The Twenty Minute VC (20VC) – March 9, 2026

Episode: “Inside Accel’s $4BN Growth Investing Machine | Cursor is Dead is Total BS: Here is Why | What Missing Rippling and ElevenLabs Taught Us | Are $2BN–$10BN IPOs Dead | Why Now is a Great Time to be Thoma Bravo with Miles Clements”
Host: Harry Stebbings
Guest: Miles Clements, Accel Partner

Episode Overview

This candid, in-person episode features Harry Stebbings in conversation with Miles Clements, leader of Accel’s growth investing practice. The episode delivers an unusually forthright look at Accel’s strategy, mistakes, and wins, focusing on current topics like disruptive AI trends, the debate about "dead" verticals and the realities of value creation at the growth stage. Key discussion threads include assessing value in fast-moving AI markets, what it means to miss a generational company like Rippling or ElevenLabs, the “Cursor is dead” meme, IPO market realities, and portfolio construction for mega funds in a dramatically changing environment.

Major Themes

• Evaluating Value in Rapidly Changing AI Markets
• The Truth about Cursor: "Cursor is dead is total BS"
• Venture Misses: Lessons from Rippling & ElevenLabs
• Growth Fund Strategy and Mega Outcomes
• IPOs, Liquidity, and the Death of the $2–10BN Public Exit
• Portfolio Construction Nuance
• The Role of the Investor/Board Member
• Regrets, Wins, and the Human Side of Venture

Key Discussion Points & Insights

1. Valuing AI Companies in a Transient Market

"Investing is an art and a science. The science is understanding how to properly value a company and the art is understanding when to break the rules."
— Miles Clements, (00:15)

• Framework for AI Company Evaluation:
  • Focus on time to value and durability of value.
    • Example: Legal/Accounting AI: long time-to-value, but durable if sticky with professionals.
    • "Vibe coding" tools: rapid time-to-value but poor durability; quick initial usage but little staying power.
  • Coding as the Key AI Vertical:
    • Coding tools (Cursor, Claude Code, etc.) shine on both axes—quick to benefit, durable, and with compound usage effects.

“[With Cursor] you can start using it in an afternoon and by that evening you’re ten times more productive. The time to value is very short, and then the durability of that value compounds.”
— Miles Clements, (05:55)

• Market Expansion:
  • AI tools are expanding user bases; "people who would not have been software developers a year ago today can be software developers with these tools." (07:22)

2. Cursor Is Dead? Miles’ Take on the Trend

• Debunking the ‘Cursor is Dead’ Meme:
  • Industry chatter (e.g., Chamath, Jerry Murdoch) is overblown.
  • Cursor is not dying; metrics show intense engagement—90% of users are daily active Agent users, agent product grew 15x in a year, new Cloud Agent feature responsible for 35% of merged PRs within three months (08:15).
• Cursor’s Multimodal Advantage:
  • 50% of developers switch AI models daily; Cursor empowers multimodal use, providing "an index of AI innovation."
• On Building Proprietary Models:
  • Cursor aims for specialized, not generalist, coding models—a distinct edge for enterprise/pro users.

“Cursor is going to build specialized coding models that are going to serve specialized coding tasks, especially for a lot of enterprise users. Their models are there for professional coders to do professional work.”
— Miles Clements, (10:23)

3. Underwriting Growth Bets and Platform Aspirations

• How Accel Underwrote the Cursor Deal:
  • First round price: $9.5M (“We were underwriting to the idea that this could be the engineering platform company, which never existed before.”)
  • Was not about near-term financials: “The financials of this company to me are purely a reflection of the product market fit and it’s unlike anything I’ve ever seen.” (12:58)
• On Mega Outcomes & Fund Size Pressure:
  • To return mega-funds, you need $50B+ companies, but the size of possible outcomes has drastically expanded in the last decade.

"A decade ago there were zero companies worth a trillion dollars. Five years later there were six…today there’s a dozen."
— Miles Clements, (16:43)

• Nuance in Portfolio Construction:
  • Balance “breakout leader” bets with differentiated, less obvious winners (e.g. bootstrapped companies in unexpected geographies).

“The best funds in the world, the best investors in the world, embrace the nuance. The right answer is always somewhere in the middle.”
— Miles Clements, (15:35)

4. Investment Discipline and “Breaking the Rules”

• When to Break the Rules:
  • The art is in judgment on when to let go of strict ownership thresholds or pricing discipline to access unique founders and markets.
  • Reflects on missing Rippling: "We stuck to our knitting on the investment framework. The ownership thresholds, the opportunity to get involved was going to be at a high valuation...would have required us to break a lot of rules." (23:00)

“Generally speaking, sticking to your rules is a good place to be...Breaking the rules is something you should do very, very rarely.”
— Miles Clements, (23:59)

5. Lessons from Missing Generational Companies

• Missing Rippling:
  • Points to underappreciating the “marginal ease of ARR accumulation”—seeing only the current product/growth and missing Parker Conrad’s margin insights.
  • “Nobody in the world does that better than Parker Conrad...he has this innate sense for pockets of margin that other people wouldn’t go build companies around.” (21:56)
• Missing ElevenLabs:
  • “We haven’t spent enough time with the founder, which is our loss. I think we really regret that one.” (55:31)
• Pain of Missing:
  • Losing—being in the running and failing—stings more than simply not seeing the deal. (56:01)

