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Working Sessions

Working Sessions

John Doherty and James Sowers

Working Sessions gives you a behind-the-scenes look at what it's like to build a six figure side hustle from scratch. You'll follow the journeys of John Doherty (EditorNinja) and James Sowers (Castaway) as we attempt to build successful productized service businesses while also being high-performing leaders, fathers, and husbands. Subscribe if you'd like to hear about the ups and downs of our experience, including everything from hiring to sales to operations and finances. Can't wait to see you at our next working session!
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Top 10 Working Sessions Episodes

Goodpods has curated a list of the 10 best Working Sessions episodes, ranked by the number of listens and likes each episode have garnered from our listeners. If you are listening to Working Sessions for the first time, there's no better place to start than with one of these standout episodes. If you are a fan of the show, vote for your favorite Working Sessions episode by adding your comments to the episode page.

Working Sessions - Entrepreneurship: Nature or Nurture?
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01/25/23 • 44 min

In this episode, we share our thoughts on whether we think entrepreneurship is a trait that's primarily driven by "Nature" (Ex: inherited through genetics) or "Nurture" (Ex: Self-taught or learned through non-familial environments). We also share business updates that cover a range of topics from conversion rate optimization to testing new ad channels.

If that sounds like something you'd be interested in, you should give it a listen!

Timestamps:

(0:00:05) - Nature vs. Nurture in Entrepreneurship
(0:06:44) - Risk-Averse Entrepreneurship
(0:12:36) - Editor Ninja's Yearly Update
(0:19:32) - Optimizing Conversion Rates
(0:27:47) - Strategies for Growing Businesses
(0:35:08) - Testing Advertising Channels
(0:43:53) - Progress and Catch Up

Key Ideas:

(0:00:05) - Nature vs. Nurture in Entrepreneurship (7 Minutes)
We explore the debate around nature versus nurture when it comes to entrepreneurship. It is suggested that, while there are certain innate tendencies that could lead someone to be an effective entrepreneur, it is the environment and people around them who will ultimately put them on the path towards entrepreneurship. It is proposed that, if someone was born into a household where entrepreneurship is already present, they will have a greater chance of becoming an entrepreneur themselves. The conversation further suggests that, while both nature and nurture have a role to play in entrepreneurship, the research on the impact of having entrepreneurial parents is yet to be seen.

(0:06:44) - Risk-Averse Entrepreneurship (6 Minutes)
'Risk aversion' and 'willingness to take risks' were discussed in the context of entrepreneurship. It was suggested that taking big risks can be dangerous as most of them crash and burn. There was also discussion on the importance of being a 'polymath' or having diverse interests, being able to learn from different areas, being okay with delayed gratification, and finding joy in the process rather than the outcome. Furthermore, the impact of parental entrepreneurship on children's entrepreneurship was discussed, citing a study from University of Chicago that found that parental entrepreneurship increases a child's probability of becoming an entrepreneur by 60%.

(0:12:36) - EditorNinja's Yearly Update (7 Minutes)
Editor Ninja' updates are discussed, with the speaker providing an overview of the business since the beginning of the year. Revenue has exceeded expectations, with three months in a row of around $8,000 in cash collected. The goal of creating a six-figure side hustle has been achieved, with volume increasing three times in the last six weeks. New offerings are being tested, along with a challenge to post content on YouTube shorts. A new conversion path was put live but is not working, prompting the speaker to consider how to rejigger it.

(0:19:32) - Optimizing Conversion Rates (8 Minutes)
This conversation covers a range of topics related to optimizing conversion rates on a website. It is suggested that the call to action should be more descriptive and that the highest burden for conversions would be if customers are asked to pay fifty dollars to start. It is also recommended to streamline the process by having customers sign up for an account, submit a document, and then have the opportunity to upgrade their account or switch to a different service package. To test this, three versions of the homepage with a different call to action should be tested. Lastly, it is suggested to offer a discounted cost or free document to get customers to try the service'

(0:27:47) - Strategies for Growing Businesses (7 Minutes)
This conversation focuses on the processes of conversion and automation, and how best to approach them. It looks at the importance of getting customers to take their first step with a business, and how to nurture them afterwards with automated emails and segmentation. The conversation then moves to the current situation of Castaway and Productize & Scale, and how leads and conversations are increasing, though difficulty arises when it comes to closing the deal. The two discuss the Black Friday promotion of Productize & Scale, which has almost reached the figure of last year, and how the funds could be used to reinvest in ads for Castaway.

