Retirementdough June Portfolio Update

Portfolio Update 7/1/22 at 9PM

It’s been a little over a month since I posted my last portfolio update found here;…

I have found doing these updates is helping me keep better records of my investing thought processes over time. Much like keeping a journal in life when you re-read in the future it helps you remember what your thoughts were at the time of writing. Hopefully others find this helpful as well.

Current Portfolio as of 7/1/22.  
Change since 5/28/22		   	  -28.0%		        YTD	-71.8%

VTI Monthly 				   -8.9%   		        YTD	-21.6%

I have decided to just benchmark versus the VTI which is Vanguard Total Stock Market Index Fund, which is probably what I would put my money into if I did not want to spend time researching stocks. VTI includes all 3600 stocks traded in market.

Stock		% Portfolio 	  % Portfolio	       % Change 	Market        Monthly Stock 
		  Current	    Previous	       Portfolio        Cap (B)       Price change %
UPST		  93.1		    79.5		+13.6	     	2.8B  	      -36.5%
UPST options	   6.9		    13.3		 -6.4
CASH		     0               6.8                 -6.8	               

New positions since last portfolio update: NONE

Exited positions since last update: NONE

Trades between 5/28/22-7/1/22

Bought: 	UPST		6/6		$47.03; 46.74; 46.79
		UPST		6/7		$44.36
		UPST		6/13		$40.00
		UPST		6/14		$34.10	
		UPST		6/28		$37.99
		UPST		6/30		$31.60
Sold: 		None

Thoughts on trades and companies for the month.

Another tough month, I may be getting use to them, as my mood is up beat. At the middle of May I began selling covered calls on my upstart position and using that cash to buying long calls on UPST. You can see from my purchases that I have also been buying stock with some of the covered call funds. I have been buying weekly covered calls and using the proceeds to make my purchases.

Though my portfolio is down big on the year and even down since my last monthly review I have increased my overall share count. I have gained 1 to 3 percent in cash of my overall portfolio value weekly by selling covered calls. I then either purchase long calls or buy more stock. My long calls have lost value since original purchase date, as have my additional shares. So my portfolio overall value is down but my number of shares is up. I currently hold 28% more shares than I did on 5/28 when I last reported. I did sell some of my long calls however I still own 89% of long calls contracts now compared to 5/28 update.

The Motley Fool did a recent interview with Dave Girouard CEO of Upstart which can be found here:…

I see a company that is executing on its business, expanding into new markets and adding new customers (banks and credit unions see press releases below). I really like the leadership team. They owned up to the mistake of upsetting Wall Street by putting loans on their balance sheet and owned the fact that they needed to improve the decision making capabilities of their software during difficult economic times (such as when war and inflation start). They seem confident that they are working in an area without competition currently. I obviously am hoping for big things in the future.

JabbokRiver just posted an excellent write up on his thoughts on UPST I am including link here for my future reference.…
Others on the boards are just much more gifted writers than myself. I find when I read their work I am like, yes I agree, but getting those same thoughts with clarity on paper is difficult.

Upstart UPST
MC 2.8B
TAM 1.4T…

Monthly performance of stock for June was -36.5%, May was -35.6% following a similarly brutal March and April. YTD -77.3%

Upstart announced first quarter 2022 results…

Revenue. Total revenue was $310 million, an increase of 156% from the first quarter of 2021. Total fee revenue was $314 million, an increase of 170% year-over-year.
Transaction Volume and Conversion Rate. Bank partners originated 465,537 loans, totaling $4.5 billion, across our platform in the first quarter, up 174% from the same quarter of the prior year. Conversion on rate requests was 21% in the first quarter of 2022, down from 22% in the same quarter of the prior year.
Income from Operations. Income from operations was $34.8 million, up from $15.6 million the prior year.
Net Income and EPS. GAAP net income was $32.7 million, up from $10.1 million in the first quarter of 2021. Adjusted net income was $58.6 million, up from $19.9 million in the same quarter of the prior year. Accordingly, GAAP diluted earnings per share was $0.34, and diluted adjusted earnings per share was $0.61 based on the weighted-average common shares outstanding during the period.
Contribution Profit. Contribution profit was $147.8 million, up 165% year-over-year in the first quarter of 2022, with a contribution margin of 47% compared to a 48% contribution margin in the same quarter of the prior year.
Adjusted EBITDA. Adjusted EBITDA was $62.6 million, up from $21.0 million in the same quarter of the prior year. The first quarter 2022 adjusted EBITDA margin was 20% of total revenue, up from 17% in the first quarter of 2021.

