How can you find — and attempt the great feat of solving — your perfect problem? That’s what I’m talking about today with my guest, Square co-founder Jim McKelvey. His book, The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time, is one of the funniest and most engaging business books I’ve read. We met at TED through our mutual friend Jon Levy, and had the great joy of recording together in person at a studio in midtown Manhattan. In the first half of this two-part episode, we delve into fending off an attack from “the perfect predator” of competition, Amazon.

Today I’m sharing the recording from our second-to-last book launch team Q&A one month after Free Time launched. I share post-launch stats, lessons learned, how I think about investments I’ve made, and share more about how helpful my “Author Support Group” (ASG) calls were with friends along the way.

Do you feel like you are wasting precious moments just finding things? Today, I’m speaking with Nick Sonnenberg, CEO of Leverage, about the importance of optimizing your business for retrievability. Nick’s sweet spot is teaching companies how to reinvent the way their work gets done by focusing on building a culture of team productivity, instead of merely focusing on individual efficiency.

It’s time to stop Franken-stringing software together. If you've read Free Time or been listening to this podcast, you know I am obsessed with software. Tools are my default go-to team member, given how much they do for my business. Today I’m sharing the top five tools that power my business . . . plus a few bonus “utility” tools that are always running in the background (I couldn’t resist).

Could you sell your business? Would you even want to once it’s optmized enough to make selling an option? Today I’m discussing the practical and emotional considerations of selling an online business with my longtime friendtor, Alexis Grant.

Stress, frustration, overwhelm: These are systems flags from your business asking for renewed attention on a bottleneck or inefficiency. In my case, it was repeating myself for the fourth time in as many months to different team members in answering the same small email-related process question. This is no one person’s fault (other than mine!).

“I’m always stumping quarterly planning for business owners. It’s the Goldilocks horizon for strategy execution, project scoping, and team alignment.” Today I’m talking with Charlie Gilkey about why the quarter is an ideal time unit for strategic planning, how to apply his stepwise Momentum process to mapping projects and goals, and striking the balance between visioning and planning. Charlie also had an interesting response on why tracking metrics matters . . . and it’s not what you might think.

There is a chicken-and-egg problem in the early days (and transitional moments) of any business: you need to earn more money in order to hire help, but hiring help is one of the only ways you can free your time to do the highest revenue-generating activities. Today I’m sharing the best investment I made in Q1 of 2022, even though it wasn’t a direct line to profitability (but pretty dang close).

Don’t bother starting a {business, blog, podcast}, the market is already too saturated! That limiting sentiment gets thrown around a lot—not least of which by our own mind. But just as there is always room to make new friends, so too can you find your best fit audience.

This week Megan Dougherty, co-founder of One Stone Creative and host of The Business Podcast Blueprint, takes over the pod again to share the benefits of podcasting, even within a seemingly-saturated topic.