World's Greatest Boss

Everyone loves to tell busy founders, “You need an assistant!” But here’s the problem not all assistants are created equal. And if you hire the wrong one, you’ll waste money, get frustrated as hell, and end up thinking assistants don’t work. In this episode of World’s Greatest Boss, I break down the three main types of assistants: Virtual Assistant (VA), Personal Assistant (PA), and Executive Assi...

In this episode of World’s Greatest Boss, we dig into one of the biggest challenges service-based business owners face: balancing client growth with team health. My guest, Borja Cuan, co-founder of 415 Digital, manages over $280 million in ad spend every year—and he’s built a thriving business by doing something most agencies won’t: keeping workloads small so his team can go deeper, deliver better...

What happens when you know someone on your team isn’t performing but you keep putting off the conversation? In this episode of World’s Greatest Boss, I break down exactly why avoiding performance conversations is one of the costliest mistakes you can make as a leader. We’ll cover six powerful reasons to address performance issues early, from keeping your top performers engaged to protecting your b...

People Strategy Is Business Strategy: The Essentials You Need Think HR should handle all the “people stuff”? Think again. In this episode, I’m calling out one of the most common mistakes founders make when trying to scale—treating people strategy like an admin function or annoyance instead of core business strategy. I break down exactly what people systems you need and why this is all a part of yo...

High-performing cultures aren’t built by rules—they’re built by leaders who take full responsibility. In this episode of World’s Greatest Boss, I’m joined by Andrew Horn, executive coach to CEOs at companies like TOMS and Hinge, and the founder of Tribute.co. After scaling his startup to 120 employees and overseeing a successful exit, Andrew now dedicates his work to helping founders, CEOs, and le...

If you’ve ever caught yourself thinking, “They should know better” about someone on your team, this episode is for you. In today’s episode I break down a trap that many founders and managers fall into: holding secret expectations—unspoken rules that frustrate you when broken but were never actually communicated in the first place. Whether it’s scheduling mid-day appointments, not replying fast eno...

What does it really take to build a team that believes in your mission…. and sticks around? In this episode of World’s Greatest Boss, I sit down with Rachel Lauren, the co-founder and COO of Debbie, a platform that flips the script on financial rewards by helping users earn points for good money habits. Rachel and her team have grown Debbie from zero to 70,000+ users and just as impressively, from...

What if the person you’re about to fire isn’t the problem… it’s the role they’re in? In this episode of World’s Greatest Boss, Jackie Koch talks with Brice Jaggars, bestselling author of Two Fish in the Tree, about how role alignment and soft skills play a huge role in team performance. Brice shares practical tips for figuring out if someone is in the wrong job, how to spot soft skill mismatches,...

If you’re still relying on job boards to hire your next great employee, this episode is your wake-up call. I break down why “post and pray” is no longer an effective hiring strategy especially if you’re trying to land top-tier talent. Instead, you’ll learn the three proactive methods recruiting teams use every day to find the right people (and how you can do it yourself as a founder, hiring manage...

In this episode I’m joined by Art Shectman, founder and CEO of Elephant Ventures, a global innovation firm helping companies unlock the full potential of AI transformation. But we don’t just talk tech: we dive into the human side of building and leading a business. Art shares how he intentionally designed a company culture built on dependability, psychological safety, and joyful work. We talk abou...

In this episode of World’s Greatest Boss , I’m joined by David Metz, CEO and founder of PrizeOut, a startup that helps credit unions and gaming platforms reward their users with high-value digital gift cards. David shares how he scaled his company from his couch to over 50 employees, what he’s learned about leadership, hiring, and culture along the way, and how AI is transforming the startup lands...

Are 1:1s a waste of time? Not if you’re leading a growing team. In this episode host Jackie Koch challenges the rising trend of skipping one-on-one meetings and explains why most leaders can’t afford to follow that advice. You’ll learn what great 1:1s actually look like, how they improve trust, performance, and retention, and how to run them without adding chaos to your calendar. Whether you’re a...

