John Rood - Beyond the Exit: what happens next

John Rood - Beyond the Exit: what happens next

NexChapter [https://nex-chapter.com/] is the home of unfiltered wisdom from post exit founders. Recorded in The Republic Studio, this show is for founders who are scaling businesses and founders who have sold and are figuring out what the hell happens next. Each episode explores the real story behind the exit, the decisions that mattered, and the personal transition that follows when the deal is done. In this episode, Raman Sehgal sits down with John Rood. John is the author of Beyond The Exit, informed by interviews with 70+ post-exit entrepreneurs. Previously, John was founder of Next Step Test Preparation, a medical education platform. John lives in the Chicago area with his wife and two kids. Beyond The Exit, Book - https://www.amazon.com/Beyond-Exit-Su... [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa2Q0c2hzUEdZWlBWVGFRUHNhMzBqOGF6NFpCQXxBQ3Jtc0tsbzF2bkJZVzdUQkkxd1M3UHoxQ2xyUFJLR3NjcEtsWmdXUVVIMWRiZmVqY2c1NWJVbXBQdDNZV3dFZ2ZJNHZrMVJ6V3R5RHdoNWtiSGg3OU41RXZ6VzllZWRGZE1aOHpuR0ZTMmFLQm1nX0RwaUlNSQ&q=https%3A%2F%2Fwww.amazon.com%2FBeyond-Exit-Successful-Entrepreneurs-Their%2Fdp%2FB0DRCWS3P6&v=HQXuaGF0G1M] Connect with John -   / johnrood1   [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqazNGN0hZdkdRVlR1TW5BN2NCRDUwSlBXVlRNZ3xBQ3Jtc0tubUVxTU90YmViT1hkZTBYWE85WUtQSzhTMF9OaTNsb0pmY1VxUUhfRkRoZ0E1ZnctOVQ1OE9Kc242VkVTV0NFUDJ5ZnVxNzQ2NmJ2UEVQTFMzaG9zcFoySkwwX1ZSTmYyNEtsM0ZNXy1rbzVVR096WQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fjohnrood1&v=HQXuaGF0G1M] What we cover * How John built and scaled a valuable education business by moving from services to software * Why surrounding yourself with better people is a critical CEO transition * How understanding what buyers value early can shape a stronger exit * The biggest mistakes founders make after they sell * The emotional reality of post exit life and why doing nothing makes entrepreneurs miserable * Why time, not money, becomes the real currency after an exit Your host Raman Sehgal is the author of the best selling book The Floundering Founder, Toronto Chapter Lead at Post Exit Founders (PEF), investor, and founder of several niche firms and platforms in the pharma and biopharma services space, one of which he sold a majority stake in to private equity. He created NexChapter to capture the hard earned wisdom of founders who have been through an exit and are willing to share what really worked, what surprised them, and what comes next. Connect with Raman. is the home of unfiltered wisdom from post exit founders. Recorded in The Republic Studio, this show is for founders who are scaling businesses and founders who have sold and are figuring out what the hell happens next. Each episode explores the real story behind the exit, the decisions that mattered, and the personal transition that follows when the deal is done. In this episode, Raman Sehgal sits down with John Rood. John is the author of Beyond The Exit, informed by interviews with 70+ post-exit entrepreneurs. Previously, John was founder of Next Step Test Preparation, a medical education platform. John lives in the Chicago area with his wife and two kids. Beyond The Exit, Book - https://www.amazon.com/Beyond-Exit-Su... [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa2Q0c2hzUEdZWlBWVGFRUHNhMzBqOGF6NFpCQXxBQ3Jtc0tsbzF2bkJZVzdUQkkxd1M3UHoxQ2xyUFJLR3NjcEtsWmdXUVVIMWRiZmVqY2c1NWJVbXBQdDNZV3dFZ2ZJNHZrMVJ6V3R5RHdoNWtiSGg3OU41RXZ6VzllZWRGZE1aOHpuR0ZTMmFLQm1nX0RwaUlNSQ&q=https%3A%2F%2Fwww.amazon.com%2FBeyond-Exit-Successful-Entrepreneurs-Their%2Fdp%2FB0DRCWS3P6&v=HQXuaGF0G1M] Connect with John -   / johnrood1   [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqazNGN0hZdkdRVlR1TW5BN2NCRDUwSlBXVlRNZ3xBQ3Jtc0tubUVxTU90YmViT1hkZTBYWE85WUtQSzhTMF9OaTNsb0pmY1VxUUhfRkRoZ0E1ZnctOVQ1OE9Kc242VkVTV0NFUDJ5ZnVxNzQ2NmJ2UEVQTFMzaG9zcFoySkwwX1ZSTmYyNEtsM0ZNXy1rbzVVR096WQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fjohnrood1&v=HQXuaGF0G1M] What we cover * How John built and scaled a valuable education business by moving from services to software * Why surrounding yourself with better people is a critical CEO transition * How understanding what buyers value early can shape a stronger exit * The biggest mistakes founders make after they sell * The emotional reality of post exit life and why doing nothing makes entrepreneurs miserable * Why time, not money, becomes the real currency after an exit Your host Raman Sehgal [https://www.ramansehgal.com/] is the author of the best selling book The Floundering Founder, [https://www.amazon.com/-/es/Floundering-Founder-Lessons-Business-Yourself/dp/1544527217] Toronto Chapter Lead at Post Exit Founders (PEF), investor, and founder of several niche firms and platforms in the pharma and biopharma services space, one of which he sold a majority stake in to private equity. He created NexChapter to capture the hard earned wisdom of founders who have been through an exit and are willing to share what really worked, what surprised them, and what comes next. Connect with Raman. [https://www.linkedin.com/in/ramansehgalus/]

