Join Dean DeBiase and Ann Winblad, Founder & Managing Director Hummer Winblad Venture Partners, the first venture firm focused exclusively on software. In her 30-year career as a venture capitalist, Ann’s firm has launched over 160 enterprise software companies and led investments that pioneered successful companies across the enterprise software sector.

Humble Beginnings

Ann is a VC pioneer starting one of the first funds to only focus on software during the tough times of the late 80's, bad timing. She had around 130 investor meetings where she was consistently turned down, but she persisted. Thirty years later she has launched almost two-hundred software companies, with hundreds of investments, and dozens of successful exits and IPO's. Ann is a hands on investor who enjoys getting to know an entrepreneur, on a personal level, and participates in numerous lunches on a weekly basis. COVID has put a dent in this approach, but she is still looking at a record number of companies to fund and help scale.

2020 Digital Transformation Final Exam

We talked about what's hot and what's next and what 2020 is doing for demand. It is clear, now more than ever companies / large enterprises are accelerating digital. This renewed interest in all things digital is providing a global opportunity for startups and investments across the enterprise software space, including supply chain, engagement platforms and digital operations.

Evaluating an Investment Through VC Eyes

Does the business idea make sense, is it solving for the right pain point and does the company have the right CEO to lead? If the answers are yes to all three questions, then a VC will be more interested in your business. Recently, Ann invested in Smart Access, this Ontario business that brings automation to “deskless workers”. These are workers on the manufacturing or distribution floor that are disconnected, keep an eye on that one. Another investment I liked was Mulesoft, which was a huge success, and IPO and a multi-billion dollar exit to Salesforce. Her company generally targets startups with less than ten employees, Mulesoft only had five.

What’s Should Entrepreneurs do Now

Entrepreneurs will be wise to consult with other entrepreneurs who have successfully raised money. Tell stories, learn from each other and share best practice tips. Don't retreat in the downturn, polish your strategy, pivot into the next-normal with a new or leading position where you can add more value. She doesn't invest in products, so build a great company and team around a product. And be patient for the yes, venture capital firms take their’s a fast NO and a slow YES.

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About The Reboot Chronicles Podcast: Hosted by Dean DeBiase, The Reboot Chronicles is a popular no-holds-barred podcast on iHeart Radio, iTunes, Spotify, Google Podcasts and YouTube that has been bringing together CEOs, entrepreneurs, authors, and global leaders, for over a decade, to discuss how organizations are rebooting their leadership-competitiveness of everything from growth, innovation, and technology to talent, culture, and governance. Tune in wherever you listen to podcasts or at

Named a “Growth Guru” by Inc. Magazine, Dean DeBiase is a Faculty Member at Kellogg School of Management and Silicon Valley serial CEO, where he has served in chief executive and chairman roles of more than a dozen emerging growth companies, CEO of Fortune 500 subsidiaries, and a director on public, private, family-enterprise, CVC, PE and VC boards. He is a Technology Fellow at Northwestern University, a Board Leadership Fellow at The National Association of Corporate Directors, and an Advisor to the National Science Foundation. A Forbes Contributor and co-author of the best-selling book The Big Moo, Dean is working on his next book, Dancing with Startups. Connect with Dean here: