Nakano Investments
Nakano Investments
Quarterly report · Q4 2022 · Nakano & Centerpitch
Confidential
2022-12-31
01 · Overview
Consolidated cash
$664k
+407.7% QoQ
Combined equity
$2.65M
Nakano $2.65M · CP —
Private portfolio (MTM)
$1.70M
on $1.70M invested · $0 returned
Public portfolio (MTM)
$978k
$164k unrealized
2022 expenses (ann.)
$36k
$36k YTD

Last year was not quite the investing disaster for us that it would have seemed if you had only listened to the financial news panic screeds. We did see our first venture fails, of course. These were relatively small, and I think there are some blazingly obvious (in retrospect) lessons to be learned. Also, two of our other venture investments hit key milestones, while also both scratching at the butt hairs of $10m of revenue. Moreover, our public portfolio did quite well, given the environment. Early defensive moves into dividend-payers paid off on both a price basis (we were ahead of the rush to safety which bid these up) and, by definition, an income basis: we received almost $90k in dividends over the course of the year. Tempering this, sadly, was my wrong-headed conviction on Alibaba, which spent the entire year being shat on by COVID and shoveled up by the Chinese state. At least we harvested some tax losses, I guess? Sigh.

One note about the report. The algo I had been using to calc the portfolio's MTM in prior reports had a flaw, which I've corrected. The flaw undercounted MTM. Consequently, you will see a boost in MTM from $3.5m in the last report to $5.0m in this one (the breakdown: roughly $1.0m in stocks, $650k in cash, $500k in Northfield (because they are already selling lots for 50% more than they anticipated), $1.5m in ScreenMeet (based on Ben's expected valuation for a next round), $1.25m for Smartemis (based on the valuation for the April round), and $200k for Lung Therapeutics (held at cost), Bloom Intelligence (held at 50% discount), and Linden Drive (held at cost). Again, none of the underlying assumptions have changed. Our "outperformance" expectations for the portfolio dropped by $600k to $9.2m based on the failure of NextAlim and The Transportation Authority as well as the more conservative reconfiguring of our stock portfolio post the Nov 10 tax-loss sales.

FY 2022 gross returns: -$145.2k (-133.6%). We ended the year down, for the first time — a drop of 4.7% on our average principal exposure over the year ($3.1m). The loss is due to the two deals that failed this year: NextAlim (-$120.4k) and Transportation Authority (-$95.0k). Perhaps surprisingly, we ended the year up on our public investments at +$70.3k (+4.4% on average exposure of $1.6m). The S&P's total return was -18.1% for the year, but who's comparing? Well, perhaps I am: for the past three years (the first three years we've been fully invested in stocks), we're outperforming the S&P by some distance. Since inception (April Fool's Day, 2016), we have earned $1.27m on average equity capital of $2.13m, or a +59.5% pre-tax return, equivalent to a +14.9% annual return.

Consolidated cash, quarterly

-$220k$252k$723k$1.2m$1.7m20182019202020212022

Balances by account

eTradeeTrade: $606,272$606kMSMS: $21,672$22kIBKRIBKR: $19,780$20kWFBWFB: $10,003$10kWFWF: $6,652$7kNewBridgeNewBridge: $20$20
Source: Nakano_Summary_CASH_EXPENSE REPORT_(2026_06_30) DRAFT.xlsx · “Running Cash Balances”
02 · Expenses
Consolidated (Nakano + Centerpitch)
2022 YTD$36,308
Annualized$36,308
2021 full year$28,031
+29.5% YoY (annualized)
2016: $0162017: $5,373172018: $12,647182019: $28,856192020: $23,494202021: $28,031212022: $36,308222023: $50,29523$50k2024: $39,759242025: $26,173252026: $17,25426$17k
Nakano
2022 YTD$36,308
Annualized$36,308
2021 full year$28,031
+29.5% YoY (annualized)
2016: $0162017: $5,373172018: $12,647182019: $28,856192020: $23,494202021: $28,031212022: $36,30822$36k2023: $21,914232024: $7,359242025: $4,631252026: $2,00626$2k
Centerpitch
2022 YTD$0
Annualized$0
2021 full year$0
2016: $0162017: $0172018: $0182019: $0192020: $0202021: $0212022: $0222023: $28,381232024: $32,40024$32k2025: $21,542252026: $15,24726$15k

2022 spend by line item (consolidated)

Office RentOffice Rent: $15,855$15,855CreditcardCreditcard: $14,340$14,340Office FurnitureOffice Furniture: $2,941$2,941Accountant FeesAccountant Fees: $1,600$1,600Bank Service FeesBank Service Fees: $382$382State/City FeesState/City Fees: $319$319Business ApplicationsBusiness Applications: $249$249Webpage EmailWebpage Email: $192$192Legal FeesLegal Fees: $164$164OtherOther: $267$267

FY 2022 expenses: $35.1k (+25.4% YoY). Expenses were sharply up in 2022, due to higher credit card expenses (Mexico) and office furniture (John's painting). All other line items were consistent with prior years. Our office rent increased slightly (+3.3%), and we signed a new three-year lease. I will start breaking out more thoroughly our credit card expenses going forward; for historical data, Wells recently made a change which now limits us to seeing 120 days of past transactions, so I need to figure that out.

Source: Nakano_Summary_CASH_EXPENSE REPORT_(2026_06_30) DRAFT.xlsx · Expenses_Summary / Expenses_Nakano / Expenses_Centerpitch · full tables in the appendix · annualization holds Accountant Fees, State/City Fees, Client Entertainment, and Internal Events at actuals
03 · Equity balances
Nakano Investments LLC
Total equity$2,654,236
Design target (D/W)80 / 20
Drexler $2,124,236 (80.0%)Wiesner $530,000 (20.0%)
$0$717k$1.4m$2.1m$2.9m201720182019202020212022
Centerpitch Investments LLC

no data

Source: Nakano_Summary_CASH_EXPENSE REPORT_(2026_06_30) DRAFT.xlsx · Nakano_Equity / Centerpitch_Equity
04 · Private portfolio

New private deals: 7, for $635.1k (+8.0% YoY). Private deals gains/losses: 2, for -$215.4k (-12.8% of private investments outstanding). Notably, we did our first two debt deals in this period in the form of promissory notes: $45k to take a piece of debt in the Assembly Authority investment, bringing our total exposure there up to $95k, and a $92k loan to partially fund a Drexler family property in Cedar Rapids. With the exception of the latter, the investments only included one new obligor: Lung Therapeutics, a biotechnology company pursuing two drugs to treat lung fibrosis, into which we invested $50k. Of particular note: we increased our investment in Smartemis this year by 2.5x, to ~$634k (€550k) from ~$185k, due to positive progression in their sign-up of vet clinics in Germany—they ended the year with 10 clinics closed with a combined revenue of €10m. Net, we ended the year with $1.70m of exposure to private deals across 6 unique deals (and 12 tranches).

DealFirst fundingInvestedCash receivedRemaining valueMOICOutperformance case
Nakano Investments LLC
Smartemis
Veterinary services — France, Germany (Principal: Bill Hughson)
Mar 2022$633,683—$633,6831.00×—
ScreenMeet
Cloud-native remote support SaaS (Principal: Ben Lilienthal)
Jun 2021$574,999—$574,9991.00×—
Northfield
Residential real-estate development (Principal: Patrick Zalupski)
Aug 2020$250,000—$250,0001.00×—
BloomIntel
Restaurant marketing — Bloom Intelligence (Principal: Will Wilson)
Aug 2021$100,000—$100,0001.00×—
LindenDebt
Oct 2022$91,893—$91,8931.00×—
LungThera
Biotech — now Rein Therapeutics, RNTX (Principal: Brian Windsor)
Mar 2022$50,000—$50,0001.00×—
Nakano subtotal$1,700,576$0$1,700,5761.00×
Consolidated$1,700,576$0$1,700,5761.00×

Invested (light) vs total value — paler segment is cash already returned

SmartemisSmartemis invested: $633,683$634kSmartemis remaining value: $633,683$634kScreenMeetScreenMeet invested: $574,999$575kScreenMeet remaining value: $574,999$575kNorthfieldNorthfield invested: $250,000$250kNorthfield remaining value: $250,000$250kBloomIntelBloomIntel invested: $100,000$100kBloomIntel remaining value: $100,000$100kLindenDebtLindenDebt invested: $91,893$92kLindenDebt remaining value: $91,893$92kLungTheraLungThera invested: $50,000$50kLungThera remaining value: $50,000$50k

The progress that Ben is making with ScreenMeet seems encouraging. They seem to be on the cusp of achieving $10m in sales, which should justify even higher valuations than the one at which we currently have them marked. Tempering this progress is the dual threat of integration and management problems at Salesforce (one of the most likely purchasers of ScreenMeet), and the general softening of the private equity bid going into 2023.

