Secrets to Building Successful Enterprise Software Startups (& AI Startups)

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. 🚀

Next Unicorn podcast episode 9. Also available on 🎙️ Spotify, 🍎 Apple Podcasts, or wherever else you get your podcasts.

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Follow Lars Leckie
🐦Twitter: https://x.com/LarsLeckie
🔗 LinkedIn:   / larsleckie  
💻 Aspenwood Ventures Website: https://aspenwoodvc.com/team/

Follow Sasha Earnheart-Gold:
🐦 Twitter: https://x.com/EarnheartGold
🔗 LinkedIn:   / 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/

Video Contents:
0:00:00 Teaser
0:00:58 Introduction
0:02:23 What Makes Aspenwood Ventures Unique
0:04:31 Definition of Enterprise Software
0:09:34 Successful Investment in MuleSoft ($0 to $9.8 Billion)
0:11:05 More Examples of Successful Aspenwood Ventures Investments
0:12:17 Aspenwood Ventures Investment Thesis
0:14:23 Inflection Points in the Market That Can Lead to Startup Successes
0:15:09 AI & Opportunities for Startups
0:22:29 AI Startups that Aspenwood Ventures is Investing in
0:27:58 Investing in Enterprise Software in a More Saturated Market
0:33:36 What Made Your Most Successful VC Investments Successful?
0:38:35 Being Non-Consensus and Right vs Timeframe for Others Agreeing Soon Enough
0:41:27 Strategically Timing Your Market Entry for Success, and to Maximizing Runway
0:42:50 How to Get Large Customers to Buy From an Early-Stage Startup
0:44:50 How to Find the Best Early-Stage Startups, Founders & Startup Ideas
0:46:49 How to Find the Best Early-Stage Enterprise Software Startup Founders
0:48:09 How to Think About a Market Map of The Enterprise Software Space
0:52:18 Additional Thoughts on How to Think About VC Investment Thesis
0:56:06 What Lars Has Learned About How to be a Great Venture Capital Investor
0:57:16 The Best Way to Contact Lars
0:58:17 Additional Thoughts on the Future of Investing in Enterprise Software & AI
1:00:23 Lars' Personal Career Background & How he Got to Where he is Today
1:04:23 An Unexpected Aspect of Lars' Career Journey
1:05:31 Bonus Round

Credits:
Video/audio editor and engineer – Oleksii Kyrkach