Inorganic Podcast

In this episode, we explore the rising influence of AI in marketing agencies, the implications of tech-forward agency models, and recent high-profile acquisitions like Grapevine AI. Discover how private equity and Silicon Valley are reshaping agency valuations, deal structures, and the future of the industry.

• The emergence of AI-native agencies as highlighted by Y Combinator's 2026 request list
• How agencies are evolving to resemble software companies with higher margins and scalability
• The challenges traditional agencies face integrating innovative, tech-led models
• Trends in agency valuations, deal structures, and the influence of private equity
• An in-depth analysis of the recent Grapevine AI acquisition and its significance
• The shifting landscape of deal valuation, cash on close, and deal structure for tech-forward agencies
• The barriers to adopting AI and modern practices within conservative client organizations
• The strategic rationale behind merging creator economies with AI-enabled marketing solutions

00:00 - Building custom Claude bots and the evolution of OpenClaw

02:12 - Silicon Valley’s focus on AI-native agencies

03:00 - How agencies will become more like software companies

03:50 - The landscape of traditional vs. modern, tech-forward agencies

07:02 - Private equity's view on services versus software investments

09:40 - Recent acquisitions: New Engine’s Grapevine AI and other strategic moves

11:32 - What makes Grapevine AI unique in creator-led content

14:10 - The impact of deal structure and valuation rigor in AI agency acquisitions

17:23 - How founders are pushing for tech-led valuations and lower risk models

18:16 - The challenges of adapting legacy agency models to AI-driven futures

20:11 - Industry response and what’s next for agency deal activity

• Grapevine AI
• New Engine
• Y Combinator - 2026 Startups List (scroll to #3)
• LinkedIn - Caroline LaVere

Connect with Christian and Ayelet

Ayelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/

Christian's LinkedIn: https://www.linkedin.com/in/hassold/

Web: https://www.inorganicpodcast.co

In/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featured

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Inorganic Podcast, hosts Christian Hassold and Ayelet Shipley are joined by Travis Johnson, co-founder and Global CEO of Podean, to talk about the incredible story behind the one of the rising star Amazon and marketplace retail media agencies, which is now backed by Mountiangate. The conversation explores the origin of Podean, their successful search for private equity backers, their acquisition of Commerce Canal and their broader point of view on  the opportunities in the retail media and marketplaces business. Travis shares insights on how Podean differentiates itself by offering integrated solutions that address not just media performance but also the broader operational needs of brands in the marketplace. He emphasizes the importance of understanding consumer behavior and the necessity for brands to adapt to the changing dynamics of e-commerce.

Takeaways

• Podean was founded to bridge gaps in the retail media landscape.
• Retail media is becoming increasingly important for brands.
• Global consistency is a priority for large brands.
• Podean's growth strategy includes a focus on social commerce.
• The partnership with Mountain Gate Capital aims to enhance Podean's capabilities.
• Navigating the M&A process requires careful preparation and cultural alignment.
• AI is seen as a transformative tool, but its implementation must be thoughtful.
• Future growth for Podean includes strategic acquisitions to enhance service offerings.

Chapters

02:28 Travis Johnson’s Background & Podean

04:55 Retail Media Today & Holdco Limits

08:00 Building a Global Marketplace Business

10:41 Social Commerce & Live Shopping

11:19 Winning Clients from Holdcos

12:47 Early M&A Talks & Learning Private Equity

16:00 Choosing the Platform Model & Mountaingate

19:08 Control, Governance & Valuation Realities

23:57 Strategic Buyers vs. Private Equity

28:26 Commerce Canal: The Right Acquisition

31:13 Closing Two Deals & Integration

39:24 Using AI Without the Hype

45:37 Growth Strategy & What’s Next

Connect with Christian and Ayelet

Ayelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/

Christian's LinkedIn: https://www.linkedin.com/in/hassold/

Web: https://www.inorganicpodcast.co

In/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featured

Connect with Travis Johnson

https://www.linkedin.com/in/travis-johnson77/ 

Follow Podean on LinkedIn

https://www.linkedin.com/company/podean/ 

Hosted on Acast. See acast.com/privacy for more information.

