Working Without Pants - Creative Entrepreneurship

Ilise has been on the show before, and I had the opportunity to catch up with her at the HOW Design Live conference to see what she is up to these days.

Ilise runs Marketing Mentor, a company focused on helping creative clients get better clients with bigger budgets.

In this episode with Ilise, we dive into her story, how she got started, some of the biggest mistakes she’s seen creatives make, and some of the best growth tactics she’s seen as well.

Ilise shares a ton of great insights in this episode, and I absolutely love having her on.

For full show notes go to ...
This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Ilise_Benum.mp3
Category:For Agency Owners and Consultants -- posted at: 1:46pm EST

I recently attended the HOW Design Live Conference and had the opportunity to meet up with Lea and Emily from Bright Umbrella. Bright Umbrella is a 2-person design and development agency that focuses on the education sector.
In our interview, I got to talk to Lea and Emily about how they started out, what they have learned, and some of the things they are doing to grow their business today.

For full show notes go to ...
This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Bright_Umbrella_mixdown.mp3
Category:For Agency Owners and Consultants -- posted at: 4:22pm EST

My guest on this week’s podcast, Gene Hammett, is an expert at growing business through speaking. He is also host of the Leaders in the Trenches podcast, which is focused on building authority through speaking engagements.
I had a great time talking with Gene. He has tons of knowledge and ideas to help you avoid the typical marketing “funnel frenzy” as he calls it. I learned a lot from this episode, and I hope you get a lot out of it as well.

For full show notes go to ...
This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Gene_Hammett.mp3
Category:For Agency Owners and Consultants -- posted at: 1:23pm EST

Over the past few years, I’ve found that about 60% of new business I get comes from my podcast in one way or another. This inspired me to write a blog post on growing your agency through podcast networking.

In addition, it also inspired me to reach out to Craig Hewitt of Podcast Motor to talk on the show about the service he offers and about how to be a successful podcaster.

Podcast Motor currently runs 30 different podcasts, so Craig has a ton of insight on creating an amazing podcast.

I hope you enjoy this episode and take some of Craig’s advice back to your own podcast. Or, I hope this episode helps you in starting a new podcast for your business.

For full show notes go to ...
This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Craig_Hewitt.mp3
Category:For Agency Owners and Consultants -- posted at: 11:40am EST

On the show this week, I had the pleasure of talking with Olivier Lambert of TactikMedia. Olivier is one of a rare breed who actually enjoys cold calling.

In this interview with him, he talks about how he approaches cold calling and how beneficial it has been for winning new clients for TactikMedia.

I had a great time talking to Olivier. He is an awesome guy with a great story. I hope you get a ton of value out of this interview and find ways to utilize cold calling in your agency.

For full show notes go to ...
This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Olivier_Lambert.mp3
Category:For Agency Owners and Consultants -- posted at: 12:45pm EST

On the podcast this week, I had Drew McLellan of the Agency Management Institute.

If you are an agency, and you haven’t heard of the Agency Management Institute, you should definitely check them out. They come alongside small to mid-sized agencies to help them run their businesses better.

Drew has been an agency owner for over 20 years now, and has a lot of experience with what makes agencies work well. In this episode, we talk about getting new clients and keeping current clients happy.

I hope you enjoy this interview as much as I do and that you can walk away with some ideas of how to keep your sales pipeline steady.

For full show notes go to ...
This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Drew_McClellan.mp3
Category:For Agency Owners and Consultants -- posted at: 1:29pm EST

On this episode of the Working Without Pants Podcast, I had the pleasure of talking with Michael Gass. Michael runs the Fuel Lines Business Development blog, which is one of the top 100 marketing blogs according to Ad Age.

In this episode, Michael goes in depth on a lot of the tactics he uses when helping companies with their inbound marketing strategies.

A ton of companies have a hard time seeing the results of inbound, or the results take forever. Michael shows us some ways that inbound can be creating impact in about 30 days.

For full show notes go to ...
This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Michael_Glass.mp3
Category:For Agency Owners and Consultants -- posted at: 11:30am EST

On this episode of the Working Without Podcast, I had the great pleasure of talking with Matt Inglot. Matt is the founder of Tilted Pixel, and he also runs the Freelance Transformation podcast.

I loved sitting down to talk with Matt about his story of how he ended up where he is today. It is a story much like my own, and it is great to hear about all he has learned from the mistakes made along the journey.

There is a lot you can take away from this week’s episode on things to do and not do when starting an agency.

For full show notes go to ...

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Matt_Inglot.mp3
Category:For Agency Owners and Consultants -- posted at: 11:57pm EST

On this episode of Working Without Pants, I had the pleasure of interviewing the former President of Crew, Michael Sacca. When Michael came to Crew, he was the head of partnerships, and we get to talk a lot about how he worked on creating valuable partnerships in that role.

We also get an in-depth look at some of his outbound campaigns and how he crafted these to best reach his audience.

This was a fun interview with a ton of insight, and I hope you enjoy it as much as I did.

For full show notes go to ...

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Michale_Sacca_Crew.mp3
Category:For Agency Owners and Consultants -- posted at: 12:24pm EST

Pia Silva and her partner are the owners of Worstofall Design, an agency that builds badass brands without the bullshit.

Pia's model is extremely unique. Instead of being a traditional branding agency, her and her partner work in a unique way. They do 1-2 day intensive branding sessions with their clients called "BrandUps" where they build the client’s entire brand and strategy right there in person.

They charge $10k per Brandup and regularly schedule 3 of these per month. That means in roughly 6 working days per month, Pia and her partner generate $30k in revenue!

In this interview, we dive into how Pia created this model, and how others can use elements of this in their own business.

For full show notes go to ...

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Pia_Silva1.mp3
Category:For Agency Owners and Consultants -- posted at: 3:45pm EST

I’m a huge proponent of using podcasts to grow your business, but I know a lot of people find the idea of creating and maintaining a podcast to be daunting.