NexChapter interview with Ray Chang - From Exit to Encore: Building a Business for Joy

NexChapter [https://nex-chapter.com/] is the home of unfiltered wisdom from post exit founders. Recorded in The Republic Studio, this show is for founders who are scaling businesses and founders who have sold and are figuring out what the hell happens next. Each episode explores the real story behind the exit, the decisions that mattered, and the personal transition that follows when the deal is done. In this episode, Raman Sehgal sits down with Ray Chang.  Ray, he is an award-winning travel and owner of Motorsport Lab. With over 1000 5-star reviews on TripAdvisor and accolades from DuPont Registry Exotic Car Magazine, Ray is the ultimate guide for motorsport enthusiasts. As an Aston Martin, Ferrari, and Lamborghini owner, Ray’s passion for motorsport shines through his unique travel adventures.  Experience the origins of iconic brands while immersing in the local culture, design, and cuisine. Enjoy driving exotic cars, visiting Formula 1 racetracks, touring auto museums with exclusive previews, dining at top restaurants, shopping at boutique stores, and even having an espresso with factory workers.  Ray’s personable nature, “help-first” attitude, and extensive knowledge of local cultures and cuisines make every trip unforgettable. Join Ray for a journey filled with thrilling motorsport experiences and rich cultural insights. From driving exotic cars and visiting Formula One racetracks, to touring auto museums with private access, dining at top restaurants, shopping at boutique stores, and even sharing an espresso with factory workers, Ray has designed experiences that feel personal, immersive, and unforgettable. After exiting his first business, Ray eventually found his way back to the world of exotic cars through what he calls an encore job. One built not around money, but around joy, curiosity, and experience. Connect with Ray [https://www.linkedin.com/in/raychang/]- https://www.linkedin.com/in/raychang/  What we cover - How Ray turned a lifelong passion for cars and racing into a business - Why language and positioning mattered more than he realised - The hidden complexity and pressure behind a sexy business - The realities of life after exit and the search for what comes next - How boredom, curiosity, and revenge travel led to an unexpected second act Your host Raman Sehgal [https://www.ramansehgal.com/]is the author of the best selling book The Floundering Founder, [https://www.amazon.com/-/es/Floundering-Founder-Lessons-Business-Yourself/dp/1544527217] Toronto Chapter Lead at Post Exit Founders (PEF), investor, and founder of several niche firms and platforms in the pharma and biopharma services space, one of which he sold a majority stake in to private equity. He created NexChapter to capture the hard earned wisdom of founders who have been through an exit and are willing to share what really worked, what surprised them, and what comes next. Connect with Raman [https://www.linkedin.com/in/ramansehgalus/].

