This Week in Startups Ep. 2204 (Nov 6, 2025)

Is Investing REALLY the Hardest Job in Tech?

TWIST VC Roundtable feat. Deedy Das (Menlo Ventures), Jay Eum (GFT Ventures), and Jason Calacanis

Overview

In this episode, host Jason Calacanis convenes a VC roundtable with Menlo Ventures' new partner Deedy Das and Global Frontier Technology Ventures co-founder Jay Eum. They dissect the seismic shifts in venture capital, from high-profile leadership changes (Sequoia’s changing of the guard) to today’s global startup explosion, debates over capital efficiency, return dynamics in venture, and the new realities of founder and investor life in an AI-powered world. The panel also discusses pre-seed funding challenges, the effect of AI-driven growth, ethics in a frothy market, and their current favorite portfolio companies.

Key Discussion Points & Insights

1. VC Succession, Legacy, and Industry Change

Timestamps: 00:00 – 13:20

• Sequoia’s Transition: Roloff Botha steps back, Alfred Lynn & Pat Grady step in as stewards of the legendary firm. The panel reflects on Sequoia’s tradition of orderly generational handoffs and the importance of planning for leadership transition.

  "They have a great tradition at Sequoia with these stewards... And they, you know, gave it over to Ruloff and Alfred and now Alfred and another partner are going to run it. So, you know, best of luck to Ruloff. He had one of the great runs in the history of venture capital."
  — Jason Calacanis (05:43)

• Menlo Ventures’ Evolution: Deedy describes Menlo’s approach: integrating operator-founders with career investors to reinvigorate a 50-year-old firm.

  "We're trying really hard to marry people who've been in the trenches running companies with investors who get the finances, who understand the long-term vision as well."
  — Deedy Das (00:22)

2. The Global Startup Boom, Too Much Capital?

Timestamps: 17:26 – 23:48

• Is Capital Overabundant?
  Jason relays Roloff Botha’s sentiment that adding more capital to Silicon Valley no longer yields more great companies.

  "In America and Silicon Valley...there's too much capital chasing too few really great ideas. And that means you can see it in the valuations."
  — Jason Calacanis (18:12)

• Non-U.S. Ecosystems Thrive: Jay points out government-led startup creation in Israel, Korea, Japan, with alternative return expectations (not just benchmarking to the S&P 500).

• Venture Firm Differentiation: With so many funds, Jay questions the need for more unless purposely focused, e.g., GFT’s thesis around frontier tech and AI.

3. Growth, Retention, and the AI-Accelerated Company

Timestamps: 23:48 – 42:34

• Bigger, Faster Milestones: Many startups—like Glean (100M ARR quickly)—quietly reach huge revenue marks. Private markets now allow "infinite" late-stage capital, changing IPO calculus.

  "Maybe in a world before, Glean could IPO, but...now let's fortify the bank balance and then try to shoot for higher [outcomes]."
  — Deedy Das (24:28)

• Global Decacorns: Jason highlights titans like Spotify (Sweden, $100B+), Atlassian (Australia), Canva—as global exemplars, showing talent and great companies now “come from anywhere.”

• Willingness to Pay for SaaS/AI: B2B and prosumer segments are ready to pay high prices for tools that create even modest productivity gains.

  "Businesses are just very frisky about that. ...Making existing high performers higher performers is better than hiring more people."
  — Jason Calacanis (33:28)

• Retention Puzzle with AI Apps: The panel discusses "smile curves," where users return to products like ChatGPT after initial churn, signaling persistent value and product-market fit.

  "A smile curve is the most beautiful one-line description of, I have product market fit. People will churn and go like, nah, just kidding, I'm back."
  — Deedy Das (40:57)

4. The Harder Life of Early-Stage Founders (and Investors)

Timestamps: 43:59 – 53:46

• Pre-Seed Paradox: Despite record capital amounts, deal counts are dropping; investors expect more traction even at pre-seed. Competition for capital is fierce, especially for less-proven teams.

  "It’s...two different proof points. 0 to 1. Then 0 to 1 million [ARR]. You can't really fake that."
  — Jason Calacanis (46:27)

• Flight to Quality: VCs are pickier; capital concentrates on breakout companies growing fast.

• Venture Returns: Spray and Pray vs. Concentrated Bets:
  Deedy: "Spray and pray" yields lower median returns but lower variance; concentrated funds (Menlo’s approach) take bigger swings.

• VC Math Gets Tougher: Jason highlights shrinking ownership stakes (now <10% at Series A) and warns that outlandish valuations can erode fund-level returns.

  "The game becomes harder and harder in terms of eventually getting a return for your LPs. So it's... perhaps the hardest job in the ecosystem is being an investor. I think it actually is."
  — Jason Calacanis (50:28)

5. FOMO, Diligence, and Market Froth

Timestamps: 62:27 – 67:03

• Speed Over Diligence: With deals closing quickly, sometimes with little to no due diligence, term sheets land before data rooms are set up.

