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Kevin Rose — The Man Who’s Seen It All

Kevin Rose is one of the most recognizable individuals in the startup world. As a founder, he and his team created the news aggregation site Digg, which became a household name, putting him on magazine covers around the world and creating an iconic brand in Silicon Valley. Since then, he has also invested in companies like: Twitter, Facebook, Square, and NextDoor to name a few. Kevin is not only incredibly honest and open about his successes and failures, but he’s enthusiastically trying to get others to share just as openly.

Updated on September 17
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Key Smash Notes In This Episode

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Kevin has made a name for himself in the startup industry by both starting massively successful businesses and financing future monopolies. While he has seen incredible success throughout his career, Kevin has experienced his fair share of failures, and he encourages others to be as open about their shortcomings as he has been.

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Kevin often finds himself switching in between brewing his own coffee and tea in the morning. Because of how fasting can decrease your chance of cancer and have other health benefits, Kevin has taken up the health trend of intermittent fasting, which involves not eating for 13 to 16 hours every day. Kevin also made an app to help thousands of others adopt the trend.

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Kevin once experiences liver pain, and found that he had too many liver enzymes. It turns out that Kevin’s excessive consumption of sage, which helps eliminate stress, had begun to damage his liver in combination with alcohol.

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Certain tools exist online that people can use to map out their genetic structure and plan their diet around their genes. Because of a genetic test he received from Ronda Patricks’ foundmyfitness.com, Kevin tries to incorporate choline into his diet to prevent memory deterioration. Focusing on incorporating all the colors of the rainbow in his daily diet is key for Kevin, so his lunch consists of various vegetables. Kevin also performs cardiovascular exercise frequently to combat his family’s history of heart troubles.

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You can get similar benefits to long-term exercise by just doing multiple separate sprints. Kevin also focuses on performing a variety of high and low intensity exercise. Saunas decrease the likelihood of cardiovascular disease and dementia, so adding some time in the sauna to a workout routine provides both rest time and health benefits. If you are willing to spend a little over a thousand dollars, saunas can be installed almost anywhere in your house, and spending some time in the sauna decreases your body temperature and helps you sleep better at night.

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Matt Walker of the Berkeley Sleep Lab published a book titled “Why We Sleep,” which dives deeply into the nature of sleeping and how important it is to us. A decade ago, we knew very little about sleep; however, today, we are beginning to understand much more about the intricacies of our sleep. Ironically, people tend to be more productive when they spend less time working and more time sleeping because sleep is essential for focus and efficiency, both of which are vital in the business world.

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Kevin once tried 5 grams of psilocybin mushrooms with the professional help of a therapist in order to further his understanding of himself and his psyche. It has been described as 5 years of therapy in 5 hours and has helped cancer patients come to terms with their mortality. Kevin describes the experience as incredibly eye-opening and entirely unique, but also acknowledges the insanity of taking “magic mushrooms” as a form of therapy.

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Understanding that asking for help is ok and being selfless were essential for Kevin’s success, especially because he never finished his degree and often found himself surrounded by graduates of prestigious universities. During a conversation with Mark Zuckerberg, Mark described how he had surrounded himself with a slew of mentors that worked alongside him to make decisions for the company. Kevin believes that not being the smartest person in the room and putting one’s ego aside can benefit them in the long run.

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When he looks back, Kevin finds himself blaming other people for his failure when everything crumbles from underneath him. However, Kevin is grateful in part for his failure because it allowed him to mature as a person and eventually grow into the composed man that he is today.

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Kevin never had a serious breakdown over how Dig failed, mostly because Reddit, Dig’s greatest competitor, didn’t beat Dig at its own game. Dig managed to hold its own as a democratic algorithm-based content website, but Reddit overtook it by focusing on smaller communities run by individual moderators.

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During a Dig board meeting that occurred after the company raised 35 million dollars in venture capital, one of the company’s members brought up the idea of having more mainstream news on the front page to promote general publicity on the site. Kevin’s had a negative gut reaction to the idea because he loved the unique news that made Dig unique, but the idea went through anyway. A combination of other issues like tech issues, the war with Reddit, and a change in media direction all took a toll on Dig.

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Kevin’s first few days at Google shocked him because of how effective and efficient every member of the staff was, and immediately recognized how much less time he had put into finding new talent than Google had. He also realized how much Google focused on copying and then improving on the ideas of competitors like Facebook.

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Google often focuses on hiring engineers and doesn’t bring in as many creative employees as other companies. This results in sophisticated and slick programs that can support billions of users but lacks an interesting and practical central concept.

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Kevin adored his time there because the organization was well-run and he got to angel invest in a variety of different startups. Although he wanted to spend more time there, Kevin yearned to build products of his own again after a few years in the program.

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After Dig, Kevin overcorrected his past mistakes and tried to dominate every aspect of his next venture. It wasn’t until Google that Kevin understood the value of a well-recruited employee. Kevin also realized the positive aspect of failure and how failure is one of the best ways to move forward.

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Many unsuccessful business founders get bogged down in their own failures and fail to see the silver lining that comes with failure. Often times a bad news cycle or little outside support can prevent the head of a company that recently sold for pennies on the dollar from trying to start again.

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Because Kevin has experienced multiple layoffs, painful decisions, and incredibly successful periods of growth, he now has the expertise to help companies during nearly every part of their development.

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In terms of his professional career, Kevin’s investments have been his most successful ventures. By trusting his gut and his connections, Kevin has managed to invest in companies as successful as Facebook and Twitter.

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It certainly has helped Kevin. Having conversations with people that have gone through similar situations is always easier than talking with someone who has little experience. Kevin prefers being the investor that sits on the sidelines most of the time

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Often times, spouses act as therapists during the development of a new company. Whenever founders offload onto their spouses, the entrepreneur may feel better but the spouse internalizes the problem and finds themselves unable to help, which leads to them feeling useless and depressed.

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