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The Double Your Freelancing Podcast


This podcast is dedicated to helping you master the business of freelancing.

Each week, we’ll dive into topics ranging from getting your first few clients to starting your own agency. Our focus is on helping you get better clients, make more money, and live a happier life freelancing.

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Here is what one loyal listener had to say about the Double Your Freelancing podcast:

Brennan is a champ. He always has actionable items to follow and his advice is spot on. With his help I’ve already snagged a new project at a rate 3X my original rate. I like his guests and they add more depth to the show.

Hopefully the fact that your show of support will keep the podcast going is reward enough for you. But we want to sweeten the deal for you even further:

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Episode 63

Today I’m talking with Joanna Wiebe, the founder of CopyHackers.com. CopyHackers is an online resource for everything you need to know about copywriting, including many informative case studies. Her new project, Airstory, is a fantastic content production tool for high-performance writing teams. Joanna taught me how to write effective sales copy and on today’s episode we discuss her Rule of One: how you can make sure…

Episode 62

My guest today is Meryl Johnston, founder of the international accounting agency Bean Ninjas. She has a background in accounting and began her first business as a consultant. She has grown her current business from the ground up and is now generating over $100,000 in recurring revenue through monthly productized bookkeeping services. We discuss her career, how she transitioned to a productized service business and…

Episode 61

Today I’m talking with Barry O’Kane on niching down and creating a location independent business. He’s a Double Your Freelancing Academy student who has been working with Philip Morgan for the past few months while living in Edinburgh, Scotland and running his online business: Happy Porch. Barry has over 15 years experience in the web development industry and became location independent four years ago.

Episode 60

My guest today is Todd Tresidder, a former hedge fund manager and founder of FinancialMentor.com. He is a personal finance and investing expert coach who teaches how to grow wealth and reach financial independence. He emphasizes the importance of personal development and fulfillment in attaining the goal of financial freedom.

Episode 59

Today I’m talking with Michael Port, author of Book Yourself Solid and four other bestselling books. I came across Book Yourself Solid at a bookstore when I first started freelancing, and loved the online marketing techniques he describes. He has been running Book Yourself Solid programs around the world and training freelancers for the past 14 years.

Episode 58

Today my guest is Jonathan Raymond the former CEO of E-Myth, he became the CEO in 2011 when the owner wanted to modernize the brand. He decided to break out on his own in 2015. The idea behind the E-Myth is that running a business is different than being great at whatever the business does. An example would be a great dancer who opens a…

Episode 57

I’m super excited to share today’s interview with Ryan Waggoner with you. Ryan has an amazing consulting business and is pushing more than a million a year in profit. Ryan is killing it with mobile consulting, where a lot of people in that space struggle to make $100,000 plus. Ryan is an all around sharp guy, but I’m specifically bringing him on because he is…

Episode 56

Hello everyone, today I am talking with Diana Huff, the President of Huff Industrial Marketing a business that helps industrial manufacturers grow and succeed. Diana just released her new book Cash Flow for Freelancers. Today we will be talking about how to manage cash flow when you have a variable income.

Episode 55

Hey everybody, this is Brennan welcome to the brand-new Double Your Freelancing podcast. Everything is now under the Double Your Freelancing umbrella. This episode doesn’t have an interview. That is intentional, because I wanted to talk to you about the biggest and most exciting thing I have ever done business wise.

Episode 54

Today our guest is Reuven Lerner, who teaches Python, Ruby, Git and PostgreSQL to companies around the world. Today we are discussing using training as a productized offering. Reuven will also be giving an extended presentation on this topic at the Double Your Freelancing Conference that we are having June 22nd through June 25th in Stockholm, Sweden.

Episode 53

Hello everyone, today I am talking to Budi Voogt. He is an awesome guy from the Netherlands. He runs a recording label consultancy. I love looking beyond the typical web designer, copywriter, marketer kind of business and seeing how other types of entrepreneurs are successfully charging more, getting better clients,  and putting systems in place.

Episode 52

Today I have an awesome interview with a long time student of mine, Eric White. When Eric started he was a typical commoditized freelancer, but he made the transition to high-value business consulting. He has a background in developing business software. He enjoyed working with people and was the guy who spoke with clients to find out what they wanted in their software products.

