Seriously Don't Do That

Send us Fan Mail Every InsurTech founder says "our AI is best in class." Every carrier on the other side of the table has heard it twelve times this month. So Dan Griffith and Chris Luiz stopped guessing what the buyer thinks. They went and got one. Innovator X is a senior insurance executive at an unnamed carrier. His face is blurred. His voice is altered. His answers are completely unf...

Send us Fan Mail In this episode of Seriously Don’t Do That, Dan Griffith sits down with David Borinstein to talk about what American companies, U.S. scale-ups, SaaS founders, technology companies, and growth-stage businesses often get wrong when they decide to “go to Europe.” Usually, this show runs in one direction. A European founder sits down with Dan, and the conversation is about why the Uni...

Send us Fan Mail In this webinar recording, Greater Gain Group and the InsurTech Association discuss how insurance, insurtech, and B2B teams can book better meetings before showing up at a major industry event. Hosted by Josh Hollander from the InsurTech Association, with Dan Griffith from Greater Gain Group as co-host, this session focuses on one of the most important parts of event strategy: Do...

Send us Fan Mail A sales forecast built on activity is not a forecast. It is a story your CRM is making look like math. In this episode of Seriously, Don’t Do That, Dan Griffith breaks down why healthy-looking pipeline can collapse under inspection, especially when the forecast is built on default close dates, rep-entered activity, vague stage definitions, and buyer movement nobody has actually ve...

Send us Fan Mail Great sales meetings do not automatically turn into revenue. In this episode of Seriously, Don’t Do That, Dan Griffith breaks down one of the most common reasons B2B sales deals, enterprise sales opportunities, SaaS sales conversations, and complex buying processes quietly die: The gap between meetings. A founder or sales leader can walk out of a meeting feeling like everything we...

Send us Fan Mail A conference isn’t a lead source. And treating it like one is one of the most expensive beliefs a founder can carry into fall event season. In this episode of Seriously, Don’t Do That, Dan Griffith breaks down why so many companies spend tens of thousands of dollars on conferences, booths, travel, badge scans, dinners, and team time, only to come home with a spreadsheet of names a...

Send us Fan Mail Entering the U.S. market with a bigger budget doesn’t mean you’re entering it the right way. Dan Griffith sits down with Chris Luiz, founder of Scout InsurTech, to break down one of the biggest mistakes international founders make when entering the U.S. insurance market: trying to buy their way into credibility. They discuss why conference booths and badge scans rarely equal pipel...

Send us Fan Mail Your product can look great and still be sitting on terrible plumbing. Dan Griffith sits down with Tom Sas, a cloud infrastructure architect with more than 20 years of experience, to explain what he calls the Golden Toilet Rule and why founders should stop treating cloud infrastructure as something that simply “runs in the background.” Tom breaks down a common trap: software devel...

Send us Fan Mail Four hundred outbound messages. Eleven replies. Three of them were "no thanks." A founder forwarded me the whole batch a couple of weeks ago and asked me one question: "Dan - is LinkedIn dead, or is it us?" Here's what I told him. It's neither. It's the thing sitting underneath both. So Thursday morning I'm going live on Seriously Don't...

Send us Fan Mail A health tech founder gets on a call with Dan last year. Good product. Real customers. Clinical workflow tool. About 90 seconds in, he says: "Dan, we've spent about $80,000 on outbound in the last year, and I have nothing to show for it." Three agencies. Three. First one: six months, $12,000 a month. Booked meetings - but with office managers when he needed the comp...

So, most founders think Latin America is one market with one playbook. It's not. And the part that surprises people most? The first move isn't picking a country — it's picking a channel strategy. In this episode, Dan sits down with Franklin J. Perez — 25+ years of commercial leadership across LATAM and the Caribbean at Medtronic, Edwards Lifesciences, and Abbott — to unpack what com...

In this tactical episode of Seriously Don't Do That™ — Week 3 of the 12-week SDDT program and Episode 3 of the ICP Sprint month — Dan Griffith breaks down the single most common (and most expensive) mistake founders make in regulated B2B sales: single-threading a deal through one champion when 22 people decide. Using research from Forrester, Gartner, HBR, HIMSS, 6sense, and Prospeo, Dan refra...

