Something big is coming!...

Water cooler conversations at the Possible conference are pointing to a major deal announcement in the next two weeks — a strategic buyer nobody has seen coming, going after independent agencies with significant media underspend. Christian and Ayelet are on the story. Stay close.

But first: two deals, two market insights from the Ad Age House session at Possible, and one very clean example of how a bootstrapped independent agency is running corp dev with zero institutional capital behind it.

Two deals. One major tease. Under 16 minutes.

⏱️ TIMESTAMPS

0:00 — Post-Possible recovery, thank yous, and let's get into it

0:37 — Market insight #1: Rollups in fragmented categories are the PE thesis right now

2:00 — Why PE backs away when two players already control 40% of a category

2:30 — Market insight #2: AI is breaking reps and warranties in M&A deals

4:00 — The 12-18 month outlook: legacy media consolidation, take privates, dry powder still parked

5:20 — Deal #1: Brkthru acquires Gigawatt — bootstrapped agency runs corp dev in-house

7:00 — Why Breakthrough's January acquisition announcement was genius top-of-funnel

8:00 — The vertical thesis: hospitality and tourism, low-risk test case deal

9:00 — You don't need institutional capital to run an M&A strategy

9:48 — Deal #2: Instacart acquires InstaLeap — grocery tech, international expansion

11:00 — What Instacart actually bought (it's not just international coverage)

12:00 — Storefront Pro vs. InstaLeap: two different operating models for two different markets

13:00 — The 100 retailer relationships across 30 countries are the real asset

13:30 — Instacart's full M&A cadence: 2021 through 2026

14:17 — Props to the corp dev team, PMI advisor, and GP Bullhound sell-side

15:47 — 🚨 The tease: a mystery strategic buyer is coming for independent agencies

🔔 Live every Friday — subscribe so you don't miss the big announcement

💬 Drop your guesses on the mystery buyer in the comments

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

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Scot Wingo has built, scaled, taken public, and sold companies through multiple waves of ecommerce and software disruption. Now he’s building again, this time around agentic commerce.

In this episode of In/organic, Christian Hassold sits down with Scot Wingo at Shoptalk to talk about ReFiBuy, AI agents, ecommerce infrastructure, SaaS moats, founder survival, and what early-stage companies should do as AI reshapes software and go-to-market.

Scot is best known as the founder and former CEO of ChannelAdvisor, which went public in 2013 and was later acquired by private equity. He is also an active investor and mentor in the North Carolina startup ecosystem, with exposure to hundreds of early-stage companies.

The conversation covers:

- Why Scot started ReFiBuy after reading about agentic AI

- How AI agents could create the next generation of ecommerce marketplaces

- Why “research, find, buy” may become a new commerce workflow

- What ChannelAdvisor taught Scot about marketplaces, infrastructure, and exits

- Why going public is exciting, but running a public company may not be for every founder

- How founders should think about defensibility and moats in the AI era

- Why proprietary data, workflow depth, and customer feedback matter more than ever

- What early-stage SaaS companies should do when capital is harder to raise

- Why go-to-market is breaking for many traditional software companies

- How founders should evaluate M&A, acquihires, mergers, and strategic exits

- What Scot expects from agentic commerce over the next 12 months

- This episode is for SaaS founders, ecommerce operators, investors, corporate development leaders, and anyone trying to understand how AI agents will change software, marketplaces, and M&A.

Chapters

00:00 Intro from Shoptalk

00:45 Meet Scot Wingo

02:00 From ChannelAdvisor to ReFiBuy

04:00 Why public-company life was not the right fit

06:00 Investing in the North Carolina startup ecosystem

09:00 What ReFiBuy is building

12:00 Agentic commerce and the next marketplace shift

16:00 Why content and thought leadership still matter

20:00 Learning from customers and following the thread

24:00 Startup survival in a tougher funding market

28:00 Why SaaS go-to-market is breaking

32:00 Defensibility and moats in the AI era

37:00 Proprietary data and workflow depth

42:00 M&A options for early-stage startups

47:00 Mergers, acquihires, and strategic exits

52:00 AI valuations and changing SaaS multiples

56:00 Scot’s predictions for agentic commerce

01:00:00 Final thoughts

Subscribe to In/organic for conversations on SaaS M&A, AI disruption, strategic acquisitions, agency M&A, and lower-middle-market dealmaking.

