In today’s corporate world, very few people can call themselves a serial entrepreneur or investor. But for Greg Isenberg, current founder and CEO of Islands, that’s exactly what his life has been to date.
With a focus on consumer products, Greg has spent his life creating marketing and social media campaigns for some of the biggest brands in the world, creating Wall Street’s most popular stock market simulator, investing in early stage startups, and building remarkable digital products – many of which have been acquired.
Most recently in 2012, Greg was founder and CEO of a startup called 5by, a startup that gave consumers a simple button to push to retrieve the most popular videos on the web. By 2015, the company was acquired by StumbleUpon. “After the acquisition, I told myself I needed some time off,” he said. “I had been working since I was the age of 13 and I wanted to take a break and do nothing.”
The break didn’t last long. Greg had met a woman in Los Angeles who had a rare cancer. She had created a group of 50-60 people that would converse daily through email. “I tried to get them all on Slack thinking it would make it easier for them,” he remembered. “The entire group said it was too difficult to use and they couldn’t figure it out.” With that, Greg’s next entrepreneurial adventure began and Islands was born. The product is still in private beta but users can sign up to join the waiting list. The concept revolves around providing a de facto community platform for communication, much like the group the women in LA created to stay in touch.
While being a serial entrepreneur and investor may sound glamorous, the pressure and continually having to be “turned on” can take its toll. When asked how Greg steps back from the daily grind or stays inspired, he noted, “Being alone is underrated.” After realizing he was getting a bit overwhelmed at work that day, Greg gave the example of starting his day with a walk in the old port of Montreal, listening to music – alone. “I even put my phone on airplane mode,” he said. Being alone allows him to regroup. “I also think nature helps a lot,” he added.
Like other interviews we have conducted, we often ask about meditation. “Depends how you define meditation,” said Greg. The point is valid. We often think of meditation as sitting, legs crossed, and chanting. However, meditation can vary be individual. For Greg, he doesn’t practice the traditional sense of the word, but rather has found his version in the form of Russian Bathhouses. “There’s this one I go to in San Francisco every time I’m there,” he said. “It’s amazing. You submerge yourself in the sauna and then do a cold bath that’s like 38 degrees.” The bathhouse offers Greg the opportunity to disconnect, but have both a mental and physical rejuvenation. “It’s one of my life hacks,” he ended.
What’s your opportunity to disconnect?
At the end of the day, Greg does a great job summing up how many people are living and working today and why types of meditation and forms of journaling are so important. “While some people are fine with just being a cog in the wheel, others are working to optimize their lifestyle and do more with their lives,” he said. “People need to find the things that keep them balanced. They need to find their sauna”
- What am I worried about?
- How am I spending my time?
Images: Marc Champagne