(0:35:08) - Testing Advertising Channels (9 Minutes)
The conversation focuses around running ads for businesses and the experience of running ads for Editor Ninja. It is discussed that Google Ads can be a great tool for driving traffic and conversions, but that it is important to be mindful of the budget allocated. It is mentioned that newsletter sponsorships can be effective, but can also be costly. The importance of understanding the market and setting realistic expectations is discussed,...

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Working Sessions - Fear or Greed

Fear or Greed

Working Sessions

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08/03/23 • 42 min

In this episode, we provide updates on our respective businesses and feeding the greed and fear index where business encountered a place of uncertainty in the economy while sharing some helpful advice on how businesses and individuals can not only survive, but thrive during an economic recession. This includes talking about the recent economic downturn and some helpful insights which will let everyone view situations in different perspective.

As always, we also provide updates on Castaway and EditorNinja, which include...

  • Updates on EditorNinja
  • Castaway Updates
  • Finding a competitive edge with Castaway

Sound interesting? You should give it a listen. We think you'll really enjoy it.

Want to support the show? [FREE]

  1. Subscribe to future episodes in your favorite podcast app
  2. Ask a question or leave us feedback on this episode
  3. Leave an honest review on your favorite podcast platform
  4. Share the show with a friend who might also enjoy it
  5. Reach out to us on Twitter and give us your unfiltered feedback

Want more regular updates? Here are other ways to follow along:

Thanks & Recognition

This episode was edited by PodcastBuffs.

TIME STAMP AND KEY IDEAS

(00:04:02) Pandemic Recession
There are winners or losers in business. Some business might have gone outside the grid during the global economic downturn as their services are getting weak demands. On the other side of the globe, there are other business who found a way through the recession and came across great opportunities especially for alcohol, soap, disinfectant and hygeine focused companies.

(00:04:48) Invest in Skills
Even with the pandemic recession, some companies which had found an opportunity with the situation has been lacking with employees so they considered hiring people and reconsidering what their market looks like. Business tend to find a person at the right time and should give the right offer for them - more like finding someone which can take the work and produce quality result.

(00:15:12) Manage Churn
Tackled one of the things to be fearful of right now which is a retraction or churn. Sort of hassle to actually need more volume in order to get the same number of customers as preceding years but churn is what kills subscription and recurring billing companies. This highlights the important to be an account manager who actually cares and monitor to have more people use the service more.

(00:19:15) AI Taking Over
AI is eating the SEO world and is commonitized. AI is somehow as good as Castaway where it can affect the business prices. This raises concern that there is a tendency to either lose business or find a competitive edge and there is no way losing is an option. Having a clear understanding of what your clients need are then it must be an easy way to go as this will open up opportunities for the business.

Lesson Takaway
Despite everything, try not hitting the panic button immediately. There are plenty of people out there who can close better deals, it is not a necessity to sacrifice too much over little things and strive as not to get locked in a job you don't enjoy too much.

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Working Sessions - Buying Back Your Time

Buying Back Your Time

Working Sessions

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08/03/23 • 41 min

In this episode, we provide updates on our respective businesses and discuss the hiring framework to help business owners who are in the process of onboarding new talents. Came up with a few sharing of book lessons, experiences in our own hiring process to keep you guys informed on the things needed to focus upon delegating roles to save you some time, effort and money.

As always, we also provide updates on Castaway and EditorNinja, which include...

  • Hiring and testing out VAs for EditorNinja
  • Announcement of EdNinja's launch of editing for ai created content service
  • Castaway Updates
  • Moving Productize and Scale website from WordPress Power to Ghost
  • James planning to launch more courses

Sound interesting? You should give it a listen. We think you'll really enjoy it.

Want to support the show? [FREE]

  1. Subscribe to future episodes in your favorite podcast app
  2. Ask a question or leave us feedback on this episode
  3. Leave an honest review on your favorite podcast platform
  4. Share the show with a friend who might also enjoy it
  5. Reach out to us on Twitter and give us your unfiltered feedback

Want more regular updates? Here are other ways to follow along:

Thanks & Recognition

This episode was edited by PodcastBuffs.

