Ad Age House ran a session called Inside the Deal — Will Lee, CEO of Adweek moderating, with Michael Kassan from 3CV, Anuj Mathur from Moelis, Leonard Tessler, and Sanford Michaelman on the panel. The conversation covered the state of M&A markets and the 12-18 month outlook. Two things stood out.

Rollups in fragmented categories are the PE thesis right now.

What they're hearing from PE firms isn't "find me this deal" — it's "find me a fragmented category to consolidate." Tech being cheaper has fragmented agency and creator-platform markets, which makes roll-up math work where it didn't before. They explicitly flagged that when two players already control 40% of a category, PE backs away — the hurdles are too high.

AI is breaking reps and warranties.

A recent deal closed April 1 where the seller flatly refused to make standard non-infringement reps because their product had AI underlying it. The logic: copyright violation is binary, but LLMs trained on infringed material produce derivative outputs you can't unscramble. Buyers are starting to mark that bucket of revenue to zero or wrap it in warranty insurance. Insurance carriers are beginning to design AI-specific products. Worth flagging this in your own diligence frameworks — it'll become standard.

12-18 month outlook:

• Legacy media: heavy consolidation, driven by cost rationalization. Warner Bros Discovery referenced as the template.

• Marketing/adtech/martech: lots of take-privates of sub-$2B public companies. Bar to remain public is rising fast, and the IPO wave (SpaceX, Anthropic, $30B+ names) will force funds to sell smaller positions to fund those allocations.

• Macro: bumpy. Tariff/geopolitical uncertainty is keeping dry powder parked. Hockey-stick recovery isn’t here until that resolves — could be November, could be two years.

Deal #1: Brkthru + Gigawatt

On April 16th, Brkthru — a Detroit-area digital media agency, roughly 170 employees, fully bootstrapped and privately owned — acquired Gigawatt, a Milwaukee-area programmatic shop founded by Adam Perrick in 2019. Estimated five to nine people, sub-$5M revenue. Financial terms not disclosed.

The press release framing: strengthening Breakthrough’s integrated media capabilities with deep expertise in hospitality and tourism.

The real story is the process.

In January 2026, Brkthru announced publicly that they were launching an acquisition program for 2026. No banker involved — fees don’t justify the time on deals this size. What the announcement did was function as top-of-funnel corp dev. They told the market what they were looking for, generated inbound, and closed their first deal three months later.

That’s a smart, capital-efficient way to run M&A as a bootstrapped operator. The announcement does the sourcing work that institutional buyers usually pay bankers to do.

The thesis is also deliberately low-risk. This isn’t a capability gap fill into unknown territory. Brkthru already plays in hospitality and tourism. Gigawatt is a programmatic shop that goes deeper into a vertical they already know. The business models are similar. The integration lift is manageable. If they can’t pull off a deal this aligned on paper, they find out now — on a small deal, while it’s still recoverable — before scaling the program.

The broader takeaway: you do not need institutional capital to run an M&A strategy. Creativity and alignment are the currency in the sub-$5M deal market. The wild west of deal making is open to any operator willing to run the process.

Deal #2: Instacart + InstaLeap

On April 14th, Instacart announced the acquisition of InstaLeap — a Bogota-founded grocery technology company started in 2019, serving nearly 100 grocery retailers across roughly 30 countries, primarily in Latin America with presence in Europe and the Middle East. The platform has powered over 100 million transactions. Financial terms not disclosed.

Most coverage framed this as Instacart going international. That’s accurate but incomplete.

What Instacart actually already had: Storefront Pro — a white label e-commerce and fulfillment platform serving 380+ grocery banners, already making its first international deployments with Costco Spain and France earlier this year.

What’s different about InstaLeap: Storefront Pro is built for retailers plugging into Instacart’s infrastructure — Instacart shoppers, Instacart fleet, the marketplace’s gravity. InstaLeap is built for retailers running their own stores, their own delivery, and orchestrating across third-party marketplaces. That’s the operational reality for international grocers, particularly in the dense urban markets of Europe and Latin America where retailers keep all of their own infrastructure. It’s almost required.

So this isn’t a gap fill on capability. It’s a gap fill on operational fit for a different kind of retailer.

The 100 retailer relationships are the actual asset — years-long enterprise contracts in markets where Instacart’s footprint is essentially zero. InstaLeap operates as a wholly owned subsidiary for continuity, with Instacart rolling its own products (e-commerce, connected stores, retail media, AI, data) into the InstaLeap retailer base over an estimated 18-24 month integration window.