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

Connect with Scot Wingo

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

Learn More about Refibuy

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

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Headlines say ad tech M&A is down. We read the actual report. The story is more nuanced — and the two deals we're covering this week prove the lower middle market is still moving fast.

Christian and Ayelet are back for Deal Review Friday with a market data deep dive and two deals that just closed — a partner-first aqui-hire by Amex that's been in the works since 2024, and the final piece of a three-part sequenced build by Viant that's been two years in the making.

Two deals. One market correction. Still under 20 minutes.

⏱️ TIMESTAMPS

0:00 — Happy Friday, conference circuit recap (Jaggly Leonis + Own It Women's Summit)

1:00 — Market insight: Luma Partners says ad tech M&A is down. Are they right?

2:30 — Breaking down the data: sub-$100M vs. $100M+ deal activity by category

3:45 — Ad tech, martech, digital content — what's actually moving and what's not

5:00 — The sub-$50M thesis: where Christian and Ayelet think the real action is

6:10 — Deal #1: Amex acquires Hyper (HyperCard) — agentic AI expense management

7:17 — The Hyper investor roster: Sam Altman, former MasterCard CEO, Netflix co-founder

8:00 — How this fits Amex's expense management platform launch later this year

9:00 — Center (2025) gave them the workflow. Hyper gives them the AI agent layer.

9:45 — Amex's direct play on Concur, Ramp, and Brex

10:10 — Was this an acqui-hire? Christian's take on the deal structure

10:44 — Deal #2: Viant acquires TVision Insights for $40M

12:00 — The trifecta: Iris TV (content) + Locker (identity) + TVision (attention)

13:18 — The data exclusivity question — and why this deal is different from Iris TV

13:58 — Props to Eric Stearns, Viant Head of Corp Dev — first deal in seat

14:22 — Deal economics: 4x revenue, $22.5M cash, clean balance sheet

15:36 — TVision raised at $80M valuation, sold for $40M — the cap table math

16:00 — Wrap + episode drops: Ep. 56 (AI Agents) and Scott Wingo episode incoming

🔔 Subscribe — we're going live every Friday

💬 Drop deals you want us to cover in the comments

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

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Strategic M&A is up 40% year-over-year on LOI volume. And this week's deals prove the closings are following.

Christian and Ayelet are back for Deal Review Friday with three deals that just crossed the wire — including Mountain Gate's fifth add-on in under five weeks, a retail intelligence merger that was clearly part of the thesis from day one, and one of the more creative dual-strategic acquisitions we've seen in a while.

Three deals. One market signal. Fifteen minutes. (Okay, twenty.)

⏱️ TIMESTAMPS

0:00 — LinkedIn buffering, as usual

0:48 — Market signal: strategic LOIs up 40% YoY per Spearhead Corp Dev

1:30 — PE deal volume Q1: $216B, up from $190B — but strategics are the real story

2:46 — Deal #1: Harvest Group (Mountain Gate) acquires Cartograph — 35 days after platform close

5:35 — Cartograph's superpower: scaling challenger brands on Amazon

6:44 — Full disclosure: Mountain Gate is not sponsoring this podcast

7:13 — Who advised? Chris Moe peels back the layers

8:30 — Deal #2: Engine + Nuqleous merge to form end-to-end retail intelligence platform

12:18 — CPG point solution fragmentation and why this merger was inevitable

13:26 — Nick Dossier: repeat offender, same playbook, larger scale

14:00 — Crisp lit up this category — and Engine is now the OG competitor

16:24 — Engine's full acquisition history: Evertech, Leftbridge, now Nuqleous

17:18 — Deal #3: Cary sells for $80M on $900K ARR — AngelList + Lettuce split the asset

19:00 — Founder's second exit (first was Teachable at $250M)

20:04 — Wrap: yes, we went over 15 minutes again

🔔 Subscribe — we're going live every Friday

💬 Drop deals you want us to cover in the comments

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

https://www.youtube.com/@InorganicPodcast

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Deal Review Fridays are here.

No guests, no fluff. Just Christian and Ayelet live with market intel and the deals that closed this week — before everyone else is talking about them.

This week: private debt markets are tightening (and it's freezing $100M+ deals), Podean just keeps buying, Mountain Gate is deploying out of Fund 3 at an alarming pace, and MIQ quietly built a mobile M&A stack nobody noticed.

Three deals, one market signal, under 15 minutes.

