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In/Organic Podcast
E59: A Mystery Strategic Buyer Is Coming for Independents, Brkthru's x Gigawatt & Instacart Deal
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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E61: BREAKING: Accenture's Next M&A Imminent, Recharge x Skio for $105M & IREN x Mirantis for $625M
17:32|We've been saying one of the big strategics was going to move on a scaled independent agency. It's happening.Christian and Ayelet are back for Deal Review Friday with breaking news on an imminent Accenture acquisition, two lower middle market deals that tell you exactly what the current M&A environment looks like, and what all of this means for the scaled independents that were planning to go to market in 2027 or 2028.The dam is breaking. Here's what you need to know.⏱️ TIMESTAMPS0:00 — Cinco de Mayo, Salsify's Digital Shelf Summit, and puppies1:53 — 🚨 Breaking news: Accenture is imminently closing a ~$500M US agency acquisition2:27 — The backstory: E52's Clay analysis and Accenture's $3B AI deployment plan3:15 — What we know, what we're not saying yet, and why this is step two of a multi-step plan4:43 — Why this deal will push Tata and others to move faster5:30 — The forcing function effect: scaled independents planning 2027-28 exits may move sooner5:56 — Why bilateral deal making is rising and what Accenture's move does to auction dynamics6:45 — Deal #1: Recharge acquires Skio — $105M cash, 3.3x ARR, direct competitor consolidation8:08 — What this multiple tells you about SaaS M&A right now8:35 — The COO announced the price on X — and why that's hilarious9:17 — Shopify ecosystem turbulence and what it means for this deal10:14 — Capital efficiency: Skio raised $4-8M and sold for $105M11:05 — Deal #2: IREN acquires Mirantis — $625M all-stock, AI infrastructure play11:30 — What Mirantis actually does and why NVIDIA is at the center of this13:27 — The NVIDIA deal sequence: founding partner in March, $3.4B contract, $2.1B investment14:30 — Why the timing of these events tells the real M&A story15:44 — 27 years to a $625M exit — what the AI era does for legacy infrastructure companies16:04 — Wrap: ep 60 with Brenda Jacobsen dropped, Salsify content coming🔔 Live every Friday — subscribe so you don't miss the big announcement💬 Drop your guesses on the mystery buyer in the commentsConnect with Christian and AyeletAyelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/Christian's LinkedIn: https://www.linkedin.com/in/hassold/
E60: The M&A Truths No One Tells Founders | Advice from an Operator w/Brenda Jacobsen
50:03|What does it really take to sell your business — and are you actually ready?In this episode of the InOrganic Podcast, we sit down with Brenda Jacobsen, Managing Director at STS Capital Partners, a sell-side M&A advisory firm focused on helping founders and operators find the right strategic buyer — not just the highest bidder. What makes Brenda unique? She's not a banker by training. She's a former operator who built and sold three companies herself, including a regional network of medical clinics and a corporate mindfulness media company. She's been on your side of the table.Brenda walks us through the full arc of what it means to navigate a business exit — from the first internal conversation with your co-founders, to closing day, and everything in between.In this episode, we cover:🧠 Why most partner misalignments happen before you ever talk to a banker📋 The "Owner's Outcome Exercise" — a simple framework to get founders aligned on what success actually looks like⏰ When to start having exit conversations (hint: it's earlier than you think)📉 How to read the hidden clauses in your equity docs that could cost you control of your exit💰 Current M&A valuation ranges for digital marketing agencies (3–6x EBITDA) and what moves the needle🤖 Why you need to stop "BS-ing your AI story" — and what buyers actually want to see🏥 A fascinating case study on data ownership in outsourced radiology and why it changed the deal conversation entirely👻 How phantom equity can keep your key operators invested all the way through close❤️ The emotional side of selling — and how the right sell-side advisor acts less like a banker and more like a witnessWhether you're planning to sell in 12 months or 12 years, this conversation is packed with practical, honest advice from someone who has lived both sides of the deal table.Connect with Christian and AyeletAyelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/Christian's LinkedIn: https://www.linkedin.com/in/hassold/Web: https://www.inorganicpodcast.co🎙️ Guest: Brenda Jacobsen, Managing Director, STS Capital Partners🌐 Learn more about STS Capital: www.stscapital.com📌 Subscribe to the InOrganic Podcast for weekly conversations on M&A, growth, and building businesses worth buying.#MergersAndAcquisitions #BusinessExit #Entrepreneurship #SellYourBusiness #PrivateEquity #MiddleMarket #MAStrategy #BusinessGrowth #Founders #InOrganicPodcast
E58: AI Commerce is Coming, SaaS Moats, and Startup Survival with Scot Wingo
42:23|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.Chapters00:00 Intro from Shoptalk00:45 Meet Scot Wingo02:00 From ChannelAdvisor to ReFiBuy04:00 Why public-company life was not the right fit06:00 Investing in the North Carolina startup ecosystem09:00 What ReFiBuy is building12:00 Agentic commerce and the next marketplace shift16:00 Why content and thought leadership still matter20:00 Learning from customers and following the thread24:00 Startup survival in a tougher funding market28:00 Why SaaS go-to-market is breaking32:00 Defensibility and moats in the AI era37:00 Proprietary data and workflow depth42:00 M&A options for early-stage startups47:00 Mergers, acquihires, and strategic exits52:00 AI valuations and changing SaaS multiples56:00 Scot’s predictions for agentic commerce01:00:00 Final thoughtsSubscribe 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 AyeletAyelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/Christian's LinkedIn: https://www.linkedin.com/in/hassold/Web: https://www.inorganicpodcast.coConnect with Scot Wingohttps://www.linkedin.com/in/thescotwingo/Learn More about Refibuyhttps://www.linkedin.com/company/refibuy/
