Kerry Anne Hoffman

Substack publication 'The Free Press,' a blog started in 2022, has grown to around 15M a year in revenue, and is now in talks to be acquired by Paramount for $200M (and founder Bari Weiss given an exec role at CBS News). I've predicted blogging is back for several years - thanks mostly to email and the fact that Substack and Beehiiv got distribution right. It turns out independent media can thrive in an environment even when social platforms like this one, Meta and Twitter/X throttle our hyperlinks. I honestly think it's a loss for these products to not show them as often as they do. As many users here are simply less informed, less educated and stuck in algo-generated filter bubbles. Of course, this isn't everyone. The smartest internet users are looking to things like email where there's less algo interference. You hope the big tech platforms catch on and remember hyperlinks are important again, at some point this will be a liability for them jamming the plumbing of the web. Anyway - if you want to start a blog, it's never been a better time. We have so much validation all around us. You can even be well-compensated for your work this time. The internet is great if you play the right games.

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Just read this Crunchbase piece about the "second wave of layoffs" and... wow. Job searches are now averaging 6-7 months. Over a third of Americans have side gigs. Here's what gets me: We're watching the entire concept of "having a job" get turned inside out, yet we still expect people to figure out health insurance like it's 1995. Picture this: You get laid off. Your job search drags on for half a year. You pick up some contract work to pay bills. Cool, you're adapting, you're hustling... but wait, how do you keep your kid's asthma medication covered? The article talks about how "workers are blending traditional jobs with side gigs." Sure. But our benefits system? Still assumes you work somewhere for 30 years and retire with a gold watch. I keep thinking about all the talented people I know who are stuck in this impossible position - turn down contract work and keep searching for "real" jobs with benefits, or take the work and pray nobody gets sick. That's insane. That's not a choice anyone should face in 2025. The good news? This chaos is forcing innovation. Companies are learning to build lean, mean machines. Maybe it's time we build support systems that actually match how people work today. #ReadyForWhen #Layoffs #Benefits #HealthInsurance #Crunchbase Read more: https://hubs.ly/Q03PHbcW0

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DTC is not dead. It just grew up. Once upon a Shopify boom, pure DTC looked unstoppable. Then: 📉 CPMs spiked, iOS crushed targeting, and lookalike gummies flooded your feed. Now? The smartest brands are done chasing ROAS. They're using DTC as leverage, not the endgame. 🧪 Your .com isn’t the profit center. It’s the R&D lab Run micro-tests, experiment with bundles, pricing, and creative. Scale only what proves it can win. 📊 Retail buyers don’t care about branding mythos They care about SKU velocity heatmaps and LTV by ZIP code. Walk in with a dashboard, not a vibe. 🛒 Omnichannel does not mean being everywhere Real operators treat Amazon, TikTok Shop, Target and their own site as connected nodes. Inventory, loyalty, and pricing are fully synced. 🤝 Influencers are shifting to equity deals Welcome to influence-for-performance. If they don’t believe in your product long term, neither will their audience. 🤖 AI is now the operating layer From AOV optimization to creative generation to real-time CX agents, AI quietly powers the entire DTC engine room. The result? Brands that start DTC, but don’t stay DTC. They test, learn, and scale profitably across every channel. Being “DTC-smart” in 2025 means this: 💡 You don’t pick between marketplaces, retail or .com You make each one smarter with the learnings from the others. #ecommerce #dtc #marketplaces #retailstrategy #shopify #omnichannel #ai #brandbuilding #growthmarketing #channelmojo

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Most delivery chaos starts with one tiny word: “yes.” Yes to another priority. Yes to another meeting. Yes to another request no one scoped or budgeted for. One client brought me in when their team was burned out and nothing was moving. The first thing I did? Said no. → No to three overlapping workstreams → No to half the Jira board → No to the mindset that busy = valuable We halved their project load. Doubled their output. And the team finally breathed again. Here’s the truth: Being fractional means I’m not scared to push back. I don’t need to play internal politics. I’m here to get things done. That’s what my offer is built on, clarity, not compliance. So if your delivery roadmap looks like a wishlist, maybe it’s time someone challenged the map.

