Working Without Pants - Creative Entrepreneurship

In this episode of the Working Without Pants Podcast, I have Jon Schumacher of Hangouts that Convert.

Jon spent several years working at a full time job while consistently hustling on the side trying to get his own business started. Over the past year, Jon has seen success with Hangouts that Convert and has now been able to quit his job and dive into being an entrepreneur full time.

In this episode, he shares his journey and the lessons he learned along the way. 

Direct download: WWP_Jon_Schumacher.mp3
Category:general -- posted at: 2:52pm EDT

In this episode, I am honored to have Brent Weaver of on the show.

At uGurus, Brent and his team have intensive bootcamps where they challenge and help web professionals reach a point where they can sell projects at price points of $10k or more. 

In this episode Brent dives into what it takes to sell those large projects as well as how he has built his business and where he is wanting to take it.


Direct download: WWP_Brent_Weaver.mp3
Category:general -- posted at: 7:16pm EDT

In this episode I am honored to have Tucker Max on the show. Tucker Max is a best selling author with one of the most unique and authentic voices out there. 

After launching several best selling books, Tucker has now created a new service called Book in a Box. The business is new but already on track to generate over $1M in revenue in it's first year. 

In this episode Tucker talks about:

  • How Book in a Box came to be
  • Why he has such a unique and raw voice in his writing style
  • How he sees the future of book publishing changing

- See more at:

Direct download: WWP_Tucker_Max.mp3
Category:creative entrepreneurship -- posted at: 2:51pm EDT

Direct download: WWP_Phillip_Morgan.mp3
Category:creative entrepreneurship -- posted at: 1:02pm EDT

In this episode I have Nick Piscitello on the show who has built up Completion Web Studios which is a video agency that specializes in explainer videos.

Nick has not just built up a succesful agency, he has built up an agency that allows him to work remotely and travel the world. As you will hear in this episode, this company has enabled Nick to travel throughout the world and have some incredible experiences.

In this episode NIck shares how he got started and how he attracts clients. 

Direct download: WWP_Nick_P.mp3
Category:creative entrepreneurship -- posted at: 12:54pm EDT

Direct download: WWP_Jennifer_Schwartz_mixdown.mp3
Category:creative entrepreneurship -- posted at: 12:47pm EDT

If there were one word to sum up this interview it would be “Authenticity”.

In this episode I bring on Allie Lehman. Allie is a co-Founder of Death To the Stock Photo, partner in The Wonder Jam and author of the book Charge Up: Build a business and manage your energy with your introversion superpowers.

What is amazing about Allie isn’t just the accomplishments that she has made, but the intentionality and authenticity that has gone into sculpting a life of meaningful work. 

This is one of those interviews that will shake up your mind and make you think twice about the work that you are doing.

Direct download: WWP_Allie_Lehman.mp3
Category:creative entrepreneurship -- posted at: 3:26pm EDT

Today I am honored to have an incredible guest on the show Keith Perhac

Keith runs a digital marketing agency called Delfi-Net, and best of all, he runs the agency while living in Japan! 

For the past 12 years Keith has been living in Japan while building up a business primarily with US based clients. 

In this episode, we dive into Keith’s journey, how he got started and built the agency to the point where it is today. 

There are lot of great insights in here on building up a successful business and living a non-traditional lifestyle.

Mentioned in this episode:

Direct download: WWP_Keith_Perhac.mp3
Category:creative entrepreneurship -- posted at: 1:47pm EDT

In this episode, Brennan shares how he built up a consulting career to justify charging those rates.Brennan also shares best practices for raising your rates and getting more clients. 

Brennan is an absolute authority and leader in the freelancing and consulting space and his advice in this episode is absolutely invaluable.

I would highly recommend picking up one of Brennan’s books Double Your Freelance Rate. I bought a copy over a year ago and since then my rate has tripled! 


Brennan also offers an incredible free email course where he shares absolutely incredible insights. Sign up for it and I know you will get a love of value out of the lessons!


Direct download: WWP_Brennan_Dunn.mp3
Category:creative entrepreneurship -- posted at: 4:59am EDT

On today’s episode of the Working Without Pants Podcast we have Ben Dolgoff. Ben is a serial entrepreneur who is currently living in Costa Rica.

Ben’s story is an inspiration to any entrepreneurial individuals. He has managed to start and sell multiple businesses all before the age of 30. Ben's latest venture Shopwin is one of the many businesses Ben has launched in the past several years. 

In this episode, Ben shares his philosophies on building businesses, travel, real estate, life and much more. This is an incredible and inspiring episode for entrepreneurs at any level. 

Direct download: WWP_Ben_Dolgoff_56k.mp3
Category:creative entrepreneurship -- posted at: 2:50am EDT

Sometimes we learn more from our failures than our successes. In this episode Marcus Blankenship takes us through his experience building up a successful agency and then experiencing it fail and fall apart. 

Marcus's lessons are invaluable to any creative individual, especially those building up an agency. Many of the mistakes that he points out are the exact same mistakes I made when building up my agency.