E57: Deal Review: Amex x Hyper, Viant x TVision, The Real Story Behind "Declining" Ad Tech M&A
17:49|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.⏱️ TIMESTAMPS0:00 — 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 category3:45 — Ad tech, martech, digital content — what's actually moving and what's not5:00 — The sub-$50M thesis: where Christian and Ayelet think the real action is6:10 — Deal #1: Amex acquires Hyper (HyperCard) — agentic AI expense management7:17 — The Hyper investor roster: Sam Altman, former MasterCard CEO, Netflix co-founder8:00 — How this fits Amex's expense management platform launch later this year9:00 — Center (2025) gave them the workflow. Hyper gives them the AI agent layer.9:45 — Amex's direct play on Concur, Ramp, and Brex10:10 — Was this an acqui-hire? Christian's take on the deal structure10:44 — Deal #2: Viant acquires TVision Insights for $40M12:00 — The trifecta: Iris TV (content) + Locker (identity) + TVision (attention)13:18 — The data exclusivity question — and why this deal is different from Iris TV13:58 — Props to Eric Stearns, Viant Head of Corp Dev — first deal in seat14:22 — Deal economics: 4x revenue, $22.5M cash, clean balance sheet15:36 — TVision raised at $80M valuation, sold for $40M — the cap table math16:00 — 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 commentsConnect with Christian and AyeletAyelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/Christian's LinkedIn: https://www.linkedin.com/in/hassold/Web: https://www.inorganicpodcast.co
E55: 3 Strategic M&A Deals: Harvest + Cartograph, Enginr + Nuqleous, and Carry’s $80M Exit
20:26|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.)⏱️ TIMESTAMPS0:00 — LinkedIn buffering, as usual0:48 — Market signal: strategic LOIs up 40% YoY per Spearhead Corp Dev1:30 — PE deal volume Q1: $216B, up from $190B — but strategics are the real story2:46 — Deal #1: Harvest Group (Mountain Gate) acquires Cartograph — 35 days after platform close5:35 — Cartograph's superpower: scaling challenger brands on Amazon6:44 — Full disclosure: Mountain Gate is not sponsoring this podcast7:13 — Who advised? Chris Moe peels back the layers8:30 — Deal #2: Engine + Nuqleous merge to form end-to-end retail intelligence platform12:18 — CPG point solution fragmentation and why this merger was inevitable13:26 — Nick Dossier: repeat offender, same playbook, larger scale14:00 — Crisp lit up this category — and Engine is now the OG competitor16:24 — Engine's full acquisition history: Evertech, Leftbridge, now Nuqleous17:18 — Deal #3: Cary sells for $80M on $900K ARR — AngelList + Lettuce split the asset19:00 — 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 commentsConnect with Christian and AyeletAyelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/Christian's LinkedIn: https://www.linkedin.com/in/hassold/Web: https://www.inorganicpodcast.cohttps://www.youtube.com/@InorganicPodcast
E54: Deal Review: Podean's 3rd Acquisition, Mountaingate's 4th Platform Play & MiQ Goes Mobile
14:26|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.TIMESTAMPS0:00 — Introducing Deal Review Fridays: why we're going live1:30 — Market signal: private debt compression and its downstream M&A impact4:11 — Ayelet on the ground: deals still closing sub-$50M EV4:54 — Deal #1: Podean adds AdMerge (UK) — third add-on, ~$30-35M revenue run rate7:37 — Deal #2: Mountain Gate platforms Upswell Marketing — Fund 3, fourth investment9:34 — Mountain Gate's portfolio thesis: multiple distinct platforms in parallel vertical lanes10:41 — Deal #3: MIQ acquires Rocket Lab — mobile gap fill + LATAM programmatic stack13:35 — 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 commentsConnect with Christian and AyeletAyelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/Christian's LinkedIn: https://www.linkedin.com/in/hassold/Web: https://www.inorganicpodcast.cohttps://www.youtube.com/@InorganicPodcast
E56: AI Agents Are Coming for Agencies: EverWorker’s $10M Bet
10:34|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 competitiveChapter Markers00:00 Intro from Shoptalk00:39 Meet Ameya from EverWorker01:00 What EverWorker does01:29 Why DIY AI agents are not enough02:55 The problem with maintaining agents04:26 Making AI workers easier to manage05:31 EverWorker’s funding and company stage06:09 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 workers09:06 Why agencies need to become AI-first10:09 Final thoughtsIf 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 AyeletAyelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/Christian's LinkedIn: https://www.linkedin.com/in/hassold/Web: https://www.inorganicpodcast.cohttps://www.youtube.com/@InorganicPodcastConnect with Ameya Deshmukhhttps://www.linkedin.com/in/ameyadeshmukh10/Learn more about EverWorkerhttps://everworker.aiSubscribe to In/organic for conversations on SaaS M&A, agency M&A, AI disruption, strategic acquisitions, and lower-middle-market dealmaking.
E53: From No Fraud to Wyllo: A $1.3B Exit Vet on Tuck-In M&A & the Future of Risk Intelligence
46:21|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?)⏱️ TIMESTAMPS1:11 — 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 partnership31:58 — 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 shortlist45:50 — Wrap-up and close🔔 Subscribe for weekly agency and SaaS M&A coverage📍 Recorded live at ShopTalk, Las VegasConnect with Christian and AyeletAyelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/Christian's LinkedIn: https://www.linkedin.com/in/hassold/Web: https://www.inorganicpodcast.coIn/organic on YouTube: https://www.youtube.com/@InorganicPodcast/featuredConnect with Scott Gifis on LinkedInhttps://www.linkedin.com/in/scottpgifis/Learn more about Wyllo: https://wyllo.ai/