I own 40+ businesses... here's my 5 "hacks"...

It’s been 2 weeks since I sent an email, and over 2,000 people have joined this newsletter since then. If you don’t remember who I am, I’m Scott Oldford, an investor and advisor who owns 40+ online businesses, and this newsletter is dedicated to giving a behind-the-scenes look.

In my last post, I spoke about cutting vs. bulking and the impact that has on your business…

And today I wanted to share a little bit about a question I get super often:

“How the heck do you manage 40+ businesses?”

Which, in truth, is a really good question, and I’m also still learning how to both grow, scale, and build all that I am.

The first thing, I believe is important to understand is the following:

The reason why business is quite difficult is because you’re likely only good at a single thing, or perhaps a couple things and due to this, you spend a massive amount of your time in business learning things that are new.

The upside of this is innovation and evolution, however, it causes you to lose a lot of time, simply because you haven’t done something before.

Take something as simple as Facebook Ads. It's a psychological and physical disaster the first time you run an advertising campaign. Simply put, you won't believe in yourself, won't understand how it operates, will doubt your judgment, and more often than not, you won't only be unsure of how to use ads but also about webinars, funnels, copy, creative, optimization, testing, life-time value, ROI-windows, and another 30 crucial factors.

Now, compare that to someone who has ran thousands of ad campaigns for over 10 years and has generated hundreds of millions of dollars. When the person who runs a campaign that has done it over and over again, they simply put out their playbook and launch the campaign. They don’t even think about it.

Inherently, as you build a business, you get better at all of what it takes to build a business. Each time you build a new business, or help build a new business, you gain a new understanding of the skills required under each pillar of the business.

And… this is perhaps the easiest “answer” to how I’m able to successfully* run a portfolio of 40+ businesses. Simply because I’ve had so many repetitions of building businesses that I’m taking things I’ve learn over the past 20+ years and simply adding them together.

_{* The jury is out if this will be successful, however, for all things considered, I consider what I’ve built even so far, fairly successful.}

I think this is an important lesson in general, as I see Entrepreneurs “skipping” the lessons all the time and, due to this, they aren’t able to create success.

Business and life are quite simple. The more you do something, the easier it becomes. The easier it becomes, the easier it is to do more and make it look effortless.

#2. The next important aspect? Doing more is generally easier than doing less.

A $500K/year business is generally more work than a business that generates $5M/year.

Having a single traffic source is more difficult than having five.

A single salesperson is more difficult than eight.

There is a certain level of efficiency that occurs with doing more, yet, as humans, we are generally afraid of more responsibility. A lot of the time, the thought of more feels like we’re drowning. However, in reality, more makes things a lot easier and creates efficiencies that couldn’t exist any other way.

For example: By September, we’ll own nearly two dozen newsletters, and a newsletter is a prime example of a business that by itself is difficult to “make sense”.

In order to make a newsletter work you need great content, someone to sell sponsorships, technology, research, design, growth… along with a lot of other things.

By itself, it’s not super easy to get a single newsletter to work, unless you’re keeping it small and running it yourself and you’re all in on that single business. Which to be clear, is a TOTALLY okay option.

However, when I decided we were going to get into the media business, I knew that we were going to need the capacity to run 100+ newsletters if we were going to make it a success.

Why? We can have a writer, write for multiple newsletters. We can have the same person run ads for all of them. We can have a sponsorship team that takes care of everything, the same outreach team, and the same email delivery team.

Instead of advertising management costing $5,000/month, it might cost $300/month for each newsletter. Instead of the world’s best email deliverability experts costing $30,000/year, it costs $500 per year. Instead of paying $4,000/month for a sponsorships person, a single person can sell sponsorship spots for 20 newsletters. Instead of Zapier costing $2,500 per year, it costs $2,500 for 20 businesses.

In total, your expenses are much less. Your waste is much less.

Of course, the downside is that building more at the beginning means you get less visible momentum and you stay in what might feel like less growth for longer, than if you focused.

However, once things work in a model where you have multiple businesses that use a similar model— and resources that can be easily shared, you’re able to create a massive growth curve, while keeping waste (expenses) low.

Further, you’re able to have a team that is likely full of far more A-players that are innovation and growth focused— simply because the upward trend of this type of business even allows for a VA to have multiple growth paths.

#3. The best choices are available when you have all of the data available.

This one has perhaps 20 different layers that is it’s own book, even. As you grow a business, you get better at growing that business because you’re able to understand data more easily and the amount of data increases.

If you do one webinar, you don’t really know what works. If you do five hundred, you almost always know what works.

Further, in most businesses, the reason why things slow down, don’t work, or the Entrepreneur or Owner is overwhelmed is the flow of information.

Too much information creates a lack of ability to make a choice.

Too little information creates the wrong choices.

To help with this inside of The Wisdom Group, I have a series of systems that help me have the right data. They include things such as…

• A daily rollup of every single important conversation that has happened in every single business, rated in priorty along with it’s importance for me to chime in.

• A daily rollup of every single thing that needs to be reviewed so I can have my eyes on what actually needs my eyes on it that is then added to my “get to it” list.