Marcus has now changed direction with his career and acts as a business advisor and coach to other agencies helping them on their path to building an agency that works. 

This is a must listen for any creative individual who is considering expanding beyond themselves and building a team. 

Direct download: WWP_Marcus_Blanken.mp3
Category:creative entrepreneurship -- posted at: 2:00pm EDT

This episode is jam packed with insights and wisdoms from one man's journey on building up a successful consulting career. 

Kai Davis has evolved his career time and time again over the past several years, each time growing to a better, higher value offering. On his journey he has learned some invaluable insights on how to build up a successful consulting career.

Currently Kai's core offering is focused around blogging and podcast outreach as a productized service and he is doing phenomenal with it.

Give this episode a listen as it is jam packed with useful information!


Direct download: WWP_Kai_Davis.mp3
Category:creative entrepreneurship -- posted at: 4:52pm EDT

Brian Honigman is a marketing consultant and writer. After leaving his job at Ecko a few years back, Brian went out on his own as a freelance marketing consultant.

In this episode he shares his story of how he got started, landed his first clients, and built his business up to the point where it is today.

Brian is also a master of PR, guest blogging and content syndication. In this episode we talk in detail about how he has landed writing opportunities at Inc, Forbes, Entrepreneur, Huffington Post, The Next Web and much more.

Direct download: WWP_Brian_Honigman.mp3
Category:creative entrepreneurship -- posted at: 2:22pm EDT

I came across Devon recently based on a blog he wrote How to explain the paid discovery process to your web design prospects

The article intreigued me because I had often hit these situations with large projects where the scope was just unclear. I had heard about charging for the discovery process before, but hadn't tried it out too much.

After reading Devon's article, I charged for my first discovery process and it was an great outcome for both the client and myself.

In this article, we dive more into discussion around charging for the paid discovery as well as a bit of background on Devon and how he built up his agency Enginate.

There is a lot of value in this episode so I know you are going to get a lot of out it!

Direct download: WWP_Devon_64kb.mp3
Category:creative entrepreneurship -- posted at: 4:24pm EDT

Nathan Powell has been working in the design industry for quite some time. In this episode he shares with us his early starts of handing out flyers for design work at a local pub, all the way to building up a flourishing career. 

He then talks about his current transition from a full time designer to buildling and working on his new proposal software product Nusii

I highly recommend Nusii

Seriously, within 5 minutes of trying the Nusii demo I was signed up as a paid customer. 

It literally fixed a problem I didn't know that I had. For years I have been creating custom proposal designs in InDesign. This would take me at least 30-60 minutes to design every proposal even though the template was already created.

Nusii fixed that problem and turned a 60 minute job into a 5 minute job. 

You just paste your proposal text into a Nusii template and it automatically fills it all out for you and generates a PDF or a web link where your customers can view your proposals.

It's awesome and I freaking love it! 

Nusii Discount code

Use this link and the discount code jakejorgovan and you will get 50% off your subscription for the first 3 months!

I'm not getting any kickbacks for this product, I seriously just love it and know you will too!

Direct download: WWP_Nathan_Powell.mp3
Category:creative entrepreneurship -- posted at: 3:19pm EDT

In this episode I interview Chris & Bryant of Authentic Form and Function on what they have learned from building a remote creative agency. 

They have great insights in this episode on starting an agency, attracting clients and handling a remote work culture.

Visit our website at

Direct download: WWP_Authentic_FF.mp3
Category:creative entrepreneurship -- posted at: 1:41pm EDT

"The Creative Freelancer Show" is now called "Working without pants"

In this episode I dive deep into my story and explain how I started my creative career, got my first clients and how my business has evolved. 

This episode is based on requests from several listeners who wanted to hear me tell a bit more about my career and my story.

Visit the shows website at

Direct download: WWP_My_Story.mp3
Category:creative entrepreneurship -- posted at: 1:02pm EDT

We are lead to believe that the price of creativity is driven by quality. 

We believe that the best work deserves the highest price.

Unfortunately, that isn't true. 

In this episode, I discuss the true drive of the price of creativity.

Direct download: The_Price_of_Creativity.mp3
Category:Creative Freelance -- posted at: 3:21am EDT

This is the final episode in this series on my book The Creative's Guide to Freelancing.

In this episode I cover working remotely. I talk about why you want to do it, the benefits that it can bring to your life and the different ways to approach it. 

Then I explain the one thing that is absolutely necessary for you to build a remote income.

Direct download: CGTF_6_-_Working_Remotely.mp3
Category:Creative Freelance -- posted at: 2:21pm EDT

This is another episode in the series on my book The Creative's Guide to Freelancing

For the most part, creative's seem to hate sales. They feel sleazy about it, or don't enjoy the process. But it doesn't have to be that way.

In this episode I cover sales strategy and a different approach on how to think about sales. You can turn sales from something you hate into something you truly enjoy.

