Best Bootstrapper Podcasts (2025)

1
How to Start a Business (Even If You're Scared Sh*tless) 7:57

5d ago7:57

7:57

Send us a text Starting a small business from scratch? Learn how to launch with no money, no connections, no fluff. Ever feel like most business advice is just recycled guru nonsense or comes from people born wealthy? This episode is for the real ones—those starting small businesses without money, privilege, or fancy degrees. This episode kicks off…

1
Growing a hosting platform to $400k ARR: Elston Baretto (Tiiny Host) 52:30

13d ago52:30

52:30

After a hiatus, The Ramen Club podcast (formerly Ramen FM) is back! For episode 10, I spoke to my good friend friend and long-time Ramen Club member, Elston Baretto (founder of Tiiny Host). Tiiny Host is the simplest way to host and share your work online - uploading HTML, PHP, PDFs & Zip files (plus more soon) in seconds. Started 4 years ago, Elst…

1
NO CASH, NO PROBLEM: HOW TO HUSTLE YOUR WAY TO THE TOP 1:17:27

3M ago1:17:27

1:17:27

Send us a text What does it really take to go from struggling to thriving? In this raw and motivating episode, e-commerce expert Zoe Khan shares her incredible journey from financial desperation to running a successful agency with over 100 employees. Zoe’s story starts with selling plasma just to afford a phone to apply for jobs. Juggling multiple …

1
Foster Care Crisis: 80% of Death Row Inmates & 60% of Traffic Victims — A Call for Reform 55:35

3M ago55:35

55:35

Send us a text Foster care crisis, systemic neglect, shocking statistics, death row, traffic fatalities, urgent reform, social justice. Lisa’s journey is a testament to resilience and the power to create change. After enduring 36 foster homes and facing homelessness at 18, she refuses to let the system’s failures define her future. Now, she’s takin…

1
ENTREPRENEURS: CAN FITNESS GIVE YOU THE EDGE? DR. SHELL HAS THE ANSWER! 1:01:20

4M ago1:01:20

1:01:20

Send us a text Want to build a thriving business? Start with your body. In this powerhouse episode, Dr. Shell—doctor, entrepreneur, and Bare Knuckle Fighting Championship competitor—shares how strength training and mental resilience give entrepreneurs the edge they need to win in business and life. Discover why fitness isn’t just about looking good…

1
EMPOWERING ENTREPRENEURS TO THRIVE WITH PALOMA 1:22:16

4M ago1:22:16

1:22:16

Send us a text Thinking about starting a business but unsure where to begin? We’re here to help. Join us as we explore the key steps to building a strong foundation, featuring insights from Paloma, an experienced business attorney. We’ll break down the importance of choosing the right business structure—like an LLC—to protect your personal assets a…

1
IS MONEY BLOCKING YOUR DREAM? HERE’S HOW TO BEGIN! WITH DAVEED BENITO 1:05:59

4M ago1:05:59

1:05:59

Send us a text People often focus on all the reasons why they can’t achieve something—lack of money, equipment, or confidence. But what if we flipped the script? Let’s talk about all the ways you can break through those barriers. 💡 We believe this is the moment for independent creators to rise, break the rules, and maybe even reshape the entertainm…

1
JUDGE LYNN TOLER: RELATIONSHIPS MAKE OR BREAK SUCCESS 1:00:57

4M ago1:00:57

1:00:57

Send us a text Prepare to be inspired by the incredible resilience and wisdom of Judge Lynn Toler, a trailblazer known for her impactful work on "Divorce Court" and "Marriage Boot Camp." We explore the remarkable story of her father, who, despite the odds stacked against him as a black man in a predominantly white industry, supported his family fro…

1
Mastering the Art of Event Planning for Business Growth 15:10

12M ago15:10

15:10

What is the true value of an event in today's digital world? The strategic value goes far beyond the execution of the event itself. In this episode, we'll cover the mindset shift event planning requires from the discipline and routine it gives you to the post promotion value in the content you get from it. Learn how events can be a catalyst for bus…