We also saw our first losses since ABBQ in the private space. Both NextAlim and Assembly Authority sent us notes that they would not be able to continue operations. This represents a total loss of $215,425.90. In both cases, there are specific lessons to learn. Irritatingly, one of the commonalities is that both raised debt instruments (in which we participated) just months before they folded. This, to me, is clearly a due diligence failure on our end. There is more work to be done here to ensure we're taking away the right lessons.

Source: Nakano_Portfolio_Data.xlsx · Deal_Registry / Deal_Transactions / Deal_Valuations · marks are total deal value (report-sourced); Remaining value = mark − cash received, which is what counts toward portfolio value (received cash already sits in the cash accounts) · MOIC = total value / invested · deals, marks, and cash received are as of the report date · open deals with no dated mark yet are carried at cost
05 · Public portfolio

All public securities are held at Nakano Investments (eTrade and Interactive Brokers). Centerpitch holds no public positions.

Open positions (MTM)
$978k
$164k vs cost
Realized G/L, 2022 YTD
-$277k
+ $84k dividends
eTrade NAV
$1.58M
broker-reported, Dec 31
IBKR NAV
$14k
broker-reported, Dec 31

NAV bridge: open positions $978k + eTrade cash $606k + IBKR cash $20k (margin loan) = $1.60M ≈ combined broker NAV $1.60M — brokerage NAV nets cash and margin against the securities.

Daily marks — securities value by account

$0$748k$1.5m$2.2m$3.0m202020212022
TotaleTradeIBKR

Performance vs indexes (time-weighted)

CumulativeCAGR2022 YTD
Portfolio+45.4%+10.9%-4.1%
Blended benchmark+37.4%+9.2%-18.2%
S&P 500+43.9%+10.6%-18.2%
MSCI ACWI+28.0%+7.1%-18.4%
Japan (EWJ)+8.1%+2.2%-17.7%
Europe (VGK)+16.8%+4.4%-16.0%

Time-weighted: daily returns of the securities book chained with buys/sells neutralized as external flows; dividends and option premiums count as return. Base 100 on 2019-05-24. The blended benchmark applies the portfolio's own daily bucket weights to matching index returns (US equities→SPY, Japan equities→EWJ, Europe equities→VGK, China equities→MCHI, US bonds/bills→BIL, Crypto→ETH-USD; dividend-adjusted USD ETFs). Current mix: US equities 100%. T-bill discounts recognize at purchase; delisted names (ALRN, LUMO) excluded.

Open positions

TickerQtyCost basisLast price (local)MTM (USD)GainWeight
eTrade
ABBV1,750$186,465$161.61$282,818+51.7%28.9%
JNJ900$138,599$176.65$158,985+14.7%16.3%
GS
Goldman Sachs Group
450$154,979$343.38$154,521-0.3%15.8%
CVS1,500$115,393$93.19$139,785+21.1%14.3%
NEE
NextEra Energy
1,000$76,467$83.60$83,600+9.3%8.5%
FMC400$44,479$124.80$49,920+12.2%5.1%
LMT100$32,995$486.49$48,649+47.4%5.0%
SBLK2,500$53,084$19.23$48,075-9.4%4.9%
UEC
Uranium Energy
3,000$11,475$3.88$11,640+1.4%1.2%
eTrade subtotal$813,936$977,992

Realized results by year

2019202020212022Total
Realized G/L$33k$169k$408k-$277k$333k
Dividends$10k$23k$59k$84k$176k

New public investments: 0, or $0.0m (-100.0% YoY). Public deals gains/losses: +$70.3k (+4.4% of public investments outstanding). We did not make any public stock or bond purchases in 2022, due to deteriorating market conditions. We did, however, sell stocks to the tune of $771k this year, mainly in early November for tax loss harvesting. Since our tax-loss sales were mainly focused on the tech sector, our public portfolio distribution has become even more heavily biased towards dividend-payers, with 98.8% of our holdings in dividend-paying stocks, and the last 1.2% in "punts" (UEC, a uranium play).

The math behind the outperformance: we took $275.3k in realized losses on Nov 10, led by Alibaba, Citigroup, and Compass Pathways; we earned $83.8k in dividends over the year; and our unrealized gains went from -$63.0k at the end of 2021 to a positive $198.8k, led by AbbVie, Lockheed Martin, and CVS. Two moments jump out: first, we dodged some of the downturn in the first part of the year because we moved from tech to dividend stocks at the end of 2021, even though BABA continued to be a drag. Then, our tax harvesting sale on Nov 10 ended up being quite defensive—our post-sale portfolio remained flat-ish over the tail end of the year (-0.8% from Nov 10 to Dec 31) as the major indices fell (S&P: -3.1% over the same period). So basically, we missed a bunch of the worst moments and sectors in 2022, while getting a boost from the dividend-heavy health and defense sectors.

