Working Without Pants - Creative Entrepreneurship (general)

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 EDT

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 EDT

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 EDT

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

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

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

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

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

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

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


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

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 EDT

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 EDT

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 EDT

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 EDT

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 EDT

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 EDT

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 EDT

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 EDT

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 EDT