1
Solopreneur Guide Part 1 (Bootstrapper Series) 4:09

12M ago4:09

4:09

Welcome to the Mafost Mashup reboot - this limited series is for small business owners and dreamers who are ready to bootstrap their way to brand growth and market domination. We'll cover everything you need to know about marketing a small business or startup. ...eventually, we'll polish up our episode endings, lol - forgive me for now. ;) In this …

1
Marketing Assistance: How VAs Can Transform Your Marketing 22:21

12M ago22:21

22:21

Are you tired of struggling with ineffective marketing tactics for your small business? Look no further! In this episode, Gwenn is joined by marketing expert Matt Tompkins and they dive deep into the world of virtual assistants and how they can transform your marketing. From understanding your ideal customer to simplifying your brand voice, Matt pr…

1
The Number One Secret To Project Management 17:20

1y ago17:20

17:20

Are you tired of projects stalling out, underperforming, or causing your team stress? Project management involves a lot of factors, but the key to successful projects happens before you even begin. In this episode, you’ll learn the strategy, execution, and people that are the secret to project management. Gwenn and Jeremy have overseen hundreds of …

1
Crafting Connections with Heart: The Art of Authentic Networking with DeLo and Sahar 49:09

1y ago49:09

49:09

Send us a text Unlock the secrets to authentic networking in an episode that delves into the heart of true connections. With DeLo's journey from music to insurance as a "connector and protector," and Sahar's passion for empowering small businesses, this discussion is a treasure trove of insights for anyone looking to build relationships with purpos…

1
The Shortest Path to Success 1:17:32

1y ago1:17:32

1:17:32

Send us a text Ever wondered how hard work truly pays off? Join me and my friend Gino as we dissect the synergy between effort, strategy, and the elusive concept of success. Our conversation uncovers the transformative power of reading and personal development, especially poignant in times like the COVID era. Gino's journey through books and self-r…

1
Email Management: How To Break Free From Your Inbox 20:51

1y ago20:51

20:51

How much time and money are your emails costing you? Checking an average of 121 emails daily costs us time, but the emotional impact can be even more costly. On this episode, Jeremy and Gwen discuss how to deal with the most problematic emails ranging from emails that cause them the most anxiety to the emails that are the most time consuming. Jerem…

1
Transforming Work Woes: Channeling Hard Work into Your Ticket to a Brighter Future 1:00:44

1y ago1:00:44

1:00:44

Send us a text Ever wonder what it takes to turn a flicker of passion into a blazing career? Essence and Adelaide join us to weave a narrative that begins with a young girl's resolve to transform hairdressing into a business empire, and another's recognition at just 15—a partnership that has since flourished. It's a conversation that celebrates the…

1
Scaling Your Business Without Breaking Your Business 27:51

1y ago27:51

27:51

Tired of hitting roadblocks while growing your business? Break free from the cycle of stress with tips on overcoming obstacles like bad emails and outdated sales structures. Join Gwenn & Jeremy as they discuss scaling challenges faced by entrepreneurs. Learn how to navigate people-related drama & optimize recruitment for successful scaling. Scaling…

1
The Art of Storytelling in Business Growth and Success with Erin Rogers 58:23

1y ago58:23

58:23

Send us a text Have you ever laughed until you cried or found yourself nodding along to a story that felt like it was plucked from your own life? That's the magic Erin Rogers brings to the table, blending comedy and cinema into storytelling that hits home. On our latest episode of Underdogs, Bootstrappers, Game Changers, we sit down with Erin to di…

1
Health And Entrepreneurs: The Solution To Stress 12:55

1y ago12:55

12:55

Are you an entrepreneur who's constantly stressed out? Do you struggle to balance your health and your business? Running a business can take a toll on your health, but it doesn't have to be that way. Join Gwenn and Jeremy as they tackle the critical link between entrepreneurship and health in this episode of Bootstrappers. Gwenn shares a personal s…

