NexChapter | Unfiltered wisdom from post exit founders

NexChapter 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.   NexChapter 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 Tyler Handley. Tyler is a Canadian entrepreneur best known for co founding Inkbox, a temporary tattoo technology and brand that redefined self expression. Under Tyler's leadership, Inkbox was one of the fastest growing companies in Canada, culminating in its acquisition by BIC for $90M in 2022. He is now redefining the car freshener category with Olauto, as well as being an active investor and advisor.   What we cover Scratching his own itch, travelling to the jungles of Panama with his brother to find the technology behind Inkbox, and turning an unusual idea into a global consumer brand Starting with just $15,000, gaming the Kickstarter algorithm, and using scrappiness, technology and branding to create early momentum Why timing mattered so much, with tattoos becoming mainstream, Instagram advertising exploding, and venture capital helping unlock growth from $8 million to $20 million Building Inkbox with his brother, growing to around $40 million in revenue and 170 people, while developing valuable IP alongside the consumer brand The unexpected approach from BIC during a Series B raise, why brand, demographic reach, IP and distribution made the deal compelling, and navigating a legitimate retrade as consumer spending softened Life inside a large corporate after the sale, losing decision making power, walking away early, and eventually building a different kind of business designed to serve his life rather than consume it https://www.linkedin.com/in/tylerhandley/   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.

NexChapter 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 Rob Hunter. Rob is an eccentric entrepreneur who's pushing 40 and still never held a full-time salaried job. He's been an entrepreneur ever since he was a kid, selling Japanese professional wrestling VHS tapes and DVD's on eBay and his own website to pay his way through an undergraduate degree at the Ivey Business School. After dabbling in real estate, Rob sold his mini student housing empire and got into the ice cream business, opening 7 Marble Slab ice cream stores by the time he was 25. Little did he know that Winter Was Coming, as bankruptcy swiftly set in. Rob embarked a fresh start by moving to Boston to do his MBA at the #1 school in the world for entrepreneurship, Babson College. Over the next several years, he built and eventually sold HigherMe, an HR Tech solution for the restaurant industry that went through Y Combinator in 2015. He also tried to solve the US student debt crisis with Reset Button / Lexria, a venture-backed fintech. Rob is back at it with Foundry, an AI startup that helps small business create, grow, and operate franchise systems. He also does some teaching back at Ivey and at the University of Waterloo.   What we cover Scaling too fast with 7 Marble Slab stores, the hard reality of franchising, and eventual bankruptcy at 29 Turning that failure into a tech wedge, using his operator scars to build HigherMe through Y Combinator - The strategic pivot from “video applications” to making mobile hiring simple, including text to apply and removing every bit of applicant friction Why focus won, narrowing to franchised restaurants and using a bottoms up foot in the door approach that eventually landed major franchise networks Choosing a realistic path over unicorn chasing, staying capital efficient, targeting cash flow positive growth, and avoiding too much dilution and liquidation preference risk The deal story, COVID as an unexpected tailwind, using strategic interest to create competitive tension, the emotional LOI moment, and the surreal bank refresh moment when the wire hit https://www.linkedin.com/in/robhunter7/   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.

NexChapter 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 Jamie Portnoff. Jamie is a high-growth executive and entrepreneur who co-founded and served as CEO of Truliant Consulting. In just 3.5 years, she scaled the firm into a premier global pharmacovigilance advisory, culminating in a successful Private Equity (PE) exit via acquisition. Currently, Jamie is a member of the senior leadership team at ELIQUENT, where she leads the global consulting practice she built while also contributing to enterprise growth strategies. With over two decades of technical authority, Jamie is highly skilled in navigating international complexity, M&A integrations, and business transformation. Known for building high-performing teams, she excels at driving success through strategic partnership and operational transparency. Jamie lives in Baltimore with her husband and daughter.   What we cover Spotting an opportunity in a pharma safety niche that big firms often underweight, then building a premium advisory around it Scaling with six co founders, being intentional about culture and diversity, and managing the human complexity that comes with that model Reputation-led growth, selling less and delivering more, with founder level ownership on projects driving word of mouth demand Navigating choppy, services based revenue while solving high stakes technical and international complexity for clients An unplanned sale process triggered by visibility and marketing, plus why staying open to conversations with investors and acquirers matters The post deal reality, integrating into a PE backed platform, adjusting to new success metrics, and deciding whether to build again https://www.linkedin.com/in/jamie-portnoff-2039008/   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.

