Why Delegating Isn't Working

Why Delegating Isn't Working

Author: Millo October 14, 2025 Duration: 20:10
As your freelance business grows, you hit an inevitable ceiling: there's only so much you can do yourself. But delegating effectively is harder than it sounds. How do you train team members to run with tasks independently without constant check-ins? How do you avoid becoming a bottleneck that slows everyone down? And how do you set boundaries without seeming hostile or unavailable? In this episode, Preston and Clay answer listener Peter's question about delegation, drawing on Clay's experience managing a 20+ person team generating over a million in recurring revenue. They share practical strategies for creating SOPs, setting communication boundaries, and hiring people who can actually think for themselves—so you can focus on growing your business instead of micromanaging every detail. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Check out Clay's business → ⁠⁠https://golinus.com Learn more about your ad choices. Visit megaphone.fm/adchoices

There’s a common gap between working for yourself and truly building something that lasts, and Freelance to Founder lives in that space. This isn’t just theory; it’s a daily conversation for freelancers who are tired of the unpredictable income and ready to create a real business. Host Preston Lee draws from his own journey from freelancer to someone who has built and sold companies, and he brings that grounded perspective to every episode. Nearly every weekday, Preston is joined by other founders and entrepreneurs who’ve navigated the same path, breaking down the practical steps you can take to scale your solo operation. The call-in format means you’re hearing real questions from people in the trenches, facing the same client issues, pricing dilemmas, and growth plateaus you might be. Listening to this podcast feels like having a direct line to a supportive and experienced mastermind group, one that focuses on actionable strategies over vague inspiration. It’s for the designer, writer, developer, or consultant who’s ready to move beyond the feast-or-famine cycle and lay the foundation for something more substantial and sustainable. The discussions are candid, the advice is tested, and the goal is always clear: helping you transition from a solo practitioner to the founder of a thriving business.
Author: Language: English Episodes: 100

Freelance to Founder
Podcast Episodes
Do Lead Magnets Work? [not-audio_url] [/not-audio_url]

Duration: 50:17
On today’s show: Do lead magnets really work? Like, can you actually get new clients by giving away something for free first? Or are they a waste of your time? I’m flying solo today on a coaching call with Garrett—who ha…
[Q&A] Cost of Starting an Agency? [not-audio_url] [/not-audio_url]

Duration: 21:34
On today’s Q&A episode — let’s talk money. Exactly how much should you save up before you can start your own agency? We do our best to answer this question, plus it got us asking: what in the world are we spending all of…
You're Dead Without a Vision [not-audio_url] [/not-audio_url]

Duration: 52:23
On today’s show: you’re dead without a vision for your business. That’s because without a vision—or a north star—to guide your business, you can very easily end up chasing the wrong things. In today’s episode, we chat wi…
[Q&A] How Do I Get US Clients? [not-audio_url] [/not-audio_url]

Duration: 16:16
On today’s Q&A episode, Travis writes in with a problem: a few years ago, he moved from Australia to the U.S. to grow his video business. And while things went well at first, work has really slowed down, and he’s wonderi…
Client Tool Craziness [not-audio_url] [/not-audio_url]

Duration: 49:24
On today’s show: should you spread yourself across each of your client’s project management tools? Or should you make them join yours? It’s a question Taylor’s facing as she grows her business. We spoke with Taylor about…
[Q&A] Is GoHighLevel Worth the Hype? [not-audio_url] [/not-audio_url]

Duration: 56:59
On today’s show, we’ve got the longest Q&A episode we’ve ever published—coming in at a whopping 50 minutes plus. Why so long? Well, I asked Clay a question that really got him riled up. It has to do with his experience u…
Where Is Your Business Going? [not-audio_url] [/not-audio_url]

Duration: 50:53
Have you ever felt like you don’t know where you’re going in your business? It can be debilitating and frustrating. Not only that, but it can leave you spinning your wheels and wishing you knew what to do next to finally…
[Q&A] Upcharge a Client for Subcontracting? [not-audio_url] [/not-audio_url]

Duration: 14:52
On today’s show: if you work with a sub-contractor, something we highly recommend—how much extra should you charge your client? And do they have to sign two different contracts? That’s what Kiki asks us in this Q&A episo…
Profit-Sharing with Agencies [not-audio_url] [/not-audio_url]

Duration: 1:00:58
In today’s episode, we learned that working with agencies is a great way to fill your client pipeline regularly. But how does the money work if an agency will “white label” your services? Who gets what? How much? And whe…
[Q&A] Lost Your Passion? [not-audio_url] [/not-audio_url]

Duration: 13:52
In today's Q&A, Rachel Stoneking, from our free Facebook Mastermind Group asked how she could get the passion for her business back. She shares her personal feelings of anxiety and disappointment after losing clients wit…