TIME STAMPS AND KEY IDEAS

(00:03:03) Hiring
EditorNinja talk's about Dan's book where it was emphasized that upon hiring, one must think at what they are good at, and do the process in terms of an energy and money kind of access. To make it short, hiring is somewhat similar to buying back your time and putting it in other stuffs which are actually of significance in the business.

(00:06:14) Hiring is a bet on oneself
Hiring is actually asking yourself if you can afford to hire somebody, or if you are in a position to actually bring somebody in. It's a process that needs to be delegated and outsourced carefully, looking for what's actually gonna move the needle. It was also tackled that oftentimes people make mistakes in hiring as they always focus on immediately hiring VA's or EA's without actually weighing in and asking themselves what roles am I delegating and I'm left to take on.

(00:08:46) Don't just delegate the task, delegate the role
It is good to get people to keep an eye on a task which is discussed by Dan highlighting how you don't just delegate task, you delegate the role and then they become responsible and accountable for that particular area. Delegating the role rather than the task will buy your time back, because it is as if you are replacing yourself by turning over that particular role to them and you just kind of move on to another role saving you 15-20% of your time which can be invested on other important matters.

(00:10;56) Focus on something you are good at
James talks about the idea of the accountability chart which kind of starts with picturing out what seats are needed to fill the in for the particular roles. Making a plan is essential and following a stairstep approach of hiring people to fill in those empty roles, as to only be left with ideally what business owners are good at. Basically focusing on what gives the highest value in the business and pouring attention into it.

(00:17:29) Updates on EditorNinja
EditorNinja is currently hiring and testing out VAs from different countries, basically observing the process for a month or so to see which one will do better. Announced the launch of editing for ai created content service, which has blown up pumping a higher demand for the service. In addition, the base price for copy editing and proofreading has been raised a bit - more or less 15-20% - but also considering on stepping up to a higher level, like adding AI content updating, developmental editing, and a full high touch level where customers give out content and EditorNinja will do everything for them.

(00:24:09) Updates from James
Sharing about how James is hiring thr...

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Working Sessions - How To Survive (& Thrive) Through A Recession
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12/28/22 • 41 min

In this episode, we provide updates on our respective businesses and share some advice for how small business owners can not only survive, but thrive during an economic downturn. This includes reviewing a viral post from Patrick Campbell (ProfitWell) about how business owners should be changing their mindset/behaviors, given all of the uncertainty in the market right now.

As always, we also provide updates on Castaway and EditorNinja, which include...

  • New homepage and editor profiles for EditorNinja
  • Insights from a round of customer interviews
  • Announcing James' acquisition of Productize & Scale
  • Plans to add on-demand services to Castaway

Sound interesting? You should give it a listen. We think you'll really enjoy it.

Want to support the show? [FREE]

  1. Subscribe to future episodes in your favorite podcast app
  2. Ask a question or leave us feedback on this episode
  3. Leave an honest review on your favorite podcast platform
  4. Share the show with a friend who might also enjoy it
  5. Reach out to us on Twitter and give us your unfiltered feedback

Want more regular updates? Here are other ways to follow along:

Thanks & Recognition

This episode was edited by PodPanda.

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Working Sessions - Setting Our Business Goals For 2023
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02/08/23 • 44 min

In this episode, we discuss our respective business goals for the new year, which include plans to attend conferences and launch marketing initiatives. We also touch on current and emerging trends, like AI tools, and explore the potential impact it might have on our work. Finally, we reflect on the lessons we learned over the past year and which ones we'll be carrying forward with us in 2023.

If that sounds interesting to you, you should give it a listen.

Timestamps:

[00:02:26] Discussing the concept of "Memento Mori"

[00:07:04] Chatting about Generative AI as a technological step-change

[00:11:50] Weighing the pros and cons of the "gold rush" around AI content

[00:14:04] Predicting increased important for human-generate content in the future

[00:20:55] Talking about outsourcing and the time cost of onboarding versus the time saved later.

[00:26:58] Balancing freelance and full-time workers to meet demand.

Key Ideas:

1. AI and its Current Status in the Industry

- AI is a step change technology but won't replace jobs yet

- AI Wrangler is a new role

- AI output is dependent on the quality of input and is still bland and lacks personality, opinion, and point of view.

2. Making the Most of Life and the Hype on Chat GPT

- Remind yourself to make the most of life

- Discussing the hype on Chat GPT.