  "There are some cases where diligence is just not happening. That's the reality."
  — Deedy Das (62:30)

• Cutthroat Froth: Stories of “VCs chasing founders at airport security lines,” term sheets at doorsteps, and high-growth companies inciting extreme FOMO.

• Rise of Poor Behavior: As in past bubbles, hot markets spawn ethical lapses, retrades, preferential deals, and short-termism.

6. The New Face of Startup Growth (AI, Social, and Content Automation)

Timestamps: 67:03 – 76:00

• AI-driven Content & Growth:

  • Didi describes bot-driven posting on Reddit/LinkedIn—entire bot farms are spamming with AI-created content that’s almost impossible to distinguish from human posts.

  • Jay notes AI tools enabling targeted video creation, auto-generated scripts, and even fundraising automation (e.g., Lizer.ai raising their round via their own chatbot).

    "Entire companies [are] built on spamming Reddit with high quality content that's completely AI generated, where they sneak your company...in there in ways that, most humans...would not know that this is fake at face value."
    — Deedy Das (67:54)

• Dead Internet Theory Debated:
  Didi warns about a tipping point where “bots watch bots”; Jason foresees a market for authenticated “100% human” content.

  "People are going to start labeling things human only or 100% human as a reaction to this."
  — Jason Calacanis (73:45)

7. Portfolio Company Shoutouts

Timestamps: 76:00 – 83:40

• Jay’s Pick:
  • Abacus: AI enterprise solution for confidential, compliant AI applications in regulated industries, already bootstrapped to $1M ARR.
• Deedy’s Picks:
  • OpenRouter: Product-led growth in the AI model distribution space, celebrated for its dominance and rapid awareness.
  • Goodfire: Cutting-edge AI interpretability (“brain surgery for AI models”).

    "It's absolutely fundamental for society for us to understand this because we cannot trust black boxes with huge decisions."

• Jason’s Pick:
  • NextVisit.AI: AI note-taker specifically for psychiatry/clinical settings, praised for their laser-focused approach.

8. The Real Workload of VCs

Timestamps: 60:15 – 61:13

• All agreed: Modern VCs are 'always on,' with crowded inboxes, constant responsiveness, and the need to keep up with founders' pace—though the intensity differs from startup life.

  "I don't not work...I work all the time. I don't think the work is as intense as it was at a startup. But...the only thing I have to add is hours."
  — Deedy Das (60:27)

• Deedy: still feels need to prove himself via hustle; Jay lives by a zero-inbox mantra.

Notable Quotes & Memorable Moments

• On Sequoia’s Legacy:
  "One of the great venture capitalists...and I didn't know [about the transition]. But I did know that the firm had some spiciness going on with Sean McGuire being very public...I'm not sure if that contributed."
  — Jason Calacanis (05:43)

• On Modern VC Ethos:
  "Now founders expect that people in venture have some scar tissue and have been in the trenches. That's a real kind of different vibe than it was."
  — Jason Calacanis (15:44)

• On Froth and FOMO:
  "I've heard stories now of high growth founders being chased at airport security lines, people showing up unannounced at doorsteps with term sheets."
  — Jay Eum (66:22)

• On Growth over IPO:
  "Why would you want to go public? You can raise infinite money in private markets if you continue to grow. You don't have to do all of this reporting to the SEC."
  — Deedy Das (24:28)

• On Automation & "Dead Internet":
  "We're going to wind up in a world when it's just bots watching bots and humans are left by the wayside."
  — Alex (Host) (72:03)

Episode Timeline & Timestamps

• 00:00–05:43: Show opens, VC succession; Sequoia’s leadership change
• 05:43–13:20: Sequoia stewardship; Menlo’s new generation; reflections on VC legacy
• 13:20–18:12: Changing work in venture; generational perspective
• 18:12–23:48: Too much capital vs. too few great companies; global startup hubs
• 23:48–33:03: Glean’s ARR; IPO vs. private markets; SaaS & AI willingness-to-pay
• 33:03–42:34: Retention “smile curve” in AI apps; global unicorns/decacorns
• 43:59–50:28: Pre-seed funding bar; flight to quality; VC strategy variance
• 50:28–53:46: VC returns and LP expectations; capital vs. deal count
• 53:47–62:27: Blind betting, lack of diligence; FOMO and bubble ethics
• 62:27–67:03: Market excesses; term sheet shenanigans; long-term trust matters
• 67:03–76:00: AI for marketing & fundraising; dead internet theory
• 76:00–83:40: Portfolio company picks; final wrap; VC lifestyles

Conclusion

This roundtable delivers a candid state-of-the-union for modern venture, blending sharp anecdotes with hard data. It questions whether investing is actually the hardest job in tech (it’s not—being a founder is), and highlights the high-velocity, high-stress, always-on nature of the business in the AI era. It warns of ethical lapses in market bubbles and marvels at the global arms race to build billion-dollar companies—increasingly with little more than product, hustle, and sometimes, whole armies of bots.