How much secondary liquidity should late-stage founders take, and when?

Alex Bouaziz · Feb 1, 2023 · hedged

Taking secondary at Series A is unwise; taking a modest amount at later rounds, systematically refreshed each round, makes more sense

The right amount is whatever makes you comfortable given your situation, and taking a lot is probably not smart because the shares are likely worth much more later

Scope: depends on the founder's personal situation; Alex has no family and only wanted a home plus diversification

33:14 20VC: From $57M in ARR to $297M in Just 12 Months; Why Speed of Execution is the Most Important Factor to Success, Hiring 2,000 People in 3 Years Remotely & Secondaries; Why, When and How Much To Take Out with Alex Bouaziz, Co-Founder & CEO @ Deel

Harry Stebbings · May 27, 2025

Founders should not take $20-30M of secondaries at early stages — the timing of secondaries matters

Scope: early-stage rounds specifically

75:41 20VC: The Most Insane Story in Startups: Airwallex: The Angel That Turned $1M into $1BN | The Fund That Pulled a Term Sheet & Lost $1BN | Rejecting Stripe's $1.2BN Offer | Scaling to $1BN in Revenue & 100% YoY Growth for 8 Years with Jack Zhang

Jack Zhang · May 27, 2025

Late-stage founders should take enough secondaries to be set for life — roughly $20-30M in a city like London

You want the founder all in on building the business rather than worrying about feeding the family, supporting kids or buying a house

Scope: late-stage founders only; amount depends on cost of living; Melbourne lower than London

75:10 20VC: The Most Insane Story in Startups: Airwallex: The Angel That Turned $1M into $1BN | The Fund That Pulled a Term Sheet & Lost $1BN | Rejecting Stripe's $1.2BN Offer | Scaling to $1BN in Revenue & 100% YoY Growth for 8 Years with Jack Zhang

Jack Zhang · May 27, 2025

Late-stage founders (companies above a $1B valuation) should take $20-30M in secondaries — enough to remove money worries but not enough to be life-setting

A founder who isn't thinking about supporting their family can be all-in on the vision, while the amount stays modest enough not to be a 'set for life' sum

Scope: applies to late-stage founders above a billion-dollar valuation; not appropriate at early stages

75:49 20VC: The Most Insane Story in Startups: Airwallex: The Angel That Turned $1M into $1BN | The Fund That Pulled a Term Sheet & Lost $1BN | Rejecting Stripe's $1.2BN Offer | Scaling to $1BN in Revenue & 100% YoY Growth for 8 Years with Jack Zhang

Harry Stebbings · Jan 4, 2024

At that stage of company trajectory a $10M secondary doesn't serve investors' needs — they need to move $150M to get a 3-4% position

Late-stage investors need to deploy meaningful capital for a meaningful stake

32:28 Late stage investors need large secondary positions to achieve meaningful ownership