Working Without Pants - Creative Entrepreneurship artwork

Working Without Pants - Creative Entrepreneurship

171 episodes - English - Latest episode: about 2 years ago - ★★★★★ - 54 ratings

Working Without Pants is the podcast for agency owners and consultants who are wanting to win more clients and better clients for their business.

Each week, Jake Jorgovan brings you interviews with industry leaders and experts on how to win more clients for your agency or consulting practice.

Past guests have included Brennan Dunn, Brent Weaver, Kai Davis, Philip Morgan, Brian Casel, Blair Enns, and many more.

Learn more at https://jake-jorgovan.com/podcast

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Episodes

213: Leading Others and Letting Go

June 27, 2022 04:00 - 13 minutes - 11.9 MB

To experience the freedom that entrepreneurship can provide, you need to learn how to let go of certain responsibilities and let others lead.    In this episode of the Working Without Pants podcast, I provide some tips on how to let team members take ownership of more responsibility and what that process looks like.    In many cases, people confuse delegation with letting others lead. Delegating new tasks can be a step toward moving someone into a different role, but you’re still ove...

212: What Got You Here Won't Get You There

June 21, 2022 04:00 - 10 minutes - 9.42 MB

There are many shifts you go through as an entrepreneur. And there most definitely will be a time when the tactics and mindsets that worked for you previously will need to be updated in order to level up.   In this episode of the Working Without Pants podcast, I discuss the importance of continuing to evolve as an entrepreneur and why there are always new challenges awaiting you throughout your entrepreneurial journey.   Many entrepreneurs think things will get easier as they reach c...

M&A for Agencies with Amanda Dixon

January 03, 2022 12:32 - 31 minutes - 29.2 MB

Digital agencies are very different from traditional businesses, thus buyers and sellers of these agencies need to approach M&A in a particular way.   In this episode of the Working Without Pants podcast, I sit down with Amanda Dixon, co-founder of Barney, to discuss how agency owners should be thinking about M&A to maximize their exit. We also talk about what buyers are looking for when acquiring digital agencies. Amanda shares that M&A for digital agencies requires a different approa...

211: M&A for Agencies with Amanda Dixon

January 03, 2022 12:32 - 31 minutes - 29.2 MB

Digital agencies are very different from traditional businesses, thus buyers and sellers of these agencies need to approach M&A in a particular way.   In this episode of the Working Without Pants podcast, I sit down with Amanda Dixon, co-founder of Barney, to discuss how agency owners should be thinking about M&A to maximize their exit. We also talk about what buyers are looking for when acquiring digital agencies. Amanda shares that M&A for digital agencies requires a different approa...

210: Finance for Agencies

December 14, 2021 14:09 - 15 minutes - 14.2 MB

Though making money is a key goal of any business, many business owners aren’t very financially savvy. If you’re a business owner that simply hands off your finances to a bookkeeper without involving yourself at all, you’ll likely have a finance problem at some point in time.   In this episode of the Working Without Pants podcast, I discuss the importance of understanding your business’s finances and provide some useful tips to start becoming more financially literate.   Many entrepr...

209: How To Think About Systems

December 07, 2021 20:45 - 17 minutes - 16.3 MB

When building a business or starting a new entrepreneurial pursuit, we tend to handle many of the day-to-day tasks ourselves. And though working this way is fine for a while, at some point you need to turn that chaos into an orderly system.   In this episode of the Working Without Pants podcast, I explore the importance of building systems and why they are needed in order to scale your business in an organized and predictable way.    If you’re new to building systems within your busi...

208: How To Think About Marketing

December 02, 2021 05:00 - 11 minutes - 10.1 MB

One of the most common mistakes I see business owners and marketers make is spreading their marketing efforts across too many channels. The focus needs to be on the scalability of a few channels instead of getting caught up in launching as many campaigns as possible.   In this episode of the Working Without Pants podcast, I share my insight on how you should be thinking about marketing in order to produce real results for your business.    To see which marketing channels will work be...

