PODCAST · business
2 Commas: The $multi-million exit show with Josh Comrie
by Josh Comrie
Welcome to 2 Commas: The $multi-million exit showI've spent over two decades helping founders scale their businesses and achieve successful, multimillion-dollar exits. I've also achieved this myself on multiple occasions. With my experience as an entrepreneur, advisor, and investor, I’ve had the privilege of guiding companies through the highs and lows of business growth and exit strategies.Each episode will bring you the previously untold stories of entrepreneurs who have successfully scaled and exited their businesses for seven-figure (2 comma's) plus returns. You’ll hear more about the journeys, challenges, and pivotal moments that led to these transformative exits. My goal is to inform and inspire founders who are looking to scale their ventures to seven, eight or nine figures and beyond.Follow me on LinkedIn: www.linkedin.com/in/joshc
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75
Ken Crosson: From milking 1 cow to designing one of the word's best 400 houses
Ken Crosson nearly became a dairy farmer milking one cow in mid-Canterbury, instead, he walked into the Christchurch Town Hall at 16 and never looked back.In this episode of 2 Commas, I sit down with Ken, founder of Crosson and Co, one of New Zealand's most quietly celebrated architects, as the firm approaches its 40th year. We cover the pivot from farm kid to globally recognised designer, what it actually looks like to build a 40-year practice from scratch with no business training and one very young first hire, and why Ken still shows up to the office on weekends with a paper diary and a pencil. We get into the realities of partnership - how they form, how they end, and how the right recruiter talked Ken into a completely different hire than the one he thought he needed.We also unpack Plan Change 120, why building in New Zealand has gone from four drawings to 959 pages, and what AI is starting to do - and not yet do - to the profession. If you've ever wondered what four decades of designing spaces that move people actually teaches you about business, relationships, and the built world around us.
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Dr. Catherine Stone: I created NZ's botox market then nearly lost it all
She was asking people if they wanted Botox before most New Zealanders knew what it was, and they were asking her if their face was going to fall off.Dr. Catherine Stone pioneered cosmetic medicine in New Zealand in 2001, set up her first clinic in Vulcan Lane for $13,500, and built one of the country's most recognised aesthetic brands from scratch. In this episode of 2 Commas, I sit down with Dr. Cat to unpack what it looks like to front-run a trend before anyone believes in it, build a high-end boutique in a space that didn't exist, and scale it through TV deals, London clinics, and a few very well-timed pivots.We also get into the stuff nobody talks about - buying 23 properties in 24 months right before the GFC, the burnout that nearly ended everything, and three separate cancer diagnoses that ultimately forced the question: what actually matters? The answer led to an eight-week exit to someone she trusted, not the biggest multiple on the table. If you're building something and wondering what it looks like to lose nearly everything, rebuild it bigger, and walk away on your own terms. This one's worth your time.
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73
Rafael Niesten: I sold my company and bought three USB-C cables
Rafael Niesten built a nine-figure exit, woke up at 5:30am to watch the money land, and celebrated by going to Indian for $62 and buying three USB-C cables.In this episode of 2 Commas, I sit down with Raf, founder of PropTech Labs, to unpack what it actually looks like to build, acquire, and sell a portfolio of PropTech businesses without an investment banker in sight. We cover three strategic acquisitions in 18 months, five months of due diligence with a giant US corporate, and why timing the market ended up mattering just as much as building the product.We also get into the exit psychology - the void that opens up after a frenetic decade, the "one-eyed dog in a meat factory" focus lesson that changed everything, and what Raf's doing with the freedom on the other side. If you're building something and wondering what the finish line actually looks like and what comes after it, this one's worth your time.
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72
Tim Boyle: Voted off the board of the company I built
He cold-called American trucking companies from a dark office in Auckland at 2am — New Zealand accent and all — and built a nine-figure SaaS exit out of it.In this episode of 2 Commas, I sit down with Tim Boyle, co-founder of Whip Around, to unpack what it really takes to go from a commercial real estate career and a half-baked idea to a fleet compliance platform operating across the US with thousands of customers. We talk about the accidental pivot to DVIR compliance that changed everything, the decision to plant their sales team in Charlotte, North Carolina, and how they scaled from $1M to $10M ARR in roughly two years.Tim also gets honest about the harder stuff — being voted off the board of the company he started, the structural mistakes that made it possible, and what he'd do differently from day one around founder rights, cap tables, and governance. He's remarkably at peace with how it all played out, and the lessons he's carrying into his next venture, HelpGenie, are worth the listen alone.We finish on the exit: what a nine-figure acquisition actually looks like from the founder's seat, why getting to a finish line matters beyond the dollars, and why Tim thinks the old-school ways of building customer trust are about to come back in a big way.