In this engaging episode, co-hosts Ayelet Shipley and Christian Hassold welcome Tom Shipley to share his journey of building and scaling businesses through acquisitions. He discusses the challenges and opportunities in mergers and acquisitions (M&A) present, emphasizing the importance of strategic thinking and relationship building. The conversation also explores partnership dynamics and the role of external partners in resolving conflicts. Tom highlights the power of acquisitions in overcoming business challenges and achieving growth, offering insights into the process of identifying and acquiring businesses.

Takeaways

• Acquisitions can solve almost every business challenge.
• Partnership dynamics often require external mediation.
• Strategic thinking is crucial in M&A.
• Building relationships is key to successful acquisitions.
• Acquisitions offer a faster path to business growth.
• Understanding seller motivation is essential in deals.
• Partnership conflicts can hinder business progress.
• Acquisitions can provide liquidity and strategic opportunities.

Chapters

00:46 Tom Shipley’s Path Into M&A

01:38 The First Acquisition That Changed Everything

05:34 Using Acquisitions to Solve Cash and Capability Gaps

08:28 Buy vs. Build: Rethinking Entrepreneurship

09:37 Seller Motivation and Why Deals Exist Everywhere

11:50 Organic Growth vs. Acquisition Math

13:41 Partnership Misalignment as a Growth Blocker

14:21 How M&A Can Resolve Partner Deadlock

19:26 Mergers as a Reset for Growth and Liquidity

28:40 The Valley of Despair for Mid-Market Founders

29:45 Buying the Next Chapter vs. Starting Over

31:50 Where to Find Acquisition Opportunities

37:49 Adding a Zero: Expanding the Mental Model

39:44 DealCon, Reources, and Community

Connect with Christian and Ayelet

Ayelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/

Christian's LinkedIn: https://www.linkedin.com/in/hassold/

Web: https://www.inorganicpodcast.co

In/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featured

Connect with Tom Shipley

https://www.linkedin.com/in/t-shipley/

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Inorganic Podcast, co-host Christian Hassled interviews Robin Skidmore, a seasoned entrepreneur and the founder and CEO of Journey Further. They discuss Robin's journey from humble beginnings to founding successful agencies, including Epiphany Search and Journey Further. The conversation explores the evolution of Journey Further, its recent acquisition of Salderson Media, and the challenges of expanding into the U.S. market. Robin shares insights on agency culture, the current state of the UK agency market, and the importance of adapting to changes in consumer behavior and technology, particularly AI. The episode concludes with a discussion on Robin's investments in startups and the significance of maintaining a strong company culture as the agency grows.

Takeaways

• Robin Skidmore's entrepreneurial journey began with a car wash at age 12.
• Journey Further was launched in 2017 with a clear roadmap for growth.
• The agency focuses on performance media and aims to be creatively driven.
• Acquisition of Salderson Media was strategic for expanding capabilities.
• Expanding to the U.S. market presented unique challenges and cultural differences.
• Maintaining a strong company culture is crucial for agency success.
• The UK agency market is experiencing consolidation and increased competition.
• AI is transforming the marketing landscape, requiring agencies to adapt.
• Investing in startups allows for a deeper understanding of client challenges.
• Cultural dynamics influence agency operations and client relationships.

Chapters

00:00 Introduction to Robin Skidmore and Journey Further

02:14 Robin's Entrepreneurial Journey and Epiphany Search

04:52 The Evolution of Journey Further

08:13 Acquisition of Salderson Media and Market Relevance

10:32 Expanding to the U.S. Market: Challenges and Insights

17:31 Cultural Differences in Agency Operations

20:16 Lessons from Epiphany to Journey Further

23:29 The State of the UK Agency Market

26:21 Future Growth Strategies and Inorganic Expansion

30:28 Cultural Dynamics in Agency Growth

34:21 Investments Beyond Agencies: The Pub and Startups

41:22 Maintaining Culture and Addressing AI Challenges

Connect with Christian and Ayelet

Ayelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/

Christian's LinkedIn: https://www.linkedin.com/in/hassold/

Web: https://www.inorganicpodcast.co

In/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featured

Hosted on Acast. See acast.com/privacy for more information.