This week, I got to talk to Jonathan Green from Sweet Fish Media, and their whole company is built around the idea of using podcasts as a means to interview your potential clients and win them over as clients for your business. They produce niche podcasts for B2B companies and take all of the pain and hassle out of managing your own.

In this episode, we talk about how podcasts can be used to reach beyond just content creation and into creating meaningful connections with your target audience.

For full show notes go to ...

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Jonathon_Green.mp3
Category:For Agency Owners and Consultants -- posted at: 6:27pm EST

On this episode of the Working Without Pants Podcast, I talk to John Ruhlin about how he wins new clients and nurtures existing clients through gift giving.

John talks about how gift giving is something that is often overlooked by companies, but if it is done right, it can have a huge effect on your business relationships and bottom line.

For full show notes go to ...

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_John_Ruhlin.mp3
Category:For Agency Owners and Consultants -- posted at: 4:00am EST

On this episode of the Working Without Pants Podcast, I talk to Arnie Malham about the success he has had in building multiple companies with rock solid cultures.

One of the things that I love about Arnie is that he is a big reader, and he attributes much of his success to what he calls R&D, ripping off and duplicating from the authors that he follows. And with a team of around 30 members and annual revenue around $10 million, I’d say he’s doing a great job of R&D.


For full show notes go to ...

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Arnie.mp3
Category:For Agency Owners and Consultants -- posted at: 9:00am EST

In this episode of Working Without Pants, we talk to Ryan Meo of about winning new clients, outsourcing and how being focused on operations has brought them the success they have today.

For full show notes go to ...

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Direct download: WWP_Ryan_Meo_Rev.mp3
Category:For Agency Owners and Consultants -- posted at: 8:30am EST

Tom Schwab is the force behind, a productized service focused on getting people on podcasts to let the world know what it is they do.

I've done tons of podcasts but had never thought deeply about the outreach strategy and sales process to the extent that Tom does. 

In this episode, we discuss how to turn podcasts into leads for your business. 



For full show notes go to ...

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at

Be kind and share with others

Direct download: WWP_TomSchwab.mp3
Category:For Agency Owners and Consultants -- posted at: 5:52am EST

Tim Conley is a business coach, was the host of the Foolish Adventure podcast, and is a high-level consultant, helping B2B entrepreneurs, agencies and consultants (from $0.5 - 5M) scale their businesses. 

In the first half of this episode, we discuss the businesses Tim works with, which range from $500K - 5M, and what it takes for them to grow and level up. 

In the second part, we discuss Tim's business model, which is quite similar to my own business, Outbound Creative, doing high-level consulting and selling group training programs. Find out how to scale your own solo consulting practice, making upwards of $200-500K a year, while only working 9 months a year and having a whole bunch of freedom during those 9 months. 

For the full show notes of this episode go to 

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at 

Be kind and share with others

Direct download: WWP_Tim_Conley.mp3
Category:For Agency Owners and Consultants -- posted at: 10:33am EST

Jake has done extensive research into how agency owners win clients. After all, his business Outbound Creative is focused on winning clients for agencies and consultancies. One strategy comes up over and over again: strategic partnerships. Many agencies get 20-70% of their revenue from strategic partnerships. In this episode Jake details:

  • 3 types of strategic partnership (including anecdotes of each type)
  • Elements of a strong partnership
  • 5 steps to creating your own partnership

The information in this podcast can be found in blog post form here.

Direct download: WWP_Strategic_Partnerships.mp3
Category:For Agency Owners and Consultants -- posted at: 9:56pm EST

Russ Perry is the founder of Design Pickle, a productized graphic design service. 

Design Pickle can free up your marketing team to work on bigger initiatives, while they take care of things like business cards, brochures, posters, etc. It’s amazingly simple: just sign up and get matched with a dedicated designer for unlimited designs at a flat rate of $370/mo.

You’ll really get some value out of this episode if you want to productize a service. We dive into how Russ started Design Pickle, scaled it to over $100K in monthly recurring revenue in 1.5 years, challenges he’s faced and big insights/ideas he’s discovered. His thought process in starting the business was fascinating.


Highlights of this episode: 

[3:25] Scratching an itch: After closing his agency, Russ sought a simple way to find vetted help for quick graphic design work (ie, business cards, brochures, etc). As a consultant, he developed a system for doing this stuff (ie, business). His clients were having success with it, so he moved into branding this service and launching it to the public. Plus, Russ loves pickles. So, voila, Design Pickle.

[6:00] Starting DP was really scary. Russ was facing unemployment and dreaded getting a job. He thought long and hard about what kind of lifestyle he desired. As a consultant, he discovered that managing production design met most of his lifestyle requirements. The business structure really came out of this clarity about his ideal lifestyle.

[9:25] A financial model is the only business plan you need (how you will make money). Russ discusses how he priced the service, and quickly raised prices, allowing for investments in growth.

[11:40] To acquire initial customers, start with a very simple solution. Then it’s all about getting out there and communicating that value. Russ was the best spammer alive. Almost got kicked out of a professional organization for it. Also, be profitable, so you can invest in strategic growth opportunities.

[14:15] In less than two years, Design Pickle has steadily and consistently grown to over $100K MRR, 1000 signups and 380 active users!

[15:15] Lessons from running a crappy business, and having a strong culture, has allowed Russ to grow the business so quickly. It’s all about the people. Keep it simple and stay the course!

[18:15] On avoiding going into other directions...Why not start Because he’s barely scratched the surface with Design Pickle.

[19:25] Being removed from day-to-day tasks is huge in ensuring the ship is running smoothly and in moving things forward. Russ’s role: Mechanic of the Pickle Machine, Voice of the Brand, Front Line of Sales, Strategic Navigator.

[21:10] On managing a team across the world. Besides the 2 others in Arizona, all the designers and managers are in the Philippines. The team is like a family, though, Russ realized when he was able to go to Philippines for the first time. Moving forward, he’ll be investing in meetups, conferences.

