Second Bite Podcast

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.