In this episode, co-hosts Ayelet Shipley and Christian Hassold delve into AI related acquisitions, particularly focusing on outsized valuation multiples and whether they are sustainable or extensible to the digital agency sector. They discuss the valuation multiples seen in recent AI focused acquisitions led by Meta, Nvidia, Cvent, and OpenAI, and opine on the race for talent in the AI era. The conversation highlights the evolving landscape of agency capabilities in the face of AI advancements and the potential for consolidation in the market. The hosts also explore the future of digital agencies and the opportunities that lie ahead for strategic acquirers in the AI domain.

Takeaways

• AI is driving significant M&A activity in the tech sector.
• Recent acquisitions show high valuation multiples for AI companies.
• The trend of acquiring talent over products is prevalent in AI M&A.
• Digital agencies must adapt to the changing landscape influenced by AI.
• There is a potential consolidation in the agency market due to AI advancements.
• Strategic acquirers are looking for speed to market through AI capabilities.
• The valuation of AI startups is often based on capital raised rather than revenue.
• The market for AI capabilities in agencies is still developing.
• Founders may need to be realistic about their exit multiples in the current environment.
• The future of digital agencies will be shaped by AI innovations.

Chapters

00:00 Introduction to AI Trends

01:03 M&A Activity in AI

05:16 Valuation Multiples in AI Acquisitions

11:00 The Talent Acquisition Race

15:18 AI's Impact on Agencies

19:07 Future of Digital Agencies

25:01 Opportunities in AI Acquisitions

Connect with Christian and Ayelet

Ayelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/

Christian's LinkedIn: https://www.linkedin.com/in/hassold/

Web: https://www.inorganicpodcast.co

In/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featured

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Inorganic Podcast, co-host Ayelet Shipley interviews Carrie Kerpen, a pioneer in social media and co-founder of Likeable Media. They discuss Carrie's journey from starting a social media agency to successfully exiting the business. Carrie shares insights on the importance of profitability, setting exit goals, choosing the right M&A advisor, and negotiating earn-outs. She reflects on her experiences and the lessons learned, particularly for women entrepreneurs, and emphasizes the need for community and support in the business world.

Takeaways

• Carrie started Likeable Media in 2007, one of the first social media agencies.
• The initial focus was not on exiting but on building a profitable business.
• Setting a target exit value can help guide business decisions.
• Timing and personal readiness are crucial when deciding to sell a business.
• Choosing the right M&A advisor can significantly impact the sale process.
• Negotiating earn-outs requires careful consideration of control and reporting.
• Reflecting on the exit process can reveal areas for improvement.
• Building a community for women founders can provide essential support.
• Women entrepreneurs often face unique challenges in the exit process.
• M&A can be a powerful tool for business growth and problem-solving.

Chapters

0:00 Introducing Carrie Kerpen

1:05 Founding Likeable Media 

3:33 Early Growth & Cash Flow Challenges

5:22 Becoming CEO and Focusing on Profitability

6:37 Market Shifts & Productizing the Agency

7:21 Building a Brand through All the Social Ladies

9:07 Financial Stability & the $20M Exit Goal 

10:43 Knowing When It's Time to Sell

12:55 Choosing an M&A Advisor vs. a Banker

15:36 Price vs. Timing After the Exit

18:22 Negotiating & Protecting an Earnout

22:02 Life After the Sale

23:12 What Carrie Would Do Differently

24:51 Acting Like a Platform and Rethinking Capital

25:58 The Exit Gap and The Whisper Group

27:45 Closing Thoughts

Connect with Christian and Ayelet

Ayelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/

Christian's LinkedIn: https://www.linkedin.com/in/hassold/

Web: https://www.inorganicpodcast.co

In/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featured

Connect with guest, Carrie Kerpen

https://www.linkedin.com/in/carriekerpen/

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Inorganic Podcast, co-host Ayelet Shipley interviews Carrie Kerpen, a pioneer in social media and co-founder of Likeable Media. They discuss Carrie's journey from starting a social media agency to successfully exiting the business. Carrie shares insights on the importance of profitability, setting exit goals, choosing the right M&A advisor, and negotiating earn-outs. She reflects on her experiences and the lessons learned, particularly for women entrepreneurs, and emphasizes the need for community and support in the business world.

