Working Without Pants - Creative Entrepreneurship

This week's episode compliments last week's chat with Dave Schneider. David Henzel is the CEO of Upcoach and co-owner of an impressive amount of businesses he runs with Dave Schneider.

David has been a huge inspiration to me and my businesses. We often hear people preaching the mindset of doing 1 thing really well, but David inspired me to act differently and take action on my natural penchant towards working on a variety of projects... ever since I took his advice, I've quadrupled my income!

Tons of value in this episode, tune in to hear how David has built core businesses with side projects that leverage the core companies.

Want to work with me as an advisor? Visit

Direct download: WWP_David_henzel.mp3
Category:For Agency Owners and Consultants -- posted at: 8:02am EDT

On today's show, I sit down with Dave Schneider of Ninja Outreach. We discuss what it's like to sell a company, and Dave shares how his journey with Ninja Outreach led him to create Shortlist, a marketing agency.

If you're interested in building and selling a software company, this episode is for you! Be sure to tune into next week's episode with David Henzel to hear how Dave and David partnered together to start a bunch of different companies... and ended up running 9 companies at the same time!

Want to work with me as an advisor? Visit

Direct download: WWP_Dave_Schneider.mp3
Category:For Agency Owners and Consultants -- posted at: 9:08am EDT

11 days… no email… no calls… no business.

Recently I returned from a vacation where I stepped completely away from my businesses.

It was a powerful milestone to hit, and one that many entrepreneurs fear of committing to.

In this podcast episode, I dive into why entrepreneurs should take more vacations… and how taking time off can accelerate your growth as an entrepreneur.

Want to work with me as an advisor? Visit

Direct download: WWP_Vacation.mp3
Category:For Agency Owners and Consultants -- posted at: 8:44am EDT

Today I chat with Sarah Weise of BIXA Research, a marketing research firm with clients like Google and other prominent Fortune 500 companies.

I came across Sarah while I was doing my own research into... marketing research. Sarah teaches the LinkedIn Learning course on Market Research.

There are tons of marketers and agencies out there, it was fascinating to learn what big companies will pay for and how much money is spent on researching how to do better marketing.

Want to work with me as an advisor? Visit

Direct download: WWP_Sarah_Weise.mp3
Category:For Agency Owners and Consultants -- posted at: 4:54am EDT

On this week's episode, I have a chat with performance-based Amazon expert Adam Weiler of Sunken Stone.

Sunken Stone is an Amazon consulting partner doing brand management services that help companies selling Amazon products to optimize their business and gain more presence.

What's interesting about Adam's business is that it runs on a performance model, which means they charge on increased new revenue. This model is quite different from cash paying marketing services, which you can hear more about in the episode 'Why selling marketing services is stupid'.

Want to work with me as an advisor? Visit

Direct download: WWP_Adam_Weiler.mp3
Category:For Agency Owners and Consultants -- posted at: 9:37am EDT

On this show I have a chat with Doug Holladay, the CEO of PathNorth and author of Rethinking Success.

We're super lucky to have Doug on the show today, he's highly successful and has a fascinating story that sees him surrounded by affluent people (think Warren Buffet level affluent) and, you guessed it, lots of success stories.

If you're interested in finding meaning in work and life, that's what Doug is all about, you'll love what we dive into on this episode.

Want to work with me as an advisor? Visit

Direct download: WWP_Doug_Holladay.mp3
Category:For Agency Owners and Consultants -- posted at: 12:38pm EDT

In this episode, I sit down with Jeroen Corthout of Salesflare, a CRM SaaS product. Jeroen has great insights to share about his journey in building a sustainable software company.

In light of starting my first software company ( - in beta), I will be reaching out to connect with more people in the software game to learn from their experiences. I'm sure you'll find tons of value in this episode!

Want to work with me as an advisor? Visit

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

On this episode of the Working Without Pants podcast, I have a chat with my friend Jason Bay of Blissful Prospecting. Outbound Prospecting SER world.

Jason and I have been working in the space outbound prospecting, SER space for some time now. His company started off providing services and eventually moved into training for larger companies.

While we both started in similar places, our journeys have taken us down very different paths. Tune in to hear the story of how two people navigated different approaches and offers to build unique outbound companies.