Source: Nakano_Portfolio_Data.xlsx · Public_Trades / Prices / Account_NAV · daily marks: nakano_reporting daily_marks engine (month-ends tie IBKR PortfolioAnalyst within ±1.1%)
06 · Appendix — expense detail
Consolidated
Line item20162017201820192020202120222023202420252026Total
Office Rent4,17014,77815,06515,39115,85516,63814,64116,0617,327119,925
Office Furniture4,3292,9413,40010,670
Office Supplies0
Office-Related Expenses4,17014,77815,06519,72118,79520,03814,64116,0617,327130,595
Webpage Email3934805781803541925227282,3451,5257,295
Subscriptions13,0978191,5894395,945
Video Meeting Services1581671481541611731841,145
Business Applications2492494413831201,442
Other Business Services2252402149625
Operational Expenses3935015783387706434,2142,0904,6292,29716,452
Client Entertainment8,0448,9702,0152,48821,517
Internal Events4,5063,1058608,471
Business Travel1,1575,4386,595
Client Expenses13,70717,5142,0153,34836,584
Legal Fees2,3768391,4591642785,115
Accountant Fees2,8901,8002,5002,5001,6002,5002,5002,5003,85022,640
State/City Fees751693192782821,122
Bank Service Fees295110175382611512341101,866
Wire Fees2252402901006065425501,455
Foreign Currency Charges20323702244
Advisory and Fees2255,5813,2244,3382,7372,5293,1143,3883,0124,29432,443
Other Expenses2,8811,400991,580
Error7061,1391,316681643844
Miscellaneous2,1752611,316780643736
Creditcard4,7552,3958,1024,0156,12014,3408,4412,1271,0991251,382
Total Expenses5,37312,64728,85623,49428,03136,30850,29539,75926,17317,254268,191
Nakano
Line item20162017201820192020202120222023202420252026Total
Office Rent4,17014,77815,06515,39115,8556,37471,633
Office Furniture4,3292,9413,40010,670
Office Supplies0
Office-Related Expenses4,17014,77815,06519,72118,7959,77482,303
Webpage Email3934805781803541925226782,3451,5257,246
Subscriptions1402393873541,723
Video Meeting Services1581671481541611731841,145
Business Applications2492493362781201,232
Other Business Services225274
Operational Expenses3935015783387706431,4141,5103,5111,76311,419
Client Entertainment3,3233,323
Internal Events2,5254222,946
Business Travel3,3223,322
Client Expenses7993,7432,944
Legal Fees2,3768391,4591641394,976
Accountant Fees2,8901,8002,5002,5001,6002,50013,790
State/City Fees75169319144706
Bank Service Fees2951101753825801802341101,706
Wire Fees2252402901006065980
Foreign Currency Charges203210228
Advisory and Fees2255,5813,2244,3382,7372,5293,0832023425522,187
Other Expenses2,8811,4001,481
Error7061,1391,3162131,096
Miscellaneous2,1752611,316213384
Creditcard4,7552,3958,1024,0156,12014,3408,4412,1271,0991251,382
Total Expenses5,37312,64728,85623,49428,03136,30821,9147,3594,6312,006170,620
Centerpitch
Line item20162017201820192020202120222023202420252026Total
Office Rent10,26414,64116,0617,32748,292
Office Furniture0
Office Supplies0
Office-Related Expenses10,26414,64116,0617,32748,292
Webpage Email5050
Subscriptions2,6954267163854,222
Video Meeting Services0
Business Applications105105210
Other Business Services402149551
Operational Expenses2,8005801,1185345,032
Client Entertainment11,3688,9702,0152,48824,841
Internal Events1,9822,6848605,525
Business Travel1,1572,1173,274
Client Expenses14,50613,7712,0153,34833,640
Legal Fees139139
Accountant Fees2,5002,5003,8508,850
State/City Fees278139416
Bank Service Fees31129160
Wire Fees42550475
Foreign Currency Charges216216
Advisory and Fees313,4082,7784,03910,256
Other Expenses9999
Error681429252
Miscellaneous780429351
Creditcard0
Total Expenses28,38132,40021,54215,24797,571
Sources: Nakano_Summary_CASH_EXPENSE REPORT_(2026_06_30) DRAFT.xlsx · Nakano_Portfolio_Data.xlsx · unmarked private deals carried at zero.