Takeaways

• Carrie started Likeable Media in 2007, one of the first social media agencies.
• The initial focus was not on exiting but on building a profitable business.
• Setting a target exit value can help guide business decisions.
• Timing and personal readiness are crucial when deciding to sell a business.
• Choosing the right M&A advisor can significantly impact the sale process.
• Negotiating earn-outs requires careful consideration of control and reporting.
• Reflecting on the exit process can reveal areas for improvement.
• Building a community for women founders can provide essential support.
• Women entrepreneurs often face unique challenges in the exit process.
• M&A can be a powerful tool for business growth and problem-solving.

Chapters

0:00 Introducing Carrie Kerpen

1:05 Founding Likeable Media 

3:33 Early Growth & Cash Flow Challenges

5:22 Becoming CEO and Focusing on Profitability

6:37 Market Shifts & Productizing the Agency

7:21 Building a Brand through All the Social Ladies

9:07 Financial Stability & the $20M Exit Goal 

10:43 Knowing When It's Time to Sell

12:55 Choosing an M&A Advisor vs. a Banker

15:36 Price vs. Timing After the Exit

18:22 Negotiating & Protecting an Earnout

22:02 Life After the Sale

23:12 What Carrie Would Do Differently

24:51 Acting Like a Platform and Rethinking Capital

25:58 The Exit Gap and The Whisper Group

27:45 Closing Thoughts

Connect with Christian and Ayelet

Ayelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/

Christian's LinkedIn: https://www.linkedin.com/in/hassold/

Web: https://www.inorganicpodcast.co

In/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featured

Connect with guest, Carrie Kerpen

https://www.linkedin.com/in/carriekerpen/

Hosted on Acast. See acast.com/privacy for more information.

Summary

In this episode of the Inorganic Podcast, co-hosts Christian Hassold and Ayelet Shipley chat with Chloe Cotoulas, Partner at Everos Group and an investment banker with a diverse background in advertising and finance. On this episode they discuss Chloe's unique career path, the evolution of holdcos in the advertising industry, and the impact of market trends on large-scale independent agencies. The conversation also explores the future outlook for deal activity in the coming quarters, emphasizing the importance of AI and experiential marketing in shaping the industry.

Takeaways

• Chloe transitioned from a creative background to investment banking.
• The convergence of creativity and business is crucial in today's market.
• Holdcos are facing challenges due to changing market dynamics.
• AI is reshaping the advertising landscape and agency operations.
• Experiential marketing is becoming central to brand strategies.
• The enterprise value of agencies is often misrepresented in the market.
• Private equity is increasingly interested in the advertising ecosystem.
• Founders are reconsidering their exit strategies in light of market changes.
• The importance of financial performance in upcoming deal activity is paramount.
• Prompt engineering is emerging as a valuable skill in the creative industry.

Chapters

00:52 Chloe Cotoulas' Presidential Writing Experience

05:07 Chloe’s Career Path from Creative to Finance

10:04 Holdco Shakeups, IPG–Omnicom, & WPP

17:26 How Market Turmoil Impacts Independents

19:03 New Buyers & Founder Mindset 

22:38 Selling to Holdcos vs. Challenger Networks

24:15 The Rising Trend of Experiential + Social

30:19 Deal Flow Outlook for the Next Two Quarters

32:45 AI Opportunity: Differentiation & Acceleration

33:24 AI Risks, Defensibility, & Prompt Engineering

36:51 Closing Thoughts 

Connect with Christian and Ayelet

Ayelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/

Christian's LinkedIn: https://www.linkedin.com/in/hassold/

Web: https://www.inorganicpodcast.co

In/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featured

Connect with guest, Chloe Cotoulas

https://www.linkedin.com/in/chloe-cotoulas-92082861/

Hosted on Acast. See acast.com/privacy for more information.