Want to work with me as an advisor? Visit

Direct download: WWP_Jason_Bay_183.mp3
Category:For Agency Owners and Consultants -- posted at: 6:52am EDT

On this episode, I sit down with Elyse Archer of Brand Builders Group. Since recording this episode, I became a customer of theirs because this discussion sold me on how awesome their service is.

In this episode, we dive into how they grew to a team of 50 (!) over only 2 years. We also chat about what makes for a strong personal brand and how to think through the process of building a brand. Tons of value here, don't miss out!

Want to work with me as an advisor? Visit



Direct download: WWP__Elyse_Archer.mp3
Category:For Agency Owners and Consultants -- posted at: 8:52am EDT

Yes… as a person who runs two marketing agencies, I am calling this business model stupid.
In this episode, I go into why.
I also share the opportunity that most service companies have to 10x their client value…
And examples on how I have done this myself.
Want to work with me as an advisor? Visit
Direct download: WWP_Why_selling_marketing_services_is_stupid.mp3
Category:For Agency Owners and Consultants -- posted at: 8:53am EDT

Hiring… this is something that most entrepreneurs struggle with.
And messing it up is an expensive mistake to make.
In this episode, I go through my framework that I have used 30+ times to make successful hires.
Want to work with me as an advisor? Visit
Direct download: WWP_how_to_succeed_in_your_next_hire.mp3
Category:For Agency Owners and Consultants -- posted at: 11:51am EDT

In today's episode, I sit down with Pia Silva of Badass Your Branding. Pia took the branding agency model and flipped it on its head - instead of doing huge branding engagements, the kind that often take tens of thousands of dollars and many months to produce, she started offering 2 day intensives with her customers.

Tune in to hear how Pia scaled up, expanded beyond just branding and built up a successful training business. Here's what's even more interesting - she did it all this with zero employees! She and her partner have pulled all this off by creating niche offers and by working with the right mix of partners and vendors.

Want to work with me as an advisor? Visit

Direct download: WWP_pia_silva.mp3
Category:For Agency Owners and Consultants -- posted at: 10:48am EDT

Scarcity mindset… this is something that has been on my mind a lot lately.
I’ve seen this in myself.
I’ve seen this in the people I advise.
And I’ve seen this in millionaires who never need to work again…
What has become apparent is that scarcity mindset never goes away.
That is what I dive into and unpack in this episode.
Want to work with me as an advisor? Visit
Direct download: WWP__Scarcity_mindset_never_goes_away.mp3
Category:For Agency Owners and Consultants -- posted at: 5:37am EDT

Chaos and order… this is possibly one of my favorite frameworks for life and business.
Feeling stressed and overwhelmed... this episode is for you. 
Feeling content and wanting more… this episode is for you.
This episode gets into another high-level mindset of how I think about my life and business.
Want to work with me as an advisor? Visit
Direct download: WWP_Chaos_and_Order_in_your_business.mp3
Category:For Agency Owners and Consultants -- posted at: 9:01am EDT

As your business grows, you inevitably become a bottleneck within your own companies' growth.
The hard thing is to identify when this happens.
We find all sorts of reasons to justify to ourselves to stay in a role that we know we should hand-off… yet there is a time and place to recognize when you are a bottleneck to your own growth.
Want to work with me as an advisor? Visit
Direct download: WWP_bottleneck.mp3
Category:For Agency Owners and Consultants -- posted at: 10:06am EDT

This simple question is a powerful one. 
In this solo episode, I dive into this question and share some exercises for you to get clear on what you want. 
Direct download: wwp_What_do_you_want_2.mp3
Category:For Agency Owners and Consultants -- posted at: 11:01am EDT

Overwhelmed… That is a good way to summarize how I felt the past few weeks.
Too many projects.
Too many opportunities. 
Too many tasks. 
Too many calls. 
As entrepreneurs, we often hit this level of “overwhelm” when we are working too hard… 
I’ve hit it many times, and many of my advising clients have experienced this also.
In this episode, I talk through how I deal with overwhelming situations.
Direct download: wwp_What_to_do_when_you_are_overwhelmed.mp3
Category:For Agency Owners and Consultants -- posted at: 7:51am EDT

There is a famous story from Charlie Munger where he talks about his early days as a lawyer.
He talks about how his focus at any given time is on doing the best job possible at the work in front of you today.
So many entrepreneurs are focused on themselves and growing their business...
Their head is in the sky instead of focusing on doing the best they can for the customers they have today.
In this solo episode of the Working Without Pants Podcast, I dive deep into this idea of "Investing in your customers".
Direct download: WWP_investing_in_your_customers.mp3
Category:For Agency Owners and Consultants -- posted at: 9:00am EDT

Here is another solo podcast episode where I talk about money, mindsets, and how my mindset has evolved with money over the course of my entrepreneurial career. 

