Oct 20, 2023 · 27m · 20vc

20VC: NEW FORMAT: Harry Stebbings on Why Seed Pricing is as High as Ever, Why Series A is the Best Place to Invest Today, Why Growth Founders Need to Reshape Expectations, Why M&A Windows Remain Shut and When Will IPO Windows Crack Open

Harry Stebbings · 25m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this special solo episode of TwentyVC, Harry Stebbings utilizes proprietary dataset insights to analyze the venture capital market, covering LP fundraising dynamics, valuation resets across seed and growth stages, liquidity roadblocks, and emerging AI trends.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 97.9% of the talking time here. How this is scored →

Harry as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Harry pushing back 0.0
05100:0010:0020:003:11–6:04 · Harry as informed peer 0/10 Special Episode Format Announcement and Data Context This is a solo monologue segment where Harry introduces the new format and outlines the three core pillars of LP fundraising. Per the prompt instructions, monologue segments receive zeroes across host and guest interaction metrics.6:04–8:16 · Harry as informed peer 0/10 Evolution of Winning Manager Profiles and Portfolio Discipline Harry delivers a solo analysis on the shift toward disciplined portfolio management and the 'end of the barbell' fund sizing trend. Since there is no guest interaction, all scores are zero.8:16–12:45 · Harry as informed peer 0/10 Proprietary Data Insights on VC Performance, Valuations, and Carry Harry presents proprietary 20VC data points regarding DPI vs NPS, temporal diversification, and markdowns in a solo monologue format, resulting in all zero interaction scores.12:46–16:38 · Harry as informed peer 0/10 Core Criteria for Evaluating Fund Managers Harry monologues on what LPs should evaluate in fund managers and transitions into his assessment of seed-stage pricing dynamics. No back-and-forth dialogue occurs.16:40–19:07 · Harry as informed peer 0/10 Series A as the Optimal Risk-Reward Entry Point Harry explains why Series A currently represents the best risk-reward profile and discusses pricing compression at the growth stage. As a monologue, all metrics are scored at zero.19:10–21:14 · Harry as informed peer 0/10 M&A Stagnation and Tech IPO Market Outlook Harry reviews the stagnation in M&A due to lack of buyer interest and regulatory scrutiny, sharing his timeline for tech IPO window openings. As a solo presentation, scores remain zero.21:14–24:28 · Harry as informed peer 0/10 Secondary Market Opportunities and Liquidity Dynamics Harry discusses the secondary market landscape across funds, LPs, and employees, concluding with five predictions for AI. As a solo monologue, all power dynamic scores are zero.3:11–6:04 · Guest teaching 0/10 Special Episode Format Announcement and Data Context This is a solo monologue segment where Harry introduces the new format and outlines the three core pillars of LP fundraising. Per the prompt instructions, monologue segments receive zeroes across host and guest interaction metrics.6:04–8:16 · Guest teaching 0/10 Evolution of Winning Manager Profiles and Portfolio Discipline Harry delivers a solo analysis on the shift toward disciplined portfolio management and the 'end of the barbell' fund sizing trend. Since there is no guest interaction, all scores are zero.8:16–12:45 · Guest teaching 0/10 Proprietary Data Insights on VC Performance, Valuations, and Carry Harry presents proprietary 20VC data points regarding DPI vs NPS, temporal diversification, and markdowns in a solo monologue format, resulting in all zero interaction scores.12:46–16:38 · Guest teaching 0/10 Core Criteria for Evaluating Fund Managers Harry monologues on what LPs should evaluate in fund managers and transitions into his assessment of seed-stage pricing dynamics. No back-and-forth dialogue occurs.16:40–19:07 · Guest teaching 0/10 Series A as the Optimal Risk-Reward Entry Point Harry explains why Series A currently represents the best risk-reward profile and discusses pricing compression at the growth stage. As a monologue, all metrics are scored at zero.19:10–21:14 · Guest teaching 0/10 M&A Stagnation and Tech IPO Market Outlook Harry reviews the stagnation in M&A due to lack of buyer interest and regulatory scrutiny, sharing his timeline for tech IPO window openings. As a solo presentation, scores remain zero.21:14–24:28 · Guest teaching 0/10 Secondary Market Opportunities and Liquidity Dynamics Harry discusses the secondary market landscape across funds, LPs, and employees, concluding with five predictions for AI. As a