Instacart’s M&A cadence tells the story of a company systematically assembling pieces: Caper AI and Food Storm in 2021, Eversight and Rosie in 2022, Shive AI in 2024, Windshop in 2025, InstaLeap in 2026. Each one adds a layer.

Props to Quad Jiwan, Head of Corp Dev at Instacart — this is his third deal as Head of M&A. Kimberly Baird at M&A Maximizer led post-merger integration. GP Bullhound ran sell-side out of their Spain office — a London-headquartered tech bank, not a Latin American firm, which signals InstaLeap was marketed as a global software asset and priced off international tech comps.

🚨 The Tease

Water cooler conversations at Possible are pointing to a major deal announcement in the next two weeks.

A strategic buyer nobody has been talking about. Going after independent agencies. Specifically those with significant media underspend.

Christian’s guesses — KKR, Apollo — have already been shot down by people who know. So we genuinely don’t know who it is yet.

Ayelet may have something. She’s confirming first.

We’re on the story. Stay close.

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We sat down with Scot at ShopTalk and covered a lot of ground: what ReFiBuy actually does, why the SaaS moat playbook is breaking, how early-stage founders should think about survival and consolidation right now, and where agentic commerce goes in the next twelve months.

Here’s the full breakdown.

What ReFiBuy Actually Does

The core insight starts with a data asymmetry problem.

For twenty years, brands and retailers operated in what Scot calls “keyword jail.” Google gave you four words of shopper intent. That was the gold standard. And because you only had four words, you only needed to provide basic product information — size, color, the fundamentals.

That world is over.

Today’s AI engines know an enormous amount about the shopper — preferences, purchase history, dietary restrictions, shoe size, lifestyle. But they know almost nothing meaningful about the products themselves. Most product catalogs are still basically spreadsheets with a handful of attributes, and there’s no standardization across them. Just the word “small” is described in over 400 different ways across the industry.

ReFiBuy fixes the product side of that equation. They help brands and retailers expand their product catalog attributes, layer in rich Q&A content that addresses shopper concerns and occasions, and incorporate review data in a way that LLMs can actually use. The goal: give the AI engine enough context about a product that it can make a confident, accurate recommendation to a shopper who’s already told the engine everything about themselves.

The same enriched catalog payload that works for ChatGPT, Perplexity, Copilot, Meta, and Gemini also works for on-site LLM search — Rufus on Amazon, Sparky on Walmart. One infrastructure investment, multiple distribution channels. That’s the bet.

The ReFiBuy Team and Why It Came Together

Scot didn’t start fresh. He went back to a problem he couldn’t solve during the ChannelAdvisor years — the canonicalization and taxonomy mapping challenge that sits underneath all of this product data work — and asked whether agentic AI frameworks could crack it now.

Turns out they can.

The engineering team includes Cameron Bo and James Frawley, both ChannelAdvisor veterans, along with Derek Conlin on go-to-market. Part of the team is drawn from a ChannelAdvisor office in Limerick, Ireland — a hotbed of canonicalization talent that traces back to Dell’s internationalization work at the University of Limerick’s computer science program. It’s a niche skill set, and Scot’s been cultivating it for twenty years.

The Buy Box for Inorganic Growth

Scot’s current thinking on acquisition is more nuanced than most operators at his stage.

Engineering talent isn’t his constraint — he has it. The traditional SaaS acquisition for GTM talent is tempting, but he’s skeptical. Anyone who built a substantial go-to-market motion before 2022 is working off a playbook that’s increasingly broken. You’d be acquiring methodology debt alongside the customer base.

What he’d actually pay for:

Customers and revenue streams from companies whose GTM is sputtering but whose install base is real. Convert ten percent of a long-tail customer list into your model and you’ve got a meaningful ROI even if you write off everything else.

Audience. The most controversial item on his buy box — and the most forward-looking. In an environment where noise is at a nine out of ten and climbing, a founder or company with a loyal, engaged audience is a genuine strategic asset. Scot openly says he wouldn’t have said this five years ago. He’s saying it now.

The underlying logic: inbound is working at ReFiBuy in a way outbound SDR motions never could in this environment. His Substack, Retail Agentic, is on track to drive half of lead generation. Content is the new cold call, and audiences are the new distribution.

Sharks in the Water: What Scot Tells Struggling Founders

Scot published a piece warning early-stage founders about the current environment. The message, synthesized:

Buy runway first. Your existing investors are your best option. Your number one job as CEO is to not run out of money. Everything else is secondary.

