The Future of this Newsletter + Blog...

I started this investment newsletter/blog in October 2022. In reality, I simply wanted a place where I could share what I was learning, as I was spending the majority of my time investing and advising.

While I have a very large email list of entrepreneurs (for www.scottoldford.com) that are interested in scaling a business, in truth, scaling a business and building a business as an investor, is completely different.

At the time, I started Substack and like most things in my life said… “LFG 🚀”.

I sent out an email and Facebook post, got my first 100 subscribers and since then I’ve been slowly building this, knowing that the “vision” for what I wanted to create would come.

Now, that vision is here 🙂.

Launching later this month, we will be relaunching this newsletter and blog as Online Business Owner: Invest.

See, I believe there is a massive need to bring the right people in front of entrepreneurs who want to invest, alongside those who want to invest in online-based businesses.

Up until this point, while I’ve grown mostly through my own organic audience and sponsorships, I’ve done a terrible job of building relevancy. I remember in Substack, we had over 27,000 unique visitors, yet less than 3,000 subscribed.

Further, I want OBO: Invest to become a center for thought leadership, authority, and help when building and buying businesses online, as I believe as we continue into the future, the trend will only continue.

I believe this will help increase the amount of help I can provide, along with being able to supercharge the growth of this platform.

The benefits of not being the only writer on a topic are massive, and it surprises me that people don’t do it more often, you get to utalize much higher levels of momentum, expertise and you’re able to build something that is truly valuable for someone to watch and listen too— I love that.

That’s not all— OBO: Invest will become the centerpiece of our collection of investment-focused businesses.

I believe that the next few years will be some of the greatest for those that are looking to invest in businesses. The reason is simple: A lot of businesses, by themselves, don’t make a lot of sense.

If the economy becomes worse (which I don’t wish for at night), it will create businesses that by themselves won’t work— which creates prime time for acquisition.

When it comes to the online space, which is the one that I primarily invest and build inside of, a few things I expect will happen in the coming years.

#1. Expansion & Growth of the market

#2. Contraction of 1st time Entrepreneurs & Under-Equipped Entrepreneurs

So… how can you grow and contract at the same time? Simple… Businesses that have an unoptimized business when times aren’t as easy, don’t work out— while at the same time, when others have their jobs displaced, they start businesses and decide to transition to online businesses.

This creates an interesting feedback loop because while things are growing, only those with the best business models, offers, marketing, sales and team are able to succeed.

Everything else, won’t work and if we are in a “recession” it means that unoptimized businesses will have a more difficult time working.

When we’re in a time when money is free-flowing, it’s much easier to run a business. If your margin is 40%, you don’t optimize the same way you do if your margin is 15%. Further, if 50% of your sale calls close, you don’t prepare the same way if it’s 10%.

When times aren’t as good— it takes more energy to optimize.

In 2012, I sold my marketing agency for $1 to escape going bankrupt.

I’ve had many businesses that haven’t worked… and it’s driven me to do much of what I do today…

See, back in 2012, I could have done a lot of better things after I realized I messed up, however, I didn’t know the difference.

In essence, my entire portfolio of businesses is optimized based on the mistakes I’ve made.

My business advisory, mentorship and education side of what I do is meant to help Entrepreneurs scale up successfully.

If they do, I want to help them be able to exit. If they don’t do it successfully, I want to help them move into their next thing quickly.

I want more Entrepreneurs to win the game of Wealth.

The only time an Entrepreneur wins is if they stay doing the same thing for a long time, if they take their capital/profit made and extract and invest it elsewhere or their company is sold.

That is how Entrepreneurs win the game of wealth.

To do this, inside of The Wisdom Group (my portfolio company) and Online Business Owner: Invest I’ll be focusing on a few different things…

1. Education for Entrepreneurs on how to build their business to both acquire businesses and sell their business.

2. Media worth consuming in the form of blogs, newsletters and podcasts that are based on helping Entrepreneurs invest and for investors to invest in Online Businesses.

Most Entrepreneurs have no idea how to build their business for sale. Further, majority of people don’t know how to acquire a business. Since I started doing this 4 years ago, my net worth has exploded, simply because I learnt what to do. I want the same for others.

To start this education and media rollup for Entrepreneurs, Business and Investors we are bringing together some interesting businesses.

#1. Acquisition of Duuce.com— the #1 marketplace for newsletters.

#2. Acquisition of Acquire.gg— which includes 2 newsletters in the online space.

#3. Minority ownership of exitDNA— which helps Entrepreneurs build a company for exit, ensuring the highest multiple (and ease) possible.

#4. The launch of OBO: Invest— which will include a blog, podcast and the newsletter you're reading right now.

This along with a few other acquisitions I can’t speak of, a few partnerships— along with one from a billionaire mentor of mine will create what I believe is one of the easiest ways to help Entrepreneurs grow, scale, acquire and sell their businesses.

This is just the start and friend, I’m excited that you’re here for it.

- Scott