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Finance

A Startup Takes Flight – Part III

Series C Round

Provisions

  • Down Rounds: A “down round” is when new shares are priced lower than in a previous round. Triggers anti-dilution protections to preserve earlier investors’ ownership and influence. Without protection, investors get diluted like common shareholders.
  • Preferred Stock Conversion: If the investor holds preferred shares without an anti dilution provision, their shares will be diluted at the same rate as common shareholders, like pro rata but in the wrong direction. 
  • Pay-to-Play Provisions: Investors must join future rounds to keep their anti-dilution rights. Under IoW’s “Pay-to-Play” provisions, those who don’t participate in the Series C round lose these protections and may be converted to common stock.

Anti-Dilution Protections

Without any anti dilution provisions in place, an investor bears the full risk of having their proportional stake in a company reduced, on an unconverted basis, in the event of a down round.

  • No Anti-Dilution Protection: Investors without this clause are diluted at the same rate as common shareholders — similar to pro rata, but in the wrong direction.
  • Full Ratchet: Maximally protective. During a down round, prior preferred shares convert as if purchased at the new, lower price—i.e., the conversion price is reset to the latest share price.
  • Weighted Average: Offers a fairer approach to dilution protection by adjusting the conversion price based on both the size and price of previous and current funding rounds—unlike full ratchet provisions, which apply a more aggressive adjustment.

Valuation & Share Calculations

  • New Share Price = Pre-money valuation ÷ Existing shares.
  • New Shares Issued = Capital raised ÷ New Share Price.
CapTable after Series C Values Formula
Pre-Money Valuation $30,000,000
Series C $ Raised $10,000,000
Post-$ $40,000,000
Shares Prior (Series B) 27,499,175
Share Price Prior (Series B) $1.82
Share Price At New Round $1.09 “= 30M / 27.49M “
Series C Share Price % Change -40% “= $1.09/$1.82 – 1”
New Shares created from Series C 9,166,392 “= 10M / $1.09”

Series C Investments

Provident Capital

  • Because Provident Capital didn’t participate in the new round, it lost its anti dilution protection under the Pay-to-Play provision, and its Series B shares converted to common stock at the original $1.818 price.

BlackBox Capital

  • BlackBox capital previously invested $3.5 million and negotiated a full ratchet clause. Due to IoW’s declining valuation, BlackBox Capital’s Series B shares will convert at the lower Series C price of $1.091 instead of the original $1.818, granting them 66% more common shares through a 1.666x conversion ratio under their full ratchet anti dilution protection where the conversion price is reset to the latest share price.
  • BlackBox Capital now is investing $4 million for 3,666,361 Series C shares, ten percent of the company, undiluted.

Cormorant Ventures

  • Cormorant Ventures is investing $6 million for 5,499,541 Series C shares, fifteen percent of the company, undiluted.
  • Broad-Based Weighted Average Formula:
    • Common formula: CP2 = CP1 * (A + B) / (A + C)
    • CP2 = New conversion price after the down round
      • $1.81 * (27,499,998 + 3,300,330) / (27,499,998 + 9,165,902) = $1.52
    • CP1: Original conversion price for prior round shares ($1.818 for Series B)
    • A: Shares outstanding at prior round (27,499,998 Series B Shares)
    • B: “The aggregate consideration received by the corporation”
      • $ Invested at Series C / Original Conversion Price for Series B Shares
      • Series C capital ($6M) ÷ original Series B price ($1.81) = 3,300,330
    • C: New Series C shares issued (9,165,902)
  • Weighted average antidilution gave Cormorant Ventures a 1.191x conversion ratio—less than BlackBox’s 1.666x under full ratchet—preserving more equity for founders and other investors.

