This is the Second Bite Podcast where we talk with top entrepreneurs and CEOs about creating valuable companies through creative transactions.
…
continue reading
From Angel To Exit is a business podcast exploring the entrepreneurial journey of scaling a business from raising your first round of funding to exiting. We cover the trials and tribulations that founders face, the pitfalls and pratfalls you want to avoid, as well as the joy and impact that success can bring. Join us on our next episode, where we speak about the challenges that real leaders face growing and scaling their organizations and how they’ve overcome them to achieve success and make ...
…
continue reading
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 ...
…
continue reading

1
02: Unlocking the Second Bite: Maximizing Business Exits with Todd Taskey
47:06
47:06
Play later
Play later
Lists
Like
Liked
47:06Todd Taskey, an M&A advisor and angel investor, joins Bruce Eckfeldt to discuss the nuances of business exits and private equity partnerships. Taskey explains the importance of structuring deals to optimize cash, equity, and earnouts. He highlights how founders can use a sale to accelerate growth rather than just exit, and shares real-world example…
…
continue reading

1
Bootstrapped to Boardroom: How Jason Hennessey & Trinity Hunt Will Impact Legal Marketing
38:07
38:07
Play later
Play later
Lists
Like
Liked
38:07Jason 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, podcas…
…
continue reading

1
10: Behind the Exit: Lessons from Ross Shanken’s Nine-Figure Journey with Jornaya
51:41
51:41
Play later
Play later
Lists
Like
Liked
51:41Ross Shanken, founder and former CEO of Jornaya, shares the story behind building a pioneering lead verification platform and guiding it to a nine-figure exit. In this episode of From Angel to Exit, Ross unpacks the strategic frameworks, operational challenges, and personal insights that fueled his success—from initial market entry to final acquisi…
…
continue reading

1
09: From Coffee Brand Success to Corporate Governance Mastery: Joshua Maidan on Scaling and Exiting Right
44:12
44:12
Play later
Play later
Lists
Like
Liked
44:12In this episode of From Angel to Exit, Bruce Eckfeldt speaks with entrepreneur and investor Joshua Maidan, whose journey from Colombia to New York led to the creation of a high-end coffee brand with international acclaim. Maidan shares how he scaled the business using real estate savvy, aggressive strategy, and deep operational structure. The episo…
…
continue reading

1
08: Inside Middle Market M&A: What Every Business Owner Must Know Before Selling
43:13
43:13
Play later
Play later
Lists
Like
Liked
43:13In this sharp and candid episode of From Angel to Exit, Bruce Eckfeldt interviews Bill Snow, Managing Director at Focus Investment Banking and author of several books on M&A. With nearly two decades of experience in the middle market, Bill shares blunt truths and practical advice on what it really takes to sell a business. From valuation myths to p…
…
continue reading

1
07: Lessons from a Failed M&A to a Successful Exit: The Founder Story Behind ClassTag
44:21
44:21
Play later
Play later
Lists
Like
Liked
44:21In this compelling episode of From Angel to Exit, Bruce Eckfeldt interviews Vlada Lotkina, founder of ClassTag, an EdTech platform that transformed parent-teacher communication. From her entrepreneurial upbringing in Ukraine to a successful exit in the U.S., Vlada shares the challenges of monetizing in the K-12 sector, navigating a failed M&A, and …
…
continue reading

1
06: From Side Hustle to Strategic Exit: Lessons from Scaling Unique World
44:44
44:44
Play later
Play later
Lists
Like
Liked
44:44In this episode of From Angel to Exit, host Bruce Eckfeldt sits down with Eddie Geller, serial entrepreneur and founder of Unique World, to unpack the gritty, insightful journey from launching early web services to a high-stakes M&A exit. Geller candidly shares the highs and lows of scaling a business, from client concentration pitfalls to post-acq…
…
continue reading

1
05: From Bootstrap to Buyout: Scaling Tech Startups with Strategic Go-to-Market and Exit Fit
49:54
49:54
Play later
Play later
Lists
Like
Liked
49:54In this episode of From Angel to Exit, Bruce Eckfeldt speaks with serial entrepreneur Shreesha Ramdas about his journey from risk-averse engineer to founder of multiple successful startups. Shreesha shares his unique “startup fitness” framework, lessons from bootstrapping LeadFormix through to its acquisition by SAP, and his current work with Lumbe…
…
continue reading

1
04: How Shawn Freeman Scaled an MSP to $5M and Exited at 1.4x Revenue
44:48
44:48
Play later
Play later
Lists
Like
Liked
44:48Shawn Freeman, founder of a successful managed service provider (MSP), joins Bruce Eckfeldt to share his journey from launching a tech side hustle to scaling a $5M business and executing a 1.4x revenue exit. He reflects on key inflection points in leadership, recurring revenue strategy, and the emotional and operational complexities of being acquir…
…
continue reading

1
03: From Clarity to Close: Strategizing Your Ideal Business Exit with Suren Kapse
38:37
38:37
Play later
Play later
Lists
Like
Liked
38:37In this episode of From Angel to Exit, Bruce Eckfeldt speaks with Suren Kapse, a seasoned advisor and coach specializing in M&A and exit strategies. Suren shares hard-earned insights on how founders can prepare for successful exits, whether selling for people, assets, scale, or client access. He also unpacks how buyers evaluate cultural fit, valuat…
…
continue reading

