You Can't Lose!

In this episode, we talk about finding the right balance between creative side projects and work. Ensuring side hustles don't become hassles. Joe shares the fun of turning art into a successful Etsy shop and the thrill of connecting with a supportive fanbase. They touch on the challenges of staying creatively fulfilled while running a business and how to keep things enjoyable without burning o...

Sometimes it feels like the only way to change something is to throw a match at it and burn it all down to start over. In this episode we talk about Gell's Law, how all complex systems are built upon simple systems. Getting the core, foundational systems "right" influences everything. Let's talk about how to manage and navigate this process. Also we talk about the dangers of the...

In this episode, we explore the intricate balance between math and qualitative insights in business operations, particularly in consulting and lead flow, highlighting the limitations of small sample sizes. We dive into how organizational structure impacts innovation, referencing Safi Bahcall's "Loonshots," and emphasize the importance of qualitative interviews for understanding compa...

Richard has an angle on agency viability and purpose in an age of highly competitive digital products and tools. He's been working this out offline for a while now, but he's sharing with the You Can't Lose! audience to stress test his hypothesis. There's something there and it's a delight to hear him talk about the promise of client services from a fresh perspective. This is th...

Adam is a biz dev pro with decades of experience in client services and after all of those years, and all of those clients, and all of that revenue, sales success comes down to trust. Clients have to trust you. Your team has to trust you. Ownership has to trust you. You can see why Adam has enjoyed such a long track record of success when you hear more about how he builds, maintains, and nourishes...

Wil Reynolds joins You Can't Lose! this week, hold onto your butts. Wil is the shot in the arm you need if you're working in client services trying to figure out how to connect with clients. He's a content marketing machine, founder of SEER interactive, and a great example of how good citizenship of you community = equity in both business and in life. This is a great glimpse into Wil&#...

Richard is fresh off his trip to Config in SF and has thoughts on what the demand for this event tells us about the value of live events, some quick thoughts on the latest Figma news, and a long conversation about the value of people connecting IRL. Let's dive in!

Somehow we got Tracey Halvorsen to join the podcast again! Tracey is the CEO at Adeo and shares her thoughts on a lifetime of client services experience, her thoughts on value pricing, the value of relationships, and the secret to a long and successful career: You gotta listen to learn more!

Warren Wilansky is founder and President of Plank, our favorite Montreal web design and dev agency, and he joins us this week to explain how to grow an agency over 25 years. 25 years!!! It's super simple, it's all about relationships. Don't think about leads or accounts or marketing or sales. Cultivate authentic relationships and BOOM you're an overnight 25-year-long success story....

Ryan Irelan reminded me of this quote he heard on Julia Luis Dreyfus's podcast Wiser Than Me when she interviewed Anne Lamott, author of Bird by Bird, who attributed it to Teddy Roosevelt. That's how information works these days btw. Comparison shopping and Keeping Up With the Jones focuses on outcomes instead of on the journey. This week we talk about ways to mitigate the risks of compari...

There are no answers. No book that solves all your problems. No operating system to save you. What will serve you is an ability to see through these remedies to the underlying lessons or principles they're built on. Apply what works. Be flexible about what doesn't. Evolve constantly and question everything. There are no golden eggs or skeleton keys. And when you accept all of that you'...

How do you grow your most valuable accounts? Is that the PM's job? Do you need account managers? What can we learn from an ad agency's account strategy playbook? This episode we go HARD into account leadership. We share recommendations and best practices. Start here: Establishing process is an act of generosity, and when it comes to defining process first dog to the bowl wins. To kick off...

How can we apply what we know about client services sales to B2B sales? To SaaS sales? To small businesses? To traditional selling environments? It's easier than you think. This episode is about applying base principles of agency and client services sales to ALL KINDS OF SALES. How can you punch above your weight? How can you break through the noise of your competitors? How can you employ Rich...

On the topic of in-person teams and distributed teams a population of unintentionally hybrid teams are struggling with their identities. Teams that embraced a distributed approach during COVID, and are now left reconciling with the remnants of their in-person culture and the reality of their distributed staff. In this episode we discuss the remedies for this existential friction, how to get starte...

Building out from Richard's Extreme Agency Playbook we dive into the issue of co-located and distributed teams. More accurately we really dig into the current state of many teams: Unintentionally Hybrid. COVID created an industry of unintentionally hybrid teams and we're only starting to deal with the aftermath. While enterprises are forcing a Return To Office policy agency owners can'...

How to run an agency? Richard has notes. Colocation over distributed. 12 year strategies. Apprenticeships. No bonuses, no profit share, no exits. Suburban campuses over city offices. This episode packs a lot of heat. We're kicking off a miniseries within the podcast this week. Over the next few weeks Richard will share his playbook for the ideal agency, and how teams can make incremental progr...

Richard meets his new best friend Jay Fanelli in this episode of You Can't Lose! Jay is an agency owner, e-commerce company owner, and enterprise design leader with a unique perspective on how teams and businesses grow and evolve. A self described "vibes" over "numbers" manager, the vibes are strong in this episode with Jay this week. What was it like living through 2021&#3...

Are your daily stand ups really valuable, or do you just not trust your team? This week we unload on performative daily stand ups, meetings that should have been fistfights instead, managers who mistake "managing" as a measure of their success, and how to start fixing your goddamn meetings.

This week Richard and Joe focus on the conscious and unconscious decisions that shape work culture. Why does your team use Slack? Why not Discord? Whatever happened to Campfire? How about Figma, and Notion, and Basecamp, and Google docs, and where was that question someone asked you? Was it in Slack Thread? Good lord then it might be lost to antiquity for all time. Intentionality is one of the cen...

Jon Lax joins the podcast this week, you're welcome. We tracked down the elusive former Meta VP of Product and cofounder of legendary Teehan+Lax in a mountain cabin where he's not planning the future of technology and spatial computing because he's earned a goddamn break. Curious about what it was like at Facebook as they built all of the other parts of Facebook? How about learning abo...

Craig Bryant CEO of Kin , formerly founder of We Are Mammoth, cyclist, Chicagoan, and generally the Sam Elliott of workplace software joins us this week! Richard has talked about his love for Craig over half of our episodes and it's immediately apparent why reconnecting with Craig a few times a year helps restore both of their batteries. Craig even calls him "Rich." Imagine! Craig jo...

This week we're joined by Dan Ostrower from 3rd Horizon . Dan shares about his experiences on both the enterprise and consulting agency sides of the client services industry and makes a great case for the value of this insider/outside perspective. He also speaks to his experience cultivating enterprise innovation through his consultancy. Is your sales leader best when they're your team&#39...

We’re joined this episode by badass Tracey Halvorsen!!! Tracey is an artist, a people connector, and she’s sold and executed more amazing web and digital client services projects than you’ve ever imagined. Tracey unpacks some of her thoughts on how relationships inform and are reflected in client engagements. She zooms out and talks about life. She describes really interesting ways her perspective...

This week Richard and Joe are back out in the wild hosting events, meeting with friends and colleagues IRL, and trying to make meaningful connections within their networks. Richard is in NYC for a Knapsack Design System Leadership summit: https://www.knapsack.cloud/design-systems-leadership-summit-nyc-february-22-2024 And Joe is back to his PhilaMade roots at a Phebruary Happy Hour: https://www.ph...

In a very special Valentine's Day episode join Joe and Richard for a deep dive into the complexities of male friendships, personal growth, and the evolving landscape of professional relationships. They explore the significance of nurturing genuine connections outside of work and the impactful role of friendships in personal and professional development. Listen as two friends talk about friends...