Working Without Pants - Creative Entrepreneurship

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. This episode is brought to you by Zapier 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.

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

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. Resources: https://www.vidyard.com/podcast/nopants/https://contentallies.com/https://www.smokymountaintax.com/https://www.financeforagencies.com/Profit FirstSimple Numbers, Straight Talk, Big Profits

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. Resources: 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 - - - This episode is brought to you by Lead Cookie 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

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

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 show by discussing the fact that more people are realizing that quality beats quantity when it comes to outbound leads. If you’re selling high-ticket packages, one client can pay for all your future outbound efforts. Though an outbound agency may guarantee you a set amount of leads, none of those deals will close if the quality isn't there. We also highlight how outbound gives you long-term brand exposure and helps you stay top of mind for when prospects are ready to buy. Though you might not close a deal today, you can gauge where a prospect is in their buying cycle. This gives you the ammo you need to nurture that lead and form a strategy for when that lead is ready. Want to learn how Lead Cookie can help with your outbound efforts? Feel free to reach out to us today. Resources: https://www.vidyard.com/podcast/nopants/https://www.leadcookie.com/ This episode is brought to you by Lead Cookie 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

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 still being able to accomplish everything I need to. My first tip if you’re feeling overwhelmed while trying to manage work with play is to take a step back and ask yourself, “What happens if I don’t get XYZ tasks done this week?” What you’ll find is that many of the things you’re stressing about can be pushed back without any consequences. Making this paradigm shift isn’t about making an excuse to be lazy, but rather it’s about supporting your mental health while being fully engaged on the days you are working. Minimizing your workweek can actually bring about more productivity on the tasks that really matter and allow you more freedom to pursue your interests outside of work. Want to work with me as an advisor? Visit jake-jorgovan.com/coaching Resources: https://www.vidyard.com/podcast/nopants/https://contentallies.com/https://www.leadcookie.com/

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 discuss the key things our research team looks for, including companies that are hiring for roles relevant to your business, decision-makers changing positions, funding or expansion news, and RFPs (request for proposals). Furthermore, you receive the exact contact information for the stakeholders you need to talk to in order to gain new business. We also talk about how Custom Data is able to help you build out a custom CRM of prospects that fit your buyer criteria. Instead of wasting time searching through mediocre databases, you’ll have a pipeline of pre-qualified leads your sales team can contact right away. If you’re interested in learning more about how Custom Data can help you get more deals, feel free to reach out to us at https://www.customdata.ai/. Want to work with me as an advisor? Visit jake-jorgovan.com/coaching Resources: https://www.vidyard.com/podcast/nopants/https://www.customdata.ai/isaac@customdata.ai

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 seen the outbound industry evolve and how agencies should be thinking about outbound. We discuss the issue of misaligned expectations between agencies and their clients regarding the results clients want to achieve. These agencies promise a certain amount of leads, but this number is really just a vanity metric. To serve clients best, you need to understand their true needs and develop a campaign that puts them in front of their ideal clients. We also describe why outbound has more benefits than just closing deals in a short amount of time. These benefits include getting precise on your ideal clients, expanding your network of influence, and creating a long-term pipeline of potential clients. Want to work with me as an advisor? Visit jake-jorgovan.com/coaching Resources: https://www.vidyard.com/podcast/nopants/isaac@leadcookie.comhttps://contentallies.com/

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 Resources: 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 Resources: 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. Resources: 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 Resources: 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 Resources: 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.comhttps://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.comSocial Media paid promotionWord of mouthRepurposing 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: Pond5Envato Elementshttps://www.upwork.com/https://www.fiverr.com/SquarespacePodcastPage.

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.