Why I decided to raise money (and how I'm doing it)

Things have been going with full-on momentum and due to that, it’s been nearly a month since I’ve had an update. So if you’re not reading this in the future, thanks for that patience.

And… if it’s been a while, as a reminder: I’m Scott Oldford and I’m the CEO of The Wisdom Group, which currently owns 36 businesses in the Education, Media and SaaS space. Further, I’ve grown over 200 online businesses past 7-figures and spend most of my time investing and advising….

Ok— just wanted to make sure you remembered who I was in the inbox, friend :)

My entire Entrepreneurial career I’ve never taken a dollar of investment… ever.

While I’ve had business partners bring in capital, I went from being 7 years old and selling eggs on my parents farm, to my first million dollar business at 16 and even an 8-figure business by the time I was 27… and I never took a single dollar of investment.

Now… I’ve had a lot of people help me… but write me a check with a return? Not so much.

Further, I’ve always done things “my way”… and so the feeling of having an investor? Simply didn’t appeal to me.

And… like most things that we “don’t do”… this is one that has now changed.

Coming into the new year, I had a “feeling” that it might be time to change the way I was spending time and attention.

As you might know, I run my mentorship & advisory business that does quite well, where people pay me a fixed amount of money and I help them scale their business.

On the low end, this is $60,000 per engagement, on the high-end, it’s $500,000. Over the past number of years, this is one of the main places I’ve been able to create capital for investing.

The problem? It’s time intensive and I’ve grown The Wisdom Group, to a point where continuing to have this as my main driver of money for investing into the future of The Wisdom Group, will hinder the growth and potential success of The Wisdom Group.

I had a few options:

1. Increase the amount of time I was working (which isn’t an option for me, having a 9-month old)

2. Decrease the speed in which we are growing The Wisdom Group (and we’re not growing it “that” quick, so again, not a great option).

3. Raise capital for The Wisdom Group (the option I chose)

As option #1 and #2 really didn’t feel like the right one’s, I slowly opened up for the third option, which was allowing for investment into The Wisdom Group.

This is going to allow me to do a lot, that I wouldn’t be able to do beforehand, which includes: 

- Focusing majority of my time on The Wisdom Group and the companies inside of The Wisdom Group

- Focusing my brand and mentorship business on the exact avatar and person that I’m looking to attract inside of The Wisdom Group (as per my investment thesis and my 12 laws of investment)

- Being able to deploy capital for the development of infrastructure.

- Being able to deploy capital when there are things that are “winning” inside of the businesses of the group.

- Being able to wait for profitability inside of certain businesses, which will create better long-term growth and profits.

It’s also going to change a lot, in the way that I do business, as going forward, having investors means a different level of planning, accountability and transparency— which will also allow me to build an even better company.

Further, it’s allowed me to create a level of structure inside of our finances, operations and legal, that I’ve never had and is also one of the major reasons why I haven’t written here for almost a month.

In raising money… I’ve taken my normal approach to most new things I do…

First, I decided that it was time to do it and so I had conversations of dozens of people who both raised money and invest in companies.

Second, I decided what I would use that capital for and how things would look different inside of the business.

Third, I took time “away” to make sure it wasn’t just my ego wanting to raise money (or something else)

Fourth, I went slowly and raised my first small amount of money, then with a bit more.

Fifth, I did the identity work required to fully go from being an Entrepreneur to being an investor (which is always the “last” step of being able to fully create a reality, in our life).

I’m really excited about this…

Largely because the more people in which I talk about The Wisdom Group and what we’re doing, the more energy I’m building around it.

Coupled with the fact that the more people I speak with, the more I realize that the “right place and time” that I talk about with those I mentor with, is exactly where I believe I am, at the moment.

And thus… you get to be part of a behind the scenes look at what we’re building, my investment strategy and all the pieces in-between and for that I’m even more excited about. 

So, how am I raising the money?

At the moment, this is a 3-step strategy:

The first part is using a promissary note, to raise the first amount of money (which is well on our way).

From here, we will be then turning that note into a convertible note, which is due sometime this Summer (as those things take a while).

And finally, from there, when the time is right, we will turn those convertible notes into equity, likely with a full raise to follow.

At the moment, I’m simply having those that I have a close relationship with invest, keeping it to accredited investors, that know me, like me and trust my vision. My intention is to keep it this way, until much later in the future when it’s time for more intuitional investing to occur.

I’m also not raising, just for the sake of raising. Meaning, I’m not raising more capital than I need. Why? Because, when money doesn’t know where it’s going, it finds a way to disappear and thus, I’m taking a more than conservative approach.

I’m an incredible Stewart of my money and I’m excited to be a Stewart of the money that is being invested. 

This also allows me to have a clear boundary…

Before The Wisdom Group and my Scott Oldford brand were directly interconnected. Shortly, they will be completely separate.

One helping the other, but not entangled.

Energetically and physically, this allows for what I believe all Entrepreneurs and Investors must strive for…

Being able to ensure that your business is an entity, that isn’t simply you. That it lives beyond just you and your energy and that it is supported by others— not simply you.

That’s a post, for a different day.

For now, thanks for being here, I’m excited to share more and hopefully help you understand how to invest as an Entrepreneur, more and more.

- Scott