Playing Monopoly: Time for Breakups? Plus, Bill Gurley on IPOs; Gusto, LivePerson and Wrike Founders on Vision; the iPhone's Legacy at Apple + More

Themes can be like a roll of the dice — some work, some don't — but this week's had to be Playing Monopoly. With the House Subcommittee on Antitrust issuing a report laying out a case against big tech, I couldn't resist. Venture investor Bill Gurley made the case for killing the IPO, and a trio of successful entrepreneurs with different backgrounds (California, New York, Russia) told me how they survived some harrowing runs around the board.

Luxury Tax: Should Big Tech Break Up?

Are Amazon, Apple, Facebook and Google monopolies? Should they be broken up? I debate both sides in the latest installment of On the Other Hand.

Go Directly to Market: Bill Gurley on IPO Alternatives

Venture capital heavyweight Bill Gurley of Benchmark Capital joined me on Squawk Alley to make his pitch for the rise of the direct listing and the fall of the traditional IPO. He also gives a shout out to last week's On the Other Hand, which he thought wasn't half bad.

Prediction Error in Your Favor: Gusto CEO on Why He Was Wrong About Software

Question the conventional wisdom to open up your career. When Gusto co-founder and CEO Josh Reeves arrived at Stanford as a freshman during the dotcom bust, the popular line was that software was dead. Now he's cofounder of a software startup that notched a $3.8 billion valuation this summer. In a Fortt Knox conversation, he told me how his thinking evolved:

Advance Token to Entrepreneurship: LivePerson CEO Got Laid Off and Went to Work

Some people aren't cut out to be employees. When LivePerson founder and CEO Rob LoCascio got laid off from his first job out of college, he realized he was one of those people. Now he leads a $3.5 billion public company. In a Fortt Knox conversation, he told me how his entrepreneurial journey started.

Go Back 3 Spaces: Wrike CEO on Learning from Tough Times

Resilience is key in leadership, too. Wrike founder and CEO Andrew Filev is riding high, with an annualized revenue run rate above $100 million, and a plan to hit $200 million and consider an #IPO in about a year. But a few years back, he hit a rough patch and shifted his mindset. He told me about it this week on Fortt Knox.

From Sale of iPhone: Apple Gets $1.5 Trillion

Before the iPhone, Apple was cool but not dominant. Ahead of next week's big iPhone announcement, I look at the impact on Apple's market value in Taking Stock:

Next week I've got two interviews you'll want to see live but that probably won't make the newsletter:

On Thursday, 10/15 at 3 p.m. ET, I've got Kara Goldin, founder of Hint. Plenty to mine there in entrepreneurship, creativity, and what to do when the competition starts copying.

Then on Friday, 10/16 at 3 p.m. ET, I've got Jeff Maggioncalda, CEO of Coursera. Online learning is more important than ever, and he's playing an important role in its evolution.

And of course we've got that Apple event on Tuesday, with new iPhones coming! We'll see what special angles I can find for Fortt Knox.