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71
Yuan Wang: Why charging $150 for nothing beats selling something for $30
He pre-sold a SaaS product for $150 before it even existed — then discovered it was harder to sell the real thing for $30/month once customers could actually touch it.In this episode of 2 Commas, I sit down with Yuan Wang, co‑founder of Studio Ninja, to unpack what bootstrapping really looks like when you choose customers over investors. We talk about the early crowdfunding-style pre-sell (including taking card payments over the phone), the painful first launch that landed with silence, and the rebuild that came from obsessive customer feedback and iteration.Yuan also breaks down how Studio Ninja grew from a niche tool for wedding photographers into a global platform across 70+ countries — driven by SEO, community, and “hero photographers” who became unofficial ambassadors — before eventually being acquired by ImageQuix. We finish with the exit side: what inbound acquisition interest actually looks like, why they turned down an early life-changing offer, and how to keep growing the business while the deal noise swirls in the background.
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Vivian Bryant-Taukiri: 23 years in, 6 weeks out: The no earn-out exit
Most founders think selling a business is a transaction. Find a buyer, get a multiple, sign the papers. In reality, it’s an identity shift, a relationship test, and a stress event that shows you what your company is really made of.In this episode of 2 Commas, I sit down with Vivian Bryant‑Taukiri, founder of Brand Spanking, to unpack what it takes to build and scale an experiential marketing agency over 20+ years, and then exit it cleanly. We talk about the shift from “promo girls in Lycra” to modern brand experience, why this is ultimately a people-and-problem-solving business, and how mergers, acquisitions, and COVID pressure-tested everything.This is a practical conversation about partnerships, agency growth, and the reality of selling a service business. You’ll hear what triggered the sale, why a simple offer beat complicated earnouts, and why the most underestimated part of an exit is learning how to sit still after the thing that once defined you is gone.
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Why 2026 is the most important year of this millennium
Most founders hear “AI” and think they get it. Smarter emails. Faster content. A few basic automations. In reality, that’s a jet engine being used as a desk fan, and it creates a dangerous illusion of progress.In this episode of 2 Commas, I lay out why 2026 is a once-in-a-generation land grab for Western businesses, and why “power is never given, only taken”. I share the moment that snapped this into focus for me, the traps that keep smart operators stuck (the free-tier trap and the tool-shopping trap), and the real shift that’s happening right now: from assistant to agent, where AI stops answering questions and starts running multi-step workflows.This is a practical call to arms. You’ll leave with a simple three-step approach to take action this week: pick your most expensive recurring problem, define what “solved” actually looks like with a measure attached, then choose one tool and build one workflow end-to-end. Not this quarter. This week.Download the Whitepaper here 👉 https://www.joshcomrie.com/2026
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Jeremy Moon: How Icebreaker went from $10M to a $300M brand
Founders often think they can tidy things up when it’s time to sell. In practice, the value is won or lost earlier—depending on how much complexity, weak infrastructure, and preventable errors are allowed to accumulate.In this episode of 2 Commas, I sit down with Jeremy Moon, founder of Icebreaker, to unpack what it takes to build a global brand from New Zealand and then execute a successful acquisition. We cover international expansion, why the “New Zealand advantage” is often a myth offshore, and why hiring local teams matters more than most founders expect.Jeremy also breaks down scaling and profitability, how brand shows up in gross margin, and what changed when he brought in Rob Fyfe as CEO to professionalise the business. We get into exit planning, sale readiness, the M&A process, and how to position a company so it attracts premium buyers and stronger valuation multiples.
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Holli Moeini: A balance sheet mistake that could cost you $millions
Most founders assume they will be able to sell their business when the time comes. In reality, many are unprepared and lose significant value during the process.In this episode of 2 Commas, I sit down with M&A expert and CPA Holli Moeini, author of Finding the Missing Millions in M&A, to unpack why deals fail, how diligence erodes valuations, and what founders must fix long before going to market. We discuss financial readiness, working capital traps, balance sheet risks, and the factors sophisticated buyers evaluate beyond revenue growth.This is a practical conversation about exit planning, business valuation, mergers and acquisitions, and building a company that is truly sale ready, not just profitable on paper.
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Rick Agraval: Sold the house, built an 8 figure business, then sold for a maximum multiple!
