This is the Second Bite Podcast where we talk with top entrepreneurs and CEOs about creating valuable companies through creative transactions.
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Welcome to The Deal Playbook Podcast — the ultimate show for entrepreneurs, CEOs, and founders who want to scale their businesses, diversify risks, and unlock multiple exit opportunities through strategic acquisitions and deals. Hosted by Tom Shipley, an experienced entrepreneur with 18 successful acquisitions and exits, this podcast offers invaluable insights into the world of M&A. Each episode features expert guests who share their knowledge on how to identify once-in-a-lifetime deals, nav ...
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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 investmen…
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When a Transaction Accelerates Growth - Avoiding Agency Building
38:37
38:37
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38:37Matthew 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…
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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 a…
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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…
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Creating Winning Business Deals: A Compilation of Strategies
8:45
8:45
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8:45Todd 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. …
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Value Created From a Process (Even Without a Transaction)
26:57
26:57
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26:57Chris 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, a…
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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 …
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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 c…
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[Agency Growth Advisors Series] Rapid-Fire Segment: Invaluable Resources From Agency Owners
30:45
30:45
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30:45In 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’…
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Selling Your Marketing Agency - Lessons From a Remarkable Story Part 2
27:54
27:54
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27:54David 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…
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Selling Your Marketing Agency - The Remarkable Story Behind the Book Part 1
19:26
19:26
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19:26David 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 fa…
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How to Achieve Agency Success Without Cheap Labor with JC Hite
37:35
37:35
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37:35This episode features JC Hite, founder of Hite Digital, sharing how he disrupted the traditional digital agency model by blending franchising with global talent acquisition. JC recounts his evolution from a white-label provider to building one of the fastest-growing agency networks, spanning 16 offices across the U.S. and Latin America. You will ga…
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[Agency Growth Advisors Series] Don’t Get Stuck With "Yes" People: Where Agency Owners Source Their Feedback
22:54
22:54
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22:54In the third segment of the Agency Growth Advisor Series, seven agency owners share where their clients gain honest feedback to propel their businesses forward. In this episode… In the early stages of growth, agency owners often leverage quick hacks from people who claim to have grown from $1 to $10 million in under a year. How can you identify har…
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[Agency Growth Advisors Series] Lessons From the Big Dogs: What Smaller Agencies Haven’t Quite Figured Out
19:39
19:39
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19:39In the second episode of the Agency Growth Advisor Series, Todd Taskey’s guests discuss what small agencies can learn from larger agencies that have overcome challenges. In this episode… In the early stages, small agencies may struggle to grow to the scale of more established agencies. What are the growth secrets of large agencies, and how can you …
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Be the Roller, Join the Roller, or Get Rolled - Winning With Private Equity Part 2
28:49
28:49
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28:49Robert Glazer is the Founder and Chairman of the Board of Acceleration Partners, a global partnership marketing agency. He is also the former Co-founder and Chairman of the Board of BrandCycle, which was acquired by Stack Commerce in 2021. As a serial entrepreneur, award-winning executive, best-selling author, and keynote speaker, Robert helps indi…
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Be the Roller, Join the Roller, or Get Rolled - Winning With Private Equity
29:25
29:25
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29:25Robert Glazer is the Founder and Chairman of the Board of Acceleration Partners, a global partnership marketing agency. He is also the former Co-founder and Chairman of the Board of BrandCycle, which was acquired by Stack Commerce in 2021. As a serial entrepreneur, award-winning executive, best-selling author, and keynote speaker, Robert helps indi…
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What Happens When the Founder Sells to Employees?
