Iterations: “We [Lucky] Few”

Editor’s Note: Semil Shah is a contributor to TechCrunch. You can follow him on Twitter at @semil.

For this week’s column, I wanted to write about something entirely different than the normal market trends and product analysis you’d see on “Iterations.” When I moved back to California in the middle of 2010, I had just spent the previous 18 months consulting and trying to get a life sciences company off the ground in Cambridge, Ma. I moved here and wasn’t really sure what I wanted to do or could do. Little did I know how dynamic and competitive it is in the Valley, even though I lived in San Francisco in a previous life before my years in Boston, I wasn’t in the technology world at that time. I try to remind myself every day that this is a very special place and that I’m lucky to be here, to not take anything for granted.

I was reminded of this while in Austin a few weeks ago, meeting old friends and new friends who don’t live in the Valley and hearing about their desire to move here. And, I was reminded of a friend that I made in Palo Alto when I moved here in 2010. His name is Ryan Bennett. He played college baseball and we watched a bunch of Giants games together at the Old Pro sports bar. And, I tried to help him with his startup, but eventually he had to shut it down. Eerily, the product he was building was quite similar to the mental model that caught fire with Pinterest, a site for people to collect items they want. It’s crazy to think back of his product insight and realize he was on the same track before it was a fad and trend. Ultimately, it didn’t pan out for him. During the playoffs of 2011, I sent him a note to watch baseball with me, and he wrote back to inform me that he had left town. I had no idea at the time. I think about Bennett from time to time, and reached out to him for this Q&A because in spending time with him, I found him to be an extremely honest, earnest, and good person. What he writes below is very hard to do, so I commend him for being open about sharing, and I think it’s a valuable reminder to all of us who are here now in the Valley, no matter for how long, to see how lucky we do have it.

1) When did you arrive to the Valley and when did you leave? I arrived in Palo Alto in February of 2010 and left in the summer of 2011.

2) What did you focus on when you were here? I dedicated my energy towards building an internet company called Liv ( The purpose of Liv was to design a simple way to collect, organize and share all your selected products in one convenient and public spot. It was very similar to what is now called Pinterest. (See below at the end for a screenshot of Liv’s old homepage.)

3) What the three accomplishments you’re most proud of during your time in the Valley? I don’t know if I have three accomplishments in the Valley, but I think there were a few things that I was able to do right. I had obtained an undergraduate business degree from Saint Louis University and I was halfway through my MBA when I decided to put my studies on hold and move to California. I personally had no technical experience but was able to recruit a talented team of individuals who held the knowledge I lacked. These individuals believed in my vision for the company and were able to build an impressive product. One of the most important things I did was learn how to code (HTML, CSS, Javascript). Although I wasn’t great, I was better able to communicate with my team and, more importantly, I was able to assist with product development from day one. However, when I look back, my proudest moment occurred when I was shutting down the business. Each person on my team was able to find a job quickly after I had to let them go. Our business relationship is still strong to this day, and they credit their experience with Liv as a bridge that helped them land new opportunities. They deserve it, and I am very happy it worked out for them.

4) What were the three hardest things you had to go through here? My decision to move from Kansas City to California was a tough one as I literally knew no one who lived locally. One of the hardest things I had to do was make friends in an unfamiliar environment while attempting to establish connections when I knew no one. I did catch a break and had a very good friend introduce me to one person named Kevin Holmes, who is the Founder of Founders Network. Kevin introduced me to a few people, and I simply started to buy people coffees and lunches, all the while talking to anyone and everyone I could. Another hard thing I had to go through while living in California was the feeling of letting my team down. We were invited to pitch Liv at an event called Founders Institute. I had prepared for weeks, and I was ready. I was two minutes into my ten-minute pitch before I realized I couldn’t see my slides, and I completely forgot my pitch on stage in front of hundreds of people including influential investors. After the rest of the companies pitched, I remember people glancing over but avoiding our table like the plague. It was a definite low point in my career. I knew I would get back up in the morning and continue to build our product, but I couldn’t help but feel extremely disappointed in myself for letting my team down. Lastly, coming to the realization that our company did not have enough money to continue was the hardest of all. I had to inform my team that I could no longer pay them and that they were without a job. I had to pack up our office, let go of my team, and make travel plans to move back in with my parents in Kansas City, Missouri.

5) When did you realize you had to leave the Valley? How quickly did you leave? I don’t the exact date  when I realized I had to leave the valley but I would review our cash position everyday and I knew the runway we had left. After I cut all expenses, except my personal rent, I stayed a few months more working out of my home. Eventually my lease ran out and I couldn’t renew. It was time to go.

