Leadership is hard. Leading while running a business, managing a team of freelancers, and trying not to burn yourself out in the process? Even harder.

In this episode, Melissa and Meredith sit down with Steve Guberman, founder of Agency Outsight, former agency owner who scaled to 12 people before selling, and now an agency coach who's helped hundreds of founders navigate the messy middle of growth.

They get into the real stuff: How do you delegate without feeling like you're losing control? What does it actually look like to shift from doer to CEO? And what happens when your ego leads you to chase a "dream client" that nearly breaks your business?

If you've ever wondered...

1. How do I hold my team accountable without micromanaging?
2. What's the difference between being a kind boss and being a pushover?
3. How do I know if I'm ready to step into the CEO role, or if I even want to?
4. What do I do when one client is taking over my entire business?

...this one's for you.

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Chapters:

(00:00:00) Intro & Meet Steve Guberman

1. From agency owner to coach helping hundreds of founders navigate the messy middle
2. The ego-driven belief that launches most agencies: "I can do it better"
3. Why designing and running a design business are two very different things

(00:05:11) Setting Expectations with Freelancers: The Lawful Way

1. The commitment-based approach to holding people accountable (without crossing legal lines)
2. Why clear expectations must come before accountability
3. The difference between empathy and being a doormat

(00:10:31) The Inner Conflict: Empathy vs. Running a Business

1. When "leading with empathy" turns into self-sabotage
2. Absorbing everyone else's failures because holding them accountable feels mean
3. The Brené Brown moment: "You can lead with empathy and still be a good boss"

(00:13:05) The Emotional Burden of Being Responsible for Others

1. "People are depending on me to eat. That's a heavy burden to carry."
2. The weight of being responsible for your team's rent, their kids' activities, their mental health
3. Why this pressure can feel crushing even when you're doing well

(00:19:21) CEO Is a Mindset, Not a Headcount

1. The founder-to-CEO identity shift (it takes at least a year, often longer)
2. Why you can be a CEO of a two-person agency
3. Being honest with yourself about what you actually want to build

(00:24:06) Steve's Agency Story: Winning the AOR That Changed Everything

1. The massive AOR that doubled his agency overnight
2. The ego that drove him to chase that client
3. The painful layoffs when it fell apart a year later

(00:36:11) The Delegation Chicken-and-Egg Problem

1. When you can't afford to delegate but can't afford not to
2. The thousand-dollar-an-hour rule for founder time
3. Getting out of a toxic client relationship without blowing everything up

(00:39:21) The Time-Tracking Exercise That Opens Founders' Eyes

1. Four highlighters: what to stop, start, delegate, and keep
2. Making delegation obvious instead of theoretical
3. Focus on the thousand-dollar-an-hour activities

(00:44:52) Final Thoughts: Intentionality and Courage in Leadership

1. The courage it takes to build the business you actually want
2. Why the hardest work isn't in scaling, it's in being honest with yourself
3. Real empathetic leadership: ask what they need, clear obstacles, hold them accountable

Want To Dive Deeper On These Topics?

1. Episode 39: The High-Performance Hiring Method Every Agency Owner Needs with Natasha Golinksky
2. Apply to join our exclusive Agency Darlings Slack Community: agencydarlings.com/community
3. Join our agency advice column: agencydarlings.myflodesk.com/signup

Connect with Steve Guberman:

1. Website: agencyoutsight.com
2. LinkedIn: linkedin.com/in/agencycoach
3. Instagram: instagram.com/mrgube

Connect with Melissa & Meredith:

1. Waverly Ave: waverlyave.com
2. Instagram: instagram.com/waverlyave.co
3. Le Chéile: lecheile.co/contact
4. Instagram: instagram.com/lecheile.co