Selling your home to fund a business is a decision most founders only talk about in theory.In this episode of 2 Commas, Rick Agraval shares the real story behind that moment and the journey that followed. After co-founding his business with his wife, Rick made the bold call to sell their home in order to finance the next stage of growth and keep full ownership of the company.What began as a scrappy, self-funded venture evolved into a fast growing digital marketing and ecommerce growth business. Along the way Rick immersed himself in the mechanics of performance marketing, from Facebook advertising and customer acquisition costs to the systems that drive scalable online sales.We explore the realities of bootstrapping a company, the learning curve of mastering digital advertising, and the mindset required to scale without outside capital. Rick also shares how founder curiosity, relentless self-education, and a willingness to take calculated risks shaped the company’s growth.This is a candid conversation about entrepreneurship, ecommerce growth, performance marketing, and the kind of decisions founders make when everything is on the line.
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Nigel Beach: 50 million mandarins a day: Inside a $150M sorting empire
50 million mandarins processed every single day.In this episode of 2 Commas, Nigel Beach shares the story behind Compac, the New Zealand engineering company that quietly became a global leader in automated fruit sorting.Nigel spent more than two decades inside the business, starting as a graduate software engineer and eventually becoming a shareholder as the company expanded across the US, Europe, and South America. What began as a small engineering firm grew into a global technology company processing millions of pieces of fruit every hour.We explore how machine vision transformed the fruit industry, the complexity of building hardware and software at industrial scale, and the strategic decisions that helped Compac grow from around $5M in revenue to $150M before its eventual sale.This is a founder journey shaped by engineering curiosity, relentless problem solving, and decades of incremental innovation in a surprisingly complex global industry.
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64
Stan Murphy: Momentum trumps all: How to create a high growth company
In this episode of 2 Commas, I sit down with Stan Murphy to unpack how he turns underperforming businesses into high-growth companies — and why momentum is the single biggest driver of enterprise value.From qualifying as a fitter and turner in Whakatāne to scaling JR Wholesale Meats to $65M in revenue before its sale to Foodstuffs, Stan shares how he identifies distressed assets, restructures broken systems, and engineers growth in mature industries.We explore how businesses spiral up or down, why exit strategy should shape decisions from day one, how diversification protected the company during COVID, and what buyers actually look for when acquiring a business at scale.If you’re 1–5 years away from selling, considering buying a business, or focused on scaling revenue and valuation, this conversation offers practical insight into business turnaround strategy, growth execution, and building a company that attracts serious capital.
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Neil Millar: 160 deals, 113 foreign buyers: What's really happening in NZ M&A
The M&A market is moving again. The question is... who’s ready?In this episode of 2 Commas, I sit down with Neil Millar, Partner of M&A at MinterEllison, to unpack what really happened in 2025 and what it signals for 2026.Global deal volume surged back toward $5 trillion, international buyers are re-entering New Zealand, and private equity still has significant dry powder. At the same time, succession challenges, health-forced exits, board hesitation, and slower processes have shaped a complex local market.We explore what’s driving renewed activity, why some deals stall while others move quickly, how corporate carve-outs are reshaping the landscape, and what regulatory shifts like OIO reform and competition law changes could mean for foreign capital.If you’re 1–3 years away from selling, or simply want to understand how market cycles influence enterprise value, this conversation will give you clarity on timing, preparation, and positioning.
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62
Ray Delany: How I turned a failing business into a 5x + exit
He bought 51% of a business that was already going down the gurgler… then the GFC hit.In this episode of 2 Commas, Ray Delany shares the full story behind turning a struggling technology services company into a 5X+ exit. What followed the acquisition wasn’t momentum. It was cash bleed, lost customers, leadership doubt, a global financial crisis, and significant personal upheaval.Ray walks through what actually changed the trajectory. Shifting from chasing growth to building profitability. Taking full ownership rather than leaning on inherited thinking. Rebuilding credibility with customers. Attracting the right people. Moving early to cloud infrastructure. And learning that selling well often matters more than building something exceptional.We also explore the original MailMarshall exit, the realities of services multiples, structuring an earn-out, and why values alignment mattered more than squeezing the last dollar from the deal.This is a grounded conversation about responsibility, resilience, and earning an outcome over a decade.
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Joaquin Cordero: My partners were secretly funding our biggest competitor
In this episode of 2 Commas, I sit down with Joaquin Cordero to unpack one of the defining moments of his entrepreneurial journey and the lessons it shaped for everything that followed.Joaquin has built businesses across twelve countries, often entering industries he’d never worked in before. We talk about how trust is built and broken in partnerships, what happens when misalignment surfaces too late, and how founders learn to assess risk beyond contracts and spreadsheets.The conversation moves through building in emerging markets, navigating fractured partnerships, stepping out of operations, and designing businesses that create freedom rather than dependency. Joaquin also reflects on how close calls changed his perspective, why service now sits at the centre of his work, and how he’s learned to treat businesses as assets, not anchors.A thoughtful conversation about judgment, resilience, and playing the long game as a founder.
