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Dave Bowen is the CEO of Purchasing Platform, an online marketplace for real estate developers to buy products for their properties. Before Purchasing Platform, Dave was the founder of Market Maker 4 (MM4), an e-sourcing tech startup, which he bootstrapped and sold for $22M in 2016. In this episode he talks about the pros and cons of bootstrapping a business, how to run a two-sided marketplace, and the pains and strategies for B2B sales.

Mark Cuban is a serial entrepreneur, investor, and owner of the Dallas Mavericks. His career began with his founding of MicroSolutions, a company he went on to sell to CompuServe in 1990. Then in 1995 Mark co-founded Broadcast.com - streaming audio over the internet. In just four short years, Broadcast.com (then Audionet) was sold to Yahoo for $5.6 billion dollars. Following the acquisition in 2000, Mark acquired the Dallas Mavericks where since his taking over they have competed in the NBA Finals for the first time in franchise history in 2006 - and becoming NBA World Champions in 2011. They are currently listed as one of Forbes' most valuable franchises in sports. If that was not enough, Mark is also one of ABC's "Sharks" on the hit show Shark Tank.

Technology is now the center of the universe and with it comes tremendous change. Om Malik, Partner at True Ventures, and Howard Lindzon discuss.

Fear, greed, hope and ignorance. Jim & Howard discuss.

Jim O’Shaughnessy is the Founder, Chairman & Co-Chief Investment Officer, OSAM LLC

Can you get a $206M valuation for a transcription business? The founder of Rev.com turned freelancers in their pajamas into a transcription powerhouse worth millions. They opened an office away from Silicon Valley, doubled-down on machine learning, and went to work.

Matt Mullenweg is the founder of Automattic and co-creator of WordPress, one of the largest open-source projects in the world, and a publishing platform that enables as much as 35 percent of the web. In this conversation, he discusses the beginnings of WordPress, the growing importance of open source in the age of cloud, the lessons he has learned as a founder and more optimistically, he is excited about the distributed workplace -- a core founding principle at Automattic.

Sahil Lavingia is the founder and CEO of Gumroad, a web platform where creators can sell products directly to consumers. He started the company while working at Pinterest in San Francisco, raised venture capital and ascended to the elites, but eventually, changed his trajectory, fired everyone and relocated to a small town in Utah. Why this was the right path for Sahil, and why venture capital is not a fit for everyone, it's all in this episode.

Ramon does not know how to code, or to write, and knows nothing, absolutely nothing about his target audience or the subject. He then goes ahead and builds a business worth $9,000,000 in three years. What?