What we cover: the private debt compression from 4.5x to 3.0-3.5x EBITDA and what it actually means for deal flow, Podean's third add-on in under six months (UK-based AdMerge), Mountain Gate's fourth platform investment out of Fund 3 (Upswell Marketing), and MIQ's mobile capability gap-fill with Rocket Lab out of Latin America.

TIMESTAMPS

0:00 — Introducing Deal Review Fridays: why we're going live

1:30 — Market signal: private debt compression and its downstream M&A impact

4:11 — Ayelet on the ground: deals still closing sub-$50M EV

4:54 — Deal #1: Podean adds AdMerge (UK) — third add-on, ~$30-35M revenue run rate

7:37 — Deal #2: Mountain Gate platforms Upswell Marketing — Fund 3, fourth investment

9:34 — Mountain Gate's portfolio thesis: multiple distinct platforms in parallel vertical lanes

10:41 — Deal #3: MIQ acquires Rocket Lab — mobile gap fill + LATAM programmatic stack

13:35 — Wrap: what Deal Review Fridays are (and what they're not)

🔔 Subscribe — we're going live every Friday

💬 Drop deals you want us to cover in the comments

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

https://www.youtube.com/@InorganicPodcast

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AI agents are moving from experiments to full-time “AI employees.” In this episode of In/organic, Christian Hassold sits down with Ameya Deshmukh from EverWorker at Shoptalk to discuss how business leaders are using AI workers to automate entire jobs, replace point solutions, and change the future of agencies, consulting, and go-to-market teams.

EverWorker is building an AI workforce platform that helps companies launch AI employees in as little as 45 days. Ameya explains why DIY agents often break down inside real organizations, why maintenance and adoption matter more than the first prototype, and how AI-first agencies may gain market share while slower agencies get left behind.

The conversation covers:

- Why building one AI agent is easy, but scaling 30-40 use cases is hard

- How EverWorker turns AI workers into modular business infrastructure

- Why vertical AI agent platforms, agencies, and consulting firms are at risk

- How EverWorker beat a traditional consulting firm in an AI strategy process

- Why early-stage startups and agencies are adopting AI workers now

- What AI-first agencies need to do to stay competitive

Chapter Markers

00:00 Intro from Shoptalk

00:39 Meet Ameya from EverWorker

01:00 What EverWorker does

01:29 Why DIY AI agents are not enough

02:55 The problem with maintaining agents

04:26 Making AI workers easier to manage

05:31 EverWorker’s funding and company stage

06:09 Will EverWorker acquire or be acquired?

06:58 Whose lunch will AI workers eat?

08:25 Could Accenture buy EverWorker?

08:39 How small businesses can start using AI workers

09:06 Why agencies need to become AI-first

10:09 Final thoughts

If you’re a founder, agency owner, SaaS operator, investor, or M&A professional trying to understand how AI agents will change business services, this episode is a practical look at where the market is going.

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

https://www.youtube.com/@InorganicPodcast

Connect with Ameya Deshmukh

https://www.linkedin.com/in/ameyadeshmukh10/

Learn more about EverWorker

https://everworker.ai

Subscribe to In/organic for conversations on SaaS M&A, agency M&A, AI disruption, strategic acquisitions, and lower-middle-market dealmaking.

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Scott Gifis has been around the block. President & COO at Frame.io through its $1.3B exit to Adobe. LP at GTM Fund and Stage 2 Capital. Now CEO of Wyllo (formerly NoFraud), a CX-first risk intelligence platform backed by PSG — and he just closed his first tuck-in acquisition. We caught up with Scott at ShopTalk in Las Vegas to go deep on how he thinks about inorganic growth as an operator, not a banker — and what it actually takes to get a tuck-in deal done right.

What we cover:

- Why Scott tried to retire after Frame.io and lasted two days

- How he reframed "fraud prevention" as a customer intelligence problem

- Kissing 150 frogs before finding Yofi — and why the partnership came first

- The exact filters he uses for M&A: product acceleration, GTM fit, buyer alignment, pricing architecture

- Why philosophical alignment matters more than the term sheet

- The rebrand from NoFraud → Wyllo and what the name actually means

- His buy box for the next acquisition (hint: $5M+ revenue, data-first)

- Who writes the $1-2B check for Wyllo in a few years (MasterCard? Visa? A help desk platform?)

