Working Sessions

In this episode, we start by talking about whether entrepreneurs should collect input from their customers and build the solution(s) they are asking for, or if they should try to build a creative solution to a specific problem and then educate customers on why they need it.

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

• Solving the riddle of a two-sided marketplace
• How to structure your demos/sales calls
• Hiring to replace yourself in a skilled role
• Marketing ideas for bootstrapped service businesses

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
• Follow John on Twitter

In this episode, we start by talking about the recent acquisition of Carthook and use that as context to discuss our own "exit strategies." We also talk about what defines a successful business outcome and what our long-term goals are for our projects.

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

• A discussion about service positioning/value propositions
• A brainstorming session around whitelabeling for agencies
• A confession about putting important work off because it feels daunting
• A quick therapy session on whether to sprint or jog when building a side hustle

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
• Follow John on Twitter

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

In this episode, we start by talking about how much time, attention, and energy you should give to competitors and copycats. (Spoiler alert: Not much!) Then, we get into our respective business updates, which include process efficiencies and hiring challenges.

If you're interested in learning about...

• How to handle competitors and copycat services
• How to figure out which pricing model is best (Ex: retainer vs. usage vs. a la carte)
• When and how to test new service ideas
• Whether you should scale up your team or scale up your revenue first

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

Resources we covered in this episode:

• Kinsta – John's preferred WordPress hosting service
• Bench – John's favorite bookkeeping service
• Asana – James' preferred project management tool
• Trello – John's preferred project management ool
• Alex Hormozi – A must-follow business builder and growth advisor
• Chris Lema – Another must-follow business coach and mentor

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
• Follow John on Twitter

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

In this episode, we jump into some company updates, which include hiring contractors, managing team availability/workload, navigating the enterprise sales process, and how narrows to focus your professional positioning. Then, we have a friendly debate about the pros and cons of on-demand services versus a monthly subscription model.

If you're interested in learning about...

• How to manage availability and capacity for your team
• How selling to enterprise clients is different from SMB sales
• How we're competing with "we do it all" firms
• How James is using the "land and expand" positioning strategy
• How to hire multi-disciplinary teams of contractors
• The merits and flaws of a la carte pricing vs. subscription services

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

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:

• Visit WorkingSessions.fm and join our newsletter
• Follow James on Twitter
• Follow John on Twitter

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

In this episode, we start by talking about a recent tweet from Kevin Indig, which suggests that leaders and business owners should treat themselves like professional athletes. We then go into some company updates, which include a handful of important topics for business owners to think through.

If you're interested in learning about...

• How to manage physical/mental health and avoid burnout
• Why specialization/positioning is an important part of business
• When you should hire your first team member (+ how fast to add more)
• When you should start paying yourself (+ how much)
• When to say no to client requests, and when to be flexible

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

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:

• Visit WorkingSessions.fm and join our newsletter
• Follow James on Twitter
• Follow John on Twitter

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:

• The Big Leap by Gay Hendricks
• The Perfect Day by Craig Ballantyne
• The Miracle Morning by Hal Elrod
• AudienceOps – The agency where James learned podcast production
• The tweet that gave James the confidence to work on Castaway

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:

• Visit WorkingSessions.fm and join our newsletter
• Follow James on Twitter
• Follow John on Twitter

In this episode, we recap how we met and came up with the idea for Working Sessions. We also provide a brief overview of our projects and how they fit into our current lifestyle.

John is working on EditorNinja, an unlimited, on-demand copy editing and proofreading service.

James is working on Castaway, a done-for-you podcast promotion and repurposing service.

We also cover our goals for the podcast, including cadence, format, and subject matter. If you have thoughts on how we can improve going forward, feel free to hit us up on Twitter.

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

• Visit WorkingSessions.fm and join our newsletter
• Follow James on Twitter
• Follow John on Twitter

You're listening to Working Sessions, a podcast by John Doherty (@dohertyjf) and James Sowers (@jamesrsowers) where we give you a behind the scenes look at what happens when two self-proclaimed "marketing guys" try to build a successful service business from scratch.

John is working on EditorNinja, an unlimited, on-demand copy editing and proofreading service.

James is working on Castaway, a done-for-you podcast promotion and repurposing service.

Each episode, we'll provide an update on how our businesses are doing and share some actionable advice around a specific topic, like...

• How to find your first customers,
• How to price your services
• How to balance being a high-performing parent, spouse, and business leader

We've both agreed to share the highs and lows of entrepreneurship, which includes being transparent about things like processes, tools, client interactions, and finances.

So, if you're interested in following along as two experienced entrepreneurs attempt to build six figure side hustles from scratch, you've come to the right place. Hit that subscribe button and we'll send you a new episode at least two to three times per month.

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

• Visit WorkingSessions.fm and join our newsletter
• Follow James on Twitter
• Follow John on Twitter