Direct download: CGTF_5_-_Sales_Strategy.mp3
Category:Creative Freelance -- posted at: 2:17pm EDT

This marks episode four in this series about my upcoming book The Creative's Guide to Freelancing. For those who haven't been listening already, I am going through my book chapter by chapter and pulling out some of the key concepts and ideas from each chapter.

This episode is specifically about pricing. Now many of you may have listened to my previous episode Unconventional Pricing for Creatives. If you haven't I actually recommend that episode as a precursor to this episode.

In this episode, I dive into some of the concepts from my unconventional pricing episode in even more detail.

And inside my upcoming book there is even more details on pricing, proposals and much more.

Direct download: CGTF_4_-_Pricing_and_Proposals.mp3
Category:Creative Freelance -- posted at: 1:23pm EDT

Here is another episode in the series for my upcoming book The Creative's Guide to Freelancing

This episode is all about marketing. It's about building demand, how to handle marketing properly and set yourself up so that you have a steady flow of work. 

Direct download: CGTF_3.mp3
Category:Creative Freelance -- posted at: 1:19pm EDT

In this second episode of the series on my upcoming book The Creative's Guide to Freelancing, I cover positioning. 

In this episode I talk about:

  • Niching, if it's right for you and the proper way to approach it
  • How to describe yourself and talk about what you do in person and on your website


Direct download: CGTF_2.mp3
Category:Creative Freelance -- posted at: 1:57am EDT

Hey Creatives, this episode marks the start of a series of episodes that I will be releasing in preparation of my upcoming book The Creative's Guide to Freelancing

I am going to be going through the book, chapter by chapter, and explaining key concepts from each chapter. 

In this episode, I cover:

  • Why I personally got into freelancing
  • Why freelancing isn't as risky as you think
  • How to get started and get your first clients
Direct download: CGTF_1.mp3
Category:Creative Freelance -- posted at: 9:04am EDT

Drew Binkley runs Grand Palace Silkscreen and is partner in Monkey Ink Design with Alicia Waters who was interviewed in episode 6. 

In this weeks episode, I interview Drew about the absolute incredible quality of his work, and how he has elevated the quality of his output over the past few years.

Drew also talks about:

  • How to make a relationship work when you are married to another designer
  • How to balance running a print shop and a design business
  • How he built up the reputation to work with artists such as Dave Matthews Band and Ray Lamontagne

Mentioned in this episode:

Direct download: CFS_Drew_Binkley.mp3
Category:Creative Freelance -- posted at: 10:33am EDT

This week I have an incredible guest Kaleigh Moore from Kaleigh has just recently made the jump to freelancing full time over the past couple years. 

In this episode, Kaleigh talks about:

  • Her journey leaving her full time job to working on her own as a freelancer
  • How she built up a client base for her business before ever quitting her job
  • How she makes a living as a social media consultant and copywriter

Mentioned in this episode:

Visit our website at

Direct download: CFS_We_Are_Lumen.mp3
Category:Creative Freelance -- posted at: 1:45am EDT

Today I am honored to have Bryce Bladon, the Editor-in-Chief of

But don't worry, we don't just complain about bad clients on this episode. Instead we dive in to talking about Bryce's freelance writing career, how he got started and how he built a career that has let him move all over the world. 

This episode is jam packed with valuable information that will help any aspiring copywriter or creative professional.

Mentioned in this episode:

Direct download: CFS_Bryce_Bladon.mp3
Category:Creative Freelance -- posted at: 12:49pm EDT

Platforms like eLance and oDesk can get a bad reputation. I personally have fought this reputation for a while given that I personally kickstarted my freelance career with oDesk. 

While I hit what I thought was ceiling with these platforms, I was proven wrong by Danny Margulies.

Danny has earned over $100k in the past year on eLance as a freelance writer.

Yes, you read correct. $100k in a year as a writer. 

Danny defies all of the myths and expectations that exist around these freelance platforms and makes an incredible income charging an average rate of $125-135 per hour. 

In this episode, Danny shares how he reached the level he did and what others can do to supplement their income or launch their careers with eLance.

Mentioned in this episode:

Check out Danny's website and sign up for his eLance hacks at

Direct download: CFS_Danny_M.mp3
Category:Creative Freelance -- posted at: 10:48pm EDT

Software applications are all the rage these days, but the truth is there is a much easier and quicker route to building a scaleable business.

That route is called productized services and in this episode of The Creative Freelancer Show, Brian Casel of Restaurant Engine and creator of the course Productize shares with us his expertise on building a productized service. 

This episode was extremely valuable and had me thinking in ways that I can products some of my own services. 

Direct download: CFS_Brian_Casel.mp3
Category:Creative Freelance -- posted at: 12:01am EDT

This is one of my favorite episodes to date. 

Paul Jarvis is an absolutely incredible writer and web designer. His weekly newsletter has inspired me for quite sometime and I am honored to have him on the show.

Talking to Paul in this episode revealed some insights that have dramatically changed how I look at my business, I know hearing this interview will do the same for you as well.

Direct download: CFS_Paul_Jarvis.mp3
Category:Creative Freelance -- posted at: 8:05pm EDT