Conviction, Cheating, AI, and (Not) Predicting with Shawn Merani
- Joe Magyer
- Jul 23
- 2 min read
Shawn Merani is the Founder and Managing Partner of Parade Ventures. Parade is a seed stage venture firm with an affinity for enterprise software. We talked about the state of seed investing, relationships, observing vs. predicting, cheating, AI and a huge win Shawn had recently with the acquisition of Moveworks.
The episode is now available on Apple Podcasts, Spotify, Amazon, and YouTube Music.
Conviction, Cheating, AI, and (Not) Predicting with Shawn Merani
00:59 Shawn Merani's Journey and Moveworks Investment
06:18 The State of AI Investing
10:33 Lessons from Fund One and the Evolving Landscape
16:54 Building Relationships with Founders
20:12 The Role of Capital Efficiency in Startups
25:02 Teaching Venture Finance at Berkeley
29:20 The Impact of AI on Venture Capital
Insights from Conviction, Cheating, AI, and (Not) Predicting with Shawn Merani
Runs a deliberately tight portfolio. Parade backs just four to six new companies per year so it can own more of each winner and stay deeply engaged with founders
Bet on Moveworks before “AI” was a buzz-word. Shawn wrote one of the first checks into the company (then called BannerTech) in 2016, years ahead of the generative-AI wave
Turned that early risk into a $2.85 B outcome. Moveworks’ 2025 sale to ServiceNow delivered Shawn a flagship exit and reinforced his “get there early, own enough” thesis
Relationship-first investing. He meets portfolio CEOs every other week, often takes a board seat, and insists on candid conversations from day one to build real conviction
“Entry point matters.” Even in today’s cash-rich seed market, Shawn argues that price discipline and meaningful ownership are must-haves; seed feels as frothy as 2021, but a Series A squeeze looms
Observe > predict. He tries to avoid hype cycles and bidding wars, focusing instead on sectors that will matter but aren’t hot yet—“I’m not smart enough to call innings on AI and don’t want to”
Enterprise software isn’t dead. Despite sensational claims, Shawn’s view is simple: “people buy software from people,” so enterprise SaaS demand will endure even as AI reshapes tooling
Uses gen-AI tactically, not for judgment. He’s experimenting with off-the-shelf LLM tools to speed diligence (market maps, competitive scans) but says no model can yet gauge founder grit
Teaches an MBA elective and warns students—don’t “cheat” with ChatGPT. Attendance and live participation with guest investors drive the grade; skipping the work just short-changes yourself
The content here is for informational purposes only and should not be construed as investment, legal or tax advice. The opinions expressed by guests are their own and do not reflect the views of Seaplane Ventures. Our host, guests and clients may hold investments discussed in this podcast. Please invest responsibly.
