Short v. Medium v. Long

If there is a single thing that you will screw up as you are scaling or building wealth?

Short v. Medium v. Long Term Investments…

Here’s what I mean 👇

By the way, it’s been a minute since I sent an email. I’m going to be sending here more often now. If you don’t remember who I am, I’m Scott Oldford. I mentor and invest in Online Businesses. By the way, are you following me on X?

Most of my investments are in privately owned or Series A-B businesses.

I went this route due to the fact that I have high monthly cash flow from mentoring other entrepreneurs and I’m 33 (27 when I started this approach).

When someone comes to me to scale a business generally it’s about decreasing their profit margin and/or taking on capital to help with being able to build and scale.

In this process there are things that have various windows of return.

Sometimes it’s 7 days…

Sometimes 90…

Sometimes years.

The same happens when you are aggressively building wealth (or net worth).

The problem comes when either:

A. You misjudged the return window.

B. You mis-labeled a specific investment

C. You made too many of a the same investment type.

Or…

All three.

When building a business too much short term means you’re always chasing the next month and in reactive mode.

While being too long term might mean that you run out of money before you’re able to get the return.

In investments it means having a lot of cash flowing investments (short term) that potentially don’t give much return, versus long term that will give a lot of return, but low upfront liquidity.

Mastering these levels in either building a business or investing isn’t easy.

A large part of this is due to the fact that many variables are not defined and you generally only know in hindsight.

Last year, this week, I found out that about $15M of investment that was intended for my portfolio wasn’t going to come to fruition.

This was a black swan moment where it was signed and done, but things out of my control prevented it.

We were on track and things were going as planned.

But instantly the medium and long term investments I made based on the context of outside investment no longer made sense.

I opt’d for a strategy that started to see a mid-long term approach and because I had invested capital I kept very little short term investments.

This created a scenario where I had to reshuffle my entire investment theory and strategy (as I wasn’t willing to take investment from those that could fill a $15M investment).

It meant exiting businesses I believed in but couldn’t take care of in the short term.

Firing a lot of people.

Changing the way I structured nearly everything in my business strategy.

I went from

10% short term

40% mid term

50% long term

To

40% short term

50% mid term

10% long term

I potentially hurt the future value of my net worth by tens of millions and arguably it was the most painful business experience of my life.

It hurt liquidity and when liquidity is hurt, your ability to make the best choices is also hurt.

It’s a year later and while I wouldn’t go the route I did before on investment strategy.

Understanding that your investment thesis for net worth or for your actual business has such an impact on it is something you should be thinking about daily.

Changing these levers take time.

The result can be amazing or very difficult.

You can have peace while scaling or be stressed to the point of no return.

But not thinking about it?

It’s a risk too many people don’t think about.

And when you’re thinking about it and analyzing you can change the sails as needed, quickly.

You become less emotional and don’t define things as failure but are able to understand that all investments are cause and effect.

If you track and understand this..

It allows you to build the business or portfolio based on the reality you desire.

That’s all for tonight… just a simple reminder from a big lesson 🙂 

-Scott