Best Startup Out Of The Box Podcasts (2025)

1
Ep. 3199 - Q&A: “How do I handle a non-compete that hurts my side hustle?” 5:09

Play Pause

14h ago5:09

5:09

A promotion with strings attached can stall a thriving side hustle. Today we’ll walk through reading the fine print, negotiating carve-outs, and keeping both your boss and your business on the road. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ye…

1
Ep. 3198 - Q&A: “I went viral, but now I can’t meet demand!” 5:23

1d ago5:23

5:23

A viral spike is great—until it breaks your capacity. Today we map a four-step triage plan to pause the chaos, satisfy customers, and turn overwhelm into long-term buzz. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free gu…

1
HEADSTART: My patent is granted, what’s next? 3:17

6h ago3:17

3:17

Congratulations! Now that your patent is granted, what arethe next steps? In this episode, you’ll learn: How to validate it, pay fees and handlechallenges, all while aligning with your business strategy. How to make the most of your newly grantedrights. Note: Holding a granted patent does not confer anabsolute right to commercially exploit the inve…

1
145 - Creating Internal Startups: Fostering Innovation Within Large Enterprises with Box's Adarsh Subramanian 23:38

1h ago23:38

23:38

Your host, Thomas Watkins, talks with the Group Manager of Product Management at Box, Adarsh Subramanian. Adarsh shares his journey from engineering to product management, discusses Box’s evolution into an AI-first enterprise content platform, and explains how Box delivers end-to-end solutions for enterprise workflows. He explores the challenges st…

1
Ep. 3197 - TBT: Turning Property Management Experience Into Digital Products 5:32

3d ago5:32

5:32

In this week’s Throwback Thursday segment, learn how one former apartment manager turned their real estate experience into a template shop for landlords, helping them boost revenue without buying new properties. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their…

1
144 - Turning Trash into Treasure: Shaping the Future of Waste Management with EcoCycle Ng's Daniel Falodun 18:24

11h ago18:24

18:24

Your host, Thomas Watkins, talks with the Founder at EcoCycle Ng, Daniel Falodun. Daniel discusses founding EcoCycle, a blockchain-based waste management system that rewards users and pickup agents with tokens for recycling, making waste collection more efficient and fair. He shares insights on his other ventures, Erase (a green AI e-commerce platf…

1
Ep. 3196 - STORY: Google Employee Makes $100,000 Using Fiverr 7:32

3d ago7:32

7:32

In just one year, this Google product manager earned an extra $100,000 by providing marketing services on Fiverr.com. Learn his tips to hack the platform for yourself! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guid…

1
143 - Breaking Barriers: How Integrated Data Improves Business Performance with Groflex's Eric Berkman 20:35

2h ago20:35

20:35

Your host, Thomas Watkins, talks with the CMO at Groflex, Eric Berkman. Eric shares his startup journey, discussing the challenges of founding Groflex and the evolution from a niche accounting tool to a broad operational intelligence platform. He discusses how Groflex integrates and analyzes data across business functions, moving beyond traditional…

1
Ep. 3195 - Q&A: “Which passive-income model fits a consultant best?” 6:13

4d ago6:13

6:13

Want to escape the billable-hour treadmill? Today we map out three proven paths—courses, content, and compounding cashflows—that turn one-time effort into long-term income. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free…

1
Morrissey cancels shows in the US following a credible threat on his life, rare unseen footage from a 1990 Nirvana concert in Mexico is up for auction, My Chemical Romance 2026 dates & more! 9/29/25 56:33

5d ago56:33

56:33

Morrissey cancels shows in the US following a credible threat on his life, rare unseen footage from a 1990 Nirvana concert in Mexico is up for auction, My Chemical Romance announce additional world tour dates in 2026 for their 20th anniversary of The Black Parade, members from R.E.M. and The Black Crowes are forming a supergroup and plan to tour ne…

1
Ep. 3194 - First $1,000: Marketer Sells Simple Fixes to Dental Clinics 5:11

5d ago5:11

5:11

In this week’s First $1,000 segment, hear how a digital marketer gets paid for cleaning up Google listings for orthodontists—fixing visibility problems most offices didn’t even realize they had. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, …

1
Fixing Broken Meetings, Managing Calendars with AI, and Redesigning the Future of Work | Matt Martin CEO & Co-Founder Clockwise 49:00

6d ago49:00

49:00

In this episode, Nataraj welcomes Matt Martin, CEO of Clockwise, to explore the science of smart scheduling. Discover how Clockwise uses AI to optimize calendars, reduce meeting overload, and create more focused work time. Matt shares insights on balancing collaboration with individual productivity, the impact of remote work on meeting culture, and…

1
Ep. 3193 - Weekend Workshop: The Art of Electronics Arbitrage 8:01

6d ago8:01

8:01

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: buy low, sell high, repeat! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mon…

1
Ep. 3192 - Q&A: “How can a freelancer pay herself a stable salary?” 5:39

7d ago5:39

5:39

Feast-or-famine income doesn’t have to mean feast-or-famine life. Today we build a simple three-bucket system that turns lumpy freelance revenue into a steady, predictable paycheck. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show incl…

1
Ep. 3191 - Q&A: “What KPIs should I track for my software biz?” 4:23

8d ago4:23

4:23

Fifty customers, fifty metrics—too many for a two-person team. Today we boil micro-SaaS analytics down to the three numbers that actually move the needle. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons an…

1
HEADSTART: Patent filing vs grant: What’s the real difference? 3:32

6d ago3:32

3:32

Filing a patent application isn’t the same as having agranted patent. In this episode, you’ll understand: The difference between submitting a request forexclusive rights and actually having enforceable patent rights. The publication process, examination rounds,search reports, and when you can actually claim: "I have a patent". The general informati…

1
142 - Reimagining Product Lifecycle Management: Breaking Free from Legacy Systems with Propel Software's Tom Shoemaker 21:26

5d ago21:26

21:26

Your host, Thomas Watkins, talks with the VP of Product Marketing at Propel Software, Tom Shoemaker. Tom discusses how Propel’s cloud-based platform, built on Salesforce, helps manufacturers of physical products streamline collaboration, ensure compliance, and maintain audit readiness—especially in regulated industries like medtech. He explains the…

1
Ep. 3190 - TBT: Helping Aspiring Film Professionals Get Hired 4:47

9d ago4:47

4:47

In this week’s Throwback Thursday segment, learn how a London-based side hustler launched a service to help aspiring film crew members get their first jobs and union credentials—and how they’re now planning to expand to Los Angeles and Vancouver. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn…

1
Ep. 3189 - STORY: College Grad Shares “More than Mac & Cheese” Student Recipes 6:45

11d ago6:45

6:45

When a college student learns to cook, she documents her recipes online, earning more than $1,000/month. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes:…

1
141 - The Shopify of Voice AI: Making Advanced Technology Accessible for All with thinkrr.ai's Mohan Gulati 20:48

7d ago20:48

20:48

Your host, Thomas Watkins, talks with the CEO at thinkrr.ai, Mohan Gulati. Mohan discusses how Thinkrr.ai uses advanced voice AI technology to help businesses reduce revenue loss from inefficiencies in sales, customer support, and operations. Mohan explains how their easy-to-deploy AI agents act as virtual receptionists, handle calls, qualify leads…

1
Shining a light on the photovoltaics boom 13:31

7d ago13:31

13:31

Solar energy is more integrated into our daily lives than ever before, powering homes, cities and even wearable devices. What’s driving this transformation, and how are innovation and policy shaping the future of photovoltaics? Join inventors, startup founders and policymakers as they discuss the latest breakthroughs in photovoltaics, from hydrogen…

1
Ep. 3188 - Q&A: “Can you run a YouTube channel with only AI voices and scripts?” 4:15

12d ago4:15

4:15

Can a faceless, AI-voiced show win viewers and ad dollars? Today we break down platform rules, audience psychology, and the tiny legal print you can’t ignore when the “host” is synthetic. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the sho…

1
Vince Neil reveals he had a stroke back in December, Matt Cameron opens up in a new interview about Soundgarden’s upcoming RRHOF induction & why he left Pearl Jam & more! Week of 9/22/25 46:40

12d ago46:40

46:40

Vince Neil reveals he had a stroke back in December and has slowly been recovering to prepare for Motley Crue’s upcoming shows, Matt Cameron opens up in a new interview about Soundgarden’s upcoming RRHOF induction & why he left Pearl Jam, Rob Halford reveals he recorded a new version of War Pigs with Ozzy Osbourne right before he passed in July, Sa…

1
Ep. 3187 - First $1,000: Typography Lover Turns Letters Into Revenue 5:19

13d ago5:19

5:19

In this week’s First $1,000 segment, learn how a font designer earned their first digital payday with a clean, subway-inspired typeface. With just two fonts and a Creative Market listing, they passed $1,000 in less than a month. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money witho…

1
Ep. 3186 - Weekend Workshop: Design Disruption in Traditional Markets 5:47

14d ago5:47

5:47

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: an astrology calendar for modern times. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ea…

1
Ep. 3185 - Q&A: “How can I sell an Amazon-only FBA brand for top dollar?” 5:05

15d ago5:05

5:05

Trying to sell an Amazon-only FBA brand? In this episode we talk valuation, “channel risk,” and a 90-day tune-up that can add tens of thousands to the sale price of a business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes …

1
Ep. 3184 - Q&A: “How can a coast-to-coast road trip pay for itself?” 4:54

16d ago4:54

4:54

A coast-to-coast road trip sounds expensive—unless you turn the highway into a revenue stream. Today we map out five travel-friendly hustles that can cover gas, motels, and maybe even a little profit. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This …

1
HEADSTART: What makes an invention “inventive”? 3:34

14d ago3:34

3:34

Not all technical advancements are patentable. 📌 Discover in this episode: What makes an invention truly “inventive” in away that meets patentability criteria. How this criterion supports technologicaldevelopment The role of the patent system in fosteringinnovation and protecting unique advancements. The general information in these videos provides…

1
140 - Taming the AI Beast: Mastering Governance and Model Management with ModelOp's Dave Trier 18:14

12d ago18:14

18:14

Your host, Thomas Watkins, talks with the VP of Product at ModelOp, Dave Trier. Dave explains how ModelOp’s platform centralizes AI governance, automates oversight, and supports diverse models, helping organizations manage risk while enabling innovation. Dave discusses the evolving need for customer support, with some clients now mature enough for …

1
Ep. 3183 - TBT: Creator Builds Instagram Mastermind Pod 5:02

17d ago5:02

5:02

In this week’s Throwback Thursday segment, hear how a social media strategist launched a private mastermind pod to help creators boost their Instagram engagement—sharing likes, comments, and algorithm tips. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job.…

1
Ep. 3182 - STORY: Personal Trainer Pumps Up Breakfast 7:36

18d ago7:36

7:36

A full-time personal trainer takes ‘breakfast of champions’ to the next level with pancakes that put the ‘pro’ in protein, earning $25,000/month. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listene…

1
139 - Empowering Employees with AI: Making Technology Work for You with StudioX's Ajay Malik 23:54

14d ago23:54

23:54

Your host, Thomas Watkins, talks with the CEO at StudioX, Ajay Malik. Ajay shares how StudioX helps companies integrate AI into daily workflows for greater efficiency and innovation. He covers industry pain points, the importance of seamless AI integration, and the value of strong UX and storytelling in communicating AI’s benefits. Learn more about…

1
Ep. 3181 - Q&A: “Should my first info product be $30 or $300?” 5:42

19d ago5:42

5:42

Should you launch your first info product at a budget price or aim for a premium market? Today we unpack perceived value, buyer psychology, and the hidden costs of “cheap” customers—so you can price with confidence. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting t…

1
60th anniversary Doors concert with Robby Krieger, Morrissey wants to sell his rights to The Smiths, Twisted Sister 50th, Bruce Springsteen 'Electric Nebraska' box set details & more! Week of 9/15/25 48:55

19d ago48:55

48:55

A 60th anniversary Doors celebration concert with Robby Krieger has been announced to take place in Los Angeles in October, Bruce Springsteen announces the release date for the long-awaited electric version of ‘Nebraska’ in a huge upcoming boxset, Twisted Sister will be celebrating their 50th anniversary with some reunion shows in 2026, Morrisey is…

1
Ep. 3180 - First $1,000: Foot Traffic Nerd Turns Public Data Into Paid Service 5:29

20d ago5:29

5:29

In this week’s First $1,000 segment, hear how a data enthusiast built foot traffic reports for small landlords and local businesses, using public tools and smart packaging. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free…

1
Ep. 3179 - Weekend Workshop: Building Systems That Sell Themselves 6:52

21d ago6:52

6:52

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: the “guest post tracker” that earned recurring revenue. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies …

1
The Future of Enterprise AI: $100M ARR, Agents, Company Building, and Scaling Unicorns | Arvind Jain (Co-founder of Glean, Rubrik, ex-Google) 54:02

21d ago54:02

54:02

Discover how Glean AI is transforming enterprise productivity with AI-powered search and intelligent agents. About the episode: Join Nataraj as he explores the evolution of enterprise AI with Arvind Jain, CEO of Glean. From its roots as an AI-powered search solution, Glean has transformed into a comprehensive AI agent platform, helping companies li…

1
Ep. 3178 - Q&A: “How do I stop every freelance project from starting in chaos?” 5:24

22d ago5:24

5:24

Do you begin every freelance project in panic-mode? In today’s episode we build a repeatable onboarding sequence that turns new clients into smooth projects—no assistant required. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includ…

1
Ep. 3177 - Q&A: “How can I make money by renting out houseplants?” 4:11

23d ago4:11

4:11

Can your living-room jungle become a revenue stream? In today’s episode, we explore the growing demand for short-term plant rentals and break down the numbers, logistics, and risks of turning leafy assets into cash. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting t…

1
HEADSTART: When is your invention ready for a patent? 3:36

19d ago3:36

3:36

Before filing a patent application, make sure your inventionis ready. It’s not just about having a great idea – you need the technical details in place. This episode explains: What to include, from your description and drawings to your claims. How to draft a clear, complete application toprotect your invention and support your business strategy. Th…

1
138 - From Data to Decisions: Transforming Local SEO Insights into Action with Local Falcon's David Hunter 21:15

19d ago21:15

21:15

Your host, Thomas Watkins, talks with the CEO at Local Falcon, David Hunter. David shares his journey from finance to digital marketing and explains how Local Falcon helps businesses visualize and improve their local SEO rankings using a geo grid system. He covers the unique challenges of local SEO, the evolution of Local Falcon from a pure SaaS an…

1
Ep. 3176 - TBT: Helping High School Dropouts Start Plumbing Careers 5:40

24d ago5:40

5:40

In this week’s Throwback Thursday segment, learn how one side hustler partnered with trade schools to help high school dropouts gain life skills and secure paid apprenticeships in the plumbing trade. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This y…

1
Ep. 3175 - STORY: Movie Industry Friends Rewrite the Credits, Earn $20,000/Month 6:40

25d ago6:40

6:40

Those long credit sequences at the ends of movies can include a LOT of names—and they also take a lot of time for producers to coordinate. When two industry friends team up to simplify the process, they crawl their way to a highly profitable side hustle. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people …

1
137 - From Startup to Enterprise: Bridging the AI Infrastructure Gap with Concrete Engine's Meltem Ballan 24:03

24d ago24:03

24:03

Your host, Thomas Watkins, talks with the CEO and Co-Founder at Concrete Engine, Meltem Ballan. Meltem discusses the company’s mission to make AI infrastructure accessible, secure, and scalable for businesses of all sizes. She explains the challenges companies face with current AI solutions and how Concrete Engine offers a managed service that simp…

1
Ep. 3174 - Q&A: “How can a first-time author stand out in a market of 4,500 books per day?” 5:25

26d ago5:25

5:25

With an estimated 4,500–6,000 English-language titles published each day, how can a first-time author avoid getting buried? Today we look at the real numbers—and a proven game plan for standing out. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ye…

1
Sting is being sued by his ex-bandmates for millions in unpaid royalties, Radiohead surprise fans by announcing their first official tour in over 7 years, Sex Pistols cancel their tour & more! 9/8/25 1:00:07

26d ago1:00:07

1:00:07

Sting is being sued by his ex-bandmates for millions in unpaid royalties, Radiohead surprise fans by announcing their first official tour in over 7 years, the Sex Pistols are forced to cancel their upcoming North & South American tour dates due to an unexpected injury in the band, the Ronnie James Dio Stand Up and Shout for Cancer fund announces th…

1
Ep. 3173 - First $1,000: Houston Homeowner Turns Studio Into Weekend Venue 6:28

27d ago6:28

6:28

In this week’s First $1,000 segment, discover how one Houston homeowner transformed a simple backyard shed into a rentable studio for photos, workshops, and quiet retreats. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free…

1
Ep. 3172 - Weekend Workshop: The Seasonal Business Goldmine 7:11

28d ago7:11

7:11

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: the six-figure, six-week business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ex…

1
Ep. 3171 - Q&A: “Managing cash flow across PayPal, Stripe, Venmo, and Etsy…” 5:11

29d ago5:11

5:11

Multiple payment platforms can feel like financial whack-a-mole. Today we lay out a four-step system to keep cash flow clear and tax time painless. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and liste…

1
Ep. 3170 - Q&A: “Do followers still matter in the age of algorithms?” 6:05

30d ago6:05

6:05

If algorithms decide who sees your content, do follower counts still matter? Today we dig into how “algorithmic feeds” really work and why a loyal subscriber base still gives side hustlers a competitive edge. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their jo…