Direct download: WWP_How_my_mindset_on_money_has_evolved.mp3
Category:For Agency Owners and Consultants -- posted at: 7:15am EDT

Yep. I have fully embraced the title of serial entrepreneur.
Currently ramping up a total of 5 new companies in partnership with others... (and more coming soon).
Want to work with me as an advisor? Visit
Direct download: WWP__How_I_am_launching_5_new_companies.mp3
Category:For Agency Owners and Consultants -- posted at: 6:42am EDT

This week I have a chat with Dani Bell of, a productized content marketing agency that does everything from planning through to production and ongoing guidance to help clients consistently boost traffic and attract leads.
Scribly is 18 months old and after a pivotal shift, they've seen a great growth. We talk about the challenges that come with big pivots and Dani shares everything she's learned along the way. With everything that's happening in the world, it seems there is a changing perception of the value of content.
Tune in to hear our thoughts on whether it's worthwhile to put your pricing on your site or not (Scribly does). Tons of value in this episode, don't miss out.
Direct download: WWP_Dani.mp3
Category:For Agency Owners and Consultants -- posted at: 5:05am EDT

Today's episode sees me chatting with Jay Baer of Convince and Convert. Jay has been working in digital since 1993 - tune in to hear a story about the sweet deal he made with Anheuser-Busch over ownership of
Jay's agency is built up of 3 parts: a content strategy firm, a media & sponsorship company, and a paid public speaking business. It's not your typical agency as it focuses on strategy only, as opposed to execution.
Did I mention Jay is a Hall of Fame speaker? Super interesting guy, tons of value in this episode. Especially for agencies wanting to go upmarket to do higher-level strategy work as opposed to just execution.
Direct download: WWP_Jay_baer.mp3
Category:For Agency Owners and Consultants -- posted at: 5:04pm EDT

This week I had the pleasure of chatting with Brian Burns, host of a network of podcasts, including The Brutal Truth About Sales & Selling podcast and the B2B Revenue Leadership podcast.
Brian worked in software enterprise sales for 25 years before going out on his own. Today, he's built up such a stellar podcast following that he's able to work full-time on creating value through podcast content.
In this episode, we discuss the complex sale and how to sell to bigger companies. If you're stuck in your comfort zone and only selling to SMBs, tune in to hear Brian's advice on how to level up and what to expect when selling to bigger companies.
Direct download: WWP_Brian_burns.mp3
Category:For Agency Owners and Consultants -- posted at: 7:46pm EDT

This week I had a chat with Kean Graham of MonetizeMore, a large ad tech company with over 140 remote workers living all over the world.
MonetizeMore serves a really unique niche in the publishing industry. They help publishers with ad monetization through the use of tech and proprietary manual optimization techniques. Tune in to hear the story of how the company grew and how they successfully niched-down. I think you'll find a ton of value in this episode.
Direct download: WWP_Kean_Graham.mp3
Category:For Agency Owners and Consultants -- posted at: 7:41pm EDT

On today's episode I chat with Alyssa Patzius, COO of Influencer & Co., a content marketing agency based in Columbia, Missouri (near where I grew up!) Influencer & Co. connects the dots between earned media PR and your on-site content so you can build an entire cohesive inbound funnel with tangible ROI.
This is a great episode for anyone interested in learning more about scaling from a small local business to a large global agency with team members all over the world. Tune in to hear how Influencer and Co. structures their content and sales procedures. I got tons of value from our conversation and I'm sure you will too!
Direct download: WWP_Alyssa_Patzius.mp3
Category:For Agency Owners and Consultants -- posted at: 7:51am EDT