solo monologue, all power dynamic scores are zero.3:11–6:04 · Guest disagreement 0/10 Special Episode Format Announcement and Data Context This is a solo monologue segment where Harry introduces the new format and outlines the three core pillars of LP fundraising. Per the prompt instructions, monologue segments receive zeroes across host and guest interaction metrics.6:04–8:16 · Guest disagreement 0/10 Evolution of Winning Manager Profiles and Portfolio Discipline Harry delivers a solo analysis on the shift toward disciplined portfolio management and the 'end of the barbell' fund sizing trend. Since there is no guest interaction, all scores are zero.8:16–12:45 · Guest disagreement 0/10 Proprietary Data Insights on VC Performance, Valuations, and Carry Harry presents proprietary 20VC data points regarding DPI vs NPS, temporal diversification, and markdowns in a solo monologue format, resulting in all zero interaction scores.12:46–16:38 · Guest disagreement 0/10 Core Criteria for Evaluating Fund Managers Harry monologues on what LPs should evaluate in fund managers and transitions into his assessment of seed-stage pricing dynamics. No back-and-forth dialogue occurs.16:40–19:07 · Guest disagreement 0/10 Series A as the Optimal Risk-Reward Entry Point Harry explains why Series A currently represents the best risk-reward profile and discusses pricing compression at the growth stage. As a monologue, all metrics are scored at zero.19:10–21:14 · Guest disagreement 0/10 M&A Stagnation and Tech IPO Market Outlook Harry reviews the stagnation in M&A due to lack of buyer interest and regulatory scrutiny, sharing his timeline for tech IPO window openings. As a solo presentation, scores remain zero.21:14–24:28 · Guest disagreement 0/10 Secondary Market Opportunities and Liquidity Dynamics Harry discusses the secondary market landscape across funds, LPs, and employees, concluding with five predictions for AI. As a solo monologue, all power dynamic scores are zero.3:11–6:04 · Harry pushing back 0/10 Special Episode Format Announcement and Data Context This is a solo monologue segment where Harry introduces the new format and outlines the three core pillars of LP fundraising. Per the prompt instructions, monologue segments receive zeroes across host and guest interaction metrics.6:04–8:16 · Harry pushing back 0/10 Evolution of Winning Manager Profiles and Portfolio Discipline Harry delivers a solo analysis on the shift toward disciplined portfolio management and the 'end of the barbell' fund sizing trend. Since there is no guest interaction, all scores are zero.8:16–12:45 · Harry pushing back 0/10 Proprietary Data Insights on VC Performance, Valuations, and Carry Harry presents proprietary 20VC data points regarding DPI vs NPS, temporal diversification, and markdowns in a solo monologue format, resulting in all zero interaction scores.12:46–16:38 · Harry pushing back 0/10 Core Criteria for Evaluating Fund Managers Harry monologues on what LPs should evaluate in fund managers and transitions into his assessment of seed-stage pricing dynamics. No back-and-forth dialogue occurs.16:40–19:07 · Harry pushing back 0/10 Series A as the Optimal Risk-Reward Entry Point Harry explains why Series A currently represents the best risk-reward profile and discusses pricing compression at the growth stage. As a monologue, all metrics are scored at zero.19:10–21:14 · Harry pushing back 0/10 M&A Stagnation and Tech IPO Market Outlook Harry reviews the stagnation in M&A due to lack of buyer interest and regulatory scrutiny, sharing his timeline for tech IPO window openings. As a solo presentation, scores remain zero.21:14–24:28 · Harry pushing back 0/10 Secondary Market Opportunities and Liquidity Dynamics Harry discusses the secondary market landscape across funds, LPs, and employees, concluding with five predictions for AI. As a solo monologue, all power dynamic scores are zero.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 91.1% · guest 8.9%0:00 · Harry 91.1% · guest 8.9%3:00 · Harry 98.7% · guest 1.3%3:00 · Harry 98.7% · guest 1.3%6:00 · Harry 100% · guest 0%6:00 · Harry 100% · guest 0%9:00 · Harry 100% · guest 0%9:00 · Harry 100% · guest 0%12:00 · Harry 100% · guest 0%12:00 · Harry 100% · guest 0%15:00 · Harry 100% · guest 0%15:00 · Harry 100% · guest 0%18:00 · Harry 100% · guest 0%18:00 · Harry 100% · guest 0%21:00 · Harry 100% · guest 0%21:00 · Harry 100% · guest 0%24:00 · Harry 91.1% · guest 8.9%24:00 · Harry 91.1% · guest 8.9%27:00 · Harry 100% · guest 0%27:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 13:40 Monologue format - no guest combativeness

