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Finance

A Startup Takes Flight – Part II

Series B + Pro Rata Rights

Pro rata rights give investors the option (but not the obligation) to maintain their ownership percentage in future funding rounds, helping them maintain their ownership percentage in future rounds, thereby avoiding dilution.

Investors benefit by:

  • Managing risk in an unpredictable asset class.
  • Retaining access to top-performing startups.
  • Preserving board seats tied to ownership thresholds.
  • Ensuring continued influence, especially for early-stage investors in later rounds.

Entrepreneurs benefit from clearer planning around future participation, but must vet pro rata investors carefully—unengaged or misaligned investors can crowd out more valuable ones.

Fred Wilson’s Example (Unrelated to Startup Takes Flight):

“You invest $50k in a seed round at a $5mm cap and own 1% of the company. The next round is a $3mm round at $9mm pre, $12mm post. If you don’t participate, you will be diluted 25% and will then own 0.75% of the company. On the other hand, if you buy 1% of the round, a $30k investment, you will continue to own 1% of the company. Your ‘pro-rata right’ in this situation is a $30k allocation in the next round.”

Fred Wilson’s Simple Example Fields Fields No Participation Participation
Investment 50,000
Seed Round – Cap 5,000,000 % Ownership Calc Pre-$ Portion / Post $ Total Investment / Post $
% 1.0% % Ownership 0.75% 1.00%
Pre-$ 9,000,000 Pre-$ Portion 90,000 90,000
Investment 3,000,000 Investment 0 30,000
Post-$ 12,000,000 Total 90,000 120,000
  • Without pro-rata rights, diluted .25%. With pro-rata rights, can invest $30K to maintain 1$ ownership.

Series B Round

  • Investment Round: $15 million
  • Pre-Money Valuation: $35 million (21.2% Series A Post $ increase)
  • Post-Money Valuation: $50 million (no discounts or caps)

Series B New Price Per Share = $1.818.

  • Pre-money valuation ($35 million) / # of shares outstanding prior to Series B (19.25 million)

Series B New Shares

  • Will need to issue $15 million worth of stock at a share price of $1.818 per share.
  • So $15 million / $1.818 = 8.25 million shares

 

Capitalization Table after Series B Values Calculation
Pre-Money Valuation $35,000,000
Series B $ Raised $15,000,000
Post-$ $50,000,000
% Change from Sr. A 21% 35M / 28.87M – 1
Share Price At New Round $1.82 35M / 19.25M Shares
New Shares from Series B 8,250,000 15M / $1.82

 

Investor Pro-Rata Rights:

  • BlackBox Capital has pro rata rights on its 3.46 percent Series A stake, but not its Seed stake
  • Provident Capital has pro rata rights on its 6.93 percent Series A stake
  • Cormorant Ventures has pro rata rights on its 13.85 percent Series A stake

Investment Required to Maintain Pro Rata Stake =

  • (% Stake You Want to Maintain) x (# of New Shares Being Issued) x Share Price at New Round
Shareholder Class Percent at Series A New Series B Shares Shares to Purchase Series B Share Price Minimum Investment
Cormorant Ventures Series A Pref. 13.9% 8,250,000 1,142,857 $1.82 $2,077,922
Provident Capital Series A Pref. 6.9% 8,250,000 571,429 $1.82 $1,038,961
Blackbox Capital Series A Pref. 3.5% 8,250,000 285,714 $1.82 $519,481

 

In this case, because the company’s valuation hasn’t increased by a huge amount and the company is raising a sufficiently large amount of money in this round, all investors are able to participate and maintain their pro rata stakes.

  • Cormorant Ventures had to put in a minimum of $2.077 million to maintain their 13.85 percentage stake from the previous round. By investing the additional $8 million, they grew their percent stake in the company to roughly 30 percent.
  • To get their 5.49M shares, divide 9,999,000 / $1.8. Same logic applies to other investors.
Shareholder Class # of Shares Percent Price Value
Jill Common 4,800,000 17.5% $1.8 $ 8,727,273
Jack Common 3,200,000 11.6% $1.8 $ 5,818,182
Employee Pool Common 2,000,000 7.3% $1.8 $ 3,636,364
Opaque Ventures Seed Pref. 2,083,333 7.6% $1.8 $ 3,787,879
Blackbox Capital Seed Pref. 2,500,000 9.1% $1.8 $ 4,545,455
Cormorant Ventures Series A Pref. 2,666,667 9.7% $1.8 $ 4,848,485
Provident Capital Series A Pref. 1,333,333 4.8% $1.8 $ 2,424,242
Blackbox Capital Series A Pref. 666,667 2.4% $1.8 $ 1,212,121
TOTAL $ 35,000,000
SERIES B
Cormorant Ventures Series B Pref. 5,499,450 20.0% $1.8 $9,999,000
Provident Capital Series B Pref. 824,918 3.0% $1.8 $1,499,850
Blackbox Capital Series B Pref. 1,924,808 7.0% $1.8 $3,499,650
$14,998,500
SERIES A + B 27,499,175 100.0% $ 49,998,500