[24:20] Clients’ deserve respect and to be shown that their work is important. Put your all into the work and build relationships.  

[26:15] To grow your agency, get out and meet people in the flesh. Be real. Russ’s secret: he goes to conferences and gives out free pickles. People eat them up.  

[28:20] Everyone want to have fun, connect with real people. Plus, engaging people with authenticity and developing real relationships helps if things go sideways.

[29:40] Going forward, it’s all about finding more people they can help, taking the time to reach them, and communicating the value in Design Pickle.

[32:30] Cash flow is a challenge in expanding with sales/marketing/advertising. Always stay ahead of hiring, so you can handle the work if you take on new clients. The current model can handle doubling or tripling, but beyond that, it may need investments in software and other things to continue growing.

[35:25]Design Pickle offers a 14-day, risk-free trial. If you email Russ and let him know you signed up from the podcast, you’ll get a free pickle!

[37:10] For agencies: You can use DP for client work...but Russ recommends getting a feel first, so the team can get to know you and your brand before taking on your client work.

Learn More: 

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at 

Be kind and share with others

Direct download: WWP_-_Russ_Perry.mp3
Category:agency owner -- posted at: 2:00pm EST

After growing Solar Velocity from nothing to an 8-figure agency, selling it and getting bored on the beach, Jason Swenk began helping other agency owners. He now teaches the lessons he’s learned along the way at 

Jason shares his incredible insights in this episode, oozing with his spunky personality. 


Highlights of this episode: 

[4:10] It all started with a NSync parody site, then he started making $500 websites, quit his job at Arthur Andersen before they destroyed the world, and in 2-3 years was making $200K websites. So thanks Justin Timberlake!

[6:00] The company really took off once he started examining what we didn’t want to do (working with clients), and put systems in place so the business could go on without him.

[7:20] He kept upgrading the offerings based on what clients needed. As your price increases, so too does the need to communicate how you are unique.

[8:40] To really scale, the Agency Owner (does everything) needs to transition to the Agency CEO (focuses on vision, strategy, coaching). The first step is hiring a project manager!

[11:50] Assume you’re project manager will screw up. If you’re scared of that, get out of business. Jason encourages (one-time) failures for learning purposes. Systems>>Talent.

[14:30] Everyone on his team took personality tests, and they tried to find people to fill in the gaps. It’s more important that a new hire shares the company’s core values, then technical know-how. Value-based hiring led to Solar Velocity’s becoming the Best Place to Work in Atlanta, which snowballed into better & better people applying.

[16:20] He replaced Quarterly Reviews with Quarterly Coaching, because employers are your #1 asset, so management’s job is not to condemn, but to help make employees better and achieve their goals. Your office environment should reflect your personality. Be yourself. He made a fun environment, and those that didn’t like it could leave.

[19:20] Growth revolved around generating the pipeline through 1) strategic partnerships (not just trading leads, but building practice areas to specialize in), 1) outbound strategy, and 2) inbound strategy (gotta capture that info!) and 3) strategic partnerships- which is not just trading leads, but actually building practice areas to specialize in. They specialized in Sitefinity.

[22:00] Partner with an up-and-coming technology (not Wordpress or Facebook). Help them out before expecting anything in return. That’s what they did with Sitefinity- when they had success with it for a client, they made a case study to help Sitefinity communicate their value better. So Finity sent them Hitachi, Legalzoom, and other amazing clients.

[24:35] Successful people make money, but significant people affect other people/businesses by helping, not just taking...Helping>>Selling

[25:40] Don’t reach out to everyone. Go after a select few. Do extensive research. Think about who would need your service (ie, companies spending $10K+ on AdWords)? Provide value in the initial touch, and make a foot-in-the-door offer. DO NOT SEND A PROPOSAL!

[31:40] Chances of making money are 20X after they buy the foot-in-the-door offer, and you can qualify them. There is no bad agency client...only a bad prospect or a bad process.

[32:20] Building processes is about diving deep after a project is completed, to see what went right and what went wrong. Map it out and make adjustments. It takes a lot of f**k-ups.

[33:45] “If something were to happen to me, would this company survive?” worried Jason. Employees are like family, so it’s not just about you.

[35:15] Jason assisted with sales, just to bring in his colorful personality and make sure everyone was doing their job.

[36:10] They sold the business to a strategic partner who wanted to get into what Solar Velocity was doing. Only 0.25% of agencies get sold, so don’t feel like that is what it takes to “make it.” Money doesn’t ensure happiness.

[37:00] When considering selling, if they ask you questions, ask the same questions to them. And if people start asking to buy on the low, go through the process and learn from it. It won’t hurt, as long as you don’t give up valuable secrets. ​

[38:55] If you don’t like the offer, stop there or waste your time. And he explains how to tell if the buyers are serious, or they just want to steal your secret sauce. And don’t get too excited during the due diligence phase--that’s when most agencies go out of business, so assume it won’t go through.

[40:45] After selling, Jason was out in 9 months. He never got his earn out (losing millions), but he learned a valuable lesson and has made that money back by teaching other agency owners through his mistakes.

[41:40] Earnouts are based on growth rate and profit margin. Agencies between $2-10M are hard to sell. Don’t sell if you’re making bank.

[44:10] So why did Jason sell? The business outgrew his partner, and he got bored and wanted something new.

[44:40] Nowadays, he helps agency owners scale, teaching them how we started, grew and sold his agency. His goal is to be the #1 resource in the world for agency owners. Check out his podcast, video show, and the Agency Playbook (12 systems to scale and grow your agency).

[47:15] Jason doesn't read. He learns from doing & failing. Just wing it.


Resources Mentioned in this Episode: 

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at 

Be kind and share with others

Direct download: WWP_-_Jason_Swenk.mp3
Category:agency owner -- posted at: 12:44pm EST

David Reske is the founder and CEO of digital marketing agency Nowspeed.