207: Building Outbound as a Sustainable Growth Channel With Isaac Marsh, Partner at Lead Cookie

November 30, 2021 05:00 - 30 minutes - 28 MB

Many people expect quick wins from outbound and if they don’t see results in a few months, they drop it altogether. This is unfortunate because the real power of outbound comes from your ability to build outbound as a long-term growth channel for your business.   In the new episode of the Working Without Pants podcast, Isaac Marsh, Partner at Lead Cookie, joins me to discuss how people should be thinking about outbound and why it's such a sustainable growth channel.   We kick off the...

206: Why To Consider a 4 Day Work Week

November 16, 2021 17:00 - 8 minutes - 7.99 MB

Traveling or engaging in other activities outside of work is always great. But trying to fit in a full week of work in a three- to four-day period to accommodate these activities can be stressful if not approached correctly. Instead of feeling anxious about getting everything done, I’ve found it’s best to re-prioritize work and focus on the essentials.   In this episode of the Working Without Pants podcast, I share my journey of how I’ve come to love a three- to four-day workweek while s...

205: Introducing my New Company, CustomData.ai

August 24, 2021 04:00 - 23 minutes - 21.3 MB

In this special episode of the Working Without Pants podcast, Isaac Marsh joins me to discuss our new business venture, CustomData.ai. At a high level, Custom Data scrapes the internet looking for prospects with your specific intent signals to buy. We gather this intent data and deliver you and your sales team hand qualified leads every single week. Not only is this data immediately actionable, but it gives you all the details you need to confidently approach your outbound efforts. We di...

204: How Lead Cookie is Navigating the Evolution of Outbound with Isaac Marsh

August 16, 2021 08:33 - 32 minutes - 30.1 MB

Many outbound agencies focus on delivering high quantities of leads but leave much to be desired in regards to the quality of those leads.  Though playing the numbers game can work to an extent, we believe there are better outbound strategies that reduce the risk of damaging your agency’s reputation and at the same time bring qualified leads to your clients. In the new episode of the Working Without Pants podcast, Isaac Marsh, Partner at Leader Cookie, joins me to explore how we have see...

203: Why We Are Happy about LinkedIn’s Limits with Isaac Marsh

August 10, 2021 03:53 - 22 minutes - 20.3 MB

If you’ve been a user of LinkedIn over the years, you’ve probably witnessed the shift from it being a very relationship-focused platform, to one where your inbox is filled with spammy messages and connection requests. For these reasons, LinkedIn has reduced the number of connection requests you can send from 2,500 per month to 100 per week. This is bad news for those that spray-and-pray connection requests, but it's extremely beneficial for those that already focus on quality outbound effo...

202: Packaging and Pricing for Productized Services

August 03, 2021 12:17 - 18 minutes - 17.3 MB

When productizing services, it can be a challenge to figure out how to package and price those services. Additionally, having the discipline to stick to a productized framework is often more difficult than people realize. In this episode of the Working Without Pants podcast, I share a methodology that has helped me productize services successfully, and the benefits it can bring to your business. In essence, I recommend building three core packages to align with different tiers of service...

201: A Framework for Improving Work-Life Balance

July 26, 2021 06:17 - 15 minutes - 14.1 MB

Work-life balance is crucial for the sustainability of any entrepreneur.  Most of us have some method, activity, or way to find this balance, but sometimes this balance can only be found through the prioritization of your tasks at hand. In this episode of the Working Without Pants Podcast, I share an effective framework of prioritization I have been using to find more work-life balance. The framework is quite simple. You start by organizing your work tasks and projects into three categ...

200: Systems Development and Credit-Based Pricing with Corey Northcutt

April 28, 2021 09:16 - 43 minutes - 39.4 MB

Building and implementing robust processes and systems for your business is a must when trying to create more efficiency and scalability within your business. In this episode of the Working Without Pants podcast, I sit down with Corey Northcutt, Founder and CEO at Northcutt, to discuss the processes he has built for his SEO enterprise agency, and why using a credit-based pricing model was the right fit for his business. Corey notes that when offering technical services with many steps su...

199: Converting from an Agency to a SaaS Company with Kane Jamison

April 20, 2021 17:00 - 40 minutes - 37.1 MB

On this episode of the Working Without Pants podcast, I sit down with Kane Jamison, Founder of Content Harmony, to discuss his journey of transforming his content marketing agency into a SaaS business. Kane shares that though his content marketing agency was successful in many respects, it wasn’t going to reach the level of self-sufficiency that he desired. He wanted to narrow his focus on an offering that could scale better and help content marketers everywhere. Thus, Kane decided to ta...

