Bootstrapped Web16 Marras 2017

"Fattening" Your Company and... Freemium?

Welcome back to Bootstrapped Web! Today we share progress reports about our respective businesses and ask the question, “Should you go freemium or not?” Jordan has begun the process of “fattening” up Carthook’s systems to add value to the company and move the business to the next stage. Carthook is also growing their team and there have been some growing pains in the communication process. There have been some hard lessons in the process that Jordan hints at that could help business owners build their systems more effectively. Brian has been putting a lot of energy and time into Ops Calendar. He is getting a lot of interest in the service and the product. This new interest has given him a reason to ask the question if freemium is a viable option for Audience Ops. There is some really useful and thoughtful discussion in today’s episode, so tune in to join the conversation. [tweetthis]I feel freemium is one of these things that a lot of bootstrappers have not given a fair shake as a strategy. - Brian[/tweetthis] Here are today’s conversation points:

The “fattening up” process of Carthook.
The struggles of building an effective team.
Audience Ops and Ops Calendar progress reports.
Ops Calendar’s features and fixing the unexpected bugs.
The usefulness of Slack.
The benefits of letting people “win.”
Working with freelancers and building a positive business culture around them.
Jordan’s marketing experiments and the results.
The pros and cons of freemium.

[tweetthis]I admire people who are super product focused because I think it's fun. It's so creative and interesting. - Jordan[/tweetthis]

Resources Mentioned Today:

Audience Ops Calendar Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

Tämä jakso on lisätty Podme-palveluun avoimen RSS-syötteen kautta eikä se ole Podmen omaa tuotantoa. Siksi jakso saattaa sisältää mainontaa.

Jaksot(172)

Just another Friday on the mics

We're cross-posting this week's episode of The Panel here in the Bootstrapped Web feed. While Justin's traveling, Jordan and Brian do a updates episode.Workout routines. Mindsets. North Stars. AI ...

30 Touko 1h 11min

We're back!

Jordan and I are back on the mics together! But it's not Bootstrapped Web.Jordan is joining Justin Jackson and me as the 3rd permanent co-host of The Panel Podcast.Be sure to subscribe to The Panel P...

21 Helmi 54min

2025 recap & 2026 outlook

Hey! Back in your feed for our bi-annual updates! It's December 2025 and that means it's time for our year-end recap and year-ahead outlook.What Jordan's up to:RosieOffiste PodcastJordan on XWhat Br...

17 Joulu 20251h 2min

2025 Mid-Year Update

We're back for a mid-year update!The last time we were on the mics together it was January 2025. So what's the outlook 8 months into the year?What we're working on:Jordan's in rocket ship mode on Ros...

21 Elo 20251h 9min

Our final episode (for now)

It's true. We're calling this a final episode—for now—but don't unsubscribe! We promise to pop into the feed every few months to catch up :) But for now, we're taking a breather and staying focused ...

9 Tammi 202539min

Year-end takeaways & goals

2024 look-back and takeaways. 2025 goals. Let's go! Connect with Brian: Follow Brian on Bluesky / Twitter Brian's products: Building! Instrumental.dev Instrumental Products Clarityflow Connect...

13 Joulu 20241h 6min

Bluesky.

Bluesky takes. Activation funnels. Retention. Delegating. Demo videos. Video marketing. Sick vacations. Connect with Jordan: Follow Jordan on Bluesky / Twitter Jordan's company, Rosie Connect...

6 Joulu 20241h 7min

Building out of a job

Putting in more hours to put in less. Building systems for delivering software. Deploying demo video(s). Listening to customers. Using a business to deepen your craft. News detox. Connect with Br...

8 Marras 202456min