He’s built a phenomenal business over the last 10-15 years. David is incredibly clearheaded and sophisticated about Nowspeed. But the journey has not been without challenges.

In this episode, we discuss his business, what's works, and what hasn't.

Highlights of this episode: 

[3:15] The kind of people you hire creates the kind of atmosphere and culture your company will have.

[3:50] Nowspeed has evolved over the years to use whatever tools are available to drive engagement, traffic and leads.

[5:00] Dave started the company with his wife, which offers great flexibility for her as a working mother. But, leave business outside the shower!

[7:20] The digital marketing landscape has grown much more sophisticated, and it’s much harder now to land the big boys as clients.

[9:00] Nowspeed differentiates itself through platinum level service and expertise that goes beyond the capabilities of most internal marketing teams.

[12:30] In his business, Dave works primarily as strategist, accountability partner, business developer, management coach, and process/service tweaker.

[14:10] It’s risky for a service business to have one customer account for a large portion of the business.

[15:25] The way Nowspeed is structured, account leads communicate and work with clients and strategy, and they manage a team of experts who work in their particular expertise to execute the campaigns.

[17:10] There’s no magic bullet to getting work. They do the stuff they offer- inbound/content marketing,  SEO, PPC, social media- to drive leads. But they are also very active in partnering with other agencies/consultants to drive referrals.

[19:20] Dave spends half of his time doing strategic sales/business development. They only reach out locally, but they have leads/clients from all over the US/world.

[20:45] Dave loves integrating all the pieces of the puzzle.

[22:18] Hiring when desperate = Big Mistake! Instead, Nowspeed hires (mainly fresh college grads) and trains in classes.

[26:30] You don’t know what systems/process you need, until you really NEED them. So it’s a continuous evolution, discovering new challenges/things that need fixing. It helps to get your team involved in this.


Resources Mentioned in this Episode: 

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at 

Be kind and share with others

Direct download: WWP_-_David_Reske.mp3
Category:agency owner -- posted at: 9:35am EST

Dan Englander is the founder of, and the author of Mastering Account Management and The B2B Sales Blueprint.

Dan is an expert on growing sales, and specifically, getting the most value out of existing clients, which is often ignored in sales.

We dive into his experiences in ramping up sales at one of the first video explainer companies and winning massive Fortune 500 accounts (like Verizon, Showtime, Bank of America, Venmo), before he started his own consultancy.

Highlights of this episode:

[1:44] In the blistering New York summer, Dan wears shorts to work from home, and will often stroll over to a coffee shop- it gets him in a different mindset and is helpful for separating tasks.

[2:20] Before he was the braggadocious founder of, Dan knew nothing about sales. As the first employee of Idea Rocket, he learned sales and made it work.

[3:50] His initial sales process was not cutting it.

[4:20] Things started to turn around. PPC and PR was effective, but winning the show opening for the Showtime Series Weeds help establish them as an authority.

[4:50] Fortune 500 companies find vendors the same way startups do. They won those initial big accounts by becoming a safe bet.

[5:45] The initial big wins gave them validation, and created a snowball effect.

[5:55] The main challenge for their first big sales was convincing them that something so unorthodox (at the time) as investing five figures in cartoon was a safe investment.

[8:15] As the market grew, the game changed from “buy a car not a horse” to “buy a Mercedes not a Honda.”

[8:55] Eventually, they got to a point (which most agencies get to) where the struggle was qualifying and prioritizing.

[9:35] How Dan goes about qualifying and prioritizing for better clients.

[11:18] Dan’s got different arrows in the quiver, that is 2 or 3 different sales processes for the different levels of clients.

[13:10] Establish immediate value by giving prospects a taste of what it’s like to worth with you.

[13:40] The biggest stopping point for many creative agencies is prep work. In order to overcome this, they would offer scripts to their videos, to get in the door and prepare the client.

[15:55] Account management is basically a role that combines client services and sales.

[17:04] Selling to existing customers should be easier than selling to new people, but its potential goes untapped, because most go about it the wrong, awkward way.

[18:25] Start with a partnership mindset. Don’t just randomly hit them up for new business. Build the next steps into your initial process. Be relevant. Find ways to help.

[20:00] Jake has found that quarterly reviews are a great way to reconnect and gauge the impact your work has had.

[20:55] Don’t send donuts.

[21:15] Partnerships are a long game- there’s more ways to pull value from an account than just selling the same product again.

[22:25] Dan discusses his approach to getting referrals from clients.

[24:10] What to look for in hiring a salesperson / account manager: if they could write well, they’re halfway there.

[25:34] Asking the right questions is the most important part of sales. Subject matter expertise is overrated.

[26:44] Aaron Ross stands out as useful to any company trying to implement a sales process.

[27:23] Neil Rackham was ahead of his time.

[28:55] While many young entrepreneurs want a step-by-step guide to succeeding, it’s more about the mindsets that enable success.

[29:35] Dan’s first book is the Chicken Soup for the Soul of account management. Check out the link below for a free copy.

[30:42] By the hard questions early on, you will save time and find more opportunities.


Resources from this episode: 

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at 

Be kind and share with others

Direct download: WWP_-_Dan_Englander.mp3
Category:general -- posted at: 10:19am EST

Ben Lee is the founder and CEO of Neon Roots, an award-winning agile development agency.

Interestingly, the majority Neon Roots’ revenue does not come from actual developing, but rather from their discovery program, called Rootstrap, which guides entrepreneurs from the vaguest idea of an app, to a development-ready prototype.

Ben dives into how Rootstrap took on a life of it’s own, why discovery is so important, his untraditional sales team and other insights into how he’s built his business.

Highlights of this episode:

[2:20] Ben has to wear pants at work now, but he did work with Snoop Dogg’s management company before moving to his new location in West Hollywood, and he talks about random run-ins with celebrities

[4:55] He and his co-founder started Neon Roots to challenge the traditional agency model, and actually practice what is preached about agile methods, lean startup, etc.

