NexChapter | Unfiltered wisdom from post exit founders

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. 

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.

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 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 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 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 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 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 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 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.