Working Without Pants - Creative Entrepreneurship – Details, episodes & analysis

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.