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In this episode, Dan Griffith sits down for a conversation about Capital BPM, automation, founder growth, sales patience, and what it really takes to build trust with customers.

The discussion covers how automation can free teams from tedious work, why the best use of technology is not just saving time but creating capacity for higher-value work, and how companies can uncover hidden value inside their operations.

The conversation also moves into the founder side of growth:

How humility helps build a stronger executive team.
Why founders do not need to be the smartest person in every room.
Why different sales plays mature on different timelines.
How trust can be built through a fixed-outcome SOW.
Why automation should create real operating value, not just sound impressive.

A key theme throughout the episode is practical growth.

Not hype.

Not vague transformation.

Not automation for the sake of automation.

Real process improvement.
Real customer trust.
Real business outcomes.
Real leadership lessons.

If you are a founder, operator, executive, consultant, or business leader thinking about automation, team building, sales trust, business process improvement, or scaling a company more intelligently, this episode is worth watching.

Topics covered:

▪️ What Capital BPM actually does
▪️ How automation frees teams from low-value work
▪️ Why tedious work blocks higher-value opportunities
▪️ How humility helps founders build stronger teams
▪️ Why results take time and multiple plays matter
▪️ How a fixed-outcome SOW can reduce buyer risk
▪️ Why trust has to become more than words
▪️ How to think about opportunity cost and “opportunity opportunity”
▪️ Why founders need patience, systems, and the right people around them

Watch the full conversation for a practical look at automation, leadership, and building trust in business.

#Automation #BusinessProcess #FounderAdvice #B2BSales #BusinessGrowth

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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 unfiltered.

In this GGG × Scout InsurTech episode, Dan and Chris interrogate Innovator X on everything InsurTech founders need to hear — and almost never do.

What's in the episode:

▪ Why "I sell to carriers" contains practically zero information — and what to say instead
▪ The AI litmus test: if you took the word AI off your homepage, would the buyer know what problem you solve?
▪ What actually lands on a carrier executive's desk vs. what gets auto-deleted
▪ The golden sales proposition: does your AI make them more profitable or help them write more premiums? If neither — it's a science project
▪ How to get your first carrier logo when you have no references — the co-build, the POC, and what "tighter relationship" actually means from the buyer's side
▪ Inside a top-ten carrier: how many people, how many committees, and the AI review trigger that adds months nobody warns you about
▪ Innovator X's conference truth bomb: "My calendar has been booked for six months. We send our junior people to the floor."
▪ Why the 24-48 hours after a conference is everything — and the follow-up mistake that wastes your entire spend

Timed for release the week before ITC Vegas 2026. On purpose.

Featuring:
Dan Griffith — Founder & CEO, Greater Gain Group
Chris Luiz — Co-Founder & CEO, Scout InsurTech
Innovator X — Anonymous Senior Insurance Executive (identity classified)

🤝 Work with Greater Gain Group: https://calendly.com/greatergaingroup/q1-revenue-pressure-test
🌐 Scout InsurTech: https://www.scoutinsurtech.com
🎙️ Seriously Don't Do That™: https://seriouslydontdothat.com

Chris Luiz on LinkedIn: https://www.linkedin.com/in/christopher-luiz
Dan Griffith on LinkedIn: https://www.linkedin.com/in/dangriffithsr/

Chapters:
00:00 — Welcome + why we did this
01:30 — "I sell to carriers" — why that statement is meaningless
03:45 — The AI litmus test: take the word off your homepage
07:00 — Innovator X enters the room
08:30 — What actually lands on a carrier exec's desk
10:15 — How to get your first logo with no references
13:00 — The golden sales proposition: profit or premium
16:00 — Inside a top-ten carrier: how many people say yes before you get a yes
22:00 — The conference truth: "my calendar's been booked for six months"
26:00 — The 24-48 hour follow-up rule
28:00 — Dan's five-point close + Chris's credibility take

(Note: confirm chapter times against the final edit before publishing)

#InsurTech #AI #InnovatorX #ITCVegas #GreaterGainGroup #ScoutInsurTech #CarrierSales #InsuranceInnovation #B2BSales #FounderLedSales

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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 United States is not one simple market. It is a hundred markets wearing a trench coat. Different buyers, different states, different sales motions, different procurement habits, different legal exposure, and a very different commercial pace.

