Second Bite Podcast

Todd Taskey
  • 5.0 (4)
  • ENTREPRENEURSHIP
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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.

  1. 3D AGO

    Behind the Scenes of M&A - BluShark Digital & Herringbone Digital

    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 CEO at Jitsu, Chief Operating Officer at Scorpion, Chief Revenue Officer at Hearst, and President of HYFN Local at Nexstar Media Group, and co-founded Loku, a local discovery startup.  Seth Price, Esq., is the Founder of BluShark Digital, a best-in-class digital agency that merged with Herringbone Digital. As an attorney, he is a Partner at Price Benowitz, LLP, which he scaled from a two-person law firm into a multi-attorney practice. Seth also delivers legal marketing, SEO, and business development speeches. In this episode… Private equity is reshaping the digital marketing landscape, especially in highly competitive, founder-led industries. How can growth capital align with culture, autonomy, and long-term vision to create a shared business? Raj Ramanan, CEO of Herringbone Digital, and Seth Price, Founder of BluShark Digital, discuss building a founder-first platform in legal marketing. With host Todd Taskey, Seth and Raj explain the importance of brand independence, how aligned incentives drive outcomes, and how AI and shared resources can fuel sustainable growth.

    32 min

  2. 12/11/2025

    A Knock at the Door Leads To "Perfect Transaction" - What's Still True 5 Years Later

    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.

    49 min

  3. 12/04/2025

    How AI Agents Are Helping Agency Founders Create 70% Margins

    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.

    31 min

  4. 11/27/2025

    Closed Transaction: The CTO's Perspective

    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.

    33 min

  5. 09/18/2025

    Trust, Equity, and AI: The Surprising Deal Behind Levergy's Sale To KickCharge

    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.

    37 min

  6. 09/04/2025

    How To Navigate Key Staff in Your Agency Exit

    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.

    32 min

  7. 07/03/2025

    From Startup to Strategic Powerhouse: Jeff Spanbauer's Journey Through the PE Growth Machine

    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.

    35 min

  8. 06/26/2025

    Behind the Scenes: How a "Search Funder" Acquired a Digital Agency

    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.

    35 min
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Ratings & Reviews

5
out of 5
4 Ratings

About

This is the Second Bite Podcast where we talk with top entrepreneurs and CEOs about creating valuable companies through creative transactions.

Information

  • Creator
    Todd Taskey
  • Years Active
    2021 - 2026
  • Episodes
    132
  • Rating
    Explicit
  • Copyright
    © Second Bite Podcast Copyright (2021)
  • Show Website
    Second Bite Podcast

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