3. Outsourcing and its Time Cost

- Consider the time cost of onboarding when outsourcing

- Outsourcing can save time later.

4. Human-Made Content will be Valued More

- AI tools will be valued less than human-made content in the future.

5. Balancing Freelance and Full-Time Workers and Hiring Writers

- Balancing freelance and full-time workers to meet demand

- Hiring writers with a bigger budget

- Subcontracting work.

6. Effective Strategies for Selling and Generating Revenue

- Successfully offering and selling a course, coaching, website audit, and lifetime membership.

- Generating almost $11,000 in revenue.

7. Unplugging and Recharging in January

- Unplug, enjoy, and recharge for January.

8. Time Flies When Raising Children

- Time passes quickly when raising children.

9. Forecasting Future Business Revenue and Growth

- Forecasting $150K revenue, 30% margin, launching a new product/service line, updating flagship course, 25K revenue from product ties.

- Consistent publishing cadence and repurposing productized podcast episodes to create a physical book.

10. AI Generated Content: The Potential "Gold Rush"

- AI generated content is a potential "gold rush" with short term gains but possible long term risks.

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Working Sessions - How To Qualify Prospects During The Sales Process
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11/16/22 • 40 min

In this episode, we provide updates on our respective businesses and share how we qualify prospects for our services during the sales process. It's tempting to take the "easy money" of a new client, especially in the early days, but it's better to focus on right-fit clients from the start to set your business up for long-term success.

As always, we also provide updates on Castaway and EditorNinja, which include...

  • Another new hire for EditorNinja!
  • Setting benchmarks for performance before investing in sales/marketing
  • Continuing to iterate on offers until you find the right option
  • Using "slow periods" to dial in your operational efficiency
  • Gearing up for a podcast promo tour

Sound interesting? You should give it a listen. We think you'll really enjoy it.

Want to support the show? [FREE]

  1. Subscribe to future episodes in your favorite podcast app
  2. Ask a question or leave us feedback on this episode
  3. Leave an honest review on your favorite podcast platform
  4. Share the show with a friend who might also enjoy it
  5. Reach out to us on Twitter and give us your unfiltered feedback

Want more regular updates? Here are other ways to follow along:

Thanks & Recognition

This episode was edited by PodPanda.

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Working Sessions - The Value Of Coaching In Life And Business
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11/02/22 • 40 min

In this episode, we provide updates on our respective businesses and talk about the value of coaching in our lives and businesses. James hasn't had a serious coach since high school, whereas John has hired multiple coaches to support him in various areas.

We discuss the merits of hiring a coaching, but also the risks or downsides of hiring the wrong coach. If you've ever considered working with one yourself, this episode should be excellent pre-work to help you make a smart decision.

As always, we also provide updates on Castaway and EditorNinja, which include...

  • Letting go of your first team member
  • A ranking update on the top-level service pages we made last time
  • How to evolve your offerings based on market demands
  • A whale client is in the pipeline for Castaway
  • What to do when competitors start to go silent

Sound interesting? You should give it a listen. We think you'll really enjoy it.

Want to support the show? [FREE]

  1. Subscribe to future episodes in your favorite podcast app
  2. Ask a question or leave us feedback on this episode
  3. Leave an honest review on your favorite podcast platform
  4. Share the show with a friend who might also enjoy it
  5. Reach out to us on Twitter and give us your unfiltered feedback

Want more regular updates? Here are other ways to follow along:

Thanks & Recognition

This episode was edited by PodPanda.

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Working Sessions - Catching up and Finding a Competitive Edge
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08/15/23 • 44 min

In this episode, we provide updates on our respective businesses, helpful lessons and scenarios to aid entrepreneurs in moving forward while standing strong amidst commoditized services. This highlights discussions of lessons about becoming competitively different which would prove useful to business that offers the same service and finding a competitive edge.

As always, we also provide updates on Castaway and EditorNinja, which include...

  • Overcoming slow pipeline and churn rates
  • Castaway recovery
  • Consider offering video editing with Castaway
  • Productize updates

Sound interesting? You should give it a listen. We think you'll really enjoy it.

Want to support the show? [FREE]

  1. Subscribe to future episodes in your favorite podcast app
  2. Ask a question or leave us feedback on this episode
  3. Leave an honest review on your favorite podcast platform
  4. Share the show with a friend who might also enjoy it
  5. Reach out to us on Twitter and give us your unfiltered feedback

Want more regular updates? Here are other ways to follow along:

Thanks & Recognition

This episode was edited by PodcastBuffs.

