You Can't Lose!

This week felt seismic. What happens when elite engineers get their hands on tools like Codex and suddenly compress four weeks of work into four hours?This is not about AI replacing developers. It is about AI amplifying the great ones and what that means for agencies, pricing, value, and the next 6 to 18 months of client services.__________In this episode of You Can’t Lose!, we break down the real-world impact of OpenAI Codex and advanced AI coding tools on software development agencies, product teams, and custom client services. This is not theoretical. This is boots-on-the-ground feedback from elite engineering leaders who are using AI to radically compress timelines and increase output quality If you run a digital agency, software consultancy, product studio, or internal dev team, this conversation is required listening.We explore:• How senior engineers are completing four weeks of work in four hours using AI-assisted development • Why AI coding tools disproportionately benefit top-tier engineers rather than average developers• What this means for pricing models, hourly billing, and value-based engagement• How agencies can dramatically increase impact without increasing headcount• Why engineering leaders should be “hair-on-fire excited” about these tools• What happens if your team is afraid instead of energizedThe core thesis: AI does not flatten talent. It amplifies it. Put Codex in the hands of a world-class engineer and you do not get marginal gains. You get exponential leverage. The gap between average and exceptional is widening.For agency founders, technical leads, and business development leaders, this episode reframes how to think about:AI in software developmentAI for agenciesValue creation in client servicesThe future of engineering leadershipAI and competitive advantageAI productivity in product teamsIf your developers are not experimenting aggressively with AI tooling, that is not a neutral signal. It is a strategic one.The past year has been an AI gold rush. This feels like a corner turned. A deeper acceleration. A shift from novelty to force multiplier. If you build digital products, websites, apps, internal tools, SaaS platforms, or custom software, this conversation is about the next 12 months of your business.For more on business development strategy, agency growth frameworks, and how to position your firm for asymmetric advantage in the AI era, visit:www.thatwasclutch.comThis is You Can’t Lose!

If someone is telling you that positioning is the best way for all agencies to improve sales, they probably sell positioning consulting. There are some universal truths, but they require a lot more hard work, and you can't pay someone to do it for you. Beware of experts, they're usually most expert at selling to you and people like you...

Hopefully y'all are experiencing what I am demanding all of my clients call a 𝗗𝗲𝗰𝗲𝗺𝗯𝗲𝗿 𝘁𝗼 𝗥𝗲𝗺𝗲𝗺𝗯𝗲𝗿 𝗦𝗮𝗹𝗲𝘀 𝗘𝘃𝗲𝗻𝘁 with an uncommon rash of sales opportunities and energy at 11:59 of the year 2025. This is bonkers. Here's some quick context and advice before EOY.

New plans & big plans for You Can't Lose! in 2026, as well as a tease for some more updates from Richard to follow about exciting new Second Harvest things too!

Joe and Richard unpack why creative work, and life, is more about steady contact than home runs. They explore the art of doing less but better, resisting the urge to please everyone, and finding meaning in risk, friction, and imperfection.

In this episode, Richard joins fresh off his Second Harvest retreat in Spain to talk about the myth of constant creativity, Joe talks about the beauty of the “average Thursday,” and Richard speaks to why resistance is the doorway to real growth. We trade stories about chasing the thrill of deadline chaos, the grind versus the high of agency life, and the trap of mistaking busyness for progress. Richard breaks down how Second Harvest helps people confront fear, embrace stillness, and integrate deep reflection into daily life, not just during a retreat, but back home amid kids, clients, and chaos. It’s a conversation about cycles of work and rest, the illusion of endless optimization, and learning to find meaning in the 80% of life that’s not the highlight reel.

This week Richard and Joe are still unpacking Second Harvest leading to some insights into the concept of hospitality as a skill. Convening the right people, the right way, and letting uncommon outcomes happen is a skill both Richard and Joe have developed over decades and applying these ideas to clients and relationships can yield profound outcomes.

Richard and Devon launched Second Harvest in Austria successfully and he's here to spill a ton of behind the scenes details, insights into the event, deeper dives into the unique philosophy behind Second Harvest, how it went, and where it goes from here. This is a must-listen if you've followed this event at all along the way!https://www.secondharvest.co/

In this episode, Joe and Richard explore the difference between community and alliance: “An alliance is going someplace… it has direction.” They trade time-travel hypotheticals, reflect on the problem-solving joy of The Martian and The Last of Us, and debate whether their businesses are behaving like nouns or verbs. “Do something with this,” Joe insists, as they revisit lessons from the Philadelphia Experiment. Along the way, they ask: what if your lease is your marketing strategy?