Cut costs relentlessly. Not selectively. Relentlessly.

Diagnose your churn data. If you’re a B2B SaaS company selling to mid-market or enterprise and you’re not seeing churn creep up, look harder. It’s probably there. When you find it, trace it back — it’s most likely a signal that your competitive moat has been eroded by AI-native alternatives, not that your product got worse.

Retool go-to-market. The outbound SDR motion is trending toward zero efficacy. If your pipeline depends on it, you need a plan B. The noise level is too high and buyers have tuned it out almost completely.

Early-Stage Consolidation: The Down-Market M&A Opportunity

One of the most interesting parts of the conversation was Scot’s framework for startup-to-startup combinations — something he walks portfolio companies through regularly.

The logic is straightforward: two companies with complementary assets (one has proprietary data, one has distribution; one has product-market fit, one has runway) can be stronger together than either is alone. Combined back office, combined capital, combined time. In a market where lead investors are pulling term sheets at the eleventh hour and FUD is driving weird behavior on all sides, buying yourself more runway through a combination isn’t giving up — it’s smart capital allocation.

The challenge is always valuation. Tech founders default to the metric that makes them look best — last raise, revenue multiple, EBITDA multiple — and they avoid the money conversation until it’s almost too late. Scot’s prescription: get to the economics conversation early, use a simple one-page MOU framework to force the issue, and build a basic model that shows the combined thesis. The acquirer builds the model. The acquirer sells the target on why a smaller piece of something real is better than a larger piece of something dying.

Cash on balance sheet, Christian noted, is increasingly a force multiplier in deal structure — especially in AI-adjacent deals where capital raised is being treated almost like a proxy for validation. Christian cited the Goldcast/Cvent deal ($300M acquisition on roughly $8-10M ARR, with $35-40M raised) as an illustration of the dynamic. The old revenue multiple framework is being supplemented, and sometimes replaced, by a capital-raised multiple in high-conviction AI categories.

The Twelve Moats Framework

When evaluating early-stage companies — either as an investor or as an operator thinking about defensive positioning — Scot uses a twelve-factor framework for AI-era competitive moats. He built it from research across a16z (Alex Rampell’s talk is worth finding), NFX, and a handful of other VC frameworks.

The most defensible moats, in his view:

Proprietary data that can’t be synthesized in parallel. The mythical man-month problem applied to data — nine women can’t make a baby in a month. If your data advantage comes from iterative customer feedback loops and workflow embedding over time, it can’t be replicated by a well-funded competitor throwing engineers at it. That’s a real moat.

Workflow embeddedness. Get deeply enough into a customer’s operational workflow and the switching cost becomes structural, not just contractual. The best companies do both simultaneously — they’re embedded in the workflow AND the workflow runs on proprietary data they’ve been building for years.

Founder-market fit. For the earliest stage, the jockey matters as much as the horse. You want founders who deeply understand the market, stay agile, and are thinking hard about go-to-market — not just product. The best mousetrap in the world is worthless if nobody can find it.

Twelve-Month Predictions on Agentic Commerce

Scot publishes an annual predictions list on the Jason and Scot show — ten years of predictions, tracked annually. His calibration note: in the old era he was always a year early. Now he’s pulling predictions in by a factor of three because the pace of change has accelerated that dramatically.

A few of his 2025/26 predictions have already come true. Notable ones:

Facebook entering agentic commerce — happened. A “super protocol” that can talk to MCP and other lower-level protocols — UCP arrived. And the big one: by this holiday season, he’s predicting ten percent of e-commerce transactions will route through agentic commerce in some form.

The underlying thesis: filtered navigation is a broken experience. Conversational commerce — whatever you call it — gets shoppers to answers faster, with more personalization, and with less friction. E-commerce has been growing in line with retail for years. Agentic commerce has the potential to re-accelerate the gap by making the digital experience meaningfully better than the physical one again.

Scot Wingo is the founder of ReFiBuy and ChannelAdvisor (IPO 2013, taken private by Insight Partners 2022). He writes the Retail Agentic Substack and co-hosts the long-running Jason and Scot Show. He’s an LP in 167 companies through the Tweener Fund, focused on the Research Triangle Park ecosystem.

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Luma Partners published a report this week with a headline that runs counter to what we’ve been saying for the last two episodes: deal activity in digital media and marketing technology has lost momentum, weighed down by geopolitical tensions, declining year over year.

We read the actual report. The headline and the charts don’t quite speak the same language.

