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 overly involved in the process. The goal is to have others take complete ownership over their role without your daily guidance. 

When moving someone into a manager-type role, it's best to set a hard deadline for when they are expected to fully take charge. It's okay to provide occasional support but you want them to be able to problem-solve on their own.

During this process, you should provide a detailed job description, clearly define a team member’s new expectations, and outline what success looks like. If problems do come up, try to avoid immediately jumping back in. If you are always there to come to the rescue, your new leader will stay reliant on you.

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching.

My companies could not do what they do without Zapier. We use Zapier to automate tasks and connect all of our various web applications together. It could be connecting Airtable to Slack, our invoicing software to Airtable, our Project Management tool to Payroll… the integrations we use it for are endless. If you aren’t using Zapier, get on the bandwagon and try it out at Zapier.com

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 certain milestones, however, new problems show up at each level of entrepreneurship. Just when you think you have a skill set mastered, things get challenging again when more money and business scale are involved. If you try to rely on the skills and attitudes that got you to this point without further growth, you’ll not only halt progress but actually shrink when faced with new market and business conditions.

For these reasons, I highly recommend working with an advisor or coach who has been through the different stages of entrepreneurship. They will help uncover your blind spots so that you’re able to evolve and tackle the next stage of your journey.

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching.

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 efforts.

In this episode of the Working Without Pants podcast, I sit down with Isaac Marsh, Partner at Lead Cookie, to discuss these changes and explore why hand-qualifying leads and boosting the quality of your outbound efforts is necessary for success when prospecting on LinkedIn.

We describe why these changes force you to respect your prospects’ time and how the reduction in “noise” is creating better engagement with outreach efforts.

We also talk about how focusing on quality with outbound ultimately saves you time, generates leads that you can actually close, and disqualifies bad leads before you waste time hopping on a call with them.

For the sustainability of the platform, we think this is the right move for LinkedIn and look forward to the benefits it will bring.

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching

• https://www.vidyard.com/podcast/nopants/
• https://www.leadcookie.com/
• https://contentallies.com/

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, as well as offering à la carte options you can use to customize packages as needed. 

This will streamline your sales process, reducing the time spent negotiating with clients. It also helps keep your operations team organized and able to scale more efficiently and quickly.

It’s also important to have your packaging and pricing information organized on a simple rate card that you can easily share with clients. There may be cases where you alter pricing for specific clients, but the line items stay the same.

If you can be diligent about following a productized framework like the one above, you’ll minimize your team’s workload and have less confusion about your services.

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching

• https://www.vidyard.com/podcast/nopants/
• https://contentallies.com/

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 categories: 1) needs, 2) shoulds, 3) wants.

Needs are those tasks that absolutely need to get done in order for your business to continue functioning without anything negative happening.

Shoulds are those tasks that don’t need to get done immediately but should get done in the near future to help grow your business.

Finally, wants are those things that could potentially help your business, but there’s really no downside to not doing them.

If you’re in need of a recharge, simply focus on your needs for a week and then see where you’re at. You would be surprised how freeing it can be to prioritize your work in this way. 

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching.

• https://www.vidyard.com/podcast/nopants/
• https://contentallies.com/

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 such as with SEO auditing, a credit-based pricing model allows you to stay more agile and helps with upfront planning of deliverables.

Another benefit of using a credit-based pricing model, according to Corey, is that it eliminates the need for time tracking. When everyone knows what needs to be done and can deliver on schedule, day-to-day tracking isn’t all that important.

He says it can initially be a challenge for clients to understand a credit-based system, but as long as you’re delivering high quality work and have your value specs properly documented, it doesn’t cause much fuss.

Corey closes the show by sharing his insight around system development lifecycles and some of the tools his team uses to streamline their workflow.

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching

• https://www.linkedin.com/in/coreynorthcutt/
• https://northcutt.com/
• https://twitter.com/corey_northcutt

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 take the comprehensive workflows Content Harmony developed for creating content briefs and turn them into a SaaS offering.

According to Kane, this shift to a SaaS model of business was a product of understanding what processes his agency excelled at, working with the right talent to build the software properly, and doing the proper market research to understand the needs of their customers.

For agencies considering developing a SaaS product, Kane encourages you to get crystal clear on the objective with the product. He advises doing whatever work you can yourself to reduce costs, and looking for opportunities to launch micro-products while building out the product’s grand vision.