NexChapter interview with Ujwal Arkalgud - Killing the Services Cash Cow to Build a SaaS Exit

NexChapter [https://nex-chapter.com/] is the home of unfiltered wisdom from post exit founders. Recorded in The Republic Studio, this show is for founders who are scaling businesses and founders who have sold and are figuring out what the hell happens next. Each episode explores the real story behind the exit, the decisions that mattered, and the personal transition that follows when the deal is done. In this episode, Raman Sehgal sits down with Ujwal Arkalgud. He is a cultural anthropologist, exited entrepreneur, and investor specializing in "Valuation Engineering" for founder-led firms. After bootstrapping MotivBase to a high eight-figure exit, he now helps leaders decode the hidden buyer psychology that often caps growth. Proven across VC, PE, and bootstrapped environments, his work ensures founders get full credit for the businesses they’ve built. Ujwal is also the author of Invisible Rules, which examines how unseen cultural architecture influences careers, creativity, and leadership. His work invites people to question inherited assumptions and consider what becomes possible once those assumptions are made visible. Invisible Rules [https://www.amazon.ca/Invisible-Rules-Outsmart-Entrepreneurial-Game/dp/177458686X/ref=asc_df_177458686X?mcid=99a8c39e19e93776b70501ed0ef90a72&tag=googleshopc0c-20&linkCode=df0&hvadid=791510599879&hvpos=&hvnetw=g&hvrand=6574676852029868345&hvpone=&hvptwo=&hvqmt=&hvdev=c&hvdvcmdl=&hvlocint=&hvlocphy=9198282&hvtargid=pla-2472498638845&psc=1&hvocijid=6574676852029868345-177458686X-&hvexpln=0&gad_source=1]is available now.  Connect with Ujwal [https://www.linkedin.com/in/ujwalarkalgud/]- https://www.linkedin.com/in/ujwalarkalgud/ What we cover - How an anthropological lens helped Ujwal cut through the ugly truth of market research and bring clarity to complex consumer behaviour - The selling approach that helped him break into major brands, including why he led with where the industry was headed rather than product features - Using services to generate cash and learn the invisible rules of decision making, then productising the methodology and turning it into SaaS - The cold turkey shift from services to SaaS, dropping revenue from $5m to $1.5m, losing clients, and riding the hockey stick back up - The 2020 failed sale process that became a silver lining, tightening the business around sales efficiency, EBITDA, and clean recurring revenue - Post exit reality, the jittery withdrawal, taking real time off, and resisting the urge to jump into the next company too fast Your host Raman Sehgal [https://www.ramansehgal.com/]is the author of the best selling book The Floundering Founder, [https://www.amazon.com/-/es/Floundering-Founder-Lessons-Business-Yourself/dp/1544527217] Toronto Chapter Lead at Post Exit Founders (PEF), investor, and founder of several niche firms and platforms in the pharma and biopharma services space, one of which he sold a majority stake in to private equity. He created NexChapter to capture the hard earned wisdom of founders who have been through an exit and are willing to share what really worked, what surprised them, and what comes next. Connect with Raman [https://www.linkedin.com/in/ramansehgalus/].

NexChapter interview with Dmitry Dragilev - 4 x Exits... working 3 Hours a Day!