Financial Outlook For the second quarter of 2022, Upstart expects:
Revenue of $295 to $305 million
Contribution Margin of approximately 45%
Net Income of ($4) to $0 million
Adjusted Net Income of $28 to $30 million
Adjusted EBITDA of $32 to $34 million
Basic Weighted-Average Share Count of approximately 85.0 million shares
Diluted Weighted-Average Share Count of approximately 96.2 million shares
For the full year 2022, Upstart now expects:
Revenue of approximately $1.25 billion
Contribution Margin of approximately 48%
Adjusted EBITDA of approximately 15%

Mascoma Bank, a $2.6 billion mutual bank and Certified B-Corporation® serving Northern New England, announced today that it has partnered with Upstart (NASDAQ: UPST), a leading artificial intelligence (AI) lending platform, to offer AI-powered personal loans to more people.…

MIDFLORIDA Credit Union, one of the largest credit unions in Florida with more than 434,000 members and assets totaling more than $6.6 billion, today announced that it has partnered with Upstart (NASDAQ: UPST), a leading artificial intelligence (AI) lending platform, to provide affordable personal loans to more Floridians.…

Firelands Federal Credit Union (Firelands FCU), an Ohio-based credit union with over 32,000 members and $385 million in assets, today announced it has partnered with Upstart (NASDAQ: UPST), a leading artificial intelligence (AI) lending platform, to offer AI-powered personal loans and auto refinance loans to its members.…

YTD return of portfolio for each month 

January  	-30.4%
February	 -9.4%
March		-19.5%
April		-41.3%
May		-58.4%  
June (July1st)	-71.8%  (low of year 6/30 -72.2%)

I think sharing ones portfolio can be a helpful endeavor but obviously I have a huge tolerance for risk. I base my investment decision on my analysis and thoughts alone. I listen and weigh others thoughts and information but never hold them accountable for any investment decisions that I make. Portfolio allocation is another unique decision for all investors. I obviously am extremely highly concentrated. This investment style is not for the faint of heart. It requires quick decision making and action if one feels there is a change in investment thesis. I state all of this to clarify that one should study and hold yourself responsible for investment decisions. New investors should take the time to learn first before investing their hard earned money.

Even though my portfolio is at all year low I am starting to feel very confident in back half of year. Short interest on the stock is extremely high currently. I continue to increase the number of shares I hold over time even though the value of my portfolio is at all time lows. I obviously think what has punished the stock was a blip on the radar of Upstarts businesses long term success. One of my favorite articles ever written on the TMF was Morgan Housel’s “The Agony of High Returns”…

It’s hard to grasp how the best-performing stock of the last 20 years could spend the majority of that time with returns that would make you want to vomit. It’s easy to think that the single-best investment to own is one that would make us smile every morning we woke up owning it.
But it wasn’t. It never is. And it never will be.

That’s the nature of the stock market. On the way to making serious money, you spend a lot of time losing serious money. It’s a reality anyone investing in stocks, no matter what you own, has to face.

I looked at the 10 best stocks to own over the past 20 years. These are all cherry-picked for their stellar returns, and the stocks you would probably choose to own if you had a time machine. On average they increased more than 28,000%.

But they all spent a majority of the time well below their previous high mark. They all had multiple declines of 50% or more. A few had multiple 70% drops.


