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For founders running multiple businesses at once

David Sherry
5 min read
For founders running multiple businesses at once

If you’re a quick starting founder type… that is, one of those people who just start, rather than doing research or thinking too much…it’s common to have multiple projects or businesses running at one time.

I have multiple clients right now, each of whom has one, two, or three businesses, at varying stages.

A common thing that is told to them by other people or the Twitter-sphere is “You can’t run more than one business.”

Of course, this is totally false, as I work with people who are currently doing that!
Ironically, some of them are the same ones that have a false belief wondering whether or not this is possible.

The above can be true whether your side-business is a 2nd job, a podcast, business consulting, or a SAAS product. The major problems are the same, too.

What are the major problems I see that do occur with this type of founder?

  1. The biggest issue with running multiple projects at once arises when you are the one who is critical to doing the work. This is quickly unsustainable.

2. Issue number two is that one, or multiple of the businesses don’t actually make any money.

You might ask how this could be possible, but trust me, it’s common. Self-funded companies need money to get off the ground and it’s typical for them to burn cash, or maybe raise money and burn cash until they can get profitable. Many businesses/projects are in survival mode.

3. Issue number 3…The companies get out of control from lack of presence and information sharing.

Managing your own energy is key, and you can only focus so many places at once. If you’re getting a new business off the ground, it’s really common/easy to not have enough mental space to be totally present for the other companies and the people running them.

All of these problems lead to other problems.

Problems like…

  1. Juggling/dropping the ball (giving 80% to one, 20% to the other, 0% to the third)
  2. Micro-managing / lack of delegation.
  3. The shit hitting the fan all at once between multiple companies.
    While not having all your eggs in one basket is great for diversification, from time to time multiple fires or cash needs can arise.
  4. Not killing/restructuring businesses that aren’t working.

The flip side is that all of the solutions to these problems lead to huge personal and professional growth.

The reason I LOVE to work with founders who run multiple companies or projects at once is because of this fact.

All of the solutions lead to huge personal and professional growth. If you put yourself in this position, you are forced to delegate to people. You are forced to have better systems in place that share information. And you’re forced to think critically.

Having some buffer room due to diversity of opportunity can (sometimes) help you think more clearly, too. By not having all of your eggs in one basket, suddenly the distance from the business helps you see it in a new light. This is especially true if you are sick of the company itself.

This objectiveness can and will allow you to make better decisions vs. being so “in” the company that you’re not thinking rationally about what needs to happen.

A role I play as a partner/advisor to companies is to help them develop their companies into businesses that can run without them, freeing their time to pursue their next venture.

If this can be done well, it can not only build on the asset they have already created, but it also can provide an awesome opportunity for work and growth for the team that gets hired.

The road map for building multiple companies starts…

Road Map
I recommend a short, month-to-quarter long sprint that begins to patch holes in the ship of the company and prepare it for growth beyond you. Monthly/Quarterly planning should always be done from the frame not just of “what needs to get done?” But rather… “What can we change structurally within the company such that it is ready to grow?”

This road map is part of a quarterly process I run with founders where we seek to not only develop the goals for the company, but also the foundational changes that need to be made to make the company ready for an upgrade in its structure.

Starting and then Delegating
There is a positive flywheel that every business owner can put into motion that will continually provide more freedom, leverage, and impact in their business, and that is delegation and hiring.

By shifting the founder’s role/mindset to being that of a “starter” but not a “pepetuator.” Every area that is done more than once within the business can be structured and delegated.

The key is to simply ask yourself: “Which part of my business takes up the most time, with the least impact/benefit? That I currently do on a regular basis?”

If every quarter you delegate or hire for one area of the business, you simultaneously give yourself that time to put towards higher leveraged work.

People are the key. Finding, trusting, and incentivizing them to step into new roles and growth within your company allows them to take on their own version of the positive flywheel, growing personally as they grow the business.

What do YOU want from the business?
If you’ve trapped yourself in your own business, it’s because you’ve lost sight of what this business is actually for, for you. This can be further clouded in moments where a company is struggling to survive.

"What do I want this business to become?"

Defining what you want from the business also allows for the team you’ve hired to have clarity on what your role is within the company and what size you are aiming to grow it. This clarity for yourself creates alignment, and without that… teams can fall apart because they get the sense that you could come in and toss a grenade in any time you please.

Make sure the team is clear with your role, what your vision is for the company, and what everyone is working towards.

Synergistic Opportunities
The highest leverage work founders often do is seeing serendipitous, synergistic opportunities between companies, people, and partners.

There are huge opportunities for growth simply by pairing up the right people and letting them run with a new partnership, or developing an overlap between companies that creates a massive impact.

Can you run multiple businesses/projects at once?

Founders can and will run multiple projects/companies at one time. In fact, this often leans into some of their strengths which is to quickly start new ideas and put them into the market.

However, It's not possible to run each one of them "full-time."

This creates an opportunity for growth, objectivity, and hiring that forces Founders to adapt and adopt new beliefs about their role and the strengths they bring.

If you're a founder/creator looking to remove yourself further from a company to start a new one or manage multiple companies and looking for help with this transition process and scaling, hit me up.

Client example (Spends less than 4hours per week on this company)
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