NexChapter [https://nex-chapter.com/] is the home of unfiltered wisdom from post exit founders. Recorded in The Republic Studio, this show is for founders who are scaling businesses and founders who have sold and are figuring out what the hell happens next. Each episode explores the real story behind the exit, the decisions that mattered, and the personal transition that follows when the deal is done. In this episode, Raman Sehgal sits down with Dmitry Dragilev. Dmitry is a 4x acquired SaaS founder and growth expert on a mission to build businesses that serve life, not the other way around. He has spent the last 15 years developing a model for high-margin, self-managing companies designed to deliver both time freedom and meaningful impact—a model validated by a decade of successful exits. Dmitry’s track record of building autonomous, high-value platforms includes: *TopicRanker (Acquired by Semrush, 2025): Originally launched as the top-performing app in the Semrush App Center, this SEO tool identified ranking weaknesses to help users dominate search results. *SmallBiz.Tools (Acquired by Semrush, 2023): A trusted affiliate and software review platform built to help entrepreneurs navigate the complex world of business tools. *JustReachOut (Acquired by SEOJet, 2020): An AI-powered PR platform that empowered 5,000+ small businesses to pitch journalists and podcasters without an agency; later re-acquired by early Slack employees in 2024. *Polar Polls (Acquired by Google, 2014): As the sole marketer on a five-person team, Dmitry used aggressive PR to scale this polling startup to 40 million monthly pageviews, leading to Google’s 166th acquisition. Beyond his own ventures, Dmitry is a master of search and AI visibility. Since 2009, he has consulted for over 500 companies—from solo founders to global giants like HubSpot, Dow Jones, Realtor.com, Pipedrive, and Wistia—helping them rank #1 on Google and LLMs for their most critical keywords. A prominent voice in the tech community, Dmitry is a frequent contributor to Forbes, Wired, and TechCrunch. He also founded the ZURBsoapbox series, where he has interviewed visionaries such as Tim Ferriss, the Winklevoss Twins, and the founders of Twitter, LinkedIn, and Eventbrite. Today, he focuses on teaching founders how to build impactful, self-sustaining businesses that leave plenty of room for what matters most: living. Connect with Dmitry [https://www.linkedin.com/in/dmitrydragilev/] - https://www.linkedin.com/in/dmitrydragilev/ What we cover - Why many “successful” founders end up unhappy, and how Dmitry deliberately chose a different model early in his career - The philosophy of building businesses that serve life rather than consume it, and how he shifted from services to scalable software to eliminate time sinks - How he reduced his working hours with each company, moving from full time founder to roughly 3 hours a day - Designing SaaS products that are autonomous, self serve, and built to run without daily founder oversight - Building inside large app marketplaces with a clear acquirer in mind from day one, and how he often identifies the likely buyer before he even builds the product - Structuring acquisitions so he avoids full time employment post sale - Why family time, health, and community are non negotiables, not rewards after an exit - How he measures success through connection, impact, and joy rather than just financial outcomes Your host Raman Sehgal [https://www.ramansehgal.com/]is the author of the best selling book The Floundering Founder, [https://www.amazon.com/-/es/Floundering-Founder-Lessons-Business-Yourself/dp/1544527217] Toronto Chapter Lead at Post Exit Founders (PEF), investor, and founder of several niche firms and platforms in the pharma and biopharma services space, one of which he sold a majority stake in to private equity. He created NexChapter to capture the hard earned wisdom of founders who have been through an exit and are willing to share what really worked, what surprised them, and what comes next. Connect with Raman [https://www.linkedin.com/in/ramansehgalus/].

NexChapter interview with Ned MacPherson - 20 Hour Rule: Growth, Exit and Life After the Deal

NexChapter [https://nex-chapter.com/] is the home of unfiltered wisdom from post exit founders. Recorded in The Republic Studio, this show is for founders who are scaling businesses and founders who have sold and are figuring out what the hell happens next. Each episode explores the real story behind the exit, the decisions that mattered, and the personal transition that follows when the deal is done. In this episode, Raman Sehgal sits down with Ned MacPherson to unpack a remarkable journey from solo operator to private equity backed exit. Ned is a growth focused operator who has held senior roles including Chief Marketing Officer, Head of Growth, and Head of Revenue. He has led growth initiatives for more than 60 businesses across Direct To Consumer, SaaS, mobile applications, B2B, and ecommerce. His work sits at the intersection of data, experimentation, behavioural psychology, and execution. After scaling his agency, Ned sold the business to a private equity backed strategic buyer, rolled meaningful equity into the next chapter, and now operates in a senior leadership role while continuing to pursue new challenges inside and outside of work. Connect with Ned [https://www.linkedin.com/in/ned-m-3029a120/]- https://www.linkedin.com/in/ned-m-3029a120/ What we cover - How Ned built and positioned a highly differentiated growth and CRO business - What made the company attractive to private equity buyers - Why the transition after the deal has been more positive than most founders expect - The 20 hour rule and how deliberate practice applies to business and life after exit Your host Raman Sehgal [https://www.ramansehgal.com/]is the author of the best selling book The Floundering Founder, [https://www.amazon.com/-/es/Floundering-Founder-Lessons-Business-Yourself/dp/1544527217] Toronto Chapter Lead at Post Exit Founders (PEF), investor, and founder of several niche firms and platforms in the pharma and biopharma services space, one of which he sold a majority stake in to private equity. He created NexChapter to capture the hard earned wisdom of founders who have been through an exit and are willing to share what really worked, what surprised them, and what comes next. Connect with Raman [https://www.linkedin.com/in/ramansehgalus/].