On this episode, I sit down with Jason Bay of Blissful Prospecting. Jason and I are in the same Outbound industry, but we took different paths. His business helps sales teams to bring in more leads through cold outreach. Sales reps are great at taking demos and doing sales calls, but the struggle is often that the marketing team isn't filling their pipeline with leads - Blissful Prospecting provides training for sales teams so they can fill their pipeline with more organic leads (and depend less on the marketing team).
If you're interested in the outbound industry, you'll enjoy being a fly on the wall as we discuss the different paths you can take within 'outbound'. We also dive into topics like the dynamics of being a business partner with your wife and the psychological and mental challenges of being an entrepreneur.
We're all navigating our businesses through tough times right now, there's tons of food for thought on that topic this conversation.
Direct download: WWP_jason_bay.mp3
Category:For Agency Owners and Consultants -- posted at: 1:05pm EDT

Today I sit down with Tristan Pelligrino of Motion, a content marketing agency that helps B2B tech companies generate demand with genuine conversations. They do this through the creation of thought leadership programs that revolve around podcasts, video series and other shareable formats.
Tristan has 15 years of experience working with agencies, which means he has tons of great advice to share when it comes to building and running agencies. We both run our companies off of the EOS model, if you're not familiar with this framework for developing your business' vision, learning about this alone will be a game changer for you!
Direct download: WWP_Tristan_Pelligrino.mp3
Category:For Agency Owners and Consultants -- posted at: 9:07am EDT

On this week's episode I sit down with John Logar, founder of John isn't just a coach, he has tons of experience building and scaling a variety of different businesses, and also runs a huge successful agency. He is a great example of someone who practices what he preaches, while he's learning at the same time.
Through Consulting Unleashed, John is known for building companies quickly using a consistent methodology (Attract, Convert, Leverage) that teaches people to scale successfully. He helps to get his clients their first 6 figures and has a wealth of ideas on both scaling and developing your offer.
John believes 'If you offer often, people are going to buy'. Don't miss out on this episode, John gives away a lot of his expert ideas for free, including advice on things you can do today to go out and start making new sales.
Direct download: WWP_John_Logar.mp3
Category:For Agency Owners and Consultants -- posted at: 2:19pm EDT

In this episode, I sit down with Dvorah Graeser, founder of KISSpatent, a productized patent service. Dvorah took what used to be an expensive, oft lengthy legal service mostly used by corporations and turned the model on its head by offering it as a fixed-price product that puts the power of patents in the hands of innovators.
This is a great episode for anyone wondering how they might able to apply a patent to their business. Tune in to us discuss a number of different forms of idea protection for innovators and startups. Access to idea protection is on the rise, thanks to great endeavors like this one.
Direct download: WWP_Dvorah_Graeser.mp3
Category:For Agency Owners and Consultants -- posted at: 11:19am EDT

This week I speak with Geoff Atkinson of Huckabuy. Geoff was previously employed in the corporate world at as the Senior VP of Marketing and successfully transitioned to running his own business at Huckabuy, which is now generating over 1M MRR.
Geoff's first entrepreneurial endeavor started as a B2C affiliate website and eventually pivoted to a performance-based SEO software company. It took at least 2-3 years to find their footing, but they eventually found a way to respond to market needs.
Don't miss out on this episode, Geoff has great advice for first-time entrepreneurs trying to build a strong revenue-driven business. Whatever your brilliant idea is, be open to the fact that it might not be what the market wants and you may need to take the time to create change so you can pivot and respond to what the market wants.
Direct download: WWP_Geoff_Atkinson.mp3
Category:For Agency Owners and Consultants -- posted at: 3:49pm EDT