27:51
27:51
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27:51Jamie Birch is the Founder of JEBCommerce, a digital marketing agency specializing in affiliate program management. As a serial entrepreneur, he is also the Co-founder of Renewed Horizons, a day program for adults with developmental disabilities, and EquineRevShare, which helps equine professionals generate revenue from product recommendations. Bef…
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Strategic Acquisitions and Long-Term Vision: E-Commerce Growth with Brian Burt
15:39
15:39
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15:39Brian Burt, founder of Canopy Management, shares his incredible journey from a scrappy Amazon seller to leading one of the fastest-growing e-commerce agencies in the country. Brian breaks down the strategic role acquisitions played in scaling his business, revealing how buying companies unlocked massive growth opportunities. From leveraging TikTok …
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[Agency Growth Advisors Series] Agency Growth Questions: A Checklist for Founders
20:25
20:25
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20:25In the second installment of the Agency Growth Advisors series, seven agency experts share what owners should consider when preparing their agency for growth. In this episode… What does it take to propel an agency to the next stage? How can agency founders transform their current strategies into high-performing growth trajectories? Bruce Eckfeldt, …
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Mastering the Art of Acquisitions: 100+ Deals a Year with Robyn Siers
22:28
22:28
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22:28Robyn Siers is a seasoned M&A attorney telling you her insights on what it takes to successfully navigate mergers and acquisitions, especially in the marketing and tech industries. She talks about the importance of having a clear buying thesis, understanding seller motivation, and using creative deal structures to close deals. Robyn also discusses …
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Reflections (10 Years Later) Selling to a Public Holding Company
34:11
34:11
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34:11Mitch Meyers is a Partner at the medical cannabis firm BeLeaf Medical and the CEO of The BeLeaf Company, which produces high-quality CBD oils to treat epilepsy patients. Mitch is also the Co-Owner and Partner at Nature's Care Company, a Chicago-based dispensary that provides premium medical cannabis. With over 25 years of experience in the marketin…
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Big Picture Marketing: Scaling Through Offers, Content, and Acquisitions with Molly Pittman
29:15
29:15
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29:15Molly Pittman, CEO and Managing Partner at Smart Marketer, shares her proven strategies for growing businesses in today’s rapidly changing digital marketing landscape. Due to how she helps brands scale from $5 million to $50 million, Molly talks about the importance of strong offers, using native ads, and thinking big-picture when navigating market…
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[Agency Growth Advisors Series] An Introduction to Agency Growth: Helping Agency Owners Identify Their Biggest Challenges
22:41
22:41
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22:41In this introduction to the Agency Growth Advisors series, Todd Taskey sits down with seven agency owners who share how they help founders accelerate growth. In this episode… When it comes to scaling an agency, there’s no one-size-fits-all approach. Strategies often depend on size, revenue, and operational structure. What insights can you learn fro…
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EBITDA, Earn-Outs, and the Exit Plan with Todd Taskey
34:20
34:20
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34:20Todd Taskey discusses the key strategies digital marketing agencies need to know when preparing for a successful exit. He explains why finding the right buyer matters more than you think and how clear messaging about your business can drive up your transaction value. Todd also covers the importance of realistic projections, navigating earn-outs, an…
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Building an Empire: Acquisitions, Leadership, and Vision in the Agency World with Jason Swenk
32:03
32:03
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32:03Jason Swenk breaks down how agency owners can scale their businesses, overcome common challenges, and position themselves for success. He shares his Eight System Framework, which has helped countless agencies grow from scratch to eight figures. Jason also dives into the power of strategic acquisitions, the importance of having a clear vision, and w…
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Building a Brand that Sells Out Through TikTok with Josh Snow
16:26
16:26
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16:26Josh Snow shares how he built a multi-million dollar brand by tapping into the power of TikTok and leveraging an army of creators. He explains the strategies that helped him generate $1 million in sales within days of launching on TikTok Shop and how this platform has become a game changer for e-commerce. Josh breaks down the importance of viral co…
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Building Multimillion-Dollar Brands with Celebrity Partners with Rudy Mawer
21:02
21:02