Here’s what the data actually shows:

Ad tech sub-$100M deals: Q4 2024 — 19 deals. Q4 2025 — 22 deals. That’s up. What’s down is $100M+ deals — 6 in Q4 2024, 4 in Q4 2025, 1 in Q1 2026. The big deals are getting harder. The lower middle market is holding.

Martech sub-$100M deals: 42 in Q4 2024, 40 in Q4 2025, 41 in Q1 2026. That’s flat. Not a collapse.

Digital content sub-$100M deals: 36 → 34 → 26. This one is genuinely declining — and the reason isn’t macro. It’s AI. If you’re a sub-$100M digital content business, the first question any buyer asks right now is whether you’re disruptible by AI. A lot of them are. That’s showing up in the deal count.

The category that’s missing from Luma’s data: sub-$50M. Both of us are busiest in the $20-50M EV range and it is moving. There has to be a data set that captures what’s happening at that level, because from where we sit, the wild west of lower middle market deals is very much alive.

The real story: large deals are harder. Small deals are fine. Digital content is structurally challenged. Everything else is roughly holding.

Deal #1: Amex + Hyper (HyperCard)

On April 16th, American Express announced an agreement to acquire Hyper — an agentic AI expense management startup founded in 2022, backed by Sam Altman, former MasterCard CEO Gene Lockhart, Netflix co-founder Mark Randolph, and One Medical founder Tom Lee.

Financial terms weren’t disclosed. This was almost certainly a sub-$20M deal. The framing here isn’t valuation. It’s sequencing.

This was a partner-first deal two years in the making. Hyper and Amex announced a co-branded card product with AI agents embedded in Amex’s platform back in late 2024. Amex has been running Hyper’s technology in production through a live card product since then. They knew the team. They knew the product. There was no competitive auction.

The strategic logic is clean: in March 2025, Amex acquired Center — an expense management software company, rumored at around $600M — which gave them the expense management workflow infrastructure. Hyper gives them the AI agent layer that sits on top of it. Together, they’re building a direct competitive platform aimed at Concur, Ramp, and whatever Brex and Capital One are assembling.

Amex did $72B in revenue in 2025, overwhelmingly from the card. What they’re building now is an adjacent software business on top of the card franchise — card plus expense platform plus agentic AI for corporate spend. The middle layer of expense management bloat — the manual approvals, the reconciliation friction, the paper receipts — is exactly what Amex has been quietly building toward eliminating since their 2019 acquisition that became AmericanExpress 1AP, through Nipendo in 2023, through Centur, and now through Hyper.

Christian’s read: this was an acqui-hire. Great team, real product, get them inside the building and go fix corporate expense management. Clean out the cap table, call it a day.

Deal #2: Viant + TVision Insights ($40M)

On April 15th, Viant Technology announced a definitive agreement to acquire TVision Insights for $40M — $22.5M in cash and $17.5M in Class A common stock, closing Q2 2026.

The headline number matters less than the sequence.

This is the third leg of a deliberate, multi-year build:

2024 — Iris TV: Content layer. CTV inventory classification at the content level — genre, emotion, brand safety — not just at the app or show level. Still broadly licensed and platform-agnostic.

March 2025 — Locker: Identity layer. Publisher first-party data, data activation, alternative ID management.

April 2026 — TVision: Attention layer. Panel-based, second-by-second eyes-on-screen measurement for linear TV, CTV, and walled gardens. Are viewers actually watching? How many? For how long?

Viant CEO Tim Vanderhook called it the trifecta: identity, context, attention — all feeding into their intelligence layer. He told Ad Exchanger that the TVision deal simply wouldn’t have been possible without the Locker acquisition. This wasn’t opportunistic. It was sequenced.

The detail that didn’t make the press release but matters: Maverick analyst Maria Ripps asked Vanderhook directly whether TVision’s data would remain available to other measurement providers. The answer was no. Existing contracts get honored, but as they expire, the data goes exclusive to Viant’s platform. That’s a meaningfully different integration playbook than Iris TV, which stayed broadly licensed. Same acquirer, two different strategic postures depending on what the asset does for competitive differentiation.

The economics are clean. TVision did approximately $10M in 2025 revenue. $40M is exactly 4x — reasonable for a strategic capability acquisition in ad tech. Viant’s balance sheet at end of 2025: $191M in cash, zero long-term debt, $75M untapped credit facility. They spent $22.5M in cash — roughly 12% of their cash pile — in a quarter where Luma is reporting ad tech multiples compressed 21%. They’re deploying capital with conviction against their own roadmap regardless of what the index is doing.