It is pretty gutsy to be this focused on one stock, but if you are right it can be amazing.

I remember nibbling on ENPH a few years ago and in hindsight wished I have been much more aggressive. Although diversification can protect, it can also hinder growth.

I like UPST. I think this is a good buying opportunity for them. I do not think that I could go 100% with them. I think my cap would be closer to 20%. But I wish you all the best with them. hope you hit a home run.

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So I was assuming you were in your early 20s and had a very modest amount to invest, so you thought heck why not just put what I have down on one stock? I have plenty of time to save and invest, so why not while I’m young go for it, gamble it on one stock.

Am I correct? I don’t think the owners, the leaders of UPST would want their entire portfolio in UPST, why would you?

Im not sure you can even call it a portfolio. I don’t own a portfolio of homes, own a home. You own a stock.



That’s a really excellent summary of Upstart, Retirementdough! :slight_smile:

We both might have to wait through most of the remainder of 2022 to see huge upside to the stock because the company itself is likely to be “less impressive than usual”. Recession perhaps reducing loan demand, higher interest rates restricting the number of approved loans, the protracted roll-out of auto loans, new initiatives (SMB loans, mortgages). All that stuff should set the company up for more incredible gains once the dust clears, although I’m a bit skeptical they will have much to offer with mortgages because it already seems to be a hyper competitive market.

I’ve been cruising along with a relatively modest 13% in our portfolio dedicated to UPST, but on Friday I was “put to” with a bunch of UPST put options (I’ve been selling puts for income with the idea of selling calls if/when put to). That share assignment merely accelerated my plan to increase my position. I’ll start selling some calls on new shares (now I’m boosted to something pretty high… maybe 50% or so) but will taper that so I’m holding shares when the company reports earnings in early August.

Will the stock pop at earnings? Maybe, maybe not. But eventually the share price should expand quite a bit.

Former RB and BL Home Fool, Supernova Portfolio Contributor & Maintenance Fool
He is no fool who gives what he cannot keep to gain what he cannot lose.

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Fair point, right now, not a portfolio of stocks.

Historically I have held 7-9 stocks in my portfolio. I have been doing these monthly updates for quite some time.

I am 47.


I’ve seen your update for a while now, so I was surprised when someone told me you were holding it only UPST.

The follow up question then is why? Are you seriously only able to find one stock you are willing to invest in? What happened to your other holdings. You seriously believe in UPST so much over those other names that you are willing to go all in on one name? A name a lot of smart investors we both know aren’t even willing to own in their portfolios?

I could see DDOG for instance, but not even that name I’d own more then 20% in a portfolio.

I’m not trying to give you a hard time, I’m really just trying to figure out why you would take such extreme risk like this.



Also, you state that if you didn’t own this individual stock, you would own that benchmark ETf that has 3600 stocks. Talk about two extremes. How can they even compare in any way.


I hope UPST will rocket high in the second half of the year. But what if it tanks? I knew a guy on twitter grew his account from $140k to $6 million in a year by investing in only one coin LUNA. He’s very confident that Luna will 10x in a year. He will diversify when his account reach $20 million. But in May this year, Luna dropped to 0 in a few hours and his account, which is almost all his networth, went to 0. So just be careful.


I hope UPST will rocket high in the second half of the year.

Hope is not an investing strategy, it’s religion. One needs a vision of where the business is going long term. If you don’t see a brilliant and achievable future then diversification is called for. Warren Buffett or his partner call diversification a remedy for ignorance, not in the pejorative sense but in lack of knowledge about your companies.

I knew a guy on twitter grew his account from $140k to $6 million in a year by investing in only one coin LUNA. He’s very confident that Luna will 10x in a year. He will diversify when his account reach $20 million.

I did something similar during the tech bubble and lost a huge part of my portfolio, the most expensive lesson I ever had. Then there was a fellow who mortgaged his home to buy more stocks on margin – bankrupt.