Listen to this week’s episode if you’re feeling stressed, overworked, or battling with finding a balance between your entrepreneurial life and your personal life. Sherry Walling has a PhD in clinical psychology and specializes in entrepreneurial health. Sherry also owns ZenFounder along with her podcast and is the author of “The Entrepreneur’s Guide to Keeping Your Sh*t Together: How to Run Your Business Without Letting it Run You”.
Now, while this particular interview actually took place before the current health events happening around the world, this couldn’t be better timing for someone that needs to hear this message. Some of us are forced to either step back and break from business or ride the waves and put added effort into our companies. Sherry dives into lots of practical tips regarding burnout, family life, depression, and the loneliness that entrepreneurship can entail.
Learn here why it’s important to our brain health, the livelihood of our businesses, and our personal lives to ‘unplug’ sometimes. You may be struggling with your sense of value and identity intertwining with your business. But where do you draw the line between your time freedom, money, and weighing what you value most out of life? Sherry will share some insightful advice that will hit home with all of us, both literally and figuratively. And don’t forget to check her out on her websites at or Also, Sherry mentions her Guide to Founder Retreats that you can check out here.
Direct download: WWP_Sherry_Walling.mp3
Category:For Agency Owners and Consultants -- posted at: 11:40pm EDT

This week, I speak with Tyler Gillespie, the “Thinking Time Chief” of Applause Lab, a company that creates great customer video testimonials and other social proof. Before Applause Lab, Tyler sold his content writing service company, and here we discuss details on what his journey of building Applause Lab was like after selling. This is super informative and a great place to be to learn about the process of starting your own company.
Tyler describes his experience with the content writing business, which remains nameless during our interview, and how he was able to continually help clients get value from his service. Sometimes, it takes a simple prompt idea or two to be proactive when preventing client churn. That was all before Tyler went through the process of acquisition. Then, as we shift into a conversation about Applause Lab, his current business venture, we’ll walk you through his experience with how the launching and execution went rather quickly. 
This episode is so worth checking out! Get some advice on how you can decipher what business you may want to get into and what questions to ask when doing so. Find out more information on Applause Lab by visiting or join the Facebook group called Productized Startups to follow Tyler on his journey with his company. 
Direct download: WWP_Tyler_Gillespie.mp3
Category:For Agency Owners and Consultants -- posted at: 4:22pm EDT

Matthew Kimberley pours out some amazing insights in this week’s episode that you won’t want to miss! With a background in sales and as an author himself, Matthew has also taken over the entire program called Book Yourself Solid, which was originally created and written by Michael Port.
With Book Yourself Solid, Matthew helps business owners figure out what path is right for them. The book offers frameworks for you to think through this and what fundamental principles and mindset you can apply to reach your business goals. If you need to convert or generate leads, Michael can help you, so long as you are actively doing these things somehow.  It’s about strategies verse the tactics- this is truly an interesting outlook on how you should question your motives. 
If people pay you for your time and your expertise, this book and this episode are for you! There are so many great pieces of advice that Matthew dives into here that are both exciting and thoughtful. I realized there are different ways to think about growth for your business… and it’s not always about more money.
Direct download: WWP_Matthew_K.mp3
Category:For Agency Owners and Consultants -- posted at: 6:40pm EDT

For those that have been reading my blog posts, you know by now that I’ve successfully handed off my sales role to a friend-turned-team member. That team member is Isaac Marsh. Isaac is not only head of sales with Lead Cookie, but he helps test new offer strategies we put on the table as well. With a passion for writing, his natural ability to talk with others, and starting his own agency with his business partner, it was a no-brainer to reach out for him to take on this position. 
The stars aligned when I approached Isaac and his business partner and asked if they could come on board with Lead Cookie a while back. That was the beginning of handing off my sales role successfully. I made mistakes trying to hand this off before, which did not work out, so I took Isaac through a different and more specific process when he came on board. 
Give this episode a listen if you’re looking to get the sales role off your plate. We share what worked and what mistakes were made as well. Isaac has some great insights into what helped him take on sales and how he adjusted the frameworks to feel more natural to him for the sales calls. Isaac is essentially our “gatekeeper” at Lead Cookie and you, as an owner, can learn why relinquishing that control will allow your business to have one as well.
Direct download: WWP_Isaac_Marsh.mp3
Category:For Agency Owners and Consultants -- posted at: 6:17pm EDT

