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Choosing a Pricing Model

Colleen and Michele workshop what the pricing model should be for Colleen's SaaS.

Raising and Setting Prices

Colleen and Michele talk about how to (and how not to) raise prices -- and think through how to set them in the first place for Colleen's new product.

Who's the villain?

Somehow, despite a tumultuous week, Michele and Colleen still get things done. Michele talks about figuring out business incorporation from abroad, and Colleen talks through finding the "villain."

Founder/Business/Lifecycle Fit (aka "The Feelings Episode")

Michele and Colleen dive into striking a balance between business, founder, and lifestyle fit, and the trade-offs of running your own business versus working for someone else.

Vendor Lock-In, Heroes, and Timezones

Colleen considers the benefits and risks of changing vendors. Michele talks about a struggle they've had in the early days of their transition to being a remote company.

Health Insurance for Bootstrappers

Health insurance is complicated and expensive in the US...especially for bootstrappers. Michele walks through their own experience buying health insurance and gives a guide to the options out there. And Colleen hits her first milestone!

Bootstrapping a Company to 130 Employees

We chat with the humble and impressive Michelle Penczak, CEO of Squared Away.

Documentation as SEO, SEO as Documentation

We continue to chew on this quote from Alex Hillman: "When done well, marketing and teaching are nearly indistinguishable from one another."

Something Boring, Something True, Something Alluring, Something New

Michele talks about the unexciting but necessary parts of running a business, and Colleen experiences one of the most exciting things -- launch!

The Reveal!

We finally get a walkthrough of Colleen's image management service in this special audio-and-video episode.

Negotiations... with Customers and Oneself

Michele talks about how she leveled up her negotiation skills, and Colleen negotiates with herself about what really needs to be ready for her launch.

BONUS: Alex Hillman Joins Our Table

Alex Hillman grabs a chair and joins our table for this special episode. We talk about his new book, The Tiny MBA.

The Drudgery of Launching and the Difficulty of Hiring

Colleen gets closer to launching her image management service, and Michele opens up about their thinking on hiring.

Don't Rearrange the Desks On Your Users

Colleen thinks about how to hone in on her MVP, and Michele talks about how to get into customers' heads.

When should you give up or pivot?

How do you know when to cut your losses or to pivot to something else? This week, Colleen learned that people are more excited about how she's building her service than the actual service, and Michele talks about a product that came back from the dead.

Selling to Big Enterprises as a Bootstrapped Company...and Figuring Out Who to Sell to In the First Place

Can you sell to very big companies as a very small company? And how do you figure out what kind of customers to target in the first place anyway?

Finding and Firing Potential Customers

Colleen tries to find potential customers to interview about her new product. Meanwhile, Michele gets reached out to by a controversial potential customer -- and rejects them.

Building What You Need & Figuring Out Pricing (Or: Our CDNs Episode)

What to build when you don't know what to build? And how do you price it? Colleen and Michele workshop these two challenges this week.

Hey, why don't you join us?

Colleen and Michele move their previously-private weekly coffee shop conversation about their businesses to podcast form. Here's what you can expect from this podcast.

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