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♦Convertible Debt Financing 
How it Works 
Benjamin M. Hron 
bhron@mccarter.com 
617.449.6584 
@HronEsq
Convertible Debt Essentials 
♦ A loan that can be converted to stock 
♦ Originally primarily used as a “bridge” between 
equity rounds 
♦ Has become a typical way to do seed stage 
deals
Cost - Benefit 
♦ Puts off discussion of valuation 
♦ Tends towards smaller deals 
– CAN be simpler, and cheaper to document, 
than equity 
– BUT can become complex; while seed equity 
getting simpler
Cycles and Styles 
♦ East Coast angel groups have evolved 
towards Preferred Stock deals 
♦ Tends to be used by friends, family, and solo 
angels 
♦ Use by superangels 
♦ Good or bad for entrepreneurs?
How it Works 
♦ Loan to (Debt of) the Company 
– Principal and interest repayable at future 
date/circumstances 
♦ May convert to equity 
– By whom (investor or company) 
– Under what conditions 
♦ Conversion typically comes with a benefit – 
most commonly a discount off next round
Basic terms and Norms 
♦ Term/due date: 1 – 2 years 
– Cash payment of principal and interest is likely 
a “fail” scenario 
♦ Interest rate: 6-10% 
– Accrues till maturity 
♦ Conversion discount: 15-25% 
– Increases every 3 – 6 months
Cap on Conversion Value 
♦ Protects investor against big increase in value 
between debt round and preferred round 
♦ Arguably more fair to activist investor who 
helps drive up value
Conversion – When and How 
♦ Automatic upon a new round of at least $X ($1M) – same 
equity as new investors 
– Discount 
♦ [Investor option to convert on smaller round] 
♦ Automatic immediately before change of control – to 
common stock 
– Discount to acquiror’s price 
♦ Investor option: At maturity or default 
– At discount from FMV or pre-agreed value 
♦ [Company option to force conversion at maturity]
Complexities 
♦ Note-holder agreement 
– Board seat 
– Protective provisions 
♦ Discount may be implemented in common 
shares warrants 
– Harder for next round to negotiate away
Subtleties 
♦ Better for entrepreneurs? For Investors? 
– Cheaper and faster than equity – maybe 
– Avoids valuing company 
– Investors may be unhappy if equity round is 
high valuation 
– Entrepreneur may also be unhappy – 
converting into a big valuation at a discount 
– If cap, effectively values company (CEILING) 
- why not lock that in as FLOOR?
Subtleties – continued 
♦ Liquidation overhang: Convertible debt 
investors get preference of $X for Y% of $X. 
♦ Special investor cases 
– Risk of discount being negotiated away by next 
round 
– Incubators – get founders stock; so aligned 
with entrepreneurs vs. debt investors 
– Superangels – quick; just an option on future 
rounds; small $ for them so valuation not a 
concern vs. home run return
McCarter & English LLP 
Questions? 
Benjamin M. Hron 
bhron@mccarter.com 
617.449.6584 
@HronEsq

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Convertible Debt - How it Works

  • 1. ♦Convertible Debt Financing How it Works Benjamin M. Hron bhron@mccarter.com 617.449.6584 @HronEsq
  • 2. Convertible Debt Essentials ♦ A loan that can be converted to stock ♦ Originally primarily used as a “bridge” between equity rounds ♦ Has become a typical way to do seed stage deals
  • 3. Cost - Benefit ♦ Puts off discussion of valuation ♦ Tends towards smaller deals – CAN be simpler, and cheaper to document, than equity – BUT can become complex; while seed equity getting simpler
  • 4. Cycles and Styles ♦ East Coast angel groups have evolved towards Preferred Stock deals ♦ Tends to be used by friends, family, and solo angels ♦ Use by superangels ♦ Good or bad for entrepreneurs?
  • 5. How it Works ♦ Loan to (Debt of) the Company – Principal and interest repayable at future date/circumstances ♦ May convert to equity – By whom (investor or company) – Under what conditions ♦ Conversion typically comes with a benefit – most commonly a discount off next round
  • 6. Basic terms and Norms ♦ Term/due date: 1 – 2 years – Cash payment of principal and interest is likely a “fail” scenario ♦ Interest rate: 6-10% – Accrues till maturity ♦ Conversion discount: 15-25% – Increases every 3 – 6 months
  • 7. Cap on Conversion Value ♦ Protects investor against big increase in value between debt round and preferred round ♦ Arguably more fair to activist investor who helps drive up value
  • 8. Conversion – When and How ♦ Automatic upon a new round of at least $X ($1M) – same equity as new investors – Discount ♦ [Investor option to convert on smaller round] ♦ Automatic immediately before change of control – to common stock – Discount to acquiror’s price ♦ Investor option: At maturity or default – At discount from FMV or pre-agreed value ♦ [Company option to force conversion at maturity]
  • 9. Complexities ♦ Note-holder agreement – Board seat – Protective provisions ♦ Discount may be implemented in common shares warrants – Harder for next round to negotiate away
  • 10. Subtleties ♦ Better for entrepreneurs? For Investors? – Cheaper and faster than equity – maybe – Avoids valuing company – Investors may be unhappy if equity round is high valuation – Entrepreneur may also be unhappy – converting into a big valuation at a discount – If cap, effectively values company (CEILING) - why not lock that in as FLOOR?
  • 11. Subtleties – continued ♦ Liquidation overhang: Convertible debt investors get preference of $X for Y% of $X. ♦ Special investor cases – Risk of discount being negotiated away by next round – Incubators – get founders stock; so aligned with entrepreneurs vs. debt investors – Superangels – quick; just an option on future rounds; small $ for them so valuation not a concern vs. home run return
  • 12. McCarter & English LLP Questions? Benjamin M. Hron bhron@mccarter.com 617.449.6584 @HronEsq