Problem Solvers

By Entrepreneur MediaBusiness Entrepreneurship

Problem Solvers episodes

October 12 GoFundMe's Problem Wasn't the Product
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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25 min
October 05 What Customers Ask For vs. What They Actually Want
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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28 min
September 28 Jon Taffer's Complete Guide to Franchising
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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51 min
September 21 The Forbidden Love Every Founder Feels
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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30 min
September 14 Why Data-Driven Is a Trap
Jason sits down with Sebastian Wernicke, data scientist and author of Data Inspired: Building an Organizational Culture of Inquiry for Lasting Transformation, to talk about why "data-driven" companies so often end up trapped inside what they already know instead of discovering what their customers actually need. They get into the sports car company that ignored its own sales numbers, the one question that reveals whether your company can actually handle being wrong, and how Jason's own newsletter taught him he'd built himself a very comfortable cage.

Timestamps
0:00 The Hit Song Formula That Failed
0:27 Welcome to Problem Solvers
0:38 Why a Song About Pop Music Matters to Your Business
2:45 Meet Sebastian Wernicke, Author of Data Inspired
3:06 Why Data Feels Like Comfort (And Why That's a Trap)
4:52 Two Ways to Use Data: Optimization vs. Innovation
5:06 Google's "50 Shades of Blue" Experiment
6:38 Data-Driven vs. Data-Inspired, Defined
7:46 The Sports Car Company's Weird Stereo
10:25 How Do You Know Which Outlier to Trust?
13:19 Use Data to Support a Bold Guiding Policy, Not a Safe One
14:20 The Medical Device Company's Real Diagnosis
16:29 Jason's Own Data Trap: A/B Testing His Newsletter
20:59 Error Reduction vs. Loss Aversion
22:24 Can a Junior Analyst Challenge the Boss in Your Company?
26:03 The Book: Data Inspired

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29 min
September 07 Pat Flynn asks "How Do You Sell A Personal Brand"
Before he was Deep Pocket Monster, Pat Flynn was the face behind Smart Passive Income. Eighteen years later, he's ready to pour everything into Pokémon, but he's not willing to abandon the community that built him. So he made a call most founders never make. Liz Wilcox, an email marketing expert with her own exit story, joins him to explain what happens next.

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43 min
August 31 How a Dying Arcade Brand Became a Nostalgia Machine
A few years ago, Jason rediscovered his love of Pop-A-Shot, the arcade basketball game. What he didn't know was the whole story behind Pop-A-Shot's sudden renaissance. Tony Stucker, the CEO of Pop-A-Shot, joined the show to unpack the brand strategy behind the turnaround and what it takes to extract new growth from a legacy asset.

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35 min
August 24 Why Your Feedback Isn't Landing
Jason once got an edit back covered in red, all caps, like he'd been screamed at on paper. He swore he'd never do that to anyone, but it turns out most of us are still getting feedback wrong. Caroline Webb, author of Leadership Intelligence, breaks down the one shift that makes people actually hear you. It's simpler than you think, and it starts with what you say before the criticism..

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30 min
August 17 How to Be Irreplaceable In an AI World
Will AI make entrepreneurship easier—or make entrepreneurs irrelevant?
In this episode of Problem Solvers, Jason Feifer sits down with LinkedIn Chief Economic Opportunity Officer Aneesh Raman, co-author of Open to Work: How to Get Ahead in the Age of AI, to rethink the biggest fear around AI and business: that technology is coming for your job, your company, and your edge.
Jason shares his “AI is a microwave” theory: it’s a powerful new tool, but we’re still learning what belongs in it—and what absolutely doesn’t. Aneesh explains why AI is lowering the cost of starting a business, making it easier to research markets, build prototypes, and test ideas fast. But as access goes up, so does the premium on something AI cannot replicate: your unique perspective, taste, curiosity, courage, communication, and lived experience.
They break down why the future of work is not about humans becoming better AI prompters. It’s about becoming more entrepreneurial, more creative, and more distinctly human. In a world flooded with AI-generated sameness and “AI slop,” the people who win will be the ones who use AI to amplify—not replace—their judgment, originality, and connection.

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31 min
August 10 You're Wasting an Hour a Day Doing This
Executive Coach Neal Schore says that fear-driven habits are quietly
stealing at least an hour from your day, every day. Drawing from
decades of coaching founders, operators, and unicorn CEOs, Neal explains
how anxiety about being fired, judged by boards, or seen as “not
enough” leads to endless Slack chains, diluted meetings, and mental
“swirls” that crush focus and time. Neal and Entrepreneur
Editor in Chief Jason Feifer unpack why good things often start with
worst-case scenarios (like getting fired), how to stop overcompensating
out of fear, and why managing you—not everyone else—is the only
way to reclaim your calendar. He shares practical tools from his new book, The 25th Hour, like the “clarifying question” that can turn a 7-hour crisis into a 7-minute conversation, the devil/angel metaphor for fear versus real performance issues, and a simple five-minute “swirl limit” to stop catastrophic thinking from hijacking your nights and weekends. If you’re a founder or senior leader stuck in loss-aversion, overcommitting to boards, or living in constant “what if I get fired?” mode, this conversation shows
you how to get out of your own way, protect your time, and even see job
loss or client churn as the start of better fits—not the end of your
career.

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25 min

About Problem Solvers

From the publisher's feed

You have business problems. This show has solutions. Each week, Entrepreneur’s Editor in Chief Jason Feifer digs deep with entrepreneurs and CEOs — identifying the major problems they faced, the…