The Upstream Leader Podcast

On May 3rd, 2021, The Upstream Leader Podcast debuted with a very special guest: Courtney De Ronde. Courtney now rejoins The Upstream Leader as its first repeat guest on Episode 130 to talk about the process of leadership and firm scaling. By her own telling, Courtney had the right strategy for her firm: She had the logic, the numbers, the business case. But what she didn't have was alignment, so when it came time to share her vision, the resistance and even the panic she was met with was immense. She picked herself up, rebuilt trust, and re-approached her partners with two visions instead of one. The result was a unanimous vote for the exact same idea she'd proposed in the beginning. The lesson she shares is that the right strategy without alignment not only won't work, it may even backfire spectacularly. Since joining Jeremy Clopton on Episode 1, Courtney has also authored a book, Planning to Scale, which was a response to how most strategic planning resources will change how you think, but also fail to tell you what to actually do on Monday morning. She views leaders as "time travelers," which brings with it a significant problem: leaders must visit the future, but when they return and start talking about what they see there, they can accidentally terrorize their teams with ideas that aren't ready yet and don't need to be discussed. Her book and Simple ScaleUp System cover these themes, and so much more, and this episode is a great introduction to both.

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Jeremy Clopton and Shane O'Hara dig into what actually changes financially when you go from employee to partner on Episode 129 of The Upstream Leader. The title shifts, and responsibilities pile on, but your cashflow situation changes overnight, even though you've been thoroughly preparing for partnership in the background. Shane breaks it into three buckets: operating, tax, and savings. Don't run out and buy the bigger house or the fancy car, but instead, give it a year of adjustment. Pay yourself first. Because if you don't, you may just find yourself ending up as one of those partners with disorganized finances who end up criticizing every business expense because they're worried about covering their own fixed costs. The last thing a leader should be doing is limiting the firm's long-term trajectory like that, and as Shane puts it, not having your finances in order "definitely makes you the leader that you don't want to be." To learn when to start preparing, why your partner needs to be on board, and what "financial readiness supports leadership readiness" really means in practice, don't miss this episode.

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On Episode 128 of The Upstream Leader, we are re-airing a conversation between Jeremy Clopton and Heath Alloway on the Common Threads Podcast to explore what legacy really means for leaders in the accounting profession. According to Jeremy, legacy isn't something recognized after the fact, but rather, you construct it meticulously and systematically through daily, intentional action. Drawing from his own five-year succession journey taking over from Upstream Academy's founder Sam Allred, Jeremy outlines five archetypes of legacy-building: the wanderer, the shapeshifter, the anti-villain, the hero, and the mentor. He traces how a drive to prove others wrong can become both a superpower and your own kryptonite, why many leaders spend more energy pleasing predecessors than improving conditions for their successors, and what you have to do to move on from accumulating personal achievements, to instead investing in others' growth. While still focusing on legacy, Jeremy also shares advice for leaders navigating firm mergers like what the constituent firms of Sorren have been going through for an extended period. Names come off buildings and identities shift, but what firm partners built before isn't lost, it's transformed. The responsibility then becomes honoring what came before by building something even better.

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On the same Saturday his grandmother passed, Jeremy Clopton's oldest daughter played her first varsity softball game. On this solo episode 127 of The Upstream Leader, Jeremy turns that collision of grief and celebration into a working case study on leadership communication. Jeremy and his wife chose to delay sharing the news until after the game, a decision made with good intentions that still slipped out of their control once family members posted online. That gap between plan and outcome becomes the entry point for a broader lesson: leaders can build the most careful timeline for sharing difficult information and still watch it unravel, which means adaptability matters more than the plan itself. From there, the conversation moves into holding conflicting emotions at once, drawing on all his daughters' unfiltered reactions to grief and joy, to make an unexpected case for why teams navigating change need room to feel contradiction rather than resolve it immediately.

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Public accounting firms have spent years treating leadership development as someone else's job: hand it to L&D, buy a program, and boom, you're done, move on. Allyson Roote, VP of Learning and Organizational Development at The Bonadio Group, has been pushing against that mindset for over a decade, as she tells Jeremy Clopton on Episode 126 of The Upstream Leader. Her team stopped manufacturing courses on demand and started consulting instead, embedding learning specialists directly inside service lines so they understand the actual business problems driving interest in L&D before prescribing training. That shift shows up most clearly in Bonadio's Future Leaders Academy, a rotating program tied directly to partner pipeline decisions rather than treated as a standalone checkbox. Plus, there's buy-in: Bonadio's executive committee doesn't just fund it, they design sessions and sponsor participants personally, signaling that leadership development sits at the center of firm strategy, not as an afterthought on the periphery. Allyson also points out that AI fits into this picture a lot differently than some imagine. AI for her is a reason to double down on human capabilities like adaptability, critical thinking, relationship-building, not a replacement for human judgment, something no algorithm can manufacture.