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching

• https://www.contentharmony.com/
• https://www.linkedin.com/in/kanejamison/

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 deals.

Dan talks about finding the right outbound/inbound sales ratio in order to meet your clients where they’re at. If you’re not gathering data on this ratio, you’re shooting in the dark and won’t know what to expect from increasing outbound or inbound efforts.

He also shares the importance of assessing who your best customers are and why they are closing. This allows you to refine who your company wants to work with, how to best serve them, and repeat the process with future clients. 

Dan closes the show by describing some of the strategies he uses when coaching sales teams, noting the benefits of talking through deals out-loud to figure out where a deal is stuck.

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching

Resources:

• Coaching Salespeople into Sales Champions 
• Mindracerconsulting.com
• https://www.linkedin.com/in/danmorrisprofile/

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 breeze.

I discuss the different tactics you can use to promote your podcast including: 

• QUUPromote.com
• Social Media paid promotion
• Word of mouth
• Repurposing podcast content

I also outline which materials you need to be sending your guests so that they can easily promote the podcast through their social channels. This will enhance your credibility and reach far more than just promoting your podcast yourself.

If you’re ready to get started on your podcasting journey, visit https://contentallies.com/ to learn more about our full-service podcast production services.

Resources: 

Anchor

QUU Promote

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 your guests in advance and taking this information to brainstorm questions about your guest’s background and experience that you want to explore deeper.

I highlight why you should let your curiosity drive the flow of your interviews and the crucial role that active listening plays in keeping your conversations engaging. 

You’ll also learn why great podcasters always have a set of fallback questions to rely on if their initial questions don’t take up as much time as they thought.

With these tips in mind, you’ll be well on your way to conducting great interviews that bring true value to your audience.

If you’re ready to get started on your podcasting journey, visit https://contentallies.com/ to learn more about our full-service podcast production services.

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 outline how to easily record audio using tools such as Zoom and Zencastr. With the right equipment in hand, you can record your intro podcast episode(s), which play an important role in familiarizing your audience with what they can expect from your show.

I also direct you to platforms you can use to find your podcast music and describe the tools we like to use to create your own podcast website. 

With these items checked off your to-do list, you’ll be more than prepared to launch your podcast.

If you’re ready to get started on your podcasting journey, visit https://contentallies.com/ to learn more about our full-service podcast production services.

Resources:

• Pond5
• Envato Elements
• https://www.upwork.com/
• https://www.fiverr.com/
• Squarespace
• PodcastPage.

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 partners instead of peers in order to generate new business. 

I also dive into the different ways you can go about selecting a name and why there’s no perfect formula you have to follow. It really comes down to what name would attract your ideal prospects and audience, and this differs from industry to industry.

I talk about why interview-based podcasts are best for the B2B sector and why the length of your show isn’t as important as being able to deliver value throughout the entirety of your show. 

If you’re ready to get started on your podcasting journey, visit https://contentallies.com/ to learn more about our full-service podcast production services.

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 approach because the focus is on the human capital of an agency versus tangible assets, which is the case with many traditional businesses. She also notes that sellers of agencies are typically younger with long careers ahead of them. This creates unique deal structures.

To minimize their risk, Amanda says buyers prefer agencies with a lot of recurring retainer revenue and a more robust management team. Smaller freelance teams with project-based revenue are inherently riskier for buyers.

For agency owners looking to sell, Amanda says not to be scared of scaling up before your exit. Reaching a few more key financial milestones can go a long way for increasing your multiple on the sale.

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching.

• https://www.vidyard.com/podcast/nopants/
• https://contentallies.com/
• https://www.wearebarney.com/

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 management skills.

In this episode of the Working Without Pants Podcast, I outline all the moving parts and people you’ll need to successfully launch and maintain a podcast.

I walk through the processes, the talent, and time commitments that go into each episode and highlight why in most cases you’ll be better off working with an outsourced team of podcast production experts.

As a leader, you only have so much time. And this time is best spent focussing on hosting great interviews instead of worrying about all the details that go into consistently delivering valuable content to your audience.

If you missed the first episode in this podcast series, be sure to go check it out and then revisit this episode.

If you’re ready to get started on your podcasting journey, visit https://contentallies.com/ to learn more about our full service podcast production services.

