Bruce Cleveland on Legends & Losers Podcast

December 21, 2017

PUBLISHED BY Legends & Losers

A lot of people who come from big “category king” companies think they can automatically build a legendary business. How has history proven this notion wrong through the failure of a lot of start-ups? Why is it so important for founders to know how to sell and market, as much as they know their products? Can a company be hard and soft at the same time?

On this episode, we are joined by Wildcat Venture Partners founding partner, Bruce Cleveland who shares on his time at Oracle and Siebel, and how he’s changing the way startups are built in Silicon Valley.

“After the point you become an individual contributor, your job is to influence behavior.” – Bruce Cleveland

Listen to the podcast on iTunes here.


Digital “oil” is data. The products that are going to let us prospect, refine, and monetize data are where wealth will be made.

There’s a lot of lip service and no action when it comes to hiring former military personnel and bringing them into the workforce.

The best leaders hold themselves to the same standards they hold other people to.

At the start of the show, we talked about the early days of Oracle and the lessons Bruce learned. Next, we juxtaposed the current culture of tech companies with the more military culture of older companies. We discussed why Bruce is passionate about hiring former military personnel, and the value of self-actualization. Towards the end, we talked about why we’re always representing the companies we work for.

We also discussed:

How the “bro culture” affects investing

Why the military is a great organization to draw inspiration from

Why technical founders need to learn how to market the product

A lot of startups fail because the team that built the product doesn’t have any experience taking the product into the market. That’s why it’s so critical that founders have the ability to sell their own products. It’s a fantasy that a technical founder can just hire a person to do this for them and have good results. Building a business is a team sport requiring different people who understand how to compete in a category. Running a business isn’t like running a frat house, so there’s a requirement to act accordingly. We have to take things seriously. We owe it to our employees, stockholders and customers .