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This is the Second Bite Podcast where we talk with top entrepreneurs and CEOs about creating valuable companies through creative transactions.
131 Episodes
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Ben Landers is the President and CEO of Ahead of Next, a company he founded after exiting his prior business. Previously, he was the Founder of Blue Corona, a data-driven digital marketing and analytics firm specializing in helping home-services companies improve marketing performance and generate leads and sales. Ben was also the Vice President of Sales and Marketing at DrinkMore Water, where he launched several websites and an e-commerce store. In this episode… High-growth founders often face pivotal moments that force them to reexamine their goals: financial freedom, operational control, or a new chapter entirely. How can an entrepreneur navigate these crossroads while keeping the business and their personal identity intact? Ben Landers, President and CEO of Ahead of Next, talks about selling his fast-growing digital marketing company. With host Todd Taskey, Ben explains how he evaluated buyers, prepared for a smooth transaction, and adapted to life after stepping away from the business.
Jordan Ross is the Founder and CEO of 8 Figure Agency, a consultancy that helps digital marketing agencies scale to seven- and eight-figure revenues through AI-powered systems. With over a decade of experience, he managed more than 2,500 employees while working at Amazon. Since founding 8 Figure Agency, Jordan has consulted with more than 1,000 agencies. In this episode… Efficiency, profitability, and AI are rewriting the growth playbook for agencies, leaving many founders wondering how to keep up. How can you transform the way your business runs — without selling more? Founder and CEO of 8 Figure Agency, Jordan Ross, discusses how AI-driven efficiency is reshaping agency operations. With host Todd Taskey, Jordan explains how agencies can unlock hidden profit, strengthen sales follow-up, and shift from service provider to business owner.
Doug Hathaway is the Co-founder and CTO/CPO of LawFi, a legal fintech platform that helps consumers and small businesses finance legal services. With over 20 years of experience in software engineering, he co-founded DadeSystems, a SaaS platform for Fortune 500 enterprises and top banks, which was acquired by Versapay, where he led its Cash Application platform. In this episode… The journey from startup to profitable exit is rarely a straight line, and the twists often reveal the most valuable lessons. How did a decade of persistence, pivots, and near-misses lead to the right acquisition at the right time? Co-founder and CTO/CPO of LawFi, Doug Hathaway, discusses building and selling his company after 11 years of growth. With host Todd Taskey, Doug talks about navigating investor influence, managing shifting board dynamics, and handling the emotional swings of a deal that nearly collapsed before closing.
Ryan Redding is the Founder and Business Growth Coach at Eightfold Advantage, a growth-coaching practice that helps entrepreneurs restore operational clarity, increase profitability, and prepare businesses for exit. Before Eightfold Advantage, Ryan was the Owner of Levergy, a nationally recognized digital marketing agency serving HVAC companies that he sold to KickCharge in 2025. In this episode… Strategic acquisitions can accelerate growth and create powerful market advantages, but navigating an unexpected offer requires careful planning and foresight. How can entrepreneurs balance risk, timing, and team integrations to ensure an effective transaction? Ryan Redding, former Owner of Levergy, shares how he scaled his digital marketing agency before selling it. With host Todd Taskey, Ryan explains his approach to valuation and deal structures, the role of cultural due diligence in merging teams, and the importance of incentivizing leadership after the transaction.
Todd Taskey is an M&A Advisor for CEOs and Entrepreneurs at Potomac Business Capital. He has been an entrepreneur, business owner, investment banker, and business finance advisor for more than 20 years. In addition to providing M&A advice, Todd has been a founding investor, board member, or part of the management team of several business ventures. He helps CEOs and entrepreneurs develop a successful exit strategy through his knowledge of the mid-market investment banking process. In this episode… Navigating key players in a transaction is critical for agency founders looking to maximize value, but how can they manage CEOs, sales leaders, and staff whose roles heavily impact a deal? M&A advisor Todd Taskey discusses the challenges of hiring key people and how private equity buyers evaluate leadership teams. With guest host Dr. Jeremy Weisz of Rise25, Todd shares real-world examples of negotiating non-competes, structuring equity with incentive units, and communicating with employees during due diligence.