Episode 51

Today I am talking with Bryce Bladon. He is the curator of “clients from hell”. Today we talk about everything from qualifying new clients to setting expectations. He runs a website whose sole purpose is to showcase crazy clients. We both feel that sometimes we can do things a bit differently to help avoid having clients from hell. So the theme of this show is…

Episode 50

Today I am interviewing Jane Portman. Jane is from Russia, and she used to work with me on Planscope which I just sold. She is an amazing designer who is very focused on the design and the copy. I recently redesigned Double Your Freelancing. Which is appropriate for today, because Jane’s expertise is building really great user experiences.

Episode 49

Today we are speaking with Alex Mathers. Alex is an illustrator who specializes in vector illustrations, maps, diagrams and landscapes. He is also a blogger and writer. He runs the Red Lemon Blog which helps creative entrepreneurs market and promote their businesses. He has worked for clients like Google, Sony and the BBC. He is also a speaker and does one on one coaching for…

Episode 48

Karl Sakas is the president of Sakas & Company which is a consulting company that specializes in helping digital marketing agencies grow. I had an opportunity to chat with Karl today, and I found myself nodding my head the entire time. The meat and potatoes of the interview focused on helping businesses grow in a holistic way not just focusing on the technical aspect of…

Episode 47

Today I am talking with Jesse Strauss. Jesse is a New York-based lawyer who owns a firm specializing in debt collection for freelancers. When it comes to things like small claims court and debt collection, freelancers are usually on their own. Jesse discovered that there were a lot of freelancers with payment disputes while he was working on wage and hour cases.

Episode 46

Today I’m talking with a good friend of mine, Keith Perhac. Keith is the founder of the digital marketing consulting agency DelfiNet and the online course software Summit Evergreen. He has managed to build a thriving consultancy agency while working remotely in Japan. Working remotely, can be an issue for many freelancers, but Keith says he is there when his clients wake up and there…

Episode 45

Today’s show features service scalability strategist, Mandi Ellefson. Mandi helps entrepreneurs develop a system to free up time and remove themselves from their business. In today’s interview we discuss scaling your business and things to consider before going down that route. Mandi has discovered that scaling is a common issue for freelancers, and she is passionate about helping them. While researching methodologies to scale her…

Episode 44

Today we’re joined by Bart Mroz: consultant, co-founder of SUMO Heavy, and long-time friend. Bart is an expert at experimenting new things in his business and using the discoveries to increasingly improve it and their strategy. Not only have they done this with billing models, but with trial periods, sales processes, and basically everything else. What he’s discovered is that experimentation is the only way of…

Episode 43

Today’s guest is Liston Witherill.  Today we got the opportunity to talk about getting into the heads of your clients. It’s important to understand your client’s mindset, the worldview of the people you work for and their values, problems and needs. It’s what separates you and allows you to position yourself as an expert consultant and reliably solve the problems of your clients. Liston’s company…

Episode 42

Today’s guest is Naveen Dittakavi.  We had a great conversation about how his business has evolved and how important it is to overcome the belief that just because you’ve read something you’re making an improvement. In actuality, you have to act on what you’ve learned to make a difference. Naveen started his software business company in 2003 out of his dorm room at Georgia Tech…

Episode 41

Taking the time to understand yourself, and manipulating your strengths to get your message out can sometimes be all it takes to push yourself over the edge, and into full-blown success. Today we’re focusing on how to have an authentic brand and establish your brand identity, so you can do just that.   Our guest today is Jeffrey Shaw. He’s a business coach, and he…

Episode 40

Today we’re having a crazy interview, but in the best way. We’ll be talking to Julia Kelly, she’s a caricature artist, and the first one we’ve had on the show. She also has a degree in Accounting, so she loves the numbers side of things. We go through how she and her team charge hundreds of dollars an hour for caricature art, and all the…

Episode 39

Today I have part two of my interview with the amazing Sean D’Souza. We needed to go deeper into the 7 bag framework that Sean’s developed that covers the 7 objectives that need to happen prior to a successful sale. In this interview, we dove deeper into all of this. I really wanted to get his perspectives on how to use the principles that were…

Episode 38

Today is the first episode of  a two-part edition with Sean D’Souza.  Sean’s book, The Brain Audit, had a big impact on me as well as countless others.  The Brain Audit is designed to give somebody the tools to understand what goes on in the brain of a customer and how to respond accordingly.  It includes the Seven Red Bags which is a sequential process…