1
01: From Founding to Exit: Scaling Mass Communications and Life After
44:42
44:42
Play later
Play later
Lists
Like
Liked
44:42In this episode of From Angel to Exit, host Bruce Eckfeldt sits down with Darren Mass, the founder of Mass Communications, to discuss his entrepreneurial journey from launch to acquisition. Darren shares how his early fascination with engineering led him to build a successful telecom company, the strategies he used to scale, and the key decision po…
…
continue reading

1
Trinity Hunt and the Future of Local Digital Marketing
24:50
24:50
Play later
Play later
Lists
Like
Liked
24:50Raj 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, i…
…
continue reading
From Angel To Exit is a business podcast exploring the entrepreneurial journey of scaling a business from raising your first round of funding to exiting. We cover the trials and tribulations that founders face, the pitfalls and pratfalls you want to avoid, as well as the joy and impact that success can bring. Join us on our next episode, where we s…
…
continue reading
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…
…
continue reading

1
When a Transaction Accelerates Growth - Avoiding Agency Building
38:37
38:37
Play later
Play later
Lists
Like
Liked
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…
…
continue reading
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…
…
continue reading
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…
…
continue reading

1
Creating Winning Business Deals: A Compilation of Strategies
8:45
8:45
Play later
Play later
Lists
Like
Liked
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. …
…
continue reading

1
Value Created From a Process (Even Without a Transaction)
26:57
26:57
Play later
Play later
Lists
Like
Liked
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…
…
continue reading
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 …
…
continue reading
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…
…
continue reading

1
[Agency Growth Advisors Series] Rapid-Fire Segment: Invaluable Resources From Agency Owners
30:45
30:45
Play later
Play later
Lists
Like
Liked
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’…
…
continue reading

1
Selling Your Marketing Agency - Lessons From a Remarkable Story Part 2
27:54
27:54
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Selling Your Marketing Agency - The Remarkable Story Behind the Book Part 1
19:26
19:26
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
How to Achieve Agency Success Without Cheap Labor with JC Hite
37:35
37:35
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
[Agency Growth Advisors Series] Don’t Get Stuck With "Yes" People: Where Agency Owners Source Their Feedback
22:54
22:54
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
[Agency Growth Advisors Series] Lessons From the Big Dogs: What Smaller Agencies Haven’t Quite Figured Out
19:39
19:39
Play later
Play later
Lists
Like
Liked
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 …
…
continue reading

1
Be the Roller, Join the Roller, or Get Rolled - Winning With Private Equity Part 2
28:49
28:49
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Be the Roller, Join the Roller, or Get Rolled - Winning With Private Equity
29:25
29:25
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
What Happens When the Founder Sells to Employees?
27:51
27:51
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Strategic Acquisitions and Long-Term Vision: E-Commerce Growth with Brian Burt
15:39
15:39
Play later
Play later
Lists
Like
Liked
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 …
…
continue reading

1
[Agency Growth Advisors Series] Agency Growth Questions: A Checklist for Founders
20:25
20:25
Play later
Play later
Lists
Like
Liked
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, …
…
continue reading

1
Mastering the Art of Acquisitions: 100+ Deals a Year with Robyn Siers
22:28
22:28
Play later
Play later
Lists
Like
Liked
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 …
…
continue reading

1
Reflections (10 Years Later) Selling to a Public Holding Company
34:11
34:11
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Big Picture Marketing: Scaling Through Offers, Content, and Acquisitions with Molly Pittman
29:15
29:15
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
[Agency Growth Advisors Series] An Introduction to Agency Growth: Helping Agency Owners Identify Their Biggest Challenges
22:41
22:41
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
EBITDA, Earn-Outs, and the Exit Plan with Todd Taskey
34:20
34:20
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Building an Empire: Acquisitions, Leadership, and Vision in the Agency World with Jason Swenk
32:03
32:03
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Building a Brand that Sells Out Through TikTok with Josh Snow
16:26
16:26
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Building Multimillion-Dollar Brands with Celebrity Partners with Rudy Mawer
21:02
21:02
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Mastering LinkedIn: Build Your Personal Brand and Double Your Business with Joshua B. Lee
35:34
35:34
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Mental Health & Money: Building Hawke Media Against All Odds with Erik Huberman
41:05
41:05
Play later
Play later
Lists
Like
Liked
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 …
…
continue reading

1
Creating Deals That Win: Leveraging Media and Exiting on Top with Max Finn
34:42
34:42
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
How to Build an Agency Without Sales Calls with Dennis Yu
41:20
41:20
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Why Most Businesses Fail to Sell—And How to Beat the Odds
21:58
21:58
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Lessons, Learnings & Freedom From Transaction #1
25:09
25:09
Play later
Play later
Lists
Like
Liked
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 …
…
continue reading

1
Deal Flow Secrets: How to Find Million-Dollar Deals in Your Own Network
21:04
21:04
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Why 90% of Agencies Are Perfect M&A Targets—And Don't Even Know It
18:41
18:41
Play later
Play later
Lists
Like
Liked
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…
…
continue reading

1
Scaling Through Acquisitions Instead of Building a Startup
25:29
25:29
Play later
Play later
Lists
Like
Liked
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…
…
continue reading
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…
…
continue reading