Unconverted Basis

Shareholder Initial Value Current Price Issued Price Common Shares (Unconverted) Series C % (Unconverted)) Series C $ (Unconverted))
Jill $1.09 $1.82 4,800,000 13.1% $5,236,521
Jack $1.09 $1.82 3,200,000 8.7% $3,491,014
Employee Pool $1.09 $1.82 2,000,000 5.5% $2,181,884
Opaque Ventures $2,500,000 $1.09 $1.82 2,083,333 5.7% $2,272,795
Blackbox Capital $2,500,000 $1.09 $1.82 2,500,000 6.8% $2,727,355
Cormorant Ventures $4,000,000 $1.09 $1.82 2,666,667 7.3% $2,909,178
Provident Capital $2,000,000 $1.09 $1.82 1,333,333 3.6% $1,454,589
Blackbox Capital $1,000,000 $1.09 $1.82 666,667 1.8% $727,295
Cormorant Ventures (Weighted Avg) $9,999,000 $1.09 $1.82 5,499,450 15.0% $5,999,580
Provident Capital (No Anti Dilution) $1,499,850 $1.09 $1.82 824,918 2.2% $899,937
Blackbox Capital (Full Ratchet) $3,499,650 $1.09 $1.82 1,924,808 5.2% $2,099,853
Cormorant Ventures $5,999,999 $1.09 5,499,834 15.0% $5,999,999
Blackbox Capital $4,000,000 $1.09 3,666,557 10.0% $4,000,000
36,665,566 100.0% $39,999,999

Cormorant Ventures

  • $9,999,999 investment / $1.82 = 5,499,450 shares
  • 5,499,450 shares x $1.09 = $5,999,580

Provident

  • $1,499,850 investment / $1.82 = 824,918 shares
  • 824,918 shares x $1.09 = $899,937

Blackbox

  • $3,499,650 investment / $1.82 = 1,924,808 shares
  • 1,924,808 shares x $ 1.09 = $2,099,853

Converted Basis

Shareholder Initial Value Current Price Conversion Price Conversion Ratio Common Shares (Converted) Series C % (Converted) Series C $ (Converted)
Jill $1.09 $1.50 1.00 4,800,000 12.3% $7,200,000
Jack $1.09 $1.50 1.00 3,200,000 8.2% $4,800,000
Employee Pool $1.09 $1.50 1.00 2,000,000 5.1% $3,000,000
Opaque Ventures $2,500,000 $1.09 $1.50 1.00 2,083,333 5.3% $3,125,000
Blackbox Capital $2,500,000 $1.09 $1.50 1.00 2,500,000 6.4% $3,750,000
Cormorant Ventures $4,000,000 $1.09 $1.50 1.00 2,666,667 6.8% $4,000,000
Provident Capital $2,000,000 $1.09 $1.50 1.00 1,333,333 3.4% $2,000,000
Blackbox Capital $1,000,000 $1.09 $1.50 1.00 666,667 1.7% $1,000,000
Cormorant Ventures (Weighted Avg) $9,999,000 $1.09 $1.53 1.19 6,546,943 16.8% $7,142,334
Provident Capital (No Anti Dilution) $1,499,850 $1.09 $1.82 1.00 824,918 2.1% $899,937
Blackbox Capital (Full Ratchet) $3,499,650 $1.09 $1.09 1.67 3,207,916 8.2% $3,499,650
Cormorant Ventures $5,999,999 $1.09 $1.09 1.00 5,499,834 14.1% $5,999,999
Blackbox Capital $4,000,000 $1.09 $1.09 1.00 3,666,557 9.4% $4,000,000
38,996,168 100.0% $50,416,920.3460

Cormorant Ventures

  • $9,999,999 investment / $1.53 = 6,546,943 shares
  • 6,546,943 shares x $1.09 = $7,142,334
  • Conversion Ratio = $1.82 / $1.53 = $1.19

Provident

  • $1,499,850 investment / $1.82 = 824,918 shares
  • 824,918 shares x $1.09 = $899,937
  • Conversion Ratio = $1.82 / $1.82 = $1.00

Blackbox

  • $3,499,650 investment / $1.09 = 3,499,650 shares
  •  3,499,650 shares x $ 1.09 = $3,499,650
  • Conversion Ratio = $1.82 / $1.09 = $1.67
Unconverted Shares Unconverted Value Converted Shares Converted Value
Cormorant Ventures 5,499,450 $5,999,580 6,546,943 $7,142,334
Provident 824,918 $899,937 824,918 $899,937
Blackbox 1,924,808 $2,099,853 3,499,650 $3,499,650