Episode 37

The Double Your Freelancing Conference that took place last month In Norfolk brought a lot of great people together to share information and ideas.  In this episode, 5 of the speakers from the conference join me to discuss what value they got from the conference and their overall impressions. The Panel: Mojca Mars – owner of Super Spicy Media, social media consultant Brian Casel –…

Episode 36

My good friend Paul Jarvis is my guest on this episode of the Business of Freelancing Podcast. Paul began as a web designer and applied what he learned in his work to writing for creative freelancers looking to better run their businesses. Today we discuss building products, especially for those freelancers who may not have a huge audience and a solid idea for a product….

Episode 35

More and more freelancers have taken to becoming nomads who live and work a location- independent lifestyle.  My guest, Paul Kortman, is a nomad who travels with his wife and four children and runs a digital marketing consulting business from various locations. On this episode Paul offers some thoughts on this lifestyle and how to make your business work in a non-traditional setting.  Paul believes…

Episode 34

Welcome to the Business of Freelancing Podcast.  Today I am talking to Nick Disabato, a good friend who is the founder of Draft Revise. As well as the author of Cadence & Slang, a guide to interaction design. Draft Revise is a service that helps companies optimize their content. Nick and I are going to discuss the company he’s built, how he’s done it, and…

Episode 33

Our guest will be one of the speakers at our Norfolk, VA for the Double Your Freelancing Conference this September. Kai Davis is an expert in building up an audience from scratch; building up your authority and targeting the clients you want to work with. If you’re looking to build an audience on your own you will love this episode. In this episode, Kai explains the…

Episode 32

Welcome to the latest episode on Business of Freelancing. One of my favorite things to do on my show is bring in niche experts, the kind of experts who are amazing at building a freelancing business and who can teach you how to get better clients. On today’s episode, I uncover what clients are thinking when they start hiring freelancers. I find out why some…

Episode 31

Welcome to Episode 31 of The Business of Freelancing Podcast.  Today I’m very excited to bring on my good friend Mojca Mars.  Mojca will be a speaker at the Double Your Freelancing Conference in September, and I will be working with her personally in the near future as well. Mojca had a quick start to her current consulting agency, Super Spicy Media, by getting those…

Episode 30

Today’s guest on the Business of Freelancing Podcast is Trajan King. I wanted to talk with Trajan because he has a consulting business built with a focus on having processes and procedures in place.  As Trajan tells us, think about processes and standard operating procedures only if you want to be efficient and make money, if that’s not important to you, then don’t worry about…

Episode 29

This is the Business of Freelancing Podcast, Episode 29. Today we’ll discuss a number of thoughts related to hiring subcontractors.  My guest is coach, advisor, project manager and author Marcus Blankenship.  If you’ve ever found yourself in the position of needing to hire and manage others,  then this podcast will definitely resonate. I’m very close to launching my new daily question and answer podcast/YouTube show,…

Episode 28

Welcome to the Business of Freelancing Podcast. My guest today is Double Your Freelancing student Matt Olpinski. Before we jump into the interview, I want to share that in addition to this show I’m going to soon begin producing a daily question and answer podcast, called Freelance Answers.  This will be a great way to share the questions that a lot of you have and show…

Episode 27

Welcome to the latest episode of the Business of Freelancing Podcast.  My guest is Jeff Steinmann, author of the book  How to Quit Working  which can be found, along with other services he offers, on his website  howtoquitworking.com. First, a reminder to sign up for ticket information for my event, The Business of Freelancing Conference.  The show will be September 16-18 in Norfolk, VA. Sign…

Episode 26

Welcome to another episode of the Business of Freelancing Podcast.  First I’d like to recognize a few recent 5-star reviews for the show. Much thanks goes to: sporkitover, rickwolf, justin_mw, jeff at ecoommercewarriors, ourumov7, kellyIriye for their reviews in iTunes. Keep those reviews coming. It’s a great way for me to know that the show is resonating with you and bringing you the resources that…

Episode 25

Welcome to another episode of the Business of Freelancing Podcast. This week I am joined by my good friend Jonathan Stark.  Jonathan is a mobile strategy consultant, having worked with flagship brands such as CVS, Staples, Time, and Nokia. Today Jonathan also focuses on helping other freelancers get the most out of their businesses by promoting the same value based approach to their agencies that…

