Neil Patel

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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.  

Listen to the full podcast episode and review the transcript here.  

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The Ultimate Guide To Pitch Decks

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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They were in the middle of an IPO when things started hitting the fan. It was called off twice in a week by the bankers as indexes rose and fell.   

They pulled it off, but he definitely learned some big lessons about business. The first being that big money can bring big distractions. If you are spending your time picking designer office furniture, partying, and celebrating all the money you’ve raised, instead of focusing on building a profitable business, you’re not really building a business.  

The brainstorm and idea, create a pitch deck, doing the Sand Hill Road tour, and then trying to sell a business that is losing money works well for Silicon Valley investors. They can sit on plenty of boards simultaneously, and only need the rare home run to make it worth it. As the entrepreneur who might have to spend everything you’ve got and ten years of your life on a startup, most can only make a limited number of bets like this. It helps when you are focused and are striving to build a profitable business.  

He also learned that taking a company public and being rich on paper doesn’t mean you are really rich. He was 28, worth millions on paper. Then it all vanished, and he ended up walking with less money than he had invested in the company, and some debt to boot.   

After taking some time off on a motorcycle, and meeting his wife, he ended up throwing himself back into startups. This includes:  

  • Asset Performance: Where he learned the value of top quality product
  • Course Advisor: Which taught him speed is a weapon
  • ConstellationCK: Taught him being too complex can crush you
  • CueNotes: A lesson in building a real product, not a feature
  • OrionCKB: The need to delegate to teams  

Carlos Cashman’s latest rocketship startup is A fast-growing company rolling up leading products and companies on Amazon.   

They’ve been buying already profitable, cash-flowing businesses. They’ve already raised $250M, with valuations of around $800M, in just two years out of the gate. They’ve been growing at 600%, with 250 employees spread out around the globe.   

Storytelling is everything which is something that Carlos was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below

The business model is simple. It finds the “top-reviewed, bestselling” essential everyday products on Amazon, and buys the brands from the small business owners.   

So far, Thrasio has acquired 43 businesses in all-cash transactions and integrated them onto its proprietary operating platform. It then works to optimize them through branding and search, for example. Products include Beast Gear, a fitness equipment brand; TrailBuddy Hiking Poles, a seller of anti-fatigue floor mats, and Pet Deodorizer.  

Listen in to the full podcast episode to find out more, including:  

  • Why Carlos says startups should share their business plan more
  • Why raising debt is a more advanced strategy than equity fundraising
  • The core of all great businesses
  • Where he gets his ideas from



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Neil Patel

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