NexChapter 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 Dr. Michael Filosi. Michael is a fully-fledged, card-carrying nerd, and he would not have it any other way. He loves to solve hard, interesting, meaningful problems and is ever curious about how to do things better and dive deeper into those areas of life and business that interest him. A dentist by profession and training, Michael turned a worn-out two surgery dental practice with a big heart and great bones into a ten surgery facility in Adelaide, Australia, before exiting via sale in September 2025. When others zigged, Michael zagged. Forget about hard sells and “pushing” dental treatment on patients, Michael decided that his business would focus on looking after people, doing the right thing, and trust that patients would tell their friends and family. Guess what? It worked. A husband to Greta (also a dentist) and father to an eight-year-old daughter, Michael spends his spare time reading and indulging his love of the twin joys of learning and play – be that a board game, a magic trick, a basketball scrimmage with friends, or building a treehouse. Not sure where he is in a crowd? Look for the tallest person in the room, and it is probably Michael.   What we cover Buying a non-sexy dental practice that “nobody wanted,” seeing the potential, then expanding a single site into a 10 chair flagship rather than chasing the multi site empire model The pivotal decision to come off the tools, park ego, recruit better clinicians, and turn a founder dependent practice into a business that could run without him How he grew a mature, local healthcare business by dominating digital trust signals, especially Google reviews, and treating it as 'word of thumb' Why the joy disappeared when the work shifted from building to fixing, and how stress has a real physical cost for founders A proactive exit process, including calling likely buyers directly to create competitive tension, and structuring a walk in walk out sale with cash up front and low key person risk Life after the deal, taking time, saying no, and waiting to fall in love with the next hard, interesting, meaningful problem rather than forcing the next move https://www.linkedin.com/in/michaelfilosi/   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.

NexChapter 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 Robin Kerbel. Robin is an entrepreneur and strategic leader with more than three decades of experience building and scaling global healthcare communications businesses. She co-founded Six Degrees Medical in 2005, growing it into an internationally recognized consultancy serving life sciences clients across North America, Europe, and beyond. After nearly 20 years at the helm, Robin led the successful sale of Six Degrees Medical to Reverba Global in 2024, helping guide the integration while serving as Chief Strategy Officer. In early 2026, Robin transitioned out of Reverba to explore her next chapter as a post-exit founder, focusing on new ventures, community-driven initiatives, and advisory work. She brings a founder’s perspective on scaling with purpose, navigating M&A, and redefining identity and impact after an exit.     What we cover How Robin built a highly respected niche medical communications agency by starting lean with contractors, then recruiting senior talent with strong reputations that naturally generated referral driven growth The power of scientific rigor and interactive education as a clear differentiator in a crowded pharma services market Why investing in leadership, process, and EOS before a sale made her operationally redundant and significantly strengthened the business - The key value drivers behind the transaction, including geographic presence in Canada and the UK, blue chip global clients, and a deeply experienced science team Why culture fit and strategic alignment mattered more than headline price when choosing the right buyer How she mentally prepared to leave after nearly 20 years, and why her next chapter now includes building a husband and wife events business rooted in community north of Toronto https://www.linkedin.com/in/robin-kerbel-479b333/ 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.