Episode 24

This week on the Business of Freelancing Podcast I am very pleased to welcome Ed Gandia to the show.  Ed is the “go-to” guy when it comes to high end freelance writing.  In a time where commoditized writing is far too frequent, Ed has mastered finding a niche for yourself and selecting only those clients who will receive immense value from your services. International Freelancers Academy is a…

Episode 23

Today I talk with my good friend Kurt Elster on how he has 8x his Revenue by Niching Down into a specialized market. Kurt has turned from a generalized web developer into a Shopify specialist, and in the process he has catapulted his business to a whole new level. To begin with, Kurt lays out a framework he follows that is necessary to specialize. He…

Episode 22

Today I sit down for a chat with Philip Morgan of Philip Morgan Consulting and My Content Sherpa to talk about positioning yourself appropriately as a freelancer in a market, and his new book, “The Positioning Manual for Technical Firms”. Philip is an expert on helping freelancers position themselves in a niche that is a good fit for their skills, goals, and ambitions. In this…

Episode 21

Have you ever wanted to get away from strictly selling your time for money? Is your long term plan to either escape consulting altogether (through something like bootstrapping your own products) or to remove yourself as a part of your “product”? Sooner or later, almost all of us get to this point. We want more control and creative input into the work we provide our clients. Productizing…

Episode 20

This week I sat down with Scott Yewell to talk about how he recently closed his first six-figure project. Scott’s a partner at Blackfin Media, who for the last 14 years has been building small ($1-10k) website projects. A few months ago, Scott joined my Consultancy Masterclass and made a lot of changes. He walked away with the class with a few pages of notes and a directive: change…

Episode 19

We all know how important communication is during the sales process, but for a lot of freelancers knowing how and when to followup is often a mystery. After you first meet someone, when should you first contact them? How long should you wait before you followup with someone you’ve sent an invoice to? When and how should you pester clients over past-due invoices? In this episode, I talked with…

Episode 18

A lot of freelancers — hell, just about every freelancer I’ve talked to — want to eventually create and sell their own products. But this is easier said than done. Usually something stands in the way: the immediacy of consulting revenue, lack of an idea, or the fear that they’ll build something and it’ll never sell.

Episode 17

I recently sat down (literally!) with my friend Steli Efti, the founder of Close.io. For about an hour we talked about how freelancers and consultants can create more referrals for their business. Steli is a master of sales — you won’t want to miss this episode! Mentioned this episode: Steli on Twitter Close.io The B2B Referral Sales System DoubleYourFreelancing.com

Episode 16

In this episode, I sat down with Matt Inglot of Tilted Pixel. He started the company over 8 years ago, and went from being a solo freelancer to opening up a brick & mortar office in Toronto. After building up a successful team and building out an office, he decided to go 100% remote. We discussed the pros and cons of having an office, along with why…

Episode 15

This week I’m joined by Dennis Field, who — like me — has struggled with burnout. Who am I kidding though? This affects ALL of us. Late nights, weekends, and being “on call” for your clients can cause you to regret ever starting your own freelancing business. Dennis’ website How to Fight Burnout as a Designer

Episode 14

This week I sat down with Jan Jones of Oozou, an agency based out of Bangkok, Thailand, and Jonathan Tarud of Koombea, another agency, this one in Colombia. We discussed what it’s like to run an agency when your clients are half a world away from you. Whether you’re in San Francisco, Topeka, or Saigon, you’re going to love this episode. Double Your Freelancing Rate Oozou…

Episode 13.5

This is the Freelancing Minute for Friday, February 14th (Valentine’s day!) 2014. When you’re creating a proposal, it’s important to contextualize our offer (what we’re building or doing) with the problem and the solution. In this short clip, I seek to define the differences between the problem, the offer, and the solution.

Episode 13

This week I had the opportunity to sit down and talk with Sherry Walling, a clinical psychologist and counselor and the wife of Rob Walling. Sherry gave a fantastic talk at MicroConf last year on ways that entrepreneurs can manage their own anxiety, and I wanted to bring her on to discuss how you can make sure that your life as a freelance consultants doesn’t end up…

Episode 12

This week my special guest was Rob Walling. He’s known for the following… Drip HitTail Startups for the Rest of Us Start Small, Stay Small Software by Rob MicroConf Micropreneur Academy DotNetInvoice Apprentice Lineman Jobs And I thought I did a lot! We chatted about how you can move — either partially or fully — from freelancing to making money from products.