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60
Joshua Parsons: The 17yr old cop who built two companies worth millions by 30
He started as a police officer, nearly lost everything in his first business, then built and sold a capital-heavy security company before going again.In this episode of 2 Commas, I sit down with Joshua Parsons to unpack a founder journey shaped by early responsibility, hard-earned judgement, and an obsession with solving problems properly. From policing at 17 to bootstrapping Crosbies Security, learning the real difference between revenue and cash, and building a business that could run without him, Joshua shares the lessons most founders only learn the hard way.We also explore how one unresolved failure inside his first company led to the creation of Watchful, a software business now scaling rapidly across international markets. This is a practical conversation about resilience, influence, succession, and building businesses that actually hold value.If you’re thinking about scale, replaceability, or going again after a hard chapter, this episode will land.
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Dear founder; Are you building the right business?
Strategy only works when it’s anchored in something that actually matters.In this episode of 2 Commas, I continue the strategy series by going deeper into direction, long-term objectives, and purpose. We start with why self-awareness on its own isn’t enough, and why founders need a clear North Star that aligns with the kind of challenge they are built to take on.The episode explores how BHAGs fail when they’re vague, generic, borrowed, or never truly communicated. Using real examples, including OpenAI, Juicero, and Quibi, I unpack what happens when purpose gets replaced by profit, and why that shift creates confusion, misalignment, and turnover.We also look at how different founder patterns require different long-term goals, why your BHAG needs to demand the right kind of challenge, and how purpose binds ambition, strategy, and team commitment together.A reflective, practical listen for founders thinking seriously about where their business is heading and why it exists at all.
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Why businesses stall (and what you can do about it)
Trying to build a business without clarity is like heading into the bush without a map.In this episode of 2 Commas, I unpack why so many founders feel stuck, exhausted, or uncertain even when the business is moving. Not because they lack effort or capability, but because they haven’t clearly answered two foundational questions: what they want from the business, and what they’re willing to sacrifice to get it.We explore the patterns that show up when ambition and sacrifice are misaligned, why businesses tend to stall at predictable points, and how different founders are playing very different games without realising it. The episode introduces four common founder patterns and explains why strategy only works once you know which one you’re in.A practical, reflective listen for founders who want clarity before pushing harder.
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Entrepreneur legends on mindset and mindfulness
Before getting into goals, it’s worth pausing.This first 2 Commas episode of 2026 is a curated compilation of insights from Linda Jenkinson, Jessie Stanley, and Debra Hall, drawn from different conversations and connected by a shared focus on mindset, ambition, and long-term thinking.The discussion stays away from tactics and frameworks, and instead returns to the internal side of building. How founders think under pressure. How ambition changes as responsibility grows. Why clarity becomes more important over time.A reflective listen for founders setting direction for the year ahead.
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56
Shane Young: A massive product failure became our vital exit multiplier
This business started with eczema, a barbershop, and a lot of trial and error.In this episode of 2 Commas, I sit down with Shane Young to unpack the long road from mixing hair wax in a flat to building, scaling, and ultimately selling a multi-brand consumer business across haircare, skincare, and natural beauty.We talk about solving your own problem first, learning manufacturing the hard way, surviving near-disasters in new markets, and why owning the hard parts of the value chain became the real source of leverage. Shane also shares what made the business attractive to buyers and how preparation shaped the exit.A candid conversation about resilience, patience, and building value over decades, not quarters.
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55
Marc Stöckli: Our near acquirer went to prison!
Most founders fear board meetings. Marc Stöckli documented more than 200 of them and turned the lessons into a playbook for builders.In this episode of 2 Commas, Marc walks through the lived reality behind Totemo’s two-decade journey. It is a story of rebuilding after a fractured founding team, competing early in a market no one understood, narrowly avoiding a disastrous sale to a Ponzi scheme, and finally exiting into a global cybersecurity group.We dig into what strong governance really looks like and why so many founders underestimate the emotional and strategic weight of the boardroom. Marc’s experience across Totemo, Kiteworks and his global leadership role at EO gives a rare window into decision-making at the edge.A grounded, insightful conversation for founders who want to build well and lead well.
