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EP 262: Honing Your Craft Using Smart Project Management With Kickass Conferences Founder Isaac Watson

The Nitty-Gritty:

  • How Kickass Conferences founder Isaac Watson manages massive projects like organizing a conference
  • The 5 phases that each event plan goes through and how project management works at each stage
  • What tools Isaac and his teams use to ensure every detail is accounted for and every guest has a fabulous experience
  • How he manages the experience on the ground during a live event

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I used to balk at project management.

It felt like the systems I was supposed to follow were imposing rules on things that didn’t need rules.

I’d get it done. And I’d do it my own way, gosh darn it.

But then, at some point…

…probably the 341st time I didn’t have enough time to execute a project the way I really wanted it to be done…

…I realized that project management is as much about honing your craft as it is about making sure you hit deadlines or don’t forget a step.

Teasing out the bits and pieces of how projects happen helps us make better stuff…

…whether what you’re making is a publicity campaign, a book, a set of complex financial reports, or a podcast.

This month, Sean and I have working hard on the next phase of our project management at Yellow House Media. Yellow House is the full-service podcast production agency we co-founded back in August.

The way we look at it, every step in the process of producing a podcast is an opportunity to make a show better—to make it more engaging for the listener and to drive more results for the business owner. But to fully take advantage of those opportunities, we have to have our process down.

We can’t just throw an episode together. We have to carefully and intentionally work each step of the process so that both the host that we’re working with and our team has the greatest freedom to innovate and improve.

The structure of project management gives us the space to hone our craft, to get creative, and to make something great.

And the better we get at making great podcasts, the better our project management gets too.

My guest today has had a similar experience learning the ins and outs of event planning and hosting kickass conferences.

Isaac Watson is the founder of Kickass Conferences, an event strategy and production studio based in the Pacific Northwest. Isaac helps community leaders develop and deliver transformative events for their audiences that inspire them to build a better world. So far, he’s planned and managed events that have touched over 21,000 lives across the US and Europe.

Isaac is a natural event planner. I know because I’ve attended a number of events that he’s planned and I hired him to plan a conference for me 4 years ago.

But Isaac hasn’t relied on his natural aptitude for creating meaningful and engaging experiences. Instead, he’s designed a process he can rely on to pull off one great event after another.

This process and the way he manages his events is clearly a product of the way he’s honed his craft over the years.

He notices what works, he notices patterns, he notices the things that go unnoticed—and then he adapts the way he manages future projects.

In this conversation, Isaac and I talk about how things have evolved since his very first event, the 5 phases that every event goes through from vision to completion, how he works with clients within that process, and what it’s like when it’s go-time and an event is live.

Now, let’s find out what works for Isaac Watson!

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EP 299: How To Design Your Own Sales System

EP 299: How To Design Your Own Sales System

This week, I’ve got 4 more stories to share with you from small business owners who have intentionally done things their own way when it comes to sales and selling. They’ve found what truly works for them–even if it bucks the prevailing wisdom or would make a bro marketing expert role his or her eyes.

These stories come from business coach Ashley Gartland, marketing expert Amy Lippmann, designer Mel Richards, and work reinvention coach Lydia Lee.

Listen for how they incorporated these same considerations into finding their own unique sales systems. They designed their systems with personal values, strong relationships, reduced anxiety, and agency in mind.

EP 298: Creating A Less Harmful Sales System with Wanderwell Founder Kate Strathmann

EP 298: Creating A Less Harmful Sales System with Wanderwell Founder Kate Strathmann

This show is called What Works for a reason.

Sometimes it’s a declaration: this is what worked for this small business. And often, it’s a question, “What works?”

Today’s episode is very much a question, many questions, really:

What works when it comes to selling when you want to avoid manipulative or exploitative practices?

What works when your values conflict with many of the best practices of selling online but you still want people to buy your stuff?

What works when it comes to sales in a business that is actively anti-racist and anti-capitalist?

And even more bluntly: Can you even sell things without causing harm or perpetuating harmful systems?

My friend Kate Strathmann is the founder of Wanderwell, a bookkeeping and consulting firm that grows thriving businesses while investigating new models for being in business.

Recently, Kate took a bit of a detour from how she’s used to building her business, which is 90% referral based and fueled by deep relationship- and community-building. She decided to offer a small group program called the Equitable Business Incubator as a way of exploring anti-capitalist business practices and how they apply to the small businesses we’re building.

To fill the program, Kate need to sell differently.

Which led her to asking the question: Can you even sell things as a anti-capitalist?

While that might not be your specific question, I have a feeling that you too have wondering how you can effectively sell your offers without causing harm, perpetuating harmful systems, or damaging relationships. And that’s why I knew Kate and I needed to explore this topic on the show.

This is a conversation about what a kinder, less harmful sales process could look like—and it probably contains more questions than answers. But I’m confident those questions can help you find the answers that are right for you and the sales system that you want to build to make your business stronger.

We start out by defining what we’re really talking about when we talk about capitalism and anti-capitalism. Then, Kate shares how the Equitable Business Incubator came to be and how she ended up selling it. And then we dig into what makes many of the sales formulas and best practices being taught today problematic—and how to think differently to create your own alternative practices.

Now, let’s take a look at what works for creating less harmful sales systems!

EP 297: Selling A New Program With Proof To Product Founder Katie Hunt

EP 297: Selling A New Program With Proof To Product Founder Katie Hunt

Today’s guest is Katie Hunt—who is a member of the former group and serves the latter group.

Katie is the founder of Proof To Product, which helps creative entrepreneurs run and grow thriving product-based businesses. She works with designers, illustrators, and artists to help them develop in-demand product lines and get them sold in stores all over the world.

Not long after the pandemic threw her business and the industry she serves for a major loop, Katie and her team launched Proof To Product Labs to provide a completely digital, ongoing support opportunity for business owners when they needed it most.

And that launch was a smash.

Katie and I get into all of the nuts and bolts of how she adjusted the offer to meet the moment and how she warmed up her audience before the campaign, as well as the exact mix of emails, podcast ads, and social media content she used to sell the offer when it went live. We also talk about how she sees the sales system evolving in the future and how the offer has been received now that people are using it!

What Works offers in-depth, well-researched content that strips away the hype of the 21st-century economy. Whether you love the podcast, the articles, or the Instagram content, we’d love your support.