Why is it so important to start thinking about what acquisition looks like for your business? You’ll want to find out here in this episode with John Warrillow. John is the Founder and President of The Value Builder System and author of the books "The Automatic Customer: Creating a Subscription Business In Any Industry" and "Built to Sell: Creating a Business That Can Thrive Without You.” 
Knowing what your intentions are for your business is of the utmost importance. If you want your company to be valuable, or transferable, it has to be able to run without you. Even if you are not planning to sell, this may trigger some lightbulbs for your business and help steer you on the right path for long-term mentality.
I’ve received a ton of value from reading John’s books that caused a huge mindset shift for me, and so I was honored to have the chance of interviewing him. This episode is recommended for anyone going down a productized service path and, I promise, this will change your perspective on your business. We discuss what “Deal Momentum” is and you’ll want to hear this! And don’t forget to check out to learn more.
Direct download: WWP_John_Warilow.mp3
Category:For Agency Owners and Consultants -- posted at: 7:09pm EDT

Wherever “Ledge” goes, sales go up! Join this week’s episode to hear what I mean by this and get some great insight into taking leads and rocking a sales execution to help grow your revenue. David Ledgerwood, Managing Partner at Add1Zero, is someone I’ve known for years and I refer to as “Ledge” here. He and his team use a proven process for a 6 to 7-digit annual growth by providing sales strategy, execution, and ops to their clients. 
Learn about the “secret sauce” Ledge speaks of here! It’s great. In fact, I just took a lot of notes while interviewing him and have action items I am excited to try.  I have already quadrupled my own sales by working with Ledge before. This is truly insightful and I think you will get tons from this episode, so hurry now and give it a listen. 
Direct download: WWP_David_Ledgerwood.mp3
Category:For Agency Owners and Consultants -- posted at: 12:13pm EDT

Listen in on this week’s episode to hear about a softer, yet super powerful skill to learn for your business: Storytelling. Kyle Gray joins us from and walks us through how he went from working for WP Curve to becoming a bestselling author who helps startups and small businesses grow with content marketing. 
Kyle specializes in helping clients of all different levels tell better stories to not only earn their audience’s trust but for the audience to trust themselves with investing in his clients’ businesses. There are specific tactics you can use to get better at storytelling and that is where Kyle came up with 3 simple steps for combining information into an outline for a great story or speech. 
If you’re an expert in your field but have difficulty in expressing your value and how you’re different, this episode is for you. You can learn the simple framework here that will help you get your message across without sounding too “salesy.” Or if you want to jump right in and read Kyle’s book, you can find it at or on Amazon.
Direct download: WWP_Kyle_Gray.mp3
Category:For Agency Owners and Consultants -- posted at: 7:08pm EDT

In this “best selling” episode, Kevin Anderson joins us from Kevin Anderson & Associates. With offices in New York City, Nashville, and Los Angeles, Kevin’s firm is made up of a team of New York Times bestselling writers, editors, and publishing consultants- offering all three of these top-notch services and producing high-quality content for their clients. 
Kevin Anderson & Associates buckle down with dedication to each client to help formulate the content to ghostwrite their books-- whether it is starting from scratch from a few ideas or helping someone edit and rewrite a book they’ve already written. Kevin’s firm is also well connected to some of the industry’s best literary agents, marketers, publicists, and more to help make a book successful once it’s written. Many clients come to Kevin’s team specifically because of connections Kevin has to a variety of people in the industry and the marketing strategies they use. 
If you are thinking about writing your own book but not sure where to start, or if you are looking into hiring ghostwriters, be sure and join us here for some great insights with Kevin!
Direct download: WWP_Kevin_Anderson.mp3
Category:For Agency Owners and Consultants -- posted at: 10:44am EDT

If you are charging hourly and have a hit ceiling, this episode is definitely for you! This week, Jonathan Stark joins me once again as we dive into his “mission to rid the world of hourly billing.” He’s a former software developer and is now the author of Hourly Billing Is Nuts, the host of a podcast called Ditching Hourly, cohost of Business of Authority, and writes a daily newsletter about pricing for independent professionals. 
Join us here to learn some awesome techniques and avenues to become an authority figure, broaden your network, connect more intimately with your audience, and command higher rates. This includes something as simple, yet huge, with daily emailing. Jonathan is determined to help consultants become authorities in their field so they can break out of that rut of trading time for money. 
This interview was truly relevant to me and has sparked some ideas for my own business. I know you’ll want to take notes on this one. Dive in here and then go check out Jonathan’s website at
Direct download: WWP_Jonathan_Stark.mp3
Category:For Agency Owners and Consultants -- posted at: 10:27pm EDT