This is a solo presentation episode by Harry Stebbings without an active guest, so no interpersonal combativeness occurred.

Hardest push from Harry ▶ 10:05 Monologue format - challenging industry dogmas

While Harry challenges the conventional industry dogma of 'leaning in' using fund data, it occurs as an analytical monologue rather than interpersonal host pushback.

Biggest teaching moment ▶ 8:50 Monologue format - no schooling of host

Because there is no guest present in the conversation, the host is not schooled or corrected by an external speaker.

Harry holds his own ▶ 9:30 Monologue format - Harry delivers proprietary data insights

Harry presents proprietary data showing an inverse correlation between founder NPS and manager DPI, showcasing deep domain analysis within his solo breakdown.

the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Special Episode Format Announcement and Data Context 0000 This is a solo monologue segment where Harry introduces the new format and outlines the three core pillars of LP fundraising. Per the prompt instructions, monologue segments receive zeroes across host and guest interaction metrics.
Evolution of Winning Manager Profiles and Portfolio Discipline 0000 Harry delivers a solo analysis on the shift toward disciplined portfolio management and the 'end of the barbell' fund sizing trend. Since there is no guest interaction, all scores are zero.
Proprietary Data Insights on VC Performance, Valuations, and Carry 0000 Harry presents proprietary 20VC data points regarding DPI vs NPS, temporal diversification, and markdowns in a solo monologue format, resulting in all zero interaction scores.
Core Criteria for Evaluating Fund Managers 0000 Harry monologues on what LPs should evaluate in fund managers and transitions into his assessment of seed-stage pricing dynamics. No back-and-forth dialogue occurs.
Series A as the Optimal Risk-Reward Entry Point 0000 Harry explains why Series A currently represents the best risk-reward profile and discusses pricing compression at the growth stage. As a monologue, all metrics are scored at zero.
M&A Stagnation and Tech IPO Market Outlook 0000 Harry reviews the stagnation in M&A due to lack of buyer interest and regulatory scrutiny, sharing his timeline for tech IPO window openings. As a solo presentation, scores remain zero.
Secondary Market Opportunities and Liquidity Dynamics 0000 Harry discusses the secondary market landscape across funds, LPs, and employees, concluding with five predictions for AI. As a solo monologue, all power dynamic scores are zero.

Statements from this episode (31)