While Richard was away Joe catches up with Anthony Colangelo, partner at Pine Works, host of Main Engine Cut Off & cohost of Off-Nominal, engineering leader, iOS product developer, birds fan, dad, and Joe's spiritual nephew. Anthony has grown a space flght, exploration, and policy podcast empire rooted in his sincere passion and strong opinions re: the topic. They discuss the MECO origin story, how Anthony's vision drove the growth of the podcast, the power of authenticity, and the impact this project has on Anthony's life and career. Also it's a love fest.

Richard and Joe break down their conversation with Chris & Aaron Quinn, more details about agency acquisitions, private equity vs venture capital, and they spill the beans about The Philadelphia Experiment April 9-11.

Chris and Aaron Quinn join to share their experiences creating, growing, and ultimately scaling eHouse through an acquisition. Thanks to our friends for being so candid and informative about their experiences!

Duolingo announced changing their job titles from UX Design to Product Experience Design and created a 2013-Twitter-era dust up so Richard and Joe chime in with their thoughts. We discuss the purpose of job titles, the way identity effs with you, and to bring it back to sales in a meta way we ask what's more important? That you achieve your objective? Or that you're properly credited and acknowledged, and THEN achieve your objective?

This episode has it all!Richard shares how embedding "brown M&M" contract requirements helps you get what you wantHe also discusses how the TNT (takes no talent) parts of a business lead to successJoe provides an example: Respond to new leads shockingly quickly and meet your clients' enthusiasmRichard describes his tantric response to awkward silences (NSFW)Joe then accuses all of you of adopting a "Waiting Super Hard!" approach to sales and biz devRichard explains you miss 100% of the shots you don't takeJoe explains in sales "You Can't Lose!" and how that opens up the freedom to do the things you're not doingIn a devastating finishing move, they describe how they know an agency is really in a bad spot: they redesign their website! It's like watching your friend decide to get bangs after a big break up. A redesigned site is a call for help!

Richard and Joe discuss the little cohort/therapy group they're in and how beneficial that relationship has become over the past year. Within that discussion Richard explains how effective it can be to manage communication patterns within a community, for example conducting types of conversations in person while conducting very different conversations within the same community online. He describes how powerful that contextualization can be as well as how that deliberate focus prevents the online conversation from cannibalizing IRL or other communities. If you manage complex communication with communities, teams, or clients this is a super practical episode.

There's a few big ideas in this week's episode. Richard makes a strong case that Pipedrive weighted outcome forecasting for open opportunities and leads is steering you wrong. It's 0% forecastable revenue until the check clears.Joe says tracking sales quarterly sets you up to fail. There are two selling seasons and two off-seasons every year, plan accordingly.Richard and Joe both illustrate how digital agencies in particular under-invest in sales, biz dev, and marketing. They discuss why this happens, the risks and challenges that follow, and alternatives worth exploring.

In our ongoing "Parenting Advice That's Not For Everyone" Richard and Joe explain in detail the benefits of arming your kids with humor, and how to make your kids funny. From the benefit of "banned books" to letting your kids funny their way out of trouble to shoving your 8-year-old into Victoria's Secret, this episode has it all.

This week Joe and Richard discuss some tactical tricks of the trade as well as examples from the industry and from popular culture. What's the value of showing a client a glimpse into a far future state of their project as a concept car? How does casting the vision far ahead dramatically improve the client's ability to be attracted to novel ideas, rather than poke holes based on their constraints? Great examples of how practitioners like Tracey Halvorsen, Dan Mall, and Anthony Colangelo are detailed along with a couple of famous superheroes Ryan Reynolds and Henry Cavill. Get inspired and inspire your collaborators!

This week Joe unpacks some old Happy Cog notebooks and they spark a conversation about our identity and relationship to our work. How revisiting previous versions of yourself and your experiences can reinvigorate your current status quo. And how to overcome the urge for perfect by embracing small experiments in progress.

This week we talk about reinforcing change with repetition. Consistently reinforcing new behaviors and processes to drive lasting change. Investing in talent growth by positioning your agency as a talent incubator. Leveraging alumni networks and expanding your agency's reputation and business opportunities. We also dig into Adapting to AI's impact and staying competitive as AI reshapes search behavior and client decision-making.

Joe and Richard discuss: The challenge and opportunity of inexperience The mistake of getting permission or seeking credentialing The risk of not taking risks Why owners tire of running agencies after 7+ years What to do about that... And Joe takes shots at luminaries in the agency consulting space, the danger of their "always do this" didactic style of best practices, and why they should go fuck themselves

In this episode, Joe and Richard explore the idea of blending work and life, highlighting the ability to mix business with pleasure on trips, and emphasize how midlife can be a time of reinvention rather than decline. The episode also touches on the benefits of running life "experiments" to explore new directions after major transitions like career changes or personal loss. Richard shares his thoughts on how turning 50 doesn’t mean slowing down—it’s an opportunity to live more creatively and intentionally. The hosts reflect on modern work flexibility, the value of staying physically fit, and the importance of making conscious choices about career, hobbies, and relationships to ensure a fulfilling second half of life.