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54
James McGlinn: How we won against powerful competitors
Some exits happen fast. James McGlinn spent twenty years earning his.In this episode of 2 Commas, I sit down with James to trace the long arc of building Eventfinda — from coding websites as a teenager, to taking on a government-funded competitor, to ultimately selling into one of the world’s major ticketing groups.We talk about the realities founders rarely share: staying alive when you are under-resourced, the power of one well-timed hire, the discipline required to play a long game, and the emotional shift that comes when you finally hand over the thing you built.A grounded, honest conversation for any founder building something that takes time.Book launch alert! Join me and other founders, leaders, and podcast guests for an evening launch of my book: 2 Commas: The Founder's Guide to Exits, Wealth, and Freedom. >> Click here to buy your tickets<<Receive weekly business insights and real exit lessons straight to your inbox by signing up for 2 Commas Journal https://www.joshcomrie.com/subscribeFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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How to keep going - when it all seems too hard
You can have drive, passion and grit, but if you’re not solving a real problem for real people, you don’t have a business.In this solo episode of Two Commas, I unpack the foundation every founder needs before thinking about product, market or funding: problem clarity. We talk about why motivation isn’t enough, why solutions-first thinking kills momentum, and the five reliable ways to uncover a problem that actually matters. I share lived examples from companies like Spanx, Dropbox and Slack, along with the patterns I’ve seen after meeting hundreds of founders.If you’re building anything right now, start here. This is the work that turns clever ideas into real companies.Book launch alert! Join me and other founders, leaders, and podcast guests for an evening launch of my book: 2 Commas: The Founder's Guide to Exits, Wealth, and Freedom. >> Click here to buy your tickets<<Receive weekly business insights and real exit lessons straight to your inbox by signing up for 2 Commas Journal https://www.joshcomrie.com/subscribeFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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Why most businesses fail before they even begin
You can have all the drive in the world — but if you’re not solving a real problem, you’ve got nothing.In this episode of 2 Commas, I break down the most important question in your entire founder journey: what problem are you actually solving?I explore why motivation isn’t enough, how to avoid building solutions in search of a problem, and the five ways to uncover a problem that truly matters. From lived experience to research, consequence mapping to daily-active-user thinking, this is the foundation every successful company is built on.If you’re building anything right now, start here.Book launch alert! Join me and other founders, leaders, and podcast guests for an evening launch of my book: 2 Commas: The Founder's Guide to Exits, Wealth, and Freedom. >> Click here to buy your tickets<<Receive weekly business insights and real exit lessons straight to your inbox by signing up for 2 Commas Journal https://www.joshcomrie.com/subscribeFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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51
Cornelius Boertjens: I built to sell, then wondered, what next?
He sold his business for millions — and found himself fixing coasters to fill the time.In this episode of 2 Commas, I sit down with Cornelius Boertjens, founder of Catchi, to talk about what really happens after you sell your business. From the grind of building and the challenges of a 5-year earnout to the strange quiet that follows the deal, Cornelius shares an honest look at identity, purpose, and what comes next for founders after the finish line.A grounded, candid conversation about freedom, success, and why so many of us struggle with both once we finally get them.
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50
Brendan Roberts: Is this NZ's first AI exit?
He had weeks of cash left, then came the call that changed everything.In this episode of 2 Commas, I sit down with Brendan Roberts, co-founder of Nine Spokes and Aider.AI, to unpack one of New Zealand’s most remarkable founder journeys.Brendan shares what it’s really like to build through crisis, recover from near collapse, and ultimately sell twice. We talk about timing, resilience, and how luck usually shows up wearing the clothes of preparation.If you’re navigating growth, pressure, or an uncertain runway, this conversation will remind you what it takes to stay in the game.Receive weekly business insights and real exit lessons straight to your inbox by signing up for 2 Commas Journal https://www.joshcomrie.com/subscribeFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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49
Chris Small: Inside the numbers: the state of NZ business sales
Building your business is one game. Selling it is another — and most founders never learn the rules.In this episode of 2 Commas, I sit down with Chris Small, Managing Director of ABC Business Sales, the firm behind nearly half of all SME business sales in New Zealand.Chris shares what really drives a successful exit — timing, risk, and what buyers truly value. With data from more than 480 business transactions, he reveals the patterns behind high-value deals, the biggest mistakes founders make, and the five things every acquirer looks for before making an offer.If you’re 1–5 years away from selling, or just want to build a business that’s worth more, this conversation will give you clarity, timing insight, and real leverage for your future deal.Receive weekly business insights and real exit lessons straight to your inbox by signing up for 2 Commas Journal https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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48
Chris Small: Inside the numbers: the state of NZ business sales
Building your business is one game. Selling it is another — and most founders never learn the rules.In this episode of 2 Commas, I sit down with Chris Small, Managing Director of ABC Business Sales, the firm behind nearly half of all SME business sales in New Zealand.Chris shares what really drives a successful exit — timing, risk, and what buyers truly value. With data from more than 480 business transactions, he reveals the patterns behind high-value deals, the biggest mistakes founders make, and the five things every acquirer looks for before making an offer.If you’re 1–5 years away from selling, or just want to build a business that’s worth more, this conversation will give you clarity, timing insight, and real leverage for your future deal.
