Additional/Secondary Income Streams

[Gamecock-YT]

Shitcoin pumping/onlyfans/bank robbery

[gfp]

7 hours ago, Parsad said:

 

What are your strengths?  Interests?  Do you have any capital to commit to build up the side hustle?  Any hobbies that you would like to turn into a part-time business?  Anything you could partner with someone on and do together through a sole proprietorship, LP or corporation?  Would you consider making it your primary hustle if it worked out?

 

About 23 years ago, this started off as a hobby...then like 15 years ago it turned into a side-hustle...which led to multiple other side hustles.  So you never know what may lead to something profitable, yet entertaining!  Cheers!

 

I'm curious to hear what side hustles were spawned by the side hustle that is this website!

[gfp]

29 minutes ago, 73 Reds said:

About 30 years ago I had an unexpected opportunity to finance a home purchase for a couple who got turned down by their bank's underwriting department at the last minute due to some unpaid medical bills that were being disputed.  This enabled me to put spare cash to work at high interest rates, earn additional fees (loan origination) and secure the loan with a desirable asset that only increases in value.  It wasn't long before the proverbial light bulb went off.  I now do 30-40 such loans every year.  Startup costs: -0- (of course you need spare cash); advertising costs:  -0- (all leads come through existing contacts); Operating expenses:  -0-.  I personally evaluate every deal and use my own loan documents.  No other professionals are required other than a title company (another business that I own).  Total time involved for each deal is typically less than a few hours from beginning to close.    

 

That's great Reds, I figured you were a hard money guy from your other posts.  A lot less work and similar risk profile to many other forms of real estate investment.  Has it been your experience that the income is taxed at a much higher rate, all in, versus a more traditional income property investment?  I feel like I barely pay any tax at all on our RE income but my impression of hard money was that it was fully taxed.

[73 Reds]

10 minutes ago, gfp said:

 

That's great Reds, I figured you were a hard money guy from your other posts.  A lot less work and similar risk profile to many other forms of real estate investment.  Has it been your experience that the income is taxed at a much higher rate, all in, versus a more traditional income property investment?  I feel like I barely pay any tax at all on our RE income but my impression of hard money was that it was fully taxed.

Yes; fully taxable income is the biggest negative.   But that is one reason why I shy away from trading stocks; haven't incurred a taxable capital gain from any stock sales since the last century.  My real estate holdings also generate a lot of taxable income since nothing is encumbered by mortgages.  Once one gets used to paying a lot of taxes it is just another cost of doing business.

Edited July 9, 2025 by 73 Reds
word

[This2ShallPass]

17 hours ago, Eng12345 said:

I'm looking into finishing my basement myself - I figure I could get another 75k of home equity out of that plus the space (though I don't need the space). That would tie me up for the next year or so to do myself I figure. 

 

If you truly enjoy DIY then go for it. If it's a financial reason, my suggestion is you might be better of having someone else do it.

 

Twitter "guru" Naval said something that really resonated with me. To become wealthy, you have to put a high hourly rate for your time. Anything above that, you do it yourself and rest pay someone else. Time is the most valuable thing we have and spending that on things we truly like and are good at will payoff in the long run.

 

[Vish_ram]

one easy thing is to get CFP and do financial planning. you can charge a decent sum. If you get a good client base, you can become a RIA (get Series 65 etc).

 

I went the harder route of getting CFA, MBA etc, still was worth it. Secondary income stream became a full time job. 

[Red Lion]

9 hours ago, 73 Reds said:

Yes; fully taxable income is the biggest negative.   But that is one reason why I shy away from trading stocks; haven't incurred a taxable capital gain from any stock sales since the last century.  My real estate holdings also generate a lot of taxable income since nothing is encumbered by mortgages.  Once one gets used to paying a lot of taxes it is just another cost of doing business.

 

A real estate professional could create tax losses by buying or building multi-family properties / using cost segregation studies / getting a lot of bonus depreciation. This has always seemed like the holy grail to me...

 

On the one hand, do a healthy hard money business.

 

On the other hand buy and hold investment properties, financing them probably 60% LTV with good terms on investment mortgages. 

 

I can't ever seem to meet the definition of a real estate professional, since I work more hours outside of real estate than I do on real estate, but I do think I may go this way in the long run if I decide to semi-retire in the future. 

[schin]

On 7/8/2025 at 8:53 PM, valueventures said:

Figured I'd revive this thread, as I view it as an interesting topic and the conversation is dated (the last response was from 2016!).

 

I'm looking for ways to supplement my income through side hustles. Curious if anyone has thoughts / suggestions on what has worked well for them.