One complication worth noting: TVision had raised $16M in VC at an $80M valuation. The $40M exit is a haircut on preference. There was almost certainly some back-room work done to make sure the founders and team got a reasonable outcome inside that structure. On a multiple of revenue it’s fine. On a multiple of last valuation, less so. But for a 12-year-old company with real revenue and a genuine strategic acquirer at the table, this is a good outcome in a difficult market.

Props to Eric Stearns, Viant’s Head of Corp Dev, who joined from RBC Capital Markets in August 2025. This appears to be his first deal in seat. First one through the door and it’s a clean, sequenced strategic buy with solid economics. Good start.

Next week: Christian may or may not spill what he heard at the JEGI-Leonis conference in New York (Chatham House rules, technically). Ayelet just spoke at the Own It Women’s Agency Ownership Summit in front of 400 people and has a lot to say.

Both will be at Possible in Miami. Come find us.

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We caught up with Ameya Deshmukh from EverWorker on the floor at ShopTalk for a quick but dense conversation about what AI workforce platforms actually do, who they replace, and why the agency stratification moment is already here. If you run an agency, a startup, or any service business with operational overhead — this one’s worth your attention.

What EverWorker Actually Is

EverWorker calls itself an AI workforce platform for business leaders. The pitch: create AI employees and delegate entire jobs to them. Platform plus services plus templates, with AI workers live inside your business in as little as 45 days.

The outcomes they’re selling aren’t abstract. Increased revenue, reduced operational expenses, and a leaner go-to-market. For early-stage companies especially, they frame it as a simple value exchange: $60-90K annually gets you the equivalent of roughly $600K in headcount replacement plus $600K in tools you’d otherwise have to buy separately. For a capital-constrained startup, that math is hard to ignore.

“I Can Just Build This Myself” — The Obvious Objection

It’s the first thing Christian asked. If I can spin up an agent in Claude Code or OpenAI Codex tomorrow, what am I actually buying from you?

The answer is more honest than most vendor pitches: most EverWorker customers come to them after they’ve already tried to build it themselves. And they’ve usually gotten pretty far. The problem isn’t the first agent. It’s everything that comes after.

Three failure modes keep showing up:

Scale and adoption. A technically proficient VP can architect an agent. Getting the rest of the organization to actually use it is a different problem entirely. Most employees will never become builders — they need something they can pick up and use without understanding what’s underneath it.

Maintenance. Every time the agent needs updating, you’re back in the code. In a business moving fast, that becomes a constant tax on your most technical people’s time.

Bandwidth. If you needed agents badly enough to build them yourself, you’re already under operational pressure. One use case is manageable. Thirty or forty use cases — which is usually what the business actually needs — is not.

EverWorker’s solution is natural language configuration, modular architecture (workflows, workers, and skills as composable building blocks), and an integrated UI that lets non-engineers deploy and iterate without touching code. The goal is making agent management feel like managing actual employees — write an operating procedure, hand it off, iterate in plain language.

Whose Lunch Gets Eaten

This is where it gets pointed.

When a customer adopts EverWorker’s go-to-market package, three categories of vendors tend to disappear from their stack:

Vertical agent platforms. EverWorker’s AIO/SEO worker does what SEMrush charges $35K for — and delivers it as part of a broader $60K annual package covering 15 workers across the entire marketing and sales function. Per-capability cost: $5K annually versus $35K standalone. That’s not a rounding error.

Agencies. Ads agencies, SDR agencies, content agencies. They’re already seeing displacement. An SEO agency is currently using EverWorker to deliver client work — the clients don’t know the platform is writing their content. The AI-first agencies that lean into this model will take share from those that don’t. That stratification is already underway.

Consulting firms. The one that raised eyebrows: EverWorker recently won a deal against BCG in the Nordics. BCG quoted €60K and two quarters just to evaluate AI strategy and recommend use cases. EverWorker walked into the first meeting with a full business analysis, four custom use cases, and a live demo worker — built in 48 to 72 hours. The consulting engagement model for AI strategy work has a real problem.

On the M&A question — whether Accenture’s $2B remaining M&A budget might eventually find its way to EverWorker — the answer was diplomatic but unambiguous: if Accenture wants to have that conversation, the CEO is open to it.

The Agency Stratification Moment

For agency operators listening, the framing Emea offered is worth sitting with.

