A Weekly Show For Founders
The growth mistakes that cost founders the most and what to do instead.
Every week, one specific mistake founders make under pressure – premature sales hires, ICP chaos, U.S. market-entry assumptions, broken pipelines, compliance blind spots, broken down by someone who’s seen the pattern play out for real. No hustle bait. No tactics without context. Just what went wrong, and what works instead.
The Premise
"Seriously Don't Do That." - the story behind the show
If growth feels harder than it should… you're probably right.
Here’s the thing. Most founders don’t fail because they aren’t working hard enough. They fail because they pour money and effort into the wrong move at the wrong time, hiring a salesperson before the motion exists, chasing every buyer instead of the right one, treating a conference like a marketing expense instead of a pipeline event.
I’ve watched this pattern play out across healthcare, fintech, insurance – the regulated, complex markets where one wrong assumption gets expensive fast. So this show does one thing: each week, we take a single mistake, look honestly at why smart people keep making it, and walk through what to do instead.
I like to say I’m blunt, but hopefully not rude. This is the conversation I wish more founders had before they learned it the hard way.
Seriously, Don’t Do That
A book about the expensive lessons founders, operators, and leaders usually learn the hard way.
This show is for you if…
- You’re a Founder, Co-founder, or Revenue leader, and the growth still mostly runs through you.
- You sell into regulated, high-trust markets- healthcare, banking, financial services, insurance, where a wrong move is costly, and committees decide.
- You’re entering the U.S. market and it feels like a black box.
- You’re getting meetings but nothing’s converting, and you’re not sure if it’s the message, the targeting, or the process.
- You want a repeatable system your team can run, not more activity, and not an agency running a black box, you never understand.
If you just nodded at two or three of those – yeah, this is the show for you.
Fresh off the mic.
Seriously, Don't Build Your US Go-To-Market Around Spend
Chris Luiz is the CEO of Scout InsurTech, where he talks to hundreds of insurance technology companies a year and puts the very best in front of carriers, brokers, and executives across the industry.
Meet Your host
Dan Griffith
CEO, Greater Gain Group · Based in Greenville, SC.
So, the short version: undergrad in accounting, then law school – where I decided pretty quickly I didn’t want to be a lawyer. From there it was Fortune 50 sales at IBM, then years in startups, exits, and helping growth-stage companies build sales and marketing engines that actually scale.
These days I help founder-led B2B software companies – mostly in healthcare, fintech, and insurance – make the jump from “the founder closes every deal” to a repeatable process the team can run. U.S. market entry is a big part of it. So is telling people, kindly, when they’re about to do something that’s going to cost them.
That’s really what this show is. The stuff I’d tell you over coffee before you spend six figures learning it yourself.
What you'll actually walk away with
One mistake, fully unpacked.
Every episode picks a single, specific failure pattern – not a vague topic – and shows you exactly how it happens and how to avoid it.
The "do this instead".
No problem without a fix.
You leave each episode with a concrete next move, not just a warning.
Pattern recognition you can borrow.
Real founder situations from regulated, complex markets – so you can spot the trap before you’re standing in it.
GREATER GAIN GROUP
The Work Behind the Conversations
Dan Griffith is the CEO of Greater Gain Group, where he helps companies turn growth challenges into practical, repeatable systems. The same lessons, mistakes, and operating realities explored on Seriously Don’t Do That are grounded in the work he does with leadership teams every day.
Our Sponsor
Be a guest!
Got a "Seriously Don't
Do That" story?
The best episodes come from founders and operators who’ve lived it – made the expensive mistake, learned from it, and can help someone else skip the lesson. If that’s you, I’d love to have you on.
It’s a relaxed, recorded conversation – no prep marathon, no gotchas. You bring one real mistake and what you’d do differently; I’ll handle the rest. We’ll send a short worksheet beforehand so the episode is sharp and your time isn’t wasted.
- ~30–45 minute recorded conversation, remote (we use StreamYard – link sent ahead of time)
- A short guest worksheet to align on your angle and key takeaways
- You review your quotes before anything publishes
- Clips and promo assets you can reshare
Want Dan on your podcast?
If you host a show for founders, operators, or anyone selling into healthcare, fintech, insurance, or other regulated markets, I’d love to come on. I bring blunt, practical takes on go-to-market, founder-led sales, U.S. market entry, and the expensive mistakes I help companies avoid. No fluff, no rehearsed talking points. Just a real conversation your audience can actually use.
- Moving from founder-led selling to a repeatable, team-run revenue engine
- Why most founders hire salespeople too early and what to build first
- U.S. market entry for international founders (the black-box problem)
- Selling into regulated, committee-driven buyers where trust is the whole game
- Turning conferences and LinkedIn into real pipeline, not just activity