In this episode, co-hosts Ayelet Shipley and Christian Hassold discuss WPromote's acquisition of Giant Spoon. They delve into the intricacies of the acquisition process, emphasizing the importance of trust and the contributions of a strong deal team. The conversation also touches on market reactions to the acquisition and the importance of post-merger integration planning. The hosts conclude with reflections on lessons learned and future goals for the newly formed agency.

Takeaways

• Thanksgiving cooking hacks can lead to perfect meals.
• The acquisition of Giant Spoon by WPromote is a significant industry move.
• Trust and communication are crucial in the deal process.
• Shared expectations workshops can enhance collaboration.
• Having a partner to navigate complex P&Ls is critical to navigating technical financial discussions in a deal process
• Market reactions can provide insights into industry perceptions.
• The integration process should be planned from the start.
• Maintaining brand identity is important post-acquisition.
• Future goals and objectives are vital for continued growth.

Chapters

00:00 Thanksgiving Reflections and Cooking Hacks

02:12 Major Acquisition Announcement: WPromote and Giant Spoon

05:05 The Search for the Right Agency: A Corporate Development Journey

10:08 Navigating the Deal Process: Trust and Communication

17:31 Building Trust: Shared Expectations Workshop

21:30 Challenges and Insights from the Deal Process

25:05 Market Reactions and Industry Perspectives

29:21 Final Thoughts and Future Goals

Connect with Christian and Ayelet

Ayelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/

Christian's LinkedIn: https://www.linkedin.com/in/hassold/

Web: https://www.inorganicpodcast.co

In/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featured

Episode References

Ad Age Deal Announcement

GE’s Opening Day Commercial by Giant Spoon

Hosted on Acast. See acast.com/privacy for more information.

Summary

In this episode of the In/organic Podcast, co-host Christian Hassold shares insights from the KPMG Technology M&A Conference, discussing the current landscape of mergers and acquisitions, particularly in the tech sector. In this episode, Christian shares highlights from the conference, including the pervasive influence of AI on M&A decisions, the challenges and opportunities presented by the AI investing landscape, and the importance of creative deal structures in navigating the current market dynamics. The episode also covers the “operator's dilemma” faced by CEOs - that is, the rise in peer pressure to do M&A, and what are the best practices are from leading strategics. Finally, Hassold provides an overview of current B2B SaaS deal activity and market trends based on Pitchbook data.

Takeaways

• The KPMG M&A Conference provided valuable insights into current market dynamics.
• AI is a major factor influencing M&A decisions and strategies.
• VCs are increasingly making investments in AI startups without getting governance rights, and not always checking the underlying economics of the business
• The operator's dilemma highlights the challenges that CEOs face in mergers and acquisitions (M&A).
• Corporate development roles are seeing a significant increase in demand.
• Top CEOs simplify their M&A strategies to focus on core problems.
• Deal activity in the tech sector is on the rise, indicating a healthy market.
• Earnouts are becoming a significant component of deal structures.

Chapters

00:00 Introduction and Context of the Episode

02:50 Insights from the KPMG M&A and Tech Conference

06:04 AI's Pervasive Influence on Tech and M&A

08:54 The AI Investing Landscape

11:40 Deal Structures Sparking Innovation

16:42 The Operator's Dilemma in M&A

21:48 Corporate Development and Deal Activity

24:38 Priorities in M&A for Corporates vs. Private Equity

29:19 Case Studies of Successful M&A Strategies

32:59 Market Update on Deal Activity and Earnouts

Connect with Christian and Ayelet

Ayelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/

Christian's LinkedIn: https://www.linkedin.com/in/hassold/

Web: https://www.inorganicpodcast.co

In/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featured

Episode References

KPMG M&A Conference Agenda

KPMG 2025 Deal Market Study (buyer priorities)

Kirkland & Ellis M&A Bring Down Report 2025 (earnout data)

Hosted on Acast. See acast.com/privacy for more information.