The agencies that survive the next three years aren’t necessarily the ones with the best people or the longest client relationships. They’re the ones that become AI-first fast enough to deliver more output with existing headcount — and use that margin to take share from competitors who didn’t move.

The laggards will lose clients to the agencies that are already doing more with less. The forward-thinking SEO agency currently running EverWorker behind the scenes for their clients isn’t the outlier. They’re the early signal.

For early-stage startups specifically, the value proposition is even cleaner. You can’t afford the headcount. You can’t afford all the tools. EverWorker is a bet on solving both problems at once, and at $60-90K annually for the equivalent of a fully staffed go-to-market function, the math works in your favor if the platform delivers.

The Bottom Line

EverWorker is a seed-stage company — $10M raised, founded by the team behind Veen (acquired for ~$2B), headquartered in Zurich with engineering in Europe and go-to-market distributed across North America, UK, and the Nordics.

They’re early. But the problem they’re solving is real, the displacement thesis is already playing out in their customer base, and the competitive vector — going after vertical SaaS point solutions, agencies, and consulting firms simultaneously — is exactly the kind of horizontal platform bet that tends to look obvious in hindsight.

Watch this space.

Recorded at ShopTalk 2026, Las Vegas.

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What he does have: a $1.3B exit (Frame.io → Adobe), seven early-stage operating roles, LP positions at GTM Fund and Stage 2 Capital, and the kind of pattern recognition that comes from building in five completely different industries. He’s now CEO of Wyllo — formerly NoFraud — a CX-first risk intelligence platform backed by PSG that just completed its first tuck-in acquisition of Yofi.

We sat down with Scott at ShopTalk in Las Vegas to break down how he thinks about inorganic growth as an operator. This one is dense. Worth reading slowly.

Reframe the Category or Don’t Bother

Scott’s first move at every company is the same: ignore how the industry describes itself and ask what problem is actually being solved.

At Frame.io, everyone said “Hollywood.” He said video — the most powerful medium on the planet, needed by everyone. At NoFraud, everyone said “payments” and “fintech.” He said trust — the first question in any decision, in any context.

That reframe became the foundation for the rebrand to Wyllo and the acquisition thesis. If the core asset is trust intelligence — the ability to assess the legitimacy and intent of any customer interaction in real time — then fraud prevention is just one application. CX orchestration, return propensity, lifetime value prediction: all of it flows from the same graph.

The category you define determines the acquirers who eventually come for you. Scott is already thinking about that list.

150 Companies. One Deal. Here’s the Filter.

Before landing on Yofi, Scott talked to roughly 150 companies. His filters, in order:

1. Product acceleration. Does this get us somewhere we couldn’t reach in 18 months on our own? If it’s a prioritization problem — something we could build if we just focused — it’s not an acquisition candidate.

2. GTM fit — and not just the obvious layer. Most people check whether you’re selling to the same customer segment. Scott goes deeper: Are you selling to the same buyer? And even below that — are your pricing architectures compatible? A $99/month widget and a $10,000/month platform don’t cross-sell. The math doesn’t work and neither does the motion.

3. Philosophical alignment on where the market is going. Not just “we agree on the roadmap” — but do we share a fundamental belief about what this space becomes? With Yofi, the answer was yes on every dimension. They believed CX would become the most strategically underleveraged asset in commerce. So did Scott.

4. Can we fight well? The one most people skip. Scott didn’t want a team that nodded along. He wanted founders who would argue, push back, and tell him he was wrong. Marriages don’t fail because people fight — they fail because people stop.

Partner First. Acquire Second.

Before Yofi became an acquisition target, they were a go-to-market partner. Wyllo was bringing them into deals. They were winning together. Customers were asking questions that only made sense if the two products were eventually one product.

That partnership did three things before the LOI was ever signed:

• Proved there was real GTM overlap (not theory)

• Gave both teams a chance to stress-test the relationship under pressure

• Gave Scott a structural advantage when Yofi ran a competitive process

When the founders eventually had enough inbound interest to run a lightweight process, Wyllo wasn’t just another bidder — they had shared history, shared customers, and a shared vocabulary. That’s a moat no term sheet can fully replicate.

The Deal They Structured

Scott won’t share specifics, but the shape of the deal was: meaningful upfront multiple, performance-based earn-out, and a rollover equity component for the founding team. The rollover wasn’t symbolic — it was meaningful, because the Yofi founders genuinely believed in what Wyllo was building. They weren’t taking chips off the table. They were buying into the next chapter.

