Undefeated Teams Are the Ones Coaches Worry About

Undefeated Teams Are the Ones Coaches Worry About

Episode Description What do Ironman triathlons, venture capital, pro track and field coaching, and falling asleep on the stairs have in common? They're all part of one of the most energizing double date conversations the Who's In Charge? podcast has ever had. This week, Stephanie and Zach sit down with KathrynKathryn O'Day, partner at Atlanta Ventures and former employee number nine at Pardot, and her husband Kyle O'Day, a professional track and field coach who has spent his career getting extraordinary performance out of human beings. Kathryn helped build Pardot through two major acquisitions — first to ExactTarget, then to Salesforce — and now spends her days vetting founders and co-building companies from scratch. Kyle spends his days doing what he's always done: getting more out of people than they thought they had. Together, they've figured out how to build two demanding careers, raise a family, and still make it to bed by eight o'clock. The throughline of this entire conversation is endurance — not the triathlon kind, though that's in here too. It's the kind that keeps you in the game for a decade when everyone else burns out and flames out at year two. Kathryn shares what she looks for in founders — including why she actually wants to invest in people whose first company didn't work out — and why core values are the only real scaling mechanism that matters. Kyle drops the most quietly devastating coaching insight of the episode: inspiration is for amateurs, professionals just show up. And Stephanie shares the moment she literally fell asleep on the stairs mid-walk and slid down on her butt — which turned out to be the wake-up call that taught her rest is not the enemy of progress. It is progress. Key Takeaways * Inspiration is for amateurs. Kyle's coaching philosophy applied directly to business: you don't wait to feel motivated. You show up, you work, you rest, you repeat. A decade later you're there. It sounds boring. It's the only thing that actually works. * The undefeated team is the one coaches worry about. Kathryn's insight from the venture world reframes failure entirely — the founders she most wants to back are the ones whose first company didn't work out, because they know what to do when they're behind. If you've never lost, you don't know how to respond when it counts. * 10 passionate, paying, unaffiliated customers. Kathryn's seed stage investment thesis is one of the most practical frameworks in the episode. Passionate means you're solving a real must-have problem. Paying means they value it enough to put real dollars behind it. Unaffiliated means you can transfer belief to a stranger — not just your network. * Core values are the only real scaling mechanism. Not technology. Not strategy. Core values are the operating system of your company — the framework that tells every team member how to make decisions in situations nobody has ever encountered before. If they're not authentic and self-reinforcing, they're just a poster on the wall. * Rest is part of progress. Stephanie's staircase moment is the most visceral illustration of what happens when you treat rest as an obstacle to progress instead of a component of it. You don't get there faster by not stopping. You burn out and stop completely. Rest is not the opposite of work. It is the work. Left Main is more than just a CRM, it's an end-to-end Real Estate Investment operations solution to run your company as an actual business with sales systems embedded. Want to find out more, book a call today, leftmainrei.co or whosinchargepodcast.com/home

The Rabid Dog Theory of Leadership

Episode Description What if the thing you've been avoiding — conflict — is actually the thing standing between you and the business you're trying to build? In this raw and refreshingly personal solo episode, Stephanie and Zach get into it on the topic of conflict: where it comes from, why most leaders handle it wrong, and what it actually looks like to turn tension into a team superpower. Stephanie grew up in a house where conflict was loud, passionate, and always landed in resolution. Zach grew up watching conflict end relationships for years at a time. Neither of those histories is wrong — but understanding where you land on that spectrum might be the most important leadership move you make this year. This is one of the most practically useful episodes the show has produced. Zach breaks down the "relationship bank" concept and why the busier you get, the more withdrawals you're making without realizing it. Stephanie makes the case that the best leaders lead with strengths, not corrections — and that most people have no idea what they're actually good at until someone tells them. They also get into real examples from this week: a difficult one-on-one after a missed quarterly goal, a team member who couldn't speak up in a leadership meeting, and what Chris Voss taught them about the difference between "you're right" and "that's right." If you've ever swept something under the rug because today felt too fragile for the truth, this one's for you. Key Takeaways * Conflict avoidance is a slow business killer. Avoiding conflict makes today smoother and tomorrow harder. If you can't address tension in your team, you will not build a scaling business — full stop. The rug only hides so much before the lumps become trip hazards. * Know your natural tendency first. Are you conflict avoidant or conflict aggressive? The answer changes everything about how you should approach hard conversations. Zach is avoidant. Stephanie is pro-conflict. Neither is wrong — but both require self-awareness to lead well. * Lead with strengths, not corrections. The biggest leadership misnomer is that your job is to coach up the bad stuff. The highest-leverage move is showing people where they're exceptional — because most people genuinely don't know. Trust gets built in the positive deposits, not the critical withdrawals. * "You're right" is not the same as "that's right." Chris Voss's distinction is one of the sharpest tools in this episode: when someone says "you're right," they're ending the conversation. When they say "that's right," they believe it. If you're hearing "you're right" a lot, you're running consensus theater — not building alignment. * Attack the problem, never the person. The only conflict worth having is the kind aimed at a shared problem. The moment it becomes personal — a deficit, an attack, a humiliation in front of the group — you've lost the thread of resolution and started tearing down trust instead of building it. Left Main is more than just a CRM, it's an end-to-end Real Estate Investment operations solution to run your company as an actual business with sales systems embedded. Want to find out more, book a call today, leftmainrei.co or whosinchargepodcast.com/home