Time Stamps and Key Ideas

00:04:59 Do what kind of works for you.
Highlights individual pursuits where focus is on things that works for oneself like how to do things at your own pace.
00:09:34 Updates on EditorNinja
Pipeline kind of slowed down and they had a little bit of churn however, EditorNinja is still slowly getting into it, constantly, steadily and healthily growing. Things came slower as they doubled prices around January or February, although sales process are tightened up, people are still closing deals. Services are priced competitively, providing quality services relieving people from the burden of doing things their own or hiring a full-time editor themselves.

00:13:50 Just Be Hard to Kill
Contains a talk highlighting what Sam Altman said about a superpower of startups which is "just be hard to kill". Meaning, whatever the changing market throws unto you, one must be ready to change and look for opportunities to strive amidst the
unforgiving sea of challenges and try to rides its waves. If one can, try to outlast everybody else until you're the only one standing by then getting hundred percent of the market's attention.

00:14:45 Catching Up
Discusses a lesson that one should be greedy while others are scared and be scared when others are greedy. This tackles being competitive while also analyzing how to ride the market trends, not only just going to where everyone else is going but also striving to stand out instead of being drawn towards commoditization.

00:25:56 Updates on Castaway and Productize
Still at a mild-mannered situation as James is still exploring on his preferred tool set, still recovering slowly and getting some clients back. Mainly focusing on produtize at this moment, updating the course and exploring community angle, slowly building a business ecosystem. James is thinking of acquiring a small business and layering it into Castaway like an editing so it could handle a full spectrum of podcast production and promotion.

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Working Sessions - What Is The Right Time (& Price) To Sell Your Company?
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06/08/22 • 45 min

In this episode, we start by talking about how to know when it's the right time to "cash in" and sell your business. When is the right time to open your mind to selling the company? How do you know when an offer is an okay deal versus a no-brainer? What can you do today to prepare yourself for an eventual sale? We share our thoughts on each of those point and more.

As always, we also provide updates on Castaway and EditorNinja, which include...

  • What to do when a marketing decision kills your sales call/demo volume
  • How to structure your website navigation when you offer numerous services
  • Whether you should be a niche specialist or an end-to-end solution
  • Where to start with process and training documentation
  • How to build a personal brand to drive new leads for your business

Sound interesting? You should give it a listen. We think you'll really enjoy it.

Want to support the show? [FREE]

  1. Subscribe to future episodes in your favorite podcast app
  2. Ask a question or leave us feedback on this episode
  3. Leave an honest review on your favorite podcast platform
  4. Share the show with a friend who might also enjoy it
  5. Reach out to us on Twitter and give us your unfiltered feedback

Want more regular updates? Here are other ways to follow along:

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Update: You can now listen to this episode and our entire back catalog over on our YouTube channel!

In this episode, we go into more detail about how we landed on our business ideas, how we're fitting them into our lives, and what goals we have for them over the next year.

If you're interested in learning about how we...

  • Came up with the ideas for EditorNinja and Castaway
  • Determined that these ideas are worth pursuing
  • Plan to fit these projects into our already-busy lives
  • Structure our day for maximum effectiveness (without burning out)
  • Define "success" for ourselves over the next year

...then you should give it a listen. We think you'll really enjoy it.

Resources Mentioned In This Episode:

Want to support the show? [FREE]

  1. Leave an honest review on your favorite podcast platform
  2. Share the show with a friend who might also enjoy it
  3. Reach out to us on Twitter and give us your unfiltered feedback

Want more regular updates? Here are other ways to follow along:

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FAQ

How many episodes does Working Sessions have?

Working Sessions currently has 28 episodes available.

What topics does Working Sessions cover?

The podcast is about Marketing, Content Marketing, Entrepreneurship, Podcasting, Podcasts and Business.

What is the most popular episode on Working Sessions?

The episode title 'How To Balance "Learning" With "Doing"' is the most popular.

What is the average episode length on Working Sessions?

The average episode length on Working Sessions is 41 minutes.

How often are episodes of Working Sessions released?

Episodes of Working Sessions are typically released every 7 days, 1 hour.

When was the first episode of Working Sessions?

The first episode of Working Sessions was released on Mar 2, 2022.

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