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21:02Rudy Mawer shares his journey of building multimillion-dollar businesses through strategic partnerships, celebrity collaborations, and leveraging AI and automation. Rudy shares insights on acquiring iconic brands during the COVID-19 pandemic, his strategic partnership with Ty Lopez, and building multi-million dollar businesses while running an expa…
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Mastering LinkedIn: Build Your Personal Brand and Double Your Business with Joshua B. Lee
35:34
35:34
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35:34Joshua B. Lee, known as the "Dopamine Dealer of LinkedIn," shares how he’s helped businesses scale by focusing on authentic human connections. He talks about the evolution from MySpace to LinkedIn, revealing why personal brands are critical for business success today. Joshua talks about content strategies that work on LinkedIn, the importance of tr…
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Mental Health & Money: Building Hawke Media Against All Odds with Erik Huberman
41:05
41:05
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41:05In this episode, Erik Huberman, founder and CEO of Hawke Media, shares his entrepreneurial journey, from starting his first business at age six to building a marketing empire that has generated over $2.9 billion in revenue for clients. He opens up about the highs and lows of running a business, including how mental health challenges nearly led him …
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Creating Deals That Win: Leveraging Media and Exiting on Top with Max Finn
34:42
34:42
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34:42Max Finn shares his journey from early success with Facebook marketing to leading the charge on TikTok. He discusses the mindset shift required to approach deals with confidence, the importance of having options, and the fine line between abundance and scarcity in negotiations. Max also talks about key strategies for leveraging media to raise capit…
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Why Most Businesses Fail to Sell—And How to Beat the Odds
21:58
21:58
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21:58Tom Shipley and Matt Bodnar break down the world of business valuations and deal structures. They talk about how valuations are more an art than a strict science, influenced by market conditions, negotiation strategies, and individual motivations. Their discussion covers examples of how businesses are bought and sold, highlighting the strategies th…
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How to Build an Agency Without Sales Calls with Dennis Yu
41:20
41:20
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41:20Digital marketing pioneer Dennis Yu shares his expert advice on how businesses can amplify their success by focusing on what works and scaling those wins. From his proven Dollar-a-Day strategy to the power of the Lighthouse model, Dennis breaks down steps for growing agencies and boosting client results. Whether you're running local campaigns or wo…
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Lessons, Learnings & Freedom From Transaction #1
25:09
25:09
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25:09Aaron Levenstadt is the Founder of Join Agency Alliance, an advisory board composed of former agency owners who have exited their businesses. He has built and sold multiple agencies, including Pedestal Search, which emerged from his experience as one of the original members of Google’s Search Analytics team. As an investor, Aaron supports agencies …
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Deal Flow Secrets: How to Find Million-Dollar Deals in Your Own Network
21:04
21:04
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21:04Tom Shipley and Matt Bodnar discuss the often-overlooked strategies for sourcing acquisition opportunities that go beyond traditional methods. They challenge the common reliance on brokers and competitive marketplaces, advocating instead for the power of off-market deals and the value of weak ties in your network. Tom and Matt provide simple and ef…
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Why 90% of Agencies Are Perfect M&A Targets—And Don't Even Know It
18:41
18:41
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18:41This episode breaks down the immense potential that agencies and e-commerce brands hold for strategic acquisitions. Tom and Matt share their insights on why these sectors are prime for investment, highlighting the overlooked opportunities that many business owners miss. They argue that now is the time to capitalize on these opportunities, with a fo…
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Scaling Through Acquisitions Instead of Building a Startup
25:29
25:29
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25:29Tom Shipley and Matt Bodnar discuss the power of acquisitions as a growth strategy that can outpace run-of-the-mill methods. They share how even in the face of financial hardship, strategic acquisitions allowed their businesses to break through barriers that would have been almost impossible otherwise. They push back against the traditional strateg…
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Adam Hanin is the Head of Business Development at eHouse, which builds and optimizes e-commerce sites for shoppers. He is also the former Founder and Operating Partner at Commerce12, which was acquired by eHouse in 2024, and the former Founder and President of Skye Associates, a full-service e-commerce company specializing in fashion brands and ret…
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PE Insight Series: What Drives TRUE Value in a Transaction?