Jeff Spanbauer is the Founder and Chairman of the Board at Relevate Health, a healthcare marketing firm. Under his leadership, Relevate Health has expanded through four acquisitions and achieved significant revenue growth, earning recognition, including the Inc. 5000 Fastest Growing Companies award. Jeff is also the Co-founder and Director of Revelocity Sports and serves as an investment advisor and partner for multiple companies. In this episode… Strategic acquisitions can rapidly accelerate growth, but how do founders know when it's time to bring in private equity, and what does it take to scale after the deal? Jeff Spanbauer, Founder and Executive Chairman of Relevate Health, shares how he led a data-driven healthcare marketing company through multiple acquisitions and a private equity partnership. With host Todd Taskey, Jeff talks about his patented regional segmentation strategy, the cultural and operational challenges of rapid growth, and how he structured equity incentives for his employees.
Nick Fraunfelder is the Owner and CEO of Sure Oak, a leading SEO agency helping B2B and tech brands grow through search. Since acquiring Sure Oak in 2023, he has led the agency's expansion into AI-powered search optimization. With over 20 years of experience in digital marketing, private equity, and technology, Nick co-founded Paulus Capital, which helped launch notable restaurants like Superica and The Optimist. In this episode… Acquiring a business through a self-funded search can offer greater autonomy and alignment with personal values but also presents unique challenges. What did a former investor learn when he walked away from traditional search funds to acquire and lead a marketing agency? Owner and CEO of Sure Oak, Nick Fraunfelder, talks about how he launched a self-funded search for a digital marketing agency. With host Todd Taskey, Nick shares the realities of sourcing and funding his acquisition, the lessons from his early career ventures, and how he shifted his leadership focus from metrics to people.
Jason Hennessey is the CEO of Hennessey Digital, a digital marketing agency specializing in legal marketing using a holistic approach. In his role, he grew the small consultancy to a multimillion-dollar business that made the Inc. 5000 list for six consecutive years. As an entrepreneur, internationally recognized SEO expert, author, speaker, podcast host, and business coach, Jason has scaled and sold multiple businesses. He has been reverse-engineering the Google algorithm since 2001. In this episode… When considering outside capital to kickstart growth, founders often turn to private equity. How can you evaluate private equity opportunities while protecting your company's culture, team, and long-term vision? Jason Hennessey, CEO of Hennessey Digital, shares how he scaled his legal SEO agency by partnering with private equity. With host Todd Taskey, Jason explains why he partnered with Trinity Hunt, the importance of assembling a strong leadership team, and how he adapted the company's culture.
Raj Ramanan is the CEO of Herringbone Digital, a digital marketing platform backed by Trinity Hunt Partners. He has led companies from startups and pre-seeds to mid-market and Fortune 1000 to achieve above-market outcomes in revenue growth, profitability, capital raises, and sales. Before joining Herringbone Digital, Raj held executive positions, including Chief Operating Officer at Scorpion, Chief Revenue Officer at Hearst, and President of HYFN Local, and co-founded Loku, a local discovery startup. In this episode… Is private equity the right path for founder-led marketing agencies? While the backing of an experienced PE firm can accelerate growth, it also brings new dynamics. What should agency owners consider before partnering in a roll-up strategy? Raj Ramanan, CEO of Herringbone Digital, discusses building a local digital marketing platform with the support of private equity. With host Todd Taskey, Raj shares how to obtain feedback from founders, how Herringbone selects and supports founder-led agencies, and what it takes to build trust with sellers.
