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Over the years, Dan has made money online in numerous ways, usually in collaboration with his business partner Ian Schoen.
As of this writing, Dan’s main businesses seem to be:
The only one of Dan’s current businesses I’ve found numbers for is The Dynamite Circle.
Cal Newport wrote in July 2019 that the DC had around 1200 members.
Members pay either a quarterly ($147) or annual ($499) membership fee, in exchange for:
(As you can see, there are both online and offline elements to the DC.)
1200 members paying $499 per year adds up to about $600,000 annual revenue, or approximately $50,000 monthly revenue.
The DC info page says they have a full-time staff on hand, so between that and the cost of hosting multiple events each year I suspect their expenses are quite high.
Per Dan’s LinkedIn, he graduated from Clemson University in 2004 with a BA in Philosophy.
From his bio on LinkedIn:
Dan Andrews started the Tropical MBA blog as a job advertisement for a paid intern to join him as he traveled the world building his business with his business partner, Ian Schoen.
Looks like e-commerce was where Dan had his first big success online, starting in 2007.
From the Tropical MBA about page:
The e-commerce business was cat furniture and it generated more than $1 million in 2011 alone, according to a blog post by Dan in December that year.
A 2013 interview with Dan noted that he was then running another store that sold portable bars.
Judging by this video from June 2011, Dan and Ian launched the Dynamite Circle around that time.
It surely helped that they already had an audience of entrepreneurs paying attention to their blog and podcast when they launched the DC.
Dan runs several online businesses.
According to our framework they can be broken down like this:
Follow the links above for more info and examples for each type of business.