NexChapter 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 Andrew Kirpalani. Andrew co-founded workforce engagement platform WorkHound with Max Farrell in 2015 . He grew the company as it's CTO through 2023 before stepping away from day-to-day operations. He remained on the board of directors from that time until WorkHound's recent acquisition by WorkStep. From 2023 though 2025, he served as an Entrepreneur in Residence at Iowa State University's Startup Factory, supporting early-stage entrepreneurs. He has nearly two decades of software development, product management, fundraising and company building experience in varied industries, along with the scars to prove it. Now he's trying to figure out what he wants to be when he grows up.   What we cover Why niching into trucking and frontline workers created a real moat, because trust takes years and does not compress even in the AI era How investor perception of market size can matter more than reality, and why “trucking is huge” versus “trucking is tiny” depends who you ask Capital efficient growth, raising just enough to get extra juice without giving away the company, and how timing and macro markets shape value more than founders like to admit The boom and bust of COVID in trucking, and how tailwinds can flip to headwinds quickly in cyclical markets - The shift from VC and angels to growth equity and private equity, including taking some chips off the table and letting employees cash in options for once The long exit journey, stepping off the operating team before the final sale, staying on the board, and the psychological challenge of giving away your toys Post exit life, the sabbatical, the black hole of time, losing the social connection that came from the team, and the slow process of figuring out what comes next https://www.linkedin.com/in/kirps/ 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.

NexChapter 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 Adam Rossi. Adam  is a tech entrepreneur who built a 250-person software company serving law enforcement and intelligence agencies—often outcompeting giants like Lockheed Martin in head-to-head bids. When a banker returned with five acquisition offers matching the “absurd” figure he and his wife had once tossed around, Adam accepted an all-cash deal from SRA International, a publicly traded defense contractor. The sale created generational wealth for his family, with no earn-out or strings attached.   After the exit, Adam learned that the hardest part of selling a company isn’t the negotiation—it’s deciding what comes next. Today, he shares his journey and insights to help other founders navigate the challenges of building, selling, and redefining success beyond the business.   https://www.linkedin.com/in/adamrossi-indie/   What we cover How 9 11 unintentionally pivoted his company into mission driven national security work with powerful tailwinds Becoming a recognised expert in a narrow niche and winning prime government contracts that created real defensibility The inflection point where removing himself as the bottleneck unlocked serious growth Accepting an all cash deal with no earn out, yet choosing to operate with honour beyond contractual obligation The emotional crash after exit, including depression, identity loss, and missing the mission Why both scarcity and abundance create stress, and how he rebuilt purpose through discipline, diligence, and family   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.

NexChapter 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 Joe Rideout. Joe is a software engineer turned entrepreneur. He co-founded Perpetua, a SaaS platform that automates advertising for brands on Amazon and other marketplaces. The company was acquired in 2021 and became part of Ascential’s digital commerce segment. In his next chapter, Joe is building at the intersection of technology and human performance while co-founding Burn Room, a Toronto-based fitness studio. He is a competitive marathoner and HYROX athlete, passionate about the intersection of ambition, health, and long-term performance. https://www.linkedin.com/in/joerideout/   What we cover: Lessons from a first exit where equity was exchanged for equity that did not fully materialise Why a great market will pull a product out of the team Discovering and doubling down on Amazon advertising at the right moment Understanding the importance of choosing the right co founder and founding team the second time around Structuring a deal with meaningful upfront consideration and an earn out aligned to performance The complexity of post acquisition integration when multiple companies merge The health cost of founder obsession and the stress that can continue after the deal Moving from intensity to intentionality in life after 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.