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Boring, basic marketing is what actually scales Shopify stores past $150k/month. Here’s what founders really need: - A creative that hits on real customer pain points. - A landing page that doesn’t confuse people and actually converts. - An offer that feels valuable enough to raise AOV. - A simple testing process to consistently find new winning ads. - A scaling structure that lets you spend $5k+ a day while keeping CAC in check. Most people get stuck because they skip the fundamentals. Instead, they chase shiny tactics—TikTok experiments, complicated funnels, weird manual bidding hacks—while their offer and creative still suck. Truth is: no platform change or cost control will fix weak messaging. If your offer isn’t strong, scaling just shows it to more people who don’t care. Customers only care about themselves. That’s why you need an offer they actually want and a creative that makes them act now. Yes, it sounds basic. That’s the point. Most founders think they’re “too advanced” for the fundamentals. That mindset is exactly what keeps them stuck. The basics are what drive results. Do them well—and everything else starts working.

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Products take years to launch. The best ones go live in 8 weeks.** Speed isn’t sloppy—it’s strategy. Here’s how to launch a product in 8 weeks: Step 1: Validate with a scrappy MVP. Launch before it’s perfect. 📌 Figma shipped its early version with bugs—users became co-creators. Step 2: Set a no-scope roadmap. Cut everything that’s not launch-critical. 📌 Basecamp’s “Shape Up” method ditched backlogs to ship faster. Step 3: Use content to build pre-launch buzz. Marketing starts at idea stage. 📌 Notion built hype by teasing features in Loom videos. Step 4: Launch soft to learn fast. Your real launch is version 2. 📌 Clubhouse invited power users first—then scaled from feedback. Step 5: Measure only what matters. Speed is useless without signal. 📌 A SaaS brand used retention rate as their only KPI post-launch. Slow launches kill momentum. Fast, focused launches build believers. P.S. What’s the fastest launch you’ve pulled off? #Leadership #Sales #Marketing

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In 2026, ABO is no longer the best way to test creatives. I didn’t want to believe it either. But after testing CBO since September across five different accounts, the data was very clear. CBO was ~27% more efficient on average. Here’s the CBO testing structure I’m running now: - Exclude all existing customers (Klaviyo + Pixel) - 100% Broad targeting - Set a minimum spend per ad set to force learning - Use Flexible Ads when I’m testing very similar creative variations What happens next is key 👇 Winners move into CBO Scaling Top performers also get pushed into Whitelisting & Partnership campaigns That said… I still see ABO outperform CBO in some accounts, especially smaller ones. So make sure to test both and see what works best for your account.

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Your acquisition team is bringing in customers. Your post-purchase flow is losing them. This is the problem I see in a lot of scaling DTC brands. Founders are pumping budget into Meta and Google. New customers are landing. The welcome flow converts. Revenue looks healthy. But three months later, those customers are gone. One order and out. So the brand spends more on acquisition to replace them. The treadmill speeds up. Margins get thinner. Growth feels harder than it should. They think they need better ads. Better targeting. Better creative. More top of funnel. But the real problem is what happens after the first purchase. The first 30 days of a customer's lifecycle will make or break the relationship. Here's what needs to happen before day 30 for a customer to come back: - They experience an actual result from your product - They gain certainty they made the right choice - They form a usage habit - They build belief in the outcome Hit one of these, and they'll probably return. Hit none, and that customer is gone. Let me break down how to engineer each one. 1. Engineering results Your job is to accelerate time-to-value. Set clear expectations on when they'll see or feel something. Day 3, day 7, day 14. Tell them what progress looks like. Most customers quit too early because nobody told them what to expect. Send usage content. How to apply it, when to take it, how much to use. Poor usage kills results and your product gets blamed for it. 2. Building certainty Every customer doubts their purchase. It's normal. Founder videos work incredibly well here. A short message addressing common concerns and explaining why you built the product this way. It's personal and builds trust fast. Show testimonials from customers with similar goals. Relevance matters more than volume. 3. Creating habits A customer who uses your product daily will reorder. A customer who uses it occasionally will forget you exist. Send reminders timed to usage. Morning supplement? Email at 7am during week one. Give them a framework. "Take with breakfast" beats "take daily." Specific cues attach to existing behaviours. Celebrate milestones. Day 7, day 14, day 21. Small acknowledgments reinforce the behaviour. 4. Building belief Customer stories are the most effective tool here. Not short reviews. Actual stories with context, struggle, and transformation. When a customer sees someone like them achieve what they want to achieve, belief follows. And belief turns customers into advocates with the highest LTV of any segment. Here's how to put it together: Map your first 30 days. Look at every email and ask which outcome it drives. If it's not driving any of them, cut it. Front-load the high-impact content. Days 1-7 are when engagement peaks and doubt is strongest. Personalise where you can. Someone focused on weight loss and someone focused on energy should not get identical sequences.