1
How to Solve The Labor Shortage Crisis For Your Business 21:14

1y ago21:14

21:14

Are you hiring low quality employees? On this episode of Bootstrappers, Jeremy and Gwenn Aspen unveil groundbreaking strategies to navigate the current labor shortage crisis, introducing listeners to the power of remote teams and why you don’t have to hire B and C employees to your team. Businesses, now more than ever, are struggling to find qualif…

1
Peach Perfect: Cultivating Success at the Roadside Stand with Shannon 1:01:48

1y ago1:01:48

1:01:48

Send us a text Have you ever reveled in the simplicity of a roadside fruit stand, the sweet aroma of peaches wafting through the air? Our latest guest, Shannon, a librarian-turned-entrepreneur, guides us through her incredible transformation into the queen of South Carolina's peach stand scene. Her journey, infused with the entrepreneurial spirit, …

1
Is Your Customer Service Helping Your Business? 18:10

1y ago18:10

18:10

Is your customer service helping your business? When the quality of your customer service is high, you will keep more clients and they will sell your services better than you can. Discover the power of quality assurance in scaling your business as we unveil three simple yet effective tips that you can start implementing today. In this episode, Gwen…

1
Braiding Paths to Success: Essence China's Journey from Underdog to Empire Builder 1:11:34

1+ y ago1:11:34

1:11:34

Send us a text When Essence China started braiding hair in her parents' laundry room, little did she know that she was twining the strands of her future empire. Our latest episode features Essence's journey from humble beginnings to a salon tycoon and beauty school founder, proving how underdogs can bite through systemic barriers with a mix of grit…

1
Calendar Management: Intentional Time, Infinite Energy 20:35

1+ y ago20:35

20:35

Is your calendar working for you or against you? On this episode of the Bootstrappers podcast, Gwen and Jeremy discuss everyone’s most precious resource: Their time. Jeremy gives advice on how he structures his work week so you can have a chill Friday. Gwen dives deep on tips and tricks on how to have your assistants save you time. All this and mor…

1
Navigating the Realities of Startup Life with E-Man and Ky 1:14:32

1+ y ago1:14:32

1:14:32

Send us a text Embark on a thrilling journey with E-Man and Ky, the dynamic duo behind Through Him, as they spill the beans on diving into the business world. Think of it like hitting the gym – it's not about quick wins but building lasting strength and skills. We're here to guide you through the ups and downs of entrepreneurship, from setting up w…

1
Charting a Legacy: Navigating the Waters of Financial Literacy and Asset Protection with Scherrie 1:03:29

1+ y ago1:03:29

1:03:29

Send us a text Picture your life's work, your legacy, slipping through your fingers because of a simple oversight. This nightmare scenario is what Shreve, a seasoned lawyer with a poignant family narrative, and I tackle in our latest podcast episode. We're dedicated to steering you away from the treacherous shoals of financial illiteracy and inadeq…

1
How to Fire Someone 19:32

1+ y ago19:32

19:32

Are you a manager dreading the difficult task of firing someone? Learn how to handle this challenging situation with professionalism and efficiency in this episode of Bootstrappers. Gwenn and Jeremy share their expertise on the best ways to handle one of the most difficult aspects of being a boss - firing someone. We'll guide you through the proces…

1
Three Questions to Increase Your Leadership Game 21:30

1+ y ago21:30

21:30

Are you a leader looking to enhance your skills and make a difference? Look no further! In this episode, Gwenn shares the three crucial questions that every leader should ask themselves to up their leadership game. Join us as we dive into these thought-provoking questions and gain valuable insights into effective leadership. Don't miss out on this …

1
Crafting the Ultimate Business Persona with James L. Bond 1:04:53

1+ y ago1:04:53

1:04:53

Send us a text Have you ever wondered what it's like to go from a technical expert to a sales sensation? Meet James L. Bond, the behavioral management guru and advertising maestro who joins us to unravel his transformative journey. He turns the sales game on its head, showing us that with the right mix of passion and a consultative approach, even t…