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 level guests on your podcast, and how these engagements lead to lasting relationships built on trust.

I also walk through the other reasons why starting a podcast is valuable, including how it positions you as an authority, leads to speaking opportunities, allows you to repurpose your material into other social content, and generates inbound leads.

If starting a podcast has ever been on your mind, this episode and the following episodes in this series are for you.

Content Allies helps B2B companies launch revenue-generating podcasts. We set you up with weekly interviews with your ideal prospects and strategic partners. You show up and have engaging conversations, we handle EVERYTHING else. 

From show strategy and guest outreach, to audio production and podcast syndication. We do it all.

With packages starting at $3k per month, we make podcasting an ideal growth channel for you. 

Learn more and say hello at ContentAllies.com

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 Co-Founder of Arkona and is an online educator who aims to impart the ability to plan, grow, and prepare your business for that lucrative exit several years before it happens. 

Ryan talks about the 5 Key Principles of Intentional Growth. This guides businesses in establishing their identity as early as their foundation and growth stage. These principles touch cover everything from what you are trying to solve to your financial targets and the value of your business.

Watch this episode to gain insight on how to prepare your business properly so you can grow it and gain financial freedom from it in the future. 

Gain and learn more essential business knowledge at the following resources to complement this episode:

• Arkona.io - Gain access to digital courses on Intentional Growth and Mastering Your Cash Flow with Ryan Tamson.

• ContentAllies.com - In today’s tight world of marketing and brand identity, providing content for people to learn differentiates you from the competition. Content Allies works with you on creating podcasts that result in revenue generation for your business. 

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching

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 jake-jorgovan.com/coaching

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 jake-jorgovan.com/coaching

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

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 jake-jorgovan.com/coaching

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 jake-jorgovan.com/coaching

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 jake-jorgovan.com/coaching

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

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 entrepreneurs don’t consider themselves “finance people,” but that line of thinking will negatively impact their business at some point or another. Though bookkeeping may not be your strong suit, it’s important to educate yourself to make informed business decisions based on your books.

Gaining a better understanding of your books and finances will allow you to set a realistic and predictable salary month after month. It will also allow you to maintain clean and actionable books, which is vital if you ever want to sell your business. Furthermore, taking control of your finances will reduce a lot of stress and chaos for you and your business.

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching.

• https://www.vidyard.com/podcast/nopants/
• https://contentallies.com/
• https://www.smokymountaintax.com/
• https://www.financeforagencies.com/
• Profit First
• Simple Numbers, Straight Talk, Big Profits

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 jake-jorgovan.com/coaching

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/coaching

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 jake-jorgovan.com/coaching

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 business, it can seem daunting. The key to remember, though, is that you don’t have to be an expert at building systems — you simply need to understand them enough to be able to eventually hire a master to optimize your basic frameworks. If a system has decent bones, a specialist will be able to come in and take that system to the next level of efficiency.

I always recommend starting your system-building efforts by focusing on lower-value work that you want off your plate and then moving on to higher-level work. This will bring you more immediate freedom, allow you to refine your system-building skills, and ultimately help you understand what it will take to systematize higher-level roles or tasks down the line.

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching.

https://www.vidyard.com/podcast/nopants/

https://contentallies.com/

https://add1zero.co/

https://www.process.st/

https://www.amazon.com/Built-Sell-Creating-Business-Without/dp/1591845823

https://www.amazon.com/Work-System-Fourth-Mechanics-Working/dp/1626347697

https://www.amazon.com/Clockwork-Design-Your-Business-Itself/dp/0525534016

- - - 

Lead Cookie is a B2B lead generation agency that focuses on quality above all else. Tired of getting burned by low-quality spammy agencies who over-promise and fail to deliver results. Then reach out to us to experience the difference at LeadCookie.com

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. 

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 best for your business, some testing is required. Typically, you should be able to see if a channel is working within about three months. Once you find a channel that works, I recommend doubling down on that channel and scaling it up. You can repeat this process with any other channel you think might work.

By focusing on a few channels that produce predictable results, you will not only have consistent leads coming in but will reduce the time and energy you need to spend on marketing. With a repeatable process in place, you can easily delegate those marketing efforts to someone other than yourself.

Want to work with me as an advisor? Visit jake-jorgovan.com/coaching.

• https://www.vidyard.com/podcast/nopants/
• https://contentallies.com/