Fractional CPO/CGO | Built $200M revenue engines at TripAdvisor and EverQuote | Now advising B2C & marketplace platforms

I have started at nine or ten companies now. The first week pattern is always the same. The client shows you everything they're proud of. You make a mental list of what they didn't show you. Then you go find those. The entry mode that works isn't the one where you arrive with answers.
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Quoted in PhocusWire today on agentic commerce and the trust gap in AI booking.
Travel brands that lead with the technology story will miss the point. The trust problem in agentic transactions is not a payments problem. It is a consumer psychology problem.

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Agentic search doesn't route traffic to comparison marketplaces. It replaces them.

Chegg: 956K searches/mo Apr 2022. Perplexity: 1. They crossed in March 2025.

Five-year data study across edtech, automotive, and solar: buff.ly/4W62yk4
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Cost per lead is the most seductive vanity metric in growth. 300 leads at $15 CPL with 2% conversion costs $750/customer. 50 leads at $80 CPL with 18% conversion costs $444. The cheaper channel is 70% more expensive. Build from the originated customer back.
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In financial products, the most overlooked growth channel isn't a channel. It's sitting in a competitor's rejection file. At EverQuote, the customers carriers declined were still in market. They weren't lost. They were motivated buyers with nowhere else to go.
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Meta cut 15,000 people and called it an AI-native transformation. The actual story: they built an org to win a bet that didn't land and held the headcount longer than the strategy required. AI is the narrative that makes the correction palatable.
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Instacart just became Aldi's entire digital commerce platform. They stopped owning the customer and started selling infrastructure. 380+ retailers on Storefront Pro. Many marketplace teams debate this exact move for years. Instacart chose the layer most marketplaces miss.
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The most expensive word in product strategy is "also." A founder turned down a nine-figure vertical because it made the company feel small. That is not a strategy problem. That is a fear problem. Specialization is a weapon most founders refuse to use.
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Every company I walk into has someone who costs too much, does too little, and reports to someone who will never fire them. The protected person is never the real problem. The signal their protection sends is.
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I've argued high traffic acquisition spend for years. Finally did the math.

5 marketplaces. 5 years of SEC filings. High S&M spend doesn't predict growth. Angi: $4.6B on marketing, revenue down 41%. DoorDash: cut S&M ratio in half, orders tripled.

matthewmamet.com/blog/paid-acquisition-trap
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Revenue per user went from $3 to $17 at a large edtech company in 18 months. The leader asked one question first: "Match the pace or set the pace?" 95% said set it. She launched five products and shifted to platform selling. Ask before you push.
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Having to use ChatGPT because Claude is down yet again.
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A client's "content affiliates" are actually SEM lead-gen operations bidding against the company on its own keywords. Saw the exact pattern at EverQuote. SEM affiliates sell you back your own customers. SEO affiliates build trust. Know which you have.
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A strategy only exists when it excludes something.

"We serve enterprise and SMB across North America with a best-in-class experience" is not a strategy. It is a market with adjectives. Any competitor could sign that document.

matthewmamet.com/blog/product-strategy/
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Solar takes 12 weeks to close. $40K and analysis paralysis. The instinct is to optimize the funnel. Wrong problem. Look at what Airbnb did - they built a guarantee that absorbed risk for both sides. Build the trust infrastructure first. The conversion follows.
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An anti-pattern I see is when product leaders product leaders walk in trying to prove they’re the smartest. With a client I’m starting with now, I’m doing the opposite. Rolling over and showing my belly. Learned this at Pearson. Trust isn’t earned by being right. It’s earned by being useful first.
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A DTC healthcare startup I advise asked how to fix their culture. I told them to stop trying. The canvas is already painted. The better move: bloom where you’re planted. Accept the tempo and do your best work inside the constraints. You don’t have to love the water. Just learn to swim in it.
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🚀 Biggest unlock in my workflow?

AI isn’t replacing me - it’s amplifying what I’m already good at.

🤖 ChatGPT drafts strategy docs ✍️
⏳ Automation buys back HOURS
🗂️ Cleaner outputs

AI doesn't make you sharper. It lets sharp people move faster.

buff.ly/Per64Uf
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"Coming together is a beginning. Keeping together is progress. Working together is success." - Henry Ford
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Founders, listen up 👂 No hack replaces strong product leaders.

You can command & control, layer in process, hand it to “proxies” - but you’ll just end up with zombie teams 🧟‍♂️🌪️

Invest in real leadership or watch your best people walk. 🚪✨

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The best pros I know have coaches.
Not because they’re “broken" - but because seeing yourself clearly is a cheat code 🤯.

Game change = awareness 🚀

You’d hire a trainer at the gym…

Why go solo when it comes to your growth? 🏋️‍♂️💡

buff.ly/ybB4aNd
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Global search volume for "Please unblock challenges.cloudflare.com to proceed." spiking.

😆
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Most founders wait for funding before launching. 🚫💸

Flip it: Get scrappy, talk to customers now, ship the value fast. 🏃‍♂️⚡

Constraints force clarity.

Revenue > round.

Your startup can start TODAY - permission not required.🔥🛠️

buff.ly/dvL9UIl
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Most teams start their experimentation journey with tools-not people or process. Andy Boyd and I dig into what happens when you flip that order: how to build the systems, incentives, and mindset that make experimentation a habit, not a project.

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"Stay away from those people who try to disparage your ambitions. Small minds will always do that, but great minds will giv eyou a feeling that you can become great too." - Mark Twain
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Ever notice it’s way cheaper to buy an AC than to fix one? 😲

Tech makes stuff cheap (thanks, Jevons 📉), but labor still isn't getting automated (hello, Baumol 💰).

The weirder our tech gets, the pricier human work becomes. 🤖➡️👷‍♂️🔥

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Want more resources from your execs? 🤝🔑

Don’t just “manage up.”
Match their intensity.
Make their top goals your goals.

Resources flow to people leaders trust - and who help them win.📈🚀

Be that person. Your future self will thank you. 🙏🧠

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Everyone blames busted deadlines on “engineering.” 😑
But 9/10 it’s messy people stuff: unclear decisions, buried objections, silent tension. 🔄🧩

Tech solves fast. Teams align slow.

Want things to finally launch? Less JIRA tweaking - more real talk up front. ⚡🤝

buff.ly/2gSxdOF
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