NexChapter 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 Shenar Wood. Shenar is a CEO and founder with a track record of building and scaling electric utility services organizations through growth, transformation, and strategic transition. As the founder of Dynetek Solutions in Tampa, he led the company through rapid expansion, building the operating cadence and capabilities that ultimately supported a successful sale and platform integration. He directed the full M&A lifecycle including valuation modeling, due diligence, negotiations, and operational readiness. Shenar has also driven enterprise modernization through the deployment of integrated operating systems that standardized workflows and strengthened compliance at scale, while improving safety performance across key metrics. A former U.S. Army rotary-wing pilot and Chief Warrant Officer, he brings high-consequence decision-making and team leadership developed in demanding environments. He holds an MBA from Emory University.   LinkedIn: https://www.linkedin.com/in/shenar-wood/   What we cover Why building culture in an unglamorous, operationally heavy business became a strategic advantage How military principles such as servant leadership, calm decision making, and disciplined budgeting translated directly into entrepreneurship The operational levers that drove value, including process automation, lean management, and investing in field teams How his MBA reshaped his understanding of capital and led him toward private equity The real value drivers behind the transaction, from future cash flows to niche capability and geographic strength The emotional side of the deal, from validation and relief to stepping into a larger platform with renewed motivation 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.

NexChapter 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 Randy Woods . Randy is a twice-exited entrepreneur and senior M&A executive who has spent more than 30 years building, acquiring, and selling technology-enabled businesses across North America, Europe, and Latin America. He co-founded Nonlinear Creations in 1995 and led it for over two decades, scaling it into a multinational digital agency before running a competitive process that culminated in its strategic sale to Valtech   He then joined Valtech’s North American executive team, helping drive strategic growth and contributing to nine acquisitions as the company expanded significantly Earlier, as co-founder and CEO of Buystream, he raised over $20M in venture capital and navigated the firm through the dot-com collapse, ultimately managing the sale of its intellectual property to Watchfire (later acquired by IBM).   Today, as Vice President at Corum Group, Randy draws on hard-won experience from every side of the table to help founders exit successfully - achieving strong valuations, thoughtful deal structures, and outcomes aligned with life beyond the transaction. Linkedin > https://www.linkedin.com/in/randwoods/   What we cover How Randy scaled a digital agency over 23 years by embracing mistakes, staying brave, and getting the timing right on offshoring before it became the norm The painful lesson that salespeople can walk out, and the pivot to a content engine that created a measurable marketing flywheel independent of founders Why he chose not to niche by vertical, instead building resilience across sectors while going deep in a capability niche through Sitecore expertise The value drivers that made the business irresistible in a strategic sale, including geographic presence through an integrated Brazil team, capability, management depth, and crystal clean books years before going to market The double transition after exit, moving into Valtech as an operator and corporate development leader, helping drive 9 acquisitions as the business grew from 2,000 to 8,000 people What he learned on the buy side, including red flags in founders and deals that led him into his new NexChapter   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.

NexChapter 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 Ryan Atkinson. Ryan is a serial entrepreneur and investor with more than 25 years of experience building, scaling, and successfully exiting recruitment and professional services companies. He’s co-founded and led some of Canada’s fastest-growing staffing and technology firms, including Redwood Global, Direqlink, and CORE Resources, a national leader in IT staff augmentation and Agile consulting. Known for his ability to spot market gaps and move fast, Ryan has built businesses through every phase of the cycle—startup, hyper-growth, acquisition, and integration. He grew Redwood Global from two founders to $30 million in annual revenue, earning multiple PROFIT 500 awards before selling to S.i. Systems. At CORE, he helped hundreds of enterprise clients modernize their workforces through Agile transformation and cloud-based staffing models.   A lifelong problem-solver, Ryan’s superpower is turning complexity into clarity—whether that means building go-to-market engines, scaling sales teams, or closing the deals others can’t. He leads with energy, candour, and a bias for action, helping founders and executives push through the noise to execute. Ryan Atkinson - Rylora Ventures   What we cover How building A player teams and A list clients became the repeatable playbook behind two high growth exits Why contract staffing created defensible, cash flowing annuity revenue that drove valuation The difference between selling exclusively the first time and creating competitive tension the second time What it really takes to be diligence ready, from clean books to ironclad client and contractor agreements The bucket of money versus cash flow dilemma that hits after exit Achieving escape velocity financially, yet still feeling the pull to build again 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.

