Emily Dong is the founder and CEO of Snout, a pet wellness plan that pays vets directly for routine care. But Snout isn't her first business. It's the third pivot inside the same company, built on a decade of expensive lessons about how founders mistake traction for a real business.

Emily started with Paw Print, the #1 pet health app. It got press, it got users, and it barely made money. She sold it, pivoted into vet software, ran into another ceiling, and pivoted again into what became Snout. Each time, the trap was the same: she'd climb a mountain, optimize her way to the top, and only then realize the whole mountain was too small. In this conversation, she walks Jason through the framework she now uses to tell whether she's on the right mountain in the first place, and the signal that changes everything: when customers stop needing to be convinced and start asking "what's the catch?"

If you're a founder deep enough into a business to feel traction but honest enough to wonder whether it's the right business, this one is for you.

Timestamps:

00:00 Cold open

01:39 Why building a business means figuring out the model while running it

03:53 What Snout actually does and how it's different from pet insurance

06:40 The Paw Print origin story: building the #1 pet health app

07:58 Why "the #1 pet health app" wasn't a good business

08:51 The local maxima trap and how founders fall into it

10:34 How to figure out how tall your mountain actually is

12:08 The pandemic sale and the pivot into vet software

14:15 "You can't sell other people's products"

15:48 The research process behind finding the right mountain

18:27 The signal that told Emily she'd found product-market fit

20:07 Convincing customers vs. providing relief

21:16 Why the same lesson applies to hiring

23:38 The metrics that separate the right mountain from a hill

25:37 When to stop experimenting on the concept and start experimenting on execution

27:32 Culture of experimentation and why only a third of experiments should succeed

30:33 Educating vets and consumers at once

33:20 Why competitors are a good sign, not a threat

35:12 The wellness plan trap that burned vets before Snout

38:10 The googly eyes on takeout containers detour (and what it teaches founders)

40:57 Where Snout is on the mountain now

Andy Grover has spent 15 years rebuilding healthcare from the patient up. He was the first real estate hire at One Medical (which IPO'd and sold to Amazon), co-founded Tend, and is now building in hyperbaric oxygen therapy space. He joins Jason Feifer to explain why the system feels broken when you walk into a doctor's office, and what it actually takes to fix it.

The short version: you don't fix a broken industry with one big move. You fix it with a thousand small ones. Pick a North Star like trust or patient experience, then redesign every detail around it, from the uniforms providers wear to the language they use, to how appointments are scheduled, to how clinicians get paid.

In this conversation, Andy walks Jason through the specific decisions that changed everything at One Medical (no medical assistants, no white coats, 20-minute appointments that actually start on time) and at Tend (dentists back in white coats, blood pressure checks, scripting that builds trust during the procedure). He also gets into why dentists are a top-suicide profession, why most healthcare innovation fails the providers as much as the patients, and what founders in any legacy industry can borrow from the Savannah Bananas playbook.

If you're building in a regulated, slow-moving, or consumer-hostile industry, this one is for you.

Timestamps:

00:00 Cold open

01:40 The Savannah Bananas and the "fans first" philosophy

03:36 Why nobody feels first in healthcare

04:42 Andy's path from real estate to One Medical

06:18 What Apple Store taught One Medical about doctor visits

07:18 Killing the medical assistant role

08:38 Why patients feel different emotions walking through the door

10:11 The reframe: meet people where they are

12:13 Picking trust as the North Star at Tend

14:07 Why nobody trusts their dentist

15:32 Building trust through environment, scripting, and uniforms

17:53 Why One Medical banned white coats but Tend brought them back

19:24 The 60-inch screen and how it changes the trust conversation

22:13 Hiring the right providers for a redesigned system

23:30 Why dentists are a top-suicide profession

26:40 Rebuilding compensation so the patient still comes first

28:20 The trap of optimizing for NPS alone

30:51 Can this approach scale to a full hospital system?

35:13 Why most "innovations" in healthcare are now table stakes

37:21 The founder takeaway: just ask your customers

40:23 How to actually listen at scale

Brenda Schamy, intellectual property attorney and co-founder of Diaz Schamy, joins Jason Feifer to break down the IP mistakes that quietly drain millions from founders who think they've already handled it.

Most experienced operators believe IP is a checkbox: trademark the name, get the contracts reviewed, move on. Brenda argues that's exactly the gap. The real work is strategic: when you file, what entity files it, what you deliberately don't register, and how a perfectly legal contract can still be the wrong contract for your actual goals.

In this conversation, she walks through the blind spots she sees every week from sophisticated founders, including the photography lawsuit waiting in your marketing files, the patent acquisition that left a founder months from being crushed by a bigger competitor, the Taylor Swift trademark timing trick, and why "being cheap is expensive" when it comes to protecting your brand.

If you've built a company, raised money, and assume your IP is locked down, this episode is the second opinion you didn't know you needed.

Timestamps:

00:00 Cold open
01:32 The nightmare scenario every founder fears
04:38 Why IP is more complicated than ever
05:30 Call your lawyer before you fall in love
07:18 What sophisticated founders still miss
07:53 The photography lawsuit hiding in your marketing
10:53 Reposting on Instagram is illegal (even with credit)
13:05 Can you own an AI-generated logo?
17:18 The defense reason for trademarks (and getting sued for your profits)
19:25 Consumer confusion explained
20:01 Timing and IP holding companies
20:40 The Taylor Swift trademark timing trick
24:10 The patent expiration story that crushed a founder
30:24 Trade secrets and why not registering can be the strategy
34:02 Owning phrases, sounds, and colors
39:07 The marketplace of ideas: can you own a phrase?
46:34 What still keeps experienced founders up at night
47:38 How to reach Brenda

Meredith Perry, CEO and co-founder of Elemind, has built something genuinely revolutionary: a wearable headband that uses real-time EEG and sound pulses to interrupt the brainwaves keeping you awake. Clinically proven. Published in Nature. The median user falls asleep in 11 minutes.

The problem? Science doesn't sell. People don't believe you.

In this episode, Meredith breaks down how she solved the trust gap that kills most innovative products. She walks Jason through the actual technology (and demos it on him live during the podcast), then unpacks the guerrilla marketing strategy that put Elemind on the map: "Sleep With Our CEO," where she goes around New York knocking out strangers in Times Square, on the Staten Island Ferry, outside Giants games, anywhere people don't expect to fall asleep.

If you're a founder with a complicated product and a skeptical market, this one is for you.

Timestamps:

00:00 Cold open

04:10 The real innovation gap: getting people to believe you

06:09 What Elemind actually is and how it works

07:18 Putting 500 people to sleep at CES

08:58 The neuroscience, explained simply

11:02 Live demo: Jason tries the headband on the podcast

17:10 Why leading with science doesn't sell

19:24 The "Sleep With Our CEO" guerrilla campaign

22:06 Why founders have to become the face of accountability

25:30 How humor became the strategy

28:32 Amplifying the truth: if it works in Times Square, it works anywhere

30:09 The language masterclass: noise cancellation for the brain, app store for the brain

34:04 Balancing humor with serious science

36:02 Customer feedback that changed the strategy

37:14 Why comfort beat futuristic design

40:26 The one question every consumer asks

41:03 Advice for founders with revolutionary products nobody understands

43:04 Where to get Elemind

Sans Thakur, CEO and Chairman of Tower Capital Group, joins Jason Feifer to explain why the longevity industry is missing the point. The real frontier is generational health: the science of how your DNA, environment, and choices create cascades that shape your descendants' health for up to 16 generations.

Sans is one of the named pioneers of generational health. She spent decades helping launch 40+ medicines that reached 6 million patients before becoming an investor. In this conversation, she breaks down what's actually possible right now: dementia prevention infusions that cut risk by 50%, bio-AI that can grow a beating heart from a drop of your blood, and why the food you eat is interacting with your cells in ways science is only beginning to understand.

If you've been skeptical of the longevity hype but curious about what real science can do, this episode is for you.

Disclaimer: The science descriptions are ultra simplified for general audience consumption.

Timestamps:

00:00 Cold open

01:25 Why longevity has become "fluffy" and what it used to mean

02:30 What Tower Capital Group actually does

09:12 Defining generational health and the 16-generation cascade

13:53 From Human Genome Project to today's bio-AI breakthroughs

18:00 The dementia prevention infusion that cuts risk by 50%

21:30 Genetic cascades explained: how your choices imprint on your DNA

24:35 Growing a beating heart from a drop of blood

28:30 Bioethics and why this technology isn't available to everyone yet

29:32 Your mother's mitochondria and why maternal health is underfunded

32:00 Why longevity influencers get it wrong

36:38 Food as medicine and the data gap between groceries and clinics

40:12 How much do we actually know about food and the body?

46:13 How to get involved with Tower Capital Group and Uncharted Pitches

52:48 The "spackle" and why small wins matter too

Sans Thakur, CEO and Chairman of Tower Capital Group, joins Jason Feifer to explain why the longevity industry is missing the point. The real frontier is generational health: the science of how your DNA, environment, and choices create cascades that shape your descendants' health for up to 16 generations.

Sans is one of the named pioneers of generational health. She spent decades helping launch 40+ medicines that reached 6 million patients before becoming an investor. In this conversation, she breaks down what's actually possible right now: dementia prevention infusions that cut risk by 50%, bio-AI that can grow a beating heart from a drop of your blood, and why the food you eat is interacting with your cells in ways science is only beginning to understand.

If you've been skeptical of the longevity hype but curious about what real science can do, this episode is for you.

Timestamps:

00:00 Cold open

01:25 Why longevity has become "fluffy" and what it used to mean

02:30 What Tower Capital Group actually does

09:12 Defining generational health and the 16-generation cascade

13:53 From Human Genome Project to today's bio-AI breakthroughs

18:00 The dementia prevention infusion that cuts risk by 50%

21:30 Genetic cascades explained: how your choices imprint on your DNA

24:35 Growing a beating heart from a drop of blood

28:30 Bioethics and why this technology isn't available to everyone yet

29:32 Your mother's mitochondria and why maternal health is underfunded

32:00 Why longevity influencers get it wrong

36:38 Food as medicine and the data gap between groceries and clinics

40:12 How much do we actually know about food and the body?

46:13 How to get involved with Tower Capital Group and Uncharted Pitches

52:48 The "spackle" and why small wins matter too

In the early days of AI products, buyers were willing to experiment and take risks. Now they expect clear ROI. That’s changing the way that AI products are taken to market.

Rachel ten Brink, GP and co-founder of Red Bike Capital, breaks down what’s actually working now: founder-led sales, distribution moats, customer adoption, enterprise champions, strategic partnerships, and why the companies that win won’t necessarily have the best models — they’ll have the best go-to-market strategy.

You don’t win on product alone. You win by recognizing the white space that’s hidden in plain sight

In this episode, Jason talks with beverage entrepreneur Michelle Ivey — who built Illegal Mezcal and sold it to Bacardi, helped Megan Thee Stallion launch her tequila, and is now building multiple beverage brands — about what it actually takes to stand out when every shelf is full.

During big technological shifts, leaders face a difficult question: How do you project calm and vision, while everything around you changes?

Raynmaker CEO Joe Gagnon has led six companies, and has an answer: You must move as fast as the change itself. He explains how to create confidence in uncertain times, where AI actually helps (not hurts), and why the fundamentals of business matter more than ever.

How do founders stay calm, think clearly, and find answers faster when everything goes wrong?In this episode, host Jason Feifer talks with Gambit Robotics cofounder and former U.S. chess player Nicole Maffeo about the real mechanics of problem solving. They break down how great operators handle ambiguity, why patience is now a competitive advantage, how to “chunk” complex problems into solvable parts, and why losing well may be one of the most valuable entrepreneurial skills.