The earn-out piece was the hardest part to align on. An earn-out is a leap of faith — it only works if the acquirer doesn’t shift priorities in a way that locks out the founders. Scott’s answer to that wasn’t contractual. It was transparency: clear role definitions upfront, honest conversations about what was fluid, and a track record of saying what he meant.

“You can’t bullshit people in this process. You spend too much time together. It comes out.”

Why the Rebrand Had to Wait

Scott wanted to rename the company from day one. He waited three years.

His rule: the brand should be a promise. You can’t make a promise you can’t keep yet. Until Yofi was integrated and the platform story was real, a rebrand would have been paint on a house that wasn’t finished.

Wyllo was chosen for specific reasons — a tree with deep roots, strong but flexible wood, healing properties, and a growth pattern that finds its way into unexpected places. It also represents an intentional departure from the clinical, fear-based branding that dominates the risk intelligence category. “Wyllo for the change makers” is a different posture than every competitor in the space.

The name change wasn’t the finish line. It was the starting gun.

The Buy Box for What Comes Next

Scott’s criteria for future acquisitions:

• Something that takes more than 18 months to build in-house

• Data-rich business with meaningful scale (he cited $5M+ revenue as a credibility threshold)

• Customer base that validates real product-market fit

• Ideally something that deepens the integration layer or expands the end-to-end risk and CX intelligence story

He’s specifically thinking about the complexity of connecting Wyllo’s platform across the fragmented e-commerce tool ecosystem. Whoever has figured out a better approach to the integration layer is on his shortlist.

Who Buys Wyllo for $1B+?

Scott’s honest answer: probably someone in the threat intelligence or CX consolidation space. Help desk platforms looking to add intelligence and orchestration capability. Payments networks like Mastercard or Visa as payment infrastructure fractures and they need to compete on value-add rather than rails. Or a PE firm with a thesis around building the e-commerce operating system from the ground up — in which case Wyllo might not be the acquired. It might be the acquirer.

Scott Gifis is CEO of Wyllo (formerly NoFraud), backed by PSG. Previously President & COO at Frame.io. LP at GTM Fund and Stage 2 Capital.

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The Forrester Frame

The Q1 2026 Forrester Commerce Services Wave dropped recently, and it’s a useful lens for this question. If you’re a scaled independent — Wpromote, Front Row, anyone with a serious commerce practice — you’re the kind of asset that could move a “strong performer” into “leader” territory overnight.

So we ran the wave through Clay and asked: which of these players has the strategic rationale and the balance sheet to actually write the check?

The verdict:

• ✅ Accenture — acquisitive, cash-rich, already paying $1B+ (see: Faculae)

• ✅ Tata Consultancy — $9B in cash, growing U.S. presence, commerce services is a gap

• ✅ Valtech — smaller war chest but actively consolidating

• 🤔 Omnicom, Publicis, WPP — maybes. WPP flips to yes if a PE sponsor comes in.

• ❌ Merkle, IBM, Capgemini, Infosys, EPAM — not happening

The dark horse call: Tata. BPO-first reputation, huge cash position, and teams actively scouting the U.S. market. A move into scaled commerce services would be a statement acquisition — and that’s exactly the kind of deal nobody sees coming.

Five Deals Worth Knowing from Q1

1. Front Row + Socium Media Charles Bank ran a clean buy-side process and found exactly what Front Row needed: scaled paid search, paid social, SEO, and shopping feeds capability to bolt onto their Amazon-first platform. ~50-person shop, NYC HQ. Textbook.

2. Podean + AdAdvance Travis, Mark, and the Commerce Canal crew continue to build. AdAdvance (Duluth, MN) brought proprietary tech built from scratch on top of Amazon — not fake-it tech — plus a customer base Podean needed. Permanent Equity was the seller. Mountaingate keeps running a clean, focused playbook.

3. OneMagnify + Optimal (carve-out) One Magnify, the AI-enabled B2B marketing and data agency backed by Crestview, carved out Optimal’s performance media and audience data business. They now have a scaled “always-on” paid media engine that feeds directly into their AI platform. Headcount is approaching 1,000. Bright Tower ran sell-side.

4. Shipyard → strategic investment in Fancy AI This is the most interesting structure of the quarter. Shipyard (Columbus, ~300 people) made a strategic investment — not an acquisition — in Fancy AI, an Austin-based GEO/AIO platform helping brands show up in LLM-driven search. Rick at Shipyard calls it a partner-first play: dip your toe in, prove the value to clients, then decide if you need to own it. Smart optionality. Could be more expensive in 18 months. Worth it.