Dan just got back from training for a sprint triathlon and realized something uncomfortable - he's not the athlete he thinks he is anymore. The video doesn't lie. The times don't lie. And that gap between who you think you are and who you actually are right now? That's the entire episode. Last week was about founders with no ICP, just a fuzzy guess. This week is harder. These a...

Welcome to Week 1 of a brand new 12-week run of Seriously Don't Do That™. We're opening with ICP Month - four episodes on your ideal customer, why they buy, and the choices you have to make to actually grow. This is the episode Dan probably should have recorded a long time ago, because it covers the single most expensive mistake he sees founders make in regulated B2B markets. The Don&apo...

A seasoned British sales leader walks into his first U.S. meeting. No deck. No slides. Just ready to have a conversation. The buyer’s response?  “Where’s your deck? You came unprepared.” In this episode of Seriously Don’t Do That, Dan Griffith sits down with Todd Jenkins, VP of Revenue at Codility, to break down what EMEA founders consistently get wrong about the U.S. market and what it actually t...

Founders entering the U.S. often do everything “right”, strong product, great meetings, smart people and still go nowhere. In this episode of Seriously Don’t Do That™, Dan Griffith sits down with Geir Arnhoff, founder of Dossier, to break down what actually went wrong in his first U.S. expansion attempt and what finally unlocked traction. We cover: Why selling to the “logical buyer” often fails in...

Entering the U.S. market isn’t just a sales problem. It’s an operational one. In this episode of Seriously Don’t Do That, Dan Griffith sits down with Sims Tullos of Amesto Global to break down the back-office mistakes that quietly derail U.S. expansion. We cover: • Why “we’ll fix ops later” becomes expensive fast • Entity setup, payroll, banking, tax, and compliance traps founders miss • The hidde...

Entering the U.S. market is not a spending problem — it’s a sequencing problem. Every year, European SaaS and healthtech founders burn six figures on activities that feel productive but don’t create pipeline: • Conference booths before ICP clarity • PR campaigns without localized messaging • Lead-gen vendors before a sales process exists • Hiring U.S. reps before the system is built In this sessio...

Most founders walk into trade shows hoping for visibility and walk out with nothing more than badge scans, swag bags, and zero pipeline. The issue isn’t the booth. It’s the missing system behind it. In this 45-minute session, I and Benjamin Griffith (Co-Founder, Grow DGTAL) break down the exact Trade Show Framework they use to turn chaotic conference floors into structured sales campaigns. You’ll...

Most founders don’t lose U.S. deals because of their product… they lose because they pitch to the wrong person. And that’s exactly what we’re breaking down live this week. If you're building or selling in healthtech and you still assume the clinician is the buyer… you’re already behind. Because the people who love your product? They’re rarely the people who sign the contract. This session is...

You’ve raised capital and your board wants traction in the US market. The gut reaction? Hire a top-notch VP of Sales immediately. But what if that move actually slows you down? In this practical 30-minute live event, Dan Griffith will unpack why hiring your sales leaders before setting up the right foundation leads to empty pipelines and frustrated teams. Based on real stories from the field, Dan...

Most founders don’t lose U.S. deals because of their product… they lose because they pitch to the wrong person. And that’s exactly what we’re breaking down live this week. If you're building or selling in healthtech and you still assume the clinician is the buyer… you’re already behind. Because the people who love your product? They’re rarely the people who sign the contract. This session is...

Join me on Thursday, October 16th at 9AM EDT for a 30-minute live session where we strip back the buzz and get real about what makes a growth pipeline trustworthy or doomed to fail. Founders too often spend big on branding, sales hiring, and outbound tools while missing the most crucial piece: a solid, agreed-upon definition of what counts as a qualified opportunity. The result? A “pipeline” that...

Spend 5 figures on slick fonts, fancy decks, and noisy agencies or spend that same $$$ to own your Go-to-Market engine? If your GTM strategy feels rented, you’re not alone and it’s time to change that. No marketing fluff. Just clear steps to ditch rented growth and start owning your future. Ready to stop paying for noise and start building momentum? #GTM #FounderWisdom #SalesStrategy #PipelineGrow...

An exclusive 30-minute session tailored for founders and sales leaders struggling with the costly hire-fire cycles in outbound sales. In "Seriously, Don't Hire a BDR in 2026," we dive deep into why traditional BDR models are failing startups operating in tightly regulated markets such as healthcare, fintech, and insurance. You’ll discover: The impact of cold outreach’s diminishing r...