What if you could eliminate the vast majority of your people problems, before they even start? In this episode of World’s Greatest Boss , I sit down with Kristian Ranta, CEO and co-founder of Meru Health, a Y Combinator-backed mental health startup, to explore how defining company values from day one helped him build a thriving team culture that actually works. Kristian shares the hard earned less...

You thought paying top dollar would take something off your plate, but here you are... staring at the payroll report wondering why things aren’t moving faster. In this episode, we’re breaking down a common leadership dilemma: should you hire someone with experience who can (theoretically) hit the ground running or bring in someone with potential and invest in their growth? Jackie unpacks the pros...

How do you go from sleeping in your office to leading a team of 30+ creatives—and still make payroll every two weeks without fail? In this episode, I sit down with Rob Kaczmark, founder and CEO of Spirit Juice Studios, an Emmy award-winning video production house, to unpack what it really takes to grow a sustainable, values-driven business. Rob gets candid about the messy, often-overlooked realiti...

What happens when an employee tells you they’re expecting—and you don’t have a leave policy in place? Cue the panic. In this episode, we’re breaking down everything you need to know to confidently respond and support your team when it’s time for parental leave. We’ll get into the basics of what’s legally required (spoiler: not much at the federal level), the states that do mandate paid leave, and...

In this episode of World’s Greatest Boss , I sit down with Lori Mihalich-Levin, healthcare attorney and founder of Mindful Return , to unpack one of the most emotionally charged and operationally challenging moments for managers: when an employee becomes a parent. We break down the real reason why one in three women don’t return to work after maternity leave—and what managers can do to create a su...

In this episode of World’s Greatest Boss, Jackie Koch chats about one of the most common and challenging issues in leadership: handling underperforming employees. As a boss, it’s tempting to make subtle changes—like cutting hours, posting a new job, or quietly giving tasks to other team members—hoping the problem will resolve itself. Spoiler: It doesn’t work. Jackie breaks down the four biggest mi...

In this episode of World’s Greatest Boss , Jackie Koch dives into the complexities of using AI in HR practices with Bryan Driscoll, a former employment attorney turned HR consultant. With AI tools like ChatGPT becoming increasingly popular for tasks like writing employee handbooks and screening job applicants, it’s crucial to understand where AI can be helpful and where it poses significant risks—...

Still using a 90-day probationary period to “test out” new hires? It might be doing more harm than good. In this solo episode, Jackie Koch breaks down why the traditional probationary period is outdated, misleading, and potentially risky for your business. You’ll learn what 90-day periods really signal to your new team members (hint: it’s not trust), why they don’t actually protect you legally, an...

In this episode of World’s Greatest Boss , I sit down with Robert Gallaher—entrepreneur, CEO, and author of Profit Sharing: The Power of Shared Success —to dive deep into how profit sharing can revolutionize your company’s culture, profits, and employee engagement. Robert shares the journey of how he went from an overworked business owner to building a thriving company culture powered by profit sh...

In this episode of World’s Greatest Boss , Jackie Koch tackles one of the biggest challenges for business owners: how to determine what to pay employees. From understanding market rates to building a compensation structure that aligns with your business goals, Jackie walks you through a practical framework that balances what your company can afford with what it takes to attract and keep great tale...

Most business owners think hiring the right people is the key to success. But even the best team members will fail or leave under bad leadership. In this episode, we’re tackling the crucial yet often overlooked challenge: how to turn field leaders into strong people leaders. My guest, Ryan Englin , has spent years helping business owners in the trades and service industries build teams that don’t...

Do you feel like you’re constantly following up, checking in, and reminding your team to do what they’re already supposed to be doing? You don’t have a team problem—you have an accountability problem. And the good news? You can fix it in the next 30 days without micromanaging. In this episode, I walk you through a five-step framework to build a culture of accountability where your team takes owner...

Are you avoiding firing an underperforming employee because you feel like the bad guy? What if I told you that avoiding it is actually the bigger leadership failure? In this episode, I break down exactly how to handle terminations with clarity, confidence, and respect—so both you and the employee can walk away feeling like the process was handled the right way. You’ll learn: How to know when it’s...