Ryan Dice, who manages 17 companies across a $200 million holding group, breaks down the 11 roles founders get trapped wearing and shares a systematic approach to delegating your way back to the CEO seat.
The 11 Hats Founders Wear
- Marketing: Writing copy, launching campaigns, crafting offers, obsessing over lead flow
- Sales: Founder-led sales, chasing invoices, closing deals yourself
- Innovation: Creating all new products, services, and intellectual property
- Fulfillment: Delivering the product, onboarding clients, solving customer issues
- Operations: Building systems, running meetings, keeping the wheels on
- Finance: Acting as CFO, bookkeeper, and collections manager
- People & Culture: Recruiting, conflict resolution, being the company therapist
- Gopher: Resetting passwords, unclogging toilets, doing all the dirty work
- Customer Support: Handling angry emails, refund requests, and the support inbox
- Partnerships: Chasing collaborations, managing vendors, courting referral partners
- CEO: Long-term thinking, protecting company vision, reviewing scorecards, making high-leverage moves
The Core Problem
Most founders don't suffer from a lack of discipline — they suffer from a lack of delegation. The solution is not better time management. Wanting "more hours in a day" just means stacking more hats on your head.
"The more valuable you are to your business, the less valuable your business is."
Key diagnostic questions:
- How many hats are you wearing right now?
- What percentage of your time is spent in the CEO hat? (If less than 50%, your company effectively has no captain.)
- Could you solve your company's biggest problem if you had 90 days of focused time?
3 Steps to Remove the Hats
Step 1: Reassign hats that already have an owner
You're likely still doing jobs someone on your team could own. If you're paying them to wear the hat, give them the opportunity. Have an honest conversation: acknowledge you haven't fully set them up for success, hand over the hat, and agree to check in if they struggle.
Step 2: Ditch the hats that don't matter now
Some hats are mission-critical today; others are distractions dressed up as obligations. Be ruthless — kill, pause, or shelve anything that isn't essential right now. You can always put it back on later.
Step 3: Identify the one hat that unblocks your company
There's always one role your business needs you to play right now. Wear that hat — and only that hat — until the bottleneck breaks. The ultimate goal: only wear the CEO hat because you've got a competent head for all 10 others.
The bottom line: The long-term fix is installing a business operating system so that once you hand off the hats, they don't come back.