5. Sol XC + Craft & Commerce Flew under the radar. Sol XC (Toronto) acquires Craft & Commerce, a fully remote paid media agency with a specialty in Amazon, Walmart, and Target retail media for CPG. Another Amazon-oriented deal. The cross-border angle is under appreciated.

Three Takeaways

1. Strategic buyers exist. It’s not if — it’s when. Accenture, Tata, and Valtech all have the money and the motivation.

2. Retail media is the hottest capability gap. Three of five deals this quarter were Amazon/retail-media oriented. This isn’t slowing down.

3. AI is in every deal. Whether it’s the stated strategy (OneMagnify), the product being acquired (Fancy AI), or the framing on the term sheet, AI-forward positioning is showing up consistently. It’s no longer a differentiator. It’s table stakes.

Ayelet is actively running a buy-side mandate — looking for a DTC performance shop and an Amazon agency, both in the $1–3M EBITDA range, U.S.-based. DM her on LinkedIn if you know a fit.

We’re also looking for the right podcast sponsors. If you’ve got a name in mind, reach out.

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

Resources & Links

• Clay AI – AI tool used for market analysis and potential acquisition insights

• Forester Commerce Services Wave – Market positioning report highlighted during the discussion

• Shipyard – Performance agency investing in Fancy AI

• Fancy AI – Generative engine optimization platform

• Front Row – Amazon-first e-commerce accelerator

• Socium – Performance marketing agency acquired by Front Row

• Podean – Amazon-focused agency expanding through acquisitions

• AdAdvance – Retail media agency acquired by Podion

• Optimal – Performance media company bought by One Magnify

• Craft and Commerce – Amazon and retail media agency acquired by Sol XC

Subscribe to In/Organic for weekly agency M&A coverage. New episodes every week.

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/
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/

Episode Highlights:

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

Connect with Yannick Lorenz on LinkedIn
https://www.linkedin.com/in/shadowyaya/

Key Topics

• 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

Timestamps

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

Resources & Links

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

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/
In/organic on YouTube: https:
https://www.linkedin.com/in/travis-johnson77/

Follow Podean on LinkedIn
https://www.linkedin.com/company/podean/

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

Connect with Tom Shipley
https://www.linkedin.com/in/t-shipley/

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

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

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

Connect with guest, Carrie Kerpen
https://www.linkedin.com/in/carriekerpen/

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

Connect with guest, Chloe Cotoulas
https://www.linkedin.com/in/chloe-cotoulas-92082861/

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

Episode References
Ad Age Deal Announcement
GE’s Opening Day Commercial by Giant Spoon

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 underscores the challenges CEOs encounter 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/

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)

In this episode of the Inorganic Podcast, co-hosts Ayelet Shipley and Christian Hassold welcome Brian Burt, founder & CEO of Canopy Management. In this episode, we discuss Brian’s entrepreneurial journey, with an emphasis on his principles for building the business and expanding through highly accretive tuck-in M&A transactions. Brian also shares the importance of cultural fit in successful integrations. He then discusses the challenges and opportunities presented by AI in the retail media space, emphasizing the need for omnichannel marketing strategies. The conversation underscores the importance of momentum in business and the role of performance-based incentives in sustaining an entrepreneurial spirit within acquired teams.

Takeaways

• Canopy Management has grown without external investment, focusing on mergers and acquisitions for expansion.

• The need for operational efficiency and scalability drove the first acquisition.

• Cultural fit and shared values are crucial in successful acquisitions.

• Integrating new teams requires clear communication and defined outcomes.

• Performance-based incentives help maintain entrepreneurial spirit in acquired teams.

• AI presents both a threat and an opportunity for the agency space.

• Omnichannel marketing is essential for modern e-commerce success.

• Building a strong personal brand aids in building an acquisition funnel

• Momentum in business is key to successful integration and growth.

Chapters
00:26 Brian Burt’s Background
02:38 Growing through M&A
12:31 Culture Fit and Founder Alignment
13:09 Integrating the First Acquisition
16:36 Defining and Executing Acquihires
20:45 Evolving the Playbook
23:46 Incentives Pods, and Integration Strategy
27:44 Scale Synergy and Sustainable Growth
31:28 Market Outlook: Retail Media Omnichannel and AI
37:14 Closing Thoughts and 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/
In/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featured

Connect with guest Brian Burt
https://www.linkedin.com/in/brianburt1/