[6:00] He discusses the bloated, risk-avoidant and unhappy lifestyle common in the service industry, and how he ditched it to start something new- pioneering AR/VR before the market was ready

[7:15] Story carding and discovery was a way to qualify clients, manage expectations, and truly aligned interests- and was incredibly successful

[10:27] How the Rootstrap offer evolved, and how it was influenced by Ben’s background in hospitality

[13:50] He discusses the psychology that goes into the Rootstrap customer experience

[16:00] The Rootstrap Swag Box is a powerful component of the whole experience, triggering positive emotions, and taking on a life of its own as a storytelling mechanism- whether it’s for a 23 year-old first time entrepreneur or Tony Robbins

[19:10] Competitors talk about the Swag Box

[19:37] Discovery and other engagement activities after kickoff are all about providing value to the customer

[21:45] Rootstrap has built a reputation among VCs, from whom they get a lot of deal flow

[22:13] Brand grows in thought-leadership

[23:30] He doesn’t hire sales people, but many former participants sell for him by simply sharing their stories

[25:10] Offering free advice over the phone for young entrepreneurs who aren’t yet a good fit is great for building relationships, which have resulted in referrals several years later

[29:20] Embarrassing sleazy sales guy vs the former participants who aren’t sure their confident enough for sales

[30:39] The sales cycle involves less commitment, or going on dates before you get engaged

[32:35] They (over)deliver so much value that other agencies resell Rootstrap

[33:05] Rootstrap vs ongoing consulting, and why many Rootstrap participants don’t convert because they don’t have an internal dev team or they need help fundraising

[35:18] The solution to a hybrid agency is proper siloing. Going forward, Neon Roots will be doing more creative stuff, which can happen because the service side is completely separate- plus Rootstrap Studios in Uruguay

[40:40] Ben gives his words of wisdom to agency owners to build their way up and increase sales

[42:25] You can reformulate lean/agile methods to any industry/business


Mentioned in this episode:

Direct download: WWP_-_Ben_Lee.mp3
Category:agency owner -- posted at: 11:39am EST

Since I last brought Brian Casel onto the podcast over a year ago, he has sold his first productized business and launched his second. Brian is truly leading the way in terms of productized services and in this interview he gives a great context as to how agency owners can begin to transition from personalized consulting to a productized service.

Currently I am mid-way through productizing my own services at Outbound Creative, so in this interview I delve deep into some of the biggest challenges and setbacks that I have had along my journey and tap into Brian's expertise to overcome them.

This is a gold nugget episode for anyone who is trying to build and scale a productized service!

Also, be sure to check out Brian's new Productize Podcast.

Direct download: WWP_Brian_Casel.mp3
Category:creative entrepreneurship -- posted at: 8:54am EST

Dobbin Buck is one of the partners of the agency GetUWired. Year after year, Dobbin's firm wins awards from Infusionsoft such as partner of the year as well as Top Sales and Revenue generation for Infusionsoft.
GetUWired is an industry leader in Infusionsoft consulting.
But that's not all, GetUWired's office just happens to be a cabin in the woods! They may wear pants and have an office, but you have to admit that is one hell of a cool approach to an office. In addition, GetUWired has won Entrepreneur Magazine's Top Company Culture award.
In this episode Dobbin shares:
  • How he has built an award winning culture at his agency
  • How he has built so much demand for a business that there is a waiting period for new clients to get started
  • The model behind GetUWired, how they bill, sell and manage projects
  • GetUWired's systematized hiring process to ensure anyone they hire is a great fit.
  • And several incredible aha-moment revelations that can change how you think about your agency.
This episode from Dobbin is one of my favorite to date and it is jam packed with value. I know you will get a ton out of it so stick through to the end.
Direct download: WWP_Dobbin_Buck.mp3
Category:agency owner -- posted at: 9:00am EST

For anyone who has been following my business over the past year, they will know about my launch of Outbound Creative which is a company that helps agency and consulting companies win their dream clients with eye-catching outreach campaigns.
For a long time, I thought I was the only one doing crazy things like this...
Then one of my friends send me Stu's book How to get a meeting with anyone. As soon as I started reading my first thoughts were "YES!!!"
Stu has literally written the book that I someday dreamed of writing. In his book he writes about a method called 'Contact Marketing' which is this concept for doing very out of the box methods of capturing someones attention so you can get in the door and start the relationship.
In preparation of this book, Stu interviewed over 100 sales leaders and gathered countless stories on interesting 'contact marketing' campaigns that have helped people get meetings that are game changers for their life or business.
In this interview, Stu and I dive into the book, the approach and how to think about creating your own contact marketing campaigns. 
Direct download: WWP_Stu.mp3
Category:agency owner -- posted at: 2:53am EST

In this episode, Damian Thompson of Salesability shares his insights into the pitfalls that most software development companies hit in their sales process and how to overcome them.

Direct download: WWP_Damian.mp3
Category:agency owner -- posted at: 8:33am EST

If your agency targets CMO’s as potential customers, then listen up because this interview is for you.

Drew Neisser is the CEO of the agency Renegade and author of The CMO’s Periodic Table.

When I came across Drew’s book, I was blown away. In The CMO’s Periodic Table, he has interviews with 64 high level CMO’s of very big companies. A majority of which are the CMO’s from Fortune 500 companies.

Each interview focuses on one key insight or topic that these CMO’s deal with on a regular basis. The end result of all of these interviews is an incredible book that covers the wide spectrum of issues these CMO’s face.

In this interview, Drew talks about his strategy for creating this book, how he got interviews with such high level CMO’s, and how this book has had a profound impact on his business.

He also discusses the challenges agencies face when trying to sell their services to CMO’s and why many fail when reaching out to them.

This interview is jam packed with incredible insights that can drastically change your agency.