Joe Zanca is the Managing Partner of DealGen Partners, a buy- and sell-side M&A advisory firm. In his role, he has sourced and closed over $200 million in acquisitions for private equity and strategic buyers. Joe launched, scaled, and exited OnDemandStorage, a full-service, technology-based storage company. In this episode… Private equity investment transactions can unlock untapped growth potential, but they also reveal your company's strengths and weaknesses. How can you determine if you're prepared for a transaction? Joe Zanca, Managing Partner of DealGen Partners, discusses how businesses can prepare for acquisitions. With host Todd Taskey, Joe shares how DealGen helps private equity firms uncover off-market opportunities, how founder motivations, deal readiness, and realistic expectations shape outcomes, and the importance of timing and transparency.
Matthew Rosenfeld is the Founder and CEO of Crush, which provides boutique Amazon management services for retail and DTC brands. He is also the Founder of Retail Racer, which leverages proprietary software to automate retail outreach for DTC brands. As a former Amazon seller, Matthew has launched, acquired, and sold multiple brands. In this episode… Selling your business can unlock critical infrastructure and resources to scale, but only if the deal aligns with your vision and values. How can you find the right partner to help you scale while maintaining service quality? Matt Rosenfeld, Founder and CEO of Crush, talks about his recent acquisition. With host Todd Taskey, he shares why he pursued a transaction early in his company's life cycle, how he navigated the due diligence process, and the criteria he used to select the ideal partner.
Joel Green is the Founding Partner of Outliant, a full-service agency building digital products for brands like Amazon, Purina, and Freedom Solar. As a serial tech entrepreneur, he is the Founder and CTO of Winona, a telemedicine company, and the Co-founder of Hardsider. Previously, Joel was the Co-founder and Chief Engineer at Cintric, which was acquired by UberMedia in 2017. In this episode… Selling an agency can catalyze opportunities, but navigating the process requires strategy, speed, and M&A partnerships. How do entrepreneurs know when it's time to make the leap? Joel Green, Founding Partner of Outliant, shares how he built an agency before selling it to private equity. With host Todd Taskey, Joel discusses how he shifted to telemedicine ventures, how he prepared the agency for sale, and the importance of transparency and fit when selecting a buyer.
Raj Khera is the Founder and CEO of MakeMEDIA, an AI-powered content marketing assistant. He is also an Executive Coach at MoreBusiness.com, a platform that helps SaaS businesses grow. As a serial entrepreneur, Raj has led three SaaS companies from startup to acquisition by public firms. He is one of the top 10 ranked SEO coaches in the US. In this episode… Entrepreneurship offers numerous growth opportunities, but knowing when to sell a business can be a complex decision. Industry consolidation, financial positioning, and market trends all play a role in timing a successful exit. How did a seasoned entrepreneur navigate multiple business sales while staying ahead of market shifts? Raj Khera, the Founder and CEO of MakeMEDIA, shares his experience building and selling successful companies. With host Todd Taskey, Raj talks about structuring equity, scaling businesses, and identifying the right time to sell.
Todd Taskey is an M&A Advisor for CEOs and Entrepreneurs at Potomac Business Capital. He has been an entrepreneur, business owner, investment banker, and business finance advisor for more than 20 years. In addition to providing M&A advice, Todd has been a founding investor, board member, or part of the management team of several business ventures. He helps CEOs and entrepreneurs develop a successful exit strategy through his knowledge of the mid-market investment banking process. In this episode… Maximizing business value through transactions requires considering factors like selecting investment bankers and partners, structuring equity, and determining your ultimate goal. How can you make informed transaction decisions for your company's growth? David Rodnitzky, Robert Glazer, Lindsay Frey of damandDrive, Kevin Wilhelm of POD Marketing, and Brian Schmidt of Court Square Capital Partners share insights on transactions in this compilation episode. With host Todd Taskey, the guests talk about the role of reps and warranties insurance, how to select investment bankers and partners, and how to structure equity in transactions.
