MeritValue

Upland Software, Inc.

UPLDdata completeness 100%14 fiscal years on file
The thesis, from the filings

Upland Software, Inc. earns about -12% on invested capital, and has bought back 6% of its shares over 5 years. The cash-flow models don't apply cleanly here — the ledger says why below.Whether it’s worth owning at today’s price is the last question — and yours to answer, below.

i. The business — what you’d actually own
FigureFY 2021FY 2022FY 2023FY 2024FY 2025
Revenue$302M1$317.3M2$297.9M3$274.8M3$216.9M3
Net income−$58.2M4−$68.4M5−$179.9M6−$112.7M6−$38.9M6
Operating cash flow$41.7M7$30M8$49.9M9$24.2M9$25.8M9
Capital expenditure$1.12M10$866,00011$1.22M12$882,00012$1.35M12
Free cash flow (derived)$40.6M7$29.1M8$48.7M9$23.4M9$24.4M9
Total debt$1.04B13$1.03B14$953.3M15$580.4M16$464.8M16
Cash & equivalents$189.2M17$248.7M18$236.6M19$56.4M20$29.4M20
Diluted shares30.3M31.5M32.1M27.8M28.6M

Superscripts are receipts. Each links to the SEC filing the number came from (full list at the bottom).

ii. Your slice — ownership made literal
If you owned
shares
Net assets behind them
−$16.9
your share of equity
Profit it earned you last year
−$13.6
Free cash flow it threw off
$8.54
Debt you’d be carrying
$162.43

10 shares is a claim on −$16.9 of net worth that earned you −$13.6 and generated $8.54 of cash last year, against $162.43 of debt.

iii. Is this a good business?
Moat signal · return on invested capital
-12% avg · 5y
FY21 -7%FY22 -7%FY23 -19%FY24 -17%FY25 -8%

It earned an average -12% on invested capital over 5 years. Compare that to what it costs to fund the business.

seeing a moat in the numbers →
Management signal · capital allocation
−6% shares · 5y

Share count is down 6% over 5 years — management has been buying back stock, quietly handing owners a bigger slice. Total debt has fallen 55% — deleveraging.

reading capital allocation →

Signals, not verdicts — read from the filings above. Numbers don’t prove a moat; they show its footprint. You decide.

iv. What it’s worth — engine v0.1.0
DCF · Growth Exit 10Y
not applicable
negative equity value — refusing to publish per-share figure
assumptions (10)
  • riskFreeRate4.7%
  • equityRiskPremium5.0%
  • beta100.0%
  • equityWeight85.0%
  • costOfDebtSpread1.5%
  • taxRate21.0%
  • terminalGrowth2.5%
  • projectionYears10
  • fcfGrowth0.0%
  • fcfBase$24.4M
DCF · Growth Exit 5Y
not applicable
negative equity value — refusing to publish per-share figure
assumptions (10)
  • riskFreeRate4.7%
  • equityRiskPremium5.0%
  • beta100.0%
  • equityWeight85.0%
  • costOfDebtSpread1.5%
  • taxRate21.0%
  • terminalGrowth2.5%
  • projectionYears5
  • fcfGrowth0.0%
  • fcfBase$24.4M
Earnings Power Value
not applicable
normalized (5y-median) earnings non-positive — EPV undefined
Graham Number
not applicable
diluted EPS missing or non-positive — Graham Number undefined

Different models answer different questions — which to trust when →

Sources — the receipts
  1. 10-K/A · period ending 2021-12-31 · accession 0001505155-24-000103 (RevenueFromContractWithCustomerExcludingAssessedTax)
  2. 10-K · period ending 2022-12-31 · accession 0001505155-25-000024 (RevenueFromContractWithCustomerExcludingAssessedTax)
  3. 10-K · period ending 2023-12-31 · accession 0001505155-26-000007 (RevenueFromContractWithCustomerExcludingAssessedTax)
  4. 10-K/A · period ending 2021-12-31 · accession 0001505155-24-000103 (NetIncomeLoss)
  5. 10-K · period ending 2022-12-31 · accession 0001505155-25-000024 (NetIncomeLoss)
  6. 10-K · period ending 2023-12-31 · accession 0001505155-26-000007 (NetIncomeLoss)
  7. 10-K/A · period ending 2021-12-31 · accession 0001505155-24-000103 (NetCashProvidedByUsedInOperatingActivities)
  8. 10-K · period ending 2022-12-31 · accession 0001505155-25-000024 (NetCashProvidedByUsedInOperatingActivities)
  9. 10-K · period ending 2023-12-31 · accession 0001505155-26-000007 (NetCashProvidedByUsedInOperatingActivities)
  10. 10-K/A · period ending 2021-12-31 · accession 0001505155-24-000103 (PaymentsToAcquirePropertyPlantAndEquipment)
  11. 10-K · period ending 2022-12-31 · accession 0001505155-25-000024 (PaymentsToAcquirePropertyPlantAndEquipment)
  12. 10-K · period ending 2023-12-31 · accession 0001505155-26-000007 (PaymentsToAcquirePropertyPlantAndEquipment)
  13. 10-K · period ending 2021-12-31 · accession 0001505155-23-000017 (LongTermDebtNoncurrent)
  14. 10-K/A · period ending 2022-12-31 · accession 0001505155-24-000103 (LongTermDebtNoncurrent)
  15. 10-K · period ending 2023-12-31 · accession 0001505155-25-000024 (LongTermDebtNoncurrent)
  16. 10-K · period ending 2024-12-31 · accession 0001505155-26-000007 (LongTermDebtNoncurrent)
  17. 10-K · period ending 2021-12-31 · accession 0001505155-23-000017 (CashAndCashEquivalentsAtCarryingValue)
  18. 10-K/A · period ending 2022-12-31 · accession 0001505155-24-000103 (CashAndCashEquivalentsAtCarryingValue)
  19. 10-K · period ending 2023-12-31 · accession 0001505155-25-000024 (CashAndCashEquivalentsAtCarryingValue)
  20. 10-K · period ending 2024-12-31 · accession 0001505155-26-000007 (CashAndCashEquivalentsAtCarryingValue)