Assertion Not checkable as stated
20VC Holds 1,000+ Investor Track Records and 10,000+ Founder References
“At TwentyVC, we have the most comprehensive data on a generation of venture investors. We have over a thousand track records, over 10,000 references with individual NPS from founders on their investors, where they added value, where they didn't add value, how …”
Harry Stebbings Oct 20, 2023 ▶ 0:05
Assertion Supported
LPs Remain Open for Business Despite Negative Public Sentiment
“First and most importantly, despite what you read on Twitter, LPs do remain open for business.”
Harry Stebbings Oct 20, 2023 ▶ 4:10
Insight
Fund Managers Need Two of Three Key Pillars to Raise Capital
“A truly differentiated model, be it on the servicing side, be it on the sourcing side, you have to have two of the three to be successful in this fundraising market.”
Harry Stebbings Oct 20, 2023 ▶ 5:33
Prediction Not checkable as stated
VC Success Will Shift From Brand Capital to Deal Picking
“So we'll see a shift in emphasis away from the aspirational capital towards the really great pickers.”
Harry Stebbings Oct 20, 2023 ▶ 6:34
Insight
Top VCs Succeed by Strategically Trimming Best Positions, Not Doubling Down
“The best actually strategically lent out of their best positions, and so I think we'll see a movement away from the momentum, portfolio management, liquidity management doesn't matter, to actually the best returning managers being incredibly disciplined around…”
Harry Stebbings Oct 20, 2023 ▶ 6:53
Assertion Partly supported
LPs Are Abandoning Sub-$100M and $1B+ Funds for $250M-$600M Range
“LPs are moving away from the sub hundred million dollar funds with little track record and little data. In a lot of cases, given the size of their check, it's not worth their time for the risk profile attached. At the same time, LPs are moving away from the bi…”
Harry Stebbings Oct 20, 2023 ▶ 7:17
Assertion Not checkable as stated
Higher Founder NPS Inversely Correlates With VC DPI Returns
“There is an inverse correlation between the NPS of the manager and the DPI provided. Most often, the higher the NPS, the lower the DPI, and vice versa.”
Harry Stebbings Oct 20, 2023 ▶ 9:23
Assertion Not checkable as stated
2021 12-Month Deployment Funds Paid 41% Higher Entry Prices
“For those that deployed funds in 12 months in twenty-twenty-one, their average entry price is 41% higher than those that deployed over a three-year period.”
Harry Stebbings Oct 20, 2023 ▶ 9:54
Assertion Not checkable as stated
Exit Timing Yields 3x Return Spread on Identical VC Positions
“Proprietary 20 VC data shows managers with the same positions, but three X different returns due to timing and size of exiting a position.”
Harry Stebbings Oct 20, 2023 ▶ 10:37
Prediction Open · timeframe Oct 2028
Gap Between TVPI and DPI Will Be Largest in Venture History
“The chasm between TVPI and DPI will be the biggest in venture history.”
Harry Stebbings Oct 20, 2023 ▶ 10:50
Assertion Not checkable as stated
Top-DPI Venture Managers Mark Down Portfolios Fastest
“There is a direct correlation between the best performing DPI managers, And the speed and accuracy with which they mark down their positions.”
Harry Stebbings Oct 20, 2023 ▶ 11:20
Insight
Rapid Fund Scaling From $300M to $2B Misaligns Manager and LPs
“If a fund today is three, three hundred million, and the manager wants to scale to two billion over the next three to five years, They might not be aligned to your long-term financing interests.”
Harry Stebbings Oct 20, 2023 ▶ 13:35
Prediction Not checkable as stated
Seed Valuations for Top Deals Will Remain High Through Late 2024
“For the best deals, in the best markets, pricing continues to remain incredibly high at seed, and I believe we will see it stay that way over the next six to 12 months.”
Harry Stebbings Oct 20, 2023 ▶ 14:57
Opinion
Sub-$75M Funds Cannot Compete in High-Priced Seed Rounds
“This is not a game that a sub-seventy-five million dollar seed fund manager can play. You simply cannot get the ownership required, or the check size often in those hot rounds, to make the business model work for that entry price and that check size if you're …”
Harry Stebbings Oct 20, 2023 ▶ 15:15
Insight
VC Checks Under 1% of Fund Size Are Not Firm Priorities
“For founders listening to this, wondering if the check size that the fund is looking to invest in their company is meaningful to the fund, a very simple heuristical question to ask is, what percent of your fund is this check going into my company? If it's unde…”