 

@valueventures - During COVID, I created a side, consulting business that was low-cap (me, my computer, and phone)... with all your work experience, there should be something you do better than others. Or as many here, have said.... create a passion project that allows you to sell or do something that doesn't feel like work.

 

The consulting work is 1099 and allows me to take on work here and there. Not having a boss is pretty cool.  I'm choosing not to scale out my business -- but, the margins are great and it actually got me to my FIRE number sooner.

[73 Reds]

13 hours ago, Red Lion said:

 

A real estate professional could create tax losses by buying or building multi-family properties / using cost segregation studies / getting a lot of bonus depreciation. This has always seemed like the holy grail to me...

 

On the one hand, do a healthy hard money business.

 

On the other hand buy and hold investment properties, financing them probably 60% LTV with good terms on investment mortgages. 

 

I can't ever seem to meet the definition of a real estate professional, since I work more hours outside of real estate than I do on real estate, but I do think I may go this way in the long run if I decide to semi-retire in the future. 

Well, start slow and grow these ventures as your comfort level rises.  The beauty of hard money is if you assess each deal correctly you can't lose.  In fact you very well make more (a lot more) if the borrower defaults.  Many years ago I used to say that this business provides Madoff-like returns.  Bad analogy but you get the point.    

[brobro777]

On 7/9/2025 at 1:20 AM, winjitsu said:

Credit cards + bank account sign ups nets me around 5-10k a year

 

Pet sitting + dog walkers make solid cash. My dog sitter charges $50-75/night and takes up to 3-4 dogs at a time. 

 

Years ago I cashed out a ton of Amex Membership Rewards points into my Charles Schwab account at 1.25 cent per point - no taxes!

 

Now they reduced the rate to 1.1 and put a limit to how much you can cash out each year. Gee I wonder why they did that haha

 

 

[winjitsu]

15 hours ago, brobro777 said:

 

Years ago I cashed out a ton of Amex Membership Rewards points into my Charles Schwab account at 1.25 cent per point - no taxes!

 

Now they reduced the rate to 1.1 and put a limit to how much you can cash out each year. Gee I wonder why they did that haha

 

 

If you like to travel, you generally can get 1.5 - 2 cents per point on economy flights, and up to 5-10 cents per point on business + class tickets! But it's a rabbit hole once you starting going into the land of points maximization. 

[TwoCitiesCapital]

10 hours ago, winjitsu said:

If you like to travel, you generally can get 1.5 - 2 cents per point on economy flights, and up to 5-10 cents per point on business + class tickets! But it's a rabbit hole once you starting going into the land of points maximization. 

 

This. 

 

I try to find the middle ground - deals are too lucrative to totally ignore, but I also don't want to spend hours planning flights (let alone hotels) to get the best redemptions available. 

 

I typically sign up for 1-2 stupidly lucrative cards a year.

 

This year it was Capital One (spend $500 and get $200 back) which I did in a single purchase. Now will be used as an balance transfer card to roll a portion of my new car loan at 0% interest for 18 months. 

 

The other was the American Express Business Platinum. Already had the personal, but got a 150k sign-up bonus AND the 35% points return immediately increases the value of the sign up bonus and the 180k of accrued points I already had. So far, have used points to book for round trip tickets to Denver, Toronto, Florida, and Hawaii for my girlfriend and I and will still be ending the year with a higher point balance than I started with as a result. 8-free round trip tickets isn't anything to sneeze at. 

 

 

Edited July 11, 2025 by TwoCitiesCapital

[lnofeisone]

5 hours ago, TwoCitiesCapital said:

 

This year it was Capital One (spend $500 and get $200 back) which I did in a single purchase. Now will be used as an balance transfer card to roll a portion of my new car loan at 0% interest for 18 months. 

 

Do you get charged 3% markup swiming the card or is there a 5% BT fee? 

[TwoCitiesCapital]

1 hour ago, lnofeisone said:

Do you get charged 3% markup swiming the card or is there a 5% BT fee? 

 

No mark-up for using the card - at least not where I made my purchase at. 

 

There is a balance transfer fee - would have to double check but I belive it's 4-5%. A great rate for 18 month financing and significantly less than what the car is financed at. 

[villainx]

On 7/9/2025 at 8:18 AM, 73 Reds said:

 Total time involved for each deal is typically less than a few hours from beginning to close.

 

I guess something in me would just assume there's going to be some big headache or moral crisis moment when you have to foreclose or just be forceful in getting payments back on track.  Has that happened?