6) How long did it take to get over the failed business idea? That is a very good question that no one has asked me before. To be completely honest, the feeling of having a failed business is very similar to that of losing a loved one. I went through the 5 stages of grief and it took an emotional toll on me. For 2.5 years, I devoted my life to analyzing, strategizing, leading, and building a company. My team and I dedicated ourselves to creating a successful business. Then one day you wake up to nothing and you have no idea what to do next. It takes a while to cope, however, I am not sure if you ever truly get over a failed business.

7) What was it like going back to the Midwest? The Midwest and Kansas City has wonderful people that will do anything for you. It is truly a hidden gem. However, like almost every other city, failure is not a badge of honor. One thing about the Valley that people take for granted is the idea that failure is okay and even highly regarded. In the Valley, when you fail, people look at you differently and put you on a small pedestal, like you won the losers’ bracket of a tournament. That is very unique and doesn’t exist anywhere else in the entire world.  One of the hardest things about moving back to Midwest (except being flat broke and moving back in with my parents at age 26) was seeing the reactions of my friends and family members when I told them I had to close down the business. They didn’t see “Ryan Bennett, a guy who put everything on the line and worked 14+ hour days for 2.5 years to try and create a profitable company.”  Instead, they saw a guy who failed and couldn’t make it. Luckily, this mentality has recently begun to shift, and the startup community in Kansas City is beginning to explode.

8) Now, with some time away, do you still think about the Valley? Of course! The Valley is a crazy bubble that has an ecosystem that can’t be replicated. When I moved back to Kansas City, people would ask me to describe my experience in the Valley. It was hard to describe fully so I tell them this story. As I was walking down University Avenue in Palo Alto after attending an event at Stanford, surrounding me are some of the first established offices of Google, Logitech, Facebook, etc. and next to me are tons of entrepreneurs trying to make their idea the next big company. As I walk down the street, coffee shops are filled with people working, pitching, and networking. I continue to walk and I see Guy Kawasaki walk past me to the left and a Lamborghini pass me on the right. What other street in the world can you find brilliant possible co- founders, angel investors, top VCs, entrepreneurial authors, and millionaire mentors who have built and sold companies in a few blocks in a small town in California. That is how I think of the Valley.

9) Based on your experience during your time here, what’s your impression of the climate here keeping up on the news? I haven’t been back for a few years so that is hard for me to answer that question. However, from witnessing and reading the news, entrepreneur has now become a fad. While I love the commitment and resources to help entrepreneurs, I know that not every college graduate should start or join a startup. Being an entrepreneur is very difficult and I am worried that when things get hard, the fad following entrepreneurs will run leaving the rest of us with a mess to clean up.

10) Do you think you’ll ever make it back here? My time in the Valley was wonderful and I love going back for work and play. However, the Midwest is my home and I don’t see myself returning to the Valley. The Valley is the heart of the startup world, but Kansas City (my home) has a thriving startup community plus I am close by to my family and friends.

11) Do you think folks here take the fact that they’re here for granted? Why? I know I did! The Valley has some of the smartest minds in the world, some of the best technical universities in the world, enjoyable weather, and a culture where people get together, collaborate, and try to build something that can change people’s lives. It’s a special place that I am glad I was able to experience. When I lived the startup life everyday, I didn’t realize what I had access to until I moved away. It’s a special environment.

12) Is the Valley all that you thought it was, or are there parts you wish would have changed? While I do believe the ecosystem is amazing, I think the downside of living in that bubble includes the fact that it is hard to get out and realize what the average person needs and is willing to pay for. When I was there (might have changed in the past few years), everyone, including myself, was building the same type of [insert next buzzworthy trend] company. After I left the Valley and reflected on my time there, I realize that we sometimes get so caught up in the hype of other exploding products that we forget why we are entrepreneurs. It could be because I was born and bred in Kansas City which has companies like Garmin, Cerner, H&R Block, AMC Theaters, Sprint, and The Kauffman Foundation. These entrepreneurs set out to build a sustainable company that was created to solve a problem with a solid revenue model. When asked for advice from other entrepreneurs, I now suggest they should put the same amount of attention on the sales channel and revenue generation that they do on building the product. That is something that I wish I did differently.

13) What are you working on now? I am now working at a startup company called Idle Smart. We have a patented product that helps reduce the idle time of a semi-truck as the driver sleeps at night. It is very similar to a thermostat in your house. The driver will set the temperature and then go to sleep. Throughout the night, we monitor the cabin temperature and literally turn the truck’s engine on and off to keep the driver comfortable in turn reducing overnight idle time by up to 70%.

[Here’s a picture of Liv’s homepage, in which you can see the rough sketches of what Pinterest became…]