Krishna Gupta: Building Startups From the Web to Your Cup

Krishna Gupta is a Los Angeles-based technology entrepreneur, occasional hard-rock guitarist, whiskey aficionado, real estate mensch and all around good-idea manufacturer.

Krishna Gupta HeadshotHe has his dad to thank for his tech nerd and entrepreneurial genetic material. Before starting his own business, Gupta, Sr., was a hardware/software engineer during the pioneer days of personal computing. He was on the Sycor team that built the first microprocessor for Intel. He would bring home the latest and greatest computers, introducing Krishna to computing before he even started kindergarten. During grade school, while his teachers were telling other kids how to turn on their Apple IIe, Krishna was drawing spirographs in Logo and programming trivia quizzes in Basic. Despite a preference for experience over formal education, he earned a bachelor’s degree from Carroll University (outside Milwaukee) in Biology and Psychology and an MBA with honors from UCLA.

Krishna is currently partner and CEO of Sortfolio, a directory of Web designers and creative agencies that represents nearly 14,000 professionals in more than 200 countries. He also just launched the startup BeanGenius as part of the Startup Spotlight at the SXSW V2V conference in Las Vegas. BeanGenius is a specialty coffee subscription service that learns your taste preferences and sends freshly roasted coffee chosen by your palate, as opposed to some “expert.” Think of it as Pandora for coffee.

You have a particularly diverse career trajectory. What was the impetus behind the great leaps between businesses?

That is a long and convoluted story, but I’ll try to keep it short. I’ve always been entrepreneurial since I was little. I grew up in a small business household and watched my immigrant parents forge their own path. I was the kid who was always trying to figure out ways to make money. I spent my adolescent years in the hospitality industry. Imagine that, an Indian working in a hotel. Crazy, right? By the time I was 15, I was managing operations for a hotel bar, where I learned the fundamentals of minimizing inventory costs, loss prevention, negotiations and economies of scale.

After completing my BA, I decided to go into business right away instead of grad school. As I dwelled over my next move, I saw one of those “no money down” late night real estate infomercials. I thought, surely if the people in this commercial are making money, I can too. Keep in mind I knew nothing about real estate. So I bought the course, re-created the forms in Excel so I could really understand them, and returned the books.

When I told my dad of my awesome plan, he suggested I go into commercial real estate. His advice was that I’d be working just as hard but the value of commercial deals was a lot larger. That made sense and since it was all the same to me, why the hell not? I got my broker’s license in several states and did pretty well. Technology was a differentiator and a major factor in my success. We were using Keyhole, the precursor to Google Earth, to provide aerial maps and overlay demographic data and drive time population radii.

When did the rock’n’roll come into play?

I put my first band together while I was in real estate but had discovered guitar just after high school. Oddly enough, I wasn’t even really into rock’n’roll until one day in 1993, or sometime when MTV still played real videos. I saw the video for Guns N’ Roses November Rain. I didn’t know much about them. I couldn’t even name the members, but I knew that the guitar player (Slash) was causing an emotional reaction in me by manipulating wood and steel. I wanted to do that. I was obsessed. I started spending insane amounts of time learning all the GnR songs and reading everything I could about them. After I was done with that I went back and learned all about Joe Perry since he influenced Slash. After that I tackled Jimmy Page since he influenced Joe Perry and so on. I discovered Led Zeppelin and got stuck in the late 1960s and 1970s and all I was playing and listening to were bands like Cream, the Stones, Black Sabbath, Lynyrd Skynyrd and the Allman Brothers.

I did all my learning by ear and some tablature, and I got to the point where the tablature would indicate a certain position on the neck, but I was so familiar with the artists that I was certain that they didn’t really play it on the indicated position on the neck. Like I said, I was obsessed.

Krishna Gupta Guitar

How did you balance work with music?

I was equally passionate about business as I was about music. Until I gave up the idea of being a professional musician, I was continuously working on new business ideas while chasing my music dreams. There was a women’s fashion jewelry line, a mobile app development company and even an exotic car timeshare concept. The car project got me to the finals of an MIT Fast Pitch competition. In the end they all failed but I learned a great deal from each failure. I got tired of failing on my own dime though, hence my getting an MBA.

Have you found a common thread through your projects?

I have. It’s people. I can confidently say that a major component of any success or failure I’ve had is due to the quality of the team and the people involved. Of course there were market factors, timing and financial issues as well but a common denominator was the quality of people and their ability to communicate. When I say “quality,” I don’t necessarily mean just academic or cognitive ability. It’s shared vision, commitment, communication and clear leadership. They say VCs would back a strong team with a mediocre idea over a mediocre team with a strong idea and I can see why. A strong team will figure things out because challenges are going to come up, and in the end it’s all about execution. Hire and partner for attitude over aptitude.

What kinds of startups stand out for you?

I’m a fan of startups that are disrupting industries whose barriers to entry are protectionary government regulations, opaque cost structures and inefficiencies in the value and distribution chains. I love companies like Warby Parker, Uber, Tesla, TrueCar, Redfin. These obviously aren’t startups anymore but you catch my meaning.

Please talk whiskey.

My strong affinity for Jack Daniels is no secret and almost a running joke at this point. It’s my go-to cocktail and a legacy from the guitar playing days. I’m a little embarrassed to say it, but it started during my religious studies of my guitar heroes. There’s countless pictures and associations of Jimmy Page and Jack Daniels, so what’s good for him must have been good for me, right? Then it just stuck.

A couple years ago I was in Beijing and a buddy of mine bought me a good scotch. I can’t remember what it was but it was the first time I really tasted whiskey and like the first time I heard November Rain, I was hooked and I became infatuated. I learned everything I could about the history, the ingredients and the distillation processes of creating whiskey and its variations. Now my special occasion scotch is Macallan 18. I actually prefer it over Macallan 25 but my daily driver is still Jack Daniels. I generally like anything from the Speyside and Highland regions, as opposed to real peaty Islay scotches. I did the Bourbon Trail in Kentucky a few years ago too and while I know quite a bit, I still learned a lot.

Any other interests? Books, movies, music?

Unfortunately, one of the casualties of leaping head first into the deep end of the entrepreneurial pool is my absence of leisure time. It’s been just over a year since I quit the band and became a full-time businessman, so I feel like I’ve got a lot to make up for. I just picked up my guitar again and am looking forward to rediscovering music without the pressures of that industry attached. I’ve been listening to more singer-songwriter stuff including Mark Lanegan, The Civil Wars, Iron & Wine and Johnny Cash.

I recently took flying lessons and I loved it but it’s a major time commitment. I’ve got a project list I want to get to as well. I’d like to restore a ’67 or ’68 Mustang fastback (I could use some advice on this, so please reach out), distill a small batch of whiskey and send a weather balloon with a camera to 90,000 or 100,000 feet. Oh yeah, and I’m addicted to Game of Thrones and Breaking Bad.

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