Harry Stebbings Oct 20, 2023 ▶ 16:02
Opinion
Series A Is Currently the Best Risk-Reward Entry Point in Venture
“I think Series A is actually the best risk to reward insertion point in venture stay.”
Harry Stebbings Oct 20, 2023 ▶ 16:41
Assertion Not checkable as stated
Gap Between Seed and Series A Valuations Has Never Been Smaller
“The price inflection between seed and Series A has actually never been smaller. Yet the de-risking that has occurred in that chasm has never been greater.”
Harry Stebbings Oct 20, 2023 ▶ 16:49
Assertion Partly supported
Multi-Stage VC Funds Are Retreating From Series A to Seed
“As mentioned, many of the multistage funds are reluctant to deploy the 20 to forty million dollar Series A and B checks, and are instead moving to seed to remain in market, still writing checks, but putting fewer dollars out the door.”
Harry Stebbings Oct 20, 2023 ▶ 17:26
Assertion Supported
Fast-Growing SaaS Startups Over $15M ARR Get 10-15x Multiples
“When at fifteen million ARR and above, 10 to 15 X revenue deals are still on offer for fast-growing SaaS companies.”
Harry Stebbings Oct 20, 2023 ▶ 18:14
Prediction Held up
Non-AI Growth Founders Will Face Valuation Compression
“Founders are going to need to reduce expectations on price if they don't have a great AI story, but they're at fifteen million in ARR, with good margins, strong revenue quality, the deals can still get done, But you're definitely going to see compression in te…”
Harry Stebbings Oct 20, 2023 ▶ 18:29
Prediction Not checkable as stated
Tech M&A Markets Will Remain Closed
“M&A markets have dried up almost completely, and I think they will continue to remain closed.”
Harry Stebbings Oct 20, 2023 ▶ 19:11
Assertion Contradicted
Small-Scale M&A Is Limited Strictly to AI Talent Acquisitions
“The only small-scale acquires that we are seeing take place currently is acquisitions where there is incredibly desirable AI talent within the startups, and incumbents are purely acquiring those companies for that AI talent and integrating them into their exis…”
Harry Stebbings Oct 20, 2023 ▶ 19:35
Prediction Held up
Stripe and SpaceX Will Not Go Public in 2024
“I don't expect Stripe or SpaceX to go out next year, and Databricks alone won't be enough to crack open the IPO windows.”
Harry Stebbings Oct 20, 2023 ▶ 20:33
Prediction Not checkable as stated
Tech IPO Market Will Not Reopen Until Q1 2025
“I think this will be a twenty-twenty-five Q. One event, but the question is what will be enough to crack them open? As I said, I think twenty-twenty-five Q. One is when we really will start to see the IPO windows open again.”
Harry Stebbings Oct 20, 2023 ▶ 21:01
Opinion
Current VC Market Is a Historic Secondary Market Opportunity
“Today is likely one of the best ever opportunities for activity in the secondary markets”
Harry Stebbings Oct 20, 2023 ▶ 21:27
Assertion Not checkable as stated
Institutional LPs Are Selling VC Fund Positions at 70-80% Discounts
“We've seen discounts from our data, either in full or as a strip sale, at as much as 70 to 80% off.”
Harry Stebbings Oct 20, 2023 ▶ 22:18
Prediction Not checkable as stated
Top VC Secondary Market Positions Will Close Within 12 Months
“I expect some of the best secondary positions to be bought in the next 12 months.”
Harry Stebbings Oct 20, 2023 ▶ 23:01
Prediction Not checkable as stated
99% of Money Invested in AI Startups Will Go to Zero
“However, 99% of the money invested into AI startups today will go to zero.”
Harry Stebbings Oct 20, 2023 ▶ 23:24
Insight
Proprietary Data Is the Single Most Important Differentiator in AI
“In AI, access to proprietary data will be the single most important differentiator.”
Harry Stebbings Oct 20, 2023 ▶ 23:35
Prediction Not checkable as stated
Incumbents Capture Short-Term AI Value, Startups Win Over 5-10 Years
“In the short term, incumbents will accrue the most value, leveraging existing distribution, To provide co-pilot products. Over the longer term, startups providing tools for new product paradigms will be best placed to win over the next five to 10 years.”
Harry Stebbings Oct 20, 2023 ▶ 23:48
Prediction Open · timeframe Oct 2028
Software Pricing Will Shift From Per-Seat SaaS to Consumption-Based
“We will move away from a traditional per-seat SaaS model to a consumption-based model, aligned much more closely to value and output.”
Harry Stebbings Oct 20, 2023 ▶ 24:21
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