6. AI, Market Extremes, & The Death of the $2B–$10B IPO

• Is the $2–$10BN IPO Dead?
  • Many strong companies going/staying private longer; public market thresholds have shifted higher ("line of sight" to $5B+ is now crucial).
  • Secondary/tender opportunities make liquidity less dependent on IPOs.
• Private vs. Public Markets:
  • "There are things that public companies can do that private companies can’t, and vice versa. But for the 10–20 best companies, they can access liquidity and capital without going public." (43:13)
  • The “casinoization” and irrationality of public markets: “The public markets are no longer rational. It’s not good or bad, it’s just a different asset class and stick to what you’re good at.” (48:03)

7. The Nature of Risk, Misses, and Investing "Where You’re Good"

• Swinging for Home Runs vs. Hitting Singles and Doubles:
  • “Focus on hitting singles and doubles and let the home runs take care of themselves.” (32:55)
• Don’t Just Momentum Chase:
  • "There are companies where it is justified to chase momentum [e.g., Anthropic]...but ascribing those characteristics to everything at Series A is dangerous." (34:16–35:18)
• On Regret:
  • Still time for generational bets: "I believed that all of the generational investments in AI had been made...That was really stupid...there is still time to be a part of some of them." (40:20–41:02)

8. Investor Role and Board Behavior

"There’s basically these bumper decisions that come up a couple of times a year...having a good investor or just a good partner to the business can be really useful."
— Miles Clements, (49:39)

• Role of Investors:
  • Not needed for every decision—only key, inflection-point calls.
  • Best board members are not most vocal—wisdom and professionalism matter.

“There’s generally an inverse correlation between how vocal somebody is and how helpful they actually are.” (50:51)

9. Human Story: Rewards, Regrets, & What Excites Miles

• Best Win:
  • Linear: “It had been the worst couple of months that I’d experienced in a long time...when Kari called and said he wanted to work together, it was pretty euphoric.” (56:48)
• What Excites Miles Most:
  • Watching younger partners at Accel flourish: “I’m not smart enough to predict where the world is going to be a decade from now, but I’m proud to know them.” (59:09)

Notable Quotes & Memorable Moments

• On Fads & Substance:
  “Growth can obscure and blind you to a lot of underlying ills in the business.” (00:09, 25:42)
• On Market Churn:
  “Cursor is going to build specialized coding models that are going to serve specialized coding tasks...Their models are there for professional coders to do professional work.” (10:23)
• On Breaking Rules:
  “The art is understanding when to break the rules.” (00:15, 23:43)
• On Missing the Generational AI Bets:
  “We beat ourselves up over it...but we’ve course corrected.” (27:32)
• On Portfolio Construction:
  “The best funds in the world, the best investors in the world, embrace the nuance.” (15:35)
• On Founder-Run Companies:
  “There is unmistakably something special about a founder-led company.” (39:47)
• On Personal Meaning in Deals:
  Linear: “That one on a personal level was maybe the best week...It had been the worst couple of months that I’d experienced in a long time.” (56:43)

Timestamps for Key Segments

| Time | Segment/Discussion Topic | |-------------|---------------------------------------------------------------| | 04:42 | How to ascertain value in AI & Miles’ frameworks | | 06:30 | “Cursor is dead” meme debunked | | 08:00 | The move to Agent-driven AI usage | | 10:08 | On Cursor building proprietary models | | 12:56 | Why financials matter but don’t drive Accel’s investment case | | 15:35 | Portfolio construction nuance & mega-fund pressure | | 17:08 | The expansion of outcome sizes in tech | | 21:13 | Missing Rippling—what was overlooked? | | 23:43 | When to break the rules in investing | | 32:55 | Focus on “singles and doubles” vs. only home runs | | 38:09 | The humbling effect of the new market reality | | 43:13 | IPOs, secondaries, and private company liquidity | | 48:03 | Rationality of public vs. private markets | | 50:45 | How to spot bad board behavior as a founder | | 55:31 | Missing ElevenLabs regret | | 56:43 | Linear win—personal impact | | 59:01 | What excites Miles about the future at Accel |

Additional Memorable Moments

• On Losing vs. Not Seeing:
  "Losing stings more." (56:01)
• On Who He’d Add to the Team:
  "I’d probably try my very hardest to talk Mike Cannon-Brooks into retiring from operating, into being an investor. He would never do it." (53:30)
• On Boardroom Wisdom:
  “The coin box that rattles loudest has the least in it.” (51:06)

Conclusion

This episode is packed with honest, practical, and philosophical lessons from building a mega-fund practice at Accel—tempered by open reflections on both missed wins and euphoric successes ("Cursor is dead is total BS"), while mapping the terrain of IPOs, portfolio nuance, and inevitable market humbling. Miles’s authenticity and the freewheeling in-person banter make this a must-listen for anyone at the growth/late-stage intersection of venture and operating in this defining era of AI and tech investing.