2 Commas: The $multi-million exit show with Josh Comrie

2 Commas: The $multi-million exit show with Josh Comrie

by Josh Comrie

Entrepreneurship

Season 5

By interviewing 20+ founders, she added 25% to the price! | Shivani Gupta | 2 Commas by Josh Comrie

Most founders sell a business once, with no idea what they're doing. Shivani Gupta refused to go in blind. Before she sold her wellness business, Shivani tracked down more than 20 founders who'd already exited and asked every one of them the same questions. What did you sell for, did you use a multiple of EBIT, what would you do again, what would you never do again. She put every answer into a spreadsheet, found the three lessons that came up most often, and applied all three. It added 25% to her final sale price, with no broker. A former electrical engineer who left corporate life after a trip to Nepal, Shivani had already built the business to 10X and exited at 11X. This conversation is the closest thing to an exit strategy masterclass you'll get from someone who taught herself the whole thing. We get into: The research process that added 25% to her exit Why squeezing every line item flows straight through to your valuation Why she turned down a higher offer that would not give her staff contracts How she brought her key leaders inside the sale rather than hiding it The scaling mindset she now uses to help founders think past incremental growth The best time to learn how to sell a business is long before you have to. 📩 Subscribe to the 2 Commas Journal → https://www.joshcomrie.com/subscribe 📖 Order the 2 Commas book → https://www.joshcomrie.com/2-commas-book-order 👤 Follow Josh on LinkedIn → https://www.linkedin.com/in/joshcomrie/

Season 4

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.

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.

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.

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.

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.

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.

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.

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.

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/subscribe⁠⁠ Follow me on LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.linkedin.com/in/joshcomrie⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Visit ⁠⁠⁠https://www.joshcomrie.com/⁠⁠⁠ to see how I can help you on your business journey.

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