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.
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 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 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 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 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 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 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 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.
 
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.