37:22
37:22
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37:22In the final segment of the PE Insight Series, eight private equity executives weigh in on what drives value in a transaction. In this episode… What factors drive true value in a private equity transaction? How can you position your company as a profitable fit for investors? Casey Swercheck, Joshua Bilmes, Nick Moritsugu, Bill Sommerschield, Trento…
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PE Insight Series: Eliminating Friction in Deal Negotiations
37:00
37:00
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37:00In this episode of the PE Insight Series, eight private equity executives talk about the primary sources of friction in deal negotiations. In this episode… Disagreements occur in many deal negotiations, but they can collapse if these disputes aren’t resolved appropriately. What causes the most friction during the negotiation process, and how can yo…
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PE Insight Series: The Inner Workings of an Investment Committee
32:51
32:51
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32:51In the third installment of the PE Insight Series, Todd Taskey’s guests offer a behind-the-scenes look into investment committees. In this episode… Most entrepreneurs aren’t familiar with investment committees, so it can be quite daunting to approach them during a transaction. What is an investment committee, and how do they facilitate the transact…
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PE Insight Series: What Kills a Deal? PE Executives Weigh In
32:28
32:28
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32:28In the second edition of the PE Insight Series, eight private equity executives discuss the #1 factor in failed deals. In this episode… Imagine being on the brink of closing a major transaction and having it fall apart unexpectedly. What causes a deal to crumble following the LOI, and how can you prevent a failed deal? Casey Swercheck, Joshua Bilme…
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PE Insight Series: First Impressions: PE Executives’ Investment Criteria
31:53
31:53
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31:53In the first installment of the PE Insight Series, Todd Taskey interviews eight private equity executives about how they make their initial assessment of a company. In this episode… Private equity executives often sift through thousands of investment decks each week. So what are their criteria for evaluating them, and how can business owners struct…
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What Makes an Acquisition Strategy Really Work?
25:08
25:08
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25:08Kevin Buerger is the CEO of Labelium, a digital marketing and performance agency. In his role, he drives the company’s growth strategy and positioning for the US market. Before Labelium, Kevin spent nearly 13 years as the Global Chief Growth Officer at Jellyfish, where he built its US presence. In this episode… What differentiates successful compan…
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From 600 Global Clients To Losing $1.1M To a Profitable Recurring Revenue Business
35:08
35:08
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35:08Jamie Shanks is the CEO of Get Levrg, a community mastermind helping founders and CEOs navigate offshoring talent. As a serial entrepreneur, he is also the CEO of Pipeline Signals, the #1 sales methodology for account-based sellers. Jamie was previously the CEO of Sales for Life, the leading social selling training company, which he scaled to 600 g…
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The Delicate Art of Transitioning From Founder to CEO
19:14
19:14
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19:14Bruce Eckfeldt is a Strategic Coach and Master Facilitator at Eckfeldt & Associates, where he works with CEOs and leadership teams to scale their businesses. As a former Inc. 500 founder and CEO, he successfully scaled and sold his business. Bruce focuses on developing leadership skills, optimizing companies for transactions, and navigating mergers…
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Kevin Wilhelm is the Founder and President of POD Marketing, a digital agency specializing in industry-specific marketing services. With a decade of experience, he has successfully led the company through dynamic growth. Kevin is also the President of several other marketing firms, including Marketing4ECPs, CITIZEN Marketing, and Lift Aesthetic Mar…
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How a 33% “Roll Forward” Results in 47.8% Equity Ownership
27:28
27:28
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27:28Lindsay Frey is the Co-founder and President of demandDrive, an industry leader in building sales development programs for B2B tech companies. She is also the Co-founder of Data Fuel, demandDrive’s former data offering providing actionable sales data. In this episode… Strategic acquisitions are an effective way to fast-track business growth, but ho…
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How Do I Know the Timing Is Right? (Founder Question Series)
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28:32In the fourth and final episode of the Founder Question Series, nine founders answer the common question of how to determine the ideal time to sell your business. In this episode… Entrepreneurs and CEOs are often caught in the conundrum of selling now or holding out for greater value in the future. How do top business minds navigate this decision? …
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When and How Do I Disclose to My Company, Customers, and the Public? (Founder Question Series)
31:51
31:51
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31:51In the third edition of the Founder Question Series, Todd Taskey asks his nine guests when to disclose a transaction to the entire company, how to relay it to customers, and when to announce it to the public. In this episode… One of the most crucial steps in any transaction is disclosure. When and how you communicate your transaction to your team, …
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When Do I Bring My Management Team Into the Loop? (Founder Question Series)
26:44
26:44
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26:44In the second installment of the Founder Question Series, Todd Taskey interviews his nine guests about when to alert your management team to a transaction. In this episode… When navigating a transaction, when should you inform your management team? Nine founders weigh in on how to effectively position a transaction for your team. Jon Morris, Matt S…
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