Chris Peer is the President and CEO of SyncShow, a B2B digital marketing and sales firm. He is also the author of The Great 8 Pillars and the Founder of G8P, where he provides marketing and sales enablement consulting for manufacturers. As a serial entrepreneur, Chris has more than 20 years of experience in B2B digital marketing, lead generation, and consulting. In this episode… Private equity investment transactions are a viable opportunity for kick-starting growth in untapped areas of your business. However, you may discover alternative growth avenues during the process. What did a marketing entrepreneur discover during the transaction process that made him postpone the deal? Chris Peer, the President and CEO of SyncShow, discusses his discoveries about postponing a private equity transaction. With host Todd Taskey, Chris shares insights on value-driven growth, how to navigate the transaction process, and the outcomes of a paused transaction.
Tim Martinez is the Founder and President of The Inside Man, an independent management consulting practice. He assists CEOs and businesses in navigating growth challenges and specializes in strategic advisory, raising capital, M&A, organizational restructuring, and strategic partnership development. As a serial entrepreneur, Tim has spent 25 years owning, operating, selling, and investing in various companies in industries, including software, retail, media, advertising, and investment banking. In this episode… Founders and CEOs are often so caught up in their daily operations that they don't consider their company's future. How should you consider strategic transactions to scale your business? Tim Martinez, the Founder and President of The Inside Man, shares how business owners can overcome growth challenges. With host Todd Taskey, Tim talks about the role of debt in transactions, the value of intentional growth, and why founders are often hesitant to sell their companies.
Dr. James Gregory is the Founder of NYLAQ Advisors, which manages intangible assets to accelerate financial performance. With over 40 years of experience in advertising and branding, he is a leading expert in corporate brand management. Dr. Gregory has developed tools and strategies, including the CoreBrand Index, for measuring brands' impacts on corporations' financial performance. In this episode… Is it worth it to sell your business to a holding company? While you may receive a high earnout, the process can be arduous. What should you consider when selling to a holding company? The Founder of NYLAQ Advisors, Dr. James Gregory, talks about selling his ad agency to a holding company. With host Todd Taskey, Dr. Gregory shares how he closed the transaction, his role after the sale, and why he decided to sell his agency.
In the final edition of the Agency Growth Advisor Series, seven agency advisors share their recommended resources for growth, including podcasts, books, and productivity tools. In this episode… With so many insights and resources available to agency owners, it can be difficult to find what works for you. What can you learn from top agency advisors' most valued resources in the space? Bruce Eckfeldt, Dr. Jeremy Weisz, Ian Garlic, Tim Kilroy, Aaron Levenstadt, Jason Swenk, and Joshua Johnston share where they gain their inspiration. With host Todd Taskey, they discuss how to select podcast guests, the value of listening to entrepreneurs' stories, and their recommended industry thought leaders.
David Rodnitzky is the Founder of David Rodnitzky Consulting, a boutique firm that helps agency owners scale and exit their businesses through M&A. Before becoming a consultant, he founded 3Q Digital, which he bought and sold multiple times. David is also the author of Selling Your Marketing Agency. In this episode… Selling a business requires more than valuing it and selecting a seller. What additional factors should you consider during the process? David Rodnitzky, the Founder of David Rodnitzky Consulting, shares insights from his agency sale. With host Todd Taskey, David covers trends in the agency M&A space, the importance of your gross margin, and why you should hire a law firm and investment banker.
David Rodnitzky is the Founder of David Rodnitzky Consulting, a boutique firm that helps agency owners scale and exit their businesses through M&A. Before becoming a consultant, he founded 3Q Digital, which he bought and sold multiple times. David is also the author of Selling Your Marketing Agency. In this episode… When your initial acquisition fails, you may try again with another method. What can you learn from an entrepreneur who sold his agency three separate times? David Rodnitzky, the Founder of David Rodnitzky Consulting, talks about his agency's sales, from private equity to international buyers. With host Todd Taskey, David details the difference between selling to private equity and public companies, how he built his agency, and how he pivoted after his initial failed transaction.
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