NexChapter 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 husband and wife team, Ryan and Kristin O'leary. Ryan is the co-founder and former CEO of Sonapay (SONA), a Canadian merchant services company he built from scratch in Bedford, Nova Scotia in 2016. Over eight years, bootstrapped and values-driven, SONA grew to serve 5,000 merchants across Canada, processing over $1B in annual volume with industry-leading retention rates and a culture built on transparency and solution selling. In 2024, SONA was acquired by Celero Commerce. Ryan is now the founder of ROKO Holdings and Investments, deploying capital into fintech, venture, and early-stage companies. He and his wife Kristin are preparing to circumnavigate the globe aboard their Oyster 625, Distraction, in the 2028 Oyster World Rally — a dream that was literally written into their wedding vows 19 years ago. LinkedIn: https://www.linkedin.com/in/ryanoleary1/   Kristin is the co-founder and former COO of Sonapay (SONA), where she built and ran the operational engine behind one of Canada's most respected merchant services brands. A CAIB-certified insurance broker turned entrepreneur, Kristin previously acquired and successfully exited her own business before joining SONA full time. She is the integrator to Ryan's visionary — the steady hand who kept the business, the family, and the mission on track through eight years of bootstrapped growth. She is now co-steering the family's next chapter, including a global sailing circumnavigation in 2028. LinkedIn: https://www.linkedin.com/in/kristin-o-leary-34176115b/   What we cover Leaving a stable day job with 4 kids at home, betting on a values driven approach to payments built on transparency and trust Building a residual revenue model that compounded over time to create a scalable distribution engine Designing an agent model that rewarded people fairly, created loyalty, and became a self sustaining fintech brand The reality of founder burnout, and why what got them here would not get them where they wanted to go next, hence the deal Running a tight, targeted sale process by preparing 2.5 years in advance, then generating multiple LOIs fast with only 5 acquirers approached Navigating the emotional complexity of staggered earn outs, including resentment, identity shift, and rebuilding routines after the exit The long term pull that anchored their decision making, a 2028 Oyster World Rally circumnavigation that was literally written into their wedding vows, plus a foundation focused on care and youth at risk 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.

NexChapter 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... Connect with John -   / johnrood1   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... Connect with John -   / johnrood1   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.

NexChapter 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/  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 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.

NexChapter 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 is available now.  Connect with Ujwal - 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 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.

NexChapter 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/ 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 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.

NexChapter 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/ 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 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.

NexChapter 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 Kristen Closson. Kristen is a 3X founder and healthcare operator with a focus on building practical, high-impact companies. She is the co-founder of Viewgol, a healthcare revenue intelligence platform and global teams acquired in 2023, as well as MonArk ABA Therapy, which provides services to autistic children, and Vlush, a women’s health brand focused on evidence-based vaginal care. Across healthcare technology, services, and consumer health, Kristen is known for building businesses grounded in real-world problems, trusted data, and thoughtful execution. Today, she’s focused on being a student of AI and supporting MonArk and Vlush. Connect with Kristen - https://www.linkedin.com/in/kristenclosson/ What we cover  - How Kristen built and scaled global teams starting in India through persistence and trust  - Why starting with contracting before hiring full time teams reduced risk and enabled scale  - How customer obsession became the ethos to drive the real engine of growth of India  - Why multi founder teams benefit from facilitation and coaching  - How building buyer relationships early created a competitive exit process  - The emotional complexity of selling a business and navigating the messy middle  - Why purpose driven work matters even more after 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.

Welcome to NexChapter! NexChapter 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.   Post exit founders are the small group of entrepreneurs who built a company, sold it, and then had to figure out what came 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.   Each episode follows the 3Ts: Trajectory: how the business was built Transaction: how the deal really happened Transition: what life looks like after the 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.   For first access and updates, join the email list: https://nex-chapter.com/, and connect with our host, Raman on LinkedIn.