small and still test effectively. That's the single biggest lesson we had from the Storably experience. That company had no redeeming value whatsoever, except for teaching us how to build and iterate on a very small scale. As we say today, it's about firing bullets instead of cannonballs.  

Before we launched Curalate, we actually came up with about 70 different ideas and then of those, seven bubbled up to the top. Of those, we ended up building three or four. One of them was called DrinkedIn. It was a whimsical play on LinkedIn. The idea was to send four people of complementary professional backgrounds to a bar for drinks, for the purposes of networking. So what we did was find a stock photo, put some basic copy on a site, and said that our algorithms would match up our customers with other professionals. Well, our algorithm was our intern. In three hours, we took it from idea to execution, but within no time we were getting press hits from around the world. We ultimately didn't pursue it because we couldn't figure out how to monetize it, but it demonstrated, I think, that we had learned something from Storably — and I think our investors appreciated that. We had the willingness to muster from those ashes something of value to apply toward building something better in the future, and that philosophy of building small has permeated everything we do at Curalate.  

Follow Apu Gupta on Curalate at @apugupta