1
Mowing Down Barriers to Build a $30 Million Tech Empire with Bryan Clayton 1:04:55

1+ y ago1:04:55

1:04:55

Send us a text Ever wondered how a teenager's lawn mowing side hustle could blossom into a multimillion-dollar landscape empire? Brian's extraordinary journey from pushing a lawn mower to piloting a tech startup unveils the untapped potential within the entrepreneurial spirit. Today, he sits down with us to map out his path to building a $10 millio…

1
How to Make a Million Dollars a Year 29:57

1+ y ago29:57

29:57

Are you tired of searching for the elusive secret to earning $1 million a year with your business? Learn the three key strategies that have helped less than 4% of businesses achieve this success. Jeremy Aspen shares his expertise and personal experience on how to make a million dollars a year. Don't miss out on this valuable information and learn h…

1
Fusing Grit and Grace: Barbie the Welder's Journey Through Metal and Mindsets 1:16:34

1+ y ago1:16:34

1:16:34

Send us a text When Barbie the Welder first struck an arc, she didn't just fuse metal; she sparked a revolution in the trades. Join us as we sit down with the powerhouse sculptor, author, and social media influencer who's cutting through steel and stereotypes alike. Our candid chat traverses her personal saga of resilience, from facing down naysaye…

1
The Grind, a Great Tool For Underdogs But at What Cost? 1:00:23

1+ y ago1:00:23

1:00:23

Send us a text Ever feel like the underdog in a world where the odds are stacked against you? That's the spirit Squalle and I embody as we reminisce about our journey from gritty training partners to trailblazers in the fitness industry. Our conversation isn't just about the hustle—it's a raw, unfiltered look at the sacrifices made and the personal…

1
How to be Organized at Work 24:59

1+ y ago24:59

24:59

Struggling to stay organized while juggling work and family life? Learn how you can stay organized at work without having to sacrifice the other important parts of your life. In this episode of Bootstrappers, Gwenn is joined by Lindsey Savage, an impressive working mom who has mastered productivity. Lindsey shares her three secrets to juggling fami…

1
How To Do A Year In Review 17:40

1+ y ago17:40

17:40

Do you want to start 2024 off with a bang? Join Gwenn as she shares her top tips on how to conduct a meaningful and practical year-end review. Learn how to rid yourself of bad habits, identify energy-sapping activities, set realistic goals, and enhance your time management and relationships. Her invaluable advice will help you take the plunge into …

1
Five Ways Virtual Assistants Fix Toxic Company Culture 19:21

1+ y ago19:21

19:21

Are you looking for ways to prevent a toxic work environment in your business? Look no further! Join Gwenn and Jeremy on this episode of Bootstrappers as they share the five ways virtual assistants can help fix toxic company cultures. Gain valuable insights on how to foster a highly productive and positive work environment, especially when working …

1
Growing an SEO Content Agency to $700k ARR: Julian Canlas 36:31

1+ y ago36:31

36:31

On this episode, we spoke to a friend and long-time Ramen Club member, Julian Canlas, the co-founder of Embarque.io. Embarque is an on-demand content marketing productised service. Started 3 years ago, it’s now making $700k+ ARR, having worked with clients like VEED, Riverside FM and Buy Me A Coffee to name just a few. We discussed the future of SE…

1
How To Deal With A Difficult Boss 21:17

1+ y ago21:17

21:17

Are you having trouble dealing with a bad boss? Whether it's your direct supervisor, an investor, or your company's board, in this episode of Bootstrappers, Gwenn will show you how to handle these difficult people in the workplace. Learn how to stay calm in stressful situations and maintain a successful relationship with those difficult bosses. Tun…

1
Is Remote Work Efficient? 18:08

1+ y ago18:08

18:08

Are you a business owner looking for ways to improve your operations and increase profitability? Working remotely has been growing in popularity, but is it actually efficient? In this episode of Bootstrappers, we’ll explore the many benefits of remote work and find out if it is indeed an efficient solution for streamlining operations, reducing cost…

