Working Sessions

By: John Doherty and James Sowers
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  • Summary

  • 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!
    © 2022 Waypoint Ventures, LLC
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Economics Leadership Marketing
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Episodes
  • Catching up and Finding a Competitive Edge

    Catching up and Finding a Competitive Edge
    Aug 15 2023

    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:

    • Join Our Email Newsletter for early access and bonus content
    • Come and hang out with us in our Slack community
    • Follow James on Twitter and LinkedIn
    • Follow John on Twitter and LinkedIn

    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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    45 mins
  • Sometimes, It Requires More Than You Think

    Sometimes, It Requires More Than You Think
    Aug 3 2023
    In this episode, we provide updates on our respective businesses and share some insights about the idea of doing more in the aspects of business and work. This highlights the idea that in order to get uncommon results, live an uncommon life which is an essential reference for a business which is striving to do a lot better in the future, always aiming to surpass expectations while also putting emphasis on work and life balance. As always, we also provide updates on Castaway and EditorNinja, which include...Updates on EditorNinjaCastaway updates Emphasizing work and life balanceSound interesting? You should give it a listen. We think you'll really enjoy it.Want to support the show? [FREE]Subscribe to future episodes in your favorite podcast appAsk a question or leave us feedback on this episodeLeave an honest review on your favorite podcast platformShare the show with a friend who might also enjoy itReach out to us on Twitter and give us your unfiltered feedbackWant more regular updates? Here are other ways to follow along:Join Our Email Newsletter for early access and bonus contentCome and hang out with us in our Slack communityFollow James on Twitter and LinkedInFollow John on Twitter and LinkedIn Thanks & RecognitionThis episode was edited by PodcastBuffs.TIME STAMPS AND KEY IDEAS(00:00:31) The idea of doing more, sometimes it requires more than you think. Discussions involve the idea that whatever you are doing or what your goal might be setting, one should multiply it by 10x because ultimately, you'll end up ahead, always striving to surpass expectations. (00:01:07) Uncommon results : uncommon effortsSharing lessons from Hormo Z's book where he likes doing more volume to learn faster, work a lot faster which will eventually result to succeding a lot faster. Most of the time, people expect that they will get uncommon result even just doing the same normal things. However, it was emphasized that if anyone wants to get uncommon results, exert an uncommon level of effort and live an uncommon life. (00:02:50) Best practice is the baselineReviewed over the base line of the things that should be done and nothing more assuring than make the best practice a standard. Key to that is always striving to take action instead of just staying stagnant, doing more effort, practicing more to be able to the get work done even faster. Moreover, one must hold oneself to imposed standrads, and act accordingly as everyone are commiting and dedicating their entire life basically to the single pursuit of whatever they are trying to do. (00:13:21) Allocate experience points like a game Compared skills updates on games with how work should be done. Increasing attributes is like allocating more experience, more hours and more focus on things which are important in a business. This is where productize and scale comes in because this will help in the idea of how to put people and processes in place. With productize, things can be brought up and turn into process rather than just randomly doing things. (00:28:06) Focus on what is important Knowing what's the focus is an advantage and a strength as it would enable the business to pave a way for the things of great significance and make sure it is done and executed well. It is also what being productive is like, alloting much time to things which are in the higher heirarchy and allocating proportionate amount of time to each, for example, tasks giving it more time, based on importance. TAKEAWAY LESSONDoing more with what you are doing is a good practice but upon working it is a must to consider a personal space as well. Strictly getting control and putting over boundaries between work and personal space is essential as to not exhaust the body and mental health. One must not bend ones life just so you can fit your employer's preferences, and remember to take into account a work and life balance.
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    39 mins
  • Fear or Greed

    Fear or Greed
    Aug 3 2023

    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:

    • Join Our Email Newsletter for early access and bonus content
    • Come and hang out with us in our Slack community
    • Follow James on Twitter and LinkedIn
    • Follow John on Twitter and LinkedIn

    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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    42 mins

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