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
Disrespectful Clients [not-audio_url] [/not-audio_url]

Duration: 57:08
On today’s show: What should you do when you’re not getting the kind of respect you deserve from your clients? That’s just one of many questions we got today from our guest, Cathal, calling in from Germany. A few times n…
[Q&A] Best Tools as I Grow? [not-audio_url] [/not-audio_url]

Duration: 16:45
On today’s Q&A episode, what are the best tools to use as your freelance business grows? That’s what Cesar asks us because his business is outgrowing tools like Google Drive. So, Clay and I launch into our best advice on…
The Risk of Referrals [not-audio_url] [/not-audio_url]

Duration: 57:23
On today’s show, if you get most of your clients from referrals, is that a good thing? Or is your business at risk of failing? You’re about to hear a coaching call with Dwaynia, who’s calling in from Alabama in the USA.…
[Q&A] Charge by Hour or Project? [not-audio_url] [/not-audio_url]

Duration: 19:35
On today’s Q&A episode, if a client is willing to pay by the hour or by the project, which one should you choose? That’s part of Pennygoo’s question, and our answer might surprise you… Here we go! This episode was origin…
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] Client-Converting Portfolio Tips [not-audio_url] [/not-audio_url]

Duration: 18:22
In this Q&A episode, Oliver asks us what it takes to create a portfolio that actually brings in new long-term clients. And since Clay and I are real marketing geeks, we have quite a few ideas for turning your sleepy port…
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] Should I hire a CPA or use a tax software? [not-audio_url] [/not-audio_url]

Duration: 14:07
Today’s question comes from our free Mastermind group on Facebook. Anna Keith asks: "I’m getting ready to do my taxes and am considering trying software rather than hiring a CPA. What insights or pros/cons about using so…
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] Can I Put In-House Work in My Portfolio? [not-audio_url] [/not-audio_url]

Duration: 11:21
This episode's question came in via email. Nico works as a designer for a company right now, and he wants to start freelancing on the side and build a business. He said, “I was thinking of creating a portfolio, including…