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We sat down with Crystal Carter, Head of SEO Comms at Wix, for an inside look at what’s winning as AI reshapes search. Organic traffic is down. CTR is slipping. But that doesn’t mean your content isn’t working. It just means the old playbook isn’t tracking the right signals. Lots of SEO teams still live in a CTR world. But LLMs like ChatGPT and Perplexity don’t care about clicks. They care about structure, citations, and semantic fit. Same keywords. Totally different results. Crystal nailed this shift: Bridge the gap by tracking both, like we’re seeing from top teams: → Tracking branded mentions + referral lift from tools like Perplexity → Tagging “ChatGPT” or “AI” in your ‘How did you hear about us?’ forms → Monitoring “Pages known to LLMs” This isn’t the death of SEO. It’s the expansion of it into places traditional analytics can’t reach. We can fight for fewer clicks or win by showing up where influence is happening. To earn citations in AI Overviews, content needs to look like a source, not just a blog post. That means structured data, schema, and unmistakable clarity. Crystal breaks it all down in this webinar: ✔️ The RAPP framework for LLM visibility ✔️ Schema markup that’s must-have ✔️ How to track AI influence without guesswork Full recording here: https://lnkd.in/gKCmCxCt

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Before we grew to over 70 customers, including Hims, Harness, and Gusto, I had to weather 100s of “no’s”. Each of them completely changed our product. There’s no amount of words I could use to describe how ridiculously hard the early days were. It was a total catch-22: We tried everything to land our first customer. We attended just about every industry event in SF and sent 100s of outbound messages just to get in front of key decision-makers. And when we finally got the occasional call booked on our calendar, I’d be freaking out, thinking, “Oh my god, I need to know everything about this person, like what sport did they play in high school?”. Still, it felt like over and over, the prospect’s answer was “no”. The problem we were solving was painfully obvious. Yet, it felt like getting even one legal department on board was nearly impossible. Analyzing it, we kept running into the same 3 issues. 1. We were problem experts but struggled to communicate how our product solved it. 2. GCs weren’t willing to stake their careers on an early-stage startup. 3. They needed a complete solution that connected with their existing stack. More than that, these integrations had to be high fidelity, built natively to ensure we can keep the tool plug-and-play, and lighten the load on customers’ IT departments. The breakthrough: Ultimately, we found someone just as innovative as we were, and willing to take a “chance” on us, if you want to call it that. Kudos to Ronak Ray, former GC of Pantheon, one of our first beta users, whose feedback helped us improve the product and build credibility with enterprise teams. Over time, we built the infrastructure to integrate seamlessly with CLMs, cloud storage, and the broader legal tech stack. That removed friction and turned the platform into a tailored solution that fits naturally into daily legal workflows. Takeaway: What started as a baby startup built from a (super) cramped office is now trusted by over 500 attorneys at some of the world’s leading tech and consumer enterprises. None of this would have been possible without absolute conviction. It’s what kept Julian Wimbush and I moving forward, even when it would’ve been easier to go back to the workforce. And of course, I’m eternally grateful to our early customers. Their belief in us laid the foundation for everything we’ve built. 🙌

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