Stop Creating Jobs, Start Building Businesses

What does it look like when someone goes from fixing and flipping houses in post-crash Las Vegas to co-founding a $165 million venture-backed real estate technology company — twice? This week, Stephanie and Zach sit down with Josh Stech, co-founder of Sundae, for one of the most framework-rich, intellectually honest conversations the podcast has ever produced. Josh brings the kind of clarity that only comes from building at scale: a 4S decision-making framework that diagnoses why most teams talk past each other, a gut-level philosophy on co-founding versus solo founding, and a warning about AI-driven marketing shifts that every real estate operator needs to hear right now. But underneath all the frameworks is something more personal — a guy who knows himself well enough to admit he needs a co-founder the same way he needs a gym buddy, who invests in the entrepreneurs that spin out of his companies rather than trying to stop them, and who believes the most dangerous thing you can tell yourself is that you don't need anyone else. Josh and Stephanie also go deep on what it means to compete from a place of passion versus a place of strategy, why the customer is the only filter that matters for innovation, and how to lead a team through the AI wave without losing their agency in the process. This one is packed. Key Takeaways * Most people don't build businesses — they create jobs for themselves. Josh's distinction is one of the sharpest in the episode: if your decision-making lens is "can I quickly turn this into active income for me," you're not thinking like a business builder. You're thinking like a self-employed person. The infrastructure, human capital, and discipline required to build at scale is a completely different game. * The 4S Framework: Sense, Seek, Solve, Start. When a team feels like it's talking past itself, it's usually because people are on different S's. Some want to jump straight to solving before anyone has asked why the problem exists. Some get stuck in sensing and never move. Naming which S you're on is one of the fastest ways to get a room aligned. * You can't sustainably beat someone who bleeds for the mission. Josh's take on passion versus strategy is unambiguous: even if you're smarter, better capitalized, and more operationally sophisticated, you cannot maintain a sustainable advantage over someone who actually cares about the problem. Passion is the only moat that compounds. * Solo founders may just be avoiding the hard work of collaboration. This is the most provocative idea in the episode — that some people convince themselves they don't need a co-founder not because they're built for it, but because recruiting collaborators and capital is hard, and it's easier to tell yourself you work better alone. * If you don't feel ahead on AI marketing, you're further behind than you think. Of the six Fs of real estate investing — find it, figure it, fund it, fix it, fill it, flip it — Josh believes the "find it" piece is about to be completely transformed by the shift from search to discovery. Operators who aren't actively ahead of this curve are already falling behind. Left Main is more than just a CRM, it's an end-to-end Real Estate Investment operations solution to run your company as an actual business with sales systems embedded. Want to find out more, book a call today, leftmainrei.co or whosinchargepodcast.com/home