Episode 11

In this episode, I talked with Marcus Blankenship of CREO Agency. If you don’t live in a tech hotbed like SF or NYC and you worry that your location will hinder your ability to recruit clients, you won’t want to miss this episode.

Episode 10

Today I talked with Nick Hance of Reenhanced about ways of setting yourself apart from your competition. If you’ve ever wondered how you, as say a Ruby developer, are any different than me (a Ruby developer) or thousands of other Ruby developers, you’ll want to listen to this discussion. I also opened the show by talking about my upcoming bootcamp with Patrick McKenzie (patio11) on how to create recurring…

Episode 9

I’ve recently been to quite a few “product” conferences (LessConf, MicroConf and soon BaconBizConf), and what I keep finding is that a LOT of freelancers are in attendance. It’s no secret that most freelancers want to one day build and sell a product or two of their own, but how? How do you figure out what to build and ultimately sell it to the right people? In this episode, I…

Episode 8

This is the first episode of 2013 for The Business of Freelancing Podcast, and inside I cover everything you need to know about dealing with those pesky clients who want to know “How much is it gonna cost me?” We explore how to qualify new leads, offer an initial consult, and how to make it known that we’re consultants — not just guns for hire. Here’s the…

Episode 7

Show Notes 00:23 – Obie Fernandez Introduction Author of The Rails Way and The Rails 3 Way Hashrocket Prominent figure in the Ruby/Agile communities Professional software developer since 1995 Started a user group in Atlanta for Extreme Programming ThoughtWorks 04:11 – Importance of building a reputation and personal brand Controversial blogging Resistance against Java and then Rails 07:03 – Building a brand Client demand for Ruby on Rails experience vs custom…

Episode 6

Show Notes 00:50 – Sales Pipeline Moving people through a series of steps to get them to be a paying customer Acquisition to qualification to scoping to clients 04:11 – Content marketing to project delivery 08:02 – Tracking leads Highrise Fat Free CRM PipelineDeals Pipedrive Whiteboard Spreadsheet 12:29 – Networking Referrals Are they a good fit? Do timelines overlap? 14:36 – Qualification Why should this project exist? Do you have…

Episode 5

Show Notes 00:10 – Content Marketing Making information available for personal gain/recognition Duct Tape Marketing: John Jantsch Getting to know you 03:51 – Getting content in front of people Blogging Screencasting Publishing eBooks/PDFs Podcasting 05:24 – Promoting and building an audience Write with the intention of appealing to a specific audience Collect email addresses Infographics 07:38 – Appealing to potential clients and peer developers Be business-focused Hold impromptu marketing…

Episode 4

Show Notes 00:19 – Nathan Barry (twitter blog) Freelance Designer OneVoice App Commit App The App Design Handbook 01:14 – Show topic goals Building a passive income stream outside a freelancing business Balancing client work while developing products How product offerings affected his freelancing business Building products while freelancing 01:53 – Nathan’s professional career background 03:35 – Products to supplement a freelancing income 05:06 – OneVoice 06:59…

Episode 3

Show Notes Fall in Virginia Writing fiction Pricing freelancing services Double Your Freelancing Rate Reverse engineering your former salary Value based pricing, value delivered to clients Origins of your price How to decide on a price Cost plus – Cost of materials, cost of equipment, labor cost, and profit. Commodity pricing Lack of major expenses for freelancers when using a cost plus model Cost of…

Episode 2

Show Notes Ways we have marketed our consulting services in our past. Blogging, forum posting, content marketing, and social networks. Technical blogging, business blogging, random thoughts blogging. Investing into marketing activities Products can drive consulting sales Marketing sales funnel Ask “how did you hear about me?” Difficult to track every single person from marketing source to sale Easier to track in teh aggerate based on…

Episode 1

Show Notes Double Your Freelancing Rate Planscope Little Stream Software Eric’s 3 ebooks: Refactoring Redmine, Redmine Tips, Authoring Ebooks Listening to podcasts as a focused way to get content Distraction free time Bettering your business Actionable information to apply to your business today Translate ideas from people and books into actionable tasks Future show ideas Marketing ROI, how to track the return of a marketing activity. Pricing Methods,…

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