New software startup founders sell themselves short when they tell me, “I never want more than 10 or 15 employees. I don’t think that would be any fun.”
Yet they still want to build a valuable software company that doesn’t rely on the founder for everything.
They think more employees are just more headaches.
But more employees can make a better business and a better life for founders—when you deliberately design your organization with the right foundations.
Brett Gilliland is the founder of Elite Entrepreneurs, which delivers coaching, workshops, and community programs to help hundreds of ambitious entrepreneurs navigate the company leadership journey from $1M to $10M in revenue.
Elite Entrepreneurs workshops and coaching show founders how to move from founder-led chaos to aligned leadership teams.
Brett has seen that co-creating a clear, practical Purpose, Values, and Mission forms the foundation of scalable organizations.
With clear meeting rhythms, disciplined execution, and strong hiring practices, overworked founders can become happy CEOs and build much larger companies that run without constant founder involvement.
There is a personal transformation for owners as they go from stressed, busy startup founders to strategic CEOs who enjoy their business more as it grows. As Brett describes it:
“All of us get stuck in some way. We know there’s a better way. We see other people figuring it out. I should be able to do this, we say, but we just didn’t know what to do.
“You have to do work on your business in a deliberate way. And those who do the work consistently make progress. We help them lay out the path from $1 to $10 million. Here are the things that you do. It’s proven, it’s practical.
“Whoever has been consistent with it, quarter after quarter, month after month, week after week, doing the things that we’re talking about, they start stacking wins.
“Then all of a sudden, 18 or 24 months later, they’re at a place where they’ve tripled in revenue, they’ve doubled in team, it’s fun, the founder has got some time back in their life. It does take time, but it’s totally doable. I’ve seen it over and over and over again.”
On the podcast this week, Brett also shares some key leadership foundations that need to be developed to grow bigger and not get stuck:
- Growth Brings Freedom: Founders who learn to let go in the right way often rediscover fun, profit, and time.
- Leadership Teams Required: Scaling past $3M–$10M depends on building a capable senior leadership team.
- Meeting Rhythms Drive Scale: Annual, quarterly, monthly, and weekly cadences keep teams aligned.
- CEO Core Roles: Set the vision, build the team, and secure resources—everything else gets delegated.
Check out this enlightening interview with Brett Gilliland on the Practical Founders Podcast.
