Working Without Pants - Creative Entrepreneurship

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

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

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 EDT

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 EDT

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 

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

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 

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

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 EDT

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 

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

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 EDT

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 EDT

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 EDT

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 EDT

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 EDT

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 EDT

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 EDT

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 EDT

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 EDT

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 EDT

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 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

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 EDT

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 EDT

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 EDT

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 EDT