Direct download: WWP_Drew_Renegade.mp3
Category:agency owner -- posted at: 10:49pm EST

After over 14 years of running his agency, Matt Schwartz has recently took his agency through an entire process of rebranding.

With his rebrand, they have focused on a specific target market and niched their business down to their key core clients.

Matt’s agency, Constructive, focuses on working with social causes and brands.

In this interview, Matt talks about the process of rebranding his agency, and how other agencies should look at positioning themselves in the market.

He also points to a few great resources that helped him through the rebrandng process.

Positioning for Professionals by Tim Williams

Zag by Marty Neumeir

Direct download: WWP_Matt_Schwartz.mp3
Category:agency owner -- posted at: 2:41am EST

If your business is not utilizing the Rockefeller Habits, then listen up because this episode is for you.

Over the course of my career, I have noticed a consistent trend across all of my best clients and successful entrepreneurs.

All of them are implementing the Rockefeller Habits.

That consistent trend I have seen across my best clients has lead me to asking Andy to come on the show. Andy is the CEO of Petra Coach which is a coaching and consulting company that helps firms implement the Rockefeller Habits.

In this interview, Andy explains what the Rockefeller Habits are. The key components, and why all companies should consider implementing these practices.

If you aren’t using the Rockefeller Habit’s already, then I highly recommend you listen to this interview and also check out many of the free resources on Andy’s website.

Direct download: WWP_Andy_Bailey.mp3
Category:creative entrepreneurship -- posted at: 3:59am EST

In an age where everyone is zigging harder, Bram Warshafsky of 5Crowd has decided to zag. While most agencies push for more sales, more revenue, and more growth as a means to profitability, Bram has approached things different.
Bram created 5Crowd which I would best describe as a mixture between Upwork and a standard agency. 5Crowd goes out and wins the business of corporate clients, and then sends that work out to their community of on demand freelancers.
This model keeps their overhead low, and profitability up, and enables them to scale up and down based on their client needs.
And 5Crowd isn't just working with small companies, they are working with corporate giants. PepsiCo, Johnson & Johnson, Hershey, InBev, and Twitter are just a few of their big name clients.
In this interview, Bram shares more about his model and we dive deep into how more agency owners can think outside of the box when building their model.
Also, if you are a freelancer wanting to work with bigger brands, then check out 5Crowd as they are eager for more talent to fill their client needs. 
Direct download: WWP_5Crowd.mp3
Category:agency owner -- posted at: 1:12am EST

Sam Shepler is the CEO of Skyscope and host of the Thoughtful Warrior Podcast. In this episode we talk about Sam's journey building up his video agency, how he got started, and how he has grown the business.
One key point we talk on is the creation of a productized service offering within their agency. Sam has nailed this down with their video testimonials productized service that is rapidly growing and accounting for a significant piece of the companies profitability.
Sam also talks about building a culture and keeping that strong as his company has grown from 3 partners to a team of employees. 
Check out Sam's company and work at
Direct download: WWP_Sam.mp3
Category:creative entrepreneurship -- posted at: 8:35am EST

Today's guest is a little different than my normal guests, but incredible none the less. While he may be wearing a suit during the interview, don't hold it against him.
On this episode I have Alan Siegel, founder of Siegel+Gale, an agency with over 250 employees, and his new consultancy SiegelVision.
Alan's entire career and business is built on the idea of helping corporations and institutions simplify. One of his most notable clients that we can all be grateful for is the IRS. Alan's agency simplified and re-created the US Tax Forms. 
In this episode, Alan talks about building his agency up to that level, how simplicity became their focus, and about his upcoming conference Call for Clarity. In the conference, Alan's firm has pulled together some of the brightest individuals throughout various industries, institutions and government agencies to talk about the accomplishments they have made by simplifying. 
In simple terms: This episode is good, you should listen to it. 
Direct download: WWP_Alan_Siegel.mp3
Category:creative entrepreneurship -- posted at: 6:30am EST

Today I am honored to have Aaron Ross on the show, author of Predictable Revenue and his brand new book From Impossible to Inevitable.
On this episode Aaron dives into his story of growing his personal income from $60k to over $800k over the past several years, and how he managed to do so while keeping a work schedule of 20-30 hours per week.
Aaron also shares his world famous sales model that can change how you look at sales and building a sales team for your agency.
He also dives into his philosophies on outbound marketing, what is effective and how you can use outbound to create predictable growth for your business.
And lastly, he shares some incredible nuggets of wisdom from his new book From Impossible to Inevitable. It's an incredible book and I highly recommend picking up a copy. I guarantee you won't walk away disappointed!
Direct download: WWP_Aarron_Ross.mp3
Category:general -- posted at: 5:50pm EST

On this episode I am excited to bring you Ryan O'donnel of SellHack. Sellhack is an incredible tool that I use on a daily basis at Outbound Creative. With SellHack you can find anyones email and contact information with the click of a button.
For years I did this manually, BUT NO MORE! Sellhack has made my outbound research so much easier.
In this episode, Ryan doesn't just talk about SellHack. We dive through and give an entire framework for creating an email prospecting system for your agency or business. 
We take it step by step from identifying who to go after, determining what messaging to use when reaching out to them, the follow pus and then how to handle the lead once you get them on the phone. 
This is an incredible episode with lots of actionable insights. 
Also, check out Sellhack's blog for tons of great insights on cold emailing. 
And download their free eBook on cold emailing which is a great resource.
And seriously, go sign up for a free trial of SellHack, you will love it!
Direct download: WWP_Ryan.mp3
Category:general -- posted at: 8:02am EST

On this episode of Working Without Pants, I am honored to have Michael Hardesty of MadeIn Network and 24Hr Records. On this episode Michael shares his journey of going from a freelance professional to running production at a rapidly growing Youtube Agency.
Michael also gets into a lot of the creative dynamics that he sees with 24 Hour Records and how constraints with creativity can create even greater end results.
Direct download: WWP_Michael_Hardesty.mp3
Category:agency owner -- posted at: 6:15am EST

I am honored to have Blair Enns of with me on today's episode. Blair has been a long time influence of mine back since I read his Win Without Pitching Manifesto several years ago.