The lesson is that one needs a sturdy portfolio which is not just good stock picking but enough cash reserves to weather Black Swans. You hear people advising to go to cash or gold. Sorry, too late, the time for that was at the top when you had sample resources, not now that you don’t.

About Upstart, it could have that brilliant and achievable future if AI can truly predict who will or will not default on their loans. Amazon’s AI did determine that a teenager shopper was pregnant. The difference is that Amazon’s AI predicted the past, not the future. The girl was doing what pregnant women do. Upstart’s borrowers are subject to many more circumstances out of their control like the Fed doing stooopid things. Personally I stay away from credit risk, too unpredictable.

I’m not against a concentrated portfolio but the companies have to be well understood and their future reasonably assured.

Denny Schlesinger


I do think if you look at growth vs. value UPST is the best deal out there. I like DDOG the company, I got out of DDOG because what I felt was compressing future value potential.

DDOG valued at ~32B with last quarter revenue of 363m which was 83% growth rate Y/Y. Predicting 63% Y/Y revenue growth for next quarter.

UPST valued at 2.8B with last quarter revenue of 311m which was 154% growth rate Y/Y. Predicting 105% Y/Y revenue growth for next quarter. (full disclosure this represent no/negative Q/Q revenue growth).

Just comparing these two companies UPST has so much more room to grow in stock price vs its producing revenue.

I once owned 3 stocks early in my investing career. One of them I did not understand well, the other I really understood and the company “spoke to me” as an investor. Unfortunately the one that I did not understand went to almost zero. The other one was NFLX and I made a small fortune.

I guess I look at it like this. I probably have spent on average of 5-10 hours a week for the last 20 years studying investing, markets, companies, analysis, etc. So if I think I know what I am doing when it comes to evaluating a company, when I see what I believe is a great opportunity why would I not take it?

My plan is to acquire enough future calls to diversity into a second stock at some point in near future, however the valuation of the company gets better and with it my conviction gets stronger.


I guess I look at it like this. I probably have spent on average of 5-10 hours a week for the last 20 years studying investing, markets, companies, analysis, etc. So if I think I know what I am doing when it comes to evaluating a company, when I see what I believe is a great opportunity why would I not take it?

Just some thoughts:

Because no matter how sure you are, you might be wrong. Humility.

Because a black swan event might wipe out your investment.

Because you don’t need to hit a grand slam to become wealthy.


I would argue that sharing one’s performance results of -71.8% is pretty humble.

Now sharing some of my thought processes maybe came off as not. Problem is I have not shared what other assets I own or what my current wealth is outside of my stock investments. If I did…you would not think of me being too humble…you are correct I do not need a grand slam to be wealthy!


If Upstart is 100% of this portfolio yet, let’s say 20%, of your overall wealth, then that certainly puts a different slant on things.

You don’t have to tell us about everything else you own but a little background would help in understanding your allocation.

Sorry I didn’t mean to insinuate you are not a humble person. I was just commenting on this particular decision (in the absence of the background info).


My portfolio hit an ATH in February 2021, now I´m down 73%.
It hurt a few months ago, but now it doesn´t hurt me anymore.
It´s only money…I don´t really need, not now, not in the next months or years.

I wouldn´t have chosen UPST, though.

I wish you all the best, GOOD LUCK!


All in, in UPST?!

You cant trust the Managment of UPST, check latest news which will bring this to a new all time low…

There business model works only with big and free money form FED. Which will not happen in next years…

This was one of the greatest pump and dumps stocks by wallstreet.
Good luck

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All I can say is…ouch.

Management really set up their investors. Poorly described what was going on with the company. I still like the business but will be the first to admit the numbers are not as good now. I will wait to see what the next quarter guidance is before making any moves in my portfolio. I will continue to sell covered calls and raise cash on my shares.


“This was one of the greatest pump and dumps stocks by wallstreet.”

Indeed, one of the biggest scams of the last years.