This week, the conversation runs in reverse.

David Borinstein is a California native who spent a decade in San Francisco commercial real estate, making 50 cold calls a day and building a business that could run over the phone and online.





When a U.S. company decides to “go to Europe,” what do they usually get wrong on day one?

David’s answer starts before day one.

Because many companies misunderstand what Europe actually is as a market.

Entering France is a project.
Entering Germany is a project.
Entering Belgium is a project.
Entering Brussels, Flanders, and Wallonia may each become its own project.


For American founders, SaaS companies, fintech companies, healthtech companies, legaltech companies, enterprise sales teams, and business development leaders, this matters.

Because the mistake is not only commercial.

It can be legal, operational, cultural, and strategic.

One of the biggest points in this conversation is that a U.S. company may already have European exposure before it officially “enters Europe.”

If you hold EU customer data, process European user information, work with European customers, sell into European accounts, or touch European personal data, you may already be dealing with European legal and regulatory obligations.

That changes the conversation.

Europe market entry is not only about hiring a salesperson, choosing a country, opening an office, or finding a few distributors.

It is about understanding the rules, the relationships, the regions, the buyer expectations, the calendar, and the dignity of the market you are entering.

David uses Belgium as the argument in miniature.

Belgium is a small country, but it has multiple regions, multiple trade agencies, multiple languages, and very specific local structures. Even within one country, you cannot always assume that one relationship, one agency, or one event gives you access to the entire market.

That is the point many U.S. companies miss.

They arrive with the posture that Europe should be grateful for the opportunity.

They assume U.S. speed will translate.

They assume capital creates access.

They assume a smaller country means a simpler buying process.

They assume if the product works in America, the market will adjust around it.

That is where things break.

In the episode, David shares a story about a major U.S. financial institution that came into Belgium with the attitude that a small country should be glad to work with them because they had money.



David also breaks down the European business calendar that many American founders are not prepared for.


What we cover:

▪️ Why “entering Europe” is not one project
▪️ Why each national and regional market needs its own strategy
▪️ Why U.S. companies may already be under European law before they officially enter Europe
▪️ How EU customer data can create exposure before a company has boots on the ground
▪️ Why Belgium is a perfect example of European complexity
▪️ How Brussels, Flanders, and Wallonia create different layers of business development
▪️ Why American confidence can become a liability in European market entry
▪️ What happens when U.S. companies assume money alone opens doors
▪️ Why July, August, and December matter more than U.S. founders expect
▪️ Why slower email response does not always mean lack of interest
▪️ How American companies should think about trust, dignity, patience, and local relationships
▪️ Where U.S. companies should spend money first if they only have one priority
▪️ Why local advisors, local context, and trusted people matter when expanding into Europe

David’s line that stuck with Dan:

“They may not make nearly as much money as you do, but they have a lot of dignity.”

That sentence is the whole episode.

It is the warning for every U.S. company trying to enter Europe with the wrong posture.




Watch the full conversation with Dan Griffith and David Borinstein on Seriously Don’t Do That.

🎙️ Seriously Don’t Do That
Hosted by Dan Griffith
Guest: David Borinstein
Firm: Liberius
Topic: U.S. companies entering Europe, European market entry, international business development, EU legal exposure, Belgium business culture, and cross-border sales strategy

#SeriouslyDontDoThat #EuropeMarketEntry #InternationalBusiness #B2BSales #GoToMarketStrategy

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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 not wait until the show starts to build your pipeline.

Before the event, companies need a clear target list, a focused outreach plan, better LinkedIn positioning, and a follow-up system that turns conversations into real sales opportunities.

This session is useful for founders, sales leaders, business development teams, insurtech companies, insurance technology firms, and B2B teams preparing for conferences, trade shows, networking events, and industry summits.

What this webinar covers:

▪️ How to think about meetings before the event
▪️ Why showing up without a plan wastes the opportunity
▪️ How to prepare your target list before the show
▪️ Why event ROI depends on pre-event outreach
▪️ How to turn conference attendance into pipeline
▪️ Why follow-up needs to be planned before the first conversation

If your company is attending an industry event, the real work starts before you walk into the room.

