Problem Solvers

Anthony Pompliano built an AI financial assistant people loved. Then his most engaged users started costing him too much money. That’s a good problem to have. But it’s still a problem. His solution came from an unlikely place. Olive Garden’s breadsticks. Here’s how Silvia cut costs without cutting what users love, and got 25% of monthly active users to pay.

Find Anthony's book here!

This episode of Problem Solvers is presented by AT&T Business. To learn more about how the right connectivity can help support your business as it grows, visit att.com/smallbusiness.

Jason wants to help solve your impossible problem! Click the link below to sign up:

https://entm.ag/levelup2026

Timestamps:

0:00 Intro

0:38 The idea of a “better problem”

2:05 Anthony’s book, How to Live an Extraordinary Life Volume Two

5:00 Silvia’s power-user problem

6:50 The Olive Garden breadstick lesson

9:15 Weighing every possible fix

11:07 Building a model router

12:55 Bracketing: a military trick for making decisions

16:50 Experiments vs. archaeology

18:15 Training their own model (97% cheaper)

19:10 Rolling out the paywall

20:40 Why people pay

21:45 How to spot this problem in your own business

24:16 Where to find Anthony and Silvia
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GoFundMe had a strange problem. About a quarter of people created fundraisers and then never shared them. Better share buttons didn't fix it. That's because the problem wasn't the product. It was human. Asking for help is really, really hard. CEO Tim Cadogan explains how GoFundMe rebuilt around that truth, and why the fix generated more than double the help they expected.

This episode of Problem Solvers is presented by AT&T Business. To learn more about how the right connectivity can help support your business as it grows, visit att.com/smallbusiness.

Jason wants to help solve your impossible problem! Click the link below to sign up:

https://entm.ag/levelup2026

Chapters:

00:00 – Intro 00:35 – GoFundMe's strange problem

02:10 – A quarter of fundraisers never get shared

03:10 – How GoFundMe spotted the gap

04:30 – Why better share buttons didn't work

05:15 – The four reasons people weren't sharing

07:00 – When the product isn't enough

08:30 – Fixing the sticking points, starting with titles

10:55 – Building the AI coach

12:45 – How the coach works day to day

14:00 – Is this just AI for AI's sake?

16:45 – A father's story

18:15 – Jason's book launch lesson: Asking is generous

19:50 – The paradox of help

20:15 – The best way to ask for help

21:30 – The results: More than double what they expected

22:15 – What's next for the coach
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SimpliSafe was built for renters. Renters didn't buy it. Homeowners did. Jason has told that story for years, because it's a perfect lesson in how founders get their customer wrong. But he never asked the obvious follow-up: once you finally find the right customer, then what? Now, 20 years in, SimpliSafe founder Chad Laurans and CEO Hilary Schneider reveal what comes after product-market fit, and why customers asking for "more cameras" didn't actually want more cameras.

This episode of Problem Solvers is presented by AT&T Business. To learn more about how the right connectivity can help support your business as it grows, visit att.com/smallbusiness.

Jason wants to help solve your impossible problem! Click the link below to sign up:

https://entm.ag/levelup2026

0:00 The "faster horses" myth

0:29 Welcome to Problem Solvers

0:46 The SimpliSafe origin story: renters vs. homeowners

2:21 What happens after product-market fit?

2:55 Meet the guests

3:47 What product-market fit actually feels like

5:11 Should you build everything customers ask for?

6:11 Why you have to keep asking "why"

7:14 From "more cameras" to crime prevention

8:17 Fact check: Henry Ford never said it

9:22 What customers really want: peace of mind

10:02 Making a costly service profitable with AI

11:44 Launching a product that doesn't scale yet

13:48 Why big companies forget to prototype

16:51 Build things you're willing to throw away

18:26 What's next for SimpliSafe

19:48 The innovator's dilemma of a cheaper product

20:31 Mining customer support calls for insight

21:52 Go back to what made you great

23:22 The mission: every home secure

23:57 Long-term value comes from creating value

26:33 Wrap-up
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Jon Taffer, host of the hit TV show "Bar Rescue", has sat on both sides of the franchising table. He's been a franchisee, including one franchise you'd never guess. Now, as founder of Taffer's Tavern, he runs his own franchise system. And even with 40-plus years in business, he's shopping for his next franchise right now. That perspective means he knows exactly what to ask before buying in. The question he says matters most is one most would-be franchisees never think to ask.

Timestamps:

00:00 Jon Taffer's surprising next business move

00:30 Why franchising made Jason nervous

03:10 Jon's franchise résumé: from Hooters franchisee to Taffer's Tavern

04:22 Turnkey vs. brand: what you're really buying

07:02 Why so many corporate pros are jumping into franchising

08:08 The biggest perk: you can sit in it before you buy it

09:53 Beyond burgers: franchises in every industry

11:12 Jon's doggy daycare hunt and Jason's franchise near-miss

14:39 The FDD: the document you can't skim

16:58 The #1 red flag Jon won't touch with a 10-foot pole

20:49 The questions that reveal a franchisor's sales muscle

22:57 Jon's six-step vetting process

25:18 What the franchisor does vs. what's on you

28:13 Who Jon wants running a Taffer's Tavern

30:31 Cutting through the noise: Doritos Locos Tacos and the five-word mission

35:52 Local store marketing: own four or five blocks

39:05 What's new in franchising: smaller footprints, fewer days

40:37 The marketing opportunity hiding in every box

43:42 What World Cup fans revealed about franchise brands

44:49 How to take your first step
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Raj Mehra had it all: a personal reason to build, a hot new technology, a sector ripe for disruption. Then he put his product in front of real users and watched them fail to use it. So he did the hard thing. He listened. What he learned wasn't just a fix. It was a completely different company. This is the story of Sage Healthcare, and it's also the story of what it takes to break up with your own idea.

0:00 – Intro: the "forbidden love" of founders and their original ideas

1:36 – Meet Raj Mehra, CEO & co-founder of Sage

2:33 – What Sage does today (senior care tech platform)

3:14 – The origin story: his grandmother's fall

3:57 – The original hypothesis — building a voice app (Alexa/Google Home era)

5:24 – Building the "expensive paperweight" before validating with users

7:56 – The co-founders join, and the decision to finally talk to users

8:56 – What they learned: hardware was outdated, but voice wasn't the answer

11:44 – Feeling relief, not defeat, when the original idea didn't hold up

12:46 – Finding the middle ground: off-the-shelf hardware + exceptional software

16:39 – Taking the product to market — first customer deployments

17:00 – Solving the hard technical and life-safety challenges

19:27 – Using design sprints to navigate every major crossroads

20:36 – Filtering ideas through the "North Star": does it improve care?

22:15 – Advice for early-stage founders navigating a new market

23:57 – Advice #2: knowing when the technology is actually ready

26:15 – Where to find Sage, and closing thoughts
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