Lars Leckie is a Managing Director at Aspenwood Ventures, a Silicon Valley venture capital firm specializing in early-stage enterprise software startups.Aspenwood Ventures was rebranded from Hummer Winblad Venture Partners, the first venture capital firm focused exclusively on software. Founded in 1989, Hummer Winblad Ventures was incredibly successful from its first fund and operated for over 30 years as a pioneer in the enterprise software space. 🚀The video version of this episode is also available on our 🎥 YouTube Channel: https://youtu.be/ZPQ5GLAYB5Y?si=oK3imhlKvY05FyiZIf you like this episode, I think you'd also like our other episodes too. Please check them out. Follow Lars Leckie🐦Twitter: @LarsLeckie🔗 LinkedIn: https://www.linkedin.com/in/larsleckie/💻 Aspenwood Ventures Website: https://aspenwoodvc.com/team/Follow Sasha Earnheart-Gold:🐦 Twitter: @EarnheartGold🔗 LinkedIn: https://www.linkedin.com/in/sashaearnheart-gold/📸 Instagram: @EarnheartGold📬 Subscribe to the Next Unicorn email newsletter on Substack: https://nextunicorn.substack.com💻 Next Unicorn Podcast website: https://www.nextunicornpodcast.com/Episode Contents:0:00:00 Teaser0:00:58 Introduction0:02:23 What Makes Aspenwood Ventures Unique0:04:31 Definition of Enterprise Software0:09:34 Successful Investment in MuleSoft ($0 to $9.8 Billion)0:11:05 More Examples of Successful Aspenwood Ventures Investments0:12:17 Aspenwood Ventures Investment Thesis0:14:23 Inflection Points in the Market That Can Lead to Startup Successes0:15:09 AI & Opportunities for Startups0:22:29 AI Startups that Aspenwood Ventures is Investing in0:27:58 Investing in Enterprise Software in a More Saturated Market0:33:36 What Made Your Most Successful VC Investments Successful?0:38:35 Being Non-Consensus and Right vs Timeframe for Others Agreeing Soon Enough0:41:27 Strategically Timing Your Market Entry for Success, and to Maximizing Runway0:42:50 How to Get Large Customers to Buy From an Early-Stage Startup0:44:50 How to Find the Best Early-Stage Startups, Founders & Startup Ideas0:46:49 How to Find the Best Early-Stage Enterprise Software Startup Founders0:48:09 How to Think About a Market Map of The Enterprise Software Space0:52:18 Additional Thoughts on How to Think About VC Investment Thesis0:56:06 What Lars Has Learned About How to be a Great Venture Capital Investor0:57:16 The Best Way to Contact Lars0:58:17 Additional Thoughts on the Future of Investing in Enterprise Software & AI1:00:23 Lars' Personal Career Background & How he Got to Where he is Today1:04:23 An Unexpected Aspect of Lars' Career Journey1:05:31 Bonus RoundTo support Next Unicorn Podcast, please press the "follow" button for the show on your podcast platform. Also, please take a moment to leave a 5-star review. And on Apple Podcasts, please also leave a few positive sentences as a written review. Thanks so much! 🙏Credits:Video/audio editor and engineer – Oleksii Kyrkach

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