Well it's not the end, but we're talking about ways the podcast's focus will evolve and change. No spoilers yet, but this week we talk more about a "Second Harvest." The opportunity to make the next 50 years of our lives a better 50 years than the first. Look for some updates over the next few weeks as You Can't Lose! evolves. Hell it might even split into two podcasts! Who knows?

When the kids are loaded on to the school bus and Richard and Joe are left alone in their houses we start digging into some bigger picture ideas... Some of which might harbinger and new direction for the podcast over the next few weeks...????

This week the boys discuss their life hacks for successful business travel that also fill your cup spiritually. The TL;DR version is spend one additional day wherever you travel, and put up a Bat Signal once your there to attract some serendipitous meetings and hangs. Lots more detail and tips in this week' episode!

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 out. Then Richard shares tips on setting up your workspace to support your creativity and how to rethink your approach to work to better fit your life.

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 Middle Management Cummerbund.

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 company culture. The conversation also touches on the dangers of imitating others' success without context, the critical role of timing and market conditions, and the need for adaptability in evolving industries.

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 the summertime recharge you're looking for.

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 trust.

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's mind.

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. Warren unpacks mentorship among team members, planning for a post-Warren & Steve Plank, baseball as biz dev, LinkedIn buttsniffing and more.

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 comparing your accomplishments to others, and instead learn to focus on the journey and the lessons to be learned along the way.

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're ready to win.

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 the episode, with EightShapes closing doors, Richard and Joe discuss the life expectancy of agencies against the back drop of their 18 year run. Would owners be happier and make better decisions if they embrace the idea that client services are finite businesses that end? A services business is fulfilling, and exhausting. Ending an agency doesn't have to be a failure if owner's embrace a business lifespan attitude from the beginning. Let's get into it.

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 Richard's "Oprah" strategy? What can we learn from Owner Camp and other experiential offerings? How can you evolve and adapt? We get tactical this week baby!

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 started solving these problems, why they need to be addressed sooner than many leaders realize, and the myths we tell ourselves that cloud our judgement. We're out here fixing things this week!

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't convince, beg, or bribe staff to come back into the office. The moral of the story is in-person interaction is worth fighting for. You may need to manufacture it more deliberately if you're a distributed team, but the value remains irreplaceable. How can your remote team draw on the benefits of in-person interactions? What experiments can we conduct to test the viability of different team structures? What is the underlying danger teams that were once co-located, but now distributed need to be scared of? Let's do it.

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 progress towards his optimal state. This week we're starting with the optimal, no-constraints, 10/10 agency playbook to have an idea our conversations are aimed at. Over the next few weeks we'll explore ways to map towards this optimal agency, but it starts here with Team, Business Models, and Incentives.

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's most successful IPO to date? What did Jay learn along the way? Design leadership with a splash of F1 talk? Let's go!

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 central themes of the podcast and today we go deep into the choices we make, and don't make, and how they define the shape and texture of things. Like Richard's upper lip.

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 about the inner workings of the Meta spatial computing team, Oculus, and VR? How did Teehan+Lax get acquired by Facebook in the first place? Where did T+L turn a corner into a value-based model? Remember how crucial the T+L iPhone GUI Templates were? Where did that come from? And finally, what can we learn about time-based billing from the single greatest resource on the topic, 1993's legal thriller Wilford Brimley star vehicle The Firm? What the hell are you waiting for? Press play.

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 joins us to talk about his work leading Kin and digs into his strong feelings about more complete mindfulness of how personal and professional lives overlap and intersect. A work/life balance makes it sound like we're living two distinct lives. Craig's company, his team, and the software and projects they create are much more mindful of our total experiences and how work and life enmesh and influence each other. There's something beautiful in considering the total person, you maximize total impact and outcomes. Sit down on Craig's podcast porch and listen up.

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's biggest fan? Can you determine the right level of innovation that the client and agency are both aiming towards? Can you design 3 party agreements where the client, the agency team members, and the agency business each fill their cup? Are you positioned specifically enough? Spoiler: If there isn't something about your team that some clients would reject, you probably aren't differentiated enough...

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 as a painter and artist informs her views on people and relationships. There’s a dumb game Joe makes Richard and Tracey play guessing client budgets. Richard says “fack” at least once. You’ll laugh. You’ll cry. It’s better than Les Miz.

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.philamade.com/ While we're on the topic of people working together we get pretty pissed off talking about the ways we let unexamined structures force ideas like scaling, growth, and other lame ass motivations on otherwise smart people. We're here for intentional, thoughtful solutions. Maybe you have some to share too?

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 friendship and about being friends. Also! Plans are hatched to organize an event of some kind...