⏱️ TIMESTAMPS

1:11 — Welcome & guest intro: Scott Gifis, CEO of Wyllo (formerly NoFraud)

1:53 — From aspiring pro hockey player to 7 early-stage startups

4:53 — Frame.io → Adobe: the $1.3B exit story

5:49 — Why Scott chose commerce after the exit (and why it's the hardest space to win)

8:10 — The contrarian playbook: always call the investors who passed on the last deal

9:20 — Reframing the category: fraud prevention isn't payments, it's trust intelligence

13:51 — What is Wyllo? The CX-first risk intelligence platform explained

16:15 — The checkout product disaster — and what it actually taught him

17:39 — Why the e-commerce tooling market is fundamentally broken

19:10 — The Shopify model: what they got right and where the Wild West begins

21:14 — M&A is like marriage: you can't just swipe right

21:58 — The original thesis: buy all the software (and why it fell apart)

23:47 — Driving alignment without an M&A background: Scott's three filters

25:10 — The GTM fit trap everyone misses: buying center and pricing architecture

26:32 — "Marriages don't die because people fight. They die because they don't."

28:26 — Partner first: why the Yofi relationship started as a go-to-market partnership

31:58 — How Wyllo won despite being the smallest bidder at the table

33:52 — Deal structure breakdown: cash, rollover equity, and the earn-out challenge

36:44 — Why Scott waited three years to rebrand (the brand must earn the promise)

38:28 — Why they chose "Wyllo": roots, flexibility, protection, and the changemaker thesis 39:18 — Buy box for the next acquisition: what Scott is actually looking for

40:30 — The $5M revenue threshold and what it signals about product-market fit

41:11 — "The complexity of GTM has become several levels harder than five years ago"

41:18 — The one capability Scott would go acquire right now if he could

42:32 — Who writes the $1-2B check for Wyllo? The strategic acquirer shortlist

45:50 — Wrap-up and close

🔔 Subscribe for weekly agency and SaaS M&A coverage

📍 Recorded live at ShopTalk, Las Vegas

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 Scott Gifis on LinkedIn

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

Learn more about Wyllo: https://wyllo.ai/

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Who's Going to Pay $1B+ for a Scaled Independent Agency? | In/Organic Ep. 53

The question every banker, founder, and PE partner is asking right now — and we used Clay to actually answer it.

Christian used Clay to run a full analysis of the Forrester Commerce Services Wave Q1 2026 and map out which players have both the strategic rationale AND the balance sheet to acquire a scaled independent. The answer might surprise you (👀 Tata).

Then we break down FIVE deals from Q1 that you need to know about:

• Front Row + Socium Media — textbook Amazon-first capability acquisition
• Podean + AdAdvance — tech + customer base play from the Mountaingate portfolio
• OneMagnify + Optimal — carve-out, vertical depth, and a now ~1,000 person agency
• Shipyard + Fancy AI — the smartest "partner before you buy" move we've seen in a while
• Sol XC + Craft & Commerce — quiet cross-border deal flying under the radar
• 
  

Plus: why WPP + a PE sponsor could flip from "maybe" to "yes" fast, and what the recurring AI-forward theme across all five deals actually signals.

Timeline

01:15 - Celebrating 10,000 YouTube views: growth milestone

02:11 - What strategic buyers are willing to pay for independent agencies

03:10 - The Forrester Commerce Services Wave and agency positioning in the market

05:55 - Analyzing the cash positions of potential acquirers like Tata and Accenture

07:18 - When do strategic players step in to make their move?

09:22 - Highlights of recent acquisitions: Front Row and Socium

10:11 - The strategic fit: Amazon-focused agencies and vertical capabilities

12:13 - Podion’s recent acquisition of AdAdvance and its strategic significance

14:01 - Clarity in deal strategy amid rising deal volume in the first quarter

15:03 - The role of PE firms like Mountain Gate building strong portfolios

16:16 - The importance of strategic clarity and data-backed decision making in M&A

17:05 - The acquisition of Optimal’s performance media by One Magnify

18:16 - Expanding capabilities through strategic acquisitions and vertical specialization

19:41 - The latest on strategic investments: Shipyard’s partnership with Fancy AI

23:16 - A hidden gem: Craft and Commerce’s acquisition by Sol XC and Amazon retail media focus

24:24 - The ongoing hunt for agencies: Opportunities in performance marketing and Amazon services

25:37 - The quest for sponsors and strategic partnerships to support industry growth

26:20 - Final insights: credible buyers are out there, retail media remains hot, and AI integration continues to shape deal flow

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.