 

 

[73 Reds]

5 minutes ago, villainx said:

 

I guess something in me would just assume there's going to be some big headache or moral crisis moment when you have to foreclose or just be forceful in getting payments back on track.  Has that happened?

 

 

On very rare occasions - yes.  In the early days I would handle a foreclosure myself.  Now if it happens I have a standing order to my lawyer:  Let me know when I have been paid off completely or own the property.  As for a moral crisis, not sure what you mean.  

[villainx]

On 7/9/2025 at 5:36 PM, This2ShallPass said:

To become wealthy, you have to put a high hourly rate for your time. Anything above that, you do it yourself and rest pay someone else. Time is the most valuable thing we have and spending that on things we truly like and are good at will payoff in the long run.

 

I tell this to my friend who has a fairly decent size NY residential RE portfolio.  Way too hands on.  For example, he insists on being there when tenants move in and out.  I'm always like, what the f' are you doing?

 

 

[73 Reds]

Just now, villainx said:

 

I tell this to my friend who has a fairly decent size NY residential RE portfolio.  Way too hands on.  For example, he insists on being there when tenants move in and out.  I'm always like, what the f' are you doing?

 

 

Rentals are different (I do that too).  Lending is strictly to investors after the GFC and Dodd-Frank.  Investors are in business for the same reason as me - to make money.  Therefore there are no moral qualms in the event of default, which occurs very rarely because we both enter a deal with the same objective.  

[villainx]

38 minutes ago, 73 Reds said:

As for a moral crisis, not sure what you mean. 

 

The usual where folks lose their home or something like that.  Or it's just another stumble from a serious of serious setback.  I know business is business, and everyone in transaction are grown up, but dealing personally with it can be different.  Though having the attorney layer helps.

 

Edit:  ah, more like lending to RE investor professionals.  That I can see being big boy (or girl) business.

 

 

 

Edited July 11, 2025 by villainx

[73 Reds]

6 minutes ago, villainx said:

 

The usual where folks lose their home or something like that.  Or it's just another stumble from a serious of serious setback.  I know business is business, and everyone in transaction are grown up, but dealing personally with it can be different.  Though having the attorney layer helps.

 

 

Hard money is a business built on convenience.  No one wants to pay mid to high double digit interest rates.  But having to qualify for a traditional loan takes time and will cause you to lose most deals.  Most contracts today around these parts are cash contracts with no contingencies - sellers don't want the hassles.  When I finance a property it is the same as cash for the seller.  If the buyer/investor has all its ducks in a row (i.e., title, insurance) I can close some deals in a matter of hours from the time the deal is brought to me.  Many of my borrowers have done dozens of deals with me which makes doing business that much easier.  Its a business that only gets better with time and experience but there is a learning curve and you've got to know the market(s) in which you do business.

Edited July 11, 2025 by 73 Reds
missed line

[This2ShallPass]

2 hours ago, villainx said:

 

I guess something in me would just assume there's going to be some big headache or moral crisis moment when you have to foreclose or just be forceful in getting payments back on track.  Has that happened?

 

 

 

This was me. Had a rental in Texas that I bought and sold sight unseen. Held it for 10 years, but I was way too lenient with the tenants. One of them was a single mom—seemed genuine, but just didn’t have her stuff together and was always dealing with some financial issue. I’d get these long emails, and since the payment being late wasn’t a huge deal to me, I always felt bad pushing her. Clearly not landlord material

It dragged on for a while, and when I finally sold, they’d left the place in rough shape (property manager didn’t tell me either). Had to spend a lot on repairs before I could sell.

Still made a solid profit—bought it with just $5k down on a great deal. But the experience kind of sucked overall, and I’ve decided rentals just aren’t for me.

[LC]

Nicer units rent to higher income tenants - less problems.

[This2ShallPass]

1 minute ago, LC said:

Nicer units rent to higher income tenants - less problems.

Yes this is the way to go. Payup to buy in a high income neighborhood with good schools. 

[Vish_ram]

Most important thing about secondary incomes is that make sure you can exit if you don’t like it, it should align with your mindset, values and skill set. 
 

 

[brobro777]

17 hours ago, winjitsu said:

If you like to travel, you generally can get 1.5 - 2 cents per point on economy flights, and up to 5-10 cents per point on business + class tickets! But it's a rabbit hole once you starting going into the land of points maximization. 

 

 

Dude I get that these international business class flights are good value but there's no availability. Like hordes of people are constantly checking for availability and they're crazy enough to book 360 days out! 

 

Besides Amex tells me I'm not eligible for sign up bonuses because I got em all years ago haha