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Jonny Mirkin: Before I sold it, it hospitalised me
He built a fast-growing tech company, raised millions, and sold it in an eight-figure exit. But before that, the business nearly killed him.In this episode of 2 Commas, I talk with Jonny Mirkin, founder of Nomos and now GivenWell, about what happens when ambition turns on you. From burnout that landed him in hospital to the years of therapy that followed, Jonny shares the brutal lessons that changed how he leads, builds, and lives.It’s not just a story about selling a company. It’s about what success really costs and how to come back from losing yourself along the way.Receive weekly business insights and real exit lessons straight to your inbox by signing up for 2 Commas Journal https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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46
Nathan Morgan French: From gambling addiction to successful exit
Every founder has a story. But few have one that takes a turn like this.In this episode of Two Commas, I talk with Nathan Morgan French, a founder who built, scaled, and sold a telco business, but only after confronting something far deeper than business itself.What Nathan went through changed how he thinks about focus, discipline, and what success really costs. It’s a story of collapse and comeback, and the quiet strength it takes to rebuild when no one’s watching.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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Justin Hamilton: I built it, then bought it back
What if the smartest way to start a company… is inside someone else’s?In this episode of Two Commas, I sit down with Justin Hamilton, co-founder of Davanti, to unpack one of the most unusual founding stories I’ve come across — how three consultants built a thriving, entrepreneurial business inside Spark, then bought it back, scaled it, and sold it in one of New Zealand’s most impressive consulting exits.We dig into how Justin and his partners turned corporate constraints into creative freedom, the art of building culture within a giant, and how to navigate buyouts, partnerships, and earnouts without losing your sanity.If you’ve ever wondered how to build something exceptional inside a big organisation — or how to know when it’s time to take it out on your own — this episode will give you the playbook.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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Why most founders aren't entrepreneurs - Part 2
I’ve seen too many founders build businesses they end up resenting, not because the idea was wrong, but because they never stopped to ask: what do I actually want from this? In this episode, I introduce the five levels of foundership—from lifestyler to entrepreneur—and explore the rewards, risks and sacrifices at each stage.Some of the happiest people I know are lifestylers who never wanted anything bigger. Some of the most miserable are entrepreneurs who should have stayed operators. Wherever you are on the journey, this framework will help you figure out which level is right for you, so you can build a business that fuels the life you want, instead of consuming it.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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43
Why most founders aren't entrepreneurs.
Season 4 kicks off with a special solo episode where I go deep on the founder’s burden: the pressure, the sacrifices, and the simple but confronting question: what do you really want from your business? Drawing on my own journey from burnout to clarity, I unpack why defining your true goals and what you’re willing to sacrifice is the key to building on your own terms.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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42
Pro services company legends: timeless business lessons
Marisa Fong, Matt Chapman, and Jovan Pavlicevic each built and exited companies on their own terms — but the lessons they share are universal. From chasing government contracts as a two-person team, to scaling a global freight train, to selling before the market turned, their stories reveal how ambition, timing, and resilience shape the founder journey.This best-of episode isn’t about theory or glossy headlines. It’s the messy, human side of building and exiting — told by founders who’ve been there, scarred, and succeeded. If you’re growing, scaling, or planning an exit, these are the insights you’ll want in your back pocket.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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41
Startup legends on how to start, scale, and sell
Mike Carden, Will Palmer, and James McCarthy each built, scaled, and sold SaaS companies in very different ways — but all with lessons that matter for founders today. From surviving the GFC with no cash, to putting profitability ahead of vanity growth, to mastering the art of storytelling as a sales weapon, their experiences cut through the myths of startup success.This “best of” episode isn’t polished theory. It’s real stories, hard scars, and the kind of wisdom you only get from the trenches of building and exiting. If you’re starting, scaling, or staring down an exit, you’ll find insights here worth stealing.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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40
Vicki Ammundsen: NZ's top Trusts Lawyer tells all
Vicki Ammundsen didn’t become one of New Zealand’s most sought-after trust and tax lawyers by playing it safe. She’s spent decades helping founders, families, and advisors navigate the uncomfortable questions most people avoid—until it’s too late.In this episode, we explore the hidden cracks in succession planning, the emotional blind spots that derail even the best-laid legacies, and why giving your kids shares in the family business might be the worst gift of all. Vicki shares the patterns she’s seen behind high-stakes exits, multi-generational wealth plans, and business transitions that either protect the founder’s vision — or slowly unravel it.Whether you’re planning to step back or just starting to build something worth passing on, this conversation is a wake-up call to plan with clarity, intention, and courage.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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39
Symon Thurlow: We 4 X'd our earn-out! Here's how.
