“If you want to go fast, go alone. If you want to go far, go with a team.”
I was 27 when I started my first agency, super excited and full of energy.
I had put together a small but super dedicated team of first employees. And together we built the agency from the ground up.
However, as the company matured, I realized something: If you grow and manage a business as the sole founder or CEO, you’re really that: Alone. Despite having a team.
Here’s why I think solo founders or CEOs can be really lonely, and how peer groups, a co-founder or a Fractional COO can help.
Why you need someone to speak to
I needed to make difficult decisions. I had to balance many different interests, manage risk and grow the company.
Some decisions were technically difficult: The decision for or against an investment, the decision on compensation structures or financial models.
Other decisions were emotionally difficult: Letting someone go or entering into a risky stream of business, for example. Or just dealing with some burdensome day-to-day challenges.
For both types of decisions, it’s valuable to have someone to talk to for three reasons.
First: Explaining your problem to someone helps you clarify your thinking. You have to structure the problem clearly. Otherwise the person you’re speaking to won’t understand you.
Second: Getting a second opinion about your problem adds a fresh perspective and sometimes gives you the solution right away.
Third: Spelling out the problem largely eliminates the emotional part of decision-making. Or at least surfaces what emotions are involved.
On top of these three reasons, you sometimes need to simply blow off steam. That employee who screwed up big time. That client who’s behaving like a douche. That strategic initiative that didn’t work as planned.
Offloading those things alone can be freeing.
Who you can’t speak to
So, there are many good reasons to discuss your entrepreneurial challenges with someone. But who can you talk to as a sole founder or CEO?
Your employees
You might have a trusted employee that you use as a sparring partner. However, there will be issues that you don’t want to or can’t share with them.
Think about
- a restructuring
- how much you want to pay that new rockstar employee
- your company is at risk of losing business or even not making it over the next quarter.
You can’t discuss these things with your employees.
Your investors or shareholders
If, like in my case, you have investors or shareholders, you can’t speak freely to them either. You might value their industry expertise and guidance. But if you have a critical problem, or just an emotionally loaded issue, they might not be the right people to speak to.
You don’t want to leave the impression that you don’t have things under control.
Industry peers
You might be well connected in your industry and have peers like other CEOs or entrepreneurs in the same field.
You’ll likely seek their advice or opinion on isolated topics that are not relevant for competition. But you likely won’t share new offers, strategic shifts or anything else you’re working on that would give you a competitive advantage, or disadvantage when shared.
Family and friends
If you’re blessed with business savvy friends and a successful spouse, you can speak to them. They’ll be able to give you input and a fresh view.
Yet, they lack context. They’ll be roughly familiar with what you do. But to really get valuable input you need to provide a lot of context. If you even get the chance to do that.
I found, there’s really no one you can easily discuss all of your problems with. Every potential sparring partner lacks a key element of what would make them the go to person.
Finding a sparring partner
There are ways to develop strong and trusting sparring partners for solo founders or CEOs.
Join small CEO networks or peer groups
I have heard great things about small CEO networks. They can be local, or remote and distributed. The good ones share these characteristics.
- No competitors: You don’t want competitors in there, but still peers who understand what you’re doing. Some networks accomplish this by geographic diversification. Others by admitting members from the same industry, but with different profiles.
- A trust-based environment: Good communities have clear rules about non-solicitation and non-disclosure. When you share what moves you, you don’t want a pitch in response to you seeking advice. You also don’t want sensitive information shared outside of the group.
- A stable set of members: You want people to stay in the group for the long run. Also, you want the group to be very selective about admitting new members. LParticipants will gather more and more context about what you do over time. Thus their advice becomes better. If new members are added sparingly, the dynamics of the group don’t change too often.
Bring in a co-founder / shareholding leadership team member
You can also bring in a second senior leader that owns shares in the business. Ownership will help bring them to the same level of involvement.
But obviously there’s a risk to choosing the wrong candidate. And you’re giving up equity.
Bring in a fractional COO
A great option is to bring in a fractional COO, as they check a lot of boxes:
- After a short white, they know the business inside out.
- While being part of your leadership team, they’re a clear number two. Hence they listen and give advice. But you call the shots. And they have no interest in questioning your role or skill.
- They’re not as attached to their position as a full-time COO would be, because the engagement is designed to be temporary. Therefore, you can even discuss things with them that affect their position.
Regardless of which option you choose, don’t build alone. I’ve experienced with later ventures how much easier it is when you’re not alone. And it’s more fun for sure.