More Problems, More Revenue, More Happy

What does it actually look like when a company turns the corner — not from a highlight reel moment, but from the slow, unglamorous work of facing what you've been avoiding? In this solo episode, Stephanie and Zach pull back the curtain on what's working right now in both Better Path Homes and Left Main REI. No guests, no polish — just a raw, honest conversation about burnout disguised as boredom, the three hires that changed everything, and why doing 10x turned out to be dramatically easier than trying to double. Zach opens up about something most CEOs won't admit: he knew exactly what it would take to grow his sales team — and he simply didn't want to do it. Stephanie unpacks why that's more common than anyone talks about, and how the right operations support doesn't just fix a business problem, it gives a leader their identity back. Along the way they get into AI as a distraction versus a force multiplier, the gold rush mentality that's pulling entrepreneurs off their core mission, and the Left Main product releases that have been two years in the making. If you've ever felt like you were drifting from your own company — or secretly hoping the pain wouldn't get bad enough to force a change — this episode is going to hit different. Key Takeaways * Knowing what to do and wanting to do it are two different problems. Zach's honest admission — that he knew how to grow the sales team and chose not to — is one of the most underdiagnosed growth killers in entrepreneurship. Pain is the motivator. Don't wait until it's catastrophic. * Operations support isn't a luxury, it's the unlock. The shift at Better Path didn't come from a new strategy. It came from three key hires — a COO, a Revenue Operations lead, and a Sales Operations manager — that gave Zach the room to operate in his zone and show up with energy again. One operations hire is never enough. * AI is the new logo design rabbit hole. Spending weeks building an AI tool instead of closing deals is the 2026 version of spending weeks on a business card instead of making calls. AI should make you more effective at the one thing you're already doing — not distract you into building a product you don't need. * Completion is the revenue. Zach's 80% clean room analogy lands hard: in business, an uncompleted task doesn't pay. Focus isn't just about choosing the right thing — it's about committing to it all the way through, not until the next shiny object appears. * Measure backwards before you spiral forward. Stephanie's moment of overwhelm — am I doing enough for the podcast, the companies, the kids, the marriage — is universal. The antidote isn't doing more. It's stopping to look at what actually got done and giving yourself credit for the distance traveled. Left Main is more than just a CRM, it's an end-to-end Real Estate Investment operations solution to run your company as an actual business with sales systems embedded. Want to find out more, book a call today, leftmainrei.co or whosinchargepodcast.com/home

No One Is Coming to Save You

What happens when two people who started as business partners — and not even friends — end up building one of the most solid entrepreneurial marriages in real estate? This week, Stephanie and Zach welcome Matt Theriault of Epic Real Estate and his partner Mercedes Torres for a double date conversation that gets refreshingly honest about ego, adaptability, and what it actually means to be a team. Mercedes admits Matt couldn't stand her when they first met. Matt admits he's been married and divorced twice before. And together, they share the one distinction that changed everything: when you love someone, why would you ever want them to lose just so you can win? What unfolds is a masterclass in partnership under pressure. Matt and Mercedes open up about the five hardest years of their business lives — COVID wiped out their thriving live events company almost overnight, and they spent two years hoping it would come back before finally accepting it wouldn't. What pulled them through wasn't a strategy. It was the same thing that built their relationship in the first place: complementary strengths, zero tolerance for "I told you so," and the discipline to focus on one thing when everything felt like it was falling apart. From eight throw pillows arranged in exactly the right order to the real reason employees stay on a team for a decade — this episode is packed with the kind of wisdom that only comes from going through the fire together. Left Main is more than just a CRM, it's an end-to-end Real Estate Investment operations solution to run your company as an actual business with sales systems embedded. Want to find out more, book a call today, leftmainrei.co or whosinchargepodcast.com/home Key Takeaways * Stop trying to win the argument. Matt's reframe is simple and devastating: if you love someone, why would you want them to lose? The moment he heard that, he called Mercedes and squashed a days-long argument immediately. Needing to be right is a relationship liability — in marriage and on your team. * Peers make the best partners. Matt and Mercedes saw each other as equals from day one — not romantically, but professionally. That peer-level respect meant their strengths and weaknesses were treated as assets, not ammunition. Whether you work together or not, how you position your partner in your mind shapes everything. * Swim in your own lane — by design. Mercedes made a deliberate choice early: separate offices, separate drives to work, separate domains. Not because they didn't trust each other, but because she refused to get sick of her husband. Intentional boundaries aren't distance — they're protection for the relationship. * No one is coming to save you. Matt's most honest moment: they had plenty of friends offering sympathy and pats on the back during the hard years. None of it improved the situation. At some point you stop waiting for the storm to pass and start building in the rain. * Humility is a strength, not a weakness. Mercedes calls it out directly — vulnerability and humility get mistaken for weakness constantly. But the leaders whose teams stay for ten years, whose partners still choose them after 17, are the ones who can say "I don't know" and "you take this one" without it costing them their identity. Left Main is more than just a CRM, it's an end-to-end Real Estate Investment operations solution to run your company as an actual business with sales systems embedded. Want to find out more, book a call today, leftmainrei.co or whosinchargepodcast.com/home