Carlos Cashman is a real serial entrepreneur with more than half a dozen startups under his belt. His latest venture has already raised a quarter of a billion dollars and is growing fast.
In his appearance on the DealMakers podcast, Carlos shared how he got hooked on technology and creating things, the lessons he’s learned through creating businesses, and what he’s up to now.
The Seeds Of Entrepreneurship
Despite his extraordinary track record in business Cashman says he was born and grew up in two of the most average cities in America. That was Peoria, Illinois and Tulsa, Oklahoma.
Carlos grew up in the years before kids were addicted to non-stop streaming on their mobile devices. You only had three TV channels and had to just get out and do things or be creative in finding ways to champion boredom.
He remembers that including a lot of reading. His father was in banking and had a lot of Forbes and BusinessWeek type magazines laying around. His mother sold sets of encyclopedias door to door for the discount so their family could have their own at home.
Of course, as soon as computers began to emerge Carlos got hooked on those. These were the days of the Apple II and HP Workstations with monochrome screens and vinyl record-sized floppy disks that could barely hold 2k of data.
He and his friend Chris Chang would pass on recess and lunch breaks at school to teach themselves basic programming. The teachers didn’t even know how to use them. So, they taught themselves out of books.
In fact, it was reading again that got him excited about MIT’s lab, where he ultimately went to school.
Landing In Startup World: Creativity Thrives In A Box
After school, he headed to NYC with the idea of being involved in the movies. He tried applying for a job selling computers for CompUSA, who wouldn’t even interview him.
Being brand new to the subway system and not having money to burn on cabs everywhere yet, Carlos turned to the old paper phone book to find companies within walking distance of his apartment.
Setting out to drop off printed resumes, he found a little startup company tucked away in an office building where they had bribed the super with a case of whiskey to get some space.
He also spent time working for design and branding firm Frankfurt Balkind. An experience that taught him about quality and bringing together top talent and unleashing them to succeed.
He learned that giving people the confines of a ‘box’ to create it can actually make them more creative. Something which certainly applies to entrepreneurship and trying to run a lean startup.
Getting Your Startup MBA In the Trenches
The best way to really learn all of the parts of being an entrepreneur is just to jump in and start doing, and start figuring it out.
Carlos did when he helped spin off Opus360 from Gray Peak. They raised $50M, acquired other companies, and had several hundred employees. Then the dot com crash came.
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