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!
What Is The Right Time (& Price) To Sell Your Company?
In this episode, we provide updates on our respective businesses and have an open-ended discussion about how to know when it's the right time to "cash in" by selling your business.
Jun 8, 2022
45 min
How To Balance "Learning" With "Doing"
In this episode, we provide updates on our respective businesses and discuss how to balance "learning" with "doing." It's important to invest in professional development, even as an entrepreneur, but you shouldn't do it at the expense of execution. So, what's the right balance?
Jun 1, 2022
42 min
The Case Against Selling Subscription Services
In this episode, we provide updates on our respective businesses and discuss a tweet from TestimonialHero's Sam Shepler suggesting that selling subscription services isn't the "obvious win" it's often made out to be.
May 25, 2022
45 min
How Long To "DIY" Before You Start Hiring
In this episode, we provide updates on our respective businesses and discuss how first time entrepreneurs are more likely to take a "do it yourself" approach to business for longer than experienced entrepreneurs – and what that might be costing them.
May 11, 2022
43 min
Building What Customers Want Vs. What Customers Need
In this episode, we provide updates on our respective businesses and discuss whether entrepreneurs should take a customer-led approach to building out their products/services or try to build a creative solution and then educate customers on why they need it.
May 4, 2022
41 min
What Makes A Business Outcome A Success?
In this episode, we provide updates on our respective businesses and use the recent acquisition of Carthook as context to discuss our own "exit strategies." What makes a business outcome successful to you?
Apr 20, 2022
42 min
Competitors: Good, Bad, or Indifferent?
In this episode, we provide updates on our respective businesses and talk about how business owners should handle competitors and copycats.
Apr 6, 2022
38 min
Should We Offer On-demand Services Or Monthly Subscriptions?
In this episode, we provide updates on our respective businesses and get into a philosophical discussion about the merits and flaws of different pricing models – namely a la carte pricing vs. monthly subscriptions.
Mar 31, 2022
43 min
Why Leaders Should Treat Themselves Like Athletes
In this episode, we cover a broad range of topics, including: How to manage your health to avoid burnout, Why specialization is a good thing, When to hire your first team members, and When to say "no" to client requests
Mar 23, 2022
52 min
Origin Stories: How We Found Our Business Ideas (+ Our Goals For Them This Year)
In this episode, we go into more detail about how we landed on our specific projects, what makes them worth pursuing, how we're fitting them into our existing lives, and what goals we have for them over the next year.
Mar 7, 2022
47 min
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