Symon Thurlow didn’t set out to sell his business — but when opportunity knocked, he took the deal and stayed on for seven more years. What followed wasn’t just a transition. It was a transformation.In this episode, we unpack what really happens when you scale a niche services business to $20M+, navigate an earnout with zero prep, and lead post-acquisition without losing your identity. From trusting your gut to learning the language of corporate, Symon’s story is proof that exits aren’t just about walking away — they’re about stepping into the next version of yourself.Whether you’re building a business, considering a sale, or already on the inside post-acquisition, this conversation offers grounded insights into navigating the long game.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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38
Ben Forman: I walked away from millions. Here's why I'm at peace.
Ben Forman built an incredible business around storytelling, intuition, and timing. From pioneering New Zealand’s first commercial drone business to selling Wrestler after years of soul-searching, Ben has seen both the magic and the messiness of entrepreneurship.In this episode, we unpack what it really means to build something meaningful, why knowing your “why” can save you millions, and how letting go at the right time can be the most powerful move of all. Whether you're scaling, stalling, or standing at the edge of an exit, Ben’s story is a masterclass in clarity, timing, and staying human in business.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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37
Kimberlee Sweeney: My first divorce wasn't my marriage. It was my business.
Kimberlee Sweeney has seen what tears relationships apart, not just in marriages. As New Zealand’s first divorce coach, she also works with business partners, co-founders, and leadership teams to stop breakdowns before they happen.In this episode, we dive into the psychology of founder dynamics: the unspoken expectations, emotional blind spots, and behavioural patterns that can quietly destroy a great business. From prenups for partnerships to navigating resentment when roles aren’t equal, Kimberlee offers a roadmap for conflict prevention, repair, and clarity, especially when the stakes are high.Whether you're in a co-founder relationship, planning an exit, or leading a team through friction, this conversation will change the way you think about trust, alignment, and emotional due diligence.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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36
Kaz Staples: $15 cereal; Impossible they said! I built the category and my empire.
Kaz Staples didn’t set out to build an iconic food brand—she just wanted to make honest muesli. But over 25 years, she turned Pure Delish into a household name. Along the way, she faced near-collapse during the GFC, fought through burnout, and rebuilt a business on gut instinct and grit.In this episode, we explore what it really takes to lead through chaos, the emotional cost of carrying a company on your back, and what happens when you finally walk away. Whether you’re building something or wondering how to let go, Kaz’s story is a masterclass in resilience, reinvention, and the power of staying true to your values.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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35
John Bolton: At 32 I walked from a $60B portfolio. Into nothing.
John Bolton (JB) walked away from managing a $60 billion portfolio at the onset of the Global Financial Crisis, betting everything—his house, savings, and future—on a dream. His journey with Squirrel wasn’t just about creating a successful mortgage and lending business; it was about embracing uncertainty, surviving near-bankruptcy, and building resilience through relentless innovation.In this episode, JB candidly shares why naivety can be an entrepreneur’s greatest asset, the critical importance of timing and capital strategy, and how stepping aside from leadership allowed his company to scale. Whether you're navigating your own startup journey or considering what comes next, JB's insights provide an authentic roadmap to taking bold risks and transforming challenges into lasting success.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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34
Ryan Sanders: $34M in revenue. Slashed by 94% overnight.
Ryan Sanders didn’t exit because the business was broken—he left because he was ready.After building one of Aotearoa’s most iconic tourism brands, he walked away on his own terms, in the middle of a pandemic.In this episode, we unpack the emotional terrain of stepping back while the business is still thriving, the quiet toll of staying too long, and the unspoken identity crisis that comes with no longer being “the founder.”Whether you’re thinking about selling or just asking yourself what comes next, this is the conversation you didn’t know you needed.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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33
AJ Wilderland: Block my company sale? I'll find a better deal!
AJ Wildland co-founded one of the coolest tech companies to come out of NZ and helped revolutionise DJing globally. From bootstrapping Serato with a groundbreaking algorithm to navigating a $100M exit and stepping into the political arena, AJ’s journey is as bold as his beliefs.In this episode, we explore how a bass guitarist’s personal pain point became a global solution, why selling Serato wasn’t just about the payday, and what happens when a tech founder decides to fix the country instead of another product. Whether you're a founder, creative, or voter this conversation is equal parts insight, inspiration, and provocation.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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32
Laetitia Peterson: Wall St doesn't prepare you for startup life
Laetitia Peterson sold her investment company, Liontamer, to a global banking giant - only to watch her buyer teeter on bankruptcy just months later. From navigating a sale at the peak of the market to reclaiming her business during the Global Financial Crisis, Laetitia has faced entrepreneurial highs, daunting lows, and every challenge in between.In this candid conversation, we explore the unexpected twists in exits, the resilience required to pivot amidst chaos, and why the best strategies aren’t always about predicting the future, but being prepared for uncertainty. If you're building towards an exit, or simply wondering what comes next, this episode offers real-world wisdom on managing the unpredictable journey of selling your business.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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31
Keith Davison: 0-$120m exit in 2.5 years!