198: Running a Multi-Million Dollar Sales Team with Dan Morris

April 13, 2021 09:04 - 45 minutes - 41.2 MB

On this episode of the Working Without Pants podcast, Dan Morris, Managing Partner at Mindracer Consulting, sits down with me to share his experience of growing, training, and managing world-class sales teams. Dan discusses his journey in sales and why cultivating internal motivation and curiosity are key factors for the success of any salesperson. This curiosity paired with the right training and market research are what bring down the walls for clients and can position you to close more ...

Part 6 - How to host, syndicate, and promote your podcast

April 06, 2021 15:18 - 12 minutes - 11.3 MB

To get your podcast out to the world, proper hosting and promotion are a must. In this episode of the Working Without Pants podcast, I’ll cover the essential details you need to consider when hosting, syndicating, and promoting your B2B podcast. I walk through some of the available hosting platforms and recommend using Anchor because it’s easy to use, budget-friendly, and utilizes up-to-date technologies. Anchor also makes syndicating your podcast to iTunes, Spotify, or other channels a ...

Part 5 - How to Conduct a Great Podcast Interview

March 30, 2021 08:20 - 11 minutes - 10.4 MB

Though hosting your podcast and interviewing guests may seem a little intimidating when you’re just starting out, it’s much easier than you think. As a host, you’ll actually only be speaking a small portion of the time. It’s your guests and their insight that fills most of the conversation. On this episode of the Working Without Pants podcast, I’ll cover the tips and strategies you can use to conduct engaging interviews with world-class guests. I discuss the importance of researching y...

Part 4 - Preparing for Your B2B Podcast Launch

March 23, 2021 10:21 - 15 minutes - 14.5 MB

In between the ideation phase of your podcast and your first guest interview, there are important details you need to get in order. On this episode of the Working Without Pants podcast, I’ll dive into everything you need to accomplish to be well prepared for your B2B podcast launch. Beginning with podcast artwork, I discuss how to find a graphic designer and what details you need to communicate to them. I provide suggestions for which podcast microphones will suit your purposes and outli...

Part 3 - How to Build Your B2B Podcast Strategy and Plan

March 16, 2021 15:16 - 16 minutes - 14.9 MB

All great podcasts start with an idea to share valuable information. But, the idea alone isn’t enough.  You need to refine this idea into a functional strategy for targeting a specific audience with a distinct message. In this episode of the Working Without Pants Podcast, I’ll explore some of the things you need to consider before ever hitting record on your first podcast episode. I discuss why when deciding on your podcast’s subject matter, it’s important to appeal to prospects and pa...

Part 2 - How to Build Your B2B Podcast Production Team

March 09, 2021 18:05 - 17 minutes - 15.7 MB

Any great podcast is backed by a full podcast production team. From conceptualizing your strategy all the way through publishing and promoting a finished product, there are many moving parts that need to be organized. Typically, you either outsource this work to a full service podcast production agency, or you can choose to hire individuals to build an in-house team. Though it may be more cost effective to try and tackle this in-house, it takes a tremendous amount of time and project man...

Part 1 - Why Launch a B2B Podcast

March 02, 2021 14:00 - 20 minutes - 18.5 MB

The biggest myth around starting a podcast is that you need to build a large following in order to be successful. Building an audience is part of the equation, but it is far from the greatest value driver of starting a podcast. In this episode of the Working Without Pants Podcast, I describe why the number one value driver from podcasting is how it amplifies your ability to network with strategic partners, prospects, and influencers. I discuss why it’s easier than you think to get high l...

191: Building for a Lucrative Exit with Ryan Tansom

January 14, 2021 17:13 - 46 minutes - 42.9 MB

A multitude of startup founders who take the plunge into entrepreneurship do so with the goal of financial freedom and independence. But when faced with the prospect of an investment, an acquisition, or a merger, most entrepreneurs don’t realize what needs to be done. This can lead to a shattered realization of a broken dream as the vision of that financial gain from all your hard work begins to fade into obscurity. Today’s episode of Work Without Pants features Ryan Tansom. Ryan is the ...

