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=oK3imhlKvY05FyiZ

If 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 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

To 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

Ian Chiu is a Managing Director at Owl Ventures, the largest EdTech (education technology) venture capital firm in the world, with over $2 billion under management. Owl Ventures is stage-flexible, investing in EdTech startups from seed through growth. The firm is also international, investing in EdTech startups throughout the world. Ian received an MBA at the Stanford Graduate School of Business (GSB), as well as a BS and MS from Stanford University.

To 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. On Apple Podcasts, please consider also leaving a few positive sentences as a written review. Thanks so much! 🙏

📬 To keep up to date with new episodes, please consider subscribing to the Next Unicorn email newsletter on Substack: https://nextunicorn.substack.com

🎥 Next Unicorn Podcast is also available in video on our YouTube channel (Next Unicorn: The Next Great Startups & Founders). Just search for "Next Unicorn" on YouTube. YouTube channel link: https://www.youtube.com/@NextUnicorn

This is Next Unicorn Podcast episode 8. The video version of this episode is available on the Next Unicorn YouTube channel: https://youtu.be/U_ZYwHqkWiA?si=p15gEznpG5pNlo0Q

If you like this episode, you may also like episode 7 (Top Startup Accelerator Reveals How it Helps Startups Succeed), an interview with Ajay Kamat, the head of PearX, one of the top startup accelerators in the San Francisco Bay Area. The video version of that episode is available on YouTube: https://youtu.be/SNbS7mTW2PE?si=TysiEHVFgmKZSf8y

Follow Ian Chiu:
🐦Twitter: https://x.com/OwlVC

Follow Sasha Earnheart-Gold:
🐦Twitter: https://x.com/EarnheartGold
📸Instagram: https://www.instagram.com/earnheartgold/
📬Subscribe to the Next Unicorn email newsletter on Substack: https://nextunicorn.substack.com
💻Next Unicorn website: https://www.nextunicornpodcast.com/

Video Contents:
0:00:00 Teaser Clip
0:00:58 Introduction
0:01:46 How Owl Ventures is a Unique EdTech VC Firm
0:04:36 Owl Ventures Investment Thesis around EdTech
0:05:53 Types of EdTech Startups Owl Ventures is Currently Focused on
0:06:50 Examples of EdTech Startups in the Owl Ventures Portfolio
0:09:41 The Future of Education – will Education in 10-20 Years Look Dramatically Different?
0:22:23 Does Remote Learning Really Work? What Did we Learn During Covid about Remote Learning?
0:28:21 Use of Remote Learning and EdTech vs. Socialization, Emotional Growth, and Mental Health
0:32:33 How to Think About a Market Map of EdTech
0:35:20 The Most Intriguing Areas of EdTech for Aspiring Founders to Focus on Right Now
0:40:23 How Will AI Change Education? And How Can AI Improve Education?
0:44:50 Avoiding the Dystopian Vision of AI in Education
0:51:19 How Does Education Need to Change to Prepare Students for a World Where AI is Very Present?
0:54:02 How LLMs (Large Language Models), like Chat GPT, are Affecting Owl Ventures' Investment Decisions
0:58:52 The Best Opportunities for AI EdTech Startups Right Now (Given the Strength of LLMs)
1:03:15 The Most Intriguing Areas for AI in EdTech for Aspiring Founders & Most Interesting Kinds of AI EdTech Startups Right Now
1:08:02 Final Thoughts on the Future of EdTech
1:13:13 Ian's Personal & Career Journey
1:17:41 An Unexpected Aspect of Ian's Career Path
1:21:29 Bonus Round

Credits:
Video/audio editor and engineer – Oleksii Kyrkach

Ajay Kamat is a Partner at Pear VC, where he runs PearX, one of the top startup accelerators in the San Francisco Bay Area. Pear VC has been an early investor in many successful startup companies. In this episode, we talk about the PearX method of startup success, and how the team at PearX helps startup founders avoid common mistakes, find product-market fit, land their first hires, find venture capital funding, and quickly scale into successful unicorn companies. Later in the interview, we discuss Ajay’s personal career background, his time as a founder, and how he became the head of PearX. Also, stick around to the end of the interview, because Ajay participates in the Next Unicorn Podcast bonus round!

This is Next Unicorn Podcast episode 7. The video version of this episode is available on the Next Unicorn YouTube channel: https://youtu.be/SNbS7mTW2PE?si=fDJr7IxJ-PKEk3b5

If you like this episode, I think you'd also like episode 5 (Are Startup Accelerators Worth It For Founders?), an interview with the former head of Techstars startup accelerator's San Francisco Bay Area location. The YouTube version of that episode is available at: https://youtu.be/sGBS8w0iLv0?si=8pb0dzPJqVeBZXPA

Follow Ajay Kamat:
🐦Twitter: @ajaykam

Follow Sasha Earnheart-Gold:
🐦Twitter: @EarnheartGold
📸Instagram: @EarnheartGold
📬Subscribe to the Next Unicorn email newsletter on Substack: https://nextunicorn.substack.com
💻Next Unicorn website: https://www.nextunicornpodcast.com/

Timestamps:
0:00:00 Teaser Clip
0:00:11 Introduction
0:00:20 Pear VC, PearX, & the difference between the two
0:02:18 How PearX is different than other startup accelerators
0:05:55 What PearX looks for in startups
0:07:13 How PearX evaluates and selects startup teams
0:09:01 Geographic locations of PearX startup teams & their market focus
0:10:12 At what stage is PearX most effective for startups?
0:12:11 The PearX method of startup success
0:15:22 How PearX helps B2B vs B2C startups
0:19:05 How to know when it's time for a startup to pivot
0:20:55 PearX startups that pivoted & became successful
0:23:33 The most successful PearX startups & what made them successful
0:27:30 How the PearX approach has changed over time
0:29:00 AI startup opportunities & changes in PearX startups
0:32:45 How to avoid common startup mistakes
0:35:52 What made PearX one of the top startup accelerators?
0:38:59 Additional comments about PearX and Pear VC
0:40:45 Ajay's personal career journey
0:47:37 Bonus round

Our recording setup:
-Pro webcam used to film this episode: https://amzn.to/3NZNOhH
-Mid-tier webcam option: https://amzn.to/3KPrntv
-Cheaper version of the webcam (if you just want to level up your Zoom calls): https://amzn.to/3Sb4QMe
-USB-C microphone used to film this episode: https://amzn.to/3Sf9o40
-Roost laptop stand to bring the webcam up to eye level (also alleviates back pain from bad posture and hunching over your computer): https://amzn.to/3XrYqvj

Credits:
Video/audio editor and engineer – Oleksii Kyrkach