Keith Davison persevered through five failed startups before achieving a remarkable $120 million exit (in under 3 years from first revenue!). From hustling without a salary for over two years to strategically navigating market timing, Keith’s story reveals the gritty truths behind entrepreneurial success.In this candid episode, we explore what it truly takes to scale a startup, the risks and realities of exiting at the right moment, and how relentless resilience can transform failures into life-changing outcomes. Whether you’re an aspiring entrepreneur or contemplating your next business move, Keith’s insights offer a practical and inspiring blueprint for navigating the highs, lows, and unexpected turns of entrepreneurship.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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30
Jessie Stanley: From pies to flies. Passion, purpose & problems!
Jessie Stanley built a thriving pie empire from scratch—only to realise that success wasn’t what she imagined. In this candid conversation, Jessie shares her journey from obsessively hand-making pies to the complexities of scaling, the emotional rollercoaster of selling her beloved brand, and finding identity beyond the exit.From navigating burnout and balancing motherhood to reinventing herself in the world of sustainable food innovation, Jessie’s story explores the personal side of entrepreneurship—showing that sometimes, exits aren't endings, but rather new beginnings.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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29
Gary Gordon: $1B of property developed. Here's what I know.
Gary Gordon didn’t sell his company—he made the impossible call to shut it down. After two decades in property development and over $1B in completed projects, Gary walked away at the peak.In this episode, we unpack the real reasons why, the lessons behind the numbers, and what it means to choose integrity over inertia. If you’ve ever questioned the cost of scale—or what it truly means to exit—this one will stay with you.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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28
Kelly Brown: 18 yrs of leadership; leave a legacy
Kelly Brown didn’t just grow a profitable business, she exited on her own terms. From a failed M&A attempt to a four-month sprint that led to a clean, quiet sale, she shares what it really takes to build a company that’s not just valuable, but truly sellable.In this episode, we dive into what founders get wrong about exits, why culture without accountability doesn’t work, and how to create a business that thrives without you. Whether you're years away from selling or simply want to lead with more intention, this conversation is a masterclass in long-game leadership.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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27
Alliv Samson: $300m NZ success story "NO silicon valley"
Alliv Samson didn’t just build a startup, she redefined how classrooms work around the world. As the co-founder of Kami, she navigated massive growth during the global pandemic, scaling from 7 million to 40 million users almost overnight. From nearly shutting down to becoming one of the fastest-growing EdTech companies globally, Alliv shares candid insights on knowing when to pivot, handling rapid success, and why money should never distract you from your mission.Whether you're growing your startup, considering an exit, or just curious about the resilience needed to thrive through uncertainty, this conversation will inspire and equip you for the road ahead.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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26
Mark Clare: You set the price, l'll set the terms!
Mark Clare hasn't just advised on hundreds of successful business exits; he’s seen firsthand the pivotal moments that make or break multi-million dollar deals. As the founding partner of Clare Capital, Mark has become the go-to expert for Kiwi founders navigating the complex world of mergers and acquisitions, particularly in the SaaS space.In this episode, Mark shares why competitive tension is your best friend (and why many New Zealand founders miss the mark here), what truly drives company valuations, and the hidden pitfalls in negotiations that can cost you millions. Whether you're planning your exit or just curious about the strategies behind successful deals, Mark's insights offer essential guidance to maximise your outcome and avoid costly mistakes.Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPUDownload the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYoFollow me on LinkedIn: www.linkedin.com/in/joshcomrieVisit https://www.joshcomrie.com/ to see how I can help you on your business journey.
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ABOUT THIS SHOW
Welcome to 2 Commas: The $multi-million exit showI've spent over two decades helping founders scale their businesses and achieve successful, multimillion-dollar exits. I've also achieved this myself on multiple occasions. With my experience as an entrepreneur, advisor, and investor, I’ve had the privilege of guiding companies through the highs and lows of business growth and exit strategies.Each episode will bring you the previously untold stories of entrepreneurs who have successfully scaled and exited their businesses for seven-figure (2 comma's) plus returns. You’ll hear more about the journeys, challenges, and pivotal moments that led to these transformative exits. My goal is to inform and inspire founders who are looking to scale their ventures to seven, eight or nine figures and beyond.Follow me on LinkedIn: www.linkedin.com/in/joshc
HOSTED BY
Josh Comrie
CATEGORIES
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