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Every retreat season brings the same conversation: How do we develop our people fast enough to keep pace with a changing profession? On this solo Episode 125 of The Upstream Leader, Jeremy Clopton argues that the answer isn't another program or a better piece of technology, because technology will eventually democratize across firms, and learning and development systems can be redesigned all day long. None of that matters if leaders don't fundamentally believe their people can rise to the challenge. Drawing on Henry Ford's observation that "whether you believe you can or can't, you're right," Jeremy applies the same logic to leadership. When partners withhold opportunities because they doubt the next generation is ready, they create a self-fulfilling prophecy that stifles growth and extends the path to partnership far beyond what it once was. So be pro-the next generation, and give them the chance to stretch, to struggle, to develop judgment through experience. The resulting upside of your belief in them will far outweigh the only guaranteed downside, which is the stagnation that comes from never trying.

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When the status quo disappears, leadership stops being about comparing yourself to other firms and starts being an exercise in self-knowledge. On Episode 124 of The Upstream Leader, Jeremy walks through what happens once "staying the same" gets pulled off the table, and firms have to choose between paths nobody asked for. He breaks down the mental discipline required, namely separating personal opinion, from ownership duty, from managing-partner obligation. Those three roles pull in different directions during high-stakes decisions, and you have to try your best to make it clear which hat you're wearing at any given time. There's a practical framework for stress-testing options too, pushing to the extremes to find real risk and upside, then figuring out exactly what information is actually necessary versus what's just comfort-seeking. A quick nod to Annie Duke's Thinking in Bets grounds everything in real decision theory, and reveals that underneath the tactics is a bigger idea: Uncertainty forced on a firm can become the very lever that finally drives the change its leaders have wanted all along.

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Jeremy Clopton steps away from conference season and the recently concluded HeadWaters Conference, joining forces with Randy Crabtree of The Unique CPA for a crossover conversation, a first for The Upstream Leader on Episode 123. AI dominates firm conversations right now, but Jeremy argues the real anxiety comes from chasing an uncertain future instead of holding onto what won't change: being the protector of public trust. That anchor reframes everything from staffing fears to succession planning. They dig into leadership structures at growing firms, the false choice between serving clients and running the business, and why hiring managers instead of developing them rarely works. Private equity and M&A come up too, with the two sharing conviction that independent firms aren't going anywhere, and that the choice between selling, scaling, or staying small comes down to knowing who you actually want to be. Randy closes by dismantling the doom-and-gloom narrative around recruiting, pointing to rising enrollment numbers as proof the pipeline is healthier than the algorithm-driven headlines suggest.

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"The accounting profession is in decline." That's what the headlines would have you believe. Jeremy Clopton and producer Justin Grant push back hard on that narrative on Episode 122 of The Upstream Leader, arguing that what looks like collapse is actually a profession shedding its lowest-value work and repositioning for something far more interesting. In accounting's history, measuring billable hours created metrics in accordance with something called Goodhart's Law, and the result was an entire industry optimizing for the wrong things. In the modern era, the "how" of what accountants do has shifted: they now don't just process information, they interpret it for their clients. Private equity interest, rising enrollments, and the explosion of automation aren't signs of a profession in trouble, but rather, they show that accounting is expanding what it can do and who it can hire. The fear is real, yes, driven by algorithms and clickbait, but the underlying reality is considerably more encouraging.

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Most firms heading into retreat season aren't dreaming of a radical reinvention. What Jeremy Clopton has found, working with firm after firm this season, is something more grounded: leaders first look at who they are, and then decide they want to become a better version of that. Not a different firm, just a better one. That sounds simple, but the hard part is what it actually requires. Becoming a better version of your firm means finally doing the things that have shown up on the strategic planning list year after year, investing real time in developing people, committing to ideal clients, and holding the partner group to a genuine standard of excellence rather than tolerating the comfortable drift toward good enough. On Episode 121 of The Upstream Leader, Jeremy makes the case that raising the floor of performance in the partner room is where that work has to start, that accountability among owners is the hardest and most consequential thing a firm can do.

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