Watch the full webinar to learn how to book better meetings before the show.

Presented by Greater Gain Group and InsurTech Association.

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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 verified.

The story starts with a founder preparing for a Series B board meeting.

The CRM showed 41 open opportunities and $4.3M in weighted pipeline.

It looked fine.

Then the close dates told the real story.

34 of the 41 opportunities were set to close on the last day of the quarter.

Same date.

Every one of them.

Nobody was trying to mislead the board.

The team was filling required fields and choosing the value that made the CRM turn green.

That is the problem.

The pipeline was driving hiring plans, cash conversations, and board expectations. But the number underneath it was not a forecast.

It was a default value with a dollar sign in front of it.

In this episode, Dan covers:

Why forecast accuracy is usually a process problem, not a rep honesty problem
Why CRM stages should come from the buyer journey, not the software default
Why “demo completed” and “proposal sent” do not tell you where the buyer actually is
How to rebuild pipeline stages around buyer evidence
Why compliance, legal, finance, security, and procurement are distinct buyers in complex sales
Why every stage needs entry and exit criteria
How to run the two-person test on a live deal
Why forecast categories like commit, best case, and pipeline need evidence-based definitions
Why deals stall and how to build for that instead of panicking
Why “Is it still closing?” is the wrong deal review question
Why “What changed?” creates a better forecast conversation

The key idea:

Activity data is bark.

Buyer evidence is the thermometer.

If your stages describe what your team did, your forecast will always be fragile.

If your stages describe what the buyer proved, your pipeline becomes something leadership can actually inspect.

This week’s assignment:

Review your last five wins and last five losses.
Write down how they actually moved and where they died.
Rewrite your stage definitions around buyer behavior.
Run the two-person test on one deal.
In your next deal review, stop asking “Is it still closing?” and start asking “What changed?”

A pipeline you cannot inspect is not a system.

It is a story.

Seriously, don’t do that.

🎙️ Seriously Don’t Do That™
Hosted by Dan Griffith
🌐 greatergaingroup.com

#SeriouslyDontDoThat #SalesForecasting #SalesPipeline

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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 went perfectly.

The buyer asked real questions.
The room was engaged.
The champion said, “This is exactly what we need.”
Everyone agreed the conversation was valuable.

Then nothing happens.

No next meeting on the calendar.
No mutual action plan.
No confirmed go-live date.
No stage-specific nurture.
No presence with the buying committee.
No live proposal walkthrough.
No reason to show up again in the buyer’s world.

Five weeks later, the email arrives:

“We’ve decided to revisit this next year.”

That is not always a bad meeting problem.

It is usually a pipeline management problem, a follow-up problem, a sales process problem, and a deal control problem.

Deals almost never die inside the meeting.

They die in the gap between meetings.

In this episode, Dan walks through five ways to keep B2B deals moving after a strong sales conversation:

Book the next meeting before you leave the current meeting
Build a mutual action plan backward from the buyer’s go-live date
Attach nurture to your pipeline stages
Stay engaged with people between conversations
Walk the proposal through live instead of emailing it into the void

This matters for founders, CEOs, sales leaders, RevOps teams, enterprise sales teams, fintech companies, healthtech companies, SaaS companies, consulting firms, and any B2B company selling into complex buying committees.

Because your buyer is not going to carry your deal for you.

Not because they are difficult.

Because they have a day job.

Your project is not the only thing on their desk.

If you want better sales follow-up, stronger pipeline management, more accurate deal progression, better enterprise sales execution, and fewer deals dying quietly after good meetings, this is the shift:

Stop running your pipeline on hope.

Control the gap between meetings.

Seriously, don’t do that.

🎙️ Seriously Don’t Do That™
          Hosted by Dan Griffith
🌐 greatergaingroup.com

#SeriouslyDontDoThat #SalesPipeline #B2BSales #SalesProcess #EnterpriseSales

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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 and no real pipeline.

The problem usually is not the event.

The right buyers are often in the room.