• A weekly rollup of everything that has been completed, the issues in the businesses, the things that worked, and what will occur in the next week.

• A weekly rollup of a snapshot of the most important data from all businesses, based on business type.

This is added on top of other daily/weekly elements, along with those that happen more on a monthly or quarterly basis. However, instead of talking to a lot of people, I don’t. I talk to very few.

Instead of seeing a lot of emails, I don’t—I see very few.

Instead of reading anything on social media, I don’t—I only post.

Instead of having a lot of meetings, I don’t—I use them only for visioning or 30,000ft strategy.

This snapshot of data and communication allows me to protect my energy and productivity, while giving me a clear amount of information as needed. However, behind our operating system that we’ve built (and still building) is the ability for me to go as deep as I want.

Want to go into the P&L of a specific business? 2 clicks.

Want to go into the exact stats for a single newsletter? 1 click.

Simply put, the systems for the flow of information from what a VA does to being able to understand what that VA does are hyper-critical.

And… in many businesses, even more so those under $5M/year, none of this will ever happen simply because there isn’t enough resources, you can’t attract the right people, you don’t see the value, or… another dozen reasons.

Yet… it’s one of the largest parts of the puzzle for being able to run and scale all the businesses that we own.

#4. Having a great A+ player team doesn’t solve all your problems, but it solves most of your problems

Building and running the business I own would be impossible without the team that we have.

I’m all for having a small agile team, I ran my personal brand business with just a few team members and I believe for the size of what we do, the size of the team we have is relatively small.

However, it doesn’t matter if it’s a virtual assistant, a project manager, ads manager or anything in-between. The level of gratitude I have for a having the right people on a team, is truly what allows me to work as much or as less as I desire.

When we have problems— it simply is fixed. When I have a vision, it comes to life. When I have a strategy, I simply can describe it in 10 minutes.

If you’re manifesting your reality, you’re only able to create it at the level of the people you surround yourself with and perhaps one of the most important parts for a visionary Entrepreneur is to have an amazing team.

Further, having that team setup in the right way.

We have two models that we run inside of The Wisdom Group.

The first is the partnership model, in this model, we’re working with someone else who is generally the majority owner of the company. They are responsible completely for the day to day and are the complete leader and owner of the business.

The second is the wholly owned model in which we have an operator that is responsible for a specific business (or a rollup) of businesses.

From here, each business has specific resources that they have access too, along with a specific vision and growth plan. Keep in mind, this continues to be iterated, reviewed and built. To be clear— I DON’T have all the answers in building this, I simply have helped build these things in companies long enough to know what works and what doesn’t.

In building in this way, there are segmented “teams” of people that then have resourced “sub-teams” allowing for those people inside of the business to be fully focused on their outcomes, their vision and the entire business.

Most people have very little understanding of what’s happening throughout the other sides of The Wisdom Group and I believe that is important, as too much information creates a lack of clarity.

#5. The fifth (and final for today) thing that allows me to build these companies in succession at once? Time horizon.

Perhaps the biggest blessing of success is that it allows you to see further into the future.

If you have 30 days of money in the bank. You can see about 60 days into the future.

If you have 6 months, generally about a year.

The more resources you have, the easier it is to see into the future. Further, the more you understand an industry and business model (like we do) the easier it is to see what the world will look like in 3 or 5 years.

This is perhaps our largest unfair advantage. It’s one that allows us to build things not for today, or tomorrow, but knowing where it will lead. It allows us to build certain businesses not for profit, but for growth.

It allows us to build other businesses for cashflow and yet others to be ready to be sold to help us fund the development of what we’re building.

In most businesses, the largest difficulty is being able to align systems, operations, structure and team with being able to create revenue and delivering on that revenue.

Most of the time, Entrepreneurs either are “too good” at marketing and sales, creating high levels of false momentum, selling things they can’t deliver on, or that will break the business.

Or they are “too good” at systems and structure, building a world-class structure with not a single customer in sight.

However, when you marry both, due to having the right team, experience, resources and time horizon view, your ability to increase the chances of success continue to increase.

And this is why time horizon is so important. The further you look into the future and you can build for the future, the easier it is to see the vision of each individual business and how they tie together.

For example: With our OnlineBusinessOwner.com business, I knew that this would be a brand that extended into potentially a dozen business lines.

We bought this business about a year ago and we’ve been slowly building the infrastructure behind it.

Now we’re growing the audience for less than $1.50 a subscriber, our Summit with over 50 speakers will be live in September. We’re launching 6 different sub-brands inside of Online Business Owner and in 2024, we’ll likely launch our first conference.

The vision for OBO for me is dialed in up to 2027 which allows for the choices in that business today to be obvious.

In conclusion, these are some of the things that make it possible to build and scale 40+ businesses.

However, these things are also what can easily help you grow your current business. Why? Everything I spoke about can be applied to a single business, or a couple of businesses.

It simply comes down to you rethinking the way you currently do what you do and bringing a new version into the future.

Oh… and information flow. I promise you. Information flow might be the most important lesson if you ever want to have massive success 🙂 

That’s all for now.

- Scott