Legendary Investor and Entrepreneur Gary Swart Joins the Blood, Sweat & Balance Sheets Podcast

For most professionals, becoming a manager is something we aspire to become. 

Though it comes with more responsibilities, longer hours, and many more meetings, it’s the ultimate signal that you add value to the organization and are trusted to help others operate at peak efficiency. 

When Gary Swart was approached by Pure Software’s CEO, a guy named Reed Hastings (Yes, that Reed Hastings) about taking on a managerial position on the company’s sales team, Swart’s response was hardly what Hastings expected.

“I asked him, ‘ Reed, why would I want to be a manager, I’m making money,’” recalled Gary recently on Blood, Sweat & Balance Sheets, hosted by FloQast Co-founder and CEO Mike Whitmire. “It took probably three or four weeks to take the job. HR had to ask, the head of sales reached out, and they actually had to convince me to take that manager’s position.”

Of course, things worked out for Pure Software, Hastings, and Swart. Pure Software went public in 1995. Hastings, who has spoken candidly about his struggles with managing a growing company, having never previously managed employees, saw the company go public, merge with Atria Software, and then went on to start Netflix with former Pure Software employee Marc Randolph. 

Swart’s trajectory looked a little different, but no less successful. After becoming a manager, Gary ultimately became Director of Corporate Sales at Pure Software and, after the merger, Pure Atria. After a few stops with Rational Software (which had acquired Pure Atria), IBM (which acquired Rational Software), and Intellibank, Gary joined oDesk, overseeing the company’s growth and eventual merger with Elance to become Upwork, which went public in 2018. 

On this episode of Blood, Sweat & Balance Sheets, Gary and Mike discuss the ins and outs of building and scaling an effective sales team, why some employees don’t make good managers, and why his VC firm, Polaris Partners, decided to invest in a Los Angeles-based startup called FloQast. 

Check out the episode, and don’t forget to subscribe on your favorite podcast service!


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