In this episode, Blair talks about some of the biggest mistakes that agencies make when selling their services and how to remedy those mistakes. He also shares more information about his own entrepreneurial journey and how he got to where he is today. 

Direct download: WWP_Blair_Enns.mp3
Category:agency owner -- posted at: 6:21am EST

Liam Veitch of completely changed my mindset on freelancing when I read his book 'Stop thinking like a freelancer'.

In this book Liam talks about the topic of evolution, and for anyone who has followed my own journey over the past year, I have drastically evolved from a web designer to running Outbound Creative which helps agencies and freelancers win their dream clients.

Liam's mindset was extremely valuable for me when I read his book, and in this episode we discuss some of the key points from his book and how freelancers should be approaching their business.

Direct download: WWP_Liam_at_64.mp3
Category:Creative Freelancing -- posted at: 1:34am EST

Greg How is a partner at Happy Cog, a Philadelphia based digital agency, and he is a partner in the Bureau of Digital which is an organization that puts on events for owners and leaders of digital agency.

In this interview Greg shares the lessons he learned building up Happy Cog over the past 15 years, as well as sharing stories of the expriences his team has had with Bureau of Digital.

You can learn more about Greg and the amazing events he puts on at

Direct download: WWP_Greg_Hoy.mp3
Category:agency owner -- posted at: 2:00pm EST

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 EST

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 EST

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 EST

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

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 EST

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

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

"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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

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 EST

Tristan King is the founder of Shopify Ninjas, a web design agency focused exclusively on the Shopify platform.

In this episode, Tristan and I discuss:

  • Finding your niche and the benefits of working with a channel partner
  • How to work remotely and travel
  • The benefits of remote working even if you aren't a world traveler
  • How Tristan has grown the business at a rapid pace
Direct download: CFS_Tristan_King.mp3
Category:creative -- posted at: 3:56pm EST

Ilise Benun is the creator of where she focused on helping freelancers and creative professionals learn how to market themselves. 

In this episode, Ilise shares what she calls a marketing machine.

This is a fundamental strategy that I have used in my business since the day I first learned it. My hopes are that it can help you in your business as well.

Mentioned in this episode:

Visit our website at

Direct download: Ilise_Part_2.mp3
Category:Creative Freelance -- posted at: 8:00am EST

Kurt Elster is a co-founder of the web design agency EtherCycle. In this episode Kurt shares insight and wisdom from his experience starting an agency and attracting high quality clients.

In this episode, Kurt and I cover:

  • His unique direct outreach strategy and what made it succesful
  • How he made starting a business far too complicated
  • The benefits of working a channel partner
  • Creative ways for attracting new clients
  • How to build an agency model that works

Mentioned in this episode:

Direct download: CFS_Kurt_Elster.mp3
Category:Creative Freelance -- posted at: 3:00am EST

This is a very special episode of The Creative Freelancer Show. While most of my episodes are recorded via Skype, this interview was recorded in person.

A few weeks ago, I was spending some time in Berlin, Germany. While I was there I was introduced to an illustrator named Mars Dorian.

Mars is an incredibly talented illustrator with an outrageously unique style. 

In this episode of The Creative Freelancer Show Mars and I discuss:

  • How to create a unique style for your work
  • The advantages and challenges of unique style
  • How to utilize freelancing to fund other passionate projects
  • And much more

This interview is packed with valuable insights that any creative will benefit from. 

Mentioned in this episode:

Direct download: Interview_Mars_Dorian.mp3
Category:Creative Freelance -- posted at: 3:00am EST

Preston D Lee is the creator of, a blog that focuses on helping designers and freelancers build better businesses. 

Preston has been a designer and consultant for several years, and has built a business on the side along the way.

In this episode you will learn:

  • Common excuses to starting your business and how to overcome them
  • How to make freelancing not that risky
  • Why you don't need to be an expert to start freelancing
  • How you can freelance while still maintaining a full time job

Mentioned in this episode:

Visit our website at

Direct download: CFS_Preston_D_Lee.mp3
Category:Creative Freelance -- posted at: 4:00am EST

Pricing isn't just about the money.

It is about the quality of life.

It is about earning more money in less time.

It is about making a decent income so you aren't stressed and you can put time toward the projects you love.

In this episode, I cover everything I know about pricing and share with you the methods that have helped me triple my income over the past six months.

Learn more at

Direct download: CFS_Pricing.mp3
Category:Creative Freelance -- posted at: 3:00am EST

John McIntyre is a copywriter who goes by the nickname “The Autoresponder Guy”.

To set himself apart from other copywriters, John has focused his business exclusively on writing e-mail autoresponders.

In addition, John is a digital nomad who runs his copywriting business all the way from Chiang Mai, Thailand.

In this episode, John discusses:

  • How he got started and landed his first clients

  • His ‘break shit’ mentality on starting businesses

  • Actionable tips for anyone seeking to write better copy

Mentioned in this episode:

Direct download: CFS_John_McIntyre.mp3
Category:Creative Freelance -- posted at: 4:00am EST

Friends and acquaintances can be a great source of client work although you must be careful when entering into professional relationships with them.

In this episode I cover:

  • Why working with your friends can actually be a great idea
  • How to reach out to friends who may be good prospects
  • Why you should never work for friends for free
  • How to handle payment and project communication with friends

For more on this topic, read my blog post How to work without friends and not end up hating each other

Direct download: CFS_Working_with_friends.mp3
Category:Creative Freelance -- posted at: 2:00am EST

This episode is one of those conversations that left me rethinking my approach life. 

Dane Sanders is an incredibly inspirational and creative individual. He started his creative career as a photographer and has seen the shift from the analog to the digital world.