The real problem is that most companies treat the conference like a one-time lead source instead of a sales sequence.

There is a sale you make internally before the show.
There is a meeting you sell before the show.
There is a next conversation you sell on-site.
And only after that does the product sale belong in the follow-up.

Most teams skip the front of the sequence, show up cold, and try to sell the product to a stranger in a hallway while they are holding coffee and watching the clock.

Seriously, don’t do that.

In this episode, Dan covers:

Why “bad show” is usually the wrong diagnosis
Why the room is not the problem
Why badge scans are not pipeline
Why a booth is optional, but the sequence is not
How to sell meetings before the event
How to use LinkedIn and the conference app before you arrive
Why the hallway conversation should close the next conversation, not the product
Why follow-up must happen within 24 to 48 hours
How to calculate real conference ROI
The 4-question audit to run before your next event

If you already paid for the booth, use it.

But do not let the booth become the strategy.

The booth is optional.

The sequence isn’t.

Run the 4-question audit on your next event before you fly:

Is there a written plan, and does everyone know what they are responsible for producing?
How many meetings are booked right now, and who is selling meetings between today and the show?
What is the exact sentence your people say to close the next conversation, and does it have a date in it?
Whose calendar has the follow-up block on it before the trip?

Most teams find the gap before they ever leave for the airport.

That is the point.

🎙️ Seriously Don’t Do That™

Hosted by Dan Griffith
🌐 greatergaingroup.com

Live Thursday at 9 AM EDT.

#SeriouslyDontDoThat #GTMStrategy #SalesPipeline

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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 pipeline, why founders need to build relationships before scaling spend, and why selling into U.S. insurance means understanding an entire buying committee, not just finding one champion.

Dan and Chris also cover:

• Why U.S. insurance market entry is a credibility problem, not a marketing problem
• Where companies waste money when expanding into the U.S.
• Why founders should lead early market validation
• How relationships outperform one-off conference interactions
• Why compliance, security, procurement, and governance can quietly kill a deal
• How to build a focused target-account map before spending on market presence
• What founders should validate before hiring a U.S. sales team

If you’re entering the U.S. market, especially in insurance or another complex enterprise industry, this episode will help you avoid an expensive mistake: scaling spend before you’ve built the relationships and system to support it.

Seriously, don’t do that.™

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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 developers build the product, keep the infrastructure working, and everything seems fine.

Until the company starts scaling.

Then costs rise, security gaps appear, systems become harder to manage, and nobody is quite sure who actually owns the problem.

Dan and Tom discuss:

• Why “it works” can be a dangerous standard
• Why developers shouldn’t automatically own cloud infrastructure
• How poor cloud visibility leads to unnecessary spend
• Why every company needs clear infrastructure ownership
• How regular audits expose unused resources, rising costs, and security risks
• The difference between guardrails and roadblocks
• When it makes sense to bring in a DevOps or cloud specialist
• Why backup, disaster recovery, permissions, and cost controls need ongoing attention

Tom also shares a simple five-step framework founders can use to assess their cloud environment:

Assign ownership. Create visibility. Audit regularly. Build guardrails. Know when to call a specialist.

Because great software running on weak infrastructure is still a weak business foundation.

Seriously, don’t do that.™

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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 Do That, and I'm going to prove it to you.

What I'll walk through:

▪ Why the merge field isn't the villain and neither is the rep who sent it
▪ The eight-seat buying committee blueprint every outbound sequence should be built against (screenshot-able)
▪ Why "advanced personalization" isn't a writing skill, read the actual research and it describes the output of an architecture, not a better sentence
▪ The 3-7-7 cadence that captures 93% of replies by Day 10 and why my founder was missing 93% of his own pipeline
▪ The four-point check to run on your very next message (two real elements beat four filler ones, every time)
▪ The one-role, one-week assignment you can start Tuesday

Two founders are showing up to this one.

The founder who's about to conclude the channel is dead.

And the founder who quietly knows it isn't and can't quite explain why nothing's landing.

If you're either of them, this is the eleven minutes you want on your calendar.

🔔 Register to watch live 

Live on LinkedIn, YouTube, and Facebook. See you Thursday.

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