1
How to be Confident at Work 23:36

1+ y ago23:36

23:36

Do you often feel like you're lacking confidence at work? Are you curious how successful entrepreneurs find their self-assurance? On this episode of Bootstrappers, Gwenn will share her journey and the two key ways that she overcame her struggles with confidence. Find out how to be confident at work and become the leader you've always wanted to be. …

1
The Answer Is A Virtual Executive Assistant 21:52

1+ y ago21:52

21:52

Are you feeling overwhelmed and overworked as a business owner? It may feel like there aren't enough hours in the day to keep your business running, but don't despair! In this episode of Bootstrappers, we'll uncover the secret weapon that can revolutionize your business: a virtual executive assistant. Join us as Gwenn is joined by Julie Hockney as …

1
Is Remote Work The Future of Business? 23:12

1+ y ago23:12

23:12

Are you curious about the future of remote work? With more and more people working from home over the last few years, it's interesting to look at the pros and cons of staying put versus returning to in-person offices. In this episode of Bootstrappers, we'll dive into these factors to see if remote work is here to stay. Join us as we explore the tre…

1
Building Your Remote Team So They Don't Need You 15:04

1+ y ago15:04

15:04

Struggling with how to build a remote team that works without your constant attention? Discover the secrets and strategies of successful remote teams in this episode of Bootrappers. Learn the best practices for boosting productivity, staying connected, and creating a successful remote team you can trust. Don't miss out on building your remote team …

1
Knocking out Challenges in Business with Ryan Diaz 32:04

2y ago32:04

32:04

Send us a text Embrace the thrill of the fight and the grit of entrepreneurship as we welcome the extraordinary Ryan Diaz, a former MMA fighter turned business gladiator. This episode promises an immersive experience into the mind of a man who has conquered not just opponents in the ring, but also the challenges of the business world. In our invigo…

1
Building Fathom Analytics to 450k+ Sites: Jack Ellis 49:51

2y ago49:51

49:51

We spoke to Jack Ellis, Jack is the co-founder of Fathom Analytics, along with Paul Jarvis, and host of the Above Board podcast. Fathom is a privacy-focused web analytics SaaS and excellent Google Analytics alternative. I use Fathom personally on about 5 different websites and can confirm that it’s far easier to navigate and use, in addition to bei…

1
Boostrapping to $25k/month: Dominic Monn (MentorCruise) 53:40

2y ago53:40

53:40

We spoke to Dominic Monn, a longtime Ramen Club member, about bootstrapping MentorCruise - the go-to marketplace to find a career coach or mentor. They help career professionals turn their knowledge into a marketable coaching business, and also make it possible for mentees to find a perfect mentor with just a few clicks. Covering all sorts of topic…

1
How to Motivate Gen Z 20:29

2y ago20:29

20:29

Struggling to understand and connect with Generation Z on your team? Don't miss out on this special episode of Bootstrappers, where we provide insights into how to effectively motivate Generation Z for maximum team success. Join us as we explore how to create an inspiring work environment that enables these young adults to reach their full potentia…

1
Psychological Security To Grow Your Business 24:32

2y ago24:32

24:32

Are you a business leader looking to promote a culture of psychological safety while also having high expectations for your employees? In this episode of Bootstrappers, we discuss what it takes to ensure that your team has both psychological security and high standards. Find out the best practices to empower employees, foster creativity, and set up…

1
The 20 Minute Time Hacking Technique For Time Management 9:24

2y ago9:24

9:24

Do you ever wish that you had more time in your day? Join Gwenn and Jeremy as they show you how to gain control of your schedule and become more productive through easy, step-by-step tips. Discover how to make the most out of your day with The 20 Minute Time Hacking Technique For Time Management - start increasing your efficiency now! Click here fo…

1
How to Stop Hating Meetings: Virtual Assistants 17:34

2y ago17:34

17:34

Are you fed up with the same old monotonous virtual meetings? Has your team's morale and productivity declined during video calls? In this episode, Gwenn and Jeremy share tested tips on how to make meetings more enjoyable and how virtual assistants can supercharge their effectiveness. Forget about dreading meetings, learn how to stop hating them to…

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