Zach Swinehart

DYF Co-Owner & CEO

Freelancing Specialties:

Lifestyle design & time optimization. Conversion-oriented design. Email marketing automation. Content creation, lead magnets, etc. Transitioning from working a day job to freelancing. Freelancing as a highly-leveraged soloist. Running a small agency.

About Zach

Hi, I'm Zach.

I've been running my freelance web design + dev business for 14 years, and I've been fortunate enough to get to work with many clients at the top of their fields.

Over the course of my time freelancing, my rates and client quality have increased enough that I can now travel the world and freelance only part time, while still saving, investing, and feeding my cat spendy-ass raw food.

I spent the first 5 years of my freelancing career struggling and pretty much always broke. In hindsight, I could have avoided a lot of that if only I'd had a solid path to follow. It's my mission to help give you that path so that you can avoid the pitfalls I ran into.

My true passion is teaching people how to leverage freelancing to create more freedom and optionality in their lives — when done right, freelancing can provide a solid financial base with a minimal time requirement, freeing you up to spend your time on the stuff you're really interested in. I want to help you get there.

At DYF, I've had the privilege of getting to interview a bunch of freelancers who are kicking ass in their individual businesses, and I love getting to parse that knowledge out into repeatable frameworks that you can incorporate immediately into your own business.

My Back Story

A rough timeline of important milestones on my freelancing journey...


Wrote my first HTML code

  • It was for my store. 😂

Built my very first website

  • It was for my high school heavy metal band — I built it in Microsoft FrontPage, lol.

Did my first website for a client

  • I believe I charged $150 for it. 😬😬😬 

Started my website business

  • I didn't even want to be a coder or do WP at first. I just wanted to make more $ from my college dorm than I could make from answering questions on ChaCha.

Dropped out of university to run my business full-time

  • I had no idea what I was doing. I still to this day curse Past Zach for naming his business "Websites for Less."

StrugglingAF as an agency

  • I did all the stuff they say you're "supposed" to. I got an office. Employees. Even bought a house. But I was overworked, had terrible clients, and was always super broke. Also racked up $20k in debt to the IRS that I couldn't afford to pay. Fun!

StrugglingAF as a solo freelancer

  • When my primary employee left with 1 week's notice and my personal workload doubled, I ended up having a mental breakdown and decided to scale down the agency, staff, etc. and just go freelance. I still had crappy clients and was broke and burnt out. Also got to experience lots of overdraft fees and a growing stack of increasingly-urgent IRS letters about that $20k they wanted.

Got a dev job

  • After being burnt out and hating my work life for long enough, I eventually decided to get a job. Turns out it was the best decision I ever made for my business.

Building a solid business as a side hustle

  • With the job covering my bills, suddenly I wasn't constantly spinning my wheels chasing the next crappy client, and could build a better business with higher quality clients.

Escape velocity + quit my job

  • I did some work for a then-fledgling internet marketer friend of mine, Rick Mulready, who was in a mastermind with me. He sent me some great referrals, one of whom was Entrepreneur on Fire. This was my lucky break, and things started snowballing. I quit my job in July, almost exactly 2 years after I got it.

Small contractor-based agency + more mental breakdowns + becoming a digital nomad

  • I was making more money than I'd ever made, and had reached all my financial goals. But I was still unhappy and had low self-worth. A new mental breakdown and journey of self-discovery ensued. I left the USA in July 2015 to travel the world.

Running my agency from abroad + spending too much $ traveling + eventual disillusionment with digital nomad life

  • All that money I made in 2015? I spent most of it traveling. Because here's the thing about going to a new country every few days or weeks or whatever: it's not cheap! And it struck me that my "journey of self discovery" had mostly become a frivolous distraction. Was I some special Elizabeth Gilbert snowflake on his own "Eat, Pray, Love" quest, or was I just some asshole with a gigantic carbon footprint from all these flights I was taking?

Scaling back to solo freelance

  • I decided that the extra time, money, and stress of managing a team and having to oversee all their work wasn't worth it. It struck me that I could keep running a small team and need to take on several projects a month to pay the bills and earn what I wanted... *orrrr* I could just work alone and only need one project per month to earn the same amount.

Freelancing part time + trying to find my passion + growing SaaS products as a technical co-founder

  • At this point I had been freelancing for quite a while and was kinda bored. I thought perhaps I should try to "find my passion." I explored a lot of different projects and tried to start several SaaS companies. I invested hundreds of hours building various SaaS products that never went anywhere. It struck me what what I really needed to do next was not rely on business partners to market things, and instead to learn how to build my own audience.
Early 2022

Appreciating what I have + disillusionment with the concept of finding your passion + committing to what I know

  • I have ADHD, and also learned I am an enneagram type 7. With these in mind, it struck me that perhaps there's no *one* passion out there for me, and that for me, passion maybe just = novelty. (Which is tricky, because nothing's new and exciting forever!) A friend recommended reading So Good They Can't Ignore You and it was exactly what I needed to hear. I decided that instead of trying to "find my passion" I could instead appreciate all the great things freelancing has done for me and distill my experience to help others create lives of freedom and financial comfort.
Late 2022

Freelancing ~5-10 hrs/week; spending the rest of my time on my own projects. First chats with Brennan & Laura about coming on board to run DYF

  • I signed on with a client of mine to run all of their marketing and product launches on an ongoing basis, and have stopped taking on new client website projects. (I still support past clients when they need updates, etc.) I now have the time freedom to be able to spend mornings working on client work, and the rest of the day however I like. Be it exploring my new expat home city of Tallinn, Estonia, doing music production for ZSwine, or creating cool stuff for Double Your Freelancing.
Early 2023

Getting the "DYF engine running again," improving & modernizing our content and courses

July 2023

Started my "agency from scratch" project, where I put our flagship marketing course, The Blueprint, into practice in my own fresh agency (Conversion Wizard 🧙‍♂️). Prior to this I'd just coasted on word of mouth, but I knew I needed to level up my marketing skills to support our students better.


Running DYF alongside the Conversion Wizard agency, which I'm using as the "marketing testing ground" for DYF marketing concepts, which I'll report on to augment The Blueprint.

Working on getting better at delegating in both businesses because it's a bit too much to manage running the two of them at once!