Summary

In this episode, Azim Nagree, head of M&A at Herringbone Digital, shares insights on building a successful origination engine, the importance of early and honest communication in M&A, and how agencies can prepare for sale by focusing on retention, growth, and profitability.

Takeaways

• Open and honest conversations early in the process streamline deals.
• Retention rate of 80% is a key indicator of business health.
• Growth of 15-20% and EBITDA of 20-25% are desirable benchmarks.
• AI should improve core business metrics to add value.
• Founders should focus on building a strong foundation before sale.

Chapters

00:00 Introduction and Milestone Celebration

01:10 Azim Nagree’s Background and Herringbone's Focus

05:42 Herringbone's Acquisition Strategy and Ideal Targets

07:49 Relationship with Private Equity and Deal Support

09:21 Lessons from Deal Experience and Early Communication

13:43 Deal Origination Process and Tech Stack

15:00 Defining the Prospect Universe and Narrowing the Buy Box

16:33 Balancing Organic and Broker Deal Sourcing

18:43 Assessing Seller Readiness and Valuation Expectations

20:01 Using the 'Magic Number' to Evaluate Sellers

23:57 The Triangle of Value: Retention, Growth, Profitability

25:21 Evaluating EBITDA and Adjusted EBITDA

28:57 Retention and Growth Benchmarks for Agencies

29:59 The Leaky Bucket Problem in Agencies

30:05 Identifying Signs of Retention Issues

30:36 Impact of AI on Agency Valuation and Performance

34:09 Common Mistakes Before Selling an Agency

35:36 Advice for Founders Considering Exit

36:47 Managing Communications with Potential Buyers

39:51 Closing Remarks and Key Takeaways

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 Azim Nagree on LinkedIn

Herringbone Digital - https://herringbonedigital.com 

Azim Nagree on LinkedIn https://www.linkedin.com/in/azimnagree/ 

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In this episode, Yannick Lorenz uncovers his remarkable transition from building Shadow Digital to leading Vesa Digital’s aggressive M&A and growth strategy. He talks openly about the ups and downs of agency life, the importance of building a sellable business, and stepping into a strategic role in acquisitions—all fueled by lessons learned the hard way.

Key Topics:

• How Yannick built Shadow Digital from a freelance side hustle into a successful agency
• The pivotal moment when he realized the value of making his business sellable
• The lessons learned from hitting rock bottom during a major agency crisis in 2020
• The unique approach Vesa Digital takes to agency roll-ups and the concept of the VAN (Vesa Agency Network) strategy
• Creative deal structures and the importance of leaving chips on the table during acquisitions
• How Yannick is leveraging his CEO experience to now lead Vesa’s inorganic & M&A efforts
• The impact of self-sourcing deals and avoiding traditional private equity pathways
• Navigating culture fit, valuation, and deal negotiations with founders
• Practical advice for founders about financial literacy, recurring revenue focus, and deal-making mindset

Timestamps:

(0:13) The rapid evolution of Claude AI and setting up local coding interfaces

(1:27) The magic of task stacking versus answer approximation in Claude

(3:05) Introducing Yannick Lorenz and his entry into agency growth and exit

(4:26) Yannick’s background: from Germany to founder in California

(6:10) Building Shadow Digital: from side hustle to agency

(8:38) The turning point: landing a $20,000 deal and scaling

(11:26) Navigating the 2020 crisis and the push toward specialization

(12:24) Scaling rapidly with Webflow before the crash

(13:47) A major realization: building a business to sell and the importance of cash flow

(15:15) How Yannick connected with Vesa during a cold outreach mistake

(17:19) The evaluation process: fit, culture, and professionalism

(20:05) From lifestyle agency to a growth-focused exit plan

(22:14) Strategies for leaving cash in the business before an exit

(23:23) Reflecting on the emotional rollercoaster of entrepreneurship

(25:21) Learning the inorganic & M&A game from top experts

(27:48) Vesa’s current inorganic growth strategy and future plans

(29:55) Creative deal structures in agency acquisitions ($500K–$1M range)

(34:15) Lessons on being an empathetic versus aggressive acquirer

(36:25) Why financial literacy and recurring revenue are vital for deals

(38:35) How interested founders can connect with Yannick for opportunities

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 Yannick Lorenz on LinkedIn

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

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