190: Running 9 companies at the same time with David Henzel

December 10, 2020 13:02 - 36 minutes - 33.6 MB

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 inco...

189: Selling your first company with Dave Schneider

December 04, 2020 14:08 - 42 minutes - 38.8 MB

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 sam...

188: Why entrepreneurs should take more vacations

November 20, 2020 13:44 - 12 minutes - 11.7 MB

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 jake-jorgovan.com/coaching

187: Building a market research firm with Sarah Weise

November 05, 2020 09:54 - 38 minutes - 35.4 MB

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...

186: Building a performance-based marketing agency with Adam Weiler

October 29, 2020 13:37 - 41 minutes - 38.2 MB

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...

185: Rethinking success with Doug Holladay

October 22, 2020 16:38 - 44 minutes - 40.9 MB

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 ...

184: The slow build of a SaaS product with Jeroen Corthout

October 09, 2020 16:45 - 46 minutes - 42.2 MB

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 (Passaroo.com - 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 jake-jorgovan.com/coaching

183: Building an outbound training company with Jason Bay

October 01, 2020 10:52 - 50 minutes - 45.8 MB

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...

182: Building your personal brand with Elyse Archer

September 24, 2020 12:52 - 39 minutes - 35.9 MB

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 jake-jorgovan.com/c...

181: Why selling marketing services is stupid

September 10, 2020 12:53 - 13 minutes - 12.3 MB

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 jake-jorgovan.com/coaching

180: How to succeed in your next hire

September 03, 2020 15:51 - 10 minutes - 9.95 MB

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 jake-jorgovan.com/coaching

179: Building a business that scales without employees featuring Pia Silva

August 27, 2020 14:48 - 36 minutes - 33.2 MB

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 ze...

178: Scarcity mindset never goes away

August 20, 2020 09:37 - 10 minutes - 9.78 MB

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 jake-jorgovan.com/coaching

177: Chaos and Order in your business

August 13, 2020 13:01 - 8 minutes - 7.97 MB

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 jake-jorgovan.com/coaching

176: How to spot when you are a bottleneck in your own business

July 16, 2020 14:06 - 9 minutes - 8.61 MB

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 jake-jorgovan.com/coaching

175: What do you want

July 09, 2020 15:01 - 11 minutes - 10.4 MB

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. 

174: What to do when you are overwhelmed

July 02, 2020 11:51 - 13 minutes - 12.5 MB

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.

173: Invest in your customers

June 25, 2020 13:00 - 7 minutes - 6.86 MB

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 th...

172: How my mindset on money has evolved

June 11, 2020 11:15 - 21 minutes - 19.8 MB

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. 

171: How I am launching 5 new companies

June 04, 2020 10:42 - 18 minutes - 17.4 MB

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 jake-jorgovan.com/coaching

170: Building a productized content agency with Dani Bell

June 03, 2020 09:05 - 43 minutes - 39.4 MB

This week I have a chat with Dani Bell of Scribly.io, 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 ...

168: Building an agency / media company / speaking firm with Jay Baer

May 28, 2020 21:04 - 40 minutes - 37 MB

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 Budweiser.com.   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? ...

167: Selling to enterprises with Brian Burns

May 20, 2020 23:46 - 43 minutes - 40 MB

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. I...

166: Scaling to 140+ remote team members with Kean Graham

May 13, 2020 23:41 - 43 minutes - 39.7 MB

This week I had a chat with Kean Grahamof MonitizeMore, a large ad tech company with over 140 remote workers living all over the world.   MonitizeMore 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.

166: Scaling to 140+ remote team members with Kean Graham

May 13, 2020 23:41 - 43 minutes - 39.7 MB

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.

165: Scaling a content agency to 100+ team members with Alyssa Patzius

May 06, 2020 11:51 - 44 minutes - 40.6 MB

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 h...

Guests

Jonathan Stark
2 Episodes
Chris Ducker
1 Episode
David Turner
1 Episode
Drew McLellan
1 Episode
Josh Elledge
1 Episode
Mandi Ellefson
1 Episode

Twitter Mentions

@benleenr 1 Episode
@nowspeed 1 Episode
@mikemcderment 1 Episode
@corey_northcutt 1 Episode
@neonroots 1 Episode