In this episode Dane discusses:

  • How to stay relevant in a changing creative world
  • How simple daily habits can completely change your life
  • A unique perspective on the purpose of the work that we do

Also be sure to check out Dane's Podcast Converge and his new writing course Weavewriter.

Mentioned in this episode:

Learn more at


Direct download: CFS_Dane_Sanders.mp3
Category:general -- posted at: 3:00am EST

Freelancing doesn't have to be a one way road. Instead, you can use it as a means of trying out different things while you seek your next employment opportunity.

This weeks guest, Clark Buckner, began his career doing freelance design and branding work, yet ultimately his freelancing lifestyle lead him to an opportunity for full time employment that was too good to pass up.

In this episode Clark discusses:

  • What it is like to start a freelance career as a college student
  • How Podcasting helped him land new clients and expand his network
  • How freelancing helped him land the job of his dreams
Direct download: CFS_Clark_Buckner.mp3
Category:general -- posted at: 3:00am EST

Mat Newton is a web professional who ran a sucessful SEO business for several years before shifting his mindset toward building his own platform and products.

In this episode Mat reveals.

  • How to build a lifestyle that allows you to work from anywhere
  • Methods for aquiring a client base very quickly
  • How to use freelancing as a means of building products

Learn more at

Direct download: CFS_Matt_Newton.mp3
Category:general -- posted at: 9:40pm EST

One of the biggest mistakes new freelancers make is in how they describe what they do. 

In this episode of The Creative Freelancer Show, Ilise Benun of teaches a framework for how to talk about what you do to new clients.

This is a framework that can be used online, at networking events or even in casual conversation.

See more at

Direct download: Ilise_Part_1.mp3
Category:general -- posted at: 4:00am EST

Constant improvement is a value that I attribute a large portion of my success to. I am constantly learning, constantly improving and I am never satisfied.

My goal with this episode is to share with you my theories on improvement and discuss the different ways and areas you need to be consistently growing in as a creative professional.

In this episode you will learn:

  • Resources for enhancing and improving your creative skills
  • Resources for enhancing your business knowledge
  • Resources for improving as a creative professional
  • The go to tools for personal growth

Mentioned in this episode:

Direct download: Consistent_Improvement_mixdown.mp3
Category:general -- posted at: 12:00pm EST

Alicia Binkley / Waters is a freelance designer and artist from Nashville, TN. She wasn’t always a freelancer though and recently made the jump just a few months ago. 

In this episode 

- Alicia talks about what it was like to make that jump from having a full time job for seven years to finally going freelance.

- Discusses what it is like to be married to another artist and collaborate with them regularly on projects 

This episode is great for anyone making that jump to freelancing full time, as well as any creative who may be married or dating another creative professional. 

Direct download: Alicia_Waters.mp3
Category:general -- posted at: 12:00pm EST

A portfolio in your creative career is more than just a collection of your past works. 

A portfolio is like a carefully curated art gallery. It is meant to showcase your work and put it in the best possible light.

In this episode:

  • I discuss what makes up a good portfolio
  • Three criteria to consider before taking on any project
  • How to turn yourself into a portfolio piece


Regardless of if you are new to the freelancing business or have been freelancing for a while, this episode has some insights which may make you rethink how you showcase your work to the world. 

Direct download: Episode_-_Building_a_portfolio_mixdown.mp3
Category:general -- posted at: 4:00am EST

005: Grant Spanier

Grant Spanier is an inspiring and genuine individual. He holds nothing back and refuses to censor himself in the sake of being him true self.

In this expletive filled episode:

  • Grant goes through his journey on building a successful creative career
  • Grant shares his philosophies and practices on creativity. 


Grant’s story is one that will change your perspective on creativity and making a living as a freelancer. 

Direct download: CFS_Grant_Spainer.mp3
Category:general -- posted at: 9:00am EST

At the core of any succesful creative career is a mastery and continued practice of ones craft.

In this episodes we dive into the philosophies behind mastering your craft as well as some actionable methods on practicing and learning your craft at a rapid pace.

Direct download: 004__Mastering_your_craft.mp3
Category:general -- posted at: 7:05am EST

003: Maggie Appleton

Maggie Appleton is a young illustrator based out of Saigon, Vietnam. At a very young age, Maggie has already accomplished a lot.


If you look at her portfolio, you would assume that she has dedicated her entire life to this craft of illustration, but in reality Maggie set herself on a path of deliberate practice and learning and mastered a craft very quickly.


Join us for this episode as Maggie shares her strategy for rapid learning, how she got her first freelance clients and how she is building her career with the freedom to travel anywhere.


Sign up for our e-mail list and see the shownotes for this episode at

Direct download: 003__Maggie_Appleton.mp3
Category:Creative Freelancing -- posted at: 2:47am EST

002: Why freelancing

Some people believe that freelancing isn't a real business.


Other's call it just trading time for money.


But the truth is, there are some major reasons why freelancing is an amazing route to go with your life and your business career.


In today's episode I will dive into many of the reasons why you should consider freelancing if you aren't already doing it.


I will also get into some perspectives on freelancing that may change how you look at your career even if you are already a freelancer.


Visit our website to sign up for our e-mail list at

Direct download: 002__Why_Freelancing.mp3
Category:Creative Freelancing -- posted at: 2:46am EST

001: About the show and Jake's background

The mission of the Creative Freelancer Show is to help creative professionals launch their freelance career, get more clients and work from anywhere.

We will cover a wide range of topics including acquiring new clients, finding your niche, practicing your craft, pricing your work, marketing yourself, mastering the creative process and much more more.

In this episode, we will discuss the mission of The Creative Freelancer Show as well as going into a bit of background about your host Jake Jorgovan. 

The purpose of this episode is to prep you for future shows to come, give you some context about what you will be learning and a brief introduction to my story.

Sign up for our newsletter and learn how to launch your freelance career, get more clients and work from anywhere at 

Direct download: 001__About_the_show.mp3
Category:Creative Freelancing -- posted at: 2:44am EST